2-Chloro-4-methyl­quinoline

The structure of the title compound, C₁₀H₈ClN, comprises planar mol­ecules that form stacked columns parallel to the b cell direction. Two symmetry-related mol­ecules associate via C—H...N interactions to form a non-planar R₂²(8) dimer.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.115
• Data-to-parameter ratio = 17.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

NO COMMENT

S2. Experimental

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from a methanol solution.

S3. Refinement

All H atoms were included in the refinement at calculated positions as riding models, with C—-H set to 0.95 (Ar—H) and 0.98 Å (CH₃).

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular configuration and atom-numbering scheme for (I), showing 30% probability displacement ellipsoids.

'2-Chloro-4-methylquinoline'

Crystal data

C10H8ClN	Dx = 1.414 Mg m^−3
Mr = 177.62	Melting point: 329-331 K K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 12.721 (3) Å	Cell parameters from 3728 reflections
b = 7.8961 (16) Å	θ = 2.9–27.5°
c = 16.617 (3) Å	µ = 0.39 mm^−1
V = 1669.1 (6) Å^3	T = 150 K
Z = 8	Plate, colourless
F(000) = 736	0.20 × 0.15 × 0.07 mm

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	1892 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1466 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ and ω scans	h = −16→16
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −10→10
Tmin = 0.926, Tmax = 0.973	l = −21→17
7671 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0699P)^2] where P = (Fo^2 + 2Fc^2)/3
1892 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.65826 (10)	−0.06443 (14)	0.49091 (8)	0.0262 (3)
C2	0.75263 (12)	−0.04143 (18)	0.46408 (11)	0.0263 (4)
Cl2	0.76408 (4)	0.05756 (5)	0.37023 (2)	0.03468 (19)
C3	0.84655 (13)	−0.08847 (18)	0.50317 (10)	0.0270 (4)
H3	0.9128	−0.0657	0.4791	0.034*
C4	0.84099 (12)	−0.16720 (17)	0.57612 (9)	0.0255 (4)
C41	0.93894 (13)	−0.2178 (2)	0.62011 (10)	0.0327 (4)
H41	0.9995	−0.2074	0.5840	0.041*
H42	0.9325	−0.3354	0.6383	0.041*
H43	0.9488	−0.1436	0.6668	0.041*
C5	0.72124 (13)	−0.27871 (19)	0.68369 (10)	0.0291 (4)
H5	0.7796	−0.3161	0.7146	0.036*
C6	0.62223 (13)	−0.30384 (19)	0.71223 (10)	0.0328 (4)
H6	0.6122	−0.3583	0.7626	0.041*
C7	0.53455 (13)	−0.24940 (19)	0.66735 (10)	0.0328 (4)
H7	0.4657	−0.2675	0.6877	0.041*
C8	0.54789 (12)	−0.17088 (17)	0.59497 (11)	0.0293 (4)
H8	0.4884	−0.1343	0.5651	0.037*
C9	0.65001 (12)	−0.14378 (17)	0.56429 (9)	0.0250 (4)
C10	0.73904 (11)	−0.19804 (17)	0.60897 (11)	0.0246 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0247 (8)	0.0258 (7)	0.0280 (7)	0.0007 (5)	−0.0037 (6)	−0.0021 (5)
C2	0.0310 (10)	0.0222 (8)	0.0258 (9)	−0.0001 (5)	−0.0023 (7)	−0.0035 (6)
Cl2	0.0395 (3)	0.0365 (3)	0.0280 (3)	−0.00297 (16)	−0.00131 (17)	0.00304 (15)
C3	0.0223 (9)	0.0276 (7)	0.0310 (8)	−0.0019 (6)	−0.0008 (7)	−0.0047 (6)
C4	0.0222 (8)	0.0239 (7)	0.0305 (9)	0.0012 (6)	−0.0038 (7)	−0.0076 (6)
C41	0.0264 (9)	0.0344 (8)	0.0373 (10)	0.0022 (7)	−0.0072 (7)	−0.0016 (7)
C5	0.0306 (9)	0.0286 (8)	0.0281 (9)	0.0013 (6)	−0.0046 (7)	−0.0022 (6)
C6	0.0366 (10)	0.0338 (9)	0.0279 (9)	−0.0007 (7)	0.0007 (8)	−0.0008 (7)
C7	0.0273 (9)	0.0377 (9)	0.0335 (10)	−0.0023 (7)	0.0037 (7)	−0.0019 (7)
C8	0.0228 (9)	0.0299 (8)	0.0351 (9)	0.0022 (6)	−0.0032 (7)	−0.0039 (6)
C9	0.0247 (9)	0.0232 (7)	0.0272 (8)	0.0002 (6)	−0.0021 (7)	−0.0046 (6)
C10	0.0260 (9)	0.0200 (8)	0.0280 (8)	0.0009 (6)	−0.0050 (6)	−0.0064 (6)

Geometric parameters (Å, º)

N1—C2	1.293 (2)	C5—C6	1.360 (2)
N1—C9	1.375 (2)	C5—C10	1.414 (2)
C2—C3	1.410 (2)	C5—H5	0.95
C2—Cl2	1.7504 (18)	C6—C7	1.409 (2)
C3—C4	1.364 (2)	C6—H6	0.95
C3—H3	0.95	C7—C8	1.364 (2)
C4—C10	1.428 (2)	C7—H7	0.95
C4—C41	1.499 (2)	C8—C9	1.412 (2)
C41—H41	0.98	C8—H8	0.95
C41—H42	0.98	C9—C10	1.420 (2)
C41—H43	0.98
C2—N1—C9	116.14 (13)	C6—C5—H5	119.3
N1—C2—C3	126.21 (15)	C10—C5—H5	119.3
N1—C2—Cl2	116.56 (12)	C5—C6—C7	120.27 (16)
C3—C2—Cl2	117.23 (12)	C5—C6—H6	119.9
C4—C3—C2	119.05 (14)	C7—C6—H6	119.9
C4—C3—H3	120.5	C8—C7—C6	120.46 (15)
C2—C3—H3	120.5	C8—C7—H7	119.8
C3—C4—C10	117.68 (14)	C6—C7—H7	119.8
C3—C4—C41	120.78 (14)	C7—C8—C9	120.12 (14)
C10—C4—C41	121.54 (14)	C7—C8—H8	119.9
C4—C41—H41	109.5	C9—C8—H8	119.9
C4—C41—H42	109.5	N1—C9—C8	117.36 (13)
H41—C41—H42	109.5	N1—C9—C10	122.70 (14)
C4—C41—H43	109.5	C8—C9—C10	119.95 (15)
H41—C41—H43	109.5	C5—C10—C9	117.86 (14)
H42—C41—H43	109.5	C5—C10—C4	123.92 (14)
C6—C5—C10	121.34 (15)	C9—C10—C4	118.22 (16)
C9—N1—C2—C3	−0.6 (2)	C7—C8—C9—C10	−0.1 (2)
C9—N1—C2—Cl2	179.38 (10)	C6—C5—C10—C9	0.0 (2)
N1—C2—C3—C4	0.5 (2)	C6—C5—C10—C4	179.61 (14)
Cl2—C2—C3—C4	−179.46 (11)	N1—C9—C10—C5	−179.85 (12)
C2—C3—C4—C10	0.1 (2)	C8—C9—C10—C5	0.1 (2)
C2—C3—C4—C41	−179.38 (13)	N1—C9—C10—C4	0.5 (2)
C10—C5—C6—C7	0.0 (2)	C8—C9—C10—C4	−179.57 (12)
C5—C6—C7—C8	−0.1 (2)	C3—C4—C10—C5	179.80 (13)
C6—C7—C8—C9	0.1 (2)	C41—C4—C10—C5	−0.7 (2)
C2—N1—C9—C8	−179.87 (13)	C3—C4—C10—C9	−0.6 (2)
C2—N1—C9—C10	0.1 (2)	C41—C4—C10—C9	178.93 (12)
C7—C8—C9—N1	179.80 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1^i	0.95	2.61	3.517 (2)	160

Symmetry code: (i) −x+1, −y, −z+1.