Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160057671401303X/kk5170sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160057671401303X/kk5170Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S160057671401303X/kk5170sup3.pdf |
CCDC reference: 952239
Data collection: Win X-POW; cell refinement: Topas Academic v.5; data reduction: Topas Academic v.5; program(s) used to solve structure: ab initio algorithm; program(s) used to refine structure: TOPAS ACADEMIC 5; molecular graphics: Mercury 3.1; software used to prepare material for publication: TOPAS ACADEMIC 5.
2(C17H16F6N2O)·2(Cl)·H2O | Tetragonal |
Mr = 845.55 | Dx = 1.457 Mg m−3 |
Tetragonal, P42/n | Melting point: 456 K |
Hall symbol: -P 4bc | Cu Kα1 radiation, λ = 1.54056 Å |
a = 24.5663 (3) Å | µ = 2.40 mm−1 |
c = 6.38601 (12) Å | T = 298 K |
V = 3853.97 (13) Å3 | Particle morphology: powder |
Z = 4 | white |
F(000) = 1728 |
Stoe STADI-P powder diffractometer | Scan method: step |
Radiation source: sealed X-ray tube, Stoe STADI-P | Absorption correction: analytical Correction based on shape and thickness |
Curved Ge(111) monochromator | |
Specimen mounting: "Ultraphan" acetate foils | 2θmin = 2°, 2θmax = 60°, 2θstep = 0.015° |
Data collection mode: transmission |
Refinement on F | 138 parameters |
Least-squares matrix: full | 0 restraints |
Rp = 0.029 | 42 constraints |
Rwp = 0.041 | Hydrogen site location: inferred from neighbouring sites |
Rexp = 0.019 | All H-atom parameters refined |
RBragg = 0.014 | Weighting scheme based on measured s.u.'s |
3850 data points | (Δ/σ)max = 0.0001 |
Excluded region(s): none | Background function: 20-term Chebyschev polynomial |
Profile function: Fundamental parameters approach | Preferred orientation correction: 4 terms spherical harmonics |
Refinement. A Rietveld refinement was performed with the TOPAS package using the fundamental parameters approach as reflection profiles (convolution of appropriate source emission profiles with axial instrument contributions as well as crystallite microstructure effects). In order to describe small peak half width and shape anisotropy effects, the approach of Le Bail and Jouanneaux was implemented into the TOPAS program and the according parameters were allowed to refine freely. Preferred orientation of the crystallites was described with a spherical harmonics function of 4th order. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.3752 (8) | 0.4111 (7) | 0.334 (3) | 0.09870 | |
C2 | 0.3939 (11) | 0.4527 (14) | 0.440 (4) | 0.09870 | |
C3 | 0.3833 (10) | 0.5075 (11) | 0.393 (3) | 0.09870 | |
C4 | 0.3488 (10) | 0.5206 (11) | 0.235 (4) | 0.09870 | |
C5 | 0.2909 (8) | 0.4848 (9) | −0.056 (3) | 0.09870 | |
C6 | 0.2713 (10) | 0.4418 (10) | −0.162 (3) | 0.09870 | |
C7 | 0.2839 (9) | 0.3881 (10) | −0.109 (3) | 0.09870 | |
C8 | 0.3170 (11) | 0.3773 (11) | 0.057 (5) | 0.09870 | |
C9 | 0.3410 (12) | 0.4218 (15) | 0.171 (4) | 0.09870 | |
C10 | 0.3269 (12) | 0.4767 (15) | 0.114 (4) | 0.09870 | |
C11 | 0.3387 (9) | 0.5801 (10) | 0.178 (3) | 0.09870 | |
C12 | 0.3769 (9) | 0.5992 (9) | 0.003 (4) | 0.09870 | |
N13 | 0.3640 (7) | 0.6563 (7) | −0.049 (2) | 0.09870 | |
C14 | 0.3968 (8) | 0.6777 (9) | −0.226 (3) | 0.09870 | |
C15 | 0.4577 (9) | 0.6728 (8) | −0.185 (3) | 0.09870 | |
C16 | 0.4724 (9) | 0.6140 (10) | −0.125 (3) | 0.09870 | |
C17 | 0.4369 (7) | 0.5947 (9) | 0.058 (3) | 0.09870 | |
C18 | 0.3332 (11) | 0.3196 (14) | 0.105 (3) | 0.09870 | |
C19 | 0.4327 (12) | 0.4393 (10) | 0.616 (4) | 0.09870 | |
O20 | 0.3458 (5) | 0.6160 (5) | 0.3495 (18) | 0.09870 | |
F21 | 0.3108 (5) | 0.2835 (5) | −0.0261 (17) | 0.09870 | |
F22 | 0.3869 (6) | 0.3125 (5) | 0.0921 (13) | 0.09870 | |
F23 | 0.3178 (5) | 0.3056 (5) | 0.2989 (17) | 0.09870 | |
F24 | 0.4834 (5) | 0.4392 (5) | 0.5565 (17) | 0.09870 | |
F25 | 0.4257 (4) | 0.3899 (5) | 0.6930 (19) | 0.09870 | |
F26 | 0.4297 (5) | 0.4727 (5) | 0.7750 (17) | 0.09870 | |
Cl27 | 0.2587 (3) | 0.6167 (2) | 0.7083 (7) | 0.09870 | |
O44 | 0.2170 (8) | 0.7327 (10) | 0.726 (3) | 0.09870 | 0.5 |
H28 | 0.2858 (8) | 0.5208 (9) | −0.112 (3) | 0.11845 | |
H29 | 0.2705 (9) | 0.3594 (10) | −0.197 (3) | 0.11845 | |
H30 | 0.3975 (10) | 0.5379 (11) | 0.469 (3) | 0.11845 | |
H31 | 0.3007 (9) | 0.5854 (10) | 0.153 (3) | 0.11845 | |
H32 | 0.2534 (10) | 0.4497 (10) | −0.292 (3) | 0.11845 | |
H33 | 0.3185 (5) | 0.6104 (5) | 0.4605 (18) | 0.11845 | |
H34 | 0.3609 (9) | 0.5795 (9) | −0.111 (4) | 0.11845 | |
H35 | 0.3297 (7) | 0.6621 (7) | −0.069 (2) | 0.11845 | |
H36 | 0.4455 (7) | 0.5568 (9) | 0.088 (3) | 0.11845 | |
H37 | 0.4447 (7) | 0.6160 (9) | 0.179 (3) | 0.11845 | |
H38 | 0.3882 (8) | 0.7150 (9) | −0.246 (3) | 0.11845 | |
H39 | 0.3883 (8) | 0.6573 (9) | −0.350 (3) | 0.11845 | |
H40 | 0.4667 (9) | 0.5908 (10) | −0.244 (3) | 0.11845 | |
H41 | 0.5103 (9) | 0.6121 (10) | −0.085 (3) | 0.11845 | |
H42 | 0.4676 (9) | 0.6964 (8) | −0.070 (3) | 0.11845 | |
H43 | 0.4777 (9) | 0.6832 (8) | −0.307 (3) | 0.11845 | |
H45 | 0.2451 (8) | 0.7172 (10) | 0.631 (3) | 0.11845 | 0.5 |
H46 | 0.2109 (8) | 0.7076 (10) | 0.845 (3) | 0.11845 | 0.5 |
N1—C2 | 1.31 (4) | C12—H34 | 0.96 (3) |
N1—C9 | 1.36 (3) | N13—C14 | 1.48 (2) |
C2—C3 | 1.40 (4) | N13—H35 | 0.86 (2) |
C2—C19 | 1.51 (4) | C14—C15 | 1.52 (3) |
C3—C4 | 1.36 (3) | C14—H38 | 0.95 (3) |
C3—H30 | 0.96 (4) | C14—H39 | 0.96 (3) |
C4—C10 | 1.43 (4) | C15—C16 | 1.54 (3) |
C4—C11 | 1.53 (4) | C15—H42 | 0.97 (3) |
C5—C6 | 1.34 (3) | C15—H43 | 0.96 (3) |
C5—C10 | 1.41 (3) | C16—C17 | 1.53 (3) |
C5—H28 | 0.96 (3) | C16—H40 | 0.96 (3) |
C6—C7 | 1.40 (3) | C16—H41 | 0.97 (3) |
C6—H32 | 0.96 (3) | C17—H36 | 0.97 (3) |
C7—C8 | 1.36 (4) | C17—H37 | 0.95 (3) |
C7—H29 | 0.96 (3) | C18—F21 | 1.34 (3) |
C8—C9 | 1.44 (4) | C18—F22 | 1.33 (3) |
C8—C18 | 1.50 (4) | C18—F23 | 1.34 (2) |
C9—C10 | 1.44 (5) | C19—F24 | 1.30 (3) |
C11—C12 | 1.53 (3) | C19—F25 | 1.32 (3) |
C11—O20 | 1.42 (2) | C19—F26 | 1.31 (3) |
C11—H31 | 0.96 (3) | O20—H33 | 0.99 (2) |
C12—N13 | 1.48 (3) | O44—H45 | 0.99 (3) |
C12—C17 | 1.52 (3) | O44—H46 | 0.99 (3) |
C2—N1—C9 | 117 (2) | C12—N13—H35 | 114 (2) |
N1—C2—C3 | 125 (3) | C14—N13—H35 | 111 (2) |
N1—C2—C19 | 116 (2) | N13—C14—C15 | 112 (2) |
C3—C2—C19 | 119 (2) | N13—C14—H38 | 109 (2) |
C2—C3—C4 | 120 (2) | N13—C14—H39 | 109 (2) |
C2—C3—H30 | 125 (3) | C15—C14—H38 | 109 (2) |
C4—C3—H30 | 115 (3) | C15—C14—H39 | 108 (2) |
C3—C4—C10 | 117 (2) | H38—C14—H39 | 110 (3) |
C3—C4—C11 | 120 (2) | C14—C15—C16 | 110 (2) |
C10—C4—C11 | 122 (2) | C14—C15—H42 | 109 (2) |
C6—C5—C10 | 120 (2) | C14—C15—H43 | 110 (2) |
C6—C5—H28 | 119 (2) | C16—C15—H42 | 108 (2) |
C10—C5—H28 | 120 (2) | C16—C15—H43 | 109 (2) |
C5—C6—C7 | 123 (2) | H42—C15—H43 | 109 (3) |
C5—C6—H32 | 116 (3) | C15—C16—C17 | 110 (2) |
C7—C6—H32 | 120 (3) | C15—C16—H40 | 109 (2) |
C6—C7—C8 | 120 (2) | C15—C16—H41 | 110 (2) |
C6—C7—H29 | 118 (2) | C17—C16—H40 | 110 (2) |
C8—C7—H29 | 121 (3) | C17—C16—H41 | 109 (2) |
C7—C8—C9 | 119 (3) | H40—C16—H41 | 109 (3) |
C7—C8—C18 | 120 (2) | C12—C17—C16 | 111 (2) |
C9—C8—C18 | 120 (3) | C12—C17—H36 | 109 (2) |
N1—C9—C8 | 119 (3) | C12—C17—H37 | 110 (2) |
N1—C9—C10 | 121 (3) | C16—C17—H36 | 109 (2) |
C8—C9—C10 | 119 (3) | C16—C17—H37 | 110 (2) |
C4—C10—C5 | 123 (3) | H36—C17—H37 | 109 (2) |
C4—C10—C9 | 119 (3) | C8—C18—F21 | 113 (2) |
C5—C10—C9 | 118 (3) | C8—C18—F22 | 112 (2) |
C4—C11—C12 | 112 (2) | C8—C18—F23 | 111 (2) |
C4—C11—O20 | 113 (2) | F21—C18—F22 | 106 (2) |
C4—C11—H31 | 109 (2) | F21—C18—F23 | 107 (2) |
C12—C11—O20 | 107 (2) | F22—C18—F23 | 108 (2) |
C12—C11—H31 | 116 (2) | C2—C19—F24 | 113 (2) |
O20—C11—H31 | 99 (2) | C2—C19—F25 | 113 (2) |
C11—C12—N13 | 109 (2) | C2—C19—F26 | 114 (2) |
C11—C12—C17 | 114 (2) | F24—C19—F25 | 103 (2) |
C11—C12—H34 | 99 (2) | F24—C19—F26 | 106 (2) |
N13—C12—C17 | 109 (2) | F25—C19—F26 | 106 (2) |
N13—C12—H34 | 103 (2) | C11—O20—H33 | 113 (2) |
C17—C12—H34 | 122 (3) | H45—O44—H46 | 110 (3) |
C12—N13—C14 | 113 (2) |