(E)-1-Nitro-4-(2-nitro­ethen­yl)benzene

Jing, L.-H.

doi:10.1107/S1600536809042561

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2809

https://doi.org/10.1107/S1600536809042561

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(E)-1-Nitro-4-(2-nitroethenyl)benzene

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jhrkk20060220@yahoo.com.cn

(Received 15 October 2009; accepted 16 October 2009; online 23 October 2009)

The asymmetric unit of the title compound, C₈H₆N₂O₄, consists of two independent molecules with similar geometries, each adopting a trans configuration about the olefinic double bond. The two molecules are both almost planar (r.m.s. deviations = 0.034 and 0.035 Å) and form a dihedral angle of 83.62 (2)°. Short N⋯O contacts [2.834 (3)–2.861 (3) Å] are observed between the nitro groups of neighbouring molecules, with the O atom located directly atop the p orbital of the N atom. In the crystal, the molecules are linked into a three-dimensional network by the N⋯O interactions and by C—H⋯O hydrogen bonds.

Related literature

For general background to β-nitroolefins, see: Barrett & Graboski (1986 ). For the synthesis, see: Valdes et al. (2007 ).

Experimental

Crystal data

C₈H₆N₂O₄
M_r = 194.15
Orthorhombic, P n a 2₁
a = 15.847 (4) Å
b = 4.9991 (11) Å
c = 20.495 (5) Å
V = 1623.6 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 93 K
0.43 × 0.17 × 0.17 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: none
12157 measured reflections
1921 independent reflections
1821 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 1.13
1921 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5ⁱ	0.95	2.57	3.389 (3)	144
C5—H5⋯O6ⁱⁱ	0.95	2.43	3.234 (3)	143
C6—H6⋯O7ⁱⁱⁱ	0.95	2.56	3.469 (3)	160
C7—H7⋯O5ⁱ	0.95	2.45	3.304 (3)	150
C10—H10⋯O4^iv	0.95	2.41	3.352 (3)	174
C11—H11⋯O1^v	0.95	2.44	3.243 (3)	142
C14—H14⋯O2^vi	0.95	2.57	3.381 (3)	144
C15—H15⋯O2^vi	0.95	2.44	3.296 (3)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, -y+2, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042561/ci2942sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042561/ci2942Isup2.hkl

checkCIF report

Comment top

β-Nitroolefins are a class of useful and versatile building blocks in organic synthesis (Barrett & Graboski, 1986). The author reports here, the crystal structure of the title compound.

The asymmetric unit of the title compound consists of two crystallographically independent molecules (Fig. 1) each of which adopts a trans configuration about the olefinic double bond. All atoms in each independent molecule are almost coplanar. The N2/O3/O4 and C1-C6 (r.m.s. deviation 0.001 Å) planes form a dihedral angle of 1.4 (4)°. The dihedral angle between the C1-C6 and N1/O1/O2/C7/C8 (r.m.s. deviation 0.031 Å) planes is 2.9 (1)°. The N4/O7/O8 and C9-C14 (r.m.s. deviation 0.004 Å) planes form a dihedral angle of 2.9 (4)°. The dihedral angle between the C9-C14 and N3/O5/O6/C15/C16 (r.m.s. deviation 0.028 Å) planes is 2.9 (1)°. The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1) and N···O short contacts.

Related literature top

For general background to β-nitroolefins, see: Barrett & Graboski (1986). For the synthesis, see: Valdes et al. (2007).

Experimental top

The title compound was synthesized according to the method reported in the literature (Valdes et al., 2007). Yellow single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Structure description top

β-Nitroolefins are a class of useful and versatile building blocks in organic synthesis (Barrett & Graboski, 1986). The author reports here, the crystal structure of the title compound.

For general background to β-nitroolefins, see: Barrett & Graboski (1986). For the synthesis, see: Valdes et al. (2007).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound showing the atomic numbering. Displacement ellipsoids are drawn at the 50% probability level.

(E)-1-Nitro-4-(2-nitroethenyl)benzene top

Crystal data top

C₈H₆N₂O₄	F(000) = 800
M_r = 194.15	D_x = 1.588 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5000 reflections
a = 15.847 (4) Å	θ = 3.3–27.5°
b = 4.9991 (11) Å	µ = 0.13 mm⁻¹
c = 20.495 (5) Å	T = 93 K
V = 1623.6 (7) Å³	Prism, yellow
Z = 8	0.43 × 0.17 × 0.17 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1821 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
Detector resolution: 28.5714 pixels mm^-1	h = −20→20
multi–scan	k = −6→6
12157 measured reflections	l = −20→26
1921 independent 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0583P)² + 0.0124P] where P = (F_o² + 2F_c²)/3
1921 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₈H₆N₂O₄	V = 1623.6 (7) Å³
M_r = 194.15	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 15.847 (4) Å	µ = 0.13 mm⁻¹
b = 4.9991 (11) Å	T = 93 K
c = 20.495 (5) Å	0.43 × 0.17 × 0.17 mm

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	1821 reflections with I > 2σ(I)
12157 measured reflections	R_int = 0.032
1921 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.090	H-atom parameters constrained
S = 1.13	Δρ_max = 0.26 e Å⁻³
1921 reflections	Δρ_min = −0.17 e Å⁻³
253 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	0.00934 (11)	−0.2104 (4)	0.37970 (9)	0.0256 (4)
O2	0.03415 (11)	−0.1404 (4)	0.27702 (8)	0.0227 (4)
O3	0.40990 (11)	1.2126 (4)	0.30965 (8)	0.0231 (4)
O4	0.39197 (11)	1.1786 (3)	0.41409 (8)	0.0227 (4)
N1	0.04305 (12)	−0.0847 (4)	0.33513 (10)	0.0181 (4)
N2	0.37733 (12)	1.1093 (4)	0.35767 (10)	0.0172 (4)
C1	0.20144 (14)	0.4859 (5)	0.32540 (12)	0.0201 (5)
C2	0.24209 (16)	0.6078 (5)	0.27306 (12)	0.0212 (5)
H2	0.2299	0.5506	0.2299	0.025*
C3	0.29987 (15)	0.8108 (5)	0.28293 (12)	0.0194 (5)
H3	0.3273	0.8938	0.2470	0.023*
C4	0.31691 (14)	0.8909 (5)	0.34625 (11)	0.0170 (5)
C5	0.27766 (15)	0.7755 (5)	0.39972 (12)	0.0195 (5)
H5	0.2901	0.8348	0.4427	0.023*
C6	0.21957 (15)	0.5709 (5)	0.38928 (12)	0.0214 (5)
H6	0.1922	0.4887	0.4253	0.026*
C7	0.14131 (14)	0.2682 (5)	0.31123 (13)	0.0200 (5)
H7	0.1345	0.2178	0.2669	0.024*
C8	0.09642 (15)	0.1380 (5)	0.35480 (12)	0.0198 (5)
H8	0.0988	0.1896	0.3994	0.024*
O5	0.69565 (11)	0.3595 (4)	0.15876 (8)	0.0214 (4)
O6	0.72313 (10)	0.2899 (4)	0.05672 (9)	0.0234 (4)
O7	0.33698 (11)	1.6608 (4)	0.01863 (8)	0.0239 (4)
O8	0.31958 (11)	1.7112 (3)	0.12274 (9)	0.0222 (4)
N3	0.68809 (12)	0.4151 (4)	0.10092 (10)	0.0167 (4)
N4	0.35187 (12)	1.6000 (4)	0.07547 (10)	0.0167 (4)
C9	0.52828 (13)	0.9813 (5)	0.11027 (11)	0.0170 (5)
C10	0.51094 (15)	1.0658 (5)	0.04660 (12)	0.0203 (5)
H10	0.5396	0.9851	0.0110	0.024*
C11	0.45240 (14)	1.2658 (5)	0.03503 (12)	0.0204 (5)
H11	0.4398	1.3216	−0.0082	0.024*
C12	0.41275 (14)	1.3822 (5)	0.08803 (11)	0.0167 (5)
C13	0.42840 (15)	1.3075 (5)	0.15165 (12)	0.0184 (5)
H13	0.4004	1.3928	0.1870	0.022*
C14	0.48642 (15)	1.1037 (5)	0.16264 (12)	0.0173 (5)
H14	0.4978	1.0470	0.2060	0.021*
C15	0.58824 (14)	0.7649 (5)	0.12470 (12)	0.0175 (5)
H15	0.5946	0.7135	0.1691	0.021*
C16	0.63421 (15)	0.6356 (5)	0.08075 (11)	0.0191 (5)
H16	0.6320	0.6871	0.0362	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (9)	0.0291 (9)	0.0220 (9)	−0.0036 (8)	0.0025 (7)	0.0041 (8)
O2	0.0238 (9)	0.0263 (10)	0.0180 (9)	0.0004 (7)	0.0000 (7)	−0.0033 (8)
O3	0.0225 (8)	0.0260 (9)	0.0209 (8)	−0.0040 (8)	0.0013 (7)	0.0046 (7)
O4	0.0261 (10)	0.0234 (9)	0.0186 (8)	−0.0004 (7)	−0.0041 (7)	−0.0025 (7)
N1	0.0155 (10)	0.0182 (10)	0.0204 (10)	−0.0008 (8)	−0.0018 (8)	0.0016 (8)
N2	0.0149 (9)	0.0170 (9)	0.0198 (9)	0.0004 (8)	−0.0016 (8)	0.0031 (8)
C1	0.0159 (11)	0.0164 (11)	0.0279 (14)	0.0038 (10)	−0.0002 (9)	0.0024 (10)
C2	0.0216 (12)	0.0197 (11)	0.0224 (12)	0.0023 (10)	−0.0031 (10)	−0.0033 (9)
C3	0.0171 (11)	0.0220 (12)	0.0191 (12)	0.0024 (9)	−0.0008 (9)	0.0019 (10)
C4	0.0131 (10)	0.0152 (10)	0.0228 (12)	0.0038 (9)	0.0001 (9)	0.0005 (10)
C5	0.0210 (11)	0.0217 (13)	0.0159 (12)	0.0028 (11)	−0.0022 (9)	0.0007 (9)
C6	0.0210 (11)	0.0216 (12)	0.0217 (12)	0.0017 (10)	0.0021 (10)	0.0060 (10)
C7	0.0199 (11)	0.0186 (12)	0.0215 (11)	0.0032 (11)	−0.0011 (10)	−0.0011 (10)
C8	0.0199 (12)	0.0184 (11)	0.0210 (11)	−0.0013 (9)	−0.0021 (9)	−0.0019 (9)
O5	0.0235 (9)	0.0239 (9)	0.0167 (8)	0.0021 (7)	−0.0017 (7)	0.0045 (7)
O6	0.0237 (9)	0.0237 (9)	0.0230 (9)	0.0051 (7)	−0.0005 (7)	−0.0066 (8)
O7	0.0249 (9)	0.0249 (10)	0.0218 (9)	0.0030 (7)	−0.0035 (7)	0.0067 (8)
O8	0.0210 (8)	0.0215 (8)	0.0241 (9)	0.0057 (7)	0.0001 (7)	−0.0039 (7)
N3	0.0147 (9)	0.0161 (9)	0.0193 (10)	−0.0008 (8)	−0.0003 (8)	0.0003 (8)
N4	0.0156 (9)	0.0149 (9)	0.0194 (10)	−0.0017 (8)	−0.0019 (7)	0.0014 (8)
C9	0.0149 (10)	0.0178 (11)	0.0184 (12)	−0.0025 (9)	0.0007 (9)	−0.0020 (9)
C10	0.0216 (12)	0.0212 (12)	0.0182 (11)	0.0032 (10)	0.0029 (9)	−0.0007 (10)
C11	0.0213 (11)	0.0220 (12)	0.0179 (12)	0.0006 (11)	−0.0023 (9)	0.0002 (9)
C12	0.0135 (10)	0.0143 (10)	0.0222 (12)	0.0017 (9)	−0.0020 (9)	0.0011 (9)
C13	0.0180 (12)	0.0195 (10)	0.0176 (11)	−0.0009 (9)	0.0032 (9)	−0.0006 (10)
C14	0.0168 (11)	0.0206 (11)	0.0146 (11)	−0.0001 (10)	0.0005 (9)	0.0000 (9)
C15	0.0157 (10)	0.0195 (12)	0.0172 (11)	−0.0007 (10)	−0.0014 (9)	0.0005 (9)
C16	0.0181 (11)	0.0210 (12)	0.0182 (11)	0.0009 (9)	−0.0015 (9)	0.0008 (9)

Geometric parameters (Å, º) top

O1—N1	1.231 (3)	O5—N3	1.223 (3)
O2—N1	1.231 (3)	O6—N3	1.233 (3)
O3—N2	1.225 (3)	O7—N4	1.227 (3)
O4—N2	1.229 (3)	O8—N4	1.229 (3)
N1—C8	1.455 (3)	N3—C16	1.455 (3)
N2—C4	1.471 (3)	N4—C12	1.477 (3)
C1—C2	1.392 (3)	C9—C10	1.399 (3)
C1—C6	1.406 (3)	C9—C14	1.402 (3)
C1—C7	1.476 (3)	C9—C15	1.470 (3)
C2—C3	1.382 (3)	C10—C11	1.385 (3)
C2—H2	0.95	C10—H10	0.95
C3—C4	1.385 (3)	C11—C12	1.383 (3)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.386 (3)	C12—C13	1.379 (3)
C5—C6	1.392 (4)	C13—C14	1.391 (3)
C5—H5	0.95	C13—H13	0.95
C6—H6	0.95	C14—H14	0.95
C7—C8	1.314 (4)	C15—C16	1.327 (3)
C7—H7	0.95	C15—H15	0.95
C8—H8	0.95	C16—H16	0.95

O2—N1—O1	123.6 (2)	O5—N3—O6	123.5 (2)
O2—N1—C8	120.5 (2)	O5—N3—C16	120.3 (2)
O1—N1—C8	115.9 (2)	O6—N3—C16	116.11 (19)
O3—N2—O4	123.9 (2)	O7—N4—O8	123.8 (2)
O3—N2—C4	117.33 (19)	O7—N4—C12	118.28 (19)
O4—N2—C4	118.79 (19)	O8—N4—C12	117.89 (19)
C2—C1—C6	119.4 (2)	C10—C9—C14	119.3 (2)
C2—C1—C7	118.0 (2)	C10—C9—C15	122.5 (2)
C6—C1—C7	122.6 (2)	C14—C9—C15	118.2 (2)
C3—C2—C1	121.0 (2)	C11—C10—C9	120.6 (2)
C3—C2—H2	119.5	C11—C10—H10	119.7
C1—C2—H2	119.5	C9—C10—H10	119.7
C2—C3—C4	118.6 (2)	C12—C11—C10	118.3 (2)
C2—C3—H3	120.7	C12—C11—H11	120.9
C4—C3—H3	120.7	C10—C11—H11	120.9
C3—C4—C5	122.2 (2)	C13—C12—C11	123.2 (2)
C3—C4—N2	119.4 (2)	C13—C12—N4	118.8 (2)
C5—C4—N2	118.4 (2)	C11—C12—N4	118.0 (2)
C4—C5—C6	118.7 (2)	C12—C13—C14	118.1 (2)
C4—C5—H5	120.6	C12—C13—H13	121.0
C6—C5—H5	120.6	C14—C13—H13	121.0
C5—C6—C1	120.0 (2)	C13—C14—C9	120.6 (2)
C5—C6—H6	120.0	C13—C14—H14	119.7
C1—C6—H6	120.0	C9—C14—H14	119.7
C8—C7—C1	125.5 (2)	C16—C15—C9	125.2 (2)
C8—C7—H7	117.2	C16—C15—H15	117.4
C1—C7—H7	117.2	C9—C15—H15	117.4
C7—C8—N1	120.3 (2)	C15—C16—N3	119.9 (2)
C7—C8—H8	119.8	C15—C16—H16	120.0
N1—C8—H8	119.8	N3—C16—H16	120.0

C6—C1—C2—C3	0.0 (4)	C14—C9—C10—C11	−0.8 (4)
C7—C1—C2—C3	−179.2 (2)	C15—C9—C10—C11	178.3 (2)
C1—C2—C3—C4	0.2 (4)	C9—C10—C11—C12	1.0 (4)
C2—C3—C4—C5	−0.4 (4)	C10—C11—C12—C13	−0.4 (4)
C2—C3—C4—N2	−179.1 (2)	C10—C11—C12—N4	178.6 (2)
O3—N2—C4—C3	0.4 (3)	O7—N4—C12—C13	−178.4 (2)
O4—N2—C4—C3	−180.0 (2)	O8—N4—C12—C13	2.2 (3)
O3—N2—C4—C5	−178.4 (2)	O7—N4—C12—C11	2.6 (3)
O4—N2—C4—C5	1.2 (3)	O8—N4—C12—C11	−176.8 (2)
C3—C4—C5—C6	0.4 (4)	C11—C12—C13—C14	−0.5 (4)
N2—C4—C5—C6	179.2 (2)	N4—C12—C13—C14	−179.5 (2)
C4—C5—C6—C1	−0.3 (4)	C12—C13—C14—C9	0.8 (3)
C2—C1—C6—C5	0.1 (4)	C10—C9—C14—C13	−0.2 (3)
C7—C1—C6—C5	179.3 (2)	C15—C9—C14—C13	−179.3 (2)
C2—C1—C7—C8	−178.2 (2)	C10—C9—C15—C16	2.9 (4)
C6—C1—C7—C8	2.6 (4)	C14—C9—C15—C16	−178.0 (2)
C1—C7—C8—N1	−176.1 (2)	C9—C15—C16—N3	−176.7 (2)
O2—N1—C8—C7	−5.7 (3)	O5—N3—C16—C15	−4.9 (3)
O1—N1—C8—C7	173.6 (2)	O6—N3—C16—C15	173.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.95	2.57	3.389 (3)	144
C5—H5···O6ⁱⁱ	0.95	2.43	3.234 (3)	143
C6—H6···O7ⁱⁱⁱ	0.95	2.56	3.469 (3)	160
C7—H7···O5ⁱ	0.95	2.45	3.304 (3)	150
C10—H10···O4^iv	0.95	2.41	3.352 (3)	174
C11—H11···O1^v	0.95	2.44	3.243 (3)	142
C14—H14···O2^vi	0.95	2.57	3.381 (3)	144
C15—H15···O2^vi	0.95	2.44	3.296 (3)	150

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

Experimental details

Crystal data
Chemical formula	C₈H₆N₂O₄
M_r	194.15
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	93
a, b, c (Å)	15.847 (4), 4.9991 (11), 20.495 (5)
V (Å³)	1623.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.43 × 0.17 × 0.17

Data collection
Diffractometer	Rigaku AFC10/Saturn724+
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12157, 1921, 1821
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.090, 1.13
No. of reflections	1921
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5ⁱ	0.95	2.57	3.389 (3)	144
C5—H5···O6ⁱⁱ	0.95	2.43	3.234 (3)	143
C6—H6···O7ⁱⁱⁱ	0.95	2.56	3.469 (3)	160
C7—H7···O5ⁱ	0.95	2.45	3.304 (3)	150
C10—H10···O4^iv	0.95	2.41	3.352 (3)	174
C11—H11···O1^v	0.95	2.44	3.243 (3)	142
C14—H14···O2^vi	0.95	2.57	3.381 (3)	144
C15—H15···O2^vi	0.95	2.44	3.296 (3)	150

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

Acknowledgements

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Barrett, A. G. M. & Graboski, G. G. (1986). Chem. Rev. 86, 751–762. CrossRef CAS Web of Science Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Valdes, A. C., Pina-Luis, G. & Rivero, I. A. (2007). J. Mex. Chem. Soc. 51, 87–95. CAS Google Scholar