2-Methyl-N-p-tolyl-benzamide: a second monoclinic polymorph.

The title compound, C(15)H(15)NO, (I), is a polymorph of the structure (II) reported by Gowda et al. [Acta Cryst. (2008), E64, o1494]. Compound (II) crystalllizes in the space group C2/c (Z = 8), whereas the title compound occurs in space group P2(1)/c (Z = 4). The two mol-ecular structures differ slightly in the relative orientations of their central amide group with respect to the benzoyl ring [dihedral angles of 55.99 (7) for (I) and 59.96 (11)° for (II)] and in the inclination of the benzoyl and aniline rings [88.67 (8) for (I) and 81.44 (5)° for (II)]. In the crystal structure of (I), mol-ecules are linked by N-H⋯O hydrogen bonds, forming C(4) chains, which are augmented by weak C-H⋯O inter-actions. The structure is further stabilized by C-H⋯π contacts involving both of the aromatic rings.

Related literature

For the biological activity of N-substituted benzamides, see: Olsson et al. (2002 ▶); Lindgren et al. (2001 ▶). For the use of heterocyclic analogs of benzanilide derivatives as potassium channel activators, see: Calderone et al. (2006 ▶). For the use of 2-nitro­benzamides in organic synthesis, see: Zhichkin et al. (2007 ▶); Beccalli et al. (2005 ▶). For the original monoclinic polymorph, see: Gowda et al. (2008 ▶). For the related N-(2,4-dimethyl­phen­yl)-2-methyl­benzamide, see: Gowda et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 20.259 (3) Å

b = 7.0681 (10) Å

c = 8.7941 (13) Å

β = 95.942 (9)°

V = 1252.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 89 K

0.30 × 0.19 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.803, T max = 1.000

8447 measured reflections

1283 independent reflections

1028 reflections with I > 2σ(I)

R int = 0.052

θmax = 20.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.108

S = 1.07

1283 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.23 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 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010378/hb5364sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010378/hb5364Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.195 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1469 reflections
a = 20.259 (3) Å	θ = 3.1–20.2°
b = 7.0681 (10) Å	µ = 0.08 mm−1
c = 8.7941 (13) Å	T = 89 K
β = 95.942 (9)°	Rectangular plate, colourless
V = 1252.5 (3) Å3	0.30 × 0.19 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	1283 independent reflections
Radiation source: fine-focus sealed tube	1028 reflections with I > 2σ(I)
graphite	Rint = 0.052
ω scans	θmax = 20.7°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −20→20
Tmin = 0.803, Tmax = 1.000	k = −7→7
8447 measured reflections	l = −8→8

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.3937P] where P = (Fo2 + 2Fc2)/3
1283 reflections	(Δ/σ)max = 0.002
159 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.73575 (10)	0.2686 (3)	0.6898 (2)	0.0250 (6)
H1N	0.7455 (11)	0.297 (3)	0.789 (3)	0.030*
O1	0.76424 (8)	0.0912 (2)	0.48978 (19)	0.0301 (5)
C1	0.77164 (12)	0.1340 (3)	0.6268 (3)	0.0231 (7)
C2	0.82221 (12)	0.0392 (3)	0.7367 (3)	0.0207 (7)
C3	0.88871 (13)	0.0342 (3)	0.7074 (3)	0.0232 (7)
C31	0.91234 (13)	0.1250 (4)	0.5675 (3)	0.0327 (7)
H31A	0.8943	0.0557	0.4760	0.049*
H31B	0.9609	0.1217	0.5753	0.049*
H31C	0.8972	0.2567	0.5602	0.049*
C4	0.93384 (13)	−0.0562 (3)	0.8148 (3)	0.0269 (7)
H4	0.9795	−0.0597	0.7988	0.032*
C5	0.91342 (14)	−0.1405 (3)	0.9437 (3)	0.0302 (7)
H5	0.9450	−0.2013	1.0149	0.036*
C6	0.84744 (13)	−0.1368 (3)	0.9697 (3)	0.0285 (7)
H6	0.8334	−0.1961	1.0579	0.034*
C7	0.80182 (12)	−0.0460 (3)	0.8663 (3)	0.0239 (7)
H7	0.7564	−0.0419	0.8840	0.029*
C8	0.68730 (12)	0.3892 (4)	0.6124 (3)	0.0230 (7)
C9	0.68482 (12)	0.5755 (4)	0.6619 (3)	0.0278 (7)
H9	0.7146	0.6179	0.7455	0.033*
C10	0.63886 (13)	0.6993 (4)	0.5893 (3)	0.0330 (7)
H10	0.6381	0.8270	0.6228	0.040*
C11	0.59398 (13)	0.6409 (4)	0.4687 (3)	0.0327 (8)
C111	0.54250 (14)	0.7756 (4)	0.3928 (3)	0.0466 (9)
H11A	0.5237	0.7223	0.2949	0.070*
H11B	0.5634	0.8975	0.3751	0.070*
H11C	0.5071	0.7939	0.4594	0.070*
C12	0.59739 (13)	0.4542 (4)	0.4208 (3)	0.0345 (8)
H12	0.5677	0.4116	0.3370	0.041*
C13	0.64310 (12)	0.3286 (4)	0.4923 (3)	0.0285 (7)
H13	0.6440	0.2009	0.4588	0.034*

	U11	U22	U33	U12	U13	U23
N1	0.0360 (14)	0.0248 (14)	0.0135 (12)	0.0036 (11)	−0.0006 (11)	−0.0010 (11)
O1	0.0457 (12)	0.0259 (11)	0.0182 (12)	0.0017 (9)	0.0006 (9)	−0.0010 (8)
C1	0.0349 (17)	0.0173 (16)	0.0170 (17)	−0.0079 (13)	0.0029 (13)	−0.0008 (12)
C2	0.0319 (17)	0.0133 (14)	0.0163 (15)	0.0013 (12)	−0.0004 (13)	−0.0022 (12)
C3	0.0354 (18)	0.0108 (14)	0.0232 (16)	0.0002 (12)	0.0020 (13)	−0.0042 (12)
C31	0.0396 (17)	0.0253 (17)	0.0341 (17)	−0.0008 (13)	0.0079 (13)	0.0024 (13)
C4	0.0317 (16)	0.0177 (16)	0.0309 (18)	0.0009 (12)	0.0015 (13)	−0.0073 (13)
C5	0.042 (2)	0.0206 (16)	0.0259 (18)	0.0066 (13)	−0.0043 (14)	−0.0010 (13)
C6	0.046 (2)	0.0204 (16)	0.0196 (16)	0.0028 (13)	0.0045 (14)	0.0034 (12)
C7	0.0310 (16)	0.0193 (15)	0.0214 (16)	0.0020 (12)	0.0018 (13)	−0.0006 (12)
C8	0.0278 (15)	0.0261 (17)	0.0154 (15)	0.0022 (13)	0.0034 (13)	0.0045 (13)
C9	0.0325 (16)	0.0289 (18)	0.0217 (16)	0.0044 (13)	0.0020 (13)	−0.0007 (13)
C10	0.0418 (18)	0.0284 (17)	0.0299 (17)	0.0083 (14)	0.0088 (15)	0.0023 (14)
C11	0.0317 (17)	0.040 (2)	0.0267 (17)	0.0069 (14)	0.0062 (14)	0.0112 (14)
C111	0.0442 (19)	0.054 (2)	0.0430 (19)	0.0141 (16)	0.0079 (15)	0.0182 (16)
C12	0.0324 (17)	0.043 (2)	0.0271 (17)	−0.0043 (14)	−0.0004 (13)	0.0054 (14)
C13	0.0330 (16)	0.0273 (17)	0.0252 (17)	−0.0013 (14)	0.0020 (14)	0.0045 (13)

N1—C1	1.351 (3)	C6—H6	0.9500
N1—C8	1.420 (3)	C7—H7	0.9500
N1—H1N	0.90 (3)	C8—C13	1.380 (3)
O1—C1	1.236 (3)	C8—C9	1.389 (3)
C1—C2	1.493 (3)	C9—C10	1.385 (3)
C2—C7	1.389 (3)	C9—H9	0.9500
C2—C3	1.398 (3)	C10—C11	1.387 (4)
C3—C4	1.399 (3)	C10—H10	0.9500
C3—C31	1.509 (4)	C11—C12	1.389 (4)
C31—H31A	0.9800	C11—C111	1.515 (4)
C31—H31B	0.9800	C111—H11A	0.9800
C31—H31C	0.9800	C111—H11B	0.9800
C4—C5	1.381 (4)	C111—H11C	0.9800
C4—H4	0.9500	C12—C13	1.386 (4)
C5—C6	1.380 (4)	C12—H12	0.9500
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.386 (3)
C1—N1—C8	126.9 (2)	C6—C7—C2	120.3 (2)
C1—N1—H1N	118.9 (16)	C6—C7—H7	119.8
C8—N1—H1N	113.8 (16)	C2—C7—H7	119.8
O1—C1—N1	123.8 (2)	C13—C8—C9	119.5 (2)
O1—C1—C2	121.8 (2)	C13—C8—N1	122.8 (2)
N1—C1—C2	114.4 (2)	C9—C8—N1	117.7 (2)
C7—C2—C3	121.0 (2)	C10—C9—C8	119.9 (2)
C7—C2—C1	118.9 (2)	C10—C9—H9	120.0
C3—C2—C1	120.1 (2)	C8—C9—H9	120.0
C2—C3—C4	117.5 (2)	C9—C10—C11	121.4 (3)
C2—C3—C31	122.2 (2)	C9—C10—H10	119.3
C4—C3—C31	120.3 (2)	C11—C10—H10	119.3
C3—C31—H31A	109.5	C10—C11—C12	117.8 (2)
C3—C31—H31B	109.5	C10—C11—C111	121.1 (3)
H31A—C31—H31B	109.5	C12—C11—C111	121.1 (3)
C3—C31—H31C	109.5	C11—C111—H11A	109.5
H31A—C31—H31C	109.5	C11—C111—H11B	109.5
H31B—C31—H31C	109.5	H11A—C111—H11B	109.5
C5—C4—C3	121.4 (2)	C11—C111—H11C	109.5
C5—C4—H4	119.3	H11A—C111—H11C	109.5
C3—C4—H4	119.3	H11B—C111—H11C	109.5
C6—C5—C4	120.4 (2)	C13—C12—C11	121.5 (2)
C6—C5—H5	119.8	C13—C12—H12	119.2
C4—C5—H5	119.8	C11—C12—H12	119.2
C5—C6—C7	119.4 (2)	C8—C13—C12	119.9 (3)
C5—C6—H6	120.3	C8—C13—H13	120.0
C7—C6—H6	120.3	C12—C13—H13	120.0
C8—N1—C1—O1	−3.8 (4)	C3—C2—C7—C6	0.4 (3)
C8—N1—C1—C2	175.9 (2)	C1—C2—C7—C6	179.3 (2)
O1—C1—C2—C7	−124.6 (3)	C1—N1—C8—C13	38.7 (4)
N1—C1—C2—C7	55.7 (3)	C1—N1—C8—C9	−141.7 (2)
O1—C1—C2—C3	54.3 (3)	C13—C8—C9—C10	−0.9 (4)
N1—C1—C2—C3	−125.4 (2)	N1—C8—C9—C10	179.4 (2)
C7—C2—C3—C4	−1.3 (3)	C8—C9—C10—C11	1.1 (4)
C1—C2—C3—C4	179.8 (2)	C9—C10—C11—C12	−1.2 (4)
C7—C2—C3—C31	179.9 (2)	C9—C10—C11—C111	178.2 (2)
C1—C2—C3—C31	1.0 (3)	C10—C11—C12—C13	1.2 (4)
C2—C3—C4—C5	1.1 (3)	C111—C11—C12—C13	−178.1 (2)
C31—C3—C4—C5	−180.0 (2)	C9—C8—C13—C12	1.0 (4)
C3—C4—C5—C6	−0.2 (4)	N1—C8—C13—C12	−179.4 (2)
C4—C5—C6—C7	−0.7 (4)	C11—C12—C13—C8	−1.1 (4)
C5—C6—C7—C2	0.6 (4)

Cg1 and Cg2 are the centroids of the C3–C7 and C8–C13 benzene rings, repectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.90 (3)	1.94 (3)	2.821 (3)	169 (2)
C9—H9···O1i	0.95	2.71	3.366 (3)	127
C7—H7···Cg2ii	0.95	2.84	3.751 (3)	160
C31—H31C···Cg1iii	0.98	2.86	3.676 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C7 and C8–C13 benzene rings, repectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.90 (3)	1.94 (3)	2.821 (3)	169 (2)
C9—H9⋯O1i	0.95	2.71	3.366 (3)	127
C7—H7⋯Cg2ii	0.95	2.84	3.751 (3)	160
C31—H31C⋯Cg1iii	0.98	2.86	3.676 (3)	141

Symmetry codes: (i) ; (ii) ; (iii) .