N-(3-Chloro-phen-yl)-3-methyl-benzamide hemihydrate.

In the title compound, C(14)H(12)ClNO·0.5H(2)O, the N-H bond is in an anti conformation to the C=O bond. The two aromatic rings make a dihedral angle of 49.5 (1)°. The water mol-ecule lies on a twofold rotation axis. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds connect the mol-ecules into a three-dimensional network.

Related literature

For the preparation of the title compound and related structures, see: Gowda et al. (2008 ▶); Bowes et al. (2003 ▶); Rodrigues et al. (2010 ▶).

Experimental

Crystal data

C14H12ClNO·0.5H2O

M = 254.71

Monoclinic,

a = 7.6497 (3) Å

b = 12.6829 (5) Å

c = 25.9694 (10) Å

β = 95.365 (3)°

V = 2508.54 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.52 × 0.16 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.860, T max = 0.984

19774 measured reflections

2277 independent reflections

1894 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.095

S = 1.07

2277 reflections

164 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010354/bt5221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010354/bt5221Isup2.hkl

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

C14H12ClNO·0.5H2O	F(000) = 1064
Mr = 254.71	Dx = 1.349 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9097 reflections
a = 7.6497 (3) Å	θ = 2.4–29.6°
b = 12.6829 (5) Å	µ = 0.29 mm−1
c = 25.9694 (10) Å	T = 295 K
β = 95.365 (3)°	Rod, colourless
V = 2508.54 (16) Å3	0.52 × 0.16 × 0.06 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector	2277 independent reflections
graphite	1894 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.029
ω scans	θmax = 25.3°, θmin = 3.1°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.860, Tmax = 0.984	k = −15→15
19774 measured reflections	l = −31→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.037P)2 + 1.9211P] where P = (Fo2 + 2Fc2)/3
2277 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.16 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.2652 (2)	0.58130 (14)	0.27335 (7)	0.0377 (4)
C2	0.2321 (2)	0.59925 (13)	0.21633 (6)	0.0357 (4)
C3	0.1655 (2)	0.69364 (13)	0.19574 (6)	0.0369 (4)
H3	0.1451	0.749	0.2179	0.044*
C4	0.1286 (2)	0.70707 (14)	0.14252 (7)	0.0384 (4)
C5	0.1625 (2)	0.62336 (15)	0.11091 (7)	0.0447 (4)
H5	0.1389	0.6307	0.0753	0.054*
C6	0.2302 (3)	0.52944 (15)	0.13046 (7)	0.0485 (5)
H6	0.2535	0.4748	0.1082	0.058*
C7	0.2633 (2)	0.51674 (14)	0.18334 (7)	0.0435 (4)
H7	0.3064	0.4529	0.1968	0.052*
C8	0.3568 (2)	0.67382 (13)	0.35616 (6)	0.0330 (4)
C9	0.2973 (2)	0.59967 (14)	0.38974 (7)	0.0392 (4)
H9	0.2362	0.5402	0.3772	0.047*
C10	0.3311 (2)	0.61650 (15)	0.44221 (7)	0.0450 (4)
C11	0.4205 (3)	0.70309 (16)	0.46236 (7)	0.0524 (5)
H11	0.4424	0.7123	0.4979	0.063*
C12	0.4770 (3)	0.77618 (16)	0.42818 (7)	0.0516 (5)
H12	0.5371	0.8359	0.4409	0.062*
C13	0.4461 (2)	0.76231 (14)	0.37559 (7)	0.0407 (4)
H13	0.4851	0.8123	0.3531	0.049*
C14	0.0552 (3)	0.80902 (15)	0.12042 (8)	0.0542 (5)
H14A	0.0834	0.865	0.1446	0.081*	0.52 (9)
H14B	−0.07	0.8032	0.1138	0.081*	0.52 (9)
H14C	0.1053	0.824	0.0887	0.081*	0.52 (9)
H14D	0.1418	0.8436	0.1019	0.081*	0.48 (9)
H14E	0.0242	0.8537	0.148	0.081*	0.48 (9)
H14F	−0.0474	0.7949	0.0972	0.081*	0.48 (9)
N1	0.32473 (17)	0.66596 (11)	0.30168 (5)	0.0362 (3)
H1N	0.3456	0.7217	0.2845	0.043*
O1	0.24049 (18)	0.49471 (10)	0.29259 (5)	0.0516 (4)
O2W	0	0.34503 (13)	0.25	0.0413 (4)
H2W	0.077 (2)	0.3837 (15)	0.2631 (7)	0.05*
Cl1	0.25269 (9)	0.52457 (5)	0.48445 (2)	0.0763 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0362 (9)	0.0364 (10)	0.0401 (9)	−0.0005 (7)	0.0012 (7)	−0.0016 (8)
C2	0.0340 (9)	0.0362 (10)	0.0368 (9)	−0.0055 (7)	0.0030 (7)	−0.0004 (7)
C3	0.0350 (9)	0.0368 (9)	0.0389 (10)	−0.0028 (7)	0.0028 (7)	−0.0064 (8)
C4	0.0356 (9)	0.0388 (10)	0.0401 (10)	−0.0050 (7)	−0.0005 (7)	−0.0018 (8)
C5	0.0503 (10)	0.0495 (11)	0.0337 (9)	−0.0073 (9)	0.0010 (8)	−0.0041 (9)
C6	0.0611 (12)	0.0412 (11)	0.0438 (11)	−0.0018 (9)	0.0090 (9)	−0.0111 (9)
C7	0.0514 (10)	0.0354 (10)	0.0440 (10)	−0.0002 (8)	0.0057 (8)	−0.0023 (8)
C8	0.0322 (8)	0.0330 (9)	0.0339 (9)	0.0055 (7)	0.0028 (7)	−0.0017 (7)
C9	0.0442 (10)	0.0344 (9)	0.0389 (10)	−0.0013 (8)	0.0035 (8)	−0.0021 (8)
C10	0.0534 (11)	0.0441 (11)	0.0381 (10)	0.0026 (9)	0.0077 (8)	0.0044 (8)
C11	0.0641 (12)	0.0601 (13)	0.0321 (10)	−0.0029 (10)	−0.0007 (9)	−0.0071 (9)
C12	0.0566 (12)	0.0477 (11)	0.0497 (11)	−0.0101 (9)	0.0014 (9)	−0.0113 (9)
C13	0.0456 (10)	0.0380 (10)	0.0388 (10)	−0.0027 (8)	0.0051 (8)	−0.0012 (8)
C14	0.0607 (12)	0.0472 (12)	0.0529 (12)	0.0029 (10)	−0.0041 (9)	0.0026 (9)
N1	0.0435 (8)	0.0319 (7)	0.0331 (8)	−0.0034 (6)	0.0025 (6)	0.0023 (6)
O1	0.0757 (9)	0.0354 (7)	0.0417 (7)	−0.0116 (6)	−0.0055 (6)	0.0036 (6)
O2W	0.0476 (10)	0.0314 (10)	0.0442 (10)	0	−0.0003 (8)	0
Cl1	0.1181 (5)	0.0692 (4)	0.0436 (3)	−0.0204 (3)	0.0181 (3)	0.0103 (3)

C1—O1	1.228 (2)	C9—C10	1.380 (2)
C1—N1	1.356 (2)	C9—H9	0.93
C1—C2	1.496 (2)	C10—C11	1.371 (3)
C2—C7	1.387 (2)	C10—Cl1	1.7451 (19)
C2—C3	1.389 (2)	C11—C12	1.380 (3)
C3—C4	1.395 (2)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.375 (2)
C4—C5	1.382 (2)	C12—H12	0.93
C4—C14	1.502 (3)	C13—H13	0.93
C5—C6	1.377 (3)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—C7	1.382 (3)	C14—H14C	0.96
C6—H6	0.93	C14—H14D	0.96
C7—H7	0.93	C14—H14E	0.96
C8—C13	1.384 (2)	C14—H14F	0.96
C8—C9	1.388 (2)	N1—H1N	0.86
C8—N1	1.417 (2)	O2W—H2W	0.813 (18)
O1—C1—N1	122.95 (16)	C8—C9—H9	120.9
O1—C1—C2	121.35 (15)	C11—C10—C9	122.79 (17)
N1—C1—C2	115.69 (15)	C11—C10—Cl1	118.93 (14)
C7—C2—C3	119.37 (16)	C9—C10—Cl1	118.27 (14)
C7—C2—C1	118.28 (15)	C10—C11—C12	117.86 (17)
C3—C2—C1	122.30 (15)	C10—C11—H11	121.1
C2—C3—C4	121.33 (16)	C12—C11—H11	121.1
C2—C3—H3	119.3	C13—C12—C11	121.16 (18)
C4—C3—H3	119.3	C13—C12—H12	119.4
C5—C4—C3	117.58 (16)	C11—C12—H12	119.4
C5—C4—C14	121.24 (16)	C12—C13—C8	119.93 (17)
C3—C4—C14	121.17 (16)	C12—C13—H13	120
C6—C5—C4	122.05 (17)	C8—C13—H13	120
C6—C5—H5	119	C4—C14—H14A	109.5
C4—C5—H5	119	C4—C14—H14B	109.5
C5—C6—C7	119.67 (17)	C4—C14—H14C	109.5
C5—C6—H6	120.2	C4—C14—H14D	109.5
C7—C6—H6	120.2	C4—C14—H14E	109.5
C6—C7—C2	119.98 (17)	H14D—C14—H14E	109.5
C6—C7—H7	120	C4—C14—H14F	109.5
C2—C7—H7	120	H14D—C14—H14F	109.5
C13—C8—C9	119.99 (15)	H14E—C14—H14F	109.5
C13—C8—N1	117.04 (15)	C1—N1—C8	127.99 (14)
C9—C8—N1	122.92 (15)	C1—N1—H1N	116
C10—C9—C8	118.26 (16)	C8—N1—H1N	116
C10—C9—H9	120.9
O1—C1—C2—C7	−33.4 (2)	C13—C8—C9—C10	−0.6 (2)
N1—C1—C2—C7	146.10 (16)	N1—C8—C9—C10	−178.05 (15)
O1—C1—C2—C3	144.07 (17)	C8—C9—C10—C11	0.1 (3)
N1—C1—C2—C3	−36.4 (2)	C8—C9—C10—Cl1	178.80 (13)
C7—C2—C3—C4	0.2 (2)	C9—C10—C11—C12	0.5 (3)
C1—C2—C3—C4	−177.18 (15)	Cl1—C10—C11—C12	−178.23 (15)
C2—C3—C4—C5	−0.7 (2)	C10—C11—C12—C13	−0.5 (3)
C2—C3—C4—C14	179.53 (16)	C11—C12—C13—C8	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C9—C8—C13—C12	0.6 (3)
C14—C4—C5—C6	179.83 (17)	N1—C8—C13—C12	178.17 (16)
C4—C5—C6—C7	1.0 (3)	O1—C1—N1—C8	−4.7 (3)
C5—C6—C7—C2	−1.5 (3)	C2—C1—N1—C8	175.85 (14)
C3—C2—C7—C6	0.9 (3)	C13—C8—N1—C1	169.04 (16)
C1—C2—C7—C6	178.40 (16)	C9—C8—N1—C1	−13.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2Wi	0.86	2.2	3.0155 (19)	158
O2W—H2W···O1	0.813 (18)	1.991 (18)	2.7984 (17)	171.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2Wi	0.86	2.2	3.0155 (19)	158
O2W—H2W⋯O1	0.813 (18)	1.991 (18)	2.7984 (17)	171.9 (19)

Symmetry code: (i) .