Cocrystals of 2,3,5,6-tetra­fluoro­benzene-1,4-diol with diaza aromatic compounds

2,3,5,6-Tetra­fluoro­benzene-1,4-diol easily forms cocrystals with heteroaromatic bases containing the pyrazine unit. In the 1:1 complexes with pyrazine, C₆H₂F₄O₂·C₄H₄N₂, (I), and quinoxaline, C₆H₂F₄O₂·C₈H₆N₂, (II), the crystal components are linked via O-H...N hydrogen bonds into one-dimensional chains. With the largest base, phenazine, the 1:2 benzenediol-phenazine complex, C₆H₂F₄O₂·2C₁₂H₈N₂, (III), was obtained, with the mol­ecules linked via O-H...N inter­actions into a discrete heterotrimer. In all three cocrystals, the two types of mol­ecules are organized into layers via softer C-H...O and C-H...F inter­actions and [pi]-[pi] stacking inter­actions, with stronger hydrogen bonds linking mol­ecules of adjacent layers. In (II) and (III), mol­ecules are arranged into heterostacks, whereas in (I) separate stacks are formed by the heterocyclic base and the benzene­diol molecule.

Computing details

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis CCD (Oxford Diffraction, 2004); data reduction: CrysAlis RED (Oxford Diffraction, 2004); 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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(I) pyrazine–2,3,5,6-tetrafluorobenzene-1,4-diol (1/1)

Crystal data

C6H2F4O2·C4H4N2	Z = 1
Mr = 262.17	F(000) = 132
Triclinic, P1	Dx = 1.679 Mg m^−3
Hall symbol: -P 1	Melting point = 444–446 K
a = 3.6671 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.585 (2) Å	Cell parameters from 1281 reflections
c = 9.582 (2) Å	θ = 4–25°
α = 88.14 (2)°	µ = 0.17 mm^−1
β = 85.67 (2)°	T = 294 K
γ = 77.41 (2)°	Needle, colourless
V = 259.34 (11) Å^3	0.60 × 0.15 × 0.05 mm

Data collection

Kuma KM-4 CCD κ geometry diffractometer	791 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 25.0°, θmin = 3.5°
ω scans	h = −3→4
1921 measured reflections	k = −8→9
917 independent reflections	l = −9→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: difference Fourier map
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0994P)^2] where P = (Fo^2 + 2Fc^2)/3
917 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.7507 (4)	0.47473 (16)	0.21929 (11)	0.0489 (4)
H1O	0.7952	0.3679	0.1883	0.059*
F2	0.5369 (4)	0.18462 (13)	0.37105 (11)	0.0566 (4)
F3	0.6964 (3)	0.78291 (13)	0.35828 (10)	0.0503 (4)
C1	0.6268 (4)	0.4821 (2)	0.35599 (15)	0.0334 (4)
C2	0.5227 (5)	0.3426 (2)	0.43377 (16)	0.0357 (4)
C3	0.5985 (4)	0.6411 (2)	0.42691 (16)	0.0337 (4)
N1A	0.9210 (4)	0.15481 (19)	0.08028 (13)	0.0400 (4)
C2A	1.0880 (5)	−0.0050 (2)	0.13160 (16)	0.0398 (5)
H2A	1.1431	−0.0128	0.2282	0.048*
C3A	0.8336 (5)	0.1583 (2)	−0.05265 (16)	0.0410 (5)
H3A	0.7227	0.2747	−0.0906	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0776 (9)	0.0364 (8)	0.0306 (7)	−0.0117 (6)	0.0095 (6)	−0.0048 (5)
F2	0.0937 (9)	0.0318 (6)	0.0470 (6)	−0.0225 (6)	0.0105 (6)	−0.0148 (4)
F3	0.0744 (8)	0.0310 (6)	0.0462 (6)	−0.0176 (5)	0.0070 (5)	0.0043 (4)
C1	0.0379 (9)	0.0317 (9)	0.0292 (8)	−0.0044 (7)	−0.0018 (6)	−0.0021 (6)
C2	0.0438 (9)	0.0259 (9)	0.0372 (9)	−0.0060 (7)	−0.0025 (7)	−0.0067 (6)
C3	0.0381 (9)	0.0267 (9)	0.0359 (8)	−0.0068 (6)	−0.0009 (7)	0.0025 (6)
N1A	0.0463 (9)	0.0385 (9)	0.0344 (8)	−0.0088 (7)	0.0036 (6)	−0.0057 (6)
C2A	0.0449 (10)	0.0459 (10)	0.0286 (8)	−0.0101 (8)	−0.0008 (7)	−0.0011 (6)
C3A	0.0462 (10)	0.0385 (10)	0.0349 (8)	−0.0035 (7)	0.0017 (7)	0.0009 (7)

Geometric parameters (Å, º)

O1—C1	1.352 (2)	C3—C2^i	1.375 (2)
O1—H1O	0.8500	N1A—C2A	1.330 (2)
F2—C2	1.3473 (19)	N1A—C3A	1.335 (2)
F3—C3	1.3438 (19)	C2A—C3A^ii	1.373 (2)
C1—C2	1.379 (2)	C2A—H2A	0.9600
C1—C3	1.383 (2)	C3A—H3A	0.9601
C1—O1—H1O	112.3	C2^i—C3—C1	121.86 (15)
O1—C1—C2	125.50 (15)	C2A—N1A—C3A	116.30 (14)
O1—C1—C3	118.87 (14)	N1A—C2A—C3A^ii	122.05 (14)
C2—C1—C3	115.62 (15)	N1A—C2A—H2A	118.2
F2—C2—C3^i	118.52 (15)	C3A^ii—C2A—H2A	119.7
F2—C2—C1	118.96 (14)	N1A—C3A—C2A^ii	121.64 (15)
C3^i—C2—C1	122.51 (16)	N1A—C3A—H3A	116.1
F3—C3—C2^i	119.02 (15)	C2A^ii—C3A—H3A	122.2
F3—C3—C1	119.11 (14)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.85	1.90	2.7343 (19)	167
C2A—H2A···F3^iii	0.96	2.64	3.350 (2)	131
C3A—H3A···O1^iv	0.96	2.62	3.538 (2)	159

Symmetry codes: (iii) x+1, y−1, z; (iv) −x+1, −y+1, −z.

(II) quinoxaline–2,3,5,6-tetrafluorobenzene-1,4-diol (1/1)

Crystal data

C8H6N2·C6H2F4O2	Dx = 1.642 Mg m^−3
Mr = 312.22	Melting point = 439–441 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4532 reflections
a = 7.2094 (5) Å	θ = 4–25°
b = 7.4290 (4) Å	µ = 0.15 mm^−1
c = 23.585 (13) Å	T = 294 K
V = 1263.2 (7) Å^3	Block, colourless
Z = 4	0.60 × 0.40 × 0.40 mm
F(000) = 632

Data collection

Kuma KM-4 CCD κ geometry diffractometer	1208 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.0°, θmin = 3.8°
ω scans	h = −4→8
6629 measured reflections	k = −8→8
1324 independent reflections	l = −27→28

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.0889P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1324 reflections	Δρmax = 0.17 e Å^−3
200 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.062 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4547 (2)	0.3567 (3)	0.76926 (6)	0.0568 (5)
H1O	0.4780	0.3742	0.7344	0.068*
F2	0.79605 (19)	0.4874 (2)	0.73004 (5)	0.0558 (5)
F3	1.0550 (2)	0.6061 (3)	0.80186 (5)	0.0620 (5)
O4	0.9993 (2)	0.6086 (3)	0.91562 (6)	0.0518 (5)
H4O	0.9760	0.5872	0.9503	0.062*
F5	0.65782 (19)	0.4845 (2)	0.95518 (5)	0.0500 (4)
F6	0.3983 (2)	0.3604 (2)	0.88326 (6)	0.0576 (4)
C1	0.5882 (3)	0.4213 (3)	0.80398 (8)	0.0367 (5)
C2	0.7587 (3)	0.4858 (3)	0.78606 (8)	0.0370 (5)
C3	0.8915 (3)	0.5472 (3)	0.82274 (9)	0.0380 (5)
C4	0.8635 (3)	0.5477 (3)	0.88086 (9)	0.0357 (5)
C5	0.6933 (3)	0.4851 (3)	0.89873 (8)	0.0343 (5)
C6	0.5597 (3)	0.4221 (3)	0.86215 (9)	0.0372 (5)
N1A	0.4814 (3)	0.3946 (3)	0.65244 (7)	0.0382 (5)
C2A	0.6234 (3)	0.3385 (3)	0.62236 (10)	0.0420 (6)
H2A	0.7269	0.2851	0.6417	0.050*
C3A	0.6283 (3)	0.3531 (3)	0.56264 (10)	0.0429 (6)
H3A	0.7349	0.3081	0.5428	0.051*
N4A	0.4930 (3)	0.4245 (3)	0.53347 (7)	0.0393 (5)
C5A	0.1906 (3)	0.5625 (3)	0.53483 (9)	0.0398 (5)
H5A	0.1920	0.5722	0.4942	0.048*
C6A	0.0414 (3)	0.6228 (3)	0.56504 (10)	0.0443 (6)
H6A	−0.0609	0.6775	0.5455	0.053*
C7A	0.0358 (3)	0.6069 (3)	0.62460 (10)	0.0442 (6)
H7A	−0.0705	0.6503	0.6450	0.053*
C8A	0.1790 (3)	0.5310 (3)	0.65327 (9)	0.0399 (5)
H8A	0.1735	0.5192	0.6938	0.048*
C9A	0.3366 (3)	0.4690 (3)	0.62353 (8)	0.0325 (5)
C10A	0.3422 (3)	0.4848 (3)	0.56344 (9)	0.0333 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0464 (9)	0.0918 (14)	0.0321 (8)	−0.0208 (11)	−0.0045 (7)	0.0018 (9)
F2	0.0572 (9)	0.0879 (11)	0.0224 (6)	−0.0160 (9)	0.0062 (6)	−0.0016 (7)
F3	0.0508 (8)	0.0993 (12)	0.0359 (7)	−0.0306 (9)	0.0093 (7)	−0.0020 (8)
O4	0.0494 (9)	0.0770 (12)	0.0289 (8)	−0.0214 (10)	−0.0010 (7)	−0.0008 (8)
F5	0.0511 (8)	0.0746 (10)	0.0242 (7)	−0.0024 (8)	0.0083 (6)	−0.0010 (6)
F6	0.0390 (7)	0.0939 (11)	0.0400 (7)	−0.0141 (8)	0.0083 (6)	0.0030 (8)
C1	0.0369 (11)	0.0458 (12)	0.0274 (10)	−0.0015 (11)	−0.0030 (9)	0.0020 (9)
C2	0.0437 (12)	0.0443 (12)	0.0231 (9)	−0.0014 (11)	0.0035 (9)	0.0001 (9)
C3	0.0368 (12)	0.0452 (13)	0.0320 (11)	−0.0059 (10)	0.0058 (9)	0.0013 (10)
C4	0.0400 (11)	0.0393 (11)	0.0280 (10)	−0.0018 (10)	0.0000 (9)	−0.0017 (9)
C5	0.0419 (12)	0.0393 (11)	0.0217 (10)	0.0027 (11)	0.0041 (8)	0.0013 (8)
C6	0.0321 (11)	0.0449 (12)	0.0345 (10)	0.0019 (11)	0.0068 (9)	0.0029 (10)
N1A	0.0423 (10)	0.0445 (11)	0.0279 (9)	−0.0032 (10)	−0.0051 (8)	0.0005 (8)
C2A	0.0403 (13)	0.0484 (13)	0.0372 (12)	0.0015 (11)	−0.0060 (10)	0.0001 (10)
C3A	0.0391 (11)	0.0524 (14)	0.0372 (12)	0.0022 (12)	0.0021 (10)	−0.0028 (10)
N4A	0.0398 (10)	0.0501 (11)	0.0279 (8)	−0.0026 (9)	0.0024 (8)	−0.0014 (9)
C5A	0.0407 (12)	0.0484 (13)	0.0303 (10)	−0.0039 (11)	−0.0074 (9)	0.0030 (10)
C6A	0.0395 (12)	0.0481 (14)	0.0453 (13)	−0.0025 (11)	−0.0095 (11)	0.0021 (11)
C7A	0.0359 (11)	0.0477 (13)	0.0490 (13)	−0.0031 (11)	0.0046 (10)	−0.0031 (11)
C8A	0.0442 (12)	0.0455 (12)	0.0300 (11)	−0.0068 (12)	0.0040 (9)	−0.0013 (9)
C9A	0.0350 (11)	0.0359 (10)	0.0265 (10)	−0.0080 (10)	−0.0021 (8)	−0.0013 (8)
C10A	0.0358 (11)	0.0370 (11)	0.0270 (10)	−0.0073 (10)	−0.0025 (9)	−0.0001 (8)

Geometric parameters (Å, º)

O1—C1	1.352 (3)	C2A—C3A	1.413 (3)
O1—H1O	0.8500	C2A—H2A	0.9601
F2—C2	1.348 (2)	C3A—N4A	1.306 (3)
F3—C3	1.350 (2)	C3A—H3A	0.9600
O4—C4	1.355 (3)	N4A—C10A	1.372 (3)
O4—H4O	0.8501	C5A—C6A	1.365 (3)
F5—C5	1.356 (2)	C5A—C10A	1.409 (3)
F6—C6	1.346 (3)	C5A—H5A	0.9600
C1—C2	1.385 (3)	C6A—C7A	1.410 (3)
C1—C6	1.387 (3)	C6A—H6A	0.9600
C2—C3	1.369 (3)	C7A—C8A	1.357 (3)
C3—C4	1.385 (3)	C7A—H7A	0.9600
C4—C5	1.379 (3)	C8A—C9A	1.412 (3)
C5—C6	1.375 (3)	C8A—H8A	0.9600
N1A—C2A	1.313 (3)	C9A—C10A	1.423 (3)
N1A—C9A	1.364 (3)
C1—O1—H1O	113.0	C3A—C2A—H2A	119.1
C4—O4—H4O	112.1	N4A—C3A—C2A	122.5 (2)
O1—C1—C2	124.73 (19)	N4A—C3A—H3A	118.8
O1—C1—C6	119.7 (2)	C2A—C3A—H3A	118.7
C2—C1—C6	115.6 (2)	C3A—N4A—C10A	116.94 (18)
F2—C2—C3	118.5 (2)	C6A—C5A—C10A	119.7 (2)
F2—C2—C1	118.6 (2)	C6A—C5A—H5A	120.3
C3—C2—C1	122.90 (19)	C10A—C5A—H5A	120.0
F3—C3—C2	119.21 (19)	C5A—C6A—C7A	121.0 (2)
F3—C3—C4	119.2 (2)	C5A—C6A—H6A	119.6
C2—C3—C4	121.6 (2)	C7A—C6A—H6A	119.4
O4—C4—C5	124.83 (18)	C8A—C7A—C6A	120.6 (2)
O4—C4—C3	119.6 (2)	C8A—C7A—H7A	119.8
C5—C4—C3	115.5 (2)	C6A—C7A—H7A	119.6
F5—C5—C6	118.89 (19)	C7A—C8A—C9A	120.0 (2)
F5—C5—C4	117.97 (19)	C7A—C8A—H8A	120.2
C6—C5—C4	123.14 (18)	C9A—C8A—H8A	119.8
F6—C6—C5	119.30 (19)	N1A—C9A—C8A	119.98 (18)
F6—C6—C1	119.5 (2)	N1A—C9A—C10A	120.63 (19)
C5—C6—C1	121.2 (2)	C8A—C9A—C10A	119.4 (2)
C2A—N1A—C9A	117.08 (18)	N4A—C10A—C5A	120.13 (19)
N1A—C2A—C3A	122.2 (2)	N4A—C10A—C9A	120.6 (2)
N1A—C2A—H2A	118.6	C5A—C10A—C9A	119.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.85	1.94	2.776 (3)	168
O4—H4O···N4A^i	0.85	1.98	2.791 (3)	160
C2A—H2A···F3^ii	0.96	2.45	3.399 (3)	169
C3A—H3A···O4^ii	0.96	2.61	3.282 (3)	127
C7A—H7A···F2^iii	0.96	2.53	3.156 (3)	123
C6A—H6A···F5^iv	0.96	2.54	3.068 (3)	114

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

(III) phenazine–2,3,5,6-tetrafluorobenzene-1,4-diol (2/1)

Crystal data

2C12H8N2·C6H2F4O2	F(000) = 556
Mr = 542.48	Dx = 1.472 Mg m^−3
Monoclinic, P21/n	Melting point = 474–475 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.1482 (5) Å	Cell parameters from 4663 reflections
b = 11.0393 (6) Å	θ = 4–25°
c = 12.4185 (8) Å	µ = 0.12 mm^−1
β = 102.585 (5)°	T = 294 K
V = 1224.01 (12) Å^3	Prism, yellow
Z = 2	0.40 × 0.40 × 0.30 mm

Data collection

Kuma KM-4 CCD κ geometry diffractometer	1862 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.4°, θmin = 4.6°
ω scans	h = −7→11
8327 measured reflections	k = −13→13
2476 independent reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0803P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2476 reflections	Δρmax = 0.23 e Å^−3
182 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.21884 (10)	0.41473 (9)	0.39769 (8)	0.0511 (3)
H1O	0.2102	0.3950	0.3304	0.061*
F2	0.41476 (9)	0.51907 (8)	0.27740 (6)	0.0551 (3)
F3	0.68533 (9)	0.59817 (8)	0.38071 (6)	0.0561 (3)
C1	0.35657 (14)	0.45670 (11)	0.44484 (10)	0.0360 (3)
C2	0.45577 (14)	0.50828 (11)	0.38841 (10)	0.0363 (3)
C3	0.59460 (14)	0.54945 (11)	0.44136 (10)	0.0369 (3)
N1A	0.14220 (11)	0.34095 (9)	0.18331 (8)	0.0381 (3)
C2A	0.23286 (13)	0.29055 (11)	0.12365 (10)	0.0366 (3)
C3A	0.38075 (15)	0.25496 (12)	0.17667 (13)	0.0475 (4)
H3	0.4142	0.2654	0.2549	0.057*
C4A	0.47266 (17)	0.20697 (14)	0.11650 (15)	0.0587 (4)
H4	0.5721	0.1833	0.1530	0.070*
C5A	0.42575 (17)	0.19064 (15)	0.00123 (15)	0.0617 (5)
H5	0.4939	0.1575	−0.0398	0.074*
C6A	0.28522 (17)	0.22220 (14)	−0.05211 (13)	0.0531 (4)
H6	0.2541	0.2101	−0.1303	0.064*
C7A	0.18352 (14)	0.27264 (11)	0.00752 (11)	0.0373 (3)
N8A	0.04448 (12)	0.30270 (10)	−0.04654 (8)	0.0408 (3)
C9A	−0.04640 (14)	0.35099 (11)	0.01354 (11)	0.0368 (3)
C10A	−0.19506 (16)	0.38402 (13)	−0.03941 (13)	0.0485 (4)
H10	−0.2291	0.3720	−0.1174	0.058*
C11A	−0.28754 (17)	0.43271 (14)	0.01974 (15)	0.0581 (4)
H11	−0.3885	0.4524	−0.0165	0.070*
C12A	−0.23948 (17)	0.45313 (15)	0.13443 (14)	0.0576 (4)
H12	−0.3073	0.4891	0.1743	0.069*
C13A	−0.09857 (16)	0.42389 (13)	0.18818 (12)	0.0481 (4)
H13	−0.0669	0.4390	0.2659	0.058*
C14A	0.00251 (13)	0.37098 (11)	0.12967 (10)	0.0358 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0369 (5)	0.0785 (7)	0.0372 (5)	−0.0142 (5)	0.0068 (4)	−0.0101 (5)
F2	0.0577 (6)	0.0756 (6)	0.0284 (4)	−0.0122 (4)	0.0015 (4)	0.0024 (4)
F3	0.0534 (5)	0.0765 (6)	0.0422 (5)	−0.0212 (4)	0.0191 (4)	−0.0020 (4)
C1	0.0313 (7)	0.0412 (7)	0.0346 (7)	−0.0011 (5)	0.0049 (5)	−0.0059 (5)
C2	0.0409 (7)	0.0412 (7)	0.0255 (6)	0.0000 (5)	0.0045 (5)	−0.0009 (5)
C3	0.0384 (7)	0.0406 (7)	0.0342 (7)	−0.0044 (5)	0.0132 (5)	−0.0017 (5)
N1A	0.0357 (6)	0.0462 (6)	0.0311 (6)	−0.0033 (5)	0.0043 (5)	0.0010 (5)
C2A	0.0353 (7)	0.0373 (7)	0.0360 (7)	−0.0033 (5)	0.0055 (5)	0.0031 (5)
C3A	0.0372 (7)	0.0549 (9)	0.0472 (8)	0.0000 (6)	0.0019 (6)	0.0035 (7)
C4A	0.0385 (8)	0.0637 (10)	0.0726 (11)	0.0071 (7)	0.0094 (7)	0.0010 (8)
C5A	0.0496 (9)	0.0692 (10)	0.0716 (12)	0.0052 (8)	0.0248 (8)	−0.0111 (8)
C6A	0.0540 (9)	0.0627 (9)	0.0457 (8)	−0.0024 (7)	0.0175 (7)	−0.0102 (7)
C7A	0.0377 (7)	0.0382 (7)	0.0355 (7)	−0.0043 (5)	0.0069 (5)	−0.0011 (5)
N8A	0.0429 (6)	0.0451 (6)	0.0321 (6)	−0.0031 (5)	0.0030 (5)	−0.0032 (5)
C9A	0.0357 (7)	0.0360 (7)	0.0365 (7)	−0.0033 (5)	0.0028 (5)	0.0017 (5)
C10A	0.0411 (8)	0.0508 (8)	0.0470 (8)	−0.0003 (6)	−0.0047 (6)	0.0004 (7)
C11A	0.0363 (8)	0.0612 (9)	0.0726 (11)	0.0071 (7)	0.0024 (7)	0.0006 (8)
C12A	0.0455 (9)	0.0616 (10)	0.0690 (11)	0.0063 (7)	0.0201 (8)	−0.0016 (8)
C13A	0.0473 (8)	0.0563 (8)	0.0426 (8)	0.0002 (7)	0.0136 (6)	−0.0027 (6)
C14A	0.0341 (7)	0.0371 (7)	0.0349 (7)	−0.0044 (5)	0.0050 (5)	0.0013 (5)

Geometric parameters (Å, º)

O1—C1	1.3504 (15)	C5A—C6A	1.357 (2)
O1—H1O	0.8500	C5A—H5	0.9600
F2—C2	1.3528 (14)	C6A—C7A	1.4227 (19)
F3—C3	1.3483 (14)	C6A—H6	0.9601
C1—C2	1.3843 (18)	C7A—N8A	1.3441 (16)
C1—C3^i	1.3879 (18)	N8A—C9A	1.3425 (16)
C2—C3	1.3740 (18)	C9A—C10A	1.4231 (18)
C3—C1^i	1.3879 (18)	C9A—C14A	1.4309 (18)
N1A—C2A	1.3469 (16)	C10A—C11A	1.347 (2)
N1A—C14A	1.3475 (15)	C10A—H10	0.9600
C2A—C3A	1.4248 (18)	C11A—C12A	1.414 (2)
C2A—C7A	1.4280 (17)	C11A—H11	0.9601
C3A—C4A	1.349 (2)	C12A—C13A	1.355 (2)
C3A—H3	0.9601	C12A—H12	0.9600
C4A—C5A	1.413 (2)	C13A—C14A	1.4202 (18)
C4A—H4	0.9601	C13A—H13	0.9601
C1—O1—H1O	113.1	C5A—C6A—H6	119.9
O1—C1—C2	125.05 (12)	C7A—C6A—H6	119.8
O1—C1—C3^i	119.19 (11)	N8A—C7A—C6A	119.45 (12)
C2—C1—C3^i	115.76 (12)	N8A—C7A—C2A	121.79 (11)
F2—C2—C3	118.73 (11)	C6A—C7A—C2A	118.76 (12)
F2—C2—C1	119.03 (11)	C9A—N8A—C7A	116.98 (11)
C3—C2—C1	122.23 (12)	N8A—C9A—C10A	119.35 (12)
F3—C3—C2	118.81 (11)	N8A—C9A—C14A	121.73 (11)
F3—C3—C1^i	119.18 (11)	C10A—C9A—C14A	118.92 (12)
C2—C3—C1^i	122.00 (11)	C11A—C10A—C9A	120.05 (14)
C2A—N1A—C14A	117.46 (11)	C11A—C10A—H10	120.1
N1A—C2A—C3A	119.76 (12)	C9A—C10A—H10	119.9
N1A—C2A—C7A	121.04 (11)	C10A—C11A—C12A	121.22 (14)
C3A—C2A—C7A	119.20 (12)	C10A—C11A—H11	119.3
C4A—C3A—C2A	119.74 (14)	C12A—C11A—H11	119.5
C4A—C3A—H3	120.6	C13A—C12A—C11A	120.78 (14)
C2A—C3A—H3	119.7	C13A—C12A—H12	119.8
C3A—C4A—C5A	121.51 (14)	C11A—C12A—H12	119.4
C3A—C4A—H4	119.1	C12A—C13A—C14A	120.10 (13)
C5A—C4A—H4	119.4	C12A—C13A—H13	120.0
C6A—C5A—C4A	120.52 (14)	C14A—C13A—H13	119.9
C6A—C5A—H5	119.7	N1A—C14A—C13A	120.09 (12)
C4A—C5A—H5	119.8	N1A—C14A—C9A	120.99 (11)
C5A—C6A—C7A	120.25 (14)	C13A—C14A—C9A	118.92 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1A	0.85	1.89	2.7257 (14)	166
C3A—H3···N8A^ii	0.96	2.60	3.4958 (18)	155
C5A—H5···O1^iii	0.96	2.48	3.4203 (18)	165
C4A—H4···F3^iv	0.96	2.53	3.3445 (17)	143

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