N-(3-Chloro-phen-yl)benzamide.

The conformation of the N-H bond in the structure of the title compound (N3CPBA), C(13)H(10)ClNO, is anti to the meta chloro substituent in the aniline benzene ring, similar to that observed with respect to the ortho chloro substituent in N-(2-chloro-phen-yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro-phen-yl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to both the ortho and the meta chloro substituents in N-(2,3-dichloro-phen-yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl-benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group -NHCO- makes a dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings is 61.0 (1)°. The mol-ecules are linked into chains along the b axis by N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶); Gowda, Sowmya, Kožíšek et al. (2007 ▶); Gowda, Sowmya, Tokarčík et al. (2007 ▶).

Experimental

Crystal data

C13H10ClNO

M = 231.67

Orthorhombic,

a = 9.3585 (2) Å

b = 9.7851 (2) Å

c = 25.1419 (6) Å

V = 2302.34 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 295 (2) K

0.41 × 0.13 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 ▶). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995 ▶). T min = 0.915, T max = 0.984

53566 measured reflections

2252 independent reflections

1639 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.101

S = 1.08

2252 reflections

148 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.25 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/S1600536808001311/dn2311sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001311/dn2311Isup2.hkl

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

C13H10ClNO	F000 = 960
Mr = 231.67	Dx = 1.337 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14003 reflections
a = 9.3585 (2) Å	θ = 3.0–29.5º
b = 9.7851 (2) Å	µ = 0.31 mm−1
c = 25.1419 (6) Å	T = 295 (2) K
V = 2302.34 (9) Å3	Prism, colourless
Z = 8	0.41 × 0.13 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer	2252 independent reflections
Monochromator: graphite	1639 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.047
T = 295(2) K	θmax = 26.0º
φ scans, and ω scans with κ offsets	θmin = 4.7º
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction, 2007). Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995).	h = −11→11
Tmin = 0.915, Tmax = 0.984	k = −12→12
53566 measured reflections	l = −31→31

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2808P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2252 reflections	Δρmax = 0.19 e Å−3
148 parameters	Δρmin = −0.25 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	0.27214 (14)	0.48267 (13)	0.12047 (5)	0.0462 (4)
H1N	0.2650 (19)	0.4004 (17)	0.1287 (6)	0.055*
O1	0.19225 (12)	0.69327 (10)	0.14128 (5)	0.0565 (3)
Cl1	0.54083 (6)	0.81350 (6)	−0.00120 (2)	0.0875 (2)
C1	0.17675 (16)	0.56906 (15)	0.14234 (6)	0.0405 (4)
C2	0.05098 (15)	0.50735 (14)	0.16988 (6)	0.0392 (4)
C3	−0.02405 (19)	0.58822 (17)	0.20536 (7)	0.0546 (5)
H3	0.0038	0.6784	0.2108	0.065*
C4	−0.1391 (2)	0.53666 (19)	0.23252 (8)	0.0671 (5)
H4	−0.1877	0.5916	0.2567	0.081*
C5	−0.1830 (2)	0.4050 (2)	0.22432 (8)	0.0684 (6)
H5	−0.2613	0.3706	0.2427	0.082*
C6	−0.1111 (2)	0.32411 (18)	0.18890 (8)	0.0654 (5)
H6	−0.1414	0.2349	0.1829	0.079*
C7	0.00613 (18)	0.37454 (17)	0.16203 (7)	0.0519 (4)
H7	0.0553	0.3185	0.1384	0.062*
C8	0.40219 (17)	0.52388 (15)	0.09631 (6)	0.0444 (4)
C9	0.40661 (17)	0.63258 (16)	0.06157 (6)	0.0471 (4)
H9	0.3235	0.6796	0.0528	0.056*
C10	0.53533 (19)	0.67062 (18)	0.04005 (7)	0.0544 (5)
C11	0.6590 (2)	0.6017 (2)	0.05099 (8)	0.0719 (6)
H11	0.7453	0.6288	0.0359	0.086*
C12	0.6527 (2)	0.4918 (2)	0.08464 (10)	0.0808 (6)
H12	0.7355	0.4428	0.092	0.097*
C13	0.5255 (2)	0.4528 (2)	0.10771 (8)	0.0657 (5)
H13	0.523	0.3788	0.1309	0.079*

	U11	U22	U33	U12	U13	U23
N1	0.0440 (8)	0.0309 (6)	0.0636 (9)	0.0007 (6)	0.0069 (7)	0.0025 (6)
O1	0.0570 (7)	0.0299 (6)	0.0827 (8)	−0.0007 (5)	0.0119 (6)	0.0004 (5)
Cl1	0.0668 (4)	0.0990 (5)	0.0968 (4)	−0.0134 (3)	0.0102 (3)	0.0423 (3)
C1	0.0405 (9)	0.0349 (8)	0.0462 (9)	0.0023 (7)	−0.0054 (7)	0.0006 (7)
C2	0.0387 (8)	0.0353 (8)	0.0437 (8)	0.0030 (6)	−0.0031 (7)	0.0027 (6)
C3	0.0621 (11)	0.0407 (9)	0.0609 (10)	0.0035 (8)	0.0091 (9)	−0.0026 (8)
C4	0.0711 (13)	0.0596 (11)	0.0707 (12)	0.0091 (10)	0.0291 (11)	0.0013 (9)
C5	0.0605 (12)	0.0658 (12)	0.0789 (13)	−0.0021 (10)	0.0232 (11)	0.0136 (10)
C6	0.0615 (12)	0.0485 (10)	0.0862 (14)	−0.0122 (9)	0.0123 (11)	0.0001 (9)
C7	0.0495 (10)	0.0433 (9)	0.0628 (11)	−0.0030 (8)	0.0084 (8)	−0.0081 (8)
C8	0.0418 (9)	0.0393 (8)	0.0521 (9)	0.0005 (7)	0.0040 (7)	−0.0044 (7)
C9	0.0392 (9)	0.0500 (9)	0.0520 (9)	−0.0007 (8)	−0.0016 (8)	−0.0003 (8)
C10	0.0489 (11)	0.0621 (11)	0.0521 (10)	−0.0090 (8)	0.0025 (8)	0.0038 (8)
C11	0.0435 (11)	0.0900 (14)	0.0824 (14)	−0.0024 (10)	0.0133 (10)	0.0107 (12)
C12	0.0461 (12)	0.0917 (15)	0.1046 (16)	0.0207 (11)	0.0101 (11)	0.0216 (13)
C13	0.0528 (12)	0.0615 (11)	0.0827 (13)	0.0112 (9)	0.0081 (10)	0.0170 (10)

N1—C1	1.3468 (19)	C6—C7	1.380 (2)
N1—C8	1.419 (2)	C6—H6	0.93
N1—H1N	0.834 (16)	C7—H7	0.93
O1—C1	1.2244 (17)	C8—C9	1.377 (2)
Cl1—C10	1.7415 (18)	C8—C13	1.378 (2)
C1—C2	1.493 (2)	C9—C10	1.372 (2)
C2—C7	1.380 (2)	C9—H9	0.93
C2—C3	1.384 (2)	C10—C11	1.368 (3)
C3—C4	1.371 (2)	C11—C12	1.369 (3)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.368 (3)	C12—C13	1.378 (3)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.368 (3)	C13—H13	0.93
C5—H5	0.93
C1—N1—C8	124.41 (13)	C2—C7—C6	120.57 (16)
C1—N1—H1N	116.9 (12)	C2—C7—H7	119.7
C8—N1—H1N	116.7 (12)	C6—C7—H7	119.7
O1—C1—N1	122.38 (14)	C9—C8—C13	119.78 (15)
O1—C1—C2	120.33 (14)	C9—C8—N1	121.12 (14)
N1—C1—C2	117.26 (13)	C13—C8—N1	119.10 (14)
C7—C2—C3	118.46 (15)	C10—C9—C8	119.09 (15)
C7—C2—C1	123.66 (14)	C10—C9—H9	120.5
C3—C2—C1	117.88 (13)	C8—C9—H9	120.5
C4—C3—C2	120.60 (16)	C11—C10—C9	122.00 (17)
C4—C3—H3	119.7	C11—C10—Cl1	119.38 (14)
C2—C3—H3	119.7	C9—C10—Cl1	118.60 (14)
C5—C4—C3	120.47 (17)	C10—C11—C12	118.36 (18)
C5—C4—H4	119.8	C10—C11—H11	120.8
C3—C4—H4	119.8	C12—C11—H11	120.8
C4—C5—C6	119.71 (17)	C11—C12—C13	120.98 (19)
C4—C5—H5	120.1	C11—C12—H12	119.5
C6—C5—H5	120.1	C13—C12—H12	119.5
C5—C6—C7	120.18 (17)	C8—C13—C12	119.76 (18)
C5—C6—H6	119.9	C8—C13—H13	120.1
C7—C6—H6	119.9	C12—C13—H13	120.1
C8—N1—C1—O1	3.0 (2)	C5—C6—C7—C2	−1.0 (3)
C8—N1—C1—C2	−175.25 (14)	C1—N1—C8—C9	−45.2 (2)
O1—C1—C2—C7	163.26 (16)	C1—N1—C8—C13	135.30 (17)
N1—C1—C2—C7	−18.5 (2)	C13—C8—C9—C10	−1.9 (2)
O1—C1—C2—C3	−17.0 (2)	N1—C8—C9—C10	178.61 (14)
N1—C1—C2—C3	161.30 (14)	C8—C9—C10—C11	1.7 (3)
C7—C2—C3—C4	0.8 (3)	C8—C9—C10—Cl1	−176.82 (12)
C1—C2—C3—C4	−178.95 (15)	C9—C10—C11—C12	−0.2 (3)
C2—C3—C4—C5	−1.1 (3)	Cl1—C10—C11—C12	178.29 (17)
C3—C4—C5—C6	0.3 (3)	C10—C11—C12—C13	−1.1 (3)
C4—C5—C6—C7	0.8 (3)	C9—C8—C13—C12	0.6 (3)
C3—C2—C7—C6	0.2 (3)	N1—C8—C13—C12	−179.87 (18)
C1—C2—C7—C6	179.94 (16)	C11—C12—C13—C8	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.834 (16)	2.089 (17)	2.8989 (17)	163.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.834 (16)	2.089 (17)	2.8989 (17)	163.5 (17)

Symmetry code: (i) .