N-(2-Chloro­phen­yl)benzamide

In the structure of the title compound (N2CPBA), C₁₃H₁₀ClNO, the conformation of the N—H bond is anti to the ortho-Cl substituent in the aniline benzene ring. It closely resembles the structure of 2-chloro-N-phenyl­benzamide (NP2CBA), although the two amides crystallize in different crystal systems. The mol­ecules of N2CPBA are linked into a chain through an N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.051
• wR factor = 0.171
• Data-to-parameter ratio = 14.6

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S1. Comment

In the present work, the structure of N-(2-chlorophenyl)-benzamide (N2CPBA) has been determined to explore the substituent effects on the structure of N-aromatic amides (Gowda et al., 2003; 2007a-d). In the structure of N2CPBA the N—H bond is anti to the ortho-Cl substituent in the aniline phenyl ring (Fig. 1). The structure of N2CPBA closely resembles the structure of N-(phenyl)-2-chlorobenzamide (NP2CBA) (Gowda et al., 2003), although the two amides, N2CPBA and NP2CBA crystallize in different crystal systems: orthorhombic Pbca and tetragonal P4₃ space groups, respectively. The packing diagram of N2CPBA molecules showing the hydrogen bonds N1—H1N···O1ⁱ, generating a chain along [010] [symmetry operation (i): -x + 1/2, y + 1/2, z] (Table 1, Fig. 2).

Related literature

For related literature, see: Gowda et al. (2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (2007); Gowda et al. (2007a, 2007b).

S2. Experimental

The title compound was prepared according to the literature (Gowda et al., 2003). The purity of the compound was checked by its melting point. It was characterized by IR and NMR spectra. Single crystals of the title compound were obtained from an ethanolic solution at room temperature and used for X-ray diffraction studies.

S3. Refinement

H atoms were placed geometrically and refined using a riding model with C—H distances 0.93 Å for the ring H atoms, and N—H 0.86Å for the NH hydrogen atom.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Detail of crystal packing showing the hydrogen bonds N1—H1N···O1 generating a chain along [010] [symmetry operation: (i) -x + 1/2, y + 1/2, z].

N-(2-Chlorophenyl)benzamide

Crystal data

C13H10ClNO	F(000) = 960
Mr = 231.67	Dx = 1.346 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3908 reflections
a = 8.1122 (2) Å	θ = 3.2–29.5°
b = 9.3093 (2) Å	µ = 0.31 mm^−1
c = 30.2818 (8) Å	T = 295 K
V = 2286.85 (10) Å^3	Prism, colourless
Z = 8	0.44 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	2224 independent reflections
Graphite monochromator	1630 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	Rint = 0.022
φ scans, and ω scans with κ offsets	θmax = 26.0°, θmin = 5.0°
Absorption correction: analytical (Clark & Reid, 1995)	h = −9→9
Tmin = 0.879, Tmax = 0.994	k = −11→11
23061 measured reflections	l = −37→37

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.099P)^2 + 0.48P] where P = (Fo^2 + 2Fc^2)/3
2224 reflections	(Δ/σ)max = 0.01
152 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.15606 (9)	0.39267 (9)	0.45504 (2)	0.0871 (3)
O1	0.16921 (19)	0.36964 (15)	0.35146 (6)	0.0637 (5)
N1	0.2540 (2)	0.58328 (16)	0.37875 (6)	0.0528 (5)
H1N	0.2364	0.6743	0.3799	0.063*
C1	0.1565 (2)	0.5005 (2)	0.35303 (6)	0.0476 (5)
C2	0.0327 (2)	0.57676 (19)	0.32524 (6)	0.0463 (5)
C3	−0.0134 (3)	0.5129 (2)	0.28601 (7)	0.0555 (5)
H3	0.035 (3)	0.423 (3)	0.2796 (8)	0.067*
C4	−0.1259 (3)	0.5798 (3)	0.25857 (8)	0.0644 (6)
H4	−0.1542	0.5378	0.2318	0.077*
C5	−0.1957 (3)	0.7079 (3)	0.27083 (9)	0.0704 (7)
H5	−0.2724	0.752	0.2525	0.085*
C6	−0.1530 (3)	0.7706 (3)	0.30982 (10)	0.0726 (7)
H6	−0.2016	0.8569	0.3181	0.087*
C7	−0.0373 (3)	0.7065 (2)	0.33722 (8)	0.0606 (6)
H7	−0.010 (3)	0.750 (3)	0.3651 (9)	0.073*
C8	0.3846 (3)	0.5237 (2)	0.40398 (6)	0.0511 (5)
C9	0.3559 (3)	0.4297 (2)	0.43837 (7)	0.0590 (6)
C10	0.4858 (4)	0.3669 (3)	0.46060 (9)	0.0776 (7)
H10	0.4648	0.3007	0.4829	0.093*
C11	0.6447 (4)	0.4011 (3)	0.45009 (10)	0.0819 (8)
H11	0.7317	0.3581	0.4651	0.098*
C12	0.6751 (3)	0.4993 (3)	0.41732 (10)	0.0781 (8)
H12	0.783	0.5251	0.4106	0.094*
C13	0.5455 (3)	0.5601 (3)	0.39423 (8)	0.0660 (6)
H13	0.567	0.6261	0.3719	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0785 (5)	0.1082 (7)	0.0747 (5)	−0.0152 (3)	0.0059 (3)	0.0285 (4)
O1	0.0778 (11)	0.0361 (8)	0.0771 (11)	0.0031 (6)	−0.0165 (8)	0.0041 (6)
N1	0.0603 (10)	0.0347 (8)	0.0634 (10)	0.0006 (7)	−0.0096 (8)	0.0067 (7)
C1	0.0520 (10)	0.0375 (10)	0.0534 (11)	−0.0006 (7)	0.0015 (8)	0.0060 (8)
C2	0.0462 (10)	0.0385 (9)	0.0541 (10)	−0.0032 (7)	0.0021 (8)	0.0085 (8)
C3	0.0528 (11)	0.0469 (11)	0.0670 (13)	−0.0038 (9)	−0.0023 (9)	−0.0007 (9)
C4	0.0628 (13)	0.0671 (14)	0.0634 (13)	−0.0115 (10)	−0.0128 (10)	0.0036 (11)
C5	0.0667 (13)	0.0571 (14)	0.0875 (16)	−0.0012 (11)	−0.0243 (12)	0.0165 (12)
C6	0.0749 (15)	0.0500 (12)	0.0930 (17)	0.0143 (10)	−0.0166 (12)	0.0027 (12)
C7	0.0662 (13)	0.0479 (11)	0.0678 (13)	0.0069 (9)	−0.0089 (10)	0.0018 (10)
C8	0.0581 (11)	0.0396 (10)	0.0556 (11)	−0.0012 (8)	−0.0048 (8)	0.0017 (8)
C9	0.0661 (13)	0.0558 (13)	0.0552 (12)	−0.0026 (9)	−0.0056 (9)	0.0056 (10)
C10	0.0890 (19)	0.0765 (16)	0.0673 (15)	0.0076 (14)	−0.0182 (13)	0.0206 (12)
C11	0.0736 (18)	0.087 (2)	0.0855 (19)	0.0151 (13)	−0.0237 (14)	0.0040 (15)
C12	0.0573 (13)	0.0841 (18)	0.0928 (19)	−0.0010 (12)	−0.0082 (12)	−0.0025 (15)
C13	0.0643 (14)	0.0599 (13)	0.0739 (14)	−0.0082 (10)	−0.0031 (11)	0.0062 (11)

Geometric parameters (Å, º)

Cl1—C9	1.733 (2)	C6—C7	1.387 (3)
O1—C1	1.224 (2)	C6—H6	0.93
N1—C1	1.351 (3)	C7—H7	0.96 (3)
N1—C8	1.419 (3)	C8—C9	1.379 (3)
N1—H1N	0.86	C8—C13	1.381 (3)
C1—C2	1.490 (3)	C9—C10	1.380 (3)
C2—C3	1.380 (3)	C10—C11	1.365 (4)
C2—C7	1.383 (3)	C10—H10	0.93
C3—C4	1.382 (3)	C11—C12	1.372 (4)
C3—H3	0.95 (3)	C11—H11	0.93
C4—C5	1.372 (4)	C12—C13	1.383 (4)
C4—H4	0.93	C12—H12	0.93
C5—C6	1.362 (4)	C13—H13	0.93
C5—H5	0.93
C1—N1—C8	121.61 (16)	C2—C7—C6	119.8 (2)
C1—N1—H1N	119.2	C2—C7—H7	120.3 (15)
C8—N1—H1N	119.2	C6—C7—H7	119.8 (15)
O1—C1—N1	122.76 (18)	C9—C8—C13	118.5 (2)
O1—C1—C2	120.59 (18)	C9—C8—N1	121.90 (19)
N1—C1—C2	116.64 (16)	C13—C8—N1	119.65 (18)
C3—C2—C7	119.37 (19)	C8—C9—C10	120.6 (2)
C3—C2—C1	117.64 (17)	C8—C9—Cl1	120.24 (17)
C7—C2—C1	122.99 (18)	C10—C9—Cl1	119.18 (19)
C2—C3—C4	120.2 (2)	C11—C10—C9	120.5 (2)
C2—C3—H3	116.5 (15)	C11—C10—H10	119.7
C4—C3—H3	123.3 (15)	C9—C10—H10	119.7
C5—C4—C3	120.1 (2)	C10—C11—C12	119.6 (2)
C5—C4—H4	120	C10—C11—H11	120.2
C3—C4—H4	120	C12—C11—H11	120.2
C6—C5—C4	120.1 (2)	C11—C12—C13	120.1 (2)
C6—C5—H5	119.9	C11—C12—H12	119.9
C4—C5—H5	119.9	C13—C12—H12	119.9
C5—C6—C7	120.4 (2)	C8—C13—C12	120.7 (2)
C5—C6—H6	119.8	C8—C13—H13	119.7
C7—C6—H6	119.8	C12—C13—H13	119.7
C8—N1—C1—O1	3.6 (3)	C1—N1—C8—C9	−65.3 (3)
C8—N1—C1—C2	−175.03 (17)	C1—N1—C8—C13	114.8 (2)
O1—C1—C2—C3	−27.7 (3)	C13—C8—C9—C10	−4.0 (3)
N1—C1—C2—C3	151.00 (19)	N1—C8—C9—C10	176.1 (2)
O1—C1—C2—C7	151.9 (2)	C13—C8—C9—Cl1	174.40 (18)
N1—C1—C2—C7	−29.4 (3)	N1—C8—C9—Cl1	−5.5 (3)
C7—C2—C3—C4	1.4 (3)	C8—C9—C10—C11	2.6 (4)
C1—C2—C3—C4	−179.02 (19)	Cl1—C9—C10—C11	−175.8 (2)
C2—C3—C4—C5	−1.9 (3)	C9—C10—C11—C12	0.4 (5)
C3—C4—C5—C6	0.8 (4)	C10—C11—C12—C13	−1.9 (4)
C4—C5—C6—C7	0.7 (4)	C9—C8—C13—C12	2.5 (4)
C3—C2—C7—C6	0.1 (3)	N1—C8—C13—C12	−177.6 (2)
C1—C2—C7—C6	−179.4 (2)	C11—C12—C13—C8	0.4 (4)
C5—C6—C7—C2	−1.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.86	2.15	2.860 (2)	139

Symmetry code: (i) −x+1/2, y+1/2, z.