4-Chloro-2-methyl-N-phenyl-benzene-sulfonamide.

There are two mol-ecules in the asymmetric unit of the title compound, C(13)H(12)ClNO(2)S, with similar conformations. The orientations of the ortho-methyl groups in the sulfonyl benzene rings are in the direction of the N-H bonds of the sulfonamide groups. In the crystal, the mol-ecules are each linked into centrosymmetric dimers through N-H⋯O hydrogen bonds and packed into a layered structure diagonally in the bc plane.

Related literature

For related structures, see: Gelbrich et al. (2007 ▶); Gowda et al. (2008 ▶, 2009 ▶); Perlovich et al. (2006 ▶)

Experimental

Crystal data

C13H12ClNO2S

M = 281.75

Triclinic,

a = 8.609 (1) Å

b = 11.143 (1) Å

c = 14.726 (2) Å

α = 98.618 (7)°

β = 90.951 (8)°

γ = 105.79 (1)°

V = 1341.6 (3) Å3

Z = 4

Cu Kα radiation

μ = 3.93 mm−1

T = 299 (2) K

0.33 × 0.23 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.350, T max = 0.729

7620 measured reflections

4784 independent reflections

2980 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.176

S = 1.03

4784 reflections

333 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003845/fj2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003845/fj2192Isup2.hkl

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

C13H12ClNO2S	Z = 4
Mr = 281.75	F(000) = 584
Triclinic, P1	Dx = 1.395 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.609 (1) Å	Cell parameters from 25 reflections
b = 11.143 (1) Å	θ = 5.6–21.8°
c = 14.726 (2) Å	µ = 3.93 mm−1
α = 98.618 (7)°	T = 299 K
β = 90.951 (8)°	Prism, colourless
γ = 105.79 (1)°	0.33 × 0.23 × 0.08 mm
V = 1341.6 (3) Å3

Enraf–Nonius CAD-4 diffractometer	2980 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 67.0°, θmin = 3.0°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = −13→13
Tmin = 0.350, Tmax = 0.729	l = −17→7
7620 measured reflections	3 standard reflections every 120 min
4784 independent reflections	intensity decay: 1.0%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0962P)2 + 0.1233P] where P = (Fo2 + 2Fc2)/3
4784 reflections	(Δ/σ)max = 0.005
333 parameters	Δρmax = 0.41 e Å−3
12 restraints	Δρmin = −0.42 e Å−3

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
Cl1	0.4618 (4)	0.43860 (18)	0.24063 (15)	0.1670 (10)
S1	0.46343 (11)	0.96896 (11)	0.15504 (7)	0.0586 (3)
O1	0.4383 (4)	1.0364 (3)	0.2403 (2)	0.0802 (9)
O2	0.3532 (3)	0.9562 (3)	0.07717 (19)	0.0722 (8)
N1	0.6377 (4)	1.0345 (3)	0.1199 (2)	0.0611 (9)
H1N	0.647 (5)	1.039 (4)	0.059 (3)	0.073*
C1	0.4664 (4)	0.8182 (4)	0.1749 (3)	0.0565 (10)
C2	0.4758 (8)	0.7240 (5)	0.1044 (3)	0.0907 (16)
C3	0.4778 (10)	0.6088 (5)	0.1273 (4)	0.120 (2)
H3	0.4876	0.5444	0.0816	0.144*
C4	0.4653 (7)	0.5877 (5)	0.2179 (4)	0.0910 (16)
C5	0.4560 (6)	0.6791 (5)	0.2862 (3)	0.0768 (13)
H5	0.4494	0.6642	0.3467	0.092*
C6	0.4563 (5)	0.7946 (5)	0.2653 (3)	0.0663 (11)
H6	0.4495	0.8586	0.3122	0.080*
C7	0.7894 (4)	1.0635 (3)	0.1698 (3)	0.0522 (9)
C8	0.9247 (5)	1.0883 (4)	0.1201 (3)	0.0701 (12)
H8	0.9151	1.0848	0.0567	0.084*
C9	1.0763 (6)	1.1187 (5)	0.1656 (4)	0.0865 (15)
H9	1.1685	1.1358	0.1323	0.104*
C10	1.0914 (6)	1.1239 (5)	0.2591 (4)	0.0834 (15)
H10	1.1933	1.1440	0.2891	0.100*
C11	0.9570 (6)	1.0995 (4)	0.3074 (3)	0.0718 (12)
H11	0.9671	1.1026	0.3707	0.086*
C12	0.8054 (5)	1.0701 (4)	0.2639 (3)	0.0653 (11)
H12	0.7141	1.0547	0.2980	0.078*
C13	0.4894 (9)	0.7419 (4)	0.0007 (3)	0.102 (2)
H13A	0.5834	0.8097	−0.0050	0.123*
H13B	0.3947	0.7616	−0.0205	0.123*
H13C	0.4985	0.6653	−0.0357	0.123*
Cl2	0.1160 (4)	0.3570 (3)	0.99174 (14)	0.1919 (12)
S2	−0.06931 (11)	0.32374 (9)	0.57752 (8)	0.0560 (3)
O3	−0.1468 (3)	0.4185 (3)	0.5635 (2)	0.0703 (8)
O4	−0.1553 (3)	0.1953 (3)	0.5486 (2)	0.0727 (8)
N2	0.0946 (4)	0.3586 (3)	0.5248 (2)	0.0581 (9)
H2N	0.114 (5)	0.431 (4)	0.503 (3)	0.070*
C14	−0.0126 (5)	0.3404 (4)	0.6948 (3)	0.0569 (10)
C15	0.0592 (7)	0.4573 (4)	0.7478 (4)	0.0803 (13)
C16	0.0983 (8)	0.4591 (6)	0.8395 (4)	0.115 (2)
H16	0.1457	0.5359	0.8770	0.138*
C17	0.0679 (8)	0.3489 (7)	0.8762 (4)	0.110 (2)
C18	−0.0041 (7)	0.2348 (6)	0.8243 (4)	0.0906 (16)
H18	−0.0267	0.1612	0.8502	0.109*
C19	−0.0424 (5)	0.2309 (4)	0.7334 (3)	0.0679 (11)
H19	−0.0894	0.1533	0.6967	0.081*
C20	0.2114 (4)	0.2902 (3)	0.5100 (2)	0.0477 (8)
C21	0.1911 (5)	0.1719 (4)	0.5338 (3)	0.0610 (10)
H21	0.0998	0.1346	0.5632	0.073*
C22	0.3085 (6)	0.1093 (4)	0.5135 (3)	0.0692 (12)
H22	0.2954	0.0292	0.5286	0.083*
C23	0.4443 (6)	0.1657 (5)	0.4708 (3)	0.0742 (13)
H23	0.5231	0.1238	0.4574	0.089*
C24	0.4630 (5)	0.2827 (5)	0.4484 (3)	0.0723 (12)
H24	0.5551	0.3209	0.4201	0.087*
C25	0.3464 (4)	0.3451 (4)	0.4674 (3)	0.0577 (10)
H25	0.3596	0.4247	0.4513	0.069*
C26	0.0961 (9)	0.5821 (4)	0.7100 (4)	0.111 (2)
H26A	0.1530	0.5749	0.6548	0.133*
H26B	0.1619	0.6486	0.7550	0.133*
H26C	−0.0033	0.6010	0.6965	0.133*

	U11	U22	U33	U12	U13	U23
Cl1	0.280 (3)	0.1079 (13)	0.1210 (15)	0.0456 (15)	0.0296 (16)	0.0575 (11)
S1	0.0529 (5)	0.0868 (7)	0.0417 (5)	0.0282 (5)	0.0004 (4)	0.0114 (5)
O1	0.092 (2)	0.114 (3)	0.0494 (17)	0.0576 (19)	0.0072 (15)	0.0056 (16)
O2	0.0544 (16)	0.121 (3)	0.0516 (17)	0.0361 (16)	−0.0077 (13)	0.0244 (16)
N1	0.0573 (19)	0.085 (2)	0.0421 (18)	0.0178 (17)	−0.0045 (15)	0.0176 (17)
C1	0.052 (2)	0.076 (3)	0.039 (2)	0.0125 (18)	0.0021 (16)	0.0133 (18)
C2	0.146 (5)	0.079 (3)	0.047 (3)	0.030 (3)	0.012 (3)	0.017 (2)
C3	0.230 (8)	0.074 (3)	0.057 (3)	0.036 (4)	0.021 (4)	0.018 (3)
C4	0.123 (4)	0.081 (3)	0.066 (3)	0.017 (3)	0.006 (3)	0.025 (3)
C5	0.082 (3)	0.098 (4)	0.053 (3)	0.018 (3)	0.012 (2)	0.030 (3)
C6	0.059 (2)	0.091 (3)	0.048 (2)	0.015 (2)	0.0018 (19)	0.018 (2)
C7	0.057 (2)	0.051 (2)	0.049 (2)	0.0156 (17)	−0.0071 (17)	0.0100 (16)
C8	0.062 (3)	0.088 (3)	0.062 (3)	0.026 (2)	0.003 (2)	0.009 (2)
C9	0.058 (3)	0.112 (4)	0.089 (4)	0.024 (3)	0.002 (3)	0.012 (3)
C10	0.070 (3)	0.080 (3)	0.096 (4)	0.025 (2)	−0.029 (3)	−0.001 (3)
C11	0.081 (3)	0.063 (3)	0.065 (3)	0.012 (2)	−0.025 (2)	0.010 (2)
C12	0.065 (3)	0.074 (3)	0.050 (2)	0.007 (2)	−0.0075 (19)	0.015 (2)
C13	0.226 (7)	0.068 (3)	0.026 (2)	0.061 (4)	0.018 (3)	0.0116 (19)
Cl2	0.244 (3)	0.239 (3)	0.0830 (12)	0.035 (2)	−0.0157 (15)	0.0602 (15)
S2	0.0490 (5)	0.0529 (5)	0.0731 (7)	0.0173 (4)	0.0041 (4)	0.0259 (5)
O3	0.0608 (16)	0.0743 (19)	0.095 (2)	0.0364 (14)	0.0125 (15)	0.0398 (16)
O4	0.0641 (17)	0.0545 (17)	0.097 (2)	0.0071 (13)	−0.0088 (16)	0.0213 (15)
N2	0.0595 (19)	0.0517 (19)	0.078 (2)	0.0282 (16)	0.0181 (17)	0.0319 (17)
C14	0.057 (2)	0.055 (2)	0.066 (3)	0.0187 (18)	0.0156 (19)	0.0258 (19)
C15	0.103 (4)	0.063 (3)	0.073 (3)	0.019 (3)	0.007 (3)	0.015 (2)
C16	0.152 (6)	0.096 (4)	0.081 (4)	0.010 (4)	0.001 (4)	0.009 (3)
C17	0.131 (5)	0.131 (6)	0.071 (4)	0.027 (4)	0.003 (4)	0.041 (4)
C18	0.093 (4)	0.103 (4)	0.089 (4)	0.029 (3)	0.011 (3)	0.053 (3)
C19	0.070 (3)	0.063 (3)	0.079 (3)	0.021 (2)	0.007 (2)	0.032 (2)
C20	0.053 (2)	0.0466 (19)	0.046 (2)	0.0183 (16)	−0.0057 (16)	0.0085 (15)
C21	0.062 (2)	0.057 (2)	0.070 (3)	0.0214 (19)	0.001 (2)	0.019 (2)
C22	0.081 (3)	0.057 (2)	0.076 (3)	0.032 (2)	−0.010 (2)	0.008 (2)
C23	0.076 (3)	0.089 (3)	0.070 (3)	0.051 (3)	−0.004 (2)	0.001 (2)
C24	0.063 (3)	0.087 (3)	0.078 (3)	0.032 (2)	0.015 (2)	0.024 (3)
C25	0.056 (2)	0.061 (2)	0.058 (2)	0.0166 (18)	−0.0001 (18)	0.0164 (19)
C26	0.171 (6)	0.045 (3)	0.104 (4)	0.007 (3)	−0.003 (4)	0.010 (3)

Cl1—C4	1.735 (6)	Cl2—C17	1.727 (6)
S1—O1	1.415 (3)	S2—O4	1.417 (3)
S1—O2	1.441 (3)	S2—O3	1.431 (3)
S1—N1	1.611 (4)	S2—N2	1.604 (3)
S1—C1	1.754 (4)	S2—C14	1.756 (4)
N1—C7	1.419 (5)	N2—C20	1.419 (4)
N1—H1N	0.91 (5)	N2—H2N	0.88 (4)
C1—C2	1.382 (6)	C14—C19	1.385 (5)
C1—C6	1.395 (5)	C14—C15	1.389 (6)
C2—C3	1.380 (7)	C15—C16	1.383 (7)
C2—C13	1.571 (6)	C15—C26	1.529 (7)
C3—C4	1.390 (7)	C16—C17	1.378 (8)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.340 (7)	C17—C18	1.360 (8)
C5—C6	1.367 (6)	C18—C19	1.366 (7)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.372 (5)	C20—C25	1.367 (5)
C7—C12	1.380 (5)	C20—C21	1.381 (5)
C8—C9	1.388 (6)	C21—C22	1.389 (5)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.372 (7)	C22—C23	1.379 (6)
C9—H9	0.9300	C22—H22	0.9300
C10—C11	1.353 (7)	C23—C24	1.361 (6)
C10—H10	0.9300	C23—H23	0.9300
C11—C12	1.377 (6)	C24—C25	1.378 (5)
C11—H11	0.9300	C24—H24	0.9300
C12—H12	0.9300	C25—H25	0.9300
C13—H13A	0.9600	C26—H26A	0.9600
C13—H13B	0.9600	C26—H26B	0.9600
C13—H13C	0.9600	C26—H26C	0.9600
O1—S1—O2	118.88 (18)	O4—S2—O3	118.30 (18)
O1—S1—N1	110.6 (2)	O4—S2—N2	110.14 (19)
O2—S1—N1	103.80 (17)	O3—S2—N2	104.50 (17)
O1—S1—C1	106.88 (19)	O4—S2—C14	107.02 (18)
O2—S1—C1	109.17 (19)	O3—S2—C14	109.55 (19)
N1—S1—C1	107.02 (18)	N2—S2—C14	106.81 (18)
C7—N1—S1	126.6 (3)	C20—N2—S2	128.7 (3)
C7—N1—H1N	113 (3)	C20—N2—H2N	116 (3)
S1—N1—H1N	119 (3)	S2—N2—H2N	115 (3)
C2—C1—C6	120.1 (4)	C19—C14—C15	120.7 (4)
C2—C1—S1	122.2 (3)	C19—C14—S2	117.1 (3)
C6—C1—S1	117.7 (3)	C15—C14—S2	122.3 (3)
C3—C2—C1	117.7 (4)	C16—C15—C14	117.3 (5)
C3—C2—C13	118.5 (4)	C16—C15—C26	119.1 (5)
C1—C2—C13	123.8 (4)	C14—C15—C26	123.6 (5)
C2—C3—C4	120.8 (5)	C17—C16—C15	121.0 (6)
C2—C3—H3	119.6	C17—C16—H16	119.5
C4—C3—H3	119.6	C15—C16—H16	119.5
C5—C4—C3	121.4 (5)	C18—C17—C16	121.4 (6)
C5—C4—Cl1	120.5 (4)	C18—C17—Cl2	119.5 (5)
C3—C4—Cl1	118.0 (4)	C16—C17—Cl2	119.1 (6)
C4—C5—C6	118.7 (4)	C17—C18—C19	118.4 (5)
C4—C5—H5	120.6	C17—C18—H18	120.8
C6—C5—H5	120.6	C19—C18—H18	120.8
C5—C6—C1	121.2 (4)	C18—C19—C14	121.1 (5)
C5—C6—H6	119.4	C18—C19—H19	119.4
C1—C6—H6	119.4	C14—C19—H19	119.4
C8—C7—C12	119.8 (4)	C25—C20—C21	120.2 (3)
C8—C7—N1	116.9 (4)	C25—C20—N2	116.9 (3)
C12—C7—N1	123.3 (4)	C21—C20—N2	123.0 (3)
C7—C8—C9	119.3 (4)	C20—C21—C22	119.3 (4)
C7—C8—H8	120.4	C20—C21—H21	120.4
C9—C8—H8	120.4	C22—C21—H21	120.4
C10—C9—C8	120.7 (5)	C23—C22—C21	120.1 (4)
C10—C9—H9	119.7	C23—C22—H22	120.0
C8—C9—H9	119.7	C21—C22—H22	120.0
C11—C10—C9	119.5 (4)	C24—C23—C22	119.9 (4)
C11—C10—H10	120.2	C24—C23—H23	120.1
C9—C10—H10	120.2	C22—C23—H23	120.1
C10—C11—C12	120.9 (4)	C23—C24—C25	120.5 (4)
C10—C11—H11	119.6	C23—C24—H24	119.7
C12—C11—H11	119.6	C25—C24—H24	119.7
C11—C12—C7	119.9 (4)	C20—C25—C24	120.1 (4)
C11—C12—H12	120.1	C20—C25—H25	119.9
C7—C12—H12	120.1	C24—C25—H25	119.9
C2—C13—H13A	109.5	C15—C26—H26A	109.5
C2—C13—H13B	109.5	C15—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C2—C13—H13C	109.5	C15—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
O1—S1—N1—C7	54.0 (4)	O4—S2—N2—C20	−46.3 (4)
O2—S1—N1—C7	−177.4 (3)	O3—S2—N2—C20	−174.3 (3)
C1—S1—N1—C7	−62.0 (4)	C14—S2—N2—C20	69.6 (4)
O1—S1—C1—C2	174.7 (4)	O4—S2—C14—C19	6.9 (4)
O2—S1—C1—C2	44.9 (5)	O3—S2—C14—C19	136.3 (3)
N1—S1—C1—C2	−66.8 (4)	N2—S2—C14—C19	−111.1 (3)
O1—S1—C1—C6	−4.2 (4)	O4—S2—C14—C15	−173.1 (4)
O2—S1—C1—C6	−134.0 (3)	O3—S2—C14—C15	−43.7 (4)
N1—S1—C1—C6	114.2 (3)	N2—S2—C14—C15	68.9 (4)
C6—C1—C2—C3	−1.2 (8)	C19—C14—C15—C16	−0.3 (7)
S1—C1—C2—C3	179.9 (5)	S2—C14—C15—C16	179.7 (4)
C6—C1—C2—C13	−179.3 (5)	C19—C14—C15—C26	179.9 (5)
S1—C1—C2—C13	1.7 (8)	S2—C14—C15—C26	−0.1 (7)
C1—C2—C3—C4	2.1 (10)	C14—C15—C16—C17	0.5 (9)
C13—C2—C3—C4	−179.7 (6)	C26—C15—C16—C17	−179.6 (6)
C2—C3—C4—C5	−2.0 (11)	C15—C16—C17—C18	−1.3 (11)
C2—C3—C4—Cl1	177.8 (6)	C15—C16—C17—Cl2	−178.9 (5)
C3—C4—C5—C6	1.0 (9)	C16—C17—C18—C19	1.8 (10)
Cl1—C4—C5—C6	−178.9 (4)	Cl2—C17—C18—C19	179.4 (4)
C4—C5—C6—C1	−0.1 (7)	C17—C18—C19—C14	−1.5 (8)
C2—C1—C6—C5	0.3 (7)	C15—C14—C19—C18	0.8 (7)
S1—C1—C6—C5	179.2 (3)	S2—C14—C19—C18	−179.2 (4)
S1—N1—C7—C8	163.5 (3)	S2—N2—C20—C25	−176.1 (3)
S1—N1—C7—C12	−17.8 (6)	S2—N2—C20—C21	5.9 (6)
C12—C7—C8—C9	0.5 (6)	C25—C20—C21—C22	−0.5 (6)
N1—C7—C8—C9	179.2 (4)	N2—C20—C21—C22	177.4 (4)
C7—C8—C9—C10	0.1 (7)	C20—C21—C22—C23	0.7 (6)
C8—C9—C10—C11	−0.2 (8)	C21—C22—C23—C24	−0.2 (7)
C9—C10—C11—C12	−0.3 (7)	C22—C23—C24—C25	−0.5 (7)
C10—C11—C12—C7	0.9 (7)	C21—C20—C25—C24	−0.2 (6)
C8—C7—C12—C11	−1.0 (6)	N2—C20—C25—C24	−178.2 (4)
N1—C7—C12—C11	−179.7 (4)	C23—C24—C25—C20	0.7 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.91 (5)	2.02 (5)	2.922 (4)	175 (4)
N2—H2N···O3ii	0.88 (4)	2.03 (5)	2.906 (4)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.91 (5)	2.02 (5)	2.922 (4)	175 (4)
N2—H2N⋯O3ii	0.88 (4)	2.03 (5)	2.906 (4)	173 (4)

Symmetry codes: (i) ; (ii) .