2-[2-(2,4-Dinitro­phen­yl)eth­yl]-1,3,5-trinitro­benzene

Wei, Z.-H.; Wang, W.-Y.; Diao, Y.; Wang, J.-L.

doi:10.1107/S1600536811041031

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2898

doi:10.1107/S1600536811041031

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2-[2-(2,4-Dinitrophenyl)ethyl]-1,3,5-trinitrobenzene

Zhi-Hua Wei,^a Wen-Yan Wang,^a Ying Diao ^a and Jian-Long Wang ^a ^*

^aSchool of Chemical Engineering and Environment, North University of China, Taiyuan, People's Republic of China
^*Correspondence e-mail: wangjianlong@nuc.edu.cn

(Received 2 October 2011; accepted 5 October 2011; online 8 October 2011)

In the title compound, C₁₄H₉N₅O₁₀, the two benzene rings are inclined at a dihedral angle of 14.81 (5)°, and the nitro groups are twisted with respect to the benzene rings to which they are attached, making dihedral angles of 57.89 (7), 14.93 (7), 62.58 (7), 2.80 (12) and 22.38 (12)°. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

The title compound is an intermediate in the synthesis of the high energy density compound 2,2′,4,4′,6,6′-hexanitrostilbene, see: Shipp (1964 ). For the synthesis, see: Blatt & Rytina (1950 ).

Experimental

Crystal data

C₁₄H₉N₅O₁₀
M_r = 407.26
Monoclinic, P 2₁ /n
a = 14.099 (7) Å
b = 8.227 (4) Å
c = 15.356 (8) Å
β = 114.758 (7)°
V = 1617.6 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2000 ) T_min = 0.971, T_max = 0.983
16454 measured reflections
3823 independent reflections
2847 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.03
3823 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O8ⁱ	0.95	2.39	3.249 (2)	151
C10—H10⋯O2ⁱⁱ	0.95	2.58	3.508 (3)	167
C11—H11⋯O9ⁱⁱ	0.95	2.40	3.353 (3)	176
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536811041031/xu5347sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041031/xu5347Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041031/xu5347Isup3.cml

checkCIF report

Comment top

2,2',4,4',6,6'-Hexantanitrobibenzyl, which can be prepared from bibenzyl by nitration (Blatt & Rytina, 1950), is a intermediate for synthesizing high energy density compound 2,2',4,4',6,6'-hexanitrostilbene (Shipp, 1964). As a byproduct, 2,2',4,4',6–pentantanitrobibenzyl is separated from the nitrate product. Here we report the crystal structure of the title compound.

In the crystal structure, because the number of nitro group is not identical in two benzene rings, the two benzene rings are inclined at a dihedral angle 14.811 (48)°, For the interaction of nitro groups, the nitro groups is rotated out the benzene plane, making dihedral angles of 57.885 (65)°(N1/O1, O2), 14.934 (68)°(N2/O3, O4), 62.579 (71)° (N3/O5, O6), 2.799 (121)°(N4/O7, O8) and 22.376 (115)° (N5/O9, O10).

Related literature top

The title compound is an intermediate in the synthesis of the high

energy density compound 2,2',4,4',6,6'-hexanitrostilbene, see: Shipp (1964). For the synthesis, see: Blatt & Rytina (1950).

Experimental top

The title compound was prepared according to literature method (Blatt et al., 1950). Single crystals were obtained by evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2000); cell refinement: CrystalClear (Rigaku/MSC, 2000); data reduction: CrystalClear (Rigaku/MSC, 2000); 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 the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound.

2-[2-(2,4-Dinitrophenyl)ethyl]-1,3,5-trinitrobenzene top

Crystal data top

C₁₄H₉N₅O₁₀	F(000) = 832
M_r = 407.26	D_x = 1.672 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5515 reflections
a = 14.099 (7) Å	θ = 1.6–27.9°
b = 8.227 (4) Å	µ = 0.15 mm⁻¹
c = 15.356 (8) Å	T = 113 K
β = 114.758 (7)°	Prism, colorless
V = 1617.6 (14) Å³	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection top

Rigaku Saturn724 CCD diffractometer	3823 independent reflections
Radiation source: rotating anode	2847 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.043
Detector resolution: 14.22 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω and ϕ scans	h = −18→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2000)	k = −10→10
T_min = 0.971, T_max = 0.983	l = −20→19
16454 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0594P)²] where P = (F_o² + 2F_c²)/3
3823 reflections	(Δ/σ)_max = 0.002
262 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₄H₉N₅O₁₀	V = 1617.6 (14) Å³
M_r = 407.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.099 (7) Å	µ = 0.15 mm⁻¹
b = 8.227 (4) Å	T = 113 K
c = 15.356 (8) Å	0.20 × 0.18 × 0.12 mm
β = 114.758 (7)°

Data collection top

Rigaku Saturn724 CCD diffractometer	3823 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2000)	2847 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.983	R_int = 0.043
16454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
3823 reflections	Δρ_min = −0.33 e Å⁻³
262 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
O1	0.64474 (9)	0.08191 (14)	1.03105 (8)	0.0325 (3)
O2	0.68105 (8)	0.33883 (14)	1.06099 (7)	0.0270 (3)
O3	0.86607 (8)	0.48825 (14)	0.85862 (7)	0.0273 (3)
O4	0.79057 (8)	0.43068 (14)	0.70657 (7)	0.0283 (3)
O5	0.39540 (8)	0.33811 (14)	0.60692 (8)	0.0291 (3)
O6	0.40895 (9)	0.07989 (14)	0.63732 (8)	0.0369 (3)
O7	−0.06620 (8)	0.15196 (13)	0.84028 (8)	0.0264 (3)
O8	0.02060 (9)	0.19441 (17)	0.99188 (8)	0.0408 (3)
O9	0.37441 (8)	0.36062 (14)	1.11500 (7)	0.0281 (3)
O10	0.46932 (9)	0.29102 (18)	1.04226 (9)	0.0450 (4)
N1	0.65521 (9)	0.22023 (16)	1.00726 (9)	0.0217 (3)
N2	0.79545 (9)	0.42757 (15)	0.78811 (8)	0.0199 (3)
N3	0.43956 (9)	0.21995 (16)	0.65550 (8)	0.0204 (3)
N4	0.01476 (10)	0.18383 (16)	0.91063 (9)	0.0224 (3)
N5	0.38449 (10)	0.31254 (16)	1.04428 (9)	0.0227 (3)
C1	0.63893 (11)	0.24823 (17)	0.90684 (10)	0.0171 (3)
C2	0.72280 (11)	0.31584 (17)	0.89544 (10)	0.0186 (3)
H2	0.7866	0.3392	0.9490	0.022*
C3	0.71003 (11)	0.34782 (17)	0.80322 (10)	0.0163 (3)
C4	0.61836 (11)	0.31584 (17)	0.72466 (10)	0.0174 (3)
H4	0.6110	0.3381	0.6614	0.021*
C5	0.53752 (11)	0.25001 (17)	0.74139 (10)	0.0166 (3)
C6	0.54234 (11)	0.21345 (17)	0.83201 (10)	0.0168 (3)
C7	0.44685 (11)	0.16298 (17)	0.84700 (11)	0.0193 (3)
H7A	0.4687	0.1085	0.9099	0.023*
H7B	0.4046	0.0853	0.7964	0.023*
C8	0.38085 (11)	0.31511 (19)	0.84336 (11)	0.0224 (3)
H8A	0.4257	0.3962	0.8901	0.027*
H8B	0.3553	0.3642	0.7787	0.027*
C9	0.28820 (11)	0.27651 (17)	0.86572 (10)	0.0184 (3)
C10	0.19285 (11)	0.24056 (18)	0.78975 (10)	0.0206 (3)
H10	0.1892	0.2383	0.7266	0.025*
C11	0.10317 (11)	0.20795 (18)	0.80267 (10)	0.0207 (3)
H11	0.0392	0.1831	0.7497	0.025*
C12	0.10966 (10)	0.21278 (17)	0.89524 (10)	0.0168 (3)
C13	0.20092 (11)	0.24750 (17)	0.97324 (10)	0.0184 (3)
H13	0.2037	0.2512	1.0361	0.022*
C14	0.28871 (11)	0.27693 (17)	0.95696 (10)	0.0174 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0369 (7)	0.0277 (7)	0.0361 (7)	0.0037 (5)	0.0186 (5)	0.0142 (5)
O2	0.0267 (6)	0.0344 (7)	0.0198 (6)	−0.0049 (5)	0.0096 (5)	−0.0043 (5)
O3	0.0223 (6)	0.0302 (7)	0.0264 (6)	−0.0099 (5)	0.0074 (5)	−0.0005 (5)
O4	0.0273 (6)	0.0392 (7)	0.0234 (6)	−0.0053 (5)	0.0156 (5)	0.0023 (5)
O5	0.0249 (6)	0.0293 (7)	0.0249 (6)	0.0011 (5)	0.0023 (5)	0.0041 (5)
O6	0.0293 (7)	0.0235 (7)	0.0455 (7)	−0.0058 (5)	0.0035 (6)	−0.0108 (5)
O7	0.0151 (6)	0.0305 (6)	0.0307 (6)	−0.0029 (4)	0.0069 (5)	−0.0059 (5)
O8	0.0273 (7)	0.0792 (10)	0.0204 (6)	−0.0048 (6)	0.0143 (5)	0.0012 (6)
O9	0.0260 (6)	0.0374 (7)	0.0180 (5)	0.0030 (5)	0.0063 (5)	−0.0062 (5)
O10	0.0147 (6)	0.0825 (11)	0.0368 (7)	−0.0038 (6)	0.0097 (5)	−0.0248 (7)
N1	0.0182 (7)	0.0254 (7)	0.0224 (7)	0.0017 (5)	0.0094 (5)	0.0051 (5)
N2	0.0185 (7)	0.0211 (7)	0.0211 (7)	−0.0016 (5)	0.0094 (5)	0.0018 (5)
N3	0.0172 (6)	0.0243 (7)	0.0216 (6)	−0.0020 (5)	0.0100 (5)	−0.0048 (5)
N4	0.0180 (7)	0.0263 (7)	0.0227 (7)	−0.0004 (5)	0.0083 (6)	0.0007 (5)
N5	0.0170 (7)	0.0268 (7)	0.0228 (7)	−0.0007 (5)	0.0069 (5)	−0.0055 (5)
C1	0.0193 (7)	0.0166 (7)	0.0172 (7)	0.0013 (5)	0.0094 (6)	0.0021 (5)
C2	0.0168 (7)	0.0186 (7)	0.0185 (7)	0.0007 (6)	0.0056 (6)	0.0011 (6)
C3	0.0144 (7)	0.0162 (7)	0.0213 (7)	−0.0004 (5)	0.0103 (6)	0.0005 (5)
C4	0.0195 (7)	0.0178 (7)	0.0158 (7)	0.0017 (6)	0.0083 (6)	−0.0005 (5)
C5	0.0127 (7)	0.0178 (7)	0.0183 (7)	0.0007 (5)	0.0053 (6)	−0.0032 (5)
C6	0.0173 (7)	0.0136 (7)	0.0203 (7)	0.0006 (5)	0.0089 (6)	−0.0012 (5)
C7	0.0179 (8)	0.0194 (8)	0.0242 (8)	−0.0028 (6)	0.0122 (6)	−0.0015 (6)
C8	0.0221 (8)	0.0217 (8)	0.0269 (8)	−0.0003 (6)	0.0137 (7)	0.0000 (6)
C9	0.0190 (8)	0.0160 (7)	0.0223 (8)	0.0013 (5)	0.0107 (6)	0.0001 (6)
C10	0.0229 (8)	0.0247 (8)	0.0163 (7)	0.0015 (6)	0.0101 (6)	−0.0007 (6)
C11	0.0181 (8)	0.0239 (8)	0.0171 (7)	0.0005 (6)	0.0044 (6)	−0.0027 (6)
C12	0.0148 (7)	0.0176 (7)	0.0199 (7)	0.0003 (5)	0.0091 (6)	0.0000 (6)
C13	0.0203 (8)	0.0194 (7)	0.0164 (7)	0.0015 (6)	0.0084 (6)	0.0003 (5)
C14	0.0138 (7)	0.0172 (7)	0.0186 (7)	0.0004 (5)	0.0041 (6)	−0.0024 (6)

Geometric parameters (Å, º) top

O1—N1	1.2229 (17)	C4—C5	1.380 (2)
O2—N1	1.2305 (17)	C4—H4	0.9500
O3—N2	1.2289 (15)	C5—C6	1.397 (2)
O4—N2	1.2252 (16)	C6—C7	1.516 (2)
O5—N3	1.2248 (17)	C7—C8	1.547 (2)
O6—N3	1.2211 (17)	C7—H7A	0.9900
O7—N4	1.2272 (16)	C7—H7B	0.9900
O8—N4	1.2187 (18)	C8—C9	1.517 (2)
O9—N5	1.2187 (16)	C8—H8A	0.9900
O10—N5	1.2222 (17)	C8—H8B	0.9900
N1—C1	1.4789 (19)	C9—C10	1.394 (2)
N2—C3	1.4727 (18)	C9—C14	1.398 (2)
N3—C5	1.4774 (18)	C10—C11	1.386 (2)
N4—C12	1.472 (2)	C10—H10	0.9500
N5—C14	1.4801 (19)	C11—C12	1.386 (2)
C1—C2	1.383 (2)	C11—H11	0.9500
C1—C6	1.395 (2)	C12—C13	1.372 (2)
C2—C3	1.376 (2)	C13—C14	1.383 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.374 (2)

O1—N1—O2	125.21 (13)	C5—C6—C7	122.30 (12)
O1—N1—C1	118.10 (13)	C6—C7—C8	109.39 (12)
O2—N1—C1	116.66 (12)	C6—C7—H7A	109.8
O4—N2—O3	124.75 (12)	C8—C7—H7A	109.8
O4—N2—C3	118.08 (12)	C6—C7—H7B	109.8
O3—N2—C3	117.16 (12)	C8—C7—H7B	109.8
O6—N3—O5	124.67 (13)	H7A—C7—H7B	108.2
O6—N3—C5	118.09 (12)	C9—C8—C7	112.61 (12)
O5—N3—C5	117.23 (12)	C9—C8—H8A	109.1
O8—N4—O7	123.76 (13)	C7—C8—H8A	109.1
O8—N4—C12	118.46 (12)	C9—C8—H8B	109.1
O7—N4—C12	117.78 (12)	C7—C8—H8B	109.1
O9—N5—O10	123.38 (13)	H8A—C8—H8B	107.8
O9—N5—C14	117.97 (13)	C10—C9—C14	115.96 (13)
O10—N5—C14	118.65 (13)	C10—C9—C8	118.37 (13)
C2—C1—C6	124.74 (13)	C14—C9—C8	125.65 (13)
C2—C1—N1	115.28 (12)	C11—C10—C9	122.64 (14)
C6—C1—N1	119.91 (13)	C11—C10—H10	118.7
C3—C2—C1	117.19 (13)	C9—C10—H10	118.7
C3—C2—H2	121.4	C10—C11—C12	117.96 (13)
C1—C2—H2	121.4	C10—C11—H11	121.0
C4—C3—C2	122.44 (13)	C12—C11—H11	121.0
C4—C3—N2	118.51 (13)	C13—C12—C11	122.44 (13)
C2—C3—N2	118.96 (12)	C13—C12—N4	118.48 (13)
C3—C4—C5	117.27 (13)	C11—C12—N4	119.06 (12)
C3—C4—H4	121.4	C12—C13—C14	117.52 (13)
C5—C4—H4	121.4	C12—C13—H13	121.2
C4—C5—C6	124.78 (13)	C14—C13—H13	121.2
C4—C5—N3	115.83 (13)	C13—C14—C9	123.46 (13)
C6—C5—N3	119.38 (13)	C13—C14—N5	114.64 (13)
C1—C6—C5	113.57 (13)	C9—C14—N5	121.89 (13)
C1—C6—C7	123.63 (13)

O1—N1—C1—C2	−122.42 (14)	N3—C5—C6—C7	−7.6 (2)
O2—N1—C1—C2	55.76 (17)	C1—C6—C7—C8	93.28 (16)
O1—N1—C1—C6	60.38 (18)	C5—C6—C7—C8	−78.03 (17)
O2—N1—C1—C6	−121.44 (15)	C6—C7—C8—C9	−175.40 (12)
C6—C1—C2—C3	−1.3 (2)	C7—C8—C9—C10	−92.16 (15)
N1—C1—C2—C3	−178.37 (12)	C7—C8—C9—C14	89.32 (18)
C1—C2—C3—C4	0.4 (2)	C14—C9—C10—C11	0.4 (2)
C1—C2—C3—N2	176.88 (12)	C8—C9—C10—C11	−178.27 (14)
O4—N2—C3—C4	−15.38 (19)	C9—C10—C11—C12	0.4 (2)
O3—N2—C3—C4	163.70 (13)	C10—C11—C12—C13	−0.3 (2)
O4—N2—C3—C2	167.96 (13)	C10—C11—C12—N4	178.04 (13)
O3—N2—C3—C2	−12.96 (19)	O8—N4—C12—C13	1.2 (2)
C2—C3—C4—C5	0.3 (2)	O7—N4—C12—C13	−179.59 (13)
N2—C3—C4—C5	−176.20 (12)	O8—N4—C12—C11	−177.28 (13)
C3—C4—C5—C6	−0.2 (2)	O7—N4—C12—C11	2.0 (2)
C3—C4—C5—N3	178.94 (12)	C11—C12—C13—C14	−0.6 (2)
O6—N3—C5—C4	117.21 (15)	N4—C12—C13—C14	−178.95 (12)
O5—N3—C5—C4	−62.02 (17)	C12—C13—C14—C9	1.5 (2)
O6—N3—C5—C6	−63.64 (18)	C12—C13—C14—N5	−179.64 (13)
O5—N3—C5—C6	117.13 (15)	C10—C9—C14—C13	−1.4 (2)
C2—C1—C6—C5	1.4 (2)	C8—C9—C14—C13	177.18 (14)
N1—C1—C6—C5	178.36 (12)	C10—C9—C14—N5	179.81 (13)
C2—C1—C6—C7	−170.56 (14)	C8—C9—C14—N5	−1.6 (2)
N1—C1—C6—C7	6.4 (2)	O9—N5—C14—C13	−21.49 (19)
C4—C5—C6—C1	−0.7 (2)	O10—N5—C14—C13	157.85 (15)
N3—C5—C6—C1	−179.73 (12)	O9—N5—C14—C9	157.42 (14)
C4—C5—C6—C7	171.45 (13)	O10—N5—C14—C9	−23.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8ⁱ	0.95	2.39	3.249 (2)	151
C10—H10···O2ⁱⁱ	0.95	2.58	3.508 (3)	167
C11—H11···O9ⁱⁱ	0.95	2.40	3.353 (3)	176

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

Experimental details

Crystal data
Chemical formula	C₁₄H₉N₅O₁₀
M_r	407.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	14.099 (7), 8.227 (4), 15.356 (8)
β (°)	114.758 (7)
V (Å³)	1617.6 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Rigaku Saturn724 CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2000)
T_min, T_max	0.971, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16454, 3823, 2847
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.03
No. of reflections	3823
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.33

Computer programs: CrystalClear (Rigaku/MSC, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O8ⁱ	0.95	2.39	3.249 (2)	151
C10—H10···O2ⁱⁱ	0.95	2.58	3.508 (3)	167
C11—H11···O9ⁱⁱ	0.95	2.40	3.353 (3)	176

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

Acknowledgements

The authors thank China North Industries Group Corporation for financial support.

References

Blatt, A. H. & Rytina, A. W. (1950). J. Am. Chem. Soc. 72, 403–405. CrossRef CAS Web of Science Google Scholar
Rigaku/MSC (2000). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shipp, K. G. (1964). J. Org. Chem. 29, 2620–2623. CrossRef CAS Web of Science Google Scholar