7-(3-Nitro-phen-yl)-9,10-dihydro-7H-benzo[h]cyclo-penta-[b]quinolin-8(11H)-one.

In the title compound, C(22)H(16)N(2)O(3), the naphthalene ring, the 1,4-dihydro-pyridine ring and the cyclo-pent-2-enone ring are nearly coplanar, with the dihedral angles between the neighbouring rings being 1.93 (11) and 2.30 (9)°, respectively. The benzene ring group at position 7 and the 1,4-dihydro-pyridine ring form a dihedral angle of 78.75 (4)°. Inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions stabilize the crystal packing.

Related literature

For the medicinal use of 1,4-dihydro­pyridine derivatives, see: Zheng et al. (2011 ▶); Ginsberg & Kummer (2011 ▶); Nadaraj et al. (2009 ▶); Husson et al. (2011 ▶). For the preparation of the title compound, see: Heravi et al. (2010 ▶).

Experimental

Crystal data

C22H16N2O3

M = 356.37

Monoclinic,

a = 10.256 (1) Å

b = 13.7570 (14) Å

c = 11.9830 (12) Å

β = 104.827 (5)°

V = 1634.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 113 K

0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009 ▶) T min = 0.977, T max = 0.983

16937 measured reflections

3897 independent reflections

3094 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.130

S = 1.12

3897 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClearSM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClearSM Expert; data reduction: CrystalClearSM Expert; 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/S1600536811043546/hg5109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043546/hg5109Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043546/hg5109Isup3.cml

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

C22H16N2O3	F(000) = 744
Mr = 356.37	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 4977 reflections
a = 10.256 (1) Å	θ = 1.8–28.0°
b = 13.7570 (14) Å	µ = 0.10 mm−1
c = 11.9830 (12) Å	T = 113 K
β = 104.827 (5)°	Prism, colorless
V = 1634.4 (3) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	3897 independent reflections
Radiation source: rotating anode	3094 reflections with I > 2σ(I)
multilayer	Rint = 0.046
Detector resolution: 14.222 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)	k = −18→16
Tmin = 0.977, Tmax = 0.983	l = −14→15
16937 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.0399P] where P = (Fo2 + 2Fc2)/3
3897 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.49879 (12)	0.27956 (8)	0.21675 (10)	0.0302 (3)
O2	0.22400 (14)	0.05360 (8)	0.50038 (12)	0.0396 (3)
O3	0.05702 (14)	0.00451 (9)	0.36064 (13)	0.0555 (5)
N1	0.40366 (13)	0.59115 (10)	0.34262 (12)	0.0204 (3)
N2	0.14286 (15)	0.06518 (10)	0.40583 (15)	0.0333 (4)
C1	0.32624 (14)	0.56590 (10)	0.42002 (13)	0.0182 (3)
C2	0.30280 (15)	0.46920 (11)	0.44074 (14)	0.0210 (3)
C3	0.36250 (15)	0.38501 (11)	0.38630 (13)	0.0205 (3)
H3	0.4315	0.3524	0.4494	0.025*
C4	0.43418 (15)	0.42402 (11)	0.30100 (14)	0.0209 (3)
C5	0.45220 (14)	0.52071 (11)	0.28614 (13)	0.0192 (3)
C6	0.53292 (16)	0.54216 (11)	0.20092 (14)	0.0237 (4)
H6A	0.6177	0.5766	0.2382	0.028*
H6B	0.4805	0.5820	0.1360	0.028*
C7	0.56175 (17)	0.44056 (11)	0.15962 (15)	0.0249 (4)
H7A	0.5219	0.4336	0.0756	0.030*
H7B	0.6601	0.4290	0.1761	0.030*
C8	0.49657 (16)	0.36910 (12)	0.22699 (14)	0.0232 (4)
C9	0.22432 (16)	0.44723 (11)	0.51891 (14)	0.0261 (4)
H9	0.2063	0.3811	0.5322	0.031*
C10	0.17360 (16)	0.51798 (11)	0.57591 (14)	0.0269 (4)
H10	0.1210	0.5004	0.6275	0.032*
C11	0.19893 (15)	0.61746 (11)	0.55856 (13)	0.0212 (3)
C12	0.27526 (14)	0.64231 (10)	0.47886 (13)	0.0191 (3)
C13	0.29923 (16)	0.74235 (11)	0.46203 (14)	0.0226 (4)
H13	0.3481	0.7607	0.4079	0.027*
C14	0.25244 (15)	0.81264 (12)	0.52334 (14)	0.0251 (4)
H14	0.2696	0.8792	0.5112	0.030*
C15	0.17967 (16)	0.78757 (12)	0.60362 (14)	0.0251 (4)
H15	0.1493	0.8369	0.6464	0.030*
C16	0.15242 (15)	0.69215 (12)	0.62036 (14)	0.0248 (4)
H16	0.1018	0.6757	0.6739	0.030*
C17	0.25581 (15)	0.30911 (11)	0.33354 (13)	0.0202 (3)
C18	0.24757 (15)	0.22350 (11)	0.39195 (14)	0.0219 (4)
H18	0.3082	0.2114	0.4650	0.026*
C19	0.14954 (15)	0.15545 (11)	0.34252 (14)	0.0235 (4)
C20	0.05978 (16)	0.16991 (12)	0.23582 (15)	0.0289 (4)
H20	−0.0061	0.1223	0.2032	0.035*
C21	0.06897 (17)	0.25572 (13)	0.17830 (15)	0.0307 (4)
H21	0.0088	0.2675	0.1049	0.037*
C22	0.16534 (16)	0.32482 (12)	0.22678 (14)	0.0264 (4)
H22	0.1696	0.3837	0.1865	0.032*
H1	0.4201 (19)	0.6518 (14)	0.3272 (16)	0.041 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0399 (7)	0.0183 (6)	0.0395 (8)	0.0010 (5)	0.0233 (6)	−0.0023 (5)
O2	0.0559 (8)	0.0246 (7)	0.0386 (8)	−0.0027 (6)	0.0127 (7)	0.0029 (6)
O3	0.0480 (8)	0.0283 (7)	0.0848 (12)	−0.0197 (6)	0.0072 (8)	−0.0018 (7)
N1	0.0254 (7)	0.0159 (6)	0.0234 (8)	−0.0002 (5)	0.0123 (6)	0.0007 (5)
N2	0.0336 (8)	0.0184 (7)	0.0514 (11)	−0.0038 (6)	0.0173 (8)	−0.0044 (7)
C1	0.0190 (7)	0.0197 (8)	0.0172 (8)	0.0000 (6)	0.0069 (6)	0.0007 (6)
C2	0.0241 (8)	0.0196 (8)	0.0208 (9)	−0.0011 (6)	0.0082 (7)	0.0002 (6)
C3	0.0240 (8)	0.0184 (8)	0.0207 (8)	0.0007 (6)	0.0086 (7)	0.0012 (6)
C4	0.0234 (7)	0.0194 (8)	0.0217 (9)	0.0008 (6)	0.0094 (7)	0.0007 (6)
C5	0.0200 (7)	0.0201 (8)	0.0183 (8)	0.0017 (6)	0.0066 (6)	0.0013 (6)
C6	0.0288 (8)	0.0211 (8)	0.0256 (9)	0.0012 (7)	0.0148 (7)	0.0019 (7)
C7	0.0299 (8)	0.0232 (8)	0.0259 (9)	0.0027 (7)	0.0150 (7)	0.0001 (7)
C8	0.0253 (8)	0.0229 (8)	0.0233 (9)	0.0011 (7)	0.0095 (7)	0.0001 (7)
C9	0.0347 (9)	0.0199 (8)	0.0287 (10)	−0.0043 (7)	0.0172 (8)	−0.0005 (7)
C10	0.0340 (9)	0.0246 (9)	0.0277 (10)	−0.0037 (7)	0.0182 (8)	−0.0013 (7)
C11	0.0211 (7)	0.0230 (8)	0.0207 (9)	0.0005 (6)	0.0074 (7)	−0.0013 (7)
C12	0.0189 (7)	0.0188 (8)	0.0199 (8)	0.0008 (6)	0.0056 (6)	−0.0011 (6)
C13	0.0218 (8)	0.0215 (8)	0.0266 (9)	0.0005 (6)	0.0101 (7)	−0.0008 (7)
C14	0.0260 (8)	0.0188 (8)	0.0318 (10)	0.0004 (6)	0.0098 (7)	−0.0031 (7)
C15	0.0240 (8)	0.0245 (8)	0.0283 (10)	0.0013 (7)	0.0093 (7)	−0.0069 (7)
C16	0.0233 (8)	0.0295 (9)	0.0236 (9)	0.0005 (7)	0.0099 (7)	−0.0032 (7)
C17	0.0222 (8)	0.0189 (8)	0.0222 (9)	0.0031 (6)	0.0110 (7)	−0.0018 (6)
C18	0.0230 (8)	0.0195 (8)	0.0246 (9)	0.0018 (6)	0.0085 (7)	−0.0012 (6)
C19	0.0235 (8)	0.0177 (8)	0.0325 (10)	0.0001 (6)	0.0129 (7)	−0.0045 (7)
C20	0.0226 (8)	0.0311 (9)	0.0345 (10)	−0.0027 (7)	0.0101 (8)	−0.0149 (8)
C21	0.0246 (8)	0.0416 (11)	0.0248 (10)	0.0045 (8)	0.0043 (7)	−0.0041 (8)
C22	0.0257 (8)	0.0294 (9)	0.0261 (9)	0.0039 (7)	0.0099 (7)	0.0014 (7)

O1—C8	1.2387 (18)	C9—H9	0.9500
O2—N2	1.2325 (18)	C10—C11	1.418 (2)
O3—N2	1.2333 (18)	C10—H10	0.9500
N1—C5	1.3481 (19)	C11—C16	1.419 (2)
N1—C1	1.4101 (19)	C11—C12	1.423 (2)
N1—H1	0.881 (19)	C12—C13	1.421 (2)
N2—C19	1.466 (2)	C13—C14	1.373 (2)
C1—C2	1.385 (2)	C13—H13	0.9500
C1—C12	1.437 (2)	C14—C15	1.403 (2)
C2—C9	1.415 (2)	C14—H14	0.9500
C2—C3	1.532 (2)	C15—C16	1.368 (2)
C3—C4	1.503 (2)	C15—H15	0.9500
C3—C17	1.528 (2)	C16—H16	0.9500
C3—H3	1.0000	C17—C18	1.384 (2)
C4—C5	1.361 (2)	C17—C22	1.392 (2)
C4—C8	1.434 (2)	C18—C19	1.390 (2)
C5—C6	1.499 (2)	C18—H18	0.9500
C6—C7	1.536 (2)	C19—C20	1.386 (2)
C6—H6A	0.9900	C20—C21	1.382 (2)
C6—H6B	0.9900	C20—H20	0.9500
C7—C8	1.530 (2)	C21—C22	1.387 (2)
C7—H7A	0.9900	C21—H21	0.9500
C7—H7B	0.9900	C22—H22	0.9500
C9—C10	1.366 (2)
C5—N1—C1	119.70 (13)	C2—C9—H9	118.9
C5—N1—H1	117.4 (13)	C9—C10—C11	120.44 (15)
C1—N1—H1	122.9 (13)	C9—C10—H10	119.8
O2—N2—O3	123.67 (15)	C11—C10—H10	119.8
O2—N2—C19	118.37 (14)	C10—C11—C16	121.59 (15)
O3—N2—C19	117.95 (16)	C10—C11—C12	118.89 (14)
C2—C1—N1	120.48 (14)	C16—C11—C12	119.51 (14)
C2—C1—C12	120.86 (14)	C13—C12—C11	118.21 (14)
N1—C1—C12	118.65 (13)	C13—C12—C1	122.74 (14)
C1—C2—C9	118.55 (14)	C11—C12—C1	119.04 (13)
C1—C2—C3	122.89 (14)	C14—C13—C12	120.60 (15)
C9—C2—C3	118.52 (13)	C14—C13—H13	119.7
C4—C3—C17	112.70 (12)	C12—C13—H13	119.7
C4—C3—C2	109.77 (13)	C13—C14—C15	120.91 (15)
C17—C3—C2	111.79 (12)	C13—C14—H14	119.5
C4—C3—H3	107.4	C15—C14—H14	119.5
C17—C3—H3	107.4	C16—C15—C14	120.06 (15)
C2—C3—H3	107.4	C16—C15—H15	120.0
C5—C4—C8	109.70 (14)	C14—C15—H15	120.0
C5—C4—C3	122.99 (14)	C15—C16—C11	120.67 (15)
C8—C4—C3	127.29 (14)	C15—C16—H16	119.7
N1—C5—C4	123.85 (15)	C11—C16—H16	119.7
N1—C5—C6	122.65 (13)	C18—C17—C22	118.99 (14)
C4—C5—C6	113.49 (13)	C18—C17—C3	120.16 (13)
C5—C6—C7	103.04 (12)	C22—C17—C3	120.85 (14)
C5—C6—H6A	111.2	C17—C18—C19	119.25 (15)
C7—C6—H6A	111.2	C17—C18—H18	120.4
C5—C6—H6B	111.2	C19—C18—H18	120.4
C7—C6—H6B	111.2	C20—C19—C18	122.26 (15)
H6A—C6—H6B	109.1	C20—C19—N2	119.42 (15)
C8—C7—C6	105.57 (13)	C18—C19—N2	118.32 (15)
C8—C7—H7A	110.6	C21—C20—C19	117.95 (15)
C6—C7—H7A	110.6	C21—C20—H20	121.0
C8—C7—H7B	110.6	C19—C20—H20	121.0
C6—C7—H7B	110.6	C20—C21—C22	120.57 (16)
H7A—C7—H7B	108.8	C20—C21—H21	119.7
O1—C8—C4	127.41 (15)	C22—C21—H21	119.7
O1—C8—C7	124.41 (14)	C21—C22—C17	120.97 (16)
C4—C8—C7	108.18 (13)	C21—C22—H22	119.5
C10—C9—C2	122.19 (15)	C17—C22—H22	119.5
C10—C9—H9	118.9
C5—N1—C1—C2	1.7 (2)	C10—C11—C12—C13	179.71 (13)
C5—N1—C1—C12	−179.79 (13)	C16—C11—C12—C13	−1.6 (2)
N1—C1—C2—C9	−179.88 (13)	C10—C11—C12—C1	−1.1 (2)
C12—C1—C2—C9	1.7 (2)	C16—C11—C12—C1	177.64 (13)
N1—C1—C2—C3	2.5 (2)	C2—C1—C12—C13	178.67 (14)
C12—C1—C2—C3	−175.93 (13)	N1—C1—C12—C13	0.2 (2)
C1—C2—C3—C4	−5.9 (2)	C2—C1—C12—C11	−0.5 (2)
C9—C2—C3—C4	176.43 (14)	N1—C1—C12—C11	−178.97 (13)
C1—C2—C3—C17	−131.76 (15)	C11—C12—C13—C14	1.5 (2)
C9—C2—C3—C17	50.61 (19)	C1—C12—C13—C14	−177.67 (14)
C17—C3—C4—C5	131.30 (15)	C12—C13—C14—C15	−0.2 (2)
C2—C3—C4—C5	6.0 (2)	C13—C14—C15—C16	−1.1 (2)
C17—C3—C4—C8	−50.8 (2)	C14—C15—C16—C11	1.0 (2)
C2—C3—C4—C8	−176.06 (14)	C10—C11—C16—C15	179.01 (14)
C1—N1—C5—C4	−1.8 (2)	C12—C11—C16—C15	0.3 (2)
C1—N1—C5—C6	178.78 (13)	C4—C3—C17—C18	134.40 (14)
C8—C4—C5—N1	179.14 (14)	C2—C3—C17—C18	−101.41 (16)
C3—C4—C5—N1	−2.6 (2)	C4—C3—C17—C22	−45.87 (19)
C8—C4—C5—C6	−1.35 (18)	C2—C3—C17—C22	78.32 (18)
C3—C4—C5—C6	176.90 (13)	C22—C17—C18—C19	0.1 (2)
N1—C5—C6—C7	−179.01 (14)	C3—C17—C18—C19	179.86 (13)
C4—C5—C6—C7	1.47 (17)	C17—C18—C19—C20	0.5 (2)
C5—C6—C7—C8	−0.98 (16)	C17—C18—C19—N2	179.86 (14)
C5—C4—C8—O1	−179.08 (15)	O2—N2—C19—C20	179.70 (15)
C3—C4—C8—O1	2.8 (3)	O3—N2—C19—C20	0.5 (2)
C5—C4—C8—C7	0.62 (18)	O2—N2—C19—C18	0.3 (2)
C3—C4—C8—C7	−177.54 (14)	O3—N2—C19—C18	−178.90 (15)
C6—C7—C8—O1	180.00 (15)	C18—C19—C20—C21	−0.5 (2)
C6—C7—C8—C4	0.29 (17)	N2—C19—C20—C21	−179.87 (14)
C1—C2—C9—C10	−1.3 (2)	C19—C20—C21—C22	−0.1 (2)
C3—C2—C9—C10	176.39 (14)	C20—C21—C22—C17	0.7 (2)
C2—C9—C10—C11	−0.3 (3)	C18—C17—C22—C21	−0.7 (2)
C9—C10—C11—C16	−177.23 (15)	C3—C17—C22—C21	179.55 (14)
C9—C10—C11—C12	1.5 (2)

Cg is the centroid of the ring of C11/C12/C13/C14/C15/C16. [ok as edited?]

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.881 (19)	2.07 (2)	2.9307 (17)	165.9 (18)
C21—H21···Cgii	0.95	2.69	3.5090 (19)	145.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the ring of C11–C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.881 (19)	2.07 (2)	2.9307 (17)	165.9 (18)
C21—H21⋯Cgii	0.95	2.69	3.5090 (19)	145

Symmetry codes: (i) ; (ii) .