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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/4/50/64/4506488.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_4506488
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            Hexa(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                 122.8800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.970(3)
_cell_length_b                   7.9375(8)
_cell_length_c                   17.1585(16)
_cell_measurement_reflns_used    1703
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      20.309
_cell_measurement_theta_min      2.374
_cell_volume                     3542.3(6)
_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      273(2)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.896
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7842
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9292
_exptl_absorpt_correction_T_min  0.9138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0511
_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)+(0.0683P)²+3.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                1782
_reflns_number_total             3078
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300503p_si_002.cif
_cod_data_source_block           Gamma_273K.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_sg_symbol_H-M      C2/c
_cod_database_code               4506488
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 0.46328(4) 0.27386(12) 0.65614(6) 0.0858(4) Uani 1 1 d . A .
O1 O 0.40683(11) 0.3341(3) 0.61912(17) 0.1069(9) Uani 1 1 d D . .
N1 N 0.5000 0.3686(5) 0.7500 0.0982(14) Uani 1 2 d S . .
P2 P 0.5000 -0.02760(16) 0.7500 0.0852(5) Uani 1 2 d S . .
F2 F 0.26195(12) -0.1556(5) 0.6242(3) 0.2044(17) Uani 1 1 d . . .
O2 O 0.46608(10) -0.1629(3) 0.7600(2) 0.1254(12) Uani 1 1 d . . .
N2 N 0.46687(10) 0.0763(3) 0.65798(17) 0.0796(8) Uani 1 1 d . . .
F3 F 0.64720(14) 0.2698(5) 0.5883(2) 0.1641(12) Uani 1 1 d . A .
O3 O 0.46904(11) 0.3480(3) 0.57673(15) 0.0931(8) Uani 1 1 d . . .
C7 C 0.41368(14) -0.1494(5) 0.7248(3) 0.0864(11) Uani 1 1 d . . .
C8 C 0.3953(2) -0.0481(6) 0.7612(3) 0.1129(15) Uani 1 1 d . . .
H8 H 0.4173 0.0237 0.8097 0.135 Uiso 1 1 calc R . .
C9 C 0.3441(2) -0.0493(8) 0.7275(4) 0.1415(19) Uani 1 1 d . . .
H9 H 0.3306 0.0231 0.7516 0.170 Uiso 1 1 calc R . .
C10 C 0.31344(18) -0.1560(7) 0.6591(4) 0.1208(15) Uani 1 1 d . . .
C11 C 0.33114(19) -0.2619(6) 0.6223(4) 0.1304(18) Uani 1 1 d . . .
H11 H 0.3090 -0.3355 0.5751 0.156 Uiso 1 1 calc R . .
C12 C 0.38296(18) -0.2599(6) 0.6558(3) 0.1171(15) Uani 1 1 d . . .
H12 H 0.3966 -0.3324 0.6319 0.140 Uiso 1 1 calc R . .
C13 C 0.51530(17) 0.3288(4) 0.5808(2) 0.0866(11) Uani 1 1 d . A .
C14 C 0.51621(19) 0.2239(5) 0.5185(3) 0.0981(12) Uani 1 1 d . . .
H14 H 0.4866 0.1662 0.4749 0.118 Uiso 1 1 calc R A .
C15 C 0.5604(2) 0.2036(6) 0.5201(3) 0.1128(14) Uani 1 1 d . A .
H15 H 0.5616 0.1318 0.4785 0.135 Uiso 1 1 calc R . .
C16 C 0.6027(2) 0.2919(7) 0.5846(3) 0.1161(14) Uani 1 1 d . . .
C17 C 0.6025(2) 0.3988(6) 0.6458(3) 0.1159(15) Uani 1 1 d . A .
H17 H 0.6321 0.4576 0.6885 0.139 Uiso 1 1 calc R . .
C18 C 0.55812(19) 0.4188(5) 0.6437(3) 0.1010(12) Uani 1 1 d . . .
H18 H 0.5569 0.4926 0.6846 0.121 Uiso 1 1 calc R A .
F1A F 0.2335(2) 0.1169(12) 0.2829(5) 0.160(3) Uani 0.490(7) 1 d P A 1
C1A C 0.3634(8) 0.277(3) 0.5374(13) 0.084(11) Uiso 0.490(7) 1 d PD A 1
C2A C 0.3416(3) 0.1007(12) 0.5184(5) 0.106(4) Uani 0.490(7) 1 d P A 1
H2A H 0.3577 0.0219 0.5660 0.128 Uiso 0.490(7) 1 calc PR A 1
C3A C 0.2989(4) 0.0494(16) 0.4341(7) 0.113(3) Uani 0.490(7) 1 d P A 1
H3A H 0.2872 -0.0612 0.4251 0.136 Uiso 0.490(7) 1 calc PR A 1
C4A C 0.2750(5) 0.164(2) 0.3658(9) 0.102(4) Uani 0.490(7) 1 d P A 1
C5A C 0.2928(5) 0.3235(17) 0.3765(8) 0.109(4) Uani 0.490(7) 1 d P A 1
H5A H 0.2761 0.4004 0.3281 0.130 Uiso 0.490(7) 1 calc PR A 1
C6A C 0.3354(4) 0.3702(12) 0.4587(6) 0.096(3) Uani 0.490(7) 1 d P A 1
H6A H 0.3468 0.4797 0.4616 0.115 Uiso 0.490(7) 1 calc PR A 1
F1B F 0.2270(2) 0.1179(11) 0.3450(6) 0.167(3) Uani 0.510(7) 1 d P A 2
C1B C 0.3626(7) 0.271(3) 0.5408(12) 0.095(14) Uani 0.510(7) 1 d PD A 2
C2B C 0.3309(4) 0.2598(13) 0.5676(6) 0.111(3) Uani 0.510(7) 1 d P A 2
H2B H 0.3392 0.2870 0.6270 0.133 Uiso 0.510(7) 1 calc PR A 2
C3B C 0.2835(4) 0.2028(15) 0.4980(9) 0.135(4) Uani 0.510(7) 1 d P A 2
H3B H 0.2581 0.1822 0.5100 0.162 Uiso 0.510(7) 1 calc PR A 2
C4B C 0.2740(5) 0.1773(19) 0.4151(12) 0.113(4) Uani 0.510(7) 1 d P A 2
C5B C 0.3096(6) 0.199(3) 0.3941(10) 0.153(7) Uani 0.510(7) 1 d P A 2
H5B H 0.3023 0.1762 0.3349 0.183 Uiso 0.510(7) 1 calc PR A 2
C6B C 0.3587(4) 0.257(2) 0.4658(8) 0.133(4) Uani 0.510(7) 1 d P A 2
H6B H 0.3851 0.2819 0.4571 0.159 Uiso 0.510(7) 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 116.98(16) . .
N1 P1 O1 107.18(13) . .
N2 P1 O1 111.22(16) . .
N1 P1 O3 110.38(14) . .
N2 P1 O3 110.41(15) . .
O1 P1 O3 99.17(14) . .
C1B O1 C1A 4(3) . .
C1B O1 P1 125.1(14) . .
C1A O1 P1 124.1(14) . .
P1 N1 P1 122.7(3) . 2_656
N2 P2 N2 116.6(2) 2_656 .
N2 P2 O2 110.91(13) 2_656 2_656
N2 P2 O2 111.05(16) . 2_656
N2 P2 O2 111.05(16) 2_656 .
N2 P2 O2 110.91(13) . .
O2 P2 O2 94.0(2) 2_656 .
C7 O2 P2 126.0(2) . .
P2 N2 P1 123.01(17) . .
C13 O3 P1 120.4(2) . .
C8 C7 C12 121.7(4) . .
C8 C7 O2 122.7(4) . .
C12 C7 O2 115.3(4) . .
C7 C8 C9 119.7(4) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C10 C9 C8 119.1(5) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
C9 C10 C11 122.4(5) . .
C9 C10 F2 119.1(6) . .
C11 C10 F2 118.4(5) . .
C10 C11 C12 118.6(4) . .
C10 C11 H11 120.7 . .
C12 C11 H11 120.7 . .
C7 C12 C11 118.4(5) . .
C7 C12 H12 120.8 . .
C11 C12 H12 120.8 . .
C14 C13 C18 120.8(5) . .
C14 C13 O3 118.7(4) . .
C18 C13 O3 120.5(4) . .
C15 C14 C13 120.2(4) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 117.9(5) . .
C14 C15 H15 121.1 . .
C16 C15 H15 121.1 . .
F3 C16 C17 118.5(5) . .
F3 C16 C15 118.5(5) . .
C17 C16 C15 123.0(5) . .
C16 C17 C18 118.8(4) . .
C16 C17 H17 120.6 . .
C18 C17 H17 120.6 . .
C17 C18 C13 119.3(4) . .
C17 C18 H18 120.3 . .
C13 C18 H18 120.3 . .
C6A C1A O1 124.6(18) . .
C6A C1A C2A 108.7(6) . .
O1 C1A C2A 126.5(17) . .
C3A C2A C1A 123.9(10) . .
C3A C2A H2A 118.1 . .
C1A C2A H2A 118.1 . .
C4A C3A C2A 118.1(11) . .
C4A C3A H3A 121.0 . .
C2A C3A H3A 121.0 . .
C5A C4A F1A 119.2(14) . .
C5A C4A C3A 121.6(11) . .
F1A C4A C3A 119.1(15) . .
C4A C5A C6A 119.4(10) . .
C4A C5A H5A 120.3 . .
C6A C5A H5A 120.3 . .
C1A C6A C5A 128.2(11) . .
C1A C6A H6A 115.9 . .
C5A C6A H6A 115.9 . .
C6B C1B C2B 134.6(9) . .
C6B C1B O1 122(2) . .
C2B C1B O1 102.8(19) . .
C1B C2B C3B 111.9(9) . .
C1B C2B H2B 124.0 . .
C3B C2B H2B 124.0 . .
C4B C3B C2B 120.1(10) . .
C4B C3B H3B 119.9 . .
C2B C3B H3B 119.9 . .
C5B C4B C3B 122.8(13) . .
C5B C4B F1B 116.3(17) . .
C3B C4B F1B 120.8(13) . .
C4B C5B C6B 117.3(13) . .
C4B C5B H5B 121.4 . .
C6B C5B H5B 121.4 . .
C1B C6B C5B 112.8(12) . .
C1B 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 1.570(2) .
P1 N2 1.571(3) .
P1 O1 1.576(3) .
P1 O3 1.581(3) .
O1 C1B 1.390(2) .
O1 C1A 1.391(2) .
N1 P1 1.570(2) 2_656
P2 N2 1.571(3) 2_656
P2 N2 1.571(3) .
P2 O2 1.575(3) 2_656
P2 O2 1.575(3) .
F2 C10 1.366(5) .
O2 C7 1.395(4) .
F3 C16 1.355(6) .
O3 C13 1.404(5) .
C7 C8 1.322(6) .
C7 C12 1.361(5) .
C8 C9 1.363(6) .
C8 H8 0.9300 .
C9 C10 1.335(6) .
C9 H9 0.9300 .
C10 C11 1.335(7) .
C11 C12 1.380(6) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.368(5) .
C13 C18 1.371(5) .
C14 C15 1.363(6) .
C14 H14 0.9300 .
C15 C16 1.364(6) .
C15 H15 0.9300 .
C16 C17 1.353(6) .
C17 C18 1.366(6) .
C17 H17 0.9300 .
C18 H18 0.9300 .
F1A C4A 1.353(13) .
C1A C6A 1.36(2) .
C1A C2A 1.51(2) .
C2A C3A 1.390(11) .
C2A H2A 0.9300 .
C3A C4A 1.35(2) .
C3A H3A 0.9300 .
C4A C5A 1.35(2) .
C5A C6A 1.358(16) .
C5A H5A 0.9300 .
C6A H6A 0.9300 .
F1B C4B 1.373(14) .
C1B C6B 1.23(3) .
C1B C2B 1.30(4) .
C2B C3B 1.371(13) .
C2B H2B 0.9300 .
C3B C4B 1.304(18) .
C3B H3B 0.9300 .
C4B C5B 1.34(2) .
C5B C6B 1.42(2) .
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 C1B -175.4(13) . .
N2 P1 O1 C1B -46.4(13) . .
O3 P1 O1 C1B 69.8(13) . .
N1 P1 O1 C1A -179.5(16) . .
N2 P1 O1 C1A -50.5(16) . .
O3 P1 O1 C1A 65.7(16) . .
N2 P1 N1 P1 -3.57(12) . 2_656
O1 P1 N1 P1 122.06(13) . 2_656
O3 P1 N1 P1 -130.92(13) . 2_656
N2 P2 O2 C7 101.9(4) 2_656 .
N2 P2 O2 C7 -29.6(4) . .
O2 P2 O2 C7 -143.9(4) 2_656 .
N2 P2 N2 P1 -3.91(13) 2_656 .
O2 P2 N2 P1 -132.3(2) 2_656 .
O2 P2 N2 P1 124.5(2) . .
N1 P1 N2 P2 7.5(3) . .
O1 P1 N2 P2 -116.1(2) . .
O3 P1 N2 P2 134.8(2) . .
N1 P1 O3 C13 66.1(3) . .
N2 P1 O3 C13 -64.7(3) . .
O1 P1 O3 C13 178.4(3) . .
P2 O2 C7 C8 -73.1(5) . .
P2 O2 C7 C12 113.1(4) . .
C12 C7 C8 C9 -2.2(7) . .
O2 C7 C8 C9 -175.6(4) . .
C7 C8 C9 C10 1.4(8) . .
C8 C9 C10 C11 -0.1(9) . .
C8 C9 C10 F2 -179.0(5) . .
C9 C10 C11 C12 -0.5(9) . .
F2 C10 C11 C12 178.5(5) . .
C8 C7 C12 C11 1.6(7) . .
O2 C7 C12 C11 175.5(4) . .
C10 C11 C12 C7 -0.3(8) . .
P1 O3 C13 C14 110.4(3) . .
P1 O3 C13 C18 -72.1(4) . .
C18 C13 C14 C15 1.9(6) . .
O3 C13 C14 C15 179.4(3) . .
C13 C14 C15 C16 -0.6(6) . .
C14 C15 C16 F3 178.4(4) . .
C14 C15 C16 C17 -0.6(7) . .
F3 C16 C17 C18 -178.5(4) . .
C15 C16 C17 C18 0.5(8) . .
C16 C17 C18 C13 0.8(7) . .
C14 C13 C18 C17 -2.0(6) . .
O3 C13 C18 C17 -179.5(4) . .
C1B O1 C1A C6A 144(43) . .
P1 O1 C1A C6A -109(3) . .
C1B O1 C1A C2A -41(38) . .
P1 O1 C1A C2A 67(4) . .
C6A C1A C2A C3A -2(3) . .
O1 C1A C2A C3A -178(2) . .
C1A C2A C3A C4A -1(3) . .
C2A C3A C4A C5A 3(3) . .
C2A C3A C4A F1A 179.5(10) . .
F1A C4A C5A C6A -177.9(11) . .
C3A C4A C5A C6A -1(3) . .
O1 C1A C6A C5A 180(2) . .
C2A C1A C6A C5A 4(4) . .
C4A C5A C6A C1A -2(3) . .
C1A O1 C1B C6B 26(39) . .
P1 O1 C1B C6B -49(2) . .
C1A O1 C1B C2B -147(41) . .
P1 O1 C1B C2B 138.6(12) . .
C6B C1B C2B C3B 8(3) . .
O1 C1B C2B C3B 178.5(10) . .
C1B C2B C3B C4B -4.2(19) . .
C2B C3B C4B C5B 2(2) . .
C2B C3B C4B F1B 179.1(11) . .
C3B C4B C5B C6B -2(3) . .
F1B C4B C5B C6B -178.9(15) . .
C2B C1B C6B C5B -8(4) . .
O1 C1B C6B C5B -176.9(18) . .
C4B C5B C6B C1B 4(3) . .
loop_
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1 PubChem 11297331
