Crystal structure of 4-meth-oxy-N-phenyl-benzamide.

In the title mol-ecule, 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-meth-oxy-benzene rings, respectively. The C atom of the meth-oxy group is close to being coplanar with its attached ring [deviation = -0.112 (2) Å]. In the crystal, mol-ecules are linked by inter-amide N-H⋯O hydrogen bonds, which generate C(4) chains propagating in the [100] direction. Adajcent mol-ecules in the chain are related by translational symmetry.

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 ▶).

Experimental

Crystal data

C14H13NO2

M = 227.25

Triclinic,

a = 5.308 (3) Å

b = 7.709 (4) Å

c = 14.109 (7) Å

α = 96.911 (8)°

β = 99.210 (8)°

γ = 90.511 (9)°

V = 565.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.974, T max = 0.982

3188 measured reflections

2005 independent reflections

1605 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.03

2005 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814016420/hb7253sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016420/hb7253Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016420/hb7253Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814016420/hb7253fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814016420/hb7253fig2.tif

Part of the crystal structure of (I) with the donor-acceptor distances of hydrogen bonds drawn as dashed lines. H atoms are not shown.

CCDC reference: 1014108

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H13NO2	V = 565.5 (5) Å3
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

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 on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.045P)2 + 0.1154P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (5)

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	0.2321 (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*

	U11	U22	U33	U12	U13	U23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.31	3.110 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.31	3.110 (2)	154

Symmetry code: (i) .