2-Amino-N-(4-methyl­phenyl­sulfon­yl)-N-phenyl­benzene­sulfonamide

Song, Z.-W.

doi:10.1107/S1600536808007447

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o744

doi:10.1107/S1600536808007447

Open

access

2-Amino-N-(4-methylphenylsulfonyl)-N-phenylbenzenesulfonamide

Zu-Wei Song ^a ^*

^aCollege of Science, Qingdao Agricultural University, Qingdao 266109, People's Republic of China
^*Correspondence e-mail: songzuwei2008@yahoo.cn

(Received 20 February 2008; accepted 18 March 2008; online 29 March 2008)

In the title molecule, C₁₉H₁₈N₂O₄S₂, the phenyl ring makes dihedral angles of 33.99 (2) and 43.70 (3)° with the two methyl-substituted benzene rings. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Henschel et al. (1996 ). For details of the biological activities of sulfonamide-containing compounds, see: Kamoshita et al. (1987 ). For related literature, see: Allen et al. (1987 ); Zhang et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₈N₂O₄S₂
M_r = 402.47
Monoclinic, P 2₁ /c
a = 14.6245 (3) Å
b = 10.0454 (2) Å
c = 13.4735 (4) Å
β = 107.478 (2)°
V = 1887.99 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 (2) K
0.52 × 0.32 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi 1995 ) T_min = 0.855, T_max = 0.926
17437 measured reflections
4312 independent reflections
3531 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.121
S = 1.07
4312 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O3ⁱ	0.86	2.20	3.062 (2)	176
C19—H19A⋯O1ⁱⁱ	0.96	2.57	3.517 (3)	169
C19—H19C⋯O4ⁱⁱⁱ	0.96	2.58	3.538 (3)	174
N2—H2C⋯O2	0.86	2.23	2.893 (2)	133
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007447/cv2388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007447/cv2388Isup2.hkl

checkCIF report

Comment top

Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalysts (Zhang et al., 2007). Herein we report the crystal structure of the title compound, (I).

In (I) (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and in a good agreement with those reported previously (Henschel et al., 1996). The phenyl ring (C7—C12) makes the dihedral angles of 33.99 (2) and 43.70 (3)°, respectively, with two benzene rings (C1—C6/N1 and C13—C19). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For the crystal structures of related compounds, see: Henschel et al. (1996). For details of the biological activities of sulfonimide-containing compounds, see: Kamoshita et al. (1987). For related literature, see: Allen et al. (1987); Zhang et al. (2007).

Experimental top

A solution of methylsulfonyl chloride (1 mmol) was dissolved in anhydrous CH₂Cl₂ (10 ml), and dropwise added over a period of 10 min to a solution of 2-amino-N-methyl-benzenesulfonamide (1 mmol) and DMAP₂ (3 mmol) in CH₂Cl₂ (10 ml) at 273 K. The mixture was stirred for 4 h at room temperature. The organic phase was washed with 2 N HCl twice, and dried over anhydrous Na₂SO₄. The solvent was removed and the residue was purified by flash chromatography (1:1 cyclohexane:dichloromethane) to give (I) as a white solid (294 mg, 73%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol and dichloromethane at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

2-Amino-N-(4-methylphenylsulfonyl)-N-phenylbenzenesulfonamide top

Crystal data top

C₁₉H₁₈N₂O₄S₂	F(000) = 840
M_r = 402.47	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2652 reflections
a = 14.6245 (3) Å	θ = 2.6–25.6°
b = 10.0454 (2) Å	µ = 0.31 mm⁻¹
c = 13.4735 (4) Å	T = 293 K
β = 107.478 (2)°	Platelet, yellow
V = 1887.99 (7) Å³	0.52 × 0.32 × 0.25 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4312 independent reflections
Radiation source: Rotating Anode	3531 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω oscillation scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	h = −18→18
T_min = 0.855, T_max = 0.927	k = −13→13
17437 measured reflections	l = −17→17

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0647P)² + 0.3731P] where P = (F_o² + 2F_c²)/3
4312 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₁₈N₂O₄S₂	V = 1887.99 (7) Å³
M_r = 402.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.6245 (3) Å	µ = 0.31 mm⁻¹
b = 10.0454 (2) Å	T = 293 K
c = 13.4735 (4) Å	0.52 × 0.32 × 0.25 mm
β = 107.478 (2)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	4312 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi 1995)	3531 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.927	R_int = 0.038
17437 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
4312 reflections	Δρ_min = −0.26 e Å⁻³
245 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.18008 (3)	0.28081 (5)	0.24068 (4)	0.04085 (14)
S2	0.24948 (3)	0.51762 (5)	0.14469 (3)	0.04136 (14)
O1	0.24248 (10)	0.20876 (14)	0.32523 (12)	0.0550 (4)
O2	0.16312 (11)	0.23184 (16)	0.13781 (11)	0.0573 (4)
O3	0.18520 (10)	0.46901 (19)	0.05005 (10)	0.0595 (4)
O4	0.24789 (12)	0.65454 (14)	0.17142 (12)	0.0571 (4)
N1	0.22958 (11)	0.43445 (16)	0.24350 (11)	0.0386 (3)
N2	−0.00565 (13)	0.3985 (2)	0.09409 (13)	0.0651 (6)
H2B	−0.0542	0.4371	0.0515	0.078*
H2C	0.0415	0.3727	0.0731	0.078*
C1	−0.00348 (13)	0.3782 (2)	0.19378 (15)	0.0431 (4)
C2	−0.08053 (14)	0.4204 (2)	0.22702 (18)	0.0541 (5)
H2D	−0.1332	0.4599	0.1794	0.065*
C3	−0.08033 (17)	0.4052 (3)	0.3272 (2)	0.0667 (6)
H3B	−0.1326	0.4346	0.3469	0.080*
C4	−0.00295 (18)	0.3463 (3)	0.4010 (2)	0.0691 (7)
H4B	−0.0034	0.3370	0.4696	0.083*
C5	0.07352 (16)	0.3022 (2)	0.37162 (16)	0.0540 (5)
H5A	0.1251	0.2618	0.4202	0.065*
C6	0.07447 (12)	0.31772 (19)	0.26886 (14)	0.0399 (4)
C7	0.25885 (13)	0.49745 (18)	0.34475 (13)	0.0375 (4)
C8	0.19747 (14)	0.5849 (2)	0.37156 (16)	0.0459 (4)
H8A	0.1393	0.6076	0.3234	0.055*
C9	0.22318 (18)	0.6384 (2)	0.47042 (19)	0.0586 (6)
H9A	0.1821	0.6970	0.4894	0.070*
C10	0.3098 (2)	0.6048 (3)	0.54093 (18)	0.0650 (6)
H10A	0.3268	0.6406	0.6077	0.078*
C11	0.37175 (19)	0.5185 (3)	0.51344 (18)	0.0640 (6)
H11A	0.4302	0.4969	0.5615	0.077*
C12	0.34685 (14)	0.4643 (2)	0.41479 (15)	0.0497 (5)
H12A	0.3883	0.4066	0.3956	0.060*
C13	0.36661 (12)	0.47731 (19)	0.14622 (13)	0.0384 (4)
C14	0.44113 (15)	0.5618 (2)	0.19508 (16)	0.0514 (5)
H14A	0.4301	0.6370	0.2301	0.062*
C15	0.53243 (15)	0.5326 (2)	0.19103 (18)	0.0562 (5)
H15A	0.5829	0.5890	0.2239	0.067*
C16	0.55032 (14)	0.4216 (2)	0.13933 (16)	0.0494 (5)
C17	0.47460 (17)	0.3389 (2)	0.09216 (19)	0.0590 (6)
H17A	0.4860	0.2635	0.0576	0.071*
C18	0.38235 (15)	0.3642 (2)	0.09434 (18)	0.0523 (5)
H18A	0.3322	0.3071	0.0620	0.063*
C19	0.64941 (17)	0.3926 (3)	0.1334 (2)	0.0718 (7)
H19A	0.6850	0.4742	0.1402	0.108*
H19B	0.6451	0.3521	0.0676	0.108*
H19C	0.6815	0.3331	0.1887	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0370 (2)	0.0369 (2)	0.0459 (3)	0.00456 (18)	0.00835 (18)	−0.00020 (18)
S2	0.0365 (2)	0.0506 (3)	0.0373 (2)	0.00913 (19)	0.01168 (18)	0.00992 (19)
O1	0.0466 (8)	0.0449 (8)	0.0664 (9)	0.0112 (6)	0.0064 (7)	0.0118 (7)
O2	0.0573 (9)	0.0564 (9)	0.0567 (8)	0.0020 (7)	0.0148 (7)	−0.0172 (7)
O3	0.0401 (7)	0.0969 (12)	0.0360 (7)	0.0060 (8)	0.0031 (6)	0.0088 (7)
O4	0.0668 (10)	0.0444 (8)	0.0697 (9)	0.0160 (7)	0.0354 (8)	0.0182 (7)
N1	0.0390 (8)	0.0422 (8)	0.0361 (7)	−0.0013 (6)	0.0133 (6)	0.0008 (6)
N2	0.0426 (9)	0.1027 (17)	0.0438 (9)	0.0165 (10)	0.0037 (7)	0.0140 (10)
C1	0.0340 (8)	0.0449 (10)	0.0468 (10)	−0.0028 (8)	0.0067 (7)	0.0042 (8)
C2	0.0347 (9)	0.0589 (13)	0.0679 (13)	0.0040 (9)	0.0145 (9)	0.0136 (11)
C3	0.0513 (12)	0.0765 (16)	0.0834 (16)	0.0059 (12)	0.0371 (12)	0.0146 (14)
C4	0.0654 (15)	0.0889 (19)	0.0633 (14)	0.0073 (14)	0.0350 (12)	0.0226 (13)
C5	0.0492 (11)	0.0615 (13)	0.0510 (11)	0.0031 (10)	0.0147 (9)	0.0201 (10)
C6	0.0326 (8)	0.0389 (9)	0.0460 (9)	−0.0015 (7)	0.0085 (7)	0.0053 (8)
C7	0.0395 (9)	0.0388 (9)	0.0352 (8)	−0.0038 (7)	0.0128 (7)	−0.0001 (7)
C8	0.0444 (10)	0.0430 (10)	0.0532 (11)	0.0009 (8)	0.0189 (8)	−0.0003 (8)
C9	0.0690 (14)	0.0522 (12)	0.0646 (13)	−0.0004 (11)	0.0353 (11)	−0.0124 (10)
C10	0.0861 (18)	0.0632 (14)	0.0464 (12)	−0.0049 (13)	0.0208 (11)	−0.0143 (10)
C11	0.0643 (14)	0.0713 (15)	0.0459 (11)	0.0031 (12)	0.0005 (10)	−0.0055 (11)
C12	0.0429 (10)	0.0574 (12)	0.0459 (10)	0.0052 (9)	0.0089 (8)	−0.0034 (9)
C13	0.0341 (8)	0.0462 (10)	0.0355 (8)	0.0042 (7)	0.0116 (7)	0.0048 (7)
C14	0.0454 (11)	0.0551 (12)	0.0541 (11)	−0.0023 (9)	0.0157 (9)	−0.0107 (10)
C15	0.0390 (10)	0.0646 (14)	0.0620 (13)	−0.0083 (10)	0.0104 (9)	−0.0056 (11)
C16	0.0384 (10)	0.0553 (12)	0.0573 (12)	0.0063 (9)	0.0189 (9)	0.0121 (9)
C17	0.0546 (12)	0.0540 (12)	0.0748 (15)	0.0035 (10)	0.0291 (11)	−0.0118 (11)
C18	0.0416 (10)	0.0533 (12)	0.0627 (12)	−0.0037 (9)	0.0168 (9)	−0.0106 (10)
C19	0.0484 (12)	0.0763 (17)	0.100 (2)	0.0100 (12)	0.0359 (13)	0.0127 (15)

Geometric parameters (Å, º) top

S1—O2	1.4206 (15)	C8—C9	1.379 (3)
S1—O1	1.4248 (14)	C8—H8A	0.9300
S1—N1	1.7002 (16)	C9—C10	1.378 (3)
S1—C6	1.7378 (19)	C9—H9A	0.9300
S2—O4	1.4237 (16)	C10—C11	1.382 (4)
S2—O3	1.4241 (15)	C10—H10A	0.9300
S2—N1	1.6698 (15)	C11—C12	1.380 (3)
S2—C13	1.7543 (18)	C11—H11A	0.9300
N1—C7	1.447 (2)	C12—H12A	0.9300
N2—C1	1.349 (3)	C13—C14	1.382 (3)
N2—H2B	0.8600	C13—C18	1.389 (3)
N2—H2C	0.8600	C14—C15	1.384 (3)
C1—C2	1.398 (3)	C14—H14A	0.9300
C1—C6	1.414 (2)	C15—C16	1.380 (3)
C2—C3	1.357 (3)	C15—H15A	0.9300
C2—H2D	0.9300	C16—C17	1.377 (3)
C3—C4	1.394 (3)	C16—C19	1.504 (3)
C3—H3B	0.9300	C17—C18	1.382 (3)
C4—C5	1.367 (3)	C17—H17A	0.9300
C4—H4B	0.9300	C18—H18A	0.9300
C5—C6	1.397 (3)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C7—C8	1.380 (3)	C19—H19C	0.9600
C7—C12	1.389 (3)

O2—S1—O1	119.11 (10)	C9—C8—C7	119.4 (2)
O2—S1—N1	106.54 (9)	C9—C8—H8A	120.3
O1—S1—N1	106.09 (8)	C7—C8—H8A	120.3
O2—S1—C6	112.39 (9)	C10—C9—C8	119.9 (2)
O1—S1—C6	109.36 (9)	C10—C9—H9A	120.1
N1—S1—C6	101.64 (8)	C8—C9—H9A	120.1
O4—S2—O3	120.08 (10)	C9—C10—C11	120.6 (2)
O4—S2—N1	105.17 (8)	C9—C10—H10A	119.7
O3—S2—N1	108.43 (9)	C11—C10—H10A	119.7
O4—S2—C13	108.07 (9)	C12—C11—C10	120.1 (2)
O3—S2—C13	108.12 (9)	C12—C11—H11A	120.0
N1—S2—C13	106.17 (8)	C10—C11—H11A	120.0
C7—N1—S2	117.37 (12)	C11—C12—C7	118.8 (2)
C7—N1—S1	114.93 (11)	C11—C12—H12A	120.6
S2—N1—S1	127.69 (9)	C7—C12—H12A	120.6
C1—N2—H2B	120.0	C14—C13—C18	121.05 (18)
C1—N2—H2C	120.0	C14—C13—S2	119.43 (15)
H2B—N2—H2C	120.0	C18—C13—S2	119.45 (15)
N2—C1—C2	119.54 (18)	C13—C14—C15	118.9 (2)
N2—C1—C6	123.36 (18)	C13—C14—H14A	120.6
C2—C1—C6	117.10 (18)	C15—C14—H14A	120.6
C3—C2—C1	121.5 (2)	C16—C15—C14	121.5 (2)
C3—C2—H2D	119.2	C16—C15—H15A	119.3
C1—C2—H2D	119.2	C14—C15—H15A	119.3
C2—C3—C4	121.1 (2)	C17—C16—C15	118.16 (19)
C2—C3—H3B	119.5	C17—C16—C19	120.9 (2)
C4—C3—H3B	119.5	C15—C16—C19	121.0 (2)
C5—C4—C3	119.3 (2)	C16—C17—C18	122.3 (2)
C5—C4—H4B	120.3	C16—C17—H17A	118.9
C3—C4—H4B	120.3	C18—C17—H17A	118.9
C4—C5—C6	120.2 (2)	C17—C18—C13	118.12 (19)
C4—C5—H5A	119.9	C17—C18—H18A	120.9
C6—C5—H5A	119.9	C13—C18—H18A	120.9
C5—C6—C1	120.73 (18)	C16—C19—H19A	109.5
C5—C6—S1	117.82 (14)	C16—C19—H19B	109.5
C1—C6—S1	120.92 (14)	H19A—C19—H19B	109.5
C8—C7—C12	121.20 (18)	C16—C19—H19C	109.5
C8—C7—N1	119.59 (16)	H19A—C19—H19C	109.5
C12—C7—N1	119.15 (17)	H19B—C19—H19C	109.5

O4—S2—N1—C7	−27.73 (15)	S2—N1—C7—C8	85.99 (19)
O3—S2—N1—C7	−157.36 (13)	S1—N1—C7—C8	−95.07 (18)
C13—S2—N1—C7	86.67 (14)	S2—N1—C7—C12	−96.67 (19)
O4—S2—N1—S1	153.48 (12)	S1—N1—C7—C12	82.28 (19)
O3—S2—N1—S1	23.85 (15)	C12—C7—C8—C9	−1.3 (3)
C13—S2—N1—S1	−92.12 (13)	N1—C7—C8—C9	176.02 (18)
O2—S1—N1—C7	−175.64 (13)	C7—C8—C9—C10	0.4 (3)
O1—S1—N1—C7	−47.78 (15)	C8—C9—C10—C11	0.4 (4)
C6—S1—N1—C7	66.53 (14)	C9—C10—C11—C12	−0.4 (4)
O2—S1—N1—S2	3.18 (14)	C10—C11—C12—C7	−0.4 (4)
O1—S1—N1—S2	131.04 (12)	C8—C7—C12—C11	1.2 (3)
C6—S1—N1—S2	−114.65 (12)	N1—C7—C12—C11	−176.1 (2)
N2—C1—C2—C3	−178.3 (2)	O4—S2—C13—C14	16.10 (18)
C6—C1—C2—C3	0.6 (3)	O3—S2—C13—C14	147.52 (16)
C1—C2—C3—C4	−0.2 (4)	N1—S2—C13—C14	−96.30 (17)
C2—C3—C4—C5	−0.6 (4)	O4—S2—C13—C18	−161.03 (16)
C3—C4—C5—C6	0.8 (4)	O3—S2—C13—C18	−29.62 (19)
C4—C5—C6—C1	−0.4 (3)	N1—S2—C13—C18	86.56 (17)
C4—C5—C6—S1	171.3 (2)	C18—C13—C14—C15	0.5 (3)
N2—C1—C6—C5	178.5 (2)	S2—C13—C14—C15	−176.61 (17)
C2—C1—C6—C5	−0.3 (3)	C13—C14—C15—C16	0.1 (3)
N2—C1—C6—S1	7.1 (3)	C14—C15—C16—C17	−0.6 (3)
C2—C1—C6—S1	−171.74 (16)	C14—C15—C16—C19	178.6 (2)
O2—S1—C6—C5	148.79 (17)	C15—C16—C17—C18	0.6 (4)
O1—S1—C6—C5	14.18 (19)	C19—C16—C17—C18	−178.7 (2)
N1—S1—C6—C5	−97.68 (17)	C16—C17—C18—C13	0.0 (4)
O2—S1—C6—C1	−39.51 (19)	C14—C13—C18—C17	−0.5 (3)
O1—S1—C6—C1	−174.13 (15)	S2—C13—C18—C17	176.55 (17)
N1—S1—C6—C1	74.01 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3ⁱ	0.86	2.20	3.062 (2)	176
C19—H19A···O1ⁱⁱ	0.96	2.57	3.517 (3)	169
C19—H19C···O4ⁱⁱⁱ	0.96	2.58	3.538 (3)	174
N2—H2C···O2	0.86	2.23	2.893 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₂O₄S₂
M_r	402.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.6245 (3), 10.0454 (2), 13.4735 (4)
β (°)	107.478 (2)
V (Å³)	1887.99 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.52 × 0.32 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi 1995)
T_min, T_max	0.855, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	17437, 4312, 3531
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.121, 1.07
No. of reflections	4312
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O3ⁱ	0.86	2.20	3.062 (2)	175.6
C19—H19A···O1ⁱⁱ	0.96	2.57	3.517 (3)	169.3
C19—H19C···O4ⁱⁱⁱ	0.96	2.58	3.538 (3)	173.6
N2—H2C···O2	0.86	2.23	2.893 (2)	133.3

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Henschel, D., Hiemisch, O., Blaschette, A. & Jones, P. G. (1996). Z. Naturforsch. Teil B, 51, 1313–1315. CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kamoshita, K., Matsumoto, H. & Nagano, E. (1987). US Patent 4 670 046. Google Scholar
Rigaku (2004). RAPID-AUTO. Version 3.0. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z. B., Zhou, S. Y. & Nie, J. (2007). J. Mol. Catal. A Chem. 265, 9–14. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o744

doi:10.1107/S1600536808007447

Open

access