Crystal structure of 4-meth­oxy-N-phenyl­benzamide

Wang, Z.; Lei, H.; Jin, L.; Zhu, R.

doi:10.1107/S1600536814016420

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Page o921

doi:10.1107/S1600536814016420

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Crystal structure of 4-methoxy-N-phenylbenzamide

Zhijun Wang,^a Haiying Lei,^b Linhua Jin ^c and Ruitao Zhu ^c ^*

^aDepartment of Chemistry, Changzhi University, Changzhi 046011, People's Republic of China, ^bDepartment of Biological Science and Technology, Changzhi University, Changzhi 046011, People's Republic of China, and ^cDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: ruitaozhu@126.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 14 July 2014; accepted 15 July 2014; online 1 August 2014)

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.

Keywords: crystal structure; amide; C(4) chain; hydrogen bonding.

CCDC reference: 1014108

1. 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 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₃NO₂
M_r = 227.25
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
2005 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

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) x-1, y, z.

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 ).

Supporting information

CCDC reference: 1014108

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814016420/hb7253sup1.cif

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

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

checkCIF report

Related literature top

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 top

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.

Computing details top

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 top

	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 top

Crystal data top

C₁₄H₁₃NO₂	V = 565.5 (5) Å³
M_r = 227.25	Z = 2
Triclinic, P1	F(000) = 240
Hall symbol: -P 1	D_x = 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 top

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

Refinement top

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(F_o²) + (0.045P)² + 0.1154P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2005 reflections	Δρ_max = 0.16 e Å⁻³
156 parameters	Δρ_min = −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)

Crystal data top

C₁₄H₁₃NO₂	γ = 90.511 (9)°
M_r = 227.25	V = 565.5 (5) Å³
Triclinic, P1	Z = 2
a = 5.308 (3) Å	Mo Kα radiation
b = 7.709 (4) Å	µ = 0.09 mm⁻¹
c = 14.109 (7) Å	T = 296 K
α = 96.911 (8)°	0.30 × 0.20 × 0.20 mm
β = 99.210 (8)°

Data collection top

Bruker SMART CCD diffractometer	2005 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1605 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.982	R_int = 0.013
3188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
2005 reflections	Δρ_min = −0.13 e Å⁻³
156 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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) top

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) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Acknowledgements

We gratefully acknowledge the Natural Science Foundation of China (grant No. 21201024), the Natural Science Foundation of Shanxi province (grant No. 2012021009-1) and the College Student's Innovation Traning Project in Shanxi Province (grant No. 2013319).

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