12-Benzoyl-2-methyl­naphtho­[2,3-b]indolizine-6,11-dione

Liu, Y.; Wang, S.-H.; Shen, S.-R.; Yang, Z.-H.

doi:10.1107/S1600536811019623

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1550

doi:10.1107/S1600536811019623

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12-Benzoyl-2-methylnaphtho[2,3-b]indolizine-6,11-dione

Yun Liu,^a Su-Hui Wang,^a ^* Shu-Ren Shen ^a and Zong-Hui Yang ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: liu__yun3@sina.com.cn

(Received 9 May 2011; accepted 24 May 2011; online 28 May 2011)

In the title compound, C₂₄H₁₅NO₃, the fused naphthaquinone–pyrrole unit is approximately planar, the naphthaquinone ring system making a dihedral angle of 2.91 (10)° with the pyrrole ring. The plane of the pyrrole ring makes a dihedral angle 61.64 (14)° with that of the benzene ring of the benzoylmethylene group. The crystal structure is stablized by intramolecular C—H⋯O interactions.

Related literature

For the properties of indolizine, see Olden et al. (1991 ); Jaffrezou et al. (1992 ). For the preparation of benzo[f]pyrido[1,2-a]indole-6,11-dione, see Pratt et al. (1957 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₄H₁₅NO₃
M_r = 365.37
Monoclinic, P 2₁ /c
a = 7.1260 (14) Å
b = 10.125 (2) Å
c = 24.352 (5) Å
β = 90.22 (3)°
V = 1757.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995 ) T_min = 0.973, T_max = 0.991
3371 measured reflections
3103 independent reflections
1555 reflections with I > 2σ(I)
R_int = 0.062
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.169
S = 1.02
3103 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3ⁱ	0.93	2.45	3.305 (5)	152
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019623/ds2112sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019623/ds2112Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019623/ds2112Isup3.cml

checkCIF report

Comment top

The natural and many synthetic indolizines have a diversity of biological activity and are playing an increasingly important role in developing new pharmaceuticals [Olden et al., 1991; Jaffrezou et al., 1992]. Benzo[f]pyrido[1,2-a]indole-6,11-diones are benzo-fused indolizines and occur in several marine alkaloids. The synthesis of these compounds has drawn much research interest [Pratt et al., 1957]. In our ongoing research work on the direct one pot syntheses of benzo[f]pyrido[1,2-a]indole-6,11-diones, we have prepared the title compound (I). As part of this study, we have undertaken an X-ray crystallographic analysis of (I) in order to confirm its structure.

The bond lengths and angles of the title molecule (Fig. 1) are within normal ranges (Allen et al., 1987). The naphthaquinone ring is essentially planar to the pyrrole ring with the dihedral angel being 2.91 (10)°. The pyrrole ring makes the dihedral angle 61.64 (14)° with the benzene ring of the benzoylmethylene group. Although atoms C16, C20 and C24 attached to atom N are all of sp² hybridization, their different environments cause slight differences in the N—C16, N—C20 and N—C24 bond lengths, and in the C16—N—C20, C16— N—C24, and C20—N—C24 angles (Table 1). The molecular packing is stabilized by weak intermolecular C—H···O hydrogen bonds.

Related literature top

For the properties of indolizine, see Olden et al. (1991); Jaffrezou et al. (1992). For the preparation of benzo[f]pyrido[1,2-a]indole-6,11-dione, see Pratt et al. (1957). For bond-length data, see: Allen et al. (1987).

Experimental top

The compound (I) was prepared by the reaction of 4-methyl pyridine (1.0 mmol), benzoylacetone (1.0 mmol), and 2,3-dichloro-1,4-naphthaquionone (1.0 mmol) mixed in 10 mL CH3CN. The reaction mixture were heated to reflux for 24 h and was isolated by column chromatography after evaporation of the solvent. Single crystals of (I) were obtained by slow evaporation from an petroleum ether-ethyl acetate(3:1) solvent system (yield 62%).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis.

12-Benzoyl-2-methylnaphtho[2,3-b]indolizine-6,11-dione top

Crystal data top

C₂₄H₁₅NO₃	F(000) = 760
M_r = 365.37	D_x = 1.381 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 538 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.1260 (14) Å	Cell parameters from 25 reflections
b = 10.125 (2) Å	θ = 9–12°
c = 24.352 (5) Å	µ = 0.09 mm⁻¹
β = 90.22 (3)°	T = 295 K
V = 1757.0 (6) Å³	Block, red
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1555 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ω/2θ scans	h = −8→0
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = −12→0
T_min = 0.973, T_max = 0.991	l = −28→28
3371 measured reflections	3 standard reflections every 200 reflections
3103 independent reflections	intensity decay: none

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) = 0.169	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0675P)² + 0.0651P] where P = (F_o² + 2F_c²)/3
3103 reflections	(Δ/σ)_max = 0.006
254 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₄H₁₅NO₃	V = 1757.0 (6) Å³
M_r = 365.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1260 (14) Å	µ = 0.09 mm⁻¹
b = 10.125 (2) Å	T = 295 K
c = 24.352 (5) Å	0.30 × 0.20 × 0.10 mm
β = 90.22 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1555 reflections with I > 2σ(I)
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	R_int = 0.062
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
3371 measured reflections	intensity decay: none
3103 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3103 reflections	Δρ_min = −0.22 e Å⁻³
254 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
N	0.1808 (3)	0.6115 (3)	0.44928 (11)	0.0478 (7)
C24	0.2311 (4)	0.4972 (3)	0.47630 (13)	0.0446 (8)
O3	0.2792 (4)	0.5789 (3)	0.56513 (10)	0.0699 (8)
O2	0.2339 (4)	0.1643 (3)	0.42739 (10)	0.0806 (9)
C23	0.3188 (4)	0.2429 (3)	0.51506 (14)	0.0492 (9)
C22	0.3265 (4)	0.3501 (3)	0.55128 (14)	0.0494 (9)
C21	0.2309 (4)	0.3959 (3)	0.43837 (13)	0.0470 (8)
C20	0.1497 (4)	0.5816 (3)	0.39425 (14)	0.0490 (9)
C19	0.3601 (5)	0.1177 (4)	0.53431 (16)	0.0630 (10)
H19	0.3511	0.0459	0.5107	0.076*
C18	0.2598 (5)	0.2599 (4)	0.45665 (15)	0.0571 (10)
C17	0.2775 (5)	0.4848 (4)	0.53324 (14)	0.0508 (9)
C16	0.1643 (5)	0.7379 (4)	0.46870 (15)	0.0553 (9)
H16	0.1848	0.7557	0.5057	0.066*
C15	0.1807 (5)	0.4458 (4)	0.38678 (13)	0.0525 (9)
C14	0.3024 (6)	0.2844 (3)	0.31344 (13)	0.0572 (10)
O1	0.0328 (4)	0.4141 (3)	0.30306 (11)	0.0967 (10)
C13	0.1000 (5)	0.6856 (4)	0.35921 (15)	0.0594 (10)
H13	0.0775	0.6684	0.3223	0.071*
C12	0.1184 (5)	0.8354 (4)	0.43411 (17)	0.0633 (11)
H12	0.1092	0.9213	0.4475	0.076*
C11	0.3777 (5)	0.3285 (4)	0.60562 (14)	0.0621 (10)
H11	0.3820	0.3988	0.6302	0.075*
C10	0.4852 (6)	0.2881 (4)	0.33161 (15)	0.0648 (11)
H10	0.5208	0.3493	0.3582	0.078*
C9	0.0840 (5)	0.8116 (4)	0.37831 (17)	0.0617 (10)
C8	0.1615 (5)	0.3819 (4)	0.33307 (15)	0.0611 (10)
C7	0.4220 (5)	0.2029 (5)	0.62324 (17)	0.0725 (12)
H7	0.4577	0.1894	0.6596	0.087*
C6	0.2519 (7)	0.1918 (4)	0.27499 (15)	0.0780 (13)
H6	0.1291	0.1897	0.2619	0.094*
C5	0.3799 (9)	0.1024 (5)	0.25553 (18)	0.0969 (17)
H5	0.3424	0.0377	0.2307	0.116*
C4	0.4142 (5)	0.0979 (4)	0.58804 (17)	0.0733 (12)
H4	0.4453	0.0137	0.6003	0.088*
C3	0.6168 (7)	0.2010 (4)	0.31047 (18)	0.0839 (13)
H3	0.7413	0.2054	0.3219	0.101*
C2	0.5615 (9)	0.1081 (5)	0.2725 (2)	0.0987 (17)
H2	0.6488	0.0491	0.2583	0.118*
C1	0.0376 (6)	0.9245 (4)	0.34044 (18)	0.0885 (14)
H1A	0.0216	0.8917	0.3037	0.133*
H1B	0.1379	0.9877	0.3412	0.133*
H1C	−0.0765	0.9660	0.3523	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0436 (17)	0.0484 (18)	0.0514 (18)	−0.0055 (14)	0.0046 (13)	−0.0026 (15)
C24	0.0354 (18)	0.048 (2)	0.050 (2)	0.0007 (16)	0.0012 (16)	−0.0009 (18)
O3	0.083 (2)	0.0695 (18)	0.0574 (16)	−0.0013 (15)	−0.0041 (13)	−0.0141 (14)
O2	0.123 (3)	0.0532 (17)	0.0652 (17)	−0.0080 (16)	−0.0049 (16)	−0.0040 (14)
C23	0.0345 (19)	0.055 (2)	0.058 (2)	0.0068 (17)	0.0040 (15)	0.0040 (19)
C22	0.037 (2)	0.059 (2)	0.051 (2)	0.0021 (17)	0.0061 (16)	0.0020 (19)
C21	0.040 (2)	0.049 (2)	0.052 (2)	−0.0050 (17)	0.0013 (16)	−0.0032 (18)
C20	0.039 (2)	0.058 (2)	0.050 (2)	−0.0035 (17)	0.0000 (16)	0.0002 (19)
C19	0.056 (2)	0.061 (3)	0.072 (3)	0.010 (2)	0.004 (2)	0.003 (2)
C18	0.058 (2)	0.058 (2)	0.055 (2)	−0.008 (2)	0.0059 (18)	−0.003 (2)
C17	0.041 (2)	0.056 (2)	0.055 (2)	−0.0032 (17)	0.0051 (17)	−0.005 (2)
C16	0.050 (2)	0.055 (2)	0.060 (2)	−0.0076 (18)	0.0073 (18)	−0.007 (2)
C15	0.052 (2)	0.059 (2)	0.046 (2)	−0.0061 (18)	−0.0012 (16)	−0.0006 (19)
C14	0.079 (3)	0.053 (2)	0.040 (2)	−0.011 (2)	0.0035 (19)	0.0030 (18)
O1	0.099 (2)	0.114 (3)	0.077 (2)	0.009 (2)	−0.0381 (18)	−0.0112 (18)
C13	0.054 (2)	0.067 (3)	0.057 (2)	−0.001 (2)	−0.0025 (18)	0.009 (2)
C12	0.062 (3)	0.050 (2)	0.077 (3)	−0.011 (2)	0.004 (2)	0.004 (2)
C11	0.054 (2)	0.081 (3)	0.051 (2)	−0.002 (2)	0.0008 (18)	0.006 (2)
C10	0.082 (3)	0.055 (2)	0.057 (2)	−0.001 (2)	0.004 (2)	−0.001 (2)
C9	0.050 (2)	0.059 (3)	0.076 (3)	−0.002 (2)	0.0022 (19)	0.011 (2)
C8	0.068 (3)	0.065 (3)	0.049 (2)	−0.011 (2)	−0.012 (2)	0.003 (2)
C7	0.058 (3)	0.098 (3)	0.062 (3)	0.007 (2)	0.002 (2)	0.020 (3)
C6	0.119 (4)	0.069 (3)	0.046 (2)	−0.012 (3)	−0.001 (2)	−0.004 (2)
C5	0.166 (6)	0.070 (3)	0.056 (3)	−0.010 (4)	0.017 (3)	−0.015 (2)
C4	0.072 (3)	0.076 (3)	0.072 (3)	0.018 (2)	0.008 (2)	0.020 (3)
C3	0.089 (3)	0.079 (3)	0.084 (3)	0.012 (3)	0.025 (3)	0.009 (3)
C2	0.143 (5)	0.075 (3)	0.079 (4)	0.014 (4)	0.046 (3)	−0.002 (3)
C1	0.091 (3)	0.072 (3)	0.102 (3)	0.000 (3)	−0.003 (3)	0.030 (3)

Geometric parameters (Å, º) top

N—C16	1.369 (4)	O1—C8	1.215 (4)
N—C24	1.379 (4)	C13—C9	1.363 (5)
N—C20	1.391 (4)	C13—H13	0.9300
C24—C21	1.380 (4)	C12—C9	1.401 (5)
C24—C17	1.430 (5)	C12—H12	0.9300
O3—C17	1.230 (4)	C11—C7	1.378 (5)
O2—C18	1.215 (4)	C11—H11	0.9300
C23—C19	1.382 (5)	C10—C3	1.388 (5)
C23—C22	1.400 (4)	C10—H10	0.9300
C23—C18	1.492 (5)	C9—C1	1.505 (5)
C22—C11	1.389 (5)	C7—C4	1.366 (5)
C22—C17	1.474 (5)	C7—H7	0.9300
C21—C15	1.399 (4)	C6—C5	1.372 (6)
C21—C18	1.462 (5)	C6—H6	0.9300
C20—C13	1.400 (4)	C5—C2	1.358 (6)
C20—C15	1.404 (5)	C5—H5	0.9300
C19—C4	1.377 (5)	C4—H4	0.9300
C19—H19	0.9300	C3—C2	1.376 (6)
C16—C12	1.338 (5)	C3—H3	0.9300
C16—H16	0.9300	C2—H2	0.9300
C15—C8	1.465 (5)	C1—H1A	0.9600
C14—C6	1.372 (5)	C1—H1B	0.9600
C14—C10	1.375 (5)	C1—H1C	0.9600
C14—C8	1.488 (5)

C16—N—C24	130.0 (3)	C16—C12—C9	121.7 (4)
C16—N—C20	121.5 (3)	C16—C12—H12	119.2
C24—N—C20	108.5 (3)	C9—C12—H12	119.2
N—C24—C21	107.7 (3)	C7—C11—C22	120.1 (4)
N—C24—C17	126.5 (3)	C7—C11—H11	120.0
C21—C24—C17	125.7 (3)	C22—C11—H11	120.0
C19—C23—C22	119.3 (3)	C14—C10—C3	120.3 (4)
C19—C23—C18	119.2 (3)	C14—C10—H10	119.9
C22—C23—C18	121.4 (3)	C3—C10—H10	119.9
C11—C22—C23	119.2 (3)	C13—C9—C12	118.5 (4)
C11—C22—C17	119.4 (3)	C13—C9—C1	121.3 (4)
C23—C22—C17	121.4 (3)	C12—C9—C1	120.1 (4)
C24—C21—C15	109.4 (3)	O1—C8—C15	119.1 (4)
C24—C21—C18	119.8 (3)	O1—C8—C14	119.6 (3)
C15—C21—C18	130.5 (3)	C15—C8—C14	121.3 (3)
N—C20—C13	117.6 (3)	C4—C7—C11	120.9 (4)
N—C20—C15	108.3 (3)	C4—C7—H7	119.6
C13—C20—C15	134.2 (3)	C11—C7—H7	119.5
C23—C19—C4	120.9 (4)	C14—C6—C5	120.9 (5)
C23—C19—H19	119.5	C14—C6—H6	119.5
C4—C19—H19	119.5	C5—C6—H6	119.5
O2—C18—C21	123.4 (3)	C2—C5—C6	120.1 (5)
O2—C18—C23	120.6 (3)	C2—C5—H5	120.0
C21—C18—C23	116.0 (3)	C6—C5—H5	120.0
O3—C17—C24	123.1 (3)	C7—C4—C19	119.6 (4)
O3—C17—C22	121.8 (3)	C7—C4—H4	120.2
C24—C17—C22	115.1 (3)	C19—C4—H4	120.2
C12—C16—N	119.6 (3)	C2—C3—C10	119.5 (5)
C12—C16—H16	120.2	C2—C3—H3	120.3
N—C16—H16	120.2	C10—C3—H3	120.3
C21—C15—C20	106.1 (3)	C5—C2—C3	120.2 (5)
C21—C15—C8	131.6 (3)	C5—C2—H2	119.9
C20—C15—C8	122.3 (3)	C3—C2—H2	119.9
C6—C14—C10	119.0 (4)	C9—C1—H1A	109.5
C6—C14—C8	119.8 (4)	C9—C1—H1B	109.5
C10—C14—C8	121.2 (3)	H1A—C1—H1B	109.5
C9—C13—C20	121.1 (4)	C9—C1—H1C	109.5
C9—C13—H13	119.4	H1A—C1—H1C	109.5
C20—C13—H13	119.4	H1B—C1—H1C	109.5

C16—N—C24—C21	−178.7 (3)	C24—C21—C15—C20	−0.1 (4)
C20—N—C24—C21	−0.2 (3)	C18—C21—C15—C20	172.7 (3)
C16—N—C24—C17	0.7 (5)	C24—C21—C15—C8	179.2 (3)
C20—N—C24—C17	179.2 (3)	C18—C21—C15—C8	−8.0 (6)
C19—C23—C22—C11	0.7 (5)	N—C20—C15—C21	0.0 (4)
C18—C23—C22—C11	178.3 (3)	C13—C20—C15—C21	178.8 (4)
C19—C23—C22—C17	−177.9 (3)	N—C20—C15—C8	−179.4 (3)
C18—C23—C22—C17	−0.2 (5)	C13—C20—C15—C8	−0.6 (6)
N—C24—C21—C15	0.2 (4)	N—C20—C13—C9	0.4 (5)
C17—C24—C21—C15	−179.2 (3)	C15—C20—C13—C9	−178.3 (4)
N—C24—C21—C18	−173.5 (3)	N—C16—C12—C9	0.9 (5)
C17—C24—C21—C18	7.1 (5)	C23—C22—C11—C7	0.7 (5)
C16—N—C20—C13	−0.2 (4)	C17—C22—C11—C7	179.3 (3)
C24—N—C20—C13	−178.9 (3)	C6—C14—C10—C3	1.2 (5)
C16—N—C20—C15	178.8 (3)	C8—C14—C10—C3	−176.3 (3)
C24—N—C20—C15	0.1 (3)	C20—C13—C9—C12	0.0 (5)
C22—C23—C19—C4	−2.1 (5)	C20—C13—C9—C1	177.8 (3)
C18—C23—C19—C4	−179.7 (3)	C16—C12—C9—C13	−0.7 (5)
C24—C21—C18—O2	168.7 (3)	C16—C12—C9—C1	−178.5 (4)
C15—C21—C18—O2	−3.5 (6)	C21—C15—C8—O1	140.5 (4)
C24—C21—C18—C23	−9.5 (5)	C20—C15—C8—O1	−40.3 (5)
C15—C21—C18—C23	178.3 (3)	C21—C15—C8—C14	−43.1 (6)
C19—C23—C18—O2	5.7 (5)	C20—C15—C8—C14	136.1 (4)
C22—C23—C18—O2	−171.9 (3)	C6—C14—C8—O1	−27.8 (5)
C19—C23—C18—C21	−176.0 (3)	C10—C14—C8—O1	149.7 (4)
C22—C23—C18—C21	6.4 (4)	C6—C14—C8—C15	155.8 (3)
N—C24—C17—O3	−0.8 (5)	C10—C14—C8—C15	−26.7 (5)
C21—C24—C17—O3	178.5 (3)	C22—C11—C7—C4	−0.8 (6)
N—C24—C17—C22	−179.9 (3)	C10—C14—C6—C5	1.3 (5)
C21—C24—C17—C22	−0.7 (5)	C8—C14—C6—C5	178.8 (4)
C11—C22—C17—O3	−0.5 (5)	C14—C6—C5—C2	−2.9 (7)
C23—C22—C17—O3	178.1 (3)	C11—C7—C4—C19	−0.5 (6)
C11—C22—C17—C24	178.6 (3)	C23—C19—C4—C7	1.9 (6)
C23—C22—C17—C24	−2.8 (4)	C14—C10—C3—C2	−2.1 (6)
C24—N—C16—C12	177.9 (3)	C6—C5—C2—C3	2.0 (7)
C20—N—C16—C12	−0.5 (5)	C10—C3—C2—C5	0.5 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.93	2.45	3.305 (5)	152
C16—H16···O3	0.93	2.40	2.960 (5)	119

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₅NO₃
M_r	365.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.1260 (14), 10.125 (2), 24.352 (5)
β (°)	90.22 (3)
V (Å³)	1757.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (XCAD4; Harms & Wocadlo, 1995)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3371, 3103, 1555
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.169, 1.02
No. of reflections	3103
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

N—C16	1.369 (4)	N—C20	1.391 (4)
N—C24	1.379 (4)

C16—N—C24	130.0 (3)	C24—N—C20	108.5 (3)
C16—N—C20	121.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.93	2.45	3.305 (5)	152

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Xuzhou Normal University for financial support (08XLR07). This work was also sponsored by the Qing Lan Project (08QLT001).

References

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