3-Chloro-N-phenyl-benzamide.

In the title compound, C(13)H(10)ClNO, the meta-chloro group on the benzoyl ring is positioned syn to the C=O bond. The two aromatic rings make a dihedral angle of 88.5 (3)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains propagating in [010].

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Bowes et al. (2003 ▶); Gowda et al. (2008 ▶); 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-amides, see: Gowda & Weiss (1994 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Monoclinic,

a = 25.0232 (9) Å

b = 5.3705 (2) Å

c = 8.1289 (3) Å

β = 98.537 (3)°

V = 1080.32 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.90 × 0.79 × 0.05 mm

Data collection

Oxford Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.752, T max = 0.984

18170 measured reflections

3020 independent reflections

2270 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.124

S = 1.03

3020 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.34 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/S1600536811047805/ds2154sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047805/ds2154Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047805/ds2154Isup3.cml

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

C13H10ClNO	F(000) = 480
Mr = 231.67	Dx = 1.424 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6202 reflections
a = 25.0232 (9) Å	θ = 3.8–29.5°
b = 5.3705 (2) Å	µ = 0.33 mm−1
c = 8.1289 (3) Å	T = 293 K
β = 98.537 (3)°	Rod, colorless
V = 1080.32 (7) Å3	0.90 × 0.79 × 0.05 mm
Z = 4

Oxford Xcalibur Ruby Gemini diffractometer	3020 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2270 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.4340 pixels mm-1	θmax = 29.5°, θmin = 3.8°
ω scans	h = −34→34
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −7→7
Tmin = 0.752, Tmax = 0.984	l = −11→11
18170 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.063P)2 + 0.3141P] where P = (Fo2 + 2Fc2)/3
3020 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.34 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
C1	0.24828 (6)	0.1506 (3)	0.40582 (19)	0.0408 (3)
C2	0.19382 (5)	0.0662 (3)	0.44101 (18)	0.0387 (3)
C3	0.14947 (6)	0.2149 (3)	0.38313 (19)	0.0408 (3)
H3A	0.1539	0.3624	0.3268	0.049*
C4	0.09844 (6)	0.1399 (3)	0.41060 (19)	0.0421 (3)
C5	0.09099 (6)	−0.0774 (3)	0.4947 (2)	0.0474 (4)
H5A	0.0565	−0.1266	0.5109	0.057*
C6	0.13523 (7)	−0.2200 (3)	0.5540 (2)	0.0505 (4)
H6A	0.1306	−0.3650	0.6129	0.061*
C7	0.18657 (6)	−0.1510 (3)	0.5275 (2)	0.0451 (3)
H7A	0.2161	−0.2500	0.5675	0.054*
C8	0.33745 (5)	−0.0128 (3)	0.35872 (18)	0.0374 (3)
C9	0.35764 (6)	−0.1981 (3)	0.2665 (2)	0.0445 (3)
H9A	0.3354	−0.3283	0.2231	0.053*
C10	0.41083 (7)	−0.1893 (3)	0.2391 (2)	0.0511 (4)
H10A	0.4242	−0.3134	0.1767	0.061*
C11	0.44399 (6)	0.0017 (3)	0.3037 (2)	0.0505 (4)
H11A	0.4798	0.0069	0.2853	0.061*
C12	0.42390 (6)	0.1857 (3)	0.3960 (2)	0.0497 (4)
H12A	0.4464	0.3147	0.4400	0.060*
C13	0.37059 (6)	0.1805 (3)	0.4241 (2)	0.0451 (4)
H13A	0.3573	0.3053	0.4862	0.054*
Cl1	0.042556 (15)	0.32323 (9)	0.33863 (6)	0.06042 (18)
N1	0.28327 (5)	−0.0372 (2)	0.38904 (16)	0.0421 (3)
H1A	0.2714	−0.1863	0.3976	0.051*
O1	0.25904 (5)	0.3707 (2)	0.39138 (18)	0.0587 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0323 (7)	0.0365 (8)	0.0530 (8)	0.0019 (5)	0.0046 (6)	0.0003 (6)
C2	0.0340 (7)	0.0361 (7)	0.0465 (7)	0.0002 (5)	0.0074 (6)	−0.0040 (6)
C3	0.0342 (7)	0.0363 (7)	0.0528 (8)	−0.0005 (5)	0.0088 (6)	−0.0001 (6)
C4	0.0328 (7)	0.0417 (8)	0.0522 (8)	−0.0004 (6)	0.0079 (6)	−0.0051 (6)
C5	0.0405 (8)	0.0457 (9)	0.0589 (9)	−0.0068 (6)	0.0174 (7)	−0.0050 (7)
C6	0.0564 (10)	0.0402 (8)	0.0584 (10)	−0.0030 (7)	0.0199 (8)	0.0050 (7)
C7	0.0439 (8)	0.0399 (8)	0.0521 (8)	0.0052 (6)	0.0096 (6)	0.0025 (6)
C8	0.0306 (6)	0.0353 (7)	0.0461 (7)	0.0018 (5)	0.0047 (5)	0.0036 (6)
C9	0.0384 (8)	0.0397 (8)	0.0549 (9)	0.0003 (6)	0.0053 (6)	−0.0042 (6)
C10	0.0427 (8)	0.0525 (10)	0.0600 (10)	0.0074 (7)	0.0133 (7)	−0.0040 (7)
C11	0.0342 (7)	0.0553 (10)	0.0634 (10)	0.0011 (7)	0.0118 (7)	0.0063 (8)
C12	0.0375 (8)	0.0454 (9)	0.0650 (10)	−0.0074 (6)	0.0035 (7)	0.0014 (7)
C13	0.0383 (7)	0.0392 (8)	0.0573 (9)	−0.0003 (6)	0.0059 (6)	−0.0043 (6)
Cl1	0.0316 (2)	0.0611 (3)	0.0886 (4)	0.00427 (16)	0.00877 (19)	0.0092 (2)
N1	0.0326 (6)	0.0342 (6)	0.0599 (7)	−0.0004 (5)	0.0085 (5)	−0.0018 (5)
O1	0.0390 (6)	0.0354 (6)	0.1034 (10)	0.0009 (4)	0.0155 (6)	0.0043 (6)

C1—O1	1.2220 (18)	C8—C13	1.384 (2)
C1—N1	1.3558 (18)	C8—C9	1.385 (2)
C1—C2	1.5033 (19)	C8—N1	1.4195 (18)
C2—C7	1.387 (2)	C9—C10	1.382 (2)
C2—C3	1.391 (2)	C9—H9A	0.9300
C3—C4	1.3881 (19)	C10—C11	1.374 (2)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.379 (2)	C11—C12	1.380 (2)
C4—Cl1	1.7390 (15)	C11—H11A	0.9300
C5—C6	1.374 (2)	C12—C13	1.387 (2)
C5—H5A	0.9300	C12—H12A	0.9300
C6—C7	1.384 (2)	C13—H13A	0.9300
C6—H6A	0.9300	N1—H1A	0.8600
C7—H7A	0.9300
O1—C1—N1	123.72 (14)	C13—C8—C9	120.04 (13)
O1—C1—C2	121.93 (13)	C13—C8—N1	122.38 (13)
N1—C1—C2	114.34 (12)	C9—C8—N1	117.51 (13)
C7—C2—C3	119.74 (13)	C10—C9—C8	119.99 (15)
C7—C2—C1	122.71 (13)	C10—C9—H9A	120.0
C3—C2—C1	117.55 (13)	C8—C9—H9A	120.0
C4—C3—C2	119.06 (14)	C11—C10—C9	120.34 (15)
C4—C3—H3A	120.5	C11—C10—H10A	119.8
C2—C3—H3A	120.5	C9—C10—H10A	119.8
C5—C4—C3	121.36 (14)	C10—C11—C12	119.62 (15)
C5—C4—Cl1	118.99 (11)	C10—C11—H11A	120.2
C3—C4—Cl1	119.65 (12)	C12—C11—H11A	120.2
C6—C5—C4	118.99 (14)	C11—C12—C13	120.81 (15)
C6—C5—H5A	120.5	C11—C12—H12A	119.6
C4—C5—H5A	120.5	C13—C12—H12A	119.6
C5—C6—C7	120.94 (15)	C8—C13—C12	119.20 (14)
C5—C6—H6A	119.5	C8—C13—H13A	120.4
C7—C6—H6A	119.5	C12—C13—H13A	120.4
C6—C7—C2	119.88 (15)	C1—N1—C8	126.62 (13)
C6—C7—H7A	120.1	C1—N1—H1A	116.7
C2—C7—H7A	120.1	C8—N1—H1A	116.7
O1—C1—C2—C7	−150.79 (16)	C1—C2—C7—C6	−179.20 (15)
N1—C1—C2—C7	30.3 (2)	C13—C8—C9—C10	−0.3 (2)
O1—C1—C2—C3	29.3 (2)	N1—C8—C9—C10	−177.28 (14)
N1—C1—C2—C3	−149.65 (14)	C8—C9—C10—C11	0.4 (3)
C7—C2—C3—C4	−1.2 (2)	C9—C10—C11—C12	−0.2 (3)
C1—C2—C3—C4	178.75 (13)	C10—C11—C12—C13	−0.1 (3)
C2—C3—C4—C5	0.4 (2)	C9—C8—C13—C12	0.0 (2)
C2—C3—C4—Cl1	−179.84 (11)	N1—C8—C13—C12	176.84 (14)
C3—C4—C5—C6	0.9 (2)	C11—C12—C13—C8	0.2 (3)
Cl1—C4—C5—C6	−178.89 (13)	O1—C1—N1—C8	2.4 (3)
C4—C5—C6—C7	−1.3 (3)	C2—C1—N1—C8	−178.75 (13)
C5—C6—C7—C2	0.5 (3)	C13—C8—N1—C1	34.8 (2)
C3—C2—C7—C6	0.7 (2)	C9—C8—N1—C1	−148.36 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.40	3.2377 (17)	165.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.40	3.2377 (17)	165

Symmetry code: (i) .