N-(2,3-Dimethyl-phen-yl)benzamide.

The conformation of the N-H bond in the structure of the title compound, C(15)H(15)NO, is anti to the ortho and meta-methyl substituents in the aniline benzene ring, in contrast to the syn conformation observed with respect to the ortho and meta-chloro substituents in N-(2,3-dichloro-phen-yl)benzamide. Furthermore, the conformations of N-H and C=O bonds in the amide group are anti to each other, similar to those observed in other benzanilides. The dihedral angle between the benzoyl and aniline rings is 84.1 (2)°. The amide group is twisted by 23.0 (3)° out of the plane of the benzoyl ring. The structure exhibits positional disorder over the aniline ring, with site occupancies of 0.80 (1) and 0.20 (1) for the major and minor components, respectively. In the crystal, mol-ecules are connected through N-H⋯O hydrogen bonds into chains running along the b axis. An intra-molecular C-H⋯O close contact occurs.

Related literature

For related structures, see Azumaya et al. (1994 ▶); Gowda et al. (2003 ▶, 2007 ▶, 2008a ▶,b ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Orthorhombic,

a = 8.4656 (2) Å

b = 9.4848 (2) Å

c = 31.0957 (9) Å

V = 2496.81 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.52 × 0.16 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.963, T max = 0.996

48994 measured reflections

2409 independent reflections

1572 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.146

S = 1.05

2409 reflections

222 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809012112/dn2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012112/dn2440Isup2.hkl

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

C15H15NO	F(000) = 960
Mr = 225.28	Dx = 1.199 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 12625 reflections
a = 8.4656 (2) Å	θ = 3.1–29.2°
b = 9.4848 (2) Å	µ = 0.08 mm−1
c = 31.0957 (9) Å	T = 295 K
V = 2496.81 (11) Å3	Rod, colourless
Z = 8	0.52 × 0.16 × 0.05 mm

Oxford Diffraction Xcalibur System diffractometer	2409 independent reflections
graphite	1572 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.052
ω scans with κ offsets	θmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −10→10
Tmin = 0.963, Tmax = 0.996	k = −11→11
48994 measured reflections	l = −38→38

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.6303P] where P = (Fo2 + 2Fc2)/3
2409 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.10 e Å−3
14 restraints	Δρmin = −0.14 e Å−3

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	Occ. (<1)
N1	0.2585 (2)	0.60702 (17)	0.37113 (6)	0.0562 (5)
H1N	0.273 (3)	0.6973 (18)	0.3654 (7)	0.067*
O1	0.1702 (2)	0.39655 (14)	0.34744 (5)	0.0676 (5)
C1	0.1605 (2)	0.52512 (19)	0.34747 (6)	0.0496 (5)
C2	0.0397 (2)	0.59716 (19)	0.32076 (6)	0.0461 (5)
C3	−0.0200 (2)	0.5254 (2)	0.28599 (7)	0.0549 (5)
H3	0.0147	0.4342	0.2804	0.066*
C4	−0.1302 (3)	0.5859 (2)	0.25935 (7)	0.0635 (6)
H4	−0.1678	0.5369	0.2356	0.076*
C5	−0.1844 (3)	0.7196 (2)	0.26811 (8)	0.0701 (7)
H5	−0.2597	0.7609	0.2504	0.084*
C6	−0.1277 (3)	0.7913 (2)	0.30275 (8)	0.0729 (7)
H6	−0.1657	0.8812	0.3087	0.087*
C7	−0.0153 (3)	0.7326 (2)	0.32897 (7)	0.0581 (6)
H7	0.0242	0.7833	0.3522	0.07*
C8	0.3938 (5)	0.5547 (4)	0.39290 (14)	0.0517 (10)	0.8
C9	0.3754 (4)	0.4635 (4)	0.42634 (13)	0.0567 (8)	0.8
C10	0.5108 (6)	0.4031 (5)	0.44545 (16)	0.0718 (10)	0.8
C11	0.6555 (6)	0.4480 (7)	0.4303 (2)	0.0842 (13)	0.8
H11	0.7458	0.4096	0.4427	0.101*	0.8
C12	0.6745 (5)	0.5444 (5)	0.39867 (14)	0.0910 (11)	0.8
H12	0.7754	0.5718	0.3903	0.109*	0.8
C13	0.5457 (5)	0.6012 (5)	0.37902 (16)	0.0713 (12)	0.8
H13	0.5563	0.668	0.3573	0.086*	0.8
C14	0.2156 (5)	0.4279 (4)	0.44389 (12)	0.0748 (10)	0.8
H14A	0.2122	0.4502	0.474	0.112*	0.8
H14B	0.1955	0.3292	0.4399	0.112*	0.8
H14C	0.1367	0.4817	0.429	0.112*	0.8
C15	0.4970 (6)	0.2939 (4)	0.48009 (12)	0.1080 (14)	0.8
H15A	0.4326	0.2174	0.4701	0.162*	0.8
H15B	0.4493	0.3352	0.5051	0.162*	0.8
H15C	0.6002	0.2593	0.4873	0.162*	0.8
C8D	0.3513 (13)	0.5282 (12)	0.4010 (3)	0.051 (4)	0.2
C9D	0.5124 (14)	0.5487 (12)	0.3951 (3)	0.053 (3)	0.2
C10D	0.6201 (10)	0.4779 (17)	0.4211 (5)	0.082 (5)	0.2
C11D	0.5667 (12)	0.3865 (16)	0.4528 (5)	0.078 (5)	0.2
H11D	0.6387	0.3392	0.4702	0.094*	0.2
C12D	0.4055 (14)	0.3660 (9)	0.4587 (3)	0.067 (3)	0.2
H12D	0.3698	0.3048	0.4799	0.081*	0.2
C13D	0.2978 (10)	0.4368 (12)	0.4328 (3)	0.048 (3)	0.2
H13D	0.19	0.423	0.4367	0.057*	0.2
C14D	0.5865 (19)	0.648 (2)	0.3617 (7)	0.090 (6)	0.2
H14D	0.5112	0.6671	0.3393	0.135*	0.2
H14E	0.6786	0.6049	0.3496	0.135*	0.2
H14F	0.6157	0.7352	0.3754	0.135*	0.2
C15D	0.7999 (14)	0.4840 (15)	0.4207 (5)	0.081 (4)	0.2
H15D	0.8375	0.4718	0.3918	0.121*	0.2
H15E	0.8414	0.4102	0.4386	0.121*	0.2
H15F	0.8343	0.5737	0.4315	0.121*	0.2

	U11	U22	U33	U12	U13	U23
N1	0.0656 (11)	0.0354 (8)	0.0678 (11)	−0.0015 (8)	−0.0083 (9)	0.0018 (8)
O1	0.0834 (11)	0.0337 (8)	0.0856 (11)	0.0058 (7)	−0.0171 (9)	−0.0005 (7)
C1	0.0582 (12)	0.0324 (10)	0.0582 (12)	0.0000 (9)	0.0030 (10)	0.0016 (9)
C2	0.0481 (11)	0.0361 (10)	0.0540 (11)	−0.0031 (8)	0.0055 (9)	0.0046 (9)
C3	0.0558 (12)	0.0377 (10)	0.0711 (14)	−0.0031 (9)	−0.0009 (11)	−0.0025 (10)
C4	0.0614 (14)	0.0581 (13)	0.0710 (15)	−0.0079 (11)	−0.0129 (11)	−0.0011 (11)
C5	0.0702 (15)	0.0527 (13)	0.0874 (17)	−0.0020 (11)	−0.0219 (13)	0.0114 (13)
C6	0.0815 (16)	0.0444 (12)	0.0928 (18)	0.0126 (12)	−0.0174 (14)	0.0009 (12)
C7	0.0700 (14)	0.0386 (11)	0.0659 (13)	0.0030 (10)	−0.0054 (11)	−0.0014 (10)
C8	0.053 (3)	0.0387 (15)	0.063 (2)	0.0004 (17)	−0.0032 (18)	−0.0055 (14)
C9	0.067 (2)	0.0446 (18)	0.059 (2)	−0.0009 (18)	−0.005 (2)	−0.0083 (15)
C10	0.076 (3)	0.064 (2)	0.076 (3)	0.003 (2)	−0.015 (2)	−0.0052 (19)
C11	0.081 (3)	0.088 (3)	0.083 (3)	0.015 (3)	−0.023 (3)	−0.006 (2)
C12	0.060 (2)	0.101 (3)	0.112 (3)	−0.012 (2)	0.003 (2)	−0.009 (2)
C13	0.057 (3)	0.070 (3)	0.088 (4)	−0.014 (2)	−0.003 (3)	−0.006 (2)
C14	0.094 (3)	0.066 (2)	0.064 (2)	−0.009 (2)	0.008 (2)	0.0078 (17)
C15	0.150 (4)	0.085 (3)	0.088 (3)	0.019 (3)	−0.035 (2)	0.018 (2)
C8D	0.050 (7)	0.067 (10)	0.037 (7)	−0.007 (7)	−0.002 (6)	0.006 (6)
C9D	0.053 (7)	0.053 (9)	0.052 (8)	−0.020 (6)	0.018 (5)	−0.025 (5)
C10D	0.052 (8)	0.085 (16)	0.108 (17)	−0.008 (7)	−0.015 (7)	−0.031 (9)
C11D	0.061 (7)	0.090 (12)	0.083 (12)	0.029 (9)	−0.026 (9)	−0.020 (7)
C12D	0.082 (8)	0.061 (7)	0.059 (7)	0.005 (6)	−0.019 (6)	0.013 (5)
C13D	0.037 (7)	0.052 (8)	0.054 (9)	−0.001 (7)	0.002 (7)	0.012 (5)
C14D	0.051 (9)	0.083 (12)	0.135 (16)	−0.009 (7)	0.029 (9)	0.033 (10)
C15D	0.046 (7)	0.101 (10)	0.096 (10)	−0.004 (6)	−0.009 (7)	0.022 (8)

N1—C1	1.354 (3)	C12—H12	0.93
N1—C8	1.419 (4)	C13—H13	0.93
N1—C8D	1.428 (4)	C14—H14A	0.96
N1—H1N	0.883 (16)	C14—H14B	0.96
O1—C1	1.222 (2)	C14—H14C	0.96
C1—C2	1.484 (3)	C15—H15A	0.96
C2—C3	1.374 (3)	C15—H15B	0.96
C2—C7	1.390 (3)	C15—H15C	0.96
C3—C4	1.373 (3)	C8D—C9D	1.39
C3—H3	0.93	C8D—C13D	1.39
C4—C5	1.376 (3)	C9D—C10D	1.39
C4—H4	0.93	C9D—C14D	1.538 (16)
C5—C6	1.361 (3)	C10D—C11D	1.39
C5—H5	0.93	C10D—C15D	1.523 (15)
C6—C7	1.372 (3)	C11D—C12D	1.39
C6—H6	0.93	C11D—H11D	0.93
C7—H7	0.93	C12D—C13D	1.39
C8—C9	1.361 (4)	C12D—H12D	0.93
C8—C13	1.426 (6)	C13D—H13D	0.93
C9—C10	1.412 (6)	C14D—H14D	0.96
C9—C14	1.497 (5)	C14D—H14E	0.96
C10—C11	1.379 (7)	C14D—H14F	0.96
C10—C15	1.499 (5)	C15D—H15D	0.96
C11—C12	1.353 (6)	C15D—H15E	0.96
C11—H11	0.93	C15D—H15F	0.96
C12—C13	1.361 (6)
C1—N1—C8	123.6 (2)	C10—C11—H11	117.9
C1—N1—C8D	113.0 (6)	C11—C12—C13	119.9 (4)
C1—N1—H1N	122.1 (14)	C11—C12—H12	120
C8—N1—H1N	108.8 (15)	C13—C12—H12	120
C8D—N1—H1N	124.2 (15)	C12—C13—C8	117.6 (4)
O1—C1—N1	122.11 (19)	C12—C13—H13	121.2
O1—C1—C2	120.35 (18)	C8—C13—H13	121.2
N1—C1—C2	117.54 (16)	C9D—C8D—C13D	120
C3—C2—C7	118.64 (19)	C9D—C8D—N1	112.4 (8)
C3—C2—C1	117.75 (17)	C13D—C8D—N1	127.6 (8)
C7—C2—C1	123.60 (18)	C10D—C9D—C8D	120
C4—C3—C2	121.16 (19)	C10D—C9D—C14D	114.9 (11)
C4—C3—H3	119.4	C8D—C9D—C14D	125.1 (11)
C2—C3—H3	119.4	C9D—C10D—C11D	120
C3—C4—C5	119.5 (2)	C9D—C10D—C15D	129.3 (10)
C3—C4—H4	120.3	C11D—C10D—C15D	110.7 (10)
C5—C4—H4	120.3	C12D—C11D—C10D	120
C6—C5—C4	120.0 (2)	C12D—C11D—H11D	120
C6—C5—H5	120	C10D—C11D—H11D	120
C4—C5—H5	120	C11D—C12D—C13D	120
C5—C6—C7	120.8 (2)	C11D—C12D—H12D	120
C5—C6—H6	119.6	C13D—C12D—H12D	120
C7—C6—H6	119.6	C12D—C13D—C8D	120
C6—C7—C2	119.9 (2)	C12D—C13D—H13D	120
C6—C7—H7	120.1	C8D—C13D—H13D	120
C2—C7—H7	120.1	C9D—C14D—H14D	109.5
C9—C8—N1	119.6 (4)	C9D—C14D—H14E	109.5
C9—C8—C13	122.0 (3)	H14D—C14D—H14E	109.5
N1—C8—C13	118.3 (3)	C9D—C14D—H14F	109.5
C8—C9—C10	119.1 (4)	H14D—C14D—H14F	109.5
C8—C9—C14	121.6 (4)	H14E—C14D—H14F	109.5
C10—C9—C14	119.2 (4)	C10D—C15D—H15D	109.5
C11—C10—C9	116.9 (4)	C10D—C15D—H15E	109.5
C11—C10—C15	121.8 (5)	H15D—C15D—H15E	109.5
C9—C10—C15	121.3 (4)	C10D—C15D—H15F	109.5
C12—C11—C10	124.2 (4)	H15D—C15D—H15F	109.5
C12—C11—H11	117.9	H15E—C15D—H15F	109.5
C8—N1—C1—O1	9.3 (4)	C8—C9—C10—C15	−175.3 (4)
C8D—N1—C1—O1	−10.7 (6)	C14—C9—C10—C15	5.9 (7)
C8—N1—C1—C2	−170.1 (3)	C9—C10—C11—C12	−0.4 (8)
C8D—N1—C1—C2	169.9 (6)	C15—C10—C11—C12	178.8 (6)
O1—C1—C2—C3	−22.5 (3)	C10—C11—C12—C13	−1.4 (9)
N1—C1—C2—C3	156.95 (19)	C11—C12—C13—C8	−0.4 (8)
O1—C1—C2—C7	157.7 (2)	C9—C8—C13—C12	4.0 (6)
N1—C1—C2—C7	−22.8 (3)	N1—C8—C13—C12	−176.6 (4)
C7—C2—C3—C4	0.9 (3)	C1—N1—C8D—C9D	122.9 (7)
C1—C2—C3—C4	−178.90 (19)	C8—N1—C8D—C9D	−2.8 (14)
C2—C3—C4—C5	−1.5 (3)	C1—N1—C8D—C13D	−55.9 (9)
C3—C4—C5—C6	0.6 (4)	C8—N1—C8D—C13D	178 (3)
C4—C5—C6—C7	0.8 (4)	C13D—C8D—C9D—C10D	0
C5—C6—C7—C2	−1.3 (4)	N1—C8D—C9D—C10D	−178.9 (12)
C3—C2—C7—C6	0.5 (3)	C13D—C8D—C9D—C14D	−179.0 (17)
C1—C2—C7—C6	−179.7 (2)	N1—C8D—C9D—C14D	2.1 (18)
C1—N1—C8—C9	−66.2 (4)	C8D—C9D—C10D—C11D	0
C8D—N1—C8—C9	−2.2 (18)	C14D—C9D—C10D—C11D	179.1 (15)
C1—N1—C8—C13	114.4 (4)	C8D—C9D—C10D—C15D	−179.8 (18)
C8D—N1—C8—C13	178 (2)	C14D—C9D—C10D—C15D	−0.7 (19)
N1—C8—C9—C10	174.8 (4)	C9D—C10D—C11D—C12D	0
C13—C8—C9—C10	−5.8 (6)	C15D—C10D—C11D—C12D	179.8 (15)
N1—C8—C9—C14	−6.4 (6)	C10D—C11D—C12D—C13D	0
C13—C8—C9—C14	173.0 (4)	C11D—C12D—C13D—C8D	0
C8—C9—C10—C11	3.9 (6)	C9D—C8D—C13D—C12D	0
C14—C9—C10—C11	−174.9 (4)	N1—C8D—C13D—C12D	178.7 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88 (2)	2.03 (2)	2.907 (2)	173 (2)
C14—H14C···N1	0.96	2.39	2.852 (4)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.883 (16)	2.028 (17)	2.907 (2)	173 (2)
C14—H14C⋯N1	0.96	2.39	2.852 (4)	109

Symmetry code: (i) .