N-Ethyl-N′-(3-methyl­benzo­yl)-S,S-di­phenyl­sulfo­diimide

The asymmetric unit of the title sulfodi­imide, C₂₂H₂₂N₂OS, consists of two crystallographically independent mol­ecules with similar conformations The environment around each sulfur atom is a slightly distorted tetra­hedron with two S=N bonds and two S—C bonds. The S= N(m-methyl­benzo­yl) and S=N(NEt) bond lengths are 1.584 (3) and 1.528 (2) Å, respectively, for one mol­ecule, and 1.575 (2) and 1.529 (3) Å, respectively, for the other. The dihedral angles between the two phenyl rings in the mol­ecules are 86.76 (8) and 82.49 (8)°. The N—S—N—C(m-methyl­benzo­yl) and N—S—N—C(eth­yl) torsion angles are −60.5 (2) and −50.28 (19)°, respectively, for one mol­ecule, and 62.9 (2) and 44.2 (3)°, respectively, for the other. In the crystal, each independent mol­ecule is linked to its inversion-related mol­ecule via a pair of C—H...O hydrogen bonds, forming a dimer.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.151
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1       --C8       .        6.0 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1       --C8       .        5.5 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S2       --N4       .        5.6 s.u.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00462 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.026 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600        123 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ......     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         14 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

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

   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

N-[(Ethylimino)diphenyl-λ⁶-sulfanylidene]-3-methylbenzamide

Crystal data

C22H22N2OS	Z = 4
Mr = 362.49	F(000) = 768.00
Triclinic, P1	Dx = 1.252 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 11.0780 (2) Å	Cell parameters from 17291 reflections
b = 13.2775 (3) Å	θ = 3.3–68.4°
c = 13.3258 (3) Å	µ = 1.58 mm^−1
α = 91.717 (1)°	T = 173 K
β = 100.9442 (10)°	Platelet, colorless
γ = 90.9017 (10)°	0.46 × 0.27 × 0.17 mm
V = 1923.08 (6) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	4159 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.099
ω scans	θmax = 68.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.436, Tmax = 0.770	k = −15→15
22182 measured reflections	l = −16→16
6901 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.151	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0704P)^2] where P = (Fo^2 + 2Fc^2)/3
6901 reflections	(Δ/σ)max < 0.001
473 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
S1	0.05317 (6)	0.61479 (5)	0.25436 (5)	0.0437 (2)
S2	0.33971 (6)	0.11964 (5)	0.24369 (5)	0.0437 (2)
O1	0.23346 (16)	0.48853 (14)	0.36079 (15)	0.0633 (6)
O2	0.20456 (16)	−0.01130 (14)	0.34751 (16)	0.0650 (6)
N1	0.19221 (19)	0.61318 (16)	0.24099 (16)	0.0475 (6)
N2	−0.03602 (18)	0.52441 (15)	0.23212 (16)	0.0493 (6)
N3	0.19529 (18)	0.11556 (15)	0.23012 (15)	0.0434 (6)
N4	0.41579 (19)	0.03189 (16)	0.21521 (16)	0.0509 (6)
C1	0.3969 (3)	0.54786 (19)	0.28407 (19)	0.0428 (7)
C2	0.4785 (3)	0.4807 (2)	0.3372 (2)	0.0473 (7)
C3	0.6002 (3)	0.4774 (2)	0.3254 (2)	0.0494 (7)
C4	0.6399 (3)	0.5449 (2)	0.2601 (2)	0.0511 (8)
C5	0.5604 (3)	0.6128 (2)	0.2073 (2)	0.0505 (8)
C6	0.4386 (3)	0.61333 (19)	0.21783 (19)	0.0447 (7)
C7	0.6861 (3)	0.4019 (3)	0.3822 (3)	0.0671 (9)
C8	0.2661 (3)	0.5456 (2)	0.2999 (2)	0.0481 (7)
C9	0.0020 (3)	0.71746 (19)	0.17606 (18)	0.0422 (7)
C10	0.0785 (3)	0.77799 (19)	0.1321 (2)	0.0516 (8)
C11	0.0294 (3)	0.8534 (3)	0.0691 (3)	0.0599 (9)
C12	−0.0948 (3)	0.8698 (2)	0.0508 (2)	0.0580 (8)
C13	−0.1718 (3)	0.8105 (2)	0.0952 (3)	0.0575 (8)
C14	−0.1240 (3)	0.7346 (2)	0.1581 (2)	0.0519 (8)
C15	0.0389 (3)	0.65915 (18)	0.37817 (19)	0.0414 (7)
C16	−0.0374 (3)	0.6097 (2)	0.4320 (2)	0.0491 (7)
C17	−0.0476 (3)	0.6478 (3)	0.5276 (2)	0.0583 (8)
C18	0.0186 (3)	0.7323 (3)	0.5676 (3)	0.0623 (9)
C19	0.0957 (3)	0.7809 (2)	0.5137 (3)	0.0603 (8)
C20	0.1065 (3)	0.7447 (2)	0.4187 (2)	0.0516 (8)
C21	−0.0438 (3)	0.4717 (3)	0.1319 (3)	0.0648 (9)
C22	−0.1434 (4)	0.3937 (3)	0.1150 (3)	0.0992 (13)
C23	0.0078 (3)	0.04398 (19)	0.26800 (19)	0.0415 (7)
C24	−0.0516 (3)	−0.02016 (19)	0.3237 (2)	0.0476 (7)
C25	−0.1792 (3)	−0.0255 (2)	0.3110 (3)	0.0520 (8)
C26	−0.2467 (3)	0.0374 (2)	0.2409 (3)	0.0551 (8)
C27	−0.1889 (3)	0.1027 (2)	0.1847 (2)	0.0554 (8)
C28	−0.0613 (3)	0.10573 (19)	0.19778 (19)	0.0466 (7)
C29	−0.2404 (3)	−0.0967 (3)	0.3727 (3)	0.0743 (10)
C30	0.1458 (3)	0.0460 (2)	0.2862 (2)	0.0464 (7)
C31	0.3579 (3)	0.22967 (19)	0.17269 (18)	0.0424 (7)
C32	0.4696 (3)	0.2423 (2)	0.1429 (2)	0.0575 (8)
C33	0.4901 (3)	0.3245 (3)	0.0867 (3)	0.0638 (9)
C34	0.3985 (3)	0.3937 (3)	0.0621 (2)	0.0575 (8)
C35	0.2879 (3)	0.3818 (2)	0.0925 (2)	0.0543 (8)
C36	0.2668 (3)	0.2995 (2)	0.14851 (19)	0.0495 (7)
C37	0.4115 (3)	0.15642 (19)	0.36964 (19)	0.0418 (7)
C38	0.5126 (3)	0.1052 (2)	0.4187 (2)	0.0504 (7)
C39	0.5688 (3)	0.1355 (3)	0.5173 (3)	0.0567 (8)
C40	0.5238 (3)	0.2155 (3)	0.5649 (3)	0.0590 (9)
C41	0.4221 (3)	0.2665 (2)	0.5160 (2)	0.0577 (8)
C42	0.3656 (3)	0.2374 (2)	0.4175 (2)	0.0501 (7)
C43	0.3710 (3)	−0.0217 (3)	0.1178 (3)	0.0690 (9)
C44	0.4426 (4)	−0.1135 (3)	0.1098 (3)	0.0883 (12)
H1	0.4503	0.4361	0.3826	0.0568*
H2	0.7231	0.5444	0.2517	0.0613*
H3	0.5895	0.6590	0.1638	0.0606*
H4	0.3833	0.6584	0.1798	0.0537*
H5	0.7504	0.3859	0.3433	0.0805*
H6	0.6396	0.3403	0.3905	0.0805*
H7	0.7239	0.4306	0.4497	0.0805*
H8	0.1647	0.7677	0.1452	0.0620*
H9	0.0820	0.8944	0.0379	0.0719*
H10	−0.1277	0.9222	0.0074	0.0697*
H11	−0.2577	0.8219	0.0825	0.0690*
H12	−0.1769	0.6938	0.1891	0.0622*
H13	−0.0821	0.5505	0.4039	0.0589*
H14	−0.1006	0.6153	0.5655	0.0700*
H15	0.0114	0.7580	0.6334	0.0748*
H16	0.1414	0.8394	0.5426	0.0723*
H17	0.1593	0.7776	0.3810	0.0619*
H18	0.0356	0.4397	0.1290	0.0777*
H19	−0.0598	0.5210	0.0769	0.0777*
H20	−0.1292	0.3463	0.1709	0.1190*
H21	−0.1440	0.3572	0.0499	0.1190*
H22	−0.2227	0.4260	0.1132	0.1190*
H23	−0.0039	−0.0618	0.3721	0.0571*
H24	−0.3339	0.0357	0.2312	0.0662*
H25	−0.2365	0.1453	0.1373	0.0665*
H26	−0.0216	0.1499	0.1588	0.0559*
H27	−0.1934	−0.1587	0.3825	0.0892*
H28	−0.3242	−0.1129	0.3363	0.0892*
H29	−0.2433	−0.0648	0.4395	0.0892*
H30	0.5323	0.1945	0.1609	0.0690*
H31	0.5665	0.3333	0.0652	0.0766*
H32	0.4123	0.4504	0.0236	0.0690*
H33	0.2256	0.4300	0.0750	0.0652*
H34	0.1905	0.2912	0.1702	0.0594*
H35	0.5431	0.0497	0.3852	0.0605*
H36	0.6382	0.1008	0.5516	0.0680*
H37	0.5628	0.2363	0.6323	0.0708*
H38	0.3913	0.3215	0.5501	0.0693*
H39	0.2964	0.2723	0.3832	0.0601*
H40	0.3784	0.0228	0.0609	0.0828*
H41	0.2831	−0.0404	0.1123	0.0828*
H42	0.5293	−0.0947	0.1135	0.1059*
H43	0.4109	−0.1492	0.0444	0.1059*
H44	0.4351	−0.1575	0.1661	0.1059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0368 (4)	0.0468 (5)	0.0487 (4)	0.0005 (4)	0.0104 (3)	0.0066 (3)
S2	0.0351 (4)	0.0450 (5)	0.0502 (4)	−0.0014 (4)	0.0059 (3)	0.0022 (3)
O1	0.0473 (12)	0.0719 (14)	0.0776 (14)	0.0055 (11)	0.0248 (11)	0.0311 (12)
O2	0.0406 (13)	0.0670 (14)	0.0849 (15)	−0.0002 (11)	0.0018 (11)	0.0298 (12)
N1	0.0337 (13)	0.0506 (15)	0.0601 (15)	0.0050 (11)	0.0124 (11)	0.0101 (12)
N2	0.0435 (14)	0.0503 (14)	0.0543 (14)	−0.0071 (12)	0.0104 (11)	0.0021 (12)
N3	0.0329 (12)	0.0484 (14)	0.0472 (13)	−0.0028 (11)	0.0029 (10)	0.0073 (11)
N4	0.0430 (14)	0.0478 (14)	0.0606 (15)	0.0072 (12)	0.0080 (11)	−0.0079 (12)
C1	0.0372 (16)	0.0416 (16)	0.0501 (16)	0.0009 (13)	0.0100 (13)	−0.0017 (13)
C2	0.0413 (17)	0.0468 (18)	0.0541 (17)	−0.0002 (14)	0.0088 (13)	0.0064 (14)
C3	0.0395 (17)	0.0508 (18)	0.0555 (18)	0.0010 (15)	0.0032 (14)	0.0020 (14)
C4	0.0345 (16)	0.060 (2)	0.0595 (19)	−0.0004 (15)	0.0108 (14)	−0.0010 (15)
C5	0.0459 (18)	0.0523 (19)	0.0552 (18)	−0.0005 (15)	0.0136 (14)	0.0083 (15)
C6	0.0395 (16)	0.0447 (17)	0.0503 (17)	0.0019 (14)	0.0089 (13)	0.0029 (13)
C7	0.0442 (19)	0.075 (3)	0.080 (3)	0.0084 (17)	0.0045 (16)	0.0207 (18)
C8	0.0434 (17)	0.0464 (18)	0.0567 (18)	0.0009 (15)	0.0150 (14)	−0.0009 (14)
C9	0.0386 (16)	0.0466 (17)	0.0407 (15)	0.0033 (14)	0.0046 (12)	0.0064 (12)
C10	0.0458 (17)	0.0529 (19)	0.0572 (18)	0.0003 (15)	0.0104 (14)	0.0137 (15)
C11	0.059 (2)	0.057 (2)	0.061 (2)	−0.0041 (17)	0.0020 (16)	0.0190 (16)
C12	0.071 (3)	0.0489 (19)	0.0479 (17)	0.0053 (17)	−0.0070 (16)	0.0093 (14)
C13	0.0493 (19)	0.055 (2)	0.066 (2)	0.0063 (16)	0.0028 (15)	0.0111 (16)
C14	0.0441 (18)	0.0521 (18)	0.0597 (18)	0.0032 (15)	0.0085 (14)	0.0141 (15)
C15	0.0362 (15)	0.0406 (16)	0.0469 (16)	0.0051 (13)	0.0061 (12)	0.0041 (12)
C16	0.0492 (18)	0.0465 (17)	0.0529 (17)	−0.0006 (14)	0.0118 (14)	0.0087 (14)
C17	0.063 (2)	0.063 (2)	0.0549 (19)	0.0086 (17)	0.0235 (16)	0.0096 (16)
C18	0.079 (3)	0.058 (2)	0.0496 (18)	0.0191 (19)	0.0106 (17)	0.0015 (16)
C19	0.071 (3)	0.0470 (18)	0.0581 (19)	−0.0004 (16)	0.0003 (16)	−0.0026 (15)
C20	0.0476 (18)	0.0503 (18)	0.0556 (18)	−0.0015 (15)	0.0063 (14)	0.0066 (14)
C21	0.060 (2)	0.073 (3)	0.061 (2)	0.0001 (18)	0.0128 (16)	−0.0069 (17)
C22	0.100 (3)	0.094 (3)	0.106 (3)	−0.034 (3)	0.035 (3)	−0.044 (3)
C23	0.0391 (16)	0.0403 (16)	0.0441 (15)	−0.0012 (13)	0.0060 (12)	0.0008 (12)
C24	0.0432 (17)	0.0441 (17)	0.0553 (17)	0.0013 (14)	0.0084 (14)	0.0062 (14)
C25	0.0433 (18)	0.0495 (18)	0.0651 (19)	−0.0038 (15)	0.0152 (15)	0.0020 (15)
C26	0.0357 (17)	0.060 (2)	0.070 (2)	0.0021 (15)	0.0112 (15)	0.0031 (16)
C27	0.0390 (17)	0.063 (2)	0.0614 (19)	0.0046 (16)	0.0019 (14)	0.0091 (15)
C28	0.0402 (17)	0.0474 (17)	0.0516 (17)	0.0003 (14)	0.0072 (13)	0.0041 (13)
C29	0.055 (2)	0.076 (3)	0.098 (3)	−0.0025 (18)	0.0288 (18)	0.020 (2)
C30	0.0430 (17)	0.0460 (18)	0.0481 (17)	−0.0022 (15)	0.0037 (13)	0.0019 (14)
C31	0.0392 (16)	0.0481 (17)	0.0384 (14)	−0.0050 (14)	0.0036 (12)	0.0024 (12)
C32	0.0473 (18)	0.056 (2)	0.072 (2)	−0.0020 (16)	0.0183 (15)	0.0036 (16)
C33	0.057 (2)	0.064 (3)	0.075 (3)	−0.0103 (18)	0.0264 (17)	0.0026 (17)
C34	0.070 (3)	0.054 (2)	0.0514 (18)	−0.0129 (18)	0.0221 (16)	0.0007 (15)
C35	0.058 (2)	0.0527 (19)	0.0525 (18)	0.0007 (16)	0.0100 (15)	0.0089 (14)
C36	0.0432 (17)	0.0552 (19)	0.0505 (17)	0.0015 (15)	0.0093 (13)	0.0071 (14)
C37	0.0342 (15)	0.0418 (16)	0.0496 (16)	−0.0034 (13)	0.0083 (12)	0.0053 (13)
C38	0.0414 (17)	0.0487 (18)	0.0579 (18)	−0.0032 (15)	0.0018 (14)	0.0014 (14)
C39	0.0503 (19)	0.055 (2)	0.0588 (19)	−0.0025 (16)	−0.0042 (15)	0.0085 (16)
C40	0.070 (3)	0.054 (2)	0.0495 (18)	−0.0111 (18)	0.0039 (16)	0.0067 (16)
C41	0.075 (3)	0.0490 (19)	0.0515 (18)	−0.0055 (17)	0.0188 (16)	−0.0025 (15)
C42	0.0478 (18)	0.0502 (18)	0.0538 (18)	0.0025 (15)	0.0128 (14)	0.0039 (14)
C43	0.069 (3)	0.067 (3)	0.069 (3)	−0.0003 (19)	0.0100 (17)	−0.0142 (17)
C44	0.101 (3)	0.064 (3)	0.094 (3)	0.017 (3)	0.006 (3)	−0.024 (2)

Geometric parameters (Å, º)

S1—N1	1.584 (3)	C37—C42	1.386 (4)
S1—N2	1.528 (2)	C38—C39	1.387 (4)
S1—C9	1.776 (3)	C39—C40	1.370 (5)
S1—C15	1.771 (3)	C40—C41	1.388 (5)
S2—N3	1.575 (2)	C41—C42	1.384 (4)
S2—N4	1.529 (3)	C43—C44	1.476 (5)
S2—C31	1.793 (3)	C2—H1	0.950
S2—C37	1.766 (3)	C4—H2	0.950
O1—C8	1.226 (4)	C5—H3	0.950
O2—C30	1.234 (4)	C6—H4	0.950
N1—C8	1.383 (4)	C7—H5	0.980
N2—C21	1.477 (4)	C7—H6	0.980
N3—C30	1.376 (4)	C7—H7	0.980
N4—C43	1.458 (4)	C10—H8	0.950
C1—C2	1.391 (4)	C11—H9	0.950
C1—C6	1.391 (4)	C12—H10	0.950
C1—C8	1.504 (4)	C13—H11	0.950
C2—C3	1.387 (4)	C14—H12	0.950
C3—C4	1.391 (4)	C16—H13	0.950
C3—C7	1.512 (4)	C17—H14	0.950
C4—C5	1.382 (4)	C18—H15	0.950
C5—C6	1.383 (4)	C19—H16	0.950
C9—C10	1.379 (4)	C20—H17	0.950
C9—C14	1.394 (4)	C21—H18	0.990
C10—C11	1.378 (4)	C21—H19	0.990
C11—C12	1.373 (5)	C22—H20	0.980
C12—C13	1.377 (5)	C22—H21	0.980
C13—C14	1.378 (4)	C22—H22	0.980
C15—C16	1.379 (4)	C24—H23	0.950
C15—C20	1.387 (4)	C26—H24	0.950
C16—C17	1.381 (4)	C27—H25	0.950
C17—C18	1.369 (4)	C28—H26	0.950
C18—C19	1.380 (5)	C29—H27	0.980
C19—C20	1.368 (5)	C29—H28	0.980
C21—C22	1.482 (5)	C29—H29	0.980
C23—C24	1.384 (4)	C32—H30	0.950
C23—C28	1.388 (4)	C33—H31	0.950
C23—C30	1.501 (4)	C34—H32	0.950
C24—C25	1.391 (4)	C35—H33	0.950
C25—C26	1.389 (4)	C36—H34	0.950
C25—C29	1.506 (5)	C38—H35	0.950
C26—C27	1.387 (5)	C39—H36	0.950
C27—C28	1.391 (4)	C40—H37	0.950
C31—C32	1.379 (5)	C41—H38	0.950
C31—C36	1.380 (4)	C42—H39	0.950
C32—C33	1.383 (5)	C43—H40	0.990
C33—C34	1.380 (5)	C43—H41	0.990
C34—C35	1.369 (5)	C44—H42	0.980
C35—C36	1.383 (4)	C44—H43	0.980
C37—C38	1.384 (4)	C44—H44	0.980
N1—S1—N2	124.42 (12)	C5—C6—H4	119.968
N1—S1—C9	99.34 (13)	C3—C7—H5	109.471
N1—S1—C15	111.93 (12)	C3—C7—H6	109.464
N2—S1—C9	111.85 (12)	C3—C7—H7	109.468
N2—S1—C15	104.30 (13)	H5—C7—H6	109.476
C9—S1—C15	103.29 (12)	H5—C7—H7	109.473
N3—S2—N4	123.76 (12)	H6—C7—H7	109.476
N3—S2—C31	99.52 (12)	C9—C10—H8	120.147
N3—S2—C37	112.11 (12)	C11—C10—H8	120.146
N4—S2—C31	112.28 (13)	C10—C11—H9	119.703
N4—S2—C37	104.46 (12)	C12—C11—H9	119.707
C31—S2—C37	103.05 (12)	C11—C12—H10	119.929
S1—N1—C8	115.9 (2)	C13—C12—H10	119.927
S1—N2—C21	116.3 (2)	C12—C13—H11	120.065
S2—N3—C30	116.68 (17)	C14—C13—H11	120.058
S2—N4—C43	117.30 (18)	C9—C14—H12	120.002
C2—C1—C6	119.1 (3)	C13—C14—H12	120.010
C2—C1—C8	118.2 (3)	C15—C16—H13	120.622
C6—C1—C8	122.7 (3)	C17—C16—H13	120.632
C1—C2—C3	121.5 (3)	C16—C17—H14	120.016
C2—C3—C4	118.2 (3)	C18—C17—H14	120.021
C2—C3—C7	120.4 (3)	C17—C18—H15	119.515
C4—C3—C7	121.5 (3)	C19—C18—H15	119.521
C3—C4—C5	121.2 (3)	C18—C19—H16	120.020
C4—C5—C6	120.0 (3)	C20—C19—H16	120.030
C1—C6—C5	120.1 (3)	C15—C20—H17	120.536
O1—C8—N1	125.9 (3)	C19—C20—H17	120.541
O1—C8—C1	120.8 (3)	N2—C21—H18	109.481
N1—C8—C1	113.3 (3)	N2—C21—H19	109.485
S1—C9—C10	124.0 (2)	C22—C21—H18	109.482
S1—C9—C14	116.3 (2)	C22—C21—H19	109.486
C10—C9—C14	119.7 (3)	H18—C21—H19	108.061
C9—C10—C11	119.7 (3)	C21—C22—H20	109.477
C10—C11—C12	120.6 (3)	C21—C22—H21	109.473
C11—C12—C13	120.1 (3)	C21—C22—H22	109.473
C12—C13—C14	119.9 (3)	H20—C22—H21	109.466
C9—C14—C13	120.0 (3)	H20—C22—H22	109.468
S1—C15—C16	120.58 (19)	H21—C22—H22	109.471
S1—C15—C20	118.0 (2)	C23—C24—H23	119.002
C16—C15—C20	121.4 (3)	C25—C24—H23	119.002
C15—C16—C17	118.7 (3)	C25—C26—H24	119.443
C16—C17—C18	120.0 (3)	C27—C26—H24	119.445
C17—C18—C19	121.0 (3)	C26—C27—H25	119.967
C18—C19—C20	120.0 (3)	C28—C27—H25	119.963
C15—C20—C19	118.9 (3)	C23—C28—H26	120.158
N2—C21—C22	110.8 (3)	C27—C28—H26	120.160
C24—C23—C28	119.3 (3)	C25—C29—H27	109.470
C24—C23—C30	119.0 (3)	C25—C29—H28	109.465
C28—C23—C30	121.6 (3)	C25—C29—H29	109.464
C23—C24—C25	122.0 (3)	H27—C29—H28	109.481
C24—C25—C26	117.8 (3)	H27—C29—H29	109.477
C24—C25—C29	120.3 (3)	H28—C29—H29	109.472
C26—C25—C29	121.8 (3)	C31—C32—H30	120.054
C25—C26—C27	121.1 (3)	C33—C32—H30	120.045
C26—C27—C28	120.1 (3)	C32—C33—H31	120.370
C23—C28—C27	119.7 (3)	C34—C33—H31	120.363
O2—C30—N3	125.7 (3)	C33—C34—H32	119.564
O2—C30—C23	120.1 (3)	C35—C34—H32	119.555
N3—C30—C23	114.2 (3)	C34—C35—H33	119.978
S2—C31—C32	116.4 (2)	C36—C35—H33	119.972
S2—C31—C36	123.0 (3)	C31—C36—H34	120.341
C32—C31—C36	120.6 (3)	C35—C36—H34	120.338
C31—C32—C33	119.9 (3)	C37—C38—H35	120.260
C32—C33—C34	119.3 (3)	C39—C38—H35	120.266
C33—C34—C35	120.9 (3)	C38—C39—H36	120.115
C34—C35—C36	120.0 (3)	C40—C39—H36	120.121
C31—C36—C35	119.3 (3)	C39—C40—H37	119.601
S2—C37—C38	120.1 (2)	C41—C40—H37	119.611
S2—C37—C42	118.89 (19)	C40—C41—H38	120.000
C38—C37—C42	121.0 (3)	C42—C41—H38	120.006
C37—C38—C39	119.5 (3)	C37—C42—H39	120.527
C38—C39—C40	119.8 (3)	C41—C42—H39	120.529
C39—C40—C41	120.8 (3)	N4—C43—H40	109.587
C40—C41—C42	120.0 (3)	N4—C43—H41	109.584
C37—C42—C41	118.9 (3)	C44—C43—H40	109.585
N4—C43—C44	110.3 (3)	C44—C43—H41	109.593
C1—C2—H1	119.237	H40—C43—H41	108.124
C3—C2—H1	119.239	C43—C44—H42	109.477
C3—C4—H2	119.421	C43—C44—H43	109.462
C5—C4—H2	119.429	C43—C44—H44	109.467
C4—C5—H3	120.008	H42—C44—H43	109.471
C6—C5—H3	120.017	H42—C44—H44	109.475
C1—C6—H4	119.971	H43—C44—H44	109.475
N1—S1—N2—C21	−50.28 (19)	C1—C2—C3—C7	−178.5 (2)
N2—S1—N1—C8	−60.5 (2)	C2—C3—C4—C5	−0.7 (4)
N1—S1—C9—C10	−6.6 (2)	C7—C3—C4—C5	179.1 (3)
N1—S1—C9—C14	172.15 (16)	C3—C4—C5—C6	−0.9 (4)
C9—S1—N1—C8	174.73 (15)	C4—C5—C6—C1	2.1 (4)
N1—S1—C15—C16	−134.65 (17)	S1—C9—C10—C11	177.38 (16)
N1—S1—C15—C20	45.4 (2)	S1—C9—C14—C13	−177.73 (16)
C15—S1—N1—C8	66.22 (18)	C10—C9—C14—C13	1.1 (4)
N2—S1—C9—C10	−139.73 (18)	C14—C9—C10—C11	−1.4 (4)
N2—S1—C9—C14	39.1 (2)	C9—C10—C11—C12	1.0 (4)
C9—S1—N2—C21	68.84 (17)	C10—C11—C12—C13	−0.3 (4)
N2—S1—C15—C16	2.3 (2)	C11—C12—C13—C14	0.0 (4)
N2—S1—C15—C20	−177.61 (16)	C12—C13—C14—C9	−0.4 (4)
C15—S1—N2—C21	179.80 (13)	S1—C15—C16—C17	−178.83 (15)
C9—S1—C15—C16	119.40 (18)	S1—C15—C20—C19	179.27 (16)
C9—S1—C15—C20	−60.56 (19)	C16—C15—C20—C19	−0.7 (4)
C15—S1—C9—C10	108.68 (19)	C20—C15—C16—C17	1.1 (4)
C15—S1—C9—C14	−72.53 (18)	C15—C16—C17—C18	−0.9 (4)
N3—S2—N4—C43	44.2 (3)	C16—C17—C18—C19	0.2 (5)
N4—S2—N3—C30	62.9 (2)	C17—C18—C19—C20	0.2 (5)
N3—S2—C31—C32	−162.49 (16)	C18—C19—C20—C15	0.0 (4)
N3—S2—C31—C36	17.8 (2)	C24—C23—C28—C27	0.3 (4)
C31—S2—N3—C30	−172.07 (14)	C28—C23—C24—C25	0.6 (4)
N3—S2—C37—C38	135.29 (18)	C24—C23—C30—O2	2.5 (4)
N3—S2—C37—C42	−45.2 (3)	C24—C23—C30—N3	−177.3 (2)
C37—S2—N3—C30	−63.70 (18)	C30—C23—C24—C25	179.7 (2)
N4—S2—C31—C32	−29.83 (19)	C28—C23—C30—O2	−178.4 (3)
N4—S2—C31—C36	150.48 (16)	C28—C23—C30—N3	1.8 (4)
C31—S2—N4—C43	−75.06 (18)	C30—C23—C28—C27	−178.8 (2)
N4—S2—C37—C38	−1.1 (3)	C23—C24—C25—C26	−1.0 (4)
N4—S2—C37—C42	178.40 (18)	C23—C24—C25—C29	179.7 (3)
C37—S2—N4—C43	173.98 (16)	C24—C25—C26—C27	0.6 (4)
C31—S2—C37—C38	−118.6 (2)	C29—C25—C26—C27	179.9 (3)
C31—S2—C37—C42	60.9 (2)	C25—C26—C27—C28	0.2 (4)
C37—S2—C31—C32	82.01 (18)	C26—C27—C28—C23	−0.7 (4)
C37—S2—C31—C36	−97.68 (19)	S2—C31—C32—C33	179.12 (16)
S1—N1—C8—O1	−0.5 (4)	S2—C31—C36—C35	−179.28 (15)
S1—N1—C8—C1	−179.82 (14)	C32—C31—C36—C35	1.0 (4)
S1—N2—C21—C22	−173.34 (15)	C36—C31—C32—C33	−1.2 (4)
S2—N3—C30—O2	1.8 (4)	C31—C32—C33—C34	0.7 (4)
S2—N3—C30—C23	−178.52 (14)	C32—C33—C34—C35	−0.1 (4)
S2—N4—C43—C44	−170.70 (17)	C33—C34—C35—C36	0.0 (4)
C2—C1—C6—C5	−1.5 (4)	C34—C35—C36—C31	−0.4 (4)
C6—C1—C2—C3	−0.2 (4)	S2—C37—C38—C39	179.39 (17)
C2—C1—C8—O1	2.5 (4)	S2—C37—C42—C41	−179.71 (17)
C2—C1—C8—N1	−178.1 (2)	C38—C37—C42—C41	−0.2 (4)
C8—C1—C2—C3	179.1 (2)	C42—C37—C38—C39	−0.1 (4)
C6—C1—C8—O1	−178.2 (3)	C37—C38—C39—C40	0.0 (5)
C6—C1—C8—N1	1.2 (4)	C38—C39—C40—C41	0.3 (5)
C8—C1—C6—C5	179.2 (2)	C39—C40—C41—C42	−0.7 (5)
C1—C2—C3—C4	1.3 (4)	C40—C41—C42—C37	0.6 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H14···O1^i	0.95	2.37	3.307 (4)	170
C39—H36···O2^ii	0.95	2.35	3.296 (4)	173

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