2-(3,4-Dichloro-phen-yl)-4-phenyl-benzo[h]quinoline.

In the title compound, C(25)H(15)Cl(2)N, the benzo[h]quinoline system exhibits an approximately planar conformation with an r.m.s. deviation of 0.0202Å and a maximum deviation of 0.039 (1) Å. The aryl group at position 2 is nearly coplanar with the parent ring [dihedral angle = 6.68 (7)°] while the parent ring and the phenyl subsitituent at position 4 form a dihedral angle of 67.11 (4)°. Inter-molecular C-H⋯π inter-actions stabilize the crystal packing.

Related literature

For the uses of metal complexes of benzo[h]quinoline as electronic materials and organic electronic devices, see: Cho et al. (2010 ▶). For the medicinal uses of benzo[h]quinoline and its complexes, see: Pantoom et al. (2011 ▶); Liu et al. (2011 ▶). For the preparation of the title compound, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C25H15Cl2N

M = 400.28

Monoclinic,

a = 10.6066 (14) Å

b = 9.5667 (12) Å

c = 18.824 (2) Å

β = 94.264 (7)°

V = 1904.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002) ▶ T min = 0.933, T max = 0.959

23687 measured reflections

4523 independent reflections

3630 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.07

4523 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002) ▶; cell refinement: CrystalClear ▶; data reduction: CrystalClear ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040049/hg5101sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040049/hg5101Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811040049/hg5101Isup3.cml

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

C25H15Cl2N	F(000) = 824
Mr = 400.28	Dx = 1.396 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6694 reflections
a = 10.6066 (14) Å	θ = 1.9–27.9°
b = 9.5667 (12) Å	µ = 0.35 mm−1
c = 18.824 (2) Å	T = 113 K
β = 94.264 (7)°	Prism, colorless
V = 1904.8 (4) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	4523 independent reflections
Radiation source: rotating anode	3630 reflections with I > 2σ(I)
multilayer	Rint = 0.045
Detector resolution: 14.22 pixels mm-1	θmax = 27.8°, θmin = 1.9°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −12→12
Tmin = 0.933, Tmax = 0.959	l = −24→24
23687 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0602P)2] where P = (Fo2 + 2Fc2)/3
4523 reflections	(Δ/σ)max = 0.002
253 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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	0.52078 (4)	0.42736 (4)	1.09062 (2)	0.03323 (13)
Cl2	0.56082 (4)	0.57108 (5)	1.24136 (2)	0.03876 (14)
N1	0.09940 (11)	0.64203 (12)	0.98050 (6)	0.0220 (3)
C1	−0.00408 (13)	0.66067 (15)	0.93439 (8)	0.0217 (3)
C2	−0.00284 (14)	0.59559 (15)	0.86472 (8)	0.0226 (3)
C3	0.10040 (15)	0.51461 (17)	0.84545 (8)	0.0270 (4)
H3	0.1729	0.5043	0.8778	0.032*
C4	0.09621 (16)	0.45062 (16)	0.78003 (9)	0.0310 (4)
H4	0.1656	0.3950	0.7678	0.037*
C5	−0.00939 (16)	0.46621 (17)	0.73071 (9)	0.0318 (4)
H5	−0.0110	0.4210	0.6857	0.038*
C6	−0.11019 (16)	0.54695 (16)	0.74773 (9)	0.0292 (4)
H6	−0.1807	0.5586	0.7141	0.035*
C7	−0.10939 (14)	0.61255 (16)	0.81487 (8)	0.0239 (3)
C8	−0.21411 (14)	0.69559 (16)	0.83422 (8)	0.0260 (3)
H8	−0.2849	0.7073	0.8008	0.031*
C9	−0.21506 (14)	0.75764 (15)	0.89867 (8)	0.0264 (3)
H9	−0.2853	0.8136	0.9092	0.032*
C10	−0.11070 (13)	0.73999 (15)	0.95172 (8)	0.0231 (3)
C11	−0.10774 (14)	0.79943 (15)	1.02076 (8)	0.0236 (3)
C12	−0.00148 (14)	0.78015 (16)	1.06638 (8)	0.0249 (3)
H12	0.0027	0.8206	1.1126	0.030*
C13	0.10125 (14)	0.70060 (15)	1.04485 (8)	0.0229 (3)
C14	0.21694 (14)	0.67568 (15)	1.09325 (8)	0.0231 (3)
C15	0.23628 (14)	0.73938 (16)	1.15973 (8)	0.0291 (4)
H15	0.1761	0.8048	1.1745	0.035*
C16	0.34251 (14)	0.70838 (17)	1.20477 (8)	0.0311 (4)
H16	0.3546	0.7529	1.2499	0.037*
C17	0.43053 (14)	0.61299 (17)	1.18414 (8)	0.0276 (4)
C18	0.41328 (14)	0.55001 (15)	1.11722 (8)	0.0250 (3)
C19	0.30761 (14)	0.58159 (15)	1.07252 (8)	0.0238 (3)
H19	0.2967	0.5385	1.0270	0.029*
C20	−0.21559 (14)	0.88347 (16)	1.04496 (8)	0.0245 (3)
C21	−0.33198 (14)	0.82296 (18)	1.05638 (9)	0.0328 (4)
H21	−0.3450	0.7260	1.0476	0.039*
C22	−0.42876 (16)	0.90333 (19)	1.08044 (9)	0.0361 (4)
H22	−0.5078	0.8614	1.0881	0.043*
C23	−0.41049 (16)	1.04477 (17)	1.09328 (9)	0.0335 (4)
H23	−0.4769	1.0996	1.1100	0.040*
C24	−0.29624 (16)	1.10611 (18)	1.08182 (9)	0.0330 (4)
H24	−0.2842	1.2034	1.0899	0.040*
C25	−0.19865 (15)	1.02549 (16)	1.05835 (8)	0.0274 (4)
H25	−0.1195	1.0678	1.0514	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.0260 (2)	0.0342 (2)	0.0393 (3)	0.01057 (17)	0.00126 (18)	−0.00259 (18)
Cl2	0.0285 (2)	0.0490 (3)	0.0374 (3)	0.00308 (19)	−0.00704 (18)	−0.0028 (2)
N1	0.0228 (7)	0.0176 (6)	0.0260 (7)	0.0012 (5)	0.0046 (5)	0.0016 (5)
C1	0.0220 (8)	0.0166 (7)	0.0269 (8)	−0.0008 (6)	0.0039 (6)	0.0018 (6)
C2	0.0223 (8)	0.0188 (7)	0.0270 (8)	−0.0010 (6)	0.0047 (6)	0.0022 (6)
C3	0.0245 (8)	0.0254 (8)	0.0312 (9)	0.0021 (7)	0.0023 (7)	−0.0014 (7)
C4	0.0302 (9)	0.0294 (9)	0.0339 (9)	0.0042 (7)	0.0059 (7)	−0.0066 (7)
C5	0.0343 (9)	0.0322 (9)	0.0292 (9)	−0.0019 (8)	0.0046 (7)	−0.0052 (7)
C6	0.0278 (9)	0.0296 (9)	0.0298 (9)	−0.0028 (7)	−0.0002 (7)	0.0016 (7)
C7	0.0232 (8)	0.0202 (8)	0.0287 (8)	−0.0026 (6)	0.0038 (6)	0.0033 (6)
C8	0.0214 (8)	0.0260 (8)	0.0306 (8)	−0.0008 (6)	0.0006 (6)	0.0066 (7)
C9	0.0210 (7)	0.0234 (8)	0.0354 (9)	0.0028 (6)	0.0055 (7)	0.0040 (7)
C10	0.0205 (7)	0.0194 (7)	0.0298 (8)	0.0005 (6)	0.0055 (6)	0.0032 (6)
C11	0.0234 (8)	0.0184 (7)	0.0297 (8)	0.0003 (6)	0.0078 (6)	0.0038 (6)
C12	0.0281 (8)	0.0215 (8)	0.0259 (8)	0.0024 (6)	0.0072 (6)	0.0007 (6)
C13	0.0238 (8)	0.0173 (7)	0.0279 (8)	−0.0009 (6)	0.0051 (6)	0.0027 (6)
C14	0.0239 (8)	0.0188 (7)	0.0272 (8)	−0.0008 (6)	0.0054 (6)	0.0022 (6)
C15	0.0288 (9)	0.0267 (8)	0.0323 (9)	0.0042 (7)	0.0050 (7)	−0.0027 (7)
C16	0.0329 (9)	0.0313 (9)	0.0291 (9)	−0.0019 (7)	0.0024 (7)	−0.0055 (7)
C17	0.0235 (8)	0.0284 (9)	0.0302 (9)	−0.0026 (7)	−0.0022 (7)	0.0029 (7)
C18	0.0228 (8)	0.0214 (8)	0.0314 (9)	0.0013 (6)	0.0060 (7)	0.0008 (7)
C19	0.0256 (8)	0.0217 (8)	0.0242 (8)	0.0004 (6)	0.0030 (6)	0.0001 (6)
C20	0.0246 (8)	0.0245 (8)	0.0249 (8)	0.0049 (6)	0.0052 (6)	0.0037 (6)
C21	0.0291 (9)	0.0256 (9)	0.0447 (10)	−0.0001 (7)	0.0105 (8)	0.0016 (7)
C22	0.0276 (9)	0.0366 (10)	0.0458 (11)	0.0022 (8)	0.0142 (8)	0.0046 (8)
C23	0.0307 (9)	0.0345 (10)	0.0368 (10)	0.0113 (8)	0.0129 (7)	0.0052 (8)
C24	0.0345 (9)	0.0256 (9)	0.0399 (10)	0.0085 (7)	0.0096 (8)	0.0018 (7)
C25	0.0252 (8)	0.0253 (8)	0.0324 (9)	0.0021 (7)	0.0073 (7)	0.0036 (7)

Cl1—C18	1.7356 (15)	C12—C13	1.413 (2)
Cl2—C17	1.7347 (16)	C12—H12	0.9500
N1—C13	1.3334 (18)	C13—C14	1.492 (2)
N1—C1	1.3595 (19)	C14—C15	1.393 (2)
C1—C10	1.420 (2)	C14—C19	1.394 (2)
C1—C2	1.453 (2)	C15—C16	1.391 (2)
C2—C3	1.411 (2)	C15—H15	0.9500
C2—C7	1.423 (2)	C16—C17	1.382 (2)
C3—C4	1.373 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.396 (2)
C4—C5	1.409 (2)	C18—C19	1.384 (2)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.376 (2)	C20—C25	1.391 (2)
C5—H5	0.9500	C20—C21	1.395 (2)
C6—C7	1.411 (2)	C21—C22	1.385 (2)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.435 (2)	C22—C23	1.386 (2)
C8—C9	1.351 (2)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.378 (2)
C9—C10	1.444 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—C25	1.389 (2)
C10—C11	1.417 (2)	C24—H24	0.9500
C11—C12	1.378 (2)	C25—H25	0.9500
C11—C20	1.497 (2)
C13—N1—C1	118.79 (12)	N1—C13—C14	116.32 (13)
N1—C1—C10	122.84 (14)	C12—C13—C14	121.84 (14)
N1—C1—C2	117.34 (13)	C15—C14—C19	118.38 (14)
C10—C1—C2	119.82 (13)	C15—C14—C13	122.55 (14)
C3—C2—C7	119.10 (14)	C19—C14—C13	119.04 (14)
C3—C2—C1	121.79 (14)	C16—C15—C14	120.85 (14)
C7—C2—C1	119.10 (13)	C16—C15—H15	119.6
C4—C3—C2	120.10 (14)	C14—C15—H15	119.6
C4—C3—H3	119.9	C17—C16—C15	120.21 (15)
C2—C3—H3	119.9	C17—C16—H16	119.9
C3—C4—C5	121.00 (15)	C15—C16—H16	119.9
C3—C4—H4	119.5	C16—C17—C18	119.52 (14)
C5—C4—H4	119.5	C16—C17—Cl2	120.12 (12)
C6—C5—C4	119.97 (15)	C18—C17—Cl2	120.36 (12)
C6—C5—H5	120.0	C19—C18—C17	120.01 (14)
C4—C5—H5	120.0	C19—C18—Cl1	119.47 (12)
C5—C6—C7	120.35 (15)	C17—C18—Cl1	120.48 (12)
C5—C6—H6	119.8	C18—C19—C14	121.01 (14)
C7—C6—H6	119.8	C18—C19—H19	119.5
C6—C7—C2	119.45 (14)	C14—C19—H19	119.5
C6—C7—C8	121.38 (14)	C25—C20—C21	118.78 (14)
C2—C7—C8	119.18 (14)	C25—C20—C11	119.24 (14)
C9—C8—C7	121.92 (14)	C21—C20—C11	121.95 (14)
C9—C8—H8	119.0	C22—C21—C20	120.39 (16)
C7—C8—H8	119.0	C22—C21—H21	119.8
C8—C9—C10	120.86 (14)	C20—C21—H21	119.8
C8—C9—H9	119.6	C21—C22—C23	120.11 (16)
C10—C9—H9	119.6	C21—C22—H22	119.9
C11—C10—C1	117.49 (13)	C23—C22—H22	119.9
C11—C10—C9	123.43 (13)	C24—C23—C22	120.12 (15)
C1—C10—C9	119.08 (14)	C24—C23—H23	119.9
C12—C11—C10	118.65 (13)	C22—C23—H23	119.9
C12—C11—C20	119.37 (14)	C23—C24—C25	119.88 (16)
C10—C11—C20	121.98 (13)	C23—C24—H24	120.1
C11—C12—C13	120.39 (14)	C25—C24—H24	120.1
C11—C12—H12	119.8	C24—C25—C20	120.71 (15)
C13—C12—H12	119.8	C24—C25—H25	119.6
N1—C13—C12	121.83 (13)	C20—C25—H25	119.6
C13—N1—C1—C10	0.0 (2)	C1—N1—C13—C14	179.61 (12)
C13—N1—C1—C2	179.91 (13)	C11—C12—C13—N1	0.0 (2)
N1—C1—C2—C3	0.8 (2)	C11—C12—C13—C14	−179.01 (13)
C10—C1—C2—C3	−179.29 (14)	N1—C13—C14—C15	174.74 (13)
N1—C1—C2—C7	179.98 (13)	C12—C13—C14—C15	−6.2 (2)
C10—C1—C2—C7	−0.1 (2)	N1—C13—C14—C19	−7.5 (2)
C7—C2—C3—C4	−1.5 (2)	C12—C13—C14—C19	171.63 (14)
C1—C2—C3—C4	177.67 (14)	C19—C14—C15—C16	−0.9 (2)
C2—C3—C4—C5	1.1 (2)	C13—C14—C15—C16	176.90 (14)
C3—C4—C5—C6	0.2 (2)	C14—C15—C16—C17	−0.3 (2)
C4—C5—C6—C7	−1.0 (2)	C15—C16—C17—C18	1.2 (2)
C5—C6—C7—C2	0.6 (2)	C15—C16—C17—Cl2	−178.31 (13)
C5—C6—C7—C8	−179.10 (15)	C16—C17—C18—C19	−1.0 (2)
C3—C2—C7—C6	0.7 (2)	Cl2—C17—C18—C19	178.52 (11)
C1—C2—C7—C6	−178.51 (13)	C16—C17—C18—Cl1	−178.77 (12)
C3—C2—C7—C8	−179.61 (14)	Cl2—C17—C18—Cl1	0.77 (19)
C1—C2—C7—C8	1.2 (2)	C17—C18—C19—C14	−0.2 (2)
C6—C7—C8—C9	179.24 (15)	Cl1—C18—C19—C14	177.60 (12)
C2—C7—C8—C9	−0.4 (2)	C15—C14—C19—C18	1.1 (2)
C7—C8—C9—C10	−1.4 (2)	C13—C14—C19—C18	−176.76 (13)
N1—C1—C10—C11	−1.0 (2)	C12—C11—C20—C25	65.91 (19)
C2—C1—C10—C11	179.08 (13)	C10—C11—C20—C25	−113.34 (17)
N1—C1—C10—C9	178.24 (13)	C12—C11—C20—C21	−112.36 (17)
C2—C1—C10—C9	−1.7 (2)	C10—C11—C20—C21	68.4 (2)
C8—C9—C10—C11	−178.35 (14)	C25—C20—C21—C22	0.2 (2)
C8—C9—C10—C1	2.5 (2)	C11—C20—C21—C22	178.44 (15)
C1—C10—C11—C12	1.5 (2)	C20—C21—C22—C23	0.1 (3)
C9—C10—C11—C12	−177.71 (14)	C21—C22—C23—C24	0.3 (3)
C1—C10—C11—C20	−179.25 (13)	C22—C23—C24—C25	−0.9 (3)
C9—C10—C11—C20	1.5 (2)	C23—C24—C25—C20	1.2 (2)
C10—C11—C12—C13	−1.1 (2)	C21—C20—C25—C24	−0.8 (2)
C20—C11—C12—C13	179.67 (13)	C11—C20—C25—C24	−179.11 (14)
C1—N1—C13—C12	0.5 (2)

Cg1, Cg2 and Cg3 are the centroids of the C20–C25, C14–C19 and N1/C1/C10–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1i	0.95	2.98	3.8577 (19)	154.
C22—H22···Cg2ii	0.95	2.94	3.8204 (19)	156.
C25—H25···Cg3iii	0.95	2.63	3.4738 (17)	148.
C19—H19···N1	0.95	2.42	2.765 (2)	101.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C20–C25, C14–C19 and N1/C1/C10–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1i	0.95	2.98	3.8577 (19)	154
C22—H22⋯Cg2ii	0.95	2.94	3.8204 (19)	156
C25—H25⋯Cg3iii	0.95	2.63	3.4738 (17)	148

Symmetry codes: (i) ; (ii) ; (iii) .