N-(4-Chloro­phen­yl)-4-meth­oxy­benzamide

In the title compound, C₁₄H₁₂ClNO₂, the mean plane through the amide group [–N—C=O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with the meth­oxy- 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 mol­ecules into chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.100
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.305
            Value of mu given      =     0.309
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00300 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Aromatic amides have been utilized as versatile fragments to construct frameworks that have numerous functions such as molecular recognition, conformational switching, and biological activities which include in vitro xanthine oxidase (XO), tyrosinase and melanin production inhibitory activity. Further, benzanilides and their metal complexes have also been known for their marked biological activities such as antifungal,antibacterial and genotoxic effect (Chen et al., 2011). Globally, multidrug-resistant bacteria are a major health problem leading to severe consequences; anilides have shown antimycobacterial activity against classical mycobacterium tuberculosis (El Rayes et al., 2008), thiobenzanilides also belong to a group of biologically active compounds possessing antimicobacterial activities. In addition, N-substituted carboxamide isothiazoles (Regiec et al., 2006) produced a remarkable immunotropic, antiviral and anti-inflammatory activities, N-acylamino benzamides (Kuroda et al., 2006), constitute an important class of potent insecticides.

The molecular structure of the title compound (I) is shown in Fig. 1. All bond lengths and angles are normal and correspond to those observed in the related structures (Gowda et al., 2008; Saeed et al., 2008). The amide group [–N—C═O–] forms dihedral angles of 27.55 (8) and 31.94 (7)° with methoxy-substituted benzene [C1-C6] and chloro-substitued benzene [C9-C14] rings, respectively. The two benzene rings are twisted by 59.24 (4)° with respect to each other. In the crystal, N1—H1···O1ⁱ and C14—H14A···O1ⁱ hydrogen bonds link the molecules into chains along the a axis (Fig. 2) (Table 1).

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).

S2. Experimental

To a mixture of 4-chloroaniline (0.127 g, 1 mmol) and aq. sodium hydroxide solution (10%, 20 ml) in a round bottom flask (50 ml), 4-methoxybenzoyl chloride (0.170 g, 1 mmol) was added in portions during stirring at room temperature. After the complete addition of 4-methoxybenzoyl chloride, the reaction mixture was further stirred for 30 minutes and then poured into ice-cold water (25 ml). It was further stirred for 10 min. and filtered. Finally, the product was obtained after drying followed by crystallization from ethanol (0.224 g, 86%) to give X-ray quality crystals.

S3. Refinement

The H atom bonded to the N atom was located in a difference map and refined independently with an isotropic displacement parameter. Other H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.96 Å and with with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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).

Figures

	Fig. 1. The molecular structure of (I) shown with 40% probability ellipsoids. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules with dashed lines to show intermolecular N—H···O and weak C—H···O hydrogen bonds. Only H atoms involved in hydrogen bonds are shown.

N-(4-Chlorophenyl)-4-methoxybenzamide

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0427P)^2 + 0.2321P] where P = (Fo^2 + 2Fc^2)/3
2407 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.83 (4)	2.47 (2)	3.222 (2)	151 (2)
C14—H14···O1^i	0.93	2.56	3.251 (2)	131

Symmetry code: (i) x+1, y, z.