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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506487.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4506487
loop_
_publ_author_name
'Wahl, Helene'
'Haynes, Delia A.'
'le Roex, Tanya'
_publ_section_title
;
 A Series of Polymorphs of Hexakis(4-fluorophenoxy)cyclotriphosphazene
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4031
_journal_paper_doi               10.1021/cg300503p
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C36 H24 F6 N3 O6 P3'
_chemical_formula_sum            'C36 H24 F6 N3 O6 P3'
_chemical_formula_weight         801.49
_chemical_name_common            Hexakis(4-fluorophenoxy)cyclotriphosphazene
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 122.820(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.949(4)
_cell_length_b                   7.9159(9)
_cell_length_c                   17.106(2)
_cell_measurement_reflns_used    2625
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      22.683
_cell_measurement_theta_min      2.382
_cell_volume                     3521.8(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      253(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12435
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.28
_diffrn_reflns_theta_min         1.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9438
_exptl_absorpt_correction_T_min  0.9111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0669P)²+3.1609P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                2087
_reflns_number_total             3634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300503p_si_002.cif
_cod_data_source_block           Gamma_253K.CIF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3521.7(7)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4506487
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.46332(4) 0.27350(11) 0.65594(5) 0.0775(3) Uani 1 1 d . . .
O1 O 0.40702(11) 0.3342(3) 0.61907(16) 0.1008(9) Uani 1 1 d . A .
N1 N 0.5000 0.3687(4) 0.7500 0.0949(14) Uani 1 2 d S . .
C1 C 0.36298(15) 0.2717(4) 0.5392(3) 0.0781(10) Uani 1 1 d . . .
P2 P 0.5000 -0.02864(14) 0.7500 0.0752(4) Uani 1 2 d S . .
F2 F 0.26154(11) -0.1513(4) 0.6240(3) 0.1771(14) Uani 1 1 d . . .
O2 O 0.46586(9) -0.1640(3) 0.7595(2) 0.1111(10) Uani 1 1 d . . .
N2 N 0.46706(9) 0.0754(3) 0.65760(16) 0.0702(7) Uani 1 1 d . . .
F3 F 0.64765(13) 0.2726(4) 0.5886(2) 0.1496(11) Uani 1 1 d . . .
O3 O 0.46912(10) 0.3483(3) 0.57625(14) 0.0845(7) Uani 1 1 d D . .
C7 C 0.41362(12) -0.1502(4) 0.7245(2) 0.0762(10) Uani 1 1 d . . .
C8 C 0.39538(18) -0.0454(6) 0.7605(3) 0.1001(13) Uani 1 1 d . . .
H8 H 0.4175 0.0276 0.8084 0.120 Uiso 1 1 calc R . .
C9 C 0.3439(2) -0.0449(7) 0.7271(3) 0.1246(17) Uani 1 1 d . . .
H9 H 0.3306 0.0287 0.7514 0.150 Uiso 1 1 calc R . .
C10 C 0.31310(17) -0.1530(6) 0.6587(3) 0.1051(13) Uani 1 1 d . . .
C11 C 0.33039(17) -0.2617(5) 0.6223(3) 0.1142(16) Uani 1 1 d . . .
H11 H 0.3081 -0.3361 0.5755 0.137 Uiso 1 1 calc R . .
C12 C 0.38225(16) -0.2606(5) 0.6559(3) 0.1070(14) Uani 1 1 d . . .
H12 H 0.3956 -0.3345 0.6319 0.128 Uiso 1 1 calc R . .
C13 C 0.51507(12) 0.3299(4) 0.5805(2) 0.0799(10) Uani 1 1 d D . .
C14 C 0.51660(18) 0.2236(5) 0.5180(2) 0.0897(12) Uani 1 1 d . . .
H14 H 0.4872 0.1648 0.4744 0.108 Uiso 1 1 calc R . .
C15 C 0.5608(2) 0.2046(5) 0.5200(3) 0.1027(13) Uani 1 1 d . . .
H15 H 0.5623 0.1324 0.4786 0.123 Uiso 1 1 calc R . .
C16 C 0.6029(2) 0.2943(6) 0.5843(3) 0.1054(13) Uani 1 1 d . . .
C17 C 0.60272(19) 0.4020(6) 0.6455(3) 0.1050(13) Uani 1 1 d . . .
H17 H 0.6322 0.4616 0.6880 0.126 Uiso 1 1 calc R . .
C18 C 0.55807(18) 0.4215(4) 0.6435(2) 0.0921(12) Uani 1 1 d . . .
H18 H 0.5568 0.4958 0.6843 0.110 Uiso 1 1 calc R . .
F1A F 0.23252(19) 0.1131(9) 0.2822(4) 0.136(2) Uani 0.492(5) 1 d P A 1
C2A C 0.3414(3) 0.0964(9) 0.5167(5) 0.085(2) Uani 0.492(5) 1 d P A 1
H2A H 0.3578 0.0155 0.5633 0.102 Uiso 0.492(5) 1 calc PR A 1
C3A C 0.2990(3) 0.0445(12) 0.4324(5) 0.092(3) Uani 0.492(5) 1 d P A 1
H3A H 0.2877 -0.0669 0.4230 0.110 Uiso 0.492(5) 1 calc PR A 1
C4A C 0.2749(4) 0.1597(15) 0.3652(7) 0.085(3) Uani 0.492(5) 1 d P A 1
C5A C 0.2915(4) 0.3221(14) 0.3753(6) 0.094(3) Uani 0.492(5) 1 d P A 1
H5A H 0.2742 0.3990 0.3268 0.112 Uiso 0.492(5) 1 calc PR A 1
C6A C 0.3341(3) 0.3700(10) 0.4581(5) 0.081(2) Uani 0.492(5) 1 d P A 1
H6A H 0.3454 0.4802 0.4613 0.098 Uiso 0.492(5) 1 calc PR A 1
F1B F 0.22770(19) 0.1159(9) 0.3471(5) 0.139(2) Uani 0.508(5) 1 d P A 2
C2B C 0.3310(3) 0.2634(11) 0.5684(5) 0.090(2) Uani 0.508(5) 1 d P A 2
H2B H 0.3397 0.2924 0.6279 0.109 Uiso 0.508(5) 1 calc PR A 2
C3B C 0.2839(3) 0.2067(12) 0.4997(7) 0.107(3) Uani 0.508(5) 1 d P A 2
H3B H 0.2582 0.1899 0.5115 0.128 Uiso 0.508(5) 1 calc PR A 2
C4B C 0.2748(3) 0.1758(14) 0.4165(8) 0.091(3) Uani 0.508(5) 1 d P A 2
C5B C 0.3102(5) 0.1916(19) 0.3943(7) 0.120(4) Uani 0.508(5) 1 d P A 2
H5B H 0.3029 0.1636 0.3355 0.144 Uiso 0.508(5) 1 calc PR A 2
C6B C 0.3591(3) 0.2531(15) 0.4651(5) 0.107(3) Uani 0.508(5) 1 d P A 2
H6B H 0.3855 0.2767 0.4558 0.128 Uiso 0.508(5) 1 calc PR A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 P1 N2 117.07(15) . .
N1 P1 O1 107.03(12) . .
N2 P1 O1 111.53(15) . .
N1 P1 O3 110.27(13) . .
N2 P1 O3 110.31(14) . .
O1 P1 O3 99.12(14) . .
C1 O1 P1 124.4(2) . .
P1 N1 P1 122.6(2) . 2_656
C6B C1 C2B 135.5(6) . .
C6B C1 O1 123.7(5) . .
C2B C1 O1 100.4(5) . .
C6B C1 C6A 52.3(5) . .
C2B C1 C6A 101.2(5) . .
O1 C1 C6A 122.0(4) . .
C6B C1 C2A 80.9(6) . .
C2B C1 C2A 74.4(5) . .
O1 C1 C2A 130.0(3) . .
C6A C1 C2A 107.6(5) . .
N2 P2 N2 116.76(18) 2_656 .
N2 P2 O2 110.79(13) 2_656 2_656
N2 P2 O2 111.02(15) . 2_656
N2 P2 O2 111.02(15) 2_656 .
N2 P2 O2 110.80(13) . .
O2 P2 O2 94.2(2) 2_656 .
C7 O2 P2 126.21(19) . .
P1 N2 P2 122.86(15) . .
C13 O3 P1 120.4(2) . .
C8 C7 C12 121.2(4) . .
C8 C7 O2 122.4(3) . .
C12 C7 O2 116.2(4) . .
C7 C8 C9 119.9(4) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C10 C9 C8 118.5(4) . .
C10 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
C11 C10 C9 122.9(4) . .
C11 C10 F2 118.2(4) . .
C9 C10 F2 118.8(5) . .
C10 C11 C12 118.2(4) . .
C10 C11 H11 120.9 . .
C12 C11 H11 120.9 . .
C7 C12 C11 119.2(4) . .
C7 C12 H12 120.4 . .
C11 C12 H12 120.4 . .
C18 C13 C14 120.1(4) . .
C18 C13 O3 120.8(3) . .
C14 C13 O3 119.1(3) . .
C15 C14 C13 120.3(4) . .
C15 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
C14 C15 C16 118.1(4) . .
C14 C15 H15 121.0 . .
C16 C15 H15 121.0 . .
C17 C16 F3 118.0(4) . .
C17 C16 C15 123.4(5) . .
F3 C16 C15 118.5(4) . .
C16 C17 C18 118.5(4) . .
C16 C17 H17 120.7 . .
C18 C17 H17 120.7 . .
C17 C18 C13 119.5(4) . .
C17 C18 H18 120.2 . .
C13 C18 H18 120.2 . .
C3A C2A C1 125.5(6) . .
C3A C2A H2A 117.2 . .
C1 C2A H2A 117.2 . .
C4A C3A C2A 117.8(8) . .
C4A C3A H3A 121.1 . .
C2A C3A H3A 121.1 . .
C3A C4A C5A 122.7(9) . .
C3A C4A F1A 119.1(10) . .
C5A C4A F1A 118.2(10) . .
C4A C5A C6A 118.7(8) . .
C4A C5A H5A 120.6 . .
C6A C5A H5A 120.6 . .
C5A C6A C1 127.5(7) . .
C5A C6A H6A 116.3 . .
C1 C6A H6A 116.3 . .
C1 C2B C3B 111.0(7) . .
C1 C2B H2B 124.5 . .
C3B C2B H2B 124.5 . .
C4B C3B C2B 119.8(8) . .
C4B C3B H3B 120.1 . .
C2B C3B H3B 120.1 . .
C3B C4B C5B 124.0(10) . .
C3B C4B F1B 120.3(9) . .
C5B C4B F1B 115.6(12) . .
C4B C5B C6B 116.5(10) . .
C4B C5B H5B 121.7 . .
C6B C5B H5B 121.7 . .
C1 C6B C5B 112.8(8) . .
C1 C6B H6B 123.6 . .
C5B C6B H6B 123.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 N1 1.5701(19) .
P1 N2 1.571(3) .
P1 O1 1.573(3) .
P1 O3 1.583(3) .
O1 C1 1.397(5) .
N1 P1 1.5702(19) 2_656
C1 C6B 1.216(8) .
C1 C2B 1.331(8) .
C1 C6A 1.409(7) .
C1 C2A 1.497(8) .
P2 N2 1.572(3) 2_656
P2 N2 1.572(2) .
P2 O2 1.574(3) 2_656
P2 O2 1.574(3) .
F2 C10 1.368(5) .
O2 C7 1.391(4) .
F3 C16 1.358(5) .
O3 C13 1.3920(19) .
C7 C8 1.328(5) .
C7 C12 1.360(5) .
C8 C9 1.370(6) .
C8 H8 0.9300 .
C9 C10 1.343(6) .
C9 H9 0.9300 .
C10 C11 1.333(6) .
C11 C12 1.381(6) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C18 1.380(5) .
C13 C14 1.381(5) .
C14 C15 1.359(6) .
C14 H14 0.9300 .
C15 C16 1.363(6) .
C15 H15 0.9300 .
C16 C17 1.352(6) .
C17 C18 1.372(6) .
C17 H17 0.9300 .
C18 H18 0.9300 .
F1A C4A 1.361(10) .
C2A C3A 1.385(9) .
C2A H2A 0.9300 .
C3A C4A 1.334(15) .
C3A H3A 0.9300 .
C4A C5A 1.360(15) .
C5A C6A 1.365(11) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
F1B C4B 1.373(10) .
C2B C3B 1.360(11) .
C2B H2B 0.9300 .
C3B C4B 1.315(14) .
C3B H3B 0.9300 .
C4B C5B 1.345(15) .
C5B C6B 1.419(14) .
C5B H5B 0.9300 .
C6B H6B 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 P1 O1 C1 -176.6(3) . .
N2 P1 O1 C1 -47.3(3) . .
O3 P1 O1 C1 68.8(3) . .
N2 P1 N1 P1 -3.86(12) . 2_656
O1 P1 N1 P1 122.13(12) . 2_656
O3 P1 N1 P1 -131.03(12) . 2_656
P1 O1 C1 C6B -46.6(8) . .
P1 O1 C1 C2B 139.9(4) . .
P1 O1 C1 C6A -109.9(5) . .
P1 O1 C1 C2A 61.6(6) . .
N2 P2 O2 C7 101.4(3) 2_656 .
N2 P2 O2 C7 -30.0(4) . .
O2 P2 O2 C7 -144.4(4) 2_656 .
N1 P1 N2 P2 8.1(2) . .
O1 P1 N2 P2 -115.64(19) . .
O3 P1 N2 P2 135.24(19) . .
N2 P2 N2 P1 -4.21(13) 2_656 .
O2 P2 N2 P1 -132.50(19) 2_656 .
O2 P2 N2 P1 124.2(2) . .
N1 P1 O3 C13 66.0(3) . .
N2 P1 O3 C13 -64.8(3) . .
O1 P1 O3 C13 178.1(2) . .
P2 O2 C7 C8 -71.5(5) . .
P2 O2 C7 C12 113.9(4) . .
C12 C7 C8 C9 -1.4(6) . .
O2 C7 C8 C9 -175.8(4) . .
C7 C8 C9 C10 0.7(7) . .
C8 C9 C10 C11 0.5(8) . .
C8 C9 C10 F2 -178.9(4) . .
C9 C10 C11 C12 -0.9(8) . .
F2 C10 C11 C12 178.5(4) . .
C8 C7 C12 C11 1.0(6) . .
O2 C7 C12 C11 175.7(4) . .
C10 C11 C12 C7 0.2(7) . .
P1 O3 C13 C18 -72.5(4) . .
P1 O3 C13 C14 110.2(3) . .
C18 C13 C14 C15 2.0(5) . .
O3 C13 C14 C15 179.4(3) . .
C13 C14 C15 C16 -0.7(6) . .
C14 C15 C16 C17 -0.6(7) . .
C14 C15 C16 F3 178.2(4) . .
F3 C16 C17 C18 -178.2(4) . .
C15 C16 C17 C18 0.5(7) . .
C16 C17 C18 C13 0.8(6) . .
C14 C13 C18 C17 -2.1(5) . .
O3 C13 C18 C17 -179.4(3) . .
C6B C1 C2A C3A -48.6(10) . .
C2B C1 C2A C3A 94.0(9) . .
O1 C1 C2A C3A -175.4(7) . .
C6A C1 C2A C3A -3.0(10) . .
C1 C2A C3A C4A -0.3(15) . .
C2A C3A C4A C5A 2(2) . .
C2A C3A C4A F1A -178.7(8) . .
C3A C4A C5A C6A -1(2) . .
F1A C4A C5A C6A -179.7(9) . .
C4A C5A C6A C1 -3.4(16) . .
C6B C1 C6A C5A 67.9(10) . .
C2B C1 C6A C5A -72.1(11) . .
O1 C1 C6A C5A 178.0(8) . .
C2A C1 C6A C5A 4.9(11) . .
C6B C1 C2B C3B 6.6(13) . .
O1 C1 C2B C3B 179.0(6) . .
C6A C1 C2B C3B 53.2(8) . .
C2A C1 C2B C3B -52.2(7) . .
C1 C2B C3B C4B -2.9(12) . .
C2B C3B C4B C5B 2.2(18) . .
C2B C3B C4B F1B 178.9(9) . .
C3B C4B C5B C6B -3(2) . .
F1B C4B C5B C6B -179.9(10) . .
C2B C1 C6B C5B -7.6(17) . .
O1 C1 C6B C5B -178.6(8) . .
C6A C1 C6B C5B -71.8(10) . .
C2A C1 C6B C5B 48.9(10) . .
C4B C5B C6B C1 4.9(18) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11297331
