3,3′-(p-Phenyl­enedimethyl­ene)di-1H-imidazol-1-ium bis­(4-nitro­benzoate)–4-nitro­benzoic acid (1/2)

Dong, G.-Y.; Liu, X.-H.; Liu, T.-F.; Khan, I.U.

doi:10.1107/S160053681001929X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1485

https://doi.org/10.1107/S160053681001929X

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3,3′-(p-Phenylenedimethylene)di-1H-imidazol-1-ium bis(4-nitrobenzoate)–4-nitrobenzoic acid (1/2)

Gui-Ying Dong,^a ‡ Xin-Hua Liu,^b Tong-Fei Liu ^a and Islam Ullah Khan ^c ^*

^aCollege of Chemical Engineering and Biotechnology, Hebei Polytechnic University, Tangshan 063009, People's Republic of China, ^bCollege of Light Industry, Hebei Polytechnic University, Tangshan 063009, People's Republic of China, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: iukhangcu@126.com

(Received 4 May 2010; accepted 23 May 2010; online 29 May 2010)

The asymmetric unit of the title compound, C₁₄H₁₆N₄²⁺·2C₇H₄NO₄⁻·2C₇H₅NO₄, comprises one-half of the 3,3′-(p-phenylenedimethylene)di-1H-imidazol-1-ium dication, which lies on an inversion centre, one 4-nitrobenzoate anion and one 4-nitrobenzoic acid molecule. In the crystal, the components are linked into a two-dimensional network parallel to (110) by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the synthesis of 1,4-bis(imidazol-1-ylmethyl)benzene, see: Hoskins et al. (1997 ). For a related structure, see: Chen et al. (2010 ).

Experimental

Crystal data

C₁₄H₁₆N₄²⁺·2C₇H₄NO⁴⁻·2C₇H₅NO₄
M_r = 906.77
Triclinic, $[P \overline 1]$
a = 7.2659 (15) Å
b = 12.689 (3) Å
c = 13.028 (3) Å
α = 112.94 (3)°
β = 102.49 (3)°
γ = 101.94 (3)°
V = 1021.8 (6) Å³
Z = 1
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.968, T_max = 0.971
8835 measured reflections
3590 independent reflections
2019 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.081
wR(F²) = 0.191
S = 1.19
3590 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H2A⋯O3ⁱ	0.85	2.57	3.167 (5)	128
O7—H2A⋯O4ⁱ	0.85	1.65	2.494 (5)	173
N4—H4A⋯O8	0.86	2.03	2.690 (5)	133
C15—H15⋯O3	0.93	2.23	3.073 (7)	150
C17—H17⋯O5ⁱⁱ	0.93	2.46	3.228 (7)	140
C21—H21⋯O3ⁱⁱⁱ	0.93	2.46	3.321 (6)	154
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y-1, z-1; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); 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 I, global. DOI: https://doi.org/10.1107/S160053681001929X/ci5093sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001929X/ci5093Isup2.hkl

checkCIF report

Comment top

Over the past few years, efforts have been focused on the investigation of coordination polymers with flexible ligands. Di-imidazole flexbile ligands such as 1,4-bis(1H-imidazol-1-yl)methylbenzene (bix) find numerous applications in constructing metal-organic coordination polymers as they can rotate freely about methylene carbon atoms to adjust to the coordination environment. We report here the crystal structure of the title compound.

The asymmetric unit comprises one-half of a bix²⁺ dication lying on an inversion centre, one 4-nitrobenzoate anion and one neutral 4-nitrobenzoic acid molecule (Fig. 1). Bond distances and angles are normal (Chen et al., 2010).

In the crystal structure, the dications, anions and neutral 4-nitrobenzoic acid molecule are interlinked by O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1), forming a two-dimensional hydrogen-bonded network parallel to the (110).

Related literature top

For the synthesis of 1,4-bis(imidazol-1-ylmethyl)benzene, see: Hoskins et al. (1997). For a related structure, see: Chen et al. (2010).

Experimental top

1,4-Bis(imidazol-1-ylmethyl)benzene (bix) was prepared according to a literature method (Hoskins et al., 1997). 1:4 molar amounts of bix (23.8 mg, 0.1 mmol) and 4-nitrobenzoic acid (66.9 mg , 0.4 mmol) were dissolved in 95% ethanol (30 ml). The mixture was stirred and refluxed for 1 h and then filtered. The resulting colourless solution was allowed to stand in air for two weeks. Colourless crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of the solution.

Structure description top

For the synthesis of 1,4-bis(imidazol-1-ylmethyl)benzene, see: Hoskins et al. (1997). For a related structure, see: Chen et al. (2010).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 asymmetric unit of the title compound, showing the atomic numbering and 30% probability displacement ellipsoids. Atoms labelled with the suffix A are generated by the symmetry operation (-x, 1-y, -z).

3,3'-(p-Phenylenedimethylene)di-1H-imidazol-1-ium bis(4-nitrobenzoate)–4-nitrobenzoic acid (1/2) top

Crystal data top

C₁₄H₁₆N₄²⁺·2C₇H₄NO⁴⁻·2C₇H₅NO₄	Z = 1
M_r = 906.77	F(000) = 470
Triclinic, P1	D_x = 1.474 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2659 (15) Å	Cell parameters from 3889 reflections
b = 12.689 (3) Å	θ = 4.6–22.7°
c = 13.028 (3) Å	µ = 0.12 mm⁻¹
α = 112.94 (3)°	T = 295 K
β = 102.49 (3)°	Prism, colourless
γ = 101.94 (3)°	0.20 × 0.20 × 0.20 mm
V = 1021.8 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3590 independent reflections
Radiation source: fine–focus sealed tube	2019 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
φ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.968, T_max = 0.971	k = −15→15
8835 measured reflections	l = −15→15

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0648P)² + 0.2399P] where P = (F_o² + 2F_c²)/3
3590 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₁₆N₄²⁺·2C₇H₄NO⁴⁻·2C₇H₅NO₄	γ = 101.94 (3)°
M_r = 906.77	V = 1021.8 (6) Å³
Triclinic, P1	Z = 1
a = 7.2659 (15) Å	Mo Kα radiation
b = 12.689 (3) Å	µ = 0.12 mm⁻¹
c = 13.028 (3) Å	T = 295 K
α = 112.94 (3)°	0.20 × 0.20 × 0.20 mm
β = 102.49 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3590 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2019 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.971	R_int = 0.066
8835 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.19	Δρ_max = 0.42 e Å⁻³
3590 reflections	Δρ_min = −0.24 e Å⁻³
298 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
O7	0.1748 (5)	0.3773 (3)	0.6201 (3)	0.0628 (9)
O8	0.2413 (5)	0.4626 (3)	0.5069 (3)	0.0636 (9)
N4	0.2722 (5)	0.3310 (3)	0.2960 (3)	0.0468 (9)
H4A	0.2596	0.3328	0.3607	0.056*
N3	0.3203 (4)	0.3884 (3)	0.1672 (3)	0.0341 (8)
C11	0.2099 (5)	0.5846 (3)	0.6892 (3)	0.0346 (10)
C12	0.1960 (6)	0.5971 (4)	0.7973 (3)	0.0378 (10)
H12	0.1787	0.5305	0.8124	0.045*
C20	0.0546 (6)	0.4031 (4)	−0.0614 (3)	0.0417 (11)
H20	0.0910	0.3371	−0.1031	0.050*
C10	0.2349 (6)	0.6835 (4)	0.6673 (4)	0.0454 (11)
H10	0.2447	0.6753	0.5947	0.054*
C21	−0.1173 (6)	0.4176 (4)	−0.1146 (4)	0.0417 (11)
H21	−0.1952	0.3621	−0.1918	0.050*
C13	0.2074 (6)	0.7074 (4)	0.8830 (4)	0.0426 (11)
H13	0.1981	0.7160	0.9558	0.051*
C17	0.2842 (6)	0.2657 (4)	0.1182 (4)	0.0397 (10)
H17	0.2808	0.2161	0.0427	0.048*
C8	0.2328 (6)	0.8040 (4)	0.8581 (4)	0.0423 (11)
C14	0.2070 (6)	0.4663 (4)	0.5962 (4)	0.0417 (11)
C19	0.1743 (6)	0.4850 (4)	0.0531 (3)	0.0359 (10)
C9	0.2457 (6)	0.7939 (4)	0.7505 (4)	0.0510 (12)
H9	0.2612	0.8603	0.7351	0.061*
N2	0.2409 (6)	0.9230 (4)	0.9474 (4)	0.0642 (12)
C15	0.3111 (6)	0.4252 (4)	0.2754 (4)	0.0405 (10)
H15	0.3291	0.5044	0.3279	0.049*
O6	0.2194 (6)	0.9302 (3)	1.0400 (3)	0.0946 (14)
C16	0.2548 (6)	0.2308 (4)	0.1995 (4)	0.0445 (11)
H16	0.2277	0.1525	0.1913	0.053*
O5	0.2639 (7)	1.0065 (3)	0.9231 (4)	0.1088 (16)
C18	0.3622 (6)	0.4672 (4)	0.1113 (4)	0.0472 (11)
H18A	0.4226	0.4318	0.0525	0.057*
H18B	0.4567	0.5452	0.1706	0.057*
C4	0.4933 (6)	0.8837 (3)	0.5529 (3)	0.0360 (10)
O3	0.4409 (5)	0.7026 (3)	0.3853 (3)	0.0731 (11)
O2	0.4178 (6)	1.2399 (3)	0.8522 (3)	0.0791 (11)
O4	0.7429 (5)	0.7925 (3)	0.5183 (3)	0.0700 (10)
C1	0.3648 (7)	1.0618 (4)	0.6869 (4)	0.0423 (11)
N1	0.2961 (7)	1.1562 (4)	0.7606 (4)	0.0616 (11)
C5	0.6275 (6)	0.9830 (3)	0.6549 (3)	0.0417 (11)
H5	0.7610	0.9887	0.6779	0.050*
C3	0.2940 (6)	0.8758 (4)	0.5190 (3)	0.0432 (11)
H3	0.2041	0.8099	0.4503	0.052*
C2	0.2281 (7)	0.9650 (4)	0.5863 (4)	0.0473 (11)
H2	0.0947	0.9596	0.5642	0.057*
C6	0.5638 (7)	1.0733 (4)	0.7224 (4)	0.0451 (11)
H6	0.6533	1.1403	0.7903	0.054*
C7	0.5608 (8)	0.7845 (4)	0.4785 (4)	0.0470 (11)
O1	0.1202 (7)	1.1467 (4)	0.7276 (4)	0.1083 (15)
H2A	0.2107	0.3206	0.5773	0.162*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O7	0.086 (3)	0.0432 (19)	0.072 (2)	0.0297 (18)	0.0469 (19)	0.0238 (18)
O8	0.086 (3)	0.065 (2)	0.0381 (19)	0.0274 (19)	0.0290 (18)	0.0162 (17)
N4	0.048 (2)	0.062 (3)	0.035 (2)	0.0202 (19)	0.0143 (17)	0.025 (2)
N3	0.035 (2)	0.038 (2)	0.032 (2)	0.0177 (16)	0.0105 (15)	0.0157 (17)
C11	0.028 (2)	0.039 (2)	0.032 (2)	0.0081 (18)	0.0080 (18)	0.013 (2)
C12	0.039 (3)	0.042 (3)	0.041 (3)	0.016 (2)	0.019 (2)	0.023 (2)
C20	0.049 (3)	0.041 (3)	0.043 (3)	0.023 (2)	0.018 (2)	0.021 (2)
C10	0.058 (3)	0.047 (3)	0.034 (3)	0.017 (2)	0.017 (2)	0.019 (2)
C21	0.049 (3)	0.038 (3)	0.032 (2)	0.013 (2)	0.008 (2)	0.013 (2)
C13	0.041 (3)	0.053 (3)	0.034 (2)	0.017 (2)	0.016 (2)	0.016 (2)
C17	0.045 (3)	0.034 (2)	0.037 (3)	0.020 (2)	0.012 (2)	0.011 (2)
C8	0.038 (3)	0.036 (2)	0.041 (3)	0.013 (2)	0.009 (2)	0.007 (2)
C14	0.029 (2)	0.045 (3)	0.042 (3)	0.009 (2)	0.008 (2)	0.013 (2)
C19	0.036 (3)	0.040 (2)	0.037 (3)	0.008 (2)	0.011 (2)	0.025 (2)
C9	0.064 (3)	0.043 (3)	0.053 (3)	0.019 (2)	0.020 (2)	0.026 (3)
N2	0.065 (3)	0.050 (3)	0.059 (3)	0.022 (2)	0.013 (2)	0.008 (3)
C15	0.033 (3)	0.040 (3)	0.035 (3)	0.015 (2)	0.0044 (19)	0.006 (2)
O6	0.138 (4)	0.083 (3)	0.046 (2)	0.055 (3)	0.026 (2)	0.006 (2)
C16	0.046 (3)	0.034 (3)	0.050 (3)	0.014 (2)	0.010 (2)	0.018 (2)
O5	0.177 (5)	0.046 (2)	0.115 (4)	0.046 (3)	0.072 (3)	0.029 (2)
C18	0.041 (3)	0.054 (3)	0.053 (3)	0.015 (2)	0.014 (2)	0.032 (2)
C4	0.053 (3)	0.025 (2)	0.032 (2)	0.012 (2)	0.015 (2)	0.0134 (19)
O3	0.082 (3)	0.047 (2)	0.051 (2)	0.0251 (18)	−0.0019 (19)	−0.0063 (17)
O2	0.091 (3)	0.054 (2)	0.066 (2)	0.023 (2)	0.032 (2)	−0.001 (2)
O4	0.057 (2)	0.047 (2)	0.076 (2)	0.0193 (17)	0.0156 (19)	0.0005 (18)
C1	0.056 (3)	0.036 (2)	0.046 (3)	0.021 (2)	0.025 (2)	0.021 (2)
N1	0.067 (3)	0.049 (3)	0.065 (3)	0.023 (2)	0.035 (3)	0.015 (2)
C5	0.044 (3)	0.033 (2)	0.042 (3)	0.010 (2)	0.010 (2)	0.014 (2)
C3	0.050 (3)	0.036 (3)	0.033 (2)	0.009 (2)	0.004 (2)	0.013 (2)
C2	0.047 (3)	0.044 (3)	0.043 (3)	0.013 (2)	0.011 (2)	0.016 (2)
C6	0.059 (3)	0.033 (2)	0.034 (2)	0.012 (2)	0.014 (2)	0.009 (2)
C7	0.066 (4)	0.028 (2)	0.042 (3)	0.012 (2)	0.015 (3)	0.014 (2)
O1	0.072 (3)	0.086 (3)	0.129 (4)	0.040 (2)	0.037 (3)	0.003 (3)

Geometric parameters (Å, º) top

O7—C14	1.274 (5)	C8—N2	1.484 (5)
O7—H2A	0.85	C19—C21ⁱ	1.387 (5)
O8—C14	1.227 (5)	C19—C18	1.519 (5)
N4—C15	1.313 (5)	C9—H9	0.93
N4—C16	1.354 (5)	N2—O5	1.210 (5)
N4—H4A	0.86	N2—O6	1.220 (5)
N3—C15	1.324 (5)	C15—H15	0.93
N3—C17	1.373 (5)	C16—H16	0.93
N3—C18	1.469 (5)	C18—H18A	0.97
C11—C10	1.378 (5)	C18—H18B	0.97
C11—C12	1.383 (5)	C4—C5	1.389 (5)
C11—C14	1.510 (5)	C4—C3	1.389 (5)
C12—C13	1.380 (5)	C4—C7	1.509 (6)
C12—H12	0.93	O3—C7	1.224 (5)
C20—C21	1.376 (5)	O2—N1	1.225 (5)
C20—C19	1.385 (5)	O4—C7	1.279 (5)
C20—H20	0.93	C1—C2	1.374 (6)
C10—C9	1.370 (6)	C1—C6	1.377 (6)
C10—H10	0.93	C1—N1	1.472 (5)
C21—C19ⁱ	1.387 (5)	N1—O1	1.221 (5)
C21—H21	0.93	C5—C6	1.382 (5)
C13—C8	1.373 (5)	C5—H5	0.93
C13—H13	0.93	C3—C2	1.382 (5)
C17—C16	1.336 (5)	C3—H3	0.93
C17—H17	0.93	C2—H2	0.93
C8—C9	1.382 (6)	C6—H6	0.93

C14—O7—H2A	111.6	O5—N2—O6	123.9 (4)
C15—N4—C16	109.4 (3)	O5—N2—C8	118.0 (5)
C15—N4—H4A	125.3	O6—N2—C8	118.1 (5)
C16—N4—H4A	125.3	N4—C15—N3	108.4 (4)
C15—N3—C17	108.0 (3)	N4—C15—H15	125.8
C15—N3—C18	125.0 (3)	N3—C15—H15	125.8
C17—N3—C18	127.0 (3)	C17—C16—N4	107.0 (4)
C10—C11—C12	119.4 (4)	C17—C16—H16	126.5
C10—C11—C14	119.0 (4)	N4—C16—H16	126.5
C12—C11—C14	121.6 (4)	N3—C18—C19	111.7 (3)
C13—C12—C11	120.7 (4)	N3—C18—H18A	109.3
C13—C12—H12	119.7	C19—C18—H18A	109.3
C11—C12—H12	119.7	N3—C18—H18B	109.3
C21—C20—C19	121.1 (4)	C19—C18—H18B	109.3
C21—C20—H20	119.4	H18A—C18—H18B	107.9
C19—C20—H20	119.4	C5—C4—C3	119.5 (4)
C9—C10—C11	121.2 (4)	C5—C4—C7	121.0 (4)
C9—C10—H10	119.4	C3—C4—C7	119.6 (4)
C11—C10—H10	119.4	C2—C1—C6	122.6 (4)
C20—C21—C19ⁱ	120.0 (4)	C2—C1—N1	118.9 (4)
C20—C21—H21	120.0	C6—C1—N1	118.5 (4)
C19ⁱ—C21—H21	120.0	O1—N1—O2	123.3 (4)
C8—C13—C12	118.3 (4)	O1—N1—C1	118.3 (4)
C8—C13—H13	120.8	O2—N1—C1	118.4 (5)
C12—C13—H13	120.8	C6—C5—C4	120.4 (4)
C16—C17—N3	107.1 (4)	C6—C5—H5	119.8
C16—C17—H17	126.4	C4—C5—H5	119.8
N3—C17—H17	126.4	C2—C3—C4	120.7 (4)
C13—C8—C9	122.2 (4)	C2—C3—H3	119.7
C13—C8—N2	119.5 (4)	C4—C3—H3	119.7
C9—C8—N2	118.2 (4)	C1—C2—C3	118.4 (4)
O8—C14—O7	124.9 (4)	C1—C2—H2	120.8
O8—C14—C11	119.4 (4)	C3—C2—H2	120.8
O7—C14—C11	115.7 (4)	C1—C6—C5	118.5 (4)
C20—C19—C21ⁱ	118.8 (4)	C1—C6—H6	120.7
C20—C19—C18	120.6 (4)	C5—C6—H6	120.7
C21ⁱ—C19—C18	120.5 (4)	O3—C7—O4	124.3 (4)
C10—C9—C8	118.2 (4)	O3—C7—C4	119.0 (5)
C10—C9—H9	120.9	O4—C7—C4	116.7 (4)
C8—C9—H9	120.9

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
O7—H2A···O3ⁱⁱ	0.85	2.57	3.167 (5)	128
O7—H2A···O4ⁱⁱ	0.85	1.65	2.494 (5)	173
N4—H4A···O8	0.86	2.03	2.690 (5)	133
C15—H15···O3	0.93	2.23	3.073 (7)	150
C17—H17···O5ⁱⁱⁱ	0.93	2.46	3.228 (7)	140
C21—H21···O3ⁱ	0.93	2.46	3.321 (6)	154

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₄²⁺·2C₇H₄NO⁴⁻·2C₇H₅NO₄
M_r	906.77
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.2659 (15), 12.689 (3), 13.028 (3)
α, β, γ (°)	112.94 (3), 102.49 (3), 101.94 (3)
V (Å³)	1021.8 (6)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	8835, 3590, 2019
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.191, 1.19
No. of reflections	3590
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.24

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H2A···O3ⁱ	0.85	2.57	3.167 (5)	128
O7—H2A···O4ⁱ	0.85	1.65	2.494 (5)	173
N4—H4A···O8	0.86	2.03	2.690 (5)	133
C15—H15···O3	0.93	2.23	3.073 (7)	150
C17—H17···O5ⁱⁱ	0.93	2.46	3.228 (7)	140
C21—H21···O3ⁱⁱⁱ	0.93	2.46	3.321 (6)	154

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

Footnotes

‡Additional corresponding author, e-mail: tsdgying@126.com.

Acknowledgements

The authors thank Hebei Polytechnic University and Government College University for support of this work.

References

Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison,Wisconsin, USA. Google Scholar
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Hoskins, B. F., Robson, R. & Slizys, D. A. (1997). J. Am. Chem. Soc. 119, 2952–2953. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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