N-(3-Chloro-phen-yl)-N'-(2-methyl-phenyl)succinamide monohydrate.

In the title compound, C(17)H(17)ClN(2)O(2)·H(2)O, the dihedral angles formed by the aromatic rings of the chloro-benzene and methyl-benzene groups with the mean planes of the attached NH-C(O)-CH(2) fragments are 9.4 (4) and 62.9 (2)°, respectively. In the crystal, mol-ecules are packed into layers parallel to the bc plane by O-H⋯O and N-H⋯O hydrogen-bond inter-actions.

Related literature

For our study on the effects of substituents on the structures of N-(ar­yl)amides, see: Gowda et al. (2004 ▶); Saraswathi et al. (2011 ▶). For the oxidative strengths of N-chloro-N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C17H17ClN2O2·H2O

M = 334.79

Monoclinic,

a = 14.875 (4) Å

b = 13.908 (3) Å

c = 8.088 (2) Å

β = 90.11 (2)°

V = 1673.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.44 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.900, T max = 0.981

6273 measured reflections

3080 independent reflections

1436 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.115

wR(F 2) = 0.285

S = 1.14

3080 reflections

221 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.66 e Å−3

Δρmin = −0.27 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 datablocks I, global. DOI: 10.1107/S1600536811014942/rz2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014942/rz2582Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811014942/rz2582Isup3.cml

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

C17H17ClN2O2·H2O	F(000) = 704
Mr = 334.79	Dx = 1.329 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1620 reflections
a = 14.875 (4) Å	θ = 2.7–27.9°
b = 13.908 (3) Å	µ = 0.24 mm−1
c = 8.088 (2) Å	T = 293 K
β = 90.11 (2)°	Needle, colourless
V = 1673.3 (7) Å3	0.44 × 0.12 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3080 independent reflections
Radiation source: fine-focus sealed tube	1436 reflections with I > 2σ(I)
graphite	Rint = 0.074
Rotation method data acquisition using ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→14
Tmin = 0.900, Tmax = 0.981	k = −16→16
6273 measured reflections	l = −9→8

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)] = 0.115	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.285	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.104P)2 + 1.4616P] where P = (Fo2 + 2Fc2)/3
3080 reflections	(Δ/σ)max = 0.010
221 parameters	Δρmax = 0.66 e Å−3
5 restraints	Δρmin = −0.27 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
Cl1	0.24505 (16)	0.43031 (14)	0.5534 (3)	0.0888 (8)
O1	0.4988 (3)	0.2577 (3)	0.2806 (6)	0.0588 (13)
O2	0.6939 (3)	0.1531 (3)	0.3675 (5)	0.0509 (12)
N1	0.4157 (4)	0.1301 (4)	0.3620 (7)	0.0526 (14)
H1N	0.414 (4)	0.0680 (15)	0.367 (8)	0.063*
N2	0.7588 (4)	0.2301 (4)	0.1544 (6)	0.0511 (15)
H2N	0.757 (4)	0.246 (4)	0.052 (3)	0.061*
C1	0.3450 (4)	0.1731 (5)	0.4498 (8)	0.0480 (17)
C2	0.3334 (4)	0.2716 (4)	0.4599 (8)	0.0497 (17)
H2	0.3746	0.3134	0.4120	0.060*
C3	0.2595 (5)	0.3062 (5)	0.5426 (9)	0.0571 (19)
C4	0.1978 (5)	0.2489 (6)	0.6174 (9)	0.0622 (19)
H4	0.1488	0.2749	0.6729	0.075*
C5	0.2105 (5)	0.1503 (5)	0.6079 (10)	0.072 (2)
H5	0.1695	0.1093	0.6582	0.087*
C6	0.2826 (5)	0.1127 (5)	0.5254 (9)	0.062 (2)
H6	0.2900	0.0464	0.5198	0.074*
C7	0.4836 (4)	0.1708 (5)	0.2793 (8)	0.0446 (16)
C8	0.5394 (4)	0.1008 (5)	0.1842 (8)	0.0542 (18)
H8A	0.5022	0.0715	0.0994	0.065*
H8B	0.5591	0.0502	0.2585	0.065*
C9	0.6221 (5)	0.1455 (5)	0.1022 (8)	0.0540 (18)
H9A	0.6479	0.0991	0.0263	0.065*
H9B	0.6033	0.2009	0.0380	0.065*
C10	0.6931 (4)	0.1764 (4)	0.2227 (8)	0.0404 (15)
C11	0.8362 (5)	0.2665 (5)	0.2395 (7)	0.0478 (17)
C12	0.9000 (5)	0.2044 (5)	0.3062 (8)	0.059 (2)
C13	0.9760 (5)	0.2453 (7)	0.3794 (9)	0.073 (2)
H13	1.0195	0.2058	0.4264	0.087*
C14	0.9870 (6)	0.3428 (8)	0.3827 (10)	0.083 (3)
H14	1.0384	0.3685	0.4312	0.100*
C15	0.9247 (6)	0.4031 (6)	0.3169 (11)	0.081 (3)
H15	0.9335	0.4693	0.3196	0.097*
C16	0.8483 (6)	0.3649 (5)	0.2460 (9)	0.066 (2)
H16	0.8047	0.4056	0.2024	0.079*
C17	0.8932 (6)	0.0992 (6)	0.2956 (10)	0.087 (3)
H17A	0.8438	0.0775	0.3621	0.131*
H17B	0.9479	0.0708	0.3352	0.131*
H17C	0.8834	0.0807	0.1827	0.131*
O3	0.5938 (4)	0.0811 (3)	0.6426 (6)	0.0690 (15)
H31O	0.614 (5)	0.098 (5)	0.549 (5)	0.104*
H32O	0.561 (5)	0.125 (4)	0.679 (8)	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.0963 (17)	0.0478 (12)	0.1224 (19)	0.0147 (12)	0.0074 (14)	−0.0092 (12)
O1	0.062 (3)	0.036 (3)	0.079 (3)	−0.011 (2)	0.007 (2)	−0.005 (2)
O2	0.054 (3)	0.055 (3)	0.044 (3)	0.002 (2)	0.006 (2)	0.005 (2)
N1	0.047 (3)	0.036 (3)	0.074 (4)	−0.002 (3)	0.006 (3)	0.004 (3)
N2	0.059 (4)	0.056 (4)	0.039 (3)	0.004 (3)	0.006 (3)	0.005 (3)
C1	0.046 (4)	0.046 (4)	0.052 (4)	−0.007 (3)	−0.006 (3)	0.001 (3)
C2	0.044 (4)	0.042 (4)	0.062 (4)	−0.001 (3)	−0.001 (4)	−0.001 (3)
C3	0.059 (5)	0.048 (4)	0.065 (4)	−0.001 (4)	−0.006 (4)	−0.008 (4)
C4	0.053 (4)	0.069 (5)	0.066 (5)	0.005 (4)	0.007 (4)	−0.003 (4)
C5	0.067 (5)	0.059 (5)	0.091 (6)	−0.009 (4)	0.017 (5)	0.003 (4)
C6	0.064 (5)	0.048 (4)	0.075 (5)	−0.004 (4)	0.013 (4)	−0.001 (4)
C7	0.040 (4)	0.042 (4)	0.052 (4)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C8	0.055 (4)	0.040 (4)	0.067 (4)	−0.007 (3)	−0.006 (4)	−0.011 (3)
C9	0.068 (5)	0.048 (4)	0.046 (4)	0.004 (4)	0.003 (4)	−0.010 (3)
C10	0.049 (4)	0.036 (3)	0.036 (4)	0.004 (3)	0.004 (3)	−0.007 (3)
C11	0.047 (4)	0.058 (4)	0.039 (4)	0.002 (4)	0.002 (3)	−0.002 (3)
C12	0.062 (5)	0.058 (5)	0.056 (4)	0.002 (4)	0.019 (4)	0.002 (4)
C13	0.046 (5)	0.098 (7)	0.073 (5)	0.002 (5)	0.000 (4)	−0.008 (5)
C14	0.057 (5)	0.111 (8)	0.082 (6)	−0.019 (6)	0.007 (5)	−0.016 (6)
C15	0.082 (6)	0.061 (5)	0.099 (7)	−0.014 (5)	0.008 (6)	−0.006 (5)
C16	0.069 (5)	0.051 (5)	0.076 (5)	−0.009 (4)	0.007 (4)	−0.006 (4)
C17	0.089 (7)	0.071 (6)	0.102 (7)	0.010 (5)	0.014 (5)	0.000 (5)
O3	0.091 (4)	0.034 (3)	0.083 (4)	0.008 (3)	0.028 (3)	0.008 (3)

Cl1—C3	1.742 (7)	C8—H8A	0.9700
O1—C7	1.230 (7)	C8—H8B	0.9700
O2—C10	1.215 (7)	C9—C10	1.499 (9)
N1—C7	1.338 (8)	C9—H9A	0.9700
N1—C1	1.404 (8)	C9—H9B	0.9700
N1—H1N	0.86 (2)	C11—C16	1.381 (9)
N2—C10	1.350 (8)	C11—C12	1.391 (9)
N2—C11	1.432 (8)	C12—C13	1.396 (10)
N2—H2N	0.86 (2)	C12—C17	1.469 (10)
C1—C2	1.384 (9)	C13—C14	1.366 (11)
C1—C6	1.393 (9)	C13—H13	0.9300
C2—C3	1.375 (9)	C14—C15	1.357 (11)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.358 (9)	C15—C16	1.378 (11)
C4—C5	1.386 (9)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.368 (10)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.494 (9)	O3—H31O	0.85 (2)
C8—C9	1.531 (9)	O3—H32O	0.84 (2)
C7—N1—C1	129.7 (6)	C10—C9—H9A	108.9
C7—N1—H1N	118 (4)	C8—C9—H9A	108.8
C1—N1—H1N	113 (4)	C10—C9—H9B	108.8
C10—N2—C11	125.5 (5)	C8—C9—H9B	108.8
C10—N2—H2N	121 (5)	H9A—C9—H9B	107.7
C11—N2—H2N	113 (5)	O2—C10—N2	122.4 (6)
C2—C1—C6	119.2 (6)	O2—C10—C9	123.8 (6)
C2—C1—N1	123.0 (6)	N2—C10—C9	113.7 (5)
C6—C1—N1	117.8 (6)	C16—C11—C12	120.8 (7)
C3—C2—C1	118.3 (6)	C16—C11—N2	118.2 (6)
C3—C2—H2	120.8	C12—C11—N2	120.9 (6)
C1—C2—H2	120.8	C11—C12—C13	117.6 (7)
C4—C3—C2	123.6 (7)	C11—C12—C17	123.3 (7)
C4—C3—Cl1	118.4 (6)	C13—C12—C17	119.1 (8)
C2—C3—Cl1	118.0 (6)	C14—C13—C12	120.6 (8)
C3—C4—C5	117.6 (7)	C14—C13—H13	119.7
C3—C4—H4	121.2	C12—C13—H13	119.7
C5—C4—H4	121.2	C15—C14—C13	121.6 (9)
C6—C5—C4	120.8 (7)	C15—C14—H14	119.2
C6—C5—H5	119.6	C13—C14—H14	119.2
C4—C5—H5	119.6	C14—C15—C16	119.1 (8)
C5—C6—C1	120.5 (7)	C14—C15—H15	120.4
C5—C6—H6	119.7	C16—C15—H15	120.4
C1—C6—H6	119.7	C15—C16—C11	120.3 (8)
O1—C7—N1	123.5 (6)	C15—C16—H16	119.8
O1—C7—C8	122.8 (6)	C11—C16—H16	119.8
N1—C7—C8	113.7 (6)	C12—C17—H17A	109.5
C7—C8—C9	114.0 (5)	C12—C17—H17B	109.5
C7—C8—H8A	108.8	H17A—C17—H17B	109.5
C9—C8—H8A	108.8	C12—C17—H17C	109.5
C7—C8—H8B	108.8	H17A—C17—H17C	109.5
C9—C8—H8B	108.8	H17B—C17—H17C	109.5
H8A—C8—H8B	107.7	H31O—O3—H32O	108 (3)
C10—C9—C8	113.6 (5)
C7—N1—C1—C2	2.1 (11)	C11—N2—C10—O2	−0.2 (10)
C7—N1—C1—C6	−180.0 (7)	C11—N2—C10—C9	−177.8 (6)
C6—C1—C2—C3	−1.0 (10)	C8—C9—C10—O2	13.0 (9)
N1—C1—C2—C3	177.0 (6)	C8—C9—C10—N2	−169.4 (5)
C1—C2—C3—C4	1.1 (10)	C10—N2—C11—C16	−119.5 (7)
C1—C2—C3—Cl1	−179.5 (5)	C10—N2—C11—C12	63.9 (8)
C2—C3—C4—C5	−0.4 (11)	C16—C11—C12—C13	0.1 (9)
Cl1—C3—C4—C5	−179.9 (6)	N2—C11—C12—C13	176.6 (6)
C3—C4—C5—C6	−0.2 (12)	C16—C11—C12—C17	−176.8 (7)
C4—C5—C6—C1	0.3 (12)	N2—C11—C12—C17	−0.2 (9)
C2—C1—C6—C5	0.3 (11)	C11—C12—C13—C14	−0.8 (10)
N1—C1—C6—C5	−177.7 (7)	C17—C12—C13—C14	176.2 (7)
C1—N1—C7—O1	6.9 (11)	C12—C13—C14—C15	0.6 (13)
C1—N1—C7—C8	−173.0 (6)	C13—C14—C15—C16	0.4 (13)
O1—C7—C8—C9	5.4 (9)	C14—C15—C16—C11	−1.2 (12)
N1—C7—C8—C9	−174.7 (6)	C12—C11—C16—C15	0.9 (10)
C7—C8—C9—C10	69.5 (7)	N2—C11—C16—C15	−175.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N···O2ii	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O···O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O···O1iii	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86 (2)	2.08 (2)	2.940 (7)	175 (6)
N2—H2N⋯O2ii	0.86 (2)	2.25 (4)	2.991 (7)	145 (6)
O3—H31O⋯O2	0.85 (2)	2.04 (3)	2.861 (6)	163 (8)
O3—H32O⋯O1iii	0.84 (2)	2.05 (3)	2.877 (6)	171 (9)

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