2-(4-Flouroanilino)tropone

Steyl, G.

doi:10.1107/S1600536807050271

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2-(4-Flouroanilino)tropone

G. Steyl

The title compound, C₁₃H₁₀FNO, which was synthesized from the reaction of tosyloxytropone and 4-fluoroaniline, has two independent molecules of similar bond dimensions in the asymmetric unit. Adjacent molecules are linked by hydrogen bonds and C—H

F interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050271/ng2336sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050271/ng2336Isup2.hkl Contains datablock I

CCDC reference: 667383

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.083
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H45    ..  F24     ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H23    ..  F44     ..       2.57 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the current paper the title compound, (I), is presented as an example of a product formed during the exchange reaction of tosyloxytropone and the corresponding 4-flouroaniline. The compound is the first of a series of halogenated derivatives of tropolone type molecules, see Fig. 1. Two closely related derivatives of N-alkyl (Roesky & Burgstein, 1999) and N-aryl (Hicks & Brookhart, 2001) have been reported. The addition of a halogen moiety to the compound can drastically affect the packing of the molecule in the solid state.

Two independent molecules are present in the asymmetric unit, with the only observable difference being the rotation of the phenyl moiety compared to the tropone molecule. This is clearly illustrated by the torsional twist of the C—N—C—C (see Table 1) and the interplanar dihedral angle formed by the phenyl and seven membered tropone ring systems of 46.04 (3) and 41.45 (4) °, respectively.

Weak intra- and intermolecular interactions is observed in the solid state, see Table 2. The weak intermolecular hydrogen bonds form dimeric systems in the solid state consisting of the two independent units. The flouro moieties do have a significant effect on the packing of the molecule in the solid state, with C—F···H interactions being observed.

Related literature top

For general background, see: Hicks & Brookhart (2001); Kubo et al. (2005, 2006); Polonsky et al. (1981); Roesky & Burgstein (1999); Yamamoto et al. (2001). For related diketonato complexes, see: Janse van Rensburg & Roodt (2006); Janse van Rensburg et al. (2006).

Experimental top

The title compound was obtained during the coupling tosyloxytropone and 4-flouroaniline in a 1:1 ration in toluene. On evaporation of the solvent; crystals suitable for X-Ray crystallography was obtained.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. : Representation of the title compound (I), showing the numbering scheme and displacement ellipsoids (50% probability).

2-(4-Flouroanilino)tropone top

Crystal data top

C₁₃H₁₀FNO	F(000) = 896
M_r = 215.22	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9979 reflections
a = 9.9075 (3) Å	θ = 2.4–28.3°
b = 17.5746 (5) Å	µ = 0.10 mm⁻¹
c = 12.2212 (4) Å	T = 100 K
β = 96.714 (1)°	Cuboid, yellow
V = 2113.37 (11) Å³	0.19 × 0.18 × 0.18 mm
Z = 8

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4116 independent reflections
Radiation source: fine-focus sealed tube	3581 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 512 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 1998)	k = −20→21
T_min = 0.982, T_max = 0.983	l = −14→14
37801 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0338P)² + 0.8256P] where P = (F_o² + 2F_c²)/3
4116 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₁₀FNO	V = 2113.37 (11) Å³
M_r = 215.22	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9075 (3) Å	µ = 0.10 mm⁻¹
b = 17.5746 (5) Å	T = 100 K
c = 12.2212 (4) Å	0.19 × 0.18 × 0.18 mm
β = 96.714 (1)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	4116 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3581 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.983	R_int = 0.026
37801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
4116 reflections	Δρ_min = −0.20 e Å⁻³
289 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
F24	0.33924 (10)	0.60818 (5)	0.00722 (6)	0.0470 (2)
F44	0.09980 (9)	0.38655 (5)	−0.11523 (7)	0.0468 (2)
O31	0.32909 (8)	0.31212 (5)	0.52144 (7)	0.0265 (2)
O11	0.50514 (8)	0.63320 (5)	0.65968 (7)	0.0294 (2)
N32	0.20137 (9)	0.33470 (6)	0.33231 (8)	0.0213 (2)
H32	0.2874	0.3423	0.3569	0.018*
N12	0.42537 (10)	0.59783 (6)	0.46111 (8)	0.0221 (2)
H12	0.5013	0.6202	0.4887	0.019*
C21	0.39972 (12)	0.59728 (6)	0.34498 (10)	0.0210 (2)
C46	0.23044 (12)	0.40892 (7)	0.17152 (10)	0.0256 (3)
H46	0.2902	0.4412	0.2168	0.031*
C41	0.16614 (11)	0.34861 (7)	0.21878 (10)	0.0208 (2)
C26	0.50927 (12)	0.59112 (7)	0.28413 (10)	0.0240 (3)
H26	0.5982	0.5839	0.3210	0.029*
C42	0.07791 (11)	0.30169 (7)	0.15148 (10)	0.0225 (3)
H42	0.0340	0.2604	0.1830	0.027*
C11	0.39801 (11)	0.59507 (7)	0.64867 (10)	0.0214 (2)
C22	0.26927 (12)	0.60873 (7)	0.29035 (10)	0.0250 (3)
H22	0.1941	0.6137	0.3315	0.030*
C15	0.13306 (12)	0.49457 (7)	0.67800 (10)	0.0260 (3)
H15	0.0593	0.4683	0.7039	0.031*
C13	0.24472 (12)	0.51698 (7)	0.50645 (10)	0.0218 (2)
H13	0.2353	0.5017	0.4314	0.026*
C31	0.20423 (12)	0.29945 (6)	0.51716 (10)	0.0222 (3)
C32	0.12203 (11)	0.31135 (6)	0.40904 (10)	0.0207 (2)
C44	0.12025 (13)	0.37460 (8)	−0.00410 (11)	0.0307 (3)
C14	0.15145 (12)	0.48383 (7)	0.56961 (10)	0.0236 (3)
H14	0.0912	0.4482	0.5313	0.028*
C16	0.21218 (12)	0.54045 (7)	0.75443 (10)	0.0252 (3)
H16	0.1821	0.5431	0.8254	0.030*
C17	0.32642 (12)	0.58199 (7)	0.74198 (10)	0.0237 (3)
H17	0.3652	0.6067	0.8074	0.028*
C25	0.48976 (14)	0.59541 (7)	0.17019 (11)	0.0296 (3)
H25	0.5643	0.5913	0.1282	0.035*
C12	0.34890 (11)	0.56856 (6)	0.53560 (9)	0.0200 (2)
C23	0.24943 (14)	0.61280 (7)	0.17668 (11)	0.0301 (3)
H23	0.1610	0.6204	0.1390	0.036*
C34	−0.11526 (12)	0.27952 (7)	0.45227 (11)	0.0290 (3)
H34	−0.2057	0.2774	0.4166	0.035*
C37	0.14884 (13)	0.27657 (7)	0.61475 (11)	0.0292 (3)
H37	0.2136	0.2740	0.6784	0.035*
C43	0.05403 (12)	0.31496 (7)	0.03915 (10)	0.0272 (3)
H43	−0.0066	0.2836	−0.0069	0.033*
C24	0.35972 (15)	0.60573 (7)	0.11933 (10)	0.0310 (3)
C45	0.20782 (13)	0.42200 (7)	0.05935 (11)	0.0309 (3)
H45	0.2518	0.4628	0.0268	0.037*
C35	−0.10052 (13)	0.25745 (7)	0.56042 (12)	0.0320 (3)
H35	−0.1802	0.2401	0.5890	0.038*
C33	−0.01810 (12)	0.30469 (7)	0.38593 (11)	0.0242 (3)
H33	−0.0538	0.3196	0.3136	0.029*
C36	0.01932 (14)	0.25768 (7)	0.63340 (12)	0.0327 (3)
H36	0.0094	0.2425	0.7066	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F24	0.0714 (6)	0.0513 (5)	0.0165 (4)	−0.0117 (5)	−0.0026 (4)	0.0076 (3)
F44	0.0561 (5)	0.0553 (6)	0.0255 (5)	−0.0206 (4)	−0.0100 (4)	0.0137 (4)
O31	0.0221 (4)	0.0298 (5)	0.0274 (5)	−0.0002 (3)	0.0023 (3)	0.0019 (4)
O11	0.0238 (4)	0.0413 (5)	0.0232 (5)	−0.0093 (4)	0.0032 (3)	−0.0070 (4)
N32	0.0170 (5)	0.0237 (5)	0.0233 (5)	−0.0024 (4)	0.0026 (4)	0.0001 (4)
N12	0.0195 (5)	0.0287 (5)	0.0178 (5)	−0.0012 (4)	0.0005 (4)	−0.0028 (4)
C21	0.0264 (6)	0.0172 (6)	0.0188 (6)	0.0018 (4)	0.0007 (5)	−0.0002 (4)
C46	0.0262 (6)	0.0231 (6)	0.0271 (7)	−0.0047 (5)	0.0015 (5)	−0.0001 (5)
C41	0.0181 (5)	0.0209 (6)	0.0237 (6)	0.0023 (4)	0.0029 (4)	0.0011 (5)
C26	0.0278 (6)	0.0216 (6)	0.0226 (7)	0.0030 (5)	0.0031 (5)	0.0010 (5)
C42	0.0180 (5)	0.0213 (6)	0.0282 (7)	−0.0003 (4)	0.0035 (5)	0.0019 (5)
C11	0.0203 (6)	0.0225 (6)	0.0208 (6)	0.0016 (5)	0.0004 (4)	−0.0020 (4)
C22	0.0263 (6)	0.0223 (6)	0.0257 (7)	0.0025 (5)	0.0000 (5)	−0.0002 (5)
C15	0.0222 (6)	0.0253 (6)	0.0302 (7)	−0.0018 (5)	0.0019 (5)	0.0057 (5)
C13	0.0234 (6)	0.0211 (6)	0.0199 (6)	0.0037 (5)	−0.0021 (5)	−0.0018 (4)
C31	0.0241 (6)	0.0161 (6)	0.0271 (7)	0.0030 (4)	0.0059 (5)	0.0002 (4)
C32	0.0225 (6)	0.0146 (5)	0.0261 (6)	0.0016 (4)	0.0072 (5)	−0.0004 (4)
C44	0.0330 (7)	0.0353 (7)	0.0218 (7)	−0.0042 (6)	−0.0044 (5)	0.0080 (5)
C14	0.0209 (6)	0.0186 (6)	0.0297 (7)	0.0015 (4)	−0.0044 (5)	0.0012 (5)
C16	0.0268 (6)	0.0272 (6)	0.0220 (6)	0.0012 (5)	0.0050 (5)	0.0031 (5)
C17	0.0266 (6)	0.0252 (6)	0.0190 (6)	0.0000 (5)	0.0016 (5)	−0.0018 (5)
C25	0.0411 (7)	0.0261 (7)	0.0230 (7)	−0.0010 (5)	0.0101 (5)	0.0006 (5)
C12	0.0192 (5)	0.0209 (6)	0.0196 (6)	0.0056 (4)	0.0010 (4)	−0.0002 (4)
C23	0.0354 (7)	0.0254 (6)	0.0265 (7)	−0.0003 (5)	−0.0087 (5)	0.0042 (5)
C34	0.0216 (6)	0.0251 (6)	0.0419 (8)	0.0019 (5)	0.0107 (5)	−0.0026 (5)
C37	0.0326 (7)	0.0276 (7)	0.0280 (7)	0.0057 (5)	0.0068 (5)	0.0067 (5)
C43	0.0230 (6)	0.0290 (6)	0.0281 (7)	−0.0041 (5)	−0.0034 (5)	0.0009 (5)
C24	0.0512 (8)	0.0248 (6)	0.0157 (6)	−0.0043 (6)	−0.0019 (6)	0.0036 (5)
C45	0.0343 (7)	0.0271 (7)	0.0306 (7)	−0.0078 (5)	0.0007 (5)	0.0078 (5)
C35	0.0285 (6)	0.0276 (7)	0.0435 (8)	0.0010 (5)	0.0190 (6)	0.0026 (6)
C33	0.0222 (6)	0.0217 (6)	0.0293 (7)	0.0031 (5)	0.0059 (5)	−0.0002 (5)
C36	0.0398 (7)	0.0273 (7)	0.0343 (8)	0.0060 (6)	0.0179 (6)	0.0081 (5)

Geometric parameters (Å, º) top

F24—C24	1.3621 (15)	C13—C12	1.3886 (16)
F44—C44	1.3658 (15)	C13—C14	1.3985 (17)
O11—C11	1.2491 (14)	C13—H13	0.9500
N12—C12	1.3522 (15)	C31—C37	1.4277 (17)
N12—C21	1.4124 (15)	C31—C32	1.4837 (17)
O31—C31	1.2520 (14)	C32—C33	1.3890 (16)
N32—C32	1.3558 (15)	C44—C43	1.3746 (18)
N32—C41	1.4118 (15)	C44—C45	1.3750 (18)
N32—H32	0.8800	C14—H14	0.9500
N12—H12	0.8800	C16—C17	1.3702 (17)
C21—C26	1.3898 (17)	C16—H16	0.9500
C21—C22	1.3982 (16)	C17—H17	0.9500
C46—C45	1.3821 (18)	C25—C24	1.375 (2)
C46—C41	1.3961 (16)	C25—H25	0.9500
C46—H46	0.9500	C23—C24	1.371 (2)
C41—C42	1.3973 (16)	C23—H23	0.9500
C26—C25	1.3853 (18)	C34—C35	1.3689 (19)
C26—H26	0.9500	C34—C33	1.4007 (17)
C42—C43	1.3852 (18)	C34—H34	0.9500
C42—H42	0.9500	C37—C36	1.3701 (18)
C11—C17	1.4302 (17)	C37—H37	0.9500
C11—C12	1.4853 (16)	C43—H43	0.9500
C22—C23	1.3819 (18)	C45—H45	0.9500
C22—H22	0.9500	C35—C36	1.399 (2)
C15—C14	1.3712 (18)	C35—H35	0.9500
C15—C16	1.4020 (18)	C33—H33	0.9500
C15—H15	0.9500	C36—H36	0.9500

C12—N12—C21	128.67 (10)	C15—C14—C13	130.31 (11)
C32—N32—C41	129.45 (10)	C15—C14—H14	114.8
C32—N32—H32	115.3	C13—C14—H14	114.8
C41—N32—H32	115.3	C17—C16—C15	129.59 (12)
C12—N12—H12	115.7	C17—C16—H16	115.2
C21—N12—H12	115.7	C15—C16—H16	115.2
C26—C21—C22	119.46 (11)	C16—C17—C11	131.85 (11)
C26—C21—N12	118.57 (10)	C16—C17—H17	114.1
C22—C21—N12	121.77 (11)	C11—C17—H17	114.1
C45—C46—C41	120.51 (11)	C24—C25—C26	118.34 (12)
C45—C46—H46	119.7	C24—C25—H25	120.8
C41—C46—H46	119.7	C26—C25—H25	120.8
C46—C41—C42	119.26 (11)	N12—C12—C13	122.26 (11)
C46—C41—N32	117.76 (10)	N12—C12—C11	111.02 (10)
C42—C41—N32	122.83 (10)	C13—C12—C11	126.60 (11)
C25—C26—C21	120.51 (12)	C24—C23—C22	118.75 (12)
C25—C26—H26	119.7	C24—C23—H23	120.6
C21—C26—H26	119.7	C22—C23—H23	120.6
C43—C42—C41	120.44 (11)	C35—C34—C33	130.19 (12)
C43—C42—H42	119.8	C35—C34—H34	114.9
C41—C42—H42	119.8	C33—C34—H34	114.9
O11—C11—C17	119.65 (11)	C36—C37—C31	131.77 (13)
O11—C11—C12	116.76 (10)	C36—C37—H37	114.1
C17—C11—C12	123.53 (10)	C31—C37—H37	114.1
C23—C22—C21	120.15 (12)	C44—C43—C42	118.39 (11)
C23—C22—H22	119.9	C44—C43—H43	120.8
C21—C22—H22	119.9	C42—C43—H43	120.8
C14—C15—C16	126.56 (11)	F24—C24—C23	118.52 (12)
C14—C15—H15	116.7	F24—C24—C25	118.70 (12)
C16—C15—H15	116.7	C23—C24—C25	122.78 (12)
C12—C13—C14	130.51 (11)	C44—C45—C46	118.49 (12)
C12—C13—H13	114.7	C44—C45—H45	120.8
C14—C13—H13	114.7	C46—C45—H45	120.8
O31—C31—C37	119.31 (11)	C34—C35—C36	126.98 (12)
O31—C31—C32	116.68 (10)	C34—C35—H35	116.5
C37—C31—C32	123.99 (11)	C36—C35—H35	116.5
N32—C32—C33	122.10 (11)	C32—C33—C34	130.33 (12)
N32—C32—C31	110.88 (10)	C32—C33—H33	114.8
C33—C32—C31	126.92 (11)	C34—C33—H33	114.8
F44—C44—C43	118.53 (11)	C37—C36—C35	129.50 (13)
F44—C44—C45	118.56 (11)	C37—C36—H36	115.2
C43—C44—C45	122.90 (12)	C35—C36—H36	115.2

C12—N12—C21—C26	−145.61 (12)	C21—N12—C12—C11	−168.38 (10)
C12—N12—C21—C22	39.51 (17)	C14—C13—C12—N12	−176.39 (11)
C45—C46—C41—C42	−0.32 (18)	C14—C13—C12—C11	7.9 (2)
C45—C46—C41—N32	175.26 (11)	O11—C11—C12—N12	−5.99 (15)
C32—N32—C41—C46	143.54 (12)	C17—C11—C12—N12	171.17 (11)
C32—N32—C41—C42	−41.05 (18)	O11—C11—C12—C13	170.11 (11)
C22—C21—C26—C25	−0.71 (18)	C17—C11—C12—C13	−12.73 (18)
N12—C21—C26—C25	−175.71 (11)	C21—C22—C23—C24	−0.27 (18)
C46—C41—C42—C43	−0.23 (17)	O31—C31—C37—C36	−178.35 (13)
N32—C41—C42—C43	−175.56 (11)	C32—C31—C37—C36	3.2 (2)
C26—C21—C22—C23	0.91 (18)	F44—C44—C43—C42	178.23 (11)
N12—C21—C22—C23	175.74 (11)	C45—C44—C43—C42	−0.7 (2)
C41—N32—C32—C33	−6.94 (18)	C41—C42—C43—C44	0.72 (18)
C41—N32—C32—C31	176.37 (10)	C22—C23—C24—F24	178.64 (11)
O31—C31—C32—N32	−0.01 (14)	C22—C23—C24—C25	−0.6 (2)
C37—C31—C32—N32	178.46 (11)	C26—C25—C24—F24	−178.45 (11)
O31—C31—C32—C33	−176.51 (11)	C26—C25—C24—C23	0.79 (19)
C37—C31—C32—C33	1.97 (19)	F44—C44—C45—C46	−178.76 (12)
C16—C15—C14—C13	−3.7 (2)	C43—C44—C45—C46	0.2 (2)
C12—C13—C14—C15	2.4 (2)	C41—C46—C45—C44	0.3 (2)
C14—C15—C16—C17	−2.9 (2)	C33—C34—C35—C36	2.6 (2)
C15—C16—C17—C11	3.2 (2)	N32—C32—C33—C34	177.67 (12)
O11—C11—C17—C16	−176.82 (13)	C31—C32—C33—C34	−6.2 (2)
C12—C11—C17—C16	6.1 (2)	C35—C34—C33—C32	3.3 (2)
C21—C26—C25—C24	−0.12 (18)	C31—C37—C36—C35	−2.1 (2)
C21—N12—C12—C13	15.32 (18)	C34—C35—C36—C37	−2.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O31ⁱ	0.88	2.07	2.8891 (13)	154
N32—H32···O11ⁱ	0.88	2.13	2.9524 (12)	155
C45—H45···F24	0.95	2.72	3.6058 (15)	156
C23—H23···F44ⁱⁱ	0.95	2.57	3.4538 (16)	155

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀FNO
M_r	215.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.9075 (3), 17.5746 (5), 12.2212 (4)
β (°)	96.714 (1)
V (Å³)	2113.37 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.19 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.982, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	37801, 4116, 3581
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.083, 1.05
No. of reflections	4116
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004) and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···O31ⁱ	0.88	2.07	2.8891 (13)	153.6
N32—H32···O11ⁱ	0.88	2.13	2.9524 (12)	154.7
C45—H45···F24	0.95	2.72	3.6058 (15)	156.0
C23—H23···F44ⁱⁱ	0.95	2.57	3.4538 (16)	155.0

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

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