Supporting information
CCDC references: 131747; 131748; 131749
For all compounds, data collection: Siemens software; cell refinement: Siemens software; data reduction: in-house program; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I); SHELXL93 (Sheldrick, 1993) for (II), (III).
C2H2F3NO | Z = 4 |
Mr = 113.05 | F(000) = 224 |
Orthorhombic, P212121 | Dx = 1.885 Mg m−3 |
a = 4.547 (2) Å | Mo Kα radiation, λ = 0.71068 Å |
b = 5.947 (3) Å | µ = 0.23 mm−1 |
c = 14.731 (9) Å | T = 143 K |
V = 398.3 (4) Å3 | Cylinder with diameter 0.5 mm |
Siemens four circle diffractometer, N2 gas stream cooled | 779 reflections with I > 2σ(I) |
Radiation source: fine-focus x-ray tube | Rint = 0.050 |
None monochromator | θmax = 30.0°, θmin = 2.8° |
ω/2θ scans | h = 0→6 |
Absorption correction: no | k = −8→8 |
l = −20→20 | |
2446 measured reflections | 4 standard reflections every 90 min |
1170 independent reflections | intensity decay: 4% |
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)] = 0.070 | Calculated w = 1/[σ2(Fo2) +
(0.0749P)2 + 0.5432P]
where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.226 | (Δ/σ)max = 0.086 |
S = 1.11 | Δρmax = 0.40 e Å−3 |
1170 reflections | Δρmin = −0.39 e Å−3 |
70 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
2 restraints | Absolute structure parameter: −2.88 (2.96) |
Primary atom site location: structure-invariant direct methods |
C2H2F3NO | V = 398.3 (4) Å3 |
Mr = 113.05 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.547 (2) Å | µ = 0.23 mm−1 |
b = 5.947 (3) Å | T = 143 K |
c = 14.731 (9) Å |
Siemens four circle diffractometer, N2 gas stream cooled | 779 reflections with I > 2σ(I) |
Absorption correction: no | Rint = 0.050 |
4 standard reflections every 90 min | |
2446 measured reflections | intensity decay: 4% |
1170 independent reflections |
R[F2 > 2σ(F2)] = 0.070 | 2 restraints |
wR(F2) = 0.226 | Δρmax = 0.40 e Å−3 |
S = 1.11 | Δρmin = −0.39 e Å−3 |
1170 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
70 parameters | Absolute structure parameter: −2.88 (2.96) |
Experimental. Nb filtered |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only= used when they are defined by crystal symmetry. An approximate (isotropic)= treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.= |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and= goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is= not relevant to the choice of reflections for refinement. R-factors based= on F2 are statistically about twice as large as those based on F, and R-= factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0942 (7) | 0.5366 (6) | 0.4321 (3) | 0.029 (1) | |
C1 | 0.8260 (9) | 0.5368 (8) | 0.4309 (3) | 0.025 (1) | |
H1 | 0.70 (2) | 0.66 (1) | 0.46 (1) | 0.030* | |
N2 | 0.6592 (8) | 0.3786 (6) | 0.3883 (3) | 0.026 (1) | |
H2 | 0.45 (2) | 0.38 (1) | 0.39 (1) | 0.031* | |
C3 | 0.7820 (9) | 0.1974 (7) | 0.3408 (3) | 0.026 (1) | |
F1 | 0.9606 (7) | 0.0725 (4) | 0.3916 (2) | 0.034 (1) | |
F2 | 0.9435 (9) | 0.2611 (5) | 0.2699 (2) | 0.040 (1) | |
F3 | 0.5689 (7) | 0.0657 (6) | 0.3109 (3) | 0.060 (1) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0183 (14) | 0.0292 (14) | 0.0395 (16) | 0.0008 (12) | −0.0028 (13) | −0.0073 (13) |
C1 | 0.0213 (18) | 0.0233 (18) | 0.0311 (19) | 0.0034 (15) | −0.0004 (18) | −0.0024 (16) |
N2 | 0.0141 (13) | 0.0290 (16) | 0.0350 (19) | 0.0019 (13) | −0.0002 (15) | −0.0073 (15) |
C3 | 0.0179 (18) | 0.0278 (19) | 0.033 (2) | 0.0026 (15) | 0.0001 (16) | −0.0059 (16) |
F1 | 0.0400 (15) | 0.0279 (12) | 0.0351 (13) | 0.0117 (12) | −0.0002 (13) | 0.0033 (10) |
F2 | 0.055 (2) | 0.0333 (13) | 0.0308 (13) | 0.0089 (14) | 0.0168 (14) | 0.0006 (11) |
F3 | 0.0249 (14) | 0.054 (2) | 0.099 (3) | −0.0030 (15) | −0.0078 (19) | −0.047 (2) |
O1—C1 | 1.219 (5) | N2—H2 | 0.96 (7) |
C1—N2 | 1.366 (6) | C3—F3 | 1.320 (5) |
C1—H1 | 1.01 (6) | C3—F1 | 1.332 (5) |
N2—C3 | 1.402 (5) | C3—F2 | 1.330 (5) |
O1—C1—N2 | 124.0 (5) | F3—C3—F1 | 107.7 (4) |
O1—C1—H1 | 124 (4) | F3—C3—F2 | 108.2 (4) |
N2—C1—H1 | 112 (4) | F1—C3—F2 | 105.3 (4) |
C1—N2—C3 | 122.6 (4) | F3—C3—N2 | 109.2 (4) |
C1—N2—H2 | 125 (3) | F1—C3—N2 | 113.0 (4) |
C3—N2—H2 | 112 (3) | F2—C3—N2 | 113.2 (4) |
O1—C1—N2—C3 | 0.3 (8) | C1—N2—C3—F1 | 56.6 (6) |
C1—N2—C3—F3 | 176.5 (5) | C1—N2—C3—F2 | −62.9 (6) |
C3H4F3NO | Z = 4 |
Mr = 127.07 | F(000) = 256 |
Monoclinic, P21/n | Dx = 1.666 Mg m−3 |
a = 4.807 (1) Å | Mo Kα radiation, λ = 0.71068 Å |
b = 16.707 (3) Å | µ = 0.19 mm−1 |
c = 6.708 (1) Å | T = 141 K |
β = 109.90 (1)° | Cylinder with diameter 0.5 mm |
V = 506.6 (2) Å3 |
Siemens four circle diffractometer, N2 gas stream cooled | 1018 reflections with I > 2σ(I) |
Radiation source: fine-focus x-ray tube | Rint = 0.031 |
None monochromator | θmax = 30.1°, θmin = 2.4° |
ω/2θ scans | h = −6→4 |
Absorption correction: no | k = −23→19 |
l = −9→9 | |
2983 measured reflections | 3 standard reflections every 90 min |
1484 independent reflections | intensity decay: 4% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | Calculated w = 1/[σ2(Fo2) +
(0.0587P)2 + 0.2157P]
where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.043 |
1484 reflections | Δρmax = 0.30 e Å−3 |
89 parameters | Δρmin = −0.29 e Å−3 |
0 restraints |
C3H4F3NO | β = 109.90 (1)° |
Mr = 127.07 | V = 506.6 (2) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 4.807 (1) Å | Mo Kα radiation |
b = 16.707 (3) Å | µ = 0.19 mm−1 |
c = 6.708 (1) Å | T = 141 K |
Siemens four circle diffractometer, N2 gas stream cooled | 1018 reflections with I > 2σ(I) |
Absorption correction: no | Rint = 0.031 |
3 standard reflections every 90 min | |
2983 measured reflections | intensity decay: 4% |
1484 independent reflections |
R[F2 > 2σ(F2)] = 0.051 | 89 parameters |
wR(F2) = 0.140 | 0 restraints |
S = 1.09 | Δρmax = 0.30 e Å−3 |
1484 reflections | Δρmin = −0.29 e Å−3 |
Experimental. Nb filtered |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only= used when they are defined by crystal symmetry. An approximate (isotropic)= treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.= |
Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2= or flagged by the user for potential systematic errors. Weighted R-factors= wR and all goodnesses of fit S are based on F2, conventional R-factors R= are based on F, with F set to zero for negative F2. The observed= criterion of F2 > σ(F2) is used only for calculating _R_factor_obs etc. and= is not relevant to the choice of reflections for refinement. R-factors based= on F2 are statistically about twice as large as those based on F, and R-= factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0908 (3) | 0.2117 (1) | 0.3539 (2) | 0.027 (1) | |
C1 | 0.9939 (4) | 0.2445 (1) | 0.4805 (3) | 0.021 (1) | |
H1 | 1.016 (6) | 0.298 (2) | 0.509 (4) | 0.027 (6)* | |
N2 | 0.8317 (3) | 0.2082 (1) | 0.5793 (2) | 0.022 (1) | |
H2 | 0.766 (5) | 0.235 (1) | 0.666 (4) | 0.013 (5)* | |
C3 | 0.7452 (4) | 0.1256 (1) | 0.5396 (3) | 0.023 (1) | |
H31 | 0.780 (7) | 0.108 (2) | 0.411 (5) | 0.034 (7)* | |
H32 | 0.550 (7) | 0.121 (2) | 0.524 (5) | 0.041 (8)* | |
C4 | 0.9133 (4) | 0.0737 (1) | 0.7229 (3) | 0.026 (1) | |
F1 | 1.2041 (3) | 0.0744 (1) | 0.7593 (2) | 0.040 (1) | |
F2 | 0.8787 (4) | 0.0967 (1) | 0.9037 (2) | 0.041 (1) | |
F3 | 0.8245 (4) | −0.0020 (1) | 0.6893 (3) | 0.042 (1) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0278 (6) | 0.0326 (7) | 0.0256 (6) | 0.0004 (5) | 0.0153 (5) | 0.0029 (5) |
C1 | 0.0194 (7) | 0.0233 (8) | 0.0202 (7) | 0.0009 (6) | 0.0053 (5) | 0.0032 (6) |
N2 | 0.0247 (7) | 0.0225 (7) | 0.0214 (6) | 0.0007 (6) | 0.0120 (5) | −0.0006 (5) |
C3 | 0.0216 (8) | 0.0245 (8) | 0.0241 (7) | −0.0016 (6) | 0.0086 (6) | 0.0011 (6) |
C4 | 0.0263 (8) | 0.0245 (9) | 0.0285 (8) | −0.0001 (7) | 0.0107 (6) | 0.0015 (7) |
F1 | 0.0251 (6) | 0.0457 (8) | 0.0466 (7) | 0.0078 (5) | 0.0088 (5) | 0.0054 (6) |
F2 | 0.0547 (8) | 0.0449 (8) | 0.0266 (6) | 0.0094 (6) | 0.0193 (5) | 0.0080 (5) |
F3 | 0.0517 (8) | 0.0250 (6) | 0.0480 (8) | −0.0037 (6) | 0.0130 (6) | 0.0068 (5) |
O1—C1 | 1.228 (2) | C3—H31 | 0.98 (3) |
C1—N2 | 1.329 (2) | C3—H32 | 0.91 (3) |
C1—H1 | 0.90 (3) | C4—F3 | 1.329 (2) |
N2—C3 | 1.440 (2) | C4—F1 | 1.334 (2) |
N2—H2 | 0.86 (2) | C4—F2 | 1.335 (2) |
C3—C4 | 1.498 (3) | ||
O1—C1—N2 | 124.5 (2) | C4—C3—H31 | 109 (2) |
O1—C1—H1 | 123 (2) | C4—C3—H32 | 107 (2) |
N2—C1—H1 | 113 (2) | H31—C3—H32 | 110 (3) |
C1—N2—C3 | 121.7 (2) | F3—C4—F1 | 107.2 (2) |
C1—N2—H2 | 120 (2) | F3—C4—F2 | 107.2 (2) |
C3—N2—H2 | 118 (2) | F1—C4—F2 | 106.1 (2) |
N2—C3—C4 | 111 (2) | F3—C4—C3 | 111.0 (2) |
N2—C3—H31 | 110 (2) | F1—C4—C3 | 112.6 (2) |
N2—C3—H32 | 109 (2) | F2—C4—C3 | 112.3 (2) |
O1—C1—N2—C3 | −2.2 (3) | N2—C3—C4—F1 | −62.3 (2) |
C1—N2—C3—C4 | 107.5 (2) | N2—C3—C4—F2 | 57.4 (2) |
N2—C3—C4—F3 | 177.5 (2) |
C3H2F3N | Z = 4 |
Mr = 109.06 | F(000) = 216 |
Orthorhombic, P212121 | Dx = 1.599 Mg m−3 |
a = 5.668 (2) Å | Mo Kα radiation, λ = 0.71068 Å |
b = 9.266 (3) Å | µ = 0.19 mm−1 |
c = 8.626 (2) Å | T = 163 K |
V = 453.0 (2) Å3 | Cylinder with diameter 0.5 mm |
Siemens four circle diffractometer, N2 gas stream cooled | 1092 reflections with I > 2σ(I) |
Radiation source: fine-focus x-ray tube | Rint = 0.022 |
None monochromator | θmax = 35.0°, θmin = 3.2° |
ω/2θ scans | h = −4→9 |
Absorption correction: no | k = −14→14 |
l = −11→13 | |
1856 measured reflections | 4 standard reflections every 90 min |
1556 independent reflections | intensity decay: 58% |
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)] = 0.033 | Calculated w = 1/[σ2(Fo2) +
(0.0452P)2 + 0.0656P]
where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max = 0.006 |
S = 1.01 | Δρmax = 0.22 e Å−3 |
1556 reflections | Δρmin = −0.14 e Å−3 |
72 parameters | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
0 restraints | Absolute structure parameter: −0.18 (91) |
Primary atom site location: structure-invariant direct methods |
C3H2F3N | V = 453.0 (2) Å3 |
Mr = 109.06 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.668 (2) Å | µ = 0.19 mm−1 |
b = 9.266 (3) Å | T = 163 K |
c = 8.626 (2) Å |
Siemens four circle diffractometer, N2 gas stream cooled | 1092 reflections with I > 2σ(I) |
Absorption correction: no | Rint = 0.022 |
4 standard reflections every 90 min | |
1856 measured reflections | intensity decay: 58% |
1556 independent reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.098 | Δρmax = 0.22 e Å−3 |
S = 1.01 | Δρmin = −0.14 e Å−3 |
1556 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
72 parameters | Absolute structure parameter: −0.18 (91) |
Experimental. Nb filtered |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only= used when they are defined by crystal symmetry. An approximate (isotropic)= treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.= |
Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2= or flagged by the user for potential systematic errors. Weighted R-factors= wR and all goodnesses of fit S are based on F2, conventional R-factors R= are based on F, with F set to zero for negative F2. The observed= criterion of F2 > σ(F2) is used only for calculating _R_factor_obs etc. and= is not relevant to the choice of reflections for refinement. R-factors based= on F2 are statistically about twice as large as those based on F, and R-= factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0245 (3) | 0.2436 (2) | −0.1439 (2) | 0.054 (1) | |
N2 | 0.0359 (2) | 0.1328 (1) | −0.1005 (1) | 0.042 (1) | |
C3 | 0.1126 (3) | −0.0044 (2) | −0.0460 (2) | 0.042 (1) | |
H31 | 0.276 (4) | 0.000 (2) | −0.0088 (2) | 0.051 (5)* | |
H32 | 0.103 (4) | −0.074 (2) | −0.127 (2) | 0.057 (5)* | |
C4 | −0.0476 (3) | −0.0568 (2) | 0.0807 (1) | 0.039 (1) | |
F1 | −0.0465 (2) | 0.0293 (1) | 0.2027 (1) | 0.056 (1) | |
F2 | −0.2697 (2) | −0.0675 (1) | 0.0346 (1) | 0.058 (1) | |
F3 | 0.0198 (3) | −0.1866 (1) | 0.1278 (1) | 0.073 (1) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0529 (9) | 0.0510 (8) | 0.0585 (8) | −0.0088 (8) | −0.0054 (8) | 0.0125 (7) |
N2 | 0.0452 (6) | 0.0430 (6) | 0.0374 (5) | −0.0077 (6) | 0.0001 (5) | 0.0016 (5) |
C3 | 0.0480 (9) | 0.0386 (6) | 0.0405 (6) | 0.0056 (6) | 0.0056 (6) | −0.0051 (6) |
C4 | 0.0469 (7) | 0.0349 (6) | 0.0365 (6) | 0.0052 (6) | −0.0027 (5) | −0.0014 (5) |
F1 | 0.0679 (6) | 0.0661 (6) | 0.0348 (4) | −0.0029 (5) | 0.0026 (4) | −0.0135 (4) |
F2 | 0.0498 (5) | 0.0660 (6) | 0.0588 (5) | −0.0174 (5) | −0.0069 (4) | 0.0055 (5) |
F3 | 0.0943 (9) | 0.0471 (5) | 0.0775 (7) | 0.0210 (6) | 0.0154 (7) | 0.0229 (5) |
C1—N2 | 1.145 (2) | C3—H32 | 0.95 (2) |
N2—C3 | 1.424 (2) | C4—F1 | 1.321 (2) |
C3—C4 | 1.502 (2) | C4—F2 | 1.324 (2) |
C3—H31 | 0.98 (2) | C4—F3 | 1.326 (2) |
C1—N2—C3 | 179.5 (2) | F1—C4—C3 | 112.5 (1) |
N2—C3—C4 | 110.1 (1) | F2—C4—C3 | 112.4 (1) |
N2—C3—H31 | 111 (1) | F3—C4—C3 | 110.0 (1) |
N2—C3—H32 | 110 (1) | F2—C4—F3 | 107.3 (1) |
C4—C3—H31 | 110 (1) | F1—C4—F3 | 107.6 (1) |
C4—C3—H32 | 107 (1) | F1—C4—F2 | 106.8 (1) |
H31—C3—H32 | 109 (2) | ||
C1—N2—C3—C4 | 111 (19) | N2—C3—C4—F2 | 58.5 (2) |
N2—C3—C4—F1 | −62.1 (2) | N2—C3—C4—F3 | 178.0 (1) |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C2H2F3NO | C3H4F3NO | C3H2F3N |
Mr | 113.05 | 127.07 | 109.06 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21/n | Orthorhombic, P212121 |
Temperature (K) | 143 | 141 | 163 |
a, b, c (Å) | 4.547 (2), 5.947 (3), 14.731 (9) | 4.807 (1), 16.707 (3), 6.708 (1) | 5.668 (2), 9.266 (3), 8.626 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 109.90 (1), 90 | 90, 90, 90 |
V (Å3) | 398.3 (4) | 506.6 (2) | 453.0 (2) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.23 | 0.19 | 0.19 |
Crystal size (mm) | × × | × × | × × |
Data collection | |||
Diffractometer | Siemens four circle diffractometer, N2 gas stream cooled | Siemens four circle diffractometer, N2 gas stream cooled | Siemens four circle diffractometer, N2 gas stream cooled |
Absorption correction | No | No | No |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2446, 1170, 779 | 2983, 1484, 1018 | 1856, 1556, 1092 |
Rint | 0.050 | 0.031 | 0.022 |
(sin θ/λ)max (Å−1) | 0.704 | 0.705 | 0.807 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.226, 1.11 | 0.051, 0.140, 1.09 | 0.033, 0.098, 1.01 |
No. of reflections | 1170 | 1484 | 1556 |
No. of parameters | 70 | 89 | 72 |
No. of restraints | 2 | 0 | 0 |
Δρmax, Δρmin (e Å−3) | 0.40, −0.39 | 0.30, −0.29 | 0.22, −0.14 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | ? | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −2.88 (2.96) | ? | −0.18 (91) |
Computer programs: Siemens software, in-house program, SHELXS86 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL93 (Sheldrick, 1993).
Theoretical calculations on the ab initio level HF/6-31 G(d,p). In the calculations for I, done by Madappat, Clark and Thrasher (1993), the molecule geometry was constrained to a Cs symmetry. |
I | X-ray | Theory | II | X-ray | Theory | III | X-ray | Theory |
O1-C1 | 1.219 (5) | 1.185 | O1-C1 | 1.228 (2) | 1.192 | C1-N2 | 1.145 (2) | 1.155 |
C1-N2 | 1.366 (6) | 1.370 | C1-N2 | 1.329 (2) | 1.355 | N2-C3 | 1.424 (2) | 1.413 |
C1-H1 | 1.01 (6) | 1.090 | C1-H1 | 0.90 (3) | 1.091 | C3-C4 | 1.502 (2) | 1.514 |
N2-C3 | 1.402 (5) | 1.406 | N2-C3 | 1.440 (2) | 1.436 | C3-H31 | 0.98 (2) | 1.081 |
N2-H2 | 0.96 (7) | 0.994 | N2-H2 | 0.87 (2) | 0.994 | C3-H32 | 0.96 (2) | 1.081 |
C3-F1 | 1.332 (5) | 1.314 | C3-C4 | 1.498 (3) | 1.510 | C4-F1 | 1.321 (2) | 1.316 |
C3-F2 | 1.330 (5) | 1.314 | C3-H31 | 0.98 (3) | 1.079 | C4-F2 | 1.324 (2) | 1.316 |
C3-F3 | 1.320 (5) | 1.317 | C3-H32 | 0.91 (3) | 1.084 | C4-F3 | 1.326 (2) | 1.322 |
C4-F3 | 1.329 (2) | |||||||
C4-F1 | 1.334 (2) | |||||||
C4-F2 | 1.335 (2) | |||||||
O1-C1-N2 | 124.0 (5) | 124.9 | O1-C1-N2 | 124.5 (2) | 125.04 | C1-N2-C3 | 179.5 (2) | 179.82 |
O1-C1-H1 | 124 (4) | O1-C1-H1 | 123 (2) | 122.56 | N2-C3-C4 | 110.1 (1) | 111.30 | |
N2-C1-H1 | 112 (4) | 111.7 | N2-C1-H1 | 113 (2) | 112.40 | N2-C3-H31 | 111 (1) | 109.93 |
C1-N2-C3 | 122.6 (4) | 123.7 | C1-N2-C3 | 121.7 (2) | 122.45 | N2-C3-H32 | 110 (1) | 109.94 |
C1-N2-H2 | 125 (3) | C1-N2-H2 | 120 (2) | 118.54 | C4-C3-H31 | 110 (1) | 108.22 | |
C3-N2-H2 | 112 (3) | 116.3 | C3-N2-H2 | 118 (2) | 118.86 | C4-C3-H32 | 107 (1) | 108.23 |
F1-C3-N2 | 113.0 (4) | 112.3 | N2-C3-C4 | 111 (2) | 111.58 | H31-C3-H32 | 109 (2) | 109.16 |
F2-C3-N2 | 113.2 (4) | 112.3 | N2-C3-H31 | 110 (2) | 108.69 | F1-C4-C3 | 112.5 (1) | 111.83 |
F3-C3-N2 | 109.2 (4) | 108.2 | N2-C3-H32 | 109 (2) | 111.19 | F2-C4-C3 | 112.4 (1) | 111.83 |
F2-C3-F3 | 108.2 (4) | C4-C3-H31 | 109 (2) | 108.69 | F3-C4-C3 | 110.0 (1) | 108.77 | |
F1-C3-F3 | 107.7 (4) | C4-C3-H32 | 107 (2) | 107.55 | F2-C4-F3 | 107.3 (1) | 108.07 | |
F1-C3-F2 | 105.3 (4) | H31-C3-H32 | 110 (3) | 109.08 | F1-C4-F3 | 107.6 (1) | 108.09 | |
F1-C4-C3 | 112.6 (2) | 112.40 | F1-C4-F2 | 106.8 (1) | 108.12 | |||
F2-C4-C3 | 112.3 (2) | 110.95 | ||||||
F3-C4-C3 | 111.0 (2) | 110.42 | ||||||
F3-C4-F2 | 107.2 (2) | 107.53 | ||||||
F3-C4-F1 | 107.2 (2) | 108.02 | ||||||
F1-C4-F2 | 106.1 (2) | 107.33 | ||||||
O1-C1-N2-C3 | 0.3 (8) | 0.00 | O1-C1-N2-C3 | -2.2 (3) | 3.00 | N2-C3-C4-F1 | -62.1 (2) | -60.73 |
C1-N2-C3-F1 | 56.6 (6) | 60.00 | N2-C3-C4-F1 | -62.3 (2) | -61.50 | N2-C3-C4-F2 | 58.5 (2) | 60.69 |
C1-N2-C3-F2 | -62.9 (6) | -60 | N2-C3-C4-F2 | 57.4 (2) | 58.68 | N2-C3-C4-F3 | 178.0 (1) | 179.97 |
C1-N2-C3-F3 | 176.5 (5) | 60.00 | N2-C3-C4-F3 | 177.5 (2) | 177.80 | |||
C1-N2-C3-C4 | 107.5 (2) |