N-(2,6-Dimethyl-phen-yl)benzamide.

The title compound, C(15)H(15)NO, crystallizes with two mol-ecules in the asymmetric unit. The H-N-C=O units are in a trans conformation, similar to that observed in N-(3,4-dimethyl-phen-yl)benzamide, N-(2,6-dichloro-phen-yl)benz-amide and other benzanilides. The central -NHCO- bridging unit is tilted at angles of 17.1 (3) and 16.4 (3)° to the benzoyl ring in the two mol-ecules. The two rings (benzoyl and aniline) are almost orthogonal with respect to each other, making dihedral angles of 86.3 (1) and 86.0 (1)° in the two mol-ecules. N-H⋯O hydrogen bonds link mol-ecules into infinite chains running along the c axis.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 16.4389 (8) Å

b = 8.2903 (4) Å

c = 9.4902 (3) Å

β = 98.165 (4)°

V = 1280.25 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.52 × 0.46 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.924, T max = 0.985

38015 measured reflections

2504 independent reflections

2110 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 0.98

2504 reflections

307 parameters

35 restraints

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018230/bt2724sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018230/bt2724Isup2.hkl

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

C15H15NO	F000 = 480
Mr = 225.28	Dx = 1.169 Mg m−3
Monoclinic, Pc	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P -2 y c	Cell parameters from 18913 reflections
a = 16.4389 (8) Å	θ = 3.1–29.3º
b = 8.2903 (4) Å	µ = 0.07 mm−1
c = 9.4902 (3) Å	T = 295 (2) K
β = 98.165 (4)º	Block, colourless
V = 1280.25 (10) Å3	0.52 × 0.46 × 0.22 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	2504 independent reflections
Monochromator: graphite	2110 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.059
T = 295(2) K	θmax = 26.0º
ω scans with κ offsets	θmin = 5.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −20→20
Tmin = 0.924, Tmax = 0.985	k = −10→10
38015 measured reflections	l = −11→11

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0851P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
2504 reflections	Δρmax = 0.13 e Å−3
307 parameters	Δρmin = −0.14 e Å−3
35 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 2493 Friedel pairs

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	0.32493 (12)	0.0027 (2)	0.63912 (17)	0.0476 (4)
H1N	0.324	−0.0067	0.7291	0.057*
O1	0.27687 (12)	−0.0838 (2)	0.41847 (15)	0.0654 (5)
C1	0.27534 (13)	−0.0900 (2)	0.5470 (2)	0.0446 (5)
C2	0.21752 (13)	−0.2015 (2)	0.6052 (2)	0.0435 (5)
C3	0.15307 (16)	−0.2637 (3)	0.5109 (2)	0.0523 (5)
H3	0.1478	−0.2349	0.4153	0.063*
C4	0.09687 (16)	−0.3669 (3)	0.5561 (3)	0.0601 (6)
H4	0.0532	−0.4056	0.492	0.072*
C5	0.10537 (18)	−0.4130 (3)	0.6967 (3)	0.0664 (7)
H5	0.0679	−0.4843	0.7276	0.08*
C6	0.16901 (17)	−0.3537 (3)	0.7909 (3)	0.0655 (7)
H6	0.1745	−0.3852	0.8859	0.079*
C7	0.22549 (17)	−0.2472 (3)	0.7468 (2)	0.0534 (5)
H7	0.2683	−0.2068	0.8118	0.064*
C8	0.37898 (15)	0.1165 (3)	0.5877 (2)	0.0523 (5)
C9	0.36263 (18)	0.2796 (3)	0.5956 (3)	0.0611 (6)
C10	0.4128 (2)	0.3869 (4)	0.5370 (4)	0.0872 (10)
H10	0.4028	0.4971	0.5414	0.105*
C11	0.4773 (3)	0.3323 (6)	0.4721 (5)	0.1051 (13)
H11	0.5097	0.4056	0.431	0.126*
C12	0.4940 (2)	0.1719 (6)	0.4678 (4)	0.0922 (10)
H12	0.5382	0.1373	0.4245	0.111*
C13	0.44632 (17)	0.0583 (4)	0.5268 (3)	0.0714 (7)
C14	0.46683 (19)	−0.1163 (3)	0.5241 (4)	0.0916 (10)
H14A	0.5245	−0.1288	0.5198	0.137*
H14B	0.4358	−0.1657	0.4421	0.137*
H14C	0.4535	−0.1671	0.6088	0.137*
C15	0.29134 (19)	0.3401 (3)	0.6634 (3)	0.0813 (8)
H15A	0.3035	0.329	0.7649	0.122*
H15B	0.2817	0.4516	0.6394	0.122*
H15C	0.2432	0.2782	0.6291	0.122*
N2	0.82433 (12)	0.5011 (2)	0.52006 (18)	0.0491 (4)
H2N	0.8272	0.4924	0.6109	0.059*
O2	0.87411 (12)	0.4211 (2)	0.32326 (16)	0.0615 (5)
C21	0.87462 (13)	0.4123 (3)	0.4518 (2)	0.0432 (5)
C22	0.93234 (13)	0.2984 (2)	0.5387 (2)	0.0432 (5)
C23	0.99704 (15)	0.2371 (3)	0.4762 (2)	0.0524 (5)
H23	1.0031	0.268	0.3841	0.063*
C24	1.05223 (16)	0.1314 (3)	0.5484 (3)	0.0617 (6)
H24	1.0959	0.0927	0.5058	0.074*
C25	1.04286 (19)	0.0830 (4)	0.6833 (3)	0.0695 (7)
H25	1.0798	0.0102	0.7319	0.083*
C26	0.9794 (2)	0.1416 (4)	0.7462 (3)	0.0706 (7)
H26	0.9733	0.1089	0.8379	0.085*
C27	0.92362 (17)	0.2497 (3)	0.6748 (2)	0.0552 (6)
H27	0.8805	0.2892	0.7185	0.066*
C28	0.76616 (16)	0.6096 (3)	0.4456 (3)	0.0574 (6)
C29	0.69959 (18)	0.5439 (5)	0.3541 (3)	0.0782 (8)
C30	0.6445 (3)	0.6494 (8)	0.2804 (4)	0.1161 (14)
H30	0.5997	0.6093	0.2198	0.139*
C31	0.6549 (4)	0.8115 (8)	0.2950 (5)	0.1338 (18)
H31	0.6174	0.8807	0.2432	0.161*
C32	0.7200 (3)	0.8750 (5)	0.3850 (5)	0.1149 (14)
H32	0.7256	0.9862	0.3944	0.138*
C33	0.7778 (2)	0.7734 (4)	0.4626 (3)	0.0749 (8)
C34	0.8494 (3)	0.8415 (4)	0.5588 (4)	0.0956 (11)
H34A	0.8985	0.7854	0.5439	0.143*
H34B	0.8406	0.8288	0.6561	0.143*
H34C	0.855	0.954	0.5383	0.143*
C35	0.6868 (2)	0.3667 (5)	0.3381 (4)	0.0944 (11)
H35A	0.6348	0.3462	0.2812	0.142*
H35B	0.6876	0.3186	0.4303	0.142*
H35C	0.73	0.3209	0.2924	0.142*

	U11	U22	U33	U12	U13	U23
N1	0.0636 (11)	0.0502 (11)	0.0299 (8)	−0.0042 (8)	0.0098 (7)	−0.0009 (7)
O1	0.0973 (13)	0.0703 (11)	0.0302 (8)	−0.0220 (9)	0.0143 (8)	−0.0006 (7)
C1	0.0622 (13)	0.0405 (11)	0.0317 (10)	0.0035 (9)	0.0088 (9)	0.0025 (8)
C2	0.0584 (12)	0.0382 (10)	0.0354 (10)	0.0056 (9)	0.0121 (9)	−0.0022 (8)
C3	0.0676 (14)	0.0524 (12)	0.0370 (10)	0.0002 (11)	0.0074 (10)	−0.0012 (9)
C4	0.0624 (14)	0.0608 (15)	0.0580 (14)	−0.0097 (12)	0.0113 (11)	−0.0109 (11)
C5	0.0785 (16)	0.0621 (15)	0.0651 (16)	−0.0169 (13)	0.0318 (13)	−0.0066 (12)
C6	0.0941 (19)	0.0658 (15)	0.0404 (12)	−0.0114 (14)	0.0224 (12)	0.0041 (11)
C7	0.0704 (15)	0.0549 (13)	0.0356 (10)	−0.0044 (11)	0.0096 (10)	0.0001 (9)
C8	0.0583 (12)	0.0603 (14)	0.0375 (11)	−0.0109 (10)	0.0040 (9)	0.0008 (9)
C9	0.0758 (16)	0.0583 (14)	0.0465 (13)	−0.0119 (12)	−0.0011 (11)	0.0019 (10)
C10	0.112 (2)	0.0695 (19)	0.077 (2)	−0.0283 (17)	0.0019 (18)	0.0093 (15)
C11	0.102 (3)	0.116 (3)	0.099 (3)	−0.047 (2)	0.021 (2)	0.018 (2)
C12	0.0732 (18)	0.118 (3)	0.089 (2)	−0.0255 (19)	0.0234 (17)	0.001 (2)
C13	0.0634 (15)	0.090 (2)	0.0615 (16)	−0.0082 (14)	0.0117 (13)	−0.0007 (14)
C14	0.083 (2)	0.097 (2)	0.100 (3)	0.0162 (18)	0.0284 (18)	−0.0079 (19)
C15	0.116 (2)	0.0602 (16)	0.0685 (17)	0.0098 (16)	0.0150 (16)	0.0055 (14)
N2	0.0646 (11)	0.0517 (11)	0.0318 (9)	0.0042 (9)	0.0095 (7)	0.0007 (7)
O2	0.0854 (11)	0.0690 (11)	0.0316 (8)	0.0136 (8)	0.0131 (7)	0.0056 (7)
C21	0.0534 (11)	0.0406 (11)	0.0354 (11)	−0.0037 (9)	0.0056 (9)	0.0006 (8)
C22	0.0566 (12)	0.0389 (10)	0.0337 (10)	−0.0058 (9)	0.0050 (9)	−0.0026 (8)
C23	0.0650 (14)	0.0505 (13)	0.0431 (11)	0.0003 (11)	0.0126 (10)	−0.0022 (9)
C24	0.0620 (14)	0.0627 (15)	0.0594 (14)	0.0096 (12)	0.0054 (11)	−0.0100 (11)
C25	0.0839 (18)	0.0638 (16)	0.0554 (15)	0.0191 (14)	−0.0085 (13)	−0.0017 (12)
C26	0.103 (2)	0.0713 (16)	0.0367 (12)	0.0173 (16)	0.0076 (12)	0.0101 (11)
C27	0.0738 (15)	0.0550 (13)	0.0378 (11)	0.0078 (11)	0.0109 (11)	0.0026 (10)
C28	0.0638 (14)	0.0676 (15)	0.0428 (12)	0.0141 (11)	0.0149 (10)	0.0050 (10)
C29	0.0598 (15)	0.117 (2)	0.0581 (16)	0.0097 (16)	0.0087 (12)	0.0036 (16)
C30	0.083 (2)	0.167 (4)	0.093 (3)	0.041 (3)	−0.006 (2)	0.006 (3)
C31	0.133 (4)	0.157 (4)	0.105 (3)	0.079 (3)	−0.006 (3)	0.026 (3)
C32	0.163 (4)	0.086 (2)	0.098 (3)	0.058 (3)	0.025 (3)	0.015 (2)
C33	0.106 (2)	0.0647 (17)	0.0579 (16)	0.0229 (15)	0.0245 (15)	0.0070 (12)
C34	0.155 (3)	0.0564 (17)	0.078 (2)	−0.009 (2)	0.024 (2)	−0.0030 (15)
C35	0.0733 (19)	0.114 (3)	0.094 (3)	−0.0303 (19)	0.0074 (18)	−0.014 (2)

N1—C1	1.348 (3)	N2—C21	1.341 (3)
N1—C8	1.429 (3)	N2—C28	1.425 (3)
N1—H1N	0.86	N2—H2N	0.86
O1—C1	1.225 (2)	O2—C21	1.221 (3)
C1—C2	1.487 (3)	C21—C22	1.500 (3)
C2—C3	1.385 (3)	C22—C27	1.380 (3)
C2—C7	1.385 (3)	C22—C23	1.386 (3)
C3—C4	1.373 (4)	C23—C24	1.372 (4)
C3—H3	0.93	C23—H23	0.93
C4—C5	1.376 (4)	C24—C25	1.372 (4)
C4—H4	0.93	C24—H24	0.93
C5—C6	1.368 (4)	C25—C26	1.364 (4)
C5—H5	0.93	C25—H25	0.93
C6—C7	1.389 (4)	C26—C27	1.388 (4)
C6—H6	0.93	C26—H26	0.93
C7—H7	0.93	C27—H27	0.93
C8—C9	1.383 (4)	C28—C33	1.378 (4)
C8—C13	1.405 (4)	C28—C29	1.406 (4)
C9—C10	1.382 (4)	C29—C30	1.376 (5)
C9—C15	1.501 (4)	C29—C35	1.489 (6)
C10—C11	1.376 (6)	C30—C31	1.359 (8)
C10—H10	0.93	C30—H30	0.93
C11—C12	1.360 (6)	C31—C32	1.375 (8)
C11—H11	0.93	C31—H31	0.93
C12—C13	1.392 (5)	C32—C33	1.398 (5)
C12—H12	0.93	C32—H32	0.93
C13—C14	1.488 (4)	C33—C34	1.494 (5)
C14—H14A	0.96	C34—H34A	0.96
C14—H14B	0.96	C34—H34B	0.96
C14—H14C	0.96	C34—H34C	0.96
C15—H15A	0.96	C35—H35A	0.96
C15—H15B	0.96	C35—H35B	0.96
C15—H15C	0.9599	C35—H35C	0.96
C1—N1—C8	120.20 (17)	C21—N2—C28	121.55 (17)
C1—N1—H1N	119.9	C21—N2—H2N	119.2
C8—N1—H1N	119.9	C28—N2—H2N	119.2
O1—C1—N1	121.7 (2)	O2—C21—N2	122.2 (2)
O1—C1—C2	120.00 (19)	O2—C21—C22	120.06 (19)
N1—C1—C2	118.25 (17)	N2—C21—C22	117.74 (17)
C3—C2—C7	118.9 (2)	C27—C22—C23	118.8 (2)
C3—C2—C1	117.52 (18)	C27—C22—C21	123.8 (2)
C7—C2—C1	123.5 (2)	C23—C22—C21	117.35 (17)
C4—C3—C2	121.1 (2)	C24—C23—C22	120.9 (2)
C4—C3—H3	119.4	C24—C23—H23	119.6
C2—C3—H3	119.4	C22—C23—H23	119.6
C3—C4—C5	119.8 (2)	C23—C24—C25	120.0 (2)
C3—C4—H4	120.1	C23—C24—H24	120
C5—C4—H4	120.1	C25—C24—H24	120
C6—C5—C4	119.8 (2)	C26—C25—C24	119.9 (2)
C6—C5—H5	120.1	C26—C25—H25	120
C4—C5—H5	120.1	C24—C25—H25	120
C5—C6—C7	120.9 (2)	C25—C26—C27	120.7 (2)
C5—C6—H6	119.6	C25—C26—H26	119.7
C7—C6—H6	119.6	C27—C26—H26	119.7
C2—C7—C6	119.4 (2)	C22—C27—C26	119.8 (2)
C2—C7—H7	120.3	C22—C27—H27	120.1
C6—C7—H7	120.3	C26—C27—H27	120.1
C9—C8—C13	121.9 (2)	C33—C28—C29	122.5 (3)
C9—C8—N1	119.5 (2)	C33—C28—N2	119.5 (3)
C13—C8—N1	118.6 (2)	C29—C28—N2	118.1 (3)
C10—C9—C8	118.4 (3)	C30—C29—C28	117.8 (4)
C10—C9—C15	120.3 (3)	C30—C29—C35	120.2 (4)
C8—C9—C15	121.3 (2)	C28—C29—C35	122.1 (3)
C11—C10—C9	120.6 (3)	C31—C30—C29	120.8 (4)
C11—C10—H10	119.7	C31—C30—H30	119.6
C9—C10—H10	119.7	C29—C30—H30	119.6
C12—C11—C10	120.5 (3)	C30—C31—C32	121.1 (4)
C12—C11—H11	119.8	C30—C31—H31	119.4
C10—C11—H11	119.8	C32—C31—H31	119.4
C11—C12—C13	121.5 (3)	C31—C32—C33	120.5 (4)
C11—C12—H12	119.3	C31—C32—H32	119.8
C13—C12—H12	119.3	C33—C32—H32	119.8
C12—C13—C8	117.0 (3)	C28—C33—C32	117.3 (4)
C12—C13—C14	120.6 (3)	C28—C33—C34	121.9 (3)
C8—C13—C14	122.3 (2)	C32—C33—C34	120.8 (3)
C13—C14—H14A	109.5	C33—C34—H34A	109.5
C13—C14—H14B	109.5	C33—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C13—C14—H14C	109.5	C33—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C9—C15—H15A	109.5	C29—C35—H35A	109.5
C9—C15—H15B	109.5	C29—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C9—C15—H15C	109.4	C29—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C8—N1—C1—O1	2.5 (3)	C28—N2—C21—O2	1.0 (3)
C8—N1—C1—C2	−177.4 (2)	C28—N2—C21—C22	−178.5 (2)
O1—C1—C2—C3	−16.4 (3)	O2—C21—C22—C27	−162.8 (2)
N1—C1—C2—C3	163.44 (19)	N2—C21—C22—C27	16.7 (3)
O1—C1—C2—C7	162.8 (2)	O2—C21—C22—C23	15.9 (3)
N1—C1—C2—C7	−17.3 (3)	N2—C21—C22—C23	−164.55 (19)
C7—C2—C3—C4	1.0 (3)	C27—C22—C23—C24	−0.8 (3)
C1—C2—C3—C4	−179.8 (2)	C21—C22—C23—C24	−179.6 (2)
C2—C3—C4—C5	−1.5 (4)	C22—C23—C24—C25	1.2 (4)
C3—C4—C5—C6	1.0 (4)	C23—C24—C25—C26	−0.9 (4)
C4—C5—C6—C7	0.0 (4)	C24—C25—C26—C27	0.3 (5)
C3—C2—C7—C6	0.0 (3)	C23—C22—C27—C26	0.2 (3)
C1—C2—C7—C6	−179.2 (2)	C21—C22—C27—C26	178.9 (2)
C5—C6—C7—C2	−0.5 (4)	C25—C26—C27—C22	0.1 (4)
C1—N1—C8—C9	108.7 (2)	C21—N2—C28—C33	−110.2 (3)
C1—N1—C8—C13	−69.7 (3)	C21—N2—C28—C29	68.3 (3)
C13—C8—C9—C10	2.4 (4)	C33—C28—C29—C30	−0.3 (4)
N1—C8—C9—C10	−175.9 (2)	N2—C28—C29—C30	−178.8 (3)
C13—C8—C9—C15	−178.9 (3)	C33—C28—C29—C35	−179.0 (3)
N1—C8—C9—C15	2.8 (3)	N2—C28—C29—C35	2.5 (4)
C8—C9—C10—C11	0.1 (4)	C28—C29—C30—C31	0.6 (6)
C15—C9—C10—C11	−178.7 (3)	C35—C29—C30—C31	179.4 (4)
C9—C10—C11—C12	−1.6 (6)	C29—C30—C31—C32	−0.9 (8)
C10—C11—C12—C13	0.7 (6)	C30—C31—C32—C33	0.8 (8)
C11—C12—C13—C8	1.6 (5)	C29—C28—C33—C32	0.3 (4)
C11—C12—C13—C14	−178.5 (3)	N2—C28—C33—C32	178.7 (3)
C9—C8—C13—C12	−3.2 (4)	C29—C28—C33—C34	−179.2 (3)
N1—C8—C13—C12	175.1 (2)	N2—C28—C33—C34	−0.8 (4)
C9—C8—C13—C14	176.9 (3)	C31—C32—C33—C28	−0.5 (6)
N1—C8—C13—C14	−4.8 (4)	C31—C32—C33—C34	179.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.19	2.949 (2)	147
N2—H2N···O2ii	0.86	2.17	2.949 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.19	2.949 (2)	147
N2—H2N⋯O2ii	0.86	2.17	2.949 (2)	150

Symmetry codes: (i) ; (ii) .