4-Chloro-N-(3-methyl-benzo-yl)benzene-sulfonamide monohydrate.

In the title compound, C(14)H(12)ClNO(3)S·H(2)O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 84.4 (2)°. In the crystal, every water mol-ecule forms four hydrogen bonds with three different mol-ecules of 4-chloro-N-(3-methyl-benzo-yl)benzene-sulfonamide. One of the water H atoms forms a bifurcated hydrogen bond with both the sulfonyl and the carbonyl O atoms of the same mol-ecule. Mol-ecules are linked into layers in the ab plane through N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2003 ▶), on N-(substitutedbenzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2011 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C14H12ClNO3S·H2O

M = 327.77

Orthorhombic,

a = 5.0148 (6) Å

b = 12.864 (2) Å

c = 46.314 (5) Å

V = 2987.7 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.46 × 0.14 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.834, T max = 0.976

5972 measured reflections

2684 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.105

wR(F 2) = 0.185

S = 1.35

2684 reflections

200 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051932/bt5739sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051932/bt5739Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051932/bt5739Isup3.cml

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

C14H12ClNO3S·H2O	F(000) = 1360
Mr = 327.77	Dx = 1.457 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1913 reflections
a = 5.0148 (6) Å	θ = 2.6–27.8°
b = 12.864 (2) Å	µ = 0.41 mm−1
c = 46.314 (5) Å	T = 293 K
V = 2987.7 (7) Å3	Needle, colourless
Z = 8	0.46 × 0.14 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2684 independent reflections
Radiation source: fine-focus sealed tube	1959 reflections with I > 2σ(I)
graphite	Rint = 0.037
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −3→6
Tmin = 0.834, Tmax = 0.976	k = −9→15
5972 measured reflections	l = −55→55

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)] = 0.105	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.35	w = 1/[σ2(Fo2) + (0.P)2 + 17.7362P] where P = (Fo2 + 2Fc2)/3
2684 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.33 e Å−3
3 restraints	Δρmin = −0.34 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.3419 (12)	−0.0253 (5)	0.07777 (12)	0.0283 (14)
C2	0.4759 (15)	0.0400 (6)	0.05920 (14)	0.0469 (19)
H2	0.4533	0.1117	0.0604	0.056*
C3	0.6448 (16)	−0.0027 (6)	0.03877 (15)	0.051 (2)
H3	0.7378	0.0403	0.0262	0.061*
C4	0.6751 (15)	−0.1085 (6)	0.03706 (14)	0.0423 (18)
C5	0.5420 (15)	−0.1736 (6)	0.05504 (14)	0.0437 (18)
H5	0.5650	−0.2451	0.0536	0.052*
C6	0.3717 (14)	−0.1325 (5)	0.07558 (13)	0.0367 (16)
H6	0.2776	−0.1764	0.0879	0.044*
C7	0.4414 (13)	−0.0406 (5)	0.14890 (13)	0.0323 (15)
C8	0.6298 (13)	−0.0066 (5)	0.17281 (13)	0.0308 (15)
C9	0.7972 (13)	−0.0844 (5)	0.18361 (13)	0.0335 (16)
H9	0.7884	−0.1511	0.1759	0.040*
C10	0.9761 (14)	−0.0630 (6)	0.20566 (14)	0.0403 (18)
C11	0.9834 (16)	0.0360 (7)	0.21646 (15)	0.055 (2)
H11	1.1054	0.0517	0.2309	0.066*
C12	0.8156 (18)	0.1131 (7)	0.20656 (16)	0.059 (2)
H12	0.8217	0.1791	0.2148	0.071*
C13	0.6372 (16)	0.0924 (5)	0.18426 (14)	0.0437 (18)
H13	0.5253	0.1441	0.1772	0.052*
C14	1.1601 (16)	−0.1458 (7)	0.21706 (17)	0.063 (2)
H14A	1.2381	−0.1830	0.2012	0.075*
H14B	1.0610	−0.1933	0.2289	0.075*
H14C	1.2986	−0.1141	0.2283	0.075*
N1	0.3383 (10)	0.0427 (4)	0.13292 (11)	0.0302 (12)
H1N	0.429 (11)	0.099 (3)	0.1325 (14)	0.036*
O1	−0.0632 (9)	−0.0465 (3)	0.11239 (9)	0.0360 (11)
O2	0.0653 (10)	0.1296 (3)	0.09642 (10)	0.0441 (13)
O3	0.3853 (10)	−0.1289 (3)	0.14414 (9)	0.0387 (12)
O4	0.5930 (12)	0.2319 (4)	0.12531 (16)	0.0649 (17)
H41	0.533 (17)	0.289 (4)	0.1312 (18)	0.078*
H42	0.756 (6)	0.234 (7)	0.1210 (18)	0.078*
Cl1	0.8942 (5)	−0.1606 (2)	0.01180 (5)	0.0729 (7)
S1	0.1393 (3)	0.02651 (13)	0.10489 (3)	0.0315 (4)

	U11	U22	U33	U12	U13	U23
C1	0.031 (3)	0.027 (3)	0.027 (3)	−0.002 (3)	−0.003 (3)	0.006 (3)
C2	0.056 (5)	0.040 (4)	0.045 (4)	−0.006 (4)	0.008 (4)	−0.001 (4)
C3	0.059 (5)	0.051 (5)	0.043 (4)	−0.020 (4)	0.021 (4)	0.001 (4)
C4	0.043 (4)	0.049 (5)	0.035 (4)	−0.003 (4)	0.004 (3)	−0.008 (3)
C5	0.053 (5)	0.035 (4)	0.044 (4)	−0.001 (4)	0.005 (4)	−0.004 (3)
C6	0.042 (4)	0.037 (4)	0.031 (3)	−0.005 (4)	0.005 (3)	0.005 (3)
C7	0.030 (3)	0.037 (4)	0.030 (3)	0.002 (3)	0.005 (3)	0.002 (3)
C8	0.035 (4)	0.032 (4)	0.026 (3)	−0.003 (3)	0.004 (3)	−0.002 (3)
C9	0.040 (4)	0.032 (4)	0.028 (3)	0.000 (3)	0.004 (3)	−0.001 (3)
C10	0.036 (4)	0.056 (5)	0.029 (3)	−0.001 (4)	0.001 (3)	0.002 (4)
C11	0.045 (5)	0.087 (7)	0.033 (4)	−0.009 (5)	−0.011 (4)	−0.010 (4)
C12	0.072 (6)	0.058 (5)	0.048 (5)	−0.011 (5)	−0.004 (5)	−0.017 (4)
C13	0.055 (5)	0.038 (4)	0.038 (4)	−0.001 (4)	−0.005 (4)	−0.009 (3)
C14	0.045 (5)	0.088 (7)	0.055 (5)	0.005 (5)	−0.008 (4)	0.018 (5)
N1	0.029 (3)	0.028 (3)	0.033 (3)	−0.006 (3)	−0.005 (2)	−0.002 (2)
O1	0.032 (2)	0.039 (3)	0.037 (2)	−0.006 (2)	0.002 (2)	−0.001 (2)
O2	0.047 (3)	0.030 (3)	0.055 (3)	0.012 (2)	−0.009 (3)	0.004 (2)
O3	0.050 (3)	0.023 (3)	0.043 (3)	−0.004 (2)	−0.012 (2)	−0.001 (2)
O4	0.051 (4)	0.036 (3)	0.107 (5)	−0.003 (3)	−0.004 (4)	0.009 (3)
Cl1	0.0690 (15)	0.0909 (17)	0.0590 (12)	−0.0093 (14)	0.0315 (12)	−0.0208 (13)
S1	0.0309 (8)	0.0296 (8)	0.0338 (8)	0.0019 (8)	−0.0033 (7)	0.0031 (8)

C1—C2	1.377 (9)	C9—H9	0.9300
C1—C6	1.392 (9)	C10—C11	1.369 (10)
C1—S1	1.747 (6)	C10—C14	1.505 (10)
C2—C3	1.384 (10)	C11—C12	1.380 (11)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.371 (10)	C12—C13	1.392 (10)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.357 (10)	C13—H13	0.9300
C4—Cl1	1.739 (7)	C14—H14A	0.9600
C5—C6	1.383 (9)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
C6—H6	0.9300	N1—S1	1.651 (5)
C7—O3	1.192 (7)	N1—H1N	0.86 (2)
C7—N1	1.400 (8)	O1—S1	1.426 (4)
C7—C8	1.520 (9)	O2—S1	1.432 (5)
C8—C13	1.380 (9)	O4—H41	0.84 (2)
C8—C9	1.398 (9)	O4—H42	0.84 (2)
C9—C10	1.387 (9)
C2—C1—C6	120.5 (6)	C11—C10—C14	120.9 (7)
C2—C1—S1	120.0 (5)	C9—C10—C14	121.0 (7)
C6—C1—S1	119.5 (5)	C10—C11—C12	122.1 (7)
C1—C2—C3	118.9 (7)	C10—C11—H11	118.9
C1—C2—H2	120.6	C12—C11—H11	118.9
C3—C2—H2	120.6	C11—C12—C13	120.0 (7)
C4—C3—C2	120.1 (7)	C11—C12—H12	120.0
C4—C3—H3	119.9	C13—C12—H12	120.0
C2—C3—H3	119.9	C8—C13—C12	118.6 (7)
C5—C4—C3	121.5 (7)	C8—C13—H13	120.7
C5—C4—Cl1	119.0 (6)	C12—C13—H13	120.7
C3—C4—Cl1	119.4 (6)	C10—C14—H14A	109.5
C4—C5—C6	119.4 (7)	C10—C14—H14B	109.5
C4—C5—H5	120.3	H14A—C14—H14B	109.5
C6—C5—H5	120.3	C10—C14—H14C	109.5
C5—C6—C1	119.7 (6)	H14A—C14—H14C	109.5
C5—C6—H6	120.2	H14B—C14—H14C	109.5
C1—C6—H6	120.2	C7—N1—S1	122.9 (4)
O3—C7—N1	123.0 (6)	C7—N1—H1N	118 (4)
O3—C7—C8	123.7 (6)	S1—N1—H1N	114 (4)
N1—C7—C8	113.3 (6)	H41—O4—H42	113 (9)
C13—C8—C9	120.4 (6)	O1—S1—O2	119.5 (3)
C13—C8—C7	124.2 (6)	O1—S1—N1	108.8 (3)
C9—C8—C7	115.4 (6)	O2—S1—N1	104.8 (3)
C10—C9—C8	120.7 (6)	O1—S1—C1	109.8 (3)
C10—C9—H9	119.7	O2—S1—C1	107.9 (3)
C8—C9—H9	119.7	N1—S1—C1	105.2 (3)
C11—C10—C9	118.1 (7)
C6—C1—C2—C3	−1.4 (11)	C9—C10—C11—C12	1.5 (11)
S1—C1—C2—C3	177.0 (6)	C14—C10—C11—C12	−179.5 (7)
C1—C2—C3—C4	0.5 (12)	C10—C11—C12—C13	−2.1 (12)
C2—C3—C4—C5	0.2 (13)	C9—C8—C13—C12	0.5 (11)
C2—C3—C4—Cl1	−178.5 (6)	C7—C8—C13—C12	178.7 (6)
C3—C4—C5—C6	0.0 (12)	C11—C12—C13—C8	1.0 (12)
Cl1—C4—C5—C6	178.6 (5)	O3—C7—N1—S1	−2.9 (9)
C4—C5—C6—C1	−0.8 (11)	C8—C7—N1—S1	177.3 (4)
C2—C1—C6—C5	1.5 (10)	C7—N1—S1—O1	46.8 (6)
S1—C1—C6—C5	−176.9 (5)	C7—N1—S1—O2	175.7 (5)
O3—C7—C8—C13	−159.8 (7)	C7—N1—S1—C1	−70.7 (5)
N1—C7—C8—C13	19.9 (9)	C2—C1—S1—O1	153.9 (5)
O3—C7—C8—C9	18.5 (9)	C6—C1—S1—O1	−27.6 (6)
N1—C7—C8—C9	−161.7 (5)	C2—C1—S1—O2	22.2 (6)
C13—C8—C9—C10	−1.0 (10)	C6—C1—S1—O2	−159.4 (5)
C7—C8—C9—C10	−179.4 (6)	C2—C1—S1—N1	−89.2 (6)
C8—C9—C10—C11	0.1 (10)	C6—C1—S1—N1	89.2 (6)
C8—C9—C10—C14	−179.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.86 (2)	1.93 (2)	2.771 (8)	169 (6)
O4—H41···O1i	0.84 (2)	2.29 (7)	2.916 (7)	131 (8)
O4—H41···O3i	0.84 (2)	2.42 (6)	3.117 (8)	140 (8)
O4—H42···O2ii	0.84 (2)	2.35 (6)	3.022 (8)	137 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.86 (2)	1.93 (2)	2.771 (8)	169 (6)
O4—H41⋯O1i	0.84 (2)	2.29 (7)	2.916 (7)	131 (8)
O4—H41⋯O3i	0.84 (2)	2.42 (6)	3.117 (8)	140 (8)
O4—H42⋯O2ii	0.84 (2)	2.35 (6)	3.022 (8)	137 (8)

Symmetry codes: (i) ; (ii) .