N-(4-Sulfamoylphen-yl)acetamide.

In the title compound, C(8)H(10)N(2)O(3)S, the dihedral angle between the acetamide group and the benzene ring is 15.59 (12)° and the amino group is close to being perpendicular to the benzene ring [N-S-C(ar)-C(ar) (ar = aromatic) torsion angle = 109.4 (2)°]. In the crystal, mol-ecules are linked into supra-molecular tubes parallel to [001] by amine-amide N-H⋯O inter-actions and these are connected into the three-dimensional architecture by amide-sulfonamide N-H⋯O hydrogen bonds. The crystal studied was a racemic twin.

Related literature

For background to the biological applications of related sulfonamides, see: Croitoru et al. (2004 ▶); Dogruer et al. (2010 ▶). For related structures, see: Asiri et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C8H10N2O3S

M = 214.24

Tetragonal,

a = 15.2631 (4) Å

c = 8.0571 (4) Å

V = 1877.00 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.40 × 0.05 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.880, T max = 0.984

3827 measured reflections

1862 independent reflections

1698 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.079

S = 1.02

1862 reflections

140 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 625 Friedel pairs

Flack parameter: 0.48 (9)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011701/hb6682sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011701/hb6682Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011701/hb6682Isup3.cml

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

C8H10N2O3S	Dx = 1.516 Mg m−3
Mr = 214.24	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 2081 reflections
Hall symbol: P -4 2n	θ = 2.7–27.5°
a = 15.2631 (4) Å	µ = 0.33 mm−1
c = 8.0571 (4) Å	T = 100 K
V = 1877.00 (11) Å3	Prism, colourless
Z = 8	0.40 × 0.05 × 0.05 mm
F(000) = 896

Agilent SuperNova Dual diffractometer with an Atlas detector	1862 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1698 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.028
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −12→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→10
Tmin = 0.880, Tmax = 0.984	l = −10→6
3827 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.7254P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
1862 reflections	Δρmax = 0.25 e Å−3
140 parameters	Δρmin = −0.27 e Å−3
3 restraints	Absolute structure: Flack (1983), 625 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.48 (9)

	x	y	z	Uiso*/Ueq
S1	0.42050 (3)	0.72593 (3)	0.79689 (8)	0.01459 (14)
O1	0.38712 (11)	0.72467 (12)	0.6291 (2)	0.0220 (4)
O2	0.43783 (11)	0.64415 (10)	0.8775 (2)	0.0212 (4)
O3	0.71401 (10)	1.06596 (10)	0.73297 (19)	0.0184 (4)
N1	0.34929 (12)	0.77773 (13)	0.9064 (3)	0.0165 (4)
H1	0.364 (2)	0.783 (2)	1.0119 (16)	0.038 (9)*
H2	0.329 (2)	0.8243 (14)	0.853 (4)	0.053 (11)*
N2	0.75181 (12)	0.92922 (13)	0.8186 (2)	0.0165 (4)
H3	0.7976 (12)	0.8991 (16)	0.852 (3)	0.025 (8)*
C1	0.51900 (14)	0.78616 (14)	0.7979 (3)	0.0153 (4)
C2	0.59105 (15)	0.75505 (15)	0.8838 (3)	0.0163 (5)
H2A	0.5884	0.7002	0.9394	0.020*
C3	0.66665 (15)	0.80408 (14)	0.8881 (3)	0.0164 (5)
H3A	0.7165	0.7826	0.9459	0.020*
C4	0.67072 (14)	0.88484 (15)	0.8086 (3)	0.0155 (5)
C5	0.59846 (15)	0.91651 (16)	0.7215 (4)	0.0227 (5)
H5	0.6011	0.9714	0.6662	0.027*
C6	0.52250 (16)	0.86653 (15)	0.7170 (4)	0.0226 (5)
H6	0.4727	0.8873	0.6583	0.027*
C7	0.77054 (15)	1.01386 (14)	0.7821 (3)	0.0158 (4)
C8	0.86506 (15)	1.03931 (15)	0.8005 (3)	0.0196 (5)
H8A	0.8689	1.1001	0.8392	0.029*
H8B	0.8946	1.0339	0.6930	0.029*
H8C	0.8934	1.0006	0.8813	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0124 (3)	0.0141 (3)	0.0172 (2)	−0.0010 (2)	0.0011 (2)	−0.0006 (3)
O1	0.0201 (8)	0.0260 (9)	0.0199 (8)	−0.0028 (8)	−0.0005 (7)	−0.0042 (8)
O2	0.0197 (9)	0.0116 (8)	0.0323 (9)	−0.0012 (7)	0.0006 (8)	0.0017 (7)
O3	0.0197 (8)	0.0153 (8)	0.0202 (8)	0.0024 (6)	0.0016 (7)	0.0017 (7)
N1	0.0122 (9)	0.0199 (10)	0.0176 (9)	0.0014 (8)	0.0033 (9)	0.0026 (9)
N2	0.0103 (9)	0.0147 (9)	0.0247 (10)	0.0011 (7)	0.0004 (8)	0.0038 (9)
C1	0.0129 (10)	0.0167 (10)	0.0163 (9)	−0.0010 (9)	0.0012 (10)	−0.0009 (11)
C2	0.0174 (11)	0.0119 (10)	0.0197 (11)	0.0028 (9)	0.0001 (10)	0.0017 (9)
C3	0.0138 (11)	0.0140 (11)	0.0215 (11)	0.0039 (9)	−0.0002 (10)	0.0041 (10)
C4	0.0119 (10)	0.0148 (10)	0.0197 (11)	0.0010 (8)	0.0020 (10)	−0.0012 (10)
C5	0.0167 (11)	0.0188 (11)	0.0326 (13)	−0.0003 (9)	−0.0011 (11)	0.0109 (12)
C6	0.0147 (11)	0.0237 (12)	0.0296 (12)	0.0015 (10)	−0.0034 (12)	0.0107 (12)
C7	0.0180 (11)	0.0145 (10)	0.0150 (10)	0.0012 (9)	0.0035 (10)	−0.0010 (10)
C8	0.0188 (11)	0.0186 (11)	0.0214 (11)	−0.0034 (9)	0.0003 (11)	0.0012 (11)

S1—O2	1.4316 (17)	C2—C3	1.376 (3)
S1—O1	1.4446 (17)	C2—H2A	0.9500
S1—N1	1.608 (2)	C3—C4	1.391 (3)
S1—C1	1.762 (2)	C3—H3A	0.9500
O3—C7	1.238 (3)	C4—C5	1.394 (3)
N1—H1	0.880 (10)	C5—C6	1.388 (3)
N1—H2	0.885 (10)	C5—H5	0.9500
N2—C7	1.355 (3)	C6—H6	0.9500
N2—C4	1.413 (3)	C7—C8	1.501 (3)
N2—H3	0.878 (10)	C8—H8A	0.9800
C1—C2	1.384 (3)	C8—H8B	0.9800
C1—C6	1.390 (3)	C8—H8C	0.9800
O2—S1—O1	118.55 (11)	C4—C3—H3A	119.7
O2—S1—N1	107.74 (11)	C3—C4—C5	120.3 (2)
O1—S1—N1	106.36 (10)	C3—C4—N2	115.9 (2)
O2—S1—C1	107.16 (10)	C5—C4—N2	123.8 (2)
O1—S1—C1	108.19 (11)	C6—C5—C4	118.9 (2)
N1—S1—C1	108.52 (11)	C6—C5—H5	120.5
S1—N1—H1	114 (2)	C4—C5—H5	120.5
S1—N1—H2	111 (2)	C5—C6—C1	120.3 (2)
H1—N1—H2	119 (3)	C5—C6—H6	119.9
C7—N2—C4	128.99 (19)	C1—C6—H6	119.9
C7—N2—H3	113.4 (18)	O3—C7—N2	122.3 (2)
C4—N2—H3	117.6 (18)	O3—C7—C8	122.33 (19)
C2—C1—C6	120.5 (2)	N2—C7—C8	115.34 (19)
C2—C1—S1	120.10 (17)	C7—C8—H8A	109.5
C6—C1—S1	119.40 (18)	C7—C8—H8B	109.5
C3—C2—C1	119.5 (2)	H8A—C8—H8B	109.5
C3—C2—H2A	120.2	C7—C8—H8C	109.5
C1—C2—H2A	120.2	H8A—C8—H8C	109.5
C2—C3—C4	120.5 (2)	H8B—C8—H8C	109.5
C2—C3—H3A	119.7
O2—S1—C1—C2	−6.7 (2)	C2—C3—C4—N2	−179.1 (2)
O1—S1—C1—C2	−135.60 (19)	C7—N2—C4—C3	−166.2 (2)
N1—S1—C1—C2	109.4 (2)	C7—N2—C4—C5	15.6 (4)
O2—S1—C1—C6	175.7 (2)	C3—C4—C5—C6	0.5 (4)
O1—S1—C1—C6	46.8 (2)	N2—C4—C5—C6	178.6 (2)
N1—S1—C1—C6	−68.2 (2)	C4—C5—C6—C1	−0.1 (4)
C6—C1—C2—C3	−0.3 (4)	C2—C1—C6—C5	0.0 (4)
S1—C1—C2—C3	−177.88 (19)	S1—C1—C6—C5	177.6 (2)
C1—C2—C3—C4	0.7 (3)	C4—N2—C7—O3	0.5 (4)
C2—C3—C4—C5	−0.8 (4)	C4—N2—C7—C8	−177.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88 (1)	2.08 (1)	2.935 (3)	163 (3)
N1—H2···O3ii	0.89 (1)	2.04 (1)	2.929 (3)	178 (3)
N2—H3···O1iii	0.88 (1)	2.34 (2)	3.156 (3)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88 (1)	2.08 (1)	2.935 (3)	163 (3)
N1—H2⋯O3ii	0.89 (1)	2.04 (1)	2.929 (3)	178 (3)
N2—H3⋯O1iii	0.88 (1)	2.34 (2)	3.156 (3)	155 (2)

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