N-(3,4-Dimethyl-phen-yl)benzamide.

The conformation of the NH bond in the structure of the title compound (N34DMPBA), C(15)H(15)NO, is anti to the meta-methyl substituent in the aniline ring, similar to that observed with respect to the meta-chloro substituent in N-(3,4-dichloro-phen-yl)benzamide (N34DCPBA), but in contrast to the syn conformation observed with respect to the meta-methyl substituent in N-(3,4-dimethyl-phen-yl)acetamide. The bond parameters in N34DMPBA are similar to those in N34DCPBA and other benzanilides. The mol-ecules in N34DMPBA are packed into a column-like structure in the direction of the a axis through N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda, Foro & Fuess (2007 ▶); Gowda et al. (2003 ▶); Gowda, Sowmya et al. (2007 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Orthorhombic,

a = 9.1082 (2) Å

b = 9.8123 (2) Å

c = 28.5126 (8) Å

V = 2548.24 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.33 × 0.11 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: none

21605 measured reflections

2527 independent reflections

1448 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.194

S = 0.97

2527 reflections

159 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.19 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, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); 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/S1600536807066937/dn2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066937/dn2302Isup2.hkl

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

C15H15NO	F000 = 960
Mr = 225.28	Dx = 1.174 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6829 reflections
a = 9.1082 (2) Å	θ = 3.0–29.5º
b = 9.8123 (2) Å	µ = 0.07 mm−1
c = 28.5126 (8) Å	T = 295 (2) K
V = 2548.24 (10) Å3	Prism, colourless
Z = 8	0.33 × 0.11 × 0.08 mm

Oxford Diffraction Xcalibur System diffractometer	2527 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1448 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 10.4340 pixels mm-1	θmax = 26.2º
T = 295(2) K	θmin = 5.1º
ω scans with κ offsets	h = −11→9
Absorption correction: none	k = −12→12
21605 measured reflections	l = −32→35

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.1315P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2527 reflections	Δρmax = 0.37 e Å−3
159 parameters	Δρmin = −0.18 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1	0.1683 (2)	0.51852 (17)	0.15178 (7)	0.0543 (5)
C2	0.04493 (19)	0.58368 (18)	0.17772 (7)	0.0526 (5)
C3	−0.0315 (2)	0.5050 (2)	0.21000 (8)	0.0651 (6)
H3	−0.0063	0.4139	0.2141	0.078*
C4	−0.1439 (3)	0.5599 (2)	0.23587 (9)	0.0762 (7)
H4	−0.1931	0.5068	0.2578	0.091*
C5	−0.1835 (3)	0.6937 (2)	0.22926 (9)	0.0766 (7)
H5	−0.2602	0.7307	0.2466	0.092*
C6	−0.1109 (2)	0.7724 (2)	0.19736 (9)	0.0724 (7)
H6	−0.1384	0.8627	0.1929	0.087*
C7	0.0038 (2)	0.71760 (19)	0.17159 (8)	0.0608 (6)
H7	0.0534	0.7717	0.1500	0.073*
C8	0.4041 (2)	0.55741 (19)	0.11157 (8)	0.0631 (6)
C9	0.4082 (3)	0.4574 (2)	0.07867 (8)	0.0728 (7)
H9	0.3209	0.4171	0.0690	0.087*
C10	0.5432 (3)	0.4126 (2)	0.05859 (8)	0.0762 (7)
C11	0.6702 (3)	0.4749 (2)	0.07412 (9)	0.0804 (7)
C12	0.6653 (3)	0.5762 (3)	0.10680 (10)	0.0874 (8)
H12	0.7520	0.6175	0.1165	0.105*
C13	0.5336 (2)	0.6185 (3)	0.12574 (10)	0.0751 (7)
H13	0.5319	0.6878	0.1480	0.090*
C14	0.8200 (4)	0.4325 (3)	0.05424 (14)	0.1195 (12)
H14A	0.8943	0.4939	0.0655	0.179*
H14B	0.8169	0.4358	0.0206	0.179*
H14C	0.8426	0.3415	0.0642	0.179*
C15	0.5398 (4)	0.3011 (3)	0.02331 (12)	0.1179 (11)
H15A	0.6176	0.3142	0.0010	0.177*
H15B	0.4471	0.3020	0.0073	0.177*
H15C	0.5525	0.2150	0.0388	0.177*
N1	0.26924 (19)	0.60131 (17)	0.13237 (7)	0.0614 (5)
H1N	0.268 (2)	0.685 (2)	0.1389 (8)	0.074*
O1	0.17788 (16)	0.39356 (13)	0.14930 (6)	0.0777 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0539 (11)	0.0379 (10)	0.0710 (13)	−0.0013 (8)	−0.0095 (9)	0.0014 (8)
C2	0.0473 (11)	0.0428 (11)	0.0677 (13)	−0.0043 (7)	−0.0114 (9)	0.0008 (8)
C3	0.0660 (14)	0.0438 (11)	0.0854 (15)	−0.0053 (9)	−0.0009 (11)	0.0047 (10)
C4	0.0789 (16)	0.0630 (14)	0.0869 (16)	−0.0100 (11)	0.0189 (13)	0.0031 (11)
C5	0.0701 (15)	0.0670 (15)	0.0927 (17)	0.0000 (11)	0.0149 (12)	−0.0082 (12)
C6	0.0709 (14)	0.0501 (11)	0.0963 (16)	0.0082 (10)	0.0072 (13)	−0.0006 (11)
C7	0.0604 (12)	0.0439 (11)	0.0781 (14)	−0.0018 (9)	0.0001 (10)	0.0058 (10)
C8	0.0752 (15)	0.0450 (11)	0.0692 (13)	0.0032 (10)	0.0047 (11)	0.0064 (10)
C9	0.0859 (17)	0.0577 (13)	0.0748 (14)	−0.0017 (11)	−0.0030 (12)	0.0058 (11)
C10	0.107 (2)	0.0519 (13)	0.0697 (15)	0.0122 (12)	0.0034 (13)	0.0056 (11)
C11	0.0936 (19)	0.0621 (14)	0.0855 (16)	0.0091 (12)	0.0067 (14)	0.0044 (12)
C12	0.0704 (16)	0.0881 (17)	0.1036 (19)	0.0007 (13)	0.0041 (14)	−0.0054 (15)
C13	0.0639 (14)	0.0710 (15)	0.0903 (17)	−0.0011 (11)	0.0054 (12)	−0.0065 (12)
C14	0.106 (2)	0.108 (2)	0.145 (3)	0.0300 (18)	0.039 (2)	0.0006 (19)
C15	0.174 (3)	0.085 (2)	0.095 (2)	0.0096 (18)	0.011 (2)	−0.0201 (16)
N1	0.0628 (11)	0.0394 (9)	0.0821 (12)	0.0001 (8)	0.0098 (9)	−0.0019 (8)
O1	0.0706 (10)	0.0401 (9)	0.1224 (14)	0.0007 (6)	0.0090 (9)	0.0026 (8)

C1—O1	1.231 (2)	C9—C10	1.425 (4)
C1—N1	1.346 (2)	C9—H9	0.9300
C1—C2	1.490 (3)	C10—C11	1.382 (4)
C2—C7	1.377 (3)	C10—C15	1.487 (4)
C2—C3	1.389 (3)	C11—C12	1.363 (4)
C3—C4	1.372 (3)	C11—C14	1.535 (4)
C3—H3	0.9300	C12—C13	1.379 (4)
C4—C5	1.374 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.364 (3)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.386 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C9	1.358 (3)	C15—H15C	0.9600
C8—C13	1.384 (3)	N1—H1N	0.84 (2)
C8—N1	1.430 (3)
O1—C1—N1	121.96 (18)	C11—C10—C9	117.2 (2)
O1—C1—C2	120.61 (17)	C11—C10—C15	124.1 (3)
N1—C1—C2	117.41 (15)	C9—C10—C15	118.7 (3)
C7—C2—C3	118.57 (18)	C12—C11—C10	120.9 (2)
C7—C2—C1	123.48 (17)	C12—C11—C14	118.6 (3)
C3—C2—C1	117.95 (16)	C10—C11—C14	120.4 (3)
C4—C3—C2	120.78 (19)	C11—C12—C13	121.0 (2)
C4—C3—H3	119.6	C11—C12—H12	119.5
C2—C3—H3	119.6	C13—C12—H12	119.5
C3—C4—C5	119.8 (2)	C12—C13—C8	119.8 (2)
C3—C4—H4	120.1	C12—C13—H13	120.1
C5—C4—H4	120.1	C8—C13—H13	120.1
C6—C5—C4	120.3 (2)	C11—C14—H14A	109.5
C6—C5—H5	119.8	C11—C14—H14B	109.5
C4—C5—H5	119.8	H14A—C14—H14B	109.5
C5—C6—C7	120.0 (2)	C11—C14—H14C	109.5
C5—C6—H6	120.0	H14A—C14—H14C	109.5
C7—C6—H6	120.0	H14B—C14—H14C	109.5
C2—C7—C6	120.50 (19)	C10—C15—H15A	109.5
C2—C7—H7	119.7	C10—C15—H15B	109.5
C6—C7—H7	119.7	H15A—C15—H15B	109.5
C9—C8—C13	119.4 (2)	C10—C15—H15C	109.5
C9—C8—N1	121.9 (2)	H15A—C15—H15C	109.5
C13—C8—N1	118.7 (2)	H15B—C15—H15C	109.5
C8—C9—C10	121.6 (2)	C1—N1—C8	125.11 (16)
C8—C9—H9	119.2	C1—N1—H1N	119.4 (16)
C10—C9—H9	119.2	C8—N1—H1N	113.3 (16)
O1—C1—C2—C7	−161.5 (2)	C8—C9—C10—C15	179.0 (2)
N1—C1—C2—C7	19.9 (3)	C9—C10—C11—C12	−0.9 (4)
O1—C1—C2—C3	19.0 (3)	C15—C10—C11—C12	−179.6 (2)
N1—C1—C2—C3	−159.59 (19)	C9—C10—C11—C14	180.0 (2)
C7—C2—C3—C4	−1.2 (3)	C15—C10—C11—C14	1.3 (4)
C1—C2—C3—C4	178.3 (2)	C10—C11—C12—C13	0.8 (4)
C2—C3—C4—C5	1.3 (4)	C14—C11—C12—C13	179.9 (3)
C3—C4—C5—C6	−0.5 (4)	C11—C12—C13—C8	0.1 (4)
C4—C5—C6—C7	−0.3 (4)	C9—C8—C13—C12	−0.7 (3)
C3—C2—C7—C6	0.4 (3)	N1—C8—C13—C12	178.9 (2)
C1—C2—C7—C6	−179.1 (2)	O1—C1—N1—C8	−7.0 (3)
C5—C6—C7—C2	0.3 (3)	C2—C1—N1—C8	171.52 (18)
C13—C8—C9—C10	0.6 (3)	C9—C8—N1—C1	51.0 (3)
N1—C8—C9—C10	−179.02 (19)	C13—C8—N1—C1	−128.6 (2)
C8—C9—C10—C11	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.12 (2)	2.948 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.12 (2)	2.948 (2)	165 (2)

Symmetry code: (i) .