4-Chloro-N-phenyl-benzamide.

In the title compound, C(13)H(10)ClNO, the dihedral angle between the two benzene rings is 59.6 (1)°. The crystal structure features N-H⋯O hydrogen bonds, which link the mol-ecules into C(4) chains running along the a axis.

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, Gowda & Weiss (1994 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Triclinic,

a = 5.3934 (3) Å

b = 7.7679 (5) Å

c = 13.7831 (8) Å

α = 105.887 (5)°

β = 100.849 (4)°

γ = 90.023 (4)°

V = 544.64 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 298 K

0.99 × 0.51 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.821, T max = 0.953

8972 measured reflections

3010 independent reflections

2330 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.07

3010 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.38 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/S1600536811045107/bt5692sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045107/bt5692Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045107/bt5692Isup3.cml

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

C13H10ClNO	Z = 2
Mr = 231.67	F(000) = 240
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3934 (3) Å	Cell parameters from 3954 reflections
b = 7.7679 (5) Å	θ = 3.5–29.4°
c = 13.7831 (8) Å	µ = 0.33 mm−1
α = 105.887 (5)°	T = 298 K
β = 100.849 (4)°	Plate, colourless
γ = 90.023 (4)°	0.99 × 0.51 × 0.15 mm
V = 544.64 (5) Å3

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3010 independent reflections
Radiation source: fine-focus sealed tube	2330 reflections with I > 2σ(I)
graphite	Rint = 0.013
Detector resolution: 10.4340 pixels mm-1	θmax = 29.4°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −10→10
Tmin = 0.821, Tmax = 0.953	l = −18→18
8972 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.2195P] where P = (Fo2 + 2Fc2)/3
3010 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.38 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	0.0813 (3)	0.2427 (2)	0.47100 (11)	0.0338 (3)
C2	0.0923 (3)	0.24248 (19)	0.36321 (11)	0.0309 (3)
C3	0.2913 (3)	0.3259 (2)	0.33873 (12)	0.0354 (3)
H3A	0.4279	0.3806	0.3902	0.042*
C4	0.2871 (3)	0.3280 (2)	0.23842 (12)	0.0381 (3)
H4A	0.4191	0.3849	0.2223	0.046*
C5	0.0845 (3)	0.2446 (2)	0.16262 (11)	0.0368 (3)
C6	−0.1146 (3)	0.1601 (2)	0.18473 (12)	0.0394 (3)
H6A	−0.2494	0.1037	0.1328	0.047*
C7	−0.1100 (3)	0.1608 (2)	0.28539 (12)	0.0358 (3)
H7A	−0.2442	0.1058	0.3013	0.043*
C8	0.3529 (3)	0.25180 (19)	0.63918 (11)	0.0302 (3)
C9	0.1937 (3)	0.3348 (2)	0.70443 (11)	0.0352 (3)
H9A	0.0466	0.3833	0.6787	0.042*
C10	0.2563 (3)	0.3443 (2)	0.80795 (12)	0.0397 (3)
H10A	0.1506	0.4001	0.8518	0.048*
C11	0.4737 (3)	0.2720 (2)	0.84716 (12)	0.0421 (4)
H11A	0.5144	0.2794	0.9169	0.050*
C12	0.6304 (3)	0.1886 (2)	0.78171 (13)	0.0410 (4)
H12A	0.7766	0.1392	0.8076	0.049*
C13	0.5711 (3)	0.1780 (2)	0.67819 (12)	0.0352 (3)
H13A	0.6771	0.1216	0.6346	0.042*
N1	0.3086 (2)	0.24555 (17)	0.53357 (9)	0.0340 (3)
H1A	0.4398	0.2433	0.5063	0.041*
O1	−0.1215 (2)	0.2392 (2)	0.49853 (9)	0.0507 (3)
Cl1	0.07987 (11)	0.24911 (8)	0.03678 (3)	0.06247 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0306 (7)	0.0405 (8)	0.0314 (7)	0.0001 (6)	0.0075 (5)	0.0109 (6)
C2	0.0292 (6)	0.0351 (7)	0.0299 (7)	0.0041 (5)	0.0073 (5)	0.0105 (5)
C3	0.0301 (7)	0.0422 (8)	0.0342 (7)	−0.0018 (6)	0.0043 (6)	0.0126 (6)
C4	0.0367 (7)	0.0430 (8)	0.0397 (8)	0.0003 (6)	0.0129 (6)	0.0161 (7)
C5	0.0436 (8)	0.0413 (8)	0.0284 (7)	0.0086 (6)	0.0109 (6)	0.0121 (6)
C6	0.0364 (8)	0.0465 (8)	0.0317 (7)	−0.0011 (6)	0.0025 (6)	0.0080 (6)
C7	0.0294 (7)	0.0439 (8)	0.0347 (7)	−0.0020 (6)	0.0066 (6)	0.0116 (6)
C8	0.0285 (6)	0.0340 (7)	0.0292 (7)	−0.0019 (5)	0.0058 (5)	0.0106 (5)
C9	0.0306 (7)	0.0427 (8)	0.0339 (7)	0.0052 (6)	0.0082 (6)	0.0121 (6)
C10	0.0376 (8)	0.0496 (9)	0.0334 (8)	0.0020 (6)	0.0131 (6)	0.0101 (7)
C11	0.0410 (8)	0.0565 (10)	0.0313 (7)	−0.0044 (7)	0.0053 (6)	0.0177 (7)
C12	0.0319 (7)	0.0517 (9)	0.0427 (9)	0.0034 (6)	0.0031 (6)	0.0217 (7)
C13	0.0301 (7)	0.0414 (8)	0.0368 (8)	0.0041 (6)	0.0095 (6)	0.0132 (6)
N1	0.0285 (6)	0.0470 (7)	0.0293 (6)	0.0034 (5)	0.0081 (5)	0.0135 (5)
O1	0.0287 (5)	0.0897 (10)	0.0361 (6)	−0.0018 (6)	0.0085 (4)	0.0204 (6)
Cl1	0.0798 (4)	0.0789 (4)	0.0331 (2)	0.0003 (3)	0.0155 (2)	0.0199 (2)

C1—O1	1.2257 (17)	C8—C13	1.390 (2)
C1—N1	1.3558 (19)	C8—C9	1.391 (2)
C1—C2	1.4976 (19)	C8—N1	1.4173 (17)
C2—C7	1.389 (2)	C9—C10	1.384 (2)
C2—C3	1.3933 (19)	C9—H9A	0.9300
C3—C4	1.383 (2)	C10—C11	1.382 (2)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.380 (2)	C11—C12	1.384 (2)
C4—H4A	0.9300	C11—H11A	0.9300
C5—C6	1.382 (2)	C12—C13	1.382 (2)
C5—Cl1	1.7398 (15)	C12—H12A	0.9300
C6—C7	1.382 (2)	C13—H13A	0.9300
C6—H6A	0.9300	N1—H1A	0.8600
C7—H7A	0.9300
O1—C1—N1	123.61 (14)	C13—C8—C9	119.85 (13)
O1—C1—C2	121.13 (13)	C13—C8—N1	117.54 (12)
N1—C1—C2	115.26 (12)	C9—C8—N1	122.54 (13)
C7—C2—C3	119.09 (13)	C10—C9—C8	119.35 (14)
C7—C2—C1	118.05 (12)	C10—C9—H9A	120.3
C3—C2—C1	122.82 (13)	C8—C9—H9A	120.3
C4—C3—C2	120.48 (14)	C11—C10—C9	120.98 (14)
C4—C3—H3A	119.8	C11—C10—H10A	119.5
C2—C3—H3A	119.8	C9—C10—H10A	119.5
C5—C4—C3	119.13 (14)	C10—C11—C12	119.37 (15)
C5—C4—H4A	120.4	C10—C11—H11A	120.3
C3—C4—H4A	120.4	C12—C11—H11A	120.3
C4—C5—C6	121.55 (14)	C13—C12—C11	120.46 (14)
C4—C5—Cl1	118.82 (12)	C13—C12—H12A	119.8
C6—C5—Cl1	119.62 (12)	C11—C12—H12A	119.8
C7—C6—C5	118.82 (14)	C12—C13—C8	119.98 (14)
C7—C6—H6A	120.6	C12—C13—H13A	120.0
C5—C6—H6A	120.6	C8—C13—H13A	120.0
C6—C7—C2	120.92 (13)	C1—N1—C8	126.94 (12)
C6—C7—H7A	119.5	C1—N1—H1A	116.5
C2—C7—H7A	119.5	C8—N1—H1A	116.5
O1—C1—C2—C7	−28.3 (2)	C1—C2—C7—C6	178.28 (14)
N1—C1—C2—C7	151.19 (14)	C13—C8—C9—C10	0.7 (2)
O1—C1—C2—C3	149.28 (16)	N1—C8—C9—C10	−176.47 (14)
N1—C1—C2—C3	−31.2 (2)	C8—C9—C10—C11	−0.3 (2)
C7—C2—C3—C4	0.3 (2)	C9—C10—C11—C12	−0.2 (2)
C1—C2—C3—C4	−177.34 (14)	C10—C11—C12—C13	0.3 (2)
C2—C3—C4—C5	−0.7 (2)	C11—C12—C13—C8	0.1 (2)
C3—C4—C5—C6	0.4 (2)	C9—C8—C13—C12	−0.6 (2)
C3—C4—C5—Cl1	179.60 (12)	N1—C8—C13—C12	176.70 (13)
C4—C5—C6—C7	0.4 (2)	O1—C1—N1—C8	−2.5 (3)
Cl1—C5—C6—C7	−178.78 (12)	C2—C1—N1—C8	177.96 (13)
C5—C6—C7—C2	−0.9 (2)	C13—C8—N1—C1	152.65 (15)
C3—C2—C7—C6	0.6 (2)	C9—C8—N1—C1	−30.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.39	3.1987 (16)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.39	3.1987 (16)	157

Symmetry code: (i) .