Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003589/jx3028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003589/jx3028formIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003589/jx3028formIIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003589/jx3028formIsup4.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619003589/jx3028sup5.pdf |
CCDC references: 1877354; 1877353
For both structures, data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
C18H14F2NO3P | F(000) = 744 |
Mr = 361.27 | Dx = 1.431 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2037 (3) Å | Cell parameters from 7646 reflections |
b = 9.1372 (3) Å | θ = 3.0–28.3° |
c = 17.9981 (5) Å | µ = 0.20 mm−1 |
β = 92.260 (1)° | T = 100 K |
V = 1676.72 (9) Å3 | Block, colorless |
Z = 4 | 0.24 × 0.14 × 0.10 mm |
Bruker APEXII CCD diffractometer | 2724 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.026 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 25.0°, θmin = 2.0° |
Tmin = 0.685, Tmax = 0.746 | h = −12→12 |
12986 measured reflections | k = −10→10 |
2935 independent reflections | l = −21→21 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.6978P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2935 reflections | Δρmax = 0.27 e Å−3 |
229 parameters | Δρmin = −0.36 e Å−3 |
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. All the single-crystal diffraction data have been collected on a Bruker Smart APEX II diffractometer equipped with a CCD area detector using monochromatic Mo Kα radiation at 100K under the flow of liquid nitrogen. Bruker Apex II program (Bruker, 2012) was used for the data collection. The data reduction and cell refinements were done using the Bruker SAINT suite of programs and absorption corrections using SADABS programs (Bruker, 2012). The structures were refined by the full matrix least squares method using SHELXL-2018/3 (Sheldrick, 2015) present in the WinGX program (version 2014.1) (Farrugia, 2014). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.69854 (3) | 0.55364 (4) | 0.45512 (2) | 0.01971 (12) | |
O1 | 0.76245 (9) | 0.57544 (11) | 0.37749 (5) | 0.0229 (2) | |
O2 | 0.83001 (9) | 0.57334 (10) | 0.50351 (5) | 0.0220 (2) | |
O3 | 0.59246 (9) | 0.65535 (10) | 0.47204 (6) | 0.0247 (2) | |
F1 | 1.03376 (8) | 0.11956 (10) | 0.39419 (5) | 0.0344 (2) | |
F2 | 0.91966 (9) | −0.13348 (9) | 0.42936 (5) | 0.0343 (2) | |
N1 | 0.64940 (11) | 0.38495 (13) | 0.46164 (7) | 0.0216 (3) | |
H1A | 0.5741 (17) | 0.3758 (18) | 0.4813 (9) | 0.026* | |
C1 | 0.69334 (14) | 0.54882 (16) | 0.30941 (8) | 0.0249 (3) | |
C2 | 0.75696 (16) | 0.46668 (19) | 0.25802 (9) | 0.0345 (4) | |
H2 | 0.841140 | 0.426620 | 0.269808 | 0.041* | |
C3 | 0.69662 (19) | 0.4431 (2) | 0.18880 (10) | 0.0450 (4) | |
H3 | 0.739539 | 0.386642 | 0.152722 | 0.054* | |
C4 | 0.57445 (18) | 0.5015 (2) | 0.17213 (10) | 0.0463 (5) | |
H4 | 0.532859 | 0.484492 | 0.124759 | 0.056* | |
C5 | 0.51299 (17) | 0.5841 (2) | 0.22397 (10) | 0.0489 (5) | |
H5 | 0.429061 | 0.624598 | 0.211993 | 0.059* | |
C6 | 0.57171 (15) | 0.6093 (2) | 0.29384 (10) | 0.0377 (4) | |
H6 | 0.529191 | 0.666633 | 0.329756 | 0.045* | |
C7 | 0.72206 (13) | 0.25549 (15) | 0.45390 (7) | 0.0189 (3) | |
C8 | 0.84869 (13) | 0.25457 (15) | 0.42702 (8) | 0.0220 (3) | |
H8 | 0.890205 | 0.343202 | 0.413524 | 0.026* | |
C9 | 0.91183 (13) | 0.12261 (16) | 0.42056 (8) | 0.0232 (3) | |
C10 | 0.85381 (14) | −0.00689 (16) | 0.43892 (8) | 0.0239 (3) | |
C11 | 0.72971 (14) | −0.00755 (16) | 0.46600 (8) | 0.0267 (3) | |
H11 | 0.689347 | −0.096980 | 0.479304 | 0.032* | |
C12 | 0.66449 (14) | 0.12405 (15) | 0.47358 (8) | 0.0227 (3) | |
H12 | 0.578928 | 0.124521 | 0.492565 | 0.027* | |
C13 | 0.83067 (13) | 0.54108 (15) | 0.58046 (8) | 0.0226 (3) | |
C14 | 0.76192 (16) | 0.62747 (18) | 0.62802 (9) | 0.0341 (4) | |
H14 | 0.710335 | 0.707214 | 0.609753 | 0.041* | |
C15 | 0.77000 (19) | 0.5950 (2) | 0.70300 (10) | 0.0475 (5) | |
H15 | 0.722759 | 0.652520 | 0.736854 | 0.057* | |
C16 | 0.84617 (18) | 0.4798 (2) | 0.72918 (10) | 0.0471 (5) | |
H16 | 0.851298 | 0.458516 | 0.780883 | 0.057* | |
C17 | 0.91476 (16) | 0.3955 (2) | 0.68050 (9) | 0.0365 (4) | |
H17 | 0.967236 | 0.316401 | 0.698749 | 0.044* | |
C18 | 0.90742 (13) | 0.42563 (17) | 0.60516 (8) | 0.0260 (3) | |
H18 | 0.954283 | 0.368002 | 0.571201 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01632 (19) | 0.0135 (2) | 0.0298 (2) | −0.00068 (13) | 0.00687 (14) | 0.00162 (14) |
O1 | 0.0182 (5) | 0.0211 (5) | 0.0296 (5) | −0.0019 (4) | 0.0049 (4) | 0.0029 (4) |
O2 | 0.0192 (5) | 0.0189 (5) | 0.0284 (5) | −0.0022 (4) | 0.0072 (4) | 0.0011 (4) |
O3 | 0.0197 (5) | 0.0157 (5) | 0.0395 (6) | 0.0001 (4) | 0.0092 (4) | 0.0018 (4) |
F1 | 0.0222 (4) | 0.0281 (5) | 0.0539 (6) | 0.0050 (4) | 0.0130 (4) | −0.0019 (4) |
F2 | 0.0345 (5) | 0.0170 (5) | 0.0515 (6) | 0.0091 (4) | 0.0023 (4) | −0.0026 (4) |
N1 | 0.0159 (6) | 0.0155 (6) | 0.0338 (7) | −0.0013 (5) | 0.0077 (5) | 0.0011 (5) |
C1 | 0.0213 (7) | 0.0233 (8) | 0.0301 (8) | −0.0042 (6) | 0.0018 (6) | 0.0075 (6) |
C2 | 0.0324 (8) | 0.0368 (9) | 0.0342 (8) | 0.0075 (7) | −0.0010 (7) | 0.0005 (7) |
C3 | 0.0488 (11) | 0.0503 (12) | 0.0355 (9) | 0.0067 (9) | −0.0028 (8) | −0.0023 (8) |
C4 | 0.0391 (10) | 0.0653 (13) | 0.0340 (9) | −0.0055 (9) | −0.0065 (8) | 0.0088 (9) |
C5 | 0.0258 (9) | 0.0754 (14) | 0.0450 (10) | 0.0053 (9) | −0.0028 (7) | 0.0196 (10) |
C6 | 0.0265 (8) | 0.0481 (11) | 0.0388 (9) | 0.0077 (7) | 0.0058 (7) | 0.0112 (8) |
C7 | 0.0196 (7) | 0.0157 (7) | 0.0213 (6) | 0.0006 (5) | −0.0002 (5) | −0.0013 (5) |
C8 | 0.0202 (7) | 0.0159 (7) | 0.0302 (7) | −0.0024 (5) | 0.0041 (6) | 0.0007 (6) |
C9 | 0.0182 (7) | 0.0246 (8) | 0.0271 (7) | 0.0020 (6) | 0.0028 (5) | −0.0027 (6) |
C10 | 0.0272 (7) | 0.0156 (7) | 0.0285 (7) | 0.0056 (6) | −0.0029 (6) | −0.0029 (6) |
C11 | 0.0294 (8) | 0.0157 (7) | 0.0350 (8) | −0.0028 (6) | 0.0014 (6) | 0.0026 (6) |
C12 | 0.0200 (7) | 0.0195 (7) | 0.0289 (7) | −0.0022 (6) | 0.0026 (6) | 0.0013 (6) |
C13 | 0.0194 (7) | 0.0209 (7) | 0.0278 (7) | −0.0067 (6) | 0.0059 (5) | −0.0022 (6) |
C14 | 0.0341 (8) | 0.0296 (9) | 0.0392 (9) | 0.0031 (7) | 0.0080 (7) | −0.0081 (7) |
C15 | 0.0486 (11) | 0.0583 (13) | 0.0363 (10) | 0.0039 (9) | 0.0130 (8) | −0.0170 (9) |
C16 | 0.0433 (10) | 0.0715 (14) | 0.0268 (9) | −0.0014 (10) | 0.0046 (7) | 0.0000 (8) |
C17 | 0.0289 (8) | 0.0462 (10) | 0.0344 (9) | −0.0013 (7) | 0.0010 (7) | 0.0068 (7) |
C18 | 0.0197 (7) | 0.0271 (8) | 0.0314 (8) | −0.0013 (6) | 0.0050 (6) | −0.0015 (6) |
P1—O3 | 1.4677 (10) | C7—C12 | 1.3890 (19) |
P1—O1 | 1.5776 (10) | C7—C8 | 1.3974 (19) |
P1—O2 | 1.5807 (10) | C8—C9 | 1.374 (2) |
P1—N1 | 1.6266 (12) | C8—H8 | 0.9500 |
O1—C1 | 1.4105 (17) | C9—C10 | 1.369 (2) |
O2—C13 | 1.4156 (17) | C10—C11 | 1.375 (2) |
F1—C9 | 1.3492 (16) | C11—C12 | 1.384 (2) |
F2—C10 | 1.3521 (16) | C11—H11 | 0.9500 |
N1—C7 | 1.4059 (17) | C12—H12 | 0.9500 |
N1—H1A | 0.863 (17) | C13—C14 | 1.377 (2) |
C1—C2 | 1.374 (2) | C13—C18 | 1.377 (2) |
C1—C6 | 1.377 (2) | C14—C15 | 1.381 (3) |
C2—C3 | 1.384 (2) | C14—H14 | 0.9500 |
C2—H2 | 0.9500 | C15—C16 | 1.381 (3) |
C3—C4 | 1.378 (3) | C15—H15 | 0.9500 |
C3—H3 | 0.9500 | C16—C17 | 1.378 (3) |
C4—C5 | 1.371 (3) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—C18 | 1.383 (2) |
C5—C6 | 1.391 (3) | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | C18—H18 | 0.9500 |
C6—H6 | 0.9500 | ||
O3—P1—O1 | 115.97 (6) | C9—C8—H8 | 120.7 |
O3—P1—O2 | 115.49 (6) | C7—C8—H8 | 120.7 |
O1—P1—O2 | 95.87 (5) | F1—C9—C10 | 118.71 (13) |
O3—P1—N1 | 110.67 (6) | F1—C9—C8 | 119.33 (13) |
O1—P1—N1 | 108.84 (6) | C10—C9—C8 | 121.95 (13) |
O2—P1—N1 | 108.99 (6) | F2—C10—C9 | 119.13 (13) |
C1—O1—P1 | 122.52 (8) | F2—C10—C11 | 120.71 (13) |
C13—O2—P1 | 119.11 (8) | C9—C10—C11 | 120.16 (13) |
C7—N1—P1 | 128.67 (10) | C10—C11—C12 | 118.98 (13) |
C7—N1—H1A | 116.2 (11) | C10—C11—H11 | 120.5 |
P1—N1—H1A | 113.8 (11) | C12—C11—H11 | 120.5 |
C2—C1—C6 | 121.88 (15) | C11—C12—C7 | 121.09 (13) |
C2—C1—O1 | 116.47 (13) | C11—C12—H12 | 119.5 |
C6—C1—O1 | 121.54 (14) | C7—C12—H12 | 119.5 |
C1—C2—C3 | 119.04 (16) | C14—C13—C18 | 122.39 (14) |
C1—C2—H2 | 120.5 | C14—C13—O2 | 120.40 (14) |
C3—C2—H2 | 120.5 | C18—C13—O2 | 117.13 (12) |
C4—C3—C2 | 120.15 (18) | C13—C14—C15 | 118.19 (16) |
C4—C3—H3 | 119.9 | C13—C14—H14 | 120.9 |
C2—C3—H3 | 119.9 | C15—C14—H14 | 120.9 |
C5—C4—C3 | 119.93 (17) | C16—C15—C14 | 120.54 (16) |
C5—C4—H4 | 120.0 | C16—C15—H15 | 119.7 |
C3—C4—H4 | 120.0 | C14—C15—H15 | 119.7 |
C4—C5—C6 | 120.96 (16) | C17—C16—C15 | 120.17 (16) |
C4—C5—H5 | 119.5 | C17—C16—H16 | 119.9 |
C6—C5—H5 | 119.5 | C15—C16—H16 | 119.9 |
C1—C6—C5 | 118.03 (17) | C16—C17—C18 | 120.18 (17) |
C1—C6—H6 | 121.0 | C16—C17—H17 | 119.9 |
C5—C6—H6 | 121.0 | C18—C17—H17 | 119.9 |
C12—C7—C8 | 119.29 (12) | C13—C18—C17 | 118.52 (14) |
C12—C7—N1 | 118.18 (12) | C13—C18—H18 | 120.7 |
C8—C7—N1 | 122.54 (12) | C17—C18—H18 | 120.7 |
C9—C8—C7 | 118.53 (13) | ||
O3—P1—O1—C1 | −67.23 (12) | N1—C7—C8—C9 | −179.29 (12) |
O2—P1—O1—C1 | 170.68 (10) | C7—C8—C9—F1 | 179.52 (12) |
N1—P1—O1—C1 | 58.30 (11) | C7—C8—C9—C10 | 0.7 (2) |
O3—P1—O2—C13 | 67.21 (11) | F1—C9—C10—F2 | −0.7 (2) |
O1—P1—O2—C13 | −170.34 (10) | C8—C9—C10—F2 | 178.17 (13) |
N1—P1—O2—C13 | −58.09 (11) | F1—C9—C10—C11 | 179.94 (13) |
O3—P1—N1—C7 | −176.21 (11) | C8—C9—C10—C11 | −1.2 (2) |
O1—P1—N1—C7 | 55.24 (13) | F2—C10—C11—C12 | −178.71 (12) |
O2—P1—N1—C7 | −48.16 (13) | C9—C10—C11—C12 | 0.6 (2) |
P1—O1—C1—C2 | −132.55 (12) | C10—C11—C12—C7 | 0.4 (2) |
P1—O1—C1—C6 | 51.14 (18) | C8—C7—C12—C11 | −0.9 (2) |
C6—C1—C2—C3 | −0.5 (3) | N1—C7—C12—C11 | 178.77 (13) |
O1—C1—C2—C3 | −176.81 (15) | P1—O2—C13—C14 | −68.15 (16) |
C1—C2—C3—C4 | −0.1 (3) | P1—O2—C13—C18 | 114.98 (12) |
C2—C3—C4—C5 | 0.6 (3) | C18—C13—C14—C15 | −0.7 (2) |
C3—C4—C5—C6 | −0.5 (3) | O2—C13—C14—C15 | −177.39 (14) |
C2—C1—C6—C5 | 0.6 (3) | C13—C14—C15—C16 | 0.6 (3) |
O1—C1—C6—C5 | 176.68 (15) | C14—C15—C16—C17 | −0.2 (3) |
C4—C5—C6—C1 | −0.1 (3) | C15—C16—C17—C18 | −0.2 (3) |
P1—N1—C7—C12 | 169.82 (11) | C14—C13—C18—C17 | 0.3 (2) |
P1—N1—C7—C8 | −10.5 (2) | O2—C13—C18—C17 | 177.15 (13) |
C12—C7—C8—C9 | 0.4 (2) | C16—C17—C18—C13 | 0.1 (2) |
C18H14F2NO3P | Dx = 1.412 Mg m−3 |
Mr = 361.27 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 4055 reflections |
a = 35.0582 (8) Å | θ = 2.3–23.1° |
b = 7.2554 (1) Å | µ = 0.20 mm−1 |
c = 13.3647 (3) Å | T = 100 K |
V = 3399.46 (12) Å3 | Needle, colorless |
Z = 8 | 0.32 × 0.10 × 0.08 mm |
F(000) = 1488 |
Bruker APEXII CCD diffractometer | 7943 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.064 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | θmax = 30.2°, θmin = 1.9° |
Tmin = 0.677, Tmax = 0.746 | h = −49→48 |
38761 measured reflections | k = −9→10 |
9964 independent reflections | l = −18→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.56 e Å−3 |
9964 reflections | Δρmin = −0.39 e Å−3 |
423 parameters | Absolute structure: Refined as an inversion twin |
1 restraint | Absolute structure parameter: 0.32 (11) |
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. All the single-crystal diffraction data have been collected on a Bruker Smart APEX II diffractometer equipped with a CCD area detector using monochromatic Mo Kα radiation at 100K under the flow of liquid nitrogen. Bruker Apex II program (Bruker, 2012) was used for the data collection. The data reduction and cell refinements were done using the Bruker SAINT suite of programs and absorption corrections using SADABS programs (Bruker, 2012). The structures were refined by the full matrix least squares method using SHELXL-2018/3 (Sheldrick, 2015) present in the WinGX program (version 2014.1) (Farrugia, 2014). All non-H atoms were refined anisotropically. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
P1 | 0.36203 (2) | 0.48593 (10) | 0.40749 (6) | 0.01605 (17) | |
P2 | 0.38317 (2) | −0.00834 (10) | 0.60365 (7) | 0.01560 (17) | |
F1 | 0.36208 (7) | 1.1959 (3) | 0.13530 (18) | 0.0411 (6) | |
F2 | 0.34765 (7) | 0.9715 (3) | −0.01831 (16) | 0.0326 (5) | |
O1 | 0.39551 (6) | 0.3860 (3) | 0.35036 (18) | 0.0193 (5) | |
O2 | 0.32947 (6) | 0.3618 (3) | 0.36171 (18) | 0.0187 (5) | |
O3 | 0.36452 (7) | 0.4889 (3) | 0.51713 (18) | 0.0199 (5) | |
O4 | 0.42351 (6) | −0.0976 (3) | 0.62402 (18) | 0.0194 (5) | |
O5 | 0.36088 (6) | −0.1387 (3) | 0.67819 (17) | 0.0170 (5) | |
O6 | 0.36990 (7) | −0.0087 (3) | 0.49995 (18) | 0.0210 (5) | |
N1 | 0.35828 (8) | 0.6955 (3) | 0.3665 (2) | 0.0180 (6) | |
H1A | 0.356604 | 0.781176 | 0.412964 | 0.022* | |
N2 | 0.38293 (8) | 0.2007 (3) | 0.6476 (2) | 0.0168 (6) | |
H2A | 0.375197 | 0.286157 | 0.605547 | 0.020* | |
C1 | 0.43126 (10) | 0.4686 (4) | 0.3354 (3) | 0.0197 (7) | |
C2 | 0.44869 (10) | 0.5765 (4) | 0.4080 (3) | 0.0242 (7) | |
H2 | 0.436504 | 0.598886 | 0.470343 | 0.029* | |
C3 | 0.48398 (11) | 0.6503 (5) | 0.3877 (3) | 0.0294 (8) | |
H3 | 0.496173 | 0.725736 | 0.436186 | 0.035* | |
C4 | 0.50202 (11) | 0.6159 (5) | 0.2970 (3) | 0.0302 (9) | |
H4 | 0.526406 | 0.667418 | 0.283644 | 0.036* | |
C5 | 0.48419 (12) | 0.5055 (5) | 0.2260 (3) | 0.0315 (9) | |
H5 | 0.496518 | 0.480949 | 0.164086 | 0.038* | |
C6 | 0.44842 (10) | 0.4310 (5) | 0.2452 (3) | 0.0245 (7) | |
H6 | 0.436070 | 0.355596 | 0.196906 | 0.029* | |
C7 | 0.35731 (9) | 0.7602 (4) | 0.2666 (2) | 0.0165 (6) | |
C8 | 0.36145 (9) | 0.9497 (4) | 0.2502 (2) | 0.0182 (6) | |
H8 | 0.366179 | 1.031378 | 0.304399 | 0.022* | |
C9 | 0.35851 (10) | 1.0148 (4) | 0.1542 (3) | 0.0226 (7) | |
C10 | 0.35152 (10) | 0.8991 (5) | 0.0744 (3) | 0.0230 (7) | |
C11 | 0.34843 (10) | 0.7138 (5) | 0.0890 (3) | 0.0230 (7) | |
H11 | 0.344450 | 0.633649 | 0.033796 | 0.028* | |
C12 | 0.35116 (9) | 0.6421 (4) | 0.1865 (2) | 0.0200 (7) | |
H12 | 0.348810 | 0.513235 | 0.197536 | 0.024* | |
C13 | 0.29148 (10) | 0.3682 (4) | 0.3976 (3) | 0.0200 (7) | |
C14 | 0.26516 (11) | 0.4717 (5) | 0.3454 (3) | 0.0304 (9) | |
H14 | 0.272923 | 0.546577 | 0.290749 | 0.036* | |
C15 | 0.22760 (13) | 0.4646 (5) | 0.3736 (4) | 0.0418 (11) | |
H15 | 0.209100 | 0.532953 | 0.337294 | 0.050* | |
C16 | 0.21639 (11) | 0.3588 (5) | 0.4545 (3) | 0.0353 (10) | |
H16 | 0.190365 | 0.355026 | 0.474179 | 0.042* | |
C17 | 0.24353 (12) | 0.2584 (5) | 0.5064 (3) | 0.0360 (9) | |
H17 | 0.236009 | 0.185533 | 0.562064 | 0.043* | |
C18 | 0.28130 (11) | 0.2630 (5) | 0.4783 (3) | 0.0292 (8) | |
H18 | 0.299912 | 0.194546 | 0.514149 | 0.035* | |
C19 | 0.45822 (9) | −0.0143 (4) | 0.5973 (3) | 0.0220 (7) | |
C20 | 0.48839 (11) | −0.0476 (5) | 0.6600 (3) | 0.0294 (9) | |
H20 | 0.485254 | −0.120532 | 0.718484 | 0.035* | |
C21 | 0.52378 (11) | 0.0280 (5) | 0.6359 (4) | 0.0385 (11) | |
H21 | 0.545011 | 0.006380 | 0.678530 | 0.046* | |
C22 | 0.52831 (12) | 0.1330 (5) | 0.5516 (4) | 0.0408 (11) | |
H22 | 0.552574 | 0.183945 | 0.536193 | 0.049* | |
C23 | 0.49802 (12) | 0.1648 (5) | 0.4897 (4) | 0.0391 (11) | |
H23 | 0.501267 | 0.238689 | 0.431631 | 0.047* | |
C24 | 0.46225 (11) | 0.0892 (5) | 0.5113 (3) | 0.0294 (8) | |
H24 | 0.441212 | 0.108725 | 0.467731 | 0.035* | |
C25A | 0.39326 (14) | 0.2646 (5) | 0.7430 (2) | 0.0185 (3) | 0.892 (4) |
C26A | 0.39294 (10) | 0.4534 (4) | 0.76047 (19) | 0.0185 (3) | 0.892 (4) |
H26A | 0.385702 | 0.535850 | 0.708602 | 0.022* | 0.892 (4) |
C27A | 0.40323 (9) | 0.5217 (3) | 0.8538 (2) | 0.0185 (3) | 0.892 (4) |
C28A | 0.41382 (9) | 0.4011 (3) | 0.92971 (17) | 0.0185 (3) | 0.892 (4) |
C29A | 0.41414 (11) | 0.2123 (3) | 0.9122 (2) | 0.0185 (3) | 0.892 (4) |
H29A | 0.421381 | 0.129843 | 0.964106 | 0.022* | 0.892 (4) |
C30A | 0.40386 (14) | 0.1440 (3) | 0.8189 (3) | 0.0185 (3) | 0.892 (4) |
H30A | 0.404072 | 0.014921 | 0.806938 | 0.022* | 0.892 (4) |
F3A | 0.40330 (9) | 0.7010 (3) | 0.87205 (19) | 0.0417 (8) | 0.892 (4) |
F4A | 0.42420 (13) | 0.4698 (5) | 1.0186 (3) | 0.0330 (8) | 0.892 (4) |
C25B | 0.3925 (12) | 0.263 (4) | 0.7445 (19) | 0.0185 (3) | 0.108 (4) |
C26B | 0.4056 (12) | 0.164 (3) | 0.827 (2) | 0.0185 (3) | 0.108 (4) |
H26B | 0.411339 | 0.036498 | 0.820275 | 0.022* | 0.108 (4) |
C27B | 0.4103 (9) | 0.252 (3) | 0.9184 (19) | 0.0185 (3) | 0.108 (4) |
C28B | 0.4019 (8) | 0.438 (3) | 0.9278 (15) | 0.0185 (3) | 0.108 (4) |
C29B | 0.3888 (8) | 0.537 (3) | 0.8456 (19) | 0.0185 (3) | 0.108 (4) |
H29B | 0.383045 | 0.664159 | 0.852041 | 0.022* | 0.108 (4) |
C30B | 0.3841 (8) | 0.449 (4) | 0.7539 (17) | 0.0185 (3) | 0.108 (4) |
H30B | 0.375173 | 0.516654 | 0.697713 | 0.022* | 0.108 (4) |
F3B | 0.4194 (7) | 0.139 (2) | 0.9938 (15) | 0.0417 (8) | 0.108 (4) |
F4B | 0.4155 (14) | 0.510 (5) | 1.018 (3) | 0.0330 (8) | 0.108 (4) |
C31 | 0.32072 (9) | −0.1272 (4) | 0.6836 (2) | 0.0168 (6) | |
C32 | 0.29908 (10) | −0.2353 (4) | 0.6208 (3) | 0.0242 (7) | |
H32 | 0.310891 | −0.314146 | 0.573196 | 0.029* | |
C33 | 0.25994 (11) | −0.2266 (5) | 0.6284 (3) | 0.0296 (8) | |
H33 | 0.244534 | −0.297924 | 0.584574 | 0.035* | |
C34 | 0.24292 (10) | −0.1155 (5) | 0.6991 (3) | 0.0259 (8) | |
H34 | 0.215903 | −0.110939 | 0.704092 | 0.031* | |
C35 | 0.26519 (11) | −0.0105 (5) | 0.7628 (3) | 0.0299 (9) | |
H35 | 0.253467 | 0.064689 | 0.812260 | 0.036* | |
C36 | 0.30457 (11) | −0.0150 (4) | 0.7546 (3) | 0.0248 (8) | |
H36 | 0.320085 | 0.058106 | 0.797266 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0212 (4) | 0.0117 (4) | 0.0152 (4) | 0.0010 (3) | −0.0019 (4) | −0.0001 (3) |
P2 | 0.0193 (4) | 0.0115 (4) | 0.0160 (4) | 0.0000 (3) | −0.0012 (3) | −0.0003 (3) |
F1 | 0.0705 (18) | 0.0200 (11) | 0.0328 (13) | −0.0057 (10) | −0.0021 (12) | 0.0057 (9) |
F2 | 0.0491 (15) | 0.0329 (12) | 0.0160 (11) | −0.0052 (10) | −0.0022 (10) | 0.0081 (8) |
O1 | 0.0199 (12) | 0.0162 (11) | 0.0220 (12) | 0.0006 (8) | 0.0006 (10) | −0.0014 (9) |
O2 | 0.0213 (12) | 0.0153 (11) | 0.0194 (12) | −0.0017 (8) | 0.0003 (10) | −0.0022 (9) |
O3 | 0.0278 (14) | 0.0156 (11) | 0.0164 (12) | 0.0019 (9) | −0.0026 (10) | 0.0000 (8) |
O4 | 0.0187 (12) | 0.0162 (11) | 0.0233 (13) | 0.0006 (8) | 0.0021 (10) | 0.0028 (9) |
O5 | 0.0172 (11) | 0.0142 (11) | 0.0196 (12) | −0.0005 (8) | 0.0000 (9) | 0.0019 (9) |
O6 | 0.0299 (14) | 0.0153 (12) | 0.0179 (13) | −0.0033 (9) | −0.0020 (10) | −0.0024 (8) |
N1 | 0.0275 (16) | 0.0121 (13) | 0.0143 (13) | 0.0023 (10) | −0.0017 (12) | −0.0019 (10) |
N2 | 0.0248 (15) | 0.0123 (13) | 0.0133 (13) | 0.0018 (10) | −0.0034 (11) | 0.0006 (9) |
C1 | 0.0217 (18) | 0.0150 (15) | 0.0224 (18) | 0.0011 (12) | −0.0013 (14) | 0.0014 (12) |
C2 | 0.0252 (18) | 0.0215 (16) | 0.0258 (18) | 0.0033 (13) | −0.0027 (16) | −0.0060 (14) |
C3 | 0.028 (2) | 0.0230 (18) | 0.037 (2) | −0.0016 (14) | −0.0046 (17) | −0.0049 (15) |
C4 | 0.023 (2) | 0.0261 (19) | 0.042 (2) | −0.0012 (14) | 0.0036 (17) | 0.0058 (16) |
C5 | 0.032 (2) | 0.038 (2) | 0.025 (2) | −0.0015 (16) | 0.0064 (17) | 0.0035 (15) |
C6 | 0.030 (2) | 0.0221 (17) | 0.0209 (18) | −0.0021 (13) | −0.0006 (15) | −0.0002 (13) |
C7 | 0.0143 (15) | 0.0171 (15) | 0.0181 (17) | 0.0020 (11) | 0.0005 (13) | 0.0014 (11) |
C8 | 0.0220 (17) | 0.0168 (15) | 0.0158 (16) | −0.0029 (11) | 0.0005 (13) | −0.0011 (12) |
C9 | 0.0278 (19) | 0.0129 (16) | 0.027 (2) | −0.0026 (12) | −0.0002 (15) | 0.0050 (12) |
C10 | 0.0256 (19) | 0.0282 (19) | 0.0151 (17) | −0.0008 (13) | 0.0008 (14) | 0.0035 (13) |
C11 | 0.0278 (19) | 0.0221 (16) | 0.0193 (18) | −0.0006 (13) | −0.0006 (14) | −0.0026 (13) |
C12 | 0.0275 (18) | 0.0155 (15) | 0.0170 (16) | 0.0008 (12) | −0.0013 (14) | −0.0019 (12) |
C13 | 0.0231 (17) | 0.0135 (14) | 0.0233 (17) | −0.0020 (11) | 0.0026 (14) | −0.0022 (12) |
C14 | 0.029 (2) | 0.0231 (18) | 0.039 (2) | 0.0035 (14) | 0.0020 (18) | 0.0122 (16) |
C15 | 0.030 (2) | 0.028 (2) | 0.068 (3) | 0.0079 (16) | −0.002 (2) | 0.010 (2) |
C16 | 0.024 (2) | 0.027 (2) | 0.055 (3) | −0.0033 (15) | 0.0102 (19) | −0.0083 (17) |
C17 | 0.035 (2) | 0.039 (2) | 0.034 (2) | −0.0067 (17) | 0.0082 (18) | 0.0030 (18) |
C18 | 0.031 (2) | 0.031 (2) | 0.026 (2) | −0.0031 (15) | −0.0027 (16) | 0.0065 (15) |
C19 | 0.0211 (16) | 0.0141 (15) | 0.031 (2) | −0.0009 (11) | 0.0090 (15) | −0.0025 (13) |
C20 | 0.027 (2) | 0.0244 (19) | 0.037 (2) | 0.0031 (14) | 0.0006 (17) | −0.0013 (15) |
C21 | 0.021 (2) | 0.037 (2) | 0.058 (3) | −0.0001 (16) | 0.0020 (19) | −0.005 (2) |
C22 | 0.026 (2) | 0.021 (2) | 0.076 (3) | −0.0002 (15) | 0.019 (2) | −0.0032 (19) |
C23 | 0.038 (2) | 0.0187 (19) | 0.061 (3) | 0.0042 (15) | 0.021 (2) | 0.0072 (18) |
C24 | 0.031 (2) | 0.0203 (17) | 0.037 (2) | 0.0040 (14) | 0.0096 (17) | 0.0067 (15) |
C25A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C26A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C27A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C28A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C29A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C30A | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
F3A | 0.090 (2) | 0.0108 (11) | 0.0241 (13) | 0.0081 (11) | −0.0180 (14) | −0.0055 (9) |
F4A | 0.059 (3) | 0.023 (2) | 0.0175 (12) | 0.0010 (13) | −0.0115 (15) | −0.0049 (14) |
C25B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C26B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C27B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C28B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C29B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
C30B | 0.0253 (8) | 0.0156 (7) | 0.0147 (7) | −0.0010 (6) | −0.0042 (7) | −0.0008 (5) |
F3B | 0.090 (2) | 0.0108 (11) | 0.0241 (13) | 0.0081 (11) | −0.0180 (14) | −0.0055 (9) |
F4B | 0.059 (3) | 0.023 (2) | 0.0175 (12) | 0.0010 (13) | −0.0115 (15) | −0.0049 (14) |
C31 | 0.0160 (15) | 0.0142 (14) | 0.0202 (16) | −0.0020 (11) | −0.0005 (13) | 0.0022 (12) |
C32 | 0.0232 (18) | 0.0235 (17) | 0.0260 (19) | −0.0019 (13) | 0.0036 (15) | −0.0098 (14) |
C33 | 0.026 (2) | 0.033 (2) | 0.030 (2) | −0.0067 (14) | 0.0003 (16) | −0.0059 (15) |
C34 | 0.0205 (18) | 0.0255 (19) | 0.032 (2) | −0.0007 (13) | 0.0020 (15) | 0.0050 (15) |
C35 | 0.028 (2) | 0.028 (2) | 0.033 (2) | 0.0018 (14) | 0.0064 (17) | −0.0073 (16) |
C36 | 0.0263 (19) | 0.0233 (18) | 0.0249 (19) | −0.0007 (13) | −0.0017 (15) | −0.0057 (14) |
P1—O3 | 1.468 (2) | C15—C16 | 1.382 (6) |
P1—O1 | 1.577 (2) | C16—C17 | 1.385 (6) |
P1—O2 | 1.578 (2) | C17—C18 | 1.377 (5) |
P1—N1 | 1.622 (3) | C19—C20 | 1.371 (5) |
P2—O6 | 1.462 (2) | C19—C24 | 1.380 (5) |
P2—O4 | 1.579 (2) | C20—C21 | 1.394 (5) |
P2—O5 | 1.581 (2) | C21—C22 | 1.370 (6) |
P2—N2 | 1.627 (3) | C22—C23 | 1.366 (6) |
F1—C9 | 1.344 (4) | C23—C24 | 1.399 (5) |
F2—C10 | 1.353 (4) | C25A—C26A | 1.3900 |
O1—C1 | 1.403 (4) | C25A—C30A | 1.3900 |
O2—C13 | 1.417 (4) | C26A—C27A | 1.3900 |
O4—C19 | 1.405 (4) | C27A—F3A | 1.324 (3) |
O5—C31 | 1.412 (4) | C27A—C28A | 1.3900 |
N1—C7 | 1.416 (4) | C28A—F4A | 1.339 (5) |
N2—C25A | 1.403 (3) | C28A—C29A | 1.3900 |
N2—C25B | 1.411 (19) | C29A—C30A | 1.3900 |
C1—C6 | 1.375 (5) | C25B—C26B | 1.3900 |
C1—C2 | 1.389 (5) | C25B—C30B | 1.3900 |
C2—C3 | 1.375 (5) | C26B—C27B | 1.3900 |
C3—C4 | 1.389 (6) | C27B—F3B | 1.34 (3) |
C4—C5 | 1.390 (6) | C27B—C28B | 1.3900 |
C5—C6 | 1.390 (5) | C28B—C29B | 1.3900 |
C7—C12 | 1.388 (4) | C28B—F4B | 1.40 (5) |
C7—C8 | 1.400 (4) | C29B—C30B | 1.3900 |
C8—C9 | 1.372 (5) | C31—C36 | 1.372 (5) |
C9—C10 | 1.379 (5) | C31—C32 | 1.377 (4) |
C10—C11 | 1.363 (5) | C32—C33 | 1.378 (5) |
C11—C12 | 1.406 (5) | C33—C34 | 1.378 (5) |
C13—C18 | 1.368 (5) | C34—C35 | 1.384 (5) |
C13—C14 | 1.379 (5) | C35—C36 | 1.385 (5) |
C14—C15 | 1.371 (6) | ||
O3—P1—O1 | 116.48 (13) | C15—C16—C17 | 119.2 (4) |
O3—P1—O2 | 116.01 (14) | C18—C17—C16 | 120.7 (4) |
O1—P1—O2 | 95.07 (13) | C13—C18—C17 | 118.7 (4) |
O3—P1—N1 | 109.13 (14) | C20—C19—C24 | 121.7 (3) |
O1—P1—N1 | 109.15 (14) | C20—C19—O4 | 115.9 (3) |
O2—P1—N1 | 110.23 (13) | C24—C19—O4 | 122.3 (3) |
O6—P2—O4 | 116.59 (14) | C19—C20—C21 | 118.4 (4) |
O6—P2—O5 | 116.04 (13) | C22—C21—C20 | 120.8 (4) |
O4—P2—O5 | 95.09 (12) | C23—C22—C21 | 120.2 (4) |
O6—P2—N2 | 110.05 (14) | C22—C23—C24 | 120.4 (4) |
O4—P2—N2 | 108.94 (13) | C19—C24—C23 | 118.5 (4) |
O5—P2—N2 | 109.13 (13) | C26A—C25A—C30A | 120.0 |
C1—O1—P1 | 122.53 (19) | C26A—C25A—N2 | 118.4 (3) |
C13—O2—P1 | 122.0 (2) | C30A—C25A—N2 | 121.6 (3) |
C19—O4—P2 | 123.8 (2) | C25A—C26A—C27A | 120.0 |
C31—O5—P2 | 119.34 (19) | F3A—C27A—C28A | 118.9 (2) |
C7—N1—P1 | 129.1 (2) | F3A—C27A—C26A | 121.1 (2) |
C25A—N2—P2 | 129.4 (2) | C28A—C27A—C26A | 120.0 |
C25B—N2—P2 | 128.9 (13) | F4A—C28A—C27A | 119.1 (2) |
C6—C1—C2 | 122.2 (3) | F4A—C28A—C29A | 120.9 (2) |
C6—C1—O1 | 115.6 (3) | C27A—C28A—C29A | 120.0 |
C2—C1—O1 | 122.2 (3) | C30A—C29A—C28A | 120.0 |
C3—C2—C1 | 118.5 (3) | C29A—C30A—C25A | 120.0 |
C2—C3—C4 | 120.8 (4) | C26B—C25B—C30B | 120.0 |
C3—C4—C5 | 119.6 (4) | C26B—C25B—N2 | 130 (2) |
C6—C5—C4 | 120.3 (4) | C30B—C25B—N2 | 110 (2) |
C1—C6—C5 | 118.7 (3) | C27B—C26B—C25B | 120.0 |
C12—C7—C8 | 120.1 (3) | F3B—C27B—C26B | 114.5 (19) |
C12—C7—N1 | 121.8 (3) | F3B—C27B—C28B | 125.2 (19) |
C8—C7—N1 | 118.0 (3) | C26B—C27B—C28B | 120.0 |
C9—C8—C7 | 118.5 (3) | C27B—C28B—C29B | 120.0 |
F1—C9—C8 | 120.4 (3) | C27B—C28B—F4B | 112 (2) |
F1—C9—C10 | 117.8 (3) | C29B—C28B—F4B | 127 (2) |
C8—C9—C10 | 121.8 (3) | C30B—C29B—C28B | 120.0 |
F2—C10—C11 | 120.4 (3) | C29B—C30B—C25B | 120.0 |
F2—C10—C9 | 119.3 (3) | C36—C31—C32 | 122.2 (3) |
C11—C10—C9 | 120.2 (3) | C36—C31—O5 | 118.8 (3) |
C10—C11—C12 | 119.5 (3) | C32—C31—O5 | 118.9 (3) |
C7—C12—C11 | 119.8 (3) | C31—C32—C33 | 118.5 (3) |
C18—C13—C14 | 121.9 (3) | C32—C33—C34 | 120.6 (3) |
C18—C13—O2 | 119.6 (3) | C33—C34—C35 | 120.0 (3) |
C14—C13—O2 | 118.4 (3) | C34—C35—C36 | 120.0 (3) |
C15—C14—C13 | 118.9 (4) | C31—C36—C35 | 118.7 (3) |
C14—C15—C16 | 120.6 (4) | ||
O3—P1—O1—C1 | −78.0 (3) | C14—C13—C18—C17 | 1.3 (5) |
O2—P1—O1—C1 | 159.5 (2) | O2—C13—C18—C17 | −174.2 (3) |
N1—P1—O1—C1 | 46.1 (3) | C16—C17—C18—C13 | −0.3 (6) |
O3—P1—O2—C13 | 47.5 (3) | P2—O4—C19—C20 | 146.8 (3) |
O1—P1—O2—C13 | 170.2 (2) | P2—O4—C19—C24 | −35.5 (4) |
N1—P1—O2—C13 | −77.2 (3) | C24—C19—C20—C21 | 0.8 (5) |
O6—P2—O4—C19 | 73.3 (3) | O4—C19—C20—C21 | 178.5 (3) |
O5—P2—O4—C19 | −164.2 (2) | C19—C20—C21—C22 | 0.0 (6) |
N2—P2—O4—C19 | −51.9 (3) | C20—C21—C22—C23 | −0.1 (6) |
O6—P2—O5—C31 | −51.9 (3) | C21—C22—C23—C24 | −0.5 (6) |
O4—P2—O5—C31 | −174.8 (2) | C20—C19—C24—C23 | −1.5 (5) |
N2—P2—O5—C31 | 73.1 (2) | O4—C19—C24—C23 | −179.0 (3) |
O3—P1—N1—C7 | 176.0 (3) | C22—C23—C24—C19 | 1.3 (6) |
O1—P1—N1—C7 | 47.7 (3) | P2—N2—C25A—C26A | 175.8 (2) |
O2—P1—N1—C7 | −55.5 (3) | P2—N2—C25A—C30A | −3.8 (5) |
O6—P2—N2—C25A | 179.9 (3) | C30A—C25A—C26A—C27A | 0.0 |
O4—P2—N2—C25A | −51.2 (4) | N2—C25A—C26A—C27A | −179.6 (4) |
O5—P2—N2—C25A | 51.4 (4) | C25A—C26A—C27A—F3A | 179.7 (3) |
O6—P2—N2—C25B | 178 (2) | C25A—C26A—C27A—C28A | 0.0 |
O4—P2—N2—C25B | −53 (2) | F3A—C27A—C28A—F4A | −0.7 (4) |
O5—P2—N2—C25B | 50 (2) | C26A—C27A—C28A—F4A | 179.0 (4) |
P1—O1—C1—C6 | −143.3 (3) | F3A—C27A—C28A—C29A | −179.7 (3) |
P1—O1—C1—C2 | 38.6 (4) | C26A—C27A—C28A—C29A | 0.0 |
C6—C1—C2—C3 | 1.2 (5) | F4A—C28A—C29A—C30A | −178.9 (4) |
O1—C1—C2—C3 | 179.1 (3) | C27A—C28A—C29A—C30A | 0.0 |
C1—C2—C3—C4 | −0.8 (5) | C28A—C29A—C30A—C25A | 0.0 |
C2—C3—C4—C5 | 0.0 (5) | C26A—C25A—C30A—C29A | 0.0 |
C3—C4—C5—C6 | 0.4 (6) | N2—C25A—C30A—C29A | 179.6 (4) |
C2—C1—C6—C5 | −0.8 (5) | P2—N2—C25B—C26B | 2 (3) |
O1—C1—C6—C5 | −178.8 (3) | P2—N2—C25B—C30B | −173.0 (9) |
C4—C5—C6—C1 | −0.1 (5) | C30B—C25B—C26B—C27B | 0.0 |
P1—N1—C7—C12 | 14.5 (5) | N2—C25B—C26B—C27B | −175 (3) |
P1—N1—C7—C8 | −167.6 (2) | C25B—C26B—C27B—F3B | 174 (3) |
C12—C7—C8—C9 | 1.3 (5) | C25B—C26B—C27B—C28B | 0.0 |
N1—C7—C8—C9 | −176.6 (3) | F3B—C27B—C28B—C29B | −173 (3) |
C7—C8—C9—F1 | 179.6 (3) | C26B—C27B—C28B—C29B | 0.0 |
C7—C8—C9—C10 | 0.2 (5) | F3B—C27B—C28B—F4B | 19 (4) |
F1—C9—C10—F2 | −1.6 (5) | C26B—C27B—C28B—F4B | −168 (3) |
C8—C9—C10—F2 | 177.8 (3) | C27B—C28B—C29B—C30B | 0.0 |
F1—C9—C10—C11 | 178.7 (3) | F4B—C28B—C29B—C30B | 166 (3) |
C8—C9—C10—C11 | −1.9 (5) | C28B—C29B—C30B—C25B | 0.0 |
F2—C10—C11—C12 | −177.7 (3) | C26B—C25B—C30B—C29B | 0.0 |
C9—C10—C11—C12 | 2.1 (5) | N2—C25B—C30B—C29B | 176 (3) |
C8—C7—C12—C11 | −1.1 (5) | P2—O5—C31—C36 | −93.6 (3) |
N1—C7—C12—C11 | 176.7 (3) | P2—O5—C31—C32 | 89.4 (3) |
C10—C11—C12—C7 | −0.6 (5) | C36—C31—C32—C33 | 1.5 (5) |
P1—O2—C13—C18 | −85.3 (3) | O5—C31—C32—C33 | 178.3 (3) |
P1—O2—C13—C14 | 99.0 (3) | C31—C32—C33—C34 | −1.6 (5) |
C18—C13—C14—C15 | −1.8 (6) | C32—C33—C34—C35 | 0.4 (5) |
O2—C13—C14—C15 | 173.7 (3) | C33—C34—C35—C36 | 1.0 (5) |
C13—C14—C15—C16 | 1.4 (6) | C32—C31—C36—C35 | −0.2 (5) |
C14—C15—C16—C17 | −0.5 (6) | O5—C31—C36—C35 | −177.0 (3) |
C15—C16—C17—C18 | −0.1 (6) | C34—C35—C36—C31 | −1.1 (5) |
Form | Solvent | Temperature (°C) | Crystal habit |
Concomitant (I and II) | Toluene | 22–25 | Block + needle |
DCM–Hexane | 4 | Block + needle | |
Form II | Methanol, DCM–hexane, ethanol | 22–25 | Needle |
Torsion | Form I | Form II |
P1—O2—C13—C18/P2—O4—C19—C20 | 114.98 (12) | 85.3 (3) |
146.8 (3) | ||
P1—N1—C7—C12/P2—N2—C25A—C30A | 169.82 (11) | 14.5 (5) |
3.8 (5) | ||
P1—O1—C1—C2/P2—O5—C31—C36 | 132.55 (12) | 38.6 (4) |
93.6 (3) |