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

In the title compound, C(14)H(12)ClNO(2), the mean plane through the amide group [-N-C=O-] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the meth-oxy- and chloro-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 59.24 (4)°. In the crystal, N-H⋯O and weak C-H⋯O hydrogen bonds link the mol-ecules into chains along the a axis.

Related literature

For the biological activity of amides, see: Chen et al. (2011 ▶); El Rayes et al. (2008 ▶); Regiec et al. (2006 ▶); Kuroda et al. (2006 ▶). For related structures, see: Gowda et al. (2008 ▶); Saeed et al. (2008 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Triclinic,

a = 5.4394 (2) Å

b = 7.7754 (3) Å

c = 14.9262 (6) Å

α = 78.759 (3)°

β = 80.712 (3)°

γ = 88.821 (3)°

V = 611.01 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.952, T max = 1.000

14438 measured reflections

2407 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.03

2407 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041384/lh5539sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041384/lh5539Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041384/lh5539Isup3.cml

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

C14H12ClNO2	Z = 2
Mr = 261.70	F(000) = 272
Triclinic, P1	Dx = 1.422 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4394 (2) Å	Cell parameters from 6498 reflections
b = 7.7754 (3) Å	θ = 3.5–29.0°
c = 14.9262 (6) Å	µ = 0.31 mm−1
α = 78.759 (3)°	T = 293 K
β = 80.712 (3)°	Rectangular, white
γ = 88.821 (3)°	0.3 × 0.2 × 0.2 mm
V = 611.01 (4) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2407 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.952, Tmax = 1.000	l = −18→18
14438 measured reflections

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) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3
2407 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.17726 (10)	0.35695 (7)	0.41886 (3)	0.05640 (19)
O1	−0.1117 (2)	0.74773 (19)	0.00401 (9)	0.0527 (4)
O2	0.3921 (2)	1.08846 (18)	−0.40006 (8)	0.0512 (4)
N1	0.2890 (3)	0.73483 (19)	0.02965 (10)	0.0361 (3)
C1	0.3419 (3)	1.0184 (2)	−0.30831 (11)	0.0352 (4)
C2	0.1256 (3)	0.9169 (2)	−0.27999 (12)	0.0389 (4)
H2	0.0280	0.9000	−0.3234	0.047*
C3	0.0551 (3)	0.8416 (2)	−0.18864 (12)	0.0364 (4)
H3	−0.0911	0.7753	−0.1706	0.044*
C4	0.1999 (3)	0.8631 (2)	−0.12239 (11)	0.0319 (4)
C5	0.4163 (3)	0.9639 (2)	−0.15134 (11)	0.0343 (4)
H5	0.5157	0.9788	−0.1082	0.041*
C6	0.4869 (3)	1.0425 (2)	−0.24313 (12)	0.0361 (4)
H6	0.6309	1.1113	−0.2611	0.043*
C7	0.1095 (3)	0.7782 (2)	−0.02462 (12)	0.0350 (4)
C9	0.2519 (3)	0.6449 (2)	0.12294 (11)	0.0311 (3)
C10	0.0413 (3)	0.6671 (2)	0.18553 (12)	0.0381 (4)
H10	−0.0846	0.7411	0.1663	0.046*
C11	0.0182 (3)	0.5794 (2)	0.27654 (12)	0.0391 (4)
H11	−0.1230	0.5940	0.3186	0.047*
C12	0.2064 (3)	0.4700 (2)	0.30466 (12)	0.0366 (4)
C13	0.4176 (3)	0.4487 (2)	0.24347 (12)	0.0381 (4)
H13	0.5441	0.3758	0.2632	0.046*
C14	0.4404 (3)	0.5361 (2)	0.15282 (12)	0.0362 (4)
H14	0.5830	0.5222	0.1113	0.043*
C15	0.6246 (4)	1.1737 (3)	−0.43646 (14)	0.0596 (6)
H15A	0.6329	1.2787	−0.4122	0.089*
H15B	0.6418	1.2033	−0.5027	0.089*
H15C	0.7567	1.0970	−0.4192	0.089*
H1	0.435 (4)	0.741 (2)	0.0024 (12)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0657 (4)	0.0623 (3)	0.0364 (3)	−0.0082 (2)	−0.0090 (2)	0.0036 (2)
O1	0.0295 (7)	0.0825 (10)	0.0405 (7)	−0.0090 (6)	−0.0035 (5)	0.0011 (7)
O2	0.0480 (8)	0.0676 (9)	0.0339 (7)	−0.0103 (6)	−0.0082 (6)	0.0022 (6)
N1	0.0262 (7)	0.0446 (8)	0.0345 (8)	−0.0009 (6)	−0.0015 (6)	−0.0026 (6)
C1	0.0342 (9)	0.0362 (9)	0.0347 (9)	0.0031 (7)	−0.0061 (7)	−0.0054 (7)
C2	0.0340 (9)	0.0461 (10)	0.0394 (9)	−0.0005 (7)	−0.0140 (7)	−0.0084 (8)
C3	0.0272 (8)	0.0396 (9)	0.0428 (10)	−0.0034 (7)	−0.0074 (7)	−0.0068 (7)
C4	0.0284 (8)	0.0315 (8)	0.0357 (9)	0.0027 (6)	−0.0049 (7)	−0.0067 (6)
C5	0.0306 (8)	0.0380 (9)	0.0359 (9)	−0.0012 (7)	−0.0096 (7)	−0.0077 (7)
C6	0.0303 (8)	0.0378 (9)	0.0391 (9)	−0.0056 (7)	−0.0052 (7)	−0.0047 (7)
C7	0.0297 (9)	0.0390 (9)	0.0361 (9)	−0.0016 (7)	−0.0046 (7)	−0.0070 (7)
C9	0.0283 (8)	0.0317 (8)	0.0331 (8)	−0.0041 (6)	−0.0052 (6)	−0.0051 (6)
C10	0.0299 (9)	0.0446 (10)	0.0400 (9)	0.0065 (7)	−0.0066 (7)	−0.0089 (7)
C11	0.0303 (8)	0.0501 (10)	0.0364 (9)	0.0006 (7)	0.0002 (7)	−0.0118 (8)
C12	0.0389 (9)	0.0373 (9)	0.0338 (9)	−0.0088 (7)	−0.0075 (7)	−0.0047 (7)
C13	0.0341 (9)	0.0357 (9)	0.0433 (10)	0.0025 (7)	−0.0093 (7)	−0.0026 (7)
C14	0.0271 (8)	0.0382 (9)	0.0413 (9)	−0.0002 (7)	−0.0006 (7)	−0.0072 (7)
C15	0.0558 (13)	0.0737 (14)	0.0414 (11)	−0.0162 (11)	−0.0041 (9)	0.0068 (10)

Cl1—C12	1.7430 (17)	C5—H5	0.9300
O1—C7	1.222 (2)	C6—H6	0.9300
O2—C1	1.357 (2)	C9—C10	1.387 (2)
O2—C15	1.417 (2)	C9—C14	1.390 (2)
N1—C7	1.363 (2)	C10—C11	1.383 (2)
N1—C9	1.416 (2)	C10—H10	0.9300
N1—H1	0.831 (19)	C11—C12	1.383 (2)
C1—C6	1.388 (2)	C11—H11	0.9300
C1—C2	1.391 (2)	C12—C13	1.376 (2)
C2—C3	1.370 (2)	C13—C14	1.378 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.395 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.389 (2)	C15—H15B	0.9600
C4—C7	1.488 (2)	C15—H15C	0.9600
C5—C6	1.383 (2)
C1—O2—C15	118.93 (14)	C10—C9—C14	119.44 (15)
C7—N1—C9	126.38 (14)	C10—C9—N1	122.65 (14)
C7—N1—H1	116.3 (13)	C14—C9—N1	117.86 (14)
C9—N1—H1	115.8 (13)	C11—C10—C9	120.10 (15)
O2—C1—C6	125.11 (15)	C11—C10—H10	120.0
O2—C1—C2	115.52 (14)	C9—C10—H10	120.0
C6—C1—C2	119.37 (15)	C12—C11—C10	119.59 (16)
C3—C2—C1	120.48 (15)	C12—C11—H11	120.2
C3—C2—H2	119.8	C10—C11—H11	120.2
C1—C2—H2	119.8	C13—C12—C11	120.83 (16)
C2—C3—C4	120.88 (15)	C13—C12—Cl1	119.26 (13)
C2—C3—H3	119.6	C11—C12—Cl1	119.91 (14)
C4—C3—H3	119.6	C12—C13—C14	119.51 (15)
C5—C4—C3	118.26 (15)	C12—C13—H13	120.2
C5—C4—C7	124.18 (14)	C14—C13—H13	120.2
C3—C4—C7	117.56 (14)	C13—C14—C9	120.52 (15)
C6—C5—C4	121.25 (15)	C13—C14—H14	119.7
C6—C5—H5	119.4	C9—C14—H14	119.7
C4—C5—H5	119.4	O2—C15—H15A	109.5
C5—C6—C1	119.75 (15)	O2—C15—H15B	109.5
C5—C6—H6	120.1	H15A—C15—H15B	109.5
C1—C6—H6	120.1	O2—C15—H15C	109.5
O1—C7—N1	122.75 (16)	H15A—C15—H15C	109.5
O1—C7—C4	121.52 (15)	H15B—C15—H15C	109.5
N1—C7—C4	115.72 (14)
C15—O2—C1—C6	9.0 (3)	C3—C4—C7—O1	−26.4 (2)
C15—O2—C1—C2	−171.69 (17)	C5—C4—C7—N1	−28.3 (2)
O2—C1—C2—C3	−179.17 (15)	C3—C4—C7—N1	152.68 (15)
C6—C1—C2—C3	0.2 (3)	C7—N1—C9—C10	−35.0 (3)
C1—C2—C3—C4	−0.8 (3)	C7—N1—C9—C14	147.70 (17)
C2—C3—C4—C5	0.5 (2)	C14—C9—C10—C11	−0.9 (2)
C2—C3—C4—C7	179.57 (15)	N1—C9—C10—C11	−178.21 (15)
C3—C4—C5—C6	0.5 (2)	C9—C10—C11—C12	0.1 (3)
C7—C4—C5—C6	−178.52 (15)	C10—C11—C12—C13	0.7 (3)
C4—C5—C6—C1	−1.1 (3)	C10—C11—C12—Cl1	−179.24 (13)
O2—C1—C6—C5	−179.93 (15)	C11—C12—C13—C14	−0.7 (3)
C2—C1—C6—C5	0.8 (2)	Cl1—C12—C13—C14	179.24 (13)
C9—N1—C7—O1	2.7 (3)	C12—C13—C14—C9	−0.1 (3)
C9—N1—C7—C4	−176.35 (15)	C10—C9—C14—C13	0.9 (2)
C5—C4—C7—O1	152.67 (17)	N1—C9—C14—C13	178.35 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.83 (4)	2.47 (2)	3.222 (2)	151 (2)
C14—H14···O1i	0.93	2.56	3.251 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.83 (4)	2.47 (2)	3.222 (2)	151 (2)
C14—H14⋯O1i	0.93	2.56	3.251 (2)	131

Symmetry code: (i) .