Crystal structure, Hirshfeld surface analysis, inter­action energy and DFT studies of (2Z)-2-(2,4-di­chloro­benzyl­idene)-4-nonyl-3,4-di­hydro-2H-1,4-benzo­thia­zin-3-one

The title compound contains 1,4-benzo­thia­zine and 2,4-di­chloro­phenyl­methyl­idene units in which the di­hydro­thia­zine ring adopts a screw-boat conformation. In the crystal, inter­molecular C—H_Bnz...O_Thz (Bnz = benzene and Thz = thia­zine) hydrogen bonds form chains of mol­ecules extending along the a-axis direction which are connected to their inversion-related counterparts by C—H_Bnz...Cl_Dchlphy (Dchlphy = 2,4-di­chloro­phen­yl) hydrogen bonds and C—H_Dchlphy...π (ring) inter­actions. These double chains are further linked by C—H_Dchlphy...O_Thz hydrogen bonds to form stepped layers approximately parallel to (012).

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.107
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full value Low .      0.964 Why?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5       ..CL1      .       2.86 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        144 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C23      --C24      .       12.0 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         7% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         14 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        117 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   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
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(2Z)-2-(2,4-Dichlorobenzylidene)-4-nonyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

Crystal data

C24H27Cl2NOS	Z = 2
Mr = 448.42	F(000) = 472
Triclinic, P1	Dx = 1.304 Mg m^−3
a = 8.9961 (3) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.3755 (3) Å	Cell parameters from 7317 reflections
c = 13.2565 (4) Å	θ = 3.5–72.4°
α = 73.857 (1)°	µ = 3.52 mm^−1
β = 88.119 (1)°	T = 150 K
γ = 74.182 (1)°	Column, colourless
V = 1142.32 (6) Å^3	0.20 × 0.14 × 0.08 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4246 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3772 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4167 pixels mm^-1	θmax = 72.4°, θmin = 3.5°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −12→12
Tmin = 0.54, Tmax = 0.76	l = −13→15
8788 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual space
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: mixed
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0512P)^2 + 0.6585P] where P = (Fo^2 + 2Fc^2)/3
4246 reflections	(Δ/σ)max < 0.001
349 parameters	Δρmax = 0.32 e Å^−3
14 restraints	Δρmin = −0.50 e Å^−3

Special details

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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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. The two carbons at the end of the nonyl chain, C23 and C24, are disordered in a 0.562 (4)/0.438 (4) ratio. These were refined with restraints that the two components have comparable geometries. The H-atoms on these carbons as well as those on C22 were included as riding contributions in idealized positions.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.49354 (7)	0.17182 (5)	0.85050 (4)	0.04871 (16)
Cl2	0.90576 (10)	−0.32166 (6)	1.00981 (5)	0.0707 (2)
S1	0.74621 (5)	0.09525 (4)	0.49738 (4)	0.03192 (13)
O1	0.30841 (14)	0.26156 (14)	0.47052 (11)	0.0350 (3)
N1	0.49478 (16)	0.35999 (15)	0.39383 (12)	0.0290 (3)
C1	0.77339 (19)	0.26057 (18)	0.43712 (14)	0.0278 (4)
C2	0.9224 (2)	0.2768 (2)	0.43323 (15)	0.0330 (4)
H2	1.005 (3)	0.196 (3)	0.4656 (18)	0.042 (6)*
C3	0.9469 (2)	0.4057 (2)	0.38810 (17)	0.0380 (4)
H3	1.051 (3)	0.414 (3)	0.387 (2)	0.052 (7)*
C4	0.8221 (2)	0.5199 (2)	0.34844 (18)	0.0410 (5)
H4	0.837 (3)	0.613 (3)	0.316 (2)	0.056 (7)*
C5	0.6730 (2)	0.5053 (2)	0.35211 (17)	0.0366 (4)
H5	0.589 (3)	0.587 (2)	0.3270 (18)	0.039 (6)*
C6	0.64689 (19)	0.37512 (19)	0.39486 (14)	0.0287 (4)
C7	0.4449 (2)	0.26179 (18)	0.46805 (14)	0.0286 (4)
C8	0.5633 (2)	0.15326 (18)	0.54591 (15)	0.0291 (4)
C9	0.5205 (2)	0.1027 (2)	0.64295 (16)	0.0344 (4)
H9	0.408 (3)	0.145 (3)	0.656 (2)	0.057 (7)*
C10	0.6193 (2)	−0.0020 (2)	0.73085 (15)	0.0331 (4)
C11	0.6141 (2)	0.0188 (2)	0.83067 (16)	0.0361 (4)
C12	0.7034 (3)	−0.0761 (2)	0.91616 (17)	0.0418 (5)
H12	0.700 (3)	−0.059 (3)	0.986 (2)	0.056 (7)*
C13	0.8000 (3)	−0.1984 (2)	0.90162 (17)	0.0429 (5)
C14	0.8106 (3)	−0.2233 (2)	0.80462 (17)	0.0407 (5)
H14	0.880 (3)	−0.309 (3)	0.797 (2)	0.050 (7)*
C15	0.7214 (2)	−0.1252 (2)	0.72000 (16)	0.0363 (4)
H15	0.729 (3)	−0.149 (3)	0.655 (2)	0.046 (6)*
C16	0.3799 (2)	0.4592 (2)	0.31152 (15)	0.0309 (4)
H16A	0.315 (3)	0.405 (2)	0.2923 (17)	0.036 (6)*
H16B	0.434 (2)	0.491 (2)	0.2491 (17)	0.028 (5)*
C17	0.2769 (2)	0.5837 (2)	0.34303 (15)	0.0313 (4)
H17A	0.225 (3)	0.548 (2)	0.4065 (18)	0.036 (6)*
H17B	0.342 (3)	0.636 (2)	0.3630 (17)	0.032 (5)*
C18	0.1618 (2)	0.6778 (2)	0.25291 (16)	0.0325 (4)
H18A	0.104 (3)	0.623 (2)	0.2318 (17)	0.036 (6)*
H18B	0.217 (3)	0.703 (2)	0.1916 (19)	0.040 (6)*
C19	0.0581 (2)	0.8062 (2)	0.27852 (17)	0.0348 (4)
H19A	0.004 (3)	0.776 (2)	0.3390 (18)	0.035 (6)*
H19B	0.123 (3)	0.859 (3)	0.2959 (19)	0.045 (6)*
C20	−0.0531 (2)	0.9040 (2)	0.18839 (17)	0.0372 (4)
H20A	−0.125 (3)	0.853 (2)	0.1714 (18)	0.039 (6)*
H20B	0.010 (3)	0.934 (2)	0.1228 (19)	0.043 (6)*
C21	−0.1479 (2)	1.0373 (2)	0.21183 (18)	0.0383 (4)
H21A	−0.205 (3)	1.011 (3)	0.274 (2)	0.059 (8)*
H21B	−0.080 (3)	1.087 (2)	0.2266 (18)	0.042 (6)*
C22	−0.2613 (3)	1.1333 (2)	0.12285 (19)	0.0493 (6)
H22A	−0.325994	1.078902	0.104683	0.059*
H22B	−0.201418	1.161858	0.060625	0.059*
C23	−0.3697 (8)	1.2661 (4)	0.1422 (6)	0.0440 (18)	0.562 (4)
H23A	−0.458686	1.305117	0.090467	0.053*	0.562 (4)
H23B	−0.409306	1.245547	0.213838	0.053*	0.562 (4)
C24	−0.2717 (6)	1.3686 (5)	0.1297 (4)	0.0630 (10)	0.562 (4)
H24A	−0.335043	1.455992	0.141231	0.094*	0.562 (4)
H24B	−0.184022	1.328099	0.181244	0.094*	0.562 (4)
H24C	−0.233125	1.387336	0.058565	0.094*	0.562 (4)
C23A	−0.3282 (12)	1.2751 (6)	0.1453 (7)	0.0440 (18)	0.438 (4)
H23C	−0.388048	1.262316	0.209642	0.053*	0.438 (4)
H23D	−0.242430	1.312260	0.158121	0.053*	0.438 (4)
C24A	−0.4333 (8)	1.3801 (6)	0.0534 (5)	0.0630 (10)	0.438 (4)
H24D	−0.474134	1.469164	0.069938	0.094*	0.438 (4)
H24E	−0.373809	1.394060	−0.010101	0.094*	0.438 (4)
H24F	−0.519298	1.344161	0.041374	0.094*	0.438 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0592 (3)	0.0364 (3)	0.0409 (3)	−0.0014 (2)	0.0109 (2)	−0.0080 (2)
Cl2	0.1011 (6)	0.0441 (3)	0.0459 (3)	0.0100 (3)	−0.0229 (3)	−0.0052 (2)
S1	0.0281 (2)	0.0251 (2)	0.0361 (3)	−0.00014 (16)	0.00197 (17)	−0.00517 (17)
O1	0.0233 (6)	0.0393 (7)	0.0427 (8)	−0.0097 (5)	−0.0023 (5)	−0.0104 (6)
N1	0.0200 (7)	0.0281 (7)	0.0351 (8)	−0.0032 (6)	−0.0043 (6)	−0.0054 (6)
C1	0.0231 (8)	0.0284 (8)	0.0289 (9)	−0.0028 (7)	0.0005 (6)	−0.0074 (7)
C2	0.0207 (8)	0.0363 (10)	0.0357 (10)	0.0002 (7)	−0.0005 (7)	−0.0076 (8)
C3	0.0217 (9)	0.0421 (11)	0.0473 (12)	−0.0077 (8)	0.0014 (8)	−0.0088 (9)
C4	0.0275 (9)	0.0339 (10)	0.0569 (13)	−0.0089 (8)	0.0019 (8)	−0.0049 (9)
C5	0.0244 (9)	0.0276 (9)	0.0502 (12)	−0.0032 (7)	−0.0027 (8)	−0.0020 (8)
C6	0.0198 (8)	0.0299 (9)	0.0338 (9)	−0.0038 (7)	−0.0009 (7)	−0.0076 (7)
C7	0.0248 (8)	0.0282 (8)	0.0336 (9)	−0.0058 (7)	−0.0016 (7)	−0.0111 (7)
C8	0.0248 (8)	0.0264 (8)	0.0359 (10)	−0.0063 (7)	−0.0018 (7)	−0.0087 (7)
C9	0.0295 (9)	0.0343 (10)	0.0384 (10)	−0.0093 (8)	0.0010 (8)	−0.0081 (8)
C10	0.0312 (9)	0.0335 (9)	0.0345 (10)	−0.0129 (8)	0.0021 (7)	−0.0055 (8)
C11	0.0403 (10)	0.0294 (9)	0.0358 (10)	−0.0091 (8)	0.0067 (8)	−0.0057 (8)
C12	0.0550 (13)	0.0372 (11)	0.0312 (11)	−0.0117 (9)	0.0019 (9)	−0.0077 (8)
C13	0.0527 (12)	0.0326 (10)	0.0382 (11)	−0.0078 (9)	−0.0058 (9)	−0.0045 (8)
C14	0.0463 (12)	0.0320 (10)	0.0434 (12)	−0.0083 (9)	−0.0026 (9)	−0.0117 (8)
C15	0.0402 (11)	0.0361 (10)	0.0361 (10)	−0.0141 (8)	0.0009 (8)	−0.0122 (8)
C16	0.0240 (8)	0.0312 (9)	0.0326 (10)	−0.0018 (7)	−0.0053 (7)	−0.0058 (7)
C17	0.0230 (8)	0.0306 (9)	0.0374 (10)	−0.0033 (7)	−0.0048 (7)	−0.0080 (8)
C18	0.0253 (9)	0.0322 (9)	0.0359 (10)	−0.0033 (7)	−0.0033 (8)	−0.0067 (8)
C19	0.0295 (9)	0.0320 (10)	0.0396 (11)	−0.0032 (8)	−0.0058 (8)	−0.0089 (8)
C20	0.0332 (10)	0.0318 (10)	0.0406 (11)	0.0006 (8)	−0.0052 (8)	−0.0088 (8)
C21	0.0350 (10)	0.0321 (10)	0.0440 (12)	−0.0017 (8)	−0.0041 (9)	−0.0113 (8)
C22	0.0505 (13)	0.0366 (11)	0.0476 (13)	0.0079 (10)	−0.0053 (10)	−0.0095 (9)
C23	0.033 (4)	0.0350 (13)	0.0547 (15)	0.0018 (17)	0.001 (2)	−0.0088 (11)
C24	0.064 (2)	0.0489 (19)	0.061 (2)	0.0064 (17)	−0.0022 (17)	−0.0126 (16)
C23A	0.033 (4)	0.0350 (13)	0.0547 (15)	0.0018 (17)	0.001 (2)	−0.0088 (11)
C24A	0.064 (2)	0.0489 (19)	0.061 (2)	0.0064 (17)	−0.0022 (17)	−0.0126 (16)

Geometric parameters (Å, º)

Cl1—C11	1.744 (2)	C16—H16B	0.97 (2)
Cl2—C13	1.733 (2)	C17—C18	1.528 (2)
S1—C8	1.7578 (18)	C17—H17A	0.98 (2)
S1—C1	1.7589 (18)	C17—H17B	0.98 (2)
O1—C7	1.228 (2)	C18—C19	1.521 (3)
N1—C7	1.368 (2)	C18—H18A	0.96 (2)
N1—C6	1.420 (2)	C18—H18B	0.95 (2)
N1—C16	1.479 (2)	C19—C20	1.519 (3)
C1—C2	1.393 (3)	C19—H19A	0.95 (2)
C1—C6	1.398 (2)	C19—H19B	0.97 (3)
C2—C3	1.379 (3)	C20—C21	1.522 (3)
C2—H2	0.96 (2)	C20—H20A	1.00 (2)
C3—C4	1.382 (3)	C20—H20B	1.04 (2)
C3—H3	0.96 (3)	C21—C22	1.515 (3)
C4—C5	1.388 (3)	C21—H21A	0.97 (3)
C4—H4	0.99 (3)	C21—H21B	0.96 (3)
C5—C6	1.392 (3)	C22—C23	1.537 (4)
C5—H5	0.96 (2)	C22—C23A	1.537 (4)
C7—C8	1.497 (2)	C22—H22A	0.9900
C8—C9	1.334 (3)	C22—H22B	0.9900
C9—C10	1.471 (3)	C23—C24	1.530 (7)
C9—H9	1.02 (3)	C23—H23A	0.9900
C10—C11	1.396 (3)	C23—H23B	0.9900
C10—C15	1.397 (3)	C24—H24A	0.9800
C11—C12	1.381 (3)	C24—H24B	0.9800
C12—C13	1.388 (3)	C24—H24C	0.9800
C12—H12	0.99 (3)	C23A—C24A	1.530 (8)
C13—C14	1.376 (3)	C23A—H23C	0.9900
C14—C15	1.385 (3)	C23A—H23D	0.9900
C14—H14	0.97 (3)	C24A—H24D	0.9800
C15—H15	0.96 (3)	C24A—H24E	0.9800
C16—C17	1.525 (3)	C24A—H24F	0.9800
C16—H16A	0.99 (2)
Cl1···C5^i	3.634 (2)	C21···H24B	2.86
Cl1···C12^ii	3.548 (2)	C24···H21B	2.91
Cl1···H9	2.82 (3)	C24A···H24E^viii	2.44
Cl1···H5^i	2.86 (2)	C24A···H24F^viii	2.70
Cl1···H12^ii	2.92 (3)	C24A···H24D^viii	1.94
Cl2···H20A^iii	3.13 (2)	H3···H17A^ix	2.42 (4)
Cl2···H24C^i	3.01	H5···H17B	2.21 (4)
S1···N1	3.0439 (16)	H5···H16B	2.33 (3)
S1···C15	3.236 (2)	H12···H22A^iii	2.37
S1···H15	2.84 (3)	H16A···H18A	2.47 (3)
S1···H2^iv	3.15 (3)	H16B···H24D^vii	2.54
O1···C3^v	3.268 (2)	H16B···H18B	2.46 (3)
O1···C17	3.238 (2)	H16B···H24A^vii	2.49
O1···C15^vi	3.270 (2)	H17A···H19A	2.59 (3)
O1···H3^v	2.51 (3)	H17B···H19B	2.55 (4)
O1···H16A	2.43 (2)	H18B···H20B	2.55 (3)
O1···H17A	2.75 (2)	H19A···H21A	2.58 (4)
O1···H9	2.49 (3)	H19B···H21B	2.51 (4)
O1···H15^vi	2.36 (3)	H20A···H22A	2.49
C5···C17	3.430 (3)	H20B···H22B	2.54
C5···C24^vii	3.58	H21A···H23B	2.55
C6···C24^vii	3.58	H21A···H23C	2.60
C24A···C24A^viii	2.48	H21B···H24B	2.32
C2···H19A^i	2.98 (2)	H21B···H23D	2.34
C5···H24A^vii	2.99	H22B···H24C	2.27
C5···H16B	2.64 (2)	H22B···H24E	2.43
C5···H17B	2.93 (3)	H24D···C24A^viii	1.94
C7···H15^vi	2.95 (3)	H24D···H24D^viii	1.82
C7···H17A	2.99 (2)	H24D···H24E^viii	1.70
C16···H5	2.62 (3)	H24D···H24F^viii	2.07
C17···H3^v	2.98 (3)	H24E···H24F^viii	2.54
C17···H5	2.82 (3)
C8—S1—C1	97.27 (8)	C16—C17—H17B	109.2 (13)
C7—N1—C6	123.67 (14)	C18—C17—H17B	110.8 (12)
C7—N1—C16	117.19 (14)	H17A—C17—H17B	106.0 (18)
C6—N1—C16	119.07 (15)	C19—C18—C17	113.07 (16)
C2—C1—C6	120.22 (17)	C19—C18—H18A	112.5 (13)
C2—C1—S1	119.25 (13)	C17—C18—H18A	109.3 (13)
C6—C1—S1	120.52 (13)	C19—C18—H18B	111.2 (14)
C3—C2—C1	120.53 (17)	C17—C18—H18B	108.8 (14)
C3—C2—H2	122.3 (14)	H18A—C18—H18B	101.4 (19)
C1—C2—H2	117.1 (14)	C20—C19—C18	113.91 (17)
C2—C3—C4	119.53 (18)	C20—C19—H19A	110.8 (14)
C2—C3—H3	118.7 (16)	C18—C19—H19A	108.3 (14)
C4—C3—H3	121.7 (16)	C20—C19—H19B	107.2 (14)
C3—C4—C5	120.51 (19)	C18—C19—H19B	108.7 (15)
C3—C4—H4	120.8 (16)	H19A—C19—H19B	107.7 (19)
C5—C4—H4	118.7 (16)	C19—C20—C21	113.55 (18)
C4—C5—C6	120.58 (17)	C19—C20—H20A	108.8 (13)
C4—C5—H5	118.4 (14)	C21—C20—H20A	109.2 (13)
C6—C5—H5	121.0 (14)	C19—C20—H20B	109.1 (13)
C5—C6—C1	118.59 (16)	C21—C20—H20B	107.1 (13)
C5—C6—N1	120.19 (15)	H20A—C20—H20B	109.1 (19)
C1—C6—N1	121.22 (16)	C22—C21—C20	113.53 (18)
O1—C7—N1	121.48 (16)	C22—C21—H21A	108.6 (17)
O1—C7—C8	121.01 (16)	C20—C21—H21A	107.9 (17)
N1—C7—C8	117.51 (15)	C22—C21—H21B	108.5 (14)
C9—C8—C7	118.51 (17)	C20—C21—H21B	109.6 (14)
C9—C8—S1	125.47 (14)	H21A—C21—H21B	109 (2)
C7—C8—S1	115.89 (13)	C21—C22—C23	117.2 (4)
C8—C9—C10	126.86 (18)	C21—C22—C23A	109.3 (4)
C8—C9—H9	114.5 (15)	C21—C22—H22A	108.0
C10—C9—H9	118.6 (15)	C23—C22—H22A	108.0
C11—C10—C15	116.75 (18)	C21—C22—H22B	108.0
C11—C10—C9	120.39 (18)	C23—C22—H22B	108.0
C15—C10—C9	122.85 (18)	H22A—C22—H22B	107.2
C12—C11—C10	122.93 (19)	C24—C23—C22	105.7 (4)
C12—C11—Cl1	117.26 (16)	C24—C23—H23A	110.6
C10—C11—Cl1	119.80 (15)	C22—C23—H23A	110.6
C11—C12—C13	117.9 (2)	C24—C23—H23B	110.6
C11—C12—H12	121.9 (16)	C22—C23—H23B	110.6
C13—C12—H12	120.1 (16)	H23A—C23—H23B	108.7
C14—C13—C12	121.42 (19)	C23—C24—H24A	109.5
C14—C13—Cl2	120.33 (17)	C23—C24—H24B	109.5
C12—C13—Cl2	118.25 (17)	H24A—C24—H24B	109.5
C13—C14—C15	119.3 (2)	C23—C24—H24C	109.5
C13—C14—H14	119.4 (15)	H24A—C24—H24C	109.5
C15—C14—H14	121.3 (15)	H24B—C24—H24C	109.5
C14—C15—C10	121.63 (19)	C24A—C23A—C22	111.3 (6)
C14—C15—H15	116.3 (15)	C24A—C23A—H23C	109.4
C10—C15—H15	121.9 (15)	C22—C23A—H23C	109.4
N1—C16—C17	115.05 (15)	C24A—C23A—H23D	109.4
N1—C16—H16A	106.7 (13)	C22—C23A—H23D	109.4
C17—C16—H16A	109.8 (13)	H23C—C23A—H23D	108.0
N1—C16—H16B	108.8 (12)	C23A—C24A—H24D	109.5
C17—C16—H16B	110.0 (12)	C23A—C24A—H24E	109.5
H16A—C16—H16B	106.0 (18)	H24D—C24A—H24E	109.5
C16—C17—C18	110.52 (16)	C23A—C24A—H24F	109.5
C16—C17—H17A	107.9 (13)	H24D—C24A—H24F	109.5
C18—C17—H17A	112.2 (13)	H24E—C24A—H24F	109.5
C8—S1—C1—C2	147.58 (16)	S1—C8—C9—C10	5.5 (3)
C8—S1—C1—C6	−31.51 (17)	C8—C9—C10—C11	133.9 (2)
C6—C1—C2—C3	0.2 (3)	C8—C9—C10—C15	−46.2 (3)
S1—C1—C2—C3	−178.87 (16)	C15—C10—C11—C12	−0.3 (3)
C1—C2—C3—C4	1.3 (3)	C9—C10—C11—C12	179.60 (19)
C2—C3—C4—C5	−1.1 (3)	C15—C10—C11—Cl1	178.39 (14)
C3—C4—C5—C6	−0.6 (4)	C9—C10—C11—Cl1	−1.7 (3)
C4—C5—C6—C1	2.1 (3)	C10—C11—C12—C13	−1.3 (3)
C4—C5—C6—N1	−177.04 (19)	Cl1—C11—C12—C13	179.99 (17)
C2—C1—C6—C5	−1.9 (3)	C11—C12—C13—C14	1.9 (3)
S1—C1—C6—C5	177.16 (15)	C11—C12—C13—Cl2	−177.07 (17)
C2—C1—C6—N1	177.25 (17)	C12—C13—C14—C15	−1.0 (3)
S1—C1—C6—N1	−3.7 (2)	Cl2—C13—C14—C15	178.02 (17)
C7—N1—C6—C5	−150.53 (19)	C13—C14—C15—C10	−0.7 (3)
C16—N1—C6—C5	26.4 (3)	C11—C10—C15—C14	1.3 (3)
C7—N1—C6—C1	30.3 (3)	C9—C10—C15—C14	−178.57 (19)
C16—N1—C6—C1	−152.76 (17)	C7—N1—C16—C17	82.7 (2)
C6—N1—C7—O1	172.26 (17)	C6—N1—C16—C17	−94.4 (2)
C16—N1—C7—O1	−4.7 (3)	N1—C16—C17—C18	−179.23 (15)
C6—N1—C7—C8	−8.3 (3)	C16—C17—C18—C19	−178.51 (17)
C16—N1—C7—C8	174.73 (16)	C17—C18—C19—C20	177.77 (17)
O1—C7—C8—C9	−32.8 (3)	C18—C19—C20—C21	−175.70 (18)
N1—C7—C8—C9	147.71 (18)	C19—C20—C21—C22	−178.7 (2)
O1—C7—C8—S1	143.15 (15)	C20—C21—C22—C23	176.0 (3)
N1—C7—C8—S1	−36.3 (2)	C20—C21—C22—C23A	−169.4 (5)
C1—S1—C8—C9	−133.86 (18)	C21—C22—C23—C24	78.1 (5)
C1—S1—C8—C7	50.47 (14)	C21—C22—C23A—C24A	175.2 (6)
C7—C8—C9—C10	−178.89 (17)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+2; (iii) x+1, y−1, z+1; (iv) −x+2, −y, −z+1; (v) x−1, y, z; (vi) −x+1, −y, −z+1; (vii) x+1, y−1, z; (viii) −x−1, −y+3, −z; (ix) x+1, y, z.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the ring A (C1–C6).

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^ix	0.96 (3)	2.51 (3)	3.268 (2)	136 (2)
C5—H5···Cl1^i	0.96 (2)	2.86 (2)	3.634 (2)	138.8 (17)
C15—H15···O1^vi	0.96 (3)	2.36 (3)	3.270 (2)	159 (2)
C17—H17A···Cg1^i	0.98 (2)	2.90 (2)	3.619 (2)	131.2 (17)

Symmetry codes: (i) −x+1, −y+1, −z+1; (vi) −x+1, −y, −z+1; (ix) x+1, y, z.