Crystal structure of 2-cyano-1-methyl­pyridinium tetra­fluoro­borate

Vaccaro, F.A.; Koplitz, L.V.; Mague, J.T.

doi:10.1107/S2056989015016011

organic compounds

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ISSN: 2056-9890

Volume 71| Part 10| October 2015| Pages o697-o698

doi:10.1107/S2056989015016011

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Crystal structure of 2-cyano-1-methylpyridinium tetrafluoroborate

Francesca A. Vaccaro,^a Lynn V. Koplitz ^a and Joel T. Mague ^b ^*

^aDepartment of Chemistry, Loyola University, New Orleans, LA 70118, USA, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: joelt@tulane.edu

Edited by E. R. T. Tiekink, University of Malaya, Malaysia (Received 26 August 2015; accepted 26 August 2015; online 12 September 2015)

The asymmetric unit of the title salt, C₇H₇N₂⁺·BF₄⁻, comprises two independent but nearly identical formula units. The solid-state structure comprises corrugated layers of cations and anions, formed by C—H⋯F hydrogen bonding, that are approximately parallel to (010). Further C—H⋯F hydrogen bonding consolidates the three-dimensional architecture. The sample was refined as a two-component non-merohedral twin.

Keywords: crystal structure; salt; C—H⋯F interactions.

CCDC reference: 1420782

1. Related literature

For structures of other salts of the 2-cyano-1-methylpyridinium cation, see: Koplitz et al. (2012 ); Kammer et al. (2013 ). For structures of salts of the isomeric 2-cyanoanilinium cation, see: Zhang (2009 ); Cui & Chen (2010 ).

2. Experimental

2.1. Crystal data

C₇H₇N₂⁺·BF₄⁻
M_r = 205.96
Monoclinic, P 2₁
a = 7.9704 (16) Å
b = 7.5527 (15) Å
c = 14.570 (3) Å
β = 90.312 (3)°
V = 877.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 150 K
0.14 × 0.13 × 0.08 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.70, T_max = 0.99
16120 measured reflections
4566 independent reflections
3779 reflections with I > 2σ(I)
R_int = 0.057

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.122
S = 1.08
4566 reflections
256 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: the absolute structure could not be determined with certainty in this light-atom structure

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯F7ⁱ	0.98	2.50	3.407 (6)	154
C1—H1B⋯F8ⁱⁱ	0.98	2.54	3.498 (6)	166
C1—H1C⋯F3ⁱⁱⁱ	0.98	2.47	3.214 (5)	132
C2—H2⋯F7ⁱ	0.95	2.29	3.190 (5)	157
C3—H3⋯F1^iv	0.95	2.46	3.294 (6)	147
C5—H5⋯F1^v	0.95	2.45	3.306 (5)	149
C8—H8A⋯F2ⁱ	0.98	2.48	3.159 (6)	126
C8—H8C⋯F3ⁱⁱ	0.98	2.55	3.437 (6)	151
C9—H9⋯F3ⁱⁱ	0.95	2.52	3.392 (6)	152
C9—H9⋯F4ⁱⁱ	0.95	2.59	3.476 (6)	156
C10—H10⋯F6ⁱⁱ	0.95	2.54	3.167 (6)	123
C12—H12⋯F5ⁱ	0.95	2.49	3.277 (6)	141
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (iii) x, y-1, z; (iv) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (v) $[-x+1, y-{\script{1\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1420782

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015016011/tk5380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015016011/tk5380Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015016011/tk5380Isup3.cml

checkCIF report

Comment top

The asymmetric unit consists of two independent formula units. A portion of the C—H···F hydrogen bonding network which aids the packing of the several ions is shown in Fig. 1 with fuller depictions appearing in Figs 2 and 3. The solid state structure comprises corrugated layers of cations and anions formed by C—H···F hydrogen bonding between them and approximately parallel to (010). These layers are held to one another by additional C—H···F interactions.

Related literature top

For structures of other salts of the 2-cyano-1-methylpyridinium cation, see: Koplitz et al. (2012); Kammer et al. (2013). For structures of salts of the isomeric 2-cyanoanilinium cation, see: Zhang (2009); Cui & Chen (2010).

Experimental top

To 0.64 g (0.5 mmol) of 2-cyano-1-methylpyridinium iodide dissolved in 8.5 ml of 95% ethanol was added 1.08 g (0.55 mmol) of solid silver tetrafluoroborate with stirring. The reaction mixture was filtered to remove the precipitated AgI and the filtrate allowed to evaporate to dryness. From the resulting mass, crystals suitable for X-ray diffraction were selected.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the asymmetric unit with 50% probability ellipsoids. The C—H···F interaction is shown by a dotted line.
	Fig. 2. Packing viewed down the a axis showing an edge view of two corrugated layers and the C—H···F interactions (dotted lines) holding them together.
	Fig. 3. Packing viewed down the b axis providing a plan view of the corrugated sheets with C—H···F interactions shown as dotted lines.

2-Cyano-1-methylpyridinium tetrafluoroborate top

Crystal data top

C₇H₇N₂⁺·BF₄⁻	F(000) = 416
M_r = 205.96	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.9704 (16) Å	Cell parameters from 8457 reflections
b = 7.5527 (15) Å	θ = 2.6–29.0°
c = 14.570 (3) Å	µ = 0.15 mm⁻¹
β = 90.312 (3)°	T = 150 K
V = 877.1 (3) Å³	Block, colourless
Z = 4	0.14 × 0.13 × 0.08 mm

Data collection top

Bruker SMART APEX CCD diffractometer	4566 independent reflections
Radiation source: fine-focus sealed tube	3779 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 8.3660 pixels mm^-1	θ_max = 29.3°, θ_min = 2.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→10
T_min = 0.70, T_max = 0.99	l = −19→19
16120 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0572P)² + 0.091P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4566 reflections	Δρ_max = 0.33 e Å⁻³
256 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Absolute structure: The absolute structure could not be determined with certainty in this light-atom structure
Primary atom site location: structure-invariant direct methods

Crystal data top

C₇H₇N₂⁺·BF₄⁻	V = 877.1 (3) Å³
M_r = 205.96	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 7.9704 (16) Å	µ = 0.15 mm⁻¹
b = 7.5527 (15) Å	T = 150 K
c = 14.570 (3) Å	0.14 × 0.13 × 0.08 mm
β = 90.312 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	4566 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	3779 reflections with I > 2σ(I)
T_min = 0.70, T_max = 0.99	R_int = 0.057
16120 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.122	H-atom parameters constrained
S = 1.08	Δρ_max = 0.33 e Å⁻³
4566 reflections	Δρ_min = −0.27 e Å⁻³
256 parameters	Absolute structure: The absolute structure could not be determined with certainty in this light-atom structure

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 10 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. In the late stages of the refinement a consistent pattern of F_o² >> F_c² suggested twinning not yet accounted for. Use of the TwinRotMat routine in PLATON (Spek, 2009) generated the twin law -1 0 0 0 - 1 0 0 0 1, inclusion of which enabled satisfactory refinement as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.7369 (5)	0.1294 (4)	0.8819 (3)	0.0220 (7)
N2	0.3067 (5)	0.0851 (7)	0.8963 (3)	0.0416 (11)
C1	0.6868 (6)	0.1642 (6)	0.7854 (3)	0.0273 (10)
H1A	0.7826	0.2126	0.7518	0.041*
H1B	0.5943	0.2497	0.7841	0.041*
H1C	0.6504	0.0534	0.7565	0.041*
C2	0.8990 (6)	0.1331 (6)	0.9067 (3)	0.0264 (9)
H2	0.9807	0.1629	0.8620	0.032*
C3	0.9511 (6)	0.0952 (7)	0.9947 (3)	0.0299 (10)
H3	1.0671	0.0973	1.0100	0.036*
C4	0.8341 (6)	0.0543 (6)	1.0601 (3)	0.0283 (10)
H4	0.8678	0.0281	1.1213	0.034*
C5	0.6652 (6)	0.0520 (6)	1.0352 (3)	0.0274 (9)
H5	0.5819	0.0254	1.0795	0.033*
C6	0.6204 (5)	0.0884 (6)	0.9464 (3)	0.0232 (8)
C7	0.4472 (6)	0.0856 (7)	0.9165 (3)	0.0295 (10)
B1	0.7236 (7)	0.6589 (6)	0.8140 (3)	0.0242 (10)
F1	0.7151 (4)	0.5195 (3)	0.8770 (2)	0.0328 (6)
F2	0.8600 (4)	0.7654 (4)	0.8350 (2)	0.0361 (7)
F3	0.5771 (3)	0.7603 (4)	0.8200 (2)	0.0389 (7)
F4	0.7353 (4)	0.5925 (4)	0.72573 (19)	0.0446 (8)
N3	0.7497 (5)	0.3325 (5)	0.3758 (2)	0.0246 (8)
N4	1.1617 (6)	0.4550 (8)	0.3990 (3)	0.0454 (12)
C8	0.8099 (6)	0.3192 (7)	0.2807 (3)	0.0316 (10)
H8A	0.9110	0.2455	0.2790	0.047*
H8B	0.8361	0.4378	0.2575	0.047*
H8C	0.7225	0.2655	0.2421	0.047*
C9	0.5886 (6)	0.2988 (6)	0.3939 (3)	0.0292 (10)
H9	0.5148	0.2630	0.3460	0.035*
C10	0.5294 (6)	0.3159 (6)	0.4825 (3)	0.0302 (10)
H10	0.4148	0.2926	0.4954	0.036*
C11	0.6365 (6)	0.3668 (7)	0.5519 (3)	0.0310 (10)
H11	0.5962	0.3775	0.6129	0.037*
C12	0.8039 (6)	0.4028 (6)	0.5327 (3)	0.0304 (10)
H12	0.8794	0.4387	0.5798	0.036*
C13	0.8566 (6)	0.3847 (6)	0.4439 (3)	0.0255 (9)
C14	1.0267 (7)	0.4226 (7)	0.4190 (3)	0.0327 (10)
B2	0.7732 (7)	0.8421 (7)	0.3142 (3)	0.0273 (10)
F5	0.8153 (4)	0.9543 (4)	0.3856 (2)	0.0435 (8)
F6	0.6889 (5)	0.6960 (4)	0.3476 (2)	0.0500 (9)
F7	0.9153 (4)	0.7890 (6)	0.2691 (2)	0.0569 (10)
F8	0.6664 (4)	0.9294 (4)	0.2535 (2)	0.0464 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0256 (18)	0.0142 (16)	0.0263 (17)	0.0013 (14)	0.0025 (15)	−0.0004 (14)
N2	0.029 (2)	0.059 (3)	0.038 (2)	0.004 (2)	0.0041 (18)	−0.002 (2)
C1	0.037 (3)	0.022 (2)	0.023 (2)	−0.0010 (18)	−0.0026 (18)	0.0022 (17)
C2	0.023 (2)	0.023 (2)	0.033 (2)	−0.0011 (16)	0.0046 (19)	−0.0008 (19)
C3	0.025 (2)	0.033 (2)	0.032 (2)	0.0022 (19)	−0.0025 (19)	−0.002 (2)
C4	0.031 (2)	0.029 (2)	0.025 (2)	0.0000 (18)	−0.0006 (18)	−0.0012 (18)
C5	0.031 (2)	0.024 (2)	0.027 (2)	0.0002 (18)	0.0039 (19)	−0.0005 (18)
C6	0.023 (2)	0.0174 (19)	0.029 (2)	0.0007 (16)	0.0041 (17)	−0.0020 (17)
C7	0.029 (2)	0.028 (2)	0.032 (2)	0.0002 (18)	0.0046 (19)	−0.001 (2)
B1	0.029 (2)	0.018 (2)	0.026 (2)	−0.0007 (19)	0.001 (2)	0.0018 (18)
F1	0.0440 (15)	0.0189 (12)	0.0355 (14)	−0.0006 (12)	−0.0028 (13)	0.0047 (10)
F2	0.0336 (15)	0.0254 (14)	0.0492 (17)	−0.0069 (12)	−0.0028 (13)	0.0005 (12)
F3	0.0311 (15)	0.0235 (13)	0.062 (2)	0.0040 (12)	0.0021 (14)	0.0036 (13)
F4	0.069 (2)	0.0343 (16)	0.0304 (14)	−0.0020 (16)	0.0062 (15)	−0.0067 (13)
N3	0.0326 (19)	0.0141 (15)	0.0270 (18)	0.0007 (14)	0.0007 (15)	−0.0004 (14)
N4	0.034 (2)	0.060 (3)	0.042 (2)	−0.008 (2)	0.000 (2)	0.005 (2)
C8	0.041 (3)	0.025 (2)	0.028 (2)	−0.004 (2)	0.004 (2)	0.0001 (19)
C9	0.031 (2)	0.023 (2)	0.034 (2)	−0.0023 (17)	−0.005 (2)	0.0003 (19)
C10	0.029 (2)	0.023 (2)	0.039 (3)	−0.0003 (18)	0.0034 (19)	0.005 (2)
C11	0.037 (2)	0.029 (2)	0.027 (2)	0.0017 (19)	0.001 (2)	0.0019 (19)
C12	0.034 (2)	0.026 (2)	0.032 (2)	0.000 (2)	−0.003 (2)	0.0016 (19)
C13	0.029 (2)	0.0147 (18)	0.033 (2)	0.0023 (16)	−0.0026 (19)	0.0026 (17)
C14	0.035 (3)	0.031 (2)	0.032 (2)	−0.001 (2)	−0.002 (2)	0.002 (2)
B2	0.033 (3)	0.023 (2)	0.026 (2)	−0.002 (2)	0.002 (2)	0.004 (2)
F5	0.061 (2)	0.0328 (16)	0.0363 (16)	0.0103 (14)	−0.0076 (16)	−0.0078 (13)
F6	0.072 (2)	0.0196 (14)	0.059 (2)	0.0019 (15)	0.0198 (17)	0.0098 (14)
F7	0.0376 (17)	0.072 (3)	0.061 (2)	0.0042 (17)	0.0157 (15)	−0.0251 (19)
F8	0.057 (2)	0.0294 (16)	0.0522 (18)	−0.0021 (14)	−0.0197 (17)	0.0099 (14)

Geometric parameters (Å, º) top

N1—C2	1.340 (6)	N3—C9	1.336 (6)
N1—C6	1.360 (6)	N3—C13	1.362 (6)
N1—C1	1.484 (6)	N3—C8	1.473 (6)
N2—C7	1.157 (6)	N4—C14	1.143 (7)
C1—H1A	0.9800	C8—H8A	0.9800
C1—H1B	0.9800	C8—H8B	0.9800
C1—H1C	0.9800	C8—H8C	0.9800
C2—C3	1.376 (7)	C9—C10	1.382 (7)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.372 (7)	C10—C11	1.375 (7)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.392 (6)	C11—C12	1.392 (7)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.369 (6)	C12—C13	1.370 (6)
C5—H5	0.9500	C12—H12	0.9500
C6—C7	1.446 (6)	C13—C14	1.434 (7)
B1—F4	1.384 (6)	B2—F7	1.372 (6)
B1—F2	1.385 (6)	B2—F6	1.382 (6)
B1—F1	1.398 (5)	B2—F5	1.382 (6)
B1—F3	1.400 (6)	B2—F8	1.391 (6)

C2—N1—C6	118.7 (4)	C9—N3—C13	120.6 (4)
C2—N1—C1	120.4 (4)	C9—N3—C8	119.4 (4)
C6—N1—C1	120.9 (4)	C13—N3—C8	119.9 (4)
N1—C1—H1A	109.5	N3—C8—H8A	109.5
N1—C1—H1B	109.5	N3—C8—H8B	109.5
H1A—C1—H1B	109.5	H8A—C8—H8B	109.5
N1—C1—H1C	109.5	N3—C8—H8C	109.5
H1A—C1—H1C	109.5	H8A—C8—H8C	109.5
H1B—C1—H1C	109.5	H8B—C8—H8C	109.5
N1—C2—C3	122.1 (4)	N3—C9—C10	119.9 (5)
N1—C2—H2	118.9	N3—C9—H9	120.0
C3—C2—H2	118.9	C10—C9—H9	120.0
C4—C3—C2	119.5 (4)	C11—C10—C9	120.0 (4)
C4—C3—H3	120.3	C11—C10—H10	120.0
C2—C3—H3	120.3	C9—C10—H10	120.0
C3—C4—C5	118.8 (4)	C10—C11—C12	119.9 (4)
C3—C4—H4	120.6	C10—C11—H11	120.0
C5—C4—H4	120.6	C12—C11—H11	120.0
C6—C5—C4	119.4 (4)	C13—C12—C11	118.0 (5)
C6—C5—H5	120.3	C13—C12—H12	121.0
C4—C5—H5	120.3	C11—C12—H12	121.0
N1—C6—C5	121.5 (4)	N3—C13—C12	121.5 (4)
N1—C6—C7	116.7 (4)	N3—C13—C14	117.6 (4)
C5—C6—C7	121.7 (4)	C12—C13—C14	120.9 (5)
N2—C7—C6	177.1 (5)	N4—C14—C13	179.1 (6)
F4—B1—F2	111.1 (4)	F7—B2—F6	109.9 (4)
F4—B1—F1	109.9 (4)	F7—B2—F5	110.0 (4)
F2—B1—F1	109.5 (4)	F6—B2—F5	110.0 (4)
F4—B1—F3	108.5 (4)	F7—B2—F8	109.7 (4)
F2—B1—F3	108.8 (4)	F6—B2—F8	107.8 (4)
F1—B1—F3	109.1 (4)	F5—B2—F8	109.5 (4)

C6—N1—C2—C3	0.7 (7)	C13—N3—C9—C10	−0.4 (7)
C1—N1—C2—C3	−177.6 (4)	C8—N3—C9—C10	−178.0 (4)
N1—C2—C3—C4	−0.9 (8)	N3—C9—C10—C11	−0.3 (7)
C2—C3—C4—C5	0.2 (8)	C9—C10—C11—C12	0.7 (8)
C3—C4—C5—C6	0.7 (7)	C10—C11—C12—C13	−0.3 (7)
C2—N1—C6—C5	0.2 (6)	C9—N3—C13—C12	0.7 (7)
C1—N1—C6—C5	178.5 (4)	C8—N3—C13—C12	178.4 (4)
C2—N1—C6—C7	−179.9 (4)	C9—N3—C13—C14	−178.6 (4)
C1—N1—C6—C7	−1.6 (6)	C8—N3—C13—C14	−0.9 (7)
C4—C5—C6—N1	−0.9 (7)	C11—C12—C13—N3	−0.3 (7)
C4—C5—C6—C7	179.2 (5)	C11—C12—C13—C14	178.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F7ⁱ	0.98	2.50	3.407 (6)	154
C1—H1B···F8ⁱⁱ	0.98	2.54	3.498 (6)	166
C1—H1C···F3ⁱⁱⁱ	0.98	2.47	3.214 (5)	132
C2—H2···F7ⁱ	0.95	2.29	3.190 (5)	157
C3—H3···F1^iv	0.95	2.46	3.294 (6)	147
C5—H5···F1^v	0.95	2.45	3.306 (5)	149
C8—H8A···F2ⁱ	0.98	2.48	3.159 (6)	126
C8—H8C···F3ⁱⁱ	0.98	2.55	3.437 (6)	151
C9—H9···F3ⁱⁱ	0.95	2.52	3.392 (6)	152
C9—H9···F4ⁱⁱ	0.95	2.59	3.476 (6)	156
C10—H10···F6ⁱⁱ	0.95	2.54	3.167 (6)	123
C12—H12···F5ⁱ	0.95	2.49	3.277 (6)	141

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F7ⁱ	0.98	2.50	3.407 (6)	154
C1—H1B···F8ⁱⁱ	0.98	2.54	3.498 (6)	166
C1—H1C···F3ⁱⁱⁱ	0.98	2.47	3.214 (5)	132
C2—H2···F7ⁱ	0.95	2.29	3.190 (5)	157
C3—H3···F1^iv	0.95	2.46	3.294 (6)	147
C5—H5···F1^v	0.95	2.45	3.306 (5)	149
C8—H8A···F2ⁱ	0.98	2.48	3.159 (6)	126
C8—H8C···F3ⁱⁱ	0.98	2.55	3.437 (6)	151
C9—H9···F3ⁱⁱ	0.95	2.52	3.392 (6)	152
C9—H9···F4ⁱⁱ	0.95	2.59	3.476 (6)	156
C10—H10···F6ⁱⁱ	0.95	2.54	3.167 (6)	123
C12—H12···F5ⁱ	0.95	2.49	3.277 (6)	141

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

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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