3-Methyl-2-(3,3,3-tri-chloro-2-hy-droxy-prop-yl)quinazolin-4(3H)-one.

The title mol-ecule, C12H11Cl3N2O2, contains planar quinazolin-4(3H)-one (r.m.s. deviation = 0.0257 Å) and propyl fragments, forming a dihedral angle of 10.4 (2)°. An intra-molecular O-H⋯N hydorgen bond occurs. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into an infinite chain running parallel to the b axis.

Related literature

For the biological properties of quinazolin-4(3H)-one deriv­atives, see: Yang et al. (2009 ▶). For the fungicidal and insecticidal activity and syntheses of quinazolin-4(3H)-one derivatives, see: Shakhidoyatov (1988 ▶). For related structures of quinazolin-4(3H)-one derivatives, see: Tashkhodjaev et al. (2001 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H11Cl3N2O2

M = 321.58

Orthorhombic,

a = 9.3440 (19) Å

b = 11.352 (2) Å

c = 25.719 (5) Å

V = 2728.2 (10) Å3

Z = 8

Cu Kα radiation

μ = 6.09 mm−1

T = 291 K

0.23 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.284, T max = 0.334

8631 measured reflections

2833 independent reflections

2273 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.03

2833 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016073/pv2636sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016073/pv2636Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016073/pv2636Isup3.cml

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

C12H11Cl3N2O2	Dx = 1.566 Mg m−3
Mr = 321.58	Melting point: 423(2) K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1044 reflections
a = 9.3440 (19) Å	θ = 3.4–35.8°
b = 11.352 (2) Å	µ = 6.09 mm−1
c = 25.719 (5) Å	T = 291 K
V = 2728.2 (10) Å3	Prizmatic, colorless
Z = 8	0.23 × 0.20 × 0.18 mm
F(000) = 1312

Oxford Diffraction Xcalibur Ruby diffractometer	2833 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2273 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.2576 pixels mm-1	θmax = 76.4°, θmin = 3.4°
ω scans	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→14
Tmin = 0.284, Tmax = 0.334	l = −32→31
8631 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0775P)2] where P = (Fo2 + 2Fc2)/3
2833 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. 1H NMR (400 MHz, DMSO): 8.11 (1H, d, J═7.9 Hz, H-5), 7.80 (1H, t, J═7.9 Hz, H-7), 7.64 (1H, d, J═7.9 Hz, H-8), 7.50 (1H, t, J═7.9 Hz, H-6), 7.06 (1H, b.d, J═4.8 Hz, OH), 4.84 (1H, b.d, J═8.6 Hz, CH-10), 3.46 (1H, m, H-9 e), 3.22 (1H, dd, J═15.6, J═9.2 Hz, H-9a), 3.6 (3H, s, CH3-12).In the IR spectrum of the title compound were observed absorption bands due to the stretching vibrations of 3401 sm-1 for OH, 2829 sm-1 for CH3, 1657 sm-1 for C═O, 1594 sm-1 for C═N, 1563 sm-1 for C═C– groups. Additionally, at 695 sm-1 was observed p–p valence vibrations of the C—Cl group.The UV spectrum of title compound in ethanol is characterized by absorption bands at 225, 266, 305 and 316 nm.

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	0.5628 (2)	0.70184 (16)	0.27949 (7)	0.0607 (5)
N1	0.27902 (19)	0.46334 (15)	0.22269 (6)	0.0373 (4)
C2	0.3539 (2)	0.53163 (17)	0.19344 (7)	0.0331 (4)
N3	0.44671 (19)	0.61703 (15)	0.21185 (6)	0.0375 (4)
C4	0.4735 (2)	0.62977 (19)	0.26492 (8)	0.0418 (5)
C4A	0.3879 (2)	0.5557 (2)	0.29826 (8)	0.0427 (5)
C5	0.3995 (3)	0.5667 (2)	0.35264 (9)	0.0573 (7)
H5A	0.4627	0.6208	0.3671	0.069*
C6	0.3168 (3)	0.4969 (3)	0.38393 (9)	0.0682 (8)
H6A	0.3253	0.5021	0.4199	0.082*
C7	0.2197 (3)	0.4179 (3)	0.36200 (10)	0.0640 (8)
H7A	0.1631	0.3715	0.3836	0.077*
C8	0.2063 (3)	0.4073 (2)	0.30879 (9)	0.0508 (6)
H8A	0.1406	0.3548	0.2946	0.061*
C8A	0.2923 (2)	0.47628 (19)	0.27638 (8)	0.0396 (5)
C9	0.3415 (2)	0.52114 (18)	0.13538 (7)	0.0379 (4)
H9A	0.4362	0.5114	0.1206	0.046*
H9B	0.3010	0.5933	0.1215	0.046*
C10	0.2482 (2)	0.41768 (17)	0.11937 (7)	0.0345 (4)
H10A	0.1545	0.4256	0.1361	0.041*
C11	0.2271 (2)	0.41360 (18)	0.06012 (7)	0.0388 (4)
C12	0.5242 (3)	0.6964 (2)	0.17710 (9)	0.0499 (6)
H12A	0.4707	0.7066	0.1455	0.075*
H12B	0.6163	0.6635	0.1692	0.075*
H12C	0.5365	0.7714	0.1938	0.075*
O2	0.3064 (2)	0.30816 (13)	0.13248 (6)	0.0496 (4)
Cl1	0.10438 (8)	0.30035 (5)	0.04356 (2)	0.0569 (2)
Cl2	0.15423 (7)	0.54822 (5)	0.03761 (2)	0.05238 (19)
Cl3	0.38904 (8)	0.38646 (8)	0.02721 (3)	0.0712 (2)
H2	0.326 (3)	0.299 (3)	0.1623 (13)	0.075 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0610 (10)	0.0636 (11)	0.0576 (10)	−0.0084 (10)	−0.0205 (8)	−0.0186 (8)
N1	0.0407 (9)	0.0369 (9)	0.0343 (8)	0.0009 (8)	−0.0039 (7)	−0.0022 (7)
C2	0.0328 (9)	0.0323 (9)	0.0342 (9)	0.0032 (8)	−0.0072 (7)	−0.0039 (7)
N3	0.0378 (8)	0.0373 (9)	0.0372 (8)	−0.0012 (8)	−0.0083 (7)	−0.0037 (7)
C4	0.0425 (11)	0.0428 (11)	0.0401 (10)	0.0062 (10)	−0.0121 (9)	−0.0116 (8)
C4A	0.0443 (11)	0.0494 (12)	0.0345 (10)	0.0150 (10)	−0.0070 (8)	−0.0056 (8)
C5	0.0608 (15)	0.0744 (17)	0.0365 (11)	0.0162 (13)	−0.0099 (11)	−0.0098 (11)
C6	0.0766 (18)	0.093 (2)	0.0348 (11)	0.0242 (18)	−0.0023 (12)	0.0001 (13)
C7	0.0720 (18)	0.0722 (17)	0.0479 (13)	0.0240 (15)	0.0159 (13)	0.0142 (12)
C8	0.0552 (14)	0.0496 (13)	0.0477 (12)	0.0098 (11)	0.0052 (10)	0.0040 (10)
C8A	0.0423 (11)	0.0411 (10)	0.0355 (9)	0.0117 (9)	−0.0026 (8)	−0.0018 (8)
C9	0.0425 (10)	0.0406 (10)	0.0307 (9)	−0.0041 (9)	−0.0069 (8)	−0.0016 (8)
C10	0.0406 (10)	0.0345 (10)	0.0285 (8)	0.0006 (8)	−0.0059 (8)	0.0008 (7)
C11	0.0468 (11)	0.0369 (10)	0.0326 (9)	0.0005 (9)	−0.0060 (8)	−0.0012 (8)
C12	0.0498 (13)	0.0456 (12)	0.0544 (12)	−0.0112 (11)	−0.0069 (10)	0.0012 (10)
O2	0.0734 (11)	0.0352 (7)	0.0403 (8)	0.0076 (8)	−0.0213 (8)	0.0016 (6)
Cl1	0.0771 (4)	0.0438 (3)	0.0499 (3)	−0.0108 (3)	−0.0273 (3)	−0.0026 (2)
Cl2	0.0730 (4)	0.0420 (3)	0.0421 (3)	0.0013 (3)	−0.0189 (3)	0.0088 (2)
Cl3	0.0643 (4)	0.0993 (6)	0.0499 (3)	0.0099 (4)	0.0118 (3)	−0.0174 (3)

O1—C4	1.227 (3)	C8—C8A	1.398 (3)
N1—C2	1.287 (3)	C8—H8A	0.9300
N1—C8A	1.394 (2)	C9—C10	1.520 (3)
C2—N3	1.384 (3)	C9—H9A	0.9700
C2—C9	1.503 (2)	C9—H9B	0.9700
N3—C4	1.395 (2)	C10—O2	1.398 (2)
N3—C12	1.462 (3)	C10—C11	1.537 (3)
C4—C4A	1.443 (3)	C10—H10A	0.9800
C4A—C8A	1.388 (3)	C11—Cl3	1.761 (2)
C4A—C5	1.408 (3)	C11—Cl2	1.770 (2)
C5—C6	1.369 (4)	C11—Cl1	1.774 (2)
C5—H5A	0.9300	C12—H12A	0.9600
C6—C7	1.395 (4)	C12—H12B	0.9600
C6—H6A	0.9300	C12—H12C	0.9600
C7—C8	1.380 (3)	O2—H2	0.80 (3)
C7—H7A	0.9300
C2—N1—C8A	117.84 (18)	N1—C8A—C8	118.7 (2)
N1—C2—N3	124.22 (17)	C2—C9—C10	112.01 (16)
N1—C2—C9	119.43 (17)	C2—C9—H9A	109.2
N3—C2—C9	116.35 (17)	C10—C9—H9A	109.2
C2—N3—C4	121.31 (18)	C2—C9—H9B	109.2
C2—N3—C12	122.21 (17)	C10—C9—H9B	109.2
C4—N3—C12	116.47 (18)	H9A—C9—H9B	107.9
O1—C4—N3	119.3 (2)	O2—C10—C9	113.49 (17)
O1—C4—C4A	125.7 (2)	O2—C10—C11	105.21 (16)
N3—C4—C4A	114.95 (18)	C9—C10—C11	111.45 (16)
C8A—C4A—C5	120.6 (2)	O2—C10—H10A	108.9
C8A—C4A—C4	119.60 (19)	C9—C10—H10A	108.9
C5—C4A—C4	119.7 (2)	C11—C10—H10A	108.9
C6—C5—C4A	119.3 (3)	C10—C11—Cl3	111.79 (15)
C6—C5—H5A	120.4	C10—C11—Cl2	110.34 (14)
C4A—C5—H5A	120.4	Cl3—C11—Cl2	108.92 (12)
C5—C6—C7	120.1 (2)	C10—C11—Cl1	110.05 (14)
C5—C6—H6A	119.9	Cl3—C11—Cl1	108.24 (11)
C7—C6—H6A	119.9	Cl2—C11—Cl1	107.38 (12)
C8—C7—C6	121.1 (3)	N3—C12—H12A	109.5
C8—C7—H7A	119.5	N3—C12—H12B	109.5
C6—C7—H7A	119.5	H12A—C12—H12B	109.5
C7—C8—C8A	119.4 (3)	N3—C12—H12C	109.5
C7—C8—H8A	120.3	H12A—C12—H12C	109.5
C8A—C8—H8A	120.3	H12B—C12—H12C	109.5
C4A—C8A—N1	121.8 (2)	C10—O2—H2	116 (2)
C4A—C8A—C8	119.5 (2)
C8A—N1—C2—N3	0.0 (3)	C5—C4A—C8A—N1	−179.8 (2)
C8A—N1—C2—C9	−179.45 (18)	C4—C4A—C8A—N1	1.8 (3)
N1—C2—N3—C4	4.6 (3)	C5—C4A—C8A—C8	0.5 (3)
C9—C2—N3—C4	−175.97 (19)	C4—C4A—C8A—C8	−178.0 (2)
N1—C2—N3—C12	−176.9 (2)	C2—N1—C8A—C4A	−3.1 (3)
C9—C2—N3—C12	2.6 (3)	C2—N1—C8A—C8	176.62 (19)
C2—N3—C4—O1	175.7 (2)	C7—C8—C8A—C4A	−1.2 (3)
C12—N3—C4—O1	−2.9 (3)	C7—C8—C8A—N1	179.1 (2)
C2—N3—C4—C4A	−5.5 (3)	N1—C2—C9—C10	−5.9 (3)
C12—N3—C4—C4A	175.87 (18)	N3—C2—C9—C10	174.59 (16)
O1—C4—C4A—C8A	−178.8 (2)	C2—C9—C10—O2	−65.8 (2)
N3—C4—C4A—C8A	2.5 (3)	C2—C9—C10—C11	175.64 (17)
O1—C4—C4A—C5	2.7 (3)	O2—C10—C11—Cl3	−58.26 (19)
N3—C4—C4A—C5	−176.0 (2)	C9—C10—C11—Cl3	65.1 (2)
C8A—C4A—C5—C6	0.9 (4)	O2—C10—C11—Cl2	−179.63 (14)
C4—C4A—C5—C6	179.3 (2)	C9—C10—C11—Cl2	−56.2 (2)
C4A—C5—C6—C7	−1.5 (4)	O2—C10—C11—Cl1	62.0 (2)
C5—C6—C7—C8	0.8 (4)	C9—C10—C11—Cl1	−174.54 (14)
C6—C7—C8—C8A	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.79 (3)	2.47 (3)	2.924 (2)	118 (3)
O2—H2···O1i	0.79 (3)	2.13 (3)	2.842 (2)	149 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.79 (3)	2.47 (3)	2.924 (2)	118 (3)
O2—H2⋯O1i	0.79 (3)	2.13 (3)	2.842 (2)	149 (3)

Symmetry code: (i) .