12-Di­methyl­amino-2,2-di­fluoro-8-phenyl-1λ5,3-di­aza-2λ4-boratri­cyclo­[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium

Wang, Z.-Y.

doi:10.1107/S1600536813010404

organic compounds

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Volume 69| Part 5| May 2013| Page o781

https://doi.org/10.1107/S1600536813010404

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12-Dimethylamino-2,2-difluoro-8-phenyl-1λ⁵,3-diaza-2λ⁴-boratricyclo[7.3.0.0^3,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium

Zhao-Yun Wang ^a ^*

^aSchool of Chemistry and Material Science, Anhui Normal University, Wuhu, People's Republic of China
^*Correspondence e-mail: shine_zywang@yahoo.com.cn

(Received 2 April 2013; accepted 16 April 2013; online 24 April 2013)

In the title boron–dipyrromethene derivative, C₁₇H₁₆BF₂N₃, the benzene ring and the boron–dipyrromethene mean plane form a dihedral angle of 55.82 (8)°. In the crystal, pairs of C—H⋯F interactions link the molecules, forming inversion dimers. Further C—H⋯F interactions link the dimers into a three-dimensional network.

Related literature

For the synthesis and applications of related 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivatives, see: Trieflinger et al. (2005 ). For related structures, see: Jiao et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₆BF₂N₃
M_r = 311.14
Monoclinic, P 2₁ /c
a = 7.8033 (6) Å
b = 25.524 (2) Å
c = 9.9776 (5) Å
β = 128.671 (4)°
V = 1551.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.981
11054 measured reflections
2736 independent reflections
2025 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.03
2736 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F2ⁱ	0.93	2.51	3.291 (3)	142
C17—H17C⋯F2ⁱⁱ	0.96	2.49	3.282 (3)	140
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+2, -z+2.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536813010404/rk2400sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813010404/rk2400Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813010404/rk2400Isup3.cml

checkCIF report

Comment top

Fluorescent dyes, especially 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), have been led to the increased research interest in these molecules lately, BODIPYs have found wide applications in fluorescence labels and biomolecular sensors (Trieflinger et al., 2005), due to their remarkable properties, including large molar absorption coefficient, sharp fluorescence emissions, high fluorescence quantum yields, and high photophysical stability. As part of our ongoing studies (Jiao et al., 2011), we have obtained the title compound, and report its molecular structure here (Fig. 1). The bond lengths and angles are within normal ranges. By short contact C1—H1···F2ⁱ = 2.512Å, molecule forms 10-members centrosymmetrical dimers. Next short contact C17—H17···F2ⁱⁱ = 2.491Å form a three-dimensional network, which seem to be very effective in the stabilization of the crystal structure (Fig. 2). Symmetry codes: (i) -x, 2-y, 1-z; (ii) -x, 2-y, 2-z.

Related literature top

For the synthesis and applications of related 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivatives, see: Trieflinger et al. (2005). For related structures, see: Jiao et al. (2011).

Experimental top

To 4,4-difluoro-8-phenyl-4-bora-3a,4a-diaza-s-indacene (134 mg, 0.5 mmol) in 3 ml of DMF. was added Potassium tert-butoxide (561 mg, 5 mmol). After stirring at 323 k for 3 h, the reaction was monitored by TLC, then the mixture was poured into water (50 ml), adjusted pH value to 7 with hydrochloric acid and extracted with CH₂Cl₂ (3×30 ml). Organic layers were combined, dried over Mg₂SO₄, and evaporated to dryness under vacuum. Purification was performed by column chromatography on silica gel using hexane / CH₂Cl₂ (v/v, 2:1) as eluent, from which the desired product was obtained in 51% yield (80 mg).

Structure description top

For the synthesis and applications of related 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene derivatives, see: Trieflinger et al. (2005). For related structures, see: Jiao et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 molecular structure of title molecule showing the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing diagram of the title compound. Short H···F contacts are showed by dashed lines.

12-Dimethylamino-2,2-difluoro-8-phenyl-1λ⁵,3-diaza-2λ⁴-boratricyclo[7.3.0.0^3,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium top

Crystal data top

C₁₇H₁₆BF₂N₃	F(000) = 648
M_r = 311.14	D_x = 1.332 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4251 reflections
a = 7.8033 (6) Å	θ = 2.7–24.3°
b = 25.524 (2) Å	µ = 0.10 mm⁻¹
c = 9.9776 (5) Å	T = 295 K
β = 128.671 (4)°	Block, colourless
V = 1551.5 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2736 independent reflections
Radiation source: fine-focus sealed tube	2025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.972, T_max = 0.981	k = −30→30
11054 measured reflections	l = −11→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0582P)² + 0.2638P] where P = (F_o² + 2F_c²)/3
2736 reflections	(Δ/σ)_max = 0.005
210 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₇H₁₆BF₂N₃	V = 1551.5 (2) Å³
M_r = 311.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8033 (6) Å	µ = 0.10 mm⁻¹
b = 25.524 (2) Å	T = 295 K
c = 9.9776 (5) Å	0.30 × 0.20 × 0.20 mm
β = 128.671 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	2736 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2025 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.027
11054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
2736 reflections	Δρ_min = −0.14 e Å⁻³
210 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
F1	−0.28223 (17)	0.91338 (5)	0.54009 (14)	0.0842 (4)
F2	−0.0433 (2)	0.98113 (4)	0.67169 (16)	0.0884 (4)
N1	0.0902 (2)	0.90034 (6)	0.65707 (18)	0.0593 (4)
N2	−0.0100 (2)	0.91017 (5)	0.84906 (17)	0.0543 (4)
N3	−0.2640 (3)	0.95619 (7)	0.8700 (2)	0.0779 (5)
C1	0.1083 (4)	0.91003 (9)	0.5324 (3)	0.0760 (6)
H1	0.0217	0.9335	0.4423	0.091*
C2	0.2720 (4)	0.88033 (10)	0.5591 (3)	0.0821 (6)
H2	0.3155	0.8798	0.4910	0.098*
C3	0.3621 (3)	0.85096 (8)	0.7062 (2)	0.0685 (5)
H3	0.4772	0.8272	0.7554	0.082*
C4	0.2477 (3)	0.86380 (7)	0.7662 (2)	0.0552 (4)
C5	0.2796 (3)	0.84981 (6)	0.9186 (2)	0.0510 (4)
C6	0.4562 (3)	0.81223 (7)	1.0379 (2)	0.0563 (4)
C7	0.4630 (4)	0.76322 (7)	0.9807 (3)	0.0757 (6)
H7	0.3519	0.7533	0.8678	0.091*
C8	0.6331 (5)	0.72935 (9)	1.0903 (4)	0.0968 (8)
H8	0.6366	0.6966	1.0513	0.116*
C9	0.7971 (5)	0.74379 (12)	1.2564 (4)	0.1039 (9)
H9	0.9126	0.7209	1.3295	0.125*
C10	0.7929 (4)	0.79204 (11)	1.3165 (3)	0.0923 (7)
H10	0.9040	0.8015	1.4300	0.111*
C11	0.6232 (3)	0.82612 (8)	1.2073 (2)	0.0696 (5)
H11	0.6203	0.8587	1.2474	0.084*
C12	0.1544 (3)	0.87210 (6)	0.9555 (2)	0.0512 (4)
C13	0.1508 (3)	0.86084 (7)	1.0927 (2)	0.0629 (5)
H13	0.2419	0.8372	1.1811	0.075*
C14	−0.0056 (3)	0.88989 (8)	1.0739 (3)	0.0705 (5)
H14	−0.0427	0.8897	1.1462	0.085*
C15	−0.1061 (3)	0.92141 (7)	0.9228 (2)	0.0621 (5)
C16	−0.3699 (4)	0.99063 (10)	0.7212 (4)	0.1032 (8)
H16A	−0.2601	1.0099	0.7266	0.155*
H16B	−0.4650	1.0146	0.7208	0.155*
H16C	−0.4545	0.9700	0.6181	0.155*
C17	−0.3488 (4)	0.96200 (12)	0.9644 (3)	0.1063 (9)
H17A	−0.3107	0.9317	1.0349	0.159*
H17B	−0.5057	0.9655	0.8847	0.159*
H17C	−0.2860	0.9926	1.0356	0.159*
B1	−0.0669 (3)	0.92741 (8)	0.6751 (3)	0.0601 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0555 (6)	0.1025 (9)	0.0600 (7)	0.0046 (6)	0.0193 (6)	−0.0029 (6)
F2	0.1155 (10)	0.0568 (7)	0.0922 (9)	0.0042 (6)	0.0646 (8)	0.0128 (6)
N1	0.0582 (8)	0.0667 (9)	0.0467 (8)	−0.0010 (7)	0.0297 (7)	0.0060 (7)
N2	0.0504 (8)	0.0549 (8)	0.0527 (8)	0.0015 (6)	0.0299 (7)	−0.0012 (6)
N3	0.0586 (9)	0.0861 (12)	0.0789 (12)	0.0042 (9)	0.0379 (9)	−0.0200 (9)
C1	0.0825 (14)	0.0895 (14)	0.0521 (11)	−0.0032 (12)	0.0402 (11)	0.0119 (10)
C2	0.0860 (15)	0.1096 (17)	0.0647 (13)	−0.0059 (13)	0.0539 (12)	0.0010 (12)
C3	0.0648 (11)	0.0866 (13)	0.0593 (11)	0.0004 (10)	0.0414 (10)	−0.0020 (10)
C4	0.0523 (9)	0.0622 (10)	0.0466 (9)	−0.0033 (8)	0.0287 (8)	−0.0012 (8)
C5	0.0501 (9)	0.0512 (9)	0.0462 (9)	−0.0036 (7)	0.0274 (8)	−0.0015 (7)
C6	0.0579 (10)	0.0579 (10)	0.0564 (11)	0.0046 (8)	0.0373 (9)	0.0069 (8)
C7	0.0912 (15)	0.0622 (11)	0.0837 (14)	0.0110 (11)	0.0595 (13)	0.0051 (10)
C8	0.122 (2)	0.0736 (14)	0.128 (2)	0.0338 (15)	0.094 (2)	0.0272 (15)
C9	0.0907 (18)	0.109 (2)	0.126 (2)	0.0468 (16)	0.0742 (19)	0.0593 (18)
C10	0.0657 (13)	0.1115 (19)	0.0761 (15)	0.0170 (13)	0.0327 (12)	0.0309 (14)
C11	0.0610 (11)	0.0743 (12)	0.0601 (12)	0.0052 (10)	0.0312 (10)	0.0095 (10)
C12	0.0515 (9)	0.0515 (9)	0.0472 (9)	−0.0021 (7)	0.0292 (8)	−0.0016 (7)
C13	0.0655 (11)	0.0714 (11)	0.0520 (10)	−0.0016 (9)	0.0368 (9)	0.0004 (9)
C14	0.0677 (12)	0.0925 (14)	0.0606 (12)	−0.0045 (11)	0.0446 (10)	−0.0108 (10)
C15	0.0522 (10)	0.0667 (11)	0.0604 (11)	−0.0061 (9)	0.0317 (9)	−0.0164 (9)
C16	0.0863 (16)	0.0873 (16)	0.119 (2)	0.0278 (14)	0.0557 (16)	0.0073 (15)
C17	0.0768 (15)	0.141 (2)	0.1026 (19)	0.0081 (15)	0.0569 (15)	−0.0398 (16)
B1	0.0562 (12)	0.0545 (11)	0.0519 (12)	−0.0006 (9)	0.0253 (10)	0.0022 (9)

Geometric parameters (Å, º) top

F1—B1	1.392 (2)	C6—C7	1.390 (3)
F2—B1	1.387 (2)	C7—C8	1.375 (3)
N1—C1	1.359 (2)	C7—H7	0.9300
N1—C4	1.376 (2)	C8—C9	1.368 (4)
N1—B1	1.513 (3)	C8—H8	0.9300
N2—C15	1.369 (2)	C9—C10	1.379 (4)
N2—C12	1.420 (2)	C9—H9	0.9300
N2—B1	1.562 (3)	C10—C11	1.376 (3)
N3—C15	1.331 (2)	C10—H10	0.9300
N3—C17	1.458 (3)	C11—H11	0.9300
N3—C16	1.458 (3)	C12—C13	1.416 (2)
C1—C2	1.361 (3)	C13—C14	1.337 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.386 (3)	C14—C15	1.435 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.388 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.425 (2)	C16—H16C	0.9600
C5—C12	1.365 (2)	C17—H17A	0.9600
C5—C6	1.479 (2)	C17—H17B	0.9600
C6—C11	1.389 (3)	C17—H17C	0.9600

C1—N1—C4	107.13 (16)	C11—C10—C9	119.5 (2)
C1—N1—B1	125.53 (16)	C11—C10—H10	120.2
C4—N1—B1	127.26 (14)	C9—C10—H10	120.2
C15—N2—C12	106.50 (14)	C10—C11—C6	120.6 (2)
C15—N2—B1	131.83 (15)	C10—C11—H11	119.7
C12—N2—B1	121.37 (14)	C6—C11—H11	119.7
C15—N3—C17	119.6 (2)	C5—C12—C13	128.79 (16)
C15—N3—C16	126.89 (19)	C5—C12—N2	123.22 (15)
C17—N3—C16	113.53 (19)	C13—C12—N2	107.89 (15)
N1—C1—C2	109.95 (18)	C14—C13—C12	108.66 (17)
N1—C1—H1	125.0	C14—C13—H13	125.7
C2—C1—H1	125.0	C12—C13—H13	125.7
C1—C2—C3	107.53 (18)	C13—C14—C15	108.04 (17)
C1—C2—H2	126.2	C13—C14—H14	126.0
C3—C2—H2	126.2	C15—C14—H14	126.0
C2—C3—C4	106.95 (19)	N3—C15—N2	127.54 (18)
C2—C3—H3	126.5	N3—C15—C14	123.55 (18)
C4—C3—H3	126.5	N2—C15—C14	108.89 (16)
N1—C4—C3	108.44 (16)	N3—C16—H16A	109.5
N1—C4—C5	119.19 (15)	N3—C16—H16B	109.5
C3—C4—C5	132.08 (17)	H16A—C16—H16B	109.5
C12—C5—C4	120.46 (15)	N3—C16—H16C	109.5
C12—C5—C6	121.14 (15)	H16A—C16—H16C	109.5
C4—C5—C6	118.36 (15)	H16B—C16—H16C	109.5
C11—C6—C7	118.84 (18)	N3—C17—H17A	109.5
C11—C6—C5	120.53 (16)	N3—C17—H17B	109.5
C7—C6—C5	120.58 (17)	H17A—C17—H17B	109.5
C8—C7—C6	120.3 (2)	N3—C17—H17C	109.5
C8—C7—H7	119.8	H17A—C17—H17C	109.5
C6—C7—H7	119.8	H17B—C17—H17C	109.5
C9—C8—C7	120.1 (2)	F2—B1—F1	109.21 (15)
C9—C8—H8	119.9	F2—B1—N1	108.58 (16)
C7—C8—H8	119.9	F1—B1—N1	110.18 (16)
C8—C9—C10	120.6 (2)	F2—B1—N2	110.87 (15)
C8—C9—H9	119.7	F1—B1—N2	109.63 (16)
C10—C9—H9	119.7	N1—B1—N2	108.35 (14)

C4—N1—C1—C2	0.4 (2)	C15—N2—C12—C5	177.30 (15)
B1—N1—C1—C2	177.39 (18)	B1—N2—C12—C5	2.9 (2)
N1—C1—C2—C3	−0.4 (3)	C15—N2—C12—C13	0.65 (18)
C1—C2—C3—C4	0.2 (2)	B1—N2—C12—C13	−173.74 (15)
C1—N1—C4—C3	−0.3 (2)	C5—C12—C13—C14	−176.43 (17)
B1—N1—C4—C3	−177.21 (16)	N2—C12—C13—C14	0.0 (2)
C1—N1—C4—C5	174.28 (16)	C12—C13—C14—C15	−0.6 (2)
B1—N1—C4—C5	−2.6 (3)	C17—N3—C15—N2	178.89 (18)
C2—C3—C4—N1	0.1 (2)	C16—N3—C15—N2	−0.4 (3)
C2—C3—C4—C5	−173.55 (19)	C17—N3—C15—C14	−2.5 (3)
N1—C4—C5—C12	0.4 (2)	C16—N3—C15—C14	178.2 (2)
C3—C4—C5—C12	173.53 (18)	C12—N2—C15—N3	177.73 (17)
N1—C4—C5—C6	−177.34 (15)	B1—N2—C15—N3	−8.7 (3)
C3—C4—C5—C6	−4.2 (3)	C12—N2—C15—C14	−1.01 (18)
C12—C5—C6—C11	−56.0 (2)	B1—N2—C15—C14	172.56 (17)
C4—C5—C6—C11	121.79 (18)	C13—C14—C15—N3	−177.78 (17)
C12—C5—C6—C7	126.68 (19)	C13—C14—C15—N2	1.0 (2)
C4—C5—C6—C7	−55.6 (2)	C1—N1—B1—F2	−51.6 (2)
C11—C6—C7—C8	−0.4 (3)	C4—N1—B1—F2	124.74 (18)
C5—C6—C7—C8	177.02 (19)	C1—N1—B1—F1	68.0 (2)
C6—C7—C8—C9	−0.1 (4)	C4—N1—B1—F1	−115.69 (19)
C7—C8—C9—C10	0.7 (4)	C1—N1—B1—N2	−172.08 (16)
C8—C9—C10—C11	−0.8 (4)	C4—N1—B1—N2	4.2 (2)
C9—C10—C11—C6	0.3 (3)	C15—N2—B1—F2	63.9 (2)
C7—C6—C11—C10	0.3 (3)	C12—N2—B1—F2	−123.27 (17)
C5—C6—C11—C10	−177.12 (18)	C15—N2—B1—F1	−56.7 (2)
C4—C5—C12—C13	175.20 (16)	C12—N2—B1—F1	116.07 (17)
C6—C5—C12—C13	−7.1 (3)	C15—N2—B1—N1	−176.99 (16)
C4—C5—C12—N2	−0.7 (2)	C12—N2—B1—N1	−4.2 (2)
C6—C5—C12—N2	176.99 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F2ⁱ	0.93	2.51	3.291 (3)	142
C17—H17C···F2ⁱⁱ	0.96	2.49	3.282 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆BF₂N₃
M_r	311.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8033 (6), 25.524 (2), 9.9776 (5)
β (°)	128.671 (4)
V (Å³)	1551.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	11054, 2736, 2025
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.03
No. of reflections	2736
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.14

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
C1—H1···F2ⁱ	0.93	2.512	3.291 (3)	142
C17—H17C···F2ⁱⁱ	0.96	2.491	3.282 (3)	140

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

Acknowledgements

This work was supported by the Research Culture Funds of Anhui Normal University (160–721137).

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jiao, L. J., Pang, W. D., Zhou, J. Y., Wei, Y., Mu, X. L., Bai, G. F. & Hao, E. H. (2011). J. Org. Chem. 76, 9988–9996. Web of Science CSD CrossRef CAS PubMed 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
Trieflinger, C., Rurack, K. & Daub, J. (2005). Angew. Chem. Int. Ed. 44, 2288–2291. Web of Science CrossRef CAS Google Scholar

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