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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2732.
Published online 2009 October 17. doi:  10.1107/S1600536809041282
PMCID: PMC2971218

1-(4-Chloro­phen­yl)-2-phenyl-2-(3-phenyl-1-isoquinolylsulfan­yl)ethanone

Abstract

The title compound, C29H20ClNOS, is a 1-substituted-3-phenyl­isoquinoline that crystallizes with four independent mol­ecules in the asymmtric unit. The four mol­ecules have similar C—S—C angles. The most noteworthy differences between the mol­ecules relate to the inclination of the 3-phenyl subsituent with respect to the isoquinoline fused-ring [dihedral angles of 21.2 (1), 25.6 (2), 34.3 (1) and 36.5 (2)°].

Related literature

For the crystal structure of 1-(4-chloro-3-fluoro­phen­yl)-2-[(3-phenyl­isoquinolin-1-yl)sulfan­yl]ethanone, see: Manivel et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2732-scheme1.jpg

Experimental

Crystal data

  • C29H20ClNOS
  • M r = 465.97
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2732-efi1.jpg
  • a = 10.2808 (6) Å
  • b = 11.1145 (7) Å
  • c = 42.169 (3) Å
  • α = 97.562 (1)°
  • β = 96.647 (2)°
  • γ = 90.043 (1)°
  • V = 4743.9 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 290 K
  • 0.30 × 0.24 × 0.17 mm

Data collection

  • Bruker SMART area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.923, T max = 0.955
  • 45825 measured reflections
  • 16659 independent reflections
  • 10228 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.170
  • S = 1.18
  • 16659 reflections
  • 1189 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041282/tk2556sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041282/tk2556Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Department of Science and Technology, India, for use of the diffraction facility at IISc under the IRHPA–DST program. FNK thanks the DST for Fast Track Proposal funding. We thank VIT University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

1-Mercapto-3-phenylisoquinoline (10.0 mmol) and 2-bromo-1-(4-chlorophenyl)-2-phenylethanone (10.5 mmol) were heated in ethanol (50 ml) under a nitrogen atmosphere for 2 h. The solid product was collected and dissolved in chloroform. The chloroform solution was washed with water and dried; the dry solution was concentrated. The solid material was purified by recrystallization from ether.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.98 Å) and were included in the refinement in the riding model approximation with Uiso(H) set to 1.2Ueq(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of one of the four independent molecules of C29H20NOS at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C29H20ClNOSZ = 8
Mr = 465.97F(000) = 1936
Triclinic, P1Dx = 1.305 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.2808 (6) ÅCell parameters from 1324 reflections
b = 11.1145 (7) Åθ = 1.6–24.3°
c = 42.169 (3) ŵ = 0.27 mm1
α = 97.562 (1)°T = 290 K
β = 96.647 (2)°Block, colorless
γ = 90.043 (1)°0.30 × 0.24 × 0.17 mm
V = 4743.9 (5) Å3

Data collection

Bruker SMART area-detector diffractometer16659 independent reflections
Radiation source: fine-focus sealed tube10228 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.923, Tmax = 0.955k = −13→13
45825 measured reflectionsl = −50→50

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.18w = 1/[σ2(Fo2) + (0.0369P)2 + 2.6389P] where P = (Fo2 + 2Fc2)/3
16659 reflections(Δ/σ)max = 0.001
1189 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.20 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.42109 (11)0.61616 (11)0.07142 (3)0.0553 (3)
S20.14531 (11)0.11317 (11)0.06884 (3)0.0579 (3)
S30.07836 (11)0.54707 (11)0.42913 (3)0.0567 (3)
S40.35545 (11)0.04298 (11)0.43006 (3)0.0585 (3)
Cl10.10000 (18)1.01418 (16)0.22600 (4)0.1147 (6)
Cl20.61254 (15)0.50839 (14)0.22440 (3)0.0899 (5)
Cl30.39882 (16)0.78415 (17)0.27399 (4)0.1059 (6)
Cl4−0.10384 (17)0.28896 (15)0.27441 (4)0.1043 (5)
O10.2278 (3)0.5609 (3)0.11499 (8)0.0651 (9)
O20.3808 (3)0.0567 (3)0.11194 (8)0.0649 (9)
O30.2759 (3)0.4471 (3)0.38692 (7)0.0641 (9)
O40.1214 (3)−0.0536 (3)0.38623 (8)0.0676 (9)
N10.5469 (3)0.7207 (3)0.12701 (8)0.0449 (8)
N20.0699 (3)0.2136 (3)0.12441 (9)0.0497 (9)
N3−0.0485 (3)0.5935 (3)0.37340 (8)0.0443 (8)
N40.4325 (3)0.0908 (3)0.37470 (8)0.0488 (9)
C10.5563 (4)0.6405 (4)0.10171 (10)0.0442 (10)
C20.6565 (4)0.7432 (4)0.14938 (11)0.0513 (11)
C30.7697 (4)0.6814 (4)0.14609 (12)0.0599 (13)
H30.84140.69820.16170.072*
C40.8947 (5)0.5242 (5)0.11514 (15)0.0709 (15)
H40.96860.53840.13010.085*
C50.8961 (5)0.4388 (5)0.08922 (15)0.0751 (15)
H50.97150.39400.08680.090*
C60.7863 (5)0.4157 (5)0.06576 (15)0.0820 (16)
H60.78970.35710.04800.098*
C70.6758 (5)0.4798 (4)0.06949 (12)0.0651 (13)
H70.60300.46430.05420.078*
C80.6694 (4)0.5695 (4)0.09612 (11)0.0503 (11)
C90.7796 (4)0.5918 (4)0.11926 (12)0.0535 (12)
C100.6416 (5)0.8365 (4)0.17693 (11)0.0534 (12)
C110.7456 (5)0.9117 (5)0.19087 (12)0.0718 (15)
H110.82580.90460.18270.086*
C120.7303 (7)0.9976 (5)0.21713 (14)0.0850 (18)
H120.80121.04690.22660.102*
C130.6139 (7)1.0107 (5)0.22922 (12)0.0787 (17)
H130.60561.06830.24700.094*
C140.5096 (6)0.9402 (5)0.21551 (12)0.0765 (16)
H140.42950.94970.22370.092*
C150.5225 (5)0.8539 (4)0.18924 (11)0.0645 (13)
H150.45010.80670.17970.077*
C160.3010 (4)0.7185 (4)0.08743 (10)0.0469 (11)
H160.34270.79770.09540.056*
C170.1996 (4)0.7312 (4)0.05883 (10)0.0496 (11)
C180.2187 (5)0.8173 (4)0.03890 (11)0.0610 (13)
H180.29070.86990.04370.073*
C190.1304 (6)0.8252 (5)0.01176 (12)0.0798 (17)
H190.14320.8839−0.00140.096*
C200.0249 (7)0.7478 (7)0.00426 (14)0.0926 (19)
H20−0.03260.7525−0.01430.111*
C210.0041 (6)0.6640 (6)0.02393 (15)0.0936 (19)
H21−0.06910.61290.01930.112*
C220.0919 (5)0.6549 (5)0.05077 (13)0.0753 (15)
H220.07810.59570.06370.090*
C230.2408 (4)0.6697 (4)0.11495 (10)0.0482 (11)
C240.1986 (4)0.7581 (4)0.14110 (10)0.0457 (10)
C250.1895 (4)0.8808 (4)0.13938 (11)0.0604 (13)
H250.20560.91080.12060.073*
C260.1565 (5)0.9601 (5)0.16544 (13)0.0741 (15)
H260.15001.04280.16430.089*
C270.1340 (5)0.9144 (5)0.19270 (13)0.0713 (15)
C280.1417 (5)0.7926 (5)0.19530 (13)0.0746 (15)
H280.12650.76350.21430.090*
C290.1725 (4)0.7147 (5)0.16909 (12)0.0633 (13)
H290.17590.63170.17020.076*
C300.0383 (4)0.1341 (4)0.09883 (10)0.0474 (11)
C31−0.0183 (4)0.2355 (4)0.14699 (11)0.0530 (12)
C32−0.1345 (5)0.1720 (4)0.14294 (13)0.0637 (13)
H32−0.19210.18740.15840.076*
C33−0.2871 (5)0.0162 (5)0.11128 (14)0.0670 (14)
H33−0.34710.02900.12620.080*
C34−0.3135 (5)−0.0676 (5)0.08507 (15)0.0759 (16)
H34−0.3916−0.11210.08230.091*
C35−0.2260 (5)−0.0891 (5)0.06191 (14)0.0786 (16)
H35−0.2461−0.14720.04400.094*
C36−0.1107 (5)−0.0242 (4)0.06574 (13)0.0694 (14)
H36−0.0522−0.03820.05040.083*
C37−0.0807 (4)0.0637 (4)0.09289 (11)0.0503 (11)
C38−0.1695 (4)0.0842 (4)0.11611 (12)0.0556 (12)
C390.0227 (5)0.3273 (4)0.17488 (11)0.0524 (11)
C40−0.0677 (5)0.3925 (5)0.19212 (13)0.0769 (15)
H40−0.15680.37880.18590.092*
C41−0.0271 (6)0.4763 (5)0.21811 (14)0.0840 (17)
H41−0.08940.51740.22950.101*
C420.1039 (6)0.5015 (5)0.22784 (12)0.0741 (15)
H420.13070.55870.24560.089*
C430.1937 (5)0.4391 (5)0.21048 (12)0.0710 (14)
H430.28270.45410.21650.085*
C440.1530 (5)0.3547 (4)0.18427 (11)0.0637 (13)
H440.21550.31510.17260.076*
C450.2801 (4)0.2157 (4)0.08546 (10)0.0477 (11)
H450.24530.29370.09410.057*
C460.3547 (4)0.2334 (4)0.05736 (10)0.0482 (11)
C470.3183 (5)0.3232 (4)0.03839 (11)0.0622 (13)
H470.25040.37480.04350.075*
C480.3820 (6)0.3371 (6)0.01172 (13)0.0824 (17)
H480.35730.3982−0.00070.099*
C490.4815 (7)0.2608 (7)0.00379 (13)0.091 (2)
H490.52440.2700−0.01400.109*
C500.5168 (6)0.1716 (6)0.02208 (15)0.0924 (19)
H500.58370.11930.01660.111*
C510.4549 (5)0.1579 (5)0.04858 (13)0.0778 (16)
H510.48100.09670.06090.093*
C520.3672 (4)0.1656 (4)0.11212 (10)0.0466 (11)
C530.4354 (4)0.2524 (4)0.13870 (10)0.0444 (10)
C540.4428 (4)0.3758 (4)0.13719 (11)0.0572 (12)
H540.40970.40650.11850.069*
C550.4995 (5)0.4535 (4)0.16347 (12)0.0643 (13)
H550.50430.53640.16230.077*
C560.5484 (4)0.4096 (5)0.19114 (11)0.0602 (13)
C570.5453 (5)0.2867 (5)0.19298 (11)0.0633 (13)
H570.58060.25640.21160.076*
C580.4886 (4)0.2090 (4)0.16647 (11)0.0552 (12)
H580.48640.12590.16750.066*
C59−0.0568 (4)0.5391 (4)0.39884 (11)0.0469 (11)
C60−0.1576 (4)0.5924 (4)0.35095 (11)0.0512 (11)
C61−0.2698 (4)0.5344 (4)0.35485 (12)0.0602 (13)
H61−0.34190.53550.33940.072*
C62−0.3943 (4)0.4108 (4)0.38677 (13)0.0650 (14)
H62−0.46910.41030.37210.078*
C63−0.3958 (5)0.3520 (5)0.41298 (15)0.0745 (16)
H63−0.47180.31170.41600.089*
C64−0.2857 (5)0.3513 (5)0.43526 (14)0.0769 (15)
H64−0.28780.30900.45280.092*
C65−0.1745 (5)0.4121 (4)0.43169 (13)0.0689 (14)
H65−0.10170.41250.44700.083*
C66−0.1693 (4)0.4742 (4)0.40486 (11)0.0514 (11)
C67−0.2806 (4)0.4724 (4)0.38164 (12)0.0534 (12)
C68−0.1420 (4)0.6565 (4)0.32276 (10)0.0501 (11)
C69−0.2493 (5)0.6979 (5)0.30449 (13)0.0786 (16)
H69−0.33290.68630.31010.094*
C70−0.2342 (6)0.7561 (5)0.27811 (14)0.0853 (17)
H70−0.30770.78140.26590.102*
C71−0.1128 (6)0.7768 (4)0.26987 (12)0.0688 (14)
H71−0.10260.81590.25210.083*
C72−0.0060 (5)0.7390 (4)0.28833 (12)0.0678 (14)
H720.07750.75380.28310.081*
C73−0.0196 (5)0.6797 (4)0.31429 (11)0.0584 (12)
H730.05460.65470.32640.070*
C740.2000 (4)0.6320 (4)0.41328 (10)0.0469 (11)
H740.15880.70260.40490.056*
C750.3000 (4)0.6750 (4)0.44182 (10)0.0482 (11)
C760.4083 (5)0.6089 (5)0.45012 (13)0.0773 (16)
H760.42530.53770.43710.093*
C770.4928 (6)0.6470 (6)0.47773 (16)0.0961 (19)
H770.56390.59920.48330.115*
C780.4744 (7)0.7507 (7)0.49652 (14)0.096 (2)
H780.53380.77660.51450.115*
C790.3670 (7)0.8181 (6)0.48887 (13)0.0870 (18)
H790.35190.88910.50220.104*
C800.2798 (5)0.7818 (4)0.46142 (11)0.0625 (13)
H800.20800.82940.45630.075*
C810.2611 (4)0.5553 (4)0.38657 (10)0.0472 (11)
C820.3034 (4)0.6155 (4)0.35966 (10)0.0447 (10)
C830.3152 (4)0.7404 (4)0.36117 (11)0.0596 (12)
H830.30110.78990.38000.071*
C840.3475 (5)0.7917 (5)0.33525 (12)0.0681 (14)
H840.35680.87550.33660.082*
C850.3660 (4)0.7189 (5)0.30744 (12)0.0635 (13)
C860.3579 (5)0.5957 (5)0.30527 (12)0.0692 (14)
H860.37290.54710.28640.083*
C870.3269 (4)0.5436 (4)0.33184 (11)0.0578 (12)
H870.32200.45960.33070.069*
C880.4639 (4)0.0348 (4)0.40022 (10)0.0458 (10)
C890.5224 (4)0.0906 (4)0.35278 (11)0.0526 (11)
C900.6387 (5)0.0307 (4)0.35657 (12)0.0630 (13)
H900.69690.03150.34130.076*
C910.7890 (5)−0.0957 (5)0.38808 (14)0.0703 (14)
H910.8493−0.09740.37320.084*
C920.8152 (5)−0.1544 (5)0.41401 (16)0.0795 (16)
H920.8933−0.19600.41680.095*
C930.7265 (5)−0.1536 (5)0.43686 (15)0.0801 (16)
H930.7455−0.19490.45460.096*
C940.6115 (5)−0.0917 (4)0.43297 (12)0.0674 (14)
H940.5529−0.09050.44820.081*
C950.5820 (4)−0.0305 (4)0.40621 (11)0.0514 (11)
C960.6712 (4)−0.0315 (4)0.38316 (12)0.0556 (12)
C970.4834 (5)0.1576 (4)0.32549 (11)0.0552 (12)
C980.5761 (5)0.2219 (5)0.31243 (12)0.0709 (14)
H980.66350.22280.32110.085*
C990.5390 (7)0.2846 (5)0.28655 (14)0.0857 (18)
H990.60150.32790.27820.103*
C1000.4091 (7)0.2830 (5)0.27303 (13)0.0848 (18)
H1000.38410.32310.25530.102*
C1010.3186 (6)0.2213 (5)0.28635 (14)0.0843 (17)
H1010.23110.22070.27770.101*
C1020.3546 (5)0.1608 (5)0.31200 (12)0.0690 (14)
H1020.29060.12050.32070.083*
C1030.2225 (4)0.1309 (4)0.41367 (10)0.0470 (11)
H1030.25860.20100.40560.056*
C1040.1470 (4)0.1752 (4)0.44165 (10)0.0510 (11)
C1050.1837 (5)0.2833 (4)0.46091 (11)0.0619 (13)
H1050.25140.33050.45590.074*
C1060.1194 (6)0.3217 (6)0.48775 (13)0.0834 (17)
H1060.14440.39450.50060.100*
C1070.0206 (7)0.2535 (7)0.49527 (14)0.097 (2)
H107−0.02240.28010.51310.116*
C108−0.0157 (6)0.1463 (6)0.47688 (16)0.098 (2)
H108−0.08230.09900.48230.118*
C1090.0469 (5)0.1076 (5)0.45008 (13)0.0753 (15)
H1090.02100.03460.43750.090*
C1100.1354 (4)0.0551 (4)0.38612 (11)0.0501 (11)
C1110.0696 (4)0.1168 (4)0.35991 (10)0.0467 (11)
C1120.0135 (5)0.0459 (4)0.33201 (11)0.0608 (13)
H1120.0133−0.03820.33090.073*
C113−0.0416 (5)0.0984 (5)0.30600 (12)0.0707 (14)
H113−0.07780.05040.28730.085*
C114−0.0425 (5)0.2222 (5)0.30788 (12)0.0665 (14)
C1150.0082 (5)0.2946 (4)0.33513 (13)0.0690 (14)
H1150.00520.37860.33610.083*
C1160.0638 (4)0.2421 (4)0.36114 (11)0.0614 (13)
H1160.09790.29130.37980.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0443 (7)0.0687 (8)0.0495 (7)0.0062 (6)0.0026 (5)−0.0020 (6)
S20.0463 (7)0.0730 (8)0.0533 (7)−0.0078 (6)0.0113 (6)−0.0007 (6)
S30.0434 (7)0.0755 (9)0.0520 (7)−0.0070 (6)0.0014 (5)0.0147 (6)
S40.0492 (7)0.0738 (9)0.0550 (7)0.0076 (6)0.0096 (6)0.0142 (6)
Cl10.1194 (14)0.1273 (14)0.0909 (12)−0.0069 (11)0.0413 (10)−0.0355 (10)
Cl20.0963 (11)0.0992 (11)0.0664 (9)−0.0146 (9)−0.0021 (8)−0.0074 (8)
Cl30.1045 (12)0.1482 (15)0.0782 (11)0.0078 (11)0.0266 (9)0.0498 (10)
Cl40.1242 (14)0.1077 (12)0.0787 (11)0.0035 (10)−0.0172 (9)0.0288 (9)
O10.073 (2)0.050 (2)0.077 (2)0.0054 (17)0.0175 (18)0.0164 (17)
O20.069 (2)0.049 (2)0.080 (2)0.0000 (16)0.0094 (18)0.0180 (17)
O30.074 (2)0.045 (2)0.073 (2)−0.0001 (17)0.0129 (18)0.0022 (16)
O40.072 (2)0.048 (2)0.080 (2)−0.0001 (17)0.0017 (18)0.0042 (17)
N10.041 (2)0.048 (2)0.045 (2)−0.0026 (16)0.0011 (17)0.0085 (17)
N20.045 (2)0.054 (2)0.053 (2)0.0075 (18)0.0102 (18)0.0140 (19)
N30.038 (2)0.046 (2)0.047 (2)0.0000 (16)0.0005 (17)0.0034 (17)
N40.046 (2)0.052 (2)0.048 (2)−0.0023 (17)0.0098 (18)0.0003 (18)
C10.036 (2)0.049 (3)0.049 (3)−0.002 (2)0.004 (2)0.014 (2)
C20.051 (3)0.050 (3)0.053 (3)−0.006 (2)0.002 (2)0.012 (2)
C30.044 (3)0.068 (3)0.066 (3)−0.002 (2)−0.006 (2)0.017 (3)
C40.045 (3)0.066 (4)0.107 (5)0.009 (3)0.010 (3)0.030 (3)
C50.060 (4)0.067 (4)0.104 (5)0.019 (3)0.023 (3)0.021 (3)
C60.068 (4)0.073 (4)0.104 (5)0.015 (3)0.019 (4)0.002 (3)
C70.048 (3)0.076 (4)0.070 (3)0.009 (3)0.008 (3)0.003 (3)
C80.042 (3)0.050 (3)0.061 (3)0.000 (2)0.012 (2)0.011 (2)
C90.045 (3)0.052 (3)0.067 (3)0.001 (2)0.009 (2)0.018 (2)
C100.056 (3)0.053 (3)0.050 (3)0.000 (2)−0.006 (2)0.014 (2)
C110.067 (3)0.073 (4)0.066 (3)−0.005 (3)−0.019 (3)0.000 (3)
C120.100 (5)0.070 (4)0.071 (4)0.005 (3)−0.030 (4)−0.005 (3)
C130.112 (5)0.066 (4)0.051 (3)0.025 (4)−0.012 (4)−0.001 (3)
C140.099 (5)0.078 (4)0.052 (3)0.016 (3)0.006 (3)0.009 (3)
C150.071 (4)0.069 (3)0.053 (3)−0.004 (3)0.004 (3)0.011 (3)
C160.046 (3)0.048 (3)0.047 (3)0.000 (2)0.006 (2)0.007 (2)
C170.045 (3)0.060 (3)0.044 (3)0.009 (2)0.002 (2)0.008 (2)
C180.061 (3)0.069 (3)0.056 (3)0.013 (3)0.012 (3)0.012 (3)
C190.100 (5)0.093 (4)0.052 (3)0.034 (4)0.016 (3)0.026 (3)
C200.091 (5)0.117 (6)0.062 (4)0.026 (4)−0.016 (3)0.004 (4)
C210.077 (4)0.104 (5)0.089 (5)−0.001 (4)−0.028 (4)0.008 (4)
C220.063 (4)0.083 (4)0.078 (4)−0.006 (3)−0.012 (3)0.020 (3)
C230.037 (2)0.054 (3)0.056 (3)0.002 (2)0.002 (2)0.014 (2)
C240.041 (3)0.057 (3)0.042 (3)0.004 (2)0.007 (2)0.017 (2)
C250.071 (3)0.063 (3)0.052 (3)0.013 (3)0.017 (3)0.016 (2)
C260.083 (4)0.062 (3)0.081 (4)0.021 (3)0.026 (3)0.008 (3)
C270.059 (3)0.081 (4)0.070 (4)−0.003 (3)0.013 (3)−0.009 (3)
C280.081 (4)0.088 (4)0.057 (3)−0.010 (3)0.021 (3)0.007 (3)
C290.063 (3)0.068 (3)0.062 (3)−0.005 (3)0.010 (3)0.016 (3)
C300.044 (3)0.049 (3)0.050 (3)0.005 (2)0.005 (2)0.012 (2)
C310.049 (3)0.060 (3)0.056 (3)0.015 (2)0.016 (2)0.019 (2)
C320.050 (3)0.070 (3)0.078 (4)0.007 (3)0.023 (3)0.021 (3)
C330.050 (3)0.068 (3)0.088 (4)−0.004 (3)0.015 (3)0.023 (3)
C340.051 (3)0.069 (4)0.109 (5)−0.008 (3)0.005 (3)0.021 (3)
C350.069 (4)0.073 (4)0.089 (4)−0.016 (3)0.005 (3)−0.003 (3)
C360.049 (3)0.074 (4)0.084 (4)−0.010 (3)0.009 (3)0.002 (3)
C370.042 (3)0.052 (3)0.060 (3)0.001 (2)0.004 (2)0.018 (2)
C380.041 (3)0.057 (3)0.073 (3)0.002 (2)0.011 (2)0.021 (3)
C390.055 (3)0.056 (3)0.051 (3)0.011 (2)0.017 (2)0.013 (2)
C400.064 (3)0.095 (4)0.072 (4)0.004 (3)0.026 (3)−0.003 (3)
C410.083 (4)0.094 (4)0.075 (4)0.014 (3)0.030 (3)−0.007 (3)
C420.092 (4)0.075 (4)0.055 (3)−0.002 (3)0.017 (3)0.002 (3)
C430.066 (3)0.087 (4)0.060 (3)0.009 (3)0.004 (3)0.008 (3)
C440.061 (3)0.078 (4)0.052 (3)0.016 (3)0.011 (3)0.005 (3)
C450.043 (3)0.051 (3)0.051 (3)0.001 (2)0.010 (2)0.009 (2)
C460.044 (3)0.055 (3)0.044 (3)−0.008 (2)0.006 (2)0.003 (2)
C470.062 (3)0.066 (3)0.060 (3)−0.008 (3)0.001 (3)0.016 (3)
C480.093 (5)0.102 (5)0.054 (3)−0.036 (4)−0.005 (3)0.027 (3)
C490.100 (5)0.124 (6)0.050 (4)−0.037 (4)0.026 (3)0.000 (4)
C500.092 (5)0.108 (5)0.087 (5)0.005 (4)0.050 (4)0.013 (4)
C510.076 (4)0.083 (4)0.083 (4)0.012 (3)0.034 (3)0.020 (3)
C520.042 (3)0.050 (3)0.051 (3)0.000 (2)0.013 (2)0.015 (2)
C530.040 (2)0.052 (3)0.043 (3)0.004 (2)0.008 (2)0.012 (2)
C540.063 (3)0.056 (3)0.055 (3)−0.002 (2)−0.001 (2)0.021 (2)
C550.073 (3)0.059 (3)0.061 (3)−0.012 (3)−0.001 (3)0.019 (3)
C560.050 (3)0.076 (4)0.056 (3)−0.003 (3)0.012 (2)0.009 (3)
C570.073 (3)0.074 (4)0.046 (3)0.016 (3)0.008 (3)0.019 (3)
C580.059 (3)0.055 (3)0.054 (3)0.010 (2)0.009 (2)0.015 (2)
C590.040 (3)0.043 (3)0.055 (3)0.005 (2)0.003 (2)0.000 (2)
C600.041 (3)0.048 (3)0.060 (3)0.000 (2)−0.001 (2)−0.003 (2)
C610.042 (3)0.064 (3)0.069 (3)0.000 (2)−0.007 (2)0.002 (3)
C620.041 (3)0.065 (3)0.084 (4)−0.009 (2)0.006 (3)−0.007 (3)
C630.050 (3)0.065 (4)0.112 (5)−0.008 (3)0.023 (3)0.012 (3)
C640.065 (4)0.083 (4)0.089 (4)−0.010 (3)0.020 (3)0.025 (3)
C650.053 (3)0.078 (4)0.078 (4)−0.010 (3)0.007 (3)0.019 (3)
C660.043 (3)0.046 (3)0.063 (3)−0.001 (2)0.008 (2)0.000 (2)
C670.038 (3)0.048 (3)0.071 (3)0.000 (2)0.006 (2)−0.003 (2)
C680.051 (3)0.046 (3)0.049 (3)0.003 (2)−0.008 (2)0.002 (2)
C690.058 (3)0.091 (4)0.086 (4)−0.003 (3)−0.013 (3)0.029 (3)
C700.067 (4)0.099 (5)0.089 (4)0.002 (3)−0.023 (3)0.037 (4)
C710.086 (4)0.058 (3)0.059 (3)−0.001 (3)−0.005 (3)0.007 (2)
C720.066 (3)0.075 (4)0.062 (3)0.010 (3)0.007 (3)0.007 (3)
C730.049 (3)0.067 (3)0.057 (3)0.009 (2)−0.004 (2)0.009 (2)
C740.043 (3)0.049 (3)0.048 (3)0.000 (2)0.004 (2)0.007 (2)
C750.047 (3)0.057 (3)0.042 (3)−0.011 (2)0.009 (2)0.008 (2)
C760.064 (4)0.082 (4)0.078 (4)0.001 (3)−0.019 (3)0.004 (3)
C770.080 (4)0.111 (5)0.090 (5)−0.003 (4)−0.027 (4)0.015 (4)
C780.090 (5)0.125 (6)0.065 (4)−0.038 (4)−0.022 (4)0.011 (4)
C790.111 (5)0.092 (4)0.052 (4)−0.044 (4)0.013 (3)−0.013 (3)
C800.067 (3)0.067 (3)0.052 (3)−0.009 (3)0.011 (3)0.001 (3)
C810.036 (2)0.050 (3)0.052 (3)−0.005 (2)−0.003 (2)−0.002 (2)
C820.036 (2)0.047 (3)0.049 (3)−0.001 (2)0.006 (2)−0.002 (2)
C830.061 (3)0.058 (3)0.058 (3)−0.003 (2)0.009 (2)0.002 (2)
C840.078 (4)0.061 (3)0.067 (4)−0.016 (3)0.012 (3)0.013 (3)
C850.051 (3)0.088 (4)0.053 (3)−0.002 (3)0.009 (2)0.012 (3)
C860.070 (4)0.092 (4)0.044 (3)0.014 (3)0.009 (3)0.001 (3)
C870.059 (3)0.054 (3)0.057 (3)0.010 (2)0.002 (2)−0.003 (2)
C880.041 (3)0.049 (3)0.046 (3)−0.006 (2)0.007 (2)0.001 (2)
C890.051 (3)0.051 (3)0.056 (3)−0.006 (2)0.015 (2)−0.001 (2)
C900.060 (3)0.064 (3)0.067 (3)0.000 (3)0.023 (3)0.001 (3)
C910.043 (3)0.070 (4)0.096 (4)0.005 (3)0.012 (3)0.001 (3)
C920.058 (4)0.063 (4)0.118 (5)0.019 (3)0.008 (4)0.013 (3)
C930.064 (4)0.077 (4)0.102 (5)0.017 (3)0.002 (3)0.026 (3)
C940.059 (3)0.071 (3)0.073 (4)0.011 (3)0.007 (3)0.013 (3)
C950.042 (3)0.048 (3)0.062 (3)−0.002 (2)0.003 (2)0.002 (2)
C960.046 (3)0.048 (3)0.070 (3)−0.004 (2)0.011 (2)−0.002 (2)
C970.065 (3)0.050 (3)0.051 (3)0.004 (2)0.017 (3)−0.003 (2)
C980.074 (4)0.080 (4)0.065 (3)0.004 (3)0.026 (3)0.014 (3)
C990.119 (6)0.081 (4)0.067 (4)0.008 (4)0.044 (4)0.016 (3)
C1000.117 (5)0.084 (4)0.056 (4)0.028 (4)0.019 (4)0.011 (3)
C1010.092 (5)0.090 (4)0.068 (4)0.013 (4)0.004 (3)0.003 (3)
C1020.071 (4)0.076 (4)0.060 (3)0.000 (3)0.006 (3)0.013 (3)
C1030.043 (3)0.049 (3)0.049 (3)−0.002 (2)0.005 (2)0.007 (2)
C1040.049 (3)0.055 (3)0.048 (3)0.009 (2)0.002 (2)0.005 (2)
C1050.065 (3)0.065 (3)0.052 (3)0.010 (3)−0.001 (3)0.002 (2)
C1060.100 (5)0.088 (4)0.055 (4)0.026 (4)−0.005 (3)−0.008 (3)
C1070.106 (5)0.125 (6)0.065 (4)0.045 (5)0.031 (4)0.016 (4)
C1080.106 (5)0.105 (5)0.094 (5)0.011 (4)0.054 (4)0.016 (4)
C1090.080 (4)0.075 (4)0.075 (4)−0.003 (3)0.027 (3)0.005 (3)
C1100.042 (3)0.049 (3)0.058 (3)0.002 (2)0.012 (2)−0.004 (2)
C1110.043 (3)0.047 (3)0.047 (3)0.000 (2)0.005 (2)−0.004 (2)
C1120.071 (3)0.053 (3)0.055 (3)−0.013 (2)0.008 (3)−0.004 (2)
C1130.077 (4)0.071 (4)0.059 (3)−0.012 (3)0.002 (3)−0.006 (3)
C1140.058 (3)0.070 (4)0.070 (4)0.000 (3)0.000 (3)0.008 (3)
C1150.074 (4)0.049 (3)0.079 (4)0.012 (3)−0.006 (3)0.003 (3)
C1160.066 (3)0.053 (3)0.058 (3)0.002 (2)−0.008 (3)−0.007 (2)

Geometric parameters (Å, °)

S1—C11.770 (4)C51—H510.9300
S1—C161.807 (4)C52—C531.487 (6)
S2—C301.763 (4)C53—C581.380 (6)
S2—C451.809 (4)C53—C541.384 (5)
S3—C591.769 (4)C54—C551.382 (6)
S3—C741.805 (4)C54—H540.9300
S4—C881.769 (4)C55—C561.367 (6)
S4—C1031.806 (4)C55—H550.9300
Cl1—C271.740 (5)C56—C571.379 (6)
Cl2—C561.728 (5)C57—C581.390 (6)
Cl3—C851.735 (5)C57—H570.9300
Cl4—C1141.735 (5)C58—H580.9300
O1—C231.217 (5)C59—C661.428 (6)
O2—C521.217 (5)C60—C611.359 (6)
O3—C811.214 (5)C60—C681.488 (6)
O4—C1101.218 (5)C61—C671.413 (6)
N1—C11.310 (5)C61—H610.9300
N1—C21.383 (5)C62—C631.357 (7)
N2—C301.311 (5)C62—C671.407 (6)
N2—C311.389 (5)C62—H620.9300
N3—C591.309 (5)C63—C641.386 (7)
N3—C601.380 (5)C63—H630.9300
N4—C881.322 (5)C64—C651.360 (6)
N4—C891.380 (5)C64—H640.9300
C1—C81.430 (5)C65—C661.407 (6)
C2—C31.364 (6)C65—H650.9300
C2—C101.475 (6)C66—C671.416 (6)
C3—C91.419 (6)C68—C731.380 (6)
C3—H30.9300C68—C691.385 (6)
C4—C51.351 (7)C69—C701.382 (7)
C4—C91.418 (6)C69—H690.9300
C4—H40.9300C70—C711.361 (7)
C5—C61.412 (7)C70—H700.9300
C5—H50.9300C71—C721.371 (6)
C6—C71.355 (6)C71—H710.9300
C6—H60.9300C72—C731.370 (6)
C7—C81.408 (6)C72—H720.9300
C7—H70.9300C73—H730.9300
C8—C91.406 (6)C74—C811.517 (6)
C10—C111.382 (6)C74—C751.515 (6)
C10—C151.388 (6)C74—H740.9800
C11—C121.387 (7)C75—C761.372 (6)
C11—H110.9300C75—C801.384 (6)
C12—C131.355 (7)C76—C771.387 (7)
C12—H120.9300C76—H760.9300
C13—C141.355 (7)C77—C781.337 (8)
C13—H130.9300C77—H770.9300
C14—C151.386 (7)C78—C791.366 (8)
C14—H140.9300C78—H780.9300
C15—H150.9300C79—C801.394 (7)
C16—C171.522 (5)C79—H790.9300
C16—C231.534 (6)C80—H800.9300
C16—H160.9800C81—C821.496 (6)
C17—C221.377 (6)C82—C871.375 (6)
C17—C181.382 (6)C82—C831.386 (6)
C18—C191.389 (7)C83—C841.371 (6)
C18—H180.9300C83—H830.9300
C19—C201.365 (8)C84—C851.367 (7)
C19—H190.9300C84—H840.9300
C20—C211.358 (8)C85—C861.362 (6)
C20—H200.9300C86—C871.394 (6)
C21—C221.378 (7)C86—H860.9300
C21—H210.9300C87—H870.9300
C22—H220.9300C88—C951.429 (6)
C23—C241.482 (6)C89—C901.373 (6)
C24—C251.378 (6)C89—C971.470 (6)
C24—C291.386 (6)C90—C961.402 (6)
C25—C261.390 (6)C90—H900.9300
C25—H250.9300C91—C921.346 (7)
C26—C271.359 (7)C91—C961.415 (6)
C26—H260.9300C91—H910.9300
C27—C281.374 (7)C92—C931.400 (7)
C28—C291.379 (6)C92—H920.9300
C28—H280.9300C93—C941.373 (6)
C29—H290.9300C93—H930.9300
C30—C371.430 (6)C94—C951.397 (6)
C31—C321.369 (6)C94—H940.9300
C31—C391.473 (6)C95—C961.410 (6)
C32—C381.405 (6)C97—C1021.383 (6)
C32—H320.9300C97—C981.395 (6)
C33—C341.350 (7)C98—C991.388 (7)
C33—C381.406 (6)C98—H980.9300
C33—H330.9300C99—C1001.389 (8)
C34—C351.401 (7)C99—H990.9300
C34—H340.9300C100—C1011.368 (8)
C35—C361.369 (6)C100—H1000.9300
C35—H350.9300C101—C1021.363 (7)
C36—C371.409 (6)C101—H1010.9300
C36—H360.9300C102—H1020.9300
C37—C381.412 (6)C103—C1041.516 (6)
C39—C441.374 (6)C103—C1101.537 (6)
C39—C401.391 (6)C103—H1030.9800
C40—C411.367 (7)C104—C1091.379 (6)
C40—H400.9300C104—C1051.385 (6)
C41—C421.379 (7)C105—C1061.395 (7)
C41—H410.9300C105—H1050.9300
C42—C431.375 (6)C106—C1071.358 (8)
C42—H420.9300C106—H1060.9300
C43—C441.377 (6)C107—C1081.360 (8)
C43—H430.9300C107—H1070.9300
C44—H440.9300C108—C1091.385 (7)
C45—C461.518 (5)C108—H1080.9300
C45—C521.519 (6)C109—H1090.9300
C45—H450.9800C110—C1111.475 (6)
C46—C511.382 (6)C111—C1161.388 (6)
C46—C471.385 (6)C111—C1121.392 (6)
C47—C481.391 (7)C112—C1131.375 (6)
C47—H470.9300C112—H1120.9300
C48—C491.372 (8)C113—C1141.368 (6)
C48—H480.9300C113—H1130.9300
C49—C501.359 (8)C114—C1151.362 (6)
C49—H490.9300C115—C1161.376 (6)
C50—C511.373 (7)C115—H1150.9300
C50—H500.9300C116—H1160.9300
C1—S1—C16102.4 (2)C58—C57—H57120.6
C30—S2—C45102.6 (2)C53—C58—C57121.4 (4)
C59—S3—C74103.3 (2)C53—C58—H58119.3
C88—S4—C103102.6 (2)C57—C58—H58119.3
C1—N1—C2117.8 (4)N3—C59—C66125.1 (4)
C30—N2—C31118.9 (4)N3—C59—S3119.2 (3)
C59—N3—C60118.3 (4)C66—C59—S3115.7 (3)
C88—N4—C89117.8 (4)C61—C60—N3120.8 (4)
N1—C1—C8125.0 (4)C61—C60—C68123.6 (4)
N1—C1—S1119.0 (3)N3—C60—C68115.6 (4)
C8—C1—S1116.0 (3)C60—C61—C67122.1 (4)
C3—C2—N1121.7 (4)C60—C61—H61118.9
C3—C2—C10122.8 (4)C67—C61—H61118.9
N1—C2—C10115.6 (4)C63—C62—C67120.6 (5)
C2—C3—C9120.9 (4)C63—C62—H62119.7
C2—C3—H3119.5C67—C62—H62119.7
C9—C3—H3119.5C62—C63—C64120.8 (5)
C5—C4—C9119.4 (5)C62—C63—H63119.6
C5—C4—H4120.3C64—C63—H63119.6
C9—C4—H4120.3C65—C64—C63120.6 (5)
C4—C5—C6121.8 (5)C65—C64—H64119.7
C4—C5—H5119.1C63—C64—H64119.7
C6—C5—H5119.1C64—C65—C66120.1 (5)
C7—C6—C5119.2 (5)C64—C65—H65119.9
C7—C6—H6120.4C66—C65—H65119.9
C5—C6—H6120.4C65—C66—C67119.3 (4)
C6—C7—C8121.1 (5)C65—C66—C59124.3 (4)
C6—C7—H7119.4C67—C66—C59116.4 (4)
C8—C7—H7119.4C62—C67—C61124.4 (5)
C7—C8—C9119.1 (4)C62—C67—C66118.4 (5)
C7—C8—C1124.3 (4)C61—C67—C66117.2 (4)
C9—C8—C1116.6 (4)C73—C68—C69117.4 (5)
C8—C9—C3117.8 (4)C73—C68—C60121.1 (4)
C8—C9—C4119.4 (5)C69—C68—C60121.4 (4)
C3—C9—C4122.8 (5)C70—C69—C68121.1 (5)
C11—C10—C15117.8 (5)C70—C69—H69119.5
C11—C10—C2120.8 (5)C68—C69—H69119.5
C15—C10—C2121.4 (4)C71—C70—C69120.7 (5)
C10—C11—C12120.0 (5)C71—C70—H70119.7
C10—C11—H11120.0C69—C70—H70119.7
C12—C11—H11120.0C70—C71—C72118.6 (5)
C13—C12—C11121.1 (6)C70—C71—H71120.7
C13—C12—H12119.5C72—C71—H71120.7
C11—C12—H12119.5C73—C72—C71121.4 (5)
C14—C13—C12120.1 (5)C73—C72—H72119.3
C14—C13—H13120.0C71—C72—H72119.3
C12—C13—H13120.0C72—C73—C68120.8 (4)
C13—C14—C15119.8 (6)C72—C73—H73119.6
C13—C14—H14120.1C68—C73—H73119.6
C15—C14—H14120.1C81—C74—C75112.1 (3)
C14—C15—C10121.1 (5)C81—C74—S3111.7 (3)
C14—C15—H15119.4C75—C74—S3105.5 (3)
C10—C15—H15119.4C81—C74—H74109.2
C17—C16—C23112.3 (3)C75—C74—H74109.2
C17—C16—S1105.0 (3)S3—C74—H74109.2
C23—C16—S1111.6 (3)C76—C75—C80117.9 (4)
C17—C16—H16109.3C76—C75—C74122.4 (4)
C23—C16—H16109.3C80—C75—C74119.7 (4)
S1—C16—H16109.3C75—C76—C77120.7 (5)
C22—C17—C18118.0 (4)C75—C76—H76119.7
C22—C17—C16122.3 (4)C77—C76—H76119.7
C18—C17—C16119.6 (4)C78—C77—C76121.6 (6)
C17—C18—C19120.0 (5)C78—C77—H77119.2
C17—C18—H18120.0C76—C77—H77119.2
C19—C18—H18120.0C77—C78—C79118.9 (6)
C20—C19—C18120.7 (5)C77—C78—H78120.6
C20—C19—H19119.7C79—C78—H78120.6
C18—C19—H19119.7C78—C79—C80120.9 (6)
C21—C20—C19119.7 (6)C78—C79—H79119.5
C21—C20—H20120.1C80—C79—H79119.5
C19—C20—H20120.1C75—C80—C79120.0 (5)
C20—C21—C22119.9 (6)C75—C80—H80120.0
C20—C21—H21120.1C79—C80—H80120.0
C22—C21—H21120.1O3—C81—C82120.3 (4)
C21—C22—C17121.6 (5)O3—C81—C74120.9 (4)
C21—C22—H22119.2C82—C81—C74118.8 (4)
C17—C22—H22119.2C87—C82—C83118.8 (4)
O1—C23—C24121.2 (4)C87—C82—C81118.4 (4)
O1—C23—C16120.3 (4)C83—C82—C81122.8 (4)
C24—C23—C16118.5 (4)C84—C83—C82120.7 (4)
C25—C24—C29118.9 (4)C84—C83—H83119.6
C25—C24—C23123.2 (4)C82—C83—H83119.6
C29—C24—C23117.8 (4)C83—C84—C85119.5 (5)
C24—C25—C26120.6 (4)C83—C84—H84120.2
C24—C25—H25119.7C85—C84—H84120.2
C26—C25—H25119.7C86—C85—C84121.4 (5)
C27—C26—C25118.8 (5)C86—C85—Cl3119.1 (4)
C27—C26—H26120.6C84—C85—Cl3119.5 (4)
C25—C26—H26120.6C85—C86—C87118.9 (4)
C26—C27—C28122.3 (5)C85—C86—H86120.6
C26—C27—Cl1118.9 (5)C87—C86—H86120.6
C28—C27—Cl1118.7 (5)C82—C87—C86120.6 (5)
C27—C28—C29118.3 (5)C82—C87—H87119.7
C27—C28—H28120.9C86—C87—H87119.7
C29—C28—H28120.9N4—C88—C95124.8 (4)
C28—C29—C24121.0 (5)N4—C88—S4118.6 (3)
C28—C29—H29119.5C95—C88—S4116.5 (3)
C24—C29—H29119.5C90—C89—N4121.5 (4)
N2—C30—C37124.3 (4)C90—C89—C97123.3 (4)
N2—C30—S2119.0 (3)N4—C89—C97115.1 (4)
C37—C30—S2116.7 (3)C89—C90—C96121.0 (4)
C32—C31—N2120.2 (4)C89—C90—H90119.5
C32—C31—C39123.8 (4)C96—C90—H90119.5
N2—C31—C39116.0 (4)C92—C91—C96121.0 (5)
C31—C32—C38122.0 (4)C92—C91—H91119.5
C31—C32—H32119.0C96—C91—H91119.5
C38—C32—H32119.0C91—C92—C93120.9 (5)
C34—C33—C38120.4 (5)C91—C92—H92119.5
C34—C33—H33119.8C93—C92—H92119.5
C38—C33—H33119.8C94—C93—C92119.8 (5)
C33—C34—C35121.5 (5)C94—C93—H93120.1
C33—C34—H34119.2C92—C93—H93120.1
C35—C34—H34119.2C93—C94—C95120.4 (5)
C36—C35—C34119.7 (5)C93—C94—H94119.8
C36—C35—H35120.1C95—C94—H94119.8
C34—C35—H35120.1C94—C95—C96119.9 (4)
C35—C36—C37119.9 (5)C94—C95—C88123.8 (4)
C35—C36—H36120.0C96—C95—C88116.3 (4)
C37—C36—H36120.0C90—C96—C95118.5 (4)
C36—C37—C38119.8 (4)C90—C96—C91123.3 (5)
C36—C37—C30123.3 (4)C95—C96—C91118.2 (5)
C38—C37—C30116.9 (4)C102—C97—C98117.4 (5)
C33—C38—C32123.7 (5)C102—C97—C89121.8 (4)
C33—C38—C37118.6 (5)C98—C97—C89120.8 (5)
C32—C38—C37117.7 (4)C99—C98—C97120.6 (5)
C44—C39—C40117.2 (5)C99—C98—H98119.7
C44—C39—C31120.9 (4)C97—C98—H98119.7
C40—C39—C31121.9 (4)C98—C99—C100120.4 (6)
C41—C40—C39120.8 (5)C98—C99—H99119.8
C41—C40—H40119.6C100—C99—H99119.8
C39—C40—H40119.6C101—C100—C99118.5 (6)
C40—C41—C42121.7 (5)C101—C100—H100120.7
C40—C41—H41119.1C99—C100—H100120.7
C42—C41—H41119.1C102—C101—C100121.2 (6)
C43—C42—C41117.7 (5)C102—C101—H101119.4
C43—C42—H42121.1C100—C101—H101119.4
C41—C42—H42121.1C101—C102—C97121.8 (5)
C42—C43—C44120.7 (5)C101—C102—H102119.1
C42—C43—H43119.7C97—C102—H102119.1
C44—C43—H43119.7C104—C103—C110111.8 (3)
C39—C44—C43121.8 (5)C104—C103—S4105.8 (3)
C39—C44—H44119.1C110—C103—S4111.6 (3)
C43—C44—H44119.1C104—C103—H103109.2
C46—C45—C52111.6 (3)C110—C103—H103109.2
C46—C45—S2105.7 (3)S4—C103—H103109.2
C52—C45—S2111.9 (3)C109—C104—C105118.0 (5)
C46—C45—H45109.2C109—C104—C103122.2 (4)
C52—C45—H45109.2C105—C104—C103119.7 (4)
S2—C45—H45109.2C104—C105—C106120.2 (5)
C51—C46—C47117.6 (4)C104—C105—H105119.9
C51—C46—C45122.2 (4)C106—C105—H105119.9
C47—C46—C45120.1 (4)C107—C106—C105120.4 (6)
C46—C47—C48120.7 (5)C107—C106—H106119.8
C46—C47—H47119.6C105—C106—H106119.8
C48—C47—H47119.6C108—C107—C106120.3 (6)
C49—C48—C47120.0 (5)C108—C107—H107119.9
C49—C48—H48120.0C106—C107—H107119.9
C47—C48—H48120.0C107—C108—C109119.8 (6)
C50—C49—C48119.6 (5)C107—C108—H108120.1
C50—C49—H49120.2C109—C108—H108120.1
C48—C49—H49120.2C104—C109—C108121.4 (5)
C49—C50—C51120.7 (6)C104—C109—H109119.3
C49—C50—H50119.7C108—C109—H109119.3
C51—C50—H50119.7O4—C110—C111121.3 (4)
C50—C51—C46121.3 (5)O4—C110—C103120.1 (4)
C50—C51—H51119.3C111—C110—C103118.7 (4)
C46—C51—H51119.3C116—C111—C112118.0 (4)
O2—C52—C53120.4 (4)C116—C111—C110123.6 (4)
O2—C52—C45121.0 (4)C112—C111—C110118.4 (4)
C53—C52—C45118.6 (4)C113—C112—C111120.9 (5)
C58—C53—C54118.7 (4)C113—C112—H112119.5
C58—C53—C52118.7 (4)C111—C112—H112119.5
C54—C53—C52122.5 (4)C114—C113—C112119.2 (5)
C55—C54—C53120.1 (4)C114—C113—H113120.4
C55—C54—H54119.9C112—C113—H113120.4
C53—C54—H54119.9C115—C114—C113121.5 (5)
C56—C55—C54120.5 (5)C115—C114—Cl4119.0 (4)
C56—C55—H55119.7C113—C114—Cl4119.5 (4)
C54—C55—H55119.7C114—C115—C116119.3 (5)
C55—C56—C57120.5 (5)C114—C115—H115120.3
C55—C56—Cl2120.1 (4)C116—C115—H115120.3
C57—C56—Cl2119.4 (4)C115—C116—C111121.0 (4)
C56—C57—C58118.7 (4)C115—C116—H116119.5
C56—C57—H57120.6C111—C116—H116119.5
C2—N1—C1—C83.4 (6)C60—N3—C59—C662.4 (6)
C2—N1—C1—S1−176.2 (3)C60—N3—C59—S3−176.2 (3)
C16—S1—C1—N1−1.2 (4)C74—S3—C59—N3−2.1 (4)
C16—S1—C1—C8179.2 (3)C74—S3—C59—C66179.2 (3)
C1—N1—C2—C3−2.4 (6)C59—N3—C60—C61−1.2 (6)
C1—N1—C2—C10178.4 (4)C59—N3—C60—C68179.5 (4)
N1—C2—C3—C90.6 (7)N3—C60—C61—C67−0.3 (7)
C10—C2—C3—C9179.7 (4)C68—C60—C61—C67178.8 (4)
C9—C4—C5—C60.7 (8)C67—C62—C63—C640.0 (8)
C4—C5—C6—C7−0.8 (8)C62—C63—C64—C651.5 (8)
C5—C6—C7—C80.6 (8)C63—C64—C65—C66−1.4 (8)
C6—C7—C8—C9−0.5 (7)C64—C65—C66—C67−0.2 (7)
C6—C7—C8—C1−179.8 (4)C64—C65—C66—C59−179.2 (5)
N1—C1—C8—C7177.0 (4)N3—C59—C66—C65177.2 (4)
S1—C1—C8—C7−3.4 (6)S3—C59—C66—C65−4.1 (6)
N1—C1—C8—C9−2.4 (6)N3—C59—C66—C67−1.8 (6)
S1—C1—C8—C9177.2 (3)S3—C59—C66—C67176.8 (3)
C7—C8—C9—C3−179.0 (4)C63—C62—C67—C61179.1 (5)
C1—C8—C9—C30.4 (6)C63—C62—C67—C66−1.6 (7)
C7—C8—C9—C40.4 (6)C60—C61—C67—C62−179.9 (4)
C1—C8—C9—C4179.8 (4)C60—C61—C67—C660.9 (7)
C2—C3—C9—C80.4 (6)C65—C66—C67—C621.7 (6)
C2—C3—C9—C4−179.0 (4)C59—C66—C67—C62−179.2 (4)
C5—C4—C9—C8−0.6 (7)C65—C66—C67—C61−179.0 (4)
C5—C4—C9—C3178.9 (5)C59—C66—C67—C610.1 (6)
C3—C2—C10—C1134.8 (7)C61—C60—C68—C73−158.9 (4)
N1—C2—C10—C11−146.1 (4)N3—C60—C68—C7320.3 (6)
C3—C2—C10—C15−146.7 (5)C61—C60—C68—C6922.7 (7)
N1—C2—C10—C1532.4 (6)N3—C60—C68—C69−158.1 (4)
C15—C10—C11—C122.6 (7)C73—C68—C69—C702.3 (8)
C2—C10—C11—C12−178.9 (4)C60—C68—C69—C70−179.2 (5)
C10—C11—C12—C13−1.0 (8)C68—C69—C70—C71−1.6 (9)
C11—C12—C13—C14−0.6 (8)C69—C70—C71—C72−0.1 (8)
C12—C13—C14—C150.5 (8)C70—C71—C72—C731.0 (8)
C13—C14—C15—C101.1 (8)C71—C72—C73—C68−0.2 (7)
C11—C10—C15—C14−2.6 (7)C69—C68—C73—C72−1.4 (7)
C2—C10—C15—C14178.8 (4)C60—C68—C73—C72−179.9 (4)
C1—S1—C16—C17163.3 (3)C59—S3—C74—C81−75.1 (3)
C1—S1—C16—C23−74.8 (3)C59—S3—C74—C75162.9 (3)
C23—C16—C17—C22−31.6 (6)C81—C74—C75—C76−30.6 (6)
S1—C16—C17—C2289.8 (5)S3—C74—C75—C7691.1 (5)
C23—C16—C17—C18152.3 (4)C81—C74—C75—C80152.6 (4)
S1—C16—C17—C18−86.3 (4)S3—C74—C75—C80−85.7 (4)
C22—C17—C18—C190.3 (7)C80—C75—C76—C771.5 (8)
C16—C17—C18—C19176.5 (4)C74—C75—C76—C77−175.4 (5)
C17—C18—C19—C20−0.7 (8)C75—C76—C77—C78−2.3 (10)
C18—C19—C20—C211.6 (9)C76—C77—C78—C792.5 (10)
C19—C20—C21—C22−2.1 (10)C77—C78—C79—C80−2.0 (9)
C20—C21—C22—C171.8 (9)C76—C75—C80—C79−1.0 (7)
C18—C17—C22—C21−0.8 (8)C74—C75—C80—C79175.9 (4)
C16—C17—C22—C21−177.0 (5)C78—C79—C80—C751.3 (8)
C17—C16—C23—O185.8 (5)C75—C74—C81—O385.2 (5)
S1—C16—C23—O1−31.8 (5)S3—C74—C81—O3−32.9 (5)
C17—C16—C23—C24−93.8 (4)C75—C74—C81—C82−94.6 (4)
S1—C16—C23—C24148.6 (3)S3—C74—C81—C82147.3 (3)
O1—C23—C24—C25−168.1 (4)O3—C81—C82—C8716.5 (6)
C16—C23—C24—C2511.5 (6)C74—C81—C82—C87−163.6 (4)
O1—C23—C24—C2914.7 (6)O3—C81—C82—C83−165.9 (4)
C16—C23—C24—C29−165.7 (4)C74—C81—C82—C8314.0 (6)
C29—C24—C25—C260.9 (7)C87—C82—C83—C841.1 (6)
C23—C24—C25—C26−176.3 (4)C81—C82—C83—C84−176.5 (4)
C24—C25—C26—C270.3 (8)C82—C83—C84—C851.1 (7)
C25—C26—C27—C28−0.5 (8)C83—C84—C85—C86−2.5 (8)
C25—C26—C27—Cl1177.1 (4)C83—C84—C85—Cl3176.8 (4)
C26—C27—C28—C29−0.5 (8)C84—C85—C86—C871.6 (7)
Cl1—C27—C28—C29−178.1 (4)Cl3—C85—C86—C87−177.7 (4)
C27—C28—C29—C241.7 (7)C83—C82—C87—C86−2.0 (6)
C25—C24—C29—C28−1.9 (7)C81—C82—C87—C86175.7 (4)
C23—C24—C29—C28175.4 (4)C85—C86—C87—C820.7 (7)
C31—N2—C30—C37−2.3 (6)C89—N4—C88—C95−2.7 (6)
C31—N2—C30—S2175.9 (3)C89—N4—C88—S4175.6 (3)
C45—S2—C30—N21.8 (4)C103—S4—C88—N41.5 (4)
C45—S2—C30—C37−179.8 (3)C103—S4—C88—C95179.9 (3)
C30—N2—C31—C322.0 (6)C88—N4—C89—C902.3 (6)
C30—N2—C31—C39−179.1 (4)C88—N4—C89—C97−178.2 (4)
N2—C31—C32—C38−0.5 (7)N4—C89—C90—C96−0.7 (7)
C39—C31—C32—C38−179.4 (4)C97—C89—C90—C96179.8 (4)
C38—C33—C34—C35−0.3 (8)C96—C91—C92—C930.0 (8)
C33—C34—C35—C360.1 (8)C91—C92—C93—C94−0.4 (8)
C34—C35—C36—C37−0.1 (8)C92—C93—C94—C950.6 (8)
C35—C36—C37—C380.3 (7)C93—C94—C95—C96−0.4 (7)
C35—C36—C37—C30179.2 (4)C93—C94—C95—C88179.2 (4)
N2—C30—C37—C36−177.8 (4)N4—C88—C95—C94−178.3 (4)
S2—C30—C37—C363.9 (6)S4—C88—C95—C943.4 (6)
N2—C30—C37—C381.2 (6)N4—C88—C95—C961.4 (6)
S2—C30—C37—C38−177.1 (3)S4—C88—C95—C96−176.9 (3)
C34—C33—C38—C32−179.3 (5)C89—C90—C96—C95−0.6 (7)
C34—C33—C38—C370.6 (7)C89—C90—C96—C91179.3 (4)
C31—C32—C38—C33179.2 (4)C94—C95—C96—C90180.0 (4)
C31—C32—C38—C37−0.6 (7)C88—C95—C96—C900.3 (6)
C36—C37—C38—C33−0.5 (7)C94—C95—C96—C910.1 (6)
C30—C37—C38—C33−179.5 (4)C88—C95—C96—C91−179.6 (4)
C36—C37—C38—C32179.3 (4)C92—C91—C96—C90−179.8 (5)
C30—C37—C38—C320.4 (6)C92—C91—C96—C950.1 (7)
C32—C31—C39—C44155.4 (5)C90—C89—C97—C102144.5 (5)
N2—C31—C39—C44−23.5 (6)N4—C89—C97—C102−35.0 (6)
C32—C31—C39—C40−26.7 (7)C90—C89—C97—C98−36.2 (7)
N2—C31—C39—C40154.4 (4)N4—C89—C97—C98144.3 (4)
C44—C39—C40—C41−2.7 (8)C102—C97—C98—C99−1.0 (7)
C31—C39—C40—C41179.3 (5)C89—C97—C98—C99179.7 (4)
C39—C40—C41—C421.4 (9)C97—C98—C99—C100−0.7 (8)
C40—C41—C42—C430.0 (9)C98—C99—C100—C1011.8 (8)
C41—C42—C43—C440.1 (8)C99—C100—C101—C102−1.1 (8)
C40—C39—C44—C432.7 (7)C100—C101—C102—C97−0.8 (8)
C31—C39—C44—C43−179.2 (4)C98—C97—C102—C1011.8 (7)
C42—C43—C44—C39−1.5 (8)C89—C97—C102—C101−178.9 (5)
C30—S2—C45—C46−162.6 (3)C88—S4—C103—C104−162.9 (3)
C30—S2—C45—C5275.8 (3)C88—S4—C103—C11075.3 (3)
C52—C45—C46—C5132.9 (6)C110—C103—C104—C10933.8 (6)
S2—C45—C46—C51−88.9 (5)S4—C103—C104—C109−87.9 (5)
C52—C45—C46—C47−150.8 (4)C110—C103—C104—C105−150.4 (4)
S2—C45—C46—C4787.4 (4)S4—C103—C104—C10588.0 (4)
C51—C46—C47—C48−0.8 (7)C109—C104—C105—C106−0.5 (7)
C45—C46—C47—C48−177.2 (4)C103—C104—C105—C106−176.6 (4)
C46—C47—C48—C490.6 (8)C104—C105—C106—C1070.1 (8)
C47—C48—C49—C500.1 (9)C105—C106—C107—C1080.7 (9)
C48—C49—C50—C51−0.6 (9)C106—C107—C108—C109−1.1 (10)
C49—C50—C51—C460.4 (9)C105—C104—C109—C1080.2 (8)
C47—C46—C51—C500.3 (8)C103—C104—C109—C108176.1 (5)
C45—C46—C51—C50176.6 (5)C107—C108—C109—C1040.7 (9)
C46—C45—C52—O2−87.7 (5)C104—C103—C110—O4−87.2 (5)
S2—C45—C52—O230.5 (5)S4—C103—C110—O431.0 (5)
C46—C45—C52—C5392.7 (4)C104—C103—C110—C11192.7 (4)
S2—C45—C52—C53−149.2 (3)S4—C103—C110—C111−149.1 (3)
O2—C52—C53—C58−14.9 (6)O4—C110—C111—C116168.7 (4)
C45—C52—C53—C58164.8 (4)C103—C110—C111—C116−11.1 (6)
O2—C52—C53—C54167.9 (4)O4—C110—C111—C112−13.2 (6)
C45—C52—C53—C54−12.4 (6)C103—C110—C111—C112166.9 (4)
C58—C53—C54—C55−1.7 (7)C116—C111—C112—C1132.4 (7)
C52—C53—C54—C55175.5 (4)C110—C111—C112—C113−175.8 (4)
C53—C54—C55—C56−0.1 (7)C111—C112—C113—C114−0.9 (8)
C54—C55—C56—C571.8 (7)C112—C113—C114—C115−1.0 (8)
C54—C55—C56—Cl2−177.2 (4)C112—C113—C114—Cl4176.5 (4)
C55—C56—C57—C58−1.6 (7)C113—C114—C115—C1161.2 (8)
Cl2—C56—C57—C58177.4 (4)Cl4—C114—C115—C116−176.3 (4)
C54—C53—C58—C571.9 (7)C114—C115—C116—C1110.4 (8)
C52—C53—C58—C57−175.4 (4)C112—C111—C116—C115−2.2 (7)
C56—C57—C58—C53−0.3 (7)C110—C111—C116—C115175.9 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2556).

References

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