2-(4-Chloro-phen-yl)-4-phenyl-1,2-di-hydro-quinazoline.

In the title compound, C20H15ClN2, the pyrimidine ring is in a flattened half-chair conformation. The phenyl and chloro-substituted benzene rings form dihedral angles of 84.97 (5) and 80.23 (4)°, respectively, with the benzene ring of the di-hydro-quinazoline group. The dihedral angle between the phenyl and chloro-substituted benzene rings is 61.71 (5)°. In the crystal, mol-ecules are arranged in inter-secting layers parallel to (101) and (-102), with N-H⋯N hydrogen bonds linking mol-ecules along [010]. In addition, a weak C-H⋯π inter-action is observed.

Related literature

For the preparation and applications of quinazoline derivatives, see: Gundla et al. (2008 ▶); Luth & Lowe (2008 ▶); Fry et al. (1994 ▶); Kunes et al. (2000 ▶); Michael (2002 ▶); Frère et al. (2003 ▶); Langer & Bodtke (2003 ▶).

Experimental

Crystal data

C20H15ClN2

M = 318.79

Monoclinic,

a = 9.2563 (10) Å

b = 10.6283 (11) Å

c = 17.6230 (19) Å

β = 116.775 (7)°

V = 1547.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.18 × 0.04 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.948, T max = 1.000

8914 measured reflections

2724 independent reflections

2462 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.05

2724 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); 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, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813027839/lh5660sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027839/lh5660Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027839/lh5660Isup3.cml

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

C20H15ClN2	F(000) = 664
Mr = 318.79	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4726 reflections
a = 9.2563 (10) Å	θ = 2.5–25.1°
b = 10.6283 (11) Å	µ = 0.25 mm−1
c = 17.6230 (19) Å	T = 150 K
β = 116.775 (7)°	Needle, colourless
V = 1547.8 (3) Å3	0.18 × 0.04 × 0.03 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→11
Tmin = 0.948, Tmax = 1.000	k = −12→12
8914 measured reflections	l = −17→21
2724 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.033P)2 + 0.9522P] where P = (Fo2 + 2Fc2)/3
2724 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. Spectroscopic data: IR (KBr) ν 3320, 2364 1620, 1537, 1486, 1321, 1263, 1155, 1015, 964, 805, 741, 697 cm-1; 1H NMR (CDCl3, 400 MHz) δ 7.72–7.61 (m, 5H, arom.), 7.49–7.36 (m, 4H, arom.), 7.32–7.21 (m, 2H, arom.), 6.77 (td, J=8.0,1.0 Hz, 1H, arom.), 6.72 (d, J=8.0 Hz, 1H), 6.02 (s, 1H, CH), 4.38 (s, 1H, NH); 13 C NMR (CDCl3, 100 MHz) δ 165.8, 146.9, 141.5, 141.4, 140.9, 138.1, 132.9, 130.2, 129.4, 129.3, 129.1, 128.1, 127.8, 127.5, 127.3, 127.2, 118.3, 117.9, 114.3, 72.4. Anal. calcd for C20H15N2Cl: C, 75.35; H, 4.74; N, 8.79; Found: C, 75.75; H, 4.95; N, 9.42. HRMS calcd for C20H16N2Cl (MH+) 319.0924; found 319.0863.

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	0.53121 (17)	0.77886 (14)	0.50548 (10)	0.0165 (3)
C2	0.44580 (18)	0.66972 (14)	0.49960 (9)	0.0168 (3)
H2	0.4841	0.6114	0.5437	0.02*
C3	0.30186 (17)	0.64835 (14)	0.42695 (10)	0.0153 (3)
H3	0.244	0.5748	0.4223	0.018*
C4	0.24323 (17)	0.73546 (13)	0.36111 (9)	0.0130 (3)
C5	0.33457 (18)	0.84305 (14)	0.36800 (10)	0.0161 (3)
H5	0.2981	0.9009	0.3237	0.019*
C6	0.47870 (18)	0.86503 (14)	0.43980 (10)	0.0177 (3)
H6	0.5393	0.9367	0.4438	0.021*
C7	0.07957 (17)	0.71954 (13)	0.28323 (9)	0.0131 (3)
H7	0.0982	0.72	0.2327	0.016*
C8	−0.10527 (16)	0.82529 (13)	0.31836 (9)	0.0124 (3)
C9	−0.18848 (17)	0.94230 (13)	0.32554 (9)	0.0129 (3)
C10	−0.35237 (19)	0.96183 (15)	0.27479 (11)	0.0239 (4)
H10	−0.4123	0.903	0.2334	0.029*
C11	−0.42727 (19)	1.06843 (15)	0.28539 (11)	0.0258 (4)
H11	−0.5367	1.0821	0.2503	0.031*
C12	−0.33965 (19)	1.15455 (14)	0.34810 (10)	0.0208 (3)
H12	−0.3906	1.2252	0.356	0.025*
C13	−0.1764 (2)	1.13562 (15)	0.39897 (10)	0.0228 (4)
H13	−0.1174	1.1936	0.4412	0.027*
C14	−0.10031 (18)	1.03001 (14)	0.38718 (10)	0.0188 (3)
H14	0.0101	1.0182	0.4208	0.023*
C15	−0.08004 (16)	0.59670 (13)	0.33333 (9)	0.0119 (3)
C16	−0.12929 (16)	0.70970 (13)	0.35624 (9)	0.0129 (3)
C17	−0.20595 (17)	0.70602 (14)	0.40861 (9)	0.0160 (3)
H17	−0.2382	0.7806	0.424	0.019*
C18	−0.23427 (18)	0.59305 (14)	0.43764 (10)	0.0180 (3)
H18	−0.2842	0.5913	0.4731	0.022*
C19	−0.18758 (18)	0.48132 (14)	0.41355 (10)	0.0171 (3)
H19	−0.2075	0.405	0.4329	0.021*
C20	−0.11248 (17)	0.48210 (13)	0.36158 (9)	0.0140 (3)
H20	−0.0834	0.4068	0.3453	0.017*
N1	−0.00529 (14)	0.60480 (12)	0.28194 (8)	0.0135 (3)
N2	−0.01662 (14)	0.83324 (11)	0.27983 (7)	0.0129 (3)
Cl1	0.70928 (4)	0.80771 (4)	0.59784 (2)	0.02398 (13)
H1N	0.018 (2)	0.5377 (18)	0.2660 (11)	0.023 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0120 (7)	0.0221 (8)	0.0148 (7)	0.0023 (6)	0.0053 (6)	−0.0041 (6)
C2	0.0180 (7)	0.0189 (8)	0.0154 (7)	0.0047 (6)	0.0093 (6)	0.0039 (6)
C3	0.0161 (7)	0.0135 (7)	0.0193 (8)	0.0010 (6)	0.0107 (6)	0.0008 (6)
C4	0.0143 (7)	0.0136 (7)	0.0146 (7)	0.0027 (5)	0.0095 (6)	−0.0015 (5)
C5	0.0191 (8)	0.0151 (7)	0.0161 (7)	0.0019 (6)	0.0095 (6)	0.0024 (6)
C6	0.0168 (8)	0.0150 (7)	0.0221 (8)	−0.0014 (6)	0.0096 (6)	−0.0028 (6)
C7	0.0158 (7)	0.0122 (7)	0.0137 (7)	0.0001 (5)	0.0088 (6)	0.0001 (5)
C8	0.0122 (7)	0.0127 (7)	0.0098 (7)	−0.0014 (5)	0.0027 (6)	−0.0017 (5)
C9	0.0166 (7)	0.0106 (7)	0.0137 (7)	0.0001 (5)	0.0090 (6)	0.0029 (5)
C10	0.0194 (8)	0.0181 (8)	0.0263 (9)	0.0000 (6)	0.0034 (7)	−0.0073 (7)
C11	0.0157 (8)	0.0223 (8)	0.0329 (9)	0.0061 (6)	0.0050 (7)	0.0001 (7)
C12	0.0269 (9)	0.0144 (7)	0.0254 (9)	0.0071 (6)	0.0156 (7)	0.0023 (6)
C13	0.0283 (9)	0.0155 (8)	0.0203 (8)	0.0015 (6)	0.0073 (7)	−0.0045 (6)
C14	0.0169 (8)	0.0157 (8)	0.0197 (8)	0.0022 (6)	0.0047 (6)	−0.0002 (6)
C15	0.0101 (7)	0.0142 (7)	0.0097 (7)	−0.0006 (5)	0.0029 (5)	−0.0016 (5)
C16	0.0124 (7)	0.0125 (7)	0.0131 (7)	−0.0002 (5)	0.0051 (6)	−0.0005 (5)
C17	0.0184 (8)	0.0143 (7)	0.0184 (8)	0.0031 (6)	0.0109 (6)	−0.0007 (6)
C18	0.0217 (8)	0.0176 (8)	0.0219 (8)	0.0020 (6)	0.0162 (7)	0.0021 (6)
C19	0.0192 (8)	0.0129 (7)	0.0210 (8)	−0.0008 (6)	0.0105 (6)	0.0034 (6)
C20	0.0158 (7)	0.0100 (7)	0.0156 (7)	0.0012 (5)	0.0066 (6)	−0.0019 (5)
N1	0.0171 (6)	0.0115 (6)	0.0155 (6)	−0.0005 (5)	0.0104 (5)	−0.0031 (5)
N2	0.0139 (6)	0.0122 (6)	0.0118 (6)	−0.0003 (5)	0.0052 (5)	−0.0007 (5)
Cl1	0.0168 (2)	0.0295 (2)	0.0186 (2)	−0.00015 (15)	0.00177 (16)	−0.00224 (15)

C1—C2	1.381 (2)	C10—H10	0.93
C1—C6	1.381 (2)	C11—C12	1.382 (2)
C1—Cl1	1.7443 (15)	C11—H11	0.93
C2—C3	1.389 (2)	C12—C13	1.381 (2)
C2—H2	0.93	C12—H12	0.93
C3—C4	1.389 (2)	C13—C14	1.390 (2)
C3—H3	0.93	C13—H13	0.93
C4—C5	1.395 (2)	C14—H14	0.93
C4—C7	1.528 (2)	C15—N1	1.3678 (19)
C5—C6	1.384 (2)	C15—C20	1.399 (2)
C5—H5	0.93	C15—C16	1.407 (2)
C6—H6	0.93	C16—C17	1.395 (2)
C7—N1	1.4452 (18)	C17—C18	1.376 (2)
C7—N2	1.4861 (18)	C17—H17	0.93
C7—H7	0.98	C18—C19	1.394 (2)
C8—N2	1.2820 (19)	C18—H18	0.93
C8—C16	1.462 (2)	C19—C20	1.377 (2)
C8—C9	1.4979 (19)	C19—H19	0.93
C9—C14	1.384 (2)	C20—H20	0.93
C9—C10	1.386 (2)	N1—H1N	0.831 (19)
C10—C11	1.384 (2)
C2—C1—C6	121.37 (14)	C12—C11—H11	120
C2—C1—Cl1	119.08 (12)	C10—C11—H11	120
C6—C1—Cl1	119.56 (12)	C13—C12—C11	119.94 (14)
C1—C2—C3	119.04 (13)	C13—C12—H12	120
C1—C2—H2	120.5	C11—C12—H12	120
C3—C2—H2	120.5	C12—C13—C14	120.04 (15)
C2—C3—C4	120.82 (14)	C12—C13—H13	120
C2—C3—H3	119.6	C14—C13—H13	120
C4—C3—H3	119.6	C9—C14—C13	120.12 (14)
C3—C4—C5	118.71 (14)	C9—C14—H14	119.9
C3—C4—C7	122.18 (13)	C13—C14—H14	119.9
C5—C4—C7	119.07 (13)	N1—C15—C20	122.97 (13)
C6—C5—C4	121.00 (14)	N1—C15—C16	117.54 (12)
C6—C5—H5	119.5	C20—C15—C16	119.47 (13)
C4—C5—H5	119.5	C17—C16—C15	119.54 (13)
C1—C6—C5	119.00 (14)	C17—C16—C8	123.56 (13)
C1—C6—H6	120.5	C15—C16—C8	116.78 (13)
C5—C6—H6	120.5	C18—C17—C16	120.62 (13)
N1—C7—N2	111.97 (11)	C18—C17—H17	119.7
N1—C7—C4	114.81 (12)	C16—C17—H17	119.7
N2—C7—C4	106.24 (11)	C17—C18—C19	119.54 (14)
N1—C7—H7	107.9	C17—C18—H18	120.2
N2—C7—H7	107.9	C19—C18—H18	120.2
C4—C7—H7	107.9	C20—C19—C18	121.08 (13)
N2—C8—C16	124.23 (13)	C20—C19—H19	119.5
N2—C8—C9	117.79 (12)	C18—C19—H19	119.5
C16—C8—C9	117.99 (12)	C19—C20—C15	119.72 (13)
C14—C9—C10	119.50 (14)	C19—C20—H20	120.1
C14—C9—C8	118.79 (13)	C15—C20—H20	120.1
C10—C9—C8	121.65 (13)	C15—N1—C7	118.43 (12)
C11—C10—C9	120.30 (14)	C15—N1—H1N	117.2 (13)
C11—C10—H10	119.8	C7—N1—H1N	120.4 (13)
C9—C10—H10	119.8	C8—N2—C7	116.09 (12)
C12—C11—C10	120.06 (15)
C6—C1—C2—C3	−1.8 (2)	C12—C13—C14—C9	−1.2 (2)
Cl1—C1—C2—C3	178.36 (11)	N1—C15—C16—C17	−179.97 (12)
C1—C2—C3—C4	−0.5 (2)	C20—C15—C16—C17	1.7 (2)
C2—C3—C4—C5	2.2 (2)	N1—C15—C16—C8	3.85 (19)
C2—C3—C4—C7	−175.49 (13)	C20—C15—C16—C8	−174.52 (12)
C3—C4—C5—C6	−1.8 (2)	N2—C8—C16—C17	170.14 (14)
C7—C4—C5—C6	176.00 (13)	C9—C8—C16—C17	−9.4 (2)
C2—C1—C6—C5	2.2 (2)	N2—C8—C16—C15	−13.8 (2)
Cl1—C1—C6—C5	−177.93 (11)	C9—C8—C16—C15	166.65 (12)
C4—C5—C6—C1	−0.4 (2)	C15—C16—C17—C18	−0.3 (2)
C3—C4—C7—N1	−2.54 (19)	C8—C16—C17—C18	175.64 (14)
C5—C4—C7—N1	179.78 (12)	C16—C17—C18—C19	−0.8 (2)
C3—C4—C7—N2	121.79 (14)	C17—C18—C19—C20	0.4 (2)
C5—C4—C7—N2	−55.89 (16)	C18—C19—C20—C15	1.0 (2)
N2—C8—C9—C14	−79.22 (17)	N1—C15—C20—C19	179.72 (13)
C16—C8—C9—C14	100.32 (16)	C16—C15—C20—C19	−2.0 (2)
N2—C8—C9—C10	103.78 (17)	C20—C15—N1—C7	−155.71 (13)
C16—C8—C9—C10	−76.68 (18)	C16—C15—N1—C7	25.99 (18)
C14—C9—C10—C11	0.3 (2)	N2—C7—N1—C15	−45.39 (17)
C8—C9—C10—C11	177.24 (15)	C4—C7—N1—C15	75.86 (16)
C9—C10—C11—C12	−1.6 (3)	C16—C8—N2—C7	−6.74 (19)
C10—C11—C12—C13	1.5 (3)	C9—C8—N2—C7	172.77 (12)
C11—C12—C13—C14	−0.1 (2)	N1—C7—N2—C8	34.69 (16)
C10—C9—C14—C13	1.1 (2)	C4—C7—N2—C8	−91.38 (14)
C8—C9—C14—C13	−175.93 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2i	0.830 (19)	2.316 (19)	3.1234 (18)	164.3 (19)
C3—H3···N1	0.93	2.53	2.878 (2)	102
C11—H11···Cgii	0.93	2.76	3.666 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2i	0.830 (19)	2.316 (19)	3.1234 (18)	164.3 (19)
C11—H11⋯Cg ii	0.93	2.76	3.666 (2)	165

Symmetry codes: (i) ; (ii) .