Methyl 2-[(methyl-sulfon-yl)(prop-yl)amino]benzoate.

The asymmetric unit of the title compound, C(12)H(17)NO(4)S, contains two mol-ecules, both of which show disorder of the two terminal C atoms of the propyl chain over two sets of sites with an occupancy ratio of 0.581 (6):0.419 (6). Intra-molecular C-H⋯O inter-actions help to establish the mol-ecular conformations: in one mol-ecule, the dihedral angle between the methyl ester group and the benzene ring is 41.0 (2)°, whereas in the other mol-ecule it is 36.12 (17)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O and C-H⋯π inter-actions.

Related literature

For related structures, see: Shafiq et al. (2008 ▶, 2009a ▶,b ▶).

Experimental

Crystal data

C12H17NO4S

M = 271.33

Monoclinic,

a = 10.1762 (4) Å

b = 15.0178 (6) Å

c = 18.0900 (8) Å

β = 92.787 (2)°

V = 2761.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.955, T max = 0.968

25991 measured reflections

5409 independent reflections

2607 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.193

S = 1.01

5409 reflections

328 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054920/hb5288sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054920/hb5288Isup2.hkl

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

C12H17NO4S	F(000) = 1152
Mr = 271.33	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2607 reflections
a = 10.1762 (4) Å	θ = 2.0–26.0°
b = 15.0178 (6) Å	µ = 0.24 mm−1
c = 18.0900 (8) Å	T = 296 K
β = 92.787 (2)°	Prismatic, white
V = 2761.3 (2) Å3	0.25 × 0.12 × 0.10 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	5409 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
graphite	Rint = 0.078
Detector resolution: 7.70 pixels mm-1	θmax = 26.0°, θmin = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
Tmin = 0.955, Tmax = 0.968	l = −22→22
25991 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0837P)2 + 1.0657P] where P = (Fo2 + 2Fc2)/3
5409 reflections	(Δ/σ)max < 0.001
328 parameters	Δρmax = 0.50 e Å−3
7 restraints	Δρmin = −0.40 e Å−3

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 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	Occ. (<1)
S1	0.56276 (10)	0.24818 (8)	0.18894 (6)	0.0513 (4)
O1	0.3570 (3)	0.1598 (3)	0.0442 (2)	0.0822 (15)
O2	0.3266 (3)	0.2903 (2)	−0.01117 (18)	0.0740 (13)
O3	0.4772 (3)	0.3112 (2)	0.15293 (16)	0.0706 (13)
O4	0.5151 (3)	0.1951 (2)	0.24718 (17)	0.0744 (13)
N1	0.6139 (3)	0.1809 (2)	0.12571 (18)	0.0499 (11)
C1	0.4009 (4)	0.2243 (3)	0.0166 (2)	0.0544 (19)
C2	0.5427 (4)	0.2403 (3)	0.0037 (2)	0.0444 (14)
C3	0.5756 (4)	0.2752 (3)	−0.0643 (2)	0.0527 (16)
C4	0.7044 (5)	0.2844 (3)	−0.0819 (3)	0.0598 (17)
C5	0.8031 (4)	0.2615 (3)	−0.0303 (3)	0.0632 (19)
C6	0.7722 (4)	0.2291 (3)	0.0375 (3)	0.0557 (16)
C7	0.6419 (4)	0.2167 (3)	0.0549 (2)	0.0450 (14)
C8	0.1861 (4)	0.2808 (4)	−0.0041 (3)	0.097 (3)
C9	0.6872 (5)	0.0997 (3)	0.1507 (3)	0.079 (2)
C10A	0.6733 (13)	0.0159 (9)	0.1078 (9)	0.132 (3)	0.581 (6)
C11A	0.5345 (13)	−0.0144 (10)	0.1283 (8)	0.132 (3)	0.581 (6)
C12	0.6994 (4)	0.3062 (3)	0.2254 (3)	0.0604 (17)
C11B	0.616 (2)	−0.0690 (11)	0.1372 (10)	0.132 (3)	0.419 (6)
C10B	0.6124 (19)	0.0243 (11)	0.1107 (12)	0.132 (3)	0.419 (6)
S2	0.06182 (10)	0.20113 (8)	0.25426 (7)	0.0580 (4)
O5	−0.1063 (3)	−0.0120 (3)	0.2656 (2)	0.0812 (14)
O6	−0.1371 (3)	−0.0088 (2)	0.38509 (17)	0.0717 (13)
O7	−0.0179 (3)	0.1979 (2)	0.31664 (18)	0.0755 (11)
O8	0.0053 (3)	0.2294 (3)	0.1850 (2)	0.0885 (14)
N2	0.1202 (3)	0.1019 (2)	0.24272 (18)	0.0494 (12)
C13	−0.0629 (4)	−0.0033 (3)	0.3280 (3)	0.0556 (17)
C14	0.0786 (4)	0.0076 (3)	0.3503 (2)	0.0449 (16)
C15	0.1667 (4)	0.0543 (3)	0.3081 (2)	0.0448 (16)
C16	0.2983 (4)	0.0561 (3)	0.3294 (3)	0.0548 (17)
C17	0.3441 (4)	0.0123 (3)	0.3916 (3)	0.0661 (19)
C18	0.2600 (5)	−0.0339 (3)	0.4335 (3)	0.0649 (17)
C19	0.1271 (4)	−0.0351 (3)	0.4137 (3)	0.0569 (17)
C20	−0.2745 (4)	−0.0294 (4)	0.3686 (3)	0.089 (2)
C21	0.1850 (5)	0.0829 (4)	0.1726 (3)	0.082 (2)
C22A	0.1036 (14)	0.0153 (10)	0.1341 (8)	0.132 (3)	0.581 (6)
C23A	0.1593 (14)	−0.0270 (9)	0.0668 (7)	0.132 (3)	0.581 (6)
C24	0.1951 (5)	0.2699 (3)	0.2772 (3)	0.0776 (19)
C23B	0.0401 (17)	−0.0269 (13)	0.1068 (10)	0.132 (3)	0.419 (6)
C22B	0.1746 (18)	−0.0121 (14)	0.1428 (12)	0.132 (3)	0.419 (6)
H4	0.72516	0.30591	−0.12807	0.0720*
H3	0.50905	0.29256	−0.09837	0.0634*
H8A	0.15863	0.22292	−0.02137	0.1453*
H8B	0.14059	0.32570	−0.03309	0.1453*
H8C	0.16584	0.28730	0.04692	0.1453*
H9A	0.77999	0.11479	0.15369	0.0946*
H9B	0.66248	0.08683	0.20068	0.0946*
H10A	0.73989	−0.02731	0.12339	0.1582*	0.581 (6)
H10B	0.67740	0.02645	0.05509	0.1582*	0.581 (6)
H11A	0.53481	−0.02692	0.18035	0.1977*	0.581 (6)
H11B	0.51025	−0.06709	0.10089	0.1977*	0.581 (6)
H11C	0.47223	0.03209	0.11640	0.1977*	0.581 (6)
H12A	0.74009	0.33773	0.18643	0.0906*
H12B	0.76128	0.26493	0.24797	0.0906*
H12C	0.67209	0.34778	0.26191	0.0906*
H5	0.89078	0.26802	−0.04155	0.0756*
H6	0.83923	0.21524	0.07235	0.0665*
H10C	0.52060	0.04192	0.10716	0.1582*	0.419 (6)
H10D	0.64197	0.02323	0.06052	0.1582*	0.419 (6)
H11D	0.61294	−0.10870	0.09558	0.1977*	0.419 (6)
H11E	0.54081	−0.07986	0.16638	0.1977*	0.419 (6)
H11F	0.69491	−0.07898	0.16696	0.1977*	0.419 (6)
H17	0.43332	0.01407	0.40544	0.0795*
H16	0.35661	0.08746	0.30122	0.0657*
H20A	−0.31611	0.01976	0.34291	0.1338*
H20B	−0.31734	−0.03998	0.41394	0.1338*
H20C	−0.28119	−0.08168	0.33812	0.1338*
H21A	0.18963	0.13638	0.14277	0.0977*
H21B	0.27359	0.06069	0.18276	0.0977*
H22A	0.01994	0.04238	0.11918	0.1582*	0.581 (6)
H22B	0.08591	−0.03154	0.16917	0.1582*	0.581 (6)
H23A	0.14796	0.01266	0.02539	0.1977*	0.581 (6)
H23B	0.11414	−0.08189	0.05589	0.1977*	0.581 (6)
H23C	0.25133	−0.03867	0.07639	0.1977*	0.581 (6)
H24A	0.25346	0.27095	0.23705	0.1170*
H24B	0.24125	0.24753	0.32089	0.1170*
H24C	0.16432	0.32910	0.28629	0.1170*
H18	0.29179	−0.06454	0.47530	0.0778*
H19	0.06943	−0.06503	0.44334	0.0684*
H22C	0.24098	−0.02177	0.10690	0.1582*	0.419 (6)
H22D	0.18982	−0.05415	0.18295	0.1582*	0.419 (6)
H23D	−0.02474	−0.02240	0.14340	0.1977*	0.419 (6)
H23E	0.03615	−0.08499	0.08474	0.1977*	0.419 (6)
H23F	0.02312	0.01742	0.06925	0.1977*	0.419 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0426 (6)	0.0712 (8)	0.0403 (6)	0.0018 (5)	0.0048 (4)	0.0047 (6)
O1	0.0583 (19)	0.100 (3)	0.088 (3)	−0.0200 (19)	0.0010 (18)	0.031 (2)
O2	0.0456 (17)	0.096 (3)	0.080 (2)	0.0064 (17)	−0.0020 (16)	0.028 (2)
O3	0.0594 (18)	0.098 (3)	0.054 (2)	0.0344 (17)	−0.0012 (15)	−0.0018 (18)
O4	0.0695 (19)	0.106 (3)	0.0490 (19)	−0.0232 (18)	0.0167 (16)	0.0120 (19)
N1	0.0535 (19)	0.056 (2)	0.040 (2)	0.0046 (17)	−0.0007 (16)	0.0079 (17)
C1	0.049 (3)	0.072 (4)	0.042 (3)	−0.005 (2)	0.000 (2)	0.008 (2)
C2	0.048 (2)	0.048 (3)	0.037 (2)	−0.0028 (19)	0.0003 (19)	0.001 (2)
C3	0.061 (3)	0.059 (3)	0.038 (2)	−0.007 (2)	0.001 (2)	0.001 (2)
C4	0.074 (3)	0.064 (3)	0.043 (3)	−0.015 (2)	0.018 (2)	−0.005 (2)
C5	0.051 (3)	0.083 (4)	0.057 (3)	−0.007 (2)	0.018 (2)	−0.008 (3)
C6	0.051 (2)	0.067 (3)	0.049 (3)	0.004 (2)	0.003 (2)	−0.003 (2)
C7	0.048 (2)	0.050 (3)	0.037 (2)	−0.0003 (19)	0.0030 (19)	−0.0008 (19)
C8	0.049 (3)	0.143 (6)	0.099 (5)	0.006 (3)	0.001 (3)	0.022 (4)
C9	0.106 (4)	0.059 (4)	0.072 (4)	0.008 (3)	0.005 (3)	0.012 (3)
C10A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C11A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C12	0.063 (3)	0.064 (3)	0.054 (3)	−0.006 (2)	0.000 (2)	0.000 (2)
C11B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C10B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
S2	0.0460 (6)	0.0661 (8)	0.0621 (8)	0.0074 (5)	0.0061 (5)	0.0158 (6)
O5	0.065 (2)	0.116 (3)	0.062 (2)	−0.028 (2)	−0.0037 (18)	0.012 (2)
O6	0.0513 (18)	0.103 (3)	0.062 (2)	−0.0208 (17)	0.0156 (16)	−0.0030 (19)
O7	0.0662 (19)	0.086 (2)	0.077 (2)	0.0189 (17)	0.0312 (18)	0.0109 (19)
O8	0.076 (2)	0.114 (3)	0.074 (2)	0.023 (2)	−0.0118 (19)	0.035 (2)
N2	0.051 (2)	0.057 (2)	0.041 (2)	0.0002 (17)	0.0104 (16)	0.0067 (17)
C13	0.055 (3)	0.060 (3)	0.052 (3)	−0.016 (2)	0.004 (3)	0.004 (2)
C14	0.048 (2)	0.044 (3)	0.043 (3)	−0.0025 (19)	0.004 (2)	0.002 (2)
C15	0.047 (2)	0.044 (3)	0.044 (3)	0.0004 (19)	0.0072 (19)	−0.001 (2)
C16	0.048 (3)	0.049 (3)	0.068 (3)	0.000 (2)	0.010 (2)	0.006 (2)
C17	0.048 (3)	0.063 (3)	0.086 (4)	0.003 (2)	−0.010 (3)	0.001 (3)
C18	0.078 (3)	0.056 (3)	0.059 (3)	0.007 (3)	−0.013 (3)	0.007 (2)
C19	0.065 (3)	0.054 (3)	0.052 (3)	−0.006 (2)	0.005 (2)	0.006 (2)
C20	0.054 (3)	0.119 (5)	0.096 (4)	−0.029 (3)	0.014 (3)	−0.009 (4)
C21	0.103 (4)	0.089 (4)	0.054 (3)	0.002 (3)	0.017 (3)	0.001 (3)
C22A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C23A	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C24	0.070 (3)	0.055 (3)	0.108 (4)	−0.002 (2)	0.006 (3)	0.008 (3)
C23B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)
C22B	0.156 (6)	0.125 (5)	0.116 (4)	0.008 (4)	0.018 (4)	−0.031 (4)

S1—O3	1.422 (3)	C11A—H11B	0.9600
S1—O4	1.425 (3)	C11A—H11C	0.9600
S1—N1	1.630 (3)	C11A—H11A	0.9600
S1—C12	1.743 (5)	C11B—H11D	0.9600
S2—O7	1.422 (3)	C11B—H11E	0.9600
S2—O8	1.418 (4)	C11B—H11F	0.9600
S2—N2	1.622 (3)	C12—H12C	0.9600
S2—C24	1.739 (5)	C12—H12A	0.9600
O1—C1	1.187 (6)	C12—H12B	0.9600
O2—C1	1.330 (5)	C13—C14	1.485 (6)
O2—C8	1.449 (5)	C14—C15	1.395 (6)
O5—C13	1.199 (6)	C14—C19	1.384 (6)
O6—C13	1.311 (6)	C15—C16	1.376 (6)
O6—C20	1.449 (5)	C16—C17	1.366 (7)
N1—C7	1.431 (5)	C17—C18	1.361 (7)
N1—C9	1.488 (6)	C18—C19	1.382 (7)
N2—C21	1.486 (6)	C21—C22A	1.465 (16)
N2—C15	1.442 (5)	C21—C22B	1.53 (2)
C1—C2	1.492 (6)	C22A—C23A	1.51 (2)
C2—C3	1.393 (5)	C22B—C23B	1.50 (3)
C2—C7	1.383 (6)	C16—H16	0.9300
C3—C4	1.371 (7)	C17—H17	0.9300
C4—C5	1.381 (7)	C18—H18	0.9300
C5—C6	1.370 (7)	C19—H19	0.9300
C6—C7	1.390 (6)	C20—H20A	0.9600
C9—C10A	1.482 (15)	C20—H20B	0.9600
C9—C10B	1.527 (19)	C20—H20C	0.9600
C10A—C11A	1.546 (19)	C21—H21A	0.9700
C10B—C11B	1.48 (2)	C21—H21B	0.9700
C3—H3	0.9300	C22A—H22A	0.9700
C4—H4	0.9300	C22A—H22B	0.9700
C5—H5	0.9300	C22B—H22D	0.9700
C6—H6	0.9300	C22B—H22C	0.9700
C8—H8C	0.9600	C23A—H23B	0.9600
C8—H8A	0.9600	C23A—H23C	0.9600
C8—H8B	0.9600	C23A—H23A	0.9600
C9—H9B	0.9700	C23B—H23D	0.9600
C9—H9A	0.9700	C23B—H23F	0.9600
C10A—H10A	0.9700	C23B—H23E	0.9600
C10A—H10B	0.9700	C24—H24B	0.9600
C10B—H10C	0.9700	C24—H24C	0.9600
C10B—H10D	0.9700	C24—H24A	0.9600
O3—S1—O4	119.22 (19)	H11D—C11B—H11F	110.00
O3—S1—N1	107.47 (17)	H11E—C11B—H11F	109.00
O3—S1—C12	107.5 (2)	C10B—C11B—H11D	110.00
O4—S1—N1	107.69 (18)	H11D—C11B—H11E	109.00
O4—S1—C12	107.1 (2)	H12B—C12—H12C	109.00
N1—S1—C12	107.4 (2)	S1—C12—H12A	109.00
O7—S2—O8	119.26 (19)	S1—C12—H12B	109.00
O7—S2—N2	107.31 (18)	S1—C12—H12C	109.00
O7—S2—C24	107.4 (2)	H12A—C12—H12B	109.00
O8—S2—N2	107.3 (2)	H12A—C12—H12C	110.00
O8—S2—C24	108.1 (2)	O5—C13—O6	122.3 (4)
N2—S2—C24	106.9 (2)	O5—C13—C14	125.1 (4)
C1—O2—C8	116.0 (4)	O6—C13—C14	112.4 (4)
C13—O6—C20	116.0 (4)	C13—C14—C15	123.2 (4)
S1—N1—C7	118.7 (3)	C13—C14—C19	118.4 (4)
S1—N1—C9	117.8 (3)	C15—C14—C19	118.3 (4)
C7—N1—C9	117.5 (3)	N2—C15—C14	120.3 (3)
S2—N2—C15	117.2 (3)	N2—C15—C16	119.8 (4)
S2—N2—C21	117.9 (3)	C14—C15—C16	120.0 (4)
C15—N2—C21	117.6 (3)	C15—C16—C17	120.7 (4)
O1—C1—O2	123.3 (4)	C16—C17—C18	120.4 (4)
O1—C1—C2	125.7 (4)	C17—C18—C19	119.8 (5)
O2—C1—C2	110.9 (4)	C14—C19—C18	120.9 (4)
C1—C2—C3	118.3 (3)	N2—C21—C22A	106.0 (7)
C1—C2—C7	122.3 (3)	N2—C21—C22B	117.1 (9)
C3—C2—C7	119.3 (4)	C21—C22A—C23A	116.7 (11)
C2—C3—C4	121.1 (4)	C21—C22B—C23B	109.7 (14)
C3—C4—C5	119.4 (5)	C15—C16—H16	120.00
C4—C5—C6	120.2 (4)	C17—C16—H16	120.00
C5—C6—C7	120.9 (4)	C16—C17—H17	120.00
C2—C7—C6	119.2 (4)	C18—C17—H17	120.00
N1—C7—C6	119.1 (4)	C17—C18—H18	120.00
N1—C7—C2	121.7 (4)	C19—C18—H18	120.00
N1—C9—C10A	120.2 (7)	C14—C19—H19	119.00
N1—C9—C10B	103.5 (8)	C18—C19—H19	120.00
C9—C10A—C11A	100.9 (10)	O6—C20—H20A	110.00
C9—C10B—C11B	123.0 (16)	O6—C20—H20B	109.00
C2—C3—H3	119.00	O6—C20—H20C	109.00
C4—C3—H3	119.00	H20A—C20—H20B	109.00
C3—C4—H4	120.00	H20A—C20—H20C	109.00
C5—C4—H4	120.00	H20B—C20—H20C	109.00
C6—C5—H5	120.00	N2—C21—H21A	111.00
C4—C5—H5	120.00	N2—C21—H21B	111.00
C5—C6—H6	120.00	C22A—C21—H21A	111.00
C7—C6—H6	120.00	C22A—C21—H21B	111.00
O2—C8—H8B	110.00	H21A—C21—H21B	109.00
O2—C8—H8A	109.00	C22B—C21—H21A	126.00
H8B—C8—H8C	109.00	C22B—C21—H21B	78.00
H8A—C8—H8C	109.00	C21—C22A—H22A	108.00
O2—C8—H8C	109.00	C21—C22A—H22B	108.00
H8A—C8—H8B	109.00	C23A—C22A—H22A	108.00
N1—C9—H9A	107.00	C23A—C22A—H22B	108.00
N1—C9—H9B	107.00	H22A—C22A—H22B	107.00
C10A—C9—H9A	107.00	C23B—C22B—H22D	110.00
C10A—C9—H9B	107.00	H22C—C22B—H22D	108.00
C10B—C9—H9A	131.00	C21—C22B—H22C	110.00
C10B—C9—H9B	99.00	C21—C22B—H22D	110.00
H9A—C9—H9B	107.00	C23B—C22B—H22C	110.00
C9—C10A—H10A	112.00	C22A—C23A—H23C	109.00
C11A—C10A—H10A	112.00	H23A—C23A—H23B	110.00
C11A—C10A—H10B	112.00	H23A—C23A—H23C	109.00
C9—C10A—H10B	112.00	C22A—C23A—H23A	109.00
H10A—C10A—H10B	109.00	C22A—C23A—H23B	109.00
C9—C10B—H10C	107.00	H23B—C23A—H23C	109.00
C9—C10B—H10D	107.00	C22B—C23B—H23D	109.00
H10C—C10B—H10D	107.00	C22B—C23B—H23E	109.00
C11B—C10B—H10D	106.00	H23D—C23B—H23F	109.00
C11B—C10B—H10C	107.00	H23E—C23B—H23F	109.00
H11A—C11A—H11C	109.00	C22B—C23B—H23F	109.00
H11B—C11A—H11C	109.00	H23D—C23B—H23E	110.00
C10A—C11A—H11B	109.00	S2—C24—H24C	110.00
C10A—C11A—H11A	109.00	H24B—C24—H24C	110.00
H11A—C11A—H11B	109.00	H24A—C24—H24B	109.00
C10A—C11A—H11C	109.00	H24A—C24—H24C	109.00
C10B—C11B—H11E	109.00	S2—C24—H24A	109.00
C10B—C11B—H11F	110.00	S2—C24—H24B	109.00
O3—S1—N1—C7	38.0 (3)	O1—C1—C2—C7	−40.1 (7)
O3—S1—N1—C9	−170.0 (3)	O2—C1—C2—C3	−40.3 (5)
O4—S1—N1—C7	167.6 (3)	C1—C2—C7—C6	176.5 (4)
O4—S1—N1—C9	−40.4 (3)	C1—C2—C3—C4	−174.5 (4)
C12—S1—N1—C7	−77.4 (3)	C7—C2—C3—C4	1.7 (7)
C12—S1—N1—C9	74.6 (3)	C1—C2—C7—N1	−4.3 (7)
C24—S2—N2—C21	−76.9 (4)	C3—C2—C7—N1	179.7 (4)
O8—S2—N2—C15	−171.7 (3)	C3—C2—C7—C6	0.6 (7)
O7—S2—N2—C15	−42.4 (3)	C2—C3—C4—C5	−2.2 (7)
O7—S2—N2—C21	168.1 (3)	C3—C4—C5—C6	0.6 (7)
O8—S2—N2—C21	38.8 (4)	C4—C5—C6—C7	1.6 (7)
C24—S2—N2—C15	72.6 (3)	C5—C6—C7—C2	−2.1 (7)
C8—O2—C1—C2	178.1 (4)	C5—C6—C7—N1	178.7 (4)
C8—O2—C1—O1	1.8 (6)	N1—C9—C10A—C11A	−74.2 (11)
C20—O6—C13—O5	2.2 (7)	O5—C13—C14—C15	35.4 (7)
C20—O6—C13—C14	−173.4 (4)	O5—C13—C14—C19	−140.6 (5)
S1—N1—C7—C6	103.8 (4)	O6—C13—C14—C15	−149.2 (4)
C9—N1—C7—C2	132.5 (4)	O6—C13—C14—C19	34.9 (6)
C9—N1—C7—C6	−48.3 (5)	C13—C14—C15—N2	5.8 (6)
S1—N1—C9—C10A	146.0 (7)	C13—C14—C15—C16	−175.2 (4)
C7—N1—C9—C10A	−61.7 (8)	C19—C14—C15—N2	−178.3 (4)
S1—N1—C7—C2	−75.4 (5)	C19—C14—C15—C16	0.8 (6)
C15—N2—C21—C22A	95.0 (7)	C13—C14—C19—C18	174.2 (4)
S2—N2—C15—C14	83.4 (4)	C15—C14—C19—C18	−2.0 (7)
S2—N2—C15—C16	−95.7 (4)	N2—C15—C16—C17	179.3 (4)
C21—N2—C15—C14	−127.0 (4)	C14—C15—C16—C17	0.2 (7)
C21—N2—C15—C16	53.9 (6)	C15—C16—C17—C18	0.0 (7)
S2—N2—C21—C22A	−115.6 (7)	C16—C17—C18—C19	−1.2 (7)
O1—C1—C2—C3	135.9 (5)	C17—C18—C19—C14	2.2 (7)
O2—C1—C2—C7	143.7 (4)	N2—C21—C22A—C23A	−170.3 (10)

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O8i	0.93	2.59	3.483 (6)	161
C11A—H11C···O1	0.96	2.57	3.486 (15)	159
C16—H16···O4	0.93	2.51	3.429 (5)	168
C20—H20C···O3ii	0.96	2.57	3.172 (6)	121
C21—H21A···O1	0.97	2.55	3.192 (6)	124
C12—H12A···Cg2iii	0.96	2.84	3.660 (5)	144
C18—H18···Cg1iv	0.93	2.87	3.588 (5)	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C14–C19 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O8i	0.93	2.59	3.483 (6)	161
C11A—H11C⋯O1	0.96	2.57	3.486 (15)	159
C16—H16⋯O4	0.93	2.51	3.429 (5)	168
C20—H20C⋯O3ii	0.96	2.57	3.172 (6)	121
C21—H21A⋯O1	0.97	2.55	3.192 (6)	124
C12—H12A⋯Cg2iii	0.96	2.84	3.660 (5)	144
C18—H18⋯Cg1iv	0.93	2.87	3.588 (5)	135

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