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

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ISSN: 2414-3146

5,13-Bis(4-meth­­oxy­phen­yl)di­naphtho­[2,3-b:2′,3′-d]thio­phene S,S-dioxide di­chloro­methane hemisolvate

aPG and Research Department of Physics, Government Arts College for Men (Autonomous), University of Madras, Nandanam, Chennai 600 035, India, bDepartment of Physics, Jeppiaar Engineering College, Jeppiaar Nagar, OMR, Chennai 600 119, India, cDepartment of Chemistry, National College (Autonomous), Tiruchirappalli 620 001, India, and dDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: agsv71@yahoo.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 13 August 2019; accepted 11 October 2019; online 19 November 2019)

The title com­pound, C34H24O4S·0.5CH2Cl2, crystallizes with two independent mol­ecules and one di­chloro­methane solvent mol­ecule in the asymmetric unit. The crystal packing is consolidated by C—H⋯O hydrogen bonds.

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

Structure description

In order to ascertain the structure of the title com­pound, a crystallographic study has been carried out. The displacement ellipsoid plot of the mol­ecule is shown in Fig. 1[link].

[Figure 1]
Figure 1
The mol­ecular structure of the title com­pound, showing the atomic numbering and displacement ellipsoids drawn at the 30% probability level.

The asymmetric unit com­prises two mol­ecules of the di­naphtho­thio­phene com­pound and one di­chloro­methane (DCM) solvent mol­ecule. The solvent mol­ecule is disordered over three sets of sites, with refined site occupancies of 0.279 (3), 0.330 (3) and 0.391 (3).

The central di­naphtho­thio­phene ring system is essentially planar in both molecules, with maximum deviations of 0.010 (3) and 0.005 (3) Å.

The plane of the naphthalene ring (atoms C1–C10) makes dihedral angles of 72.43 (8) and 85.05 (7)° with the planes of phenyl rings C21–C26 and C27–C32, respectively. In the second mol­ecule, these dihedral angles are 72.17 (8)° between C1′–C10′ and C21′–C26′, and 88.71 (7)° between C1′–C10′ and C27′-C32′.

The packing of the mol­ecules in the unit cell is consolidated by C—H⋯O inter­actions (Table 1[link]). The C34′—H34B⋯O2′ and C34—H34E⋯O1 inter­actions lead to the formation of a C(12) chain running along the a-axis direction, as shown in Fig. 2[link]. Furthermore, the mol­ecules are linked by pairs of C6—H6⋯O4 and C13′—H13′⋯O2′ hydrogen bonds, forming inversion dimers with R22(10) and R22(20) ring motifs (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O2i 0.93 2.46 3.330 (3) 156
C26′—H26′⋯O2i 0.93 2.59 3.329 (4) 137
C6—H6⋯O4ii 0.93 2.56 3.304 (4) 137
C13′—H13′⋯O1′iii 0.93 2.59 3.500 (3) 165
C34′—H34B⋯O2′iv 0.96 2.45 3.191 (4) 134
C34—H34E⋯O1v 0.96 2.60 3.177 (4) 119
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y, -z+1; (iii) -x, -y+1, -z+2; (iv) x, y+1, z; (v) x-1, y, z.
[Figure 2]
Figure 2
Part of the crystal structure, showing a C(12) chain formed via C—H⋯O hydrogen-bond inter­actions. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.
[Figure 3]
Figure 3
Part of the crystal structure, showing the R22(10) and R22(20) dimers. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Synthesis and crystallization

To a solution of dianisylbenzo[c]furan (0.24 g, 0.72 mmol) in dry toluene (15 ml), naphtho­[b]thio­phene S,S-dioxide (0.25 g, 1.48 mmol) was added and the resulting solution refluxed until the disappearance of the fluorescent colour of the benzo[c]furan (12 h). To this, p-toluenesulfonic acid (PTSA; 0.56 g, 2.90 mmol) was added and the solution further refluxed for 10 h. The reaction mixture was then poured into a saturated solution of NaHCO3 (50 ml), extracted with ethyl acetate (3 × 20 ml) and dried (Na2SO4). Removal of the solvent was followed by column chromatographic purification (silica gel; 10% ethyl acetate in hexa­ne), affording dibenzo­thio­phene S,S-dioxide as a brown solid.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula 2C34H24O4S·CH2Cl2
Mr 1142.11
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 13.7369 (5), 13.8077 (5), 16.4824 (6)
α, β, γ (°) 78.442 (2), 68.211 (2), 80.216 (2)
V3) 2828.35 (18)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.25
Crystal size (mm) 0.30 × 0.30 × 0.25
 
Data collection
Diffractometer Bruker SMART APEXII area-detector
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
No. of measured, independent and observed [I > 2σ(I)] reflections 41656, 11698, 6066
Rint 0.042
(sin θ/λ)max−1) 0.631
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.169, 1.01
No. of reflections 11698
No. of parameters 791
No. of restraints 52
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.28, −0.26
Computer programs: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

5,13-Bis(4-methoxyphenyl)dinaphtho[2,3-b:2',3'-d]thiophene S,S-dioxide dichloromethane hemisolvate top
Crystal data top
2C34H24O4S·CH2Cl2Z = 2
Mr = 1142.11F(000) = 1188
Triclinic, P1Dx = 1.341 Mg m3
a = 13.7369 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.8077 (5) ÅCell parameters from 6066 reflections
c = 16.4824 (6) Åθ = 0.9–0.9°
α = 78.442 (2)°µ = 0.25 mm1
β = 68.211 (2)°T = 293 K
γ = 80.216 (2)°Block, brown
V = 2828.35 (18) Å30.30 × 0.30 × 0.25 mm
Data collection top
Bruker SMART APEXII area-detector
diffractometer
6066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
ω and φ scansθmax = 26.7°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1517
k = 1717
41656 measured reflectionsl = 1920
11698 independent reflections
Refinement top
Refinement on F252 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.071P)2 + 0.6749P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
11698 reflectionsΔρmax = 0.28 e Å3
791 parametersΔρmin = 0.26 e Å3
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.

Refinement. The C—Cl bond lengths were restrained to a distance of 1.72 (1) Å. Atomic displacement parameters of the disordered atoms were made similar in each moiety using similarity restraints (SIMU) with an effective s.u. of 0.01 Å2. In addition, a rigid bond restraint (DELU) with an effective s.u. of 0.01 Å2 was applied for bonded atoms in the dichloromethane solvent molecules.

H atoms were allowed to ride on the parent atoms, with a C—H distance of 0.96 Å for methyl, 0.97 Å for methylene and 0.93 Å for aromatic H atoms, and with Uiso(H) = 1.5Ueq(Cmethyl) and Uiso(H) = 1.2Ueq(C) for the remaining H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.3976 (2)0.23726 (19)0.45563 (17)0.0597 (7)
C1'0.2493 (2)0.64646 (19)0.97637 (17)0.0622 (7)
C2'0.3509 (2)0.62006 (19)0.92568 (17)0.0632 (7)
C20.4515 (2)0.16277 (19)0.40718 (17)0.0621 (7)
C30.3888 (3)0.1006 (2)0.39185 (18)0.0698 (8)
C3'0.4244 (2)0.6913 (2)0.90502 (18)0.0636 (7)
C4'0.5306 (2)0.6720 (2)0.8519 (2)0.0787 (9)
H4'0.5539960.6111610.8313310.094*
C40.4361 (3)0.0182 (2)0.34648 (19)0.0880 (10)
H40.5091360.0056890.3241380.106*
C50.3750 (4)0.0431 (3)0.3352 (2)0.1040 (13)
H50.4066860.0985640.3074450.125*
C5'0.5994 (3)0.7407 (3)0.8302 (2)0.0930 (10)
H5'0.6691910.7266830.7947100.112*
C6'0.5664 (3)0.8318 (3)0.8608 (2)0.0897 (10)
H6'0.6140680.8786510.8451770.108*
C60.2665 (4)0.0230 (3)0.3651 (2)0.1059 (13)
H60.2261290.0637550.3549990.127*
C70.2182 (3)0.0549 (2)0.4085 (2)0.0855 (10)
H70.1450690.0665310.4282260.103*
C7'0.4651 (2)0.8528 (2)0.91310 (19)0.0728 (8)
H7'0.4443160.9136910.9336800.087*
C80.2772 (3)0.1193 (2)0.42465 (18)0.0678 (8)
C8'0.3900 (2)0.78333 (19)0.93714 (17)0.0620 (7)
C90.2252 (2)0.19790 (19)0.47470 (18)0.0627 (7)
C9'0.2837 (2)0.80587 (17)0.99138 (16)0.0577 (7)
C100.2864 (2)0.25688 (18)0.49045 (17)0.0574 (6)
C10'0.2124 (2)0.73788 (17)1.01103 (17)0.0571 (6)
C11'0.0990 (2)0.74440 (18)1.06453 (17)0.0565 (6)
C110.2513 (2)0.34299 (18)0.53960 (17)0.0559 (6)
C120.33786 (19)0.38690 (18)0.53821 (17)0.0571 (6)
C12'0.0523 (2)0.65912 (18)1.06699 (18)0.0636 (7)
C13'0.0509 (2)0.6466 (2)1.11355 (19)0.0697 (8)
H13'0.0780790.5894751.1133500.084*
C130.3276 (2)0.46544 (19)0.58033 (17)0.0621 (7)
H130.3869120.4918940.5773520.075*
C140.2265 (2)0.50587 (19)0.62817 (18)0.0633 (7)
C14'0.1161 (2)0.7211 (2)1.16213 (18)0.0637 (7)
C15'0.2237 (2)0.7130 (2)1.2117 (2)0.0785 (9)
H15'0.2536550.6569411.2127950.094*
C150.2095 (3)0.5854 (2)0.6759 (2)0.0803 (9)
H150.2667020.6145760.6739750.096*
C160.1107 (3)0.6193 (3)0.7243 (2)0.0911 (10)
H160.1006340.6709550.7560430.109*
C16'0.2841 (3)0.7864 (3)1.2580 (2)0.0848 (9)
H16'0.3548010.7797921.2909610.102*
C17'0.2411 (3)0.8713 (3)1.2566 (2)0.0815 (9)
H17'0.2832340.9210161.2883340.098*
C170.0237 (3)0.5777 (3)0.7272 (2)0.0936 (10)
H170.0437390.6012850.7612750.112*
C18'0.1384 (2)0.8819 (2)1.20922 (19)0.0693 (8)
H18'0.1108810.9391861.2086250.083*
C180.0370 (2)0.5031 (2)0.6808 (2)0.0834 (9)
H180.0219420.4773820.6819130.100*
C190.1384 (2)0.4635 (2)0.63067 (19)0.0660 (7)
C19'0.0721 (2)0.80730 (19)1.16051 (17)0.0599 (7)
C20'0.0352 (2)0.81714 (19)1.11112 (18)0.0604 (7)
H20'0.0633440.8742491.1101490.073*
C200.1529 (2)0.3834 (2)0.58504 (19)0.0657 (7)
H200.0943270.3573950.5858840.079*
C210.5687 (2)0.14822 (19)0.37220 (17)0.0633 (7)
C21'0.3850 (2)0.5212 (2)0.89553 (18)0.0659 (7)
C22'0.3929 (3)0.4370 (2)0.9547 (2)0.0825 (9)
H22'0.3768680.4429191.0136110.099*
C220.6268 (3)0.1139 (2)0.4259 (2)0.0844 (9)
H220.5916670.0968950.4861960.101*
C23'0.4241 (3)0.3443 (2)0.9290 (2)0.0836 (9)
H23'0.4294900.2887280.9702550.100*
C230.7358 (3)0.1035 (2)0.3938 (2)0.0863 (10)
H230.7728160.0794220.4320850.104*
C240.7886 (3)0.1289 (2)0.3057 (2)0.0750 (8)
C24'0.4471 (2)0.3341 (2)0.8426 (2)0.0707 (8)
C25'0.4396 (2)0.4170 (2)0.78204 (19)0.0756 (8)
H25'0.4552610.4104230.7233400.091*
C250.7320 (3)0.1628 (2)0.2507 (2)0.0857 (9)
H250.7673230.1799040.1904800.103*
C260.6247 (3)0.1717 (2)0.2831 (2)0.0821 (9)
H260.5881260.1941570.2442740.098*
C26'0.4092 (2)0.5096 (2)0.80782 (19)0.0732 (8)
H26'0.4047280.5650340.7662420.088*
C27'0.2519 (2)0.90197 (18)1.02690 (17)0.0579 (7)
C270.1087 (2)0.2121 (2)0.51208 (19)0.0663 (7)
C280.0558 (2)0.1720 (2)0.5987 (2)0.0810 (9)
H280.0943510.1350050.6325120.097*
C28'0.2169 (2)0.9864 (2)0.98020 (19)0.0733 (8)
H28'0.2131830.9827870.9257060.088*
C29'0.1875 (3)1.0754 (2)1.0120 (2)0.0787 (9)
H29'0.1633121.1309240.9795790.094*
C290.0521 (3)0.1857 (2)0.6359 (2)0.0846 (9)
H290.0857050.1577020.6940000.102*
C300.1108 (3)0.2408 (2)0.5873 (2)0.0773 (9)
C30'0.1939 (2)1.0821 (2)1.0913 (2)0.0705 (8)
C310.0605 (3)0.2810 (2)0.5012 (2)0.0827 (9)
H310.0994610.3178320.4676390.099*
C31'0.2278 (2)0.9990 (2)1.13941 (19)0.0697 (8)
H31'0.2314651.0030811.1938260.084*
C320.0480 (3)0.2665 (2)0.4646 (2)0.0784 (9)
H320.0812140.2942200.4062810.094*
C32'0.2562 (2)0.9101 (2)1.10755 (18)0.0637 (7)
H32'0.2788200.8544041.1408040.076*
C330.9578 (3)0.1065 (3)0.3238 (3)0.1202 (14)
H33A0.9333290.1553470.3629630.180*
H33B1.0306160.1120930.2883670.180*
H33C0.9505810.0412490.3577680.180*
C33'0.4654 (3)0.1576 (2)0.8741 (3)0.1088 (13)
H33D0.5138210.1518730.9048870.163*
H33E0.4790730.1007990.8446530.163*
H33F0.3945050.1608470.9156170.163*
C34'0.1305 (4)1.2547 (3)1.0821 (3)0.1463 (19)
H34A0.1804831.2679511.0232730.219*
H34B0.1205681.3100361.1124600.219*
H34C0.0644311.2447541.0791470.219*
C340.2836 (3)0.2993 (3)0.5812 (3)0.1273 (15)
H34D0.2730840.3685290.5647530.191*
H34E0.3561300.2926000.6170100.191*
H34F0.2658990.2695680.5290060.191*
O10.51147 (15)0.27997 (17)0.54193 (14)0.0872 (6)
O1'0.1225 (2)0.5637 (2)0.93012 (17)0.1185 (9)
O2'0.15741 (19)0.48388 (14)1.06430 (17)0.1143 (9)
O20.51534 (16)0.38610 (15)0.40331 (14)0.0903 (7)
O3'0.47846 (18)0.24479 (16)0.81125 (15)0.0913 (7)
O30.89614 (19)0.12260 (17)0.26712 (16)0.0995 (7)
O4'0.1691 (2)1.16739 (16)1.12854 (16)0.0991 (7)
O40.21771 (18)0.25056 (17)0.63039 (17)0.0976 (7)
S10.45820 (5)0.32462 (5)0.48161 (5)0.0654 (2)
S1'0.14417 (7)0.57256 (6)1.00631 (6)0.0797 (3)
C350.288 (3)0.5232 (14)0.2124 (14)0.189 (9)0.279 (3)
H35A0.2763270.4891350.1711440.226*0.279 (3)
H35B0.3625060.5295110.1940210.226*0.279 (3)
Cl10.2157 (5)0.6368 (5)0.2187 (5)0.165 (2)0.279 (3)
Cl20.2420 (10)0.4615 (13)0.3172 (13)0.148 (5)0.279 (3)
C35A0.2299 (12)0.5629 (17)0.2512 (11)0.151 (6)0.330 (3)
H35C0.1961330.5279540.2250650.181*0.330 (3)
H35D0.1823910.6221440.2671830.181*0.330 (3)
Cl1A0.2223 (12)0.4901 (9)0.3503 (8)0.185 (4)0.330 (3)
Cl2A0.3358 (3)0.6060 (3)0.1648 (2)0.1120 (13)0.330 (3)
C35B0.2897 (13)0.5696 (10)0.2624 (7)0.120 (3)0.391 (3)
H35E0.3630260.5813480.2434360.144*0.391 (3)
H35F0.2450110.6221990.2942360.144*0.391 (3)
Cl1B0.2545 (4)0.5556 (5)0.1757 (3)0.166 (2)0.391 (3)
Cl2B0.2670 (11)0.4546 (10)0.3227 (7)0.180 (4)0.391 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0622 (17)0.0607 (16)0.0629 (16)0.0212 (13)0.0272 (14)0.0012 (13)
C1'0.0718 (19)0.0561 (16)0.0575 (16)0.0154 (13)0.0213 (15)0.0009 (13)
C2'0.077 (2)0.0568 (16)0.0542 (16)0.0102 (14)0.0253 (15)0.0010 (13)
C20.0761 (19)0.0593 (16)0.0522 (15)0.0147 (14)0.0245 (14)0.0010 (13)
C30.103 (2)0.0577 (17)0.0558 (16)0.0222 (16)0.0347 (17)0.0005 (13)
C3'0.0668 (18)0.0620 (17)0.0570 (16)0.0072 (14)0.0230 (14)0.0052 (13)
C4'0.073 (2)0.080 (2)0.076 (2)0.0056 (16)0.0233 (17)0.0015 (16)
C40.130 (3)0.070 (2)0.0641 (19)0.0239 (19)0.029 (2)0.0089 (16)
C50.174 (4)0.076 (2)0.071 (2)0.040 (3)0.038 (3)0.0147 (17)
C5'0.072 (2)0.103 (3)0.090 (2)0.017 (2)0.0181 (19)0.004 (2)
C6'0.080 (2)0.087 (2)0.096 (2)0.0325 (18)0.027 (2)0.014 (2)
C60.172 (4)0.094 (3)0.079 (2)0.061 (3)0.057 (3)0.007 (2)
C70.123 (3)0.079 (2)0.074 (2)0.0439 (19)0.049 (2)0.0014 (17)
C7'0.074 (2)0.0700 (18)0.0735 (19)0.0228 (15)0.0286 (17)0.0095 (15)
C80.095 (2)0.0622 (17)0.0616 (17)0.0311 (16)0.0411 (17)0.0039 (14)
C8'0.0692 (18)0.0595 (16)0.0589 (16)0.0156 (13)0.0289 (15)0.0075 (13)
C90.0734 (18)0.0626 (16)0.0644 (17)0.0275 (14)0.0374 (15)0.0063 (14)
C9'0.0753 (19)0.0474 (14)0.0554 (15)0.0165 (13)0.0302 (15)0.0040 (12)
C100.0610 (16)0.0597 (16)0.0604 (16)0.0203 (12)0.0299 (13)0.0002 (13)
C10'0.0687 (17)0.0481 (14)0.0567 (15)0.0141 (12)0.0250 (14)0.0002 (12)
C11'0.0647 (17)0.0493 (14)0.0594 (16)0.0141 (12)0.0255 (14)0.0026 (12)
C110.0554 (16)0.0565 (15)0.0620 (16)0.0184 (12)0.0265 (13)0.0003 (13)
C120.0555 (15)0.0578 (15)0.0621 (16)0.0192 (12)0.0230 (13)0.0022 (13)
C12'0.0752 (19)0.0509 (15)0.0713 (18)0.0194 (13)0.0309 (15)0.0030 (13)
C13'0.0732 (19)0.0604 (17)0.082 (2)0.0262 (15)0.0317 (17)0.0005 (15)
C130.0568 (17)0.0641 (17)0.0706 (18)0.0203 (13)0.0247 (14)0.0051 (14)
C140.0693 (18)0.0577 (16)0.0666 (17)0.0144 (13)0.0275 (15)0.0037 (13)
C14'0.0625 (17)0.0638 (17)0.0679 (17)0.0149 (14)0.0291 (15)0.0024 (14)
C15'0.071 (2)0.085 (2)0.082 (2)0.0244 (17)0.0306 (18)0.0045 (18)
C150.089 (2)0.0696 (19)0.089 (2)0.0086 (17)0.0357 (19)0.0186 (17)
C160.102 (3)0.082 (2)0.087 (2)0.002 (2)0.030 (2)0.0241 (19)
C16'0.0628 (19)0.104 (3)0.081 (2)0.0104 (19)0.0248 (17)0.001 (2)
C17'0.070 (2)0.094 (2)0.080 (2)0.0040 (18)0.0314 (18)0.0144 (18)
C170.082 (2)0.095 (3)0.086 (2)0.004 (2)0.0123 (19)0.018 (2)
C18'0.071 (2)0.0726 (18)0.0707 (19)0.0028 (15)0.0327 (16)0.0133 (15)
C180.065 (2)0.087 (2)0.092 (2)0.0092 (16)0.0191 (18)0.0122 (19)
C190.0591 (17)0.0650 (17)0.0698 (18)0.0102 (13)0.0210 (15)0.0011 (14)
C19'0.0634 (17)0.0637 (16)0.0603 (16)0.0103 (13)0.0327 (14)0.0018 (13)
C20'0.0690 (18)0.0518 (15)0.0696 (17)0.0152 (13)0.0322 (15)0.0062 (13)
C200.0537 (17)0.0697 (18)0.0790 (19)0.0171 (13)0.0271 (15)0.0065 (15)
C210.080 (2)0.0594 (16)0.0518 (16)0.0055 (14)0.0250 (15)0.0075 (13)
C21'0.0709 (18)0.0666 (18)0.0558 (17)0.0058 (14)0.0191 (14)0.0064 (14)
C22'0.116 (3)0.069 (2)0.0587 (18)0.0057 (17)0.0326 (18)0.0098 (15)
C220.090 (2)0.095 (2)0.0557 (18)0.0063 (18)0.0246 (18)0.0023 (16)
C23'0.111 (3)0.0659 (19)0.068 (2)0.0078 (17)0.0321 (19)0.0084 (15)
C230.090 (3)0.094 (2)0.070 (2)0.0131 (19)0.0366 (19)0.0050 (17)
C240.081 (2)0.0654 (18)0.073 (2)0.0043 (15)0.0206 (19)0.0190 (15)
C24'0.0713 (19)0.0720 (19)0.0687 (19)0.0017 (15)0.0222 (16)0.0192 (16)
C25'0.079 (2)0.091 (2)0.0548 (17)0.0079 (17)0.0188 (16)0.0149 (17)
C250.088 (2)0.103 (2)0.0553 (18)0.0130 (19)0.0135 (19)0.0065 (17)
C260.089 (2)0.098 (2)0.0572 (18)0.0088 (18)0.0285 (18)0.0025 (16)
C26'0.078 (2)0.076 (2)0.0600 (18)0.0103 (15)0.0206 (16)0.0019 (15)
C27'0.0655 (16)0.0527 (15)0.0619 (16)0.0230 (12)0.0292 (14)0.0051 (13)
C270.0761 (19)0.0662 (17)0.0730 (19)0.0336 (14)0.0423 (16)0.0065 (14)
C280.081 (2)0.092 (2)0.084 (2)0.0394 (17)0.0499 (18)0.0240 (17)
C28'0.104 (2)0.0570 (17)0.0688 (18)0.0156 (15)0.0462 (18)0.0044 (14)
C29'0.106 (2)0.0509 (17)0.083 (2)0.0090 (15)0.0447 (19)0.0032 (15)
C290.078 (2)0.095 (2)0.086 (2)0.0395 (17)0.0394 (19)0.0212 (18)
C300.074 (2)0.0717 (19)0.099 (2)0.0304 (16)0.043 (2)0.0022 (17)
C30'0.078 (2)0.0541 (17)0.082 (2)0.0194 (14)0.0246 (17)0.0103 (15)
C310.084 (2)0.084 (2)0.096 (2)0.0185 (17)0.057 (2)0.0080 (18)
C31'0.083 (2)0.0712 (19)0.0655 (18)0.0239 (15)0.0327 (16)0.0062 (15)
C320.089 (2)0.083 (2)0.075 (2)0.0275 (17)0.0455 (18)0.0107 (16)
C32'0.0729 (18)0.0570 (16)0.0683 (18)0.0185 (13)0.0343 (15)0.0031 (14)
C330.091 (3)0.120 (3)0.152 (4)0.007 (2)0.051 (3)0.023 (3)
C33'0.135 (3)0.072 (2)0.111 (3)0.002 (2)0.033 (3)0.025 (2)
C34'0.211 (5)0.054 (2)0.141 (4)0.008 (3)0.031 (4)0.018 (2)
C340.082 (3)0.136 (3)0.170 (4)0.000 (2)0.067 (3)0.002 (3)
O10.0653 (12)0.1178 (17)0.0988 (15)0.0044 (11)0.0479 (12)0.0362 (13)
O1'0.1149 (19)0.148 (2)0.1134 (19)0.0487 (16)0.0227 (16)0.0702 (17)
O2'0.1077 (18)0.0480 (12)0.141 (2)0.0151 (11)0.0039 (16)0.0020 (13)
O20.0857 (14)0.0934 (14)0.0819 (14)0.0497 (12)0.0016 (12)0.0172 (12)
O3'0.1037 (17)0.0791 (15)0.0862 (15)0.0017 (12)0.0220 (13)0.0324 (13)
O30.0783 (16)0.1057 (17)0.1039 (18)0.0073 (13)0.0199 (14)0.0292 (14)
O4'0.1255 (19)0.0648 (14)0.1042 (17)0.0168 (13)0.0299 (15)0.0207 (13)
O40.0757 (15)0.1009 (16)0.1211 (19)0.0234 (12)0.0422 (14)0.0003 (14)
S10.0543 (4)0.0764 (5)0.0716 (5)0.0222 (3)0.0194 (4)0.0168 (4)
S1'0.0862 (6)0.0602 (5)0.0895 (6)0.0262 (4)0.0144 (5)0.0202 (4)
C350.160 (13)0.169 (11)0.168 (12)0.014 (10)0.019 (13)0.026 (11)
Cl10.192 (6)0.134 (4)0.152 (5)0.012 (4)0.060 (4)0.017 (4)
Cl20.073 (4)0.139 (8)0.174 (10)0.022 (5)0.001 (5)0.033 (6)
C35A0.139 (11)0.120 (10)0.151 (11)0.032 (10)0.017 (9)0.024 (9)
Cl1A0.192 (11)0.168 (8)0.186 (8)0.047 (7)0.075 (7)0.037 (6)
Cl2A0.098 (2)0.118 (2)0.115 (3)0.0189 (19)0.044 (2)0.0132 (19)
C35B0.100 (7)0.157 (8)0.118 (8)0.028 (7)0.038 (6)0.038 (6)
Cl1B0.158 (4)0.219 (5)0.108 (3)0.050 (4)0.061 (3)0.026 (3)
Cl2B0.164 (9)0.204 (6)0.112 (4)0.019 (5)0.025 (5)0.036 (4)
Geometric parameters (Å, º) top
C1—C21.369 (4)C21—C261.381 (4)
C1—C101.417 (4)C21'—C22'1.377 (4)
C1—S11.773 (3)C21'—C26'1.394 (4)
C1'—C2'1.364 (4)C22'—C23'1.378 (4)
C1'—C10'1.426 (3)C22'—H22'0.9300
C1'—S1'1.772 (3)C22—C231.382 (4)
C2'—C3'1.432 (4)C22—H220.9300
C2'—C21'1.487 (4)C23'—C24'1.372 (4)
C2—C31.429 (4)C23'—H23'0.9300
C2—C211.487 (4)C23—C241.364 (4)
C3—C41.415 (4)C23—H230.9300
C3—C81.420 (4)C24—C251.368 (4)
C3'—C4'1.407 (4)C24—O31.370 (4)
C3'—C8'1.414 (4)C24'—O3'1.371 (3)
C4'—C5'1.356 (4)C24'—C25'1.377 (4)
C4'—H4'0.9300C25'—C26'1.376 (4)
C4—C51.369 (5)C25'—H25'0.9300
C4—H40.9300C25—C261.362 (4)
C5—C61.382 (5)C25—H250.9300
C5—H50.9300C26—H260.9300
C5'—C6'1.391 (5)C26'—H26'0.9300
C5'—H5'0.9300C27'—C32'1.380 (4)
C6'—C7'1.355 (4)C27'—C28'1.381 (3)
C6'—H6'0.9300C27—C321.382 (4)
C6—C71.350 (5)C27—C281.387 (4)
C6—H60.9300C28—C291.373 (4)
C7—C81.420 (4)C28—H280.9300
C7—H70.9300C28'—C29'1.370 (4)
C7'—C8'1.422 (4)C28'—H28'0.9300
C7'—H7'0.9300C29'—C30'1.366 (4)
C8—C91.424 (4)C29'—H29'0.9300
C8'—C9'1.420 (4)C29—C301.376 (4)
C9—C101.385 (3)C29—H290.9300
C9—C271.479 (4)C30—O41.370 (4)
C9'—C10'1.379 (3)C30—C311.374 (4)
C9'—C27'1.490 (3)C30'—O4'1.370 (3)
C10—C111.484 (4)C30'—C31'1.375 (4)
C10'—C11'1.475 (4)C31—C321.380 (4)
C11'—C20'1.370 (3)C31—H310.9300
C11'—C12'1.421 (3)C31'—C32'1.370 (4)
C11—C201.363 (3)C31'—H31'0.9300
C11—C121.415 (3)C32—H320.9300
C12—C131.362 (3)C32'—H32'0.9300
C12—S11.742 (3)C33—O31.442 (4)
C12'—C13'1.360 (4)C33—H33A0.9600
C12'—S1'1.747 (3)C33—H33B0.9600
C13'—C14'1.410 (4)C33—H33C0.9600
C13'—H13'0.9300C33'—O3'1.411 (4)
C13—C141.400 (4)C33'—H33D0.9600
C13—H130.9300C33'—H33E0.9600
C14—C151.415 (4)C33'—H33F0.9600
C14—C191.416 (4)C34'—O4'1.427 (4)
C14'—C15'1.410 (4)C34'—H34A0.9600
C14'—C19'1.415 (4)C34'—H34B0.9600
C15'—C16'1.362 (4)C34'—H34C0.9600
C15'—H15'0.9300C34—O41.431 (4)
C15—C161.352 (4)C34—H34D0.9600
C15—H150.9300C34—H34E0.9600
C16—C171.392 (5)C34—H34F0.9600
C16—H160.9300O1—S11.430 (2)
C16'—C17'1.392 (4)O1'—S1'1.426 (3)
C16'—H16'0.9300O2'—S1'1.425 (2)
C17'—C18'1.351 (4)O2—S11.427 (2)
C17'—H17'0.9300C35—Cl21.700 (10)
C17—C181.352 (5)C35—Cl11.707 (10)
C17—H170.9300C35—H35A0.9700
C18'—C19'1.416 (4)C35—H35B0.9700
C18'—H18'0.9300C35A—Cl2A1.708 (9)
C18—C191.410 (4)C35A—Cl1A1.714 (9)
C18—H180.9300C35A—H35C0.9700
C19—C201.406 (4)C35A—H35D0.9700
C19'—C20'1.409 (4)C35B—Cl2B1.707 (9)
C20'—H20'0.9300C35B—Cl1B1.722 (8)
C20—H200.9300C35B—H35E0.9700
C21—C221.369 (4)C35B—H35F0.9700
C2—C1—C10125.2 (2)C26'—C21'—C2'122.1 (3)
C2—C1—S1124.4 (2)C21'—C22'—C23'121.8 (3)
C10—C1—S1110.45 (19)C21'—C22'—H22'119.1
C2'—C1'—C10'124.9 (2)C23'—C22'—H22'119.1
C2'—C1'—S1'124.5 (2)C21—C22—C23122.4 (3)
C10'—C1'—S1'110.5 (2)C21—C22—H22118.8
C1'—C2'—C3'116.7 (2)C23—C22—H22118.8
C1'—C2'—C21'122.0 (2)C24'—C23'—C22'119.9 (3)
C3'—C2'—C21'121.3 (3)C24'—C23'—H23'120.1
C1—C2—C3116.3 (3)C22'—C23'—H23'120.1
C1—C2—C21121.6 (2)C24—C23—C22119.6 (3)
C3—C2—C21122.1 (3)C24—C23—H23120.2
C4—C3—C8119.0 (3)C22—C23—H23120.2
C4—C3—C2121.0 (3)C23—C24—C25118.9 (3)
C8—C3—C2119.9 (3)C23—C24—O3124.4 (3)
C4'—C3'—C8'119.1 (3)C25—C24—O3116.7 (3)
C4'—C3'—C2'121.1 (3)O3'—C24'—C23'123.8 (3)
C8'—C3'—C2'119.8 (2)O3'—C24'—C25'116.7 (3)
C5'—C4'—C3'121.0 (3)C23'—C24'—C25'119.5 (3)
C5'—C4'—H4'119.5C26'—C25'—C24'120.4 (3)
C3'—C4'—H4'119.5C26'—C25'—H25'119.8
C5—C4—C3120.5 (4)C24'—C25'—H25'119.8
C5—C4—H4119.8C26—C25—C24120.9 (3)
C3—C4—H4119.8C26—C25—H25119.6
C4—C5—C6120.3 (4)C24—C25—H25119.6
C4—C5—H5119.9C25—C26—C21121.7 (3)
C6—C5—H5119.9C25—C26—H26119.1
C4'—C5'—C6'120.5 (3)C21—C26—H26119.1
C4'—C5'—H5'119.7C25'—C26'—C21'120.8 (3)
C6'—C5'—H5'119.7C25'—C26'—H26'119.6
C7'—C6'—C5'120.3 (3)C21'—C26'—H26'119.6
C7'—C6'—H6'119.9C32'—C27'—C28'117.5 (2)
C5'—C6'—H6'119.9C32'—C27'—C9'121.4 (2)
C7—C6—C5121.2 (3)C28'—C27'—C9'121.1 (2)
C7—C6—H6119.4C32—C27—C28117.0 (3)
C5—C6—H6119.4C32—C27—C9122.7 (3)
C6—C7—C8121.1 (4)C28—C27—C9120.3 (3)
C6—C7—H7119.4C29—C28—C27121.6 (3)
C8—C7—H7119.4C29—C28—H28119.2
C6'—C7'—C8'121.2 (3)C27—C28—H28119.2
C6'—C7'—H7'119.4C29'—C28'—C27'121.8 (3)
C8'—C7'—H7'119.4C29'—C28'—H28'119.1
C3—C8—C7117.9 (3)C27'—C28'—H28'119.1
C3—C8—C9121.5 (2)C30'—C29'—C28'119.8 (3)
C7—C8—C9120.6 (3)C30'—C29'—H29'120.1
C3'—C8'—C9'121.1 (2)C28'—C29'—H29'120.1
C3'—C8'—C7'117.9 (3)C28—C29—C30120.2 (3)
C9'—C8'—C7'121.1 (3)C28—C29—H29119.9
C10—C9—C8118.3 (3)C30—C29—H29119.9
C10—C9—C27121.5 (3)O4—C30—C31124.8 (3)
C8—C9—C27120.2 (2)O4—C30—C29115.8 (3)
C10'—C9'—C8'119.4 (2)C31—C30—C29119.5 (3)
C10'—C9'—C27'121.3 (2)C29'—C30'—O4'124.9 (3)
C8'—C9'—C27'119.3 (2)C29'—C30'—C31'119.6 (3)
C9—C10—C1118.9 (2)O4'—C30'—C31'115.6 (3)
C9—C10—C11128.4 (2)C30—C31—C32119.7 (3)
C1—C10—C11112.7 (2)C30—C31—H31120.1
C9'—C10'—C1'118.1 (2)C32—C31—H31120.1
C9'—C10'—C11'129.5 (2)C32'—C31'—C30'120.3 (3)
C1'—C10'—C11'112.4 (2)C32'—C31'—H31'119.8
C20'—C11'—C12'117.3 (2)C30'—C31'—H31'119.8
C20'—C11'—C10'130.6 (2)C31—C32—C27121.9 (3)
C12'—C11'—C10'112.2 (2)C31—C32—H32119.0
C20—C11—C12117.2 (2)C27—C32—H32119.0
C20—C11—C10131.1 (2)C31'—C32'—C27'121.1 (3)
C12—C11—C10111.6 (2)C31'—C32'—H32'119.5
C13—C12—C11123.6 (2)C27'—C32'—H32'119.5
C13—C12—S1124.3 (2)O3—C33—H33A109.5
C11—C12—S1112.09 (19)O3—C33—H33B109.5
C13'—C12'—C11'123.3 (3)H33A—C33—H33B109.5
C13'—C12'—S1'125.0 (2)O3—C33—H33C109.5
C11'—C12'—S1'111.7 (2)H33A—C33—H33C109.5
C12'—C13'—C14'119.4 (2)H33B—C33—H33C109.5
C12'—C13'—H13'120.3O3'—C33'—H33D109.5
C14'—C13'—H13'120.3O3'—C33'—H33E109.5
C12—C13—C14119.2 (2)H33D—C33'—H33E109.5
C12—C13—H13120.4O3'—C33'—H33F109.5
C14—C13—H13120.4H33D—C33'—H33F109.5
C13—C14—C15122.5 (3)H33E—C33'—H33F109.5
C13—C14—C19118.5 (2)O4'—C34'—H34A109.5
C15—C14—C19119.0 (3)O4'—C34'—H34B109.5
C13'—C14'—C15'122.3 (3)H34A—C34'—H34B109.5
C13'—C14'—C19'118.7 (2)O4'—C34'—H34C109.5
C15'—C14'—C19'119.0 (3)H34A—C34'—H34C109.5
C16'—C15'—C14'120.5 (3)H34B—C34'—H34C109.5
C16'—C15'—H15'119.7O4—C34—H34D109.5
C14'—C15'—H15'119.7O4—C34—H34E109.5
C16—C15—C14120.5 (3)H34D—C34—H34E109.5
C16—C15—H15119.8O4—C34—H34F109.5
C14—C15—H15119.8H34D—C34—H34F109.5
C15—C16—C17120.8 (3)H34E—C34—H34F109.5
C15—C16—H16119.6C24'—O3'—C33'117.4 (2)
C17—C16—H16119.6C24—O3—C33118.2 (3)
C15'—C16'—C17'120.6 (3)C30'—O4'—C34'117.3 (3)
C15'—C16'—H16'119.7C30—O4—C34118.5 (3)
C17'—C16'—H16'119.7O2—S1—O1117.46 (14)
C18'—C17'—C16'120.4 (3)O2—S1—C12111.10 (13)
C18'—C17'—H17'119.8O1—S1—C12109.52 (13)
C16'—C17'—H17'119.8O2—S1—C1110.65 (13)
C18—C17—C16120.3 (3)O1—S1—C1112.36 (13)
C18—C17—H17119.9C12—S1—C193.13 (12)
C16—C17—H17119.9O2'—S1'—O1'117.94 (17)
C17'—C18'—C19'121.2 (3)O2'—S1'—C12'109.59 (14)
C17'—C18'—H18'119.4O1'—S1'—C12'111.38 (16)
C19'—C18'—H18'119.4O2'—S1'—C1'111.66 (15)
C17—C18—C19121.3 (3)O1'—S1'—C1'110.40 (14)
C17—C18—H18119.4C12'—S1'—C1'93.13 (13)
C19—C18—H18119.4Cl2—C35—Cl1103.8 (10)
C20—C19—C18121.6 (3)Cl2—C35—H35A111.0
C20—C19—C14120.2 (3)Cl1—C35—H35A111.0
C18—C19—C14118.1 (3)Cl2—C35—H35B111.0
C20'—C19'—C14'119.9 (2)Cl1—C35—H35B111.0
C20'—C19'—C18'121.8 (2)H35A—C35—H35B109.0
C14'—C19'—C18'118.3 (3)Cl2A—C35A—Cl1A130.9 (12)
C11'—C20'—C19'121.4 (2)Cl2A—C35A—H35C104.5
C11'—C20'—H20'119.3Cl1A—C35A—H35C104.5
C19'—C20'—H20'119.3Cl2A—C35A—H35D104.5
C11—C20—C19121.3 (2)Cl1A—C35A—H35D104.5
C11—C20—H20119.4H35C—C35A—H35D105.7
C19—C20—H20119.4Cl2B—C35B—Cl1B98.2 (7)
C22—C21—C26116.4 (3)Cl2B—C35B—H35E112.1
C22—C21—C2122.4 (3)Cl1B—C35B—H35E112.1
C26—C21—C2121.1 (3)Cl2B—C35B—H35F112.1
C22'—C21'—C26'117.5 (3)Cl1B—C35B—H35F112.1
C22'—C21'—C2'120.3 (2)H35E—C35B—H35F109.8
C10'—C1'—C2'—C3'1.2 (4)C13'—C14'—C19'—C20'0.2 (4)
S1'—C1'—C2'—C3'177.4 (2)C15'—C14'—C19'—C20'179.8 (3)
C10'—C1'—C2'—C21'176.8 (2)C13'—C14'—C19'—C18'179.7 (2)
S1'—C1'—C2'—C21'4.6 (4)C15'—C14'—C19'—C18'0.1 (4)
C10—C1—C2—C30.4 (4)C17'—C18'—C19'—C20'179.7 (3)
S1—C1—C2—C3179.0 (2)C17'—C18'—C19'—C14'0.4 (4)
C10—C1—C2—C21179.3 (2)C12'—C11'—C20'—C19'0.9 (4)
S1—C1—C2—C210.6 (4)C10'—C11'—C20'—C19'178.2 (3)
C1—C2—C3—C4176.7 (2)C14'—C19'—C20'—C11'0.4 (4)
C21—C2—C3—C43.6 (4)C18'—C19'—C20'—C11'179.7 (2)
C1—C2—C3—C81.4 (4)C12—C11—C20—C191.8 (4)
C21—C2—C3—C8178.3 (2)C10—C11—C20—C19177.0 (3)
C1'—C2'—C3'—C4'178.9 (3)C18—C19—C20—C11177.4 (3)
C21'—C2'—C3'—C4'3.0 (4)C14—C19—C20—C111.8 (4)
C1'—C2'—C3'—C8'0.1 (4)C1—C2—C21—C2270.3 (4)
C21'—C2'—C3'—C8'178.0 (2)C3—C2—C21—C22110.1 (3)
C8'—C3'—C4'—C5'1.0 (4)C1—C2—C21—C26107.8 (3)
C2'—C3'—C4'—C5'178.0 (3)C3—C2—C21—C2671.8 (4)
C8—C3—C4—C50.7 (4)C1'—C2'—C21'—C22'71.8 (4)
C2—C3—C4—C5177.4 (3)C3'—C2'—C21'—C22'106.2 (3)
C3—C4—C5—C62.6 (5)C1'—C2'—C21'—C26'107.7 (3)
C3'—C4'—C5'—C6'0.5 (5)C3'—C2'—C21'—C26'74.3 (4)
C4'—C5'—C6'—C7'0.5 (5)C26'—C21'—C22'—C23'0.3 (5)
C4—C5—C6—C72.5 (6)C2'—C21'—C22'—C23'179.9 (3)
C5—C6—C7—C80.4 (5)C26—C21—C22—C230.5 (5)
C5'—C6'—C7'—C8'0.8 (5)C2—C21—C22—C23177.7 (3)
C4—C3—C8—C71.3 (4)C21'—C22'—C23'—C24'0.6 (5)
C2—C3—C8—C7179.4 (2)C21—C22—C23—C240.6 (5)
C4—C3—C8—C9176.7 (2)C22—C23—C24—C251.0 (5)
C2—C3—C8—C91.4 (4)C22—C23—C24—O3179.3 (3)
C6—C7—C8—C31.4 (4)C22'—C23'—C24'—O3'179.9 (3)
C6—C7—C8—C9176.6 (3)C22'—C23'—C24'—C25'0.5 (5)
C4'—C3'—C8'—C9'179.6 (3)O3'—C24'—C25'—C26'179.7 (3)
C2'—C3'—C8'—C9'1.3 (4)C23'—C24'—C25'—C26'0.1 (5)
C4'—C3'—C8'—C7'0.6 (4)C23—C24—C25—C260.4 (5)
C2'—C3'—C8'—C7'178.4 (3)O3—C24—C25—C26179.9 (3)
C6'—C7'—C8'—C3'0.3 (4)C24—C25—C26—C210.7 (5)
C6'—C7'—C8'—C9'179.5 (3)C22—C21—C26—C251.1 (5)
C3—C8—C9—C100.4 (4)C2—C21—C26—C25177.1 (3)
C7—C8—C9—C10178.3 (3)C24'—C25'—C26'—C21'0.3 (5)
C3—C8—C9—C27176.7 (2)C22'—C21'—C26'—C25'0.2 (5)
C7—C8—C9—C271.2 (4)C2'—C21'—C26'—C25'179.4 (3)
C3'—C8'—C9'—C10'1.8 (4)C10'—C9'—C27'—C32'88.6 (3)
C7'—C8'—C9'—C10'178.0 (3)C8'—C9'—C27'—C32'90.6 (3)
C3'—C8'—C9'—C27'177.4 (2)C10'—C9'—C27'—C28'91.5 (3)
C7'—C8'—C9'—C27'2.8 (4)C8'—C9'—C27'—C28'89.4 (3)
C8—C9—C10—C10.6 (4)C10—C9—C27—C3297.3 (3)
C27—C9—C10—C1177.6 (2)C8—C9—C27—C3285.7 (3)
C8—C9—C10—C11179.4 (2)C10—C9—C27—C2881.2 (3)
C27—C9—C10—C113.5 (4)C8—C9—C27—C2895.8 (3)
C2—C1—C10—C90.6 (4)C32—C27—C28—C290.0 (4)
S1—C1—C10—C9178.2 (2)C9—C27—C28—C29178.6 (3)
C2—C1—C10—C11179.6 (2)C32'—C27'—C28'—C29'0.1 (4)
S1—C1—C10—C110.8 (3)C9'—C27'—C28'—C29'179.9 (3)
C8'—C9'—C10'—C1'0.7 (4)C27'—C28'—C29'—C30'0.9 (5)
C27'—C9'—C10'—C1'178.5 (2)C27—C28—C29—C300.4 (5)
C8'—C9'—C10'—C11'179.4 (3)C28—C29—C30—O4179.7 (3)
C27'—C9'—C10'—C11'1.4 (4)C28—C29—C30—C310.7 (5)
C2'—C1'—C10'—C9'0.9 (4)C28'—C29'—C30'—O4'178.4 (3)
S1'—C1'—C10'—C9'177.9 (2)C28'—C29'—C30'—C31'1.3 (5)
C2'—C1'—C10'—C11'179.1 (3)O4—C30—C31—C32179.8 (3)
S1'—C1'—C10'—C11'2.2 (3)C29—C30—C31—C320.6 (5)
C9'—C10'—C11'—C20'2.5 (5)C29'—C30'—C31'—C32'0.8 (4)
C1'—C10'—C11'—C20'177.4 (3)O4'—C30'—C31'—C32'179.0 (3)
C9'—C10'—C11'—C12'178.4 (3)C30—C31—C32—C270.2 (5)
C1'—C10'—C11'—C12'1.7 (3)C28—C27—C32—C310.1 (4)
C9—C10—C11—C203.7 (5)C9—C27—C32—C31178.4 (3)
C1—C10—C11—C20177.4 (3)C30'—C31'—C32'—C27'0.2 (4)
C9—C10—C11—C12177.5 (3)C28'—C27'—C32'—C31'0.6 (4)
C1—C10—C11—C121.4 (3)C9'—C27'—C32'—C31'179.4 (2)
C20—C11—C12—C130.8 (4)C23'—C24'—O3'—C33'13.5 (5)
C10—C11—C12—C13178.2 (2)C25'—C24'—O3'—C33'167.0 (3)
C20—C11—C12—S1177.6 (2)C23—C24—O3—C3312.4 (5)
C10—C11—C12—S11.4 (3)C25—C24—O3—C33167.9 (3)
C20'—C11'—C12'—C13'0.7 (4)C29'—C30'—O4'—C34'2.1 (5)
C10'—C11'—C12'—C13'178.5 (3)C31'—C30'—O4'—C34'178.1 (3)
C20'—C11'—C12'—S1'178.8 (2)C31—C30—O4—C345.1 (5)
C10'—C11'—C12'—S1'0.4 (3)C29—C30—O4—C34174.5 (3)
C11'—C12'—C13'—C14'0.1 (4)C13—C12—S1—O268.9 (3)
S1'—C12'—C13'—C14'178.0 (2)C11—C12—S1—O2114.3 (2)
C11—C12—C13—C140.2 (4)C13—C12—S1—O162.5 (3)
S1—C12—C13—C14176.2 (2)C11—C12—S1—O1114.3 (2)
C12—C13—C14—C15178.0 (3)C13—C12—S1—C1177.5 (2)
C12—C13—C14—C190.2 (4)C11—C12—S1—C10.8 (2)
C12'—C13'—C14'—C15'179.9 (3)C2—C1—S1—O264.9 (3)
C12'—C13'—C14'—C19'0.3 (4)C10—C1—S1—O2113.9 (2)
C13'—C14'—C15'—C16'179.8 (3)C2—C1—S1—O168.5 (3)
C19'—C14'—C15'—C16'0.6 (4)C10—C1—S1—O1112.7 (2)
C13—C14—C15—C16177.1 (3)C2—C1—S1—C12178.9 (2)
C19—C14—C15—C161.1 (5)C10—C1—S1—C120.0 (2)
C14—C15—C16—C170.9 (5)C13'—C12'—S1'—O2'63.1 (3)
C14'—C15'—C16'—C17'0.7 (5)C11'—C12'—S1'—O2'115.0 (2)
C15'—C16'—C17'—C18'0.2 (5)C13'—C12'—S1'—O1'69.3 (3)
C15—C16—C17—C180.6 (5)C11'—C12'—S1'—O1'112.7 (2)
C16'—C17'—C18'—C19'0.3 (5)C13'—C12'—S1'—C1'177.4 (3)
C16—C17—C18—C192.0 (5)C11'—C12'—S1'—C1'0.7 (2)
C17—C18—C19—C20177.4 (3)C2'—C1'—S1'—O2'67.1 (3)
C17—C18—C19—C141.7 (5)C10'—C1'—S1'—O2'114.2 (2)
C13—C14—C19—C200.7 (4)C2'—C1'—S1'—O1'66.2 (3)
C15—C14—C19—C20179.0 (3)C10'—C1'—S1'—O1'112.6 (2)
C13—C14—C19—C18178.5 (3)C2'—C1'—S1'—C12'179.6 (3)
C15—C14—C19—C180.2 (4)C10'—C1'—S1'—C12'1.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.463.330 (3)156
C26—H26···O2i0.932.593.329 (4)137
C6—H6···O4ii0.932.563.304 (4)137
C13—H13···O1iii0.932.593.500 (3)165
C34—H34B···O2iv0.962.453.191 (4)134
C34—H34E···O1v0.962.603.177 (4)119
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x, y+1, z+2; (iv) x, y+1, z; (v) x1, y, z.
 

Acknowledgements

The authors thank TBI consultancy, University of Madras, India, for the data collection

References

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals 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. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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