Quantitative analysis of solid-state diversity in tri­fluoro­methyl­ated phenylhydrazones

The cooperative roles of various structural motifs associated with the presence of different intermolecular interactions in the formation of molecular crystals are investigated in a series of tri­fluoro­methyl­ated phenyl­hydrazones. Out of the six compounds analysed, two exhibit three-dimensional structural similarities with geometrically equivalent building blocks, while a third exists as two polymorphic forms crystallized from ethanol solutions at low temperature (277 K) and room temperature (298 K), respectively. The compounds were characterized via single-crystal and powder X-ray diffraction techniques and differential scanning calorimetry. In the absence of any strong hydrogen bonding, the supramolecular constructs are primarily stabilized via molecular pairs with a high dispersion-energy contribution, due to the presence of molecular stacking along the molecular backbone along with C—H...π interactions in the solid state, in preference to an electrostatic contribution. The interaction energies for the most stabilizing molecular building blocks are in the range −29 to −43 kJ mol⁻¹. In addition, weak N—H...F, C—H...F and N—H...C interactions and F...F, F...C, F...N and C...N contacts act as secondary motifs, providing additional stability to the crystal packing. The overall molecular arrangements are carefully analysed in terms of their nature and energetics, and the roles of different molecular pairs towards the crystal structure are delineated. A topological study using the quantum theory of atoms in molecules was used to characterize all the atomic interactions in the solid state. It established the presence of (3, −1) bond critical points and the closed-shell nature of all the interactions.

Computing details

Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016) for HT03, HT33C, HT33P; SHELXL2014/7 (Sheldrick, 2014) for HT11, HT13, HT20, HT31.

(HT03)

Crystal data

C14H11F3N2	Z = 4
Mr = 264.25	F(000) = 544
Triclinic, P1	Dx = 1.425 Mg m^−3
a = 9.6399 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3142 (14) Å	Cell parameters from 9812 reflections
c = 13.4202 (18) Å	θ = 2.3–30.9°
α = 99.961 (4)°	µ = 0.12 mm^−1
β = 107.306 (4)°	T = 100 K
γ = 97.321 (4)°	Plate, colorless
V = 1231.8 (3) Å^3	0.23 × 0.16 × 0.14 mm

Data collection

Bruker APEX-II CCD diffractometer	4928 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.055
Absorption correction: multi-scan SADABS	θmax = 28.4°, θmin = 2.3°
Tmin = 0.703, Tmax = 0.737	h = −12→12
30881 measured reflections	k = −13→13
6111 independent reflections	l = −17→17

Refinement

Refinement on F^2	548 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.124	w = 1/[σ^2(Fo^2) + (0.055P)^2 + 0.6217P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
6111 reflections	Δρmax = 0.44 e Å^−3
405 parameters	Δρmin = −0.33 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.23936 (13)	0.62820 (11)	0.54396 (9)	0.0167 (2)
H1	0.2395 (18)	0.5622 (15)	0.5750 (13)	0.020*
N2	0.16039 (12)	0.60842 (11)	0.43844 (9)	0.0150 (2)
C1	0.33177 (14)	0.75036 (13)	0.59865 (10)	0.0146 (3)
C2	0.42060 (14)	0.76117 (13)	0.70445 (11)	0.0158 (3)
H2	0.413982	0.686968	0.737131	0.019*
C3	0.51780 (15)	0.87919 (13)	0.76154 (11)	0.0169 (3)
H3A	0.578121	0.885902	0.833234	0.020*
C4	0.52747 (15)	0.98833 (13)	0.71413 (11)	0.0176 (3)
C5	0.43638 (15)	0.97912 (13)	0.60999 (11)	0.0185 (3)
H5	0.441109	1.054611	0.578551	0.022*
C6	0.33865 (15)	0.86086 (13)	0.55151 (11)	0.0168 (3)
H6	0.277134	0.855011	0.480289	0.020*
C7	−0.01590 (14)	0.46567 (13)	0.28024 (10)	0.0149 (3)
C8	−0.11617 (15)	0.34381 (13)	0.23482 (11)	0.0167 (3)
H8	−0.125967	0.281426	0.277875	0.020*
C9	−0.20148 (15)	0.31347 (14)	0.12722 (12)	0.0206 (3)
H9	−0.270156	0.231060	0.097239	0.025*
C10	−0.18654 (17)	0.40317 (15)	0.06361 (12)	0.0233 (3)
H10	−0.244507	0.382183	−0.010031	0.028*
C11	−0.08605 (17)	0.52454 (14)	0.10800 (12)	0.0223 (3)
H11	−0.075266	0.585736	0.064212	0.027*
C12	−0.00211 (15)	0.55618 (13)	0.21538 (11)	0.0179 (3)
H12	0.065051	0.639464	0.245244	0.021*
C13	0.07305 (14)	0.49443 (13)	0.39366 (10)	0.0148 (3)
H13	0.066250	0.428599	0.434384	0.018*
C14	0.63196 (17)	1.11600 (15)	0.77569 (12)	0.0239 (3)
F1A	0.7513 (12)	1.0972 (13)	0.8470 (10)	0.062 (2)	0.52 (3)
F2A	0.6828 (8)	1.1842 (7)	0.7131 (5)	0.0326 (13)	0.52 (3)
F3A	0.5726 (9)	1.2001 (8)	0.8287 (9)	0.0603 (19)	0.52 (3)
F1B	0.7327 (14)	1.1018 (12)	0.8623 (9)	0.059 (2)	0.48 (3)
F2B	0.7044 (14)	1.1698 (11)	0.7195 (8)	0.071 (2)	0.48 (3)
F3B	0.5636 (9)	1.2113 (7)	0.8104 (7)	0.0412 (14)	0.48 (3)
N3	0.34435 (13)	0.46537 (12)	0.24783 (10)	0.0209 (3)
H3	0.2836 (18)	0.4659 (18)	0.2838 (13)	0.025*
N4	0.48449 (13)	0.53773 (11)	0.29437 (9)	0.0177 (2)
C15	0.30515 (15)	0.37512 (13)	0.15058 (11)	0.0164 (3)
C16	0.17094 (15)	0.28393 (14)	0.11733 (11)	0.0183 (3)
H16	0.108563	0.286905	0.160428	0.022*
C17	0.12891 (15)	0.18950 (13)	0.02187 (11)	0.0189 (3)
H17	0.037374	0.128204	−0.000757	0.023*
C18	0.22011 (16)	0.18417 (14)	−0.04081 (11)	0.0199 (3)
C19	0.35307 (16)	0.27573 (14)	−0.00898 (11)	0.0201 (3)
H19	0.414702	0.272473	−0.052632	0.024*
C20	0.39576 (15)	0.37159 (14)	0.08619 (11)	0.0183 (3)
H20	0.485960	0.434452	0.107501	0.022*
C21	0.66223 (15)	0.69155 (13)	0.44605 (11)	0.0171 (3)
C22	0.69568 (16)	0.75596 (14)	0.55336 (11)	0.0194 (3)
H22	0.624654	0.742538	0.588587	0.023*
C23	0.83248 (16)	0.83967 (14)	0.60895 (12)	0.0218 (3)
H23	0.854127	0.883751	0.681607	0.026*
C24	0.93690 (16)	0.85853 (14)	0.55810 (12)	0.0220 (3)
H24	1.030284	0.915382	0.595941	0.026*
C25	0.90481 (16)	0.79407 (14)	0.45147 (12)	0.0202 (3)
H25	0.976772	0.806820	0.416928	0.024*
C26	0.76847 (15)	0.71136 (13)	0.39536 (11)	0.0181 (3)
H26	0.747157	0.668158	0.322530	0.022*
C27	0.51562 (15)	0.60782 (14)	0.38946 (11)	0.0184 (3)
H27	0.442520	0.605470	0.423810	0.022*
C28	0.17097 (19)	0.08438 (16)	−0.14493 (13)	0.0292 (3)
F4A	0.0779 (8)	−0.0231 (7)	−0.1451 (8)	0.0322 (12)	0.509 (19)
F5A	0.1186 (19)	0.1286 (7)	−0.2270 (5)	0.083 (3)	0.509 (19)
F6A	0.2884 (6)	0.0254 (6)	−0.1564 (9)	0.0600 (19)	0.509 (19)
F4B	0.1032 (13)	−0.0328 (8)	−0.1446 (9)	0.051 (2)	0.491 (19)
F5B	0.0608 (6)	0.1258 (6)	−0.2210 (5)	0.0393 (12)	0.491 (19)
F6B	0.2697 (5)	0.0756 (13)	−0.1940 (6)	0.065 (3)	0.491 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0192 (6)	0.0140 (5)	0.0137 (5)	−0.0004 (4)	0.0015 (5)	0.0038 (4)
N2	0.0140 (5)	0.0168 (5)	0.0130 (5)	0.0022 (4)	0.0038 (4)	0.0018 (4)
C1	0.0118 (6)	0.0162 (6)	0.0156 (6)	0.0023 (5)	0.0054 (5)	0.0014 (5)
C2	0.0151 (6)	0.0172 (6)	0.0165 (6)	0.0040 (5)	0.0061 (5)	0.0050 (5)
C3	0.0149 (6)	0.0205 (6)	0.0139 (6)	0.0039 (5)	0.0038 (5)	0.0013 (5)
C4	0.0157 (6)	0.0159 (6)	0.0186 (7)	0.0009 (5)	0.0057 (5)	−0.0009 (5)
C5	0.0209 (7)	0.0148 (6)	0.0200 (7)	0.0026 (5)	0.0073 (6)	0.0043 (5)
C6	0.0172 (7)	0.0177 (6)	0.0152 (6)	0.0038 (5)	0.0045 (5)	0.0035 (5)
C7	0.0136 (6)	0.0155 (6)	0.0153 (6)	0.0036 (5)	0.0054 (5)	0.0013 (5)
C8	0.0155 (6)	0.0161 (6)	0.0186 (7)	0.0022 (5)	0.0067 (5)	0.0025 (5)
C9	0.0168 (7)	0.0188 (6)	0.0214 (7)	0.0002 (5)	0.0038 (6)	−0.0018 (5)
C10	0.0230 (7)	0.0246 (7)	0.0167 (7)	0.0071 (6)	−0.0006 (6)	0.0007 (6)
C11	0.0276 (8)	0.0198 (7)	0.0197 (7)	0.0069 (6)	0.0054 (6)	0.0071 (5)
C12	0.0189 (7)	0.0141 (6)	0.0186 (7)	0.0021 (5)	0.0044 (5)	0.0018 (5)
C13	0.0140 (6)	0.0155 (6)	0.0161 (6)	0.0037 (5)	0.0063 (5)	0.0037 (5)
C14	0.0247 (8)	0.0203 (7)	0.0211 (7)	−0.0022 (6)	0.0050 (6)	−0.0008 (6)
F1A	0.031 (2)	0.041 (3)	0.081 (5)	−0.0117 (17)	−0.026 (3)	0.019 (4)
F2A	0.040 (2)	0.0220 (17)	0.0269 (19)	−0.0106 (15)	0.0050 (15)	0.0058 (14)
F3A	0.052 (3)	0.044 (3)	0.072 (4)	−0.025 (2)	0.045 (3)	−0.039 (2)
F1B	0.070 (5)	0.024 (2)	0.039 (2)	−0.014 (3)	−0.034 (3)	0.0036 (15)
F2B	0.069 (4)	0.068 (4)	0.057 (4)	−0.049 (3)	0.042 (3)	−0.024 (3)
F3B	0.051 (3)	0.0140 (17)	0.050 (2)	0.0083 (17)	0.008 (2)	−0.0029 (18)
N3	0.0138 (6)	0.0259 (6)	0.0194 (6)	0.0004 (5)	0.0063 (5)	−0.0029 (5)
N4	0.0143 (5)	0.0175 (5)	0.0184 (6)	0.0022 (4)	0.0028 (4)	0.0011 (4)
C15	0.0170 (6)	0.0166 (6)	0.0143 (6)	0.0054 (5)	0.0030 (5)	0.0020 (5)
C16	0.0167 (7)	0.0194 (6)	0.0187 (7)	0.0038 (5)	0.0061 (5)	0.0032 (5)
C17	0.0170 (7)	0.0164 (6)	0.0208 (7)	0.0018 (5)	0.0040 (5)	0.0028 (5)
C18	0.0225 (7)	0.0179 (6)	0.0169 (6)	0.0043 (5)	0.0041 (6)	0.0010 (5)
C19	0.0207 (7)	0.0228 (7)	0.0181 (7)	0.0059 (5)	0.0083 (6)	0.0036 (5)
C20	0.0157 (6)	0.0198 (6)	0.0182 (7)	0.0022 (5)	0.0040 (5)	0.0044 (5)
C21	0.0170 (7)	0.0150 (6)	0.0189 (7)	0.0056 (5)	0.0043 (5)	0.0032 (5)
C22	0.0186 (7)	0.0206 (6)	0.0192 (7)	0.0053 (5)	0.0072 (5)	0.0021 (5)
C23	0.0230 (7)	0.0193 (7)	0.0185 (7)	0.0041 (5)	0.0029 (6)	−0.0012 (5)
C24	0.0195 (7)	0.0159 (6)	0.0251 (7)	0.0003 (5)	0.0010 (6)	0.0037 (5)
C25	0.0187 (7)	0.0186 (6)	0.0242 (7)	0.0028 (5)	0.0073 (6)	0.0073 (5)
C26	0.0209 (7)	0.0167 (6)	0.0168 (6)	0.0047 (5)	0.0061 (5)	0.0031 (5)
C27	0.0160 (7)	0.0196 (6)	0.0189 (7)	0.0044 (5)	0.0058 (5)	0.0016 (5)
C28	0.0346 (9)	0.0249 (7)	0.0245 (8)	−0.0015 (6)	0.0129 (7)	−0.0044 (6)
F4A	0.0323 (18)	0.029 (3)	0.026 (2)	−0.0080 (15)	0.0092 (13)	−0.0101 (18)
F5A	0.184 (8)	0.0357 (17)	0.0163 (15)	0.003 (4)	0.022 (3)	0.0047 (12)
F6A	0.0490 (19)	0.044 (2)	0.079 (4)	−0.0083 (15)	0.044 (2)	−0.034 (2)
F4B	0.095 (6)	0.0132 (16)	0.032 (2)	0.002 (2)	0.006 (3)	0.0010 (14)
F5B	0.060 (3)	0.0294 (15)	0.0146 (17)	0.0110 (15)	−0.0056 (14)	−0.0013 (12)
F6B	0.0395 (18)	0.086 (5)	0.049 (3)	−0.013 (2)	0.0248 (18)	−0.042 (3)

Geometric parameters (Å, º)

N1—N2	1.3586 (16)	N3—N4	1.3609 (16)
N1—C1	1.3873 (17)	N3—C15	1.3817 (18)
N1—H1	0.857 (13)	N3—H3	0.863 (14)
N2—C13	1.2862 (17)	N4—C27	1.2802 (18)
C1—C6	1.3996 (18)	C15—C20	1.399 (2)
C1—C2	1.3998 (18)	C15—C16	1.3996 (19)
C2—C3	1.3806 (19)	C16—C17	1.3831 (19)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.3918 (19)	C17—C18	1.386 (2)
C3—H3A	0.9500	C17—H17	0.9500
C4—C5	1.3914 (19)	C18—C19	1.394 (2)
C4—C14	1.4905 (19)	C18—C28	1.490 (2)
C5—C6	1.3883 (19)	C19—C20	1.387 (2)
C5—H5	0.9500	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.4001 (18)	C21—C22	1.3991 (19)
C7—C12	1.4017 (19)	C21—C26	1.401 (2)
C7—C13	1.4638 (18)	C21—C27	1.4640 (19)
C8—C9	1.3896 (19)	C22—C23	1.394 (2)
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.385 (2)	C23—C24	1.386 (2)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.396 (2)	C24—C25	1.393 (2)
C10—H10	0.9500	C24—H24	0.9500
C11—C12	1.384 (2)	C25—C26	1.388 (2)
C11—H11	0.9500	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—H13	0.9500	C27—H27	0.9500
C14—F2B	1.313 (7)	C28—F5A	1.256 (6)
C14—F1B	1.319 (7)	C28—F4B	1.300 (7)
C14—F3A	1.320 (6)	C28—F6B	1.313 (4)
C14—F1A	1.321 (7)	C28—F4A	1.334 (6)
C14—F2A	1.343 (5)	C28—F6A	1.386 (5)
C14—F3B	1.344 (6)	C28—F5B	1.405 (5)
N2—N1—C1	120.38 (11)	N4—N3—C15	120.71 (12)
N2—N1—H1	119.6 (11)	N4—N3—H3	119.5 (12)
C1—N1—H1	119.7 (11)	C15—N3—H3	119.0 (12)
C13—N2—N1	117.10 (11)	C27—N4—N3	116.51 (12)
N1—C1—C6	122.28 (12)	N3—C15—C20	122.13 (12)
N1—C1—C2	117.89 (12)	N3—C15—C16	118.11 (12)
C6—C1—C2	119.82 (12)	C20—C15—C16	119.75 (12)
C3—C2—C1	120.30 (12)	C17—C16—C15	120.15 (13)
C3—C2—H2	119.8	C17—C16—H16	119.9
C1—C2—H2	119.8	C15—C16—H16	119.9
C2—C3—C4	120.05 (12)	C16—C17—C18	120.10 (13)
C2—C3—H3A	120.0	C16—C17—H17	120.0
C4—C3—H3A	120.0	C18—C17—H17	120.0
C5—C4—C3	119.77 (12)	C17—C18—C19	120.12 (13)
C5—C4—C14	120.04 (12)	C17—C18—C28	119.33 (13)
C3—C4—C14	120.16 (13)	C19—C18—C28	120.48 (13)
C6—C5—C4	120.76 (12)	C20—C19—C18	120.26 (13)
C6—C5—H5	119.6	C20—C19—H19	119.9
C4—C5—H5	119.6	C18—C19—H19	119.9
C5—C6—C1	119.25 (12)	C19—C20—C15	119.60 (13)
C5—C6—H6	120.4	C19—C20—H20	120.2
C1—C6—H6	120.4	C15—C20—H20	120.2
C8—C7—C12	119.02 (12)	C22—C21—C26	119.16 (13)
C8—C7—C13	119.21 (12)	C22—C21—C27	118.82 (13)
C12—C7—C13	121.77 (12)	C26—C21—C27	122.01 (13)
C9—C8—C7	120.48 (13)	C23—C22—C21	120.47 (13)
C9—C8—H8	119.8	C23—C22—H22	119.8
C7—C8—H8	119.8	C21—C22—H22	119.8
C10—C9—C8	120.11 (13)	C24—C23—C22	119.93 (13)
C10—C9—H9	119.9	C24—C23—H23	120.0
C8—C9—H9	119.9	C22—C23—H23	120.0
C9—C10—C11	119.83 (13)	C23—C24—C25	119.95 (13)
C9—C10—H10	120.1	C23—C24—H24	120.0
C11—C10—H10	120.1	C25—C24—H24	120.0
C12—C11—C10	120.38 (13)	C26—C25—C24	120.46 (14)
C12—C11—H11	119.8	C26—C25—H25	119.8
C10—C11—H11	119.8	C24—C25—H25	119.8
C11—C12—C7	120.18 (13)	C25—C26—C21	120.03 (13)
C11—C12—H12	119.9	C25—C26—H26	120.0
C7—C12—H12	119.9	C21—C26—H26	120.0
N2—C13—C7	120.32 (12)	N4—C27—C21	120.97 (13)
N2—C13—H13	119.8	N4—C27—H27	119.5
C7—C13—H13	119.8	C21—C27—H27	119.5
F2B—C14—F1B	106.4 (7)	F4B—C28—F6B	112.1 (5)
F3A—C14—F1A	106.2 (7)	F5A—C28—F4A	110.1 (7)
F3A—C14—F2A	105.7 (5)	F5A—C28—F6A	108.0 (4)
F1A—C14—F2A	105.2 (7)	F4A—C28—F6A	100.0 (4)
F2B—C14—F3B	105.4 (6)	F4B—C28—F5B	101.5 (5)
F1B—C14—F3B	105.3 (7)	F6B—C28—F5B	100.3 (5)
F2B—C14—C4	113.2 (4)	F5A—C28—C18	116.0 (4)
F1B—C14—C4	113.1 (5)	F4B—C28—C18	115.3 (5)
F3A—C14—C4	113.4 (3)	F6B—C28—C18	115.6 (3)
F1A—C14—C4	112.9 (6)	F4A—C28—C18	112.0 (4)
F2A—C14—C4	112.8 (3)	F6A—C28—C18	109.6 (4)
F3B—C14—C4	112.8 (4)	F5B—C28—C18	109.9 (3)
C1—N1—N2—C13	−177.66 (12)	C15—N3—N4—C27	−172.59 (13)
N2—N1—C1—C6	5.5 (2)	N4—N3—C15—C20	−12.4 (2)
N2—N1—C1—C2	−174.27 (11)	N4—N3—C15—C16	166.81 (12)
N1—C1—C2—C3	178.08 (12)	N3—C15—C16—C17	−178.34 (13)
C6—C1—C2—C3	−1.7 (2)	C20—C15—C16—C17	0.9 (2)
C1—C2—C3—C4	0.2 (2)	C15—C16—C17—C18	0.5 (2)
C2—C3—C4—C5	1.5 (2)	C16—C17—C18—C19	−1.3 (2)
C2—C3—C4—C14	179.81 (13)	C16—C17—C18—C28	−178.22 (13)
C3—C4—C5—C6	−1.9 (2)	C17—C18—C19—C20	0.8 (2)
C14—C4—C5—C6	179.88 (13)	C28—C18—C19—C20	177.65 (14)
C4—C5—C6—C1	0.4 (2)	C18—C19—C20—C15	0.6 (2)
N1—C1—C6—C5	−178.38 (13)	N3—C15—C20—C19	177.79 (13)
C2—C1—C6—C5	1.4 (2)	C16—C15—C20—C19	−1.4 (2)
C12—C7—C8—C9	−0.4 (2)	C26—C21—C22—C23	0.5 (2)
C13—C7—C8—C9	−179.64 (12)	C27—C21—C22—C23	−178.08 (12)
C7—C8—C9—C10	0.8 (2)	C21—C22—C23—C24	−0.6 (2)
C8—C9—C10—C11	−0.3 (2)	C22—C23—C24—C25	0.2 (2)
C9—C10—C11—C12	−0.5 (2)	C23—C24—C25—C26	0.3 (2)
C10—C11—C12—C7	0.9 (2)	C24—C25—C26—C21	−0.4 (2)
C8—C7—C12—C11	−0.4 (2)	C22—C21—C26—C25	0.0 (2)
C13—C7—C12—C11	178.79 (13)	C27—C21—C26—C25	178.51 (12)
N1—N2—C13—C7	179.90 (11)	N3—N4—C27—C21	−178.71 (12)
C8—C7—C13—N2	−176.47 (12)	C22—C21—C27—N4	−173.82 (13)
C12—C7—C13—N2	4.3 (2)	C26—C21—C27—N4	7.6 (2)
C5—C4—C14—F2B	−44.7 (8)	C17—C18—C28—F5A	100.5 (9)
C3—C4—C14—F2B	137.0 (8)	C19—C18—C28—F5A	−76.4 (9)
C5—C4—C14—F1B	−165.8 (8)	C17—C18—C28—F4B	−39.4 (7)
C3—C4—C14—F1B	15.9 (8)	C19—C18—C28—F4B	143.7 (6)
C5—C4—C14—F3A	88.1 (7)	C17—C18—C28—F6B	−172.9 (8)
C3—C4—C14—F3A	−90.2 (7)	C19—C18—C28—F6B	10.2 (8)
C5—C4—C14—F1A	−151.1 (8)	C17—C18—C28—F4A	−27.0 (5)
C3—C4—C14—F1A	30.7 (8)	C19—C18—C28—F4A	156.2 (5)
C5—C4—C14—F2A	−32.0 (4)	C17—C18—C28—F6A	−137.0 (5)
C3—C4—C14—F2A	149.7 (3)	C19—C18—C28—F6A	46.2 (5)
C5—C4—C14—F3B	74.8 (4)	C17—C18—C28—F5B	74.6 (3)
C3—C4—C14—F3B	−103.5 (4)	C19—C18—C28—F5B	−102.3 (3)

(HT11)

Crystal data

C15H10F6N2	F(000) = 672
Mr = 332.25	Dx = 1.621 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 15.2831 (9) Å	Cell parameters from 3889 reflections
b = 4.8177 (3) Å	θ = 2.7–29.3°
c = 19.0386 (11) Å	µ = 0.16 mm^−1
β = 103.740 (3)°	T = 100 K
V = 1361.69 (14) Å^3	Needle, colorless
Z = 4	0.20 × 0.07 × 0.05 mm

Data collection

Bruker APEX-II CCD diffractometer	2757 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan SADABS	θmax = 27.1°, θmin = 2.2°
Tmin = 0.678, Tmax = 0.746	h = −19→19
9984 measured reflections	k = −6→6
2939 independent reflections	l = −24→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + (0.0328P)^2 + 0.2219P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.069	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.22 e Å^−3
2939 reflections	Δρmin = −0.24 e Å^−3
207 parameters	Absolute structure: Refined as an inversion twin.
2 restraints	Absolute structure parameter: 0.3 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.2455 (13)	0.913 (2)	0.1997 (6)	0.0173 (5)	0.530 (16)
H1A	0.3041	0.9178	0.2174	0.021*	0.530 (16)
N2A	0.1982 (8)	0.740 (5)	0.2269 (16)	0.0173 (5)	0.530 (16)
C13A	0.2373 (16)	0.564 (3)	0.2747 (6)	0.0173 (5)	0.530 (16)
H13A	0.3011	0.5503	0.2858	0.021*	0.530 (16)
N1B	0.2376 (15)	0.581 (3)	0.2818 (5)	0.0173 (5)	0.470 (16)
H1B	0.2964	0.5954	0.2977	0.021*	0.470 (16)
N2B	0.1915 (9)	0.742 (6)	0.2271 (18)	0.0173 (5)	0.470 (16)
C13B	0.2477 (19)	0.893 (3)	0.1946 (8)	0.0173 (5)	0.470 (16)
H13B	0.3110	0.8646	0.2067	0.021*	0.470 (16)
F1	0.39523 (9)	1.3340 (3)	0.19583 (7)	0.0342 (4)
F2	0.39901 (9)	1.3893 (3)	0.08448 (8)	0.0324 (4)
F3	0.39014 (10)	0.9814 (3)	0.12653 (9)	0.0312 (4)
F5	0.35928 (10)	0.0578 (3)	0.45536 (8)	0.0335 (4)
F4	0.36261 (9)	0.4746 (3)	0.41749 (8)	0.0298 (4)
F6	0.37466 (9)	0.1345 (3)	0.34775 (7)	0.0319 (4)
C1	0.20646 (15)	1.0945 (5)	0.14188 (12)	0.0171 (5)
C2	0.25917 (15)	1.2605 (5)	0.10773 (11)	0.0175 (5)
C3	0.21822 (17)	1.4507 (5)	0.05472 (12)	0.0213 (5)
H3	0.2544	1.5655	0.0324	0.026*
C4	0.12533 (17)	1.4730 (5)	0.03444 (12)	0.0234 (6)
H4	0.0977	1.6018	−0.0019	0.028*
C5	0.07297 (16)	1.3063 (5)	0.06741 (13)	0.0227 (5)
H5	0.0092	1.3209	0.0534	0.027*
C6	0.11246 (16)	1.1186 (5)	0.12061 (12)	0.0203 (5)
H6	0.0757	1.0057	0.1428	0.024*
C7	0.18740 (15)	0.3871 (5)	0.31236 (11)	0.0177 (5)
C8	0.23037 (15)	0.2138 (5)	0.36963 (12)	0.0188 (5)
C9	0.18003 (16)	0.0311 (5)	0.40094 (12)	0.0229 (5)
H9	0.2096	−0.0858	0.4395	0.027*
C10	0.08752 (17)	0.0184 (5)	0.37649 (14)	0.0256 (6)
H10	0.0535	−0.1072	0.3979	0.031*
C11	0.04469 (17)	0.1905 (5)	0.32051 (13)	0.0243 (6)
H11	−0.0190	0.1831	0.3038	0.029*
C12	0.09348 (16)	0.3724 (5)	0.28873 (12)	0.0211 (5)
H12	0.0630	0.4889	0.2504	0.025*
C14	0.35948 (17)	1.2428 (5)	0.12792 (13)	0.0221 (5)
C15	0.33020 (16)	0.2192 (5)	0.39745 (12)	0.0216 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
N2A	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
C13A	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
N1B	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
N2B	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
C13B	0.0175 (8)	0.0168 (9)	0.0174 (9)	0.0006 (11)	0.0038 (13)	−0.0004 (6)
F1	0.0242 (7)	0.0495 (10)	0.0264 (8)	−0.0057 (7)	0.0008 (6)	−0.0094 (7)
F2	0.0264 (8)	0.0358 (9)	0.0382 (9)	−0.0077 (7)	0.0142 (6)	0.0071 (7)
F3	0.0243 (7)	0.0256 (8)	0.0471 (9)	0.0039 (6)	0.0154 (7)	0.0015 (7)
F5	0.0342 (8)	0.0316 (9)	0.0281 (7)	−0.0005 (7)	−0.0059 (6)	0.0118 (7)
F4	0.0288 (8)	0.0223 (8)	0.0332 (9)	−0.0058 (7)	−0.0026 (6)	−0.0022 (6)
F6	0.0228 (8)	0.0424 (10)	0.0297 (8)	0.0061 (7)	0.0051 (6)	−0.0056 (7)
C1	0.0213 (11)	0.0143 (11)	0.0145 (11)	−0.0004 (9)	0.0021 (9)	−0.0037 (9)
C2	0.0205 (12)	0.0167 (12)	0.0159 (11)	−0.0005 (10)	0.0057 (9)	−0.0038 (9)
C3	0.0292 (13)	0.0180 (13)	0.0174 (12)	−0.0024 (11)	0.0072 (10)	−0.0005 (9)
C4	0.0317 (14)	0.0196 (13)	0.0179 (13)	0.0045 (11)	0.0036 (10)	0.0010 (9)
C5	0.0203 (12)	0.0253 (13)	0.0209 (11)	0.0038 (11)	0.0018 (9)	−0.0007 (10)
C6	0.0207 (11)	0.0197 (13)	0.0209 (12)	−0.0011 (10)	0.0056 (9)	−0.0004 (9)
C7	0.0214 (12)	0.0149 (12)	0.0175 (11)	−0.0007 (9)	0.0059 (9)	−0.0021 (9)
C8	0.0241 (13)	0.0164 (12)	0.0166 (11)	−0.0011 (10)	0.0062 (9)	−0.0031 (9)
C9	0.0315 (14)	0.0195 (13)	0.0181 (12)	−0.0013 (11)	0.0069 (10)	−0.0006 (9)
C10	0.0330 (14)	0.0223 (14)	0.0248 (13)	−0.0074 (11)	0.0132 (11)	−0.0013 (10)
C11	0.0218 (11)	0.0221 (14)	0.0295 (13)	−0.0036 (11)	0.0069 (10)	−0.0046 (10)
C12	0.0220 (12)	0.0197 (12)	0.0212 (12)	0.0023 (10)	0.0045 (10)	−0.0002 (10)
C14	0.0229 (12)	0.0214 (13)	0.0230 (12)	−0.0028 (10)	0.0070 (10)	0.0002 (10)
C15	0.0258 (12)	0.0181 (13)	0.0189 (12)	0.0004 (10)	0.0012 (9)	0.0012 (9)

Geometric parameters (Å, º)

N1A—N2A	1.29 (3)	C2—C3	1.396 (3)
N1A—C1	1.422 (13)	C2—C14	1.492 (3)
N1A—H1A	0.8800	C3—C4	1.384 (3)
N2A—C13A	1.28 (2)	C3—H3	0.9500
C13A—C7	1.443 (19)	C4—C5	1.385 (3)
C13A—H13A	0.9500	C4—H4	0.9500
N1B—N2B	1.36 (3)	C5—C6	1.385 (3)
N1B—C7	1.418 (18)	C5—H5	0.9500
N1B—H1B	0.8800	C6—H6	0.9500
N2B—C13B	1.38 (4)	C7—C12	1.400 (3)
C13B—C1	1.430 (18)	C7—C8	1.406 (3)
C13B—H13B	0.9500	C8—C9	1.393 (3)
F1—C14	1.352 (3)	C8—C15	1.492 (3)
F2—C14	1.336 (3)	C9—C10	1.381 (3)
F3—C14	1.346 (3)	C9—H9	0.9500
F5—C15	1.336 (3)	C10—C11	1.386 (4)
F4—C15	1.347 (3)	C10—H10	0.9500
F6—C15	1.352 (3)	C11—C12	1.380 (3)
C1—C2	1.400 (3)	C11—H11	0.9500
C1—C6	1.402 (3)	C12—H12	0.9500
N2A—N1A—C1	122.4 (15)	C1—C6—H6	119.9
N2A—N1A—H1A	118.8	C12—C7—C8	118.3 (2)
C1—N1A—H1A	118.8	C12—C7—N1B	121.0 (8)
C13A—N2A—N1A	120.0 (13)	C8—C7—N1B	120.7 (8)
N2A—C13A—C7	122.1 (17)	C12—C7—C13A	119.5 (8)
N2A—C13A—H13A	118.9	C8—C7—C13A	122.1 (8)
C7—C13A—H13A	118.9	C9—C8—C7	120.2 (2)
N2B—N1B—C7	117.4 (17)	C9—C8—C15	118.8 (2)
N2B—N1B—H1B	121.3	C7—C8—C15	121.0 (2)
C7—N1B—H1B	121.3	C10—C9—C8	120.6 (2)
N1B—N2B—C13B	112.5 (14)	C10—C9—H9	119.7
N2B—C13B—C1	117 (2)	C8—C9—H9	119.7
N2B—C13B—H13B	121.4	C9—C10—C11	119.4 (2)
C1—C13B—H13B	121.4	C9—C10—H10	120.3
C2—C1—C6	118.8 (2)	C11—C10—H10	120.3
C2—C1—N1A	122.0 (8)	C12—C11—C10	120.8 (2)
C6—C1—N1A	119.2 (8)	C12—C11—H11	119.6
C2—C1—C13B	120.5 (11)	C10—C11—H11	119.6
C6—C1—C13B	120.6 (11)	C11—C12—C7	120.7 (2)
C3—C2—C1	120.1 (2)	C11—C12—H12	119.6
C3—C2—C14	118.7 (2)	C7—C12—H12	119.6
C1—C2—C14	121.1 (2)	F2—C14—F3	105.75 (19)
C4—C3—C2	120.4 (2)	F2—C14—F1	106.30 (19)
C4—C3—H3	119.8	F3—C14—F1	105.04 (19)
C2—C3—H3	119.8	F2—C14—C2	113.47 (19)
C3—C4—C5	119.6 (2)	F3—C14—C2	112.9 (2)
C3—C4—H4	120.2	F1—C14—C2	112.65 (19)
C5—C4—H4	120.2	F5—C15—F4	105.67 (19)
C6—C5—C4	120.8 (2)	F5—C15—F6	106.13 (19)
C6—C5—H5	119.6	F4—C15—F6	105.2 (2)
C4—C5—H5	119.6	F5—C15—C8	113.2 (2)
C5—C6—C1	120.3 (2)	F4—C15—C8	113.1 (2)
C5—C6—H6	119.9	F6—C15—C8	112.83 (19)
C1—N1A—N2A—C13A	174.1 (13)	C12—C7—C8—C9	0.7 (3)
N1A—N2A—C13A—C7	173 (2)	N1B—C7—C8—C9	177.8 (6)
C7—N1B—N2B—C13B	−171 (2)	C13A—C7—C8—C9	−175.3 (6)
N1B—N2B—C13B—C1	−172.9 (14)	C12—C7—C8—C15	−180.0 (2)
N2A—N1A—C1—C2	−173 (2)	N1B—C7—C8—C15	−2.9 (6)
N2A—N1A—C1—C6	10 (2)	C13A—C7—C8—C15	4.0 (6)
N2B—C13B—C1—C2	178 (2)	C7—C8—C9—C10	−0.3 (3)
N2B—C13B—C1—C6	−5 (2)	C15—C8—C9—C10	−179.6 (2)
C6—C1—C2—C3	1.5 (3)	C8—C9—C10—C11	−0.3 (3)
N1A—C1—C2—C3	−175.4 (5)	C9—C10—C11—C12	0.4 (4)
C13B—C1—C2—C3	178.0 (6)	C10—C11—C12—C7	0.0 (3)
C6—C1—C2—C14	−179.7 (2)	C8—C7—C12—C11	−0.6 (3)
N1A—C1—C2—C14	3.3 (5)	N1B—C7—C12—C11	−177.6 (6)
C13B—C1—C2—C14	−3.2 (7)	C13A—C7—C12—C11	175.5 (6)
C1—C2—C3—C4	−1.3 (3)	C3—C2—C14—F2	−8.9 (3)
C14—C2—C3—C4	179.9 (2)	C1—C2—C14—F2	172.35 (19)
C2—C3—C4—C5	0.4 (3)	C3—C2—C14—F3	−129.2 (2)
C3—C4—C5—C6	0.3 (4)	C1—C2—C14—F3	52.0 (3)
C4—C5—C6—C1	0.0 (4)	C3—C2—C14—F1	112.0 (2)
C2—C1—C6—C5	−0.9 (3)	C1—C2—C14—F1	−66.8 (3)
N1A—C1—C6—C5	176.2 (4)	C9—C8—C15—F5	−5.5 (3)
C13B—C1—C6—C5	−177.4 (7)	C7—C8—C15—F5	175.2 (2)
N2B—N1B—C7—C12	−2.5 (14)	C9—C8—C15—F4	−125.7 (2)
N2B—N1B—C7—C8	−179.5 (15)	C7—C8—C15—F4	55.0 (3)
N2A—C13A—C7—C12	10.4 (16)	C9—C8—C15—F6	115.1 (2)
N2A—C13A—C7—C8	−173.7 (17)	C7—C8—C15—F6	−64.2 (3)

(HT13)

Crystal data

C15H10F6N2	Z = 2
Mr = 332.25	F(000) = 336
Triclinic, P1	Dx = 1.635 Mg m^−3
a = 8.189 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.376 (2) Å	Cell parameters from 3907 reflections
c = 11.623 (4) Å	θ = 2.8–27.4°
α = 72.723 (18)°	µ = 0.16 mm^−1
β = 82.222 (17)°	T = 100 K
γ = 62.417 (15)°	Plate, colorless
V = 674.7 (4) Å^3	0.25 × 0.21 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	2297 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.037
Absorption correction: multi-scan SADABS	θmax = 27.6°, θmin = 1.8°
Tmin = 0.652, Tmax = 0.746	h = −8→10
9731 measured reflections	k = −10→10
3006 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0689P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
3006 reflections	Δρmax = 0.32 e Å^−3
208 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	−0.08534 (16)	0.13161 (18)	0.64301 (10)	0.0424 (3)
F5	1.01180 (12)	0.09260 (13)	1.10761 (9)	0.0281 (3)
F4	0.90269 (12)	0.38568 (14)	1.01897 (8)	0.0288 (3)
F3	0.08720 (14)	0.12992 (17)	0.48772 (10)	0.0426 (3)
F2	−0.10402 (14)	0.38777 (15)	0.52583 (10)	0.0402 (3)
F6	1.02271 (13)	0.27945 (15)	1.19544 (9)	0.0343 (3)
N1	0.55943 (18)	0.17255 (19)	0.85231 (12)	0.0220 (3)
H1	0.6739	0.1327	0.8263	0.026*
N2	0.51622 (18)	0.22265 (18)	0.95703 (12)	0.0201 (3)
C14	0.0173 (2)	0.2117 (2)	0.57707 (15)	0.0237 (4)
C4	0.1605 (2)	0.1999 (2)	0.65025 (14)	0.0198 (3)
C5	0.1150 (2)	0.2424 (2)	0.76076 (15)	0.0222 (4)
H5	−0.0076	0.2773	0.7898	0.027*
C6	0.2454 (2)	0.2343 (2)	0.82870 (14)	0.0205 (4)
H6	0.2130	0.2632	0.9042	0.025*
C1	0.4250 (2)	0.1835 (2)	0.78591 (14)	0.0190 (3)
C13	0.6416 (2)	0.2265 (2)	1.00875 (15)	0.0209 (4)
H13	0.7603	0.1959	0.9734	0.025*
C7	0.6022 (2)	0.2785 (2)	1.12307 (14)	0.0181 (3)
C8	0.7305 (2)	0.2955 (2)	1.18163 (14)	0.0199 (4)
C15	0.9145 (2)	0.2647 (2)	1.12693 (15)	0.0226 (4)
C9	0.6868 (2)	0.3462 (2)	1.28937 (15)	0.0231 (4)
H9	0.7755	0.3563	1.3279	0.028*
C10	0.5153 (2)	0.3820 (2)	1.34076 (15)	0.0263 (4)
H10	0.4852	0.4171	1.4143	0.032*
C11	0.3875 (2)	0.3661 (2)	1.28366 (15)	0.0255 (4)
H11	0.2691	0.3910	1.3183	0.031*
C12	0.4304 (2)	0.3147 (2)	1.17750 (15)	0.0217 (4)
H12	0.3412	0.3035	1.1403	0.026*
C3	0.3386 (2)	0.1510 (2)	0.60751 (15)	0.0218 (4)
H3	0.3704	0.1230	0.5317	0.026*
C2	0.4699 (2)	0.1428 (2)	0.67455 (15)	0.0222 (4)
H2	0.5920	0.1092	0.6447	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0451 (7)	0.0676 (8)	0.0341 (6)	−0.0456 (6)	−0.0038 (5)	−0.0045 (6)
F5	0.0186 (5)	0.0272 (6)	0.0355 (6)	−0.0067 (4)	−0.0016 (4)	−0.0095 (4)
F4	0.0262 (5)	0.0328 (6)	0.0290 (6)	−0.0180 (5)	0.0040 (4)	−0.0040 (4)
F3	0.0331 (6)	0.0681 (9)	0.0430 (7)	−0.0231 (6)	0.0012 (5)	−0.0372 (6)
F2	0.0381 (7)	0.0330 (6)	0.0489 (7)	−0.0132 (5)	−0.0228 (6)	−0.0046 (5)
F6	0.0237 (5)	0.0538 (7)	0.0380 (6)	−0.0233 (5)	−0.0023 (5)	−0.0185 (5)
N1	0.0161 (7)	0.0308 (8)	0.0221 (7)	−0.0112 (6)	−0.0001 (6)	−0.0097 (6)
N2	0.0227 (7)	0.0214 (7)	0.0187 (7)	−0.0118 (6)	−0.0006 (6)	−0.0051 (5)
C14	0.0243 (9)	0.0263 (9)	0.0244 (9)	−0.0137 (8)	0.0003 (7)	−0.0081 (7)
C4	0.0214 (8)	0.0186 (8)	0.0218 (8)	−0.0110 (7)	−0.0022 (7)	−0.0042 (6)
C5	0.0199 (8)	0.0258 (9)	0.0246 (9)	−0.0132 (7)	0.0025 (7)	−0.0075 (7)
C6	0.0225 (8)	0.0254 (9)	0.0184 (8)	−0.0135 (7)	0.0023 (7)	−0.0086 (7)
C1	0.0206 (8)	0.0172 (8)	0.0214 (8)	−0.0107 (7)	−0.0032 (7)	−0.0026 (6)
C13	0.0185 (8)	0.0223 (8)	0.0238 (9)	−0.0112 (7)	0.0009 (7)	−0.0055 (7)
C7	0.0191 (8)	0.0156 (8)	0.0189 (8)	−0.0086 (7)	−0.0029 (6)	−0.0010 (6)
C8	0.0200 (8)	0.0175 (8)	0.0223 (8)	−0.0095 (7)	−0.0019 (7)	−0.0026 (6)
C15	0.0214 (8)	0.0247 (9)	0.0256 (9)	−0.0122 (7)	−0.0034 (7)	−0.0074 (7)
C9	0.0266 (9)	0.0240 (9)	0.0216 (8)	−0.0138 (8)	−0.0038 (7)	−0.0042 (7)
C10	0.0310 (10)	0.0279 (9)	0.0218 (9)	−0.0143 (8)	0.0039 (8)	−0.0089 (7)
C11	0.0217 (9)	0.0273 (9)	0.0262 (9)	−0.0122 (8)	0.0051 (7)	−0.0055 (7)
C12	0.0191 (8)	0.0220 (8)	0.0243 (9)	−0.0112 (7)	−0.0037 (7)	−0.0014 (7)
C3	0.0243 (9)	0.0232 (8)	0.0198 (8)	−0.0116 (7)	0.0009 (7)	−0.0070 (7)
C2	0.0175 (8)	0.0272 (9)	0.0225 (8)	−0.0105 (7)	0.0023 (7)	−0.0079 (7)

Geometric parameters (Å, º)

F1—C14	1.3366 (19)	C1—C2	1.394 (2)
F5—C15	1.3579 (19)	C13—C7	1.469 (2)
F4—C15	1.3406 (19)	C13—H13	0.9500
F3—C14	1.3318 (19)	C7—C12	1.396 (2)
F2—C14	1.341 (2)	C7—C8	1.406 (2)
F6—C15	1.3358 (18)	C8—C9	1.389 (2)
N1—N2	1.3535 (17)	C8—C15	1.490 (2)
N1—C1	1.3818 (19)	C9—C10	1.382 (2)
N1—H1	0.8800	C9—H9	0.9500
N2—C13	1.2751 (19)	C10—C11	1.386 (2)
C14—C4	1.490 (2)	C10—H10	0.9500
C4—C3	1.384 (2)	C11—C12	1.375 (2)
C4—C5	1.391 (2)	C11—H11	0.9500
C5—C6	1.377 (2)	C12—H12	0.9500
C5—H5	0.9500	C3—C2	1.376 (2)
C6—C1	1.393 (2)	C3—H3	0.9500
C6—H6	0.9500	C2—H2	0.9500
N2—N1—C1	120.44 (13)	C9—C8—C7	120.96 (14)
N2—N1—H1	119.8	C9—C8—C15	118.71 (14)
C1—N1—H1	119.8	C7—C8—C15	120.30 (14)
C13—N2—N1	117.74 (13)	F6—C15—F4	106.80 (12)
F3—C14—F1	106.31 (13)	F6—C15—F5	105.58 (13)
F3—C14—F2	106.07 (14)	F4—C15—F5	105.29 (13)
F1—C14—F2	104.76 (14)	F6—C15—C8	113.05 (14)
F3—C14—C4	113.29 (14)	F4—C15—C8	112.55 (14)
F1—C14—C4	112.45 (14)	F5—C15—C8	112.94 (13)
F2—C14—C4	113.27 (13)	C10—C9—C8	120.38 (15)
C3—C4—C5	119.46 (15)	C10—C9—H9	119.8
C3—C4—C14	120.27 (15)	C8—C9—H9	119.8
C5—C4—C14	120.26 (14)	C9—C10—C11	119.16 (16)
C6—C5—C4	120.91 (14)	C9—C10—H10	120.4
C6—C5—H5	119.5	C11—C10—H10	120.4
C4—C5—H5	119.5	C12—C11—C10	120.70 (15)
C5—C6—C1	119.51 (15)	C12—C11—H11	119.7
C5—C6—H6	120.2	C10—C11—H11	119.7
C1—C6—H6	120.2	C11—C12—C7	121.47 (15)
N1—C1—C6	120.97 (14)	C11—C12—H12	119.3
N1—C1—C2	119.52 (14)	C7—C12—H12	119.3
C6—C1—C2	119.50 (15)	C2—C3—C4	120.13 (15)
N2—C13—C7	119.88 (14)	C2—C3—H3	119.9
N2—C13—H13	120.1	C4—C3—H3	119.9
C7—C13—H13	120.1	C3—C2—C1	120.48 (15)
C12—C7—C8	117.32 (15)	C3—C2—H2	119.8
C12—C7—C13	119.77 (14)	C1—C2—H2	119.8
C8—C7—C13	122.92 (14)
C1—N1—N2—C13	−173.54 (14)	C13—C7—C8—C15	1.4 (2)
F3—C14—C4—C3	15.1 (2)	C9—C8—C15—F6	4.0 (2)
F1—C14—C4—C3	135.70 (16)	C7—C8—C15—F6	−177.76 (13)
F2—C14—C4—C3	−105.75 (17)	C9—C8—C15—F4	−117.10 (16)
F3—C14—C4—C5	−166.40 (15)	C7—C8—C15—F4	61.12 (19)
F1—C14—C4—C5	−45.8 (2)	C9—C8—C15—F5	123.83 (16)
F2—C14—C4—C5	72.72 (19)	C7—C8—C15—F5	−58.0 (2)
C3—C4—C5—C6	−0.7 (2)	C7—C8—C9—C10	−0.4 (2)
C14—C4—C5—C6	−179.20 (14)	C15—C8—C9—C10	177.84 (14)
C4—C5—C6—C1	0.2 (2)	C8—C9—C10—C11	0.2 (2)
N2—N1—C1—C6	−4.2 (2)	C9—C10—C11—C12	0.3 (2)
N2—N1—C1—C2	175.88 (14)	C10—C11—C12—C7	−0.6 (3)
C5—C6—C1—N1	−179.43 (14)	C8—C7—C12—C11	0.4 (2)
C5—C6—C1—C2	0.4 (2)	C13—C7—C12—C11	−179.12 (15)
N1—N2—C13—C7	−179.51 (13)	C5—C4—C3—C2	0.6 (2)
N2—C13—C7—C12	3.1 (2)	C14—C4—C3—C2	179.09 (14)
N2—C13—C7—C8	−176.45 (14)	C4—C3—C2—C1	0.0 (2)
C12—C7—C8—C9	0.0 (2)	N1—C1—C2—C3	179.33 (13)
C13—C7—C8—C9	179.59 (14)	C6—C1—C2—C3	−0.5 (2)
C12—C7—C8—C15	−178.13 (14)

(HT20)

Crystal data

C14H11F3N2	Dx = 1.466 Mg m^−3
Mr = 264.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 9925 reflections
a = 11.5823 (6) Å	θ = 2.9–30.5°
b = 13.8757 (7) Å	µ = 0.12 mm^−1
c = 7.4479 (3) Å	T = 100 K
V = 1196.97 (10) Å^3	Plate, colorless
Z = 4	0.25 × 0.13 × 0.10 mm
F(000) = 544

Data collection

Bruker APEX-II CCD diffractometer	3036 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.048
Absorption correction: multi-scan SADABS	θmax = 30.5°, θmin = 2.9°
Tmin = 0.645, Tmax = 0.734	h = −16→16
22984 measured reflections	k = −19→19
3414 independent reflections	l = −10→9

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.1985P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.090	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.33 e Å^−3
3414 reflections	Δρmin = −0.25 e Å^−3
173 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.2 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.75926 (15)	0.45385 (9)	0.8262 (2)	0.0393 (4)
F2	0.77569 (12)	0.43847 (8)	1.10965 (18)	0.0292 (3)
F3	0.60943 (10)	0.42710 (8)	0.9882 (3)	0.0367 (3)
N1	0.49483 (13)	−0.07978 (10)	1.0378 (2)	0.0183 (3)
H1	0.4401	−0.0569	1.1078	0.022*
N2	0.58217 (11)	−0.02168 (10)	0.9834 (2)	0.0160 (3)
C4	0.48248 (16)	−0.37130 (13)	0.8904 (3)	0.0201 (4)
H4	0.4798	−0.4377	0.8598	0.024*
C5	0.57785 (15)	−0.31531 (12)	0.8440 (3)	0.0187 (3)
H5	0.6402	−0.3440	0.7809	0.022*
C6	0.58311 (14)	−0.21814 (12)	0.8887 (2)	0.0163 (3)
H6	0.6483	−0.1806	0.8556	0.020*
C1	0.49170 (13)	−0.17618 (11)	0.9827 (3)	0.0142 (3)
C13	0.57933 (15)	0.06664 (11)	1.0366 (2)	0.0153 (3)
H13	0.5183	0.0884	1.1115	0.018*
C7	0.67070 (13)	0.13348 (11)	0.9811 (2)	0.0144 (3)
C8	0.65452 (14)	0.23272 (11)	1.0061 (2)	0.0147 (3)
H8	0.5873	0.2559	1.0648	0.018*
C9	0.73760 (14)	0.29681 (12)	0.9442 (2)	0.0153 (3)
C10	0.83839 (14)	0.26481 (12)	0.8620 (2)	0.0179 (3)
H10	0.8945	0.3096	0.8207	0.021*
C14	0.71941 (15)	0.40342 (12)	0.9658 (3)	0.0185 (3)
C3	0.39164 (15)	−0.32866 (12)	0.9818 (3)	0.0191 (3)
H3	0.3263	−0.3664	1.0137	0.023*
C2	0.39466 (14)	−0.23121 (12)	1.0276 (3)	0.0168 (3)
H2	0.3314	−0.2025	1.0887	0.020*
C12	0.77315 (15)	0.10110 (13)	0.8998 (3)	0.0167 (3)
H12	0.7859	0.0339	0.8850	0.020*
C11	0.85590 (15)	0.16615 (13)	0.8410 (3)	0.0185 (3)
H11	0.9247	0.1433	0.7862	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0746 (11)	0.0182 (5)	0.0253 (7)	−0.0081 (6)	0.0148 (7)	0.0038 (5)
F2	0.0395 (7)	0.0197 (5)	0.0284 (7)	0.0013 (5)	−0.0086 (6)	−0.0092 (5)
F3	0.0233 (5)	0.0163 (5)	0.0704 (10)	0.0041 (4)	−0.0029 (7)	0.0029 (6)
N1	0.0181 (7)	0.0128 (6)	0.0241 (8)	−0.0017 (5)	0.0072 (6)	−0.0026 (6)
N2	0.0175 (6)	0.0144 (6)	0.0161 (7)	−0.0016 (5)	0.0007 (6)	0.0002 (6)
C4	0.0236 (8)	0.0130 (7)	0.0236 (9)	0.0017 (6)	−0.0054 (8)	−0.0004 (6)
C5	0.0194 (8)	0.0165 (7)	0.0201 (8)	0.0045 (6)	−0.0011 (7)	−0.0015 (7)
C6	0.0152 (7)	0.0157 (7)	0.0181 (9)	−0.0012 (6)	0.0002 (6)	0.0001 (6)
C1	0.0161 (7)	0.0121 (6)	0.0146 (7)	0.0001 (5)	−0.0009 (7)	−0.0004 (6)
C13	0.0166 (7)	0.0142 (7)	0.0153 (8)	0.0002 (6)	0.0000 (6)	0.0004 (6)
C7	0.0166 (7)	0.0129 (7)	0.0135 (7)	−0.0002 (5)	−0.0010 (7)	−0.0010 (6)
C8	0.0164 (7)	0.0133 (7)	0.0144 (8)	0.0005 (5)	0.0007 (6)	−0.0008 (6)
C9	0.0189 (7)	0.0140 (7)	0.0129 (8)	−0.0007 (6)	−0.0019 (6)	−0.0007 (6)
C10	0.0171 (7)	0.0206 (8)	0.0160 (8)	−0.0047 (6)	0.0003 (6)	−0.0013 (7)
C14	0.0227 (8)	0.0142 (7)	0.0184 (8)	−0.0036 (6)	0.0002 (7)	0.0002 (7)
C3	0.0192 (7)	0.0164 (7)	0.0216 (9)	−0.0046 (6)	−0.0018 (7)	0.0017 (7)
C2	0.0155 (7)	0.0165 (7)	0.0184 (8)	0.0007 (6)	0.0019 (6)	0.0006 (6)
C12	0.0178 (7)	0.0161 (7)	0.0163 (8)	0.0022 (6)	−0.0015 (7)	−0.0020 (6)
C11	0.0144 (7)	0.0228 (8)	0.0184 (8)	0.0007 (6)	0.0011 (7)	−0.0040 (7)

Geometric parameters (Å, º)

F1—C14	1.335 (2)	C13—H13	0.9500
F2—C14	1.345 (2)	C7—C8	1.402 (2)
F3—C14	1.326 (2)	C7—C12	1.406 (2)
N1—N2	1.3555 (19)	C8—C9	1.389 (2)
N1—C1	1.400 (2)	C8—H8	0.9500
N1—H1	0.8800	C9—C10	1.391 (2)
N2—C13	1.288 (2)	C9—C14	1.503 (2)
C4—C3	1.386 (3)	C10—C11	1.393 (2)
C4—C5	1.394 (3)	C10—H10	0.9500
C4—H4	0.9500	C3—C2	1.395 (2)
C5—C6	1.390 (2)	C3—H3	0.9500
C5—H5	0.9500	C2—H2	0.9500
C6—C1	1.396 (2)	C12—C11	1.388 (2)
C6—H6	0.9500	C12—H12	0.9500
C1—C2	1.399 (2)	C11—H11	0.9500
C13—C7	1.467 (2)
N2—N1—C1	120.01 (14)	C8—C9—C10	121.54 (15)
N2—N1—H1	120.0	C8—C9—C14	119.85 (15)
C1—N1—H1	120.0	C10—C9—C14	118.61 (15)
C13—N2—N1	117.06 (14)	C9—C10—C11	119.03 (15)
C3—C4—C5	119.04 (16)	C9—C10—H10	120.5
C3—C4—H4	120.5	C11—C10—H10	120.5
C5—C4—H4	120.5	F3—C14—F1	107.47 (16)
C6—C5—C4	121.06 (17)	F3—C14—F2	105.99 (16)
C6—C5—H5	119.5	F1—C14—F2	105.25 (14)
C4—C5—H5	119.5	F3—C14—C9	113.08 (13)
C5—C6—C1	119.42 (15)	F1—C14—C9	112.59 (16)
C5—C6—H6	120.3	F2—C14—C9	111.91 (15)
C1—C6—H6	120.3	C4—C3—C2	120.99 (16)
C6—C1—C2	120.08 (14)	C4—C3—H3	119.5
C6—C1—N1	121.73 (14)	C2—C3—H3	119.5
C2—C1—N1	118.18 (15)	C3—C2—C1	119.38 (16)
N2—C13—C7	119.77 (15)	C3—C2—H2	120.3
N2—C13—H13	120.1	C1—C2—H2	120.3
C7—C13—H13	120.1	C11—C12—C7	120.73 (15)
C8—C7—C12	118.93 (15)	C11—C12—H12	119.6
C8—C7—C13	119.16 (14)	C7—C12—H12	119.6
C12—C7—C13	121.89 (14)	C12—C11—C10	120.23 (16)
C9—C8—C7	119.49 (15)	C12—C11—H11	119.9
C9—C8—H8	120.3	C10—C11—H11	119.9
C7—C8—H8	120.3
C1—N1—N2—C13	179.05 (16)	C14—C9—C10—C11	−179.86 (17)
C3—C4—C5—C6	0.3 (3)	C8—C9—C14—F3	−21.2 (3)
C4—C5—C6—C1	0.4 (3)	C10—C9—C14—F3	158.81 (18)
C5—C6—C1—C2	−1.5 (3)	C8—C9—C14—F1	−143.29 (17)
C5—C6—C1—N1	177.18 (17)	C10—C9—C14—F1	36.7 (2)
N2—N1—C1—C6	7.3 (3)	C8—C9—C14—F2	98.38 (18)
N2—N1—C1—C2	−174.06 (16)	C10—C9—C14—F2	−81.6 (2)
N1—N2—C13—C7	−179.44 (15)	C5—C4—C3—C2	−0.1 (3)
N2—C13—C7—C8	166.32 (16)	C4—C3—C2—C1	−0.9 (3)
N2—C13—C7—C12	−12.2 (3)	C6—C1—C2—C3	1.7 (3)
C12—C7—C8—C9	2.4 (2)	N1—C1—C2—C3	−177.00 (16)
C13—C7—C8—C9	−176.19 (17)	C8—C7—C12—C11	−1.6 (3)
C7—C8—C9—C10	−1.7 (3)	C13—C7—C12—C11	176.98 (17)
C7—C8—C9—C14	178.30 (16)	C7—C12—C11—C10	0.0 (3)
C8—C9—C10—C11	0.2 (3)	C9—C10—C11—C12	0.7 (3)

(HT31)

Crystal data

C15H10F6N2	Z = 2
Mr = 332.25	F(000) = 336
Triclinic, P1	Dx = 1.611 Mg m^−3
a = 8.2523 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3039 (4) Å	Cell parameters from 7617 reflections
c = 11.7930 (5) Å	θ = 3.6–30.6°
α = 82.823 (2)°	µ = 0.15 mm^−1
β = 74.769 (2)°	T = 100 K
γ = 61.428 (2)°	Plate, colorless
V = 684.78 (5) Å^3	0.27 × 0.19 × 0.11 mm

Data collection

Bruker APEX-II CCD diffractometer	2989 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan SADABS	θmax = 28.3°, θmin = 1.8°
Tmin = 0.672, Tmax = 0.746	h = −10→10
12775 measured reflections	k = −11→11
3365 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0551P)^2 + 0.1675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3365 reflections	Δρmax = 0.38 e Å^−3
208 parameters	Δρmin = −0.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F5	0.62347 (13)	−0.07084 (12)	0.14015 (7)	0.0417 (2)
F3	0.88394 (11)	0.90018 (10)	0.52754 (6)	0.03319 (19)
F6	0.61995 (14)	0.10368 (11)	−0.00975 (8)	0.0463 (2)
F4	0.88364 (11)	−0.09672 (12)	0.02874 (8)	0.0427 (2)
F1	0.58489 (10)	1.00671 (9)	0.59823 (7)	0.03223 (19)
F2	0.75744 (13)	1.03172 (10)	0.69678 (7)	0.0382 (2)
N1	0.73844 (14)	0.63879 (12)	0.51673 (8)	0.0226 (2)
H1	0.7132	0.7468	0.4838	0.027*
N2	0.73659 (13)	0.50728 (12)	0.45998 (8)	0.0213 (2)
C4	0.86588 (17)	0.53006 (18)	0.84821 (10)	0.0281 (3)
H4	0.8949	0.5047	0.9233	0.034*
C5	0.85966 (17)	0.39823 (17)	0.78996 (10)	0.0280 (2)
H5	0.8850	0.2822	0.8258	0.034*
C6	0.81712 (16)	0.43322 (15)	0.68056 (10)	0.0236 (2)
H6	0.8131	0.3416	0.6423	0.028*
C1	0.78009 (14)	0.60302 (14)	0.62630 (9)	0.0197 (2)
C13	0.69992 (15)	0.54917 (14)	0.35821 (9)	0.0219 (2)
H13	0.6732	0.6682	0.3273	0.026*
C7	0.69878 (15)	0.41539 (14)	0.28903 (9)	0.0203 (2)
C8	0.65799 (17)	0.46521 (15)	0.17848 (10)	0.0247 (2)
H8	0.6292	0.5857	0.1498	0.030*
C9	0.65913 (16)	0.33982 (15)	0.10996 (9)	0.0242 (2)
H9	0.6308	0.3746	0.0349	0.029*
C10	0.70167 (15)	0.16435 (15)	0.15161 (9)	0.0212 (2)
C15	0.70684 (17)	0.02672 (16)	0.07780 (10)	0.0256 (2)
C14	0.75457 (17)	0.91702 (15)	0.62872 (10)	0.0249 (2)
C2	0.78710 (15)	0.73623 (14)	0.68521 (9)	0.0208 (2)
C11	0.74380 (17)	0.11242 (16)	0.26174 (10)	0.0252 (2)
H11	0.7738	−0.0086	0.2898	0.030*
C12	0.74174 (17)	0.23748 (15)	0.32996 (9)	0.0235 (2)
H12	0.7697	0.2023	0.4051	0.028*
C3	0.82925 (16)	0.69861 (16)	0.79544 (10)	0.0248 (2)
H3	0.8329	0.7896	0.8348	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F5	0.0604 (5)	0.0469 (5)	0.0367 (4)	−0.0409 (4)	−0.0055 (4)	−0.0072 (3)
F3	0.0375 (4)	0.0294 (4)	0.0326 (4)	−0.0187 (3)	−0.0033 (3)	0.0033 (3)
F6	0.0737 (6)	0.0394 (4)	0.0427 (5)	−0.0274 (4)	−0.0388 (4)	0.0022 (4)
F4	0.0347 (4)	0.0440 (5)	0.0481 (5)	−0.0147 (4)	−0.0028 (3)	−0.0259 (4)
F1	0.0315 (4)	0.0213 (3)	0.0412 (4)	−0.0067 (3)	−0.0149 (3)	−0.0012 (3)
F2	0.0586 (5)	0.0274 (4)	0.0404 (4)	−0.0244 (4)	−0.0193 (4)	−0.0042 (3)
N1	0.0313 (5)	0.0181 (4)	0.0205 (4)	−0.0116 (4)	−0.0084 (4)	−0.0021 (3)
N2	0.0228 (4)	0.0211 (4)	0.0214 (4)	−0.0105 (4)	−0.0044 (3)	−0.0048 (3)
C4	0.0310 (6)	0.0351 (6)	0.0198 (5)	−0.0157 (5)	−0.0085 (4)	0.0016 (4)
C5	0.0312 (6)	0.0271 (5)	0.0246 (5)	−0.0133 (5)	−0.0068 (4)	0.0034 (4)
C6	0.0270 (5)	0.0222 (5)	0.0221 (5)	−0.0122 (4)	−0.0039 (4)	−0.0024 (4)
C1	0.0183 (5)	0.0214 (5)	0.0185 (5)	−0.0087 (4)	−0.0024 (4)	−0.0033 (4)
C13	0.0242 (5)	0.0189 (5)	0.0216 (5)	−0.0086 (4)	−0.0055 (4)	−0.0026 (4)
C7	0.0192 (5)	0.0214 (5)	0.0199 (5)	−0.0088 (4)	−0.0043 (4)	−0.0027 (4)
C8	0.0304 (6)	0.0201 (5)	0.0232 (5)	−0.0100 (4)	−0.0095 (4)	0.0006 (4)
C9	0.0281 (5)	0.0252 (5)	0.0195 (5)	−0.0108 (4)	−0.0090 (4)	−0.0003 (4)
C10	0.0217 (5)	0.0240 (5)	0.0204 (5)	−0.0117 (4)	−0.0050 (4)	−0.0039 (4)
C15	0.0300 (6)	0.0285 (5)	0.0233 (5)	−0.0155 (5)	−0.0088 (4)	−0.0031 (4)
C14	0.0288 (6)	0.0221 (5)	0.0260 (5)	−0.0118 (4)	−0.0078 (4)	−0.0043 (4)
C2	0.0203 (5)	0.0207 (5)	0.0212 (5)	−0.0094 (4)	−0.0034 (4)	−0.0036 (4)
C11	0.0342 (6)	0.0232 (5)	0.0243 (5)	−0.0166 (5)	−0.0110 (4)	0.0025 (4)
C12	0.0311 (6)	0.0257 (5)	0.0193 (5)	−0.0157 (4)	−0.0101 (4)	0.0017 (4)
C3	0.0245 (5)	0.0299 (6)	0.0222 (5)	−0.0131 (4)	−0.0052 (4)	−0.0059 (4)

Geometric parameters (Å, º)

F5—C15	1.3375 (15)	C1—C2	1.4085 (14)
F3—C14	1.3464 (14)	C13—C7	1.4630 (14)
F6—C15	1.3321 (13)	C13—H13	0.9500
F4—C15	1.3373 (14)	C7—C8	1.3952 (14)
F1—C14	1.3583 (14)	C7—C12	1.3971 (15)
F2—C14	1.3321 (12)	C8—C9	1.3907 (15)
N1—N2	1.3582 (12)	C8—H8	0.9500
N1—C1	1.3842 (13)	C9—C10	1.3821 (16)
N1—H1	0.8800	C9—H9	0.9500
N2—C13	1.2802 (14)	C10—C11	1.3955 (15)
C4—C3	1.3835 (17)	C10—C15	1.4993 (14)
C4—C5	1.3904 (17)	C14—C2	1.4927 (15)
C4—H4	0.9500	C2—C3	1.3931 (15)
C5—C6	1.3853 (15)	C11—C12	1.3823 (15)
C5—H5	0.9500	C11—H11	0.9500
C6—C1	1.3986 (15)	C12—H12	0.9500
C6—H6	0.9500	C3—H3	0.9500
N2—N1—C1	120.00 (9)	C9—C10—C11	120.38 (10)
N2—N1—H1	120.0	C9—C10—C15	120.28 (10)
C1—N1—H1	120.0	C11—C10—C15	119.34 (10)
C13—N2—N1	116.51 (9)	F6—C15—F4	106.54 (10)
C3—C4—C5	119.16 (10)	F6—C15—F5	106.46 (10)
C3—C4—H4	120.4	F4—C15—F5	105.43 (10)
C5—C4—H4	120.4	F6—C15—C10	112.77 (10)
C6—C5—C4	121.11 (11)	F4—C15—C10	112.67 (9)
C6—C5—H5	119.4	F5—C15—C10	112.42 (9)
C4—C5—H5	119.4	F2—C14—F3	106.83 (10)
C5—C6—C1	120.23 (10)	F2—C14—F1	106.29 (9)
C5—C6—H6	119.9	F3—C14—F1	104.65 (9)
C1—C6—H6	119.9	F2—C14—C2	113.54 (9)
N1—C1—C6	120.61 (9)	F3—C14—C2	112.47 (9)
N1—C1—C2	120.78 (10)	F1—C14—C2	112.43 (9)
C6—C1—C2	118.61 (10)	C3—C2—C1	120.26 (10)
N2—C13—C7	120.61 (10)	C3—C2—C14	119.41 (10)
N2—C13—H13	119.7	C1—C2—C14	120.31 (9)
C7—C13—H13	119.7	C12—C11—C10	119.85 (10)
C8—C7—C12	119.18 (10)	C12—C11—H11	120.1
C8—C7—C13	119.28 (10)	C10—C11—H11	120.1
C12—C7—C13	121.53 (9)	C11—C12—C7	120.39 (10)
C9—C8—C7	120.51 (10)	C11—C12—H12	119.8
C9—C8—H8	119.7	C7—C12—H12	119.8
C7—C8—H8	119.7	C4—C3—C2	120.63 (10)
C10—C9—C8	119.69 (10)	C4—C3—H3	119.7
C10—C9—H9	120.2	C2—C3—H3	119.7
C8—C9—H9	120.2
C1—N1—N2—C13	−178.91 (10)	C11—C10—C15—F5	43.98 (15)
C3—C4—C5—C6	−0.15 (18)	N1—C1—C2—C3	−179.97 (10)
C4—C5—C6—C1	0.23 (18)	C6—C1—C2—C3	−0.31 (16)
N2—N1—C1—C6	−1.18 (16)	N1—C1—C2—C14	−1.62 (16)
N2—N1—C1—C2	178.48 (9)	C6—C1—C2—C14	178.05 (10)
C5—C6—C1—N1	179.66 (10)	F2—C14—C2—C3	−4.37 (15)
C5—C6—C1—C2	−0.01 (16)	F3—C14—C2—C3	117.09 (11)
N1—N2—C13—C7	178.64 (9)	F1—C14—C2—C3	−125.09 (11)
N2—C13—C7—C8	179.89 (10)	F2—C14—C2—C1	177.26 (9)
N2—C13—C7—C12	−1.56 (17)	F3—C14—C2—C1	−61.28 (13)
C12—C7—C8—C9	0.30 (17)	F1—C14—C2—C1	56.55 (13)
C13—C7—C8—C9	178.88 (10)	C9—C10—C11—C12	0.44 (17)
C7—C8—C9—C10	−0.22 (18)	C15—C10—C11—C12	179.21 (10)
C8—C9—C10—C11	−0.14 (17)	C10—C11—C12—C7	−0.37 (18)
C8—C9—C10—C15	−178.91 (10)	C8—C7—C12—C11	0.00 (17)
C9—C10—C15—F6	−16.88 (16)	C13—C7—C12—C11	−178.55 (10)
C11—C10—C15—F6	164.34 (11)	C5—C4—C3—C2	−0.17 (17)
C9—C10—C15—F4	103.79 (13)	C1—C2—C3—C4	0.40 (17)
C11—C10—C15—F4	−74.99 (14)	C14—C2—C3—C4	−177.97 (11)
C9—C10—C15—F5	−137.25 (11)

(HT33C)

Crystal data

C15H10F6N2	F(000) = 672
Mr = 332.25	Dx = 1.539 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.330 (4) Å	Cell parameters from 7210 reflections
b = 13.658 (5) Å	θ = 3.0–30.1°
c = 7.938 (2) Å	µ = 0.15 mm^−1
β = 112.607 (11)°	T = 100 K
V = 1434.2 (8) Å^3	Rod, yellow
Z = 4	0.25 × 0.10 × 0.09 mm

Data collection

Bruker APEX-II CCD diffractometer	1298 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.059
Absorption correction: multi-scan SADABS	θmax = 28.7°, θmin = 4.0°
Tmin = 6.458, Tmax = 7.651	h = −19→18
8765 measured reflections	k = −17→18
1857 independent reflections	l = −10→10

Refinement

Refinement on F^2	153 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.8161P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1857 reflections	Δρmax = 0.24 e Å^−3
133 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.07197 (10)	1.02718 (10)	0.37806 (18)	0.0301 (3)	0.5
H1	0.070301	1.091594	0.376782	0.036*	0.5
C1	0.15098 (10)	0.97792 (11)	0.51595 (18)	0.0255 (3)
C2	0.15391 (11)	0.87562 (11)	0.53043 (19)	0.0292 (3)
H2	0.101047	0.837535	0.446124	0.035*
C3	0.23302 (11)	0.83002 (12)	0.6663 (2)	0.0334 (4)
H3	0.234401	0.760656	0.675810	0.040*
C4	0.31105 (11)	0.88544 (13)	0.78971 (19)	0.0335 (4)
C5	0.30827 (11)	0.98695 (13)	0.7767 (2)	0.0352 (4)
H5	0.361205	1.024782	0.861431	0.042*
C6	0.22905 (12)	1.03299 (12)	0.6415 (2)	0.0324 (4)
H6	0.227513	1.102413	0.633525	0.039*
C7	0.07197 (10)	1.02718 (10)	0.37806 (18)	0.0301 (3)	0.5
H7	0.070168	1.096718	0.376680	0.036*	0.5
N2	0.000000	0.97709 (13)	0.250000	0.0256 (4)
C8	0.39592 (12)	0.83321 (16)	0.9345 (2)	0.0461 (5)
F1A	0.4811 (5)	0.8775 (5)	1.0104 (13)	0.093 (3)	0.503 (14)
F2A	0.4246 (3)	0.7440 (4)	0.8740 (6)	0.0555 (12)	0.503 (14)
F3A	0.3715 (5)	0.7930 (5)	1.0663 (8)	0.0715 (18)	0.503 (14)
F1B	0.4531 (4)	0.9049 (4)	1.0556 (6)	0.0572 (12)	0.497 (14)
F2B	0.4537 (7)	0.7947 (11)	0.8687 (6)	0.109 (4)	0.497 (14)
F3B	0.3658 (4)	0.7795 (4)	1.0373 (9)	0.0681 (17)	0.497 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0390 (8)	0.0236 (7)	0.0336 (7)	−0.0025 (6)	0.0205 (6)	−0.0027 (5)
C1	0.0260 (7)	0.0308 (8)	0.0232 (7)	−0.0040 (6)	0.0135 (6)	−0.0029 (5)
C2	0.0269 (7)	0.0316 (8)	0.0247 (7)	−0.0065 (6)	0.0051 (6)	−0.0034 (6)
C3	0.0328 (8)	0.0322 (8)	0.0295 (8)	−0.0030 (7)	0.0058 (6)	0.0006 (6)
C4	0.0261 (8)	0.0468 (10)	0.0263 (8)	−0.0060 (7)	0.0086 (6)	−0.0021 (6)
C5	0.0287 (8)	0.0481 (10)	0.0279 (8)	−0.0145 (7)	0.0097 (6)	−0.0120 (6)
C6	0.0372 (9)	0.0315 (8)	0.0318 (8)	−0.0102 (7)	0.0168 (7)	−0.0091 (6)
C7	0.0390 (8)	0.0236 (7)	0.0336 (7)	−0.0025 (6)	0.0205 (6)	−0.0027 (5)
N2	0.0274 (8)	0.0280 (9)	0.0242 (8)	0.000	0.0129 (7)	0.000
C8	0.0290 (8)	0.0674 (13)	0.0328 (9)	−0.0022 (8)	0.0017 (7)	−0.0056 (8)
F1A	0.039 (2)	0.070 (3)	0.113 (5)	−0.025 (2)	−0.034 (2)	0.026 (3)
F2A	0.0375 (17)	0.075 (3)	0.0407 (15)	0.0222 (16)	0.0004 (11)	−0.0062 (14)
F3A	0.083 (4)	0.098 (4)	0.046 (2)	0.054 (3)	0.039 (2)	0.0273 (19)
F1B	0.0353 (19)	0.067 (2)	0.0432 (17)	−0.0027 (16)	−0.0133 (12)	0.0087 (13)
F2B	0.073 (4)	0.196 (9)	0.0484 (18)	0.090 (5)	0.012 (2)	−0.002 (3)
F3B	0.045 (2)	0.042 (2)	0.086 (3)	−0.0133 (18)	−0.0097 (19)	0.0318 (19)

Geometric parameters (Å, º)

C1—C6	1.397 (2)	C5—H5	0.9500
C1—C2	1.401 (2)	C6—H6	0.9500
C1—C7	1.407 (2)	C7—N2	1.3263 (16)
C2—C3	1.377 (2)	C7—H7	0.9500
C2—H2	0.9500	C8—F2B	1.252 (4)
C3—C4	1.393 (2)	C8—F1A	1.286 (4)
C3—H3	0.9500	C8—F3B	1.288 (5)
C4—C5	1.390 (3)	C8—F3A	1.342 (5)
C4—C8	1.495 (2)	C8—F1B	1.395 (5)
C5—C6	1.378 (2)	C8—F2A	1.427 (5)
C6—C1—C2	119.18 (14)	C1—C6—H6	119.9
C6—C1—C7	118.79 (14)	N2—C7—C1	120.37 (14)
C2—C1—C7	122.03 (13)	N2—C7—H7	119.8
C3—C2—C1	120.33 (13)	C1—C7—H7	119.8
C3—C2—H2	119.8	C7—N2—N1^i	117.89 (18)
C1—C2—H2	119.8	F2B—C8—F3B	117.4 (6)
C2—C3—C4	120.11 (15)	F1A—C8—F3A	108.2 (4)
C2—C3—H3	119.9	F2B—C8—F1B	106.0 (5)
C4—C3—H3	119.9	F3B—C8—F1B	102.3 (3)
C5—C4—C3	119.83 (15)	F1A—C8—F2A	102.4 (5)
C5—C4—C8	121.66 (15)	F3A—C8—F2A	96.2 (3)
C3—C4—C8	118.52 (16)	F2B—C8—C4	110.7 (3)
C6—C5—C4	120.30 (14)	F1A—C8—C4	118.8 (3)
C6—C5—H5	119.9	F3B—C8—C4	112.8 (3)
C4—C5—H5	119.9	F3A—C8—C4	114.6 (3)
C5—C6—C1	120.25 (15)	F1B—C8—C4	106.5 (3)
C5—C6—H6	119.9	F2A—C8—C4	113.8 (2)
C6—C1—C2—C3	−0.3 (2)	C5—C4—C8—F2B	−105.1 (9)
C7—C1—C2—C3	179.38 (13)	C3—C4—C8—F2B	75.2 (9)
C1—C2—C3—C4	−0.4 (2)	C5—C4—C8—F1A	−22.0 (8)
C2—C3—C4—C5	0.7 (2)	C3—C4—C8—F1A	158.3 (7)
C2—C3—C4—C8	−179.62 (13)	C5—C4—C8—F3B	121.0 (4)
C3—C4—C5—C6	−0.5 (2)	C3—C4—C8—F3B	−58.6 (4)
C8—C4—C5—C6	179.89 (14)	C5—C4—C8—F3A	108.0 (4)
C4—C5—C6—C1	−0.2 (2)	C3—C4—C8—F3A	−71.6 (4)
C2—C1—C6—C5	0.5 (2)	C5—C4—C8—F1B	9.6 (3)
C7—C1—C6—C5	−179.13 (12)	C3—C4—C8—F1B	−170.0 (3)
C6—C1—C7—N2	175.80 (11)	C5—C4—C8—F2A	−142.7 (3)
C2—C1—C7—N2	−3.86 (18)	C3—C4—C8—F2A	37.7 (3)
C1—C7—N2—N1^i	−179.16 (13)

Symmetry code: (i) −x, y, −z+1/2.

(HT33P)

Crystal data

C15H10F6N2	Dx = 1.583 Mg m^−3
Mr = 332.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 6485 reflections
a = 11.2082 (4) Å	θ = 2.3–30.6°
b = 16.2891 (5) Å	µ = 0.15 mm^−1
c = 15.2689 (7) Å	T = 100 K
V = 2787.67 (18) Å^3	Plate, yellow
Z = 8	0.27 × 0.24 × 0.13 mm
F(000) = 1344

Data collection

Bruker APEX-II CCD diffractometer	6821 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan SADABS	θmax = 30.5°, θmin = 2.5°
Tmin = 0.645, Tmax = 0.753	h = −15→16
36037 measured reflections	k = −22→22
8421 independent reflections	l = −21→21

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.0647P)^2 + 1.2842P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.42 e Å^−3
8421 reflections	Δρmin = −0.26 e Å^−3
444 parameters	Absolute structure: Refined as an inversion twin.
154 restraints	Absolute structure parameter: 0.5 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N2	0.6704 (2)	0.86570 (15)	0.23643 (16)	0.0217 (5)
N1	0.7356 (2)	0.79996 (16)	0.21635 (18)	0.0273 (5)
H1	0.806141	0.805895	0.191843	0.033*
C1	0.6911 (2)	0.72100 (18)	0.23451 (18)	0.0207 (6)
C2	0.7612 (3)	0.65184 (18)	0.2148 (2)	0.0247 (6)
H2	0.838268	0.658678	0.190017	0.030*
C3	0.7180 (3)	0.57393 (19)	0.2314 (2)	0.0255 (6)
H3	0.765349	0.527432	0.217085	0.031*
C4	0.6057 (3)	0.56284 (18)	0.2688 (2)	0.0229 (6)
C5	0.5369 (3)	0.63096 (18)	0.2894 (2)	0.0236 (6)
H5	0.460763	0.623689	0.315649	0.028*
C6	0.5780 (3)	0.70933 (18)	0.2721 (2)	0.0235 (6)
H6	0.529495	0.755455	0.285673	0.028*
C7	0.6433 (2)	1.01008 (17)	0.23852 (18)	0.0204 (5)
C8	0.6867 (3)	1.08751 (18)	0.2160 (2)	0.0244 (6)
H8	0.763382	1.092800	0.190108	0.029*
C9	0.6182 (3)	1.15654 (18)	0.2315 (2)	0.0256 (6)
H9	0.647770	1.209187	0.215844	0.031*
C10	0.5063 (3)	1.14928 (18)	0.2699 (2)	0.0226 (6)
C11	0.4627 (3)	1.07240 (19)	0.2935 (2)	0.0247 (6)
H11	0.386332	1.067653	0.319969	0.030*
C12	0.5305 (3)	1.00287 (18)	0.2783 (2)	0.0240 (6)
H12	0.501036	0.950394	0.294701	0.029*
C13	0.7135 (2)	0.93787 (17)	0.21903 (19)	0.0187 (5)
H13	0.790554	0.943188	0.193707	0.022*
C14	0.5600 (3)	0.47802 (19)	0.2834 (2)	0.0266 (6)
F1	0.64434 (19)	0.42569 (12)	0.30791 (18)	0.0450 (6)
F2	0.4756 (2)	0.47425 (13)	0.34551 (16)	0.0437 (5)
F3	0.5089 (3)	0.44770 (14)	0.21128 (16)	0.0547 (7)
C15	0.4316 (3)	1.22396 (19)	0.2828 (2)	0.0285 (6)
F4	0.4875 (3)	1.28266 (14)	0.3288 (2)	0.0641 (8)
F5	0.4023 (3)	1.26036 (18)	0.20802 (17)	0.0619 (8)
F6	0.3314 (3)	1.21005 (14)	0.3253 (2)	0.0719 (10)
N4	0.4060 (2)	0.63372 (14)	0.02680 (16)	0.0213 (5)
N3	0.4485 (2)	0.55848 (16)	0.04156 (18)	0.0261 (6)
H3A	0.519942	0.552021	0.064420	0.031*
C16	0.3783 (2)	0.48913 (16)	0.02033 (18)	0.0185 (5)
C17	0.4274 (2)	0.41075 (17)	0.02981 (19)	0.0204 (5)
H17	0.507787	0.404841	0.048608	0.024*
C18	0.3597 (3)	0.34178 (16)	0.01195 (19)	0.0218 (5)
H18	0.393411	0.288608	0.018483	0.026*
C19	0.2421 (2)	0.35054 (17)	−0.01563 (18)	0.0207 (5)
C20	0.1932 (2)	0.42812 (17)	−0.0266 (2)	0.0226 (6)
H20	0.113384	0.433751	−0.046590	0.027*
C21	0.2603 (2)	0.49723 (16)	−0.00847 (19)	0.0210 (5)
H21	0.226402	0.550252	−0.015577	0.025*
C22	0.4341 (3)	0.77815 (17)	0.02572 (18)	0.0200 (5)
C23	0.5038 (2)	0.84472 (18)	0.0536 (2)	0.0218 (6)
H23	0.579426	0.835222	0.079756	0.026*
C24	0.4626 (3)	0.92424 (19)	0.0430 (2)	0.0245 (6)
H24	0.508920	0.969140	0.063506	0.029*
C25	0.3528 (2)	0.93851 (17)	0.0021 (2)	0.0224 (5)
C26	0.2850 (3)	0.87208 (18)	−0.0280 (2)	0.0246 (6)
H26	0.211107	0.881526	−0.056691	0.030*
C27	0.3254 (3)	0.79285 (18)	−0.0159 (2)	0.0227 (6)
H27	0.278830	0.747965	−0.036070	0.027*
C28	0.4765 (2)	0.69677 (17)	0.04278 (19)	0.0191 (5)
H28	0.554585	0.688309	0.065320	0.023*
C29	0.1681 (3)	0.27560 (19)	−0.0308 (2)	0.0264 (6)
F7	0.2233 (2)	0.21865 (13)	−0.07827 (18)	0.0496 (6)
F8	0.1376 (2)	0.23782 (16)	0.04374 (15)	0.0505 (6)
F9	0.0658 (2)	0.29164 (13)	−0.0721 (2)	0.0568 (7)
C30	0.3056 (3)	1.02408 (19)	−0.0050 (2)	0.0278 (6)
F10A	0.2293 (3)	1.03321 (16)	−0.0731 (2)	0.0490 (9)	0.858 (7)
F11A	0.3883 (2)	1.07933 (18)	−0.0172 (4)	0.0642 (14)	0.858 (7)
F12A	0.2404 (4)	1.04626 (19)	0.0632 (2)	0.0584 (12)	0.858 (7)
F10B	0.348 (3)	1.0627 (13)	−0.0682 (17)	0.088 (9)	0.142 (7)
F11B	0.348 (2)	1.0685 (10)	0.0662 (15)	0.072 (7)	0.142 (7)
F12B	0.1985 (11)	1.0295 (12)	0.000 (2)	0.073 (7)	0.142 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2	0.0228 (11)	0.0228 (12)	0.0193 (11)	0.0007 (9)	0.0002 (9)	−0.0001 (9)
N1	0.0272 (12)	0.0252 (13)	0.0296 (13)	0.0013 (10)	0.0045 (11)	0.0033 (11)
C1	0.0202 (13)	0.0244 (15)	0.0175 (13)	0.0020 (10)	−0.0007 (10)	0.0003 (10)
C2	0.0223 (13)	0.0264 (14)	0.0253 (14)	0.0043 (11)	0.0036 (11)	0.0012 (11)
C3	0.0273 (14)	0.0240 (14)	0.0253 (15)	0.0071 (11)	0.0007 (12)	0.0000 (11)
C4	0.0228 (13)	0.0243 (14)	0.0218 (13)	−0.0021 (11)	−0.0049 (11)	0.0012 (11)
C5	0.0195 (12)	0.0278 (15)	0.0234 (14)	−0.0006 (11)	0.0004 (11)	−0.0002 (11)
C6	0.0213 (13)	0.0229 (13)	0.0263 (14)	0.0035 (11)	0.0034 (11)	−0.0013 (11)
C7	0.0197 (12)	0.0233 (13)	0.0182 (13)	−0.0005 (10)	0.0004 (10)	0.0004 (10)
C8	0.0224 (13)	0.0237 (14)	0.0271 (14)	−0.0025 (11)	0.0051 (12)	0.0032 (11)
C9	0.0289 (14)	0.0200 (13)	0.0278 (14)	−0.0041 (11)	0.0039 (12)	0.0031 (11)
C10	0.0256 (14)	0.0181 (13)	0.0242 (14)	0.0006 (10)	0.0019 (11)	−0.0012 (10)
C11	0.0196 (12)	0.0274 (14)	0.0272 (15)	−0.0017 (11)	0.0049 (11)	−0.0010 (12)
C12	0.0232 (14)	0.0195 (13)	0.0294 (15)	−0.0072 (11)	0.0039 (12)	0.0017 (11)
C13	0.0176 (12)	0.0160 (12)	0.0227 (13)	0.0003 (10)	0.0028 (10)	0.0015 (10)
C14	0.0277 (15)	0.0255 (14)	0.0268 (15)	−0.0026 (12)	−0.0041 (12)	−0.0009 (11)
F1	0.0360 (10)	0.0278 (10)	0.0714 (16)	0.0013 (9)	−0.0081 (11)	0.0105 (10)
F2	0.0479 (12)	0.0345 (11)	0.0487 (13)	−0.0088 (9)	0.0146 (11)	0.0025 (9)
F3	0.0881 (18)	0.0431 (12)	0.0331 (11)	−0.0298 (13)	−0.0221 (12)	0.0018 (10)
C15	0.0310 (15)	0.0245 (15)	0.0301 (16)	0.0013 (12)	0.0036 (13)	0.0015 (12)
F4	0.0759 (18)	0.0271 (11)	0.089 (2)	0.0140 (11)	−0.0330 (17)	−0.0203 (12)
F5	0.0775 (17)	0.0706 (17)	0.0375 (13)	0.0487 (15)	0.0010 (13)	0.0066 (12)
F6	0.0672 (16)	0.0328 (12)	0.116 (3)	0.0134 (12)	0.0602 (18)	0.0052 (14)
N4	0.0219 (11)	0.0194 (11)	0.0227 (12)	−0.0004 (9)	−0.0011 (9)	−0.0021 (9)
N3	0.0230 (12)	0.0280 (13)	0.0274 (13)	0.0038 (10)	−0.0051 (10)	−0.0042 (10)
C16	0.0177 (12)	0.0188 (12)	0.0189 (13)	0.0001 (10)	0.0026 (10)	−0.0021 (9)
C17	0.0178 (11)	0.0220 (13)	0.0213 (13)	0.0030 (10)	0.0002 (10)	−0.0011 (10)
C18	0.0234 (13)	0.0162 (12)	0.0257 (14)	0.0022 (10)	0.0021 (11)	−0.0026 (10)
C19	0.0227 (13)	0.0197 (12)	0.0197 (13)	−0.0035 (10)	0.0015 (11)	−0.0014 (10)
C20	0.0180 (12)	0.0235 (13)	0.0263 (14)	0.0013 (10)	−0.0030 (11)	−0.0004 (11)
C21	0.0201 (12)	0.0175 (12)	0.0255 (14)	0.0014 (10)	−0.0012 (11)	0.0026 (10)
C22	0.0217 (12)	0.0178 (13)	0.0204 (13)	−0.0014 (10)	0.0025 (10)	−0.0020 (10)
C23	0.0183 (12)	0.0214 (13)	0.0258 (14)	−0.0032 (10)	−0.0012 (11)	0.0003 (11)
C24	0.0226 (13)	0.0226 (14)	0.0283 (15)	−0.0041 (11)	0.0014 (12)	−0.0015 (11)
C25	0.0207 (12)	0.0201 (13)	0.0264 (14)	−0.0015 (10)	0.0050 (11)	0.0020 (10)
C26	0.0204 (13)	0.0271 (15)	0.0263 (14)	−0.0006 (11)	−0.0015 (11)	0.0004 (11)
C27	0.0214 (12)	0.0226 (13)	0.0242 (14)	−0.0025 (11)	−0.0021 (11)	−0.0014 (11)
C28	0.0151 (11)	0.0195 (13)	0.0227 (13)	−0.0002 (10)	−0.0038 (10)	−0.0002 (10)
C29	0.0299 (15)	0.0241 (15)	0.0253 (14)	−0.0047 (12)	0.0001 (12)	−0.0045 (11)
F7	0.0603 (14)	0.0282 (11)	0.0602 (14)	−0.0150 (10)	0.0239 (12)	−0.0199 (10)
F8	0.0668 (15)	0.0537 (14)	0.0310 (11)	−0.0381 (12)	0.0075 (11)	−0.0020 (10)
F9	0.0480 (13)	0.0331 (11)	0.089 (2)	−0.0112 (10)	−0.0379 (14)	−0.0027 (12)
C30	0.0214 (13)	0.0244 (14)	0.0375 (17)	−0.0003 (11)	0.0043 (12)	0.0023 (12)
F10A	0.0640 (19)	0.0319 (13)	0.0513 (18)	0.0136 (13)	−0.0239 (16)	0.0031 (13)
F11A	0.0223 (12)	0.0228 (13)	0.148 (4)	−0.0038 (9)	−0.0036 (18)	0.014 (2)
F12A	0.085 (3)	0.0449 (17)	0.0449 (17)	0.0400 (18)	0.0250 (18)	0.0110 (13)
F10B	0.14 (2)	0.035 (11)	0.090 (12)	0.038 (12)	0.066 (13)	0.044 (10)
F11B	0.100 (15)	0.025 (8)	0.091 (12)	0.030 (9)	−0.043 (11)	−0.031 (8)
F12B	0.020 (6)	0.051 (10)	0.15 (2)	0.006 (6)	0.008 (8)	−0.021 (12)

Geometric parameters (Å, º)

N2—C13	1.299 (4)	N3—C16	1.414 (4)
N2—N1	1.332 (3)	N3—H3A	0.8800
N1—C1	1.407 (4)	C16—C17	1.398 (4)
N1—H1	0.8800	C16—C21	1.399 (4)
C1—C6	1.405 (4)	C17—C18	1.383 (4)
C1—C2	1.406 (4)	C17—H17	0.9500
C2—C3	1.381 (4)	C18—C19	1.392 (4)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.395 (4)	C19—C20	1.387 (4)
C3—H3	0.9500	C19—C29	1.494 (4)
C4—C5	1.387 (4)	C20—C21	1.382 (4)
C4—C14	1.490 (4)	C20—H20	0.9500
C5—C6	1.382 (4)	C21—H21	0.9500
C5—H5	0.9500	C22—C27	1.394 (4)
C6—H6	0.9500	C22—C23	1.402 (4)
C7—C8	1.395 (4)	C22—C28	1.432 (4)
C7—C12	1.407 (4)	C23—C24	1.385 (4)
C7—C13	1.446 (4)	C23—H23	0.9500
C8—C9	1.382 (4)	C24—C25	1.400 (4)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.390 (4)	C25—C26	1.399 (4)
C9—H9	0.9500	C25—C30	1.495 (4)
C10—C11	1.392 (4)	C26—C27	1.380 (4)
C10—C15	1.490 (4)	C26—H26	0.9500
C11—C12	1.384 (4)	C27—H27	0.9500
C11—H11	0.9500	C28—H28	0.9500
C12—H12	0.9500	C29—F7	1.330 (4)
C13—H13	0.9500	C29—F9	1.333 (4)
C14—F1	1.327 (4)	C29—F8	1.339 (4)
C14—F3	1.335 (4)	C30—F12B	1.206 (13)
C14—F2	1.341 (4)	C30—F10B	1.247 (14)
C15—F6	1.317 (4)	C30—F11A	1.305 (4)
C15—F5	1.328 (4)	C30—F12A	1.322 (4)
C15—F4	1.341 (4)	C30—F10A	1.355 (4)
N4—C28	1.319 (4)	C30—F11B	1.387 (14)
N4—N3	1.334 (3)
C13—N2—N1	118.4 (2)	C16—N3—H3A	120.1
N2—N1—C1	119.7 (2)	C17—C16—C21	119.4 (2)
N2—N1—H1	120.2	C17—C16—N3	119.1 (2)
C1—N1—H1	120.2	C21—C16—N3	121.5 (2)
C6—C1—C2	118.9 (3)	C18—C17—C16	120.3 (3)
C6—C1—N1	121.6 (3)	C18—C17—H17	119.8
C2—C1—N1	119.5 (3)	C16—C17—H17	119.8
C3—C2—C1	120.1 (3)	C17—C18—C19	119.8 (3)
C3—C2—H2	119.9	C17—C18—H18	120.1
C1—C2—H2	119.9	C19—C18—H18	120.1
C2—C3—C4	120.7 (3)	C20—C19—C18	120.3 (3)
C2—C3—H3	119.7	C20—C19—C29	120.4 (3)
C4—C3—H3	119.7	C18—C19—C29	119.3 (3)
C5—C4—C3	119.4 (3)	C21—C20—C19	120.2 (3)
C5—C4—C14	121.1 (3)	C21—C20—H20	119.9
C3—C4—C14	119.4 (3)	C19—C20—H20	119.9
C6—C5—C4	120.7 (3)	C20—C21—C16	120.0 (2)
C6—C5—H5	119.7	C20—C21—H21	120.0
C4—C5—H5	119.7	C16—C21—H21	120.0
C5—C6—C1	120.2 (3)	C27—C22—C23	119.5 (3)
C5—C6—H6	119.9	C27—C22—C28	122.1 (3)
C1—C6—H6	119.9	C23—C22—C28	118.4 (3)
C8—C7—C12	119.7 (3)	C24—C23—C22	120.2 (3)
C8—C7—C13	119.7 (3)	C24—C23—H23	119.9
C12—C7—C13	120.6 (3)	C22—C23—H23	119.9
C9—C8—C7	120.0 (3)	C23—C24—C25	120.0 (3)
C9—C8—H8	120.0	C23—C24—H24	120.0
C7—C8—H8	120.0	C25—C24—H24	120.0
C8—C9—C10	120.3 (3)	C26—C25—C24	119.7 (3)
C8—C9—H9	119.9	C26—C25—C30	120.4 (3)
C10—C9—H9	119.9	C24—C25—C30	119.9 (3)
C9—C10—C11	120.2 (3)	C27—C26—C25	120.1 (3)
C9—C10—C15	119.6 (3)	C27—C26—H26	120.0
C11—C10—C15	120.2 (3)	C25—C26—H26	120.0
C12—C11—C10	120.0 (3)	C26—C27—C22	120.5 (3)
C12—C11—H11	120.0	C26—C27—H27	119.7
C10—C11—H11	120.0	C22—C27—H27	119.7
C11—C12—C7	119.8 (3)	N4—C28—C22	119.2 (2)
C11—C12—H12	120.1	N4—C28—H28	120.4
C7—C12—H12	120.1	C22—C28—H28	120.4
N2—C13—C7	119.4 (2)	F7—C29—F9	106.3 (3)
N2—C13—H13	120.3	F7—C29—F8	105.1 (3)
C7—C13—H13	120.3	F9—C29—F8	105.8 (3)
F1—C14—F3	107.5 (3)	F7—C29—C19	113.3 (3)
F1—C14—F2	105.8 (3)	F9—C29—C19	113.0 (3)
F3—C14—F2	105.3 (3)	F8—C29—C19	112.6 (3)
F1—C14—C4	113.1 (3)	F12B—C30—F10B	112.9 (19)
F3—C14—C4	111.6 (3)	F11A—C30—F12A	108.5 (4)
F2—C14—C4	113.0 (3)	F11A—C30—F10A	105.2 (3)
F6—C15—F5	106.8 (3)	F12A—C30—F10A	103.0 (3)
F6—C15—F4	105.3 (3)	F12B—C30—F11B	104.7 (16)
F5—C15—F4	104.3 (3)	F10B—C30—F11B	102.3 (16)
F6—C15—C10	113.8 (3)	F12B—C30—C25	114.6 (10)
F5—C15—C10	112.9 (3)	F10B—C30—C25	113.0 (10)
F4—C15—C10	112.9 (3)	F11A—C30—C25	113.7 (3)
C28—N4—N3	118.0 (2)	F12A—C30—C25	113.2 (3)
N4—N3—C16	119.7 (2)	F10A—C30—C25	112.4 (3)
N4—N3—H3A	120.1	F11B—C30—C25	108.0 (7)
C13—N2—N1—C1	180.0 (3)	C21—C16—C17—C18	−0.8 (4)
N2—N1—C1—C6	1.2 (4)	N3—C16—C17—C18	178.1 (3)
N2—N1—C1—C2	−178.8 (3)	C16—C17—C18—C19	0.0 (4)
C6—C1—C2—C3	0.8 (4)	C17—C18—C19—C20	1.0 (4)
N1—C1—C2—C3	−179.3 (3)	C17—C18—C19—C29	−177.3 (3)
C1—C2—C3—C4	−0.9 (5)	C18—C19—C20—C21	−1.3 (5)
C2—C3—C4—C5	0.1 (5)	C29—C19—C20—C21	177.0 (3)
C2—C3—C4—C14	178.1 (3)	C19—C20—C21—C16	0.5 (5)
C3—C4—C5—C6	0.8 (5)	C17—C16—C21—C20	0.5 (4)
C14—C4—C5—C6	−177.1 (3)	N3—C16—C21—C20	−178.4 (3)
C4—C5—C6—C1	−1.0 (5)	C27—C22—C23—C24	2.6 (4)
C2—C1—C6—C5	0.2 (4)	C28—C22—C23—C24	−176.2 (3)
N1—C1—C6—C5	−179.8 (3)	C22—C23—C24—C25	−1.9 (5)
C12—C7—C8—C9	−1.1 (5)	C23—C24—C25—C26	0.0 (5)
C13—C7—C8—C9	177.6 (3)	C23—C24—C25—C30	176.7 (3)
C7—C8—C9—C10	0.4 (5)	C24—C25—C26—C27	1.1 (5)
C8—C9—C10—C11	0.3 (5)	C30—C25—C26—C27	−175.6 (3)
C8—C9—C10—C15	−177.5 (3)	C25—C26—C27—C22	−0.4 (5)
C9—C10—C11—C12	−0.3 (5)	C23—C22—C27—C26	−1.5 (4)
C15—C10—C11—C12	177.5 (3)	C28—C22—C27—C26	177.3 (3)
C10—C11—C12—C7	−0.4 (5)	N3—N4—C28—C22	178.7 (3)
C8—C7—C12—C11	1.1 (5)	C27—C22—C28—N4	−6.9 (4)
C13—C7—C12—C11	−177.6 (3)	C23—C22—C28—N4	171.8 (3)
N1—N2—C13—C7	178.7 (3)	C20—C19—C29—F7	134.3 (3)
C8—C7—C13—N2	−176.9 (3)	C18—C19—C29—F7	−47.4 (4)
C12—C7—C13—N2	1.8 (4)	C20—C19—C29—F9	13.4 (4)
C5—C4—C14—F1	−144.8 (3)	C18—C19—C29—F9	−168.4 (3)
C3—C4—C14—F1	37.3 (4)	C20—C19—C29—F8	−106.5 (3)
C5—C4—C14—F3	93.9 (4)	C18—C19—C29—F8	71.8 (4)
C3—C4—C14—F3	−84.0 (4)	C26—C25—C30—F12B	30.6 (18)
C5—C4—C14—F2	−24.6 (4)	C24—C25—C30—F12B	−146.1 (18)
C3—C4—C14—F2	157.5 (3)	C26—C25—C30—F10B	−101 (2)
C9—C10—C15—F6	−175.5 (3)	C24—C25—C30—F10B	83 (2)
C11—C10—C15—F6	6.7 (5)	C26—C25—C30—F11A	−147.8 (4)
C9—C10—C15—F5	62.5 (4)	C24—C25—C30—F11A	35.5 (5)
C11—C10—C15—F5	−115.3 (4)	C26—C25—C30—F12A	87.8 (4)
C9—C10—C15—F4	−55.6 (4)	C24—C25—C30—F12A	−88.9 (4)
C11—C10—C15—F4	126.6 (3)	C26—C25—C30—F10A	−28.4 (4)
C28—N4—N3—C16	−176.2 (3)	C24—C25—C30—F10A	154.9 (3)
N4—N3—C16—C17	175.1 (3)	C26—C25—C30—F11B	146.9 (13)
N4—N3—C16—C21	−6.0 (4)	C24—C25—C30—F11B	−29.8 (14)