N-(4-Chloro-phen-yl)-N'-(3-methyl-phen-yl)succinamide monohydrate.

In the title hydrate, 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 their attached NH-C(O)-CH(2) fragments are 16.6 (2) and 22.8 (2)°, respectively. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the components into a two-dimensional network parallel to the ab plane.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶) and on N-chloro-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C17H17ClN2O2·H2O

M = 334.79

Monoclinic,

a = 12.210 (1) Å

b = 4.9111 (5) Å

c = 27.078 (3) Å

β = 93.104 (9)°

V = 1621.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.36 × 0.28 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.915, T max = 0.980

5592 measured reflections

3297 independent reflections

2047 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.127

S = 1.02

3297 reflections

221 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.21 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/S1600536811032685/ds2132sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032685/ds2132Isup2.hkl

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

C17H17ClN2O2·H2O	F(000) = 704
Mr = 334.79	Dx = 1.372 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1575 reflections
a = 12.210 (1) Å	θ = 2.9–27.9°
b = 4.9111 (5) Å	µ = 0.25 mm−1
c = 27.078 (3) Å	T = 293 K
β = 93.104 (9)°	Prism, colourless
V = 1621.3 (3) Å3	0.36 × 0.28 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur Single Crystal X-ray Diffractometer with Sapphire CCD Detector	3297 independent reflections
Radiation source: fine-focus sealed tube	2047 reflections with I > 2σ(I)
graphite	Rint = 0.027
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→12
Tmin = 0.915, Tmax = 0.980	k = −6→4
5592 measured reflections	l = −33→28

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.9732P] where P = (Fo2 + 2Fc2)/3
3297 reflections	(Δ/σ)max = 0.006
221 parameters	Δρmax = 0.37 e Å−3
2 restraints	Δρmin = −0.21 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	0.34943 (7)	−0.42307 (17)	0.47553 (3)	0.0622 (3)
O1	0.62296 (14)	0.4094 (4)	0.31577 (7)	0.0451 (5)
O2	0.47762 (15)	1.1220 (4)	0.19755 (8)	0.0554 (6)
N1	0.43883 (17)	0.4107 (5)	0.32510 (8)	0.0380 (5)
H1N	0.3799 (17)	0.487 (5)	0.3143 (10)	0.046*
N2	0.65157 (17)	1.1254 (5)	0.17399 (8)	0.0373 (6)
H2N	0.7152 (16)	1.057 (5)	0.1796 (10)	0.045*
C1	0.4245 (2)	0.2068 (5)	0.36099 (9)	0.0351 (6)
C2	0.3184 (2)	0.1093 (6)	0.36530 (11)	0.0457 (7)
H2	0.2618	0.1769	0.3444	0.055*
C3	0.2956 (2)	−0.0856 (6)	0.39993 (11)	0.0480 (8)
H3	0.2246	−0.1509	0.4021	0.058*
C4	0.3790 (2)	−0.1817 (6)	0.43102 (10)	0.0410 (7)
C5	0.4841 (2)	−0.0908 (6)	0.42698 (11)	0.0510 (8)
H5	0.5402	−0.1603	0.4479	0.061*
C6	0.5079 (2)	0.1033 (6)	0.39211 (11)	0.0469 (7)
H6	0.5796	0.1638	0.3896	0.056*
C7	0.5316 (2)	0.4993 (5)	0.30498 (9)	0.0322 (6)
C8	0.5080 (2)	0.7174 (6)	0.26629 (10)	0.0398 (7)
H8A	0.4700	0.8660	0.2816	0.048*
H8B	0.4585	0.6421	0.2406	0.048*
C9	0.6068 (2)	0.8327 (6)	0.24219 (10)	0.0379 (6)
H9A	0.6470	0.6861	0.2274	0.046*
H9B	0.6552	0.9190	0.2671	0.046*
C10	0.5724 (2)	1.0393 (5)	0.20277 (10)	0.0356 (6)
C11	0.6394 (2)	1.2938 (5)	0.13128 (9)	0.0336 (6)
C12	0.5546 (2)	1.4811 (5)	0.12350 (10)	0.0371 (6)
H12	0.5030	1.5018	0.1473	0.044*
C13	0.5460 (2)	1.6381 (5)	0.08064 (10)	0.0400 (7)
C14	0.6241 (2)	1.6058 (6)	0.04607 (11)	0.0515 (8)
H14	0.6194	1.7083	0.0172	0.062*
C15	0.7089 (3)	1.4234 (7)	0.05399 (11)	0.0536 (8)
H15	0.7611	1.4055	0.0304	0.064*
C16	0.7176 (2)	1.2668 (6)	0.09629 (10)	0.0436 (7)
H16	0.7752	1.1444	0.1013	0.052*
C17	0.4529 (3)	1.8381 (6)	0.07173 (12)	0.0548 (8)
H17A	0.4172	1.8673	0.1020	0.066*
H17B	0.4011	1.7662	0.0472	0.066*
H17C	0.4814	2.0078	0.0603	0.066*
O3	0.26720 (16)	0.1047 (4)	0.22674 (8)	0.0468 (5)
H31	0.334 (3)	0.112 (6)	0.2162 (11)	0.056*
H32	0.255 (3)	0.256 (7)	0.2390 (12)	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0730 (6)	0.0536 (5)	0.0616 (5)	−0.0016 (4)	0.0197 (4)	0.0174 (4)
O1	0.0285 (10)	0.0509 (12)	0.0559 (12)	−0.0002 (9)	0.0033 (8)	0.0104 (10)
O2	0.0303 (10)	0.0670 (15)	0.0701 (14)	0.0120 (10)	0.0148 (9)	0.0289 (12)
N1	0.0273 (11)	0.0412 (13)	0.0457 (13)	0.0033 (11)	0.0043 (10)	0.0110 (11)
N2	0.0237 (11)	0.0434 (14)	0.0452 (13)	0.0038 (10)	0.0050 (10)	0.0084 (11)
C1	0.0330 (14)	0.0361 (15)	0.0368 (14)	−0.0021 (12)	0.0066 (11)	0.0001 (12)
C2	0.0331 (14)	0.0499 (18)	0.0541 (18)	−0.0007 (14)	0.0023 (13)	0.0109 (15)
C3	0.0371 (15)	0.0505 (19)	0.0575 (18)	−0.0076 (14)	0.0113 (14)	0.0078 (16)
C4	0.0469 (17)	0.0359 (15)	0.0415 (16)	−0.0018 (13)	0.0133 (13)	0.0021 (13)
C5	0.0460 (17)	0.0529 (19)	0.0538 (18)	0.0040 (15)	0.0008 (14)	0.0168 (16)
C6	0.0322 (14)	0.0548 (19)	0.0536 (17)	−0.0029 (14)	0.0000 (13)	0.0136 (15)
C7	0.0278 (13)	0.0325 (14)	0.0364 (14)	−0.0034 (11)	0.0025 (11)	−0.0036 (11)
C8	0.0350 (14)	0.0384 (15)	0.0465 (16)	0.0006 (13)	0.0072 (12)	0.0058 (13)
C9	0.0300 (13)	0.0387 (15)	0.0452 (16)	−0.0001 (12)	0.0032 (12)	0.0049 (13)
C10	0.0282 (13)	0.0363 (15)	0.0426 (15)	0.0008 (12)	0.0057 (11)	0.0002 (12)
C11	0.0305 (13)	0.0323 (14)	0.0380 (14)	−0.0048 (12)	0.0012 (11)	0.0014 (12)
C12	0.0329 (14)	0.0377 (15)	0.0410 (15)	−0.0004 (12)	0.0058 (12)	−0.0033 (12)
C13	0.0401 (15)	0.0326 (15)	0.0465 (16)	−0.0006 (12)	−0.0044 (12)	0.0007 (13)
C14	0.0543 (18)	0.0526 (19)	0.0479 (17)	0.0000 (16)	0.0051 (15)	0.0115 (15)
C15	0.0505 (18)	0.064 (2)	0.0482 (18)	0.0066 (17)	0.0172 (14)	0.0094 (17)
C16	0.0334 (14)	0.0494 (18)	0.0487 (17)	0.0051 (13)	0.0077 (13)	0.0059 (14)
C17	0.0543 (19)	0.0449 (18)	0.064 (2)	0.0063 (16)	−0.0041 (16)	0.0057 (16)
O3	0.0288 (10)	0.0451 (12)	0.0670 (14)	−0.0026 (10)	0.0065 (9)	−0.0049 (11)

Cl1—C4	1.742 (3)	C8—H8A	0.9700
O1—C7	1.220 (3)	C8—H8B	0.9700
O2—C10	1.227 (3)	C9—C10	1.516 (4)
N1—C7	1.355 (3)	C9—H9A	0.9700
N1—C1	1.413 (3)	C9—H9B	0.9700
N1—H1N	0.849 (17)	C11—C16	1.388 (3)
N2—C10	1.343 (3)	C11—C12	1.392 (4)
N2—C11	1.423 (3)	C12—C13	1.392 (4)
N2—H2N	0.852 (17)	C12—H12	0.9300
C1—C6	1.382 (4)	C13—C14	1.381 (4)
C1—C2	1.393 (3)	C13—C17	1.512 (4)
C2—C3	1.379 (4)	C14—C15	1.377 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.369 (4)	C15—C16	1.379 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.369 (4)	C16—H16	0.9300
C5—C6	1.384 (4)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.515 (4)	O3—H31	0.88 (3)
C8—C9	1.513 (3)	O3—H32	0.83 (3)
C7—N1—C1	129.9 (2)	C8—C9—H9A	109.5
C7—N1—H1N	115.5 (19)	C10—C9—H9A	109.5
C1—N1—H1N	114.6 (19)	C8—C9—H9B	109.5
C10—N2—C11	127.4 (2)	C10—C9—H9B	109.5
C10—N2—H2N	116.8 (19)	H9A—C9—H9B	108.0
C11—N2—H2N	115.4 (19)	O2—C10—N2	122.2 (3)
C6—C1—C2	118.7 (2)	O2—C10—C9	121.8 (2)
C6—C1—N1	124.4 (2)	N2—C10—C9	116.0 (2)
C2—C1—N1	116.8 (2)	C16—C11—C12	119.6 (2)
C3—C2—C1	121.2 (3)	C16—C11—N2	117.0 (2)
C3—C2—H2	119.4	C12—C11—N2	123.5 (2)
C1—C2—H2	119.4	C11—C12—C13	120.9 (2)
C4—C3—C2	119.1 (3)	C11—C12—H12	119.5
C4—C3—H3	120.4	C13—C12—H12	119.5
C2—C3—H3	120.4	C14—C13—C12	118.5 (3)
C3—C4—C5	120.5 (3)	C14—C13—C17	120.5 (3)
C3—C4—Cl1	119.0 (2)	C12—C13—C17	121.0 (2)
C5—C4—Cl1	120.5 (2)	C15—C14—C13	120.6 (3)
C4—C5—C6	120.8 (3)	C15—C14—H14	119.7
C4—C5—H5	119.6	C13—C14—H14	119.7
C6—C5—H5	119.6	C14—C15—C16	121.0 (3)
C1—C6—C5	119.6 (3)	C14—C15—H15	119.5
C1—C6—H6	120.2	C16—C15—H15	119.5
C5—C6—H6	120.2	C15—C16—C11	119.3 (3)
O1—C7—N1	124.1 (2)	C15—C16—H16	120.4
O1—C7—C8	123.9 (2)	C11—C16—H16	120.4
N1—C7—C8	111.9 (2)	C13—C17—H17A	109.5
C7—C8—C9	115.9 (2)	C13—C17—H17B	109.5
C7—C8—H8A	108.3	H17A—C17—H17B	109.5
C9—C8—H8A	108.3	C13—C17—H17C	109.5
C7—C8—H8B	108.3	H17A—C17—H17C	109.5
C9—C8—H8B	108.3	H17B—C17—H17C	109.5
H8A—C8—H8B	107.4	H31—O3—H32	106 (3)
C8—C9—C10	110.9 (2)
C7—N1—C1—C6	17.5 (5)	C11—N2—C10—O2	−7.3 (5)
C7—N1—C1—C2	−163.6 (3)	C11—N2—C10—C9	172.6 (2)
C6—C1—C2—C3	0.3 (4)	C8—C9—C10—O2	9.3 (4)
N1—C1—C2—C3	−178.6 (3)	C8—C9—C10—N2	−170.6 (2)
C1—C2—C3—C4	0.9 (5)	C10—N2—C11—C16	−153.7 (3)
C2—C3—C4—C5	−1.7 (5)	C10—N2—C11—C12	26.7 (4)
C2—C3—C4—Cl1	178.8 (2)	C16—C11—C12—C13	1.3 (4)
C3—C4—C5—C6	1.2 (5)	N2—C11—C12—C13	−179.1 (2)
Cl1—C4—C5—C6	−179.2 (2)	C11—C12—C13—C14	−0.6 (4)
C2—C1—C6—C5	−0.8 (4)	C11—C12—C13—C17	178.9 (3)
N1—C1—C6—C5	178.1 (3)	C12—C13—C14—C15	−0.3 (5)
C4—C5—C6—C1	0.0 (5)	C17—C13—C14—C15	−179.9 (3)
C1—N1—C7—O1	−0.1 (5)	C13—C14—C15—C16	0.6 (5)
C1—N1—C7—C8	178.2 (3)	C14—C15—C16—C11	0.1 (5)
O1—C7—C8—C9	−2.7 (4)	C12—C11—C16—C15	−1.0 (4)
N1—C7—C8—C9	179.1 (2)	N2—C11—C16—C15	179.4 (3)
C7—C8—C9—C10	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.85 (2)	2.14 (2)	2.971 (3)	166 (3)
N2—H2N···O1ii	0.85 (2)	2.10 (2)	2.949 (3)	172 (3)
O3—H31···O2iii	0.88 (3)	1.86 (3)	2.730 (3)	177 (3)
O3—H32···O3i	0.83 (3)	1.97 (3)	2.802 (2)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.85 (2)	2.14 (2)	2.971 (3)	166 (3)
N2—H2N⋯O1ii	0.85 (2)	2.10 (2)	2.949 (3)	172 (3)
O3—H31⋯O2iii	0.88 (3)	1.86 (3)	2.730 (3)	177 (3)
O3—H32⋯O3i	0.83 (3)	1.97 (3)	2.802 (2)	175 (3)

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