6-Chloro-2-chloro-methyl-4-phenyl-quinazoline 3-oxide.

In the title compound, C15H10Cl2N2O, the dihedral angle between the mean planes of the phenyl ring and the 10-membered quinazoline ring is 63.3 (4)°. In the crystal, pairs of weak C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers, forming R 2 (2)(10) graph-set ring motifs. In addition, weak π-π stacking inter-actions [minimum centroid-centroid separation = 3.6810 (8) Å] are observed, which contribute to the formation of a supramolecular assembly in the packing array.

Related literature

For general background and the pharmacological properties of quinazoline derivatives, see: Andries et al. (2005 ▶); Al-Rashood et al. (2006 ▶); Ghorab et al. (2010a ▶,b ▶,c ▶); Harris & Thorarensen (2004 ▶); Jantova et al. (2004 ▶); Rádl et al. (2000 ▶); Klepser & Klepser (1997 ▶). For related structures, see: Brown & Gainsford (1979 ▶); El-Brollosy et al. (2012 ▶); Shi et al. (2004 ▶); Suguna et al. (1982 ▶); Xie & Li (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H10Cl2N2O

M = 305.15

Monoclinic,

a = 8.2030 (3) Å

b = 14.3203 (5) Å

c = 11.8477 (4) Å

β = 105.016 (4)°

V = 1344.22 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 173 K

0.22 × 0.16 × 0.08 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.829, T max = 1.000

17250 measured reflections

4599 independent reflections

3778 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.03

4599 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.48 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005303/zs2289sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005303/zs2289Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005303/zs2289Isup3.cml

CCDC reference: 990666

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H10Cl2N2O	F(000) = 624
Mr = 305.15	Dx = 1.508 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2030 (3) Å	Cell parameters from 5430 reflections
b = 14.3203 (5) Å	θ = 3.1–32.8°
c = 11.8477 (4) Å	µ = 0.48 mm−1
β = 105.016 (4)°	T = 173 K
V = 1344.22 (9) Å3	Irregular, colourless
Z = 4	0.22 × 0.16 × 0.08 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	4599 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3778 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 16.0416 pixels mm-1	θmax = 32.8°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −21→21
Tmin = 0.829, Tmax = 1.000	l = −17→17
17250 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.6066P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4599 reflections	Δρmax = 0.44 e Å−3
181 parameters	Δρmin = −0.48 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
Cl1	0.80516 (4)	0.57556 (2)	0.41153 (3)	0.02910 (9)
Cl2	1.25299 (5)	0.02361 (3)	0.52366 (4)	0.03835 (10)
O1	0.70795 (12)	0.42471 (7)	0.59735 (8)	0.0258 (2)
N1	0.77812 (13)	0.37116 (7)	0.53548 (8)	0.01880 (19)
N2	0.80968 (14)	0.34057 (8)	0.34467 (9)	0.0222 (2)
C1	0.75384 (16)	0.39185 (9)	0.41604 (10)	0.0206 (2)
C2	0.90492 (15)	0.26388 (9)	0.38678 (10)	0.0202 (2)
C3	0.97031 (17)	0.20909 (10)	0.31009 (11)	0.0255 (3)
H3	0.9429	0.2234	0.2308	0.031*
C4	1.07367 (17)	0.13503 (10)	0.35109 (12)	0.0269 (3)
H4	1.1158	0.0984	0.3003	0.032*
C5	1.11527 (16)	0.11514 (9)	0.47137 (12)	0.0244 (2)
C6	1.05319 (16)	0.16552 (9)	0.54919 (11)	0.0222 (2)
H6	1.0832	0.1507	0.6283	0.027*
C7	0.94247 (15)	0.24056 (8)	0.50668 (10)	0.0188 (2)
C8	0.86931 (15)	0.29543 (8)	0.58051 (10)	0.0181 (2)
C9	0.88618 (15)	0.27188 (8)	0.70445 (10)	0.0193 (2)
C10	0.96680 (16)	0.33233 (9)	0.79356 (10)	0.0229 (2)
H10	1.0080	0.3895	0.7758	0.027*
C11	0.98512 (17)	0.30648 (10)	0.90932 (11)	0.0270 (3)
H11	1.0415	0.3458	0.9693	0.032*
C12	0.91999 (18)	0.22262 (10)	0.93578 (11)	0.0282 (3)
H12	0.9316	0.2063	1.0134	0.034*
C13	0.83771 (18)	0.16286 (10)	0.84755 (12)	0.0273 (3)
H13	0.7928	0.1069	0.8657	0.033*
C14	0.82261 (17)	0.18705 (9)	0.73159 (11)	0.0233 (2)
H14	0.7699	0.1464	0.6720	0.028*
C15	0.66120 (17)	0.47967 (9)	0.37389 (11)	0.0237 (2)
H15A	0.5686	0.4876	0.4099	0.028*
H15B	0.6151	0.4771	0.2898	0.028*

	U11	U22	U33	U12	U13	U23
Cl1	0.02893 (17)	0.02459 (16)	0.03348 (17)	−0.00319 (11)	0.00757 (13)	0.00339 (12)
Cl2	0.0404 (2)	0.02622 (17)	0.0529 (2)	0.00878 (14)	0.02027 (18)	0.00153 (15)
O1	0.0310 (5)	0.0258 (5)	0.0227 (4)	0.0072 (4)	0.0109 (4)	−0.0010 (3)
N1	0.0198 (5)	0.0202 (5)	0.0164 (4)	0.0000 (4)	0.0047 (4)	−0.0005 (3)
N2	0.0224 (5)	0.0271 (5)	0.0160 (4)	−0.0036 (4)	0.0032 (4)	−0.0006 (4)
C1	0.0204 (5)	0.0232 (6)	0.0167 (5)	−0.0026 (4)	0.0021 (4)	0.0017 (4)
C2	0.0196 (5)	0.0242 (6)	0.0165 (5)	−0.0044 (4)	0.0041 (4)	−0.0027 (4)
C3	0.0258 (6)	0.0326 (7)	0.0188 (5)	−0.0067 (5)	0.0071 (5)	−0.0074 (5)
C4	0.0255 (6)	0.0295 (6)	0.0283 (6)	−0.0066 (5)	0.0116 (5)	−0.0119 (5)
C5	0.0222 (6)	0.0205 (6)	0.0323 (6)	−0.0023 (4)	0.0102 (5)	−0.0048 (5)
C6	0.0237 (6)	0.0212 (5)	0.0229 (5)	−0.0011 (4)	0.0084 (5)	−0.0002 (4)
C7	0.0194 (5)	0.0205 (5)	0.0170 (5)	−0.0033 (4)	0.0055 (4)	−0.0018 (4)
C8	0.0195 (5)	0.0196 (5)	0.0151 (4)	−0.0020 (4)	0.0044 (4)	−0.0003 (4)
C9	0.0203 (5)	0.0223 (5)	0.0162 (5)	0.0030 (4)	0.0062 (4)	0.0011 (4)
C10	0.0226 (6)	0.0269 (6)	0.0190 (5)	−0.0001 (5)	0.0052 (4)	−0.0005 (4)
C11	0.0247 (6)	0.0378 (7)	0.0176 (5)	0.0051 (5)	0.0042 (5)	−0.0021 (5)
C12	0.0284 (7)	0.0389 (7)	0.0189 (5)	0.0116 (5)	0.0089 (5)	0.0077 (5)
C13	0.0317 (7)	0.0270 (6)	0.0264 (6)	0.0066 (5)	0.0135 (5)	0.0081 (5)
C14	0.0266 (6)	0.0228 (6)	0.0218 (5)	0.0010 (5)	0.0087 (5)	0.0011 (4)
C15	0.0232 (6)	0.0238 (6)	0.0214 (5)	−0.0008 (4)	0.0011 (4)	0.0038 (4)

Cl1—C15	1.7905 (13)	C6—C7	1.4128 (17)
Cl2—C5	1.7366 (14)	C7—C8	1.4194 (16)
O1—N1	1.2943 (13)	C8—C9	1.4778 (15)
N1—C1	1.4086 (15)	C9—C10	1.3926 (17)
N1—C8	1.3467 (15)	C9—C14	1.3921 (17)
N2—C1	1.2901 (16)	C10—H10	0.9300
N2—C2	1.3651 (17)	C10—C11	1.3906 (17)
C1—C15	1.4872 (17)	C11—H11	0.9300
C2—C3	1.4076 (17)	C11—C12	1.383 (2)
C2—C7	1.4134 (16)	C12—H12	0.9300
C3—H3	0.9300	C12—C13	1.384 (2)
C3—C4	1.366 (2)	C13—H13	0.9300
C4—H4	0.9300	C13—C14	1.3909 (17)
C4—C5	1.4058 (19)	C14—H14	0.9300
C5—C6	1.3686 (17)	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
O1—N1—C1	118.46 (10)	N1—C8—C9	118.47 (10)
O1—N1—C8	122.39 (10)	C7—C8—C9	122.71 (10)
C8—N1—C1	119.13 (10)	C10—C9—C8	121.01 (11)
C1—N2—C2	119.02 (10)	C14—C9—C8	118.97 (11)
N1—C1—C15	116.24 (11)	C14—C9—C10	120.01 (11)
N2—C1—N1	123.84 (11)	C9—C10—H10	120.3
N2—C1—C15	119.90 (11)	C11—C10—C9	119.40 (12)
N2—C2—C3	119.36 (11)	C11—C10—H10	120.3
N2—C2—C7	120.83 (11)	C10—C11—H11	119.8
C3—C2—C7	119.79 (12)	C12—C11—C10	120.36 (13)
C2—C3—H3	119.7	C12—C11—H11	119.8
C4—C3—C2	120.56 (12)	C11—C12—H12	119.8
C4—C3—H3	119.7	C11—C12—C13	120.47 (12)
C3—C4—H4	120.6	C13—C12—H12	119.8
C3—C4—C5	118.88 (12)	C12—C13—H13	120.2
C5—C4—H4	120.6	C12—C13—C14	119.56 (13)
C4—C5—Cl2	118.63 (10)	C14—C13—H13	120.2
C6—C5—Cl2	118.60 (11)	C9—C14—H14	119.9
C6—C5—C4	122.76 (12)	C13—C14—C9	120.18 (12)
C5—C6—H6	120.7	C13—C14—H14	119.9
C5—C6—C7	118.54 (12)	Cl1—C15—H15A	110.0
C7—C6—H6	120.7	Cl1—C15—H15B	110.0
C2—C7—C8	118.15 (11)	C1—C15—Cl1	108.56 (9)
C6—C7—C2	119.38 (11)	C1—C15—H15A	110.0
C6—C7—C8	122.46 (11)	C1—C15—H15B	110.0
N1—C8—C7	118.80 (10)	H15A—C15—H15B	108.4
Cl2—C5—C6—C7	179.38 (9)	C3—C2—C7—C8	−177.77 (11)
O1—N1—C1—N2	−176.01 (11)	C3—C4—C5—Cl2	−177.62 (10)
O1—N1—C1—C15	5.43 (16)	C3—C4—C5—C6	1.7 (2)
O1—N1—C8—C7	−179.81 (11)	C4—C5—C6—C7	0.10 (19)
O1—N1—C8—C9	1.37 (17)	C5—C6—C7—C2	−2.69 (18)
N1—C1—C15—Cl1	80.38 (12)	C5—C6—C7—C8	178.70 (11)
N1—C8—C9—C10	−63.17 (16)	C6—C7—C8—N1	173.70 (11)
N1—C8—C9—C14	117.95 (13)	C6—C7—C8—C9	−7.54 (18)
N2—C1—C15—Cl1	−98.24 (12)	C7—C2—C3—C4	−1.82 (18)
N2—C2—C3—C4	176.35 (12)	C7—C8—C9—C10	118.06 (14)
N2—C2—C7—C6	−174.59 (11)	C7—C8—C9—C14	−60.81 (16)
N2—C2—C7—C8	4.09 (17)	C8—N1—C1—N2	2.29 (18)
C1—N1—C8—C7	1.96 (16)	C8—N1—C1—C15	−176.27 (11)
C1—N1—C8—C9	−176.85 (11)	C8—C9—C10—C11	−177.93 (12)
C1—N2—C2—C3	−178.21 (12)	C8—C9—C14—C13	179.60 (12)
C1—N2—C2—C7	−0.05 (18)	C9—C10—C11—C12	−1.71 (19)
C2—N2—C1—N1	−3.24 (18)	C10—C9—C14—C13	0.71 (19)
C2—N2—C1—C15	175.27 (11)	C10—C11—C12—C13	0.8 (2)
C2—C3—C4—C5	−0.76 (19)	C11—C12—C13—C14	0.8 (2)
C2—C7—C8—N1	−4.93 (17)	C12—C13—C14—C9	−1.6 (2)
C2—C7—C8—C9	173.83 (11)	C14—C9—C10—C11	0.93 (19)
C3—C2—C7—C6	3.56 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1i	0.97	2.57	3.4199 (16)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1i	0.97	2.57	3.4199 (16)	146

Symmetry code: (i) .