N-[(2-Chloro-8-methyl-quinolin-3-yl)meth-yl]-4-meth-oxy-aniline.

In the title compound, C(18)H(17)ClN(2)O, the quinoline ring system is essentially planar; the r.m.s. deviation for the non-H atoms is 0.04 Å with a maximum deviation from the mean plane of 0.026 (4) Å for the C atom bonded to the -CH(2)- group. The meth-oxy-substituted benzene ring forms a dihedral angle of 70.22 (4)° with this ring system. The crystal structure can be described as zigzag layers in which the quinoline ring systems are parallel to (011) and molecules are connected via inter-molecular N-H⋯N hydrogen bonds, forming chains along [100]. The crystal studied was an inversion twin with a 0.86 (5):0.14 (5) domain ratio.

Related literature

For background to quinoline compounds, see: Elderfield (1960 ▶); Wright et al. (2001 ▶); Sahu et al. (2002 ▶); Bringmann et al. (2004 ▶); Kournetsov et al. (2005 ▶). For the biological and pharmaceutical applications of quinolines, see: Albert & Ritchie (1955 ▶); Mouzine et al. (1980 ▶); Lyle & Keefer (1967 ▶). For the general synthesis of quinolines, see: Cope & Ciganek (1963 ▶); Ohta et al. (1989 ▶); Hatanaka & Ojima (1981 ▶); Smith (1994 ▶); Borch et al. (1971 ▶). For related structures, see: Boulcina et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C18H17ClN2O

M = 312.79

Orthorhombic,

a = 7.3067 (1) Å

b = 17.7803 (4) Å

c = 22.8221 (5) Å

V = 2964.94 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.41 × 0.29 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.857, T max = 0.957

15861 measured reflections

3383 independent reflections

3303 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.05

3383 reflections

205 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1557 Friedel pairs

Flack parameter: 0.14 (5)

Data collection: APEX2 (Bruker,2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041061/lh5139sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041061/lh5139Isup2.hkl

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

C18H17ClN2O	F(000) = 1312
Mr = 312.79	Dx = 1.401 Mg m−3
Orthorhombic, C2cb	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2bc 2	Cell parameters from 9705 reflections
a = 7.3067 (1) Å	θ = 2.3–27.4°
b = 17.7803 (4) Å	µ = 0.26 mm−1
c = 22.8221 (5) Å	T = 100 K
V = 2964.94 (10) Å3	Prism, colourless
Z = 8	0.41 × 0.29 × 0.17 mm

Bruker APEXII diffractometer	3303 reflections with I > 2σ(I)
graphite	Rint = 0.030
CCD rotation images, thin slices scans	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.857, Tmax = 0.957	k = −22→22
15861 measured reflections	l = −29→29
3383 independent reflections

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0402P)2 + 1.310P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3383 reflections	Δρmax = 0.30 e Å−3
205 parameters	Δρmin = −0.17 e Å−3
1 restraint	Absolute structure: Flack (1983), 1557 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.14 (5)

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
Cl1	0.66000 (6)	0.143865 (16)	0.747584 (13)	0.01770 (8)
C1	0.72948 (19)	0.05005 (8)	0.75340 (5)	0.0142 (3)
N2	0.74170 (16)	0.02403 (6)	0.80680 (5)	0.0146 (2)
C3	0.79448 (18)	−0.04968 (7)	0.81373 (6)	0.0140 (2)
C4	0.80333 (18)	−0.08019 (8)	0.87155 (6)	0.0161 (3)
C5	0.7535 (2)	−0.03278 (8)	0.92397 (6)	0.0218 (3)
H5A	0.6239	−0.0240	0.9242	0.033*
H5B	0.8168	0.0145	0.9219	0.033*
H5C	0.7881	−0.0586	0.9592	0.033*
C6	0.85641 (19)	−0.15425 (8)	0.87761 (6)	0.0187 (3)
H6	0.8633	−0.1746	0.9151	0.022*
C7	0.9006 (2)	−0.20031 (8)	0.82926 (6)	0.0206 (3)
H7	0.9356	−0.2500	0.8352	0.025*
C8	0.8918 (2)	−0.17158 (8)	0.77354 (6)	0.0187 (3)
H8	0.9215	−0.2017	0.7416	0.022*
C9	0.83755 (19)	−0.09606 (8)	0.76480 (6)	0.0150 (3)
C10	0.81977 (18)	−0.06374 (8)	0.70812 (6)	0.0161 (3)
H10	0.8462	−0.0928	0.6753	0.019*
C11	0.76461 (18)	0.00913 (8)	0.70091 (5)	0.0152 (3)
C12	0.7358 (2)	0.04066 (8)	0.64019 (5)	0.0171 (3)
H12A	0.7357	−0.0003	0.6121	0.021*
H12B	0.6170	0.0649	0.6384	0.021*
N13	0.87651 (16)	0.09478 (6)	0.62391 (5)	0.0162 (2)
C14	0.87924 (19)	0.12075 (7)	0.56569 (5)	0.0143 (3)
C15	0.74893 (19)	0.09871 (7)	0.52389 (6)	0.0161 (3)
H15	0.6604	0.0634	0.5338	0.019*
C16	0.75084 (19)	0.12924 (8)	0.46776 (6)	0.0164 (3)
H16	0.6633	0.1141	0.4406	0.020*
C17	0.88177 (19)	0.18205 (7)	0.45168 (5)	0.0159 (3)
C18	1.01471 (19)	0.20355 (8)	0.49223 (6)	0.0171 (3)
H18	1.1045	0.2381	0.4818	0.021*
C19	1.01231 (18)	0.17304 (8)	0.54846 (6)	0.0164 (3)
H19	1.1013	0.1878	0.5753	0.020*
O20	0.86737 (15)	0.21049 (6)	0.39555 (4)	0.0202 (2)
C21	0.9605 (2)	0.27960 (9)	0.38392 (6)	0.0220 (3)
H21A	0.9370	0.3145	0.4151	0.033*
H21B	0.9173	0.3003	0.3476	0.033*
H21C	1.0897	0.2704	0.3812	0.033*
H13N	0.978 (4)	0.0849 (14)	0.6370 (11)	0.050*

	U11	U22	U33	U12	U13	U23
Cl1	0.02077 (15)	0.01491 (14)	0.01743 (14)	0.00316 (14)	0.00039 (13)	0.00172 (12)
C1	0.0131 (6)	0.0119 (6)	0.0177 (6)	−0.0001 (5)	0.0003 (5)	0.0017 (5)
N2	0.0130 (5)	0.0160 (5)	0.0146 (5)	−0.0004 (4)	−0.0006 (4)	−0.0001 (4)
C3	0.0122 (6)	0.0152 (6)	0.0147 (5)	−0.0019 (5)	−0.0010 (5)	0.0015 (5)
C4	0.0153 (6)	0.0188 (6)	0.0143 (6)	−0.0008 (5)	−0.0016 (5)	0.0011 (5)
C5	0.0307 (8)	0.0225 (7)	0.0121 (6)	0.0003 (6)	−0.0002 (6)	0.0014 (5)
C6	0.0178 (6)	0.0210 (7)	0.0172 (6)	−0.0019 (5)	−0.0030 (5)	0.0062 (5)
C7	0.0208 (6)	0.0161 (6)	0.0249 (7)	0.0008 (6)	−0.0036 (6)	0.0033 (5)
C8	0.0194 (7)	0.0165 (6)	0.0202 (6)	0.0002 (6)	0.0006 (6)	−0.0018 (5)
C9	0.0134 (6)	0.0156 (6)	0.0159 (6)	−0.0018 (5)	−0.0004 (5)	0.0011 (5)
C10	0.0156 (6)	0.0183 (6)	0.0143 (6)	−0.0024 (5)	0.0015 (5)	−0.0013 (5)
C11	0.0138 (6)	0.0185 (7)	0.0133 (6)	−0.0027 (5)	−0.0002 (5)	0.0004 (5)
C12	0.0204 (6)	0.0178 (6)	0.0131 (6)	−0.0035 (5)	−0.0009 (5)	0.0020 (5)
N13	0.0162 (6)	0.0189 (6)	0.0134 (5)	−0.0011 (5)	−0.0011 (4)	0.0022 (4)
C14	0.0175 (7)	0.0135 (5)	0.0120 (6)	0.0032 (5)	0.0013 (5)	−0.0005 (5)
C15	0.0173 (6)	0.0140 (6)	0.0169 (6)	−0.0018 (5)	0.0012 (5)	−0.0004 (5)
C16	0.0175 (7)	0.0164 (6)	0.0153 (6)	0.0006 (5)	−0.0021 (5)	−0.0032 (5)
C17	0.0192 (6)	0.0164 (6)	0.0120 (6)	0.0026 (6)	0.0013 (5)	0.0006 (5)
C18	0.0174 (6)	0.0188 (7)	0.0152 (6)	−0.0016 (5)	0.0022 (5)	0.0003 (5)
C19	0.0158 (6)	0.0195 (7)	0.0140 (6)	−0.0005 (5)	−0.0009 (5)	−0.0021 (5)
O20	0.0276 (6)	0.0208 (5)	0.0122 (4)	−0.0029 (4)	−0.0006 (4)	0.0022 (4)
C21	0.0216 (7)	0.0249 (7)	0.0194 (7)	−0.0013 (6)	0.0026 (5)	0.0070 (6)

Cl1—C1	1.7486 (14)	C12—N13	1.4566 (18)
C1—N2	1.3067 (16)	C12—H12A	0.9700
C1—C11	1.4249 (18)	C12—H12B	0.9700
N2—C3	1.3752 (18)	N13—C14	1.4068 (16)
C3—C9	1.4236 (19)	N13—H13N	0.82 (3)
C3—C4	1.4281 (18)	C14—C19	1.4016 (19)
C4—C6	1.3795 (19)	C14—C15	1.4036 (19)
C4—C5	1.5082 (19)	C15—C16	1.3913 (18)
C5—H5A	0.9600	C15—H15	0.9300
C5—H5B	0.9600	C16—C17	1.390 (2)
C5—H5C	0.9600	C16—H16	0.9300
C6—C7	1.411 (2)	C17—O20	1.3812 (15)
C6—H6	0.9300	C17—C18	1.395 (2)
C7—C8	1.3718 (19)	C18—C19	1.3935 (19)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.4143 (19)	C19—H19	0.9300
C8—H8	0.9300	O20—C21	1.4294 (18)
C9—C10	1.4213 (19)	C21—H21A	0.9600
C10—C11	1.3669 (19)	C21—H21B	0.9600
C10—H10	0.9300	C21—H21C	0.9600
C11—C12	1.5097 (17)
N2—C1—C11	126.23 (13)	N13—C12—C11	112.39 (11)
N2—C1—Cl1	115.37 (10)	N13—C12—H12A	109.1
C11—C1—Cl1	118.40 (10)	C11—C12—H12A	109.1
C1—N2—C3	117.64 (11)	N13—C12—H12B	109.1
N2—C3—C9	121.59 (12)	C11—C12—H12B	109.1
N2—C3—C4	118.75 (12)	H12A—C12—H12B	107.9
C9—C3—C4	119.65 (12)	C14—N13—C12	117.89 (11)
C6—C4—C3	117.90 (12)	C14—N13—H13N	113.6 (18)
C6—C4—C5	121.45 (12)	C12—N13—H13N	114.0 (18)
C3—C4—C5	120.64 (12)	C19—C14—C15	117.72 (12)
C4—C5—H5A	109.5	C19—C14—N13	119.50 (12)
C4—C5—H5B	109.5	C15—C14—N13	122.73 (12)
H5A—C5—H5B	109.5	C16—C15—C14	120.67 (12)
C4—C5—H5C	109.5	C16—C15—H15	119.7
H5A—C5—H5C	109.5	C14—C15—H15	119.7
H5B—C5—H5C	109.5	C17—C16—C15	120.90 (12)
C4—C6—C7	122.67 (13)	C17—C16—H16	119.5
C4—C6—H6	118.7	C15—C16—H16	119.5
C7—C6—H6	118.7	O20—C17—C16	116.09 (12)
C8—C7—C6	119.86 (13)	O20—C17—C18	124.60 (12)
C8—C7—H7	120.1	C16—C17—C18	119.30 (12)
C6—C7—H7	120.1	C19—C18—C17	119.70 (13)
C7—C8—C9	119.83 (13)	C19—C18—H18	120.1
C7—C8—H8	120.1	C17—C18—H18	120.1
C9—C8—H8	120.1	C18—C19—C14	121.69 (12)
C8—C9—C10	122.55 (13)	C18—C19—H19	119.2
C8—C9—C3	120.08 (12)	C14—C19—H19	119.2
C10—C9—C3	117.36 (12)	C17—O20—C21	116.79 (11)
C11—C10—C9	121.32 (13)	O20—C21—H21A	109.5
C11—C10—H10	119.3	O20—C21—H21B	109.5
C9—C10—H10	119.3	H21A—C21—H21B	109.5
C10—C11—C1	115.84 (12)	O20—C21—H21C	109.5
C10—C11—C12	120.24 (11)	H21A—C21—H21C	109.5
C1—C11—C12	123.85 (12)	H21B—C21—H21C	109.5
C11—C1—N2—C3	0.4 (2)	N2—C1—C11—C10	−1.4 (2)
Cl1—C1—N2—C3	179.51 (10)	Cl1—C1—C11—C10	179.53 (10)
C1—N2—C3—C9	1.04 (19)	N2—C1—C11—C12	175.65 (14)
C1—N2—C3—C4	−178.05 (13)	Cl1—C1—C11—C12	−3.40 (19)
N2—C3—C4—C6	179.95 (12)	C10—C11—C12—N13	−108.76 (14)
C9—C3—C4—C6	0.83 (19)	C1—C11—C12—N13	74.30 (17)
N2—C3—C4—C5	0.7 (2)	C11—C12—N13—C14	171.73 (11)
C9—C3—C4—C5	−178.37 (13)	C12—N13—C14—C19	179.78 (13)
C3—C4—C6—C7	−0.4 (2)	C12—N13—C14—C15	2.33 (19)
C5—C4—C6—C7	178.83 (14)	C19—C14—C15—C16	−1.26 (19)
C4—C6—C7—C8	0.1 (2)	N13—C14—C15—C16	176.24 (12)
C6—C7—C8—C9	−0.3 (2)	C14—C15—C16—C17	0.2 (2)
C7—C8—C9—C10	−177.82 (13)	C15—C16—C17—O20	−177.93 (12)
C7—C8—C9—C3	0.8 (2)	C15—C16—C17—C18	1.1 (2)
N2—C3—C9—C8	179.84 (13)	O20—C17—C18—C19	177.70 (12)
C4—C3—C9—C8	−1.1 (2)	C16—C17—C18—C19	−1.3 (2)
N2—C3—C9—C10	−1.44 (19)	C17—C18—C19—C14	0.1 (2)
C4—C3—C9—C10	177.64 (12)	C15—C14—C19—C18	1.1 (2)
C8—C9—C10—C11	179.08 (14)	N13—C14—C19—C18	−176.46 (12)
C3—C9—C10—C11	0.40 (19)	C16—C17—O20—C21	161.27 (12)
C9—C10—C11—C1	0.91 (19)	C18—C17—O20—C21	−17.73 (19)
C9—C10—C11—C12	−176.27 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13N···N2i	0.82 (3)	2.56 (3)	3.3471 (16)	163 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13N⋯N2i	0.82 (3)	2.56 (3)	3.3471 (16)	163 (2)

Symmetry code: (i) .