2-(3,4-Dichloro­phen­yl)-4-phenyl­benzo[h]quinoline

Wu, N.; Xu, Z.

doi:10.1107/S1600536811040049

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2850

doi:10.1107/S1600536811040049

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2-(3,4-Dichlorophenyl)-4-phenylbenzo[h]quinoline

Nan Wu ^a and Zhou Xu ^b ^*

^aDepartment of Aviation Oil and Materials, Xuzhou Airforce College, Xuzhou Jiangsu 221110, People's Republic of China, and ^bDepartment of Chemistry, Xuzhou Medical College, Xuzhou Jiangsu 221004, People's Republic of China
^*Correspondence e-mail: wu.nanxuzhou@gmail.com

(Received 23 September 2011; accepted 29 September 2011; online 5 October 2011)

In the title compound, C₂₅H₁₅Cl₂N, 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)°. Intermolecular C—H⋯π interactions 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_r = 400.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.110
S = 1.07
4523 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x, -y+2, -z+2.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040049/hg5101sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811040049/hg5101Isup3.cml

checkCIF report

Comment top

The benzo[h]quinoline derivatives and their complexes can be used as electronic material and organic electronic device (Cho et al. ,2010), potent family-18 chitinase inhibitors (Pantoom et al., 2011), topoisomerase IIα poisons (Liu et al., 2011). Besides, They can also treat Alzheimer's disease. These properties arouse our interset in the relationship between their structures and activities. During the synthesis of benzo[h]quinoline derivatives, the title compound, (I) was isolated and its structure was determined by X-ray diffraction. Herein we shall report its crystal structure. The molecular structure of (I) is shown in Fig. 1. In the molecular structure, the benzo[h]quinoline exhibits a planar conformation with RMS of 0.0202Å and the largest deviation is 0.039 (1) Å. The 3,4-dichlorophenyl is almost coplanar with benzo[h]quinoline, since the dihedral angle between them is only 6.68 (7)°. The parent ring and the phenyl subsitituent at position 4 form a dihedral angle of 67.11 (4)°. In addition, there is a non-classical intramolecular hydrogen bond (C19—H19···N1). The crystal packing is stabilized by the intermolecular C—H···π interactions (Fig. 2, Table 1).

Related literature top

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 top

The title compound was synthesized according to the reported procedure (Zhang et al., 2010). Under an air atmosphere, a 10 ml of sealable reaction tube equipped with a magnetic stir bar was charged with an 3,4-dichlorobenzaldehyde (1.00 mmol), naphthalen-1-amine (1.00 mmol), and the mixture was heated and stirred in an oil bath at 333 K for 1 h. Then FeCl₃ (16.2 mg, 0.10 mmol), ethynylbenzene (1.10 mmol) were added. The reaction mixture was then stirred in an oil bath at 393 K until the substrates were consumed completely (about 12 h), and then it was cooled to room temperature and the solvent was evaporated, the residue was purified by flash chromatography(hexane/AcOEt = 15:1) to afford the desired product.The single-crystal suitable for X-ray diffraction was obtained through the evaporation of ethanol solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear (Rigaku/MSC, 2002); data reduction: CrystalClear (Rigaku/MSC, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Cg1 is the centroid of the ring of C20/C21/C22/C23/C24/C25. Cg2 is the centroid of the ring of C14/C15/C16/C17/C18/C19. Cg3 is the centroid of the ring of N1/C1/C10/C11/C12/C13.
	Fig. 2. The packing diagram of (I).

2-(3,4-Dichlorophenyl)-4-phenylbenzo[h]quinoline top

Crystal data top

C₂₅H₁₅Cl₂N	F(000) = 824
M_r = 400.28	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	4523 independent reflections
Radiation source: rotating anode	3630 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.045
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.8°, θ_min = 1.9°
ω and ϕ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −12→12
T_min = 0.933, T_max = 0.959	l = −24→24
23687 measured reflections

Refinement top

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(F_o²) + (0.0602P)²] where P = (F_o² + 2F_c²)/3
4523 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₅H₁₅Cl₂N	V = 1904.8 (4) Å³
M_r = 400.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6066 (14) Å	µ = 0.35 mm⁻¹
b = 9.5667 (12) Å	T = 113 K
c = 18.824 (2) Å	0.20 × 0.18 × 0.12 mm
β = 94.264 (7)°

Data collection top

Rigaku Saturn724 CCD diffractometer	4523 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	3630 reflections with I > 2σ(I)
T_min = 0.933, T_max = 0.959	R_int = 0.045
23687 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.07	Δρ_max = 0.37 e Å⁻³
4523 reflections	Δρ_min = −0.36 e Å⁻³
253 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₅Cl₂N
M_r	400.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.6066 (14), 9.5667 (12), 18.824 (2)
β (°)	94.264 (7)
V (Å³)	1904.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2002)
T_min, T_max	0.933, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	23687, 4523, 3630
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.07
No. of reflections	4523
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.36

Computer programs: CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	154.0
C22—H22···Cg2ⁱⁱ	0.95	2.94	3.8204 (19)	156.0
C25—H25···Cg3ⁱⁱⁱ	0.95	2.63	3.4738 (17)	148.0
C19—H19···N1	0.95	2.42	2.765 (2)	101.1

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x, −y+2, −z+2.

Acknowledgements

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ15) for financial support.

References

Cho, Y. J., Kwon, H. J., Kim, B. O., Kim, S. M. & Yoon, S. S. (2010). Eur. Patent No. 2182002. Google Scholar
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Pantoom, S., Vetter, I. R., Prinz, H. & Suginta, W. (2011). J. Biol. Chem. 286, 24312–24323. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
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Volume 67| Part 11| November 2011| Page o2850

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