Crystal structure of dimethyl 2,5-bis­[(di­phen­oxy­phosphor­yl)­oxy]cyclo­hexa-1,4-diene-1,4-di­carboxyl­ate

Gao, L.; Ma, Z.; Yan, H.

doi:10.1107/S2056989015008658

organic compounds

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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages o401-o402

doi:10.1107/S2056989015008658

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Crystal structure of dimethyl 2,5-bis[(diphenoxyphosphoryl)oxy]cyclohexa-1,4-diene-1,4-dicarboxylate

Lei Gao,^a Zongshan Ma ^a and Hong Yan ^a ^*

^aCollege of Life Science and Bio-engineering, Beijing University of Technology, Pingleyuan Street No. 100, Chaoyang District, Beijing 100124, People's Republic of China
^*Correspondence e-mail: hongyan@bjut.edu.cn

Edited by G. Smith, Queensland University of Technology, Australia (Received 15 April 2015; accepted 4 May 2015; online 13 May 2015)

In the title compound, C₃₄H₃₀O₁₂P₂, which was synthesized via the esterification of dimethyl 2,5-dioxo-1,4-cyclohexanedicarboxylate with diphenyl chlorophosphate, the molecule has crystallographic inversion symmetry. The dihedral angles between the plane of the cyclohexa-1,4-diene ring and those of the two benzene rings of the substituent phosphate groups are 41.0 (1) and 89.5 (1)°, while that with the ester group is 3.1 (3)°. In the crystal, only weak intermolecular C—H⋯O hydrogen bonds are present.

Keywords: crystal structure; cyclohexa-1,4-diene; C—H⋯O hydrogen bonds.

CCDC reference: 1057648

1. Related literature

For background information on cyclohexa-1,4-dienes, see: El-Rayyes & Al-Hajjar (1978 ). For the synthesis of the title compound, see: Chaignaud et al. (2008 ).

2. Experimental

2.1. Crystal data

C₃₄H₃₀O₁₂P₂
M_r = 692.52
Monoclinic, P 2₁ /c
a = 12.272 (10) Å
b = 10.629 (8) Å
c = 13.174 (10) Å
β = 113.644 (10)°
V = 1574 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

2.2. Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.960, T_max = 0.976
15948 measured reflections
3758 independent reflections
2264 reflections with I > 2σ(I)
R_int = 0.100

2.3. Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.099
S = 1.00
3758 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.50	3.345 (4)	148
C9—H9⋯O5ⁱⁱ	0.95	2.59	3.405 (4)	144
C10—H10⋯O3ⁱⁱⁱ	0.95	2.46	3.381 (4)	163
C15—H15B⋯O1^iv	0.99	2.56	3.409 (4)	144
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2005).

Supporting information

CCDC reference: 1057648

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015008658/zs2331sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015008658/zs2331Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015008658/zs2331Isup3.cml

checkCIF report

Comment top

1,4-Cyclohexadiene is a useful and fundamental structural motif found in a wide range of organic materials and biologically active molecules (El-Rayyes & Al-Hajjar, 1978). The synthetic routes for the preparation of derivatives of this parent compound have been reported (Chaignaud et al., 2008) but their crystal structures were not described.

The title compound, C₃₄H₃₀O₁₂P₂, was synthesized by the esterification of dimethyl 2,5-dioxo-1,4-cyclohexanedicarboxylate with diphenyl chlorophosphate using the reported procedure of Chaignaud et al. (2008) and the structure is reported herein.

The molecule of the title compound has crystallographic inversion symmetry (Fig. 1), with dihedral angles between the cyclohexa-1,4-diene ring and the two benzene rings of the substituent phosphate group of 41.0 (1) [C1–C6] and 89.5 (1)° [C7–C12]. The ester group is essentially coplanar with the cyclohexadiene group [dihedral angle = 3.1 (3)°]. In the crystal, only weak intermolecular C—H···O hydrogen bonds are present (Table 1).

Related literature top

For background information on cyclohexa-1,4-dienes, see: El-Rayyes & Al-Hajjar (1978). For the synthesis of the title compound, see: Chaignaud et al. (2008).

Experimental top

The title compound was synthesized using the basic procedure of Chaignaud et al. (2008) (Fig. 2), as follows: A solution of LiHMDS (1 M in THF, 7.9 mL) in THF (20 mL) was cooled to -78 °C under nitrogen. Subsequently, a mixture of dimethyl 2,5-dioxo-1,4-cyclohexanedicarboxylate (3.19 mmol), diphenyl chlorophosphate (6.67 mmol) and HMPA (8.90 mmol) in anhydrous THF (5 mL) were added dropwise over 5 min. The mixture was stirred at -78 °C for 1h under nitrogen and after completion of the reaction, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (3×15 mL), dried with anhydrous MgSO₄ and filtered. Subsequently, the product obtained by evaporation of the solvent was recrystallized from ethyl acetate giving a white solid in 10% yield (m.p. 118–120 °C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: CrystalStructure (Rigaku, 2005).

Figures top

	Fig. 1. The molecular conformation and atom numbering scheme for the title compound, with probability ellipsoids drawn at the 50% level. For symmetry code (a): -x, -y + 1, -z.
	Fig. 2. Synthetic route for the title compound.

Dimethyl 2,5-bis[(diphenoxyphosphoryl)oxy]cyclohexa-1,4-diene-1,4-dicarboxylate top

Crystal data top

C₃₄H₃₀O₁₂P₂	F(000) = 720
M_r = 692.52	D_x = 1.461 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 391–393 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.272 (10) Å	Cell parameters from 5446 reflections
b = 10.629 (8) Å	θ = 1.7–28.3°
c = 13.174 (10) Å	µ = 0.21 mm⁻¹
β = 113.644 (10)°	T = 113 K
V = 1574 (2) Å³	Prism, colorless
Z = 2	0.20 × 0.18 × 0.12 mm

Data collection top

Rigaku Saturn724 CCD diffractometer	3758 independent reflections
Radiation source: rotating anode	2264 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.100
Detector resolution: 14.22 pixels mm^-1	θ_max = 28.0°, θ_min = 1.8°
ω and ϕ scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.960, T_max = 0.976	l = −17→17
15948 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.012P)²] where P = (F_o² + 2F_c²)/3
3758 reflections	(Δ/σ)_max = 0.002
218 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₃₄H₃₀O₁₂P₂	V = 1574 (2) Å³
M_r = 692.52	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.272 (10) Å	µ = 0.21 mm⁻¹
b = 10.629 (8) Å	T = 113 K
c = 13.174 (10) Å	0.20 × 0.18 × 0.12 mm
β = 113.644 (10)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3758 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2264 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.976	R_int = 0.100
15948 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.54 e Å⁻³
3758 reflections	Δρ_min = −0.62 e Å⁻³
218 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
P1	0.17401 (5)	0.72276 (5)	0.24500 (4)	0.01714 (15)
O1	0.12748 (11)	0.81381 (12)	0.31240 (10)	0.0189 (3)
O2	0.26861 (12)	0.64338 (12)	0.34149 (11)	0.0211 (3)
O3	0.21532 (12)	0.77428 (12)	0.16508 (10)	0.0194 (3)
O4	0.06126 (12)	0.63451 (12)	0.19634 (10)	0.0187 (3)
O5	−0.16106 (13)	0.79217 (13)	−0.10725 (11)	0.0285 (4)
O6	−0.06056 (12)	0.82652 (13)	0.07360 (11)	0.0259 (4)
C1	0.20189 (18)	0.91573 (18)	0.36916 (16)	0.0181 (5)
C2	0.20083 (19)	1.02272 (19)	0.30979 (17)	0.0229 (5)
H2	0.1545	1.0266	0.2323	0.027*
C3	0.2684 (2)	1.1239 (2)	0.36526 (18)	0.0288 (6)
H3	0.2690	1.1986	0.3259	0.035*
C4	0.3353 (2)	1.1172 (2)	0.47791 (18)	0.0310 (6)
H4	0.3818	1.1873	0.5159	0.037*
C5	0.3350 (2)	1.0088 (2)	0.53572 (18)	0.0298 (6)
H5	0.3816	1.0046	0.6132	0.036*
C6	0.26714 (19)	0.90613 (19)	0.48111 (17)	0.0237 (5)
H6	0.2659	0.8313	0.5201	0.028*
C7	0.37059 (18)	0.58701 (19)	0.33647 (16)	0.0193 (5)
C8	0.45474 (17)	0.6591 (2)	0.31964 (15)	0.0221 (5)
H8	0.4432	0.7469	0.3063	0.027*
C9	0.55660 (19)	0.6006 (2)	0.32263 (17)	0.0294 (6)
H9	0.6158	0.6483	0.3105	0.035*
C10	0.5728 (2)	0.4722 (2)	0.34328 (17)	0.0317 (6)
H10	0.6431	0.4326	0.3455	0.038*
C11	0.4874 (2)	0.4024 (2)	0.36046 (17)	0.0290 (6)
H11	0.4987	0.3147	0.3747	0.035*
C12	0.38516 (19)	0.46028 (19)	0.35698 (17)	0.0247 (5)
H12	0.3256	0.4128	0.3687	0.030*
C13	0.02855 (17)	0.57494 (18)	0.09354 (16)	0.0173 (5)
C14	−0.04157 (18)	0.62776 (18)	−0.00080 (16)	0.0167 (5)
C15	−0.07850 (18)	0.55461 (17)	−0.10704 (15)	0.0186 (5)
H15A	−0.1664	0.5490	−0.1412	0.022*
H15B	−0.0532	0.6015	−0.1588	0.022*
C16	−0.09356 (18)	0.75651 (19)	−0.01748 (16)	0.0196 (5)
C17	−0.11425 (19)	0.95035 (18)	0.05728 (18)	0.0302 (6)
H17A	−0.0905	0.9985	0.0061	0.045*
H17B	−0.0876	0.9943	0.1286	0.045*
H17C	−0.2011	0.9420	0.0262	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0148 (3)	0.0166 (3)	0.0186 (3)	−0.0009 (2)	0.0052 (2)	−0.0017 (2)
O1	0.0177 (8)	0.0178 (8)	0.0225 (8)	−0.0025 (6)	0.0093 (7)	−0.0050 (6)
O2	0.0168 (8)	0.0239 (8)	0.0207 (8)	0.0035 (7)	0.0056 (7)	0.0029 (6)
O3	0.0193 (8)	0.0208 (8)	0.0194 (7)	−0.0011 (6)	0.0090 (7)	0.0005 (6)
O4	0.0166 (7)	0.0197 (8)	0.0182 (8)	−0.0054 (6)	0.0055 (6)	−0.0040 (6)
O5	0.0344 (9)	0.0248 (9)	0.0226 (8)	0.0067 (7)	0.0078 (8)	0.0036 (7)
O6	0.0235 (8)	0.0227 (8)	0.0258 (9)	0.0062 (7)	0.0038 (7)	−0.0043 (7)
C1	0.0165 (11)	0.0177 (11)	0.0200 (11)	−0.0006 (9)	0.0070 (9)	−0.0040 (9)
C2	0.0272 (13)	0.0221 (12)	0.0168 (11)	0.0012 (10)	0.0060 (10)	−0.0016 (9)
C3	0.0354 (14)	0.0208 (13)	0.0301 (13)	−0.0050 (11)	0.0131 (12)	−0.0028 (10)
C4	0.0334 (14)	0.0261 (14)	0.0310 (14)	−0.0123 (11)	0.0103 (12)	−0.0132 (11)
C5	0.0276 (13)	0.0379 (15)	0.0179 (12)	−0.0024 (11)	0.0029 (10)	−0.0045 (10)
C6	0.0271 (13)	0.0225 (13)	0.0217 (12)	0.0013 (10)	0.0101 (10)	0.0023 (10)
C7	0.0143 (11)	0.0238 (12)	0.0158 (11)	0.0044 (9)	0.0017 (9)	−0.0044 (9)
C8	0.0171 (11)	0.0216 (12)	0.0237 (12)	−0.0007 (10)	0.0041 (10)	−0.0038 (9)
C9	0.0161 (12)	0.0398 (15)	0.0307 (14)	−0.0035 (11)	0.0077 (11)	−0.0036 (11)
C10	0.0184 (12)	0.0442 (16)	0.0264 (13)	0.0096 (12)	0.0026 (11)	−0.0099 (11)
C11	0.0289 (13)	0.0248 (13)	0.0296 (13)	0.0069 (11)	0.0077 (11)	−0.0034 (11)
C12	0.0216 (12)	0.0228 (13)	0.0275 (12)	−0.0006 (10)	0.0074 (10)	−0.0010 (10)
C13	0.0147 (10)	0.0186 (11)	0.0189 (11)	−0.0052 (9)	0.0071 (9)	−0.0058 (9)
C14	0.0144 (10)	0.0169 (11)	0.0188 (11)	−0.0012 (9)	0.0066 (9)	−0.0009 (9)
C15	0.0154 (11)	0.0201 (12)	0.0182 (11)	−0.0005 (9)	0.0046 (9)	−0.0002 (9)
C16	0.0158 (11)	0.0240 (13)	0.0199 (11)	−0.0025 (9)	0.0079 (10)	0.0003 (9)
C17	0.0270 (13)	0.0246 (13)	0.0355 (14)	0.0094 (11)	0.0088 (12)	−0.0039 (11)

Geometric parameters (Å, º) top

P1—O1	1.5677 (19)	C11—C12	1.382 (4)
P1—O2	1.5785 (19)	C13—C14	1.320 (3)
P1—O3	1.4469 (19)	C13—C15ⁱ	1.489 (3)
P1—O4	1.579 (2)	C14—C15	1.503 (3)
O1—C1	1.421 (3)	C14—C16	1.489 (3)
O2—C7	1.413 (3)	C2—H2	0.9500
O4—C13	1.400 (3)	C3—H3	0.9500
O5—C16	1.201 (3)	C4—H4	0.9500
O6—C16	1.330 (3)	C5—H5	0.9500
O6—C17	1.449 (3)	C6—H6	0.9500
C1—C2	1.377 (3)	C8—H8	0.9500
C1—C6	1.371 (3)	C9—H9	0.9500
C2—C3	1.376 (3)	C10—H10	0.9500
C3—C4	1.380 (3)	C11—H11	0.9500
C4—C5	1.382 (3)	C12—H12	0.9500
C5—C6	1.386 (3)	C15—H15A	0.9900
C7—C8	1.374 (3)	C15—H15B	0.9900
C7—C12	1.371 (3)	C17—H17A	0.9800
C8—C9	1.383 (3)	C17—H17B	0.9800
C9—C10	1.390 (3)	C17—H17C	0.9800
C10—C11	1.375 (4)

O1—P1—O2	101.02 (7)	O5—C16—C14	121.40 (18)
O1—P1—O3	119.47 (8)	O6—C16—C14	115.08 (17)
O1—P1—O4	97.92 (8)	C1—C2—H2	121.00
O2—P1—O3	115.41 (9)	C3—C2—H2	121.00
O2—P1—O4	104.54 (8)	C2—C3—H3	120.00
O3—P1—O4	115.79 (8)	C4—C3—H3	120.00
P1—O1—C1	117.75 (13)	C3—C4—H4	120.00
P1—O2—C7	124.62 (13)	C5—C4—H4	120.00
P1—O4—C13	121.73 (14)	C4—C5—H5	120.00
C16—O6—C17	114.76 (16)	C6—C5—H5	120.00
O1—C1—C2	118.23 (17)	C1—C6—H6	121.00
O1—C1—C6	118.96 (17)	C5—C6—H6	121.00
C2—C1—C6	122.74 (19)	C7—C8—H8	121.00
C1—C2—C3	118.52 (19)	C9—C8—H8	121.00
C2—C3—C4	120.2 (2)	C8—C9—H9	120.00
C3—C4—C5	120.3 (2)	C10—C9—H9	120.00
C4—C5—C6	120.3 (2)	C9—C10—H10	120.00
C1—C6—C5	118.03 (19)	C11—C10—H10	120.00
O2—C7—C8	120.56 (18)	C10—C11—H11	120.00
O2—C7—C12	117.1 (2)	C12—C11—H11	120.00
C8—C7—C12	122.2 (2)	C7—C12—H12	120.00
C7—C8—C9	118.3 (2)	C11—C12—H12	120.00
C8—C9—C10	120.3 (2)	C14—C15—H15A	109.00
C9—C10—C11	120.2 (2)	C14—C15—H15B	109.00
C10—C11—C12	119.8 (2)	H15A—C15—H15B	108.00
C7—C12—C11	119.3 (2)	C13ⁱ—C15—H15A	109.00
O4—C13—C14	122.97 (18)	C13ⁱ—C15—H15B	109.00
O4—C13—C15ⁱ	110.99 (16)	O6—C17—H17A	109.00
C14—C13—C15ⁱ	125.99 (18)	O6—C17—H17B	109.00
C13—C14—C15	119.73 (18)	O6—C17—H17C	109.00
C13—C14—C16	127.52 (18)	H17A—C17—H17B	109.00
C15—C14—C16	112.75 (16)	H17A—C17—H17C	109.00
C13ⁱ—C15—C14	114.28 (16)	H17B—C17—H17C	109.00
O5—C16—O6	123.51 (19)

O2—P1—O1—C1	75.66 (14)	C3—C4—C5—C6	−0.3 (4)
O3—P1—O1—C1	−52.09 (15)	C4—C5—C6—C1	0.4 (4)
O4—P1—O1—C1	−177.76 (12)	O2—C7—C8—C9	175.83 (17)
O1—P1—O2—C7	−151.58 (15)	C12—C7—C8—C9	0.6 (3)
O3—P1—O2—C7	−21.23 (17)	O2—C7—C12—C11	−175.66 (18)
O4—P1—O2—C7	107.15 (15)	C8—C7—C12—C11	−0.3 (3)
O1—P1—O4—C13	149.57 (14)	C7—C8—C9—C10	−0.6 (3)
O2—P1—O4—C13	−106.81 (14)	C8—C9—C10—C11	0.3 (3)
O3—P1—O4—C13	21.34 (17)	C9—C10—C11—C12	0.1 (3)
P1—O1—C1—C2	81.9 (2)	C10—C11—C12—C7	−0.1 (3)
P1—O1—C1—C6	−101.1 (2)	O4—C13—C14—C15	−176.33 (19)
P1—O2—C7—C8	59.5 (2)	O4—C13—C14—C16	2.7 (4)
P1—O2—C7—C12	−125.04 (17)	C15ⁱ—C13—C14—C15	0.7 (4)
P1—O4—C13—C14	−88.2 (2)	C15ⁱ—C13—C14—C16	179.7 (2)
P1—O4—C13—C15ⁱ	94.39 (18)	O4—C13—C15ⁱ—C14ⁱ	176.67 (18)
C17—O6—C16—O5	1.1 (3)	C14—C13—C15ⁱ—C14ⁱ	−0.7 (3)
C17—O6—C16—C14	−178.27 (19)	C13—C14—C15—C13ⁱ	−0.6 (3)
O1—C1—C2—C3	177.0 (2)	C16—C14—C15—C13ⁱ	−179.77 (19)
C6—C1—C2—C3	0.2 (4)	C13—C14—C16—O5	−176.4 (2)
O1—C1—C6—C5	−177.2 (2)	C13—C14—C16—O6	2.9 (4)
C2—C1—C6—C5	−0.4 (4)	C15—C14—C16—O5	2.7 (3)
C1—C2—C3—C4	0.0 (4)	C15—C14—C16—O6	−177.98 (19)
C2—C3—C4—C5	0.1 (4)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱⁱ	0.95	2.56	3.191 (4)	124
C6—H6···O3ⁱⁱⁱ	0.95	2.50	3.345 (4)	148
C9—H9···O5^iv	0.95	2.59	3.405 (4)	144
C10—H10···O3^v	0.95	2.46	3.381 (4)	163
C15—H15B···O1^vi	0.99	2.56	3.409 (4)	144

Symmetry codes: (ii) −x, −y+2, −z; (iii) x, −y+3/2, z+1/2; (iv) x+1, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.50	3.345 (4)	148
C9—H9···O5ⁱⁱ	0.95	2.59	3.405 (4)	144
C10—H10···O3ⁱⁱⁱ	0.95	2.46	3.381 (4)	163
C15—H15B···O1^iv	0.99	2.56	3.409 (4)	144

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

Acknowledgements

This work was supported financially by the Key Projects in the National Science and Technology Pillar Program (No. 2012ZX10001007-008-002) and the Doctoral Fund of Innovation of Beijing University of Technology.

References

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