Benzyl­sulfamide

Gelbrich, T.; Haddow, M.F.; Griesser, U.J.

doi:10.1107/S1600536811019490

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1551-o1552

doi:10.1107/S1600536811019490

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Benzylsulfamide

Thomas Gelbrich,^a ^* Mairi F. Haddow ^a ‡ and Ulrich J. Griesser ^a

^aInstitute of Pharmacy, University of Innsbruck, Innrain 52, 6020 Innsbruck, Austria
^*Correspondence e-mail: thomas.gelbrich@uibk.ac.at

(Received 6 May 2011; accepted 23 May 2011; online 28 May 2011)

The crystal of the title compound [systematic name: 4-(benzylamino)benzenesulfonamide], C₁₃H₁₄N₂O₂S, displays a hydrogen-bonded framework structure. Molecules are doubly N—H⋯O hydrogen bonded to one another via their NH₂ groups and sulfonyl O atoms. These interactions generate a hydrogen-bonded ladder structure parallel to the a axis, which contains fused R₂²(8) rings. The NH group serves as the hydrogen-bond donor for a second set of intermolecular N—H⋯O=S interactions.

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_r = 262.32
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.023
wR(F²) = 0.061
S = 1.06
2364 reflections
176 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 972 Friedel pairs
Flack parameter: −0.01 (5)

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) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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 ).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811019490/ez2246Isup3.cml

checkCIF report

Comment top

The title compound (synonyms: proseptazine, septazine, benzylsulfanilamide, chemodyn; CAS No. 104–22–3), first marketed in 1936, was one of the early antibacterial agents of the sulfonamide class (Goissedet et al., 1936; Goissedet & Despois, 1938; Mellon et al., 1938; Long & Bliss, 1939). The C–N–(C₆H₄)–S fragment of the molecule (see Fig. 1) is essentially planar, and the molecular geometry is characterized by the torsion angles N1–S1–C1–C2 and N2–C7–C8–C9 of 43.6 (1)° and -65.9 (2)°, respectively.

The crystal structure contains three independent intermolecular N—H···O=S bonds which lead to the formation of an H-bonded framework. Each molecule is doubly H-bonded, via its NH₂ and sulfonyl groups, to two neighbouring molecules. These interactions generate an N—H···O=S-bonded ladder structure parallel to [100], which consists of fused R²₂(8) rings (Bernstein et al., 1995) and displays a 2₁ symmetry. This situation is illustrated in Fig. 2. The same one-dimensional structure has been found previously in only a few other compounds of the sulfonamide class, see Davis et al. (1996); Costanzo et al. (1999); Kubicki & Codding (2001);Yathirajan et al. (2005); Denehy et al. (2006); Toumieux et al. (2006).

The sulfonyl oxygen atom O2 accepts an additional H-bond from the NH group of a neighbouring molecule. This interaction links molecules which are related to one another by a 2₁ operation parallel to the c-axis (see Fig. 3).

Related literature top

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).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top

	Fig. 1. The molecular structure with displacement ellipsoids drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary size.
	Fig. 2. Ladder structure parallel to [100] formed by H-bonds involving the NH₂ group. The interactions between the NH group and O2 are indicated by arrows. O and H atoms directly engaged in N–H···O bonds are drawn as balls.
	Fig. 3. H-bonded framework structure viewed parallel to the a-axis, with H-bonds indicated by arrows.

4-(benzylamino)benzenesulfonamide top

Crystal data top

C₁₃H₁₄N₂O₂S	F(000) = 552
M_r = 262.32	D_x = 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

Data collection top

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 monochromator	R_int = 0.027
Detector resolution: 9.091 pixels mm^-1	θ_max = 26.0°, θ_min = 3.2°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −12→13
T_min = 0.950, T_max = 0.962	l = −18→18
11460 measured reflections

Refinement top

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(F_o²) + (0.032P)² + 0.3394P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.061	(Δ/σ)_max = 0.001
S = 1.06	Δρ_max = 0.19 e Å⁻³
2364 reflections	Δρ_min = −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	Absolute structure parameter: −0.01 (5)

Crystal data top

C₁₃H₁₄N₂O₂S	V = 1214.30 (13) Å³
M_r = 262.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.8426 (1) Å	µ = 0.26 mm⁻¹
b = 10.5549 (11) Å	T = 120 K
c = 14.6694 (3) Å	0.20 × 0.20 × 0.15 mm

Data collection top

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2364 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2312 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.962	R_int = 0.027
11460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.061	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.30 e Å⁻³
2364 reflections	Absolute structure: Flack (1983), 972 Friedel pairs
176 parameters	Absolute structure parameter: −0.01 (5)
3 restraints

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	0.88925 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄N₂O₂S
M_r	262.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	7.8426 (1), 10.5549 (11), 14.6694 (3)
V (Å³)	1214.30 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.950, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	11460, 2364, 2312
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.061, 1.06
No. of reflections	2364
No. of parameters	176
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.30
Absolute structure	Flack (1983), 972 Friedel pairs
Absolute structure parameter	−0.01 (5)

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and Mercury (Bruno et al., 2002), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H3N···O2ⁱ	0.867 (15)	2.199 (16)	3.0264 (16)	159.7 (19)
N1—H2N···O1ⁱⁱ	0.889 (15)	2.085 (15)	2.9613 (16)	168.3 (18)
N1—H1N···O2ⁱⁱⁱ	0.858 (14)	2.177 (14)	3.0281 (16)	171.9 (16)

Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) x−1/2, −y+1/2, −z+1; (iii) x+1/2, −y+1/2, −z+1.

Footnotes

‡Current address: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, England.

Acknowledgements

TG gratefully acknowledges funding by the Austrian Science Fund (FWF), project M1135-N17.

References

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