A monoclinic polymorph of N-(3-chloro-phen-yl)benzamide.

The title compound, C(13)H(10)ClNO, (I), is a polymorph of the structure, (II), first reported by Gowda et al. [Acta Cryst. (2008), E64, o462]. In the original report, the compound crystallized in the ortho-rhom-bic space group Pbca (Z = 8), whereas the structure reported here is monoclinic P21/c (Z = 4). The principal difference between the two forms lies in the relative orientations of the phenyl and benzene rings [dihedral angle = 8.90 (13)° for (I) and 61.0 (1)° for (II)]. The inclination of the amide -CONH- units to the benzoyl ring is more similar [15.8 (7)° for (I) and 18.2 (2)° for (II)]. In both forms, the N-H bonds are anti to the 3-chloro substituents of the aniline rings. In the crystal, inter-molecular N-H⋯O hydrogen bonds form C(4) chains along c. These chains are bolstered by weak C-H⋯O inter-actions that generate R(2) (1)(6) and R(2) (1)(7) ring motifs.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2010 ▶). For the ortho­rhom­bic polymorph of (I), see: Gowda, Tokarčík et al. (2008 ▶). For the structures of related chloro­phenyl­benzamides, see: Gowda et al. (2007a ▶,b ▶,c ▶); Gowda, Foro et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Monoclinic,

a = 12.5598 (17) Å

b = 10.2782 (14) Å

c = 9.0788 (13) Å

β = 109.421 (5)°

V = 1105.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 90 K

0.57 × 0.22 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.743, T max = 1.000

6385 measured reflections

2045 independent reflections

1475 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.04

2045 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker 2006 ▶); cell refinement: APEX2 and SAINT (Bruker 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040262/lh5145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040262/lh5145Isup2.hkl

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

C13H10ClNO	F(000) = 480
Mr = 231.67	Dx = 1.392 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1106 reflections
a = 12.5598 (17) Å	θ = 2.6–25.3°
b = 10.2782 (14) Å	µ = 0.32 mm−1
c = 9.0788 (13) Å	T = 90 K
β = 109.421 (5)°	Rectangular plate, colourless
V = 1105.3 (3) Å3	0.57 × 0.22 × 0.03 mm
Z = 4

Bruker APEXII CCD diffractometer	2045 independent reflections
Radiation source: fine-focus sealed tube	1475 reflections with I > 2σ(I)
graphite	Rint = 0.047
ω scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −15→15
Tmin = 0.743, Tmax = 1.000	k = −12→12
6385 measured reflections	l = −9→10

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) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.2503P] where P = (Fo2 + 2Fc2)/3
2045 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.26 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
N1	0.58959 (16)	0.22008 (18)	0.5519 (2)	0.0208 (4)
H1	0.5656 (19)	0.202 (2)	0.451 (3)	0.025*
C1	0.52721 (18)	0.3046 (2)	0.6039 (3)	0.0187 (5)
O1	0.55935 (12)	0.34896 (15)	0.73758 (17)	0.0223 (4)
C2	0.41446 (18)	0.3409 (2)	0.4894 (2)	0.0180 (5)
C3	0.35873 (19)	0.4469 (2)	0.5262 (3)	0.0217 (5)
H3	0.3924	0.4929	0.6211	0.026*
C4	0.25445 (19)	0.4852 (2)	0.4248 (3)	0.0233 (5)
H4	0.2167	0.5572	0.4509	0.028*
C5	0.20480 (19)	0.4194 (2)	0.2856 (3)	0.0251 (6)
H5	0.1341	0.4473	0.2151	0.030*
C7	0.36288 (18)	0.2734 (2)	0.3510 (3)	0.0215 (5)
H7	0.3992	0.1998	0.3257	0.026*
C8	0.69653 (18)	0.1670 (2)	0.6371 (2)	0.0188 (5)
C9	0.77139 (19)	0.2275 (2)	0.7677 (3)	0.0204 (5)
H9	0.7516	0.3062	0.8071	0.025*
C10	0.87564 (19)	0.1698 (2)	0.8386 (3)	0.0220 (5)
C11	0.9070 (2)	0.0546 (2)	0.7871 (3)	0.0242 (5)
H11	0.9786	0.0165	0.8393	0.029*
C12	0.8316 (2)	−0.0039 (2)	0.6576 (3)	0.0256 (6)
H12	0.8516	−0.0832	0.6200	0.031*
C13	0.72744 (19)	0.0511 (2)	0.5819 (3)	0.0232 (5)
H13	0.6767	0.0101	0.4921	0.028*
Cl1	0.96981 (5)	0.24773 (6)	1.00047 (7)	0.0317 (2)
C6	0.25863 (19)	0.3132 (2)	0.2499 (3)	0.0259 (6)
H6	0.2241	0.2669	0.1554	0.031*

	U11	U22	U33	U12	U13	U23
N1	0.0224 (10)	0.0271 (10)	0.0112 (10)	0.0031 (8)	0.0033 (9)	−0.0010 (9)
C1	0.0210 (12)	0.0203 (11)	0.0161 (12)	−0.0029 (9)	0.0079 (10)	0.0025 (10)
O1	0.0246 (9)	0.0287 (8)	0.0135 (9)	0.0002 (7)	0.0063 (7)	−0.0022 (7)
C2	0.0179 (11)	0.0220 (11)	0.0152 (12)	−0.0020 (9)	0.0067 (9)	0.0035 (9)
C3	0.0295 (13)	0.0221 (11)	0.0153 (12)	−0.0033 (10)	0.0100 (10)	0.0011 (10)
C4	0.0261 (13)	0.0247 (12)	0.0228 (13)	0.0053 (10)	0.0131 (11)	0.0038 (10)
C5	0.0184 (12)	0.0322 (13)	0.0237 (14)	0.0022 (10)	0.0056 (10)	0.0041 (11)
C7	0.0193 (12)	0.0248 (12)	0.0199 (12)	0.0003 (9)	0.0057 (10)	−0.0008 (10)
C8	0.0195 (12)	0.0229 (12)	0.0134 (12)	0.0015 (9)	0.0048 (10)	0.0052 (9)
C9	0.0252 (13)	0.0213 (12)	0.0161 (12)	0.0014 (9)	0.0085 (10)	0.0027 (10)
C10	0.0226 (12)	0.0285 (12)	0.0138 (12)	−0.0027 (10)	0.0043 (10)	0.0043 (10)
C11	0.0217 (12)	0.0309 (13)	0.0207 (13)	0.0052 (10)	0.0081 (10)	0.0081 (11)
C12	0.0329 (14)	0.0221 (12)	0.0244 (14)	0.0059 (10)	0.0129 (12)	0.0040 (10)
C13	0.0272 (13)	0.0240 (12)	0.0179 (12)	−0.0010 (10)	0.0068 (10)	0.0019 (10)
Cl1	0.0246 (3)	0.0376 (4)	0.0256 (4)	0.0006 (3)	−0.0013 (3)	−0.0033 (3)
C6	0.0227 (13)	0.0319 (13)	0.0204 (13)	−0.0038 (11)	0.0034 (10)	−0.0022 (11)

N1—C1	1.356 (3)	C7—H7	0.9500
N1—C8	1.418 (3)	C8—C9	1.392 (3)
N1—H1	0.88 (2)	C8—C13	1.396 (3)
C1—O1	1.232 (2)	C9—C10	1.386 (3)
C1—C2	1.499 (3)	C9—H9	0.9500
C2—C7	1.392 (3)	C10—C11	1.378 (3)
C2—C3	1.394 (3)	C10—Cl1	1.745 (2)
C3—C4	1.384 (3)	C11—C12	1.378 (3)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.386 (3)	C12—C13	1.381 (3)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.378 (3)	C13—H13	0.9500
C5—H5	0.9500	C6—H6	0.9500
C7—C6	1.387 (3)
C1—N1—C8	127.52 (19)	C9—C8—C13	119.9 (2)
C1—N1—H1	117.3 (16)	C9—C8—N1	122.8 (2)
C8—N1—H1	114.8 (16)	C13—C8—N1	117.3 (2)
O1—C1—N1	122.8 (2)	C10—C9—C8	118.1 (2)
O1—C1—C2	121.1 (2)	C10—C9—H9	121.0
N1—C1—C2	116.09 (19)	C8—C9—H9	121.0
C7—C2—C3	119.1 (2)	C11—C10—C9	122.9 (2)
C7—C2—C1	123.4 (2)	C11—C10—Cl1	119.38 (18)
C3—C2—C1	117.5 (2)	C9—C10—Cl1	117.77 (18)
C4—C3—C2	120.1 (2)	C12—C11—C10	118.1 (2)
C4—C3—H3	119.9	C12—C11—H11	120.9
C2—C3—H3	119.9	C10—C11—H11	120.9
C3—C4—C5	120.5 (2)	C11—C12—C13	121.0 (2)
C3—C4—H4	119.8	C11—C12—H12	119.5
C5—C4—H4	119.8	C13—C12—H12	119.5
C6—C5—C4	119.6 (2)	C12—C13—C8	120.1 (2)
C6—C5—H5	120.2	C12—C13—H13	120.0
C4—C5—H5	120.2	C8—C13—H13	120.0
C6—C7—C2	120.2 (2)	C5—C6—C7	120.4 (2)
C6—C7—H7	119.9	C5—C6—H6	119.8
C2—C7—H7	119.9	C7—C6—H6	119.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (2)	1.99 (2)	2.841 (2)	163 (2)
C7—H7···O1i	0.95	2.45	3.228 (3)	139
C13—H13···O1i	0.95	2.71	3.301 (3)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (2)	1.99 (2)	2.841 (2)	163 (2)
C7—H7⋯O1i	0.95	2.45	3.228 (3)	139
C13—H13⋯O1i	0.95	2.71	3.301 (3)	121

Symmetry code: (i) .