5-(4-Methyl-phen-yl)-2,3-diphenyl-5,6-dihydro-imidazo[1,2-c]quinazoline.

In the title compound, C(29)H(23)N(3), the pyrimidine ring adopts an envelope conformation. The dihedral angle between the phenyl rings attached to the pyrimidine-ring double bond is 62.09 (7)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming extended chains in the c-axis direction.

Related literature

For background to quinazolines, see: Blackman et al. (1987 ▶); Billimora & Cava (1994 ▶); Helissey et al. (1994 ▶); Brana et al. (1994 ▶); Riou et al. (1991 ▶); Ibrahim et al. (1988 ▶); Shi et al. (1993 ▶, 2003 ▶); McMurry (1983 ▶). For ttypical Csp 2—N bond distances, see: Lorente et al. (1995 ▶).

Experimental

Crystal data

C29H23N3

M = 413.50

Monoclinic,

a = 16.006 (4) Å

b = 11.382 (3) Å

c = 11.906 (3) Å

β = 91.810 (4)°

V = 2167.8 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.44 × 0.42 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.976

11276 measured reflections

3819 independent reflections

2071 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 0.95

3819 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038961/vm2044sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038961/vm2044Isup2.hkl

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

C29H23N3	F(000) = 872
Mr = 413.50	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2039 reflections
a = 16.006 (4) Å	θ = 2.6–23.2°
b = 11.382 (3) Å	µ = 0.08 mm−1
c = 11.906 (3) Å	T = 298 K
β = 91.810 (4)°	Block, yellow
V = 2167.8 (10) Å3	0.44 × 0.42 × 0.33 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3819 independent reflections
Radiation source: fine-focus sealed tube	2071 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
Tmin = 0.968, Tmax = 0.976	k = −10→13
11276 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.8501P] where P = (Fo2 + 2Fc2)/3
3819 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 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	0.14553 (14)	0.83172 (18)	0.85068 (18)	0.0517 (6)
H1A	0.1495	0.8943	0.8910	0.062*
N2	0.21849 (13)	0.69225 (17)	0.74512 (16)	0.0418 (5)
N3	0.16675 (13)	0.59511 (17)	0.59709 (16)	0.0429 (5)
C1	0.21383 (16)	0.7487 (2)	0.8563 (2)	0.0442 (6)
H1	0.2657	0.7927	0.8704	0.053*
C2	0.28310 (15)	0.6234 (2)	0.7078 (2)	0.0421 (6)
C3	0.24973 (16)	0.5649 (2)	0.6166 (2)	0.0423 (6)
C4	0.15000 (16)	0.6717 (2)	0.67723 (19)	0.0405 (6)
C5	0.07381 (16)	0.7354 (2)	0.6952 (2)	0.0422 (6)
C6	0.00388 (17)	0.7246 (2)	0.6248 (2)	0.0513 (7)
H6	0.0039	0.6710	0.5658	0.062*
C7	−0.06578 (18)	0.7928 (3)	0.6415 (3)	0.0618 (8)
H7	−0.1127	0.7855	0.5939	0.074*
C8	−0.06544 (19)	0.8721 (3)	0.7295 (3)	0.0640 (8)
H8	−0.1124	0.9181	0.7407	0.077*
C9	0.00313 (19)	0.8838 (2)	0.8003 (2)	0.0576 (8)
H9	0.0024	0.9371	0.8594	0.069*
C10	0.07411 (17)	0.8157 (2)	0.7839 (2)	0.0455 (7)
C11	0.20700 (16)	0.6564 (2)	0.9477 (2)	0.0435 (6)
C12	0.13376 (18)	0.5960 (2)	0.9621 (2)	0.0557 (7)
H12	0.0878	0.6108	0.9144	0.067*
C13	0.1277 (2)	0.5138 (2)	1.0465 (2)	0.0653 (8)
H13	0.0775	0.4742	1.0552	0.078*
C14	0.1946 (2)	0.4892 (2)	1.1179 (2)	0.0602 (8)
C15	0.2675 (2)	0.5504 (3)	1.1031 (2)	0.0650 (8)
H15	0.3134	0.5355	1.1508	0.078*
C16	0.27413 (18)	0.6330 (2)	1.0196 (2)	0.0557 (7)
H16	0.3242	0.6732	1.0116	0.067*
C17	0.1870 (3)	0.4005 (3)	1.2109 (3)	0.0974 (13)
H17A	0.1699	0.4394	1.2779	0.146*
H17B	0.2401	0.3631	1.2249	0.146*
H17C	0.1461	0.3424	1.1890	0.146*
C18	0.36672 (16)	0.6215 (2)	0.7620 (2)	0.0451 (6)
C19	0.41102 (18)	0.7239 (3)	0.7841 (2)	0.0558 (7)
H19	0.3885	0.7957	0.7613	0.067*
C20	0.48788 (19)	0.7208 (3)	0.8393 (3)	0.0666 (9)
H20	0.5163	0.7904	0.8552	0.080*
C21	0.5223 (2)	0.6158 (3)	0.8708 (3)	0.0735 (10)
H21	0.5742	0.6137	0.9083	0.088*
C22	0.48048 (19)	0.5135 (3)	0.8470 (3)	0.0669 (9)
H22	0.5046	0.4419	0.8673	0.080*
C23	0.40312 (17)	0.5155 (3)	0.7934 (2)	0.0559 (7)
H23	0.3751	0.4454	0.7781	0.067*
C24	0.29181 (16)	0.4794 (2)	0.5439 (2)	0.0442 (6)
C25	0.25755 (18)	0.3695 (2)	0.5252 (2)	0.0576 (8)
H25	0.2068	0.3504	0.5563	0.069*
C26	0.2981 (2)	0.2877 (3)	0.4605 (3)	0.0681 (9)
H26	0.2755	0.2131	0.4501	0.082*
C27	0.3716 (2)	0.3166 (3)	0.4118 (3)	0.0672 (9)
H27	0.3985	0.2619	0.3677	0.081*
C28	0.40545 (19)	0.4259 (3)	0.4280 (2)	0.0649 (8)
H28	0.4551	0.4457	0.3942	0.078*
C29	0.36592 (17)	0.5066 (2)	0.4945 (2)	0.0551 (7)
H29	0.3897	0.5804	0.5061	0.066*

	U11	U22	U33	U12	U13	U23
N1	0.0703 (16)	0.0421 (13)	0.0425 (13)	0.0085 (11)	0.0006 (12)	−0.0063 (10)
N2	0.0491 (13)	0.0440 (12)	0.0324 (11)	0.0006 (10)	0.0024 (10)	0.0010 (9)
N3	0.0507 (14)	0.0441 (12)	0.0340 (12)	0.0021 (10)	0.0050 (10)	0.0018 (10)
C1	0.0535 (16)	0.0445 (15)	0.0346 (14)	−0.0002 (12)	0.0033 (12)	−0.0062 (11)
C2	0.0477 (15)	0.0454 (15)	0.0334 (14)	0.0028 (12)	0.0050 (12)	0.0000 (12)
C3	0.0496 (16)	0.0445 (15)	0.0329 (14)	0.0021 (12)	0.0036 (12)	0.0033 (11)
C4	0.0503 (16)	0.0407 (14)	0.0305 (13)	−0.0015 (12)	0.0033 (12)	0.0042 (11)
C5	0.0512 (16)	0.0418 (15)	0.0339 (14)	0.0035 (12)	0.0053 (12)	0.0050 (11)
C6	0.0566 (18)	0.0525 (17)	0.0451 (16)	0.0021 (14)	0.0042 (14)	0.0006 (13)
C7	0.0556 (19)	0.068 (2)	0.062 (2)	0.0059 (15)	−0.0002 (15)	0.0038 (16)
C8	0.063 (2)	0.064 (2)	0.066 (2)	0.0167 (16)	0.0109 (17)	0.0087 (17)
C9	0.075 (2)	0.0488 (17)	0.0493 (17)	0.0156 (15)	0.0106 (16)	0.0018 (13)
C10	0.0578 (17)	0.0447 (16)	0.0344 (14)	0.0039 (13)	0.0066 (13)	0.0068 (12)
C11	0.0543 (17)	0.0443 (15)	0.0320 (14)	0.0011 (13)	0.0039 (12)	−0.0035 (11)
C12	0.0635 (19)	0.0603 (19)	0.0433 (16)	−0.0044 (15)	0.0001 (14)	0.0024 (14)
C13	0.086 (2)	0.0592 (19)	0.0513 (18)	−0.0121 (16)	0.0100 (17)	0.0038 (15)
C14	0.094 (2)	0.0461 (17)	0.0404 (17)	0.0115 (17)	0.0076 (17)	0.0023 (13)
C15	0.081 (2)	0.067 (2)	0.0462 (18)	0.0185 (18)	−0.0051 (16)	0.0047 (15)
C16	0.0615 (19)	0.0587 (18)	0.0466 (17)	0.0031 (14)	−0.0012 (14)	−0.0018 (14)
C17	0.170 (4)	0.064 (2)	0.060 (2)	0.014 (2)	0.019 (2)	0.0197 (17)
C18	0.0500 (16)	0.0529 (17)	0.0327 (14)	0.0012 (13)	0.0044 (12)	0.0007 (12)
C19	0.0572 (18)	0.0603 (19)	0.0500 (17)	−0.0040 (15)	0.0028 (14)	0.0028 (14)
C20	0.057 (2)	0.081 (2)	0.062 (2)	−0.0118 (17)	0.0015 (16)	−0.0113 (17)
C21	0.0548 (19)	0.104 (3)	0.061 (2)	0.008 (2)	−0.0094 (16)	−0.0104 (19)
C22	0.064 (2)	0.075 (2)	0.061 (2)	0.0153 (17)	−0.0085 (16)	−0.0006 (17)
C23	0.0582 (19)	0.0602 (19)	0.0491 (17)	0.0064 (15)	−0.0012 (14)	−0.0014 (14)
C24	0.0511 (16)	0.0485 (16)	0.0329 (14)	0.0051 (13)	0.0009 (12)	0.0003 (12)
C25	0.0598 (18)	0.0563 (18)	0.0571 (18)	−0.0021 (14)	0.0085 (15)	−0.0087 (14)
C26	0.078 (2)	0.0559 (19)	0.071 (2)	0.0020 (16)	0.0070 (19)	−0.0143 (16)
C27	0.070 (2)	0.072 (2)	0.059 (2)	0.0176 (18)	0.0056 (17)	−0.0183 (16)
C28	0.0555 (18)	0.082 (2)	0.0580 (19)	0.0029 (17)	0.0165 (15)	−0.0093 (17)
C29	0.0583 (19)	0.0591 (18)	0.0484 (17)	−0.0034 (14)	0.0104 (15)	−0.0071 (14)

N1—C10	1.384 (3)	C14—C15	1.374 (4)
N1—C1	1.445 (3)	C14—C17	1.506 (4)
N1—H1A	0.8600	C15—C16	1.375 (4)
N2—C4	1.362 (3)	C15—H15	0.9300
N2—C2	1.382 (3)	C16—H16	0.9300
N2—C1	1.475 (3)	C17—H17A	0.9600
N3—C4	1.326 (3)	C17—H17B	0.9600
N3—C3	1.384 (3)	C17—H17C	0.9600
C1—C11	1.519 (3)	C18—C23	1.387 (3)
C1—H1	0.9800	C18—C19	1.385 (4)
C2—C3	1.368 (3)	C19—C20	1.377 (4)
C2—C18	1.468 (3)	C19—H19	0.9300
C3—C24	1.478 (3)	C20—C21	1.365 (4)
C4—C5	1.440 (3)	C20—H20	0.9300
C5—C6	1.383 (3)	C21—C22	1.368 (4)
C5—C10	1.396 (3)	C21—H21	0.9300
C6—C7	1.378 (4)	C22—C23	1.375 (4)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.382 (4)	C23—H23	0.9300
C7—H7	0.9300	C24—C29	1.376 (3)
C8—C9	1.369 (4)	C24—C25	1.381 (4)
C8—H8	0.9300	C25—C26	1.384 (4)
C9—C10	1.394 (4)	C25—H25	0.9300
C9—H9	0.9300	C26—C27	1.366 (4)
C11—C12	1.374 (4)	C26—H26	0.9300
C11—C16	1.379 (3)	C27—C28	1.368 (4)
C12—C13	1.379 (4)	C27—H27	0.9300
C12—H12	0.9300	C28—C29	1.380 (4)
C13—C14	1.374 (4)	C28—H28	0.9300
C13—H13	0.9300	C29—H29	0.9300
C10—N1—C1	123.4 (2)	C15—C14—C17	121.5 (3)
C10—N1—H1A	118.3	C13—C14—C17	120.8 (3)
C1—N1—H1A	118.3	C14—C15—C16	121.6 (3)
C4—N2—C2	108.0 (2)	C14—C15—H15	119.2
C4—N2—C1	123.0 (2)	C16—C15—H15	119.2
C2—N2—C1	126.5 (2)	C15—C16—C11	120.3 (3)
C4—N3—C3	104.9 (2)	C15—C16—H16	119.8
N1—C1—N2	107.7 (2)	C11—C16—H16	119.8
N1—C1—C11	114.4 (2)	C14—C17—H17A	109.5
N2—C1—C11	110.40 (19)	C14—C17—H17B	109.5
N1—C1—H1	108.1	H17A—C17—H17B	109.5
N2—C1—H1	108.1	C14—C17—H17C	109.5
C11—C1—H1	108.1	H17A—C17—H17C	109.5
C3—C2—N2	104.7 (2)	H17B—C17—H17C	109.5
C3—C2—C18	132.0 (2)	C23—C18—C19	118.2 (3)
N2—C2—C18	123.2 (2)	C23—C18—C2	120.0 (2)
C2—C3—N3	111.1 (2)	C19—C18—C2	121.7 (2)
C2—C3—C24	127.7 (2)	C20—C19—C18	120.9 (3)
N3—C3—C24	121.2 (2)	C20—C19—H19	119.5
N3—C4—N2	111.3 (2)	C18—C19—H19	119.5
N3—C4—C5	129.0 (2)	C21—C20—C19	120.0 (3)
N2—C4—C5	119.7 (2)	C21—C20—H20	120.0
C6—C5—C10	120.0 (2)	C19—C20—H20	120.0
C6—C5—C4	122.5 (2)	C22—C21—C20	119.9 (3)
C10—C5—C4	117.4 (2)	C22—C21—H21	120.1
C7—C6—C5	120.4 (3)	C20—C21—H21	120.1
C7—C6—H6	119.8	C21—C22—C23	120.7 (3)
C5—C6—H6	119.8	C21—C22—H22	119.7
C6—C7—C8	119.5 (3)	C23—C22—H22	119.7
C6—C7—H7	120.2	C22—C23—C18	120.2 (3)
C8—C7—H7	120.2	C22—C23—H23	119.9
C9—C8—C7	120.9 (3)	C18—C23—H23	119.9
C9—C8—H8	119.5	C29—C24—C25	118.6 (2)
C7—C8—H8	119.5	C29—C24—C3	121.1 (2)
C8—C9—C10	120.0 (3)	C25—C24—C3	120.3 (2)
C8—C9—H9	120.0	C24—C25—C26	120.6 (3)
C10—C9—H9	120.0	C24—C25—H25	119.7
N1—C10—C5	120.2 (2)	C26—C25—H25	119.7
N1—C10—C9	120.6 (2)	C27—C26—C25	119.9 (3)
C5—C10—C9	119.1 (3)	C27—C26—H26	120.0
C12—C11—C16	118.5 (2)	C25—C26—H26	120.0
C12—C11—C1	121.1 (2)	C26—C27—C28	120.1 (3)
C16—C11—C1	120.4 (2)	C26—C27—H27	119.9
C11—C12—C13	120.6 (3)	C28—C27—H27	119.9
C11—C12—H12	119.7	C27—C28—C29	120.0 (3)
C13—C12—H12	119.7	C27—C28—H28	120.0
C14—C13—C12	121.2 (3)	C29—C28—H28	120.0
C14—C13—H13	119.4	C24—C29—C28	120.8 (3)
C12—C13—H13	119.4	C24—C29—H29	119.6
C15—C14—C13	117.7 (3)	C28—C29—H29	119.6
C10—N1—C1—N2	31.9 (3)	N1—C1—C11—C12	47.4 (3)
C10—N1—C1—C11	−91.3 (3)	N2—C1—C11—C12	−74.2 (3)
C4—N2—C1—N1	−32.5 (3)	N1—C1—C11—C16	−131.4 (3)
C2—N2—C1—N1	167.7 (2)	N2—C1—C11—C16	106.9 (3)
C4—N2—C1—C11	93.1 (3)	C16—C11—C12—C13	−0.1 (4)
C2—N2—C1—C11	−66.8 (3)	C1—C11—C12—C13	−179.0 (2)
C4—N2—C2—C3	0.7 (3)	C11—C12—C13—C14	−0.5 (4)
C1—N2—C2—C3	163.1 (2)	C12—C13—C14—C15	0.7 (4)
C4—N2—C2—C18	−179.2 (2)	C12—C13—C14—C17	179.1 (3)
C1—N2—C2—C18	−16.9 (4)	C13—C14—C15—C16	−0.4 (4)
N2—C2—C3—N3	−0.3 (3)	C17—C14—C15—C16	−178.8 (3)
C18—C2—C3—N3	179.7 (2)	C14—C15—C16—C11	−0.2 (4)
N2—C2—C3—C24	179.8 (2)	C12—C11—C16—C15	0.4 (4)
C18—C2—C3—C24	−0.3 (5)	C1—C11—C16—C15	179.3 (2)
C4—N3—C3—C2	−0.3 (3)	C3—C2—C18—C23	−52.0 (4)
C4—N3—C3—C24	179.7 (2)	N2—C2—C18—C23	127.9 (3)
C3—N3—C4—N2	0.8 (3)	C3—C2—C18—C19	128.5 (3)
C3—N3—C4—C5	177.5 (2)	N2—C2—C18—C19	−51.6 (4)
C2—N2—C4—N3	−1.0 (3)	C23—C18—C19—C20	−2.3 (4)
C1—N2—C4—N3	−164.1 (2)	C2—C18—C19—C20	177.2 (2)
C2—N2—C4—C5	−178.0 (2)	C18—C19—C20—C21	1.5 (4)
C1—N2—C4—C5	18.9 (3)	C19—C20—C21—C22	0.2 (5)
N3—C4—C5—C6	−0.9 (4)	C20—C21—C22—C23	−1.2 (5)
N2—C4—C5—C6	175.5 (2)	C21—C22—C23—C18	0.4 (5)
N3—C4—C5—C10	−177.0 (2)	C19—C18—C23—C22	1.3 (4)
N2—C4—C5—C10	−0.5 (3)	C2—C18—C23—C22	−178.2 (3)
C10—C5—C6—C7	0.0 (4)	C2—C3—C24—C29	−53.1 (4)
C4—C5—C6—C7	−176.0 (2)	N3—C3—C24—C29	127.0 (3)
C5—C6—C7—C8	−0.1 (4)	C2—C3—C24—C25	126.2 (3)
C6—C7—C8—C9	−0.1 (4)	N3—C3—C24—C25	−53.7 (3)
C7—C8—C9—C10	0.4 (4)	C29—C24—C25—C26	1.7 (4)
C1—N1—C10—C5	−17.9 (4)	C3—C24—C25—C26	−177.7 (3)
C1—N1—C10—C9	165.5 (2)	C24—C25—C26—C27	−1.9 (4)
C6—C5—C10—N1	−176.3 (2)	C25—C26—C27—C28	0.7 (5)
C4—C5—C10—N1	−0.2 (3)	C26—C27—C28—C29	0.7 (5)
C6—C5—C10—C9	0.4 (4)	C25—C24—C29—C28	−0.2 (4)
C4—C5—C10—C9	176.5 (2)	C3—C24—C29—C28	179.1 (2)
C8—C9—C10—N1	176.1 (2)	C27—C28—C29—C24	−0.9 (4)
C8—C9—C10—C5	−0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3i	0.86	2.46	3.058 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3i	0.86	2.46	3.058 (3)	127

Symmetry code: (i) .