Methyl 4-(4-chloro-phen-yl)-8-iodo-2-methyl-6-oxo-1,6-dihydro-4H-pyrimido[2,1-b]quinazoline-3-carboxyl-ate.

In the title compound, C20H15ClIN3O3, the dihedral angle between the quinazolinone ring system [r.m.s. deviation = 0.047 (2) Å] and the pendant benzene ring is 82.63 (11)°. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O inter-actions. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds into chains along the a-axis direction. Another set of chains propagating along [101] is formed due to inter-molecular I⋯Cl short contacts of 3.427 (1) Å, thus giving layers parallel to (010). The layers are connected by C-H⋯π and π-π inter-actions, the shortest distance between the centroids of aromatic rings being 3.8143 (16) Å.

Related literature

For crystal structures of dihydro­pyrimidines, see: Nayak et al. (2010 ▶, 2011a ▶,b ▶,c ▶); Venugopala et al. (2012 ▶). For applications of dihydro­pyrimidines, see: Kappe (2000 ▶). For halogen-involving inter­actions, see: Nayak et al. (2011b ▶).

Experimental

Crystal data

C20H15ClIN3O3

M = 507.70

Triclinic,

a = 7.3443 (15) Å

b = 10.847 (2) Å

c = 12.475 (3) Å

α = 106.66 (3)°

β = 103.53 (2)°

γ = 92.79 (3)°

V = 918.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.92 mm−1

T = 173 K

0.25 × 0.14 × 0.12 mm

Data collection

Bruker APEXII Kappa DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.646, T max = 0.803

7109 measured reflections

3602 independent reflections

3147 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.059

S = 1.09

3602 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.89 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812050787/yk2082sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050787/yk2082Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812050787/yk2082Isup3.cml

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

C20H15ClIN3O3	Z = 2
Mr = 507.70	F(000) = 500
Triclinic, P1	Dx = 1.836 Mg m−3
Hall symbol: -P 1	Melting point: 467(2) K
a = 7.3443 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.847 (2) Å	Cell parameters from 560 reflections
c = 12.475 (3) Å	θ = 2.9–26.0°
α = 106.66 (3)°	µ = 1.92 mm−1
β = 103.53 (2)°	T = 173 K
γ = 92.79 (3)°	Plate, yellow
V = 918.5 (4) Å3	0.25 × 0.14 × 0.12 mm

Bruker APEXII Kappa DUO CCD diffractometer	3602 independent reflections
Radiation source: fine-focus sealed tube	3147 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
0.5° φ scans and ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.646, Tmax = 0.803	k = −13→13
7109 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0285P)2 + 0.4298P] where P = (Fo2 + 2Fc2)/3
3602 reflections	(Δ/σ)max = 0.003
255 parameters	Δρmax = 0.89 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
I1	1.42667 (2)	0.047532 (17)	1.168961 (15)	0.02807 (8)
Cl1	0.75652 (11)	−0.07966 (7)	0.33638 (6)	0.03791 (19)
O1	0.6050 (3)	0.62853 (18)	0.61509 (16)	0.0272 (4)
O2	0.9047 (3)	0.59136 (19)	0.62752 (17)	0.0287 (4)
O3	1.2104 (2)	0.34709 (18)	0.86038 (16)	0.0250 (4)
N1	0.5905 (3)	0.4115 (2)	0.84598 (19)	0.0238 (5)
H1	0.4842	0.3915	0.8617	0.029*
N2	0.9040 (3)	0.3772 (2)	0.85309 (17)	0.0184 (4)
N3	0.7400 (3)	0.3144 (2)	0.97648 (19)	0.0235 (5)
C1	0.6278 (4)	0.7087 (3)	0.5443 (3)	0.0312 (7)
H1A	0.7308	0.7789	0.5874	0.047*
H1B	0.5104	0.7457	0.5232	0.047*
H1C	0.6577	0.6562	0.4738	0.047*
C2	0.7579 (4)	0.5753 (2)	0.6529 (2)	0.0205 (6)
C3	0.7317 (3)	0.4945 (2)	0.7260 (2)	0.0185 (5)
C4	0.5854 (4)	0.4883 (2)	0.7733 (2)	0.0208 (5)
C5	0.4109 (4)	0.5552 (3)	0.7604 (3)	0.0270 (6)
H5A	0.4379	0.6358	0.7432	0.041*
H5B	0.3712	0.5751	0.8326	0.041*
H5C	0.3097	0.4983	0.6969	0.041*
C6	0.8863 (3)	0.4093 (2)	0.7435 (2)	0.0182 (5)
H6	1.0084	0.4588	0.7491	0.022*
C7	0.8535 (3)	0.2847 (2)	0.6416 (2)	0.0180 (5)
C8	0.9062 (4)	0.2870 (3)	0.5422 (2)	0.0230 (6)
H8	0.9657	0.3653	0.5392	0.028*
C9	0.8728 (4)	0.1763 (3)	0.4471 (2)	0.0268 (6)
H9	0.9064	0.1790	0.3787	0.032*
C10	0.7903 (4)	0.0623 (3)	0.4531 (2)	0.0261 (6)
C11	0.7360 (4)	0.0575 (3)	0.5507 (2)	0.0270 (6)
H11	0.6781	−0.0213	0.5536	0.032*
C12	0.7672 (4)	0.1693 (3)	0.6445 (2)	0.0231 (6)
H12	0.7290	0.1669	0.7116	0.028*
C13	0.7476 (4)	0.3651 (2)	0.8947 (2)	0.0192 (5)
C14	0.8986 (4)	0.2618 (2)	1.0197 (2)	0.0212 (6)
C15	0.8893 (4)	0.1949 (3)	1.0998 (2)	0.0262 (6)
H15	0.7788	0.1913	1.1265	0.031*
C16	1.0389 (4)	0.1347 (3)	1.1397 (2)	0.0264 (6)
H16	1.0300	0.0875	1.1921	0.032*
C17	1.2046 (4)	0.1424 (3)	1.1035 (2)	0.0233 (6)
C18	1.2198 (4)	0.2091 (3)	1.0265 (2)	0.0227 (6)
H18	1.3325	0.2143	1.0022	0.027*
C19	1.0655 (4)	0.2691 (2)	0.9845 (2)	0.0194 (5)
C20	1.0732 (4)	0.3341 (2)	0.8977 (2)	0.0194 (5)

	U11	U22	U33	U12	U13	U23
I1	0.02738 (11)	0.03098 (12)	0.02945 (11)	0.00738 (8)	0.00520 (8)	0.01593 (8)
Cl1	0.0363 (4)	0.0311 (4)	0.0339 (4)	0.0142 (3)	−0.0019 (3)	−0.0018 (3)
O1	0.0242 (10)	0.0311 (11)	0.0342 (11)	0.0093 (8)	0.0084 (9)	0.0202 (9)
O2	0.0265 (11)	0.0315 (11)	0.0400 (12)	0.0078 (8)	0.0166 (9)	0.0220 (9)
O3	0.0167 (9)	0.0348 (11)	0.0314 (10)	0.0061 (8)	0.0103 (8)	0.0185 (9)
N1	0.0154 (11)	0.0320 (13)	0.0320 (13)	0.0073 (9)	0.0111 (10)	0.0173 (10)
N2	0.0153 (11)	0.0229 (12)	0.0202 (11)	0.0031 (9)	0.0065 (9)	0.0097 (9)
N3	0.0213 (12)	0.0289 (13)	0.0247 (12)	0.0064 (10)	0.0095 (10)	0.0115 (10)
C1	0.0335 (16)	0.0341 (17)	0.0321 (16)	0.0071 (13)	0.0055 (13)	0.0215 (13)
C2	0.0221 (14)	0.0174 (13)	0.0205 (13)	0.0040 (11)	0.0037 (11)	0.0044 (11)
C3	0.0159 (13)	0.0186 (13)	0.0205 (13)	0.0023 (10)	0.0037 (10)	0.0060 (11)
C4	0.0209 (14)	0.0191 (13)	0.0231 (13)	0.0042 (11)	0.0047 (11)	0.0080 (11)
C5	0.0230 (14)	0.0303 (15)	0.0363 (16)	0.0118 (12)	0.0140 (13)	0.0168 (13)
C6	0.0167 (12)	0.0228 (14)	0.0194 (13)	0.0034 (10)	0.0069 (10)	0.0113 (11)
C7	0.0121 (12)	0.0223 (14)	0.0220 (13)	0.0069 (10)	0.0039 (10)	0.0103 (11)
C8	0.0208 (14)	0.0261 (15)	0.0264 (14)	0.0047 (11)	0.0102 (11)	0.0113 (12)
C9	0.0237 (14)	0.0353 (17)	0.0237 (14)	0.0103 (13)	0.0078 (12)	0.0100 (12)
C10	0.0210 (14)	0.0263 (15)	0.0251 (14)	0.0107 (12)	−0.0004 (12)	0.0027 (12)
C11	0.0242 (15)	0.0211 (15)	0.0360 (16)	0.0041 (12)	0.0032 (12)	0.0128 (13)
C12	0.0227 (14)	0.0247 (15)	0.0254 (14)	0.0046 (11)	0.0077 (12)	0.0113 (12)
C13	0.0176 (13)	0.0205 (13)	0.0199 (13)	0.0040 (10)	0.0070 (11)	0.0046 (11)
C14	0.0221 (14)	0.0218 (14)	0.0198 (13)	0.0045 (11)	0.0056 (11)	0.0058 (11)
C15	0.0260 (15)	0.0340 (16)	0.0237 (14)	0.0041 (12)	0.0122 (12)	0.0119 (12)
C16	0.0308 (15)	0.0312 (16)	0.0217 (14)	0.0047 (12)	0.0079 (12)	0.0141 (12)
C17	0.0256 (14)	0.0240 (14)	0.0202 (13)	0.0057 (11)	0.0042 (11)	0.0075 (11)
C18	0.0223 (14)	0.0247 (14)	0.0220 (14)	0.0044 (11)	0.0066 (11)	0.0079 (11)
C19	0.0183 (13)	0.0212 (13)	0.0192 (13)	0.0014 (11)	0.0052 (10)	0.0070 (11)
C20	0.0187 (13)	0.0193 (13)	0.0190 (13)	0.0023 (10)	0.0029 (11)	0.0058 (11)

I1—C17	2.099 (3)	C5—H5C	0.9800
Cl1—C10	1.750 (3)	C6—C7	1.530 (4)
O1—C2	1.338 (3)	C6—H6	1.0000
O1—C1	1.436 (3)	C7—C12	1.389 (4)
O2—C2	1.211 (3)	C7—C8	1.390 (3)
O3—C20	1.223 (3)	C8—C9	1.389 (4)
N1—C13	1.363 (3)	C8—H8	0.9500
N1—C4	1.392 (3)	C9—C10	1.379 (4)
N1—H1	0.8800	C9—H9	0.9500
N2—C13	1.382 (3)	C10—C11	1.380 (4)
N2—C20	1.398 (3)	C11—C12	1.388 (4)
N2—C6	1.483 (3)	C11—H11	0.9500
N3—C13	1.301 (3)	C12—H12	0.9500
N3—C14	1.386 (3)	C14—C19	1.401 (4)
C1—H1A	0.9800	C14—C15	1.404 (4)
C1—H1B	0.9800	C15—C16	1.372 (4)
C1—H1C	0.9800	C15—H15	0.9500
C2—C3	1.469 (3)	C16—C17	1.401 (4)
C3—C4	1.349 (3)	C16—H16	0.9500
C3—C6	1.515 (3)	C17—C18	1.379 (4)
C4—C5	1.502 (4)	C18—C19	1.405 (4)
C5—H5A	0.9800	C18—H18	0.9500
C5—H5B	0.9800	C19—C20	1.461 (3)
C2—O1—C1	115.4 (2)	C9—C8—H8	119.6
C13—N1—C4	125.0 (2)	C7—C8—H8	119.6
C13—N1—H1	117.5	C10—C9—C8	119.3 (3)
C4—N1—H1	117.5	C10—C9—H9	120.4
C13—N2—C20	121.4 (2)	C8—C9—H9	120.4
C13—N2—C6	120.6 (2)	C9—C10—C11	121.1 (3)
C20—N2—C6	116.72 (19)	C9—C10—Cl1	119.8 (2)
C13—N3—C14	116.7 (2)	C11—C10—Cl1	119.1 (2)
O1—C1—H1A	109.5	C10—C11—C12	119.1 (3)
O1—C1—H1B	109.5	C10—C11—H11	120.4
H1A—C1—H1B	109.5	C12—C11—H11	120.4
O1—C1—H1C	109.5	C11—C12—C7	120.9 (2)
H1A—C1—H1C	109.5	C11—C12—H12	119.5
H1B—C1—H1C	109.5	C7—C12—H12	119.5
O2—C2—O1	122.5 (2)	N3—C13—N1	118.2 (2)
O2—C2—C3	123.1 (2)	N3—C13—N2	125.2 (2)
O1—C2—C3	114.4 (2)	N1—C13—N2	116.6 (2)
C4—C3—C2	126.5 (2)	N3—C14—C19	122.9 (2)
C4—C3—C6	119.8 (2)	N3—C14—C15	118.4 (2)
C2—C3—C6	113.7 (2)	C19—C14—C15	118.7 (2)
C3—C4—N1	118.3 (2)	C16—C15—C14	120.4 (2)
C3—C4—C5	129.1 (2)	C16—C15—H15	119.8
N1—C4—C5	112.6 (2)	C14—C15—H15	119.8
C4—C5—H5A	109.5	C15—C16—C17	120.3 (2)
C4—C5—H5B	109.5	C15—C16—H16	119.8
H5A—C5—H5B	109.5	C17—C16—H16	119.8
C4—C5—H5C	109.5	C18—C17—C16	120.8 (2)
H5A—C5—H5C	109.5	C18—C17—I1	121.37 (19)
H5B—C5—H5C	109.5	C16—C17—I1	117.80 (19)
N2—C6—C3	111.06 (19)	C17—C18—C19	118.7 (2)
N2—C6—C7	110.0 (2)	C17—C18—H18	120.6
C3—C6—C7	111.7 (2)	C19—C18—H18	120.6
N2—C6—H6	108.0	C14—C19—C18	121.0 (2)
C3—C6—H6	108.0	C14—C19—C20	118.9 (2)
C7—C6—H6	108.0	C18—C19—C20	120.0 (2)
C12—C7—C8	118.8 (2)	O3—C20—N2	120.3 (2)
C12—C7—C6	121.6 (2)	O3—C20—C19	125.0 (2)
C8—C7—C6	119.6 (2)	N2—C20—C19	114.7 (2)
C9—C8—C7	120.7 (3)
C1—O1—C2—O2	−1.3 (4)	C6—C7—C12—C11	179.1 (2)
C1—O1—C2—C3	179.5 (2)	C14—N3—C13—N1	176.6 (2)
O2—C2—C3—C4	168.5 (3)	C14—N3—C13—N2	−4.1 (4)
O1—C2—C3—C4	−12.4 (4)	C4—N1—C13—N3	168.0 (2)
O2—C2—C3—C6	−13.4 (4)	C4—N1—C13—N2	−11.4 (4)
O1—C2—C3—C6	165.8 (2)	C20—N2—C13—N3	0.0 (4)
C2—C3—C4—N1	−176.2 (2)	C6—N2—C13—N3	166.5 (2)
C6—C3—C4—N1	5.7 (4)	C20—N2—C13—N1	179.3 (2)
C2—C3—C4—C5	3.0 (5)	C6—N2—C13—N1	−14.2 (3)
C6—C3—C4—C5	−175.0 (3)	C13—N3—C14—C19	4.3 (4)
C13—N1—C4—C3	15.7 (4)	C13—N3—C14—C15	−173.8 (2)
C13—N1—C4—C5	−163.7 (2)	N3—C14—C15—C16	176.1 (3)
C13—N2—C6—C3	31.8 (3)	C19—C14—C15—C16	−2.0 (4)
C20—N2—C6—C3	−161.1 (2)	C14—C15—C16—C17	1.8 (4)
C13—N2—C6—C7	−92.5 (3)	C15—C16—C17—C18	−0.7 (4)
C20—N2—C6—C7	74.6 (3)	C15—C16—C17—I1	179.9 (2)
C4—C3—C6—N2	−27.2 (3)	C16—C17—C18—C19	−0.1 (4)
C2—C3—C6—N2	154.5 (2)	I1—C17—C18—C19	179.16 (19)
C4—C3—C6—C7	96.0 (3)	N3—C14—C19—C18	−176.9 (2)
C2—C3—C6—C7	−82.2 (3)	C15—C14—C19—C18	1.1 (4)
N2—C6—C7—C12	27.4 (3)	N3—C14—C19—C20	−0.5 (4)
C3—C6—C7—C12	−96.5 (3)	C15—C14—C19—C20	177.5 (2)
N2—C6—C7—C8	−154.5 (2)	C17—C18—C19—C14	−0.1 (4)
C3—C6—C7—C8	81.7 (3)	C17—C18—C19—C20	−176.4 (2)
C12—C7—C8—C9	0.2 (4)	C13—N2—C20—O3	−179.2 (2)
C6—C7—C8—C9	−178.0 (2)	C6—N2—C20—O3	13.8 (3)
C7—C8—C9—C10	−1.5 (4)	C13—N2—C20—C19	3.8 (3)
C8—C9—C10—C11	1.7 (4)	C6—N2—C20—C19	−163.2 (2)
C8—C9—C10—Cl1	−177.3 (2)	C14—C19—C20—O3	179.8 (3)
C9—C10—C11—C12	−0.6 (4)	C18—C19—C20—O3	−3.8 (4)
Cl1—C10—C11—C12	178.3 (2)	C14—C19—C20—N2	−3.4 (3)
C10—C11—C12—C7	−0.7 (4)	C18—C19—C20—N2	173.0 (2)
C8—C7—C12—C11	0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.88	2.04	2.903 (3)	167
C5—H5A···O1	0.98	2.22	2.807 (4)	117
C8—H8···O2	0.95	2.49	3.167 (4)	128
C1—H1B···Cg1ii	0.98	2.67	3.647 (4)	175

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.88	2.04	2.903 (3)	167
C5—H5A⋯O1	0.98	2.22	2.807 (4)	117
C8—H8⋯O2	0.95	2.49	3.167 (4)	128
C1—H1B⋯Cg1ii	0.98	2.67	3.647 (4)	175

Symmetry codes: (i) ; (ii) .