N-[2,6-Bis(1-methyl-eth-yl)phen-yl]pyridine-4-carboxamide.

In the title compound, C(18)H(22)N(2)O, the dihedral angle between the benzene ring and the pyridine ring is 80.0 (1)°. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules into chains along the b axis. The packing also features C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π interactions, one directed to the benzene ring and the other to the center of the pyridine ring.

Related literature

For general review and synthetic details about amide bond generation and application, see: Pattabiraman & Bode (2011 ▶). The title compound has not been reported in coordination chemistry, but complexes of similar ligands are known. For the use of such ligands in coordination chemistry, see: Baytekin et al. (2009 ▶); Hasegawa et al. (2007 ▶); Kumar et al. (2004 ▶). For related benzamide crystal structures, see: Saeed et al. (2010 ▶); Zhang & Zhao (2010 ▶); Roopan et al. (2009 ▶); Gowda et al. (2008 ▶). For background to the synthetic route, see: Boeré et al. (1998 ▶); Krajete et al. (2004 ▶); Schafer et al. (2011 ▶); Wallace et al. (1990 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

n class="Chemical">C18H22N2O

M = 282.38

Monoclinic,

a = 9.0994 (1) Å

b = 9.8039 (1) Å

c = 18.1882 (2) Å

β = 96.8650 (4)°

V = 1610.93 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.57 mm−1

T = 150 K

0.20 × 0.12 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.895, T max = 0.935

81057 measured reflections

3126 independent reflections

3000 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.04

3126 reflections

198 parameters

n class="Disease">H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: UdMX (Maris, 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038846/nk2182sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038846/nk2182Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038846/nk2182Isup3.cml

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

C18H22N2O	F(000) = 608
Mr = 282.38	Dx = 1.164 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9664 reflections
a = 9.0994 (1) Å	θ = 4.9–70.9°
b = 9.8039 (1) Å	µ = 0.57 mm−1
c = 18.1882 (2) Å	T = 150 K
β = 96.8650 (4)°	Block, colourless
V = 1610.93 (3) Å3	0.20 × 0.12 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	3126 independent reflections
Radiation source: fine-focus sealed tube	3000 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 71.3°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.895, Tmax = 0.935	k = −11→12
81057 measured reflections	l = −22→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.483P] where P = (Fo2 + 2Fc2)/3
3126 reflections	(Δ/σ)max < 0.001
198 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 4 K Charged-Coupled Device (CCD) Area Detector using the program APEX2 and a Nonius FR591 rotating anode equiped with a Montel 200 optics The crystal-to-detector distance was 5.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over four different parts of the reciprocal space (132 frames total). One complete sphere of data was collected, to better than 0.80 Å resolution.

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
C1	0.56648 (10)	0.43259 (10)	0.26398 (5)	0.0201 (2)
C2	0.68103 (10)	0.39496 (10)	0.32743 (5)	0.0195 (2)
C3	0.70323 (11)	0.26362 (10)	0.35548 (5)	0.0225 (2)
H3	0.6495	0.1886	0.3328	0.027*
C4	0.80589 (11)	0.24503 (11)	0.41754 (6)	0.0256 (2)
H4	0.8212	0.1549	0.4361	0.031*
C5	0.86349 (11)	0.47088 (11)	0.42454 (6)	0.0258 (2)
H5	0.9188	0.5440	0.4483	0.031*
C6	0.76529 (11)	0.49972 (10)	0.36234 (6)	0.0236 (2)
H6	0.7556	0.5902	0.3437	0.028*
C7	0.35237 (11)	0.35774 (10)	0.18088 (5)	0.0215 (2)
C8	0.22392 (11)	0.40448 (11)	0.20807 (6)	0.0253 (2)
C9	0.09606 (12)	0.41663 (12)	0.15761 (6)	0.0308 (3)
H9	0.0067	0.4474	0.1743	0.037*
C10	0.09807 (12)	0.38435 (12)	0.08382 (6)	0.0322 (3)
H10	0.0099	0.3923	0.0504	0.039*
C11	0.22720 (13)	0.34047 (11)	0.05807 (6)	0.0295 (2)
H11	0.2270	0.3205	0.0069	0.035*
C12	0.35778 (12)	0.32520 (10)	0.10616 (6)	0.0247 (2)
C13	0.49893 (12)	0.26737 (11)	0.08127 (6)	0.0297 (2)
H13	0.5385	0.1989	0.1193	0.036*
C14	0.61908 (13)	0.37664 (13)	0.07854 (6)	0.0345 (3)
H14A	0.5906	0.4386	0.0370	0.052*
H14B	0.7133	0.3326	0.0719	0.052*
H14C	0.6301	0.4284	0.1250	0.052*
C15	0.47312 (15)	0.19216 (13)	0.00699 (7)	0.0406 (3)
H15A	0.3950	0.1239	0.0089	0.061*
H15B	0.5648	0.1468	−0.0027	0.061*
H15C	0.4431	0.2577	−0.0327	0.061*
C16	0.21896 (12)	0.43226 (12)	0.29009 (6)	0.0307 (3)
H16	0.3236	0.4405	0.3138	0.037*
C17	0.14987 (15)	0.31045 (14)	0.32582 (7)	0.0400 (3)
H17A	0.0468	0.2997	0.3040	0.060*
H17B	0.1532	0.3261	0.3792	0.060*
H17C	0.2054	0.2275	0.3172	0.060*
C18	0.14025 (15)	0.56513 (13)	0.30479 (7)	0.0404 (3)
H18A	0.1874	0.6410	0.2815	0.061*
H18B	0.1467	0.5807	0.3583	0.061*
H18C	0.0360	0.5590	0.2840	0.061*
N1	0.48109 (9)	0.33206 (9)	0.23309 (5)	0.02100 (19)
H20	0.4927 (15)	0.2479 (16)	0.2480 (8)	0.034 (3)*
N2	0.88469 (10)	0.34533 (9)	0.45299 (5)	0.0264 (2)
O1	0.55121 (8)	0.55210 (7)	0.24345 (4)	0.02682 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0212 (5)	0.0163 (5)	0.0221 (5)	0.0015 (4)	0.0004 (4)	−0.0016 (4)
C2	0.0191 (4)	0.0190 (5)	0.0201 (5)	0.0019 (4)	0.0011 (4)	−0.0017 (4)
C3	0.0256 (5)	0.0185 (5)	0.0228 (5)	−0.0001 (4)	0.0000 (4)	−0.0015 (4)
C4	0.0301 (5)	0.0213 (5)	0.0244 (5)	0.0025 (4)	−0.0011 (4)	0.0021 (4)
C5	0.0250 (5)	0.0240 (5)	0.0270 (5)	−0.0004 (4)	−0.0032 (4)	−0.0042 (4)
C6	0.0240 (5)	0.0182 (5)	0.0275 (5)	0.0010 (4)	−0.0015 (4)	−0.0013 (4)
C7	0.0236 (5)	0.0148 (4)	0.0243 (5)	−0.0028 (4)	−0.0043 (4)	0.0012 (4)
C8	0.0244 (5)	0.0222 (5)	0.0281 (5)	−0.0029 (4)	−0.0020 (4)	0.0003 (4)
C9	0.0232 (5)	0.0303 (6)	0.0371 (6)	−0.0009 (4)	−0.0038 (4)	0.0014 (5)
C10	0.0305 (5)	0.0279 (6)	0.0341 (6)	−0.0044 (4)	−0.0126 (4)	0.0042 (4)
C11	0.0404 (6)	0.0224 (5)	0.0231 (5)	−0.0049 (4)	−0.0067 (4)	0.0011 (4)
C12	0.0323 (5)	0.0162 (5)	0.0247 (5)	−0.0032 (4)	−0.0007 (4)	0.0014 (4)
C13	0.0370 (6)	0.0247 (5)	0.0277 (5)	0.0010 (4)	0.0044 (4)	0.0005 (4)
C14	0.0360 (6)	0.0361 (6)	0.0317 (6)	−0.0025 (5)	0.0051 (5)	−0.0008 (5)
C15	0.0519 (7)	0.0347 (7)	0.0369 (6)	−0.0063 (6)	0.0126 (5)	−0.0088 (5)
C16	0.0240 (5)	0.0382 (6)	0.0294 (6)	−0.0007 (4)	0.0007 (4)	−0.0035 (5)
C17	0.0483 (7)	0.0395 (7)	0.0326 (6)	0.0046 (6)	0.0063 (5)	0.0054 (5)
C18	0.0472 (7)	0.0360 (7)	0.0402 (7)	−0.0020 (5)	0.0144 (5)	−0.0038 (5)
N1	0.0231 (4)	0.0146 (4)	0.0236 (4)	−0.0002 (3)	−0.0040 (3)	0.0009 (3)
N2	0.0271 (4)	0.0266 (5)	0.0241 (4)	0.0023 (4)	−0.0030 (3)	−0.0008 (3)
O1	0.0308 (4)	0.0150 (4)	0.0317 (4)	0.0002 (3)	−0.0081 (3)	0.0008 (3)

C1—O1	1.2325 (12)	C11—C12	1.3968 (15)
C1—N1	1.3366 (13)	C11—H11	0.9500
C1—C2	1.5057 (13)	C12—C13	1.5215 (15)
C2—C6	1.3891 (14)	C13—C15	1.5324 (16)
C2—C3	1.3908 (14)	C13—C14	1.5357 (16)
C3—C4	1.3885 (14)	C13—H13	1.0000
C3—H3	0.9500	C14—H14A	0.9800
C4—N2	1.3364 (14)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—N2	1.3402 (14)	C15—H15A	0.9800
C5—C6	1.3845 (14)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800
C6—H6	0.9500	C16—C18	1.5256 (17)
C7—C8	1.3996 (15)	C16—C17	1.5302 (17)
C7—C12	1.4025 (14)	C16—H16	1.0000
C7—N1	1.4392 (12)	C17—H17A	0.9800
C8—C9	1.3981 (14)	C17—H17B	0.9800
C8—C16	1.5224 (15)	C17—H17C	0.9800
C9—C10	1.3812 (17)	C18—H18A	0.9800
C9—H9	0.9500	C18—H18B	0.9800
C10—C11	1.3844 (17)	C18—H18C	0.9800
C10—H10	0.9500	N1—H20	0.872 (16)
O1—C1—N1	122.33 (9)	C15—C13—C14	109.99 (9)
O1—C1—C2	120.52 (9)	C12—C13—H13	107.0
N1—C1—C2	117.12 (8)	C15—C13—H13	107.0
C6—C2—C3	117.96 (9)	C14—C13—H13	107.0
C6—C2—C1	117.57 (9)	C13—C14—H14A	109.5
C3—C2—C1	124.40 (9)	C13—C14—H14B	109.5
C4—C3—C2	118.28 (9)	H14A—C14—H14B	109.5
C4—C3—H3	120.9	C13—C14—H14C	109.5
C2—C3—H3	120.9	H14A—C14—H14C	109.5
N2—C4—C3	124.45 (9)	H14B—C14—H14C	109.5
N2—C4—H4	117.8	C13—C15—H15A	109.5
C3—C4—H4	117.8	C13—C15—H15B	109.5
N2—C5—C6	123.51 (10)	H15A—C15—H15B	109.5
N2—C5—H5	118.2	C13—C15—H15C	109.5
C6—C5—H5	118.2	H15A—C15—H15C	109.5
C5—C6—C2	119.31 (9)	H15B—C15—H15C	109.5
C5—C6—H6	120.3	C8—C16—C18	113.21 (10)
C2—C6—H6	120.3	C8—C16—C17	109.78 (10)
C8—C7—C12	122.98 (9)	C18—C16—C17	111.51 (10)
C8—C7—N1	118.18 (9)	C8—C16—H16	107.4
C12—C7—N1	118.65 (9)	C18—C16—H16	107.4
C9—C8—C7	117.42 (10)	C17—C16—H16	107.4
C9—C8—C16	120.54 (10)	C16—C17—H17A	109.5
C7—C8—C16	121.91 (9)	C16—C17—H17B	109.5
C10—C9—C8	120.78 (10)	H17A—C17—H17B	109.5
C10—C9—H9	119.6	C16—C17—H17C	109.5
C8—C9—H9	119.6	H17A—C17—H17C	109.5
C9—C10—C11	120.68 (10)	H17B—C17—H17C	109.5
C9—C10—H10	119.7	C16—C18—H18A	109.5
C11—C10—H10	119.7	C16—C18—H18B	109.5
C10—C11—C12	120.95 (10)	H18A—C18—H18B	109.5
C10—C11—H11	119.5	C16—C18—H18C	109.5
C12—C11—H11	119.5	H18A—C18—H18C	109.5
C11—C12—C7	117.17 (10)	H18B—C18—H18C	109.5
C11—C12—C13	122.60 (10)	C1—N1—C7	122.32 (8)
C7—C12—C13	120.11 (9)	C1—N1—H20	121.6 (9)
C12—C13—C15	113.31 (10)	C7—N1—H20	115.5 (9)
C12—C13—C14	112.29 (9)	C4—N2—C5	116.45 (9)
O1—C1—C2—C6	1.35 (14)	C10—C11—C12—C13	175.36 (10)
N1—C1—C2—C6	−176.83 (9)	C8—C7—C12—C11	−0.33 (15)
O1—C1—C2—C3	178.24 (9)	N1—C7—C12—C11	174.69 (9)
N1—C1—C2—C3	0.05 (14)	C8—C7—C12—C13	−176.56 (9)
C6—C2—C3—C4	1.29 (14)	N1—C7—C12—C13	−1.54 (14)
C1—C2—C3—C4	−175.58 (9)	C11—C12—C13—C15	−16.18 (15)
C2—C3—C4—N2	0.63 (16)	C7—C12—C13—C15	159.84 (10)
N2—C5—C6—C2	1.24 (16)	C11—C12—C13—C14	109.19 (11)
C3—C2—C6—C5	−2.17 (15)	C7—C12—C13—C14	−74.79 (12)
C1—C2—C6—C5	174.92 (9)	C9—C8—C16—C18	−48.05 (14)
C12—C7—C8—C9	0.93 (15)	C7—C8—C16—C18	136.15 (11)
N1—C7—C8—C9	−174.12 (9)	C9—C8—C16—C17	77.27 (13)
C12—C7—C8—C16	176.85 (10)	C7—C8—C16—C17	−98.53 (12)
N1—C7—C8—C16	1.81 (15)	O1—C1—N1—C7	−8.80 (15)
C7—C8—C9—C10	−0.44 (16)	C2—C1—N1—C7	169.34 (8)
C16—C8—C9—C10	−176.43 (10)	C8—C7—N1—C1	−76.45 (12)
C8—C9—C10—C11	−0.62 (17)	C12—C7—N1—C1	108.28 (11)
C9—C10—C11—C12	1.25 (17)	C3—C4—N2—C5	−1.59 (16)
C10—C11—C12—C7	−0.76 (15)	C6—C5—N2—C4	0.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H20···O1i	0.872 (16)	1.970 (16)	2.7985 (11)	158.3 (13)
C3—H3···O1i	0.95	2.54	3.4500 (12)	161
C5—H5···N2ii	0.95	2.61	3.4983 (13)	155
C6—H6···Cg1iii	0.95	2.81	3.6467	150
C15—H15B···Cg2iv	0.98	2.97	3.7858	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the phenyl and pyridyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H20⋯O1i	0.872 (16)	1.970 (16)	2.7985 (11)	158.3 (13)
C3—H3⋯O1i	0.95	2.54	3.4500 (12)	161
C5—H5⋯N2ii	0.95	2.61	3.4983 (13)	155
C6—H6⋯Cg1iii	0.95	2.81	3.6467	150
C15—H15B⋯Cg2iv	0.98	2.97	3.7858	143

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