N-Isopropyl-6-methyl-2-phenyl-quinoline-3-carboxamide.

In the title compound, C(20)H(20)N(2)O, the dihedral angle between the quinoline ring system and the phenyl ring is 49.40 (5)°. In the crystal structure, zigzag layers of mol-ecules, in which the quinoline units are parallel to the (10) plane, are arranged perpendicular to the b axis. Inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into chains along [010], reinforcing the cohesion between the layers of the structure.

Related literature

For our previous work on the preparation of quinoline deriv­atives, see: Benzerka et al. (2008 ▶); Ladraa et al. (2009 ▶); Bouraiou et al. (2006 ▶, 2008 ▶). For the evaluation of their biological activity, see: Atwell et al. (1988 ▶,1989 ▶); Denny et al. (1990 ▶); Toshima et al. (1999 ▶); Mikata et al. (1998 ▶); Henriksen et al. (1991 ▶). For the synthetic procedure, see: Saudi et al. (2003 ▶).

Experimental

Crystal data

C20H20N2O

M = 304.38

Orthorhombic,

a = 12.0007 (3) Å

b = 9.6314 (2) Å

c = 29.4627 (8) Å

V = 3405.40 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 150 K

0.32 × 0.11 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.747, T max = 0.994

15315 measured reflections

3906 independent reflections

2839 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.04

3906 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810031582/lh5101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031582/lh5101Isup2.hkl

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

C20H20N2O	F(000) = 1296
Mr = 304.38	Dx = 1.187 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4726 reflections
a = 12.0007 (3) Å	θ = 3.0–27.3°
b = 9.6314 (2) Å	µ = 0.07 mm−1
c = 29.4627 (8) Å	T = 150 K
V = 3405.40 (14) Å3	Stick, colourless
Z = 8	0.32 × 0.11 × 0.08 mm

Bruker APEXII diffractometer	2839 reflections with I > 2σ(I)
graphite	Rint = 0.046
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→15
Tmin = 0.747, Tmax = 0.994	k = −7→12
15315 measured reflections	l = −24→38
3906 independent reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0914P)2 + 0.3352P] where P = (Fo2 + 2Fc2)/3
3906 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 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
O1	0.29293 (9)	−0.22115 (10)	0.10660 (4)	0.0378 (3)
N1	0.58409 (10)	−0.43666 (12)	0.14988 (4)	0.0288 (3)
N2	0.21063 (10)	−0.43091 (12)	0.09977 (4)	0.0309 (3)
H2N	0.2211	−0.5213	0.0984	0.037*
C1	0.47981 (11)	−0.39345 (14)	0.14808 (5)	0.0258 (3)
C2	0.40933 (11)	−0.41975 (13)	0.10973 (5)	0.0240 (3)
C3	0.44903 (12)	−0.50023 (13)	0.07517 (5)	0.0249 (3)
H3	0.4038	−0.5201	0.0504	0.030*
C4	0.55847 (12)	−0.55334 (13)	0.07693 (4)	0.0251 (3)
C5	0.60463 (12)	−0.64177 (14)	0.04333 (5)	0.0289 (3)
H5	0.5619	−0.6654	0.0182	0.035*
C6	0.71088 (13)	−0.69338 (15)	0.04705 (5)	0.0335 (4)
C7	0.77548 (13)	−0.65292 (17)	0.08495 (6)	0.0352 (4)
H7	0.8477	−0.6870	0.0878	0.042*
C8	0.73505 (13)	−0.56529 (16)	0.11750 (5)	0.0332 (4)
H8	0.7805	−0.5384	0.1415	0.040*
C9	0.62453 (11)	−0.51521 (14)	0.11490 (5)	0.0266 (3)
C10	0.75887 (16)	−0.79114 (18)	0.01255 (6)	0.0448 (4)
H10A	0.7119	−0.7928	−0.0138	0.067*
H10B	0.7633	−0.8827	0.0253	0.067*
H10C	0.8321	−0.7604	0.0041	0.067*
C11	0.43566 (13)	−0.32106 (16)	0.18883 (5)	0.0328 (4)
C12	0.33582 (14)	−0.3632 (2)	0.20819 (6)	0.0464 (5)
H12	0.2956	−0.4352	0.1950	0.056*
C13	0.29535 (17)	−0.2991 (3)	0.24697 (7)	0.0681 (7)
H13	0.2292	−0.3291	0.2602	0.082*
C14	0.3541 (2)	−0.1903 (3)	0.26577 (8)	0.0792 (8)
H14	0.3264	−0.1452	0.2913	0.095*
C15	0.4537 (2)	−0.1480 (2)	0.24698 (7)	0.0690 (7)
H15	0.4928	−0.0746	0.2599	0.083*
C16	0.49557 (16)	−0.21433 (18)	0.20900 (6)	0.0454 (4)
H16	0.5639	−0.1874	0.1970	0.055*
C17	0.29824 (12)	−0.34913 (13)	0.10575 (5)	0.0258 (3)
C18	0.09700 (12)	−0.37692 (16)	0.09527 (6)	0.0395 (4)
H18	0.1017	−0.2852	0.0810	0.047*
C19	0.03298 (16)	−0.4717 (2)	0.06337 (11)	0.0859 (9)
H19A	0.0293	−0.5633	0.0762	0.129*
H19B	0.0703	−0.4755	0.0346	0.129*
H19C	−0.0411	−0.4363	0.0592	0.129*
C20	0.04341 (19)	−0.3592 (3)	0.14068 (8)	0.0850 (9)
H20A	0.0880	−0.2983	0.1590	0.128*
H20B	0.0374	−0.4479	0.1553	0.128*
H20C	−0.0296	−0.3201	0.1369	0.128*

	U11	U22	U33	U12	U13	U23
O1	0.0403 (7)	0.0158 (5)	0.0574 (7)	−0.0006 (4)	−0.0080 (5)	0.0015 (4)
N1	0.0269 (6)	0.0314 (6)	0.0281 (6)	−0.0029 (5)	0.0000 (5)	0.0012 (5)
N2	0.0234 (6)	0.0155 (5)	0.0539 (8)	0.0019 (5)	−0.0045 (6)	0.0033 (5)
C1	0.0264 (7)	0.0220 (6)	0.0290 (7)	−0.0029 (5)	−0.0008 (6)	0.0020 (5)
C2	0.0241 (7)	0.0167 (6)	0.0312 (7)	−0.0031 (5)	−0.0019 (6)	0.0030 (5)
C3	0.0287 (7)	0.0185 (6)	0.0276 (7)	−0.0038 (5)	−0.0045 (6)	0.0018 (5)
C4	0.0285 (7)	0.0194 (6)	0.0276 (7)	−0.0035 (6)	0.0024 (6)	0.0046 (5)
C5	0.0338 (8)	0.0236 (7)	0.0293 (7)	−0.0017 (6)	0.0025 (6)	0.0039 (6)
C6	0.0369 (9)	0.0269 (7)	0.0367 (8)	0.0015 (6)	0.0116 (7)	0.0071 (6)
C7	0.0260 (8)	0.0376 (8)	0.0421 (9)	0.0049 (6)	0.0069 (7)	0.0106 (7)
C8	0.0260 (8)	0.0407 (9)	0.0328 (8)	−0.0018 (6)	−0.0001 (6)	0.0064 (6)
C9	0.0260 (7)	0.0254 (7)	0.0283 (7)	−0.0030 (6)	0.0024 (6)	0.0066 (6)
C10	0.0501 (10)	0.0400 (9)	0.0444 (10)	0.0111 (8)	0.0159 (8)	0.0012 (8)
C11	0.0324 (8)	0.0356 (8)	0.0304 (8)	0.0071 (7)	−0.0068 (6)	−0.0031 (6)
C12	0.0364 (10)	0.0642 (12)	0.0387 (10)	0.0050 (8)	0.0019 (7)	−0.0107 (8)
C13	0.0471 (12)	0.112 (2)	0.0449 (11)	0.0199 (12)	0.0061 (9)	−0.0181 (12)
C14	0.0741 (16)	0.115 (2)	0.0487 (13)	0.0337 (15)	−0.0048 (12)	−0.0389 (13)
C15	0.0828 (17)	0.0685 (14)	0.0557 (13)	0.0135 (12)	−0.0237 (12)	−0.0327 (11)
C16	0.0486 (10)	0.0439 (10)	0.0437 (10)	0.0031 (8)	−0.0122 (8)	−0.0103 (8)
C17	0.0289 (8)	0.0179 (6)	0.0307 (7)	0.0003 (5)	−0.0024 (6)	0.0015 (5)
C18	0.0243 (8)	0.0248 (7)	0.0695 (11)	0.0047 (6)	−0.0029 (8)	0.0120 (7)
C19	0.0369 (11)	0.0361 (10)	0.185 (3)	0.0037 (8)	−0.0494 (14)	−0.0047 (14)
C20	0.0510 (13)	0.112 (2)	0.0926 (18)	0.0396 (13)	0.0298 (12)	0.0511 (16)

O1—C17	1.2346 (16)	C10—H10B	0.9600
N1—C1	1.3198 (18)	C10—H10C	0.9600
N1—C9	1.3676 (18)	C11—C12	1.388 (2)
N2—C17	1.3255 (18)	C11—C16	1.388 (2)
N2—C18	1.4654 (18)	C12—C13	1.387 (3)
N2—H2N	0.8800	C12—H12	0.9300
C1—C2	1.4339 (19)	C13—C14	1.379 (4)
C1—C11	1.486 (2)	C13—H13	0.9300
C2—C3	1.3656 (19)	C14—C15	1.378 (4)
C2—C17	1.5012 (19)	C14—H14	0.9300
C3—C4	1.4104 (19)	C15—C16	1.383 (3)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.4187 (19)	C16—H16	0.9300
C4—C9	1.419 (2)	C18—C20	1.494 (3)
C5—C6	1.373 (2)	C18—C19	1.519 (3)
C5—H5	0.9300	C18—H18	0.9800
C6—C7	1.414 (2)	C19—H19A	0.9600
C6—C10	1.501 (2)	C19—H19B	0.9600
C7—C8	1.366 (2)	C19—H19C	0.9600
C7—H7	0.9300	C20—H20A	0.9600
C8—C9	1.413 (2)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C10—H10A	0.9600
C1—N1—C9	118.72 (12)	C12—C11—C1	120.19 (14)
C17—N2—C18	122.63 (11)	C16—C11—C1	120.57 (15)
C17—N2—H2N	118.7	C13—C12—C11	120.73 (19)
C18—N2—H2N	118.7	C13—C12—H12	119.6
N1—C1—C2	122.37 (13)	C11—C12—H12	119.6
N1—C1—C11	116.96 (12)	C14—C13—C12	119.3 (2)
C2—C1—C11	120.61 (12)	C14—C13—H13	120.3
C3—C2—C1	118.81 (13)	C12—C13—H13	120.3
C3—C2—C17	120.58 (12)	C13—C14—C15	120.4 (2)
C1—C2—C17	120.36 (12)	C13—C14—H14	119.8
C2—C3—C4	120.22 (13)	C15—C14—H14	119.8
C2—C3—H3	119.9	C14—C15—C16	120.2 (2)
C4—C3—H3	119.9	C14—C15—H15	119.9
C3—C4—C5	123.75 (13)	C16—C15—H15	119.9
C3—C4—C9	117.09 (12)	C15—C16—C11	120.01 (19)
C5—C4—C9	119.16 (13)	C15—C16—H16	120.0
C6—C5—C4	121.61 (13)	C11—C16—H16	120.0
C6—C5—H5	119.2	O1—C17—N2	123.72 (13)
C4—C5—H5	119.2	O1—C17—C2	119.78 (12)
C5—C6—C7	118.20 (14)	N2—C17—C2	116.46 (11)
C5—C6—C10	121.96 (15)	N2—C18—C20	111.09 (14)
C7—C6—C10	119.83 (15)	N2—C18—C19	108.26 (13)
C8—C7—C6	121.98 (14)	C20—C18—C19	113.9 (2)
C8—C7—H7	119.0	N2—C18—H18	107.8
C6—C7—H7	119.0	C20—C18—H18	107.8
C7—C8—C9	120.40 (14)	C19—C18—H18	107.8
C7—C8—H8	119.8	C18—C19—H19A	109.5
C9—C8—H8	119.8	C18—C19—H19B	109.5
N1—C9—C8	118.75 (13)	H19A—C19—H19B	109.5
N1—C9—C4	122.61 (13)	C18—C19—H19C	109.5
C8—C9—C4	118.59 (13)	H19A—C19—H19C	109.5
C6—C10—H10A	109.5	H19B—C19—H19C	109.5
C6—C10—H10B	109.5	C18—C20—H20A	109.5
H10A—C10—H10B	109.5	C18—C20—H20B	109.5
C6—C10—H10C	109.5	H20A—C20—H20B	109.5
H10A—C10—H10C	109.5	C18—C20—H20C	109.5
H10B—C10—H10C	109.5	H20A—C20—H20C	109.5
C12—C11—C16	119.20 (16)	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.88	1.95	2.804 (3)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.88	1.95	2.804 (3)	164

Symmetry code: (i) .