3-(4-Chloro-phen-yl)-1-(4-nitro-phen-yl)benzo[f]quinoline.

In the title compound, C(25)H(15)ClN(2)O(2), the pyridine ring is inclined at angles of 6.89 (7), 4.24 (9) and 66.98 (4)° with respect to the naphthalene, chloro-phenyl and nitro-phenyl 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 mol-ecules= 3.7838 (11) Å] links the mol-ecules into dimers, while the C-H⋯Cg type π-ring inter-actons link the mol-ecules 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 = 410.84

Triclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.129

S = 1.06

4467 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.47 e Å−3

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 ▶).

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

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

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

C25H15ClN2O2	Z = 2
Mr = 410.84	F(000) = 424
Triclinic, P1	Dx = 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

Rigaku Saturn diffractometer	4467 independent reflections
Radiation source: rotating anode	3779 reflections with I > 2σ(I)
confocal	Rint = 0.034
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999)	k = −12→12
Tmin = 0.926, Tmax = 0.952	l = −15→15
11798 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.2446P] where P = (Fo2 + 2Fc2)/3
4467 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.47 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	−0.44740 (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*

	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)

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)

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

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) . Cg is the centroid of the C14–C19 ring.