2,4-Dichloro-7,8-dimethyl-quinoline.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(11)H(9)Cl(2)N, both of which are essentially planar [maximum deviations of 0.072 (5) and 0.072 (7) Å]. In the crystal structure, weak π-π stacking inter-actions [centroid-centroid distances = 3.791 (3) Å and 3.855 (3) Å] link pairs of mol-ecules.

Related literature

For the properties and applications of related compounds, see: Biavatti et al. (2002 ▶); Fournet et al. (1981 ▶); McCormick et al. (1996 ▶); Towers et al. (1981 ▶); Ziegler & Gelfert (1959 ▶). For similar crystal structures, see: Subashini et al. (2009 ▶); Somvanshi et al. (2008 ▶).

Experimental

Crystal data

C11H9Cl2N

M = 226.09

Orthorhombic,

a = 20.3054 (9) Å

b = 3.9992 (2) Å

c = 25.5743 (11) Å

V = 2076.77 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.58 mm−1

T = 295 K

0.30 × 0.24 × 0.15 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 ▶) T min = 0.845, T max = 0.918

19807 measured reflections

4009 independent reflections

2599 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.119

S = 0.94

4009 reflections

257 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 1943 Friedel pairs

Flack parameter: 0.15 (10)

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 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020386/vm2029sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020386/vm2029Isup2.hkl

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

C11H9Cl2N	F(000) = 928
Mr = 226.09	Dx = 1.446 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 895 reflections
a = 20.3054 (9) Å	θ = 1.8–24.7°
b = 3.9992 (2) Å	µ = 0.58 mm−1
c = 25.5743 (11) Å	T = 295 K
V = 2076.77 (17) Å3	Needle, colourless
Z = 8	0.30 × 0.24 × 0.15 mm

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	4009 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2599 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −25→25
Tmin = 0.845, Tmax = 0.918	k = −4→4
19807 measured reflections	l = −31→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0652P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
4009 reflections	Δρmax = 0.32 e Å−3
257 parameters	Δρmin = −0.19 e Å−3
1 restraint	Absolute structure: Flack (1983), 1943 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.15 (10)

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 e.s.d.'s 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	0.68230 (6)	0.6442 (5)	0.97181 (6)	0.0916 (6)
Cl2	0.50757 (6)	0.7463 (3)	0.81738 (5)	0.0709 (4)
N1	0.56446 (17)	0.4177 (12)	0.97981 (17)	0.0530 (12)
C1	0.6040 (3)	0.5681 (15)	0.9491 (2)	0.0630 (19)
C2	0.5891 (2)	0.6763 (11)	0.89752 (18)	0.0550 (16)
C3	0.5272 (2)	0.6141 (12)	0.88079 (17)	0.0490 (14)
C4	0.4813 (3)	0.4506 (11)	0.9111 (3)	0.0510 (19)
C5	0.4158 (2)	0.3859 (13)	0.8958 (2)	0.0593 (17)
C6	0.3744 (2)	0.2192 (11)	0.9295 (2)	0.0647 (17)
C7	0.3943 (2)	0.1131 (13)	0.9795 (2)	0.0623 (19)
C8	0.4577 (2)	0.1780 (10)	0.99705 (18)	0.0553 (17)
C9	0.50171 (19)	0.3483 (10)	0.96177 (17)	0.0477 (14)
C10	0.3437 (3)	−0.0425 (13)	1.0129 (2)	0.0640 (19)
C11	0.4804 (3)	0.0815 (14)	1.0504 (2)	0.074 (2)
Cl3	0.56576 (6)	1.1324 (5)	0.69164 (6)	0.0964 (6)
Cl4	0.73974 (6)	1.2634 (3)	0.84687 (5)	0.0694 (4)
N2	0.6857 (2)	0.9027 (12)	0.68457 (18)	0.0627 (17)
C12	0.6456 (3)	1.0586 (13)	0.7160 (2)	0.0540 (17)
C13	0.6582 (2)	1.1805 (11)	0.76636 (19)	0.0553 (16)
C14	0.7208 (2)	1.1269 (12)	0.78476 (17)	0.0500 (16)
C15	0.7689 (2)	0.9656 (10)	0.7534 (3)	0.0420 (18)
C16	0.8335 (3)	0.8998 (14)	0.7678 (2)	0.0620 (17)
C17	0.8766 (2)	0.7485 (11)	0.73560 (19)	0.0590 (17)
C18	0.8568 (2)	0.6444 (12)	0.6858 (2)	0.0610 (19)
C19	0.7928 (2)	0.6889 (10)	0.66826 (18)	0.0567 (17)
C20	0.74761 (19)	0.8565 (11)	0.70266 (17)	0.0507 (16)
C21	0.9046 (4)	0.4700 (17)	0.6447 (4)	0.112 (4)
C22	0.7674 (3)	0.5740 (13)	0.6163 (2)	0.0650 (19)
H2	0.62010	0.78320	0.87660	0.0660*
H5	0.40070	0.45540	0.86320	0.0710*
H6	0.33150	0.17480	0.91870	0.0780*
H10A	0.32250	0.12660	1.03360	0.0960*
H10B	0.36400	−0.20380	1.03550	0.0960*
H10C	0.31150	−0.15180	0.99130	0.0960*
H11A	0.46530	0.24420	1.07530	0.1120*
H11B	0.52760	0.07210	1.05100	0.1120*
H11C	0.46280	−0.13390	1.05930	0.1120*
H13	0.62630	1.29030	0.78600	0.0660*
H16	0.84760	0.96260	0.80100	0.0740*
H17	0.91970	0.71310	0.74650	0.0700*
H21A	0.90020	0.57790	0.61130	0.1670*
H21B	0.89310	0.23810	0.64140	0.1670*
H21C	0.94930	0.48880	0.65650	0.1670*
H22A	0.79460	0.66330	0.58900	0.0970*
H22B	0.72290	0.65090	0.61180	0.0970*
H22C	0.76820	0.33420	0.61490	0.0970*

	U11	U22	U33	U12	U13	U23
Cl1	0.0611 (8)	0.1339 (13)	0.0798 (10)	−0.0212 (8)	−0.0161 (7)	0.0013 (12)
Cl2	0.0827 (8)	0.0806 (7)	0.0495 (6)	0.0103 (6)	−0.0061 (6)	0.0020 (6)
N1	0.047 (2)	0.068 (2)	0.044 (2)	0.004 (2)	−0.0064 (19)	−0.008 (2)
C1	0.048 (3)	0.069 (3)	0.072 (4)	−0.003 (3)	−0.001 (3)	−0.013 (3)
C2	0.062 (3)	0.056 (3)	0.047 (2)	−0.002 (2)	0.005 (2)	−0.007 (2)
C3	0.060 (3)	0.048 (2)	0.039 (2)	0.006 (2)	0.000 (2)	−0.005 (2)
C4	0.052 (3)	0.041 (3)	0.060 (4)	0.009 (2)	−0.008 (3)	−0.020 (2)
C5	0.045 (3)	0.075 (3)	0.058 (3)	0.010 (3)	−0.003 (2)	−0.019 (3)
C6	0.046 (3)	0.067 (3)	0.081 (3)	0.007 (2)	−0.004 (2)	−0.016 (3)
C7	0.054 (3)	0.054 (3)	0.079 (4)	0.005 (3)	0.012 (3)	−0.016 (3)
C8	0.066 (3)	0.048 (3)	0.052 (3)	0.004 (2)	0.008 (2)	−0.012 (2)
C9	0.055 (2)	0.038 (2)	0.050 (3)	0.001 (2)	0.011 (2)	−0.012 (2)
C10	0.062 (4)	0.062 (3)	0.068 (3)	−0.004 (2)	0.018 (3)	−0.018 (3)
C11	0.088 (4)	0.067 (3)	0.068 (4)	0.002 (3)	−0.001 (3)	−0.004 (3)
Cl3	0.0610 (8)	0.1433 (13)	0.0848 (10)	0.0298 (9)	−0.0193 (7)	−0.0122 (13)
Cl4	0.0783 (7)	0.0777 (7)	0.0523 (6)	−0.0045 (6)	−0.0028 (6)	−0.0053 (6)
N2	0.067 (3)	0.067 (3)	0.054 (3)	0.006 (2)	−0.002 (2)	−0.002 (3)
C12	0.046 (3)	0.073 (3)	0.043 (3)	0.005 (2)	−0.002 (2)	−0.006 (3)
C13	0.042 (2)	0.061 (3)	0.063 (3)	0.008 (2)	0.005 (2)	0.002 (2)
C14	0.058 (3)	0.047 (3)	0.045 (2)	−0.003 (2)	0.006 (2)	0.002 (2)
C15	0.034 (3)	0.039 (2)	0.053 (4)	0.0013 (16)	0.004 (3)	0.0138 (19)
C16	0.070 (3)	0.057 (3)	0.059 (3)	−0.014 (3)	−0.009 (3)	0.004 (3)
C17	0.050 (3)	0.060 (3)	0.067 (3)	−0.001 (2)	−0.004 (2)	0.006 (3)
C18	0.060 (3)	0.043 (3)	0.080 (4)	−0.001 (2)	0.016 (3)	0.018 (3)
C19	0.063 (3)	0.049 (3)	0.058 (3)	−0.008 (2)	0.007 (2)	0.011 (2)
C20	0.047 (2)	0.054 (3)	0.051 (3)	0.000 (2)	0.009 (2)	0.007 (2)
C21	0.084 (5)	0.086 (5)	0.166 (8)	0.018 (3)	0.056 (5)	0.007 (4)
C22	0.084 (4)	0.072 (3)	0.039 (3)	0.016 (3)	0.007 (3)	−0.002 (3)

Cl1—C1	1.720 (6)	C10—H10C	0.9600
Cl2—C3	1.752 (5)	C11—H11B	0.9600
Cl3—C12	1.762 (6)	C11—H11C	0.9600
Cl4—C14	1.723 (5)	C11—H11A	0.9600
N1—C9	1.383 (5)	C12—C13	1.401 (7)
N1—C1	1.274 (7)	C13—C14	1.372 (6)
N2—C20	1.352 (6)	C14—C15	1.419 (7)
N2—C12	1.303 (7)	C15—C16	1.388 (7)
C1—C2	1.421 (7)	C15—C20	1.436 (8)
C2—C3	1.351 (6)	C16—C17	1.345 (7)
C3—C4	1.377 (8)	C17—C18	1.399 (7)
C4—C5	1.410 (7)	C18—C19	1.386 (6)
C4—C9	1.421 (8)	C18—C21	1.592 (10)
C5—C6	1.376 (7)	C19—C20	1.437 (6)
C6—C7	1.407 (7)	C19—C22	1.498 (7)
C7—C10	1.474 (7)	C13—H13	0.9300
C7—C8	1.388 (6)	C16—H16	0.9300
C8—C11	1.491 (7)	C17—H17	0.9300
C8—C9	1.441 (6)	C21—H21A	0.9600
C2—H2	0.9300	C21—H21B	0.9600
C5—H5	0.9300	C21—H21C	0.9600
C6—H6	0.9300	C22—H22A	0.9600
C10—H10A	0.9600	C22—H22B	0.9600
C10—H10B	0.9600	C22—H22C	0.9600
Cl1···H22Ai	3.0300	H5···H16iii	2.5500
Cl2···H5	2.7300	H6···H10C	2.3100
Cl2···H13ii	3.1300	H6···Cl4iii	3.1500
Cl2···H17iii	3.1400	H10A···C22viii	3.0400
Cl3···H21Civ	2.9500	H10A···H22Bviii	2.3800
Cl4···H6v	3.1500	H10B···C11	2.6500
Cl4···H16	2.7600	H10B···H11C	2.1200
N1···H11B	2.4100	H10C···H6	2.3100
N2···H22B	2.2500	H11A···H11Cvi	2.5200
C3···C4vi	3.558 (7)	H11B···N1	2.4100
C4···C3ii	3.558 (7)	H11C···H11Aii	2.5200
C5···C6vi	3.543 (7)	H11C···C10	2.7200
C6···C5ii	3.543 (7)	H11C···H10B	2.1200
C8···C9ii	3.553 (6)	H13···Cl2vi	3.1300
C9···C8vi	3.553 (6)	H16···Cl4	2.7600
C14···C15vi	3.584 (6)	H16···H5v	2.5500
C15···C14ii	3.584 (6)	H17···H21C	2.5400
C18···C21vi	3.598 (9)	H17···Cl2v	3.1400
C19···C20ii	3.563 (6)	H21A···C22	2.7000
C20···C19vi	3.563 (6)	H21A···H22A	2.2400
C21···C18ii	3.598 (9)	H21B···C18ii	2.7300
C10···H11C	2.7200	H21B···C19ii	3.0700
C11···H10B	2.6500	H21B···C21ii	3.0800
C18···H21Bvi	2.7300	H21B···C22	2.9500
C19···H21Bvi	3.0700	H21C···H17	2.5400
C19···H22Cvi	2.9600	H21C···Cl3ix	2.9500
C20···H22Cvi	2.9800	H22A···C21	2.7600
C21···H21Bvi	3.0800	H22A···H21A	2.2400
C21···H22C	2.9200	H22A···Cl1x	3.0300
C21···H22A	2.7600	H22B···N2	2.2500
C22···H22Cvi	3.0400	H22B···H10Avii	2.3800
C22···H10Avii	3.0400	H22C···C19ii	2.9600
C22···H21B	2.9500	H22C···C20ii	2.9800
C22···H21A	2.7000	H22C···C21	2.9200
H5···Cl2	2.7300	H22C···C22ii	3.0400
C1—N1—C9	118.0 (4)	H11A—C11—H11B	110.00
C12—N2—C20	115.8 (5)	Cl3—C12—N2	115.9 (4)
Cl1—C1—N1	117.3 (4)	Cl3—C12—C13	115.8 (4)
N1—C1—C2	125.6 (5)	N2—C12—C13	128.3 (5)
Cl1—C1—C2	117.2 (4)	C12—C13—C14	115.5 (4)
C1—C2—C3	115.9 (4)	Cl4—C14—C13	118.3 (3)
Cl2—C3—C2	116.7 (3)	Cl4—C14—C15	120.8 (4)
C2—C3—C4	122.6 (5)	C13—C14—C15	121.0 (4)
Cl2—C3—C4	120.7 (4)	C14—C15—C16	125.9 (6)
C3—C4—C5	124.7 (6)	C14—C15—C20	116.2 (4)
C5—C4—C9	118.4 (5)	C16—C15—C20	117.8 (5)
C3—C4—C9	116.9 (5)	C15—C16—C17	122.5 (5)
C4—C5—C6	119.4 (5)	C16—C17—C18	120.3 (4)
C5—C6—C7	122.7 (4)	C17—C18—C19	121.7 (4)
C6—C7—C8	120.3 (4)	C17—C18—C21	123.8 (5)
C6—C7—C10	117.0 (4)	C19—C18—C21	114.5 (5)
C8—C7—C10	122.6 (5)	C18—C19—C20	117.4 (4)
C7—C8—C9	117.5 (4)	C18—C19—C22	124.8 (4)
C7—C8—C11	122.3 (4)	C20—C19—C22	117.8 (4)
C9—C8—C11	120.2 (4)	N2—C20—C15	123.2 (4)
N1—C9—C8	117.2 (4)	N2—C20—C19	116.6 (4)
C4—C9—C8	121.8 (4)	C15—C20—C19	120.2 (4)
N1—C9—C4	121.0 (4)	C12—C13—H13	122.00
C3—C2—H2	122.00	C14—C13—H13	122.00
C1—C2—H2	122.00	C15—C16—H16	119.00
C4—C5—H5	120.00	C17—C16—H16	119.00
C6—C5—H5	120.00	C16—C17—H17	120.00
C7—C6—H6	119.00	C18—C17—H17	120.00
C5—C6—H6	119.00	C18—C21—H21A	109.00
C7—C10—H10A	110.00	C18—C21—H21B	109.00
C7—C10—H10B	109.00	C18—C21—H21C	110.00
H10A—C10—H10B	110.00	H21A—C21—H21B	109.00
H10A—C10—H10C	109.00	H21A—C21—H21C	109.00
C7—C10—H10C	109.00	H21B—C21—H21C	109.00
H10B—C10—H10C	109.00	C19—C22—H22A	109.00
C8—C11—H11B	109.00	C19—C22—H22B	109.00
C8—C11—H11C	110.00	C19—C22—H22C	110.00
C8—C11—H11A	109.00	H22A—C22—H22B	110.00
H11A—C11—H11C	109.00	H22A—C22—H22C	110.00
H11B—C11—H11C	109.00	H22B—C22—H22C	109.00
C9—N1—C1—Cl1	−178.7 (4)	C7—C8—C9—C4	0.7 (6)
C9—N1—C1—C2	0.8 (8)	C11—C8—C9—N1	−0.4 (6)
C1—N1—C9—C4	−1.9 (7)	C11—C8—C9—C4	−178.6 (4)
C1—N1—C9—C8	180.0 (5)	C7—C8—C9—N1	178.9 (4)
C20—N2—C12—Cl3	177.8 (4)	Cl3—C12—C13—C14	−179.0 (4)
C20—N2—C12—C13	−0.9 (8)	N2—C12—C13—C14	−0.3 (8)
C12—N2—C20—C15	0.8 (7)	C12—C13—C14—Cl4	−178.9 (4)
C12—N2—C20—C19	−179.2 (4)	C12—C13—C14—C15	1.5 (7)
N1—C1—C2—C3	0.7 (8)	Cl4—C14—C15—C16	0.2 (7)
Cl1—C1—C2—C3	−179.8 (4)	Cl4—C14—C15—C20	178.9 (3)
C1—C2—C3—Cl2	179.8 (4)	C13—C14—C15—C16	179.7 (5)
C1—C2—C3—C4	−1.2 (7)	C13—C14—C15—C20	−1.6 (7)
Cl2—C3—C4—C5	−2.4 (7)	C14—C15—C16—C17	−179.3 (5)
Cl2—C3—C4—C9	179.2 (3)	C20—C15—C16—C17	2.0 (8)
C2—C3—C4—C9	0.2 (7)	C14—C15—C20—N2	0.3 (7)
C2—C3—C4—C5	178.7 (5)	C14—C15—C20—C19	−179.6 (4)
C3—C4—C5—C6	179.9 (5)	C16—C15—C20—N2	179.2 (5)
C9—C4—C5—C6	−1.7 (7)	C16—C15—C20—C19	−0.8 (7)
C5—C4—C9—C8	0.9 (7)	C15—C16—C17—C18	−1.3 (8)
C3—C4—C9—N1	1.4 (7)	C16—C17—C18—C19	−0.8 (7)
C3—C4—C9—C8	179.4 (4)	C16—C17—C18—C21	178.8 (5)
C5—C4—C9—N1	−177.2 (4)	C17—C18—C19—C20	1.9 (7)
C4—C5—C6—C7	1.0 (7)	C17—C18—C19—C22	−177.8 (4)
C5—C6—C7—C10	176.0 (5)	C21—C18—C19—C20	−177.7 (4)
C5—C6—C7—C8	0.7 (7)	C21—C18—C19—C22	2.6 (7)
C6—C7—C8—C9	−1.5 (7)	C18—C19—C20—N2	178.9 (4)
C6—C7—C8—C11	177.8 (4)	C18—C19—C20—C15	−1.1 (6)
C10—C7—C8—C9	−176.5 (4)	C22—C19—C20—N2	−1.3 (6)
C10—C7—C8—C11	2.8 (7)	C22—C19—C20—C15	178.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl2	0.93	2.73	3.094 (5)	104
C11—H11B···N1	0.96	2.41	2.825 (7)	106
C16—H16···Cl4	0.93	2.76	3.135 (6)	105
C22—H22B···N2	0.96	2.25	2.744 (7)	111