2-Chloro-N-(4-meth-oxy-phen-yl)benzamide.

In the title compound, C(14)H(12)ClNO(2), the chloro- and meth-oxy-substituted benzene rings are close to orthogonal [dihedral angle = 79.20 (3)°]. These rings also make angles of 45.9 (3) and 33.5 (3)° with the amide -CONH- unit. The meth-oxy substituent lies close to the meth-oxy-benzene ring plane, with a maximum deviation of 0.142 (3) Å for the methyl C atom. The N-H bond is anti to the 2-chloro substituent of the aniline ring. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form C(4) chains augmented by a weak C-H⋯O inter-action involving an ortho H atom of the meth-oxy benzene ring that generates an R(2) (1)(6) motif. The chains stack the mol-ecules into columns down the b axis. Adjacent columns are linked by additional C-H⋯O and C-H⋯π contacts, generating a three-dimensional network.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2010 ▶). For related structures, see: Saeed et al. (2008a ▶,b ▶, 2009a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Monoclinic,

a = 13.1819 (10) Å

b = 5.0823 (4) Å

c = 18.4477 (14) Å

β = 99.563 (3)°

V = 1218.72 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 90 K

0.50 × 0.23 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.885, T max = 1.000

21245 measured reflections

4228 independent reflections

3106 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.104

S = 1.06

4228 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.28 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 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL and Mercury (Macrae et al., 2008 ▶); 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/S1600536810043035/hg2733sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043035/hg2733Isup2.hkl

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

C14H12ClNO2	F(000) = 544
Mr = 261.70	Dx = 1.426 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3287 reflections
a = 13.1819 (10) Å	θ = 2.2–31.3°
b = 5.0823 (4) Å	µ = 0.31 mm−1
c = 18.4477 (14) Å	T = 90 K
β = 99.563 (3)°	Rectangular block, colourless
V = 1218.72 (16) Å3	0.50 × 0.23 × 0.08 mm
Z = 4

Bruker APEXII CCD diffractometer	4228 independent reflections
Radiation source: fine-focus sealed tube	3106 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω scans	θmax = 32.2°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −19→17
Tmin = 0.885, Tmax = 1.000	k = −7→7
21245 measured reflections	l = −27→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.2831P] where P = (Fo2 + 2Fc2)/3
4228 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.28 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	0.48415 (8)	0.3074 (2)	0.61366 (6)	0.0145 (2)
H1	0.4587 (12)	0.461 (3)	0.6155 (9)	0.017*
C1	0.42206 (10)	0.0944 (2)	0.60396 (7)	0.0137 (2)
C12	0.75384 (10)	0.5034 (3)	0.68248 (7)	0.0155 (3)
H12	0.7893	0.6365	0.7128	0.019*
C2	0.30910 (9)	0.1564 (2)	0.58872 (7)	0.0127 (2)
C3	0.23760 (10)	0.0166 (2)	0.62149 (7)	0.0150 (2)
Cl1	0.27487 (3)	−0.22099 (7)	0.688318 (18)	0.02032 (9)
C4	0.13309 (11)	0.0697 (3)	0.60386 (8)	0.0212 (3)
H4	0.0853	−0.0258	0.6270	0.025*
C5	0.09866 (11)	0.2618 (3)	0.55254 (8)	0.0219 (3)
H5	0.0271	0.2958	0.5397	0.026*
C6	0.16843 (10)	0.4055 (3)	0.51967 (7)	0.0180 (3)
H6	0.1448	0.5388	0.4848	0.022*
C7	0.27285 (10)	0.3531 (3)	0.53803 (7)	0.0148 (2)
H7	0.3205	0.4525	0.5158	0.018*
C8	0.59378 (9)	0.3016 (2)	0.62596 (7)	0.0131 (2)
C9	0.64888 (10)	0.1142 (3)	0.59279 (7)	0.0154 (2)
H9	0.6135	−0.0180	0.5620	0.019*
C10	0.75521 (10)	0.1228 (3)	0.60506 (7)	0.0167 (3)
H10	0.7927	−0.0051	0.5828	0.020*
C11	0.80807 (10)	0.3166 (3)	0.64961 (7)	0.0145 (2)
O2	0.91341 (7)	0.3080 (2)	0.65680 (5)	0.0186 (2)
C14	0.96893 (10)	0.5186 (3)	0.69682 (8)	0.0222 (3)
H14A	0.9452	0.6869	0.6742	0.033*
H14B	1.0426	0.4979	0.6958	0.033*
H14C	0.9571	0.5153	0.7479	0.033*
O1	0.45382 (7)	−0.13338 (18)	0.60577 (6)	0.0192 (2)
C13	0.64644 (10)	0.4933 (3)	0.67043 (7)	0.0159 (3)
H13	0.6090	0.6201	0.6931	0.019*

	U11	U22	U33	U12	U13	U23
N1	0.0114 (5)	0.0092 (5)	0.0221 (6)	0.0006 (4)	0.0001 (4)	−0.0005 (4)
C1	0.0123 (6)	0.0127 (5)	0.0155 (6)	0.0003 (5)	0.0003 (5)	0.0006 (4)
C12	0.0146 (6)	0.0135 (6)	0.0176 (6)	−0.0015 (5)	0.0002 (5)	−0.0013 (5)
C2	0.0117 (6)	0.0117 (5)	0.0144 (6)	−0.0002 (4)	0.0012 (4)	−0.0018 (4)
C3	0.0166 (6)	0.0118 (5)	0.0164 (6)	0.0003 (5)	0.0022 (5)	0.0008 (4)
Cl1	0.02428 (18)	0.01703 (15)	0.01980 (16)	0.00019 (13)	0.00408 (13)	0.00509 (12)
C4	0.0152 (6)	0.0225 (7)	0.0271 (7)	−0.0008 (5)	0.0073 (5)	0.0032 (6)
C5	0.0107 (6)	0.0273 (7)	0.0278 (7)	0.0032 (5)	0.0035 (5)	0.0034 (6)
C6	0.0148 (6)	0.0211 (7)	0.0179 (6)	0.0040 (5)	0.0023 (5)	0.0027 (5)
C7	0.0139 (6)	0.0144 (6)	0.0164 (6)	0.0017 (5)	0.0030 (5)	0.0009 (4)
C8	0.0108 (5)	0.0115 (5)	0.0166 (6)	0.0001 (5)	0.0014 (4)	0.0016 (4)
C9	0.0151 (6)	0.0139 (6)	0.0172 (6)	−0.0008 (5)	0.0023 (5)	−0.0021 (5)
C10	0.0157 (6)	0.0160 (6)	0.0194 (6)	0.0011 (5)	0.0058 (5)	−0.0014 (5)
C11	0.0117 (6)	0.0167 (6)	0.0150 (6)	−0.0007 (5)	0.0019 (4)	0.0027 (5)
O2	0.0105 (4)	0.0234 (5)	0.0219 (5)	−0.0011 (4)	0.0027 (4)	−0.0029 (4)
C14	0.0129 (6)	0.0278 (7)	0.0249 (7)	−0.0058 (5)	0.0001 (5)	−0.0021 (6)
O1	0.0135 (5)	0.0103 (4)	0.0329 (6)	0.0012 (4)	0.0012 (4)	0.0007 (4)
C13	0.0135 (6)	0.0124 (6)	0.0214 (6)	0.0010 (5)	0.0020 (5)	−0.0007 (5)

N1—C1	1.3506 (17)	C5—H5	0.9500
N1—C8	1.4255 (16)	C6—C7	1.3876 (18)
N1—H1	0.854 (17)	C6—H6	0.9500
C1—O1	1.2298 (15)	C7—H7	0.9500
C1—C2	1.5021 (17)	C8—C13	1.3841 (18)
C12—C11	1.3870 (18)	C8—C9	1.3985 (17)
C12—C13	1.3970 (18)	C9—C10	1.3829 (18)
C12—H12	0.9500	C9—H9	0.9500
C2—C3	1.3957 (18)	C10—C11	1.3931 (18)
C2—C7	1.3977 (17)	C10—H10	0.9500
C3—C4	1.3883 (19)	C11—O2	1.3734 (15)
C3—Cl1	1.7373 (13)	O2—C14	1.4305 (17)
Cl1—O1	3.0456 (11)	C14—H14A	0.9800
C4—C5	1.383 (2)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.3901 (19)	C13—H13	0.9500
C1—N1—C8	125.48 (11)	C6—C7—H7	119.5
C1—N1—H1	120.4 (11)	C2—C7—H7	119.5
C8—N1—H1	114.0 (11)	C13—C8—C9	119.53 (12)
O1—C1—N1	123.69 (12)	C13—C8—N1	118.37 (11)
O1—C1—C2	121.67 (11)	C9—C8—N1	122.07 (12)
N1—C1—C2	114.63 (11)	C10—C9—C8	119.53 (12)
C11—C12—C13	119.19 (12)	C10—C9—H9	120.2
C11—C12—H12	120.4	C8—C9—H9	120.2
C13—C12—H12	120.4	C9—C10—C11	120.85 (12)
C3—C2—C7	118.26 (11)	C9—C10—H10	119.6
C3—C2—C1	122.13 (11)	C11—C10—H10	119.6
C7—C2—C1	119.56 (11)	O2—C11—C12	124.46 (12)
C4—C3—C2	120.99 (12)	O2—C11—C10	115.67 (11)
C4—C3—Cl1	116.99 (10)	C12—C11—C10	119.87 (12)
C2—C3—Cl1	121.97 (10)	C11—O2—C14	116.64 (10)
C3—Cl1—O1	72.23 (5)	O2—C14—H14A	109.5
C5—C4—C3	119.83 (13)	O2—C14—H14B	109.5
C5—C4—H4	120.1	H14A—C14—H14B	109.5
C3—C4—H4	120.1	O2—C14—H14C	109.5
C4—C5—C6	120.26 (13)	H14A—C14—H14C	109.5
C4—C5—H5	119.9	H14B—C14—H14C	109.5
C6—C5—H5	119.9	C1—O1—Cl1	82.11 (8)
C7—C6—C5	119.61 (13)	C8—C13—C12	121.01 (12)
C7—C6—H6	120.2	C8—C13—H13	119.5
C5—C6—H6	120.2	C12—C13—H13	119.5
C6—C7—C2	121.04 (12)

Cg2 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.854 (17)	2.067 (17)	2.8706 (15)	156.4 (15)
C13—H13···O1i	0.95	2.69	3.2347 (16)	117
C6—H6···O2ii	0.95	2.71	3.5657 (17)	150
C12—H12···Cg2iii	0.95	2.88	3.6203 (15)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.854 (17)	2.067 (17)	2.8706 (15)	156.4 (15)
C13—H13⋯O1i	0.95	2.69	3.2347 (16)	117
C6—H6⋯O2ii	0.95	2.71	3.5657 (17)	150
C12—H12⋯Cg2iii	0.95	2.88	3.6203 (15)	136

Symmetry codes: (i) ; (ii) ; (iii) .