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The title compound, C17H11ClN2O2S, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit. In the mol­ecular structure, there are intra­molecular weak C—H...O hydrogen bonds, which consolidate the mol­ecular conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050616/lh2255sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050616/lh2255Isup2.hkl
Contains datablock I

CCDC reference: 630174

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.123
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl2 - C30 .. 7.19 su
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.91 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 600 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 - C13 .. 6.66 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C14 - C15 .. 5.01 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-[6-(2-Chlorobenzoyl)-2-oxo-2,3-dihydro-1,3-benzothiazol-3-yl]propanenitrile top
Crystal data top
C17H11ClN2O2SZ = 4
Mr = 342.80F(000) = 704
Triclinic, P1Dx = 1.464 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.089 (1) ÅCell parameters from 20093 reflections
b = 8.522 (1) Åθ = 1.6–26.1°
c = 26.042 (2) ŵ = 0.39 mm1
α = 97.724 (6)°T = 296 K
β = 91.659 (6)°Plate, colourless
γ = 93.257 (6)°0.45 × 0.29 × 0.13 mm
V = 1555.4 (3) Å3
Data collection top
Stoe IPDS-2
diffractometer
5906 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2842 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.085
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.6°
ω scansh = 88
Absorption correction: integration
(XRED32; Stoe & Cie, 2002)
k = 1010
Tmin = 0.844, Tmax = 0.951l = 3231
24878 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 0.84 w = 1/[σ2(Fo2) + (0.0646P)2]
where P = (Fo2 + 2Fc2)/3
5906 reflections(Δ/σ)max < 0.001
416 parametersΔρmax = 0.68 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.23995 (15)0.23762 (15)0.10246 (4)0.1021 (5)
S10.56566 (11)0.92236 (9)0.27922 (3)0.0527 (3)
O10.6228 (3)1.0775 (3)0.37415 (9)0.0688 (9)
O20.4892 (4)0.1808 (3)0.19915 (9)0.0819 (10)
N10.6215 (3)0.8040 (3)0.36414 (9)0.0454 (8)
N20.2537 (4)0.9502 (4)0.46343 (11)0.0703 (11)
C10.6078 (4)0.9485 (4)0.34682 (12)0.0511 (11)
C20.5702 (4)0.7175 (3)0.27626 (11)0.0442 (9)
C30.5500 (4)0.6020 (4)0.23328 (11)0.0479 (10)
C40.5573 (4)0.4440 (3)0.23937 (11)0.0454 (10)
C50.5829 (4)0.4018 (4)0.28920 (11)0.0494 (10)
C60.6060 (4)0.5152 (4)0.33264 (11)0.0469 (10)
C70.6006 (4)0.6736 (3)0.32559 (10)0.0430 (9)
C80.6727 (4)0.7939 (4)0.41821 (11)0.0503 (10)
C90.5062 (4)0.7417 (4)0.44843 (11)0.0494 (10)
C100.3640 (5)0.8591 (4)0.45648 (11)0.0522 (11)
C110.5366 (4)0.3178 (4)0.19452 (11)0.0513 (11)
C120.5834 (4)0.3586 (3)0.14206 (11)0.0536 (10)
C130.4691 (5)0.3211 (4)0.09806 (13)0.0670 (12)
C140.5217 (6)0.3522 (5)0.05071 (14)0.0770 (16)
C150.7023 (8)0.4170 (5)0.04541 (16)0.0894 (18)
C160.8213 (6)0.4546 (5)0.08754 (17)0.0798 (16)
C170.7640 (5)0.4266 (4)0.13565 (14)0.0685 (12)
Cl21.28851 (16)0.25945 (16)0.09990 (4)0.1034 (5)
S21.07754 (11)0.42819 (9)0.28098 (3)0.0527 (3)
O31.1242 (3)0.5812 (3)0.37667 (9)0.0708 (9)
O41.0869 (5)0.3107 (3)0.19985 (10)0.0920 (13)
N31.1220 (3)0.3085 (3)0.36598 (8)0.0462 (8)
N40.7472 (5)0.4481 (4)0.46335 (11)0.0741 (12)
C181.1113 (4)0.4537 (4)0.34869 (12)0.0533 (11)
C191.0747 (4)0.2238 (3)0.27858 (10)0.0437 (9)
C201.0552 (4)0.1095 (4)0.23460 (11)0.0469 (10)
C211.0588 (4)0.0496 (4)0.24095 (11)0.0473 (10)
C221.0818 (4)0.0937 (4)0.29040 (11)0.0478 (10)
C231.1029 (4)0.0198 (4)0.33393 (11)0.0463 (10)
C241.1002 (4)0.1781 (4)0.32722 (10)0.0438 (10)
C251.1689 (4)0.2948 (4)0.41997 (11)0.0523 (10)
C261.0008 (4)0.2407 (4)0.44978 (11)0.0521 (10)
C270.8585 (5)0.3581 (4)0.45712 (11)0.0531 (11)
C281.0465 (4)0.1772 (4)0.19545 (11)0.0547 (11)
C290.9777 (5)0.1378 (4)0.14402 (12)0.0597 (11)
C301.0690 (5)0.1774 (4)0.09924 (14)0.0713 (14)
C310.9970 (7)0.1501 (5)0.05164 (14)0.0798 (16)
C320.8241 (7)0.0842 (5)0.04948 (16)0.0899 (19)
C330.7287 (6)0.0428 (5)0.09411 (16)0.0812 (16)
C340.8024 (5)0.0703 (4)0.14047 (13)0.0664 (12)
H30.531600.631000.200400.0570*
H50.584400.295000.293200.0590*
H60.624600.486200.365500.0560*
H8A0.724400.896900.434600.0600*
H8B0.770600.719300.419500.0600*
H9A0.447000.644000.430000.0590*
H9B0.552500.719300.481900.0590*
H140.437700.330400.022200.0930*
H150.742200.434800.012900.1070*
H160.942000.499500.083900.0960*
H170.846400.453300.164300.0820*
H201.040100.139400.201700.0560*
H221.083100.200600.294200.0570*
H231.118400.009700.366800.0560*
H25A1.220300.397000.437100.0630*
H25B1.266500.219900.421100.0630*
H26A0.942700.142800.431200.0620*
H26B1.045700.218500.483400.0620*
H311.063600.175500.021700.0960*
H320.771600.067700.017600.1080*
H330.613800.004100.092500.0970*
H340.735800.044200.170400.0800*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0790 (7)0.1250 (10)0.0973 (8)0.0196 (6)0.0236 (5)0.0141 (7)
S10.0606 (5)0.0466 (5)0.0541 (5)0.0076 (3)0.0082 (3)0.0151 (3)
O10.0923 (17)0.0452 (14)0.0662 (15)0.0021 (11)0.0019 (11)0.0012 (11)
O20.133 (2)0.0551 (15)0.0575 (15)0.0028 (14)0.0062 (13)0.0101 (11)
N10.0504 (13)0.0424 (15)0.0429 (14)0.0045 (10)0.0023 (10)0.0032 (11)
N20.082 (2)0.0664 (19)0.0682 (19)0.0300 (16)0.0121 (14)0.0174 (14)
C10.0512 (17)0.048 (2)0.0536 (19)0.0006 (13)0.0073 (13)0.0047 (16)
C20.0438 (15)0.0469 (17)0.0429 (17)0.0082 (12)0.0043 (11)0.0072 (13)
C30.0487 (16)0.0546 (19)0.0414 (17)0.0043 (13)0.0018 (12)0.0100 (14)
C40.0463 (16)0.0485 (18)0.0417 (17)0.0059 (12)0.0034 (12)0.0062 (13)
C50.0614 (18)0.0421 (17)0.0461 (18)0.0090 (13)0.0033 (13)0.0084 (14)
C60.0528 (17)0.0493 (19)0.0397 (16)0.0099 (13)0.0003 (12)0.0071 (14)
C70.0387 (14)0.0483 (18)0.0422 (17)0.0072 (12)0.0037 (11)0.0043 (14)
C80.0534 (17)0.0534 (18)0.0422 (17)0.0045 (14)0.0028 (12)0.0002 (13)
C90.0604 (18)0.0484 (17)0.0396 (16)0.0110 (14)0.0024 (13)0.0035 (13)
C100.069 (2)0.0513 (19)0.0370 (17)0.0096 (16)0.0019 (13)0.0060 (14)
C110.0534 (17)0.050 (2)0.0509 (19)0.0075 (14)0.0011 (13)0.0073 (15)
C120.069 (2)0.0464 (17)0.0440 (17)0.0024 (14)0.0035 (14)0.0017 (13)
C130.092 (2)0.055 (2)0.052 (2)0.0073 (17)0.0049 (17)0.0010 (15)
C140.111 (3)0.073 (3)0.045 (2)0.003 (2)0.0062 (19)0.0041 (18)
C150.140 (4)0.074 (3)0.057 (2)0.014 (3)0.026 (2)0.0118 (19)
C160.088 (3)0.071 (2)0.082 (3)0.0021 (19)0.027 (2)0.012 (2)
C170.068 (2)0.067 (2)0.066 (2)0.0052 (17)0.0072 (16)0.0042 (17)
Cl20.0846 (7)0.1245 (10)0.0966 (8)0.0172 (6)0.0262 (5)0.0105 (7)
S20.0585 (5)0.0479 (5)0.0532 (5)0.0002 (3)0.0018 (3)0.0135 (3)
O30.0898 (17)0.0470 (14)0.0715 (16)0.0035 (11)0.0041 (12)0.0017 (12)
O40.158 (3)0.0555 (16)0.0623 (16)0.0287 (16)0.0046 (15)0.0003 (12)
N30.0540 (14)0.0457 (15)0.0382 (14)0.0026 (11)0.0011 (10)0.0038 (11)
N40.086 (2)0.071 (2)0.071 (2)0.0323 (17)0.0161 (15)0.0160 (15)
C180.0549 (18)0.046 (2)0.057 (2)0.0013 (14)0.0005 (14)0.0024 (16)
C190.0401 (15)0.0517 (18)0.0402 (16)0.0002 (12)0.0052 (11)0.0095 (13)
C200.0490 (16)0.0521 (19)0.0396 (16)0.0011 (13)0.0028 (12)0.0073 (14)
C210.0460 (16)0.0542 (19)0.0411 (17)0.0051 (13)0.0036 (12)0.0032 (14)
C220.0503 (16)0.0467 (18)0.0472 (18)0.0046 (13)0.0056 (12)0.0082 (14)
C230.0535 (17)0.0515 (19)0.0360 (16)0.0086 (13)0.0036 (12)0.0109 (14)
C240.0408 (15)0.0510 (19)0.0393 (17)0.0047 (12)0.0037 (11)0.0042 (14)
C250.0560 (18)0.0542 (19)0.0450 (17)0.0046 (14)0.0012 (13)0.0003 (14)
C260.0643 (19)0.0457 (17)0.0470 (18)0.0137 (14)0.0050 (14)0.0044 (13)
C270.066 (2)0.055 (2)0.0396 (17)0.0081 (17)0.0058 (13)0.0086 (14)
C280.0639 (19)0.055 (2)0.0442 (18)0.0024 (15)0.0060 (13)0.0025 (15)
C290.082 (2)0.0481 (18)0.0459 (18)0.0017 (16)0.0015 (15)0.0016 (14)
C300.098 (3)0.059 (2)0.053 (2)0.0090 (18)0.0086 (18)0.0024 (16)
C310.120 (3)0.070 (3)0.047 (2)0.012 (2)0.008 (2)0.0061 (17)
C320.136 (4)0.071 (3)0.061 (3)0.012 (2)0.028 (2)0.0169 (19)
C330.087 (3)0.073 (2)0.081 (3)0.0038 (19)0.020 (2)0.007 (2)
C340.071 (2)0.066 (2)0.059 (2)0.0051 (17)0.0017 (16)0.0031 (16)
Geometric parameters (Å, º) top
Cl1—C131.749 (4)C6—H60.9300
Cl2—C301.742 (4)C8—H8B0.9700
S1—C11.759 (3)C8—H8A0.9700
S1—C21.739 (3)C9—H9B0.9700
S2—C181.755 (3)C9—H9A0.9700
S2—C191.734 (3)C14—H140.9300
O1—C11.224 (4)C15—H150.9300
O2—C111.219 (4)C16—H160.9300
O3—C181.221 (4)C17—H170.9300
O4—C281.208 (4)C19—C201.398 (4)
N1—C81.459 (4)C19—C241.384 (4)
N1—C11.375 (4)C20—C211.389 (5)
N1—C71.392 (4)C21—C221.397 (4)
N2—C101.134 (5)C21—C281.494 (4)
N3—C241.396 (4)C22—C231.386 (4)
N3—C251.457 (4)C23—C241.385 (5)
N3—C181.378 (4)C25—C261.524 (4)
N4—C271.131 (5)C26—C271.459 (5)
C2—C31.386 (4)C28—C291.499 (4)
C2—C71.400 (4)C29—C301.362 (5)
C3—C41.381 (4)C29—C341.405 (5)
C4—C111.475 (4)C30—C311.380 (5)
C4—C51.402 (4)C31—C321.380 (7)
C5—C61.385 (4)C32—C331.377 (6)
C6—C71.389 (4)C33—C341.356 (5)
C8—C91.516 (4)C20—H200.9300
C9—C101.460 (5)C22—H220.9300
C11—C121.496 (4)C23—H230.9300
C12—C171.399 (5)C25—H25A0.9700
C12—C131.375 (4)C25—H25B0.9700
C13—C141.354 (5)C26—H26A0.9700
C14—C151.383 (7)C26—H26B0.9700
C15—C161.356 (6)C31—H310.9300
C16—C171.375 (6)C32—H320.9300
C3—H30.9300C33—H330.9300
C5—H50.9300C34—H340.9300
Cl1···O23.141 (3)C26···O1iii3.395 (4)
Cl1···C16i3.623 (4)C26···N2vii3.450 (4)
Cl2···O43.076 (3)C27···O1iii3.336 (4)
Cl2···C33ii3.552 (4)C27···C183.549 (4)
Cl2···H16iii3.0900C27···C27ix3.550 (5)
Cl2···H15iv3.1100C27···C10vii3.460 (5)
S1···C22v3.674 (3)C30···C16iii3.478 (6)
S1···O2v3.286 (3)C33···Cl2i3.552 (4)
S1···C21v3.666 (3)C34···C203.161 (5)
S1···C22vi3.447 (3)C3···H173.0300
S2···C4ii3.600 (3)C4···H172.8800
S2···C53.516 (3)C6···H8B2.8400
S2···C5ii3.604 (3)C6···H9A2.9100
S2···O4v3.267 (3)C7···H9A2.9900
S1···H5v3.1400C8···H62.7900
S1···H34v3.1500C9···H63.0300
S2···H22v3.1300C12···H32.6500
O1···C26v3.395 (4)C13···H332.9300
O1···C27v3.336 (4)C17···H32.8800
O2···Cl13.141 (3)C20···H342.9100
O2···S1iii3.286 (3)C21···H342.9000
O2···C20i3.285 (4)C23···H25B2.8300
O3···C9ii3.361 (4)C23···H26A2.9000
O3···C10ii3.291 (4)C24···H26A3.0000
O4···Cl23.076 (3)C25···H232.7700
O4···S2iii3.267 (3)C26···H233.0000
O4···C17iii3.352 (5)C29···H202.6300
O1···H26Av2.6600C30···H16iii2.8200
O1···H8A2.4700C34···H202.7000
O2···H342.7100H3···C172.8800
O2···H52.5700H3···C122.6500
O3···H9Aii2.6300H5···S1iii3.1400
O3···H25A2.4800H5···O22.5700
O4···H17iii2.6100H6···N42.7400
O4···H222.5100H6···C82.7900
N2···C26vi3.190 (5)H6···C93.0300
N2···C26vii3.450 (4)H6···H8B2.4300
N2···C25vi3.365 (5)H6···H9A2.4300
N4···C83.379 (5)H8A···N2viii2.7900
N4···C93.168 (5)H8A···O12.4700
N2···H26Bvi2.7900H8A···H26Av2.5500
N2···H25Bvi2.6800H8B···H62.4300
N2···H23vi2.7400H8B···N42.7100
N2···H8Aviii2.7900H8B···C62.8400
N4···H25Aix2.7400H9A···H62.4300
N4···H62.7400H9A···O3i2.6300
N4···H8B2.7100H9A···C72.9900
N4···H9B2.7500H9A···C62.9100
C1···C103.528 (4)H9B···N42.7500
C1···C23v3.561 (4)H15···Cl2iv3.1100
C3···C173.234 (5)H16···C30v2.8200
C4···S2i3.600 (3)H16···Cl2v3.0900
C5···S2i3.604 (3)H17···C42.8800
C5···S23.516 (3)H17···O4v2.6100
C6···C18i3.561 (4)H17···C33.0300
C6···C93.469 (4)H20···C292.6300
C8···N43.379 (5)H20···C342.7000
C9···C63.469 (4)H22···S2iii3.1300
C9···N43.168 (5)H22···O42.5100
C9···O3i3.361 (4)H23···N2x2.7400
C10···C10viii3.519 (5)H23···C252.7700
C10···C13.528 (4)H23···C263.0000
C10···C27vii3.460 (5)H23···H25B2.4200
C10···O3i3.291 (4)H23···H26A2.4000
C16···Cl1ii3.623 (4)H25A···O32.4800
C16···C30v3.478 (6)H25A···N4ix2.7400
C17···C33.234 (5)H25B···N2x2.6800
C17···O4v3.352 (5)H25B···C232.8300
C18···C273.549 (4)H25B···H232.4200
C18···C6ii3.561 (4)H26A···O1iii2.6600
C20···O2ii3.285 (4)H26A···C232.9000
C20···C343.161 (5)H26A···C243.0000
C21···S1iii3.666 (3)H26A···H8Aiii2.5500
C22···S1x3.447 (3)H26A···H232.4000
C22···S1iii3.674 (3)H26B···N2x2.7900
C23···C263.453 (4)H33···C132.9300
C23···C1iii3.561 (4)H34···S1iii3.1500
C25···N2x3.365 (5)H34···O22.7100
C26···N2x3.190 (5)H34···C202.9100
C26···C233.453 (4)H34···C212.9000
C1—S1—C291.34 (15)C17—C16—H16120.00
C18—S2—C1991.01 (15)C15—C16—H16120.00
C1—N1—C7114.8 (2)C12—C17—H17120.00
C1—N1—C8121.0 (3)C16—C17—H17120.00
C7—N1—C8124.0 (2)S2—C18—O3125.3 (3)
C18—N3—C24114.8 (2)S2—C18—N3110.1 (2)
C18—N3—C25121.9 (3)O3—C18—N3124.6 (3)
C24—N3—C25123.1 (3)S2—C19—C20127.6 (2)
S1—C1—O1124.4 (3)S2—C19—C24112.2 (2)
S1—C1—N1110.3 (2)C20—C19—C24120.2 (3)
O1—C1—N1125.3 (3)C19—C20—C21118.7 (3)
S1—C2—C3129.0 (2)C20—C21—C22120.4 (3)
S1—C2—C7111.2 (2)C20—C21—C28121.4 (3)
C3—C2—C7119.9 (3)C22—C21—C28118.2 (3)
C2—C3—C4119.9 (3)C21—C22—C23120.9 (3)
C3—C4—C5119.5 (3)C22—C23—C24118.4 (3)
C3—C4—C11121.4 (3)N3—C24—C19111.8 (3)
C5—C4—C11119.1 (3)N3—C24—C23126.7 (2)
C4—C5—C6121.6 (3)C19—C24—C23121.5 (3)
C5—C6—C7117.9 (3)N3—C25—C26113.6 (2)
N1—C7—C6126.4 (2)C25—C26—C27113.0 (3)
C2—C7—C6121.2 (2)N4—C27—C26179.1 (3)
N1—C7—C2112.4 (2)O4—C28—C21121.2 (3)
N1—C8—C9112.7 (2)O4—C28—C29120.2 (3)
C8—C9—C10113.7 (3)C21—C28—C29118.7 (3)
N2—C10—C9179.1 (3)C28—C29—C30123.0 (3)
O2—C11—C4122.2 (3)C28—C29—C34119.0 (3)
O2—C11—C12119.1 (3)C30—C29—C34117.7 (3)
C4—C11—C12118.7 (3)Cl2—C30—C29121.0 (3)
C11—C12—C17118.1 (3)Cl2—C30—C31116.7 (3)
C13—C12—C17116.6 (3)C29—C30—C31122.3 (4)
C11—C12—C13125.1 (3)C30—C31—C32118.5 (4)
C12—C13—C14123.1 (3)C31—C32—C33120.5 (4)
Cl1—C13—C12119.8 (3)C32—C33—C34120.0 (4)
Cl1—C13—C14117.1 (3)C29—C34—C33121.0 (3)
C13—C14—C15119.0 (4)C19—C20—H20121.00
C14—C15—C16120.2 (4)C21—C20—H20121.00
C15—C16—C17120.2 (4)C21—C22—H22120.00
C12—C17—C16120.9 (3)C23—C22—H22120.00
C2—C3—H3120.00C22—C23—H23121.00
C4—C3—H3120.00C24—C23—H23121.00
C4—C5—H5119.00N3—C25—H25A109.00
C6—C5—H5119.00N3—C25—H25B109.00
C5—C6—H6121.00C26—C25—H25A109.00
C7—C6—H6121.00C26—C25—H25B109.00
N1—C8—H8B109.00H25A—C25—H25B108.00
C9—C8—H8A109.00C25—C26—H26A109.00
N1—C8—H8A109.00C25—C26—H26B109.00
C9—C8—H8B109.00C27—C26—H26A109.00
H8A—C8—H8B108.00C27—C26—H26B109.00
C10—C9—H9A109.00H26A—C26—H26B108.00
C8—C9—H9A109.00C30—C31—H31121.00
C10—C9—H9B109.00C32—C31—H31121.00
H9A—C9—H9B108.00C31—C32—H32120.00
C8—C9—H9B109.00C33—C32—H32120.00
C13—C14—H14121.00C32—C33—H33120.00
C15—C14—H14121.00C34—C33—H33120.00
C14—C15—H15120.00C29—C34—H34119.00
C16—C15—H15120.00C33—C34—H34120.00
C2—S1—C1—O1179.3 (3)C4—C11—C12—C1756.2 (4)
C2—S1—C1—N10.6 (2)O2—C11—C12—C17121.3 (3)
C1—S1—C2—C3178.7 (3)C4—C11—C12—C13130.3 (3)
C1—S1—C2—C70.7 (2)C11—C12—C17—C16174.5 (3)
C19—S2—C18—N31.0 (2)C11—C12—C13—Cl17.1 (4)
C18—S2—C19—C240.6 (2)C11—C12—C13—C14176.0 (3)
C19—S2—C18—O3179.2 (3)C17—C12—C13—Cl1179.3 (2)
C18—S2—C19—C20178.8 (3)C17—C12—C13—C142.4 (5)
C7—N1—C1—O1179.6 (3)C13—C12—C17—C160.4 (5)
C8—N1—C1—O15.3 (4)Cl1—C13—C14—C15179.5 (3)
C1—N1—C7—C20.3 (3)C12—C13—C14—C153.6 (6)
C8—N1—C7—C2173.8 (2)C13—C14—C15—C162.7 (7)
C8—N1—C1—S1174.57 (19)C14—C15—C16—C170.9 (7)
C8—N1—C7—C66.7 (4)C15—C16—C17—C120.3 (6)
C1—N1—C8—C9106.4 (3)C24—C19—C20—C211.1 (4)
C1—N1—C7—C6179.2 (3)S2—C19—C20—C21179.2 (2)
C7—N1—C8—C979.9 (3)S2—C19—C24—C23179.9 (2)
C7—N1—C1—S10.3 (3)C20—C19—C24—N3178.4 (2)
C24—N3—C18—S21.3 (3)S2—C19—C24—N30.1 (3)
C18—N3—C24—C190.9 (3)C20—C19—C24—C231.5 (4)
C24—N3—C18—O3178.9 (3)C19—C20—C21—C28177.5 (3)
C25—N3—C18—O36.2 (4)C19—C20—C21—C220.1 (4)
C25—N3—C18—S2173.63 (19)C28—C21—C22—C23177.0 (3)
C18—N3—C24—C23179.3 (3)C20—C21—C22—C230.5 (4)
C25—N3—C24—C235.9 (4)C22—C21—C28—O412.4 (4)
C25—N3—C24—C19174.0 (2)C20—C21—C28—O4165.1 (3)
C24—N3—C25—C2678.6 (3)C20—C21—C28—C2916.5 (4)
C18—N3—C25—C26106.9 (3)C22—C21—C28—C29166.0 (3)
C3—C2—C7—C61.8 (4)C21—C22—C23—C240.1 (4)
S1—C2—C3—C4179.7 (2)C22—C23—C24—C190.8 (4)
S1—C2—C7—C6178.8 (2)C22—C23—C24—N3179.0 (3)
C7—C2—C3—C40.9 (4)N3—C25—C26—C2767.4 (3)
S1—C2—C7—N10.7 (3)O4—C28—C29—C3050.0 (5)
C3—C2—C7—N1178.8 (3)O4—C28—C29—C34123.9 (4)
C2—C3—C4—C50.8 (4)C21—C28—C29—C30131.6 (3)
C2—C3—C4—C11179.9 (3)C21—C28—C29—C3454.5 (4)
C3—C4—C5—C61.7 (4)C28—C29—C30—Cl26.9 (5)
C11—C4—C5—C6179.0 (3)C28—C29—C30—C31175.4 (4)
C3—C4—C11—O2158.7 (3)C34—C29—C30—Cl2179.2 (3)
C3—C4—C11—C1224.0 (4)C34—C29—C30—C311.5 (5)
C5—C4—C11—O220.6 (4)C28—C29—C34—C33175.5 (3)
C5—C4—C11—C12156.7 (3)C30—C29—C34—C331.3 (5)
C4—C5—C6—C70.9 (4)Cl2—C30—C31—C32179.6 (3)
C5—C6—C7—N1179.8 (3)C29—C30—C31—C321.7 (6)
C5—C6—C7—C20.9 (4)C30—C31—C32—C331.8 (6)
N1—C8—C9—C1068.5 (3)C31—C32—C33—C341.6 (7)
O2—C11—C12—C1352.3 (4)C32—C33—C34—C291.4 (6)
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x, y1, z; (iv) x+2, y, z; (v) x, y+1, z; (vi) x1, y+1, z; (vii) x+1, y+1, z+1; (viii) x+1, y+2, z+1; (ix) x+2, y+1, z+1; (x) x+1, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···O10.972.472.846 (4)103
C25—H25A···O30.972.482.852 (4)103
 

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