Benzyl-sulfamide.

THE CRYSTAL OF THE TITLE COMPOUND [SYSTEMATIC NAME: 4-(benzyl-amino)-benzene-sulfonamide], C(13)H(14)N(2)O(2)S, displays a hydrogen-bonded framework structure. Mol-ecules are doubly N-H⋯O hydrogen bonded to one another via their NH(2) groups and sulfonyl O atoms. These inter-actions generate a hydrogen-bonded ladder structure parallel to the a axis, which contains fused R(2) (2)(8) rings. The NH group serves as the hydrogen-bond donor for a second set of inter-molecular N-H⋯O=S inter-actions.

Related literature

For the pharmacology and synthesis of the title compound, see Goissedet et al. (1936 ▶); Goissedet & Despois (1938 ▶); Mellon et al. (1938 ▶); Long & Bliss (1939 ▶). For related structures, see: Hursthouse et al. (1998 ▶, 1999a ▶,b ▶); Gelbrich et al. (2008 ▶); Davis et al. (1996 ▶); Costanzo et al. (1999 ▶); Kubicki & Codding (2001 ▶);Yathirajan et al. (2005 ▶); Denehy et al. (2006 ▶); Toumieux et al. (2006 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H14N2O2S

M = 262.32

Orthorhombic,

a = 7.8426 (1) Å

b = 10.5549 (11) Å

c = 14.6694 (3) Å

V = 1214.30 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 120 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.950, T max = 0.962

11460 measured reflections

2364 independent reflections

2312 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.061

S = 1.06

2364 reflections

176 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 972 Friedel pairs

Flack parameter: −0.01 (5)

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and Mercury (Bruno et al., 2002 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019490/ez2246sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019490/ez2246Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019490/ez2246Isup3.cml

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

C13H14N2O2S	F(000) = 552
Mr = 262.32	Dx = 1.435 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6120 reflections
a = 7.8426 (1) Å	θ = 2.9–27.5°
b = 10.5549 (11) Å	µ = 0.26 mm−1
c = 14.6694 (3) Å	T = 120 K
V = 1214.30 (13) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.15 mm

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2364 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2312 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 9.091 pixels mm-1	θmax = 26.0°, θmin = 3.2°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→13
Tmin = 0.950, Tmax = 0.962	l = −18→18
11460 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.023	w = 1/[σ2(Fo2) + (0.032P)2 + 0.3394P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.061	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.19 e Å−3
2364 reflections	Δρmin = −0.30 e Å−3
176 parameters	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraints	Extinction coefficient: 0.021 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 972 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.01 (5)

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
S1	0.88925 (4)	0.14891 (3)	0.47921 (2)	0.00933 (11)
O1	1.04460 (12)	0.09326 (9)	0.51381 (7)	0.0132 (2)
O2	0.73029 (12)	0.08853 (9)	0.50432 (7)	0.0127 (2)
N1	0.88280 (16)	0.29082 (11)	0.51938 (8)	0.0124 (3)
H2N	0.789 (2)	0.3327 (18)	0.5037 (13)	0.027 (5)*
H1N	0.9760 (19)	0.3323 (16)	0.5125 (12)	0.016 (4)*
N2	0.94618 (16)	0.14533 (12)	0.07743 (8)	0.0141 (3)
H3N	0.879 (2)	0.0925 (18)	0.0498 (13)	0.032 (5)*
C1	0.89793 (18)	0.15385 (13)	0.36038 (9)	0.0103 (3)
C2	1.00520 (19)	0.23999 (13)	0.31668 (10)	0.0131 (3)
H2	1.0688	0.2990	0.3518	0.016*
C3	1.01965 (19)	0.24017 (13)	0.22311 (10)	0.0135 (3)
H3	1.0908	0.3008	0.1940	0.016*
C4	0.92945 (17)	0.15099 (14)	0.17015 (9)	0.0110 (3)
C5	0.82057 (18)	0.06548 (14)	0.21519 (10)	0.0115 (3)
H5	0.7574	0.0057	0.1805	0.014*
C6	0.80389 (18)	0.06679 (13)	0.30896 (9)	0.0107 (3)
H6	0.7291	0.0090	0.3383	0.013*
C9	1.15434 (18)	0.09176 (14)	−0.09378 (10)	0.0145 (3)
H9	1.2109	0.0486	−0.0456	0.017*
C7	1.03437 (19)	0.24066 (13)	0.02344 (10)	0.0138 (3)
H7A	1.1487	0.2564	0.0497	0.017*
H7B	0.9696	0.3211	0.0251	0.017*
C8	1.05223 (18)	0.19639 (14)	−0.07416 (10)	0.0119 (3)
C10	1.1744 (2)	0.04982 (15)	−0.18294 (11)	0.0182 (3)
H10	1.2445	−0.0214	−0.1957	0.022*
C11	1.0911 (2)	0.11273 (15)	−0.25348 (10)	0.0187 (3)
H11	1.1038	0.0840	−0.3145	0.022*
C12	0.9903 (2)	0.21671 (15)	−0.23489 (11)	0.0184 (3)
H12	0.9340	0.2596	−0.2832	0.022*
C13	0.97056 (19)	0.25909 (14)	−0.14530 (10)	0.0150 (3)
H13	0.9013	0.3309	−0.1329	0.018*

	U11	U22	U33	U12	U13	U23
S1	0.00952 (18)	0.01096 (17)	0.00751 (17)	0.00004 (13)	0.00065 (13)	0.00008 (13)
O1	0.0124 (5)	0.0159 (5)	0.0115 (5)	0.0029 (4)	−0.0014 (4)	0.0013 (4)
O2	0.0118 (5)	0.0143 (5)	0.0120 (5)	−0.0022 (4)	0.0026 (4)	0.0015 (4)
N1	0.0110 (6)	0.0127 (6)	0.0136 (6)	−0.0003 (5)	0.0009 (6)	−0.0031 (5)
N2	0.0181 (6)	0.0152 (6)	0.0090 (6)	−0.0072 (5)	0.0009 (5)	0.0005 (5)
C1	0.0105 (6)	0.0132 (7)	0.0073 (6)	0.0018 (6)	0.0007 (5)	0.0008 (5)
C2	0.0137 (7)	0.0134 (7)	0.0122 (7)	−0.0033 (6)	−0.0011 (6)	−0.0012 (6)
C3	0.0145 (7)	0.0136 (7)	0.0125 (7)	−0.0049 (6)	0.0011 (6)	0.0017 (6)
C4	0.0117 (6)	0.0116 (6)	0.0099 (6)	0.0011 (6)	0.0000 (5)	0.0004 (6)
C5	0.0109 (7)	0.0114 (6)	0.0123 (6)	−0.0016 (5)	−0.0006 (5)	−0.0019 (6)
C6	0.0106 (7)	0.0099 (6)	0.0117 (6)	−0.0007 (5)	0.0008 (5)	0.0006 (6)
C9	0.0132 (7)	0.0150 (7)	0.0154 (7)	−0.0002 (6)	−0.0015 (5)	0.0027 (6)
C7	0.0167 (7)	0.0139 (7)	0.0109 (7)	−0.0039 (6)	0.0016 (6)	0.0016 (6)
C8	0.0117 (7)	0.0128 (6)	0.0112 (7)	−0.0047 (5)	0.0002 (5)	0.0006 (6)
C10	0.0176 (8)	0.0158 (7)	0.0212 (8)	−0.0008 (6)	0.0041 (6)	−0.0029 (6)
C11	0.0220 (8)	0.0236 (8)	0.0105 (7)	−0.0104 (6)	0.0039 (6)	−0.0030 (6)
C12	0.0187 (8)	0.0236 (8)	0.0129 (8)	−0.0059 (6)	−0.0035 (6)	0.0058 (6)
C13	0.0128 (7)	0.0175 (8)	0.0146 (7)	0.0006 (6)	0.0002 (6)	0.0029 (6)

S1—O1	1.4447 (10)	C5—H5	0.9500
S1—O2	1.4477 (10)	C6—H6	0.9500
S1—N1	1.6104 (12)	C9—C10	1.390 (2)
S1—C1	1.7452 (13)	C9—C8	1.394 (2)
N1—H2N	0.889 (15)	C9—H9	0.9500
N1—H1N	0.858 (14)	C7—C8	1.5126 (19)
N2—C4	1.3677 (17)	C7—H7A	0.9900
N2—C7	1.4553 (17)	C7—H7B	0.9900
N2—H3N	0.867 (15)	C8—C13	1.392 (2)
C1—C2	1.3948 (19)	C10—C11	1.392 (2)
C1—C6	1.399 (2)	C10—H10	0.9500
C2—C3	1.377 (2)	C11—C12	1.380 (2)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.411 (2)	C12—C13	1.397 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.407 (2)	C13—H13	0.9500
C5—C6	1.3817 (19)
O1—S1—O2	117.25 (6)	C5—C6—C1	119.57 (13)
O1—S1—N1	106.02 (6)	C5—C6—H6	120.2
O2—S1—N1	106.81 (6)	C1—C6—H6	120.2
O1—S1—C1	109.28 (6)	C10—C9—C8	120.77 (14)
O2—S1—C1	107.51 (6)	C10—C9—H9	119.6
N1—S1—C1	109.81 (6)	C8—C9—H9	119.6
S1—N1—H2N	113.2 (13)	N2—C7—C8	110.22 (11)
S1—N1—H1N	113.9 (12)	N2—C7—H7A	109.6
H2N—N1—H1N	114.9 (17)	C8—C7—H7A	109.6
C4—N2—C7	123.82 (12)	N2—C7—H7B	109.6
C4—N2—H3N	115.7 (14)	C8—C7—H7B	109.6
C7—N2—H3N	118.6 (14)	H7A—C7—H7B	108.1
C2—C1—C6	119.88 (13)	C13—C8—C9	119.09 (14)
C2—C1—S1	120.14 (11)	C13—C8—C7	121.35 (13)
C6—C1—S1	119.89 (10)	C9—C8—C7	119.56 (13)
C3—C2—C1	120.57 (13)	C9—C10—C11	119.64 (14)
C3—C2—H2	119.7	C9—C10—H10	120.2
C1—C2—H2	119.7	C11—C10—H10	120.2
C2—C3—C4	120.44 (13)	C12—C11—C10	120.08 (14)
C2—C3—H3	119.8	C12—C11—H11	120.0
C4—C3—H3	119.8	C10—C11—H11	120.0
N2—C4—C5	119.81 (13)	C11—C12—C13	120.27 (15)
N2—C4—C3	121.92 (13)	C11—C12—H12	119.9
C5—C4—C3	118.27 (13)	C13—C12—H12	119.9
C6—C5—C4	121.22 (13)	C8—C13—C12	120.15 (14)
C6—C5—H5	119.4	C8—C13—H13	119.9
C4—C5—H5	119.4	C12—C13—H13	119.9
N1—S1—C1—C2	43.59 (14)	N2—C7—C8—C9	−65.94 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3N···O2i	0.87 (2)	2.20 (2)	3.0264 (16)	160.(2)
N1—H2N···O1ii	0.89 (2)	2.09 (2)	2.9613 (16)	168.(2)
N1—H1N···O2iii	0.86 (1)	2.18 (1)	3.0281 (16)	172.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H3N⋯O2i	0.87 (2)	2.20 (2)	3.0264 (16)	160 (2)
N1—H2N⋯O1ii	0.89 (2)	2.09 (2)	2.9613 (16)	168 (2)
N1—H1N⋯O2iii	0.86 (1)	2.18 (1)	3.0281 (16)	172 (2)

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