7-(3-Nitro­phen­yl)-9,10-dihydro-7H-benzo[h]cyclo­penta­[b]quinolin-8(11H)-one

Li, T.; Zhang, H.

doi:10.1107/S1600536811043546

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3068

doi:10.1107/S1600536811043546

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7-(3-Nitrophenyl)-9,10-dihydro-7H-benzo[h]cyclopenta[b]quinolin-8(11H)-one

Tuanjie Li ^a ^* and Honghong Zhang ^a

^aSchool of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: ltj2008@xznu.edu.cn

(Received 8 October 2011; accepted 20 October 2011; online 29 October 2011)

In the title compound, C₂₂H₁₆N₂O₃, the naphthalene ring, the 1,4-dihydropyridine ring and the cyclopent-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-dihydropyridine ring form a dihedral angle of 78.75 (4)°. Intermolecular N—H⋯O hydrogen bonds and C—H⋯π interactions 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_r = 356.37
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.130
S = 1.12
3897 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043546/hg5109sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811043546/hg5109Isup3.cml

checkCIF report

Comment top

The 1,4-dihydropyridine (1,4-DHP) derivatives exhibits various bioactivities, including sedative-hypnotic activity (Zheng et al. 2011), inhibition of the α 4-integrin-paxillin interaction (Ginsberg et al. 2011), anti-microbial activities (Nadaraj et al. 2009),and antitumor activity (Husson et al. 2011). These reports inspired us to study the relationship between their structures and activities. During the synthesis of 1,4-dihydropyridine (1,4-DHP) derivatives, the title compound, (I) was isolated and its structure was determined by X-ray diffraction. Herein we report its crystal structure.

In the molecular structure (Fig. 1), the naphthalene ring, the 1,4-dihydropyridine ring and the cyclopent-2-enone ring adopt planar conformations with RMS of 0.0201 Å, 0.0235 Å and 0.0058 Å, respectively. The largest deviation of these rings are 0.033 (1) Å(C2), 0.038 (1) Å(C3), 0.008 (1) Å(C5), respectively. The fused ring system is almost coplanar, for the dihedral angle between the neighboring rings are 1.93 (0.11) ° and 2.30 (9)° respectively. The planar 3-nitrophenyl ring at position 7 and the 1,4-dihydropyridine ring forms a dihedral angle of 78.75 (4)°. The crystal packing is stablized by the intermolecular N—H···O hydrogen bond and C—H···π interactions (Fig. 2, Table 1).

Related literature top

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

Experimental top

The title compound was synthesized according to the procedure (Heravi et al. 2010). A round-bottomed flask was charged with 3-nitrobenzaldehyde (1 mmol), cyclopentane-1,3-dione (1 mmol), 1-naphtylamine (1 mmol), acetic acid (5 ml), and H₆P₂W₁₈O_62.18H₂O (0.01 mmol). The reaction mixture was stirred until completion (monitored by TLC). Then the mixture was poured into ice water. The precipitated products were separated by filtration, washed with water, recrystallized in a dimethylformamide-ethanol (DMF-EtOH) solution. The recrystallization gave single-crystals suitable for X-ray diffraction.

Computing details top

Data collection: CrystalClearSM Expert (Rigaku/MSC, 2009); cell refinement: CrystalClearSM Expert (Rigaku/MSC, 2009); data reduction: CrystalClearSM Expert (Rigaku/MSC, 2009); 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. Cg is the centroid of the ring of C11/C12/C13/C14/C15/C16.
	Fig. 2. The packing diagram of (I), Hydrogen bond represented by the dashed line.

7-(3-Nitrophenyl)-9,10-dihydro-7H- benzo[h]cyclopenta[b]quinolin-8(11H)-one top

Crystal data top

C₂₂H₁₆N₂O₃	F(000) = 744
M_r = 356.37	D_x = 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

Data collection top

Rigaku Saturn724 CCD diffractometer	3897 independent reflections
Radiation source: rotating anode	3094 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.046
Detector resolution: 14.222 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)	k = −18→16
T_min = 0.977, T_max = 0.983	l = −14→15
16937 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)] = 0.055	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(F_o²) + (0.0585P)² + 0.0399P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₁₆N₂O₃	V = 1634.4 (3) Å³
M_r = 356.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.256 (1) Å	µ = 0.10 mm⁻¹
b = 13.7570 (14) Å	T = 113 K
c = 11.9830 (12) Å	0.24 × 0.20 × 0.18 mm
β = 104.827 (5)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3897 independent reflections
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)	3094 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.983	R_int = 0.046
16937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.27 e Å⁻³
3897 reflections	Δρ_min = −0.21 e Å⁻³
248 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
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₆N₂O₃
M_r	356.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.256 (1), 13.7570 (14), 11.9830 (12)
β (°)	104.827 (5)
V (Å³)	1634.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009)
T_min, T_max	0.977, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16937, 3897, 3094
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.130, 1.12
No. of reflections	3897
No. of parameters	248
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: CrystalClearSM Expert (Rigaku/MSC, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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)	145.0

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

References

Ginsberg, M. & Kummer, C. (2011). WO Patent No. 2011034896. Google Scholar
Heravi, M. M., Hosseini, T., Derikvand, F., Beheshtiha, S. Y. S. & Bamoharram, F. F. (2010). Synth. Commun. 40, 2402–2406. Web of Science CrossRef CAS Google Scholar
Husson, H.-P., Giorgi-Renault, S., Tratrat, C., Atassi, G., Pierre, A., Renard, P. & Pfeiffer, B. (2011). Eur. Patent No. 1103554. Google Scholar
Nadaraj, V., Thamarai Selvi, S. & Mohan, S. (2009). Eur. J. Med. Chem. 44, 976–980. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2009). CrystalClearSM Expert. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, L., Yin, X. J., Yang, C. L., Li, Y. & Yin, S. F. (2011). Chem. Nat. Compd, 47, 170–175. CrossRef CAS Google Scholar

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Volume 67| Part 11| November 2011| Page o3068

doi:10.1107/S1600536811043546

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