5-Isobutyl-4-phenyl-sulfonyl-1H-pyrazol-3(2H)-one.

The title compound, C(13)H(16)N(2)O(3)S, consists of two crystallographically independent mol-ecules with similar geometries and exists in a keto form, the C=O bond lengths being 1.267 (2) and 1.254 (2) Å. In both mol-ecules, the pyrazole rings are approximately planar, with maximum deviations of 0.017 (2) and 0.010 (2) Å, and the dihedral angles between the pyrazole and phenyl rings are 83.63 (11) and 70.07 (12)°. In one mol-ecule, an intra-molecular C-H⋯O hydrogen bond with an S(6) ring motif is observed. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into two-dimensional networks parallel to the ab plane.

Related literature

For background to pyrazole derivatives and their microbial activities, see: Ragavan et al. (2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Loh, Fun, Ragavan, Vijayakumar & Sarveswari (2010 ▶); Loh, Fun, Ragavan, Vijayakumar & Venkatesh (2010 ▶); Shahani et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H16N2O3S

M = 280.34

Triclinic,

a = 11.3423 (8) Å

b = 11.9987 (9) Å

c = 12.4657 (9) Å

α = 98.579 (3)°

β = 113.038 (3)°

γ = 112.882 (3)°

V = 1344.42 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 100 K

0.56 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.875, T max = 0.958

18458 measured reflections

5202 independent reflections

4816 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.109

S = 1.04

5202 reflections

363 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044181/is2619sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044181/is2619Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H16N2O3S	Z = 4
Mr = 280.34	F(000) = 592
Triclinic, P1	Dx = 1.385 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3423 (8) Å	Cell parameters from 9939 reflections
b = 11.9987 (9) Å	θ = 2.6–35.0°
c = 12.4657 (9) Å	µ = 0.25 mm−1
α = 98.579 (3)°	T = 100 K
β = 113.038 (3)°	Block, colourless
γ = 112.882 (3)°	0.56 × 0.20 × 0.18 mm
V = 1344.42 (17) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5202 independent reflections
Radiation source: fine-focus sealed tube	4816 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.875, Tmax = 0.958	k = −14→14
18458 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0553P)2 + 1.2051P] where P = (Fo2 + 2Fc2)/3
5202 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1A	0.61779 (4)	0.56939 (4)	0.30323 (4)	0.01287 (12)
O1A	0.52206 (14)	0.62292 (12)	0.29583 (12)	0.0177 (3)
O2A	0.56191 (14)	0.44944 (12)	0.20809 (11)	0.0176 (3)
O3A	0.81177 (13)	0.88563 (12)	0.44040 (11)	0.0155 (3)
N1A	0.96797 (17)	0.87383 (15)	0.36853 (14)	0.0144 (3)
N2A	0.97863 (17)	0.77840 (15)	0.30426 (13)	0.0146 (3)
C1A	0.7407 (2)	0.46688 (18)	0.46562 (17)	0.0190 (4)
H1AA	0.7415	0.4199	0.3996	0.023*
C2A	0.7970 (2)	0.45448 (19)	0.58116 (18)	0.0223 (4)
H2AA	0.8369	0.3998	0.5934	0.027*
C3A	0.7936 (2)	0.52380 (19)	0.67853 (17)	0.0221 (4)
H3AA	0.8317	0.5157	0.7561	0.027*
C4A	0.7335 (2)	0.60524 (19)	0.66063 (17)	0.0227 (4)
H4AA	0.7299	0.6499	0.7259	0.027*
C5A	0.6789 (2)	0.62047 (18)	0.54597 (17)	0.0192 (4)
H5AA	0.6405	0.6762	0.5341	0.023*
C6A	0.68325 (19)	0.55035 (16)	0.44963 (16)	0.0144 (3)
C7A	0.77240 (19)	0.68499 (17)	0.31001 (15)	0.0137 (3)
C8A	0.84468 (18)	0.82068 (16)	0.37900 (15)	0.0128 (3)
C9A	0.86263 (19)	0.66367 (17)	0.26817 (15)	0.0132 (3)
C10A	0.84569 (19)	0.54146 (17)	0.19624 (15)	0.0155 (3)
H10A	0.8084	0.4743	0.2277	0.019*
H10B	0.9418	0.5559	0.2107	0.019*
C11A	0.7416 (2)	0.49321 (18)	0.05437 (16)	0.0190 (4)
H11A	0.6510	0.4944	0.0407	0.023*
C12A	0.7026 (3)	0.3539 (2)	−0.0044 (2)	0.0394 (6)
H12A	0.6353	0.3223	−0.0922	0.059*
H12B	0.6576	0.3006	0.0337	0.059*
H12C	0.7905	0.3511	0.0084	0.059*
C13A	0.8111 (2)	0.5804 (2)	−0.00512 (18)	0.0249 (4)
H13A	0.7427	0.5505	−0.0924	0.037*
H13B	0.8986	0.5784	0.0054	0.037*
H13C	0.8358	0.6675	0.0341	0.037*
S1B	0.32612 (5)	0.06328 (4)	0.30231 (4)	0.01364 (12)
O1B	0.44172 (14)	0.19562 (12)	0.37062 (12)	0.0203 (3)
O2B	0.20554 (14)	0.01636 (13)	0.32778 (12)	0.0184 (3)
O3B	0.18314 (13)	−0.24470 (12)	0.26728 (12)	0.0177 (3)
N1B	0.41780 (16)	−0.21360 (15)	0.33582 (14)	0.0156 (3)
N2B	0.55364 (17)	−0.11548 (15)	0.36901 (14)	0.0158 (3)
C1B	0.1298 (2)	−0.07887 (19)	0.05619 (17)	0.0221 (4)
H1BA	0.0925	−0.1462	0.0827	0.026*
C2B	0.0666 (2)	−0.0952 (2)	−0.06954 (19)	0.0300 (5)
H2BA	−0.0139	−0.1743	−0.1280	0.036*
C3B	0.1230 (3)	0.0058 (2)	−0.10850 (19)	0.0320 (5)
H3BA	0.0792	−0.0057	−0.1928	0.038*
C4B	0.2432 (3)	0.1227 (2)	−0.0231 (2)	0.0304 (5)
H4BA	0.2810	0.1893	−0.0502	0.036*
C5B	0.3091 (2)	0.14218 (19)	0.10415 (19)	0.0224 (4)
H5BA	0.3904	0.2211	0.1623	0.027*
C6B	0.2500 (2)	0.04043 (18)	0.14147 (16)	0.0163 (4)
C7B	0.40072 (19)	−0.03787 (17)	0.32486 (15)	0.0135 (3)
C8B	0.31688 (19)	−0.17245 (17)	0.30481 (15)	0.0141 (3)
C9B	0.54630 (19)	−0.00867 (17)	0.36371 (15)	0.0139 (3)
C10B	0.68105 (19)	0.11342 (17)	0.39661 (16)	0.0166 (4)
H10C	0.7581	0.1324	0.4788	0.020*
H10D	0.6592	0.1840	0.4009	0.020*
C11B	0.7392 (2)	0.10832 (19)	0.30404 (17)	0.0207 (4)
H11B	0.7586	0.0355	0.2987	0.025*
C12B	0.6260 (2)	0.0862 (3)	0.1743 (2)	0.0346 (5)
H12D	0.6646	0.0825	0.1185	0.052*
H12E	0.6043	0.1560	0.1777	0.052*
H12F	0.5376	0.0060	0.1449	0.052*
C13B	0.8834 (2)	0.2320 (2)	0.3531 (2)	0.0273 (4)
H13D	0.9217	0.2272	0.2973	0.041*
H13E	0.9528	0.2424	0.4342	0.041*
H13F	0.8666	0.3047	0.3588	0.041*
H1NA	1.035 (3)	0.944 (3)	0.412 (2)	0.028 (6)*
H2NA	1.054 (3)	0.795 (2)	0.296 (2)	0.032 (7)*
H1NB	0.407 (3)	−0.289 (3)	0.332 (2)	0.026 (6)*
H2NB	0.632 (3)	−0.125 (2)	0.390 (2)	0.026 (6)*

	U11	U22	U33	U12	U13	U23
S1A	0.0104 (2)	0.0121 (2)	0.0158 (2)	0.00489 (17)	0.00692 (16)	0.00437 (16)
O1A	0.0132 (6)	0.0178 (6)	0.0253 (6)	0.0090 (5)	0.0106 (5)	0.0082 (5)
O2A	0.0161 (6)	0.0136 (6)	0.0181 (6)	0.0045 (5)	0.0079 (5)	0.0026 (5)
O3A	0.0119 (6)	0.0154 (6)	0.0190 (6)	0.0073 (5)	0.0082 (5)	0.0027 (5)
N1A	0.0108 (7)	0.0123 (7)	0.0174 (7)	0.0041 (6)	0.0074 (6)	0.0020 (6)
N2A	0.0122 (7)	0.0164 (7)	0.0168 (7)	0.0072 (6)	0.0088 (6)	0.0043 (6)
C1A	0.0214 (9)	0.0169 (9)	0.0207 (9)	0.0096 (8)	0.0121 (8)	0.0060 (7)
C2A	0.0231 (10)	0.0194 (9)	0.0233 (9)	0.0108 (8)	0.0095 (8)	0.0090 (7)
C3A	0.0208 (10)	0.0221 (9)	0.0176 (8)	0.0054 (8)	0.0087 (7)	0.0091 (7)
C4A	0.0219 (10)	0.0241 (10)	0.0194 (9)	0.0075 (8)	0.0131 (8)	0.0039 (7)
C5A	0.0176 (9)	0.0176 (9)	0.0222 (9)	0.0073 (7)	0.0118 (7)	0.0047 (7)
C6A	0.0124 (8)	0.0133 (8)	0.0167 (8)	0.0040 (7)	0.0085 (7)	0.0060 (6)
C7A	0.0124 (8)	0.0143 (8)	0.0156 (8)	0.0069 (7)	0.0076 (7)	0.0056 (6)
C8A	0.0103 (8)	0.0158 (8)	0.0122 (7)	0.0069 (7)	0.0047 (6)	0.0058 (6)
C9A	0.0129 (8)	0.0157 (8)	0.0123 (7)	0.0077 (7)	0.0062 (6)	0.0063 (6)
C10A	0.0152 (8)	0.0156 (8)	0.0166 (8)	0.0080 (7)	0.0085 (7)	0.0046 (7)
C11A	0.0199 (9)	0.0199 (9)	0.0149 (8)	0.0090 (8)	0.0081 (7)	0.0038 (7)
C12A	0.0616 (17)	0.0238 (11)	0.0218 (10)	0.0181 (11)	0.0157 (11)	0.0026 (9)
C13A	0.0250 (10)	0.0301 (11)	0.0193 (9)	0.0120 (9)	0.0117 (8)	0.0098 (8)
S1B	0.0122 (2)	0.0146 (2)	0.0157 (2)	0.00772 (18)	0.00735 (17)	0.00464 (16)
O1B	0.0167 (7)	0.0157 (6)	0.0240 (6)	0.0081 (6)	0.0075 (5)	0.0024 (5)
O2B	0.0166 (6)	0.0225 (7)	0.0225 (6)	0.0122 (6)	0.0126 (5)	0.0085 (5)
O3B	0.0127 (6)	0.0190 (6)	0.0234 (6)	0.0082 (5)	0.0103 (5)	0.0073 (5)
N1B	0.0123 (7)	0.0151 (8)	0.0222 (7)	0.0075 (6)	0.0098 (6)	0.0079 (6)
N2B	0.0108 (7)	0.0185 (8)	0.0188 (7)	0.0082 (6)	0.0072 (6)	0.0062 (6)
C1B	0.0190 (9)	0.0246 (10)	0.0216 (9)	0.0102 (8)	0.0099 (8)	0.0078 (8)
C2B	0.0224 (10)	0.0404 (12)	0.0197 (9)	0.0156 (10)	0.0064 (8)	0.0032 (9)
C3B	0.0368 (12)	0.0576 (15)	0.0221 (10)	0.0364 (12)	0.0170 (9)	0.0209 (10)
C4B	0.0405 (13)	0.0420 (13)	0.0377 (11)	0.0315 (11)	0.0284 (10)	0.0290 (10)
C5B	0.0237 (10)	0.0226 (10)	0.0306 (10)	0.0150 (8)	0.0167 (8)	0.0140 (8)
C6B	0.0154 (9)	0.0207 (9)	0.0179 (8)	0.0123 (8)	0.0088 (7)	0.0083 (7)
C7B	0.0127 (8)	0.0155 (8)	0.0144 (8)	0.0081 (7)	0.0075 (6)	0.0055 (6)
C8B	0.0147 (9)	0.0182 (9)	0.0136 (8)	0.0097 (7)	0.0089 (7)	0.0061 (7)
C9B	0.0137 (8)	0.0173 (8)	0.0121 (7)	0.0078 (7)	0.0075 (7)	0.0050 (6)
C10B	0.0132 (8)	0.0172 (9)	0.0186 (8)	0.0069 (7)	0.0081 (7)	0.0055 (7)
C11B	0.0183 (9)	0.0235 (10)	0.0248 (9)	0.0110 (8)	0.0133 (8)	0.0098 (8)
C12B	0.0247 (11)	0.0568 (15)	0.0258 (10)	0.0180 (11)	0.0156 (9)	0.0195 (10)
C13B	0.0229 (10)	0.0261 (10)	0.0363 (11)	0.0103 (9)	0.0191 (9)	0.0120 (9)

S1A—O2A	1.4397 (13)	S1B—O1B	1.4385 (13)
S1A—O1A	1.4428 (13)	S1B—O2B	1.4431 (13)
S1A—C7A	1.7215 (18)	S1B—C7B	1.7269 (17)
S1A—C6A	1.7691 (17)	S1B—C6B	1.7713 (18)
O3A—C8A	1.267 (2)	O3B—C8B	1.254 (2)
N1A—C8A	1.361 (2)	N1B—C8B	1.362 (2)
N1A—N2A	1.370 (2)	N1B—N2B	1.370 (2)
N1A—H1NA	0.79 (3)	N1B—H1NB	0.86 (3)
N2A—C9A	1.331 (2)	N2B—C9B	1.326 (2)
N2A—H2NA	0.84 (3)	N2B—H2NB	0.88 (3)
C1A—C2A	1.386 (3)	C1B—C2B	1.389 (3)
C1A—C6A	1.390 (3)	C1B—C6B	1.390 (3)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.388 (3)	C2B—C3B	1.389 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.390 (3)	C3B—C4B	1.375 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.390 (3)	C4B—C5B	1.398 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.389 (2)	C5B—C6B	1.391 (3)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C7A—C9A	1.402 (2)	C7B—C9B	1.399 (2)
C7A—C8A	1.433 (2)	C7B—C8B	1.440 (2)
C9A—C10A	1.498 (2)	C9B—C10B	1.496 (2)
C10A—C11A	1.544 (2)	C10B—C11B	1.541 (2)
C10A—H10A	0.9700	C10B—H10C	0.9700
C10A—H10B	0.9700	C10B—H10D	0.9700
C11A—C13A	1.521 (3)	C11B—C13B	1.520 (3)
C11A—C12A	1.528 (3)	C11B—C12B	1.522 (3)
C11A—H11A	0.9800	C11B—H11B	0.9800
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
O2A—S1A—O1A	119.07 (8)	O1B—S1B—O2B	118.68 (8)
O2A—S1A—C7A	108.50 (8)	O1B—S1B—C7B	109.29 (8)
O1A—S1A—C7A	107.89 (8)	O2B—S1B—C7B	106.75 (8)
O2A—S1A—C6A	108.27 (8)	O1B—S1B—C6B	107.72 (8)
O1A—S1A—C6A	107.77 (8)	O2B—S1B—C6B	107.22 (8)
C7A—S1A—C6A	104.39 (8)	C7B—S1B—C6B	106.56 (8)
C8A—N1A—N2A	109.89 (14)	C8B—N1B—N2B	110.67 (15)
C8A—N1A—H1NA	123.5 (19)	C8B—N1B—H1NB	130.6 (16)
N2A—N1A—H1NA	123.7 (19)	N2B—N1B—H1NB	118.5 (16)
C9A—N2A—N1A	110.01 (15)	C9B—N2B—N1B	109.61 (15)
C9A—N2A—H2NA	128.6 (17)	C9B—N2B—H2NB	126.7 (16)
N1A—N2A—H2NA	121.2 (17)	N1B—N2B—H2NB	123.7 (16)
C2A—C1A—C6A	119.19 (16)	C2B—C1B—C6B	118.48 (19)
C2A—C1A—H1AA	120.4	C2B—C1B—H1BA	120.8
C6A—C1A—H1AA	120.4	C6B—C1B—H1BA	120.8
C1A—C2A—C3A	119.87 (18)	C3B—C2B—C1B	120.4 (2)
C1A—C2A—H2AA	120.1	C3B—C2B—H2BA	119.8
C3A—C2A—H2AA	120.1	C1B—C2B—H2BA	119.8
C2A—C3A—C4A	120.31 (17)	C4B—C3B—C2B	120.35 (19)
C2A—C3A—H3AA	119.8	C4B—C3B—H3BA	119.8
C4A—C3A—H3AA	119.8	C2B—C3B—H3BA	119.8
C3A—C4A—C5A	120.56 (17)	C3B—C4B—C5B	120.6 (2)
C3A—C4A—H4AA	119.7	C3B—C4B—H4BA	119.7
C5A—C4A—H4AA	119.7	C5B—C4B—H4BA	119.7
C6A—C5A—C4A	118.31 (17)	C6B—C5B—C4B	118.23 (19)
C6A—C5A—H5AA	120.8	C6B—C5B—H5BA	120.9
C4A—C5A—H5AA	120.8	C4B—C5B—H5BA	120.9
C5A—C6A—C1A	121.74 (16)	C1B—C6B—C5B	121.91 (17)
C5A—C6A—S1A	119.60 (14)	C1B—C6B—S1B	118.50 (14)
C1A—C6A—S1A	118.65 (13)	C5B—C6B—S1B	119.57 (14)
C9A—C7A—C8A	107.66 (15)	C9B—C7B—C8B	107.90 (15)
C9A—C7A—S1A	127.02 (14)	C9B—C7B—S1B	128.47 (14)
C8A—C7A—S1A	124.58 (13)	C8B—C7B—S1B	123.63 (13)
O3A—C8A—N1A	123.49 (16)	O3B—C8B—N1B	123.41 (16)
O3A—C8A—C7A	131.50 (16)	O3B—C8B—C7B	132.46 (16)
N1A—C8A—C7A	105.00 (14)	N1B—C8B—C7B	104.14 (15)
N2A—C9A—C7A	107.31 (15)	N2B—C9B—C7B	107.66 (16)
N2A—C9A—C10A	121.56 (15)	N2B—C9B—C10B	120.20 (16)
C7A—C9A—C10A	131.14 (16)	C7B—C9B—C10B	132.14 (16)
C9A—C10A—C11A	113.81 (14)	C9B—C10B—C11B	114.21 (15)
C9A—C10A—H10A	108.8	C9B—C10B—H10C	108.7
C11A—C10A—H10A	108.8	C11B—C10B—H10C	108.7
C9A—C10A—H10B	108.8	C9B—C10B—H10D	108.7
C11A—C10A—H10B	108.8	C11B—C10B—H10D	108.7
H10A—C10A—H10B	107.7	H10C—C10B—H10D	107.6
C13A—C11A—C12A	111.09 (17)	C13B—C11B—C12B	111.52 (17)
C13A—C11A—C10A	111.16 (15)	C13B—C11B—C10B	109.50 (16)
C12A—C11A—C10A	109.05 (16)	C12B—C11B—C10B	111.26 (16)
C13A—C11A—H11A	108.5	C13B—C11B—H11B	108.1
C12A—C11A—H11A	108.5	C12B—C11B—H11B	108.1
C10A—C11A—H11A	108.5	C10B—C11B—H11B	108.1
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C8A—N1A—N2A—C9A	2.14 (19)	C8B—N1B—N2B—C9B	1.50 (19)
C6A—C1A—C2A—C3A	0.8 (3)	C6B—C1B—C2B—C3B	0.1 (3)
C1A—C2A—C3A—C4A	0.3 (3)	C1B—C2B—C3B—C4B	0.8 (3)
C2A—C3A—C4A—C5A	−1.3 (3)	C2B—C3B—C4B—C5B	−0.9 (3)
C3A—C4A—C5A—C6A	1.3 (3)	C3B—C4B—C5B—C6B	0.1 (3)
C4A—C5A—C6A—C1A	−0.2 (3)	C2B—C1B—C6B—C5B	−0.9 (3)
C4A—C5A—C6A—S1A	−178.87 (14)	C2B—C1B—C6B—S1B	177.62 (15)
C2A—C1A—C6A—C5A	−0.8 (3)	C4B—C5B—C6B—C1B	0.8 (3)
C2A—C1A—C6A—S1A	177.83 (15)	C4B—C5B—C6B—S1B	−177.67 (14)
O2A—S1A—C6A—C5A	−150.20 (15)	O1B—S1B—C6B—C1B	−176.39 (14)
O1A—S1A—C6A—C5A	−20.19 (17)	O2B—S1B—C6B—C1B	−47.59 (16)
C7A—S1A—C6A—C5A	94.35 (16)	C7B—S1B—C6B—C1B	66.43 (16)
O2A—S1A—C6A—C1A	31.11 (16)	O1B—S1B—C6B—C5B	2.15 (17)
O1A—S1A—C6A—C1A	161.12 (14)	O2B—S1B—C6B—C5B	130.95 (15)
C7A—S1A—C6A—C1A	−84.34 (15)	C7B—S1B—C6B—C5B	−115.03 (15)
O2A—S1A—C7A—C9A	−21.55 (18)	O1B—S1B—C7B—C9B	−20.70 (18)
O1A—S1A—C7A—C9A	−151.82 (15)	O2B—S1B—C7B—C9B	−150.22 (15)
C6A—S1A—C7A—C9A	93.73 (16)	C6B—S1B—C7B—C9B	95.44 (16)
O2A—S1A—C7A—C8A	169.54 (14)	O1B—S1B—C7B—C8B	159.51 (14)
O1A—S1A—C7A—C8A	39.28 (16)	O2B—S1B—C7B—C8B	29.99 (16)
C6A—S1A—C7A—C8A	−75.18 (16)	C6B—S1B—C7B—C8B	−84.35 (15)
N2A—N1A—C8A—O3A	175.65 (15)	N2B—N1B—C8B—O3B	177.71 (15)
N2A—N1A—C8A—C7A	−3.48 (18)	N2B—N1B—C8B—C7B	−1.81 (18)
C9A—C7A—C8A—O3A	−175.45 (17)	C9B—C7B—C8B—O3B	−177.96 (17)
S1A—C7A—C8A—O3A	−4.7 (3)	S1B—C7B—C8B—O3B	1.9 (3)
C9A—C7A—C8A—N1A	3.59 (18)	C9B—C7B—C8B—N1B	1.50 (18)
S1A—C7A—C8A—N1A	174.31 (12)	S1B—C7B—C8B—N1B	−178.68 (12)
N1A—N2A—C9A—C7A	0.25 (19)	N1B—N2B—C9B—C7B	−0.46 (19)
N1A—N2A—C9A—C10A	−179.75 (15)	N1B—N2B—C9B—C10B	179.60 (14)
C8A—C7A—C9A—N2A	−2.40 (19)	C8B—C7B—C9B—N2B	−0.66 (19)
S1A—C7A—C9A—N2A	−172.83 (13)	S1B—C7B—C9B—N2B	179.53 (13)
C8A—C7A—C9A—C10A	177.60 (16)	C8B—C7B—C9B—C10B	179.26 (17)
S1A—C7A—C9A—C10A	7.2 (3)	S1B—C7B—C9B—C10B	−0.5 (3)
N2A—C9A—C10A—C11A	−99.45 (19)	N2B—C9B—C10B—C11B	67.8 (2)
C7A—C9A—C10A—C11A	80.6 (2)	C7B—C9B—C10B—C11B	−112.2 (2)
C9A—C10A—C11A—C13A	71.2 (2)	C9B—C10B—C11B—C13B	−174.69 (16)
C9A—C10A—C11A—C12A	−166.01 (17)	C9B—C10B—C11B—C12B	61.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O3Ai	0.79 (3)	2.05 (3)	2.816 (2)	164 (3)
N2A—H2NA···O3Bii	0.85 (4)	1.85 (4)	2.640 (3)	155 (2)
N1B—H1NB···O1Aiii	0.86 (3)	2.10 (4)	2.733 (3)	130 (3)
N2B—H2NB···O3Aiii	0.88 (4)	1.83 (4)	2.700 (3)	170 (2)
C5A—H5AA···O1Biv	0.93	2.47	3.256 (3)	143
C5B—H5BA···O2A	0.93	2.48	3.307 (3)	149
C10A—H10B···O3Bii	0.97	2.57	3.324 (3)	135
C10B—H10D···O1B	0.97	2.41	3.152 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O3Ai	0.79 (3)	2.05 (3)	2.816 (2)	164 (3)
N2A—H2NA⋯O3Bii	0.85 (4)	1.85 (4)	2.640 (3)	155 (2)
N1B—H1NB⋯O1Aiii	0.86 (3)	2.10 (4)	2.733 (3)	130 (3)
N2B—H2NB⋯O3Aiii	0.88 (4)	1.83 (4)	2.700 (3)	170 (2)
C5A—H5AA⋯O1Biv	0.93	2.47	3.256 (3)	143
C5B—H5BA⋯O2A	0.93	2.48	3.307 (3)	149
C10A—H10B⋯O3Bii	0.97	2.57	3.324 (3)	135
C10B—H10D⋯O1B	0.97	2.41	3.152 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .