N-Benzoyl-4-nitro-benzene-sulfonamide monohydrate.

In the title compound, C(13)H(10)N(2)O(5)S·H(2)O, the dihedral angle between the sulfonyl and benzoyl benzene rings is 83.4 (1)°. In the crystal, the water mol-ecule forms four hydrogen bonds with three different mol-ecules of N-benzoyl-4-nitro-benzene-sulfonamide. One of the H atoms of H(2)O forms a bifurcated hydrogen bond with a sulfonyl and the carbonyl O atoms. Mol-ecules are linked into a three-dimensional network by 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-(substituted-benzo­yl)-aryl­sulfonamides, see: Suchetan et al. (2011 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C13H10N2O5S·H2O

M = 324.31

Monoclinic,

a = 22.687 (2) Å

b = 5.0673 (4) Å

c = 12.755 (1) Å

β = 100.04 (1)°

V = 1443.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.46 × 0.08 × 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 = 0.891, T max = 0.985

4828 measured reflections

2608 independent reflections

2039 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.110

S = 1.26

2608 reflections

208 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.36 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/S1600536811051439/bt5737sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051439/bt5737Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051439/bt5737Isup3.cml

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

C13H10N2O5S·H2O	F(000) = 672
Mr = 324.31	Dx = 1.492 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1916 reflections
a = 22.687 (2) Å	θ = 2.6–27.8°
b = 5.0673 (4) Å	µ = 0.26 mm−1
c = 12.755 (1) Å	T = 293 K
β = 100.04 (1)°	Rod, colourless
V = 1443.9 (2) Å3	0.46 × 0.08 × 0.06 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2608 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −27→24
Tmin = 0.891, Tmax = 0.985	k = −6→4
4828 measured reflections	l = −9→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ2(Fo2) + (0.0194P)2 + 1.7364P] where P = (Fo2 + 2Fc2)/3
2608 reflections	(Δ/σ)max = 0.005
208 parameters	Δρmax = 0.22 e Å−3
3 restraints	Δρmin = −0.36 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	0.16151 (12)	0.1882 (6)	0.6022 (2)	0.0291 (7)
C2	0.15709 (13)	0.1477 (6)	0.7078 (2)	0.0337 (7)
H2	0.1820	0.2393	0.7612	0.040*
C3	0.11581 (13)	−0.0285 (6)	0.7333 (2)	0.0351 (8)
H3	0.1128	−0.0596	0.8040	0.042*
C4	0.07914 (13)	−0.1576 (6)	0.6525 (2)	0.0308 (7)
C5	0.08159 (13)	−0.1161 (7)	0.5468 (2)	0.0372 (8)
H5	0.0555	−0.2036	0.4938	0.045*
C6	0.12353 (13)	0.0581 (6)	0.5209 (2)	0.0364 (8)
H6	0.1264	0.0883	0.4500	0.044*
C7	0.31104 (13)	0.1086 (6)	0.6648 (2)	0.0346 (7)
C8	0.36194 (13)	−0.0639 (7)	0.6498 (3)	0.0395 (8)
C9	0.38346 (15)	−0.2384 (8)	0.7303 (3)	0.0534 (10)
H9	0.3662	−0.2449	0.7913	0.064*
C10	0.43058 (18)	−0.4035 (9)	0.7208 (4)	0.0721 (13)
H10	0.4445	−0.5226	0.7749	0.087*
C11	0.45689 (19)	−0.3931 (10)	0.6324 (5)	0.0809 (15)
H11	0.4886	−0.5052	0.6263	0.097*
C12	0.43649 (18)	−0.2171 (10)	0.5526 (4)	0.0776 (14)
H12	0.4551	−0.2075	0.4932	0.093*
C13	0.38845 (16)	−0.0536 (9)	0.5597 (3)	0.0582 (11)
H13	0.3741	0.0622	0.5046	0.070*
N1	0.27666 (11)	0.2048 (5)	0.5716 (2)	0.0336 (6)
H1N	0.2770 (14)	0.123 (6)	0.5129 (18)	0.040*
N2	0.03640 (12)	−0.3529 (5)	0.6805 (2)	0.0397 (7)
O1	0.23142 (9)	0.5955 (4)	0.64774 (16)	0.0383 (5)
O2	0.20107 (10)	0.4686 (5)	0.45919 (16)	0.0421 (6)
O3	0.30049 (10)	0.1645 (5)	0.75190 (17)	0.0485 (6)
O4	0.04482 (11)	−0.4391 (5)	0.7715 (2)	0.0520 (7)
O5	−0.00594 (11)	−0.4144 (5)	0.61181 (19)	0.0587 (7)
O6	0.26446 (15)	−0.0825 (6)	0.3850 (2)	0.0655 (8)
H61	0.2475 (18)	−0.227 (5)	0.390 (3)	0.079*
H62	0.2696 (19)	−0.024 (8)	0.327 (2)	0.079*
S1	0.21771 (3)	0.39587 (16)	0.56867 (6)	0.0309 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0273 (15)	0.0278 (16)	0.0323 (16)	0.0009 (13)	0.0055 (12)	0.0000 (13)
C2	0.0328 (16)	0.0399 (19)	0.0276 (15)	−0.0054 (15)	0.0028 (12)	−0.0072 (15)
C3	0.0360 (17)	0.0417 (19)	0.0288 (16)	−0.0038 (15)	0.0095 (13)	−0.0014 (15)
C4	0.0294 (15)	0.0272 (17)	0.0370 (17)	−0.0008 (13)	0.0088 (13)	−0.0028 (14)
C5	0.0360 (17)	0.0400 (19)	0.0336 (17)	−0.0089 (16)	0.0010 (13)	−0.0071 (16)
C6	0.0390 (17)	0.042 (2)	0.0268 (15)	−0.0023 (16)	0.0036 (13)	0.0009 (15)
C7	0.0319 (16)	0.0332 (18)	0.0385 (18)	−0.0019 (15)	0.0054 (13)	−0.0020 (16)
C8	0.0282 (16)	0.040 (2)	0.049 (2)	0.0007 (16)	0.0036 (14)	−0.0099 (17)
C9	0.039 (2)	0.049 (2)	0.069 (3)	0.0069 (19)	0.0023 (18)	0.001 (2)
C10	0.054 (2)	0.059 (3)	0.096 (4)	0.013 (2)	−0.007 (2)	−0.001 (3)
C11	0.048 (2)	0.075 (3)	0.115 (4)	0.022 (3)	0.003 (3)	−0.032 (3)
C12	0.051 (2)	0.100 (4)	0.087 (3)	0.013 (3)	0.023 (2)	−0.029 (3)
C13	0.043 (2)	0.073 (3)	0.060 (2)	0.007 (2)	0.0139 (18)	−0.011 (2)
N1	0.0335 (14)	0.0377 (16)	0.0303 (14)	0.0004 (13)	0.0072 (11)	−0.0041 (12)
N2	0.0396 (16)	0.0376 (17)	0.0445 (17)	−0.0061 (14)	0.0149 (13)	−0.0089 (14)
O1	0.0449 (12)	0.0280 (12)	0.0420 (12)	−0.0012 (11)	0.0079 (10)	−0.0053 (10)
O2	0.0493 (13)	0.0437 (14)	0.0325 (12)	−0.0033 (11)	0.0046 (10)	0.0116 (11)
O3	0.0499 (14)	0.0608 (17)	0.0348 (13)	0.0150 (13)	0.0077 (10)	−0.0010 (12)
O4	0.0555 (15)	0.0499 (16)	0.0525 (15)	−0.0081 (13)	0.0146 (12)	0.0129 (13)
O5	0.0558 (15)	0.0691 (19)	0.0517 (15)	−0.0313 (15)	0.0112 (12)	−0.0165 (14)
O6	0.113 (2)	0.0493 (18)	0.0364 (14)	−0.0145 (17)	0.0191 (15)	0.0004 (14)
S1	0.0332 (4)	0.0290 (4)	0.0304 (4)	−0.0012 (4)	0.0054 (3)	0.0021 (4)

C1—C2	1.383 (4)	C9—C10	1.379 (5)
C1—C6	1.393 (4)	C9—H9	0.9300
C1—S1	1.762 (3)	C10—C11	1.366 (6)
C2—C3	1.373 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.372 (7)
C3—C4	1.372 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.385 (5)
C4—C5	1.375 (4)	C12—H12	0.9300
C4—N2	1.472 (4)	C13—H13	0.9300
C5—C6	1.380 (4)	N1—S1	1.646 (3)
C5—H5	0.9300	N1—H1N	0.856 (17)
C6—H6	0.9300	N2—O5	1.223 (3)
C7—O3	1.210 (3)	N2—O4	1.223 (3)
C7—N1	1.392 (4)	O1—S1	1.424 (2)
C7—C8	1.487 (4)	O2—S1	1.430 (2)
C8—C9	1.378 (5)	O6—H61	0.836 (19)
C8—C13	1.388 (5)	O6—H62	0.822 (19)
C2—C1—C6	120.9 (3)	C10—C9—H9	119.9
C2—C1—S1	120.2 (2)	C11—C10—C9	120.4 (4)
C6—C1—S1	118.8 (2)	C11—C10—H10	119.8
C3—C2—C1	119.7 (3)	C9—C10—H10	119.8
C3—C2—H2	120.2	C10—C11—C12	119.9 (4)
C1—C2—H2	120.2	C10—C11—H11	120.1
C4—C3—C2	118.8 (3)	C12—C11—H11	120.1
C4—C3—H3	120.6	C11—C12—C13	120.5 (4)
C2—C3—H3	120.6	C11—C12—H12	119.7
C3—C4—C5	122.7 (3)	C13—C12—H12	119.7
C3—C4—N2	118.5 (3)	C12—C13—C8	119.4 (4)
C5—C4—N2	118.8 (3)	C12—C13—H13	120.3
C4—C5—C6	118.7 (3)	C8—C13—H13	120.3
C4—C5—H5	120.6	C7—N1—S1	123.9 (2)
C6—C5—H5	120.6	C7—N1—H1N	119 (2)
C5—C6—C1	119.1 (3)	S1—N1—H1N	113 (2)
C5—C6—H6	120.4	O5—N2—O4	124.2 (3)
C1—C6—H6	120.4	O5—N2—C4	117.7 (3)
O3—C7—N1	122.1 (3)	O4—N2—C4	118.0 (3)
O3—C7—C8	122.5 (3)	H61—O6—H62	121 (4)
N1—C7—C8	115.4 (3)	O1—S1—O2	119.78 (14)
C9—C8—C13	119.5 (3)	O1—S1—N1	109.00 (13)
C9—C8—C7	117.6 (3)	O2—S1—N1	104.41 (13)
C13—C8—C7	122.9 (3)	O1—S1—C1	109.29 (13)
C8—C9—C10	120.2 (4)	O2—S1—C1	108.16 (13)
C8—C9—H9	119.9	N1—S1—C1	105.22 (14)
C6—C1—C2—C3	1.8 (5)	C11—C12—C13—C8	1.7 (7)
S1—C1—C2—C3	−175.6 (2)	C9—C8—C13—C12	−0.6 (6)
C1—C2—C3—C4	−1.0 (5)	C7—C8—C13—C12	178.7 (3)
C2—C3—C4—C5	−0.7 (5)	O3—C7—N1—S1	−1.6 (5)
C2—C3—C4—N2	177.9 (3)	C8—C7—N1—S1	179.2 (2)
C3—C4—C5—C6	1.5 (5)	C3—C4—N2—O5	161.0 (3)
N2—C4—C5—C6	−177.1 (3)	C5—C4—N2—O5	−20.3 (4)
C4—C5—C6—C1	−0.7 (5)	C3—C4—N2—O4	−17.6 (4)
C2—C1—C6—C5	−0.9 (5)	C5—C4—N2—O4	161.1 (3)
S1—C1—C6—C5	176.4 (2)	C7—N1—S1—O1	44.7 (3)
O3—C7—C8—C9	24.1 (5)	C7—N1—S1—O2	173.8 (2)
N1—C7—C8—C9	−156.8 (3)	C7—N1—S1—C1	−72.5 (3)
O3—C7—C8—C13	−155.3 (3)	C2—C1—S1—O1	−30.0 (3)
N1—C7—C8—C13	23.9 (5)	C6—C1—S1—O1	152.6 (2)
C13—C8—C9—C10	−0.7 (5)	C2—C1—S1—O2	−162.0 (2)
C7—C8—C9—C10	179.9 (3)	C6—C1—S1—O2	20.7 (3)
C8—C9—C10—C11	0.9 (6)	C2—C1—S1—N1	86.9 (3)
C9—C10—C11—C12	0.2 (7)	C6—C1—S1—N1	−90.5 (3)
C10—C11—C12—C13	−1.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6	0.86 (2)	1.92 (2)	2.763 (4)	170 (3)
O6—H61···O2i	0.84 (2)	2.14 (2)	2.935 (4)	158 (4)
O6—H62···O3ii	0.82 (2)	2.23 (3)	2.919 (4)	142 (4)
O6—H62···O1ii	0.82 (2)	2.33 (3)	2.988 (3)	138 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6	0.86 (2)	1.92 (2)	2.763 (4)	170 (3)
O6—H61⋯O2i	0.84 (2)	2.14 (2)	2.935 (4)	158 (4)
O6—H62⋯O3ii	0.82 (2)	2.23 (3)	2.919 (4)	142 (4)
O6—H62⋯O1ii	0.82 (2)	2.33 (3)	2.988 (3)	138 (4)

Symmetry codes: (i) ; (ii) .