4-Chloro-N-o-tolyl­benzamide

Saeed, A.; Khera, R.A.; Abbas, N.; Gotoh, K.; Ishida, H.

doi:10.1107/S1600536808030912

organic compounds

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Volume 64| Part 10| October 2008| Page o2043

doi:10.1107/S1600536808030912

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4-Chloro-N-o-tolylbenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Naeem Abbas,^a Kazuma Gotoh ^b and Hiroyuki Ishida ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 20 September 2008; accepted 25 September 2008; online 30 September 2008)

In the molecule of the title compound, C₁₄H₁₂ClNO, the two benzene rings are close to coplanar [dihedral angle = 7.85 (4)°]. The amide N—C=O plane makes dihedral angles of 34.04 (4) and 39.90 (3)°, respectively, with the 4-chloro- and 2-methylphenyl rings. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains.

Related literature

For a related structure, see: Saeed et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.71
Monoclinic, P 2₁ /n
a = 10.7906 (14) Å
b = 4.8793 (6) Å
c = 23.522 (3) Å
β = 98.125 (3)°
V = 1226.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 223 (1) K
0.40 × 0.18 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: numerical (ABSCOR; Higashi, 1999 ) T_min = 0.928, T_max = 0.974
14142 measured reflections
3461 independent reflections
1685 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.166
S = 1.06
3461 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (2)	2.07 (2)	2.9073 (18)	164.1 (17)
Symmetry code: (i) x, y-1, z.

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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 PLATON (Spek, 2003 ); software used to prepare material for publication: CrystalStructure and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030912/hk2536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030912/hk2536Isup2.hkl

checkCIF report

Comment top

The background to this study has been described in our earlier paper of 4-chloro-N-(2-chlorophenyl)-benzamide (Saeed et al., 2008).

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1–C6) and B (C8–C13) are, of course, planar and the dihedral angle between them is 7.85 (4)°. So, they are also nearly coplanar. The amide plane (N1/O1/C7) is oriented with respect to rings A and B at dihedral angles of 34.04 (4)° and 39.90 (3)°, respectively.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For a related structure, see: Saeed et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 4-chorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-methylaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq. 1 M HCl and saturated aq. NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (yield; 84%). Anal. calcd. for C₁₄H₁₂ClNO: C 58.67, H 4.92, N 5.70%; found: C 58.61, H 4.96, N 5.79%.

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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 PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

4-Chloro-N-o-tolylbenzamide top

Crystal data top

C₁₄H₁₂ClNO	F(000) = 512.00
M_r = 245.71	D_x = 1.331 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 7779 reflections
a = 10.7906 (14) Å	θ = 3.0–30.0°
b = 4.8793 (6) Å	µ = 0.29 mm⁻¹
c = 23.522 (3) Å	T = 223 K
β = 98.125 (3)°	Block, colorless
V = 1226.0 (3) Å³	0.40 × 0.18 × 0.09 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID II diffractometer	1685 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.046
ω scans	θ_max = 30.0°, θ_min = 3.0°
Absorption correction: numerical (ABSCOR; Higashi, 1999)	h = −15→15
T_min = 0.928, T_max = 0.974	k = −6→6
14142 measured reflections	l = −33→33
3461 independent reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0782P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.22 e Å⁻³
3461 reflections	Δρ_min = −0.28 e Å⁻³
159 parameters

Crystal data top

C₁₄H₁₂ClNO	V = 1226.0 (3) Å³
M_r = 245.71	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7906 (14) Å	µ = 0.29 mm⁻¹
b = 4.8793 (6) Å	T = 223 K
c = 23.522 (3) Å	0.40 × 0.18 × 0.09 mm
β = 98.125 (3)°

Data collection top

Rigaku R-AXIS RAPID II diffractometer	3461 independent reflections
Absorption correction: numerical (ABSCOR; Higashi, 1999)	1685 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.974	R_int = 0.046
14142 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	159 parameters
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
3461 reflections	Δρ_min = −0.28 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.40808 (7)	0.32489 (17)	0.27042 (3)	0.1042 (3)
O1	0.31241 (13)	0.9179 (2)	0.51539 (6)	0.0709 (4)
N1	0.25683 (14)	0.4881 (3)	0.53727 (6)	0.0523 (4)
H1	0.2591 (18)	0.319 (4)	0.5268 (8)	0.067 (6)*
C1	0.32795 (16)	0.5743 (3)	0.44582 (8)	0.0509 (4)
C2	0.42185 (17)	0.7014 (4)	0.42126 (10)	0.0653 (5)
H2	0.4689	0.8416	0.4414	0.078*
C3	0.4477 (2)	0.6259 (4)	0.36758 (10)	0.0750 (6)
H3	0.5129	0.7107	0.3515	0.090*
C4	0.3762 (2)	0.4243 (4)	0.33802 (9)	0.0676 (5)
C5	0.2816 (2)	0.2953 (4)	0.36098 (9)	0.0686 (5)
H5	0.2336	0.1583	0.3402	0.082*
C6	0.25799 (18)	0.3701 (4)	0.41517 (8)	0.0600 (5)
H6	0.1940	0.2817	0.4314	0.072*
C7	0.29972 (15)	0.6742 (3)	0.50259 (8)	0.0496 (4)
C8	0.21114 (17)	0.5490 (3)	0.58983 (7)	0.0520 (4)
C9	0.10277 (18)	0.4181 (4)	0.60191 (8)	0.0579 (5)
C10	0.0587 (2)	0.4874 (5)	0.65275 (9)	0.0779 (6)
H10	−0.0138	0.4006	0.6618	0.093*
C11	0.1170 (3)	0.6773 (6)	0.68999 (10)	0.0923 (8)
H11	0.0837	0.7228	0.7236	0.111*
C12	0.2238 (3)	0.8005 (5)	0.67811 (10)	0.0905 (8)
H12	0.2645	0.9300	0.7038	0.109*
C13	0.2728 (2)	0.7363 (4)	0.62834 (9)	0.0700 (6)
H13	0.3473	0.8191	0.6207	0.084*
C14	0.03458 (18)	0.2127 (4)	0.56166 (10)	0.0674 (5)
H14A	0.0089	0.2980	0.5246	0.101*	0.80 (2)
H14B	−0.0387	0.1481	0.5772	0.101*	0.80 (2)
H14C	0.0894	0.0592	0.5571	0.101*	0.80 (2)
H14D	0.0782	0.1894	0.5287	0.101*	0.20 (2)
H14E	−0.0498	0.2772	0.5490	0.101*	0.20 (2)
H14F	0.0312	0.0386	0.5813	0.101*	0.20 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1230 (6)	0.1310 (7)	0.0666 (4)	0.0156 (4)	0.0405 (4)	−0.0055 (3)
O1	0.0955 (10)	0.0364 (6)	0.0858 (10)	−0.0028 (6)	0.0300 (8)	−0.0084 (6)
N1	0.0646 (9)	0.0387 (7)	0.0550 (9)	0.0004 (7)	0.0135 (7)	−0.0055 (6)
C1	0.0528 (9)	0.0422 (8)	0.0589 (10)	0.0044 (7)	0.0127 (8)	0.0008 (7)
C2	0.0615 (11)	0.0564 (11)	0.0825 (14)	−0.0036 (9)	0.0262 (10)	−0.0072 (10)
C3	0.0733 (13)	0.0705 (13)	0.0893 (16)	0.0016 (11)	0.0393 (12)	0.0029 (12)
C4	0.0751 (12)	0.0740 (13)	0.0573 (11)	0.0188 (11)	0.0219 (10)	0.0049 (10)
C5	0.0737 (12)	0.0730 (13)	0.0589 (12)	−0.0012 (11)	0.0084 (10)	−0.0065 (10)
C6	0.0647 (11)	0.0613 (11)	0.0558 (11)	−0.0047 (9)	0.0148 (8)	−0.0007 (8)
C7	0.0511 (9)	0.0370 (8)	0.0618 (11)	0.0035 (7)	0.0114 (8)	−0.0008 (7)
C8	0.0647 (10)	0.0437 (9)	0.0469 (9)	0.0117 (8)	0.0061 (8)	−0.0010 (7)
C9	0.0674 (11)	0.0560 (10)	0.0516 (10)	0.0160 (9)	0.0131 (8)	0.0093 (8)
C10	0.0907 (15)	0.0869 (15)	0.0601 (13)	0.0279 (12)	0.0244 (11)	0.0179 (11)
C11	0.130 (2)	0.1023 (19)	0.0465 (12)	0.0468 (17)	0.0173 (14)	−0.0015 (12)
C12	0.127 (2)	0.0812 (15)	0.0567 (13)	0.0293 (16)	−0.0111 (14)	−0.0197 (11)
C13	0.0832 (14)	0.0610 (11)	0.0621 (13)	0.0098 (11)	−0.0027 (10)	−0.0134 (9)
C14	0.0638 (11)	0.0617 (11)	0.0782 (14)	−0.0026 (9)	0.0154 (10)	0.0057 (10)

Geometric parameters (Å, º) top

Cl1—C4	1.742 (2)	C8—C9	1.396 (3)
O1—C7	1.2299 (19)	C9—C10	1.390 (3)
N1—C7	1.346 (2)	C9—C14	1.498 (3)
N1—C8	1.426 (2)	C10—C11	1.366 (3)
N1—H1	0.86 (2)	C10—H10	0.9400
C1—C2	1.382 (3)	C11—C12	1.363 (4)
C1—C6	1.389 (2)	C11—H11	0.9400
C1—C7	1.493 (2)	C12—C13	1.387 (3)
C2—C3	1.381 (3)	C12—H12	0.9400
C2—H2	0.9400	C13—H13	0.9400
C3—C4	1.376 (3)	C14—H14A	0.9700
C3—H3	0.9400	C14—H14B	0.9700
C4—C5	1.374 (3)	C14—H14C	0.9700
C5—C6	1.384 (3)	C14—H14D	0.9699
C5—H5	0.9400	C14—H14E	0.9700
C6—H6	0.9400	C14—H14F	0.9701
C8—C13	1.388 (3)

C7—N1—C8	125.15 (15)	C9—C10—H10	118.8
C7—N1—H1	116.5 (14)	C12—C11—C10	119.6 (2)
C8—N1—H1	118.3 (14)	C12—C11—H11	120.2
C2—C1—C6	118.81 (18)	C10—C11—H11	120.2
C2—C1—C7	118.80 (16)	C11—C12—C13	120.5 (2)
C6—C1—C7	122.26 (16)	C11—C12—H12	119.7
C3—C2—C1	121.15 (19)	C13—C12—H12	119.7
C3—C2—H2	119.4	C12—C13—C8	119.7 (2)
C1—C2—H2	119.4	C12—C13—H13	120.2
C4—C3—C2	118.77 (19)	C8—C13—H13	120.2
C4—C3—H3	120.6	C9—C14—H14A	109.5
C2—C3—H3	120.6	C9—C14—H14B	109.5
C5—C4—C3	121.57 (19)	H14A—C14—H14B	109.5
C5—C4—Cl1	118.99 (17)	C9—C14—H14C	109.5
C3—C4—Cl1	119.43 (17)	H14A—C14—H14C	109.5
C4—C5—C6	119.0 (2)	H14B—C14—H14C	109.5
C4—C5—H5	120.5	C9—C14—H14D	109.5
C6—C5—H5	120.5	H14A—C14—H14D	56.0
C5—C6—C1	120.66 (19)	H14B—C14—H14D	141.0
C5—C6—H6	119.7	H14C—C14—H14D	56.5
C1—C6—H6	119.7	C9—C14—H14E	109.5
O1—C7—N1	122.69 (17)	H14A—C14—H14E	56.5
O1—C7—C1	120.33 (15)	H14B—C14—H14E	56.0
N1—C7—C1	116.95 (14)	H14C—C14—H14E	141.1
C13—C8—C9	120.40 (18)	H14D—C14—H14E	109.5
C13—C8—N1	120.71 (18)	C9—C14—H14F	109.5
C9—C8—N1	118.89 (15)	H14A—C14—H14F	141.1
C10—C9—C8	117.52 (19)	H14B—C14—H14F	56.5
C10—C9—C14	120.6 (2)	H14C—C14—H14F	56.0
C8—C9—C14	121.86 (17)	H14D—C14—H14F	109.5
C11—C10—C9	122.3 (2)	H14E—C14—H14F	109.5
C11—C10—H10	118.8

C6—C1—C2—C3	−0.9 (3)	C6—C1—C7—N1	34.7 (2)
C7—C1—C2—C3	−176.85 (16)	C7—N1—C8—C13	−42.7 (2)
C1—C2—C3—C4	1.4 (3)	C7—N1—C8—C9	136.99 (18)
C2—C3—C4—C5	−0.8 (3)	C13—C8—C9—C10	1.4 (3)
C2—C3—C4—Cl1	−179.63 (15)	N1—C8—C9—C10	−178.29 (15)
C3—C4—C5—C6	−0.1 (3)	C13—C8—C9—C14	−179.35 (17)
Cl1—C4—C5—C6	178.64 (14)	N1—C8—C9—C14	1.0 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C10—C11	0.5 (3)
C2—C1—C6—C5	−0.1 (3)	C14—C9—C10—C11	−178.77 (18)
C7—C1—C6—C5	175.69 (16)	C9—C10—C11—C12	−1.5 (3)
C8—N1—C7—O1	5.6 (3)	C10—C11—C12—C13	0.6 (4)
C8—N1—C7—C1	−172.29 (15)	C11—C12—C13—C8	1.3 (3)
C2—C1—C7—O1	32.5 (2)	C9—C8—C13—C12	−2.3 (3)
C6—C1—C7—O1	−143.28 (18)	N1—C8—C13—C12	177.40 (16)
C2—C1—C7—N1	−149.49 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (2)	2.07 (2)	2.9073 (18)	164.1 (17)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.71
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	10.7906 (14), 4.8793 (6), 23.522 (3)
β (°)	98.125 (3)
V (Å³)	1226.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.40 × 0.18 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID II diffractometer
Absorption correction	Numerical (ABSCOR; Higashi, 1999)
T_min, T_max	0.928, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	14142, 3461, 1685
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.166, 1.06
No. of reflections	3461
No. of parameters	159
No. of restraints	?
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (2)	2.07 (2)	2.9073 (18)	164.1 (17)

Symmetry code: (i) x, y−1, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1999). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure and PROCESS-AUTO. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Saeed, A., Khera, R. A., Gotoh, K. & Ishida, H. (2008). Acta Cryst. E64, o1934. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S1600536808030912

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