N-(3-Chloro­phen­yl)benzamide

Abstract

The conformation of the N—H bond in the structure of the title compound (N3CPBA), C₁₃H₁₀ClNO, 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-chloro­phen­yl)benzamide (N2CPBA) and meta chloro substituent in N-(3,4-dichloro­phen­yl)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-dichloro­phen­yl)benzamide (N23DCPBA). The bond parameters in N3CPBA are similar to those in N-phenyl­benzamide, 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 mol­ecules 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 _r = 231.67

• Orthorhombic,

• a = 9.3585 (2) Å

• b = 9.7851 (2) Å

• c = 25.1419 (6) Å

• V = 2302.34 (9) ų

• 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

• Δρ_max = 0.19 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

In the present work, the structure of N-(3-chlorophenyl)-benzamide (N3CPBA) has been determined to explore the effect of substituents on the structure of N-aromatic amides (Gowda et al., 2003; Gowda, Sowmya, Kožíšek et al., 2007; Gowda, Sowmya, Tokarčík et al., 2007). The conformation of the N—H bond in the structure of N3CPBA(Fig.1) is anti to the meta chloro substituent in the aniline phenyl ring, similar to that observed with respect to the ortho-chloro substituent in N-(2-chlorophenyl)-benzamide (N2CPBA)(Gowda, Sowmya, Kožíšek et al., 2007) and meta-chloro substituent in N-(3,4-dichlorophenyl)-benzamide (N34DCPBA) (Gowda, Sowmya, Tokarčík et al., 2007), but in contrast to the syn conformation observed with respect to both the ortho & meta-Chloro substituents in N-(2,3-dichlorophenyl)- benzamide (N23DCPBA)(Gowda, Sowmya, Tokarčík et al., 2007). The bond parameters in N3CPBA are similar to those in N-(phenyl)-benzamide, N2CPBA, N23DCPBA, N34DCPBA and other benzanilides. The amide group –NHCO– has the dihedral angle of 18.2 (2)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 61.0 (1)°. One-dimensional chains of the title compound along the base vector [0 1 0] formed by hydrogen bonds N1–H1N···O1 (Table 1) as viewed down the a axis is shown in Fig.2.

Experimental

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

Refinement

H atoms bonded to C atoms were placed in geometrically calculated positions and subsequently treated as riding with C—H bond distance 0.93 Å. H(N) atom was visible in the difference map. In refinement the N—H distance was restrained to 0.86 (4) Å. The U_iso(H) values were set at 1.2 U_eq(C,N).

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.

Crystal structure of the title compound viewed down the axis a. One-dimensional chains along the base vector [0 1 0] are formed by hydrogen bonds N1–H1N···O1(i). H atoms not involved in hydrogen bonding are omitted. [Symmetry code: (i) -x + 1/2, y - 1/2, z]

Crystal data

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

Data collection

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

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

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
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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

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 codes: (i) −x+1/2, y−1/2, z.