Crystal structure of 4-meth­oxy-N-phenyl­benzamide

In the title mol­ecule, C₁₄H₁₃NO₂, the dihedral angle between the planes of the benzene rings is 65.18 (4)°. The central amide group has about the same degree of twist with respect to both ring planes, as indicated by the dihedral angles of 34.70 (8) and 30.62 (8)° between its plane and that of the phenyl and 4-meth­oxy­benzene rings, respectively. The C atom of the meth­oxy group is close to being coplanar with its attached ring [deviation = −0.112 (2) Å]. In the crystal, mol­ecules are linked by inter-amide N—H...O hydrogen bonds, which generate C(4) chains propagating in the [100] direction. Adajcent mol­ecules in the chain are related by translational symmetry.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.097
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

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Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          64 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 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

   1 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
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Related literature

The background to this work has been described in earlier papers; see: Ren et al. (2010); Zhu et al. (2011). For related structures, see: Raza et al. (2010); Gowda et al. (2003).

S1. Experimental

To a 100 ml round flask fitted with a condenser was added aniline (0.93 g, 10 mmol), dichloromethane (15 ml) and triethylamine(0.5 ml) with magnetic stirring. 4-methoxybenzoyl chloride (1.70 g, 10 mmol) was added gradually. The reaction mixture was stirred at room temperature for 1 h and then refluxed for 2 h. The product precipitated as a white powder, which was washed three times with water and dichloromethane. Recrystallization from ethyl alcohol solution produced colourless prisms of the title compound.

S2. Refinement

H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93 Å, N—H = 0.86 Å and U_iso(H)= 1.2U_eq(C,N).

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I) with the donor-acceptor distances of hydrogen bonds drawn as dashed lines. H atoms are not shown.

4-Methoxy-N-phenylbenzamide

Crystal data

C14H13NO2	V = 565.5 (5) Å^3
Mr = 227.25	Z = 2
Triclinic, P1	F(000) = 240
Hall symbol: -P 1	Dx = 1.335 Mg m^−3
a = 5.308 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.709 (4) Å	θ = 1.5–25.1°
c = 14.109 (7) Å	µ = 0.09 mm^−1
α = 96.911 (8)°	T = 296 K
β = 99.210 (8)°	Prism, colorless
γ = 90.511 (9)°	0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer	2005 independent reflections
Radiation source: fine-focus sealed tube	1605 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
ω scans	θmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −5→6
Tmin = 0.974, Tmax = 0.982	k = −8→9
3188 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.045P)^2 + 0.1154P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2005 reflections	Δρmax = 0.16 e Å^−3
156 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (5)

Special details

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
N1	0.2321 (2)	0.27538 (17)	0.57341 (8)	0.0387 (3)
H1	0.0748	0.2753	0.5465	0.046*
O1	0.63875 (19)	0.25639 (17)	0.54382 (8)	0.0542 (4)
O2	0.0921 (2)	0.14685 (16)	0.11034 (7)	0.0520 (3)
C1	0.2818 (3)	0.29568 (19)	0.67586 (10)	0.0340 (3)
C2	0.4919 (3)	0.3893 (2)	0.72863 (11)	0.0427 (4)
H2	0.6085	0.4409	0.6971	0.051*
C3	0.5279 (3)	0.4060 (2)	0.82849 (12)	0.0504 (4)
H3	0.6693	0.4693	0.8638	0.060*
C4	0.3582 (3)	0.3307 (2)	0.87637 (11)	0.0483 (4)
H4	0.3849	0.3414	0.9436	0.058*
C5	0.1478 (3)	0.2391 (2)	0.82331 (11)	0.0468 (4)
H5	0.0306	0.1889	0.8551	0.056*
C6	0.1091 (3)	0.2210 (2)	0.72366 (11)	0.0401 (4)
H6	−0.0333	0.1585	0.6886	0.048*
C7	0.4093 (3)	0.2561 (2)	0.51365 (11)	0.0373 (4)
C8	0.3083 (3)	0.22995 (19)	0.40820 (10)	0.0345 (3)
C9	0.4522 (3)	0.1323 (2)	0.34765 (11)	0.0390 (4)
H9	0.6042	0.0850	0.3742	0.047*
C10	0.3727 (3)	0.1051 (2)	0.24959 (11)	0.0415 (4)
H10	0.4676	0.0365	0.2103	0.050*
C11	0.1516 (3)	0.1795 (2)	0.20900 (10)	0.0377 (4)
C12	0.0070 (3)	0.2788 (2)	0.26739 (11)	0.0395 (4)
H12	−0.1412	0.3297	0.2403	0.047*
C13	0.0852 (3)	0.3014 (2)	0.36659 (10)	0.0378 (4)
H13	−0.0139	0.3658	0.4060	0.045*
C14	−0.1445 (4)	0.2052 (3)	0.06486 (12)	0.0631 (5)
H14A	−0.2804	0.1623	0.0940	0.095*
H14B	−0.1707	0.1620	−0.0028	0.095*
H14C	−0.1425	0.3307	0.0726	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0288 (6)	0.0535 (8)	0.0333 (7)	0.0023 (5)	0.0034 (5)	0.0053 (6)
O1	0.0299 (6)	0.0892 (10)	0.0424 (7)	0.0060 (6)	0.0046 (5)	0.0050 (6)
O2	0.0563 (7)	0.0653 (8)	0.0327 (6)	0.0104 (6)	0.0067 (5)	0.0000 (5)
C1	0.0313 (7)	0.0364 (8)	0.0342 (8)	0.0065 (6)	0.0052 (6)	0.0035 (6)
C2	0.0360 (8)	0.0479 (10)	0.0434 (9)	−0.0027 (7)	0.0083 (7)	−0.0002 (7)
C3	0.0418 (9)	0.0583 (11)	0.0453 (10)	0.0005 (8)	0.0001 (7)	−0.0073 (8)
C4	0.0520 (10)	0.0587 (11)	0.0325 (8)	0.0115 (8)	0.0045 (7)	0.0016 (7)
C5	0.0471 (9)	0.0546 (11)	0.0418 (9)	0.0046 (8)	0.0140 (7)	0.0088 (8)
C6	0.0333 (8)	0.0477 (9)	0.0387 (8)	−0.0004 (7)	0.0055 (6)	0.0036 (7)
C7	0.0309 (8)	0.0416 (9)	0.0399 (8)	0.0030 (6)	0.0059 (6)	0.0066 (7)
C8	0.0314 (7)	0.0370 (8)	0.0358 (8)	−0.0006 (6)	0.0072 (6)	0.0051 (6)
C9	0.0313 (8)	0.0427 (9)	0.0437 (9)	0.0050 (6)	0.0072 (6)	0.0059 (7)
C10	0.0400 (8)	0.0446 (9)	0.0411 (9)	0.0060 (7)	0.0142 (7)	−0.0004 (7)
C11	0.0403 (8)	0.0390 (9)	0.0343 (8)	−0.0009 (7)	0.0087 (6)	0.0033 (6)
C12	0.0348 (8)	0.0451 (9)	0.0379 (8)	0.0062 (7)	0.0035 (6)	0.0052 (7)
C13	0.0357 (8)	0.0408 (9)	0.0372 (8)	0.0062 (6)	0.0094 (6)	0.0010 (7)
C14	0.0676 (12)	0.0819 (14)	0.0369 (9)	0.0150 (10)	0.0004 (8)	0.0059 (9)

Geometric parameters (Å, º)

N1—C7	1.3580 (19)	C6—H6	0.9300
N1—C1	1.4164 (19)	C7—C8	1.487 (2)
N1—H1	0.8600	C8—C13	1.385 (2)
O1—C7	1.2242 (18)	C8—C9	1.394 (2)
O2—C11	1.3689 (18)	C9—C10	1.370 (2)
O2—C14	1.419 (2)	C9—H9	0.9300
C1—C2	1.382 (2)	C10—C11	1.382 (2)
C1—C6	1.381 (2)	C10—H10	0.9300
C2—C3	1.381 (2)	C11—C12	1.384 (2)
C2—H2	0.9300	C12—C13	1.384 (2)
C3—C4	1.373 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.378 (2)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.378 (2)	C14—H14C	0.9600
C5—H5	0.9300
C7—N1—C1	126.16 (12)	C13—C8—C9	118.33 (14)
C7—N1—H1	116.9	C13—C8—C7	123.93 (13)
C1—N1—H1	116.9	C9—C8—C7	117.71 (13)
C11—O2—C14	118.22 (13)	C10—C9—C8	120.86 (14)
C2—C1—C6	119.58 (14)	C10—C9—H9	119.6
C2—C1—N1	122.48 (13)	C8—C9—H9	119.6
C6—C1—N1	117.92 (13)	C9—C10—C11	120.12 (14)
C1—C2—C3	119.65 (15)	C9—C10—H10	119.9
C1—C2—H2	120.2	C11—C10—H10	119.9
C3—C2—H2	120.2	O2—C11—C10	115.38 (13)
C4—C3—C2	121.03 (16)	O2—C11—C12	124.49 (14)
C4—C3—H3	119.5	C10—C11—C12	120.13 (14)
C2—C3—H3	119.5	C13—C12—C11	119.30 (14)
C3—C4—C5	119.01 (15)	C13—C12—H12	120.4
C3—C4—H4	120.5	C11—C12—H12	120.4
C5—C4—H4	120.5	C12—C13—C8	121.22 (14)
C4—C5—C6	120.70 (15)	C12—C13—H13	119.4
C4—C5—H5	119.6	C8—C13—H13	119.4
C6—C5—H5	119.6	O2—C14—H14A	109.5
C5—C6—C1	120.02 (15)	O2—C14—H14B	109.5
C5—C6—H6	120.0	H14A—C14—H14B	109.5
C1—C6—H6	120.0	O2—C14—H14C	109.5
O1—C7—N1	122.62 (14)	H14A—C14—H14C	109.5
O1—C7—C8	121.34 (13)	H14B—C14—H14C	109.5
N1—C7—C8	116.02 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.31	3.110 (2)	154

Symmetry code: (i) x−1, y, z.