organic compounds
The asymmetric unit of the title compound, C15H11F1N2, comprises two molecules with dihedral angles of 50.6 (1)/49.2 (1) and 51.5 (1)/53.3 (1)° between the pyrazole and, respectively, the phenyl and 4-fluorophenyl rings. One intermolecular C—HF close contact is noted for each unique molecule.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009911/na6165sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009911/na6165Isup2.hkl |
CCDC reference: 189891
Computing details top
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
5-(4-Fluorophenyl)-1-phenylpyrazole top
Crystal data top
C15H11FN2 | Z = 4 |
Mr = 238.26 | F(000) = 496 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
a = 7.847 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.904 (2) Å | Cell parameters from 16018 reflections |
c = 19.551 (4) Å | θ = 2.9–27.5° |
α = 90.20 (3)° | µ = 0.09 mm−1 |
β = 100.92 (3)° | T = 150 K |
γ = 90.61 (3)° | Block, yellow |
V = 1190.5 (4) Å3 | 0.20 × 0.18 × 0.10 mm |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 5311 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 3979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
φ and ω scans | h = −10→10 |
Absorption correction: multi-scan SORTAV (Blessing, 1995) | k = −10→10 |
Tmin = 0.982, Tmax = 0.991 | l = −23→25 |
17989 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.082 | H-atom parameters constrained |
wR(F2) = 0.238 | w = 1/[σ2(Fo2) + (0.0756P)2 + 2.8942P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
5311 reflections | Δρmax = 0.32 e Å−3 |
326 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.077 (9) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1A | 0.4367 (4) | 0.1330 (4) | 0.36661 (15) | 0.0218 (6) | |
N2A | 0.5261 (4) | 0.2825 (4) | 0.37098 (15) | 0.0254 (7) | |
C3A | 0.3603 (5) | 0.2688 (5) | 0.45435 (18) | 0.0256 (7) | |
H3A | 0.3092 | 0.3005 | 0.4928 | 0.032* | |
C4A | 0.4788 (5) | 0.3629 (5) | 0.42401 (19) | 0.0271 (8) | |
H4A | 0.5207 | 0.4722 | 0.4397 | 0.034* | |
C5A | 0.3341 (4) | 0.1209 (4) | 0.41656 (17) | 0.0223 (7) | |
C6A | 0.4649 (4) | 0.0060 (4) | 0.31756 (18) | 0.0232 (7) | |
C7A | 0.5048 (4) | −0.1569 (5) | 0.33972 (19) | 0.0256 (8) | |
H7A | 0.5144 | −0.1854 | 0.3875 | 0.032* | |
C8A | 0.5306 (5) | −0.2786 (5) | 0.2915 (2) | 0.0270 (8) | |
H8A | 0.5580 | −0.3911 | 0.3063 | 0.034* | |
C9A | 0.5167 (5) | −0.2375 (5) | 0.2222 (2) | 0.0290 (8) | |
H9A | 0.5338 | −0.3214 | 0.1893 | 0.036* | |
C10A | 0.4774 (5) | −0.0718 (5) | 0.2005 (2) | 0.0293 (8) | |
H10A | 0.4681 | −0.0433 | 0.1528 | 0.037* | |
C11A | 0.4517 (5) | 0.0517 (5) | 0.24812 (18) | 0.0255 (8) | |
H11A | 0.4257 | 0.1646 | 0.2336 | 0.032* | |
C12A | 0.2110 (4) | −0.0204 (4) | 0.41833 (18) | 0.0225 (7) | |
C13A | 0.2022 (5) | −0.0992 (5) | 0.48138 (19) | 0.0263 (8) | |
H13A | 0.2764 | −0.0624 | 0.5230 | 0.033* | |
C14A | 0.0851 (5) | −0.2314 (5) | 0.4834 (2) | 0.0284 (8) | |
H14A | 0.0783 | −0.2862 | 0.5260 | 0.035* | |
C15A | −0.0201 (5) | −0.2804 (5) | 0.4225 (2) | 0.0281 (8) | |
F15A | −0.1352 (3) | −0.4114 (3) | 0.42401 (13) | 0.0363 (6) | |
C16A | −0.0170 (5) | −0.2055 (5) | 0.3591 (2) | 0.0281 (8) | |
H16A | −0.0924 | −0.2427 | 0.3177 | 0.035* | |
C17A | 0.1002 (5) | −0.0743 (5) | 0.35808 (19) | 0.0255 (7) | |
H17A | 0.1050 | −0.0197 | 0.3152 | 0.032* | |
N1B | 0.1848 (4) | 0.4929 (4) | 0.13510 (15) | 0.0216 (6) | |
N2B | 0.3247 (4) | 0.3953 (4) | 0.13030 (16) | 0.0249 (7) | |
C3B | 0.3901 (5) | 0.4668 (5) | 0.07906 (19) | 0.0274 (8) | |
H3B | 0.4898 | 0.4265 | 0.0634 | 0.034* | |
C4B | 0.2963 (5) | 0.6070 (5) | 0.05110 (19) | 0.0260 (8) | |
H4B | 0.3184 | 0.6772 | 0.0143 | 0.032* | |
C5B | 0.1646 (4) | 0.6222 (4) | 0.08822 (18) | 0.0230 (7) | |
C6B | 0.0749 (4) | 0.4461 (4) | 0.18318 (18) | 0.0220 (7) | |
C7B | −0.1017 (5) | 0.4289 (4) | 0.15942 (19) | 0.0244 (7) | |
H7B | −0.1507 | 0.4487 | 0.1119 | 0.031* | |
C8B | −0.2074 (5) | 0.3820 (5) | 0.2066 (2) | 0.0268 (8) | |
H8B | −0.3291 | 0.3698 | 0.1909 | 0.034* | |
C9B | −0.1363 (5) | 0.3533 (5) | 0.2755 (2) | 0.0274 (8) | |
H9B | −0.2082 | 0.3204 | 0.3073 | 0.034* | |
C10B | 0.0423 (5) | 0.3730 (5) | 0.29814 (19) | 0.0280 (8) | |
H10B | 0.0918 | 0.3549 | 0.3457 | 0.035* | |
C11B | 0.1481 (5) | 0.4185 (4) | 0.25210 (19) | 0.0247 (7) | |
H11B | 0.2699 | 0.4308 | 0.2677 | 0.031* | |
C12B | 0.0282 (4) | 0.7509 (4) | 0.08464 (18) | 0.0225 (7) | |
C13B | −0.0794 (5) | 0.7846 (5) | 0.02086 (19) | 0.0266 (8) | |
H13B | −0.0643 | 0.7245 | −0.0197 | 0.033* | |
C14B | −0.2085 (5) | 0.9054 (5) | 0.0162 (2) | 0.0284 (8) | |
H14B | −0.2824 | 0.9288 | −0.0270 | 0.036* | |
C15B | −0.2260 (5) | 0.9902 (4) | 0.0760 (2) | 0.0274 (8) | |
F15B | −0.3533 (3) | 1.1080 (3) | 0.07171 (12) | 0.0354 (6) | |
C16B | −0.1208 (5) | 0.9627 (5) | 0.1395 (2) | 0.0298 (8) | |
H16B | −0.1352 | 1.0252 | 0.1796 | 0.037* | |
C17B | 0.0069 (5) | 0.8412 (5) | 0.14350 (19) | 0.0268 (8) | |
H17B | 0.0807 | 0.8195 | 0.1869 | 0.033* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0228 (14) | 0.0216 (14) | 0.0217 (15) | −0.0047 (11) | 0.0063 (11) | −0.0007 (11) |
N2A | 0.0278 (15) | 0.0238 (15) | 0.0243 (16) | −0.0066 (12) | 0.0048 (12) | −0.0006 (11) |
C3A | 0.0272 (18) | 0.0289 (18) | 0.0206 (17) | −0.0029 (14) | 0.0042 (14) | −0.0009 (13) |
C4A | 0.0313 (19) | 0.0239 (18) | 0.0253 (19) | −0.0051 (14) | 0.0039 (15) | −0.0034 (14) |
C5A | 0.0199 (16) | 0.0282 (18) | 0.0186 (17) | −0.0010 (13) | 0.0032 (13) | 0.0033 (13) |
C6A | 0.0188 (16) | 0.0280 (18) | 0.0231 (18) | −0.0015 (13) | 0.0050 (13) | −0.0020 (13) |
C7A | 0.0224 (17) | 0.0298 (19) | 0.0244 (18) | −0.0010 (14) | 0.0039 (14) | 0.0014 (14) |
C8A | 0.0230 (17) | 0.0240 (18) | 0.034 (2) | −0.0017 (14) | 0.0054 (15) | 0.0006 (14) |
C9A | 0.0250 (18) | 0.033 (2) | 0.030 (2) | −0.0027 (15) | 0.0089 (15) | −0.0072 (15) |
C10A | 0.0276 (18) | 0.037 (2) | 0.0241 (19) | −0.0007 (15) | 0.0076 (15) | −0.0007 (15) |
C11A | 0.0253 (17) | 0.0272 (18) | 0.0249 (18) | −0.0008 (14) | 0.0069 (14) | 0.0025 (14) |
C12A | 0.0203 (16) | 0.0223 (17) | 0.0255 (18) | 0.0006 (13) | 0.0063 (13) | 0.0007 (13) |
C13A | 0.0255 (17) | 0.0293 (19) | 0.0246 (19) | 0.0002 (14) | 0.0058 (14) | 0.0032 (14) |
C14A | 0.0316 (19) | 0.0274 (18) | 0.0283 (19) | 0.0003 (15) | 0.0108 (15) | 0.0053 (14) |
C15A | 0.0246 (17) | 0.0224 (17) | 0.040 (2) | −0.0051 (14) | 0.0143 (16) | −0.0009 (15) |
F15A | 0.0356 (12) | 0.0306 (12) | 0.0458 (14) | −0.0125 (10) | 0.0164 (10) | −0.0015 (10) |
C16A | 0.0249 (18) | 0.032 (2) | 0.0273 (19) | −0.0045 (15) | 0.0045 (14) | −0.0036 (15) |
C17A | 0.0257 (17) | 0.0281 (18) | 0.0231 (18) | −0.0022 (14) | 0.0058 (14) | 0.0015 (14) |
N1B | 0.0195 (13) | 0.0249 (15) | 0.0213 (15) | 0.0031 (11) | 0.0055 (11) | 0.0012 (11) |
N2B | 0.0217 (14) | 0.0288 (16) | 0.0248 (16) | 0.0046 (12) | 0.0053 (12) | −0.0017 (12) |
C3B | 0.0235 (17) | 0.034 (2) | 0.0257 (19) | 0.0044 (14) | 0.0068 (14) | −0.0029 (14) |
C4B | 0.0259 (17) | 0.0300 (19) | 0.0235 (18) | 0.0015 (14) | 0.0084 (14) | −0.0002 (14) |
C5B | 0.0230 (17) | 0.0250 (17) | 0.0208 (17) | 0.0009 (13) | 0.0033 (13) | 0.0014 (13) |
C6B | 0.0245 (17) | 0.0182 (16) | 0.0245 (18) | 0.0009 (13) | 0.0073 (13) | −0.0003 (12) |
C7B | 0.0234 (17) | 0.0265 (18) | 0.0231 (18) | 0.0016 (14) | 0.0033 (14) | 0.0008 (13) |
C8B | 0.0199 (16) | 0.0279 (18) | 0.033 (2) | 0.0005 (14) | 0.0062 (14) | 0.0004 (14) |
C9B | 0.0289 (18) | 0.0251 (18) | 0.031 (2) | 0.0033 (14) | 0.0131 (15) | 0.0019 (14) |
C10B | 0.0319 (19) | 0.0300 (19) | 0.0222 (18) | 0.0028 (15) | 0.0056 (15) | 0.0035 (14) |
C11B | 0.0203 (16) | 0.0269 (18) | 0.0266 (19) | 0.0013 (13) | 0.0035 (13) | 0.0001 (14) |
C12B | 0.0219 (16) | 0.0215 (17) | 0.0252 (18) | 0.0000 (13) | 0.0074 (13) | 0.0007 (13) |
C13B | 0.0256 (18) | 0.0275 (18) | 0.0267 (19) | 0.0005 (14) | 0.0046 (14) | −0.0012 (14) |
C14B | 0.0262 (18) | 0.0293 (19) | 0.028 (2) | 0.0022 (15) | 0.0009 (15) | 0.0052 (14) |
C15B | 0.0236 (17) | 0.0234 (18) | 0.037 (2) | 0.0058 (14) | 0.0089 (15) | 0.0071 (15) |
F15B | 0.0318 (12) | 0.0332 (12) | 0.0435 (14) | 0.0116 (9) | 0.0126 (10) | 0.0095 (10) |
C16B | 0.034 (2) | 0.0287 (19) | 0.028 (2) | 0.0053 (15) | 0.0110 (16) | 0.0006 (15) |
C17B | 0.0262 (18) | 0.0283 (18) | 0.0255 (19) | 0.0029 (14) | 0.0038 (14) | 0.0015 (14) |
Geometric parameters (Å, º) top
N1A—N2A | 1.362 (4) | N1B—C5B | 1.366 (4) |
N1A—C5A | 1.381 (4) | N1B—N2B | 1.366 (4) |
N1A—C6A | 1.433 (4) | N1B—C6B | 1.437 (4) |
N2A—C4A | 1.328 (5) | N2B—C3B | 1.334 (5) |
C3A—C5A | 1.373 (5) | C3B—C4B | 1.392 (5) |
C3A—C4A | 1.403 (5) | C3B—H3B | 0.95 |
C3A—H3A | 0.95 | C4B—C5B | 1.377 (5) |
C4A—H4A | 0.95 | C4B—H4B | 0.95 |
C5A—C12A | 1.474 (5) | C5B—C12B | 1.477 (5) |
C6A—C7A | 1.380 (5) | C6B—C11B | 1.380 (5) |
C6A—C11A | 1.391 (5) | C6B—C7B | 1.381 (5) |
C7A—C8A | 1.387 (5) | C7B—C8B | 1.400 (5) |
C7A—H7A | 0.95 | C7B—H7B | 0.95 |
C8A—C9A | 1.380 (5) | C8B—C9B | 1.378 (5) |
C8A—H8A | 0.95 | C8B—H8B | 0.95 |
C9A—C10A | 1.397 (6) | C9B—C10B | 1.394 (5) |
C9A—H9A | 0.9500 | C9B—H9B | 0.95 |
C10A—C11A | 1.389 (5) | C10B—C11B | 1.382 (5) |
C10A—H10A | 0.95 | C10B—H10B | 0.95 |
C11A—H11A | 0.95 | C11B—H11B | 0.95 |
C12A—C17A | 1.388 (5) | C12B—C17B | 1.390 (5) |
C12A—C13A | 1.396 (5) | C12B—C13B | 1.395 (5) |
C13A—C14A | 1.390 (5) | C13B—C14B | 1.390 (5) |
C13A—H13A | 0.95 | C13B—H13B | 0.95 |
C14A—C15A | 1.366 (6) | C14B—C15B | 1.375 (6) |
C14A—H14A | 0.95 | C14B—H14B | 0.95 |
C15A—F15A | 1.371 (4) | C15B—F15B | 1.364 (4) |
C15A—C16A | 1.381 (5) | C15B—C16B | 1.375 (5) |
C16A—C17A | 1.381 (5) | C16B—C17B | 1.387 (5) |
C16A—H16A | 0.95 | C16B—H16B | 0.95 |
C17A—H17A | 0.95 | C17B—H17B | 0.95 |
N2A—N1A—C5A | 112.0 (3) | C5B—N1B—N2B | 112.2 (3) |
N2A—N1A—C6A | 120.1 (3) | C5B—N1B—C6B | 128.4 (3) |
C5A—N1A—C6A | 127.7 (3) | N2B—N1B—C6B | 119.3 (3) |
C4A—N2A—N1A | 104.2 (3) | C3B—N2B—N1B | 103.8 (3) |
C5A—C3A—C4A | 105.1 (3) | N2B—C3B—C4B | 112.6 (3) |
C5A—C3A—H3A | 127.4 | N2B—C3B—H3B | 123.7 |
C4A—C3A—H3A | 127.4 | C4B—C3B—H3B | 123.7 |
N2A—C4A—C3A | 112.6 (3) | C5B—C4B—C3B | 105.2 (3) |
N2A—C4A—H4A | 123.7 | C5B—C4B—H4B | 127.4 |
C3A—C4A—H4A | 123.7 | C3B—C4B—H4B | 127.4 |
C3A—C5A—N1A | 106.1 (3) | N1B—C5B—C4B | 106.3 (3) |
C3A—C5A—C12A | 131.0 (3) | N1B—C5B—C12B | 123.1 (3) |
N1A—C5A—C12A | 122.5 (3) | C4B—C5B—C12B | 130.5 (3) |
C7A—C6A—C11A | 121.6 (3) | C11B—C6B—C7B | 121.3 (3) |
C7A—C6A—N1A | 120.0 (3) | C11B—C6B—N1B | 119.4 (3) |
C11A—C6A—N1A | 118.4 (3) | C7B—C6B—N1B | 119.3 (3) |
C6A—C7A—C8A | 119.3 (3) | C6B—C7B—C8B | 118.9 (3) |
C6A—C7A—H7A | 120.4 | C6B—C7B—H7B | 120.6 |
C8A—C7A—H7A | 120.4 | C8B—C7B—H7B | 120.6 |
C9A—C8A—C7A | 120.5 (3) | C9B—C8B—C7B | 120.6 (3) |
C9A—C8A—H8A | 119.8 | C9B—C8B—H8B | 119.7 |
C7A—C8A—H8A | 119.8 | C7B—C8B—H8B | 119.7 |
C8A—C9A—C10A | 119.7 (3) | C8B—C9B—C10B | 119.3 (3) |
C8A—C9A—H9A | 120.2 | C8B—C9B—H9B | 120.4 |
C10A—C9A—H9A | 120.2 | C10B—C9B—H9B | 120.4 |
C11A—C10A—C9A | 120.6 (3) | C11B—C10B—C9B | 120.8 (3) |
C11A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.6 |
C9A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.6 |
C10A—C11A—C6A | 118.4 (3) | C6B—C11B—C10B | 119.2 (3) |
C10A—C11A—H11A | 120.8 | C6B—C11B—H11B | 120.4 |
C6A—C11A—H11A | 120.8 | C10B—C11B—H11B | 120.4 |
C17A—C12A—C13A | 119.2 (3) | C17B—C12B—C13B | 119.4 (3) |
C17A—C12A—C5A | 120.7 (3) | C17B—C12B—C5B | 121.1 (3) |
C13A—C12A—C5A | 120.0 (3) | C13B—C12B—C5B | 119.5 (3) |
C14A—C13A—C12A | 120.2 (3) | C14B—C13B—C12B | 120.5 (3) |
C14A—C13A—H13A | 119.9 | C14B—C13B—H13B | 119.7 |
C12A—C13A—H13A | 119.9 | C12B—C13B—H13B | 119.7 |
C15A—C14A—C13A | 118.2 (3) | C15B—C14B—C13B | 118.1 (3) |
C15A—C14A—H14A | 120.9 | C15B—C14B—H14B | 121.0 |
C13A—C14A—H14A | 120.9 | C13B—C14B—H14B | 121.0 |
C14A—C15A—F15A | 118.6 (3) | F15B—C15B—C16B | 118.6 (3) |
C14A—C15A—C16A | 123.7 (3) | F15B—C15B—C14B | 118.2 (3) |
F15A—C15A—C16A | 117.8 (3) | C16B—C15B—C14B | 123.2 (3) |
C15A—C16A—C17A | 117.3 (3) | C15B—C16B—C17B | 118.1 (3) |
C15A—C16A—H16A | 121.4 | C15B—C16B—H16B | 120.9 |
C17A—C16A—H16A | 121.4 | C17B—C16B—H16B | 120.9 |
C16A—C17A—C12A | 121.4 (3) | C16B—C17B—C12B | 120.7 (3) |
C16A—C17A—H17A | 119.3 | C16B—C17B—H17B | 119.6 |
C12A—C17A—H17A | 119.3 | C12B—C17B—H17B | 119.6 |
C5A—N1A—N2A—C4A | 0.1 (4) | C5B—N1B—N2B—C3B | −0.3 (4) |
C6A—N1A—N2A—C4A | −175.5 (3) | C6B—N1B—N2B—C3B | 176.3 (3) |
N1A—N2A—C4A—C3A | 0.0 (4) | N1B—N2B—C3B—C4B | 0.1 (4) |
C5A—C3A—C4A—N2A | −0.2 (4) | N2B—C3B—C4B—C5B | 0.2 (4) |
C4A—C3A—C5A—N1A | 0.3 (4) | N2B—N1B—C5B—C4B | 0.5 (4) |
C4A—C3A—C5A—C12A | −172.8 (4) | C6B—N1B—C5B—C4B | −175.8 (3) |
N2A—N1A—C5A—C3A | −0.3 (4) | N2B—N1B—C5B—C12B | −177.1 (3) |
C6A—N1A—C5A—C3A | 175.0 (3) | C6B—N1B—C5B—C12B | 6.6 (5) |
N2A—N1A—C5A—C12A | 173.5 (3) | C3B—C4B—C5B—N1B | −0.4 (4) |
C6A—N1A—C5A—C12A | −11.2 (5) | C3B—C4B—C5B—C12B | 176.9 (4) |
N2A—N1A—C6A—C7A | 127.2 (3) | C5B—N1B—C6B—C11B | −131.1 (4) |
C5A—N1A—C6A—C7A | −47.7 (5) | N2B—N1B—C6B—C11B | 52.9 (4) |
N2A—N1A—C6A—C11A | −52.6 (4) | C5B—N1B—C6B—C7B | 49.1 (5) |
C5A—N1A—C6A—C11A | 132.6 (4) | N2B—N1B—C6B—C7B | −126.9 (3) |
C11A—C6A—C7A—C8A | −0.7 (5) | C11B—C6B—C7B—C8B | −0.3 (5) |
N1A—C6A—C7A—C8A | 179.6 (3) | N1B—C6B—C7B—C8B | 179.5 (3) |
C6A—C7A—C8A—C9A | 0.0 (5) | C6B—C7B—C8B—C9B | 0.0 (5) |
C7A—C8A—C9A—C10A | 0.4 (5) | C7B—C8B—C9B—C10B | 0.6 (5) |
C8A—C9A—C10A—C11A | −0.2 (5) | C8B—C9B—C10B—C11B | −0.9 (6) |
C9A—C10A—C11A—C6A | −0.4 (5) | C7B—C6B—C11B—C10B | 0.0 (5) |
C7A—C6A—C11A—C10A | 0.8 (5) | N1B—C6B—C11B—C10B | −179.8 (3) |
N1A—C6A—C11A—C10A | −179.4 (3) | C9B—C10B—C11B—C6B | 0.6 (6) |
C3A—C5A—C12A—C17A | 125.8 (4) | N1B—C5B—C12B—C17B | 52.5 (5) |
N1A—C5A—C12A—C17A | −46.3 (5) | C4B—C5B—C12B—C17B | −124.5 (4) |
C3A—C5A—C12A—C13A | −52.7 (5) | N1B—C5B—C12B—C13B | −128.6 (4) |
N1A—C5A—C12A—C13A | 135.2 (4) | C4B—C5B—C12B—C13B | 54.4 (5) |
C17A—C12A—C13A—C14A | 0.8 (5) | C17B—C12B—C13B—C14B | −1.0 (5) |
C5A—C12A—C13A—C14A | 179.3 (3) | C5B—C12B—C13B—C14B | −179.9 (3) |
C12A—C13A—C14A—C15A | −0.3 (5) | C12B—C13B—C14B—C15B | 0.2 (5) |
C13A—C14A—C15A—F15A | 179.6 (3) | C13B—C14B—C15B—F15B | −179.5 (3) |
C13A—C14A—C15A—C16A | −0.2 (6) | C13B—C14B—C15B—C16B | 0.9 (6) |
C14A—C15A—C16A—C17A | 0.2 (6) | F15B—C15B—C16B—C17B | 179.2 (3) |
F15A—C15A—C16A—C17A | −179.6 (3) | C14B—C15B—C16B—C17B | −1.2 (6) |
C15A—C16A—C17A—C12A | 0.4 (5) | C15B—C16B—C17B—C12B | 0.4 (6) |
C13A—C12A—C17A—C16A | −0.9 (5) | C13B—C12B—C17B—C16B | 0.7 (5) |
C5A—C12A—C17A—C16A | −179.4 (3) | C5B—C12B—C17B—C16B | 179.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···F15Ai | 0.95 | 2.48 | 3.415 (4) | 169 |
C4B—H4B···F15Bii | 0.95 | 2.44 | 3.385 (4) | 171 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x, −y+2, −z. |