4-(3-Chloro-2,2-dimethyl-propanamido)-benzene-sulfonamide.

In the title compound, C11H15ClN2O3S, the 3-chloro-2,2-dimethyl-propanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the anti­bacterial, anti­microbial and anti­glaucoma activity of sulfonamides and their derivatives and for their physical properties and pharmacological applications, see: Poulsen et al. (2005 ▶); Supuran & Scozzafava (2000 ▶). For related structures, see: Akkurt et al. (2010 ▶); Idemudia et al. (2012 ▶); Asiri et al. (2012 ▶). For the synthesis, see: Türkmen et al. (2011 ▶).

Experimental

Crystal data

C11H15ClN2O3S

M = 290.77

Monoclinic,

a = 20.4359 (11) Å

b = 7.2437 (4) Å

c = 9.4693 (5) Å

β = 98.222 (3)°

V = 1387.35 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 294 K

0.31 × 0.14 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶) T min = 0.931, T max = 0.946

4240 measured reflections

4240 independent reflections

2054 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.231

S = 1.02

4240 reflections

175 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812046806/sj5282sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046806/sj5282Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046806/sj5282Isup3.cml

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

C11H15ClN2O3S	F(000) = 608
Mr = 290.77	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5710 reflections
a = 20.4359 (11) Å	θ = 2.5–30.5°
b = 7.2437 (4) Å	µ = 0.43 mm−1
c = 9.4693 (5) Å	T = 294 K
β = 98.222 (3)°	Needle, white
V = 1387.35 (13) Å3	0.31 × 0.14 × 0.13 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	4240 independent reflections
Radiation source: Sealed Tube	2054 reflections with I > 2σ(I)
Graphite Monochromator monochromator	Rint = 0.000
Detector resolution: 10.0000 pixels mm-1	θmax = 30.6°, θmin = 3.0°
ω scans	h = −29→28
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→10
Tmin = 0.931, Tmax = 0.946	l = 0→13
4240 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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0751P)2 + 1.0033P] where P = (Fo2 + 2Fc2)/3
4240 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.36 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

Experimental. Absorption correction: (XABS2; Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 parameters

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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.05415 (8)	0.1450 (2)	0.13028 (15)	0.1040 (6)
S1	0.43958 (5)	−0.22940 (14)	0.07872 (10)	0.0540 (3)
O1	0.45415 (14)	−0.1736 (4)	−0.0593 (3)	0.0634 (10)
O2	0.42131 (15)	−0.4163 (4)	0.1004 (3)	0.0684 (11)
O3	0.19397 (15)	0.3907 (4)	0.0227 (3)	0.0689 (10)
N1	0.50493 (18)	−0.1856 (5)	0.1885 (3)	0.0592 (11)
N2	0.22555 (18)	0.2516 (5)	0.2354 (4)	0.0640 (13)
C1	0.37522 (19)	−0.0863 (6)	0.1199 (4)	0.0550 (14)
C2	0.3682 (2)	0.0917 (6)	0.0669 (4)	0.0603 (14)
C3	0.3193 (2)	0.2057 (6)	0.1041 (4)	0.0628 (17)
C4	0.2770 (2)	0.1406 (6)	0.1935 (4)	0.0579 (14)
C5	0.2852 (2)	−0.0344 (7)	0.2500 (4)	0.0691 (17)
C6	0.3339 (2)	−0.1493 (7)	0.2132 (4)	0.0675 (16)
C7	0.1859 (2)	0.3629 (6)	0.1465 (4)	0.0563 (14)
C8	0.1294 (2)	0.4544 (6)	0.2119 (4)	0.0643 (16)
C9	0.0901 (3)	0.5785 (8)	0.1019 (6)	0.102 (3)
C10	0.1581 (3)	0.5664 (8)	0.3447 (6)	0.102 (3)
C11	0.0849 (2)	0.3082 (7)	0.2637 (5)	0.0727 (18)
H1N	0.519 (3)	−0.074 (3)	0.174 (6)	0.1230*
H2	0.39660	0.13480	0.00580	0.0720*
H2N	0.500 (3)	−0.209 (8)	0.277 (2)	0.1230*
H3	0.31500	0.32570	0.06900	0.0750*
H3N	0.213 (3)	0.216 (8)	0.320 (6)	0.1230*
H5	0.25770	−0.07550	0.31350	0.0830*
H6	0.33890	−0.26790	0.25080	0.0810*
H9A	0.11770	0.67740	0.07780	0.1520*
H9B	0.05290	0.62860	0.14050	0.1520*
H9C	0.07470	0.50810	0.01780	0.1520*
H10A	0.18810	0.65780	0.31830	0.1530*
H10B	0.18120	0.48500	0.41480	0.1530*
H10C	0.12270	0.62620	0.38370	0.1530*
H11A	0.04780	0.36890	0.29760	0.0870*
H11B	0.10950	0.24310	0.34380	0.0870*

	U11	U22	U33	U12	U13	U23
Cl1	0.1001 (11)	0.1304 (13)	0.0862 (9)	−0.0399 (9)	0.0299 (8)	−0.0167 (8)
S1	0.0632 (6)	0.0599 (6)	0.0404 (5)	−0.0007 (5)	0.0126 (4)	0.0005 (4)
O1	0.079 (2)	0.0732 (19)	0.0411 (14)	0.0032 (15)	0.0195 (13)	−0.0002 (12)
O2	0.083 (2)	0.0627 (18)	0.0608 (17)	−0.0105 (15)	0.0144 (15)	−0.0004 (14)
O3	0.0708 (19)	0.090 (2)	0.0481 (15)	0.0074 (16)	0.0166 (13)	0.0051 (14)
N1	0.063 (2)	0.068 (2)	0.0475 (18)	−0.0015 (17)	0.0115 (16)	0.0033 (16)
N2	0.063 (2)	0.084 (3)	0.0473 (18)	0.0104 (19)	0.0163 (16)	0.0035 (18)
C1	0.058 (2)	0.066 (3)	0.0420 (19)	−0.0019 (19)	0.0104 (16)	0.0019 (17)
C2	0.061 (2)	0.070 (3)	0.053 (2)	−0.001 (2)	0.0190 (19)	0.008 (2)
C3	0.063 (3)	0.065 (3)	0.064 (3)	0.003 (2)	0.021 (2)	0.008 (2)
C4	0.056 (2)	0.075 (3)	0.044 (2)	0.001 (2)	0.0119 (17)	0.0023 (19)
C5	0.067 (3)	0.086 (3)	0.059 (3)	0.003 (2)	0.025 (2)	0.015 (2)
C6	0.067 (3)	0.079 (3)	0.059 (2)	0.008 (2)	0.018 (2)	0.017 (2)
C7	0.058 (2)	0.069 (3)	0.044 (2)	−0.003 (2)	0.0143 (17)	0.0006 (18)
C8	0.074 (3)	0.070 (3)	0.053 (2)	0.008 (2)	0.023 (2)	0.002 (2)
C9	0.113 (5)	0.104 (4)	0.098 (4)	0.042 (4)	0.048 (3)	0.032 (3)
C10	0.125 (5)	0.090 (4)	0.097 (4)	−0.007 (3)	0.035 (4)	−0.030 (3)
C11	0.073 (3)	0.095 (4)	0.054 (2)	0.008 (3)	0.023 (2)	0.002 (2)

Cl1—C11	1.778 (5)	C7—C8	1.536 (6)
S1—O1	1.439 (3)	C8—C9	1.516 (7)
S1—O2	1.427 (3)	C8—C10	1.540 (7)
S1—N1	1.602 (4)	C8—C11	1.522 (6)
S1—C1	1.762 (4)	C2—H2	0.9300
O3—C7	1.224 (5)	C3—H3	0.9300
N2—C4	1.424 (6)	C5—H5	0.9300
N2—C7	1.349 (5)	C6—H6	0.9300
N1—H1N	0.88 (3)	C9—H9A	0.9600
N1—H2N	0.88 (2)	C9—H9B	0.9600
N2—H3N	0.91 (6)	C9—H9C	0.9600
C1—C2	1.384 (6)	C10—H10A	0.9600
C1—C6	1.384 (6)	C10—H10B	0.9600
C2—C3	1.380 (6)	C10—H10C	0.9600
C3—C4	1.377 (6)	C11—H11A	0.9700
C4—C5	1.377 (6)	C11—H11B	0.9700
C5—C6	1.380 (6)
O1—S1—O2	119.30 (17)	C9—C8—C10	110.6 (4)
O1—S1—N1	105.79 (17)	C9—C8—C11	110.6 (4)
O1—S1—C1	107.08 (18)	Cl1—C11—C8	113.6 (3)
O2—S1—N1	107.79 (18)	C1—C2—H2	120.00
O2—S1—C1	107.90 (19)	C3—C2—H2	120.00
N1—S1—C1	108.62 (19)	C2—C3—H3	120.00
C4—N2—C7	124.4 (4)	C4—C3—H3	120.00
H1N—N1—H2N	115 (5)	C4—C5—H5	120.00
S1—N1—H1N	110 (4)	C6—C5—H5	120.00
S1—N1—H2N	113 (4)	C1—C6—H6	120.00
C4—N2—H3N	113 (4)	C5—C6—H6	120.00
C7—N2—H3N	120 (4)	C8—C9—H9A	110.00
S1—C1—C2	120.7 (3)	C8—C9—H9B	109.00
C2—C1—C6	119.9 (4)	C8—C9—H9C	109.00
S1—C1—C6	119.4 (3)	H9A—C9—H9B	109.00
C1—C2—C3	120.4 (4)	H9A—C9—H9C	109.00
C2—C3—C4	119.6 (4)	H9B—C9—H9C	109.00
N2—C4—C3	122.1 (4)	C8—C10—H10A	109.00
N2—C4—C5	117.7 (4)	C8—C10—H10B	109.00
C3—C4—C5	120.1 (4)	C8—C10—H10C	109.00
C4—C5—C6	120.6 (4)	H10A—C10—H10B	110.00
C1—C6—C5	119.4 (4)	H10A—C10—H10C	109.00
O3—C7—C8	121.8 (4)	H10B—C10—H10C	110.00
N2—C7—C8	115.2 (3)	Cl1—C11—H11A	109.00
O3—C7—N2	123.0 (4)	Cl1—C11—H11B	109.00
C10—C8—C11	106.2 (4)	C8—C11—H11A	109.00
C7—C8—C11	110.4 (4)	C8—C11—H11B	109.00
C7—C8—C9	109.5 (4)	H11A—C11—H11B	108.00
C7—C8—C10	109.6 (4)
O1—S1—C1—C2	−29.3 (4)	C2—C3—C4—N2	−179.9 (4)
O1—S1—C1—C6	154.6 (3)	C2—C3—C4—C5	2.7 (6)
O2—S1—C1—C2	−158.9 (3)	N2—C4—C5—C6	179.7 (4)
O2—S1—C1—C6	25.0 (4)	C3—C4—C5—C6	−2.8 (6)
N1—S1—C1—C2	84.5 (4)	C4—C5—C6—C1	0.8 (6)
N1—S1—C1—C6	−91.6 (4)	O3—C7—C8—C9	−1.1 (6)
C7—N2—C4—C3	42.6 (6)	O3—C7—C8—C10	−122.6 (4)
C7—N2—C4—C5	−139.9 (4)	O3—C7—C8—C11	120.8 (4)
C4—N2—C7—O3	−6.2 (7)	N2—C7—C8—C9	178.6 (4)
C4—N2—C7—C8	174.1 (4)	N2—C7—C8—C10	57.2 (5)
S1—C1—C2—C3	−177.4 (3)	N2—C7—C8—C11	−59.4 (5)
C6—C1—C2—C3	−1.4 (6)	C7—C8—C11—Cl1	−54.2 (4)
S1—C1—C6—C5	177.4 (3)	C9—C8—C11—Cl1	67.1 (4)
C2—C1—C6—C5	1.3 (6)	C10—C8—C11—Cl1	−172.9 (3)
C1—C2—C3—C4	−0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1—H1N···O1ii	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1—H2N···O1iii	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2—H3N···O3iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C3—H3···O3	0.93	2.49	2.896 (5)	106
C6—H6···O2	0.93	2.59	2.936 (5)	103
C11—H11B···O3iv	0.97	2.44	3.391 (5)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1—H1N⋯O1ii	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1—H2N⋯O1iii	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2—H3N⋯O3iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C11—H11B⋯O3iv	0.97	2.44	3.391 (5)	166

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