6-Phenyl-6,7-dihydro­dibenzo[c,f][1,5]aza­bis­mocin-12(5H)-yl perchlorate

Zhang, X.-W.; Fan, T.

doi:10.1107/S1600536811021039

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m875

doi:10.1107/S1600536811021039

Open

access

6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl perchlorate

Xiao-Wen Zhang ^a ^* and Ting Fan ^b

^aCollege of Environment Protection and Safety Engineering, University of South China, Hengyang 421001, People's Republic of China, and ^bKey Laboratory of Pollution Control and Resource Use of Hunan Province, University of South China, Hengyang 421001, People's Republic of China
^*Correspondence e-mail: shawn_zhang@sina.com

(Received 4 May 2011; accepted 31 May 2011; online 11 June 2011)

In the title compound, [Bi(C₂₀H₁₇N)(ClO₄)] or C₂₀H₁₇BiClNO₄, the Bi^III ion assumes a distorted ψ trigonal–bipyramidal geometry, with two C atoms and the electron lone pair of the Bi atom at the equatorial positions and an amine N atom and a perchlorate O atom at the apical positions. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the synthesis of 12-chloro-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine, see: Zhang et al. (2009 ). For general background, see: Shimada et al. (2004 ); Yin et al. (2008 ); Zhang et al. (2010 ); Tan & Zhang (2011 ). For related structures, see: Ohkata et al. (1989 ); Minoura et al. (1999 ).

Experimental

Crystal data

[Bi(C₂₀H₁₇N)(ClO₄)]
M_r = 579.78
Monoclinic, P 2₁ /c
a = 12.0635 (10) Å
b = 14.0755 (12) Å
c = 11.5121 (10) Å
β = 107.590 (2)°
V = 1863.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 9.63 mm⁻¹
T = 293 K
0.32 × 0.21 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan(SADABS; Bruker, 2001 ) T_min = 0.100, T_max = 0.145
9267 measured reflections
3279 independent reflections
2585 reflections with I > 2σ(I)
R_int = 0.166

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.163
S = 1.02
3279 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 4.89 e Å⁻³
Δρ_min = −4.14 e Å⁻³

Table 1
Selected bond lengths (Å)

Bi—N1	2.387 (10)
Bi—O1	2.546 (10)
Bi—C1	2.245 (13)
Bi—C8	2.204 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.46	3.137 (17)	130
C14—H14B⋯O2ⁱⁱ	0.97	2.55	3.398 (16)	146
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811021039/xu5208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811021039/xu5208Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811021039/xu5208Isup3.cml

checkCIF report

Comment top

Bismuth is a nontoxic and noncarcinogenic element and many of its compounds are low in toxicity and can be safely used in areas such as medicine, catalysis, and synthesis (Shimada et al., 2004; Yin et al., 2008; Zhang, Qiu, Tan et al., 2010). The 5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocine framework is highly stable as a organobismuth Fragment because the weakly coordination exists between bismuth and nitrogen atoms on 1,5-azabismocine (Ohkata et al.,1989; Minoura et al.,1999), and therefore, is suitable for the study of organobismuth compounds bearing various groups on the bismuth and nitrogen atom for potential uses.

In the present paper, we report the crystal structure of the title compound (Fig. 1). The central bismuth–containing part of the complex exhibits a distorted pseudo trigonal–bipyramidal structure. The C (8), C (1) atoms and a lone electron pair of the Bi atom exist at the equatorial positions while the N (1) and O (1) atoms are located at the apical positions. The Bi–C (8) and Bi–C (1) distance is 2.250 (13) Å and 2.204 (12) Å, respectively. The C (8)–Bi–C (1) angle is 92.5 (5) ° while the N (1)–Bi–O (1) angle is 154.0 (3)°(rather than 180°). The Bi–N (1) distance (2.388 (10) Å) is shorter than 2.607 (5) Å of the precursor, C₆H₅N(CH₂C₆H₄)₂BiCl.The Bi–O (1) distance(2.546 (10) Å) is shorter than Bi–Cl(1) distance 2.597 (19) Å also(Zhang, Xia, Yan et al., 2009).

Related literature top

For the synthesis of 12-chloro-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine, see: Zhang et al. (2009). For general background, see: Shimada et al. (2004); Yin et al. (2008); Zhang et al. (2010); Tan & Zhang (2011). For related structures, see: Ohkata et al. (1989); Minoura et al. (1999).

Experimental top

The following procedures are recommended for synthesis of the title compound (I): 12-chloro-6-phenyl-5,6,7,12-tetrahydrodibenzo[c,f][1,5]azabismocine (0.516 g, 1.0 mmol) was dissolved in 15 ml THF, then a solution of AgClO₄(0.207 g, 1.0 mmol) in 15.0 ml THF was added. After the mixture was stirred in the dark at room temperature for 2 h, it was filtered. The filtrate mixed with 1.0 ml hexane was refrigerated for 24 h, giving colorless crystals (0.539 g, 93.0%).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 with atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All hydrogen atoms are omitted for clarity.

6-Phenyl-6,7-dihydrodibenzo[c,f][1,5]azabismocin-12(5H)-yl perchlorate top

Crystal data top

[Bi(C₂₀H₁₇N)(ClO₄)]	F(000) = 1104
M_r = 579.78	D_x = 2.067 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2936 reflections
a = 12.0635 (10) Å	θ = 2.7–24.2°
b = 14.0755 (12) Å	µ = 9.63 mm⁻¹
c = 11.5121 (10) Å	T = 293 K
β = 107.590 (2)°	Prismatic, colorless
V = 1863.4 (3) Å³	0.32 × 0.21 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3279 independent reflections
Radiation source: fine-focus sealed tube	2585 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.166
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2001)	h = −10→14
T_min = 0.100, T_max = 0.145	k = −13→16
9267 measured reflections	l = −13→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0816P)²] where P = (F_o² + 2F_c²)/3
3279 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 4.89 e Å⁻³
0 restraints	Δρ_min = −4.14 e Å⁻³

Crystal data top

[Bi(C₂₀H₁₇N)(ClO₄)]	V = 1863.4 (3) Å³
M_r = 579.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0635 (10) Å	µ = 9.63 mm⁻¹
b = 14.0755 (12) Å	T = 293 K
c = 11.5121 (10) Å	0.32 × 0.21 × 0.20 mm
β = 107.590 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3279 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2001)	2585 reflections with I > 2σ(I)
T_min = 0.100, T_max = 0.145	R_int = 0.166
9267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.02	Δρ_max = 4.89 e Å⁻³
3279 reflections	Δρ_min = −4.14 e Å⁻³
244 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 > 2sigma(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
Bi	0.74646 (4)	0.77309 (3)	0.84604 (4)	0.0321 (2)
Cl1	0.7240 (3)	1.0213 (2)	0.8825 (3)	0.0378 (7)
N1	0.7225 (7)	0.6171 (8)	0.7606 (7)	0.033 (2)
O1	0.7940 (9)	0.9494 (7)	0.8480 (10)	0.063 (3)
O2	0.6291 (9)	0.9730 (7)	0.9075 (10)	0.069 (3)
O3	0.6836 (10)	1.0854 (8)	0.7850 (10)	0.071 (3)
O4	0.7937 (12)	1.0687 (8)	0.9874 (10)	0.086 (4)
C1	0.6226 (11)	0.7895 (8)	0.6574 (11)	0.037 (3)
C2	0.6002 (10)	0.8714 (8)	0.5878 (10)	0.034 (3)
H2	0.6373	0.9281	0.6181	0.041*
C3	0.5204 (11)	0.8671 (9)	0.4706 (11)	0.041 (3)
H3	0.5026	0.9222	0.4241	0.049*
C4	0.4688 (12)	0.7846 (8)	0.4240 (12)	0.042 (3)
H4	0.4163	0.7830	0.3459	0.051*
C5	0.4949 (11)	0.7005 (9)	0.4943 (11)	0.037 (3)
H5	0.4603	0.6435	0.4617	0.045*
C6	0.5695 (10)	0.7026 (9)	0.6080 (10)	0.033 (3)
C7	0.5996 (10)	0.6133 (8)	0.6827 (9)	0.031 (3)
H7A	0.5489	0.6068	0.7335	0.037*
H7B	0.5881	0.5586	0.6292	0.037*
C8	0.8978 (11)	0.7594 (8)	0.7776 (11)	0.030 (3)
C9	0.9896 (11)	0.8252 (10)	0.7942 (12)	0.047 (3)
H9	0.9914	0.8787	0.8421	0.056*
C10	1.0741 (11)	0.8122 (10)	0.7424 (14)	0.051 (4)
H10	1.1337	0.8565	0.7542	0.062*
C11	1.0723 (14)	0.7321 (10)	0.6709 (16)	0.055 (4)
H11	1.1291	0.7246	0.6321	0.066*
C12	0.9893 (10)	0.6651 (9)	0.6570 (11)	0.038 (3)
H12	0.9919	0.6101	0.6132	0.045*
C13	0.8986 (9)	0.6785 (8)	0.7091 (9)	0.030 (2)
C14	0.8015 (10)	0.6065 (8)	0.6812 (10)	0.033 (3)
H14A	0.8350	0.5433	0.6923	0.040*
H14B	0.7555	0.6128	0.5965	0.040*
C15	0.7472 (9)	0.5399 (9)	0.8534 (10)	0.033 (3)
C16	0.6852 (11)	0.4552 (9)	0.8367 (12)	0.041 (3)
H16	0.6240	0.4455	0.7659	0.049*
C17	0.7139 (13)	0.3865 (10)	0.9238 (14)	0.053 (4)
H17	0.6723	0.3298	0.9117	0.064*
C18	0.8062 (14)	0.4002 (11)	1.0325 (14)	0.058 (4)
H18	0.8251	0.3532	1.0919	0.069*
C19	0.8671 (14)	0.4831 (12)	1.0489 (13)	0.064 (4)
H19	0.9281	0.4920	1.1202	0.077*
C20	0.8408 (11)	0.5534 (11)	0.9634 (11)	0.050 (3)
H20	0.8833	0.6097	0.9763	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi	0.0313 (3)	0.0438 (3)	0.0201 (3)	0.00040 (18)	0.0062 (2)	−0.00470 (18)
Cl1	0.0407 (17)	0.0414 (16)	0.0248 (14)	0.0024 (13)	0.0001 (12)	0.0037 (13)
N1	0.018 (5)	0.070 (7)	0.007 (4)	0.002 (4)	−0.001 (4)	0.001 (4)
O1	0.047 (6)	0.064 (7)	0.079 (8)	0.005 (5)	0.020 (5)	−0.009 (6)
O2	0.054 (6)	0.076 (7)	0.086 (8)	0.001 (5)	0.036 (6)	0.026 (6)
O3	0.082 (8)	0.065 (7)	0.059 (7)	0.000 (6)	0.008 (6)	0.034 (6)
O4	0.122 (11)	0.076 (8)	0.035 (6)	−0.017 (7)	−0.015 (6)	−0.011 (6)
C1	0.038 (7)	0.045 (7)	0.033 (7)	0.005 (5)	0.016 (6)	−0.005 (6)
C2	0.041 (7)	0.038 (6)	0.025 (6)	0.005 (5)	0.012 (5)	0.003 (5)
C3	0.043 (7)	0.053 (8)	0.032 (7)	0.013 (6)	0.019 (6)	0.013 (6)
C4	0.044 (8)	0.049 (8)	0.030 (7)	0.006 (6)	0.006 (6)	−0.004 (6)
C5	0.034 (7)	0.050 (8)	0.022 (6)	0.002 (5)	−0.002 (5)	−0.008 (5)
C6	0.021 (6)	0.054 (7)	0.025 (6)	0.000 (5)	0.006 (5)	0.007 (5)
C7	0.033 (6)	0.036 (6)	0.020 (5)	−0.006 (5)	0.003 (5)	0.004 (5)
C8	0.030 (7)	0.038 (6)	0.027 (6)	0.001 (5)	0.015 (5)	0.003 (5)
C9	0.045 (8)	0.045 (8)	0.048 (8)	−0.013 (6)	0.010 (6)	−0.015 (7)
C10	0.031 (7)	0.058 (8)	0.066 (9)	−0.013 (6)	0.015 (7)	0.005 (8)
C11	0.051 (10)	0.066 (10)	0.058 (10)	0.007 (7)	0.030 (8)	0.012 (8)
C12	0.035 (7)	0.046 (7)	0.034 (6)	0.004 (5)	0.012 (5)	−0.003 (6)
C13	0.031 (6)	0.039 (6)	0.020 (5)	0.002 (5)	0.006 (5)	0.003 (5)
C14	0.034 (6)	0.042 (7)	0.026 (6)	−0.001 (5)	0.014 (5)	−0.003 (5)
C15	0.036 (7)	0.036 (7)	0.030 (6)	0.004 (5)	0.015 (5)	0.006 (5)
C16	0.038 (7)	0.045 (8)	0.039 (7)	0.005 (6)	0.010 (6)	0.010 (6)
C17	0.059 (9)	0.045 (8)	0.063 (9)	0.005 (7)	0.029 (8)	0.020 (7)
C18	0.066 (10)	0.063 (10)	0.050 (9)	0.020 (8)	0.026 (8)	0.024 (8)
C19	0.061 (10)	0.083 (12)	0.041 (8)	0.011 (9)	0.005 (7)	0.018 (8)
C20	0.042 (8)	0.069 (10)	0.027 (7)	0.000 (7)	−0.007 (6)	0.004 (7)

Geometric parameters (Å, º) top

Bi—N1	2.387 (10)	C8—C13	1.387 (17)
Bi—O1	2.546 (10)	C8—C9	1.411 (17)
Bi—C1	2.245 (13)	C9—C10	1.340 (18)
Bi—C8	2.204 (12)	C9—H9	0.9300
Cl1—O3	1.407 (10)	C10—C11	1.39 (2)
Cl1—O4	1.413 (10)	C10—H10	0.9300
Cl1—O2	1.434 (10)	C11—C12	1.349 (19)
Cl1—O1	1.448 (10)	C11—H11	0.9300
N1—C7	1.484 (13)	C12—C13	1.410 (16)
N1—C15	1.490 (15)	C12—H12	0.9300
N1—C14	1.514 (12)	C13—C14	1.508 (15)
C1—C2	1.383 (16)	C14—H14A	0.9700
C1—C6	1.418 (17)	C14—H14B	0.9700
C2—C3	1.402 (17)	C15—C16	1.389 (18)
C2—H2	0.9300	C15—C20	1.432 (16)
C3—C4	1.351 (18)	C16—C17	1.360 (18)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.414 (18)	C17—C18	1.41 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.347 (16)	C18—C19	1.36 (2)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.504 (16)	C19—C20	1.365 (19)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—H20	0.9300

C8—Bi—C1	92.5 (5)	C13—C8—C9	118.4 (11)
C8—Bi—N1	77.4 (4)	C13—C8—Bi	115.1 (8)
C1—Bi—N1	74.6 (4)	C9—C8—Bi	126.5 (9)
C8—Bi—O1	83.1 (4)	C10—C9—C8	121.5 (13)
C1—Bi—O1	89.4 (4)	C10—C9—H9	119.3
N1—Bi—O1	154.0 (3)	C8—C9—H9	119.3
O3—Cl1—O4	110.7 (7)	C9—C10—C11	119.7 (13)
O3—Cl1—O2	111.0 (7)	C9—C10—H10	120.2
O4—Cl1—O2	110.9 (7)	C11—C10—H10	120.2
O3—Cl1—O1	108.6 (7)	C12—C11—C10	120.9 (13)
O4—Cl1—O1	108.6 (8)	C12—C11—H11	119.5
O2—Cl1—O1	106.9 (6)	C10—C11—H11	119.5
C7—N1—C15	110.7 (9)	C11—C12—C13	120.0 (12)
C7—N1—C14	109.2 (8)	C11—C12—H12	120.0
C15—N1—C14	109.6 (8)	C13—C12—H12	120.0
C7—N1—Bi	104.8 (7)	C8—C13—C12	119.4 (11)
C15—N1—Bi	113.7 (6)	C8—C13—C14	122.3 (10)
C14—N1—Bi	108.6 (7)	C12—C13—C14	118.2 (10)
Cl1—O1—Bi	122.3 (6)	C13—C14—N1	113.3 (9)
C2—C1—C6	120.1 (12)	C13—C14—H14A	108.9
C2—C1—Bi	127.1 (9)	N1—C14—H14A	108.9
C6—C1—Bi	112.7 (8)	C13—C14—H14B	108.9
C1—C2—C3	118.6 (12)	N1—C14—H14B	108.9
C1—C2—H2	120.7	H14A—C14—H14B	107.7
C3—C2—H2	120.7	C16—C15—C20	119.0 (11)
C4—C3—C2	121.3 (12)	C16—C15—N1	123.0 (10)
C4—C3—H3	119.4	C20—C15—N1	118.0 (11)
C2—C3—H3	119.4	C17—C16—C15	120.1 (13)
C3—C4—C5	119.8 (13)	C17—C16—H16	119.9
C3—C4—H4	120.1	C15—C16—H16	119.9
C5—C4—H4	120.1	C16—C17—C18	120.8 (14)
C6—C5—C4	120.4 (12)	C16—C17—H17	119.6
C6—C5—H5	119.8	C18—C17—H17	119.6
C4—C5—H5	119.8	C19—C18—C17	119.2 (13)
C5—C6—C1	119.8 (12)	C19—C18—H18	120.4
C5—C6—C7	120.9 (11)	C17—C18—H18	120.4
C1—C6—C7	119.3 (11)	C18—C19—C20	121.6 (15)
N1—C7—C6	109.9 (9)	C18—C19—H19	119.2
N1—C7—H7A	109.7	C20—C19—H19	119.2
C6—C7—H7A	109.7	C19—C20—C15	119.4 (14)
N1—C7—H7B	109.7	C19—C20—H20	120.3
C6—C7—H7B	109.7	C15—C20—H20	120.3
H7A—C7—H7B	108.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.46	3.137 (17)	130
C14—H14B···O2ⁱⁱ	0.97	2.55	3.398 (16)	146

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Bi(C₂₀H₁₇N)(ClO₄)]
M_r	579.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.0635 (10), 14.0755 (12), 11.5121 (10)
β (°)	107.590 (2)
V (Å³)	1863.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	9.63
Crystal size (mm)	0.32 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Bruker, 2001)
T_min, T_max	0.100, 0.145
No. of measured, independent and observed [I > 2σ(I)] reflections	9267, 3279, 2585
R_int	0.166
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.163, 1.02
No. of reflections	3279
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	4.89, −4.14

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Bi—N1	2.387 (10)	Bi—C1	2.245 (13)
Bi—O1	2.546 (10)	Bi—C8	2.204 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.46	3.137 (17)	130
C14—H14B···O2ⁱⁱ	0.97	2.55	3.398 (16)	146

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge the National Science Foundation of China (grant No. 51074093) for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Minoura, M., Kanamori, Y., Miyake, A. & Akiba, K. (1999). Chem. Lett. pp. 861–862. Web of Science CSD CrossRef Google Scholar
Ohkata, K., Takemoto, S., Ohnishi, M. & Akiba, K. Y. (1989). Tetrahedron Lett. 30, 4841–4844. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shimada, S., Yamazaki, O., Tanaka, T., Suzuki, Y. & Tanaka, M. (2004). J. Organomet. Chem. 689, 3012–3023. Web of Science CSD CrossRef CAS Google Scholar
Tan, N. & Zhang, X. (2011). Acta Cryst. E67, m252. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yin, S., Maruyama, J., Yamashita, T. & Shimada, S. (2008). Angew. Chem. Int. Ed. 47, 6590–6593. Web of Science CSD CrossRef CAS Google Scholar
Zhang, X.-W., Qiu, R.-H., Tan, N.-Y., Yin, S.-F., Xia, J., Au, C.-T. & Luo, S.-L. (2010). Tetrahedron Lett. 51, 153–156. Web of Science CSD CrossRef CAS Google Scholar
Zhang, X.-W., Xia, J., Yan, H.-W., Luo, S.-L., Yin, S.-F., Au, C.-T. & Wong, W.-Y. (2009). J. Organomet. Chem. 694, 3019–3026. Web of Science CSD CrossRef CAS Google Scholar