organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

(RS)-Efonidipine acetone hemisolvate

CROSSMARK_Color_square_no_text.svg

aSchool of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, People's Republic of China, bSchool of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and cCollaborative Innovation Center of New Drug Research and Safety Evaluation, Henan Province, Zhengzhou 450001, People's Republic of China
*Correspondence e-mail: liwenhaozzu@126.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 20 July 2016; accepted 9 September 2016; online 16 September 2016)

The asymmetric unit of the title compound, C34H38N3O7P·0.5C3H6O {systematic name: (RS)-2-[phenyl(phenyl­meth­yl)amino]­ethyl 5-(5,5-dimethyl-2-oxo-1,3-dioxa-2λ5-phospha­cyclo­hex-2-yl)-2,6-dimethyl-4-(3-nitro­phen­yl)-1,4-di­hydropyridine-3-carboxyl­ate acetone hemisolvate}, contains one R-efonidipine mol­ecule, one S-efonidipine mol­ecule and half of a solvate acetone mol­ecule. In both efonidipine mol­ecules, the six-membered rings of the dioxaphosphinanyl moieties display a chair conformation and the di­hydro­pyridine rings display a flattened boat conformation. In the crystal, N—H⋯O, C—H⋯O hydrogen bonds and weak C—H⋯π inter­actions link the mol­ecules into a three-dimensional supra­molecular structure. A solvent-accessible void of 199 Å3 is found in the structure; the contribution of the heavily disordered solvate mol­ecule was suppressed by use of the SQUEEZE routine in PLATON [Spek (2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]). Acta Cryst. C71, 9–18].

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

(RS)-Efonidipine is an efficient and long-acting Ca2+ channel blocker with renal protection, and has been used clinically in Japan and Korea (Yamashita et al., 1991[Yamashita, T., Masuda, Y., Sakai, T., Tanaka, S. & Kasuya, Y. (1991). Jpn. J. Pharmacol. 57, 337-348.]; Saito et al., 1992[Saito, T., Arakawa, K., Iimura, O., Ogiwara, T., Kanazawa, T., Mizuno, Y., Murakami, E., Ouhashi, Y., Inagaki, Y. & Yamada, K. (1992). Curr. Ther. Res. 52, 113-123.]). (S)-efonidipine has been synthesized by asymmetric synthesis and its crystal structure reported in the space group P212121 (Guo et al., 2008[Guo, Y.-M., Wu, L.-Y., Li, Y.-Y. & Song, H.-R. (2008). Chin. J. Med. Chem, 81, 35-37.]; Sakoda et al., 1992[Sakoda, R., Kamikawaji, Y. & Seto, K. (1992). Chem. Pharm. Bull. 40, 2362-2369.]). Here we report the crystal structure of (RS)-efonidipine acetone hemisolvate. For the structure of an efonidipine analogue, 1,2,3,4,5,6,7,8-octahydro-3,3,6,6-tetramethyl-9-(2-nitrophenyl)xanthene-1,8-dione, see: Jeyakanthan et al. (1999[Jeyakanthan, J., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K. & Murugan, P. (1999). Acta Cryst. C55, 1515-1517.]).

As shown in Fig. 1[link], the asymmetric unit of the title compound contains a (R)-efonidipine mol­ecule, a (S)-efonidipine mol­ecule and half of an acetone mol­ecule. In both efonidipine mol­ecules, the six-membered rings of the dioxaphosphinanyl moieties display a chair conformation and the di­hydro­pyridine rings display a flattened boat conformation.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

In the crystal, classical N—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯π inter­actions (Table 1[link]) link the mol­ecules into a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg9 are the centroids of the C22′–C27′ and C22–C27 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O3′ 0.86 2.04 2.847 (2) 155
N1′—H1′⋯O3i 0.86 2.20 2.917 (2) 141
C1—H1A⋯O6ii 0.97 2.54 3.456 (4) 157
C1′—H1′B⋯O6′iii 0.97 2.42 3.346 (4) 160
C15′—H15′⋯O5 0.93 2.55 3.470 (7) 173
C37—H37CCg4iv 0.96 2.88 3.667 (9) 139
C3′—H3′BCg9v 0.97 2.66 3.599 (3) 163
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+1, -z+1; (v) x+1, y-1, z.

Synthesis and crystallization

(RS)-Efonidipine was prepared using a Hantzsch pyridine reaction, starting with two inter­mediates I {2-butenoic acid, 3-amino-2-[phen­yl(phenyl­meth­yl)amino] ethyl ester} and II {3-buten-2-one, 3-(5,5-dimethyl-2-oxido-1,3,2-dioxa­phos­phor­inan-2-yl)-4-(3-nitro­phen­yl)}. The inter­mediates I (7.0 g, 22.55 mmol) and II (7.6 g, 22.40 mmol) were dissolved in 150 ml of 2-propanol at 83° C with reflux, stirred for 3 h, then cooled down to room temperature and stirred for 8 h, vacuum filtration, recrystallized in 100 ml of ethanol, vacuum drying, yield 11.05 g (78.09%). Slow evaporation of a solution in acetone while left to stand for 4 days gave light-yellow rhombus-shaped columnar crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The solvent-accessible void of 199 Å3 is found in the structure, the presumed contribution of a heavily disordered solvate mol­ecule was suppressed by the SQUEEZE routine in PLATON (Spek, 2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]).

Table 2
Experimental details

Crystal data
Chemical formula C34H38N3O7P·0.5C3H6O
Mr 660.68
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 13.9972 (6), 17.2985 (4), 18.4787 (6)
α, β, γ (°) 63.725 (3), 68.593 (3), 67.115 (4)
V3) 3594.1 (3)
Z 4
Radiation type Cu Kα
μ (mm−1) 1.10
Crystal size (mm) 0.32 × 0.25 × 0.2
 
Data collection
Diffractometer Agilent Xcalibur, Eos, Gemini
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.])
Tmin, Tmax 0.575, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 56083, 12829, 10943
Rint 0.050
(sin θ/λ)max−1) 0.597
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.196, 1.05
No. of reflections 12829
No. of parameters 857
No. of restraints 38
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.93, −0.49
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), SHELXS (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

RS-2-(Phenyl(phenylmethyl)amino)ethyl 5-(5,5-dimethyl-2-oxo-1,3-dioxa-2λ5-phosphacyclohex-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate acetone hemisolvate top
Crystal data top
C34H38N3O7P·0.5C3H6OZ = 4
Mr = 660.68F(000) = 1400
Triclinic, P1Dx = 1.221 Mg m3
a = 13.9972 (6) ÅCu Kα radiation, λ = 1.54184 Å
b = 17.2985 (4) ÅCell parameters from 17758 reflections
c = 18.4787 (6) Åθ = 3.6–70.8°
α = 63.725 (3)°µ = 1.10 mm1
β = 68.593 (3)°T = 293 K
γ = 67.115 (4)°Block, yellow
V = 3594.1 (3) Å30.32 × 0.25 × 0.2 mm
Data collection top
Agilent Xcalibur, Eos, Gemini
diffractometer
12829 independent reflections
Radiation source: Enhance (Cu) X-ray Source10943 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 16.2312 pixels mm-1θmax = 67.1°, θmin = 3.5°
ω scansh = 1616
Absorption correction: multi-scan
(CrysAlis Pro; Agilent, 2014)
k = 2020
Tmin = 0.575, Tmax = 1.000l = 2222
56083 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.196 w = 1/[σ2(Fo2) + (0.1265P)2 + 0.9921P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
12829 reflectionsΔρmax = 0.93 e Å3
857 parametersΔρmin = 0.49 e Å3
38 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3215 (2)0.82686 (17)0.00144 (16)0.0549 (6)
H1A0.36870.86240.01430.066*
H1B0.26360.86530.02910.066*
C20.3824 (2)0.75075 (19)0.03425 (16)0.0561 (6)
C30.4714 (2)0.6915 (2)0.01101 (18)0.0622 (7)
H3A0.51280.64270.00990.075*
H3B0.51850.72620.00010.075*
C40.4328 (3)0.7904 (3)0.12659 (19)0.0829 (10)
H4A0.37830.83430.15500.124*
H4B0.46740.74360.14960.124*
H4C0.48430.81830.13310.124*
C50.3101 (3)0.6968 (2)0.02151 (19)0.0685 (8)
H5A0.28700.66570.03670.103*
H5B0.34860.65430.04940.103*
H5C0.24910.73650.04390.103*
C60.52984 (16)0.74078 (14)0.16638 (14)0.0419 (5)
C70.43285 (16)0.78168 (14)0.14929 (13)0.0388 (4)
C80.37752 (16)0.87938 (14)0.14128 (14)0.0403 (4)
H80.34900.90900.09150.048*
C90.45699 (16)0.92695 (14)0.12951 (13)0.0390 (4)
C100.55301 (16)0.88028 (15)0.14821 (14)0.0416 (5)
C110.5922 (2)0.64459 (16)0.1784 (2)0.0588 (6)
H11D0.64560.64120.12860.088*
H11E0.54480.61020.19080.088*
H11F0.62590.62100.22360.088*
C120.63500 (19)0.91921 (18)0.14379 (18)0.0552 (6)
H12D0.69080.87190.16860.083*
H12E0.60200.96050.17320.083*
H12F0.66460.95010.08680.083*
C130.28356 (17)0.88676 (15)0.21580 (17)0.0484 (5)
C140.3000 (2)0.85466 (18)0.29409 (18)0.0589 (6)
H140.36890.82950.30240.071*
C150.2133 (3)0.8601 (2)0.3605 (2)0.0747 (9)
C160.1102 (3)0.8963 (3)0.3506 (3)0.0912 (12)
H160.05290.89890.39610.109*
C170.0936 (2)0.9283 (3)0.2728 (3)0.0955 (13)
H170.02430.95280.26530.115*
C180.1793 (2)0.9248 (2)0.2045 (2)0.0738 (8)
H180.16740.94760.15170.089*
C190.42528 (17)1.02457 (15)0.09720 (14)0.0439 (5)
C200.2875 (2)1.15274 (16)0.04375 (17)0.0561 (6)
H20C0.26141.17230.00520.067*
H20D0.34051.18330.02980.067*
C210.1962 (2)1.17484 (15)0.11350 (15)0.0497 (5)
H21C0.15081.13560.13380.060*
H21D0.22461.16360.15890.060*
C220.1755 (2)1.33439 (16)0.07568 (16)0.0532 (6)
C230.2416 (2)1.3172 (2)0.12598 (19)0.0635 (7)
H230.25831.26070.16600.076*
C240.2818 (3)1.3827 (3)0.1168 (2)0.0782 (9)
H240.32611.36950.15030.094*
C250.2580 (3)1.4672 (3)0.0592 (3)0.0962 (13)
H250.28541.51120.05360.115*
C260.1941 (4)1.4852 (2)0.0108 (3)0.0980 (14)
H260.17721.54260.02790.118*
C270.1522 (3)1.42034 (19)0.0170 (2)0.0724 (8)
H270.10911.43450.01780.087*
C280.0648 (2)1.29038 (18)0.03193 (19)0.0622 (7)
H28C0.10811.29970.02430.075*
H28D0.01011.34590.03240.075*
C290.0127 (2)1.21837 (19)0.0569 (2)0.0649 (7)
C300.0632 (3)1.1985 (2)0.1317 (2)0.0812 (9)
H300.08401.23200.16540.097*
C310.1071 (3)1.1306 (3)0.1558 (4)0.1045 (14)
H310.15671.11730.20620.125*
C320.0786 (4)1.0820 (3)0.1062 (4)0.1177 (18)
H320.10811.03530.12280.141*
C330.0063 (5)1.1024 (3)0.0319 (4)0.1131 (15)
H330.01191.07010.00240.136*
C340.0401 (3)1.1700 (3)0.0069 (3)0.0864 (10)
H340.08971.18270.04360.104*
N10.58447 (14)0.78856 (12)0.17179 (13)0.0457 (4)
H10.64100.75960.19090.055*
N20.2307 (4)0.8258 (3)0.4430 (2)0.1114 (12)
N30.13209 (16)1.26804 (13)0.08721 (13)0.0507 (5)
O10.27786 (11)0.79476 (10)0.08821 (10)0.0451 (4)
O20.42944 (13)0.65511 (11)0.09956 (11)0.0510 (4)
O30.29406 (14)0.67610 (13)0.22736 (11)0.0563 (4)
O40.1529 (4)0.8275 (4)0.5002 (2)0.191 (2)
O50.3205 (4)0.7993 (4)0.4505 (2)0.1607 (18)
O60.47088 (17)1.07441 (12)0.09126 (15)0.0716 (6)
O70.33406 (13)1.05736 (11)0.07105 (12)0.0565 (4)
P10.35504 (4)0.72254 (4)0.14661 (3)0.03924 (16)
C1'0.8422 (2)0.46689 (17)0.34018 (16)0.0540 (6)
H1'A0.78740.43590.37400.065*
H1'B0.88220.46090.37650.065*
C2'0.9168 (2)0.42312 (18)0.27692 (17)0.0558 (6)
C3'0.99985 (19)0.47459 (17)0.22293 (17)0.0539 (6)
H3'A1.04060.47150.25730.065*
H3'B1.04880.44720.18240.065*
C4'0.8536 (3)0.4228 (3)0.2244 (2)0.0767 (9)
H4'A0.82240.48340.19250.115*
H4'B0.79830.39390.26020.115*
H4'C0.90070.39100.18760.115*
C5'0.9748 (3)0.3270 (2)0.3238 (2)0.0829 (9)
H5'A1.02450.29910.28470.124*
H5'B0.92360.29340.35880.124*
H5'C1.01240.32850.35720.124*
C6'1.02119 (17)0.66646 (15)0.25335 (13)0.0426 (5)
C7'0.92907 (16)0.64304 (14)0.29022 (13)0.0391 (4)
C8'0.86958 (16)0.64201 (15)0.37817 (13)0.0398 (4)
H8'0.84160.58940.40740.048*
C9'0.94629 (16)0.63279 (14)0.42430 (13)0.0388 (4)
C10'1.03893 (17)0.65626 (14)0.38304 (14)0.0421 (5)
C11'1.0839 (2)0.6770 (2)0.16599 (15)0.0603 (7)
H11A1.09990.73390.13990.091*
H11B1.04300.67420.13580.091*
H11C1.14920.62980.16620.091*
C12'1.1179 (2)0.6566 (2)0.42041 (17)0.0562 (6)
H12A1.14980.59630.45240.084*
H12B1.08190.69160.45580.084*
H12C1.17240.68210.37690.084*
C13'0.77520 (17)0.72550 (17)0.37620 (14)0.0480 (5)
C14'0.6721 (2)0.7201 (3)0.3965 (2)0.0778 (9)
H14'0.65960.66540.41130.093*
C15'0.5864 (3)0.7974 (4)0.3946 (3)0.1037 (14)
H15'0.51730.79310.40860.124*
C16'0.6016 (3)0.8775 (3)0.3731 (2)0.0926 (12)
H16'0.54440.92850.37200.111*
C17'0.7049 (3)0.8812 (2)0.3529 (2)0.0846 (11)
C18'0.7913 (2)0.80735 (18)0.35421 (17)0.0635 (7)
H18'0.85990.81260.34040.076*
C19'0.91776 (17)0.59837 (15)0.51501 (14)0.0429 (5)
C20'0.7868 (2)0.54706 (17)0.63447 (15)0.0538 (6)
H20A0.84630.50090.65650.065*
H20B0.73050.51950.64960.065*
C21'0.7468 (2)0.61830 (19)0.67325 (16)0.0573 (6)
H21A0.73440.58930.73310.069*
H21B0.80220.64770.65540.069*
C22'0.5513 (2)0.67157 (18)0.69936 (17)0.0568 (6)
C23'0.5416 (3)0.5900 (2)0.76480 (19)0.0659 (7)
H23'0.60280.54420.77660.079*
C24'0.4427 (3)0.5771 (3)0.8117 (2)0.0783 (9)
H24'0.43870.52300.85510.094*
C25'0.3514 (3)0.6416 (3)0.7959 (3)0.0891 (11)
H25'0.28530.63240.82810.107*
C26'0.3586 (3)0.7200 (3)0.7320 (3)0.0966 (12)
H26'0.29610.76380.71990.116*
C27'0.4559 (3)0.7371 (2)0.6842 (2)0.0791 (9)
H27'0.45770.79220.64200.095*
C28'0.6654 (3)0.7689 (2)0.58599 (19)0.0720 (8)
H28A0.59970.80240.56730.086*
H28B0.72050.75490.53970.086*
C29'0.6958 (3)0.8272 (2)0.61009 (19)0.0719 (8)
C30'0.6320 (3)0.8580 (2)0.6734 (2)0.0838 (9)
H30'0.56840.84210.70200.101*
C31'0.6573 (5)0.9111 (3)0.6965 (3)0.1077 (12)
H31'0.60950.93540.73650.129*
C32'0.7567 (7)0.9278 (4)0.6586 (5)0.141 (2)
H32'0.77560.96310.67440.169*
C33'0.8295 (6)0.8930 (5)0.5972 (6)0.165 (3)
H33'0.89660.90330.57300.198*
C34'0.7969 (5)0.8425 (4)0.5743 (4)0.131 (2)
H34'0.84350.81810.53410.158*
N1'1.06906 (15)0.68152 (14)0.29796 (12)0.0470 (4)
H1'1.11940.70760.27140.056*
N2'0.7245 (4)0.9673 (2)0.3311 (4)0.155 (2)
N3'0.65064 (18)0.68538 (15)0.65318 (15)0.0624 (6)
O1'0.79168 (12)0.56194 (12)0.30105 (10)0.0475 (4)
O2'0.94974 (12)0.56802 (11)0.18010 (9)0.0470 (4)
O3'0.80143 (13)0.70705 (12)0.18227 (11)0.0552 (4)
O4'0.8163 (4)0.9680 (2)0.3326 (5)0.220 (3)
O5'0.6487 (4)1.0330 (2)0.3217 (4)0.220 (3)
O6'0.97116 (14)0.58385 (14)0.56099 (11)0.0610 (5)
O7'0.82021 (12)0.58317 (11)0.54522 (9)0.0473 (4)
P1'0.86414 (4)0.62486 (4)0.23432 (3)0.03975 (16)
C350.4273 (4)0.5150 (4)0.4367 (3)0.1148 (15)
C360.4288 (6)0.6091 (5)0.3903 (4)0.159 (3)
H36A0.39980.63190.34270.238*
H36B0.50080.61300.37250.238*
H36C0.38660.64390.42540.238*
C370.5091 (6)0.4464 (6)0.4009 (5)0.170 (3)
H37A0.57670.45970.37990.255*
H37B0.48780.44760.35650.255*
H37C0.51520.38810.44320.255*
O80.3668 (4)0.4943 (4)0.5027 (3)0.1588 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0630 (15)0.0539 (13)0.0562 (13)0.0234 (11)0.0201 (11)0.0152 (11)
C20.0627 (15)0.0672 (16)0.0503 (13)0.0345 (13)0.0055 (11)0.0223 (11)
C30.0511 (14)0.0705 (17)0.0733 (17)0.0211 (12)0.0015 (12)0.0411 (14)
C40.104 (3)0.109 (3)0.0541 (16)0.063 (2)0.0018 (16)0.0286 (17)
C50.0800 (19)0.083 (2)0.0680 (16)0.0431 (16)0.0114 (14)0.0344 (15)
C60.0329 (10)0.0398 (11)0.0554 (12)0.0100 (8)0.0112 (9)0.0180 (9)
C70.0313 (9)0.0370 (10)0.0514 (11)0.0090 (8)0.0089 (8)0.0191 (9)
C80.0309 (10)0.0370 (10)0.0573 (12)0.0091 (8)0.0132 (9)0.0181 (9)
C90.0343 (10)0.0383 (10)0.0487 (11)0.0113 (8)0.0073 (8)0.0197 (9)
C100.0342 (10)0.0462 (11)0.0496 (11)0.0134 (9)0.0082 (8)0.0203 (9)
C110.0443 (12)0.0414 (12)0.0928 (19)0.0020 (10)0.0267 (13)0.0250 (12)
C120.0438 (12)0.0564 (14)0.0769 (16)0.0176 (10)0.0204 (11)0.0247 (12)
C130.0317 (10)0.0375 (11)0.0757 (16)0.0102 (8)0.0043 (10)0.0254 (11)
C140.0493 (13)0.0588 (15)0.0698 (16)0.0193 (11)0.0009 (12)0.0299 (13)
C150.0636 (17)0.0707 (18)0.084 (2)0.0324 (15)0.0159 (15)0.0361 (16)
C160.0591 (19)0.081 (2)0.107 (3)0.0245 (16)0.0261 (19)0.042 (2)
C170.0334 (14)0.093 (2)0.133 (4)0.0069 (14)0.0035 (17)0.044 (2)
C180.0377 (13)0.0678 (17)0.106 (2)0.0066 (12)0.0120 (14)0.0319 (16)
C190.0369 (10)0.0437 (11)0.0543 (12)0.0118 (9)0.0075 (9)0.0216 (9)
C200.0500 (13)0.0357 (11)0.0696 (15)0.0048 (10)0.0134 (11)0.0139 (11)
C210.0514 (13)0.0380 (11)0.0559 (13)0.0053 (9)0.0196 (10)0.0136 (10)
C220.0510 (13)0.0438 (12)0.0557 (13)0.0078 (10)0.0024 (10)0.0258 (10)
C230.0585 (15)0.0633 (16)0.0720 (17)0.0100 (12)0.0068 (13)0.0388 (14)
C240.0650 (18)0.088 (2)0.101 (2)0.0252 (16)0.0062 (16)0.066 (2)
C250.077 (2)0.081 (2)0.137 (4)0.036 (2)0.022 (2)0.068 (3)
C260.096 (3)0.0512 (18)0.111 (3)0.0243 (17)0.014 (2)0.0243 (18)
C270.0732 (18)0.0478 (15)0.0741 (18)0.0127 (13)0.0049 (15)0.0155 (13)
C280.0581 (15)0.0513 (14)0.0683 (16)0.0025 (11)0.0268 (13)0.0144 (12)
C290.0552 (15)0.0574 (15)0.0807 (18)0.0055 (12)0.0309 (14)0.0196 (13)
C300.0619 (18)0.078 (2)0.096 (2)0.0171 (15)0.0173 (17)0.0268 (18)
C310.075 (2)0.090 (3)0.137 (4)0.028 (2)0.028 (2)0.022 (3)
C320.106 (3)0.088 (3)0.171 (5)0.042 (3)0.063 (4)0.018 (3)
C330.137 (4)0.095 (3)0.148 (4)0.036 (3)0.065 (4)0.047 (3)
C340.089 (2)0.088 (2)0.096 (2)0.0158 (19)0.044 (2)0.034 (2)
N10.0335 (9)0.0401 (9)0.0677 (12)0.0061 (7)0.0212 (8)0.0185 (8)
N20.107 (3)0.144 (3)0.0703 (19)0.047 (3)0.015 (2)0.044 (2)
N30.0519 (11)0.0393 (10)0.0573 (11)0.0037 (8)0.0174 (9)0.0176 (8)
O10.0352 (7)0.0488 (8)0.0576 (9)0.0124 (6)0.0120 (6)0.0223 (7)
O20.0495 (9)0.0445 (8)0.0648 (10)0.0110 (7)0.0132 (7)0.0257 (7)
O30.0500 (9)0.0670 (11)0.0539 (9)0.0333 (8)0.0060 (7)0.0130 (8)
O40.138 (3)0.303 (7)0.083 (2)0.083 (4)0.042 (2)0.061 (3)
O50.120 (3)0.259 (6)0.082 (2)0.038 (3)0.013 (2)0.061 (3)
O60.0704 (12)0.0439 (9)0.1145 (17)0.0208 (9)0.0415 (12)0.0195 (10)
O70.0435 (9)0.0363 (8)0.0875 (12)0.0047 (7)0.0227 (8)0.0193 (8)
P10.0322 (3)0.0397 (3)0.0505 (3)0.0139 (2)0.0076 (2)0.0179 (2)
C1'0.0544 (13)0.0594 (14)0.0512 (12)0.0257 (11)0.0112 (10)0.0141 (11)
C2'0.0585 (14)0.0567 (14)0.0624 (14)0.0167 (11)0.0186 (12)0.0252 (12)
C3'0.0414 (12)0.0565 (14)0.0659 (14)0.0059 (10)0.0111 (11)0.0307 (12)
C4'0.084 (2)0.091 (2)0.086 (2)0.0327 (18)0.0256 (17)0.0454 (18)
C5'0.096 (2)0.0528 (16)0.094 (2)0.0149 (16)0.0293 (19)0.0203 (16)
C6'0.0345 (10)0.0520 (12)0.0431 (11)0.0159 (9)0.0097 (8)0.0141 (9)
C7'0.0324 (10)0.0470 (11)0.0402 (10)0.0121 (8)0.0096 (8)0.0152 (9)
C8'0.0327 (10)0.0472 (11)0.0422 (10)0.0128 (8)0.0073 (8)0.0173 (9)
C9'0.0350 (10)0.0399 (10)0.0446 (11)0.0089 (8)0.0099 (8)0.0180 (9)
C10'0.0395 (11)0.0426 (11)0.0494 (11)0.0104 (9)0.0139 (9)0.0184 (9)
C11'0.0473 (13)0.094 (2)0.0459 (12)0.0374 (13)0.0017 (10)0.0213 (13)
C12'0.0515 (13)0.0721 (16)0.0608 (14)0.0275 (12)0.0158 (11)0.0256 (12)
C13'0.0344 (11)0.0644 (14)0.0442 (11)0.0056 (10)0.0094 (9)0.0246 (10)
C14'0.0379 (13)0.105 (2)0.109 (2)0.0099 (14)0.0120 (14)0.065 (2)
C15'0.0346 (15)0.148 (4)0.135 (3)0.0077 (19)0.0234 (18)0.081 (3)
C16'0.068 (2)0.091 (3)0.092 (2)0.0254 (19)0.0327 (18)0.039 (2)
C17'0.0681 (19)0.0615 (18)0.0729 (19)0.0089 (15)0.0067 (15)0.0106 (14)
C18'0.0492 (14)0.0506 (14)0.0626 (15)0.0065 (11)0.0043 (11)0.0089 (12)
C19'0.0399 (11)0.0444 (11)0.0463 (11)0.0051 (9)0.0124 (9)0.0210 (9)
C20'0.0548 (13)0.0544 (13)0.0440 (12)0.0142 (11)0.0024 (10)0.0181 (10)
C21'0.0541 (14)0.0695 (16)0.0499 (13)0.0174 (12)0.0035 (11)0.0288 (12)
C22'0.0545 (14)0.0593 (15)0.0656 (15)0.0126 (11)0.0091 (12)0.0359 (12)
C23'0.0674 (17)0.0644 (16)0.0679 (16)0.0181 (13)0.0048 (13)0.0334 (14)
C24'0.086 (2)0.090 (2)0.0777 (19)0.0440 (19)0.0031 (17)0.0461 (17)
C25'0.070 (2)0.122 (3)0.104 (3)0.043 (2)0.0038 (19)0.063 (3)
C26'0.0522 (18)0.128 (3)0.120 (3)0.0054 (19)0.0224 (19)0.067 (3)
C27'0.0674 (19)0.074 (2)0.097 (2)0.0054 (15)0.0255 (17)0.0380 (18)
C28'0.084 (2)0.0671 (17)0.0580 (15)0.0199 (15)0.0076 (14)0.0237 (13)
C29'0.087 (2)0.0541 (15)0.0602 (15)0.0224 (14)0.0065 (14)0.0136 (12)
C30'0.100 (2)0.078 (2)0.0734 (19)0.0219 (17)0.0138 (17)0.0337 (16)
C31'0.158 (3)0.077 (2)0.100 (3)0.023 (2)0.044 (2)0.038 (2)
C32'0.198 (5)0.101 (3)0.156 (5)0.075 (4)0.056 (4)0.032 (3)
C33'0.154 (6)0.152 (6)0.204 (8)0.093 (5)0.009 (5)0.057 (5)
C34'0.138 (4)0.130 (4)0.138 (4)0.078 (4)0.020 (3)0.062 (3)
N1'0.0391 (9)0.0586 (11)0.0494 (10)0.0247 (8)0.0082 (8)0.0158 (9)
N2'0.126 (3)0.0446 (17)0.191 (4)0.003 (2)0.012 (3)0.013 (2)
N3'0.0561 (12)0.0555 (12)0.0674 (13)0.0110 (10)0.0066 (10)0.0245 (10)
O1'0.0333 (7)0.0649 (10)0.0509 (8)0.0184 (7)0.0062 (6)0.0244 (7)
O2'0.0406 (8)0.0581 (9)0.0443 (8)0.0130 (7)0.0070 (6)0.0222 (7)
O3'0.0419 (8)0.0616 (10)0.0622 (10)0.0066 (7)0.0248 (7)0.0180 (8)
O4'0.124 (3)0.069 (2)0.338 (7)0.034 (2)0.047 (4)0.035 (3)
O5'0.177 (4)0.066 (2)0.295 (7)0.037 (2)0.043 (4)0.029 (3)
O6'0.0511 (9)0.0853 (13)0.0502 (9)0.0164 (9)0.0183 (8)0.0235 (9)
O7'0.0429 (8)0.0573 (9)0.0428 (8)0.0166 (7)0.0041 (6)0.0208 (7)
P1'0.0282 (3)0.0511 (3)0.0426 (3)0.0096 (2)0.0105 (2)0.0178 (2)
C350.110 (3)0.153 (5)0.100 (3)0.045 (3)0.028 (3)0.049 (3)
C360.170 (6)0.160 (6)0.111 (4)0.024 (5)0.046 (4)0.025 (4)
C370.193 (7)0.210 (8)0.152 (5)0.064 (6)0.019 (5)0.112 (6)
O80.149 (3)0.180 (4)0.131 (3)0.069 (3)0.011 (3)0.054 (3)
Geometric parameters (Å, º) top
C1—H1A0.9700C2'—C4'1.536 (4)
C1—H1B0.9700C2'—C5'1.537 (4)
C1—C21.511 (4)C3'—H3'A0.9700
C1—O11.462 (3)C3'—H3'B0.9700
C2—C31.520 (4)C3'—O2'1.457 (3)
C2—C41.530 (4)C4'—H4'A0.9600
C2—C51.522 (4)C4'—H4'B0.9600
C3—H3A0.9700C4'—H4'C0.9600
C3—H3B0.9700C5'—H5'A0.9600
C3—O21.446 (3)C5'—H5'B0.9600
C4—H4A0.9600C5'—H5'C0.9600
C4—H4B0.9600C6'—C7'1.346 (3)
C4—H4C0.9600C6'—C11'1.496 (3)
C5—H5A0.9600C6'—N1'1.388 (3)
C5—H5B0.9600C7'—C8'1.527 (3)
C5—H5C0.9600C7'—P1'1.785 (2)
C6—C71.346 (3)C8'—H8'0.9800
C6—C111.505 (3)C8'—C9'1.523 (3)
C6—N11.378 (3)C8'—C13'1.529 (3)
C7—C81.524 (3)C9'—C10'1.357 (3)
C7—P11.785 (2)C9'—C19'1.462 (3)
C8—H80.9800C10'—C12'1.505 (3)
C8—C91.529 (3)C10'—N1'1.375 (3)
C8—C131.531 (3)C11'—H11A0.9600
C9—C101.351 (3)C11'—H11B0.9600
C9—C191.457 (3)C11'—H11C0.9600
C10—C121.504 (3)C12'—H12A0.9600
C10—N11.373 (3)C12'—H12B0.9600
C11—H11D0.9600C12'—H12C0.9600
C11—H11E0.9600C13'—C14'1.382 (4)
C11—H11F0.9600C13'—C18'1.376 (4)
C12—H12D0.9600C14'—H14'0.9300
C12—H12E0.9600C14'—C15'1.404 (5)
C12—H12F0.9600C15'—H15'0.9300
C13—C141.373 (4)C15'—C16'1.342 (7)
C13—C181.399 (4)C16'—H16'0.9300
C14—H140.9300C16'—C17'1.375 (6)
C14—C151.383 (4)C17'—C18'1.374 (4)
C15—C161.377 (6)C17'—N2'1.470 (6)
C15—N21.447 (6)C18'—H18'0.9300
C16—H160.9300C19'—O6'1.213 (3)
C16—C171.367 (7)C19'—O7'1.356 (3)
C17—H170.9300C20'—H20A0.9700
C17—C181.393 (5)C20'—H20B0.9700
C18—H180.9300C20'—C21'1.516 (4)
C19—O61.207 (3)C20'—O7'1.443 (3)
C19—O71.353 (3)C21'—H21A0.9700
C20—H20C0.9700C21'—H21B0.9700
C20—H20D0.9700C21'—N3'1.436 (4)
C20—C211.515 (4)C22'—C23'1.410 (4)
C20—O71.438 (3)C22'—C27'1.401 (4)
C21—H21C0.9700C22'—N3'1.390 (4)
C21—H21D0.9700C23'—H23'0.9300
C21—N31.463 (3)C23'—C24'1.382 (4)
C22—C231.406 (4)C24'—H24'0.9300
C22—C271.395 (4)C24'—C25'1.356 (6)
C22—N31.401 (3)C25'—H25'0.9300
C23—H230.9300C25'—C26'1.358 (6)
C23—C241.373 (4)C26'—H26'0.9300
C24—H240.9300C26'—C27'1.388 (6)
C24—C251.373 (6)C27'—H27'0.9300
C25—H250.9300C28'—H28A0.9700
C25—C261.348 (7)C28'—H28B0.9700
C26—H260.9300C28'—C29'1.505 (5)
C26—C271.402 (6)C28'—N3'1.459 (4)
C27—H270.9300C29'—C30'1.367 (5)
C28—H28C0.9700C29'—C34'1.401 (6)
C28—H28D0.9700C30'—H30'0.9300
C28—C291.499 (4)C30'—C31'1.366 (6)
C28—N31.466 (3)C31'—H31'0.9300
C29—C301.397 (5)C31'—C32'1.390 (9)
C29—C341.369 (5)C32'—H32'0.9300
C30—H300.9300C32'—C33'1.404 (10)
C30—C311.362 (6)C33'—H33'0.9300
C31—H310.9300C33'—C34'1.389 (9)
C31—C321.363 (8)C34'—H34'0.9300
C32—H320.9300N1'—H1'0.8600
C32—C331.367 (8)N2'—O4'1.301 (8)
C33—H330.9300N2'—O5'1.212 (5)
C33—C341.377 (6)O1'—P1'1.5784 (16)
C34—H340.9300O2'—P1'1.5767 (16)
N1—H10.8600O3'—P1'1.4670 (17)
N2—O41.210 (5)C35—C361.471 (9)
N2—O51.198 (5)C35—C371.497 (9)
O1—P11.5811 (16)C35—O81.195 (6)
O2—P11.5790 (16)C36—H36A0.9600
O3—P11.4637 (17)C36—H36B0.9600
C1'—H1'A0.9700C36—H36C0.9600
C1'—H1'B0.9700C37—H37A0.9600
C1'—C2'1.519 (4)C37—H37B0.9600
C1'—O1'1.464 (3)C37—H37C0.9600
C2'—C3'1.520 (4)
H1A—C1—H1B107.9C1'—C2'—C5'108.3 (2)
C2—C1—H1A109.2C3'—C2'—C4'111.2 (2)
C2—C1—H1B109.2C3'—C2'—C5'108.1 (2)
O1—C1—H1A109.2C4'—C2'—C5'110.7 (3)
O1—C1—H1B109.2C2'—C3'—H3'A109.4
O1—C1—C2112.1 (2)C2'—C3'—H3'B109.4
C1—C2—C3107.7 (2)H3'A—C3'—H3'B108.0
C1—C2—C4108.2 (2)O2'—C3'—C2'111.04 (19)
C1—C2—C5111.5 (2)O2'—C3'—H3'A109.4
C3—C2—C4108.4 (3)O2'—C3'—H3'B109.4
C3—C2—C5110.5 (2)C2'—C4'—H4'A109.5
C5—C2—C4110.5 (2)C2'—C4'—H4'B109.5
C2—C3—H3A109.4C2'—C4'—H4'C109.5
C2—C3—H3B109.4H4'A—C4'—H4'B109.5
H3A—C3—H3B108.0H4'A—C4'—H4'C109.5
O2—C3—C2111.4 (2)H4'B—C4'—H4'C109.5
O2—C3—H3A109.4C2'—C5'—H5'A109.5
O2—C3—H3B109.4C2'—C5'—H5'B109.5
C2—C4—H4A109.5C2'—C5'—H5'C109.5
C2—C4—H4B109.5H5'A—C5'—H5'B109.5
C2—C4—H4C109.5H5'A—C5'—H5'C109.5
H4A—C4—H4B109.5H5'B—C5'—H5'C109.5
H4A—C4—H4C109.5C7'—C6'—C11'127.1 (2)
H4B—C4—H4C109.5C7'—C6'—N1'120.0 (2)
C2—C5—H5A109.5N1'—C6'—C11'112.90 (19)
C2—C5—H5B109.5C6'—C7'—C8'121.03 (19)
C2—C5—H5C109.5C6'—C7'—P1'121.26 (16)
H5A—C5—H5B109.5C8'—C7'—P1'117.32 (14)
H5A—C5—H5C109.5C7'—C8'—H8'108.0
H5B—C5—H5C109.5C7'—C8'—C13'110.64 (17)
C7—C6—C11127.1 (2)C9'—C8'—C7'109.97 (16)
C7—C6—N1120.19 (19)C9'—C8'—H8'108.0
N1—C6—C11112.64 (18)C9'—C8'—C13'112.01 (18)
C6—C7—C8121.41 (19)C13'—C8'—H8'108.0
C6—C7—P1122.43 (16)C10'—C9'—C8'121.47 (19)
C8—C7—P1115.78 (14)C10'—C9'—C19'120.07 (19)
C7—C8—H8107.7C19'—C9'—C8'118.46 (18)
C7—C8—C9110.85 (16)C9'—C10'—C12'127.0 (2)
C7—C8—C13110.87 (18)C9'—C10'—N1'119.47 (19)
C9—C8—H8107.7N1'—C10'—C12'113.5 (2)
C9—C8—C13111.82 (18)C6'—C11'—H11A109.5
C13—C8—H8107.7C6'—C11'—H11B109.5
C10—C9—C8121.29 (19)C6'—C11'—H11C109.5
C10—C9—C19121.26 (19)H11A—C11'—H11B109.5
C19—C9—C8117.45 (18)H11A—C11'—H11C109.5
C9—C10—C12126.2 (2)H11B—C11'—H11C109.5
C9—C10—N1119.97 (19)C10'—C12'—H12A109.5
N1—C10—C12113.85 (19)C10'—C12'—H12B109.5
C6—C11—H11D109.5C10'—C12'—H12C109.5
C6—C11—H11E109.5H12A—C12'—H12B109.5
C6—C11—H11F109.5H12A—C12'—H12C109.5
H11D—C11—H11E109.5H12B—C12'—H12C109.5
H11D—C11—H11F109.5C14'—C13'—C8'120.6 (3)
H11E—C11—H11F109.5C18'—C13'—C8'120.6 (2)
C10—C12—H12D109.5C18'—C13'—C14'118.8 (3)
C10—C12—H12E109.5C13'—C14'—H14'120.1
C10—C12—H12F109.5C13'—C14'—C15'119.7 (4)
H12D—C12—H12E109.5C15'—C14'—H14'120.1
H12D—C12—H12F109.5C14'—C15'—H15'119.1
H12E—C12—H12F109.5C16'—C15'—C14'121.8 (3)
C14—C13—C8120.8 (2)C16'—C15'—H15'119.1
C14—C13—C18119.4 (3)C15'—C16'—H16'121.3
C18—C13—C8119.7 (3)C15'—C16'—C17'117.3 (3)
C13—C14—H14120.3C17'—C16'—H16'121.3
C13—C14—C15119.5 (3)C16'—C17'—N2'118.9 (3)
C15—C14—H14120.3C18'—C17'—C16'123.1 (4)
C14—C15—N2119.5 (3)C18'—C17'—N2'118.0 (4)
C16—C15—C14121.8 (4)C13'—C18'—H18'120.4
C16—C15—N2118.7 (3)C17'—C18'—C13'119.3 (3)
C15—C16—H16120.6C17'—C18'—H18'120.4
C17—C16—C15118.8 (3)O6'—C19'—C9'126.9 (2)
C17—C16—H16120.6O6'—C19'—O7'121.3 (2)
C16—C17—H17119.7O7'—C19'—C9'111.78 (18)
C16—C17—C18120.7 (3)H20A—C20'—H20B107.9
C18—C17—H17119.7C21'—C20'—H20A109.2
C13—C18—H18120.1C21'—C20'—H20B109.2
C17—C18—C13119.8 (4)O7'—C20'—H20A109.2
C17—C18—H18120.1O7'—C20'—H20B109.2
O6—C19—C9127.8 (2)O7'—C20'—C21'112.2 (2)
O6—C19—O7120.7 (2)C20'—C21'—H21A108.6
O7—C19—C9111.49 (18)C20'—C21'—H21B108.6
H20C—C20—H20D108.4H21A—C21'—H21B107.6
C21—C20—H20C110.1N3'—C21'—C20'114.7 (2)
C21—C20—H20D110.1N3'—C21'—H21A108.6
O7—C20—H20C110.1N3'—C21'—H21B108.6
O7—C20—H20D110.1C27'—C22'—C23'116.4 (3)
O7—C20—C21108.2 (2)N3'—C22'—C23'121.2 (3)
C20—C21—H21C109.1N3'—C22'—C27'122.4 (3)
C20—C21—H21D109.1C22'—C23'—H23'119.4
H21C—C21—H21D107.9C24'—C23'—C22'121.1 (3)
N3—C21—C20112.4 (2)C24'—C23'—H23'119.4
N3—C21—H21C109.1C23'—C24'—H24'119.3
N3—C21—H21D109.1C25'—C24'—C23'121.4 (4)
C27—C22—C23117.4 (3)C25'—C24'—H24'119.3
C27—C22—N3122.1 (3)C24'—C25'—H25'120.7
N3—C22—C23120.5 (2)C24'—C25'—C26'118.6 (4)
C22—C23—H23119.6C26'—C25'—H25'120.7
C24—C23—C22120.9 (3)C25'—C26'—H26'118.9
C24—C23—H23119.6C25'—C26'—C27'122.2 (4)
C23—C24—H24119.3C27'—C26'—H26'118.9
C25—C24—C23121.4 (4)C22'—C27'—H27'119.9
C25—C24—H24119.3C26'—C27'—C22'120.2 (4)
C24—C25—H25120.7C26'—C27'—H27'119.9
C26—C25—C24118.6 (4)H28A—C28'—H28B107.7
C26—C25—H25120.7C29'—C28'—H28A108.8
C25—C26—H26118.9C29'—C28'—H28B108.8
C25—C26—C27122.2 (4)N3'—C28'—H28A108.8
C27—C26—H26118.9N3'—C28'—H28B108.8
C22—C27—C26119.6 (4)N3'—C28'—C29'113.7 (3)
C22—C27—H27120.2C30'—C29'—C28'121.6 (3)
C26—C27—H27120.2C30'—C29'—C34'117.9 (4)
H28C—C28—H28D107.9C34'—C29'—C28'120.1 (3)
C29—C28—H28C109.1C29'—C30'—H30'118.5
C29—C28—H28D109.1C31'—C30'—C29'122.9 (4)
N3—C28—H28C109.1C31'—C30'—H30'118.5
N3—C28—H28D109.1C30'—C31'—H31'121.0
N3—C28—C29112.4 (2)C30'—C31'—C32'118.0 (5)
C30—C29—C28120.8 (3)C32'—C31'—H31'121.0
C34—C29—C28120.4 (3)C31'—C32'—H32'119.0
C34—C29—C30118.8 (3)C31'—C32'—C33'122.0 (5)
C29—C30—H30119.7C33'—C32'—H32'119.0
C31—C30—C29120.6 (4)C32'—C33'—H33'121.5
C31—C30—H30119.7C34'—C33'—C32'117.0 (6)
C30—C31—H31119.9C34'—C33'—H33'121.5
C30—C31—C32120.2 (5)C29'—C34'—H34'119.1
C32—C31—H31119.9C33'—C34'—C29'121.9 (6)
C31—C32—H32120.2C33'—C34'—H34'119.1
C31—C32—C33119.6 (4)C6'—N1'—H1'118.8
C33—C32—H32120.2C10'—N1'—C6'122.39 (18)
C32—C33—H33119.4C10'—N1'—H1'118.8
C32—C33—C34121.2 (5)O4'—N2'—C17'119.3 (3)
C34—C33—H33119.4O5'—N2'—C17'116.8 (6)
C29—C34—C33119.6 (4)O5'—N2'—O4'123.4 (6)
C29—C34—H34120.2C21'—N3'—C28'115.5 (2)
C33—C34—H34120.2C22'—N3'—C21'120.8 (2)
C6—N1—H1118.4C22'—N3'—C28'123.6 (2)
C10—N1—C6123.14 (18)C1'—O1'—P1'118.92 (14)
C10—N1—H1118.4C3'—O2'—P1'117.97 (14)
O4—N2—C15117.7 (5)C19'—O7'—C20'115.43 (18)
O5—N2—C15118.3 (3)O1'—P1'—C7'106.47 (9)
O5—N2—O4124.0 (5)O2'—P1'—C7'109.21 (9)
C21—N3—C28115.6 (2)O2'—P1'—O1'104.98 (9)
C22—N3—C21117.7 (2)O3'—P1'—C7'114.43 (10)
C22—N3—C28117.5 (2)O3'—P1'—O1'111.05 (9)
C1—O1—P1118.88 (14)O3'—P1'—O2'110.22 (10)
C3—O2—P1118.32 (16)C36—C35—C37117.4 (6)
C19—O7—C20118.22 (19)O8—C35—C36120.7 (6)
O1—P1—C7105.67 (9)O8—C35—C37121.8 (7)
O2—P1—C7109.22 (9)C35—C36—H36A109.5
O2—P1—O1104.83 (9)C35—C36—H36B109.5
O3—P1—C7115.41 (10)C35—C36—H36C109.5
O3—P1—O1110.54 (9)H36A—C36—H36B109.5
O3—P1—O2110.54 (10)H36A—C36—H36C109.5
H1'A—C1'—H1'B107.9H36B—C36—H36C109.5
C2'—C1'—H1'A109.1C35—C37—H37A109.5
C2'—C1'—H1'B109.1C35—C37—H37B109.5
O1'—C1'—H1'A109.1C35—C37—H37C109.5
O1'—C1'—H1'B109.1H37A—C37—H37B109.5
O1'—C1'—C2'112.3 (2)H37A—C37—H37C109.5
C1'—C2'—C3'108.2 (2)H37B—C37—H37C109.5
C1'—C2'—C4'110.3 (2)
C1—C2—C3—O260.3 (3)C1'—C2'—C3'—O2'59.7 (3)
C1—O1—P1—C774.60 (17)C1'—O1'—P1'—C7'74.34 (18)
C1—O1—P1—O240.74 (17)C1'—O1'—P1'—O2'41.40 (17)
C1—O1—P1—O3159.87 (16)C1'—O1'—P1'—O3'160.50 (16)
C2—C1—O1—P152.4 (2)C2'—C1'—O1'—P1'51.6 (2)
C2—C3—O2—P156.5 (3)C2'—C3'—O2'—P1'57.3 (2)
C3—O2—P1—C769.90 (19)C3'—O2'—P1'—C7'69.47 (18)
C3—O2—P1—O142.94 (19)C3'—O2'—P1'—O1'44.36 (17)
C3—O2—P1—O3162.08 (17)C3'—O2'—P1'—O3'164.02 (16)
C4—C2—C3—O2177.1 (2)C4'—C2'—C3'—O2'61.6 (3)
C5—C2—C3—O261.7 (3)C5'—C2'—C3'—O2'176.8 (2)
C6—C7—C8—C916.7 (3)C6'—C7'—C8'—C9'22.6 (3)
C6—C7—C8—C13108.1 (2)C6'—C7'—C8'—C13'101.7 (2)
C6—C7—P1—O1155.43 (19)C6'—C7'—P1'—O1'156.74 (18)
C6—C7—P1—O243.1 (2)C6'—C7'—P1'—O2'43.9 (2)
C6—C7—P1—O382.1 (2)C6'—C7'—P1'—O3'80.2 (2)
C7—C6—N1—C1010.3 (3)C7'—C6'—N1'—C10'13.6 (3)
C7—C8—C9—C1017.3 (3)C7'—C8'—C9'—C10'22.3 (3)
C7—C8—C9—C19162.58 (19)C7'—C8'—C9'—C19'158.11 (18)
C7—C8—C13—C1465.5 (3)C7'—C8'—C13'—C14'104.8 (3)
C7—C8—C13—C18113.0 (2)C7'—C8'—C13'—C18'75.2 (3)
C8—C7—P1—O131.62 (18)C8'—C7'—P1'—O1'30.39 (18)
C8—C7—P1—O2143.92 (16)C8'—C7'—P1'—O2'143.25 (16)
C8—C7—P1—O390.85 (18)C8'—C7'—P1'—O3'92.68 (18)
C8—C9—C10—C12176.4 (2)C8'—C9'—C10'—C12'175.5 (2)
C8—C9—C10—N15.4 (3)C8'—C9'—C10'—N1'5.8 (3)
C8—C9—C19—O6171.9 (2)C8'—C9'—C19'—O6'177.1 (2)
C8—C9—C19—O79.2 (3)C8'—C9'—C19'—O7'2.9 (3)
C8—C13—C14—C15178.2 (2)C8'—C13'—C14'—C15'179.8 (3)
C8—C13—C18—C17177.5 (3)C8'—C13'—C18'—C17'179.9 (3)
C9—C8—C13—C1458.8 (3)C9'—C8'—C13'—C14'132.1 (3)
C9—C8—C13—C18122.7 (2)C9'—C8'—C13'—C18'47.9 (3)
C9—C10—N1—C69.6 (3)C9'—C10'—N1'—C6'13.9 (3)
C9—C19—O7—C20174.9 (2)C9'—C19'—O7'—C20'178.61 (18)
C10—C9—C19—O68.2 (4)C10'—C9'—C19'—O6'3.4 (4)
C10—C9—C19—O7170.7 (2)C10'—C9'—C19'—O7'176.62 (19)
C11—C6—C7—C8178.1 (2)C11'—C6'—C7'—C8'175.2 (2)
C11—C6—C7—P15.5 (4)C11'—C6'—C7'—P1'2.6 (4)
C11—C6—N1—C10167.7 (2)C11'—C6'—N1'—C10'165.0 (2)
C12—C10—N1—C6168.7 (2)C12'—C10'—N1'—C6'165.0 (2)
C13—C8—C9—C10107.0 (2)C13'—C8'—C9'—C10'101.1 (2)
C13—C8—C9—C1973.1 (2)C13'—C8'—C9'—C19'78.4 (2)
C13—C14—C15—C160.5 (5)C13'—C14'—C15'—C16'0.3 (6)
C13—C14—C15—N2179.7 (3)C14'—C13'—C18'—C17'0.1 (4)
C14—C13—C18—C171.0 (4)C14'—C15'—C16'—C17'0.0 (6)
C14—C15—C16—C170.5 (6)C15'—C16'—C17'—C18'0.4 (6)
C14—C15—N2—O4176.3 (5)C15'—C16'—C17'—N2'178.4 (4)
C14—C15—N2—O55.1 (7)C16'—C17'—C18'—C13'0.5 (5)
C15—C16—C17—C180.2 (6)C16'—C17'—N2'—O4'162.5 (6)
C16—C15—N2—O42.9 (7)C16'—C17'—N2'—O5'9.5 (8)
C16—C15—N2—O5175.7 (5)C18'—C13'—C14'—C15'0.2 (5)
C16—C17—C18—C131.0 (6)C18'—C17'—N2'—O4'15.6 (8)
C18—C13—C14—C150.3 (4)C18'—C17'—N2'—O5'172.4 (6)
C19—C9—C10—C123.7 (4)C19'—C9'—C10'—C12'4.0 (3)
C19—C9—C10—N1174.4 (2)C19'—C9'—C10'—N1'174.68 (19)
C20—C21—N3—C2274.5 (3)C20'—C21'—N3'—C22'85.9 (3)
C20—C21—N3—C2871.7 (3)C20'—C21'—N3'—C28'98.0 (3)
C21—C20—O7—C19100.7 (2)C21'—C20'—O7'—C19'78.5 (3)
C22—C23—C24—C250.8 (4)C22'—C23'—C24'—C25'1.0 (5)
C23—C22—C27—C260.4 (4)C23'—C22'—C27'—C26'0.4 (5)
C23—C22—N3—C2133.9 (3)C23'—C22'—N3'—C21'2.9 (4)
C23—C22—N3—C28179.4 (2)C23'—C22'—N3'—C28'178.7 (3)
C23—C24—C25—C260.2 (5)C23'—C24'—C25'—C26'0.4 (5)
C24—C25—C26—C270.6 (6)C24'—C25'—C26'—C27'1.9 (6)
C25—C26—C27—C221.0 (5)C25'—C26'—C27'—C22'1.9 (6)
C27—C22—C23—C240.4 (4)C27'—C22'—C23'—C24'1.0 (4)
C27—C22—N3—C21148.7 (2)C27'—C22'—N3'—C21'176.8 (3)
C27—C22—N3—C283.2 (3)C27'—C22'—N3'—C28'1.0 (4)
C28—C29—C30—C31177.3 (3)C28'—C29'—C30'—C31'179.9 (4)
C28—C29—C34—C33178.2 (3)C28'—C29'—C34'—C33'177.5 (6)
C29—C28—N3—C2140.6 (3)C29'—C28'—N3'—C21'74.0 (3)
C29—C28—N3—C22173.1 (2)C29'—C28'—N3'—C22'102.0 (3)
C29—C30—C31—C321.1 (6)C29'—C30'—C31'—C32'5.8 (7)
C30—C29—C34—C331.0 (5)C30'—C29'—C34'—C33'4.9 (8)
C30—C31—C32—C330.5 (7)C30'—C31'—C32'—C33'1.0 (9)
C31—C32—C33—C341.5 (7)C31'—C32'—C33'—C34'1.5 (11)
C32—C33—C34—C290.7 (7)C32'—C33'—C34'—C29'0.5 (11)
C34—C29—C30—C311.9 (5)C34'—C29'—C30'—C31'7.6 (6)
N1—C6—C7—C84.2 (3)N1'—C6'—C7'—C8'6.4 (3)
N1—C6—C7—P1176.74 (17)N1'—C6'—C7'—P1'179.00 (17)
N2—C15—C16—C17179.7 (4)N2'—C17'—C18'—C13'178.5 (4)
N3—C22—C23—C24178.0 (2)N3'—C22'—C23'—C24'178.7 (3)
N3—C22—C27—C26177.1 (3)N3'—C22'—C27'—C26'179.9 (3)
N3—C28—C29—C3065.9 (3)N3'—C28'—C29'—C30'59.1 (4)
N3—C28—C29—C34113.2 (3)N3'—C28'—C29'—C34'113.3 (4)
O1—C1—C2—C358.2 (3)O1'—C1'—C2'—C3'57.0 (3)
O1—C1—C2—C4175.2 (2)O1'—C1'—C2'—C4'64.8 (3)
O1—C1—C2—C563.1 (3)O1'—C1'—C2'—C5'173.9 (2)
O6—C19—O7—C206.1 (3)O6'—C19'—O7'—C20'1.4 (3)
O7—C20—C21—N3170.3 (2)O7'—C20'—C21'—N3'65.8 (3)
P1—C7—C8—C9170.31 (15)P1'—C7'—C8'—C9'164.54 (15)
P1—C7—C8—C1364.9 (2)P1'—C7'—C8'—C13'71.2 (2)
Hydrogen-bond geometry (Å, º) top
Cg4 and Cg9 are the centroids of the C22'–C27' and C22–C27 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.862.042.847 (2)155
N1—H1···O3i0.862.202.917 (2)141
C1—H1A···O6ii0.972.543.456 (4)157
C1—H1B···O6iii0.972.423.346 (4)160
C15—H15···O50.932.553.470 (7)173
C37—H37C···Cg4iv0.962.883.667 (9)139
C3—H3B···Cg9v0.972.663.599 (3)163
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z; (iii) x+2, y+1, z+1; (iv) x+1, y+1, z+1; (v) x+1, y1, z.
 

Acknowledgements

The authors are grateful to the Analysis and Testing Center of Zhengzhou University for use of the single-crystal X-ray diffraction facility. This work was supported by the Science and Technology Bureau of Henan Province through the Cooperation Research Project Fund (No. 152107000041 for WL), the Education Bureau of Henan Province for Major Research Project Funds (No. 14 A530007 for WL), and the Graduate Student Science Research Foundation of Zhengzhou University.

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGuo, Y.-M., Wu, L.-Y., Li, Y.-Y. & Song, H.-R. (2008). Chin. J. Med. Chem, 81, 35–37.  Google Scholar
First citationJeyakanthan, J., Shanmuga Sundara Raj, S., Velmurugan, D., Fun, H.-K. & Murugan, P. (1999). Acta Cryst. C55, 1515–1517.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationSakoda, R., Kamikawaji, Y. & Seto, K. (1992). Chem. Pharm. Bull. 40, 2362–2369.  CrossRef PubMed CAS Google Scholar
First citationSaito, T., Arakawa, K., Iimura, O., Ogiwara, T., Kanazawa, T., Mizuno, Y., Murakami, E., Ouhashi, Y., Inagaki, Y. & Yamada, K. (1992). Curr. Ther. Res. 52, 113–123.  CrossRef Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2015). Acta Cryst. C71, 9–18.  Web of Science CrossRef IUCr Journals Google Scholar
First citationYamashita, T., Masuda, Y., Sakai, T., Tanaka, S. & Kasuya, Y. (1991). Jpn. J. Pharmacol. 57, 337–348.  CrossRef PubMed CAS Web of Science Google Scholar

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