N-(3-Chloro-phen-yl)-4-methyl-benzamide hemihydrate.

In the title compound, C(14)H(12)ClNO·0.5H(2)O, the water mol-ecule is located on a twofold axis of symmetry. The meta-Cl atom in the aniline ring is positioned anti to the N-H bond. The two benzene rings make a dihedral angle of 40.40 (11)°. The crystal structure is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, which link the mol-ecules into chains along the a axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (1999 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro-aryl­sulfonamides, see: Gowda & Shetty (2004 ▶).

Experimental

Crystal data

C14H12ClNO·0.5H2O

M = 254.71

Monoclinic,

a = 7.8078 (3) Å

b = 12.1704 (5) Å

c = 27.1217 (9) Å

β = 93.564 (3)°

V = 2572.24 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.76 × 0.34 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.890, T max = 0.993

3313 measured reflections

3313 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.142

S = 1.01

3313 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040992/bq2309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040992/bq2309Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040992/bq2309Isup3.cml

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

C14H12ClNO·0.5H2O	F(000) = 1064
Mr = 254.71	Dx = 1.315 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 21518 reflections
a = 7.8078 (3) Å	θ = 3.5–29.4°
b = 12.1704 (5) Å	µ = 0.29 mm−1
c = 27.1217 (9) Å	T = 298 K
β = 93.564 (3)°	Plate, colorless
V = 2572.24 (17) Å3	0.76 × 0.34 × 0.02 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3313 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.5°
ω scans	h = −10→10
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −16→16
Tmin = 0.890, Tmax = 0.993	l = −36→33
3313 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.049P)2 + 2.1399P] where P = (Fo2 + 2Fc2)/3
3313 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	Occ. (<1)
C1	0.2326 (2)	0.60328 (17)	0.27192 (7)	0.0465 (5)
C2	0.2647 (2)	0.63298 (17)	0.21979 (7)	0.0452 (5)
C3	0.3261 (2)	0.73485 (18)	0.20695 (7)	0.0502 (5)
H3A	0.3404	0.7896	0.2307	0.060*
C4	0.3664 (3)	0.7558 (2)	0.15888 (8)	0.0589 (6)
H4A	0.4091	0.8245	0.1510	0.071*
C5	0.3444 (3)	0.6770 (2)	0.12247 (8)	0.0606 (6)
C6	0.2797 (3)	0.5762 (2)	0.13527 (8)	0.0639 (7)
H6A	0.2615	0.5226	0.1111	0.077*
C7	0.2413 (3)	0.55318 (19)	0.18318 (8)	0.0566 (6)
H7A	0.1998	0.4842	0.1910	0.068*
C8	0.3887 (4)	0.7009 (3)	0.07011 (9)	0.0856 (10)
H8C	0.423 (2)	0.6369 (10)	0.0554 (3)	0.103*	0.50
H8B	0.476 (2)	0.7518 (13)	0.07042 (9)	0.103*	0.50
H8A	0.2934 (16)	0.7286 (15)	0.0525 (3)	0.103*	0.50
H8F	0.424 (2)	0.6373 (10)	0.0552 (3)	0.103*	0.50
H8E	0.476 (2)	0.7517 (13)	0.07049 (9)	0.103*	0.50
H8D	0.2940 (16)	0.7288 (15)	0.0523 (3)	0.103*	0.50
C9	0.1532 (2)	0.68527 (16)	0.35142 (7)	0.0427 (5)
C10	0.1959 (3)	0.59716 (19)	0.38225 (7)	0.0528 (5)
H10A	0.2417	0.5330	0.3699	0.063*
C11	0.1685 (3)	0.6074 (2)	0.43183 (8)	0.0582 (6)
C12	0.1025 (3)	0.6999 (2)	0.45181 (8)	0.0623 (6)
H12A	0.0851	0.7040	0.4854	0.075*
C13	0.0623 (3)	0.7868 (2)	0.42085 (8)	0.0634 (6)
H13A	0.0179	0.8509	0.4337	0.076*
C14	0.0871 (3)	0.78007 (18)	0.37099 (8)	0.0532 (5)
H14A	0.0592	0.8395	0.3505	0.064*
N1	0.1767 (2)	0.68533 (15)	0.30024 (6)	0.0446 (4)
H1N	0.142 (3)	0.7439 (19)	0.2852 (8)	0.051 (6)*
O1	0.2586 (2)	0.50930 (12)	0.28769 (6)	0.0653 (5)
O2	0.5000	0.37191 (16)	0.2500	0.0465 (5)
H2O	0.573 (3)	0.412 (2)	0.2370 (9)	0.077 (8)*
Cl1	0.22644 (12)	0.49860 (7)	0.47115 (3)	0.0998 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0489 (11)	0.0454 (12)	0.0457 (11)	0.0082 (9)	0.0073 (9)	−0.0017 (9)
C2	0.0453 (11)	0.0496 (12)	0.0410 (11)	0.0132 (9)	0.0041 (8)	0.0001 (9)
C3	0.0487 (11)	0.0564 (13)	0.0457 (12)	0.0040 (10)	0.0052 (9)	−0.0042 (10)
C4	0.0569 (13)	0.0665 (15)	0.0544 (14)	0.0037 (11)	0.0113 (10)	0.0077 (11)
C5	0.0581 (13)	0.0809 (18)	0.0433 (12)	0.0259 (12)	0.0080 (10)	0.0040 (12)
C6	0.0819 (16)	0.0681 (17)	0.0413 (12)	0.0271 (13)	0.0003 (11)	−0.0106 (11)
C7	0.0728 (14)	0.0489 (13)	0.0480 (12)	0.0141 (11)	0.0024 (10)	−0.0052 (10)
C8	0.0910 (19)	0.119 (3)	0.0488 (14)	0.0294 (18)	0.0182 (13)	0.0114 (15)
C9	0.0407 (10)	0.0486 (12)	0.0393 (10)	−0.0001 (9)	0.0055 (8)	−0.0030 (9)
C10	0.0592 (13)	0.0557 (13)	0.0443 (12)	0.0075 (10)	0.0083 (9)	−0.0005 (10)
C11	0.0606 (13)	0.0699 (16)	0.0444 (12)	0.0025 (11)	0.0071 (10)	0.0079 (11)
C12	0.0630 (14)	0.0837 (18)	0.0413 (12)	−0.0007 (12)	0.0118 (10)	−0.0086 (12)
C13	0.0734 (15)	0.0627 (15)	0.0552 (14)	0.0057 (12)	0.0145 (11)	−0.0164 (12)
C14	0.0607 (13)	0.0501 (13)	0.0494 (12)	0.0046 (10)	0.0080 (10)	−0.0047 (10)
N1	0.0525 (10)	0.0426 (10)	0.0391 (9)	0.0097 (8)	0.0062 (7)	0.0009 (8)
O1	0.0982 (12)	0.0471 (9)	0.0530 (9)	0.0223 (8)	0.0233 (8)	0.0052 (7)
O2	0.0543 (12)	0.0347 (11)	0.0513 (12)	0.000	0.0100 (10)	0.000
Cl1	0.1414 (7)	0.1010 (6)	0.0589 (4)	0.0332 (5)	0.0211 (4)	0.0276 (4)

C1—O1	1.233 (2)	C8—H8F	0.9223
C1—N1	1.349 (2)	C8—H8E	0.9222
C1—C2	1.495 (3)	C8—H8D	0.9223
C2—C3	1.382 (3)	C9—C14	1.383 (3)
C2—C7	1.393 (3)	C9—C10	1.388 (3)
C3—C4	1.384 (3)	C9—N1	1.411 (2)
C3—H3A	0.9300	C10—C11	1.380 (3)
C4—C5	1.379 (3)	C10—H10A	0.9300
C4—H4A	0.9300	C11—C12	1.365 (3)
C5—C6	1.380 (4)	C11—Cl1	1.742 (2)
C5—C8	1.511 (3)	C12—C13	1.374 (3)
C6—C7	1.380 (3)	C12—H12A	0.9300
C6—H6A	0.9300	C13—C14	1.380 (3)
C7—H7A	0.9300	C13—H13A	0.9300
C8—H8C	0.9223	C14—H14A	0.9300
C8—H8B	0.9223	N1—H1N	0.86 (2)
C8—H8A	0.9223	O2—H2O	0.84 (2)
O1—C1—N1	122.76 (19)	C5—C8—H8E	109.4
O1—C1—C2	121.22 (18)	H8C—C8—H8E	109.4
N1—C1—C2	116.01 (18)	H8A—C8—H8E	109.6
C3—C2—C7	118.55 (19)	H8F—C8—H8E	109.1
C3—C2—C1	122.43 (18)	C5—C8—H8D	109.9
C7—C2—C1	118.9 (2)	H8C—C8—H8D	109.4
C2—C3—C4	120.4 (2)	H8B—C8—H8D	109.1
C2—C3—H3A	119.8	H8F—C8—H8D	109.2
C4—C3—H3A	119.8	H8E—C8—H8D	109.2
C5—C4—C3	121.4 (2)	C14—C9—C10	119.64 (18)
C5—C4—H4A	119.3	C14—C9—N1	116.84 (18)
C3—C4—H4A	119.3	C10—C9—N1	123.51 (18)
C4—C5—C6	118.0 (2)	C11—C10—C9	118.1 (2)
C4—C5—C8	120.9 (3)	C11—C10—H10A	120.9
C6—C5—C8	121.1 (2)	C9—C10—H10A	120.9
C5—C6—C7	121.4 (2)	C12—C11—C10	123.1 (2)
C5—C6—H6A	119.3	C12—C11—Cl1	118.31 (17)
C7—C6—H6A	119.3	C10—C11—Cl1	118.56 (19)
C6—C7—C2	120.2 (2)	C11—C12—C13	118.0 (2)
C6—C7—H7A	119.9	C11—C12—H12A	121.0
C2—C7—H7A	119.9	C13—C12—H12A	121.0
C5—C8—H8C	109.5	C12—C13—C14	120.8 (2)
C5—C8—H8B	109.5	C12—C13—H13A	119.6
H8C—C8—H8B	109.5	C14—C13—H13A	119.6
C5—C8—H8A	109.5	C13—C14—C9	120.2 (2)
H8C—C8—H8A	109.5	C13—C14—H14A	119.9
H8B—C8—H8A	109.5	C9—C14—H14A	119.9
C5—C8—H8F	110.0	C1—N1—C9	128.76 (18)
H8B—C8—H8F	109.2	C1—N1—H1N	116.7 (14)
H8A—C8—H8F	109.3	C9—N1—H1N	114.3 (14)
O1—C1—C2—C3	−144.7 (2)	C14—C9—C10—C11	0.7 (3)
N1—C1—C2—C3	34.3 (3)	N1—C9—C10—C11	179.3 (2)
O1—C1—C2—C7	31.5 (3)	C9—C10—C11—C12	−0.3 (3)
N1—C1—C2—C7	−149.48 (19)	C9—C10—C11—Cl1	−178.47 (16)
C7—C2—C3—C4	−1.2 (3)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—C4	174.99 (18)	Cl1—C11—C12—C13	177.90 (18)
C2—C3—C4—C5	0.9 (3)	C11—C12—C13—C14	0.5 (4)
C3—C4—C5—C6	0.4 (3)	C12—C13—C14—C9	−0.1 (3)
C3—C4—C5—C8	179.9 (2)	C10—C9—C14—C13	−0.5 (3)
C4—C5—C6—C7	−1.5 (3)	N1—C9—C14—C13	−179.24 (19)
C8—C5—C6—C7	179.0 (2)	O1—C1—N1—C9	6.4 (3)
C5—C6—C7—C2	1.2 (3)	C2—C1—N1—C9	−172.65 (18)
C3—C2—C7—C6	0.2 (3)	C14—C9—N1—C1	−177.4 (2)
C1—C2—C7—C6	−176.16 (19)	C10—C9—N1—C1	3.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	2.11 (2)	2.947 (2)	167 (2)
O2—H2O···O1ii	0.84 (2)	1.92 (2)	2.7630 (19)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	2.11 (2)	2.947 (2)	167 (2)
O2—H2O⋯O1ii	0.84 (2)	1.92 (2)	2.7630 (19)	176 (3)

Symmetry codes: (i) ; (ii) .