N-(3-Chloro-phen-yl)-2-methyl-benzamide.

The conformation of the N-H bond in the structure of the title compound, C(14)H(12)ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N-H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methyl-phen-yl)benzamide (N3MP2MBA). The -NHC(=O)- group makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5 (1)°; the respective values for N3MP2MBA are 55.2 (7) and 36.2 (1)°. N-H⋯O hydrogen bonds link the mol-ecules into infinite chains running along the c axis.

Related literature

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

Experimental

Crystal data

C14H12ClNO

M = 245.70

Tetragonal,

a = 8.8237 (8) Å

c = 15.977 (2) Å

V = 1243.9 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.57 mm−1

T = 299 (2) K

0.60 × 0.10 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.308, T max = 0.841

4144 measured reflections

2173 independent reflections

1844 reflections with I > 2σ(I)

R int = 0.036

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.07

2173 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1020 Friedel pairs

Flack parameter: 0.00 (2)

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010143/om2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010143/om2228Isup2.hkl

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

C14H12ClNO	Z = 4
Mr = 245.70	F000 = 512
Tetragonal, P43	Dx = 1.312 Mg m−3
Hall symbol: P 4cw	Cu Kα radiation λ = 1.54180 Å
a = 8.8237 (8) Å	Cell parameters from 25 reflections
b = 8.8237 (8) Å	θ = 5.7–21.9º
c = 15.977 (2) Å	µ = 2.57 mm−1
α = 90º	T = 299 (2) K
β = 90º	Rod, colourless
γ = 90º	0.60 × 0.10 × 0.07 mm
V = 1243.9 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.036
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 5.0º
T = 299(2) K	h = −10→10
ω/2θ scans	k = −10→1
Absorption correction: Psi-scan(North et al., 1968)	l = −19→16
Tmin = 0.308, Tmax = 0.841	3 standard reflections
4144 measured reflections	every 120 min
2173 independent reflections	intensity decay: none
1844 reflections with I > 2σ(I)

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042	w = 1/[σ2(Fo2) + (0.0774P)2 + 0.019P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120	(Δ/σ)max = 0.025
S = 1.07	Δρmax = 0.19 e Å−3
2173 reflections	Δρmin = −0.29 e Å−3
159 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0079 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1020 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.00 (2)

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
C1	0.6762 (3)	0.7532 (3)	0.05087 (15)	0.0463 (6)
C2	0.7849 (3)	0.7433 (3)	0.11372 (17)	0.0528 (6)
H2	0.8336	0.6521	0.1249	0.063*
C3	0.8186 (4)	0.8716 (4)	0.15884 (17)	0.0627 (8)
C4	0.7505 (5)	1.0087 (4)	0.1436 (2)	0.0763 (10)
H4	0.7762	1.0940	0.1747	0.092*
C5	0.6440 (5)	1.0169 (4)	0.0815 (2)	0.0831 (11)
H5	0.5963	1.1088	0.0705	0.100*
C6	0.6061 (4)	0.8896 (3)	0.0346 (2)	0.0673 (8)
H6	0.5337	0.8965	−0.0075	0.081*
C7	0.6591 (3)	0.4810 (3)	0.01510 (14)	0.0452 (5)
C8	0.5994 (3)	0.3752 (3)	−0.05047 (17)	0.0516 (6)
C9	0.6935 (4)	0.2659 (3)	−0.08605 (18)	0.0644 (8)
C10	0.6279 (6)	0.1643 (4)	−0.1412 (2)	0.0887 (12)
H10	0.6885	0.0897	−0.1650	0.106*
C11	0.4808 (7)	0.1690 (4)	−0.1617 (3)	0.0992 (14)
H11	0.4415	0.0984	−0.1991	0.119*
C12	0.3864 (5)	0.2793 (5)	−0.1272 (3)	0.0955 (13)
H12	0.2841	0.2826	−0.1411	0.115*
C13	0.4472 (4)	0.3834 (4)	−0.0721 (2)	0.0695 (8)
H13	0.3863	0.4591	−0.0495	0.083*
C14	0.8575 (5)	0.2539 (5)	−0.0653 (3)	0.0923 (12)
H14A	0.8693	0.2414	−0.0059	0.111*
H14B	0.9088	0.3444	−0.0828	0.111*
H14C	0.9003	0.1680	−0.0936	0.111*
N1	0.6388 (3)	0.6279 (2)	−0.00053 (14)	0.0488 (5)
H1N	0.594 (4)	0.650 (3)	−0.045 (2)	0.059*
O1	0.7197 (2)	0.4315 (2)	0.07953 (11)	0.0598 (5)
Cl1	0.95205 (13)	0.85850 (13)	0.23813 (6)	0.0996 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0581 (14)	0.0483 (13)	0.0324 (12)	−0.0062 (11)	0.0045 (10)	0.0009 (10)
C2	0.0615 (15)	0.0546 (14)	0.0421 (13)	−0.0076 (11)	0.0013 (11)	0.0021 (11)
C3	0.0766 (18)	0.0721 (19)	0.0394 (15)	−0.0252 (15)	0.0044 (13)	−0.0071 (13)
C4	0.115 (3)	0.0605 (18)	0.0538 (19)	−0.0194 (18)	0.0127 (18)	−0.0145 (15)
C5	0.125 (3)	0.0505 (15)	0.074 (2)	0.0089 (18)	0.012 (2)	−0.0043 (16)
C6	0.092 (2)	0.0568 (16)	0.0532 (17)	0.0043 (14)	−0.0034 (16)	0.0023 (13)
C7	0.0528 (13)	0.0500 (13)	0.0327 (13)	−0.0022 (10)	0.0041 (10)	0.0020 (10)
C8	0.0721 (17)	0.0465 (13)	0.0361 (13)	−0.0069 (11)	−0.0036 (11)	0.0030 (10)
C9	0.094 (2)	0.0559 (15)	0.0434 (15)	0.0070 (15)	−0.0037 (14)	−0.0022 (12)
C10	0.149 (4)	0.0572 (18)	0.059 (2)	0.006 (2)	−0.020 (2)	−0.0159 (15)
C11	0.162 (4)	0.064 (2)	0.071 (2)	−0.034 (3)	−0.034 (3)	−0.0049 (18)
C12	0.103 (3)	0.095 (3)	0.089 (3)	−0.039 (2)	−0.039 (2)	0.009 (2)
C13	0.0712 (19)	0.0665 (17)	0.071 (2)	−0.0106 (15)	−0.0094 (15)	0.0044 (15)
C14	0.099 (3)	0.109 (3)	0.069 (2)	0.035 (2)	0.0100 (19)	−0.012 (2)
N1	0.0627 (13)	0.0512 (11)	0.0324 (10)	0.0005 (9)	−0.0063 (10)	0.0014 (9)
O1	0.0893 (13)	0.0559 (10)	0.0342 (10)	0.0054 (9)	−0.0073 (9)	0.0033 (8)
Cl1	0.1114 (7)	0.1195 (8)	0.0678 (6)	−0.0442 (6)	−0.0276 (5)	−0.0081 (5)

C1—C6	1.377 (4)	C8—C13	1.388 (4)
C1—C2	1.391 (4)	C8—C9	1.394 (4)
C1—N1	1.416 (3)	C9—C10	1.384 (5)
C2—C3	1.374 (4)	C9—C14	1.488 (5)
C2—H2	0.9300	C10—C11	1.339 (7)
C3—C4	1.373 (5)	C10—H10	0.9300
C3—Cl1	1.734 (3)	C11—C12	1.394 (7)
C4—C5	1.368 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.382 (5)
C5—C6	1.392 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—O1	1.240 (3)	C14—H14B	0.9600
C7—N1	1.332 (3)	C14—H14C	0.9600
C7—C8	1.499 (3)	N1—H1N	0.83 (4)
C6—C1—C2	120.0 (2)	C10—C9—C8	117.3 (3)
C6—C1—N1	117.9 (2)	C10—C9—C14	120.2 (3)
C2—C1—N1	122.0 (2)	C8—C9—C14	122.5 (3)
C3—C2—C1	118.4 (3)	C11—C10—C9	122.8 (4)
C3—C2—H2	120.8	C11—C10—H10	118.6
C1—C2—H2	120.8	C9—C10—H10	118.6
C4—C3—C2	122.6 (3)	C10—C11—C12	120.3 (3)
C4—C3—Cl1	119.1 (2)	C10—C11—H11	119.9
C2—C3—Cl1	118.4 (3)	C12—C11—H11	119.9
C5—C4—C3	118.4 (3)	C13—C12—C11	118.9 (4)
C5—C4—H4	120.8	C13—C12—H12	120.5
C3—C4—H4	120.8	C11—C12—H12	120.5
C4—C5—C6	120.8 (3)	C12—C13—C8	120.0 (4)
C4—C5—H5	119.6	C12—C13—H13	120.0
C6—C5—H5	119.6	C8—C13—H13	120.0
C1—C6—C5	119.7 (3)	C9—C14—H14A	109.5
C1—C6—H6	120.1	C9—C14—H14B	109.5
C5—C6—H6	120.1	H14A—C14—H14B	109.5
O1—C7—N1	123.8 (2)	C9—C14—H14C	109.5
O1—C7—C8	120.8 (2)	H14A—C14—H14C	109.5
N1—C7—C8	115.3 (2)	H14B—C14—H14C	109.5
C13—C8—C9	120.7 (3)	C7—N1—C1	128.3 (2)
C13—C8—C7	118.8 (3)	C7—N1—H1N	117 (2)
C9—C8—C7	120.5 (3)	C1—N1—H1N	115 (2)
C6—C1—C2—C3	0.5 (4)	C7—C8—C9—C10	174.9 (3)
N1—C1—C2—C3	177.7 (2)	C13—C8—C9—C14	179.4 (3)
C1—C2—C3—C4	−0.8 (4)	C7—C8—C9—C14	−3.6 (4)
C1—C2—C3—Cl1	179.1 (2)	C8—C9—C10—C11	0.9 (5)
C2—C3—C4—C5	0.7 (5)	C14—C9—C10—C11	179.5 (4)
Cl1—C3—C4—C5	−179.2 (3)	C9—C10—C11—C12	0.0 (6)
C3—C4—C5—C6	−0.4 (5)	C10—C11—C12—C13	0.3 (6)
C2—C1—C6—C5	−0.3 (5)	C11—C12—C13—C8	−1.4 (6)
N1—C1—C6—C5	−177.5 (3)	C9—C8—C13—C12	2.3 (5)
C4—C5—C6—C1	0.2 (6)	C7—C8—C13—C12	−174.7 (3)
O1—C7—C8—C13	121.7 (3)	O1—C7—N1—C1	−1.7 (4)
N1—C7—C8—C13	−56.8 (3)	C8—C7—N1—C1	176.9 (2)
O1—C7—C8—C9	−55.2 (3)	C6—C1—N1—C7	−160.9 (3)
N1—C7—C8—C9	126.2 (3)	C2—C1—N1—C7	21.9 (4)
C13—C8—C9—C10	−2.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)

Symmetry code: (i) .