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

Journal logoIUCrDATA
ISSN: 2414-3146

7-{3-Eth­­oxy-4-[2-(2-meth­­oxy­eth­­oxy)eth­­oxy]phen­yl}-5,6,8,9-tetra­hydro­dibenzo[c,h]acridine

aDepartment of Chemistry, Anhui University, Hefei, Anhui 230039, People's Republic of China
*Correspondence e-mail: jywu1957@163.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 August 2019; accepted 31 August 2019; online 6 September 2019)

In the title compound, C34H35NO4, the dihedral angle between the pyridine ring and attached benzene ring is 79.17 (8)°. The meth­oxy­eth­oxy–eth­oxy side chain is disordered over two orientations in a 0.732 (7):0.268 (7) ratio. In the crystal, very weak C—H⋯N and C—H⋯O inter­actions link the mol­ecules.

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

Structure description

Ethyl vanillin derivatives have various biological properties (Sainsbury et al. 2013[Sainsbury, P. D., Hardiman, E. M., Ahmad, M., Otani, H., Seghezzi, N., Eltis, L. D. & Bugg, T. D. H. (2013). Chem. Biol. 8, 2151-2156.]) but many of them show poor lipid solubility (Wu et al. 2018[Wu, D. J., Fang, B., Zhang, M. Z., Du, W., Zhang, J., Tian, X., Zhang, Q., Zhou, H., Wu, J. & Tian, Y. (2018). Dyes Pigments, 159, 142-150.]). In this study, an ether oxygen chain was introduced into the title compound in an attempt to improve its solublity.

In the crystal structure (Fig. 1[link]), the dihedral angle between the pyridine ring and adjacent benzene ring is 79.17 (8)°. The meth­oxy­eth­oxy-eth­oxy side chain is disordered over two orientations in a 0.732 (7):0.268 (7) ratio. In the crystal, very weak C29—H29⋯O4 (2.69 Å) and C27—H27⋯N1 (2.67 Å) inter­actions (Table 1[link], Fig. 2[link]) occur (Wang et al. 2019[Wang, Y. W., Li, H., Shen, Y. & Wu, J. (2019). IUCrData, 4, x190294.]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C27—H27⋯N1i 0.93 2.67 3.537 (2) 156
C29—H29c⋯O4ii 0.96 2.69 3.415 (6) 132
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z-1.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 50% displacement ellipsoids. Only the major disorder component of the meth­oxy­eth­oxy–eth­oxy side chain is shown.
[Figure 2]
Figure 2
Weak C—H⋯N and C—H⋯O inter­actions in the title compound (blue and red lines, respectively). Symmetry codes: (a) x, [{1\over 2}] − y, z − [{1\over 2}]; (b) x, y, z − 1.

Synthesis and crystallization

Ammonium acetate (7.7 g, 100 mmol), ethyl vanillin (1.7 g, 10 mmol), 3,4-di­hydro­naphthalen-1(2H)-one (3.0 g, 20 mmol) and 25 ml acetic acid were added to a 100 ml flask and stirred for 15 min. After dissolution, the mixture was refluxed at 403 K for 6 h and filtered to obtain a yellow solid. Then, the yellow solid (2.4 g, 5.7 mmol), K2CO3 (0.69 g, 5 mmol) and 2-(2-meth­oxy­eth­oxy)ethyl 4-methyl­benzene­sulfonate (1.67 g, 6 mmol) were dissolved in 30 ml of aceto­nitrile and the mixture was refluxed at 355 K for 12 h. After cooling to room temperature, the mixture was filtered to get a white solid (3.1 g). Colourless crystals of the title compound were recrystallized from ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C34H35NO4
Mr 521.63
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 9.1797 (13), 30.203 (4), 11.0131 (16)
β (°) 111.056 (2)
V3) 2849.6 (7)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.12 × 0.11 × 0.10
 
Data collection
Diffractometer Bruker APEXII CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.538, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 22024, 5934, 4199
Rint 0.044
(sin θ/λ)max−1) 0.646
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.150, 1.03
No. of reflections 5934
No. of parameters 401
No. of restraints 54
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.21
Computer programs: APEX2 and), SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). 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: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

7-{3-Ethoxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl}-5,6,8,9-tetrahydrodibenzo[c,h]acridine top
Crystal data top
C34H35NO4F(000) = 1112
Mr = 521.63Dx = 1.216 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.1797 (13) ÅCell parameters from 7039 reflections
b = 30.203 (4) Åθ = 2.4–23.8°
c = 11.0131 (16) ŵ = 0.08 mm1
β = 111.056 (2)°T = 296 K
V = 2849.6 (7) Å3Block, colourless
Z = 40.12 × 0.11 × 0.1 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
4199 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
phi and ω scansθmax = 27.4°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.538, Tmax = 0.746k = 3838
22024 measured reflectionsl = 1413
5934 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.0721P)2 + 0.4744P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5934 reflectionsΔρmax = 0.19 e Å3
401 parametersΔρmin = 0.21 e Å3
54 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*/UeqOcc. (<1)
O10.71434 (16)0.39493 (4)0.20577 (13)0.0743 (4)
O20.63910 (14)0.42204 (4)0.39754 (11)0.0635 (3)
O30.6825 (5)0.47955 (14)0.6935 (4)0.0755 (11)0.732 (7)
O3A0.695 (2)0.4900 (6)0.6688 (17)0.173 (8)0.268 (7)
O40.7326 (5)0.49775 (11)0.9670 (3)0.1180 (16)0.732 (7)
O4A0.8197 (10)0.5302 (3)0.9932 (7)0.119 (4)0.268 (7)
N10.10451 (15)0.22075 (4)0.09581 (13)0.0510 (3)
C10.08312 (18)0.26320 (5)0.13215 (15)0.0485 (4)
C20.03102 (18)0.27262 (5)0.26405 (15)0.0509 (4)
C30.0832 (2)0.23947 (6)0.35734 (17)0.0633 (5)
H30.0472160.2106580.3363950.076*
C40.1871 (2)0.24872 (7)0.48007 (19)0.0749 (6)
H40.2223150.2261790.5412100.090*
C50.2390 (2)0.29134 (7)0.5123 (2)0.0754 (6)
H50.3087620.2977810.5953880.090*
C60.1874 (2)0.32435 (7)0.42118 (19)0.0692 (5)
H60.2223410.3531550.4438490.083*
C70.08478 (19)0.31579 (6)0.29667 (16)0.0563 (4)
C80.0320 (2)0.35105 (6)0.19438 (19)0.0708 (5)
H8A0.0990770.3508120.1435130.085*
H8B0.0423100.3797430.2362000.085*
C90.1352 (2)0.34464 (5)0.10467 (17)0.0605 (4)
H9A0.2040760.3514830.1513680.073*
H9B0.1585040.3650840.0322180.073*
C100.16608 (18)0.29796 (5)0.05304 (15)0.0491 (4)
C110.27751 (18)0.28769 (5)0.06836 (15)0.0504 (4)
C120.30031 (19)0.24333 (5)0.10727 (15)0.0518 (4)
C130.4164 (2)0.22877 (6)0.23686 (18)0.0672 (5)
H13A0.3648110.2267320.2996530.081*
H13B0.4989750.2505990.2680640.081*
C140.4863 (2)0.18407 (7)0.2251 (2)0.0758 (6)
H14A0.5533730.1874710.1748580.091*
H14B0.5500460.1736890.3111460.091*
C150.3636 (2)0.15035 (6)0.16108 (17)0.0638 (5)
C160.3808 (3)0.10565 (7)0.1952 (2)0.0820 (6)
H160.4705040.0961990.2619700.098*
C170.2674 (4)0.07543 (7)0.1317 (2)0.0920 (8)
H170.2810800.0457000.1550370.110*
C180.1336 (3)0.08896 (7)0.0336 (2)0.0856 (7)
H180.0566370.0684140.0088150.103*
C190.1130 (2)0.13319 (6)0.00238 (19)0.0674 (5)
H190.0222520.1422570.0686360.081*
C200.2281 (2)0.16406 (5)0.06058 (16)0.0559 (4)
C210.20972 (18)0.21123 (5)0.02191 (15)0.0502 (4)
C220.37005 (19)0.32369 (5)0.15619 (15)0.0512 (4)
C230.4972 (2)0.34257 (6)0.13558 (16)0.0556 (4)
H230.5235150.3330000.0658690.067*
C240.58527 (19)0.37532 (5)0.21675 (16)0.0532 (4)
C250.54418 (19)0.39013 (5)0.32045 (15)0.0512 (4)
C260.4170 (2)0.37195 (6)0.33955 (16)0.0580 (4)
H260.3881290.3820720.4074370.070*
C270.3310 (2)0.33861 (6)0.25851 (16)0.0575 (4)
H270.2462380.3262500.2735440.069*
C280.7627 (2)0.38215 (8)0.1035 (2)0.0782 (6)
H28A0.6852890.3909370.0207480.094*
H28B0.7746430.3502450.1034020.094*
C290.9141 (3)0.40407 (9)0.1224 (2)0.0933 (7)
H29A0.9434180.3982950.0486090.140*
H29B0.9928160.3926710.1995930.140*
H29C0.9038790.4354230.1313650.140*
C300.6000 (2)0.43698 (7)0.50509 (18)0.0688 (5)
H30A0.5889850.4119290.5562530.083*
H30B0.5019330.4530360.4741770.083*
C310.7281 (3)0.46647 (7)0.58576 (19)0.0746 (5)
H31A0.8268740.4507740.6166340.090*0.732 (7)
H31B0.7379130.4921180.5362380.090*0.732 (7)
H31C0.8184570.4483880.6317570.090*0.268 (7)
H31D0.7569650.4860840.5283690.090*0.268 (7)
C320.7863 (7)0.50939 (18)0.7776 (6)0.0878 (14)0.732 (7)
H32A0.8039930.5336880.7269620.105*0.732 (7)
H32B0.8854430.4946230.8202070.105*0.732 (7)
C32A0.790 (4)0.4894 (10)0.783 (2)0.176 (11)0.268 (7)
H32C0.8793030.5079110.7901060.211*0.268 (7)
H32D0.8265630.4594740.8077280.211*0.268 (7)
C330.7328 (8)0.52691 (19)0.8746 (6)0.0969 (16)0.732 (7)
H33A0.7985370.5518030.9162780.116*0.732 (7)
H33B0.6275430.5380430.8321870.116*0.732 (7)
C33A0.697 (3)0.5091 (6)0.8795 (19)0.123 (6)0.268 (7)
H33C0.6179540.5306170.8330030.148*0.268 (7)
H33D0.6462480.4851210.9080890.148*0.268 (7)
C340.7022 (11)0.5171 (3)1.0730 (7)0.156 (3)0.732 (7)
H34A0.6111570.5355441.0404000.233*0.732 (7)
H34B0.7901320.5347441.1235880.233*0.732 (7)
H34C0.6848900.4941921.1266040.233*0.732 (7)
C34A0.752 (3)0.5412 (6)1.0832 (17)0.138 (7)0.268 (7)
H34D0.7811370.5196911.1520010.207*0.268 (7)
H34E0.6404650.5415131.0412640.207*0.268 (7)
H34F0.7874650.5699411.1185870.207*0.268 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0755 (9)0.0878 (9)0.0700 (8)0.0311 (7)0.0387 (7)0.0266 (7)
O20.0689 (8)0.0666 (7)0.0561 (7)0.0144 (6)0.0239 (6)0.0193 (6)
O30.0841 (19)0.0845 (17)0.061 (2)0.0294 (16)0.0303 (17)0.0267 (13)
O3A0.212 (15)0.171 (13)0.089 (7)0.098 (10)0.004 (7)0.065 (8)
O40.177 (4)0.103 (2)0.085 (2)0.020 (2)0.061 (2)0.0026 (17)
O4A0.139 (7)0.143 (8)0.080 (5)0.042 (5)0.045 (4)0.031 (4)
N10.0477 (7)0.0540 (8)0.0490 (8)0.0020 (6)0.0145 (6)0.0028 (6)
C10.0430 (8)0.0529 (9)0.0479 (9)0.0019 (7)0.0144 (7)0.0030 (7)
C20.0416 (8)0.0586 (9)0.0484 (9)0.0029 (7)0.0114 (7)0.0020 (7)
C30.0562 (10)0.0633 (10)0.0580 (11)0.0026 (8)0.0057 (9)0.0061 (8)
C40.0663 (12)0.0814 (13)0.0590 (12)0.0065 (10)0.0006 (10)0.0115 (10)
C50.0631 (12)0.0880 (14)0.0553 (11)0.0015 (10)0.0025 (9)0.0048 (10)
C60.0603 (11)0.0702 (11)0.0639 (12)0.0052 (9)0.0065 (9)0.0074 (9)
C70.0489 (9)0.0625 (10)0.0533 (10)0.0015 (7)0.0133 (8)0.0006 (8)
C80.0764 (13)0.0598 (10)0.0646 (12)0.0092 (9)0.0112 (10)0.0032 (8)
C90.0667 (11)0.0550 (9)0.0542 (10)0.0060 (8)0.0149 (9)0.0042 (7)
C100.0461 (9)0.0546 (9)0.0458 (9)0.0034 (7)0.0155 (7)0.0036 (7)
C110.0442 (9)0.0603 (9)0.0459 (9)0.0062 (7)0.0152 (7)0.0059 (7)
C120.0464 (9)0.0617 (10)0.0453 (9)0.0011 (7)0.0140 (7)0.0010 (7)
C130.0639 (11)0.0733 (11)0.0524 (10)0.0006 (9)0.0065 (9)0.0021 (8)
C140.0665 (12)0.0902 (14)0.0617 (12)0.0174 (10)0.0121 (10)0.0117 (10)
C150.0763 (12)0.0697 (11)0.0507 (10)0.0180 (9)0.0293 (9)0.0071 (8)
C160.1162 (18)0.0777 (14)0.0589 (12)0.0320 (13)0.0396 (12)0.0154 (10)
C170.155 (2)0.0610 (12)0.0754 (14)0.0155 (14)0.0597 (16)0.0114 (11)
C180.123 (2)0.0607 (11)0.0880 (16)0.0111 (12)0.0561 (15)0.0023 (11)
C190.0811 (13)0.0600 (10)0.0682 (12)0.0038 (9)0.0355 (10)0.0017 (9)
C200.0655 (11)0.0565 (9)0.0527 (9)0.0047 (8)0.0295 (9)0.0014 (7)
C210.0461 (9)0.0572 (9)0.0476 (9)0.0000 (7)0.0171 (7)0.0010 (7)
C220.0479 (9)0.0588 (9)0.0428 (8)0.0044 (7)0.0113 (7)0.0033 (7)
C230.0557 (10)0.0670 (10)0.0460 (9)0.0088 (8)0.0204 (8)0.0108 (7)
C240.0502 (9)0.0605 (9)0.0490 (9)0.0092 (7)0.0180 (7)0.0056 (7)
C250.0518 (9)0.0542 (9)0.0434 (8)0.0032 (7)0.0120 (7)0.0057 (7)
C260.0572 (10)0.0709 (10)0.0487 (9)0.0030 (8)0.0225 (8)0.0087 (8)
C270.0509 (10)0.0715 (11)0.0512 (10)0.0092 (8)0.0199 (8)0.0059 (8)
C280.0731 (13)0.0934 (14)0.0782 (13)0.0149 (11)0.0395 (11)0.0201 (11)
C290.0768 (14)0.1173 (18)0.0985 (17)0.0265 (13)0.0469 (13)0.0220 (14)
C300.0715 (12)0.0710 (11)0.0622 (11)0.0002 (9)0.0219 (10)0.0207 (9)
C310.0886 (14)0.0694 (11)0.0621 (12)0.0079 (10)0.0225 (11)0.0175 (9)
C320.097 (3)0.093 (3)0.072 (2)0.032 (2)0.029 (2)0.040 (2)
C32A0.224 (19)0.22 (3)0.062 (7)0.017 (19)0.030 (9)0.023 (13)
C330.132 (4)0.088 (4)0.069 (3)0.017 (3)0.034 (2)0.024 (2)
C33A0.184 (15)0.096 (12)0.068 (8)0.023 (10)0.019 (8)0.010 (8)
C340.215 (8)0.166 (6)0.122 (4)0.000 (6)0.105 (5)0.032 (5)
C34A0.23 (2)0.118 (12)0.100 (9)0.051 (12)0.103 (11)0.037 (9)
Geometric parameters (Å, º) top
O1—C241.368 (2)C16—C171.373 (3)
O1—C281.405 (2)C17—H170.9300
O2—C251.3701 (19)C17—C181.375 (4)
O2—C301.429 (2)C18—H180.9300
O3—C311.448 (4)C18—C191.387 (3)
O3—C321.394 (6)C19—H190.9300
O3A—C311.278 (14)C19—C201.393 (3)
O3A—C32A1.24 (3)C20—C211.479 (2)
O4—C331.346 (8)C22—C231.389 (2)
O4—C341.420 (6)C22—C271.375 (2)
O4A—C33A1.50 (2)C23—H230.9300
O4A—C34A1.386 (18)C23—C241.383 (2)
N1—C11.336 (2)C24—C251.399 (2)
N1—C211.340 (2)C25—C261.373 (2)
C1—C21.482 (2)C26—H260.9300
C1—C101.402 (2)C26—C271.388 (2)
C2—C31.391 (2)C27—H270.9300
C2—C71.395 (2)C28—H28A0.9700
C3—H30.9300C28—H28B0.9700
C3—C41.374 (3)C28—C291.485 (3)
C4—H40.9300C29—H29A0.9600
C4—C51.374 (3)C29—H29B0.9600
C5—H50.9300C29—H29C0.9600
C5—C61.372 (3)C30—H30A0.9700
C6—H60.9300C30—H30B0.9700
C6—C71.381 (2)C30—C311.488 (3)
C7—C81.499 (2)C31—H31A0.9700
C8—H8A0.9700C31—H31B0.9700
C8—H8B0.9700C31—H31C0.9700
C8—C91.510 (3)C31—H31D0.9700
C9—H9A0.9700C32—H32A0.9700
C9—H9B0.9700C32—H32B0.9700
C9—C101.508 (2)C32—C331.428 (9)
C10—C111.396 (2)C32A—H32C0.9700
C11—C121.399 (2)C32A—H32D0.9700
C11—C221.500 (2)C32A—C33A1.70 (3)
C12—C131.508 (2)C33—H33A0.9700
C12—C211.398 (2)C33—H33B0.9700
C13—H13A0.9700C33A—H33C0.9700
C13—H13B0.9700C33A—H33D0.9700
C13—C141.520 (3)C34—H34A0.9600
C14—H14A0.9700C34—H34B0.9600
C14—H14B0.9700C34—H34C0.9600
C14—C151.494 (3)C34A—H34D0.9600
C15—C161.395 (3)C34A—H34E0.9600
C15—C201.398 (3)C34A—H34F0.9600
C16—H160.9300
C24—O1—C28119.02 (14)C27—C22—C11120.80 (15)
C25—O2—C30116.26 (14)C27—C22—C23118.75 (15)
C32—O3—C31113.0 (3)C22—C23—H23119.4
C32A—O3A—C31116.7 (19)C24—C23—C22121.25 (15)
C33—O4—C34113.9 (4)C24—C23—H23119.4
C34A—O4A—C33A107.6 (14)O1—C24—C23125.20 (15)
C1—N1—C21118.22 (13)O1—C24—C25115.46 (14)
N1—C1—C2117.00 (14)C23—C24—C25119.33 (15)
N1—C1—C10122.95 (14)O2—C25—C24115.65 (14)
C10—C1—C2120.02 (14)O2—C25—C26124.95 (15)
C3—C2—C1121.36 (15)C26—C25—C24119.39 (14)
C3—C2—C7119.13 (15)C25—C26—H26119.7
C7—C2—C1119.49 (14)C25—C26—C27120.65 (15)
C2—C3—H3119.6C27—C26—H26119.7
C4—C3—C2120.89 (17)C22—C27—C26120.61 (15)
C4—C3—H3119.6C22—C27—H27119.7
C3—C4—H4120.1C26—C27—H27119.7
C5—C4—C3119.86 (18)O1—C28—H28A110.0
C5—C4—H4120.1O1—C28—H28B110.0
C4—C5—H5120.2O1—C28—C29108.33 (17)
C6—C5—C4119.70 (18)H28A—C28—H28B108.4
C6—C5—H5120.2C29—C28—H28A110.0
C5—C6—H6119.2C29—C28—H28B110.0
C5—C6—C7121.54 (18)C28—C29—H29A109.5
C7—C6—H6119.2C28—C29—H29B109.5
C2—C7—C8118.81 (15)C28—C29—H29C109.5
C6—C7—C2118.87 (16)H29A—C29—H29B109.5
C6—C7—C8122.31 (16)H29A—C29—H29C109.5
C7—C8—H8A109.2H29B—C29—H29C109.5
C7—C8—H8B109.2O2—C30—H30A110.2
C7—C8—C9112.27 (15)O2—C30—H30B110.2
H8A—C8—H8B107.9O2—C30—C31107.68 (16)
C9—C8—H8A109.2H30A—C30—H30B108.5
C9—C8—H8B109.1C31—C30—H30A110.2
C8—C9—H9A109.2C31—C30—H30B110.2
C8—C9—H9B109.2O3—C31—C30104.7 (2)
H9A—C9—H9B107.9O3—C31—H31A110.8
C10—C9—C8112.07 (14)O3—C31—H31B110.8
C10—C9—H9A109.2O3A—C31—C30114.7 (9)
C10—C9—H9B109.2O3A—C31—H31C108.6
C1—C10—C9118.64 (14)O3A—C31—H31D108.6
C11—C10—C1118.45 (15)C30—C31—H31A110.8
C11—C10—C9122.87 (14)C30—C31—H31B110.8
C10—C11—C12118.93 (14)C30—C31—H31C108.6
C10—C11—C22120.48 (14)C30—C31—H31D108.6
C12—C11—C22120.59 (14)H31A—C31—H31B108.9
C11—C12—C13123.11 (15)H31C—C31—H31D107.6
C21—C12—C11118.08 (14)O3—C32—H32A108.9
C21—C12—C13118.80 (15)O3—C32—H32B108.9
C12—C13—H13A109.5O3—C32—C33113.6 (5)
C12—C13—H13B109.5H32A—C32—H32B107.7
C12—C13—C14110.77 (15)C33—C32—H32A108.9
H13A—C13—H13B108.1C33—C32—H32B108.9
C14—C13—H13A109.5O3A—C32A—H32C110.3
C14—C13—H13B109.5O3A—C32A—H32D110.3
C13—C14—H14A109.2O3A—C32A—C33A107 (2)
C13—C14—H14B109.2H32C—C32A—H32D108.5
H14A—C14—H14B107.9C33A—C32A—H32C110.3
C15—C14—C13112.08 (16)C33A—C32A—H32D110.3
C15—C14—H14A109.2O4—C33—C32114.7 (5)
C15—C14—H14B109.2O4—C33—H33A108.6
C16—C15—C14122.63 (19)O4—C33—H33B108.6
C16—C15—C20118.9 (2)C32—C33—H33A108.6
C20—C15—C14118.49 (16)C32—C33—H33B108.6
C15—C16—H16119.5H33A—C33—H33B107.6
C17—C16—C15121.0 (2)O4A—C33A—C32A106.0 (18)
C17—C16—H16119.5O4A—C33A—H33C110.5
C16—C17—H17119.9O4A—C33A—H33D110.5
C16—C17—C18120.2 (2)C32A—C33A—H33C110.5
C18—C17—H17119.9C32A—C33A—H33D110.5
C17—C18—H18119.9H33C—C33A—H33D108.7
C17—C18—C19120.2 (2)O4—C34—H34A109.5
C19—C18—H18119.9O4—C34—H34B109.5
C18—C19—H19119.9O4—C34—H34C109.5
C18—C19—C20120.1 (2)H34A—C34—H34B109.5
C20—C19—H19119.9H34A—C34—H34C109.5
C15—C20—C21119.37 (16)H34B—C34—H34C109.5
C19—C20—C15119.72 (17)O4A—C34A—H34D109.5
C19—C20—C21120.91 (16)O4A—C34A—H34E109.5
N1—C21—C12123.34 (15)O4A—C34A—H34F109.5
N1—C21—C20116.95 (14)H34D—C34A—H34E109.5
C12—C21—C20119.71 (15)H34D—C34A—H34F109.5
C23—C22—C11120.45 (14)H34E—C34A—H34F109.5
O1—C24—C25—O20.4 (2)C12—C11—C22—C2778.8 (2)
O1—C24—C25—C26179.39 (15)C12—C13—C14—C1551.7 (2)
O2—C25—C26—C27177.74 (16)C13—C12—C21—N1179.38 (16)
O2—C30—C31—O3178.9 (3)C13—C12—C21—C200.6 (2)
O2—C30—C31—O3A165.3 (10)C13—C14—C15—C16145.65 (18)
O3—C32—C33—O470.8 (8)C13—C14—C15—C2036.2 (2)
O3A—C32A—C33A—O4A151 (3)C14—C15—C16—C17178.1 (2)
N1—C1—C2—C316.0 (2)C14—C15—C20—C19178.86 (17)
N1—C1—C2—C7165.48 (15)C14—C15—C20—C210.7 (2)
N1—C1—C10—C9178.78 (15)C15—C16—C17—C180.6 (3)
N1—C1—C10—C110.9 (2)C15—C20—C21—N1160.90 (15)
C1—N1—C21—C121.4 (2)C15—C20—C21—C1219.1 (2)
C1—N1—C21—C20178.62 (14)C16—C15—C20—C190.6 (3)
C1—C2—C3—C4178.93 (18)C16—C15—C20—C21178.91 (16)
C1—C2—C7—C6178.00 (16)C16—C17—C18—C190.5 (3)
C1—C2—C7—C83.4 (2)C17—C18—C19—C200.2 (3)
C1—C10—C11—C121.0 (2)C18—C19—C20—C150.7 (3)
C1—C10—C11—C22179.60 (14)C18—C19—C20—C21178.80 (17)
C2—C1—C10—C90.6 (2)C19—C20—C21—N118.6 (2)
C2—C1—C10—C11177.26 (14)C19—C20—C21—C12161.38 (16)
C2—C3—C4—C50.9 (3)C20—C15—C16—C170.0 (3)
C2—C7—C8—C936.3 (2)C21—N1—C1—C2178.51 (14)
C3—C2—C7—C60.5 (3)C21—N1—C1—C100.3 (2)
C3—C2—C7—C8178.09 (17)C21—C12—C13—C1434.3 (2)
C3—C4—C5—C60.5 (3)C22—C11—C12—C130.0 (2)
C4—C5—C6—C70.5 (3)C22—C11—C12—C21179.41 (14)
C5—C6—C7—C21.0 (3)C22—C23—C24—O1178.26 (16)
C5—C6—C7—C8177.6 (2)C22—C23—C24—C250.9 (3)
C6—C7—C8—C9145.14 (18)C23—C22—C27—C260.1 (3)
C7—C2—C3—C40.4 (3)C23—C24—C25—O2178.85 (15)
C7—C8—C9—C1049.5 (2)C23—C24—C25—C260.1 (3)
C8—C9—C10—C132.2 (2)C24—O1—C28—C29173.35 (18)
C8—C9—C10—C11150.05 (16)C24—C25—C26—C271.1 (3)
C9—C10—C11—C12178.80 (15)C25—O2—C30—C31172.29 (15)
C9—C10—C11—C221.8 (2)C25—C26—C27—C221.1 (3)
C10—C1—C2—C3162.25 (16)C27—C22—C23—C240.9 (3)
C10—C1—C2—C716.2 (2)C28—O1—C24—C231.3 (3)
C10—C11—C12—C13179.33 (16)C28—O1—C24—C25179.51 (17)
C10—C11—C12—C210.0 (2)C30—O2—C25—C24179.04 (15)
C10—C11—C22—C2379.5 (2)C30—O2—C25—C260.1 (2)
C10—C11—C22—C27100.53 (19)C31—O3—C32—C33172.4 (5)
C11—C12—C13—C14146.32 (18)C31—O3A—C32A—C33A162.8 (15)
C11—C12—C21—N11.2 (2)C32—O3—C31—C30177.1 (4)
C11—C12—C21—C20178.78 (14)C32A—O3A—C31—C30130 (2)
C11—C22—C23—C24179.01 (15)C34—O4—C33—C32170.9 (6)
C11—C22—C27—C26179.98 (16)C34A—O4A—C33A—C32A171.9 (15)
C12—C11—C22—C23101.14 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C27—H27···N1i0.932.673.537 (2)156
C29—H29c···O4ii0.962.693.415 (6)132
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y, z1.
 

Funding information

This work was supported by the National Natural Science Foundation of China (award No. 51672002).

References

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