7-p-Tolyl-10,11-dihydro­benzo[h]furo[3,4-b]quinolin-8(7H)-one

Shi, C.

doi:10.1107/S160053681000591X

organic compounds

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Volume 66| Part 3| March 2010| Page o668

doi:10.1107/S160053681000591X

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7-p-Tolyl-10,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(7H)-one

Chunling Shi ^a ^*

^aSchool of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221008, People's Republic of China
^*Correspondence e-mail: scl_78@163.com

(Received 1 February 2010; accepted 13 February 2010; online 20 February 2010)

In the title compound, C₂₂H₁₇NO₂, the fused ring system is essentially planar (r.m.s. deviation = 0.021 Å) and the dihedral angle between the dihydropyridine and tolyl rings is 80.98 (11)°. In the crystal, the molecules are linked into chains along the b axis by intermolecular N—H⋯O and C—H⋯O hydrogen bonds. Adjacent chains are linked by π–π interactions [centroid–centroid separation = 3.5748 (15) Å].

Related literature

For the biological activity of podophyllotoxin and its derivatives, see: Bosmans et al. (1989 ); Eycken et al. (1989 ); Hitosuyanagi et al. (1997 , 1999 ); Lienard et al. (1991 ); Magedov et al. (2007 ); Poli & Giambastiani (2002 ); Tomioka et al. (1989 , 1993 ); Tratrat et al. (2002 ). For a related structure, see: Shi & Ji (2009 ).

Experimental

Crystal data

C₂₂H₁₇NO₂
M_r = 327.37
Monoclinic, P 2₁ /c
a = 10.6954 (16) Å
b = 13.0566 (18) Å
c = 12.183 (2) Å
β = 107.322 (3)°
V = 1624.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 223 K
0.60 × 0.34 × 0.30 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ) T_min = 0.770, T_max = 0.975
15611 measured reflections
2978 independent reflections
2476 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.138
S = 1.18
2978 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.87	2.00	2.802 (2)	153
C12—H12⋯O1ⁱ	0.94	2.49	3.248 (3)	137
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2000 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003 ); 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 global, I. DOI: 10.1107/S160053681000591X/ci5030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000591X/ci5030Isup2.hkl

checkCIF report

Comment top

Podophyllotoxin is an antitumor lignan that inhibits microtubule assembly (Eycken et al., 1989; Tomioka et al., 1989; Bosmans et al., 1989). Extensive structural modifications have been performed in order to obtain more potent and less toxic anticancer agents (Tomioka et al., 1993; Lienard et al., 1991; Poli et al., 2002). Among them, 4-aza-podophllotoxin (9-aryl-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one) derivatives reported as powerful DNA topoisomerase II inhibitors, have recently attached considerable interest (Hitosuyanagi et al., 1997; Hitosuyanagi et al., 1999; Tratrat et al., 2002; Magedov et al., 2007). We report here the crystal structure of the title compound, which was synthesized by the three-component reaction of naphthalen-1-amine with 4-methylbenzaldehyde and tetronic acid catalyzed by L-proline using ethanol as solvent at 353 K.

In the title compound, the 1,4-dihydropyridine (C1–C5/N1) and furanone rings are planar (Fig. 1) and both are coplanar with the naphthalene ring system i.e the fused ring system is essentially planar (r.m.s. deviation 0.021 Å). The dihedral angle between C1–C5/N1 and C16–C21 planes is 80.98 (11)°. The conformation of the title molecule differs from that of a related molecule, 7-methyl-9-p-tolyl-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one (Shi et al., 2009).

In the crystal structure, the molecules are linked by N1—H1···O2 and C12—H12···O1 intermolecular hydrogen bonds (Table 1) to form chains (Fig. 2) along the b axis. The adjacent chains are linked through π-π interactions between O1/C14/C4/C5/C15 and C1/C2/C6-C8/C13 rings with a centroid-centroid separation of 3.5748 (15) Å.

Related literature top

For the biological activity of podophyllotoxin and its derivatives, see: Bosmans et al. (1989); Eycken et al. (1989); Hitosuyanagi et al. (1997, 1999); Lienard et al. (1991); Magedov et al. (2007); Poli & Giambastiani (2002); Tomioka et al. (1989, 1993); Tratrat et al. (2002). For a related structure, see: Shi & Ji (2009).

Experimental top

The title compound was prepared by the reaction of naphthalen-1-amine (1 mmol) and 4-methylbenzalhyde (1 mmol) with tetronic acid (1 mmol) in the presence of L-proline (0.1 mmol) in ethanol (2 ml) at 353 K. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethylformamide and ethanol solution. ¹H NMR (DMSO-d₆, δ): 2.21 (3H, s, CH₃), 4.98 (1H, d, J = 16.0 Hz, CH₂), 5.07 (1H, d, J = 16.0 Hz, CH₂), 5.13 (1H, s, CH), 7.05 (2H, d, J = 8.0 Hz, ArH), 7.12 (3H, dd, J₁ = 6.4 Hz, J₂ = 8.0 Hz, ArH), 7.46 (1H, d, J = 8.8 Hz, ArH), 7.51-7.55 (1H, m, ArH), 7.60-7.64 (1H, m, ArH), 7.84 (1H, d, J = 8.0 Hz, ArH), 8.21 (1H, d, J = 8.0 Hz, ArH), 10.22 (1H, s, NH).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalStructure (Rigaku/MSC, 2003); 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 molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of the title compound.

7-p-Tolyl-10,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(7H)-one top

Crystal data top

C₂₂H₁₇NO₂	F(000) = 688
M_r = 327.37	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 5302 reflections
a = 10.6954 (16) Å	θ = 3.0–25.3°
b = 13.0566 (18) Å	µ = 0.09 mm⁻¹
c = 12.183 (2) Å	T = 223 K
β = 107.322 (3)°	Block, colourless
V = 1624.1 (4) Å³	0.60 × 0.34 × 0.30 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	2978 independent reflections
Radiation source: fine-focus sealed tube	2476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.1°
ω scans	h = −12→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −15→12
T_min = 0.770, T_max = 0.975	l = −14→14
15611 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0503P)² + 0.6601P] where P = (F_o² + 2F_c²)/3
2978 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₂H₁₇NO₂	V = 1624.1 (4) Å³
M_r = 327.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6954 (16) Å	µ = 0.09 mm⁻¹
b = 13.0566 (18) Å	T = 223 K
c = 12.183 (2) Å	0.60 × 0.34 × 0.30 mm
β = 107.322 (3)°

Data collection top

Rigaku Mercury diffractometer	2978 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	2476 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.975	R_int = 0.043
15611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.18	Δρ_max = 0.22 e Å⁻³
2978 reflections	Δρ_min = −0.18 e Å⁻³
228 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.04628 (16)	0.87892 (12)	0.19046 (14)	0.0446 (4)
O2	1.02197 (17)	0.72658 (13)	0.26734 (16)	0.0520 (5)
N1	0.88595 (17)	1.05854 (13)	0.32900 (16)	0.0357 (5)
H1	0.8921	1.1200	0.3035	0.043*
C1	0.8218 (2)	1.04144 (15)	0.41266 (18)	0.0303 (5)
C2	0.8127 (2)	0.94420 (16)	0.45353 (18)	0.0321 (5)
C3	0.8734 (2)	0.84879 (15)	0.41573 (19)	0.0323 (5)
H3	0.9455	0.8252	0.4827	0.039*
C4	0.9332 (2)	0.88088 (16)	0.32405 (18)	0.0327 (5)
C5	0.9376 (2)	0.97791 (16)	0.28925 (19)	0.0330 (5)
C6	0.7450 (2)	0.93198 (18)	0.5358 (2)	0.0442 (6)
H6	0.7384	0.8661	0.5648	0.053*
C7	0.6888 (3)	1.01196 (18)	0.5748 (2)	0.0481 (7)
H7	0.6436	1.0004	0.6291	0.058*
C8	0.6977 (2)	1.11247 (17)	0.5345 (2)	0.0398 (6)
C9	0.6407 (3)	1.19767 (19)	0.5729 (2)	0.0518 (7)
H9	0.5941	1.1878	0.6264	0.062*
C10	0.6521 (3)	1.2934 (2)	0.5338 (3)	0.0570 (7)
H10	0.6140	1.3493	0.5605	0.068*
C11	0.7207 (3)	1.30888 (18)	0.4538 (2)	0.0515 (7)
H11	0.7296	1.3755	0.4279	0.062*
C12	0.7747 (2)	1.22844 (16)	0.4130 (2)	0.0413 (6)
H12	0.8189	1.2400	0.3580	0.050*
C13	0.7652 (2)	1.12779 (16)	0.45230 (19)	0.0330 (5)
C14	1.0009 (2)	0.81812 (18)	0.2636 (2)	0.0392 (6)
C15	1.0079 (2)	0.98353 (17)	0.2007 (2)	0.0410 (6)
H15A	0.9500	1.0088	0.1274	0.049*
H15B	1.0846	1.0284	0.2258	0.049*
C16	0.7751 (2)	0.76137 (15)	0.38090 (19)	0.0332 (5)
C17	0.7769 (2)	0.68286 (17)	0.4572 (2)	0.0436 (6)
H17	0.8420	0.6822	0.5288	0.052*
C18	0.6844 (3)	0.60477 (17)	0.4302 (2)	0.0463 (6)
H18	0.6875	0.5527	0.4842	0.056*
C19	0.5881 (2)	0.60229 (17)	0.3254 (2)	0.0395 (6)
C20	0.5876 (2)	0.68095 (17)	0.2488 (2)	0.0407 (6)
H20	0.5239	0.6809	0.1765	0.049*
C21	0.6785 (2)	0.75938 (17)	0.2760 (2)	0.0376 (5)
H21	0.6747	0.8121	0.2225	0.045*
C22	0.4884 (3)	0.51737 (19)	0.2961 (3)	0.0541 (7)
H22A	0.5015	0.4722	0.3618	0.081*
H22B	0.4985	0.4788	0.2312	0.081*
H22C	0.4010	0.5464	0.2763	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0519 (10)	0.0402 (9)	0.0490 (10)	0.0012 (7)	0.0264 (9)	−0.0075 (8)
O2	0.0626 (12)	0.0345 (10)	0.0664 (12)	0.0061 (8)	0.0305 (10)	−0.0097 (8)
N1	0.0415 (11)	0.0252 (9)	0.0463 (12)	0.0009 (8)	0.0222 (9)	0.0003 (8)
C1	0.0299 (11)	0.0312 (12)	0.0313 (12)	−0.0018 (9)	0.0113 (9)	−0.0033 (9)
C2	0.0358 (12)	0.0297 (12)	0.0310 (12)	−0.0014 (9)	0.0101 (10)	−0.0026 (9)
C3	0.0336 (12)	0.0266 (11)	0.0348 (12)	0.0022 (8)	0.0076 (10)	0.0009 (9)
C4	0.0306 (12)	0.0307 (12)	0.0357 (13)	−0.0018 (9)	0.0084 (10)	−0.0052 (9)
C5	0.0316 (12)	0.0320 (12)	0.0367 (13)	−0.0003 (9)	0.0119 (10)	−0.0032 (9)
C6	0.0605 (16)	0.0341 (13)	0.0444 (15)	−0.0012 (11)	0.0254 (12)	0.0034 (11)
C7	0.0632 (17)	0.0431 (14)	0.0503 (16)	0.0005 (12)	0.0355 (14)	−0.0009 (11)
C8	0.0432 (14)	0.0387 (13)	0.0404 (13)	0.0012 (10)	0.0171 (11)	−0.0048 (10)
C9	0.0601 (17)	0.0476 (16)	0.0573 (17)	0.0051 (12)	0.0321 (14)	−0.0091 (12)
C10	0.0614 (18)	0.0427 (16)	0.075 (2)	0.0090 (12)	0.0321 (16)	−0.0141 (13)
C11	0.0565 (16)	0.0305 (13)	0.0739 (19)	0.0039 (11)	0.0291 (14)	−0.0036 (12)
C12	0.0426 (13)	0.0309 (12)	0.0540 (16)	0.0001 (10)	0.0198 (12)	−0.0020 (11)
C13	0.0313 (12)	0.0312 (12)	0.0368 (13)	−0.0018 (9)	0.0108 (10)	−0.0039 (9)
C14	0.0393 (13)	0.0370 (14)	0.0409 (14)	−0.0001 (10)	0.0114 (11)	−0.0074 (10)
C15	0.0456 (14)	0.0368 (13)	0.0450 (15)	−0.0006 (10)	0.0201 (11)	−0.0048 (10)
C16	0.0366 (12)	0.0256 (11)	0.0379 (13)	0.0019 (9)	0.0118 (10)	−0.0013 (9)
C17	0.0518 (15)	0.0333 (13)	0.0394 (14)	−0.0025 (11)	0.0038 (11)	0.0035 (10)
C18	0.0605 (16)	0.0293 (12)	0.0495 (16)	−0.0050 (11)	0.0168 (13)	0.0046 (10)
C19	0.0372 (13)	0.0318 (12)	0.0523 (15)	−0.0022 (9)	0.0178 (11)	−0.0070 (10)
C20	0.0358 (13)	0.0414 (13)	0.0410 (14)	−0.0001 (10)	0.0056 (10)	−0.0050 (11)
C21	0.0418 (13)	0.0320 (12)	0.0383 (14)	0.0018 (10)	0.0109 (11)	0.0027 (10)
C22	0.0510 (15)	0.0437 (15)	0.071 (2)	−0.0125 (12)	0.0231 (14)	−0.0085 (13)

Geometric parameters (Å, º) top

O1—C14	1.385 (3)	C9—H9	0.94
O1—C15	1.442 (3)	C10—C11	1.398 (4)
O2—C14	1.215 (3)	C10—H10	0.94
N1—C5	1.344 (3)	C11—C12	1.362 (3)
N1—C1	1.406 (3)	C11—H11	0.94
N1—H1	0.87	C12—C13	1.413 (3)
C1—C2	1.378 (3)	C12—H12	0.94
C1—C13	1.430 (3)	C15—H15A	0.98
C2—C6	1.409 (3)	C15—H15B	0.98
C2—C3	1.538 (3)	C16—C17	1.380 (3)
C3—C4	1.503 (3)	C16—C21	1.384 (3)
C3—C16	1.524 (3)	C17—C18	1.390 (3)
C3—H3	0.99	C17—H17	0.94
C4—C5	1.341 (3)	C18—C19	1.382 (3)
C4—C14	1.433 (3)	C18—H18	0.94
C5—C15	1.489 (3)	C19—C20	1.387 (3)
C6—C7	1.359 (3)	C19—C22	1.506 (3)
C6—H6	0.94	C20—C21	1.383 (3)
C7—C8	1.414 (3)	C20—H20	0.94
C7—H7	0.94	C21—H21	0.94
C8—C13	1.413 (3)	C22—H22A	0.97
C8—C9	1.413 (3)	C22—H22B	0.97
C9—C10	1.356 (4)	C22—H22C	0.97

C14—O1—C15	108.88 (16)	C11—C12—C13	120.8 (2)
C5—N1—C1	118.59 (18)	C11—C12—H12	119.6
C5—N1—H1	120.7	C13—C12—H12	119.6
C1—N1—H1	120.7	C8—C13—C12	118.4 (2)
C2—C1—N1	120.70 (18)	C8—C13—C1	119.01 (19)
C2—C1—C13	121.46 (19)	C12—C13—C1	122.6 (2)
N1—C1—C13	117.83 (18)	O2—C14—O1	119.4 (2)
C1—C2—C6	117.90 (19)	O2—C14—C4	131.3 (2)
C1—C2—C3	123.82 (18)	O1—C14—C4	109.28 (19)
C6—C2—C3	118.28 (19)	O1—C15—C5	103.55 (18)
C4—C3—C16	114.39 (18)	O1—C15—H15A	111.1
C4—C3—C2	107.95 (17)	C5—C15—H15A	111.1
C16—C3—C2	111.84 (17)	O1—C15—H15B	111.1
C4—C3—H3	107.5	C5—C15—H15B	111.1
C16—C3—H3	107.5	H15A—C15—H15B	109.0
C2—C3—H3	107.5	C17—C16—C21	117.7 (2)
C5—C4—C14	107.9 (2)	C17—C16—C3	119.9 (2)
C5—C4—C3	124.11 (19)	C21—C16—C3	122.32 (19)
C14—C4—C3	127.9 (2)	C16—C17—C18	121.3 (2)
C4—C5—N1	124.7 (2)	C16—C17—H17	119.4
C4—C5—C15	110.36 (19)	C18—C17—H17	119.4
N1—C5—C15	124.93 (19)	C19—C18—C17	121.2 (2)
C7—C6—C2	122.4 (2)	C19—C18—H18	119.4
C7—C6—H6	118.8	C17—C18—H18	119.4
C2—C6—H6	118.8	C18—C19—C20	117.2 (2)
C6—C7—C8	120.6 (2)	C18—C19—C22	121.2 (2)
C6—C7—H7	119.7	C20—C19—C22	121.7 (2)
C8—C7—H7	119.7	C21—C20—C19	121.7 (2)
C13—C8—C9	119.0 (2)	C21—C20—H20	119.1
C13—C8—C7	118.6 (2)	C19—C20—H20	119.1
C9—C8—C7	122.4 (2)	C20—C21—C16	120.9 (2)
C10—C9—C8	121.1 (2)	C20—C21—H21	119.6
C10—C9—H9	119.4	C16—C21—H21	119.6
C8—C9—H9	119.4	C19—C22—H22A	109.5
C9—C10—C11	119.9 (2)	C19—C22—H22B	109.5
C9—C10—H10	120.0	H22A—C22—H22B	109.5
C11—C10—H10	120.0	C19—C22—H22C	109.5
C12—C11—C10	120.7 (2)	H22A—C22—H22C	109.5
C12—C11—H11	119.6	H22B—C22—H22C	109.5
C10—C11—H11	119.6

C5—N1—C1—C2	0.4 (3)	C9—C8—C13—C1	−179.4 (2)
C5—N1—C1—C13	−178.79 (19)	C7—C8—C13—C1	0.1 (3)
N1—C1—C2—C6	−178.9 (2)	C11—C12—C13—C8	0.3 (4)
C13—C1—C2—C6	0.3 (3)	C11—C12—C13—C1	−179.3 (2)
N1—C1—C2—C3	1.9 (3)	C2—C1—C13—C8	−0.5 (3)
C13—C1—C2—C3	−178.92 (19)	N1—C1—C13—C8	178.7 (2)
C1—C2—C3—C4	−3.7 (3)	C2—C1—C13—C12	179.1 (2)
C6—C2—C3—C4	177.1 (2)	N1—C1—C13—C12	−1.7 (3)
C1—C2—C3—C16	−130.4 (2)	C15—O1—C14—O2	179.3 (2)
C6—C2—C3—C16	50.4 (3)	C15—O1—C14—C4	−0.6 (2)
C16—C3—C4—C5	128.9 (2)	C5—C4—C14—O2	179.8 (3)
C2—C3—C4—C5	3.7 (3)	C3—C4—C14—O2	3.2 (4)
C16—C3—C4—C14	−54.9 (3)	C5—C4—C14—O1	−0.3 (3)
C2—C3—C4—C14	179.9 (2)	C3—C4—C14—O1	−176.95 (19)
C14—C4—C5—N1	−178.8 (2)	C14—O1—C15—C5	1.1 (2)
C3—C4—C5—N1	−2.0 (4)	C4—C5—C15—O1	−1.3 (3)
C14—C4—C5—C15	1.0 (3)	N1—C5—C15—O1	178.54 (19)
C3—C4—C5—C15	177.8 (2)	C4—C3—C16—C17	137.1 (2)
C1—N1—C5—C4	−0.4 (3)	C2—C3—C16—C17	−99.8 (2)
C1—N1—C5—C15	179.8 (2)	C4—C3—C16—C21	−45.9 (3)
C1—C2—C6—C7	0.4 (4)	C2—C3—C16—C21	77.3 (3)
C3—C2—C6—C7	179.6 (2)	C21—C16—C17—C18	−0.5 (3)
C2—C6—C7—C8	−0.8 (4)	C3—C16—C17—C18	176.7 (2)
C6—C7—C8—C13	0.5 (4)	C16—C17—C18—C19	0.7 (4)
C6—C7—C8—C9	−180.0 (2)	C17—C18—C19—C20	−0.1 (4)
C13—C8—C9—C10	−1.3 (4)	C17—C18—C19—C22	179.7 (2)
C7—C8—C9—C10	179.2 (3)	C18—C19—C20—C21	−0.7 (3)
C8—C9—C10—C11	0.3 (4)	C22—C19—C20—C21	179.5 (2)
C9—C10—C11—C12	1.0 (4)	C19—C20—C21—C16	0.9 (3)
C10—C11—C12—C13	−1.3 (4)	C17—C16—C21—C20	−0.3 (3)
C9—C8—C13—C12	1.0 (3)	C3—C16—C21—C20	−177.4 (2)
C7—C8—C13—C12	−179.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87	2.00	2.802 (2)	153
C12—H12···O1ⁱ	0.94	2.49	3.248 (3)	137

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇NO₂
M_r	327.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	10.6954 (16), 13.0566 (18), 12.183 (2)
β (°)	107.322 (3)
V (Å³)	1624.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.34 × 0.30

Data collection
Diffractometer	Rigaku Mercury diffractometer
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.770, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	15611, 2978, 2476
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.138, 1.18
No. of reflections	2978
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrystalClear (Rigaku, 2000), CrystalStructure (Rigaku/MSC, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.87	2.00	2.802 (2)	153
C12—H12···O1ⁱ	0.94	2.49	3.248 (3)	137

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

Acknowledgements

The author thanks the Scientific Research Item of Xuzhou Institute of Technology (grant No. XKY2009114) for financial support.

References

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