2-Methyl-N-o-tolyl-benzamide.

In the title compound, C(15)H(15)NO, the C-N-C(O)-C amide unit is planar (r.m.s. deviation = 0.003 Å) and subtends dihedral angles of 44.71 (5) and 43.33 (5)° with the two o-tolyl rings. These aromatic rings are inclined at 4.94 (7)° to one another. The ortho-methyl groups of the two tolyl rings are anti to one another. In the crystal structure, N-H⋯O hydrogen bonds augmented by C-H⋯π inter-actions link the mol-ecules in a head-to-head fashion into chains along a. Independent chains pack in a herringbone pattern along c.

Related literature

For background to our work on benzamide derivatives, see: Saeed et al. (2008 ▶). For the 2-methyl-N-(3-methyl­phen­yl)benzamide isomer, see: Gowda et al. (2008b ▶). For other related structures see: Gowda et al. (2008a ▶,c ▶, 2009 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 4.9340 (4) Å

b = 23.639 (2) Å

c = 10.0228 (8) Å

β = 91.184 (4)°

V = 1168.75 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 89 K

0.59 × 0.23 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.762, T max = 1.000

19815 measured reflections

3831 independent reflections

3010 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.168

S = 1.09

3831 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050946/tk2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050946/tk2588Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.280 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4591 reflections
a = 4.9340 (4) Å	θ = 2.2–31.3°
b = 23.639 (2) Å	µ = 0.08 mm−1
c = 10.0228 (8) Å	T = 89 K
β = 91.184 (4)°	Triangular, colourless
V = 1168.75 (17) Å3	0.59 × 0.23 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3831 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
graphite	Rint = 0.064
ω scans	θmax = 31.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→7
Tmin = 0.762, Tmax = 1.000	k = −33→22
19815 measured reflections	l = −14→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0962P)2 + 0.1512P] where P = (Fo2 + 2Fc2)/3
3831 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.33 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
N1	−0.0409 (2)	0.11397 (4)	0.02480 (10)	0.0144 (2)
H1N	−0.2109	0.1224	0.0407	0.017*
C1	0.1521 (2)	0.13178 (5)	0.11331 (11)	0.0135 (2)
O1	0.39796 (17)	0.12286 (4)	0.09903 (9)	0.0201 (2)
C2	0.0510 (2)	0.16434 (5)	0.23088 (11)	0.0125 (2)
C3	0.1575 (2)	0.15349 (5)	0.35932 (12)	0.0132 (2)
C31	0.3642 (2)	0.10786 (5)	0.38777 (13)	0.0181 (3)
H31A	0.5405	0.1197	0.3542	0.027*
H31B	0.3072	0.0728	0.3433	0.027*
H31C	0.3791	0.1015	0.4843	0.027*
C4	0.0611 (2)	0.18607 (5)	0.46491 (12)	0.0173 (2)
H4	0.1289	0.1791	0.5528	0.021*
C5	−0.1310 (3)	0.22825 (5)	0.44439 (13)	0.0201 (3)
H5	−0.1926	0.2498	0.5177	0.024*
C6	−0.2333 (3)	0.23888 (5)	0.31665 (14)	0.0201 (3)
H6	−0.3640	0.2679	0.3021	0.024*
C7	−0.1427 (2)	0.20680 (5)	0.21060 (13)	0.0160 (2)
H7	−0.2131	0.2138	0.1232	0.019*
C8	0.0152 (2)	0.08234 (5)	−0.09270 (11)	0.0127 (2)
C9	−0.1221 (2)	0.09560 (5)	−0.21238 (12)	0.0132 (2)
C91	−0.3265 (2)	0.14277 (5)	−0.22165 (13)	0.0171 (2)
H91A	−0.3488	0.1547	−0.3149	0.026*
H91B	−0.2630	0.1749	−0.1676	0.026*
H91C	−0.5008	0.1295	−0.1885	0.026*
C10	−0.0626 (2)	0.06309 (5)	−0.32468 (12)	0.0175 (3)
H10	−0.1525	0.0713	−0.4072	0.021*
C11	0.1242 (3)	0.01915 (5)	−0.31890 (13)	0.0196 (3)
H11	0.1618	−0.0021	−0.3968	0.024*
C12	0.2556 (2)	0.00638 (5)	−0.19899 (12)	0.0175 (2)
H12	0.3828	−0.0238	−0.1945	0.021*
C13	0.2009 (2)	0.03771 (5)	−0.08573 (12)	0.0154 (2)
H13	0.2896	0.0288	−0.0034	0.018*

	U11	U22	U33	U12	U13	U23
N1	0.0129 (4)	0.0156 (5)	0.0146 (5)	0.0006 (3)	0.0006 (3)	−0.0028 (3)
C1	0.0161 (5)	0.0119 (5)	0.0125 (5)	−0.0027 (4)	0.0006 (4)	0.0005 (4)
O1	0.0119 (4)	0.0272 (5)	0.0213 (5)	0.0003 (3)	0.0014 (3)	−0.0051 (3)
C2	0.0118 (5)	0.0111 (5)	0.0147 (5)	−0.0022 (3)	0.0016 (4)	−0.0014 (4)
C3	0.0119 (5)	0.0124 (5)	0.0152 (5)	−0.0014 (4)	0.0011 (4)	−0.0016 (4)
C31	0.0164 (6)	0.0188 (5)	0.0192 (6)	0.0022 (4)	−0.0003 (4)	0.0010 (4)
C4	0.0177 (6)	0.0177 (6)	0.0164 (6)	−0.0020 (4)	0.0013 (4)	−0.0045 (4)
C5	0.0211 (6)	0.0157 (5)	0.0238 (6)	−0.0007 (4)	0.0061 (5)	−0.0082 (4)
C6	0.0173 (6)	0.0124 (5)	0.0307 (7)	0.0027 (4)	0.0027 (5)	−0.0023 (4)
C7	0.0141 (5)	0.0132 (5)	0.0208 (6)	−0.0011 (4)	−0.0014 (4)	0.0010 (4)
C8	0.0127 (5)	0.0123 (5)	0.0131 (5)	−0.0015 (4)	0.0019 (4)	−0.0005 (4)
C9	0.0114 (5)	0.0128 (5)	0.0153 (5)	−0.0007 (4)	0.0008 (4)	0.0001 (4)
C91	0.0150 (5)	0.0165 (5)	0.0197 (6)	0.0030 (4)	0.0002 (4)	0.0017 (4)
C10	0.0188 (6)	0.0194 (6)	0.0143 (5)	0.0016 (4)	−0.0021 (4)	−0.0022 (4)
C11	0.0227 (6)	0.0186 (6)	0.0178 (6)	0.0019 (4)	0.0020 (5)	−0.0059 (4)
C12	0.0166 (6)	0.0148 (5)	0.0211 (6)	0.0035 (4)	0.0014 (4)	−0.0012 (4)
C13	0.0147 (5)	0.0152 (5)	0.0162 (6)	0.0008 (4)	−0.0011 (4)	0.0005 (4)

N1—C1	1.3553 (15)	C6—H6	0.9500
N1—C8	1.4270 (14)	C7—H7	0.9500
N1—H1N	0.8800	C8—C13	1.3980 (16)
C1—O1	1.2423 (14)	C8—C9	1.4007 (16)
C1—C2	1.5013 (16)	C9—C10	1.3989 (16)
C2—C7	1.3979 (16)	C9—C91	1.5054 (16)
C2—C3	1.4040 (16)	C91—H91A	0.9800
C3—C4	1.4000 (16)	C91—H91B	0.9800
C3—C31	1.5074 (16)	C91—H91C	0.9800
C31—H31A	0.9800	C10—C11	1.3891 (17)
C31—H31B	0.9800	C10—H10	0.9500
C31—H31C	0.9800	C11—C12	1.3869 (18)
C4—C5	1.3881 (17)	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.3867 (17)
C5—C6	1.3893 (19)	C12—H12	0.9500
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.3872 (17)
C1—N1—C8	123.87 (10)	C6—C7—C2	120.75 (11)
C1—N1—H1N	118.1	C6—C7—H7	119.6
C8—N1—H1N	118.1	C2—C7—H7	119.6
O1—C1—N1	123.13 (11)	C13—C8—C9	121.08 (10)
O1—C1—C2	121.24 (10)	C13—C8—N1	119.50 (10)
N1—C1—C2	115.62 (10)	C9—C8—N1	119.40 (10)
C7—C2—C3	120.41 (10)	C10—C9—C8	117.42 (10)
C7—C2—C1	119.42 (10)	C10—C9—C91	120.57 (10)
C3—C2—C1	120.12 (10)	C8—C9—C91	122.01 (10)
C4—C3—C2	117.78 (10)	C9—C91—H91A	109.5
C4—C3—C31	119.32 (11)	C9—C91—H91B	109.5
C2—C3—C31	122.89 (10)	H91A—C91—H91B	109.5
C3—C31—H31A	109.5	C9—C91—H91C	109.5
C3—C31—H31B	109.5	H91A—C91—H91C	109.5
H31A—C31—H31B	109.5	H91B—C91—H91C	109.5
C3—C31—H31C	109.5	C11—C10—C9	121.81 (11)
H31A—C31—H31C	109.5	C11—C10—H10	119.1
H31B—C31—H31C	109.5	C9—C10—H10	119.1
C5—C4—C3	121.65 (12)	C12—C11—C10	119.79 (11)
C5—C4—H4	119.2	C12—C11—H11	120.1
C3—C4—H4	119.2	C10—C11—H11	120.1
C4—C5—C6	120.02 (11)	C11—C12—C13	119.84 (11)
C4—C5—H5	120.0	C11—C12—H12	120.1
C6—C5—H5	120.0	C13—C12—H12	120.1
C7—C6—C5	119.38 (11)	C12—C13—C8	120.05 (11)
C7—C6—H6	120.3	C12—C13—H13	120.0
C5—C6—H6	120.3	C8—C13—H13	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88	2.03	2.8891 (13)	166
C31—H31A···Cg1ii	0.98	2.76	3.6522 (12)	152
C91—H91C···Cg2i	0.98	2.83	3.6999 (12)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.88	2.03	2.8891 (13)	166
C31—H31A⋯Cg1ii	0.98	2.76	3.6522 (12)	152
C91—H91C⋯Cg2i	0.98	2.83	3.6999 (12)	148

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings.