4-Acet­amidobenzene­sulfonyl azide

The title compound, C₈H₈N₄O₃S, is planar chiral in the solid state. It crystallizes with three independent mol­ecules in the asymmetric unit, two of which have the same chirality and the third is the opposite enanti­omer. Partial inversion twinning is present in the crystal which was examined. All three mol­ecules are connected via hydrogen bonds between the amide groups, forming a helix around the b axis of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.099
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.330
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.33
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.81
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2A    -   N3A     ..       5.71 su
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3C    ..  C6A     ..       3.01 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.28
           From the CIF: _reflns_number_total               7326
           Count of symmetry unique reflns         3903
           Completeness (_total/calc)            187.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3423
           Fraction of Friedel pairs measured     0.877
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-(Acetylamino)benzenesulfonyl azide

Crystal data

C8H8N4O3S	F(000) = 744
Mr = 240.24	Dx = 1.559 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6077 reflections
a = 8.0529 (5) Å	θ = 2.6–30.5°
b = 22.988 (1) Å	µ = 0.31 mm^−1
c = 8.3123 (5) Å	T = 100 K
β = 93.534 (1)°	Block, colourless
V = 1535.85 (15) Å^3	0.53 × 0.45 × 0.40 mm
Z = 6

Data collection

Bruker SMART APEX CCD diffractometer	7326 independent reflections
Radiation source: fine-focus sealed tube	7096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 2003)	h = −10→10
Tmin = 0.810, Tmax = 0.882	k = −30→30
14335 measured reflections	l = −11→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0655P)^2 + 0.1628P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
7326 reflections	Δρmax = 0.65 e Å^−3
437 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983), 3450 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.33 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	Uiso*/Ueq
C1A	0.3370 (3)	0.31132 (8)	0.5921 (2)	0.0224 (4)
C2A	0.5081 (3)	0.31502 (10)	0.6216 (2)	0.0263 (4)
H2A	0.5546	0.3210	0.7281	0.032*
C3A	0.6107 (3)	0.30992 (9)	0.4949 (2)	0.0255 (4)
H3A	0.7281	0.3120	0.5137	0.031*
C4A	0.5397 (3)	0.30171 (8)	0.3389 (2)	0.0235 (4)
C5A	0.3682 (3)	0.29655 (9)	0.3112 (2)	0.0269 (4)
H5A	0.3214	0.2896	0.2052	0.032*
C6A	0.2655 (3)	0.30150 (9)	0.4384 (2)	0.0242 (4)
H6A	0.1483	0.2982	0.4206	0.029*
C7A	0.7833 (3)	0.32513 (10)	0.1856 (3)	0.0294 (4)
C8A	0.8579 (3)	0.31486 (12)	0.0270 (3)	0.0357 (5)
H8A	0.8401	0.3492	−0.0417	0.054*
H8B	0.8048	0.2810	−0.0261	0.054*
H8C	0.9775	0.3077	0.0453	0.054*
C1B	0.3907 (2)	0.48812 (9)	0.0297 (2)	0.0245 (4)
C2B	0.3381 (3)	0.43565 (9)	0.0934 (3)	0.0270 (4)
H2B	0.4003	0.4010	0.0807	0.032*
C3B	0.1943 (3)	0.43488 (9)	0.1750 (3)	0.0278 (4)
H3B	0.1571	0.3993	0.2187	0.033*
C4B	0.1024 (2)	0.48576 (9)	0.1942 (2)	0.0237 (4)
C5B	0.1593 (3)	0.53834 (9)	0.1359 (3)	0.0290 (4)
H5B	0.1006	0.5734	0.1534	0.035*
C6B	0.3036 (3)	0.53906 (9)	0.0514 (3)	0.0294 (4)
H6B	0.3420	0.5746	0.0086	0.035*
C7B	−0.1563 (3)	0.52171 (9)	0.3099 (2)	0.0262 (4)
C8B	−0.3134 (3)	0.49950 (11)	0.3806 (3)	0.0311 (4)
H8D	−0.3062	0.5060	0.4974	0.047*
H8E	−0.3255	0.4578	0.3587	0.047*
H8F	−0.4099	0.5203	0.3316	0.047*
C1C	0.2330 (2)	0.66284 (9)	0.5771 (2)	0.0234 (4)
C2C	0.1854 (3)	0.67538 (9)	0.4179 (2)	0.0253 (4)
H2C	0.0732	0.6854	0.3885	0.030*
C3C	0.3013 (3)	0.67338 (9)	0.3012 (2)	0.0256 (4)
H3C	0.2689	0.6816	0.1917	0.031*
C4C	0.4670 (3)	0.65910 (8)	0.3472 (2)	0.0237 (4)
C5C	0.5135 (3)	0.64594 (9)	0.5082 (3)	0.0262 (4)
H5C	0.6254	0.6357	0.5382	0.031*
C6C	0.3967 (3)	0.64786 (10)	0.6241 (2)	0.0264 (4)
H6C	0.4277	0.6391	0.7335	0.032*
C7C	0.5923 (3)	0.68068 (9)	0.0876 (2)	0.0268 (4)
C8C	0.7509 (3)	0.67167 (10)	0.0028 (3)	0.0322 (4)
H8G	0.7267	0.6738	−0.1140	0.048*
H8H	0.7976	0.6334	0.0312	0.048*
H8I	0.8313	0.7020	0.0362	0.048*
N1A	0.6380 (2)	0.29638 (8)	0.2051 (2)	0.0275 (4)
H1A	0.6025	0.2725	0.1278	0.033*
N2A	0.1472 (2)	0.38905 (8)	0.7433 (2)	0.0298 (4)
N3A	0.0025 (3)	0.39598 (8)	0.6851 (2)	0.0290 (4)
N4A	−0.1280 (3)	0.40705 (10)	0.6390 (3)	0.0438 (5)
N1B	−0.0471 (2)	0.47950 (8)	0.2718 (2)	0.0248 (3)
H1B	−0.0732	0.4438	0.2990	0.030*
N2B	0.5014 (2)	0.45126 (9)	−0.2554 (2)	0.0327 (4)
N3B	0.4002 (2)	0.47963 (10)	−0.3445 (2)	0.0343 (4)
N4B	0.3078 (3)	0.50072 (13)	−0.4341 (3)	0.0506 (6)
N1C	0.5929 (2)	0.65573 (8)	0.2372 (2)	0.0259 (4)
H1C	0.6817	0.6354	0.2681	0.031*
N2C	−0.0633 (3)	0.62023 (11)	0.6648 (2)	0.0398 (5)
N3C	−0.0303 (3)	0.56989 (11)	0.7122 (3)	0.0435 (5)
N4C	−0.0145 (4)	0.52391 (13)	0.7518 (5)	0.0750 (10)
O1A	0.8469 (2)	0.35857 (7)	0.2876 (2)	0.0315 (3)
O2A	0.3014 (2)	0.31341 (8)	0.90065 (18)	0.0345 (4)
O3A	0.0612 (2)	0.28276 (7)	0.7193 (2)	0.0338 (4)
O1B	−0.1314 (2)	0.57361 (7)	0.2926 (2)	0.0362 (4)
O2B	0.6906 (2)	0.45011 (9)	−0.0149 (2)	0.0393 (4)
O3B	0.6056 (2)	0.54647 (8)	−0.1286 (2)	0.0370 (4)
O1C	0.4759 (2)	0.70885 (8)	0.0289 (2)	0.0351 (4)
O2C	0.1595 (2)	0.65156 (7)	0.87722 (18)	0.0299 (3)
O3C	0.0018 (3)	0.72287 (8)	0.7077 (2)	0.0443 (5)
S1A	0.20593 (6)	0.31786 (2)	0.75080 (6)	0.02521 (11)
S1B	0.56587 (6)	0.48809 (2)	−0.08468 (6)	0.02667 (11)
S1C	0.08692 (6)	0.66879 (2)	0.72344 (6)	0.02662 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0267 (10)	0.0207 (9)	0.0212 (8)	−0.0005 (7)	0.0116 (7)	0.0000 (7)
C2A	0.0272 (10)	0.0303 (10)	0.0219 (8)	−0.0021 (8)	0.0052 (7)	−0.0030 (8)
C3A	0.0212 (9)	0.0269 (10)	0.0290 (9)	−0.0033 (8)	0.0064 (7)	−0.0036 (8)
C4A	0.0267 (10)	0.0216 (8)	0.0233 (9)	−0.0032 (7)	0.0116 (7)	−0.0010 (7)
C5A	0.0292 (11)	0.0328 (10)	0.0193 (9)	−0.0039 (8)	0.0058 (8)	−0.0015 (7)
C6A	0.0203 (9)	0.0284 (9)	0.0246 (9)	−0.0012 (7)	0.0066 (7)	−0.0005 (7)
C7A	0.0306 (11)	0.0289 (10)	0.0304 (10)	−0.0012 (8)	0.0150 (8)	0.0001 (8)
C8A	0.0368 (12)	0.0398 (12)	0.0329 (10)	−0.0041 (10)	0.0218 (9)	−0.0004 (10)
C1B	0.0222 (9)	0.0285 (10)	0.0233 (8)	−0.0022 (8)	0.0041 (7)	−0.0006 (8)
C2B	0.0273 (11)	0.0237 (9)	0.0308 (10)	0.0021 (8)	0.0070 (8)	−0.0027 (8)
C3B	0.0306 (11)	0.0229 (9)	0.0308 (10)	−0.0012 (8)	0.0086 (8)	0.0017 (8)
C4B	0.0229 (9)	0.0266 (9)	0.0219 (8)	0.0003 (8)	0.0041 (7)	−0.0010 (7)
C5B	0.0261 (11)	0.0230 (9)	0.0387 (11)	0.0025 (8)	0.0085 (9)	−0.0019 (8)
C6B	0.0265 (11)	0.0255 (10)	0.0369 (11)	−0.0019 (8)	0.0078 (9)	0.0037 (8)
C7B	0.0244 (10)	0.0317 (10)	0.0227 (9)	0.0021 (8)	0.0032 (7)	−0.0020 (8)
C8B	0.0254 (10)	0.0400 (12)	0.0289 (10)	0.0010 (9)	0.0098 (8)	−0.0002 (9)
C1C	0.0205 (9)	0.0247 (9)	0.0260 (9)	0.0023 (7)	0.0098 (7)	0.0024 (7)
C2C	0.0193 (9)	0.0284 (10)	0.0288 (10)	0.0027 (8)	0.0050 (7)	0.0042 (8)
C3C	0.0257 (10)	0.0280 (9)	0.0234 (9)	0.0015 (8)	0.0037 (7)	0.0031 (8)
C4C	0.0245 (10)	0.0221 (9)	0.0252 (9)	−0.0001 (7)	0.0077 (7)	−0.0009 (7)
C5C	0.0195 (10)	0.0306 (10)	0.0290 (10)	0.0049 (8)	0.0042 (8)	0.0009 (8)
C6C	0.0259 (10)	0.0326 (10)	0.0210 (9)	0.0051 (8)	0.0042 (7)	0.0018 (7)
C7C	0.0284 (10)	0.0277 (10)	0.0251 (10)	−0.0057 (8)	0.0086 (8)	−0.0024 (7)
C8C	0.0381 (12)	0.0284 (10)	0.0321 (10)	−0.0030 (9)	0.0189 (9)	0.0001 (9)
N1A	0.0296 (9)	0.0317 (9)	0.0226 (8)	−0.0046 (7)	0.0121 (7)	−0.0056 (7)
N2A	0.0247 (9)	0.0242 (8)	0.0409 (10)	0.0005 (7)	0.0051 (8)	−0.0069 (7)
N3A	0.0340 (11)	0.0265 (9)	0.0271 (9)	−0.0026 (7)	0.0062 (8)	−0.0038 (7)
N4A	0.0365 (12)	0.0380 (11)	0.0553 (14)	0.0031 (9)	−0.0088 (10)	−0.0104 (10)
N1B	0.0254 (8)	0.0236 (8)	0.0263 (8)	−0.0011 (7)	0.0085 (6)	0.0002 (6)
N2B	0.0293 (10)	0.0384 (10)	0.0313 (10)	−0.0007 (8)	0.0078 (8)	−0.0049 (8)
N3B	0.0306 (10)	0.0449 (11)	0.0281 (9)	−0.0089 (9)	0.0077 (8)	−0.0012 (8)
N4B	0.0442 (13)	0.0708 (17)	0.0362 (11)	−0.0101 (12)	−0.0034 (10)	0.0075 (11)
N1C	0.0233 (9)	0.0282 (9)	0.0270 (8)	0.0036 (7)	0.0087 (7)	0.0005 (6)
N2C	0.0261 (10)	0.0624 (15)	0.0311 (10)	−0.0050 (9)	0.0041 (8)	−0.0051 (9)
N3C	0.0248 (10)	0.0494 (14)	0.0574 (14)	−0.0062 (9)	0.0099 (9)	−0.0252 (11)
N4C	0.0433 (16)	0.0376 (15)	0.145 (3)	−0.0110 (12)	0.0122 (18)	−0.0275 (16)
O1A	0.0323 (9)	0.0286 (7)	0.0352 (8)	−0.0064 (6)	0.0149 (6)	−0.0034 (6)
O2A	0.0431 (9)	0.0380 (8)	0.0237 (7)	0.0035 (8)	0.0117 (6)	−0.0003 (6)
O3A	0.0363 (9)	0.0304 (8)	0.0368 (9)	−0.0072 (7)	0.0188 (7)	−0.0048 (6)
O1B	0.0318 (9)	0.0282 (8)	0.0502 (10)	0.0040 (7)	0.0144 (7)	−0.0018 (7)
O2B	0.0260 (9)	0.0507 (10)	0.0416 (9)	0.0080 (7)	0.0054 (7)	0.0056 (8)
O3B	0.0307 (9)	0.0372 (9)	0.0439 (9)	−0.0079 (7)	0.0097 (7)	0.0006 (7)
O1C	0.0323 (9)	0.0441 (9)	0.0295 (8)	−0.0046 (7)	0.0053 (6)	0.0095 (7)
O2C	0.0285 (8)	0.0367 (8)	0.0254 (7)	0.0000 (6)	0.0084 (6)	0.0005 (6)
O3C	0.0467 (11)	0.0444 (10)	0.0442 (10)	0.0197 (8)	0.0216 (9)	0.0101 (8)
S1A	0.0292 (3)	0.0244 (2)	0.0234 (2)	−0.00106 (19)	0.01256 (18)	−0.00172 (17)
S1B	0.0198 (2)	0.0318 (3)	0.0288 (2)	−0.00115 (19)	0.00476 (17)	0.00076 (19)
S1C	0.0237 (2)	0.0319 (2)	0.0253 (2)	0.0045 (2)	0.00933 (18)	0.00261 (19)

Geometric parameters (Å, º)

C1A—C2A	1.387 (3)	C1C—C2C	1.385 (3)
C1A—C6A	1.387 (3)	C1C—C6C	1.395 (3)
C1A—S1A	1.7459 (18)	C1C—S1C	1.7490 (19)
C2A—C3A	1.383 (3)	C2C—C3C	1.387 (3)
C2A—H2A	0.95	C2C—H2C	0.95
C3A—C4A	1.397 (3)	C3C—C4C	1.405 (3)
C3A—H3A	0.95	C3C—H3C	0.95
C4A—C5A	1.392 (3)	C4C—C5C	1.400 (3)
C4A—N1A	1.409 (2)	C4C—N1C	1.408 (3)
C5A—C6A	1.386 (3)	C5C—C6C	1.388 (3)
C5A—H5A	0.95	C5C—H5C	0.95
C6A—H6A	0.95	C6C—H6C	0.95
C7A—O1A	1.232 (3)	C7C—O1C	1.217 (3)
C7A—N1A	1.363 (3)	C7C—N1C	1.369 (3)
C7A—C8A	1.501 (3)	C7C—C8C	1.511 (3)
C8A—H8A	0.98	C8C—H8G	0.98
C8A—H8B	0.98	C8C—H8H	0.98
C8A—H8C	0.98	C8C—H8I	0.98
C1B—C6B	1.383 (3)	N1A—H1A	0.88
C1B—C2B	1.393 (3)	N2A—N3A	1.244 (3)
C1B—S1B	1.749 (2)	N2A—S1A	1.7034 (19)
C2B—C3B	1.377 (3)	N3A—N4A	1.125 (3)
C2B—H2B	0.95	N1B—H1B	0.88
C3B—C4B	1.399 (3)	N2B—N3B	1.251 (3)
C3B—H3B	0.95	N2B—S1B	1.706 (2)
C4B—C5B	1.391 (3)	N3B—N4B	1.129 (3)
C4B—N1B	1.407 (3)	N1C—H1C	0.88
C5B—C6B	1.394 (3)	N2C—N3C	1.246 (4)
C5B—H5B	0.95	N2C—S1C	1.695 (2)
C6B—H6B	0.95	N3C—N4C	1.112 (4)
C7B—O1B	1.220 (3)	O2A—S1A	1.4266 (17)
C7B—N1B	1.360 (3)	O3A—S1A	1.4287 (18)
C7B—C8B	1.516 (3)	O2B—S1B	1.4266 (18)
C8B—H8D	0.98	O3B—S1B	1.4320 (18)
C8B—H8E	0.98	O2C—S1C	1.4284 (16)
C8B—H8F	0.98	O3C—S1C	1.4217 (18)
C2A—C1A—C6A	121.59 (17)	C1C—C2C—C3C	120.20 (19)
C2A—C1A—S1A	120.12 (15)	C1C—C2C—H2C	119.9
C6A—C1A—S1A	118.29 (15)	C3C—C2C—H2C	119.9
C3A—C2A—C1A	119.59 (19)	C2C—C3C—C4C	119.09 (18)
C3A—C2A—H2A	120.2	C2C—C3C—H3C	120.5
C1A—C2A—H2A	120.2	C4C—C3C—H3C	120.5
C2A—C3A—C4A	119.28 (19)	C5C—C4C—C3C	120.28 (18)
C2A—C3A—H3A	120.4	C5C—C4C—N1C	116.60 (18)
C4A—C3A—H3A	120.4	C3C—C4C—N1C	123.11 (18)
C5A—C4A—C3A	120.67 (18)	C6C—C5C—C4C	120.3 (2)
C5A—C4A—N1A	117.53 (19)	C6C—C5C—H5C	119.9
C3A—C4A—N1A	121.77 (19)	C4C—C5C—H5C	119.9
C6A—C5A—C4A	119.94 (19)	C5C—C6C—C1C	118.87 (19)
C6A—C5A—H5A	120.0	C5C—C6C—H6C	120.6
C4A—C5A—H5A	120.0	C1C—C6C—H6C	120.6
C5A—C6A—C1A	118.88 (19)	O1C—C7C—N1C	123.18 (19)
C5A—C6A—H6A	120.6	O1C—C7C—C8C	122.55 (19)
C1A—C6A—H6A	120.6	N1C—C7C—C8C	114.25 (19)
O1A—C7A—N1A	122.98 (19)	C7C—C8C—H8G	109.5
O1A—C7A—C8A	122.1 (2)	C7C—C8C—H8H	109.5
N1A—C7A—C8A	114.9 (2)	H8G—C8C—H8H	109.5
C7A—C8A—H8A	109.5	C7C—C8C—H8I	109.5
C7A—C8A—H8B	109.5	H8G—C8C—H8I	109.5
H8A—C8A—H8B	109.5	H8H—C8C—H8I	109.5
C7A—C8A—H8C	109.5	C7A—N1A—C4A	125.46 (18)
H8A—C8A—H8C	109.5	C7A—N1A—H1A	117.3
H8B—C8A—H8C	109.5	C4A—N1A—H1A	117.3
C6B—C1B—C2B	121.02 (18)	N3A—N2A—S1A	112.86 (15)
C6B—C1B—S1B	120.24 (16)	N4A—N3A—N2A	173.8 (2)
C2B—C1B—S1B	118.71 (16)	C7B—N1B—C4B	128.12 (18)
C3B—C2B—C1B	118.84 (19)	C7B—N1B—H1B	115.9
C3B—C2B—H2B	120.6	C4B—N1B—H1B	115.9
C1B—C2B—H2B	120.6	N3B—N2B—S1B	112.81 (17)
C2B—C3B—C4B	120.84 (19)	N4B—N3B—N2B	173.5 (3)
C2B—C3B—H3B	119.6	C7C—N1C—C4C	127.17 (18)
C4B—C3B—H3B	119.6	C7C—N1C—H1C	116.4
C5B—C4B—C3B	119.90 (18)	C4C—N1C—H1C	116.4
C5B—C4B—N1B	123.95 (19)	N3C—N2C—S1C	112.69 (18)
C3B—C4B—N1B	116.14 (18)	N4C—N3C—N2C	174.1 (3)
C4B—C5B—C6B	119.28 (19)	O2A—S1A—O3A	120.62 (10)
C4B—C5B—H5B	120.4	O2A—S1A—N2A	103.55 (10)
C6B—C5B—H5B	120.4	O3A—S1A—N2A	108.33 (10)
C1B—C6B—C5B	120.03 (19)	O2A—S1A—C1A	109.56 (10)
C1B—C6B—H6B	120.0	O3A—S1A—C1A	109.72 (10)
C5B—C6B—H6B	120.0	N2A—S1A—C1A	103.57 (10)
O1B—C7B—N1B	123.8 (2)	O2B—S1B—O3B	120.96 (11)
O1B—C7B—C8B	121.5 (2)	O2B—S1B—N2B	101.81 (11)
N1B—C7B—C8B	114.65 (19)	O3B—S1B—N2B	108.33 (10)
C7B—C8B—H8D	109.5	O2B—S1B—C1B	110.51 (10)
C7B—C8B—H8E	109.5	O3B—S1B—C1B	109.79 (11)
H8D—C8B—H8E	109.5	N2B—S1B—C1B	103.78 (10)
C7B—C8B—H8F	109.5	O3C—S1C—O2C	119.55 (11)
H8D—C8B—H8F	109.5	O3C—S1C—N2C	102.58 (13)
H8E—C8B—H8F	109.5	O2C—S1C—N2C	108.67 (10)
C2C—C1C—C6C	121.31 (18)	O3C—S1C—C1C	110.20 (10)
C2C—C1C—S1C	119.35 (16)	O2C—S1C—C1C	110.20 (10)
C6C—C1C—S1C	119.28 (15)	N2C—S1C—C1C	104.30 (10)
C6A—C1A—C2A—C3A	1.2 (3)	C8B—C7B—N1B—C4B	174.97 (19)
S1A—C1A—C2A—C3A	−179.83 (16)	C5B—C4B—N1B—C7B	−3.2 (3)
C1A—C2A—C3A—C4A	0.7 (3)	C3B—C4B—N1B—C7B	177.8 (2)
C2A—C3A—C4A—C5A	−2.3 (3)	O1C—C7C—N1C—C4C	−1.7 (3)
C2A—C3A—C4A—N1A	179.83 (19)	C8C—C7C—N1C—C4C	176.7 (2)
C3A—C4A—C5A—C6A	2.2 (3)	C5C—C4C—N1C—C7C	−161.0 (2)
N1A—C4A—C5A—C6A	−179.91 (19)	C3C—C4C—N1C—C7C	20.5 (3)
C4A—C5A—C6A—C1A	−0.3 (3)	N3A—N2A—S1A—O2A	−141.30 (17)
C2A—C1A—C6A—C5A	−1.4 (3)	N3A—N2A—S1A—O3A	−12.1 (2)
S1A—C1A—C6A—C5A	179.64 (15)	N3A—N2A—S1A—C1A	104.34 (18)
C6B—C1B—C2B—C3B	1.8 (3)	C2A—C1A—S1A—O2A	−13.1 (2)
S1B—C1B—C2B—C3B	−176.00 (17)	C6A—C1A—S1A—O2A	165.87 (16)
C1B—C2B—C3B—C4B	−0.1 (3)	C2A—C1A—S1A—O3A	−147.68 (17)
C2B—C3B—C4B—C5B	−2.4 (3)	C6A—C1A—S1A—O3A	31.31 (19)
C2B—C3B—C4B—N1B	176.7 (2)	C2A—C1A—S1A—N2A	96.85 (18)
C3B—C4B—C5B—C6B	3.3 (3)	C6A—C1A—S1A—N2A	−84.16 (17)
N1B—C4B—C5B—C6B	−175.7 (2)	N3B—N2B—S1B—O2B	−173.99 (16)
C2B—C1B—C6B—C5B	−1.0 (3)	N3B—N2B—S1B—O3B	−45.47 (19)
S1B—C1B—C6B—C5B	176.83 (18)	N3B—N2B—S1B—C1B	71.18 (18)
C4B—C5B—C6B—C1B	−1.6 (3)	C6B—C1B—S1B—O2B	142.18 (19)
C6C—C1C—C2C—C3C	−0.2 (3)	C2B—C1B—S1B—O2B	−40.0 (2)
S1C—C1C—C2C—C3C	177.17 (16)	C6B—C1B—S1B—O3B	6.3 (2)
C1C—C2C—C3C—C4C	−0.7 (3)	C2B—C1B—S1B—O3B	−175.88 (17)
C2C—C3C—C4C—C5C	1.3 (3)	C6B—C1B—S1B—N2B	−109.35 (19)
C2C—C3C—C4C—N1C	179.69 (19)	C2B—C1B—S1B—N2B	68.50 (19)
C3C—C4C—C5C—C6C	−1.1 (3)	N3C—N2C—S1C—O3C	−160.66 (19)
N1C—C4C—C5C—C6C	−179.59 (19)	N3C—N2C—S1C—O2C	−33.1 (2)
C4C—C5C—C6C—C1C	0.3 (3)	N3C—N2C—S1C—C1C	84.4 (2)
C2C—C1C—C6C—C5C	0.4 (3)	C2C—C1C—S1C—O3C	−48.4 (2)
S1C—C1C—C6C—C5C	−176.97 (17)	C6C—C1C—S1C—O3C	128.95 (19)
O1A—C7A—N1A—C4A	1.8 (4)	C2C—C1C—S1C—O2C	177.51 (17)
C8A—C7A—N1A—C4A	−176.0 (2)	C6C—C1C—S1C—O2C	−5.1 (2)
C5A—C4A—N1A—C7A	146.9 (2)	C2C—C1C—S1C—N2C	61.0 (2)
C3A—C4A—N1A—C7A	−35.2 (3)	C6C—C1C—S1C—N2C	−121.58 (19)
O1B—C7B—N1B—C4B	−6.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O1A^i	0.88	2.06	2.913 (2)	162
N1A—H1A···O1C^ii	0.88	2.03	2.907 (2)	172
N1C—H1C···O1B^iii	0.88	2.07	2.929 (2)	165

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