2-Chloro-8-methyl-3-[(pyrimidin-4-yl-oxy)meth-yl]quinoline.

In the title compound, C(15)H(12)ClN(3)O, the quinoline ring system is essentially planar, with a maximum deviation of 0.017 (1) Å. The crystal packing is stabilized by π-π stacking inter-actions between the quinoline rings of adjacent mol-ecule, with a centroid-centroid distance of 3.5913 (8) Å. A weak C-H⋯π contact is also observed between mol-ecules.

Related literature

For pyrimidine analogues, see: Svenstrup et al. (2008 ▶). For quinoline analogues, see: Roopan & Khan (2009 ▶); Khan et al. (2009 ▶, 2010a ▶,b ▶). For the biological activity and mode of action of alkyl­ating agent, see: Singer (1986 ▶). For the synthesis and regioselective alkyl­ation of 4(3H)-pyrimidone, see: Roopan et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a structural discussion on hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H12ClN3O

M = 285.73

Monoclinic,

a = 11.9975 (2) Å

b = 8.45037 (15) Å

c = 12.95869 (19) Å

β = 96.7619 (16)°

V = 1304.66 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.23 × 0.18 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.936, T max = 0.958

13753 measured reflections

2564 independent reflections

2005 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.07

2564 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 ▶); 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011694/fj2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011694/fj2289Isup2.hkl

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

C15H12ClN3O	F(000) = 592
Mr = 285.73	Dx = 1.455 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1065 reflections
a = 11.9975 (2) Å	θ = 2.5–26.0°
b = 8.45037 (15) Å	µ = 0.29 mm−1
c = 12.95869 (19) Å	T = 295 K
β = 96.7619 (16)°	Prism, colourless
V = 1304.66 (4) Å3	0.23 × 0.18 × 0.15 mm
Z = 4

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	2564 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2005 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.936, Tmax = 0.958	k = −10→10
13753 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3
2564 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl1	0.52448 (3)	0.22861 (5)	−0.21533 (3)	0.0452 (2)
O1	0.35909 (9)	0.13571 (11)	0.06428 (7)	0.0413 (4)
N1	0.66190 (10)	0.38546 (12)	−0.08362 (8)	0.0315 (4)
N2	0.22497 (11)	−0.02532 (14)	−0.02386 (9)	0.0398 (4)
N3	0.08616 (12)	−0.14701 (16)	0.06771 (13)	0.0569 (6)
C1	0.57162 (12)	0.30022 (16)	−0.09125 (10)	0.0297 (4)
C2	0.50756 (12)	0.25855 (14)	−0.01007 (10)	0.0282 (4)
C3	0.54805 (12)	0.31329 (15)	0.08638 (10)	0.0299 (4)
C4	0.69272 (13)	0.46034 (15)	0.20041 (11)	0.0365 (5)
C5	0.78847 (14)	0.54796 (16)	0.20983 (12)	0.0418 (5)
C6	0.84248 (13)	0.58407 (16)	0.12263 (12)	0.0399 (5)
C7	0.80215 (13)	0.53220 (16)	0.02491 (11)	0.0345 (5)
C8	0.70266 (12)	0.43947 (15)	0.01381 (10)	0.0291 (4)
C9	0.64712 (12)	0.40438 (15)	0.10159 (10)	0.0296 (4)
C10	0.40366 (12)	0.16051 (16)	−0.03229 (10)	0.0327 (5)
C11	0.26755 (13)	0.04265 (16)	0.06302 (11)	0.0344 (5)
C12	0.22415 (15)	0.02264 (18)	0.15667 (12)	0.0459 (6)
C13	0.13310 (16)	−0.0742 (2)	0.15376 (15)	0.0551 (7)
C14	0.13543 (15)	−0.11672 (19)	−0.01572 (14)	0.0514 (6)
C15	0.86040 (14)	0.57135 (18)	−0.06845 (13)	0.0465 (6)
H3	0.50970	0.29010	0.14280	0.0360*
H4	0.65740	0.43730	0.25880	0.0440*
H5	0.81850	0.58440	0.27500	0.0500*
H6	0.90750	0.64490	0.13120	0.0480*
H10A	0.34910	0.21490	−0.08100	0.0390*
H10B	0.42140	0.05980	−0.06240	0.0390*
H12	0.25520	0.07210	0.21750	0.0550*
H13	0.10170	−0.09080	0.21520	0.0660*
H14	0.10390	−0.16500	−0.07680	0.0620*
H15A	0.92390	0.63810	−0.04780	0.0700*
H15B	0.80920	0.62550	−0.11900	0.0700*
H15C	0.88530	0.47550	−0.09820	0.0700*

	U11	U22	U33	U12	U13	U23
Cl1	0.0438 (3)	0.0642 (3)	0.0278 (2)	−0.0083 (2)	0.0045 (2)	−0.0068 (2)
O1	0.0385 (7)	0.0543 (6)	0.0322 (6)	−0.0162 (5)	0.0092 (5)	−0.0009 (5)
N1	0.0286 (7)	0.0364 (6)	0.0301 (6)	0.0026 (5)	0.0059 (5)	0.0019 (5)
N2	0.0355 (8)	0.0428 (7)	0.0406 (7)	−0.0044 (6)	0.0027 (6)	0.0005 (6)
N3	0.0425 (10)	0.0507 (9)	0.0792 (11)	−0.0086 (7)	0.0143 (8)	0.0065 (8)
C1	0.0293 (8)	0.0340 (7)	0.0259 (7)	0.0036 (6)	0.0034 (6)	−0.0007 (5)
C2	0.0268 (8)	0.0278 (7)	0.0303 (7)	0.0045 (6)	0.0046 (6)	0.0023 (6)
C3	0.0307 (9)	0.0319 (7)	0.0280 (7)	0.0033 (6)	0.0078 (6)	0.0029 (6)
C4	0.0409 (10)	0.0368 (8)	0.0313 (8)	0.0009 (7)	0.0025 (7)	0.0009 (6)
C5	0.0469 (11)	0.0396 (8)	0.0362 (8)	0.0005 (7)	−0.0062 (7)	−0.0046 (6)
C6	0.0315 (9)	0.0359 (8)	0.0507 (9)	−0.0041 (7)	−0.0015 (7)	−0.0012 (7)
C7	0.0306 (9)	0.0316 (8)	0.0418 (8)	0.0017 (6)	0.0060 (7)	0.0014 (6)
C8	0.0279 (8)	0.0285 (7)	0.0309 (7)	0.0037 (6)	0.0035 (6)	0.0006 (5)
C9	0.0297 (8)	0.0279 (7)	0.0310 (7)	0.0037 (6)	0.0029 (6)	0.0021 (5)
C10	0.0310 (9)	0.0386 (8)	0.0288 (7)	−0.0009 (6)	0.0054 (6)	0.0011 (6)
C11	0.0295 (9)	0.0343 (8)	0.0399 (8)	−0.0010 (6)	0.0063 (7)	0.0045 (6)
C12	0.0498 (11)	0.0489 (9)	0.0417 (9)	−0.0058 (8)	0.0165 (8)	0.0004 (7)
C13	0.0533 (12)	0.0523 (10)	0.0647 (12)	−0.0042 (9)	0.0281 (10)	0.0087 (9)
C14	0.0422 (11)	0.0501 (10)	0.0605 (11)	−0.0089 (8)	0.0008 (9)	−0.0019 (8)
C15	0.0387 (10)	0.0498 (10)	0.0526 (10)	−0.0108 (8)	0.0119 (8)	0.0019 (7)

Cl1—C1	1.7485 (14)	C7—C8	1.421 (2)
O1—C10	1.4330 (16)	C7—C15	1.504 (2)
O1—C11	1.3493 (18)	C8—C9	1.4158 (19)
N1—C1	1.2948 (18)	C11—C12	1.386 (2)
N1—C8	1.3770 (17)	C12—C13	1.362 (3)
N2—C11	1.3126 (18)	C3—H3	0.9300
N2—C14	1.337 (2)	C4—H4	0.9300
N3—C13	1.338 (2)	C5—H5	0.9300
N3—C14	1.317 (2)	C6—H6	0.9300
C1—C2	1.4184 (19)	C10—H10A	0.9700
C2—C3	1.3672 (18)	C10—H10B	0.9700
C2—C10	1.496 (2)	C12—H12	0.9300
C3—C9	1.410 (2)	C13—H13	0.9300
C4—C5	1.360 (2)	C14—H14	0.9300
C4—C9	1.4134 (19)	C15—H15A	0.9600
C5—C6	1.401 (2)	C15—H15B	0.9600
C6—C7	1.373 (2)	C15—H15C	0.9600
Cl1···C15i	3.5264 (17)	C5···H10Avi	2.9800
Cl1···H10A	2.8900	C6···H10Avi	2.8600
Cl1···H10B	2.8400	C7···H10Avi	2.9500
Cl1···H14ii	3.0800	C10···H10Bv	2.9600
O1···H3	2.3600	C11···H15Bvi	3.0700
N1···H15B	2.7600	C12···H15Bvi	3.0300
N1···H15C	2.8100	H3···O1	2.3600
N2···H10A	2.6700	H3···H4	2.5100
N2···H10B	2.5700	H4···H3	2.5100
N2···H4iii	2.9300	H4···N2ix	2.9300
N3···H15Aiv	2.9400	H5···C3x	2.9800
N3···H15Cv	2.8200	H6···H15A	2.3500
C1···C3vi	3.5712 (19)	H10A···Cl1	2.8900
C1···C11v	3.476 (2)	H10A···N2	2.6700
C2···C8vi	3.5842 (19)	H10A···C5vi	2.9800
C2···C9vi	3.5278 (18)	H10A···C6vi	2.8600
C3···C1vi	3.5712 (19)	H10A···C7vi	2.9500
C7···C14v	3.595 (2)	H10B···Cl1	2.8400
C7···C10vi	3.592 (2)	H10B···N2	2.5700
C8···C2vi	3.5842 (19)	H10B···C2v	2.9400
C8···C14v	3.347 (2)	H10B···C10v	2.9600
C9···C2vi	3.5278 (18)	H10B···H10Bv	2.5400
C10···C7vi	3.592 (2)	H14···Cl1xi	3.0800
C10···C10v	3.598 (2)	H15A···N3xii	2.9400
C11···C1v	3.476 (2)	H15A···H6	2.3500
C14···C8v	3.347 (2)	H15B···N1	2.7600
C14···C7v	3.595 (2)	H15B···C11vi	3.0700
C15···Cl1vii	3.5264 (17)	H15B···C12vi	3.0300
C2···H10Bv	2.9400	H15C···N1	2.8100
C3···H5viii	2.9800	H15C···N3v	2.8200
C10—O1—C11	117.49 (10)	N3—C13—C12	123.83 (17)
C1—N1—C8	117.26 (11)	N2—C14—N3	128.27 (16)
C11—N2—C14	114.85 (13)	C2—C3—H3	119.00
C13—N3—C14	114.15 (15)	C9—C3—H3	119.00
Cl1—C1—N1	116.09 (10)	C5—C4—H4	120.00
Cl1—C1—C2	116.83 (10)	C9—C4—H4	120.00
N1—C1—C2	127.08 (12)	C4—C5—H5	120.00
C1—C2—C3	115.39 (12)	C6—C5—H5	120.00
C1—C2—C10	120.44 (11)	C5—C6—H6	119.00
C3—C2—C10	124.17 (12)	C7—C6—H6	119.00
C2—C3—C9	121.02 (12)	O1—C10—H10A	110.00
C5—C4—C9	119.75 (14)	O1—C10—H10B	110.00
C4—C5—C6	120.81 (14)	C2—C10—H10A	110.00
C5—C6—C7	121.88 (14)	C2—C10—H10B	110.00
C6—C7—C8	118.03 (13)	H10A—C10—H10B	108.00
C6—C7—C15	121.68 (14)	C11—C12—H12	122.00
C8—C7—C15	120.29 (13)	C13—C12—H12	122.00
N1—C8—C7	118.62 (12)	N3—C13—H13	118.00
N1—C8—C9	121.15 (12)	C12—C13—H13	118.00
C7—C8—C9	120.23 (12)	N2—C14—H14	116.00
C3—C9—C4	122.63 (12)	N3—C14—H14	116.00
C3—C9—C8	118.08 (12)	C7—C15—H15A	109.00
C4—C9—C8	119.29 (13)	C7—C15—H15B	109.00
O1—C10—C2	107.52 (10)	C7—C15—H15C	109.00
O1—C11—N2	119.96 (13)	H15A—C15—H15B	109.00
O1—C11—C12	116.72 (13)	H15A—C15—H15C	109.00
N2—C11—C12	123.31 (14)	H15B—C15—H15C	109.00
C11—C12—C13	115.58 (15)
C11—O1—C10—C2	−176.75 (11)	C2—C3—C9—C4	−178.71 (13)
C10—O1—C11—N2	2.21 (19)	C2—C3—C9—C8	0.9 (2)
C10—O1—C11—C12	−178.68 (13)	C9—C4—C5—C6	0.2 (2)
C8—N1—C1—Cl1	−178.15 (10)	C5—C4—C9—C3	−179.87 (13)
C8—N1—C1—C2	1.6 (2)	C5—C4—C9—C8	0.6 (2)
C1—N1—C8—C7	179.47 (12)	C4—C5—C6—C7	−0.5 (2)
C1—N1—C8—C9	−0.69 (19)	C5—C6—C7—C8	0.0 (2)
C14—N2—C11—O1	179.03 (13)	C5—C6—C7—C15	179.97 (14)
C14—N2—C11—C12	0.0 (2)	C6—C7—C8—N1	−179.40 (12)
C11—N2—C14—N3	−0.5 (2)	C6—C7—C8—C9	0.8 (2)
C14—N3—C13—C12	−0.3 (2)	C15—C7—C8—N1	0.6 (2)
C13—N3—C14—N2	0.6 (3)	C15—C7—C8—C9	−179.20 (13)
Cl1—C1—C2—C3	178.55 (10)	N1—C8—C9—C3	−0.48 (19)
Cl1—C1—C2—C10	−1.18 (17)	N1—C8—C9—C4	179.12 (12)
N1—C1—C2—C3	−1.2 (2)	C7—C8—C9—C3	179.36 (12)
N1—C1—C2—C10	179.08 (13)	C7—C8—C9—C4	−1.0 (2)
C1—C2—C3—C9	−0.14 (19)	O1—C11—C12—C13	−178.79 (14)
C10—C2—C3—C9	179.58 (12)	N2—C11—C12—C13	0.3 (2)
C1—C2—C10—O1	178.90 (11)	C11—C12—C13—N3	−0.1 (3)
C3—C2—C10—O1	−0.80 (18)

Cg3 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.36	2.7056 (17)	102
C10—H10A···Cg3vi	0.97	2.72	3.5132 (15)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯Cg3i	0.97	2.72	3.5132 (15)	140

Symmetry code: (i) .