3-(4-Chloro­phen­yl)-1-(4-nitro­phen­yl)benzo[f]quinoline

Wang, S.-L.; Li, Q.; Wang, X.-S.; Tu, S.-J.

doi:10.1107/S1600536809031122

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2137

doi:10.1107/S1600536809031122

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3-(4-Chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline

Shu-Liang Wang,^a ^* Qing Li,^a Xiang-Shan Wang ^a and Shu-Jiang Tu ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: slwangxznu@yahoo.cn

(Received 29 July 2009; accepted 6 August 2009; online 12 August 2009)

In the title compound, C₂₅H₁₅ClN₂O₂, the pyridine ring is inclined at angles of 6.89 (7), 4.24 (9) and 66.98 (4)° with respect to the naphthalene, chlorophenyl and nitrophenyl rings, respectively. The two substituent aromatic rings make a dihedral angle of 71.1 (1)° with one another. C—H⋯π and π–π stacking are present in the crystal structure; the π–π stacking [centroid–centroid distance between the pyridyl rings of adjacent molecules= 3.7838 (11) Å] links the molecules into dimers, while the C—H⋯Cg type π–ring interactons link the molecules into a chain structure along c.

Related literature

Quinoline and its derivatives are intermediates in organic synthesis and are useful dyes, see: Brock et al. (1999 ). They possess a broad spectrum of biological activity, such as antiasthmatic, antiinflammatory and antimalarial, see: Fokialakis et al. (2002 ); Ma et al. (2004 ); Sawada et al. (2004 ). In addition, quinoline derivatives have been evaluated as anticancer and anthelmintic agents, see: Sakata et al. (1988 ). For related structures, see: Tu et al. (2006 ); Xie et al. (2009 ).

Experimental

Crystal data

C₂₅H₁₅ClN₂O₂
M_r = 410.84
Triclinic, $[P \overline 1]$
a = 9.1390 (12) Å
b = 9.5350 (11) Å
c = 11.9668 (17) Å
α = 108.182 (4)°
β = 105.366 (4)°
γ = 92.739 (3)°
V = 945.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 113 K
0.34 × 0.32 × 0.22 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ) T_min = 0.926, T_max = 0.952
11798 measured reflections
4467 independent reflections
3779 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.129
S = 1.06
4467 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯Cgⁱ	0.95	2.72	3.510 (12)	142
Symmetry code: (i) x, y-1, z. Cg is the centroid of the C14–C19 ring.

Data collection: CrystalClear (Rigaku, 1999); 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: CrystalStructure/MSC (Rigaku/MSC (2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031122/pv2192sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031122/pv2192Isup2.hkl

checkCIF report

Comment top

Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including such as antiasthmatic, antiinflammatory and antimalarial activity (Sawada, et al., 2004; Ma et al., 2004; Fokialakis et al., 2002). In addition, quinoline derivatives have been evaluated as anticancer and anthelmintic agents (Sakata et al., 1988). We report here the preparation and crystal structure of 3-(4-chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline, (I).

In the structure of (I) (Fig. 1), the benzoquinoline moiety is not quite planar as C3 deviates by 0.169 (1) Å from the mean-plane formed by the atoms N1/C1–C13. The pyridine ring is inclined at angles 6.89 (7), 4.24 (9) and 66.98 (4) ° with respect to the naphthalene (C4–C13), and phenyl rings C14–C19 and C20–C25, respectively. The two phenyl rings make a dihedral angle of 71.1 (1) °.

The C—H···π and π–π stacking are present in the crystal structure of (I). The π–π stacking (Cg···Cg distance 3.7838 (11) Å between the pyridyl rings of adjacent molecules) links the molecules into dimmers, while the C24—H24A···Cg stacking links the molecules into polymers (Figure 2).

The following crystal structures of compounds closely related to (I) have been reported: 13-(4-fluorophenyl)-12H-benzo[f]indeno[1,2-b]quinolin-12-one (Tu et al., 2006) and 5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine (Xie et al., 2009).

Related literature top

Quinoline and its derivatives are intermediates in organic synthesis and are useful dyes, see: Brock et al. (1999). They possess a broad spectrum of biological activity, such as antiasthmatic, antiinflammatory and antimalarial, see: Fokialakis et al. (2002); Ma et al. (2004); Sawada et al. (2004). In addition, quinoline derivatives have been evaluated as anticancer and anthelmintic agents, see: Sakata et al. (1988). For related structures, see: Tu et al. (2006); Xie et al. (2009).

Experimental top

The title compound, (I), was prepared by the reaction of 4-chlorobenzaldehyde (2 mmol, 0.281 g), naphthalen-2-amine (2 mmol, 0.283 g) and 2-bromoacetophenone (2 mmol, 0.498 g) in THF (10 ml) at 338 K catalyzed by iodine. m.p. 559–561 K. The single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution of (I).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); 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: CrystalStructure/MSC (Rigaku/MSC (2003).

Figures top

	Fig. 1. The molecular structure of (I) plotted with 50% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagram showing the C—H···π and π–π stacking in the crystal of (I).

3-(4-Chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline top

Crystal data top

C₂₅H₁₅ClN₂O₂	Z = 2
M_r = 410.84	F(000) = 424
Triclinic, P1	D_x = 1.443 Mg m⁻³
Hall symbol: -P 1	Melting point = 559–561 K
a = 9.1390 (12) Å	Mo Kα radiation, λ = 0.71070 Å
b = 9.5350 (11) Å	Cell parameters from 3276 reflections
c = 11.9668 (17) Å	θ = 1.9–27.9°
α = 108.182 (4)°	µ = 0.23 mm⁻¹
β = 105.366 (4)°	T = 113 K
γ = 92.739 (3)°	Block, yellow
V = 945.6 (2) Å³	0.34 × 0.32 × 0.22 mm

Data collection top

Rigaku Saturn diffractometer	4467 independent reflections
Radiation source: rotating anode	3779 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.034
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.9°, θ_min = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	k = −12→12
T_min = 0.926, T_max = 0.952	l = −15→15
11798 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0619P)² + 0.2446P] where P = (F_o² + 2F_c²)/3
4467 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₅H₁₅ClN₂O₂	γ = 92.739 (3)°
M_r = 410.84	V = 945.6 (2) Å³
Triclinic, P1	Z = 2
a = 9.1390 (12) Å	Mo Kα radiation
b = 9.5350 (11) Å	µ = 0.23 mm⁻¹
c = 11.9668 (17) Å	T = 113 K
α = 108.182 (4)°	0.34 × 0.32 × 0.22 mm
β = 105.366 (4)°

Data collection top

Rigaku Saturn diffractometer	4467 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	3779 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.952	R_int = 0.034
11798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.06	Δρ_max = 0.36 e Å⁻³
4467 reflections	Δρ_min = −0.47 e Å⁻³
271 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	−0.44740 (5)	1.45046 (5)	0.65255 (4)	0.03265 (15)
O1	0.11873 (18)	0.19922 (14)	0.55020 (13)	0.0390 (4)
O2	0.20781 (16)	0.29045 (15)	0.43402 (12)	0.0373 (3)
N1	0.09795 (15)	1.16854 (15)	0.97919 (12)	0.0190 (3)
N2	0.16218 (16)	0.30287 (16)	0.52288 (13)	0.0237 (3)
C1	0.03104 (17)	1.11236 (17)	0.85802 (15)	0.0180 (3)
C2	0.05962 (18)	0.97511 (17)	0.78672 (15)	0.0197 (3)
H2	0.0085	0.9370	0.7008	0.024*
C3	0.16056 (18)	0.89462 (17)	0.83916 (14)	0.0178 (3)
C4	0.24330 (17)	0.95634 (17)	0.96652 (15)	0.0181 (3)
C5	0.20143 (17)	1.09302 (17)	1.03223 (15)	0.0184 (3)
C6	0.26619 (18)	1.15733 (18)	1.16297 (15)	0.0212 (3)
H6	0.2361	1.2475	1.2062	0.025*
C7	0.36952 (19)	1.09148 (19)	1.22567 (15)	0.0228 (4)
H7	0.4074	1.1337	1.3128	0.027*
C8	0.42320 (18)	0.95928 (18)	1.16351 (15)	0.0208 (3)
C9	0.36459 (18)	0.89220 (17)	1.03335 (15)	0.0193 (3)
C10	0.43260 (18)	0.77063 (18)	0.97623 (16)	0.0221 (4)
H10	0.4000	0.7273	0.8890	0.027*
C11	0.54513 (19)	0.71333 (19)	1.04391 (17)	0.0253 (4)
H11	0.5879	0.6308	1.0029	0.030*
C12	0.59711 (19)	0.7757 (2)	1.17264 (17)	0.0265 (4)
H12	0.6725	0.7342	1.2192	0.032*
C13	0.53780 (19)	0.89731 (19)	1.23024 (16)	0.0244 (4)
H13	0.5746	0.9411	1.3173	0.029*
C14	−0.08359 (18)	1.19683 (17)	0.80328 (15)	0.0187 (3)
C15	−0.17082 (19)	1.14279 (18)	0.67950 (15)	0.0224 (4)
H15	−0.1543	1.0514	0.6265	0.027*
C16	−0.28137 (19)	1.22157 (19)	0.63335 (16)	0.0237 (4)
H16	−0.3407	1.1840	0.5492	0.028*
C17	−0.30481 (18)	1.35505 (19)	0.71036 (16)	0.0222 (4)
C18	−0.21770 (19)	1.41347 (19)	0.83272 (16)	0.0236 (4)
H18	−0.2323	1.5067	0.8845	0.028*
C19	−0.10882 (19)	1.33288 (18)	0.87788 (15)	0.0209 (3)
H19	−0.0497	1.3713	0.9620	0.025*
C20	0.16339 (17)	0.74070 (17)	0.75715 (15)	0.0184 (3)
C21	0.21663 (19)	0.71865 (18)	0.65500 (15)	0.0216 (3)
H21	0.2540	0.8023	0.6383	0.026*
C22	0.21556 (18)	0.57585 (18)	0.57745 (15)	0.0214 (3)
H22	0.2528	0.5604	0.5082	0.026*
C23	0.15882 (18)	0.45621 (17)	0.60359 (14)	0.0193 (3)
C24	0.09988 (19)	0.47391 (18)	0.70168 (15)	0.0221 (4)
H24	0.0590	0.3899	0.7161	0.027*
C25	0.10213 (19)	0.61767 (18)	0.77824 (15)	0.0215 (3)
H25	0.0616	0.6326	0.8458	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0261 (2)	0.0316 (3)	0.0412 (3)	0.01053 (18)	0.0055 (2)	0.0162 (2)
O1	0.0580 (9)	0.0188 (6)	0.0367 (8)	0.0056 (6)	0.0139 (7)	0.0046 (6)
O2	0.0424 (8)	0.0319 (7)	0.0299 (7)	0.0032 (6)	0.0144 (6)	−0.0031 (6)
N1	0.0188 (7)	0.0175 (6)	0.0199 (7)	0.0015 (5)	0.0058 (6)	0.0054 (5)
N2	0.0208 (7)	0.0257 (7)	0.0182 (7)	0.0025 (6)	0.0012 (6)	0.0022 (6)
C1	0.0174 (7)	0.0159 (7)	0.0211 (8)	0.0008 (6)	0.0073 (6)	0.0057 (6)
C2	0.0201 (8)	0.0176 (7)	0.0193 (8)	0.0014 (6)	0.0053 (6)	0.0041 (6)
C3	0.0188 (7)	0.0149 (7)	0.0202 (8)	0.0015 (6)	0.0085 (6)	0.0042 (6)
C4	0.0175 (8)	0.0159 (7)	0.0216 (8)	0.0009 (6)	0.0073 (6)	0.0060 (6)
C5	0.0176 (7)	0.0166 (7)	0.0211 (8)	0.0013 (6)	0.0067 (6)	0.0056 (6)
C6	0.0229 (8)	0.0178 (7)	0.0206 (8)	0.0006 (6)	0.0070 (7)	0.0031 (6)
C7	0.0243 (8)	0.0227 (8)	0.0188 (8)	0.0001 (7)	0.0048 (7)	0.0053 (7)
C8	0.0192 (8)	0.0196 (8)	0.0249 (9)	−0.0003 (6)	0.0066 (7)	0.0094 (7)
C9	0.0176 (7)	0.0181 (7)	0.0235 (8)	0.0005 (6)	0.0075 (6)	0.0080 (7)
C10	0.0194 (8)	0.0216 (8)	0.0266 (9)	0.0029 (6)	0.0084 (7)	0.0082 (7)
C11	0.0209 (8)	0.0228 (8)	0.0354 (10)	0.0054 (7)	0.0107 (7)	0.0118 (8)
C12	0.0224 (8)	0.0281 (9)	0.0340 (10)	0.0061 (7)	0.0069 (8)	0.0182 (8)
C13	0.0235 (8)	0.0262 (9)	0.0232 (9)	0.0004 (7)	0.0033 (7)	0.0114 (7)
C14	0.0189 (8)	0.0169 (7)	0.0211 (8)	0.0016 (6)	0.0067 (6)	0.0072 (6)
C15	0.0251 (8)	0.0173 (8)	0.0231 (9)	0.0036 (6)	0.0065 (7)	0.0049 (7)
C16	0.0242 (8)	0.0232 (8)	0.0209 (9)	0.0017 (7)	0.0027 (7)	0.0072 (7)
C17	0.0182 (8)	0.0223 (8)	0.0289 (9)	0.0042 (6)	0.0074 (7)	0.0120 (7)
C18	0.0260 (9)	0.0197 (8)	0.0260 (9)	0.0055 (7)	0.0103 (7)	0.0062 (7)
C19	0.0227 (8)	0.0199 (8)	0.0188 (8)	0.0032 (6)	0.0061 (7)	0.0049 (7)
C20	0.0167 (7)	0.0165 (7)	0.0193 (8)	0.0041 (6)	0.0035 (6)	0.0037 (6)
C21	0.0239 (8)	0.0188 (8)	0.0221 (8)	0.0034 (6)	0.0067 (7)	0.0069 (7)
C22	0.0220 (8)	0.0243 (8)	0.0175 (8)	0.0057 (6)	0.0060 (7)	0.0058 (7)
C23	0.0183 (8)	0.0166 (7)	0.0175 (8)	0.0048 (6)	0.0019 (6)	0.0010 (6)
C24	0.0230 (8)	0.0175 (8)	0.0247 (9)	0.0024 (6)	0.0061 (7)	0.0064 (7)
C25	0.0240 (8)	0.0194 (8)	0.0216 (8)	0.0032 (6)	0.0097 (7)	0.0054 (7)

Geometric parameters (Å, º) top

Cl1—C17	1.7414 (17)	C11—H11	0.9500
O1—N2	1.2142 (19)	C12—C13	1.368 (2)
O2—N2	1.2165 (19)	C12—H12	0.9500
N1—C1	1.333 (2)	C13—H13	0.9500
N1—C5	1.359 (2)	C14—C19	1.396 (2)
N2—C23	1.487 (2)	C14—C15	1.398 (2)
C1—C2	1.401 (2)	C15—C16	1.388 (2)
C1—C14	1.490 (2)	C15—H15	0.9500
C2—C3	1.377 (2)	C16—C17	1.383 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.424 (2)	C17—C18	1.385 (2)
C3—C20	1.495 (2)	C18—C19	1.386 (2)
C4—C5	1.425 (2)	C18—H18	0.9500
C4—C9	1.464 (2)	C19—H19	0.9500
C5—C6	1.432 (2)	C20—C21	1.393 (2)
C6—C7	1.351 (2)	C20—C25	1.396 (2)
C6—H6	0.9500	C21—C22	1.386 (2)
C7—C8	1.432 (2)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.386 (2)
C8—C13	1.412 (2)	C22—H22	0.9500
C8—C9	1.423 (2)	C23—C24	1.384 (2)
C9—C10	1.413 (2)	C24—C25	1.386 (2)
C10—C11	1.379 (2)	C24—H24	0.9500
C10—H10	0.9500	C25—H25	0.9500
C11—C12	1.402 (3)

C1—N1—C5	118.45 (14)	C12—C13—C8	121.65 (16)
O1—N2—O2	124.78 (15)	C12—C13—H13	119.2
O1—N2—C23	117.66 (14)	C8—C13—H13	119.2
O2—N2—C23	117.56 (14)	C19—C14—C15	118.20 (15)
N1—C1—C2	121.44 (14)	C19—C14—C1	119.49 (14)
N1—C1—C14	117.00 (14)	C15—C14—C1	122.29 (14)
C2—C1—C14	121.43 (14)	C16—C15—C14	120.53 (15)
C3—C2—C1	121.03 (15)	C16—C15—H15	119.7
C3—C2—H2	119.5	C14—C15—H15	119.7
C1—C2—H2	119.5	C17—C16—C15	119.71 (15)
C2—C3—C4	119.17 (14)	C17—C16—H16	120.1
C2—C3—C20	115.55 (14)	C15—C16—H16	120.1
C4—C3—C20	125.06 (14)	C16—C17—C18	121.18 (15)
C3—C4—C5	115.47 (14)	C16—C17—Cl1	119.34 (13)
C3—C4—C9	125.96 (14)	C18—C17—Cl1	119.48 (13)
C5—C4—C9	118.57 (14)	C17—C18—C19	118.48 (15)
N1—C5—C4	124.14 (15)	C17—C18—H18	120.8
N1—C5—C6	115.65 (14)	C19—C18—H18	120.8
C4—C5—C6	120.19 (14)	C18—C19—C14	121.87 (15)
C7—C6—C5	120.86 (15)	C18—C19—H19	119.1
C7—C6—H6	119.6	C14—C19—H19	119.1
C5—C6—H6	119.6	C21—C20—C25	119.49 (15)
C6—C7—C8	121.35 (15)	C21—C20—C3	120.79 (14)
C6—C7—H7	119.3	C25—C20—C3	119.58 (14)
C8—C7—H7	119.3	C22—C21—C20	120.64 (15)
C13—C8—C9	119.58 (15)	C22—C21—H21	119.7
C13—C8—C7	120.33 (15)	C20—C21—H21	119.7
C9—C8—C7	120.06 (15)	C23—C22—C21	118.27 (15)
C10—C9—C8	117.29 (15)	C23—C22—H22	120.9
C10—C9—C4	124.07 (15)	C21—C22—H22	120.9
C8—C9—C4	118.58 (14)	C24—C23—C22	122.69 (15)
C11—C10—C9	121.62 (16)	C24—C23—N2	118.94 (15)
C11—C10—H10	119.2	C22—C23—N2	118.37 (14)
C9—C10—H10	119.2	C23—C24—C25	118.12 (15)
C10—C11—C12	120.63 (16)	C23—C24—H24	120.9
C10—C11—H11	119.7	C25—C24—H24	120.9
C12—C11—H11	119.7	C24—C25—C20	120.71 (15)
C13—C12—C11	119.08 (15)	C24—C25—H25	119.6
C13—C12—H12	120.5	C20—C25—H25	119.6
C11—C12—H12	120.5

C5—N1—C1—C2	3.2 (2)	C9—C8—C13—C12	1.5 (2)
C5—N1—C1—C14	179.07 (13)	C7—C8—C13—C12	−176.50 (15)
N1—C1—C2—C3	−1.3 (2)	N1—C1—C14—C19	3.9 (2)
C14—C1—C2—C3	−177.01 (14)	C2—C1—C14—C19	179.74 (15)
C1—C2—C3—C4	−3.6 (2)	N1—C1—C14—C15	−174.37 (15)
C1—C2—C3—C20	171.36 (14)	C2—C1—C14—C15	1.5 (2)
C2—C3—C4—C5	6.1 (2)	C19—C14—C15—C16	−1.2 (2)
C20—C3—C4—C5	−168.31 (14)	C1—C14—C15—C16	177.03 (15)
C2—C3—C4—C9	−173.89 (14)	C14—C15—C16—C17	0.3 (3)
C20—C3—C4—C9	11.7 (3)	C15—C16—C17—C18	1.3 (3)
C1—N1—C5—C4	−0.2 (2)	C15—C16—C17—Cl1	−178.25 (13)
C1—N1—C5—C6	−178.50 (14)	C16—C17—C18—C19	−1.9 (3)
C3—C4—C5—N1	−4.4 (2)	Cl1—C17—C18—C19	177.61 (12)
C9—C4—C5—N1	175.56 (14)	C17—C18—C19—C14	1.0 (3)
C3—C4—C5—C6	173.80 (14)	C15—C14—C19—C18	0.6 (2)
C9—C4—C5—C6	−6.2 (2)	C1—C14—C19—C18	−177.75 (15)
N1—C5—C6—C7	179.58 (15)	C2—C3—C20—C21	66.7 (2)
C4—C5—C6—C7	1.2 (2)	C4—C3—C20—C21	−118.66 (18)
C5—C6—C7—C8	2.9 (3)	C2—C3—C20—C25	−108.78 (17)
C6—C7—C8—C13	176.32 (15)	C4—C3—C20—C25	65.8 (2)
C6—C7—C8—C9	−1.7 (2)	C25—C20—C21—C22	−2.9 (2)
C13—C8—C9—C10	−4.0 (2)	C3—C20—C21—C22	−178.39 (15)
C7—C8—C9—C10	174.05 (14)	C20—C21—C22—C23	0.7 (2)
C13—C8—C9—C4	178.58 (14)	C21—C22—C23—C24	1.7 (2)
C7—C8—C9—C4	−3.4 (2)	C21—C22—C23—N2	−178.06 (14)
C3—C4—C9—C10	10.0 (3)	O1—N2—C23—C24	−3.1 (2)
C5—C4—C9—C10	−170.04 (15)	O2—N2—C23—C24	176.60 (14)
C3—C4—C9—C8	−172.80 (14)	O1—N2—C23—C22	176.65 (15)
C5—C4—C9—C8	7.2 (2)	O2—N2—C23—C22	−3.6 (2)
C8—C9—C10—C11	3.6 (2)	C22—C23—C24—C25	−1.8 (2)
C4—C9—C10—C11	−179.09 (15)	N2—C23—C24—C25	177.99 (14)
C9—C10—C11—C12	−0.7 (3)	C23—C24—C25—C20	−0.5 (2)
C10—C11—C12—C13	−1.9 (3)	C21—C20—C25—C24	2.8 (2)
C11—C12—C13—C8	1.5 (3)	C3—C20—C25—C24	178.38 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cgⁱ	0.95	2.72	3.510 (12)	142

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₁₅ClN₂O₂
M_r	410.84
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.1390 (12), 9.5350 (11), 11.9668 (17)
α, β, γ (°)	108.182 (4), 105.366 (4), 92.739 (3)
V (Å³)	945.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.34 × 0.32 × 0.22

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 1999)
T_min, T_max	0.926, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	11798, 4467, 3779
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.129, 1.06
No. of reflections	4467
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.47

Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure/MSC (Rigaku/MSC (2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cgⁱ	0.95	2.72	3.510 (12)	142

Symmetry code: (i) x, y−1, z.

Acknowledgements

We are grateful to the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

References

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