#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/40/7024006.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_7024006
loop_
_publ_author_name
'Beşli, Serap'
'Mutlu, Ceylan'
'Yuksel, Fatma'
_publ_section_title
;
 Nucleophilic substitution reactions of 10- and 11-membered fluorodioxy
 ansa cyclotriphosphazene derivatives.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16709
_journal_page_last               16722
_journal_paper_doi               10.1039/c3dt52461b
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C6 H7 Cl3 F6 N3 O3 P3'
_chemical_formula_weight         482.41
_chemical_name_common            cyclophosphazene
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 116.2410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.76460(10)
_cell_length_b                   12.8687(2)
_cell_length_c                   8.54690(10)
_cell_measurement_reflns_used    9126
_cell_measurement_temperature    120.(2)
_cell_measurement_theta_max      28.2914
_cell_measurement_theta_min      2.6569
_cell_volume                     765.997(19)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13812
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.66
_diffrn_source                   ImuS
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.092
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.227
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0292P)²+0.1593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0547
_reflns_number_gt                3723
_reflns_number_total             3819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52461b.txt
_cod_data_source_block           SB2a
_cod_original_cell_volume        765.997(18)
_cod_database_code               7024006
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
P P1 0.25064(7) 0.49145(4) 0.64992(6) 0.01415(10) Uani d . 1
P P2 0.22526(6) 0.28157(4) 0.57562(6) 0.01188(9) Uani d . 1
P P3 -0.09896(6) 0.39966(4) 0.44816(6) 0.01157(9) Uani d . 1
N N1 0.3470(2) 0.38265(13) 0.6557(2) 0.0172(3) Uani d . 1
N N2 -0.0021(2) 0.28832(12) 0.4960(2) 0.0135(3) Uani d . 1
N N3 0.0231(2) 0.49832(13) 0.54250(19) 0.0145(3) Uani d . 1
O O1 0.3492(2) 0.58116(12) 0.59673(18) 0.0215(3) Uani d . 1
O O2 0.28700(18) 0.24073(12) 0.43346(16) 0.0175(3) Uani d . 1
O O3 -0.18124(19) 0.41880(11) 0.24419(16) 0.0162(3) Uani d . 1
Cl Cl1 0.32712(7) 0.53762(4) 0.89655(6) 0.02291(11) Uani d . 1
Cl Cl2 0.31113(6) 0.16870(4) 0.75320(5) 0.01786(9) Uani d . 1
Cl Cl3 -0.33452(6) 0.39584(4) 0.48547(6) 0.01987(10) Uani d . 1
F F1 0.32875(17) 0.22883(11) 0.13513(15) 0.0246(3) Uani d . 1
F F2 0.05723(18) 0.14546(10) -0.00128(15) 0.0237(3) Uani d . 1
F F3 0.14474(16) 0.39733(10) 0.17567(15) 0.0220(2) Uani d . 1
F F4 0.07674(18) 0.34424(11) -0.08867(15) 0.0257(3) Uani d . 1
F F5 -0.21170(18) 0.43196(10) -0.08548(14) 0.0221(3) Uani d . 1
F F6 -0.25976(16) 0.26398(10) -0.12707(13) 0.0211(2) Uani d . 1
C C1 0.2853(3) 0.60601(17) 0.4130(3) 0.0210(4) Uani d . 1
H H1A 0.3299 0.5521 0.3585 0.031 Uiso calc R 1
H H1B 0.3382 0.6734 0.4028 0.031 Uiso calc R 1
H H1C 0.1447 0.6092 0.3542 0.031 Uiso calc R 1
C C2 0.1684(3) 0.17339(16) 0.2949(2) 0.0161(3) Uani d . 1
H H2A 0.0398 0.1676 0.2919 0.019 Uiso calc R 1
H H2B 0.2261 0.1031 0.3135 0.019 Uiso calc R 1
C C3 0.1504(3) 0.21765(16) 0.1243(2) 0.0159(4) Uani d . 1
C C4 0.0496(3) 0.32374(16) 0.0543(2) 0.0163(4) Uani d . 1
C C5 -0.1690(3) 0.33836(16) -0.0047(2) 0.0159(4) Uani d . 1
C C6 -0.2542(3) 0.33437(16) 0.1242(2) 0.0159(4) Uani d . 1
H H6A -0.3959 0.339 0.061 0.019 Uiso calc R 1
H H6B -0.2205 0.2676 0.1883 0.019 Uiso calc R 1
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'
Cl Cl 0.1484 0.1585 '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
O1 P1 N1 112.29(9)
O1 P1 N3 110.66(8)
N1 P1 N3 117.19(9)
O1 P1 Cl1 97.54(6)
N1 P1 Cl1 108.25(7)
N3 P1 Cl1 109.03(6)
N1 P2 O2 106.33(8)
N1 P2 N2 118.71(9)
O2 P2 N2 110.25(8)
N1 P2 Cl2 109.68(6)
O2 P2 Cl2 103.31(6)
N2 P2 Cl2 107.49(6)
N3 P3 N2 119.11(8)
N3 P3 O3 107.19(8)
N2 P3 O3 109.74(8)
N3 P3 Cl3 108.98(6)
N2 P3 Cl3 107.52(6)
O3 P3 Cl3 103.14(5)
P2 N1 P1 122.28(10)
P3 N2 P2 118.06(10)
P3 N3 P1 120.86(10)
C1 O1 P1 119.95(13)
C2 O2 P2 122.42(12)
C6 O3 P3 120.64(12)
O1 C1 H1A 109.5
O1 C1 H1B 109.5
H1A C1 H1B 109.5
O1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 C3 108.78(16)
O2 C2 H2A 109.9
C3 C2 H2A 109.9
O2 C2 H2B 109.9
C3 C2 H2B 109.9
H2A C2 H2B 108.3
F1 C3 F2 107.32(15)
F1 C3 C2 108.55(15)
F2 C3 C2 107.06(16)
F1 C3 C4 104.98(16)
F2 C3 C4 107.12(14)
C2 C3 C4 121.13(15)
F4 C4 F3 107.73(16)
F4 C4 C5 105.46(14)
F3 C4 C5 108.12(15)
F4 C4 C3 105.38(15)
F3 C4 C3 107.92(15)
C5 C4 C3 121.52(16)
F5 C5 F6 107.87(14)
F5 C5 C6 108.25(16)
F6 C5 C6 106.87(16)
F5 C5 C4 105.03(15)
F6 C5 C4 106.52(15)
C6 C5 C4 121.67(15)
O3 C6 C5 109.52(16)
O3 C6 H6A 109.8
C5 C6 H6A 109.8
O3 C6 H6B 109.8
C5 C6 H6B 109.8
H6A C6 H6B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.5596(15)
P1 N1 1.5777(17)
P1 N3 1.5927(16)
P1 Cl1 2.0105(6)
P2 N1 1.5753(17)
P2 O2 1.5803(13)
P2 N2 1.5888(17)
P2 Cl2 1.9907(6)
P3 N3 1.5764(16)
P3 N2 1.5855(17)
P3 O3 1.5884(12)
P3 Cl3 1.9912(6)
O1 C1 1.458(2)
O2 C2 1.427(2)
O3 C6 1.428(2)
F1 C3 1.354(2)
F2 C3 1.361(2)
F3 C4 1.357(2)
F4 C4 1.355(2)
F5 C5 1.355(2)
F6 C5 1.362(2)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C2 C3 1.513(2)
C2 H2A 0.99
C2 H2B 0.99
C3 C4 1.555(3)
C4 C5 1.554(3)
C5 C6 1.516(2)
C6 H6A 0.99
C6 H6B 0.99
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
O2 P2 N1 P1 121.31(12)
N2 P2 N1 P1 -3.56(16)
Cl2 P2 N1 P1 -127.61(10)
O1 P1 N1 P2 -135.65(11)
N3 P1 N1 P2 -5.92(16)
Cl1 P1 N1 P2 117.82(10)
N3 P3 N2 P2 -23.52(14)
O3 P3 N2 P2 100.49(11)
Cl3 P3 N2 P2 -148.00(8)
N1 P2 N2 P3 18.23(14)
O2 P2 N2 P3 -104.70(11)
Cl2 P2 N2 P3 143.36(8)
N2 P3 N3 P1 14.16(14)
O3 P3 N3 P1 -111.08(11)
Cl3 P3 N3 P1 137.93(9)
O1 P1 N3 P3 131.08(11)
N1 P1 N3 P3 0.59(15)
Cl1 P1 N3 P3 -122.76(9)
N1 P1 O1 C1 87.86(16)
N3 P1 O1 C1 -45.16(17)
Cl1 P1 O1 C1 -158.83(14)
N1 P2 O2 C2 -158.59(14)
N2 P2 O2 C2 -28.67(17)
Cl2 P2 O2 C2 85.95(14)
N3 P3 O3 C6 163.31(13)
N2 P3 O3 C6 32.62(15)
Cl3 P3 O3 C6 -81.73(13)
P2 O2 C2 C3 129.93(14)
O2 C2 C3 F1 57.0(2)
O2 C2 C3 F2 172.55(14)
O2 C2 C3 C4 -64.4(2)
F1 C3 C4 F4 50.73(17)
F2 C3 C4 F4 -63.15(18)
C2 C3 C4 F4 173.84(16)
F1 C3 C4 F3 -64.16(17)
F2 C3 C4 F3 -178.05(14)
C2 C3 C4 F3 58.9(2)
F1 C3 C4 C5 170.27(15)
F2 C3 C4 C5 56.4(2)
C2 C3 C4 C5 -66.6(2)
F4 C4 C5 F5 -49.76(18)
F3 C4 C5 F5 65.27(17)
C3 C4 C5 F5 -169.26(14)
F4 C4 C5 F6 64.52(18)
F3 C4 C5 F6 179.54(15)
C3 C4 C5 F6 -55.0(2)
F4 C4 C5 C6 -172.90(17)
F3 C4 C5 C6 -57.9(2)
C3 C4 C5 C6 67.6(2)
P3 O3 C6 C5 -131.70(14)
F5 C5 C6 O3 -57.18(18)
F6 C5 C6 O3 -173.14(14)
C4 C5 C6 O3 64.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139160902
