5-Phenyl-3,4,4a,5,6,12c-hexa­hydro-2H-benzo[f]pyrano[3,2-c]quinoline

Du, B.-X.; Zhou, J.; Li, Y.-L.; Wang, X.-S.

doi:10.1107/S1600536810020787

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1622

doi:10.1107/S1600536810020787

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5-Phenyl-3,4,4a,5,6,12c-hexahydro-2H-benzo[f]pyrano[3,2-c]quinoline

Bai-Xiang Du,^a ^* Jie Zhou,^a Yu-Ling Li ^a and Xiang-Shan Wang ^a

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou Jiangsu 221116, People's Republic of China
^*Correspondence e-mail: dbx19722@xznu.edu.cn

(Received 26 May 2010; accepted 1 June 2010; online 9 June 2010)

In the title compound, C₂₂H₂₁N, the pyridine ring adopts a distorted boat conformation, while the adjacent pyran ring adopts a chair conformation; the heterocyclic rings make a dihedral angle of 40.1 (2)° with each other.

Related literature

For the biological properties of pyranoquinoline derivatives, see: Faber et al. (1984 ); Johnson et al. (1989 ); Schiemann et al. (2007 ); Yamada et al. (1992 ). Zhao & Teng (2008 ). For related structures, see: Ramesh et al. (2008 ); Zhao & Teng (2008); Bai et al. (2009 ).

Experimental

Crystal data

C₂₂H₂₁NO
M_r = 315.40
Monoclinic, P 2₁ /c
a = 8.1106 (2) Å
b = 10.9560 (2) Å
c = 18.5020 (3) Å
β = 93.552 (1)°
V = 1640.92 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.50 × 0.33 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
11135 measured reflections
2956 independent reflections
2303 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.140
S = 1.03
2956 reflections
221 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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/S1600536810020787/pv2287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020787/pv2287Isup2.hkl

checkCIF report

Comment top

The synthesis of pyranoquinoline derivatives has been the focus of great interest, because it was reported that its derivatives possessed a broad spectrum of biological properties. Some of these activities include psychotropic activity (Yamada et al., 1992), anti-allergenic activity (Faber et al., 1984), and anti-inflammatory (Johnson et al., 1989). They are also used for the treatment of proliferative diseases, such as cancer (Schiemann et al., 2007). The title compound may be used as a new precursor for obtaining bioactive molecules. We report here the crystal structure of the title compound, (I).

In the crystal structure of (I), the pyridine ring of the pyranoquinoline moiety is slightly distorted and adopts a distorted boat conformation (Fig. 1). The atoms C1 and C2 deviate from the basal plane defined by the atoms C3—C5/N1 by 0.253 (3) and -0.495 (3) Å, respectively. This conformation is similar to that found in other hydropyridine derivatives (Ramesh et al. 2008; Zhao & Teng, 2008; Bai et al., 2009). In the adjacent pyran ring, the atoms C2, C3, C14 and C15 are coplanar, while the atoms O1 and C16 deviate from the plane by 0.659 (3) and -0.623 (3) Å, respectively. These data indicate that the pyran ring adopts a chair confirmation. The basal plane of the pyridine ring nearly parallel to the naphthalene ring C4—C13, forming a dihedral angle of 2.7 (1)°, and makes a dihedral angle of 82.2 (1)° to benzene ring. Two heterocyclic rings make a dihedral angle of 40.1 (1)°.

Related literature top

For the biological properties of pyranoquinoline derivatives, see: Faber et al. (1984); Johnson et al. (1989); Schiemann et al. (2007); Yamada et al. (1992). Zhao & Teng (2008). For related structures, see: Ramesh et al. (2008); Zhao & Teng (2008); Bai et al. (2009).

Experimental top

The title compound, (I), was prepared by the reaction of benzaldehyde (0.212 g, 2 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol), 3,4-dihydro-2H-pyran (0.252 g, 3.0 mmol), I₂ (0.026 g, 0.1 mmol) and THF (10 ml) for 14 h (yield 86%, mp. 477–478 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a dimethylformamide (dmf) solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 drawing for (I) showing 30% probability of displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The molecular packing diagram of (I).

5-Phenyl-3,4,4a,5,6,12c-hexahydro-2H-benzo[f]pyrano[3,2- c]quinoline top

Crystal data top

C₂₂H₂₁NO	F(000) = 672
M_r = 315.40	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 477–478 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.1106 (2) Å	Cell parameters from 3365 reflections
b = 10.9560 (2) Å	θ = 2.5–26.4°
c = 18.5020 (3) Å	µ = 0.08 mm⁻¹
β = 93.552 (1)°	T = 296 K
V = 1640.92 (6) Å³	Block, colourless
Z = 4	0.50 × 0.33 × 0.10 mm

Data collection top

Bruker APEXII area-detector diffractometer	2303 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.2°, θ_min = 2.2°
ϕ & ω scans	h = −9→9
11135 measured reflections	k = −13→12
2956 independent reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0712P)² + 0.4581P] where P = (F_o² + 2F_c²)/3
2956 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.30 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₂H₂₁NO	V = 1640.92 (6) Å³
M_r = 315.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1106 (2) Å	µ = 0.08 mm⁻¹
b = 10.9560 (2) Å	T = 296 K
c = 18.5020 (3) Å	0.50 × 0.33 × 0.10 mm
β = 93.552 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	2303 reflections with I > 2σ(I)
11135 measured reflections	R_int = 0.023
2956 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.140	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
2956 reflections	Δρ_min = −0.21 e Å⁻³
221 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
C4	0.3714 (2)	1.07478 (15)	0.36093 (9)	0.0408 (4)
N1	0.61481 (19)	0.95714 (14)	0.39789 (10)	0.0537 (4)
O1	0.18206 (15)	0.97459 (12)	0.43549 (7)	0.0562 (4)
C13	0.3017 (2)	1.18875 (15)	0.33707 (9)	0.0414 (4)
C5	0.5404 (2)	1.06466 (16)	0.37471 (10)	0.0439 (4)
C3	0.2648 (2)	0.96399 (16)	0.36947 (10)	0.0442 (4)
H3A	0.1808	0.9625	0.3291	0.053*
C8	0.4069 (2)	1.29013 (16)	0.32593 (9)	0.0452 (4)
C6	0.6433 (2)	1.16641 (18)	0.36261 (11)	0.0544 (5)
H6A	0.7571	1.1589	0.3711	0.065*
C1	0.5156 (2)	0.85413 (16)	0.42038 (10)	0.0470 (4)
H1A	0.4798	0.8705	0.4691	0.056*
C2	0.3629 (2)	0.84524 (16)	0.36796 (10)	0.0467 (4)
H2A	0.4012	0.8359	0.3191	0.056*
C7	0.5791 (2)	1.27409 (18)	0.33898 (11)	0.0529 (5)
H7A	0.6497	1.3390	0.3311	0.064*
C17	0.6191 (2)	0.73967 (16)	0.42288 (9)	0.0439 (4)
C10	0.1721 (3)	1.41656 (19)	0.29126 (12)	0.0623 (6)
H10A	0.1281	1.4914	0.2761	0.075*
C22	0.6980 (2)	0.69912 (17)	0.36296 (10)	0.0522 (5)
H22A	0.6887	0.7443	0.3203	0.063*
C9	0.3376 (3)	1.40304 (17)	0.30283 (10)	0.0552 (5)
H9A	0.4068	1.4690	0.2955	0.066*
C11	0.0673 (3)	1.31761 (19)	0.30220 (12)	0.0614 (5)
H11A	−0.0462	1.3270	0.2940	0.074*
C12	0.1299 (2)	1.20753 (17)	0.32474 (10)	0.0515 (5)
H12A	0.0579	1.1433	0.3322	0.062*
C16	0.2505 (3)	0.73714 (18)	0.38181 (12)	0.0603 (5)
H16A	0.1730	0.7260	0.3403	0.072*
H16B	0.3168	0.6637	0.3874	0.072*
C18	0.6379 (3)	0.6707 (2)	0.48508 (11)	0.0630 (6)
H18A	0.5869	0.6954	0.5263	0.076*
C21	0.7894 (3)	0.59365 (18)	0.36538 (11)	0.0581 (5)
H21A	0.8399	0.5676	0.3243	0.070*
C20	0.8067 (3)	0.52664 (18)	0.42770 (12)	0.0604 (5)
H20A	0.8693	0.4555	0.4293	0.073*
C15	0.1569 (3)	0.7550 (2)	0.44793 (14)	0.0697 (6)
H15A	0.2325	0.7529	0.4907	0.084*
H15B	0.0773	0.6896	0.4517	0.084*
C14	0.0693 (3)	0.8750 (2)	0.44381 (14)	0.0692 (6)
H14A	−0.0120	0.8742	0.4031	0.083*
H14B	0.0115	0.8871	0.4876	0.083*
C19	0.7316 (3)	0.5649 (2)	0.48709 (12)	0.0710 (6)
H19A	0.7431	0.5197	0.5296	0.085*
H1	0.7087	0.965	0.4204	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0409 (9)	0.0403 (9)	0.0416 (9)	−0.0009 (7)	0.0053 (7)	−0.0061 (7)
N1	0.0389 (8)	0.0454 (9)	0.0761 (11)	0.0008 (7)	−0.0021 (8)	−0.0027 (8)
O1	0.0504 (7)	0.0515 (8)	0.0685 (9)	−0.0046 (6)	0.0189 (6)	−0.0062 (6)
C13	0.0459 (9)	0.0410 (9)	0.0376 (9)	0.0006 (7)	0.0059 (7)	−0.0056 (7)
C5	0.0405 (9)	0.0423 (9)	0.0492 (10)	0.0001 (7)	0.0049 (7)	−0.0071 (8)
C3	0.0398 (9)	0.0440 (10)	0.0488 (10)	−0.0012 (7)	0.0026 (7)	−0.0022 (8)
C8	0.0532 (10)	0.0440 (10)	0.0390 (9)	−0.0010 (8)	0.0074 (8)	−0.0064 (7)
C6	0.0398 (9)	0.0557 (12)	0.0678 (13)	−0.0048 (9)	0.0050 (9)	−0.0073 (9)
C1	0.0455 (9)	0.0462 (10)	0.0496 (10)	0.0020 (8)	0.0038 (8)	−0.0062 (8)
C2	0.0476 (10)	0.0435 (10)	0.0489 (10)	0.0003 (8)	0.0019 (8)	−0.0057 (8)
C7	0.0537 (11)	0.0472 (11)	0.0589 (12)	−0.0109 (9)	0.0112 (9)	−0.0048 (9)
C17	0.0430 (9)	0.0433 (10)	0.0454 (10)	0.0001 (7)	0.0020 (7)	−0.0028 (8)
C10	0.0745 (14)	0.0462 (11)	0.0665 (13)	0.0146 (10)	0.0071 (11)	0.0003 (9)
C22	0.0618 (11)	0.0503 (11)	0.0454 (11)	0.0115 (9)	0.0096 (9)	0.0059 (8)
C9	0.0721 (13)	0.0404 (10)	0.0540 (11)	−0.0021 (9)	0.0107 (10)	−0.0030 (8)
C11	0.0552 (11)	0.0587 (13)	0.0703 (14)	0.0132 (10)	0.0037 (10)	−0.0008 (10)
C12	0.0486 (10)	0.0484 (11)	0.0578 (12)	0.0031 (8)	0.0059 (8)	−0.0018 (9)
C16	0.0605 (12)	0.0451 (11)	0.0738 (14)	−0.0038 (9)	−0.0096 (10)	0.0002 (10)
C18	0.0726 (13)	0.0731 (14)	0.0438 (11)	0.0105 (11)	0.0073 (9)	0.0028 (10)
C21	0.0641 (12)	0.0514 (11)	0.0597 (12)	0.0096 (10)	0.0108 (10)	−0.0051 (9)
C20	0.0629 (12)	0.0432 (11)	0.0742 (14)	0.0053 (9)	−0.0028 (10)	0.0043 (10)
C15	0.0634 (13)	0.0569 (13)	0.0885 (17)	−0.0110 (10)	0.0021 (12)	0.0077 (12)
C14	0.0556 (12)	0.0630 (13)	0.0909 (17)	−0.0118 (10)	0.0195 (11)	0.0038 (12)
C19	0.0862 (16)	0.0659 (14)	0.0603 (14)	0.0146 (12)	−0.0002 (12)	0.0210 (11)

Geometric parameters (Å, º) top

C4—C5	1.383 (2)	C10—C9	1.355 (3)
C4—C13	1.429 (2)	C10—C11	1.400 (3)
C4—C3	1.504 (2)	C10—H10A	0.9300
N1—C5	1.380 (2)	C22—C21	1.372 (3)
N1—C1	1.461 (2)	C22—H22A	0.9300
N1—H1	0.850	C9—H9A	0.9300
O1—C3	1.434 (2)	C11—C12	1.364 (3)
O1—C14	1.438 (2)	C11—H11A	0.9300
C13—C12	1.413 (2)	C12—H12A	0.9300
C13—C8	1.423 (2)	C16—C15	1.492 (3)
C5—C6	1.418 (3)	C16—H16A	0.9700
C3—C2	1.526 (2)	C16—H16B	0.9700
C3—H3A	0.9800	C18—C19	1.385 (3)
C8—C9	1.414 (3)	C18—H18A	0.9300
C8—C7	1.414 (3)	C21—C20	1.367 (3)
C6—C7	1.351 (3)	C21—H21A	0.9300
C6—H6A	0.9300	C20—C19	1.355 (3)
C1—C17	1.508 (2)	C20—H20A	0.9300
C1—C2	1.529 (3)	C15—C14	1.494 (3)
C1—H1A	0.9800	C15—H15A	0.9700
C2—C16	1.526 (3)	C15—H15B	0.9700
C2—H2A	0.9800	C14—H14A	0.9700
C7—H7A	0.9300	C14—H14B	0.9700
C17—C18	1.378 (3)	C19—H19A	0.9300
C17—C22	1.387 (2)

C5—C4—C13	119.71 (15)	C9—C10—H10A	120.1
C5—C4—C3	119.05 (15)	C11—C10—H10A	120.1
C13—C4—C3	121.22 (15)	C21—C22—C17	121.24 (18)
C5—N1—C1	120.68 (14)	C21—C22—H22A	119.4
C5—N1—H1	115.1	C17—C22—H22A	119.4
C1—N1—H1	115.7	C10—C9—C8	120.97 (19)
C3—O1—C14	111.34 (15)	C10—C9—H9A	119.5
C12—C13—C8	117.18 (16)	C8—C9—H9A	119.5
C12—C13—C4	122.99 (16)	C12—C11—C10	120.76 (19)
C8—C13—C4	119.82 (15)	C12—C11—H11A	119.6
N1—C5—C4	122.34 (16)	C10—C11—H11A	119.6
N1—C5—C6	118.03 (15)	C11—C12—C13	121.52 (19)
C4—C5—C6	119.60 (16)	C11—C12—H12A	119.2
O1—C3—C4	109.05 (13)	C13—C12—H12A	119.2
O1—C3—C2	110.88 (14)	C15—C16—C2	112.03 (17)
C4—C3—C2	112.49 (14)	C15—C16—H16A	109.2
O1—C3—H3A	108.1	C2—C16—H16A	109.2
C4—C3—H3A	108.1	C15—C16—H16B	109.2
C2—C3—H3A	108.1	C2—C16—H16B	109.2
C9—C8—C7	122.01 (17)	H16A—C16—H16B	107.9
C9—C8—C13	119.76 (17)	C17—C18—C19	120.90 (19)
C7—C8—C13	118.23 (16)	C17—C18—H18A	119.6
C7—C6—C5	121.22 (17)	C19—C18—H18A	119.6
C7—C6—H6A	119.4	C20—C21—C22	120.45 (19)
C5—C6—H6A	119.4	C20—C21—H21A	119.8
N1—C1—C17	109.61 (14)	C22—C21—H21A	119.8
N1—C1—C2	107.90 (15)	C19—C20—C21	119.34 (19)
C17—C1—C2	113.22 (14)	C19—C20—H20A	120.3
N1—C1—H1A	108.7	C21—C20—H20A	120.3
C17—C1—H1A	108.7	C16—C15—C14	109.77 (19)
C2—C1—H1A	108.7	C16—C15—H15A	109.7
C16—C2—C3	109.97 (15)	C14—C15—H15A	109.7
C16—C2—C1	114.33 (16)	C16—C15—H15B	109.7
C3—C2—C1	109.69 (14)	C14—C15—H15B	109.7
C16—C2—H2A	107.5	H15A—C15—H15B	108.2
C3—C2—H2A	107.5	O1—C14—C15	111.70 (17)
C1—C2—H2A	107.5	O1—C14—H14A	109.3
C6—C7—C8	121.39 (17)	C15—C14—H14A	109.3
C6—C7—H7A	119.3	O1—C14—H14B	109.3
C8—C7—H7A	119.3	C15—C14—H14B	109.3
C18—C17—C22	117.36 (17)	H14A—C14—H14B	107.9
C18—C17—C1	120.95 (17)	C20—C19—C18	120.71 (19)
C22—C17—C1	121.68 (16)	C20—C19—H19A	119.6
C9—C10—C11	119.80 (19)	C18—C19—H19A	119.6

C5—C4—C13—C12	−177.36 (16)	N1—C1—C2—C3	−59.10 (19)
C3—C4—C13—C12	4.4 (3)	C17—C1—C2—C3	179.41 (14)
C5—C4—C13—C8	1.5 (2)	C5—C6—C7—C8	0.5 (3)
C3—C4—C13—C8	−176.73 (15)	C9—C8—C7—C6	178.50 (18)
C1—N1—C5—C4	−10.1 (3)	C13—C8—C7—C6	−1.1 (3)
C1—N1—C5—C6	171.94 (17)	N1—C1—C17—C18	124.28 (19)
C13—C4—C5—N1	179.96 (16)	C2—C1—C17—C18	−115.2 (2)
C3—C4—C5—N1	−1.7 (3)	N1—C1—C17—C22	−56.2 (2)
C13—C4—C5—C6	−2.2 (3)	C2—C1—C17—C22	64.3 (2)
C3—C4—C5—C6	176.16 (16)	C18—C17—C22—C21	0.8 (3)
C14—O1—C3—C4	175.92 (15)	C1—C17—C22—C21	−178.78 (17)
C14—O1—C3—C2	−59.69 (19)	C11—C10—C9—C8	0.0 (3)
C5—C4—C3—O1	104.13 (17)	C7—C8—C9—C10	−179.42 (18)
C13—C4—C3—O1	−77.58 (19)	C13—C8—C9—C10	0.2 (3)
C5—C4—C3—C2	−19.3 (2)	C9—C10—C11—C12	0.3 (3)
C13—C4—C3—C2	158.98 (15)	C10—C11—C12—C13	−0.7 (3)
C12—C13—C8—C9	−0.6 (2)	C8—C13—C12—C11	0.8 (3)
C4—C13—C8—C9	−179.55 (15)	C4—C13—C12—C11	179.77 (17)
C12—C13—C8—C7	179.06 (16)	C3—C2—C16—C15	−51.1 (2)
C4—C13—C8—C7	0.1 (2)	C1—C2—C16—C15	72.8 (2)
N1—C5—C6—C7	179.13 (18)	C22—C17—C18—C19	−0.2 (3)
C4—C5—C6—C7	1.2 (3)	C1—C17—C18—C19	179.35 (19)
C5—N1—C1—C17	164.33 (16)	C17—C22—C21—C20	−0.9 (3)
C5—N1—C1—C2	40.6 (2)	C22—C21—C20—C19	0.5 (3)
O1—C3—C2—C16	53.87 (19)	C2—C16—C15—C14	52.5 (2)
C4—C3—C2—C16	176.28 (15)	C3—O1—C14—C15	61.8 (2)
O1—C3—C2—C1	−72.68 (18)	C16—C15—C14—O1	−57.3 (3)
C4—C3—C2—C1	49.7 (2)	C21—C20—C19—C18	0.1 (3)
N1—C1—C2—C16	176.86 (15)	C17—C18—C19—C20	−0.2 (4)
C17—C1—C2—C16	55.4 (2)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NO
M_r	315.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.1106 (2), 10.9560 (2), 18.5020 (3)
β (°)	93.552 (1)
V (Å³)	1640.92 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.33 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11135, 2956, 2303
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.140, 1.03
No. of reflections	2956
No. of parameters	221
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We are grateful to the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of the Jiangsu Education Committee for financial support.

References

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