4,4′-(1,1,1,3,3,3-Hexafluoro­propane-2,2-diyl)dibenzoic acid

Tang, L.; Wu, Y.-P.; Fu, F.; Zhang, Z.-L.; Zheng, D.

doi:10.1107/S1600536810017745

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1390

https://doi.org/10.1107/S1600536810017745

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4,4′-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)dibenzoic acid

Long Tang,^a Ya-Pan Wu,^a Feng Fu,^a ^* Zhu-Lian Zhang ^a and Dan Zheng ^a

^aDepartment of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Shaanxi 716000, People's Republic of China
^*Correspondence e-mail: yadxgncl@126.com

(Received 19 March 2010; accepted 14 May 2010; online 19 May 2010)

In the title compound, C₁₇H₁₀F₆O₄, the two benzene rings are twisted with respect to each other, making a dihedral angle of 67.43 (12)°. In the crystal, adjacent molecules are linked by O—H⋯O and C—H⋯F hydrogen bonding, forming a wave-like layered supramolecular structure.

Related literature

For the use of bibenzoic acids as bridging ligands for the synthesis of novel solid-state architectures, see: Zou et al. (2007 ). For the structures of related dibenzoic acid compounds, see: Potts et al. (2007 ); Lian et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₀F₆O₄
M_r = 392.25
Monoclinic, P 2₁ /c
a = 7.7523 (16) Å
b = 13.381 (3) Å
c = 16.134 (3) Å
β = 102.294 (4)°
V = 1635.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.35 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.972
8113 measured reflections
2904 independent reflections
1339 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.071
S = 1.00
2904 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O4ⁱ	0.82	1.85	2.661 (2)	169
O3—H3A⋯O1ⁱⁱ	0.82	1.80	2.603 (2)	165
C15—H15⋯F1ⁱⁱⁱ	0.93	2.48	3.382 (3)	163
Symmetry codes: (i) $[x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810017745/xu2737sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017745/xu2737Isup2.hkl

checkCIF report

Comment top

The rational design and synthesis of novel solid-state architectures are of current interest in the field of supramolecular chemistry and crystal engineering, due to intriguing structural motifs that can be created by various intermolecular interactions. Supramolecular chemistry uses molecular recognition processes that rely heavily on the understanding of the recognition properties of the functional groups involved in these interactions (Zou et al., 2007). Herein, we reported the organic crystal structure of C₁₇H₁₀F₆O₄, which is similar to that of the reported compounds (Potts et al. 2007; Lian et al.., 2007).

The molecular structure is shown in Fig. 1. The dihedral angle between the two benzene rings of the flexible H₂hfipbb molecule is 67.43 (12)°. Strong intermolecular O—H···O and C—H···F hydrogen bonds (Table 1) link the molecules into the 2D wave-like layer structure (Fig. 2).

Related literature top

For the use of bibenzoic acids as bridging ligands for the synthesis of novel solid-state architectures, see: Zou et al. (2007). For related dibenzoic acid compounds, see: Potts et al. (2007); Lian et al. (2007).

Experimental top

The title compound was prepared by hydrothermal method. A mixture of Zn(Ac)₂.4H₂O (0.20 mmol), 2,2'-bipyridine (bipy 0.20 mmol), 4,4'-(hexafluoroisopropylidene)bis(benzoic acid) (H₂hfipbb 0.20 mmol) and water (10 ml) was stirred for 20 min. The mixture was then transferred to a 23 ml Teflon-lined autoclave and kept at 433 K for 72 h under autogenous pressure. Then the mixture was cooled to room temperature slowly, the targeted Zn complex was not obtained. Colorless single crystals of the title compound suitable for X-ray analysis were obtained from the reaction mixture.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure and labeling of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. 2D wave-like layer of (I). Dashed lines denote hydrogen bonds.

4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)dibenzoic acid top

Crystal data top

C₁₇H₁₀F₆O₄	F(000) = 792
M_r = 392.25	D_x = 1.593 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 775 reflections
a = 7.7523 (16) Å	θ = 2.7–18.7°
b = 13.381 (3) Å	µ = 0.16 mm⁻¹
c = 16.134 (3) Å	T = 293 K
β = 102.294 (4)°	Prism, colorless
V = 1635.2 (6) Å³	0.35 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	1339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.963, T_max = 0.972	k = −15→15
8113 measured reflections	l = −13→19

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) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0135P)² + 0.190P] where P = (F_o² + 2F_c²)/3
2904 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₁₀F₆O₄	V = 1635.2 (6) Å³
M_r = 392.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7523 (16) Å	µ = 0.16 mm⁻¹
b = 13.381 (3) Å	T = 293 K
c = 16.134 (3) Å	0.35 × 0.20 × 0.18 mm
β = 102.294 (4)°

Data collection top

Bruker SMART CCD diffractometer	2904 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1339 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.972	R_int = 0.053
8113 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
2904 reflections	Δρ_min = −0.19 e Å⁻³
246 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 > 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
C1	−0.2346 (4)	0.0955 (2)	0.4514 (2)	0.0540 (8)
C2	−0.1474 (3)	0.04538 (17)	0.38975 (18)	0.0467 (7)
C3	0.0256 (3)	0.06770 (16)	0.38831 (17)	0.0482 (7)
H3	0.0908	0.1094	0.4295	0.058*
C4	0.1019 (3)	0.02807 (17)	0.32574 (17)	0.0491 (7)
H4	0.2188	0.0435	0.3254	0.059*
C5	0.0090 (3)	−0.03396 (17)	0.26363 (17)	0.0438 (7)
C6	−0.1618 (3)	−0.05959 (18)	0.26780 (19)	0.0599 (8)
H6	−0.2251	−0.1042	0.2286	0.072*
C7	−0.2381 (3)	−0.01936 (19)	0.32963 (19)	0.0612 (8)
H7	−0.3539	−0.0363	0.3309	0.073*
C8	0.1010 (3)	−0.07485 (17)	0.19469 (18)	0.0430 (7)
C9	0.2103 (4)	−0.1652 (2)	0.2347 (2)	0.0584 (8)
C10	−0.0290 (4)	−0.1105 (2)	0.1152 (2)	0.0586 (8)
C11	0.2132 (3)	0.00552 (17)	0.16376 (15)	0.0412 (7)
C12	0.1452 (3)	0.10175 (17)	0.14883 (16)	0.0489 (7)
H12	0.0372	0.1171	0.1621	0.059*
C13	0.2346 (3)	0.17475 (18)	0.11477 (16)	0.0500 (7)
H13	0.1856	0.2382	0.1045	0.060*
C14	0.3958 (3)	0.15424 (18)	0.09593 (16)	0.0460 (7)
C15	0.4658 (3)	0.05969 (19)	0.11157 (18)	0.0609 (8)
H15	0.5758	0.0454	0.1002	0.073*
C16	0.3744 (3)	−0.01372 (19)	0.14386 (17)	0.0575 (8)
H16	0.4223	−0.0776	0.1524	0.069*
C17	0.4938 (4)	0.2307 (2)	0.05836 (17)	0.0513 (8)
O1	−0.1535 (2)	0.15916 (13)	0.50126 (12)	0.0654 (6)
O2	−0.3969 (3)	0.07246 (13)	0.44691 (15)	0.0814 (7)
H2A	−0.4415	0.1127	0.4745	0.098*
O3	0.6508 (3)	0.20695 (12)	0.05373 (14)	0.0748 (6)
H3A	0.7020	0.2563	0.0408	0.090*
O4	0.4229 (2)	0.31255 (13)	0.03316 (12)	0.0628 (6)
F1	−0.14945 (18)	−0.04108 (11)	0.08519 (10)	0.0701 (5)
F2	−0.11835 (19)	−0.19326 (11)	0.12709 (10)	0.0760 (5)
F3	0.05259 (19)	−0.13151 (11)	0.05246 (11)	0.0747 (5)
F4	0.1158 (2)	−0.22673 (10)	0.27230 (11)	0.0775 (5)
F5	0.2745 (2)	−0.22093 (10)	0.17918 (11)	0.0736 (5)
F6	0.3482 (2)	−0.13628 (10)	0.29418 (11)	0.0664 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.054 (2)	0.0537 (18)	0.062 (3)	0.0027 (15)	0.0283 (19)	0.0126 (16)
C2	0.0535 (19)	0.0446 (15)	0.046 (2)	−0.0039 (14)	0.0196 (17)	0.0041 (14)
C3	0.0538 (18)	0.0478 (15)	0.044 (2)	−0.0051 (13)	0.0139 (17)	−0.0007 (14)
C4	0.0454 (17)	0.0559 (16)	0.049 (2)	−0.0061 (14)	0.0176 (17)	−0.0013 (15)
C5	0.0483 (18)	0.0442 (15)	0.041 (2)	−0.0032 (13)	0.0150 (16)	0.0021 (14)
C6	0.0547 (19)	0.0644 (17)	0.064 (3)	−0.0151 (14)	0.0211 (18)	−0.0206 (16)
C7	0.0477 (19)	0.0698 (19)	0.073 (3)	−0.0114 (15)	0.0275 (19)	−0.0068 (18)
C8	0.0423 (15)	0.0464 (15)	0.039 (2)	0.0000 (12)	0.0060 (15)	−0.0044 (14)
C9	0.055 (2)	0.0553 (19)	0.065 (3)	−0.0058 (16)	0.014 (2)	0.0039 (18)
C10	0.057 (2)	0.0604 (19)	0.059 (3)	0.0039 (16)	0.014 (2)	−0.0142 (18)
C11	0.0412 (16)	0.0499 (16)	0.0327 (19)	0.0042 (13)	0.0078 (14)	−0.0010 (13)
C12	0.0463 (17)	0.0543 (16)	0.051 (2)	0.0059 (13)	0.0216 (16)	0.0019 (15)
C13	0.0556 (18)	0.0479 (15)	0.049 (2)	0.0062 (14)	0.0162 (16)	0.0005 (14)
C14	0.0464 (17)	0.0536 (17)	0.039 (2)	0.0017 (14)	0.0107 (15)	0.0016 (14)
C15	0.0453 (17)	0.0694 (19)	0.076 (3)	0.0081 (15)	0.0307 (17)	0.0128 (17)
C16	0.0542 (19)	0.0532 (17)	0.070 (2)	0.0142 (14)	0.0240 (18)	0.0094 (16)
C17	0.0479 (19)	0.0664 (19)	0.044 (2)	−0.0031 (16)	0.0188 (17)	−0.0045 (16)
O1	0.0729 (14)	0.0669 (13)	0.0592 (16)	−0.0006 (10)	0.0205 (12)	−0.0136 (11)
O2	0.0789 (15)	0.0848 (15)	0.096 (2)	−0.0088 (12)	0.0523 (14)	−0.0270 (13)
O3	0.0644 (14)	0.0759 (14)	0.0945 (18)	−0.0037 (11)	0.0400 (13)	0.0129 (13)
O4	0.0660 (13)	0.0586 (11)	0.0685 (15)	0.0055 (10)	0.0252 (11)	0.0127 (11)
F1	0.0562 (10)	0.0868 (11)	0.0613 (13)	0.0170 (8)	−0.0013 (9)	−0.0071 (9)
F2	0.0732 (11)	0.0693 (10)	0.0835 (14)	−0.0196 (8)	0.0125 (10)	−0.0244 (10)
F3	0.0710 (11)	0.0992 (12)	0.0547 (12)	0.0075 (9)	0.0151 (10)	−0.0247 (9)
F4	0.0733 (11)	0.0613 (10)	0.1000 (16)	−0.0059 (8)	0.0231 (11)	0.0212 (9)
F5	0.0774 (12)	0.0578 (9)	0.0885 (15)	0.0155 (8)	0.0242 (11)	−0.0058 (9)
F6	0.0562 (10)	0.0689 (10)	0.0677 (13)	0.0017 (8)	−0.0013 (9)	0.0144 (9)

Geometric parameters (Å, º) top

C1—O1	1.246 (3)	C9—F5	1.340 (3)
C1—O2	1.283 (3)	C10—F1	1.333 (3)
C1—C2	1.477 (3)	C10—F3	1.332 (3)
C2—C7	1.377 (3)	C10—F2	1.341 (3)
C2—C3	1.379 (3)	C11—C16	1.379 (3)
C3—C4	1.380 (3)	C11—C12	1.393 (3)
C3—H3	0.9300	C12—C13	1.378 (3)
C4—C5	1.380 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.375 (3)
C5—C6	1.383 (3)	C13—H13	0.9300
C5—C8	1.544 (3)	C14—C15	1.379 (3)
C6—C7	1.374 (3)	C14—C17	1.479 (3)
C6—H6	0.9300	C15—C16	1.377 (3)
C7—H7	0.9300	C15—H15	0.9300
C8—C10	1.530 (3)	C16—H16	0.9300
C8—C11	1.532 (3)	C17—O4	1.254 (3)
C8—C9	1.538 (3)	C17—O3	1.276 (3)
C9—F4	1.331 (3)	O2—H2A	0.8200
C9—F6	1.333 (3)	O3—H3A	0.8200

O1—C1—O2	123.7 (3)	F6—C9—C8	111.0 (2)
O1—C1—C2	120.3 (3)	F5—C9—C8	114.0 (3)
O2—C1—C2	115.9 (3)	F1—C10—F3	106.3 (3)
C7—C2—C3	118.5 (3)	F1—C10—F2	106.5 (2)
C7—C2—C1	121.4 (3)	F3—C10—F2	106.1 (2)
C3—C2—C1	119.9 (3)	F1—C10—C8	111.9 (2)
C2—C3—C4	119.9 (2)	F3—C10—C8	111.6 (2)
C2—C3—H3	120.0	F2—C10—C8	113.9 (2)
C4—C3—H3	120.0	C16—C11—C12	117.4 (2)
C5—C4—C3	121.5 (2)	C16—C11—C8	123.4 (2)
C5—C4—H4	119.2	C12—C11—C8	119.0 (2)
C3—C4—H4	119.2	C13—C12—C11	121.4 (2)
C4—C5—C6	118.1 (2)	C13—C12—H12	119.3
C4—C5—C8	119.1 (2)	C11—C12—H12	119.3
C6—C5—C8	122.8 (2)	C14—C13—C12	120.3 (2)
C7—C6—C5	120.2 (3)	C14—C13—H13	119.9
C7—C6—H6	119.9	C12—C13—H13	119.9
C5—C6—H6	119.9	C13—C14—C15	118.9 (2)
C6—C7—C2	121.6 (2)	C13—C14—C17	121.5 (2)
C6—C7—H7	119.2	C15—C14—C17	119.5 (2)
C2—C7—H7	119.2	C14—C15—C16	120.6 (2)
C10—C8—C11	105.3 (2)	C14—C15—H15	119.7
C10—C8—C9	108.2 (2)	C16—C15—H15	119.7
C11—C8—C9	112.9 (2)	C11—C16—C15	121.3 (2)
C10—C8—C5	113.1 (2)	C11—C16—H16	119.3
C11—C8—C5	111.55 (19)	C15—C16—H16	119.3
C9—C8—C5	105.9 (2)	O4—C17—O3	123.8 (3)
F4—C9—F6	106.7 (3)	O4—C17—C14	120.6 (3)
F4—C9—F5	106.3 (2)	O3—C17—C14	115.6 (3)
F6—C9—F5	106.7 (2)	C1—O2—H2A	109.5
F4—C9—C8	111.7 (2)	C17—O3—H3A	109.5

O1—C1—C2—C7	−174.9 (2)	C11—C8—C10—F1	−70.1 (3)
O2—C1—C2—C7	2.1 (4)	C9—C8—C10—F1	168.9 (2)
O1—C1—C2—C3	1.2 (4)	C5—C8—C10—F1	51.9 (3)
O2—C1—C2—C3	178.2 (2)	C11—C8—C10—F3	48.8 (3)
C7—C2—C3—C4	2.2 (4)	C9—C8—C10—F3	−72.2 (3)
C1—C2—C3—C4	−173.9 (2)	C5—C8—C10—F3	170.8 (2)
C2—C3—C4—C5	0.1 (4)	C11—C8—C10—F2	169.0 (2)
C3—C4—C5—C6	−3.0 (4)	C9—C8—C10—F2	48.0 (3)
C3—C4—C5—C8	179.2 (2)	C5—C8—C10—F2	−69.0 (3)
C4—C5—C6—C7	3.6 (4)	C10—C8—C11—C16	−94.9 (3)
C8—C5—C6—C7	−178.7 (2)	C9—C8—C11—C16	22.9 (4)
C5—C6—C7—C2	−1.3 (4)	C5—C8—C11—C16	142.0 (2)
C3—C2—C7—C6	−1.6 (4)	C10—C8—C11—C12	80.3 (3)
C1—C2—C7—C6	174.5 (3)	C9—C8—C11—C12	−161.9 (2)
C4—C5—C8—C10	−159.9 (2)	C5—C8—C11—C12	−42.7 (3)
C6—C5—C8—C10	22.4 (3)	C16—C11—C12—C13	0.6 (4)
C4—C5—C8—C11	−41.5 (3)	C8—C11—C12—C13	−174.9 (2)
C6—C5—C8—C11	140.9 (2)	C11—C12—C13—C14	−1.1 (4)
C4—C5—C8—C9	81.7 (3)	C12—C13—C14—C15	0.1 (4)
C6—C5—C8—C9	−95.9 (3)	C12—C13—C14—C17	179.3 (2)
C10—C8—C9—F4	−73.2 (3)	C13—C14—C15—C16	1.3 (4)
C11—C8—C9—F4	170.6 (2)	C17—C14—C15—C16	−177.8 (3)
C5—C8—C9—F4	48.3 (3)	C12—C11—C16—C15	0.9 (4)
C10—C8—C9—F6	167.9 (2)	C8—C11—C16—C15	176.1 (3)
C11—C8—C9—F6	51.7 (3)	C14—C15—C16—C11	−1.9 (4)
C5—C8—C9—F6	−70.7 (3)	C13—C14—C17—O4	−8.7 (4)
C10—C8—C9—F5	47.3 (3)	C15—C14—C17—O4	170.4 (3)
C11—C8—C9—F5	−68.9 (3)	C13—C14—C17—O3	171.5 (3)
C5—C8—C9—F5	168.8 (2)	C15—C14—C17—O3	−9.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4ⁱ	0.82	1.85	2.661 (2)	169
O3—H3A···O1ⁱⁱ	0.82	1.80	2.603 (2)	165
C15—H15···F1ⁱⁱⁱ	0.93	2.48	3.382 (3)	163

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀F₆O₄
M_r	392.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.7523 (16), 13.381 (3), 16.134 (3)
β (°)	102.294 (4)
V (Å³)	1635.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.35 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	8113, 2904, 1339
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.071, 1.00
No. of reflections	2904
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4ⁱ	0.82	1.85	2.661 (2)	169
O3—H3A···O1ⁱⁱ	0.82	1.80	2.603 (2)	165
C15—H15···F1ⁱⁱⁱ	0.93	2.48	3.382 (3)	163

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

Acknowledgements

This project was supported by the Natural Scientific Foundation of Shaanxi Province, China (grant No. SJ08B11), the Key Laboratory Foundation of Shaanxi Provincial Education Office, China (Nos. 08JZ82, 07 J K435, 08 J K490, 09 J K816, 09 J K826 and 09 J K815) and the Special Scientific Research Foundation of Yan'an University (No. D2009-139).

References

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