4-Chloro-N-(2-methoxy-phen-yl)benzamide.

The title compound, C(14)H(12)ClNO(2), was prepared by refluxing 4-chloro-benzoyl chloride with o-anisidine in CHCl(3). The methoxy-phen-yl-amide segment of the mol-ecule is almost planar, with a dihedral angle of 5.10 (7)° between the benzene ring and the C-N-C(O)-C fragment. A weak intra-molecular N-H⋯O contact forms an S(5) ring and contributes to the planarity of this portion of the mol-ecule. The two benzene rings are inclined at an angle of 26.74 (7)°. In the crystal structure, inter-molecular Cl⋯O inter-actions of 3.1874 (9) Å generate centrosymmetric dimers. These are further linked by C-H⋯O and C-H⋯π inter-actions, forming inversion related sheets parallel to [001].

Related literature

For background to our work on benzamide derivatives, see: Saeed et al. (2008 ▶). For related structures, see: Balasubramanyam et al. (2003 ▶); Gowda et al. (2008 ▶); Saeed et al. (2007 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Triclinic,

a = 7.6938 (5) Å

b = 9.2339 (6) Å

c = 9.8723 (7) Å

α = 66.683 (3)°

β = 89.943 (3)°

γ = 69.536 (3)°

V = 595.69 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 89 K

0.68 × 0.55 × 0.38 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.762, T max = 1.000

9701 measured reflections

4037 independent reflections

3359 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.129

S = 1.11

4037 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905394X/bq2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905394X/bq2183Isup2.hkl

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

C14H12ClNO2	Z = 2
Mr = 261.70	F(000) = 272
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6938 (5) Å	Cell parameters from 5193 reflections
b = 9.2339 (6) Å	θ = 5.2–66.5°
c = 9.8723 (7) Å	µ = 0.31 mm−1
α = 66.683 (3)°	T = 89 K
β = 89.943 (3)°	Irregular block, colourless
γ = 69.536 (3)°	0.68 × 0.55 × 0.38 mm
V = 595.69 (7) Å3

Bruker APEXII CCD area-detector diffractometer	4037 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 33.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→11
Tmin = 0.762, Tmax = 1.000	k = −14→14
9701 measured reflections	l = −15→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0747P)2 + 0.107P] where P = (Fo2 + 2Fc2)/3
4037 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

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	0.96801 (14)	0.46684 (13)	0.22602 (12)	0.01253 (19)
H1N	0.884 (2)	0.424 (2)	0.2472 (19)	0.015*
O1	1.05224 (13)	0.67559 (12)	0.23889 (11)	0.01810 (19)
C1	0.94176 (16)	0.60270 (14)	0.25817 (13)	0.0119 (2)
C2	0.76731 (16)	0.65786 (14)	0.32264 (13)	0.0115 (2)
C3	0.60538 (16)	0.63062 (15)	0.29623 (13)	0.0128 (2)
H3	0.6034	0.5737	0.2348	0.015*
C4	0.44720 (16)	0.68559 (15)	0.35862 (14)	0.0137 (2)
H4	0.3370	0.6679	0.3396	0.016*
C5	0.45387 (16)	0.76691 (15)	0.44926 (13)	0.0134 (2)
Cl1	0.25804 (4)	0.83363 (4)	0.53040 (3)	0.01918 (10)
C6	0.61287 (17)	0.79600 (15)	0.47773 (13)	0.0141 (2)
H6	0.6148	0.8514	0.5405	0.017*
C7	0.76861 (16)	0.74244 (15)	0.41260 (13)	0.0129 (2)
H7	0.8772	0.7635	0.4294	0.015*
C8	1.12198 (15)	0.38098 (14)	0.17333 (13)	0.0111 (2)
C9	1.11216 (15)	0.24043 (14)	0.15384 (13)	0.0119 (2)
O91	0.95021 (12)	0.21277 (11)	0.18506 (10)	0.01454 (18)
C91	0.92918 (17)	0.07592 (16)	0.16205 (15)	0.0170 (2)
H91A	0.9212	0.1017	0.0554	0.026*
H91B	0.8142	0.0620	0.1967	0.026*
H91C	1.0378	−0.0297	0.2183	0.026*
C10	1.25940 (16)	0.14161 (15)	0.10850 (14)	0.0142 (2)
H10	1.2514	0.0479	0.0946	0.017*
C11	1.41951 (17)	0.18041 (16)	0.08331 (14)	0.0156 (2)
H11	1.5219	0.1115	0.0541	0.019*
C12	1.42992 (17)	0.31922 (16)	0.10069 (14)	0.0156 (2)
H12	1.5391	0.3453	0.0826	0.019*
C13	1.28124 (16)	0.42081 (15)	0.14455 (14)	0.0139 (2)
H13	1.2883	0.5167	0.1548	0.017*

	U11	U22	U33	U12	U13	U23
N1	0.0111 (4)	0.0137 (4)	0.0177 (5)	−0.0062 (3)	0.0069 (4)	−0.0100 (4)
O1	0.0149 (4)	0.0190 (4)	0.0284 (5)	−0.0099 (3)	0.0084 (4)	−0.0148 (4)
C1	0.0107 (5)	0.0131 (5)	0.0137 (5)	−0.0044 (4)	0.0027 (4)	−0.0073 (4)
C2	0.0111 (5)	0.0111 (4)	0.0125 (5)	−0.0037 (4)	0.0023 (4)	−0.0057 (4)
C3	0.0118 (5)	0.0143 (5)	0.0147 (5)	−0.0051 (4)	0.0034 (4)	−0.0084 (4)
C4	0.0115 (5)	0.0152 (5)	0.0160 (5)	−0.0054 (4)	0.0037 (4)	−0.0078 (4)
C5	0.0132 (5)	0.0130 (5)	0.0134 (5)	−0.0035 (4)	0.0047 (4)	−0.0062 (4)
Cl1	0.01588 (16)	0.02343 (17)	0.02268 (17)	−0.00678 (12)	0.00998 (12)	−0.01468 (13)
C6	0.0162 (5)	0.0139 (5)	0.0143 (5)	−0.0053 (4)	0.0037 (4)	−0.0083 (4)
C7	0.0129 (5)	0.0133 (5)	0.0145 (5)	−0.0051 (4)	0.0023 (4)	−0.0078 (4)
C8	0.0100 (4)	0.0108 (4)	0.0118 (5)	−0.0029 (4)	0.0029 (4)	−0.0052 (4)
C9	0.0103 (5)	0.0124 (5)	0.0128 (5)	−0.0039 (4)	0.0031 (4)	−0.0056 (4)
O91	0.0123 (4)	0.0148 (4)	0.0228 (5)	−0.0073 (3)	0.0080 (3)	−0.0122 (3)
C91	0.0149 (5)	0.0163 (5)	0.0261 (6)	−0.0077 (4)	0.0052 (5)	−0.0135 (5)
C10	0.0125 (5)	0.0134 (5)	0.0171 (5)	−0.0035 (4)	0.0047 (4)	−0.0082 (4)
C11	0.0113 (5)	0.0168 (5)	0.0178 (6)	−0.0028 (4)	0.0054 (4)	−0.0085 (4)
C12	0.0115 (5)	0.0177 (5)	0.0172 (5)	−0.0059 (4)	0.0048 (4)	−0.0068 (4)
C13	0.0128 (5)	0.0149 (5)	0.0161 (5)	−0.0068 (4)	0.0045 (4)	−0.0074 (4)

N1—C1	1.3613 (14)	C7—H7	0.9500
N1—C8	1.4039 (13)	C8—C13	1.3961 (15)
N1—H1N	0.860 (17)	C8—C9	1.4119 (15)
O1—C1	1.2288 (13)	C9—O91	1.3683 (13)
C1—C2	1.4977 (15)	C9—C10	1.3841 (15)
C2—C7	1.3977 (15)	O91—C91	1.4301 (13)
C2—C3	1.3982 (15)	C91—H91A	0.9800
C3—C4	1.3901 (15)	C91—H91B	0.9800
C3—H3	0.9500	C91—H91C	0.9800
C4—C5	1.3879 (16)	C10—C11	1.3947 (16)
C4—H4	0.9500	C10—H10	0.9500
C5—C6	1.3920 (16)	C11—C12	1.3873 (16)
C5—Cl1	1.7408 (11)	C11—H11	0.9500
Cl1—O91i	3.1874 (9)	C12—C13	1.3951 (16)
C6—C7	1.3891 (15)	C12—H12	0.9500
C6—H6	0.9500	C13—H13	0.9500
C1—N1—C8	128.16 (9)	C13—C8—C9	119.25 (10)
C1—N1—H1N	115.7 (11)	N1—C8—C9	115.41 (9)
C8—N1—H1N	116.0 (11)	O91—C9—C10	124.96 (10)
O1—C1—N1	123.69 (10)	O91—C9—C8	114.45 (9)
O1—C1—C2	121.14 (10)	C10—C9—C8	120.58 (10)
N1—C1—C2	115.16 (9)	C9—O91—C91	117.00 (9)
C7—C2—C3	119.14 (10)	O91—C91—H91A	109.5
C7—C2—C1	117.28 (10)	O91—C91—H91B	109.5
C3—C2—C1	123.57 (10)	H91A—C91—H91B	109.5
C4—C3—C2	120.95 (10)	O91—C91—H91C	109.5
C4—C3—H3	119.5	H91A—C91—H91C	109.5
C2—C3—H3	119.5	H91B—C91—H91C	109.5
C5—C4—C3	118.53 (10)	C9—C10—C11	119.63 (10)
C5—C4—H4	120.7	C9—C10—H10	120.2
C3—C4—H4	120.7	C11—C10—H10	120.2
C4—C5—C6	121.93 (10)	C12—C11—C10	120.28 (10)
C4—C5—Cl1	119.03 (9)	C12—C11—H11	119.9
C6—C5—Cl1	119.04 (9)	C10—C11—H11	119.9
C7—C6—C5	118.73 (10)	C11—C12—C13	120.49 (10)
C7—C6—H6	120.6	C11—C12—H12	119.8
C5—C6—H6	120.6	C13—C12—H12	119.8
C6—C7—C2	120.71 (11)	C12—C13—C8	119.75 (10)
C6—C7—H7	119.6	C12—C13—H13	120.1
C2—C7—H7	119.6	C8—C13—H13	120.1
C13—C8—N1	125.31 (10)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O91	0.855 (17)	2.165 (19)	2.5810 (16)	109.7 (15)
C4—H4···O1ii	0.95	2.37	3.3060 (15)	167
C6—H6···Cg1iii	0.95	3.33	3.911 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O91	0.855 (17)	2.165 (19)	2.5810 (16)	109.7 (15)
C4—H4⋯O1i	0.95	2.37	3.3060 (15)	167
C6—H6⋯Cg1ii	0.95	3.33	3.911 (2)	133

Symmetry codes: (i) ; (ii) .