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The concomitant occurrence of dimorphs of diphenyl (3,4-di­fluoro­phen­yl)phos­pho­ramidate, C18H14F2NO3P, was observed via a solution-mediated crystallization process with variation in the symmetry-free mol­ecules (Z′). The existence of two forms, i.e. Form I (block, Z′ = 1) and Form II (needle, Z′ = 2), was characterized by single-crystal X-ray diffraction, differential scanning calorimetry and powder X-ray diffraction. Furthermore, a qu­anti­tative analysis of the energetics of the different inter­molecular inter­actions was carried out via the energy decomposition method (PIXEL), which corroborates with inputs from the energy framework and looks at the topology of the various inter­molecular inter­actions present in both forms. The unequivocally distinguished contribution of strong N—H...O hydrogen bonds along with other inter­actions, such as C—H...O, C—H...F, π–π and C—H...π, mapped on the Hirshfeld surface is depicted by two-dimensional fingerprint plots. Apart from the major electrostatic contribution from N—H...O hydrogen bonds, the crystal structures are stabilized by contributions from the dispersion energy. The closely related melting points and opposite trends in the calculated lattice energies are inter­esting to investigate with respect to the thermodynamic stability of the observed dimorphs. The significant variation in the torsion angles in both forms helps in classifying them in the category of conformational polymorphs.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003589/jx3028sup1.cif
Contains datablocks formI, formII, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003589/jx3028formIsup2.hkl
Contains datablock formI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003589/jx3028formIIsup3.hkl
Contains datablock formII

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003589/jx3028formIsup4.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619003589/jx3028sup5.pdf
Crystallization summary, powder patterns, PIXEL calculations and energy framework information

CCDC references: 1877354; 1877353

Computing details top

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).

Diphenyl (3,4-difluorophenyl)phosphoramidate (formI) top
Crystal data top
C18H14F2NO3PF(000) = 744
Mr = 361.27Dx = 1.431 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.2037 (3) ÅCell parameters from 7646 reflections
b = 9.1372 (3) Åθ = 3.0–28.3°
c = 17.9981 (5) ŵ = 0.20 mm1
β = 92.260 (1)°T = 100 K
V = 1676.72 (9) Å3Block, colorless
Z = 40.24 × 0.14 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
2724 reflections with I > 2σ(I)
φ and ω scansRint = 0.026
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
θmax = 25.0°, θmin = 2.0°
Tmin = 0.685, Tmax = 0.746h = 1212
12986 measured reflectionsk = 1010
2935 independent reflectionsl = 2121
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H 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 reflectionsΔρmax = 0.27 e Å3
229 parametersΔρmin = 0.36 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.69854 (3)0.55364 (4)0.45512 (2)0.01971 (12)
O10.76245 (9)0.57544 (11)0.37749 (5)0.0229 (2)
O20.83001 (9)0.57334 (10)0.50351 (5)0.0220 (2)
O30.59246 (9)0.65535 (10)0.47204 (6)0.0247 (2)
F11.03376 (8)0.11956 (10)0.39419 (5)0.0344 (2)
F20.91966 (9)0.13348 (9)0.42936 (5)0.0343 (2)
N10.64940 (11)0.38495 (13)0.46164 (7)0.0216 (3)
H1A0.5741 (17)0.3758 (18)0.4813 (9)0.026*
C10.69334 (14)0.54882 (16)0.30941 (8)0.0249 (3)
C20.75696 (16)0.46668 (19)0.25802 (9)0.0345 (4)
H20.8411400.4266200.2698080.041*
C30.69662 (19)0.4431 (2)0.18880 (10)0.0450 (4)
H30.7395390.3866420.1527220.054*
C40.57445 (18)0.5015 (2)0.17213 (10)0.0463 (5)
H40.5328590.4844920.1247590.056*
C50.51299 (17)0.5841 (2)0.22397 (10)0.0489 (5)
H50.4290610.6245980.2119930.059*
C60.57171 (15)0.6093 (2)0.29384 (10)0.0377 (4)
H60.5291910.6666330.3297560.045*
C70.72206 (13)0.25549 (15)0.45390 (7)0.0189 (3)
C80.84869 (13)0.25457 (15)0.42702 (8)0.0220 (3)
H80.8902050.3432020.4135240.026*
C90.91183 (13)0.12261 (16)0.42056 (8)0.0232 (3)
C100.85381 (14)0.00689 (16)0.43892 (8)0.0239 (3)
C110.72971 (14)0.00755 (16)0.46600 (8)0.0267 (3)
H110.6893470.0969800.4793040.032*
C120.66449 (14)0.12405 (15)0.47358 (8)0.0227 (3)
H120.5789280.1245210.4925650.027*
C130.83067 (13)0.54108 (15)0.58046 (8)0.0226 (3)
C140.76192 (16)0.62747 (18)0.62802 (9)0.0341 (4)
H140.7103350.7072140.6097530.041*
C150.77000 (19)0.5950 (2)0.70300 (10)0.0475 (5)
H150.7227590.6525200.7368540.057*
C160.84617 (18)0.4798 (2)0.72918 (10)0.0471 (5)
H160.8512980.4585160.7808830.057*
C170.91476 (16)0.3955 (2)0.68050 (9)0.0365 (4)
H170.9672360.3164010.6987490.044*
C180.90742 (13)0.42563 (17)0.60516 (8)0.0260 (3)
H180.9542830.3680020.5712010.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01632 (19)0.0135 (2)0.0298 (2)0.00068 (13)0.00687 (14)0.00162 (14)
O10.0182 (5)0.0211 (5)0.0296 (5)0.0019 (4)0.0049 (4)0.0029 (4)
O20.0192 (5)0.0189 (5)0.0284 (5)0.0022 (4)0.0072 (4)0.0011 (4)
O30.0197 (5)0.0157 (5)0.0395 (6)0.0001 (4)0.0092 (4)0.0018 (4)
F10.0222 (4)0.0281 (5)0.0539 (6)0.0050 (4)0.0130 (4)0.0019 (4)
F20.0345 (5)0.0170 (5)0.0515 (6)0.0091 (4)0.0023 (4)0.0026 (4)
N10.0159 (6)0.0155 (6)0.0338 (7)0.0013 (5)0.0077 (5)0.0011 (5)
C10.0213 (7)0.0233 (8)0.0301 (8)0.0042 (6)0.0018 (6)0.0075 (6)
C20.0324 (8)0.0368 (9)0.0342 (8)0.0075 (7)0.0010 (7)0.0005 (7)
C30.0488 (11)0.0503 (12)0.0355 (9)0.0067 (9)0.0028 (8)0.0023 (8)
C40.0391 (10)0.0653 (13)0.0340 (9)0.0055 (9)0.0065 (8)0.0088 (9)
C50.0258 (9)0.0754 (14)0.0450 (10)0.0053 (9)0.0028 (7)0.0196 (10)
C60.0265 (8)0.0481 (11)0.0388 (9)0.0077 (7)0.0058 (7)0.0112 (8)
C70.0196 (7)0.0157 (7)0.0213 (6)0.0006 (5)0.0002 (5)0.0013 (5)
C80.0202 (7)0.0159 (7)0.0302 (7)0.0024 (5)0.0041 (6)0.0007 (6)
C90.0182 (7)0.0246 (8)0.0271 (7)0.0020 (6)0.0028 (5)0.0027 (6)
C100.0272 (7)0.0156 (7)0.0285 (7)0.0056 (6)0.0029 (6)0.0029 (6)
C110.0294 (8)0.0157 (7)0.0350 (8)0.0028 (6)0.0014 (6)0.0026 (6)
C120.0200 (7)0.0195 (7)0.0289 (7)0.0022 (6)0.0026 (6)0.0013 (6)
C130.0194 (7)0.0209 (7)0.0278 (7)0.0067 (6)0.0059 (5)0.0022 (6)
C140.0341 (8)0.0296 (9)0.0392 (9)0.0031 (7)0.0080 (7)0.0081 (7)
C150.0486 (11)0.0583 (13)0.0363 (10)0.0039 (9)0.0130 (8)0.0170 (9)
C160.0433 (10)0.0715 (14)0.0268 (9)0.0014 (10)0.0046 (7)0.0000 (8)
C170.0289 (8)0.0462 (10)0.0344 (9)0.0013 (7)0.0010 (7)0.0068 (7)
C180.0197 (7)0.0271 (8)0.0314 (8)0.0013 (6)0.0050 (6)0.0015 (6)
Geometric parameters (Å, º) top
P1—O31.4677 (10)C7—C121.3890 (19)
P1—O11.5776 (10)C7—C81.3974 (19)
P1—O21.5807 (10)C8—C91.374 (2)
P1—N11.6266 (12)C8—H80.9500
O1—C11.4105 (17)C9—C101.369 (2)
O2—C131.4156 (17)C10—C111.375 (2)
F1—C91.3492 (16)C11—C121.384 (2)
F2—C101.3521 (16)C11—H110.9500
N1—C71.4059 (17)C12—H120.9500
N1—H1A0.863 (17)C13—C141.377 (2)
C1—C21.374 (2)C13—C181.377 (2)
C1—C61.377 (2)C14—C151.381 (3)
C2—C31.384 (2)C14—H140.9500
C2—H20.9500C15—C161.381 (3)
C3—C41.378 (3)C15—H150.9500
C3—H30.9500C16—C171.378 (3)
C4—C51.371 (3)C16—H160.9500
C4—H40.9500C17—C181.383 (2)
C5—C61.391 (3)C17—H170.9500
C5—H50.9500C18—H180.9500
C6—H60.9500
O3—P1—O1115.97 (6)C9—C8—H8120.7
O3—P1—O2115.49 (6)C7—C8—H8120.7
O1—P1—O295.87 (5)F1—C9—C10118.71 (13)
O3—P1—N1110.67 (6)F1—C9—C8119.33 (13)
O1—P1—N1108.84 (6)C10—C9—C8121.95 (13)
O2—P1—N1108.99 (6)F2—C10—C9119.13 (13)
C1—O1—P1122.52 (8)F2—C10—C11120.71 (13)
C13—O2—P1119.11 (8)C9—C10—C11120.16 (13)
C7—N1—P1128.67 (10)C10—C11—C12118.98 (13)
C7—N1—H1A116.2 (11)C10—C11—H11120.5
P1—N1—H1A113.8 (11)C12—C11—H11120.5
C2—C1—C6121.88 (15)C11—C12—C7121.09 (13)
C2—C1—O1116.47 (13)C11—C12—H12119.5
C6—C1—O1121.54 (14)C7—C12—H12119.5
C1—C2—C3119.04 (16)C14—C13—C18122.39 (14)
C1—C2—H2120.5C14—C13—O2120.40 (14)
C3—C2—H2120.5C18—C13—O2117.13 (12)
C4—C3—C2120.15 (18)C13—C14—C15118.19 (16)
C4—C3—H3119.9C13—C14—H14120.9
C2—C3—H3119.9C15—C14—H14120.9
C5—C4—C3119.93 (17)C16—C15—C14120.54 (16)
C5—C4—H4120.0C16—C15—H15119.7
C3—C4—H4120.0C14—C15—H15119.7
C4—C5—C6120.96 (16)C17—C16—C15120.17 (16)
C4—C5—H5119.5C17—C16—H16119.9
C6—C5—H5119.5C15—C16—H16119.9
C1—C6—C5118.03 (17)C16—C17—C18120.18 (17)
C1—C6—H6121.0C16—C17—H17119.9
C5—C6—H6121.0C18—C17—H17119.9
C12—C7—C8119.29 (12)C13—C18—C17118.52 (14)
C12—C7—N1118.18 (12)C13—C18—H18120.7
C8—C7—N1122.54 (12)C17—C18—H18120.7
C9—C8—C7118.53 (13)
O3—P1—O1—C167.23 (12)N1—C7—C8—C9179.29 (12)
O2—P1—O1—C1170.68 (10)C7—C8—C9—F1179.52 (12)
N1—P1—O1—C158.30 (11)C7—C8—C9—C100.7 (2)
O3—P1—O2—C1367.21 (11)F1—C9—C10—F20.7 (2)
O1—P1—O2—C13170.34 (10)C8—C9—C10—F2178.17 (13)
N1—P1—O2—C1358.09 (11)F1—C9—C10—C11179.94 (13)
O3—P1—N1—C7176.21 (11)C8—C9—C10—C111.2 (2)
O1—P1—N1—C755.24 (13)F2—C10—C11—C12178.71 (12)
O2—P1—N1—C748.16 (13)C9—C10—C11—C120.6 (2)
P1—O1—C1—C2132.55 (12)C10—C11—C12—C70.4 (2)
P1—O1—C1—C651.14 (18)C8—C7—C12—C110.9 (2)
C6—C1—C2—C30.5 (3)N1—C7—C12—C11178.77 (13)
O1—C1—C2—C3176.81 (15)P1—O2—C13—C1468.15 (16)
C1—C2—C3—C40.1 (3)P1—O2—C13—C18114.98 (12)
C2—C3—C4—C50.6 (3)C18—C13—C14—C150.7 (2)
C3—C4—C5—C60.5 (3)O2—C13—C14—C15177.39 (14)
C2—C1—C6—C50.6 (3)C13—C14—C15—C160.6 (3)
O1—C1—C6—C5176.68 (15)C14—C15—C16—C170.2 (3)
C4—C5—C6—C10.1 (3)C15—C16—C17—C180.2 (3)
P1—N1—C7—C12169.82 (11)C14—C13—C18—C170.3 (2)
P1—N1—C7—C810.5 (2)O2—C13—C18—C17177.15 (13)
C12—C7—C8—C90.4 (2)C16—C17—C18—C130.1 (2)
Diphenyl (3,4-difluorophenyl)phosphoramidate (formII) top
Crystal data top
C18H14F2NO3PDx = 1.412 Mg m3
Mr = 361.27Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 4055 reflections
a = 35.0582 (8) Åθ = 2.3–23.1°
b = 7.2554 (1) ŵ = 0.20 mm1
c = 13.3647 (3) ÅT = 100 K
V = 3399.46 (12) Å3Needle, colorless
Z = 80.32 × 0.10 × 0.08 mm
F(000) = 1488
Data collection top
Bruker APEXII CCD
diffractometer
7943 reflections with I > 2σ(I)
φ and ω scansRint = 0.064
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
θmax = 30.2°, θmin = 1.9°
Tmin = 0.677, Tmax = 0.746h = 4948
38761 measured reflectionsk = 910
9964 independent reflectionsl = 1818
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.56 e Å3
9964 reflectionsΔρmin = 0.39 e Å3
423 parametersAbsolute structure: Refined as an inversion twin
1 restraintAbsolute structure parameter: 0.32 (11)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.36203 (2)0.48593 (10)0.40749 (6)0.01605 (17)
P20.38317 (2)0.00834 (10)0.60365 (7)0.01560 (17)
F10.36208 (7)1.1959 (3)0.13530 (18)0.0411 (6)
F20.34765 (7)0.9715 (3)0.01831 (16)0.0326 (5)
O10.39551 (6)0.3860 (3)0.35036 (18)0.0193 (5)
O20.32947 (6)0.3618 (3)0.36171 (18)0.0187 (5)
O30.36452 (7)0.4889 (3)0.51713 (18)0.0199 (5)
O40.42351 (6)0.0976 (3)0.62402 (18)0.0194 (5)
O50.36088 (6)0.1387 (3)0.67819 (17)0.0170 (5)
O60.36990 (7)0.0087 (3)0.49995 (18)0.0210 (5)
N10.35828 (8)0.6955 (3)0.3665 (2)0.0180 (6)
H1A0.3566040.7811760.4129640.022*
N20.38293 (8)0.2007 (3)0.6476 (2)0.0168 (6)
H2A0.3751970.2861570.6055470.020*
C10.43126 (10)0.4686 (4)0.3354 (3)0.0197 (7)
C20.44869 (10)0.5765 (4)0.4080 (3)0.0242 (7)
H20.4365040.5988860.4703430.029*
C30.48398 (11)0.6503 (5)0.3877 (3)0.0294 (8)
H30.4961730.7257360.4361860.035*
C40.50202 (11)0.6159 (5)0.2970 (3)0.0302 (9)
H40.5264060.6674180.2836440.036*
C50.48419 (12)0.5055 (5)0.2260 (3)0.0315 (9)
H50.4965180.4809490.1640860.038*
C60.44842 (10)0.4310 (5)0.2452 (3)0.0245 (7)
H60.4360700.3555960.1969060.029*
C70.35731 (9)0.7602 (4)0.2666 (2)0.0165 (6)
C80.36145 (9)0.9497 (4)0.2502 (2)0.0182 (6)
H80.3661791.0313780.3043990.022*
C90.35851 (10)1.0148 (4)0.1542 (3)0.0226 (7)
C100.35152 (10)0.8991 (5)0.0744 (3)0.0230 (7)
C110.34843 (10)0.7138 (5)0.0890 (3)0.0230 (7)
H110.3444500.6336490.0337960.028*
C120.35116 (9)0.6421 (4)0.1865 (2)0.0200 (7)
H120.3488100.5132350.1975360.024*
C130.29148 (10)0.3682 (4)0.3976 (3)0.0200 (7)
C140.26516 (11)0.4717 (5)0.3454 (3)0.0304 (9)
H140.2729230.5465770.2907490.036*
C150.22760 (13)0.4646 (5)0.3736 (4)0.0418 (11)
H150.2091000.5329530.3372940.050*
C160.21639 (11)0.3588 (5)0.4545 (3)0.0353 (10)
H160.1903650.3550260.4741790.042*
C170.24353 (12)0.2584 (5)0.5064 (3)0.0360 (9)
H170.2360090.1855330.5620640.043*
C180.28130 (11)0.2630 (5)0.4783 (3)0.0292 (8)
H180.2999120.1945460.5141490.035*
C190.45822 (9)0.0143 (4)0.5973 (3)0.0220 (7)
C200.48839 (11)0.0476 (5)0.6600 (3)0.0294 (9)
H200.4852540.1205320.7184840.035*
C210.52378 (11)0.0280 (5)0.6359 (4)0.0385 (11)
H210.5450110.0063800.6785300.046*
C220.52831 (12)0.1330 (5)0.5516 (4)0.0408 (11)
H220.5525740.1839450.5361930.049*
C230.49802 (12)0.1648 (5)0.4897 (4)0.0391 (11)
H230.5012670.2386890.4316310.047*
C240.46225 (11)0.0892 (5)0.5113 (3)0.0294 (8)
H240.4412120.1087250.4677310.035*
C25A0.39326 (14)0.2646 (5)0.7430 (2)0.0185 (3)0.892 (4)
C26A0.39294 (10)0.4534 (4)0.76047 (19)0.0185 (3)0.892 (4)
H26A0.3857020.5358500.7086020.022*0.892 (4)
C27A0.40323 (9)0.5217 (3)0.8538 (2)0.0185 (3)0.892 (4)
C28A0.41382 (9)0.4011 (3)0.92971 (17)0.0185 (3)0.892 (4)
C29A0.41414 (11)0.2123 (3)0.9122 (2)0.0185 (3)0.892 (4)
H29A0.4213810.1298430.9641060.022*0.892 (4)
C30A0.40386 (14)0.1440 (3)0.8189 (3)0.0185 (3)0.892 (4)
H30A0.4040720.0149210.8069380.022*0.892 (4)
F3A0.40330 (9)0.7010 (3)0.87205 (19)0.0417 (8)0.892 (4)
F4A0.42420 (13)0.4698 (5)1.0186 (3)0.0330 (8)0.892 (4)
C25B0.3925 (12)0.263 (4)0.7445 (19)0.0185 (3)0.108 (4)
C26B0.4056 (12)0.164 (3)0.827 (2)0.0185 (3)0.108 (4)
H26B0.4113390.0364980.8202750.022*0.108 (4)
C27B0.4103 (9)0.252 (3)0.9184 (19)0.0185 (3)0.108 (4)
C28B0.4019 (8)0.438 (3)0.9278 (15)0.0185 (3)0.108 (4)
C29B0.3888 (8)0.537 (3)0.8456 (19)0.0185 (3)0.108 (4)
H29B0.3830450.6641590.8520410.022*0.108 (4)
C30B0.3841 (8)0.449 (4)0.7539 (17)0.0185 (3)0.108 (4)
H30B0.3751730.5166540.6977130.022*0.108 (4)
F3B0.4194 (7)0.139 (2)0.9938 (15)0.0417 (8)0.108 (4)
F4B0.4155 (14)0.510 (5)1.018 (3)0.0330 (8)0.108 (4)
C310.32072 (9)0.1272 (4)0.6836 (2)0.0168 (6)
C320.29908 (10)0.2353 (4)0.6208 (3)0.0242 (7)
H320.3108910.3141460.5731960.029*
C330.25994 (11)0.2266 (5)0.6284 (3)0.0296 (8)
H330.2445340.2979240.5845740.035*
C340.24292 (10)0.1155 (5)0.6991 (3)0.0259 (8)
H340.2159030.1109390.7040920.031*
C350.26519 (11)0.0105 (5)0.7628 (3)0.0299 (9)
H350.2534670.0646890.8122600.036*
C360.30457 (11)0.0150 (4)0.7546 (3)0.0248 (8)
H360.3200850.0581060.7972660.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0212 (4)0.0117 (4)0.0152 (4)0.0010 (3)0.0019 (4)0.0001 (3)
P20.0193 (4)0.0115 (4)0.0160 (4)0.0000 (3)0.0012 (3)0.0003 (3)
F10.0705 (18)0.0200 (11)0.0328 (13)0.0057 (10)0.0021 (12)0.0057 (9)
F20.0491 (15)0.0329 (12)0.0160 (11)0.0052 (10)0.0022 (10)0.0081 (8)
O10.0199 (12)0.0162 (11)0.0220 (12)0.0006 (8)0.0006 (10)0.0014 (9)
O20.0213 (12)0.0153 (11)0.0194 (12)0.0017 (8)0.0003 (10)0.0022 (9)
O30.0278 (14)0.0156 (11)0.0164 (12)0.0019 (9)0.0026 (10)0.0000 (8)
O40.0187 (12)0.0162 (11)0.0233 (13)0.0006 (8)0.0021 (10)0.0028 (9)
O50.0172 (11)0.0142 (11)0.0196 (12)0.0005 (8)0.0000 (9)0.0019 (9)
O60.0299 (14)0.0153 (12)0.0179 (13)0.0033 (9)0.0020 (10)0.0024 (8)
N10.0275 (16)0.0121 (13)0.0143 (13)0.0023 (10)0.0017 (12)0.0019 (10)
N20.0248 (15)0.0123 (13)0.0133 (13)0.0018 (10)0.0034 (11)0.0006 (9)
C10.0217 (18)0.0150 (15)0.0224 (18)0.0011 (12)0.0013 (14)0.0014 (12)
C20.0252 (18)0.0215 (16)0.0258 (18)0.0033 (13)0.0027 (16)0.0060 (14)
C30.028 (2)0.0230 (18)0.037 (2)0.0016 (14)0.0046 (17)0.0049 (15)
C40.023 (2)0.0261 (19)0.042 (2)0.0012 (14)0.0036 (17)0.0058 (16)
C50.032 (2)0.038 (2)0.025 (2)0.0015 (16)0.0064 (17)0.0035 (15)
C60.030 (2)0.0221 (17)0.0209 (18)0.0021 (13)0.0006 (15)0.0002 (13)
C70.0143 (15)0.0171 (15)0.0181 (17)0.0020 (11)0.0005 (13)0.0014 (11)
C80.0220 (17)0.0168 (15)0.0158 (16)0.0029 (11)0.0005 (13)0.0011 (12)
C90.0278 (19)0.0129 (16)0.027 (2)0.0026 (12)0.0002 (15)0.0050 (12)
C100.0256 (19)0.0282 (19)0.0151 (17)0.0008 (13)0.0008 (14)0.0035 (13)
C110.0278 (19)0.0221 (16)0.0193 (18)0.0006 (13)0.0006 (14)0.0026 (13)
C120.0275 (18)0.0155 (15)0.0170 (16)0.0008 (12)0.0013 (14)0.0019 (12)
C130.0231 (17)0.0135 (14)0.0233 (17)0.0020 (11)0.0026 (14)0.0022 (12)
C140.029 (2)0.0231 (18)0.039 (2)0.0035 (14)0.0020 (18)0.0122 (16)
C150.030 (2)0.028 (2)0.068 (3)0.0079 (16)0.002 (2)0.010 (2)
C160.024 (2)0.027 (2)0.055 (3)0.0033 (15)0.0102 (19)0.0083 (17)
C170.035 (2)0.039 (2)0.034 (2)0.0067 (17)0.0082 (18)0.0030 (18)
C180.031 (2)0.031 (2)0.026 (2)0.0031 (15)0.0027 (16)0.0065 (15)
C190.0211 (16)0.0141 (15)0.031 (2)0.0009 (11)0.0090 (15)0.0025 (13)
C200.027 (2)0.0244 (19)0.037 (2)0.0031 (14)0.0006 (17)0.0013 (15)
C210.021 (2)0.037 (2)0.058 (3)0.0001 (16)0.0020 (19)0.005 (2)
C220.026 (2)0.021 (2)0.076 (3)0.0002 (15)0.019 (2)0.0032 (19)
C230.038 (2)0.0187 (19)0.061 (3)0.0042 (15)0.021 (2)0.0072 (18)
C240.031 (2)0.0203 (17)0.037 (2)0.0040 (14)0.0096 (17)0.0067 (15)
C25A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C26A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C27A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C28A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C29A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C30A0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
F3A0.090 (2)0.0108 (11)0.0241 (13)0.0081 (11)0.0180 (14)0.0055 (9)
F4A0.059 (3)0.023 (2)0.0175 (12)0.0010 (13)0.0115 (15)0.0049 (14)
C25B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C26B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C27B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C28B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C29B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
C30B0.0253 (8)0.0156 (7)0.0147 (7)0.0010 (6)0.0042 (7)0.0008 (5)
F3B0.090 (2)0.0108 (11)0.0241 (13)0.0081 (11)0.0180 (14)0.0055 (9)
F4B0.059 (3)0.023 (2)0.0175 (12)0.0010 (13)0.0115 (15)0.0049 (14)
C310.0160 (15)0.0142 (14)0.0202 (16)0.0020 (11)0.0005 (13)0.0022 (12)
C320.0232 (18)0.0235 (17)0.0260 (19)0.0019 (13)0.0036 (15)0.0098 (14)
C330.026 (2)0.033 (2)0.030 (2)0.0067 (14)0.0003 (16)0.0059 (15)
C340.0205 (18)0.0255 (19)0.032 (2)0.0007 (13)0.0020 (15)0.0050 (15)
C350.028 (2)0.028 (2)0.033 (2)0.0018 (14)0.0064 (17)0.0073 (16)
C360.0263 (19)0.0233 (18)0.0249 (19)0.0007 (13)0.0017 (15)0.0057 (14)
Geometric parameters (Å, º) top
P1—O31.468 (2)C15—C161.382 (6)
P1—O11.577 (2)C16—C171.385 (6)
P1—O21.578 (2)C17—C181.377 (5)
P1—N11.622 (3)C19—C201.371 (5)
P2—O61.462 (2)C19—C241.380 (5)
P2—O41.579 (2)C20—C211.394 (5)
P2—O51.581 (2)C21—C221.370 (6)
P2—N21.627 (3)C22—C231.366 (6)
F1—C91.344 (4)C23—C241.399 (5)
F2—C101.353 (4)C25A—C26A1.3900
O1—C11.403 (4)C25A—C30A1.3900
O2—C131.417 (4)C26A—C27A1.3900
O4—C191.405 (4)C27A—F3A1.324 (3)
O5—C311.412 (4)C27A—C28A1.3900
N1—C71.416 (4)C28A—F4A1.339 (5)
N2—C25A1.403 (3)C28A—C29A1.3900
N2—C25B1.411 (19)C29A—C30A1.3900
C1—C61.375 (5)C25B—C26B1.3900
C1—C21.389 (5)C25B—C30B1.3900
C2—C31.375 (5)C26B—C27B1.3900
C3—C41.389 (6)C27B—F3B1.34 (3)
C4—C51.390 (6)C27B—C28B1.3900
C5—C61.390 (5)C28B—C29B1.3900
C7—C121.388 (4)C28B—F4B1.40 (5)
C7—C81.400 (4)C29B—C30B1.3900
C8—C91.372 (5)C31—C361.372 (5)
C9—C101.379 (5)C31—C321.377 (4)
C10—C111.363 (5)C32—C331.378 (5)
C11—C121.406 (5)C33—C341.378 (5)
C13—C181.368 (5)C34—C351.384 (5)
C13—C141.379 (5)C35—C361.385 (5)
C14—C151.371 (6)
O3—P1—O1116.48 (13)C15—C16—C17119.2 (4)
O3—P1—O2116.01 (14)C18—C17—C16120.7 (4)
O1—P1—O295.07 (13)C13—C18—C17118.7 (4)
O3—P1—N1109.13 (14)C20—C19—C24121.7 (3)
O1—P1—N1109.15 (14)C20—C19—O4115.9 (3)
O2—P1—N1110.23 (13)C24—C19—O4122.3 (3)
O6—P2—O4116.59 (14)C19—C20—C21118.4 (4)
O6—P2—O5116.04 (13)C22—C21—C20120.8 (4)
O4—P2—O595.09 (12)C23—C22—C21120.2 (4)
O6—P2—N2110.05 (14)C22—C23—C24120.4 (4)
O4—P2—N2108.94 (13)C19—C24—C23118.5 (4)
O5—P2—N2109.13 (13)C26A—C25A—C30A120.0
C1—O1—P1122.53 (19)C26A—C25A—N2118.4 (3)
C13—O2—P1122.0 (2)C30A—C25A—N2121.6 (3)
C19—O4—P2123.8 (2)C25A—C26A—C27A120.0
C31—O5—P2119.34 (19)F3A—C27A—C28A118.9 (2)
C7—N1—P1129.1 (2)F3A—C27A—C26A121.1 (2)
C25A—N2—P2129.4 (2)C28A—C27A—C26A120.0
C25B—N2—P2128.9 (13)F4A—C28A—C27A119.1 (2)
C6—C1—C2122.2 (3)F4A—C28A—C29A120.9 (2)
C6—C1—O1115.6 (3)C27A—C28A—C29A120.0
C2—C1—O1122.2 (3)C30A—C29A—C28A120.0
C3—C2—C1118.5 (3)C29A—C30A—C25A120.0
C2—C3—C4120.8 (4)C26B—C25B—C30B120.0
C3—C4—C5119.6 (4)C26B—C25B—N2130 (2)
C6—C5—C4120.3 (4)C30B—C25B—N2110 (2)
C1—C6—C5118.7 (3)C27B—C26B—C25B120.0
C12—C7—C8120.1 (3)F3B—C27B—C26B114.5 (19)
C12—C7—N1121.8 (3)F3B—C27B—C28B125.2 (19)
C8—C7—N1118.0 (3)C26B—C27B—C28B120.0
C9—C8—C7118.5 (3)C27B—C28B—C29B120.0
F1—C9—C8120.4 (3)C27B—C28B—F4B112 (2)
F1—C9—C10117.8 (3)C29B—C28B—F4B127 (2)
C8—C9—C10121.8 (3)C30B—C29B—C28B120.0
F2—C10—C11120.4 (3)C29B—C30B—C25B120.0
F2—C10—C9119.3 (3)C36—C31—C32122.2 (3)
C11—C10—C9120.2 (3)C36—C31—O5118.8 (3)
C10—C11—C12119.5 (3)C32—C31—O5118.9 (3)
C7—C12—C11119.8 (3)C31—C32—C33118.5 (3)
C18—C13—C14121.9 (3)C32—C33—C34120.6 (3)
C18—C13—O2119.6 (3)C33—C34—C35120.0 (3)
C14—C13—O2118.4 (3)C34—C35—C36120.0 (3)
C15—C14—C13118.9 (4)C31—C36—C35118.7 (3)
C14—C15—C16120.6 (4)
O3—P1—O1—C178.0 (3)C14—C13—C18—C171.3 (5)
O2—P1—O1—C1159.5 (2)O2—C13—C18—C17174.2 (3)
N1—P1—O1—C146.1 (3)C16—C17—C18—C130.3 (6)
O3—P1—O2—C1347.5 (3)P2—O4—C19—C20146.8 (3)
O1—P1—O2—C13170.2 (2)P2—O4—C19—C2435.5 (4)
N1—P1—O2—C1377.2 (3)C24—C19—C20—C210.8 (5)
O6—P2—O4—C1973.3 (3)O4—C19—C20—C21178.5 (3)
O5—P2—O4—C19164.2 (2)C19—C20—C21—C220.0 (6)
N2—P2—O4—C1951.9 (3)C20—C21—C22—C230.1 (6)
O6—P2—O5—C3151.9 (3)C21—C22—C23—C240.5 (6)
O4—P2—O5—C31174.8 (2)C20—C19—C24—C231.5 (5)
N2—P2—O5—C3173.1 (2)O4—C19—C24—C23179.0 (3)
O3—P1—N1—C7176.0 (3)C22—C23—C24—C191.3 (6)
O1—P1—N1—C747.7 (3)P2—N2—C25A—C26A175.8 (2)
O2—P1—N1—C755.5 (3)P2—N2—C25A—C30A3.8 (5)
O6—P2—N2—C25A179.9 (3)C30A—C25A—C26A—C27A0.0
O4—P2—N2—C25A51.2 (4)N2—C25A—C26A—C27A179.6 (4)
O5—P2—N2—C25A51.4 (4)C25A—C26A—C27A—F3A179.7 (3)
O6—P2—N2—C25B178 (2)C25A—C26A—C27A—C28A0.0
O4—P2—N2—C25B53 (2)F3A—C27A—C28A—F4A0.7 (4)
O5—P2—N2—C25B50 (2)C26A—C27A—C28A—F4A179.0 (4)
P1—O1—C1—C6143.3 (3)F3A—C27A—C28A—C29A179.7 (3)
P1—O1—C1—C238.6 (4)C26A—C27A—C28A—C29A0.0
C6—C1—C2—C31.2 (5)F4A—C28A—C29A—C30A178.9 (4)
O1—C1—C2—C3179.1 (3)C27A—C28A—C29A—C30A0.0
C1—C2—C3—C40.8 (5)C28A—C29A—C30A—C25A0.0
C2—C3—C4—C50.0 (5)C26A—C25A—C30A—C29A0.0
C3—C4—C5—C60.4 (6)N2—C25A—C30A—C29A179.6 (4)
C2—C1—C6—C50.8 (5)P2—N2—C25B—C26B2 (3)
O1—C1—C6—C5178.8 (3)P2—N2—C25B—C30B173.0 (9)
C4—C5—C6—C10.1 (5)C30B—C25B—C26B—C27B0.0
P1—N1—C7—C1214.5 (5)N2—C25B—C26B—C27B175 (3)
P1—N1—C7—C8167.6 (2)C25B—C26B—C27B—F3B174 (3)
C12—C7—C8—C91.3 (5)C25B—C26B—C27B—C28B0.0
N1—C7—C8—C9176.6 (3)F3B—C27B—C28B—C29B173 (3)
C7—C8—C9—F1179.6 (3)C26B—C27B—C28B—C29B0.0
C7—C8—C9—C100.2 (5)F3B—C27B—C28B—F4B19 (4)
F1—C9—C10—F21.6 (5)C26B—C27B—C28B—F4B168 (3)
C8—C9—C10—F2177.8 (3)C27B—C28B—C29B—C30B0.0
F1—C9—C10—C11178.7 (3)F4B—C28B—C29B—C30B166 (3)
C8—C9—C10—C111.9 (5)C28B—C29B—C30B—C25B0.0
F2—C10—C11—C12177.7 (3)C26B—C25B—C30B—C29B0.0
C9—C10—C11—C122.1 (5)N2—C25B—C30B—C29B176 (3)
C8—C7—C12—C111.1 (5)P2—O5—C31—C3693.6 (3)
N1—C7—C12—C11176.7 (3)P2—O5—C31—C3289.4 (3)
C10—C11—C12—C70.6 (5)C36—C31—C32—C331.5 (5)
P1—O2—C13—C1885.3 (3)O5—C31—C32—C33178.3 (3)
P1—O2—C13—C1499.0 (3)C31—C32—C33—C341.6 (5)
C18—C13—C14—C151.8 (6)C32—C33—C34—C350.4 (5)
O2—C13—C14—C15173.7 (3)C33—C34—C35—C361.0 (5)
C13—C14—C15—C161.4 (6)C32—C31—C36—C350.2 (5)
C14—C15—C16—C170.5 (6)O5—C31—C36—C35177.0 (3)
C15—C16—C17—C180.1 (6)C34—C35—C36—C311.1 (5)
Crystallization conditions for obtaining different forms top
FormSolventTemperature (°C)Crystal habit
Concomitant (I and II)Toluene22–25Block + needle
DCM–Hexane4Block + needle
Form IIMethanol, DCM–hexane, ethanol22–25Needle
Torsion angles (°) for Forms I and II top
TorsionForm IForm II
P1—O2—C13—C18/P2—O4—C19—C20114.98 (12)85.3 (3)
146.8 (3)
P1—N1—C7—C12/P2—N2—C25A—C30A169.82 (11)14.5 (5)
3.8 (5)
P1—O1—C1—C2/P2—O5—C31—C36132.55 (12)38.6 (4)
93.6 (3)
 

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