organic compounds
The two independent molecules of C8H4N2O4F6S are linked by a pair of NamidoNpyridyl interactions [2.858 (2) and 2.880 (2) Å], giving rise to a hydrogen-bonded dimer. The conformation of the trifluoromethanesulfonate moiety is different in the two molecules.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001679/ci6333sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001679/ci6333Isup2.hkl |
CCDC reference: 234922
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.087
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact F1A .. O1 = 2.94 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact F4A .. N1 = 3.00 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Trifluoromethanesulfonic acid 2-(2,2,2-trifluoroacetylamino)pyridin-3-yl ester top
Crystal data top
C8H4F6N2O4S | Z = 4 |
Mr = 338.19 | F(000) = 672 |
Triclinic, P1 | Dx = 1.911 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8702 (5) Å | Cell parameters from 6114 reflections |
b = 10.0063 (5) Å | θ = 2.4–28.3° |
c = 12.6434 (6) Å | µ = 0.38 mm−1 |
α = 101.436 (1)° | T = 100 K |
β = 103.466 (1)° | Block, colorless |
γ = 95.981 (1)° | 0.40 × 0.35 × 0.30 mm |
V = 1175.4 (1) Å3 |
Data collection top
Bruker SMART area-detector diffractometer | 4725 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
φ and ω scans | h = −12→12 |
13584 measured reflections | k = −12→12 |
5315 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.052P)2 + 0.4147P] where P = (Fo2 + 2Fc2)/3 |
5315 reflections | (Δ/σ)max = 0.001 |
387 parameters | Δρmax = 0.51 e Å−3 |
2 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.17960 (4) | 0.31719 (4) | 0.47544 (3) | 0.0180 (1) | |
F1 | 0.4371 (1) | 0.3938 (1) | 0.6015 (1) | 0.0293 (2) | |
F2 | 0.3656 (1) | 0.1741 (1) | 0.5535 (1) | 0.0332 (3) | |
F3 | 0.2924 (1) | 0.3017 (1) | 0.6805 (1) | 0.0283 (2) | |
F4 | 0.2010 (1) | 0.6161 (1) | 0.9631 (1) | 0.0287 (2) | |
F5 | 0.3765 (1) | 0.5314 (1) | 0.9178 (1) | 0.0297 (2) | |
F6 | 0.1701 (1) | 0.4100 (1) | 0.8639 (1) | 0.0313 (2) | |
O1 | 0.0671 (1) | 0.2142 (1) | 0.4680 (1) | 0.0268 (3) | |
O2 | 0.2348 (1) | 0.3356 (1) | 0.3850 (1) | 0.0257 (3) | |
O3 | 0.1409 (1) | 0.4566 (1) | 0.5364 (1) | 0.0164 (2) | |
O4 | 0.0796 (1) | 0.5904 (1) | 0.7312 (1) | 0.0209 (2) | |
N1 | 0.3692 (1) | 0.7888 (1) | 0.6362 (1) | 0.0179 (3) | |
N2 | 0.3135 (1) | 0.6265 (1) | 0.7350 (1) | 0.0154 (3) | |
C1 | 0.3285 (2) | 0.2956 (2) | 0.5855 (1) | 0.0223 (3) | |
C2 | 0.2958 (2) | 0.6679 (2) | 0.6330 (1) | 0.0154 (3) | |
C3 | 0.2113 (2) | 0.5846 (2) | 0.5331 (1) | 0.0157 (3) | |
C4 | 0.1948 (2) | 0.6283 (2) | 0.4348 (1) | 0.0199 (3) | |
C5 | 0.2705 (2) | 0.7544 (2) | 0.4390 (1) | 0.0227 (3) | |
C6 | 0.3571 (2) | 0.8299 (2) | 0.5403 (1) | 0.0219 (3) | |
C7 | 0.2023 (2) | 0.5894 (2) | 0.7736 (1) | 0.0164 (3) | |
C8 | 0.2399 (2) | 0.5366 (2) | 0.8816 (1) | 0.0188 (3) | |
S1a | 0.88367 (4) | 1.05918 (4) | 0.79092 (3) | 0.0152 (1) | |
F1a | 1.0824 (1) | 0.9122 (1) | 0.7665 (1) | 0.0248 (2) | |
F2a | 1.1543 (1) | 1.1195 (1) | 0.8661 (1) | 0.0252 (2) | |
F3a | 1.0767 (1) | 1.0839 (1) | 0.6869 (1) | 0.0285 (2) | |
F4a | 0.3862 (1) | 1.0690 (1) | 0.7824 (1) | 0.0233 (2) | |
F5a | 0.5703 (1) | 1.2231 (1) | 0.8227 (1) | 0.0287 (2) | |
F6a | 0.4527 (1) | 1.2092 (1) | 0.9445 (1) | 0.0256 (2) | |
O1a | 0.8833 (1) | 1.2017 (1) | 0.8293 (1) | 0.0219 (2) | |
O2a | 0.7862 (1) | 0.9785 (1) | 0.6928 (1) | 0.0197 (2) | |
O3a | 0.8843 (1) | 0.9924 (1) | 0.8946 (1) | 0.0157 (2) | |
O4a | 0.6721 (1) | 1.0735 (1) | 1.0041 (1) | 0.0214 (2) | |
N1a | 0.6134 (1) | 0.6904 (1) | 0.8337 (1) | 0.0166 (3) | |
N2a | 0.5857 (1) | 0.9189 (1) | 0.8343 (1) | 0.0157 (3) | |
C1a | 1.0623 (2) | 1.0415 (2) | 0.7767 (1) | 0.0190 (3) | |
C2a | 0.6755 (2) | 0.8199 (2) | 0.8513 (1) | 0.0145 (3) | |
C3a | 0.8214 (2) | 0.8540 (2) | 0.8784 (1) | 0.0154 (3) | |
C4a | 0.9064 (2) | 0.7552 (2) | 0.8942 (1) | 0.0176 (3) | |
C5a | 0.8409 (2) | 0.6211 (2) | 0.8783 (1) | 0.0189 (3) | |
C6a | 0.6950 (2) | 0.5928 (2) | 0.8466 (1) | 0.0189 (3) | |
C7a | 0.5945 (2) | 1.0372 (2) | 0.9106 (1) | 0.0164 (3) | |
C8a | 0.4980 (2) | 1.1355 (2) | 0.8650 (1) | 0.0185 (3) | |
H2n | 0.398 (1) | 0.637 (2) | 0.774 (2) | 0.032 (6)* | |
H4 | 0.1337 | 0.5740 | 0.3668 | 0.024* | |
H5 | 0.2632 | 0.7887 | 0.3733 | 0.027* | |
H6 | 0.4108 | 0.9152 | 0.5419 | 0.026* | |
H2na | 0.518 (2) | 0.893 (2) | 0.776 (1) | 0.026 (5)* | |
H4a | 1.0063 | 0.7783 | 0.9153 | 0.021* | |
H5a | 0.8952 | 0.5495 | 0.8888 | 0.023* | |
H6a | 0.6507 | 0.5000 | 0.8335 | 0.023* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0211 (2) | 0.0142 (2) | 0.0168 (2) | 0.0013 (1) | 0.0038 (1) | 0.0010 (1) |
F1 | 0.0193 (5) | 0.0275 (5) | 0.0378 (6) | 0.0026 (4) | 0.0031 (4) | 0.0058 (4) |
F2 | 0.0402 (6) | 0.0222 (5) | 0.0373 (6) | 0.0166 (5) | 0.0075 (5) | 0.0043 (4) |
F3 | 0.0388 (6) | 0.0272 (5) | 0.0213 (5) | 0.0100 (4) | 0.0071 (4) | 0.0097 (4) |
F4 | 0.0409 (6) | 0.0296 (5) | 0.0177 (5) | 0.0088 (5) | 0.0114 (4) | 0.0045 (4) |
F5 | 0.0225 (5) | 0.0425 (6) | 0.0287 (5) | 0.0067 (4) | 0.0045 (4) | 0.0208 (5) |
F6 | 0.0426 (6) | 0.0201 (5) | 0.0284 (5) | −0.0084 (4) | 0.0079 (5) | 0.0078 (4) |
O1 | 0.0281 (6) | 0.0178 (6) | 0.0291 (6) | −0.0032 (5) | 0.0052 (5) | −0.0004 (5) |
O2 | 0.0360 (7) | 0.0219 (6) | 0.0207 (6) | 0.0067 (5) | 0.0109 (5) | 0.0033 (5) |
O3 | 0.0154 (5) | 0.0140 (5) | 0.0178 (5) | 0.0001 (4) | 0.0030 (4) | 0.0018 (4) |
O4 | 0.0160 (5) | 0.0256 (6) | 0.0204 (6) | 0.0032 (4) | 0.0048 (4) | 0.0037 (4) |
N1 | 0.0189 (6) | 0.0144 (6) | 0.0197 (6) | 0.0017 (5) | 0.0038 (5) | 0.0044 (5) |
N2 | 0.0139 (6) | 0.0160 (6) | 0.0148 (6) | 0.0000 (5) | 0.0014 (5) | 0.0038 (5) |
C1 | 0.0247 (8) | 0.0189 (8) | 0.0235 (8) | 0.0075 (6) | 0.0045 (6) | 0.0049 (6) |
C2 | 0.0142 (7) | 0.0153 (7) | 0.0173 (7) | 0.0040 (5) | 0.0038 (5) | 0.0046 (5) |
C3 | 0.0153 (7) | 0.0128 (7) | 0.0195 (7) | 0.0026 (5) | 0.0046 (6) | 0.0045 (6) |
C4 | 0.0187 (7) | 0.0225 (8) | 0.0170 (7) | 0.0044 (6) | 0.0007 (6) | 0.0049 (6) |
C5 | 0.0262 (8) | 0.0234 (8) | 0.0211 (8) | 0.0060 (7) | 0.0051 (6) | 0.0117 (6) |
C6 | 0.0237 (8) | 0.0177 (7) | 0.0261 (8) | 0.0027 (6) | 0.0065 (6) | 0.0095 (6) |
C7 | 0.0183 (7) | 0.0128 (7) | 0.0163 (7) | 0.0004 (6) | 0.0043 (6) | 0.0008 (5) |
C8 | 0.0193 (7) | 0.0187 (7) | 0.0184 (7) | 0.0000 (6) | 0.0053 (6) | 0.0049 (6) |
S1a | 0.0138 (2) | 0.0148 (2) | 0.0166 (2) | 0.0006 (1) | 0.0026 (1) | 0.0052 (1) |
F1a | 0.0233 (5) | 0.0227 (5) | 0.0298 (5) | 0.0069 (4) | 0.0094 (4) | 0.0048 (4) |
F2a | 0.0144 (4) | 0.0288 (5) | 0.0267 (5) | −0.0021 (4) | 0.0017 (4) | 0.0004 (4) |
F3a | 0.0264 (5) | 0.0375 (6) | 0.0266 (5) | 0.0017 (4) | 0.0120 (4) | 0.0143 (4) |
F4a | 0.0189 (5) | 0.0218 (5) | 0.0247 (5) | 0.0060 (4) | −0.0011 (4) | 0.0016 (4) |
F5a | 0.0248 (5) | 0.0262 (5) | 0.0419 (6) | 0.0055 (4) | 0.0110 (4) | 0.0202 (5) |
F6a | 0.0271 (5) | 0.0218 (5) | 0.0270 (5) | 0.0093 (4) | 0.0078 (4) | −0.0006 (4) |
O1a | 0.0229 (6) | 0.0156 (5) | 0.0268 (6) | 0.0024 (4) | 0.0057 (5) | 0.0056 (4) |
O2a | 0.0190 (5) | 0.0215 (6) | 0.0170 (5) | 0.0001 (4) | 0.0009 (4) | 0.0066 (4) |
O3a | 0.0148 (5) | 0.0156 (5) | 0.0148 (5) | −0.0006 (4) | 0.0014 (4) | 0.0040 (4) |
O4a | 0.0232 (6) | 0.0210 (6) | 0.0180 (5) | 0.0039 (5) | 0.0027 (4) | 0.0026 (4) |
N1a | 0.0178 (6) | 0.0160 (6) | 0.0163 (6) | 0.0012 (5) | 0.0051 (5) | 0.0042 (5) |
N2a | 0.0136 (6) | 0.0154 (6) | 0.0164 (6) | 0.0011 (5) | 0.0017 (5) | 0.0032 (5) |
C1a | 0.0166 (7) | 0.0205 (8) | 0.0199 (8) | 0.0010 (6) | 0.0057 (6) | 0.0046 (6) |
C2a | 0.0167 (7) | 0.0150 (7) | 0.0124 (7) | 0.0028 (5) | 0.0042 (5) | 0.0041 (5) |
C3a | 0.0185 (7) | 0.0151 (7) | 0.0120 (7) | 0.0001 (6) | 0.0037 (5) | 0.0035 (5) |
C4a | 0.0164 (7) | 0.0229 (8) | 0.0149 (7) | 0.0046 (6) | 0.0047 (5) | 0.0058 (6) |
C5a | 0.0223 (8) | 0.0189 (7) | 0.0190 (7) | 0.0081 (6) | 0.0072 (6) | 0.0077 (6) |
C6a | 0.0244 (8) | 0.0158 (7) | 0.0176 (7) | 0.0018 (6) | 0.0071 (6) | 0.0050 (6) |
C7a | 0.0157 (7) | 0.0162 (7) | 0.0187 (7) | 0.0017 (6) | 0.0065 (6) | 0.0054 (6) |
C8a | 0.0170 (7) | 0.0164 (7) | 0.0211 (8) | 0.0020 (6) | 0.0044 (6) | 0.0032 (6) |
Geometric parameters (Å, º) top
S1—O1 | 1.406 (1) | F1a—C1a | 1.315 (2) |
S1—O2 | 1.411 (1) | F2a—C1a | 1.318 (2) |
S1—O3 | 1.584 (1) | F3a—C1a | 1.320 (2) |
S1—C1 | 1.837 (2) | F4a—C8a | 1.336 (2) |
F1—C1 | 1.325 (2) | F5a—C8a | 1.340 (2) |
F2—C1 | 1.321 (2) | F6a—C8a | 1.319 (2) |
F3—C1 | 1.322 (2) | O3a—C3a | 1.413 (2) |
F4—C8 | 1.329 (2) | O4a—C7a | 1.211 (2) |
F5—C8 | 1.330 (2) | N1a—C2a | 1.327 (2) |
F6—C8 | 1.328 (2) | N1a—C6a | 1.340 (2) |
O3—C3 | 1.405 (2) | N2a—C7a | 1.352 (2) |
O4—C7 | 1.207 (2) | N2a—C2a | 1.411 (2) |
N1—C2 | 1.332 (2) | C2a—C3a | 1.389 (2) |
N1—C6 | 1.340 (2) | C3a—C4a | 1.376 (2) |
N2—C7 | 1.348 (2) | C4a—C5a | 1.382 (2) |
N2—C2 | 1.410 (2) | C5a—C6a | 1.384 (2) |
C2—C3 | 1.390 (2) | C7a—C8a | 1.540 (2) |
C3—C4 | 1.378 (2) | N2—H2n | 0.85 (1) |
C4—C5 | 1.383 (2) | C4—H4 | 0.95 |
C5—C6 | 1.383 (2) | C5—H5 | 0.95 |
C7—C8 | 1.540 (2) | C6—H6 | 0.95 |
S1a—O1a | 1.413 (1) | N2a—H2na | 0.85 (1) |
S1a—O2a | 1.415 (1) | C4a—H4a | 0.95 |
S1a—O3a | 1.584 (1) | C5a—H5a | 0.95 |
S1a—C1a | 1.836 (2) | C6a—H6a | 0.95 |
O1—S1—O2 | 124.4 (1) | C7a—N2a—C2a | 123.5 (1) |
O1—S1—O3 | 105.4 (1) | F1a—C1a—F2a | 109.7 (1) |
O2—S1—O3 | 111.4 (1) | F1a—C1a—F3a | 109.8 (1) |
O1—S1—C1 | 106.5 (1) | F2a—C1a—F3a | 109.9 (1) |
O2—S1—C1 | 106.4 (1) | F1a—C1a—S1a | 110.7 (1) |
O3—S1—C1 | 100.0 (1) | F2a—C1a—S1a | 108.7 (1) |
C3—O3—S1 | 120.4 (1) | F3a—C1a—S1a | 108.1 (1) |
C2—N1—C6 | 118.0 (1) | N1a—C2a—C3a | 121.3 (1) |
C7—N2—C2 | 121.6 (1) | N1a—C2a—N2a | 116.6 (1) |
F2—C1—F3 | 109.4 (1) | C3a—C2a—N2a | 122.0 (1) |
F2—C1—F1 | 109.1 (1) | C4a—C3a—C2a | 120.8 (1) |
F3—C1—F1 | 109.0 (1) | C4a—C3a—O3a | 119.3 (1) |
F2—C1—S1 | 108.5 (1) | C2a—C3a—O3a | 119.9 (1) |
F3—C1—S1 | 110.7 (1) | C3a—C4a—C5a | 117.5 (1) |
F1—C1—S1 | 110.2 (1) | C4a—C5a—C6a | 118.9 (1) |
N1—C2—C3 | 121.5 (1) | N1a—C6a—C5a | 123.0 (1) |
N1—C2—N2 | 116.5 (1) | O4a—C7a—N2a | 127.5 (1) |
C3—C2—N2 | 122.0 (1) | O4a—C7a—C8a | 119.6 (1) |
C4—C3—C2 | 120.7 (1) | N2a—C7a—C8a | 112.8 (1) |
C4—C3—O3 | 121.4 (1) | F6a—C8a—F4a | 108.5 (1) |
C2—C3—O3 | 117.8 (1) | F6a—C8a—F5a | 107.9 (1) |
C5—C4—C3 | 117.4 (1) | F4a—C8a—F5a | 106.7 (1) |
C4—C5—C6 | 119.0 (1) | F6a—C8a—C7a | 111.4 (1) |
N1—C6—C5 | 123.3 (2) | F4a—C8a—C7a | 112.7 (1) |
O4—C7—N2 | 127.0 (1) | F5a—C8a—C7a | 109.5 (1) |
O4—C7—C8 | 118.3 (1) | C7—N2—H2n | 123 (2) |
N2—C7—C8 | 114.7 (1) | C2—N2—H2n | 115 (2) |
F6—C8—F4 | 107.4 (1) | C5—C4—H4 | 121.3 |
F6—C8—F5 | 107.6 (1) | C3—C4—H4 | 121.3 |
F4—C8—F5 | 108.0 (1) | C4—C5—H5 | 120.5 |
F6—C8—C7 | 109.4 (1) | C6—C5—H5 | 120.5 |
F4—C8—C7 | 110.6 (1) | N1—C6—H6 | 118.4 |
F5—C8—C7 | 113.7 (1) | C5—C6—H6 | 118.4 |
O1a—S1a—O2a | 122.4 (1) | C7a—N2a—H2na | 122 (1) |
O1a—S1a—O3a | 106.2 (1) | C2a—N2a—H2na | 114 (1) |
O2a—S1a—O3a | 111.4 (1) | C3a—C4a—H4a | 121.2 |
O1a—S1a—C1a | 106.6 (1) | C5a—C4a—H4a | 121.2 |
O2a—S1a—C1a | 108.0 (1) | C4a—C5a—H5a | 120.6 |
O3a—S1a—C1a | 99.9 (1) | C6a—C5a—H5a | 120.6 |
C3a—O3a—S1a | 120.5 (1) | N1a—C6a—H6a | 118.5 |
C2a—N1a—C6a | 118.4 (1) | C5a—C6a—H6a | 118.5 |
O1—S1—O3—C3 | −164.0 (1) | O1a—S1a—O3a—C3a | 150.5 (1) |
O2—S1—O3—C3 | −26.4 (1) | O2a—S1a—O3a—C3a | 15.0 (1) |
C1—S1—O3—C3 | 85.7 (1) | C1a—S1a—O3a—C3a | −98.9 (1) |
O1—S1—C1—F2 | 63.7 (1) | O1a—S1a—C1a—F1a | 165.5 (1) |
O2—S1—C1—F2 | −70.9 (1) | O2a—S1a—C1a—F1a | −61.3 (1) |
O3—S1—C1—F2 | 173.1 (1) | O3a—S1a—C1a—F1a | 55.2 (1) |
O1—S1—C1—F3 | −56.3 (1) | O1a—S1a—C1a—F2a | 44.9 (1) |
O2—S1—C1—F3 | 169.1 (1) | O2a—S1a—C1a—F2a | 178.1 (1) |
O3—S1—C1—F3 | 53.1 (1) | O3a—S1a—C1a—F2a | −65.4 (1) |
O1—S1—C1—F1 | −176.9 (1) | O1a—S1a—C1a—F3a | −74.3 (1) |
O2—S1—C1—F1 | 48.6 (1) | O2a—S1a—C1a—F3a | 59.0 (1) |
O3—S1—C1—F1 | −67.5 (1) | O3a—S1a—C1a—F3a | 175.5 (1) |
C6—N1—C2—C3 | 1.4 (2) | C6a—N1a—C2a—C3a | 2.4 (2) |
C6—N1—C2—N2 | 178.6 (1) | C6a—N1a—C2a—N2a | 178.7 (1) |
C7—N2—C2—N1 | 127.0 (2) | C7a—N2a—C2a—N1a | 128.3 (2) |
C7—N2—C2—C3 | −55.8 (2) | C7a—N2a—C2a—C3a | −55.5 (2) |
N1—C2—C3—C4 | −3.6 (2) | N1a—C2a—C3a—C4a | −3.9 (2) |
N2—C2—C3—C4 | 179.3 (1) | N2a—C2a—C3a—C4a | −179.9 (1) |
N1—C2—C3—O3 | 178.0 (1) | N1a—C2a—C3a—O3a | 178.8 (1) |
N2—C2—C3—O3 | 1.0 (2) | N2a—C2a—C3a—O3a | 2.8 (2) |
S1—O3—C3—C4 | 67.2 (2) | S1a—O3a—C3a—C4a | 106.8 (1) |
S1—O3—C3—C2 | −114.5 (1) | S1a—O3a—C3a—C2a | −75.8 (2) |
C2—C3—C4—C5 | 3.1 (2) | C2a—C3a—C4a—C5a | 2.2 (2) |
O3—C3—C4—C5 | −178.7 (1) | O3a—C3a—C4a—C5a | 179.6 (1) |
C3—C4—C5—C6 | −0.5 (2) | C3a—C4a—C5a—C6a | 0.5 (2) |
C2—N1—C6—C5 | 1.3 (2) | C2a—N1a—C6a—C5a | 0.4 (2) |
C4—C5—C6—N1 | −1.7 (3) | C4a—C5a—C6a—N1a | −1.9 (2) |
C2—N2—C7—O4 | −2.5 (2) | C2a—N2a—C7a—O4a | −3.9 (2) |
C2—N2—C7—C8 | 175.6 (1) | C2a—N2a—C7a—C8a | 172.2 (1) |
O4—C7—C8—F6 | 55.7 (2) | O4a—C7a—C8a—F6a | −35.1 (2) |
N2—C7—C8—F6 | −122.5 (1) | N2a—C7a—C8a—F6a | 148.5 (1) |
O4—C7—C8—F4 | −62.4 (2) | O4a—C7a—C8a—F4a | −157.3 (1) |
N2—C7—C8—F4 | 119.4 (1) | N2a—C7a—C8a—F4a | 26.3 (2) |
O4—C7—C8—F5 | 176.0 (1) | O4a—C7a—C8a—F5a | 84.1 (2) |
N2—C7—C8—F5 | −2.2 (2) | N2a—C7a—C8a—F5a | −92.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···N1a | 0.85 (1) | 2.06 (1) | 2.880 (2) | 164 (2) |
N2a—H2na···N1 | 0.85 (1) | 2.02 (1) | 2.858 (2) | 167 (2) |