3-[6-(2-Chloro­benzo­yl)-2-oxo-2,3-dihydro-1,3-benzothia­zol-3-yl]propane­nitrile

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.

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

No syntax errors found



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

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Computing details

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

Crystal data

C17H11ClN2O2S	Z = 4
Mr = 342.80	F(000) = 704
Triclinic, P1	Dx = 1.464 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.089 (1) Å	Cell parameters from 20093 reflections
b = 8.522 (1) Å	θ = 1.6–26.1°
c = 26.042 (2) Å	µ = 0.39 mm^−1
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) Å^3

Data collection

Stoe IPDS-2 diffractometer	5906 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2842 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.085
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω scans	h = −8→8
Absorption correction: integration (XRED32; Stoe & Cie, 2002)	k = −10→10
Tmin = 0.844, Tmax = 0.951	l = −32→31
24878 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 0.84	w = 1/[σ^2(Fo^2) + (0.0646P)^2] where P = (Fo^2 + 2Fc^2)/3
5906 reflections	(Δ/σ)max < 0.001
416 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.23995 (15)	0.23762 (15)	0.10246 (4)	0.1021 (5)
S1	0.56566 (11)	0.92236 (9)	0.27922 (3)	0.0527 (3)
O1	0.6228 (3)	1.0775 (3)	0.37415 (9)	0.0688 (9)
O2	0.4892 (4)	0.1808 (3)	0.19915 (9)	0.0819 (10)
N1	0.6215 (3)	0.8040 (3)	0.36414 (9)	0.0454 (8)
N2	0.2537 (4)	0.9502 (4)	0.46343 (11)	0.0703 (11)
C1	0.6078 (4)	0.9485 (4)	0.34682 (12)	0.0511 (11)
C2	0.5702 (4)	0.7175 (3)	0.27626 (11)	0.0442 (9)
C3	0.5500 (4)	0.6020 (4)	0.23328 (11)	0.0479 (10)
C4	0.5573 (4)	0.4440 (3)	0.23937 (11)	0.0454 (10)
C5	0.5829 (4)	0.4018 (4)	0.28920 (11)	0.0494 (10)
C6	0.6060 (4)	0.5152 (4)	0.33264 (11)	0.0469 (10)
C7	0.6006 (4)	0.6736 (3)	0.32559 (10)	0.0430 (9)
C8	0.6727 (4)	0.7939 (4)	0.41821 (11)	0.0503 (10)
C9	0.5062 (4)	0.7417 (4)	0.44843 (11)	0.0494 (10)
C10	0.3640 (5)	0.8591 (4)	0.45648 (11)	0.0522 (11)
C11	0.5366 (4)	0.3178 (4)	0.19452 (11)	0.0513 (11)
C12	0.5834 (4)	0.3586 (3)	0.14206 (11)	0.0536 (10)
C13	0.4691 (5)	0.3211 (4)	0.09806 (13)	0.0670 (12)
C14	0.5217 (6)	0.3522 (5)	0.05071 (14)	0.0770 (16)
C15	0.7023 (8)	0.4170 (5)	0.04541 (16)	0.0894 (18)
C16	0.8213 (6)	0.4546 (5)	0.08754 (17)	0.0798 (16)
C17	0.7640 (5)	0.4266 (4)	0.13565 (14)	0.0685 (12)
Cl2	1.28851 (16)	−0.25945 (16)	0.09990 (4)	0.1034 (5)
S2	1.07754 (11)	0.42819 (9)	0.28098 (3)	0.0527 (3)
O3	1.1242 (3)	0.5812 (3)	0.37667 (9)	0.0708 (9)
O4	1.0869 (5)	−0.3107 (3)	0.19985 (10)	0.0920 (13)
N3	1.1220 (3)	0.3085 (3)	0.36598 (8)	0.0462 (8)
N4	0.7472 (5)	0.4481 (4)	0.46335 (11)	0.0741 (12)
C18	1.1113 (4)	0.4537 (4)	0.34869 (12)	0.0533 (11)
C19	1.0747 (4)	0.2238 (3)	0.27858 (10)	0.0437 (9)
C20	1.0552 (4)	0.1095 (4)	0.23460 (11)	0.0469 (10)
C21	1.0588 (4)	−0.0496 (4)	0.24095 (11)	0.0473 (10)
C22	1.0818 (4)	−0.0937 (4)	0.29040 (11)	0.0478 (10)
C23	1.1029 (4)	0.0198 (4)	0.33393 (11)	0.0463 (10)
C24	1.1002 (4)	0.1781 (4)	0.32722 (10)	0.0438 (10)
C25	1.1689 (4)	0.2948 (4)	0.41997 (11)	0.0523 (10)
C26	1.0008 (4)	0.2407 (4)	0.44978 (11)	0.0521 (10)
C27	0.8585 (5)	0.3581 (4)	0.45712 (11)	0.0531 (11)
C28	1.0465 (4)	−0.1772 (4)	0.19545 (11)	0.0547 (11)
C29	0.9777 (5)	−0.1378 (4)	0.14402 (12)	0.0597 (11)
C30	1.0690 (5)	−0.1774 (4)	0.09924 (14)	0.0713 (14)
C31	0.9970 (7)	−0.1501 (5)	0.05164 (14)	0.0798 (16)
C32	0.8241 (7)	−0.0842 (5)	0.04948 (16)	0.0899 (19)
C33	0.7287 (6)	−0.0428 (5)	0.09411 (16)	0.0812 (16)
C34	0.8024 (5)	−0.0703 (4)	0.14047 (13)	0.0664 (12)
H3	0.53160	0.63100	0.20040	0.0570*
H5	0.58440	0.29500	0.29320	0.0590*
H6	0.62460	0.48620	0.36550	0.0560*
H8A	0.72440	0.89690	0.43460	0.0600*
H8B	0.77060	0.71930	0.41950	0.0600*
H9A	0.44700	0.64400	0.43000	0.0590*
H9B	0.55250	0.71930	0.48190	0.0590*
H14	0.43770	0.33040	0.02220	0.0930*
H15	0.74220	0.43480	0.01290	0.1070*
H16	0.94200	0.49950	0.08390	0.0960*
H17	0.84640	0.45330	0.16430	0.0820*
H20	1.04010	0.13940	0.20170	0.0560*
H22	1.08310	−0.20060	0.29420	0.0570*
H23	1.11840	−0.00970	0.36680	0.0560*
H25A	1.22030	0.39700	0.43710	0.0630*
H25B	1.26650	0.21990	0.42110	0.0630*
H26A	0.94270	0.14280	0.43120	0.0620*
H26B	1.04570	0.21850	0.48340	0.0620*
H31	1.06360	−0.17550	0.02170	0.0960*
H32	0.77160	−0.06770	0.01760	0.1080*
H33	0.61380	0.00410	0.09250	0.0970*
H34	0.73580	−0.04420	0.17040	0.0800*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0790 (7)	0.1250 (10)	0.0973 (8)	−0.0196 (6)	−0.0236 (5)	0.0141 (7)
S1	0.0606 (5)	0.0466 (5)	0.0541 (5)	0.0076 (3)	0.0082 (3)	0.0151 (3)
O1	0.0923 (17)	0.0452 (14)	0.0662 (15)	0.0021 (11)	0.0019 (11)	−0.0012 (11)
O2	0.133 (2)	0.0551 (15)	0.0575 (15)	−0.0028 (14)	0.0062 (13)	0.0101 (11)
N1	0.0504 (13)	0.0424 (15)	0.0429 (14)	0.0045 (10)	0.0023 (10)	0.0032 (11)
N2	0.082 (2)	0.0664 (19)	0.0682 (19)	0.0300 (16)	0.0121 (14)	0.0174 (14)
C1	0.0512 (17)	0.048 (2)	0.0536 (19)	0.0006 (13)	0.0073 (13)	0.0047 (16)
C2	0.0438 (15)	0.0469 (17)	0.0429 (17)	0.0082 (12)	0.0043 (11)	0.0072 (13)
C3	0.0487 (16)	0.0546 (19)	0.0414 (17)	0.0043 (13)	0.0018 (12)	0.0100 (14)
C4	0.0463 (16)	0.0485 (18)	0.0417 (17)	0.0059 (12)	0.0034 (12)	0.0062 (13)
C5	0.0614 (18)	0.0421 (17)	0.0461 (18)	0.0090 (13)	0.0033 (13)	0.0084 (14)
C6	0.0528 (17)	0.0493 (19)	0.0397 (16)	0.0099 (13)	0.0003 (12)	0.0071 (14)
C7	0.0387 (14)	0.0483 (18)	0.0422 (17)	0.0072 (12)	0.0037 (11)	0.0043 (14)
C8	0.0534 (17)	0.0534 (18)	0.0422 (17)	0.0045 (14)	−0.0028 (12)	−0.0002 (13)
C9	0.0604 (18)	0.0484 (17)	0.0396 (16)	0.0110 (14)	0.0024 (13)	0.0035 (13)
C10	0.069 (2)	0.0513 (19)	0.0370 (17)	0.0096 (16)	0.0019 (13)	0.0060 (14)
C11	0.0534 (17)	0.050 (2)	0.0509 (19)	0.0075 (14)	−0.0011 (13)	0.0073 (15)
C12	0.069 (2)	0.0464 (17)	0.0440 (17)	0.0024 (14)	0.0035 (14)	0.0017 (13)
C13	0.092 (2)	0.055 (2)	0.052 (2)	0.0073 (17)	−0.0049 (17)	0.0010 (15)
C14	0.111 (3)	0.073 (3)	0.045 (2)	0.003 (2)	−0.0062 (19)	0.0041 (18)
C15	0.140 (4)	0.074 (3)	0.057 (2)	0.014 (3)	0.026 (2)	0.0118 (19)
C16	0.088 (3)	0.071 (2)	0.082 (3)	0.0021 (19)	0.027 (2)	0.012 (2)
C17	0.068 (2)	0.067 (2)	0.066 (2)	−0.0052 (17)	0.0072 (16)	−0.0042 (17)
Cl2	0.0846 (7)	0.1245 (10)	0.0966 (8)	0.0172 (6)	0.0262 (5)	−0.0105 (7)
S2	0.0585 (5)	0.0479 (5)	0.0532 (5)	0.0002 (3)	0.0018 (3)	0.0135 (3)
O3	0.0898 (17)	0.0470 (14)	0.0715 (16)	−0.0035 (11)	−0.0041 (12)	−0.0017 (12)
O4	0.158 (3)	0.0555 (16)	0.0623 (16)	0.0287 (16)	−0.0046 (15)	0.0003 (12)
N3	0.0540 (14)	0.0457 (15)	0.0382 (14)	0.0026 (11)	0.0011 (10)	0.0038 (11)
N4	0.086 (2)	0.071 (2)	0.071 (2)	0.0323 (17)	0.0161 (15)	0.0160 (15)
C18	0.0549 (18)	0.046 (2)	0.057 (2)	−0.0013 (14)	0.0005 (14)	0.0024 (16)
C19	0.0401 (15)	0.0517 (18)	0.0402 (16)	0.0002 (12)	0.0052 (11)	0.0095 (13)
C20	0.0490 (16)	0.0521 (19)	0.0396 (16)	0.0011 (13)	0.0028 (12)	0.0073 (14)
C21	0.0460 (16)	0.0542 (19)	0.0411 (17)	0.0051 (13)	0.0036 (12)	0.0032 (14)
C22	0.0503 (16)	0.0467 (18)	0.0472 (18)	0.0046 (13)	0.0056 (12)	0.0082 (14)
C23	0.0535 (17)	0.0515 (19)	0.0360 (16)	0.0086 (13)	0.0036 (12)	0.0109 (14)
C24	0.0408 (15)	0.0510 (19)	0.0393 (17)	0.0047 (12)	0.0037 (11)	0.0042 (14)
C25	0.0560 (18)	0.0542 (19)	0.0450 (17)	0.0046 (14)	−0.0012 (13)	0.0003 (14)
C26	0.0643 (19)	0.0457 (17)	0.0470 (18)	0.0137 (14)	0.0050 (14)	0.0044 (13)
C27	0.066 (2)	0.055 (2)	0.0396 (17)	0.0081 (17)	0.0058 (13)	0.0086 (14)
C28	0.0639 (19)	0.055 (2)	0.0442 (18)	0.0024 (15)	0.0060 (13)	0.0025 (15)
C29	0.082 (2)	0.0481 (18)	0.0459 (18)	−0.0017 (16)	−0.0015 (15)	−0.0016 (14)
C30	0.098 (3)	0.059 (2)	0.053 (2)	−0.0090 (18)	0.0086 (18)	−0.0024 (16)
C31	0.120 (3)	0.070 (3)	0.047 (2)	−0.012 (2)	0.008 (2)	0.0061 (17)
C32	0.136 (4)	0.071 (3)	0.061 (3)	−0.012 (2)	−0.028 (2)	0.0169 (19)
C33	0.087 (3)	0.073 (2)	0.081 (3)	0.0038 (19)	−0.020 (2)	0.007 (2)
C34	0.071 (2)	0.066 (2)	0.059 (2)	0.0051 (17)	−0.0017 (16)	−0.0031 (16)

Geometric parameters (Å, º)

Cl1—C13	1.749 (4)	C6—H6	0.9300
Cl2—C30	1.742 (4)	C8—H8B	0.9700
S1—C1	1.759 (3)	C8—H8A	0.9700
S1—C2	1.739 (3)	C9—H9B	0.9700
S2—C18	1.755 (3)	C9—H9A	0.9700
S2—C19	1.734 (3)	C14—H14	0.9300
O1—C1	1.224 (4)	C15—H15	0.9300
O2—C11	1.219 (4)	C16—H16	0.9300
O3—C18	1.221 (4)	C17—H17	0.9300
O4—C28	1.208 (4)	C19—C20	1.398 (4)
N1—C8	1.459 (4)	C19—C24	1.384 (4)
N1—C1	1.375 (4)	C20—C21	1.389 (5)
N1—C7	1.392 (4)	C21—C22	1.397 (4)
N2—C10	1.134 (5)	C21—C28	1.494 (4)
N3—C24	1.396 (4)	C22—C23	1.386 (4)
N3—C25	1.457 (4)	C23—C24	1.385 (5)
N3—C18	1.378 (4)	C25—C26	1.524 (4)
N4—C27	1.131 (5)	C26—C27	1.459 (5)
C2—C3	1.386 (4)	C28—C29	1.499 (4)
C2—C7	1.400 (4)	C29—C30	1.362 (5)
C3—C4	1.381 (4)	C29—C34	1.405 (5)
C4—C11	1.475 (4)	C30—C31	1.380 (5)
C4—C5	1.402 (4)	C31—C32	1.380 (7)
C5—C6	1.385 (4)	C32—C33	1.377 (6)
C6—C7	1.389 (4)	C33—C34	1.356 (5)
C8—C9	1.516 (4)	C20—H20	0.9300
C9—C10	1.460 (5)	C22—H22	0.9300
C11—C12	1.496 (4)	C23—H23	0.9300
C12—C17	1.399 (5)	C25—H25A	0.9700
C12—C13	1.375 (4)	C25—H25B	0.9700
C13—C14	1.354 (5)	C26—H26A	0.9700
C14—C15	1.383 (7)	C26—H26B	0.9700
C15—C16	1.356 (6)	C31—H31	0.9300
C16—C17	1.375 (6)	C32—H32	0.9300
C3—H3	0.9300	C33—H33	0.9300
C5—H5	0.9300	C34—H34	0.9300
Cl1···O2	3.141 (3)	C26···O1^iii	3.395 (4)
Cl1···C16^i	3.623 (4)	C26···N2^vii	3.450 (4)
Cl2···O4	3.076 (3)	C27···O1^iii	3.336 (4)
Cl2···C33^ii	3.552 (4)	C27···C18	3.549 (4)
Cl2···H16^iii	3.0900	C27···C27^ix	3.550 (5)
Cl2···H15^iv	3.1100	C27···C10^vii	3.460 (5)
S1···C22^v	3.674 (3)	C30···C16^iii	3.478 (6)
S1···O2^v	3.286 (3)	C33···Cl2^i	3.552 (4)
S1···C21^v	3.666 (3)	C34···C20	3.161 (5)
S1···C22^vi	3.447 (3)	C3···H17	3.0300
S2···C4^ii	3.600 (3)	C4···H17	2.8800
S2···C5	3.516 (3)	C6···H8B	2.8400
S2···C5^ii	3.604 (3)	C6···H9A	2.9100
S2···O4^v	3.267 (3)	C7···H9A	2.9900
S1···H5^v	3.1400	C8···H6	2.7900
S1···H34^v	3.1500	C9···H6	3.0300
S2···H22^v	3.1300	C12···H3	2.6500
O1···C26^v	3.395 (4)	C13···H33	2.9300
O1···C27^v	3.336 (4)	C17···H3	2.8800
O2···Cl1	3.141 (3)	C20···H34	2.9100
O2···S1^iii	3.286 (3)	C21···H34	2.9000
O2···C20^i	3.285 (4)	C23···H25B	2.8300
O3···C9^ii	3.361 (4)	C23···H26A	2.9000
O3···C10^ii	3.291 (4)	C24···H26A	3.0000
O4···Cl2	3.076 (3)	C25···H23	2.7700
O4···S2^iii	3.267 (3)	C26···H23	3.0000
O4···C17^iii	3.352 (5)	C29···H20	2.6300
O1···H26A^v	2.6600	C30···H16^iii	2.8200
O1···H8A	2.4700	C34···H20	2.7000
O2···H34	2.7100	H3···C17	2.8800
O2···H5	2.5700	H3···C12	2.6500
O3···H9A^ii	2.6300	H5···S1^iii	3.1400
O3···H25A	2.4800	H5···O2	2.5700
O4···H17^iii	2.6100	H6···N4	2.7400
O4···H22	2.5100	H6···C8	2.7900
N2···C26^vi	3.190 (5)	H6···C9	3.0300
N2···C26^vii	3.450 (4)	H6···H8B	2.4300
N2···C25^vi	3.365 (5)	H6···H9A	2.4300
N4···C8	3.379 (5)	H8A···N2^viii	2.7900
N4···C9	3.168 (5)	H8A···O1	2.4700
N2···H26B^vi	2.7900	H8A···H26A^v	2.5500
N2···H25B^vi	2.6800	H8B···H6	2.4300
N2···H23^vi	2.7400	H8B···N4	2.7100
N2···H8A^viii	2.7900	H8B···C6	2.8400
N4···H25A^ix	2.7400	H9A···H6	2.4300
N4···H6	2.7400	H9A···O3^i	2.6300
N4···H8B	2.7100	H9A···C7	2.9900
N4···H9B	2.7500	H9A···C6	2.9100
C1···C10	3.528 (4)	H9B···N4	2.7500
C1···C23^v	3.561 (4)	H15···Cl2^iv	3.1100
C3···C17	3.234 (5)	H16···C30^v	2.8200
C4···S2^i	3.600 (3)	H16···Cl2^v	3.0900
C5···S2^i	3.604 (3)	H17···C4	2.8800
C5···S2	3.516 (3)	H17···O4^v	2.6100
C6···C18^i	3.561 (4)	H17···C3	3.0300
C6···C9	3.469 (4)	H20···C29	2.6300
C8···N4	3.379 (5)	H20···C34	2.7000
C9···C6	3.469 (4)	H22···S2^iii	3.1300
C9···N4	3.168 (5)	H22···O4	2.5100
C9···O3^i	3.361 (4)	H23···N2^x	2.7400
C10···C10^viii	3.519 (5)	H23···C25	2.7700
C10···C1	3.528 (4)	H23···C26	3.0000
C10···C27^vii	3.460 (5)	H23···H25B	2.4200
C10···O3^i	3.291 (4)	H23···H26A	2.4000
C16···Cl1^ii	3.623 (4)	H25A···O3	2.4800
C16···C30^v	3.478 (6)	H25A···N4^ix	2.7400
C17···C3	3.234 (5)	H25B···N2^x	2.6800
C17···O4^v	3.352 (5)	H25B···C23	2.8300
C18···C27	3.549 (4)	H25B···H23	2.4200
C18···C6^ii	3.561 (4)	H26A···O1^iii	2.6600
C20···O2^ii	3.285 (4)	H26A···C23	2.9000
C20···C34	3.161 (5)	H26A···C24	3.0000
C21···S1^iii	3.666 (3)	H26A···H8A^iii	2.5500
C22···S1^x	3.447 (3)	H26A···H23	2.4000
C22···S1^iii	3.674 (3)	H26B···N2^x	2.7900
C23···C26	3.453 (4)	H33···C13	2.9300
C23···C1^iii	3.561 (4)	H34···S1^iii	3.1500
C25···N2^x	3.365 (5)	H34···O2	2.7100
C26···N2^x	3.190 (5)	H34···C20	2.9100
C26···C23	3.453 (4)	H34···C21	2.9000
C1—S1—C2	91.34 (15)	C17—C16—H16	120.00
C18—S2—C19	91.01 (15)	C15—C16—H16	120.00
C1—N1—C7	114.8 (2)	C12—C17—H17	120.00
C1—N1—C8	121.0 (3)	C16—C17—H17	120.00
C7—N1—C8	124.0 (2)	S2—C18—O3	125.3 (3)
C18—N3—C24	114.8 (2)	S2—C18—N3	110.1 (2)
C18—N3—C25	121.9 (3)	O3—C18—N3	124.6 (3)
C24—N3—C25	123.1 (3)	S2—C19—C20	127.6 (2)
S1—C1—O1	124.4 (3)	S2—C19—C24	112.2 (2)
S1—C1—N1	110.3 (2)	C20—C19—C24	120.2 (3)
O1—C1—N1	125.3 (3)	C19—C20—C21	118.7 (3)
S1—C2—C3	129.0 (2)	C20—C21—C22	120.4 (3)
S1—C2—C7	111.2 (2)	C20—C21—C28	121.4 (3)
C3—C2—C7	119.9 (3)	C22—C21—C28	118.2 (3)
C2—C3—C4	119.9 (3)	C21—C22—C23	120.9 (3)
C3—C4—C5	119.5 (3)	C22—C23—C24	118.4 (3)
C3—C4—C11	121.4 (3)	N3—C24—C19	111.8 (3)
C5—C4—C11	119.1 (3)	N3—C24—C23	126.7 (2)
C4—C5—C6	121.6 (3)	C19—C24—C23	121.5 (3)
C5—C6—C7	117.9 (3)	N3—C25—C26	113.6 (2)
N1—C7—C6	126.4 (2)	C25—C26—C27	113.0 (3)
C2—C7—C6	121.2 (2)	N4—C27—C26	179.1 (3)
N1—C7—C2	112.4 (2)	O4—C28—C21	121.2 (3)
N1—C8—C9	112.7 (2)	O4—C28—C29	120.2 (3)
C8—C9—C10	113.7 (3)	C21—C28—C29	118.7 (3)
N2—C10—C9	179.1 (3)	C28—C29—C30	123.0 (3)
O2—C11—C4	122.2 (3)	C28—C29—C34	119.0 (3)
O2—C11—C12	119.1 (3)	C30—C29—C34	117.7 (3)
C4—C11—C12	118.7 (3)	Cl2—C30—C29	121.0 (3)
C11—C12—C17	118.1 (3)	Cl2—C30—C31	116.7 (3)
C13—C12—C17	116.6 (3)	C29—C30—C31	122.3 (4)
C11—C12—C13	125.1 (3)	C30—C31—C32	118.5 (4)
C12—C13—C14	123.1 (3)	C31—C32—C33	120.5 (4)
Cl1—C13—C12	119.8 (3)	C32—C33—C34	120.0 (4)
Cl1—C13—C14	117.1 (3)	C29—C34—C33	121.0 (3)
C13—C14—C15	119.0 (4)	C19—C20—H20	121.00
C14—C15—C16	120.2 (4)	C21—C20—H20	121.00
C15—C16—C17	120.2 (4)	C21—C22—H22	120.00
C12—C17—C16	120.9 (3)	C23—C22—H22	120.00
C2—C3—H3	120.00	C22—C23—H23	121.00
C4—C3—H3	120.00	C24—C23—H23	121.00
C4—C5—H5	119.00	N3—C25—H25A	109.00
C6—C5—H5	119.00	N3—C25—H25B	109.00
C5—C6—H6	121.00	C26—C25—H25A	109.00
C7—C6—H6	121.00	C26—C25—H25B	109.00
N1—C8—H8B	109.00	H25A—C25—H25B	108.00
C9—C8—H8A	109.00	C25—C26—H26A	109.00
N1—C8—H8A	109.00	C25—C26—H26B	109.00
C9—C8—H8B	109.00	C27—C26—H26A	109.00
H8A—C8—H8B	108.00	C27—C26—H26B	109.00
C10—C9—H9A	109.00	H26A—C26—H26B	108.00
C8—C9—H9A	109.00	C30—C31—H31	121.00
C10—C9—H9B	109.00	C32—C31—H31	121.00
H9A—C9—H9B	108.00	C31—C32—H32	120.00
C8—C9—H9B	109.00	C33—C32—H32	120.00
C13—C14—H14	121.00	C32—C33—H33	120.00
C15—C14—H14	121.00	C34—C33—H33	120.00
C14—C15—H15	120.00	C29—C34—H34	119.00
C16—C15—H15	120.00	C33—C34—H34	120.00
C2—S1—C1—O1	179.3 (3)	C4—C11—C12—C17	56.2 (4)
C2—S1—C1—N1	−0.6 (2)	O2—C11—C12—C17	−121.3 (3)
C1—S1—C2—C3	−178.7 (3)	C4—C11—C12—C13	−130.3 (3)
C1—S1—C2—C7	0.7 (2)	C11—C12—C17—C16	174.5 (3)
C19—S2—C18—N3	1.0 (2)	C11—C12—C13—Cl1	7.1 (4)
C18—S2—C19—C24	−0.6 (2)	C11—C12—C13—C14	−176.0 (3)
C19—S2—C18—O3	−179.2 (3)	C17—C12—C13—Cl1	−179.3 (2)
C18—S2—C19—C20	−178.8 (3)	C17—C12—C13—C14	−2.4 (5)
C7—N1—C1—O1	−179.6 (3)	C13—C12—C17—C16	0.4 (5)
C8—N1—C1—O1	−5.3 (4)	Cl1—C13—C14—C15	−179.5 (3)
C1—N1—C7—C2	0.3 (3)	C12—C13—C14—C15	3.6 (6)
C8—N1—C7—C2	−173.8 (2)	C13—C14—C15—C16	−2.7 (7)
C8—N1—C1—S1	174.57 (19)	C14—C15—C16—C17	0.9 (7)
C8—N1—C7—C6	6.7 (4)	C15—C16—C17—C12	0.3 (6)
C1—N1—C8—C9	106.4 (3)	C24—C19—C20—C21	1.1 (4)
C1—N1—C7—C6	−179.2 (3)	S2—C19—C20—C21	179.2 (2)
C7—N1—C8—C9	−79.9 (3)	S2—C19—C24—C23	−179.9 (2)
C7—N1—C1—S1	0.3 (3)	C20—C19—C24—N3	178.4 (2)
C24—N3—C18—S2	−1.3 (3)	S2—C19—C24—N3	−0.1 (3)
C18—N3—C24—C19	0.9 (3)	C20—C19—C24—C23	−1.5 (4)
C24—N3—C18—O3	178.9 (3)	C19—C20—C21—C28	−177.5 (3)
C25—N3—C18—O3	−6.2 (4)	C19—C20—C21—C22	−0.1 (4)
C25—N3—C18—S2	173.63 (19)	C28—C21—C22—C23	177.0 (3)
C18—N3—C24—C23	−179.3 (3)	C20—C21—C22—C23	−0.5 (4)
C25—N3—C24—C23	5.9 (4)	C22—C21—C28—O4	−12.4 (4)
C25—N3—C24—C19	−174.0 (2)	C20—C21—C28—O4	165.1 (3)
C24—N3—C25—C26	−78.6 (3)	C20—C21—C28—C29	−16.5 (4)
C18—N3—C25—C26	106.9 (3)	C22—C21—C28—C29	166.0 (3)
C3—C2—C7—C6	−1.8 (4)	C21—C22—C23—C24	0.1 (4)
S1—C2—C3—C4	−179.7 (2)	C22—C23—C24—C19	0.8 (4)
S1—C2—C7—C6	178.8 (2)	C22—C23—C24—N3	−179.0 (3)
C7—C2—C3—C4	0.9 (4)	N3—C25—C26—C27	−67.4 (3)
S1—C2—C7—N1	−0.7 (3)	O4—C28—C29—C30	−50.0 (5)
C3—C2—C7—N1	178.8 (3)	O4—C28—C29—C34	123.9 (4)
C2—C3—C4—C5	0.8 (4)	C21—C28—C29—C30	131.6 (3)
C2—C3—C4—C11	−179.9 (3)	C21—C28—C29—C34	−54.5 (4)
C3—C4—C5—C6	−1.7 (4)	C28—C29—C30—Cl2	−6.9 (5)
C11—C4—C5—C6	179.0 (3)	C28—C29—C30—C31	175.4 (4)
C3—C4—C11—O2	−158.7 (3)	C34—C29—C30—Cl2	179.2 (3)
C3—C4—C11—C12	24.0 (4)	C34—C29—C30—C31	1.5 (5)
C5—C4—C11—O2	20.6 (4)	C28—C29—C34—C33	−175.5 (3)
C5—C4—C11—C12	−156.7 (3)	C30—C29—C34—C33	−1.3 (5)
C4—C5—C6—C7	0.9 (4)	Cl2—C30—C31—C32	−179.6 (3)
C5—C6—C7—N1	−179.8 (3)	C29—C30—C31—C32	−1.7 (6)
C5—C6—C7—C2	0.9 (4)	C30—C31—C32—C33	1.8 (6)
N1—C8—C9—C10	−68.5 (3)	C31—C32—C33—C34	−1.6 (7)
O2—C11—C12—C13	52.3 (4)	C32—C33—C34—C29	1.4 (6)

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+2, −y, −z; (v) x, y+1, z; (vi) x−1, 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, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1	0.97	2.47	2.846 (4)	103
C25—H25A···O3	0.97	2.48	2.852 (4)	103