1-Benzyl-3-(2-methoxy­phen­yl)imidazolium tetra­fluoro­borate

Jiang, P.

doi:10.1107/S1600536809031602

organic compounds

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Volume 65| Part 9| September 2009| Page o2178

doi:10.1107/S1600536809031602

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1-Benzyl-3-(2-methoxyphenyl)imidazolium tetrafluoroborate

Ping Jiang ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jphdp868@126.com

(Received 29 July 2009; accepted 11 August 2009; online 19 August 2009)

In the title compound, C₁₇H₁₇N₂O⁺·BF₄⁻, the central imidazolium ring makes dihedral angles of 74.58 (9) and 40.10 (6)° with the phenyl and 2-methoxyphenyl rings, respectively. In the crystal, a strong π–π interaction is observed between the imidazolium and 2-methoxyphenyl rings, with a centroid–centroid distance of 3.5115 (15) Å. In addition, C—H⋯F and C—H⋯O hydrogen bonds and C—H⋯π interactions involving the phenyl ring are observed.

Related literature

For the synthesis, see: Liu et al.. (2003 ). For general background to N-heterocyclic carbenes, see: Arduengo et al. (1991 ). For the biological activity of imidazolium salts, see: Vik et al. (2007 ); Demberelnyamba et al. (2004 ); Dallas et al. (2007 ); Ballistreri et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₇N₂O⁺·BF₄⁻
M_r = 352.14
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.1880 (13) Å
b = 15.114 (3) Å
c = 15.358 (3) Å
V = 1668.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.33 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
13633 measured reflections
2197 independent reflections
2069 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.00
2197 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.85 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
C7—H7B⋯F3ⁱ	0.99	2.30	3.268 (3)	167
C8—H8⋯F4ⁱ	0.95	2.34	3.220 (3)	154
C9—H9⋯F1	0.95	2.21	3.122 (3)	161
C10—H10⋯F1ⁱⁱ	0.95	2.37	3.236 (3)	150
C10—H10⋯F2ⁱⁱ	0.95	2.38	3.221 (3)	147
C12—H12⋯O1ⁱⁱ	0.95	2.57	3.292 (3)	133
C14—H14⋯F3ⁱⁱⁱ	0.95	2.48	3.274 (3)	140
C13—H13⋯Cg1ⁱⁱ	0.94	2.61	3.460 (3)	149
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

Data collection: RAPID-AUTO (Rigaku/MSC, 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031602/ci2870sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031602/ci2870Isup2.hkl

checkCIF report

Comment top

Since the synthesis and isolation of the first stable, crystalline N-heterocyclic carbene (NHC) was disclosed by Arduengo et al. (1991) scientists have paid much attention to this field. In recent years, a large number of N-heterocyclic carbene (NHC) precursors have been synthesized 1,3-Disubstituted imidazolium salts are potential precursors for the synthesis of various transition metal NHCs. In addition, a number of biological activities of imidazolium salts have been reported including antimicrobial, antifungal, antitumor activities (Vik et al., 2007; Demberelnyamba et al., 2004; Dallas et al., 2007; Ballistreri et al., 2004). We report here crystal structure of a NHC precursor, the title compound.

Bond lengths and angles in title molecule (Fig. 1) are normal. The imidazolium ring makes dihedral angles of 74.58 (9)° and 40.10 (6)°, respectively, with the phenyl ring and 2-methoxyphenyl ring. The methoxy group is slightly twisted away from the attached ring [C17—O1—C16—C15 = -7.8 (4)°].

In the crystal, there are strong π-π interactions between imidazolium and 2-methoxyphenyl rings, with a Cg2···Cg2ⁱⁱ distance of 3.5115 (15) Å [symmetry code: (ii) x - 1/2, 1/2 - y, 1 - z] where Cg2 and Cg3 are centroids of the imidazolium and methoxyphenyl rings, respectively. In addition, C—H···F and C—H···O hydrogen bonds and C—H···π interactions involving the C1—C6 phenyl ring are observed (Table 1).

Related literature top

For the synthesis, see: Liu et al.. (2003). For general background to N-heterocyclic carbenes, see: Arduengo et al. (1991). For the biological activity of imidazolium salts, see: Vik et al. (2007); Demberelnyamba et al. (2004); Dallas et al. (2007); Ballistreri et al. (2004). Cg1 is the centroid of the C1–C6 ring.

Experimental top

The title compound was prepared according to the reported procedure of Liu et al.. (2003). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane and petroleum ether.

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering scheme.

1-Benzyl-3-(2-methoxyphenyl)imidazolium tetrafluoroborate top

Crystal data top

C₁₇H₁₇N₂O⁺·BF₄⁻	F(000) = 728
M_r = 352.14	D_x = 1.402 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5660 reflections
a = 7.1880 (13) Å	θ = 3.0–27.5°
b = 15.114 (3) Å	µ = 0.12 mm⁻¹
c = 15.358 (3) Å	T = 93 K
V = 1668.4 (5) Å³	Block, colourless
Z = 4	0.40 × 0.33 × 0.33 mm

Data collection top

Rigaku SPIDER diffractometer	2069 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.032
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −9→9
13633 measured reflections	k = −19→19
2197 independent reflections	l = −19→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.068P)² + 0.46P] where P = (F_o² + 2F_c²)/3
2197 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₁₇N₂O⁺·BF₄⁻	V = 1668.4 (5) Å³
M_r = 352.14	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.1880 (13) Å	µ = 0.12 mm⁻¹
b = 15.114 (3) Å	T = 93 K
c = 15.358 (3) Å	0.40 × 0.33 × 0.33 mm

Data collection top

Rigaku SPIDER diffractometer	2069 reflections with I > 2σ(I)
13633 measured reflections	R_int = 0.032
2197 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.00	Δρ_max = 0.85 e Å⁻³
2197 reflections	Δρ_min = −0.19 e Å⁻³
227 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
B1	0.6858 (5)	0.1082 (2)	0.2432 (2)	0.0349 (7)
F1	0.7005 (2)	0.18357 (10)	0.29508 (10)	0.0360 (4)
F2	0.7661 (3)	0.03715 (11)	0.28690 (12)	0.0520 (5)
F3	0.7771 (3)	0.12215 (13)	0.16519 (11)	0.0601 (6)
F4	0.4996 (3)	0.09039 (13)	0.22721 (13)	0.0555 (6)
O1	0.6091 (3)	0.27395 (12)	0.65713 (11)	0.0314 (4)
N1	0.4482 (3)	0.45145 (13)	0.48559 (13)	0.0226 (4)
N2	0.4930 (3)	0.31030 (12)	0.49196 (12)	0.0203 (4)
C1	0.6888 (4)	0.63622 (15)	0.48138 (17)	0.0291 (5)
H1	0.6486	0.6402	0.4226	0.035*
C2	0.8534 (5)	0.67656 (17)	0.5060 (2)	0.0390 (7)
H2	0.9262	0.7075	0.4642	0.047*
C3	0.9113 (5)	0.67162 (19)	0.5918 (2)	0.0453 (8)
H3	1.0237	0.6996	0.6091	0.054*
C4	0.8069 (5)	0.6263 (2)	0.6522 (2)	0.0460 (8)
H4	0.8471	0.6232	0.7111	0.055*
C5	0.6423 (5)	0.58515 (17)	0.62717 (18)	0.0359 (6)
H5	0.5710	0.5535	0.6689	0.043*
C6	0.5814 (4)	0.59003 (16)	0.54127 (16)	0.0264 (5)
C7	0.4059 (4)	0.54316 (16)	0.51345 (18)	0.0289 (5)
H7A	0.3167	0.5419	0.5626	0.035*
H7B	0.3475	0.5758	0.4647	0.035*
C8	0.5203 (3)	0.42622 (15)	0.40606 (16)	0.0230 (5)
H8	0.5458	0.4638	0.3579	0.028*
C9	0.5478 (3)	0.33788 (15)	0.40976 (15)	0.0211 (5)
H9	0.5956	0.3015	0.3646	0.025*
C10	0.4336 (3)	0.38076 (16)	0.53617 (15)	0.0227 (5)
H10	0.3883	0.3803	0.5943	0.027*
C11	0.4976 (3)	0.22050 (15)	0.52293 (15)	0.0213 (5)
C12	0.4486 (3)	0.15283 (16)	0.46744 (16)	0.0235 (5)
H12	0.4116	0.1657	0.4094	0.028*
C13	0.4533 (3)	0.06574 (16)	0.49642 (18)	0.0288 (5)
H13	0.4208	0.0188	0.4582	0.035*
C14	0.5056 (4)	0.04793 (17)	0.58102 (19)	0.0317 (6)
H14	0.5070	−0.0116	0.6010	0.038*
C15	0.5562 (3)	0.11531 (17)	0.63726 (18)	0.0305 (6)
H15	0.5918	0.1019	0.6953	0.037*
C16	0.5549 (3)	0.20287 (16)	0.60874 (15)	0.0246 (5)
C17	0.6499 (5)	0.2592 (2)	0.74763 (17)	0.0423 (7)
H17A	0.5385	0.2369	0.7771	0.051*
H17B	0.6885	0.3151	0.7746	0.051*
H17C	0.7504	0.2158	0.7529	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0408 (16)	0.0351 (15)	0.0287 (15)	0.0150 (14)	−0.0110 (14)	−0.0110 (13)
F1	0.0441 (9)	0.0332 (8)	0.0308 (8)	0.0046 (7)	0.0012 (7)	−0.0122 (7)
F2	0.0711 (13)	0.0394 (9)	0.0455 (11)	0.0217 (9)	−0.0260 (10)	−0.0105 (8)
F3	0.0828 (15)	0.0669 (13)	0.0306 (10)	0.0258 (12)	0.0078 (10)	−0.0132 (9)
F4	0.0473 (10)	0.0555 (11)	0.0638 (13)	0.0119 (10)	−0.0236 (10)	−0.0256 (10)
O1	0.0325 (10)	0.0403 (10)	0.0214 (9)	−0.0103 (8)	−0.0031 (8)	0.0036 (7)
N1	0.0221 (9)	0.0230 (9)	0.0228 (10)	0.0009 (8)	0.0009 (8)	−0.0030 (8)
N2	0.0206 (9)	0.0208 (9)	0.0194 (9)	−0.0025 (7)	0.0009 (8)	0.0011 (7)
C1	0.0393 (13)	0.0219 (10)	0.0261 (13)	0.0020 (11)	−0.0057 (11)	0.0006 (10)
C2	0.0464 (16)	0.0290 (13)	0.0415 (16)	−0.0099 (12)	−0.0037 (14)	0.0027 (11)
C3	0.0506 (18)	0.0347 (14)	0.0504 (18)	−0.0131 (13)	−0.0161 (15)	−0.0031 (13)
C4	0.065 (2)	0.0432 (16)	0.0298 (15)	−0.0067 (16)	−0.0153 (15)	−0.0046 (13)
C5	0.0518 (17)	0.0313 (12)	0.0245 (13)	−0.0014 (13)	0.0000 (13)	−0.0046 (10)
C6	0.0333 (13)	0.0212 (10)	0.0247 (12)	0.0035 (10)	−0.0001 (10)	−0.0039 (9)
C7	0.0308 (12)	0.0237 (11)	0.0321 (14)	0.0052 (10)	0.0025 (11)	−0.0077 (10)
C8	0.0252 (11)	0.0238 (10)	0.0200 (11)	−0.0005 (9)	0.0021 (10)	−0.0004 (9)
C9	0.0220 (11)	0.0225 (10)	0.0187 (11)	0.0002 (9)	0.0019 (9)	0.0000 (9)
C10	0.0214 (10)	0.0265 (11)	0.0202 (11)	−0.0009 (9)	0.0030 (9)	−0.0009 (9)
C11	0.0150 (9)	0.0244 (10)	0.0245 (12)	−0.0011 (9)	0.0010 (9)	0.0044 (9)
C12	0.0181 (10)	0.0250 (11)	0.0275 (13)	0.0007 (9)	−0.0002 (9)	0.0017 (9)
C13	0.0233 (11)	0.0254 (11)	0.0377 (15)	−0.0009 (10)	0.0034 (11)	0.0012 (10)
C14	0.0242 (11)	0.0274 (11)	0.0435 (15)	0.0009 (10)	0.0027 (12)	0.0092 (11)
C15	0.0218 (11)	0.0378 (13)	0.0321 (14)	0.0019 (10)	−0.0002 (10)	0.0134 (11)
C16	0.0179 (10)	0.0328 (12)	0.0230 (12)	−0.0045 (10)	−0.0004 (9)	0.0038 (9)
C17	0.0478 (17)	0.0537 (17)	0.0253 (14)	−0.0128 (15)	−0.0092 (13)	0.0070 (13)

Geometric parameters (Å, º) top

B1—F3	1.382 (4)	C5—H5	0.95
B1—F4	1.388 (4)	C6—C7	1.509 (4)
B1—F2	1.392 (3)	C7—H7A	0.99
B1—F1	1.394 (3)	C7—H7B	0.99
O1—C16	1.363 (3)	C8—C9	1.351 (3)
O1—C17	1.438 (3)	C8—H8	0.95
N1—C10	1.325 (3)	C9—H9	0.95
N1—C8	1.381 (3)	C10—H10	0.95
N1—C7	1.482 (3)	C11—C12	1.377 (3)
N2—C10	1.333 (3)	C11—C16	1.406 (3)
N2—C9	1.387 (3)	C12—C13	1.390 (3)
N2—C11	1.439 (3)	C12—H12	0.95
C1—C2	1.383 (4)	C13—C14	1.379 (4)
C1—C6	1.389 (4)	C13—H13	0.95
C1—H1	0.95	C14—C15	1.384 (4)
C2—C3	1.385 (4)	C14—H14	0.95
C2—H2	0.95	C15—C16	1.394 (3)
C3—C4	1.376 (5)	C15—H15	0.95
C3—H3	0.95	C17—H17A	0.98
C4—C5	1.391 (5)	C17—H17B	0.98
C4—H4	0.95	C17—H17C	0.98
C5—C6	1.392 (4)

F3—B1—F4	109.5 (2)	C6—C7—H7B	109.6
F3—B1—F2	109.8 (3)	H7A—C7—H7B	108.1
F4—B1—F2	109.6 (3)	C9—C8—N1	106.9 (2)
F3—B1—F1	109.6 (3)	C9—C8—H8	126.5
F4—B1—F1	109.4 (2)	N1—C8—H8	126.5
F2—B1—F1	108.9 (2)	C8—C9—N2	107.1 (2)
C16—O1—C17	117.6 (2)	C8—C9—H9	126.5
C10—N1—C8	109.00 (19)	N2—C9—H9	126.5
C10—N1—C7	124.7 (2)	N1—C10—N2	108.67 (19)
C8—N1—C7	126.2 (2)	N1—C10—H10	125.7
C10—N2—C9	108.33 (19)	N2—C10—H10	125.7
C10—N2—C11	126.33 (19)	C12—C11—C16	121.0 (2)
C9—N2—C11	125.33 (19)	C12—C11—N2	119.4 (2)
C2—C1—C6	121.1 (2)	C16—C11—N2	119.7 (2)
C2—C1—H1	119.5	C11—C12—C13	119.9 (2)
C6—C1—H1	119.5	C11—C12—H12	120.0
C1—C2—C3	119.6 (3)	C13—C12—H12	120.0
C1—C2—H2	120.2	C14—C13—C12	119.6 (2)
C3—C2—H2	120.2	C14—C13—H13	120.2
C4—C3—C2	120.3 (3)	C12—C13—H13	120.2
C4—C3—H3	119.8	C13—C14—C15	121.1 (2)
C2—C3—H3	119.8	C13—C14—H14	119.5
C3—C4—C5	120.0 (3)	C15—C14—H14	119.5
C3—C4—H4	120.0	C14—C15—C16	120.1 (2)
C5—C4—H4	120.0	C14—C15—H15	120.0
C4—C5—C6	120.4 (3)	C16—C15—H15	120.0
C4—C5—H5	119.8	O1—C16—C15	125.1 (2)
C6—C5—H5	119.8	O1—C16—C11	116.4 (2)
C1—C6—C5	118.7 (3)	C15—C16—C11	118.4 (2)
C1—C6—C7	120.9 (2)	O1—C17—H17A	109.5
C5—C6—C7	120.4 (2)	O1—C17—H17B	109.5
N1—C7—C6	110.4 (2)	H17A—C17—H17B	109.5
N1—C7—H7A	109.6	O1—C17—H17C	109.5
C6—C7—H7A	109.6	H17A—C17—H17C	109.5
N1—C7—H7B	109.6	H17B—C17—H17C	109.5

C6—C1—C2—C3	−0.6 (4)	C9—N2—C10—N1	0.1 (3)
C1—C2—C3—C4	0.5 (5)	C11—N2—C10—N1	−179.0 (2)
C2—C3—C4—C5	0.1 (5)	C10—N2—C11—C12	139.7 (2)
C3—C4—C5—C6	−0.5 (5)	C9—N2—C11—C12	−39.2 (3)
C2—C1—C6—C5	0.2 (4)	C10—N2—C11—C16	−41.3 (3)
C2—C1—C6—C7	−177.6 (2)	C9—N2—C11—C16	139.7 (2)
C4—C5—C6—C1	0.4 (4)	C16—C11—C12—C13	0.8 (3)
C4—C5—C6—C7	178.2 (3)	N2—C11—C12—C13	179.7 (2)
C10—N1—C7—C6	96.0 (3)	C11—C12—C13—C14	0.6 (4)
C8—N1—C7—C6	−79.3 (3)	C12—C13—C14—C15	−1.0 (4)
C1—C6—C7—N1	89.0 (3)	C13—C14—C15—C16	0.0 (4)
C5—C6—C7—N1	−88.8 (3)	C17—O1—C16—C15	−7.8 (4)
C10—N1—C8—C9	0.4 (3)	C17—O1—C16—C11	173.7 (2)
C7—N1—C8—C9	176.3 (2)	C14—C15—C16—O1	−177.2 (2)
N1—C8—C9—N2	−0.4 (3)	C14—C15—C16—C11	1.4 (4)
C10—N2—C9—C8	0.2 (3)	C12—C11—C16—O1	176.9 (2)
C11—N2—C9—C8	179.3 (2)	N2—C11—C16—O1	−2.0 (3)
C8—N1—C10—N2	−0.3 (3)	C12—C11—C16—C15	−1.7 (3)
C7—N1—C10—N2	−176.3 (2)	N2—C11—C16—C15	179.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···F3ⁱ	0.99	2.30	3.268 (3)	167
C8—H8···F4ⁱ	0.95	2.34	3.220 (3)	154
C9—H9···F1	0.95	2.21	3.122 (3)	161
C10—H10···F1ⁱⁱ	0.95	2.37	3.236 (3)	150
C10—H10···F2ⁱⁱ	0.95	2.38	3.221 (3)	147
C12—H12···O1ⁱⁱ	0.95	2.57	3.292 (3)	133
C14—H14···F3ⁱⁱⁱ	0.95	2.48	3.274 (3)	140
C13—H13···Cg1ⁱⁱ	0.94	2.61	3.460 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₂O⁺·BF₄⁻
M_r	352.14
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	93
a, b, c (Å)	7.1880 (13), 15.114 (3), 15.358 (3)
V (Å³)	1668.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.40 × 0.33 × 0.33

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13633, 2197, 2069
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.00
No. of reflections	2197
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.19

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLEASE PROVIDE.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···F3ⁱ	0.99	2.30	3.268 (3)	167
C8—H8···F4ⁱ	0.95	2.34	3.220 (3)	154
C9—H9···F1	0.95	2.21	3.122 (3)	161
C10—H10···F1ⁱⁱ	0.95	2.37	3.236 (3)	150
C10—H10···F2ⁱⁱ	0.95	2.38	3.221 (3)	147
C12—H12···O1ⁱⁱ	0.95	2.57	3.292 (3)	133
C14—H14···F3ⁱⁱⁱ	0.95	2.48	3.274 (3)	140
C13—H13···Cg1ⁱⁱ	0.94	2.61	3.460 (3)	149

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

Acknowledgements

The authors thank the Fund Projects of Sichuan Educational Department (grant No. 2005 A104).

References

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