N-(4-Chloro-phen-yl)benzamide.

The structure of the title compound, C(13)H(10)ClNO, resembles those of N-phen-ylbenzamide, N-(2-chloro-phenyl)-benzamide and other benzanilides, with similar bond parameters. The amide group -NHCO- makes a dihedral angle of 29.95 (9)° with the benzoyl ring, while the benzoyl and aniline rings form a dihedral angle of 60.76 (3)°. The structure shows both intra- and inter-molecular hydrogen bonding. The mol-ecules are linked by N-H⋯O hydrogen bonds into chains running along the [100] direction.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Triclinic,

a = 5.3789 (1) Å

b = 7.8501 (2) Å

c = 13.6318 (4) Å

α = 106.509 (2)°

β = 98.380 (2)°

γ = 90.631 (2)°

V = 545.15 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 295 (2) K

0.52 × 0.25 × 0.08 mm

Data collection

Oxford Xcalibur diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007 ▶), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.852, T max = 0.975

23656 measured reflections

2087 independent reflections

1773 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.08

2087 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008155/dn2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008155/dn2327Isup2.hkl

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

C13H10ClNO	Z = 2
Mr = 231.67	F000 = 240
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.3789 (1) Å	Cell parameters from 13860 reflections
b = 7.8501 (2) Å	θ = 3.1–29.3º
c = 13.6318 (4) Å	µ = 0.33 mm−1
α = 106.509 (2)º	T = 295 (2) K
β = 98.380 (2)º	Block, colorless
γ = 90.631 (2)º	0.52 × 0.25 × 0.08 mm
V = 545.15 (2) Å3

Oxford Xcalibur diffractometer	2087 independent reflections
Radiation source: fine-focus sealed tube	1773 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 10.434 pixels mm-1	θmax = 25.8º
T = 295(2) K	θmin = 5.6º
φ scans, and ω scans with κ offsets	h = −6→6
Absorption correction: analytical[CrysAlis RED (Oxford Diffraction, 2007). Analytical absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	k = −9→9
Tmin = 0.852, Tmax = 0.975	l = −16→16
23656 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0494P)2 + 0.0939P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2087 reflections	Δρmax = 0.19 e Å−3
148 parameters	Δρmin = −0.23 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.3126 (2)	0.77177 (16)	0.02982 (9)	0.0381 (3)
H1N	0.443 (3)	0.757 (2)	0.0010 (13)	0.046*
O1	−0.11350 (19)	0.74813 (17)	0.00041 (8)	0.0563 (3)
C1	0.0870 (2)	0.71549 (18)	−0.03078 (10)	0.0370 (3)
C2	0.0976 (2)	0.61312 (17)	−0.14032 (10)	0.0343 (3)
C3	−0.1018 (2)	0.62387 (19)	−0.21496 (11)	0.0396 (3)
H3	−0.2346	0.6941	−0.1956	0.047*
C4	−0.1045 (3)	0.5314 (2)	−0.31747 (11)	0.0450 (3)
H4	−0.2376	0.5409	−0.3671	0.054*
C5	0.0893 (3)	0.4249 (2)	−0.34662 (11)	0.0460 (4)
H5	0.0871	0.3621	−0.4158	0.055*
C6	0.2867 (3)	0.41171 (19)	−0.27281 (12)	0.0452 (3)
H6	0.4167	0.3387	−0.2924	0.054*
C7	0.2930 (3)	0.50593 (18)	−0.17026 (11)	0.0392 (3)
H7	0.4281	0.4977	−0.1211	0.047*
C8	0.3531 (2)	0.87653 (17)	0.13439 (10)	0.0337 (3)
C9	0.1943 (3)	0.86476 (19)	0.20396 (10)	0.0396 (3)
H9	0.0509	0.7884	0.1818	0.048*
C10	0.2490 (3)	0.96646 (19)	0.30619 (11)	0.0415 (3)
H10	0.1426	0.9588	0.353	0.05*
C11	0.4617 (3)	1.07920 (18)	0.33843 (10)	0.0396 (3)
C12	0.6211 (3)	1.09201 (19)	0.27047 (11)	0.0419 (3)
H12	0.7643	1.1685	0.293	0.05*
C13	0.56679 (8)	0.99040 (5)	0.16848 (3)	0.0391 (3)
H13	0.6744	0.9983	0.1222	0.047*
Cl1	0.53006 (8)	1.20876 (5)	0.46690 (3)	0.06227 (17)

	U11	U22	U33	U12	U13	U23
N1	0.0320 (6)	0.0455 (7)	0.0326 (6)	0.0003 (5)	0.0068 (5)	0.0037 (5)
O1	0.0336 (5)	0.0849 (8)	0.0394 (6)	0.0060 (5)	0.0073 (4)	−0.0005 (5)
C1	0.0337 (7)	0.0404 (7)	0.0347 (7)	0.0024 (5)	0.0045 (5)	0.0076 (6)
C2	0.0328 (7)	0.0340 (7)	0.0345 (7)	−0.0022 (5)	0.0060 (5)	0.0069 (5)
C3	0.0328 (7)	0.0422 (7)	0.0400 (7)	0.0032 (5)	0.0043 (5)	0.0066 (6)
C4	0.0402 (8)	0.0505 (8)	0.0379 (7)	−0.0029 (6)	−0.0035 (6)	0.0075 (6)
C5	0.0487 (8)	0.0474 (8)	0.0342 (7)	−0.0054 (6)	0.0074 (6)	−0.0009 (6)
C6	0.0394 (8)	0.0436 (8)	0.0471 (8)	0.0043 (6)	0.0117 (6)	0.0020 (6)
C7	0.0335 (7)	0.0412 (7)	0.0394 (7)	0.0023 (5)	0.0026 (5)	0.0077 (6)
C8	0.0325 (6)	0.0343 (7)	0.0323 (6)	0.0043 (5)	0.0039 (5)	0.0067 (5)
C9	0.0343 (7)	0.0451 (8)	0.0369 (7)	−0.0042 (6)	0.0026 (5)	0.0097 (6)
C10	0.0404 (7)	0.0510 (8)	0.0333 (7)	0.0031 (6)	0.0084 (6)	0.0113 (6)
C11	0.0442 (8)	0.0378 (7)	0.0317 (7)	0.0065 (6)	0.0004 (6)	0.0043 (5)
C12	0.0369 (7)	0.0385 (7)	0.0441 (8)	−0.0035 (6)	0.0005 (6)	0.0051 (6)
C13	0.0347 (7)	0.0416 (7)	0.0401 (7)	0.0007 (5)	0.0091 (6)	0.0089 (6)
Cl1	0.0764 (3)	0.0615 (3)	0.0352 (2)	−0.0009 (2)	−0.00138 (18)	−0.00280 (18)

N1—C1	1.3560 (18)	C6—H6	0.93
N1—C8	1.4125 (17)	C7—H7	0.93
N1—H1N	0.845 (16)	C8—C13	1.3862 (13)
O1—C1	1.2196 (16)	C8—C9	1.3862 (18)
C1—C2	1.4909 (18)	C9—C10	1.3817 (19)
C2—C3	1.3876 (19)	C9—H9	0.93
C2—C7	1.3885 (19)	C10—C11	1.377 (2)
C3—C4	1.377 (2)	C10—H10	0.93
C3—H3	0.93	C11—C12	1.373 (2)
C4—C5	1.376 (2)	C11—Cl1	1.7402 (14)
C4—H4	0.93	C12—C13	1.3786 (15)
C5—C6	1.379 (2)	C12—H12	0.93
C5—H5	0.93	C13—H13	0.93
C6—C7	1.379 (2)
C1—N1—C8	126.64 (11)	C6—C7—C2	120.02 (13)
C1—N1—H1N	117.7 (11)	C6—C7—H7	120
C8—N1—H1N	115.0 (12)	C2—C7—H7	120
O1—C1—N1	123.02 (12)	C13—C8—C9	119.42 (11)
O1—C1—C2	121.31 (12)	C13—C8—N1	117.74 (10)
N1—C1—C2	115.66 (11)	C9—C8—N1	122.80 (12)
C3—C2—C7	119.04 (12)	C10—C9—C8	120.05 (12)
C3—C2—C1	117.62 (11)	C10—C9—H9	120
C7—C2—C1	123.33 (12)	C8—C9—H9	120
C4—C3—C2	120.51 (12)	C11—C10—C9	119.65 (12)
C4—C3—H3	119.7	C11—C10—H10	120.2
C2—C3—H3	119.7	C9—C10—H10	120.2
C5—C4—C3	120.17 (13)	C12—C11—C10	120.97 (13)
C5—C4—H4	119.9	C12—C11—Cl1	119.21 (11)
C3—C4—H4	119.9	C10—C11—Cl1	119.82 (11)
C4—C5—C6	119.71 (13)	C11—C12—C13	119.40 (12)
C4—C5—H5	120.1	C11—C12—H12	120.3
C6—C5—H5	120.1	C13—C12—H12	120.3
C7—C6—C5	120.53 (13)	C12—C13—C8	120.52 (9)
C7—C6—H6	119.7	C12—C13—H13	119.7
C5—C6—H6	119.7	C8—C13—H13	119.7
C8—N1—C1—O1	−1.4 (2)	C1—C2—C7—C6	178.39 (12)
C8—N1—C1—C2	177.27 (12)	C1—N1—C8—C13	−149.06 (12)
O1—C1—C2—C3	28.33 (19)	C1—N1—C8—C9	33.4 (2)
N1—C1—C2—C3	−150.35 (12)	C13—C8—C9—C10	0.24 (18)
O1—C1—C2—C7	−150.27 (14)	N1—C8—C9—C10	177.75 (12)
N1—C1—C2—C7	31.06 (18)	C8—C9—C10—C11	0.0 (2)
C7—C2—C3—C4	−0.8 (2)	C9—C10—C11—C12	−0.1 (2)
C1—C2—C3—C4	−179.47 (12)	C9—C10—C11—Cl1	179.53 (10)
C2—C3—C4—C5	1.0 (2)	C10—C11—C12—C13	0.0 (2)
C3—C4—C5—C6	−0.3 (2)	Cl1—C11—C12—C13	−179.61 (9)
C4—C5—C6—C7	−0.7 (2)	C11—C12—C13—C8	0.18 (17)
C5—C6—C7—C2	1.0 (2)	C9—C8—C13—C12	−0.32 (15)
C3—C2—C7—C6	−0.2 (2)	N1—C8—C13—C12	−177.95 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.93	2.43	2.9090 (17)	112
N1—H1N···O1i	0.845 (16)	2.390 (16)	3.1710 (15)	154.0 (15)
C13—H13···O1i	0.93	2.58	3.2507 (11)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1	0.93	2.43	2.9090 (17)	112
N1—H1N⋯O1i	0.845 (16)	2.390 (16)	3.1710 (15)	154.0 (15)
C13—H13⋯O1i	0.93	2.58	3.2507 (11)	129

Symmetry code: (i) .