#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/40/7024016.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_7024016
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            'C10 H16 F8 N3 O6 P3'
_chemical_formula_weight         519.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.967(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8998(7)
_cell_length_b                   6.4328(3)
_cell_length_c                   20.6068(10)
_cell_measurement_reflns_used    6862
_cell_measurement_temperature    130.(2)
_cell_measurement_theta_max      28.3166
_cell_measurement_theta_min      2.8744
_cell_volume                     1878.79(16)
_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      130.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16140
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.49
_diffrn_source                   ImuS
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         2.018
_refine_diff_density_min         -0.691
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0582
_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)+(0.0664P)²+8.1590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1557
_reflns_number_gt                3559
_reflns_number_total             4140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52461b.txt
_cod_data_source_block           SB8b
_cod_original_cell_volume        1878.79(15)
_cod_database_code               7024016
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.81973(6) 0.49592(13) 1.13537(4) 0.0146(2) Uani d . 1
P P2 0.67119(6) 0.36750(13) 1.02614(4) 0.0151(2) Uani d . 1
P P3 0.85386(6) 0.36050(13) 1.01788(4) 0.0149(2) Uani d . 1
N N1 0.71011(19) 0.4587(5) 1.10089(14) 0.0176(6) Uani d . 1
N N2 0.74620(19) 0.2957(4) 0.99032(14) 0.0165(6) Uani d . 1
N N3 0.88802(19) 0.4668(5) 1.09058(14) 0.0171(6) Uani d . 1
O O1 0.83966(18) 0.7223(4) 1.16579(12) 0.0207(5) Uani d . 1
O O2 0.84858(18) 0.3478(4) 1.20000(12) 0.0212(5) Uani d . 1
O O3 0.59829(16) 0.1869(4) 1.02208(13) 0.0200(5) Uani d . 1
O O4 0.60065(17) 0.5373(4) 0.98222(12) 0.0192(5) Uani d . 1
O O5 0.88184(17) 0.5168(4) 0.96788(12) 0.0186(5) Uani d . 1
O O6 0.91751(17) 0.1699(4) 1.01330(13) 0.0200(5) Uani d . 1
F F1 0.53395(18) 0.8579(4) 0.89182(13) 0.0370(6) Uani d . 1
F F2 0.5128(2) 0.6551(5) 0.80498(13) 0.0475(7) Uani d . 1
F F3 0.72638(14) 0.7606(3) 0.93618(10) 0.0215(4) Uani d . 1
F F4 0.6670(2) 0.9470(4) 0.84477(13) 0.0426(7) Uani d . 1
F F5 0.6753(2) 0.6677(5) 0.76226(13) 0.0506(8) Uani d . 1
F F6 0.68280(18) 0.4126(4) 0.83234(12) 0.0326(5) Uani d . 1
F F7 0.8418(2) 0.5740(5) 0.78969(12) 0.0464(7) Uani d . 1
F F8 0.8555(2) 0.8122(4) 0.86740(13) 0.0388(6) Uani d . 1
C C1 0.7946(3) 0.7902(6) 1.21497(19) 0.0264(8) Uani d . 1
H H1A 0.7278 0.7514 1.1991 0.04 Uiso calc R 1
H H1B 0.8002 0.9416 1.2201 0.04 Uiso calc R 1
H H1C 0.8253 0.7238 1.259 0.04 Uiso calc R 1
C C2 0.9473(3) 0.3385(7) 1.2406(2) 0.0329(9) Uani d . 1
H H2A 0.9803 0.2382 1.2202 0.049 Uiso calc R 1
H H2B 0.9523 0.2948 1.2871 0.049 Uiso calc R 1
H H2C 0.976 0.4761 1.2418 0.049 Uiso calc R 1
C C3 0.6318(3) -0.0048(6) 1.0574(2) 0.0265(8) Uani d . 1
H H3A 0.6817 -0.0628 1.041 0.04 Uiso calc R 1
H H3B 0.5795 -0.104 1.0487 0.04 Uiso calc R 1
H H3C 0.657 0.0222 1.1065 0.04 Uiso calc R 1
C C4 0.5534(3) 0.4991(6) 0.91167(18) 0.0231(7) Uani d . 1
H H4A 0.4853 0.4758 0.9045 0.028 Uiso calc R 1
H H4B 0.5796 0.3729 0.8968 0.028 Uiso calc R 1
C C5 0.5666(3) 0.6859(7) 0.8700(2) 0.0317(9) Uani d . 1
C C6 0.6696(3) 0.7528(7) 0.8707(2) 0.0338(9) Uani d . 1
C C7 0.7130(3) 0.6105(7) 0.8283(2) 0.0324(9) Uani d . 1
C C8 0.8233(3) 0.6181(7) 0.8490(2) 0.0316(9) Uani d . 1
C C9 0.8765(3) 0.4595(6) 0.89982(17) 0.0224(7) Uani d . 1
H H9A 0.8447 0.323 0.8888 0.027 Uiso calc R 1
H H9B 0.9411 0.4452 0.8965 0.027 Uiso calc R 1
C C10 0.9149(3) -0.0140(6) 1.0534(2) 0.0251(8) Uani d . 1
H H10A 0.9447 0.0166 1.1018 0.038 Uiso calc R 1
H H10B 0.9491 -0.1272 1.0395 0.038 Uiso calc R 1
H H10C 0.8492 -0.0557 1.0458 0.038 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 P1 N3 105.38(15)
O1 P1 O2 104.59(14)
N3 P1 O2 111.26(15)
O1 P1 N1 111.06(15)
N3 P1 N1 118.67(15)
O2 P1 N1 105.10(15)
O3 P2 N1 111.41(15)
O3 P2 N2 109.50(15)
N1 P2 N2 117.50(15)
O3 P2 O4 98.77(13)
N1 P2 O4 106.20(15)
N2 P2 O4 111.83(14)
O6 P3 N3 111.75(15)
O6 P3 N2 109.68(15)
N3 P3 N2 116.61(15)
O6 P3 O5 99.87(13)
N3 P3 O5 105.62(15)
N2 P3 O5 111.99(15)
P2 N1 P1 120.66(17)
P3 N2 P2 122.53(18)
P3 N3 P1 121.81(18)
C1 O1 P1 119.1(2)
C2 O2 P1 118.2(2)
C3 O3 P2 118.6(2)
C4 O4 P2 119.5(2)
C9 O5 P3 121.9(2)
C10 O6 P3 118.7(2)
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 H2A 109.5
O2 C2 H2B 109.5
H2A C2 H2B 109.5
O2 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O3 C3 H3A 109.5
O3 C3 H3B 109.5
H3A C3 H3B 109.5
O3 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
O4 C4 C5 109.2(3)
O4 C4 H4A 109.8
C5 C4 H4A 109.8
O4 C4 H4B 109.8
C5 C4 H4B 109.8
H4A C4 H4B 108.3
F1 C5 F2 106.8(3)
F1 C5 C4 109.7(3)
F2 C5 C4 107.7(4)
F1 C5 C6 102.8(3)
F2 C5 C6 109.1(3)
C4 C5 C6 120.0(3)
F3 C6 F4 107.0(3)
F3 C6 C7 110.2(3)
F4 C6 C7 106.9(3)
F3 C6 C5 108.9(3)
F4 C6 C5 109.6(4)
C7 C6 C5 114.0(4)
F5 C7 F6 105.9(3)
F5 C7 C6 107.0(3)
F6 C7 C6 108.5(3)
F5 C7 C8 109.9(3)
F6 C7 C8 110.6(3)
C6 C7 C8 114.6(4)
F8 C8 F7 106.9(3)
F8 C8 C9 111.6(3)
F7 C8 C9 105.9(3)
F8 C8 C7 111.0(4)
F7 C8 C7 103.6(3)
C9 C8 C7 116.9(3)
O5 C9 C8 111.5(3)
O5 C9 H9A 109.3
C8 C9 H9A 109.3
O5 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
O6 C10 H10A 109.5
O6 C10 H10B 109.5
H10A C10 H10B 109.5
O6 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.577(3)
P1 N3 1.582(3)
P1 O2 1.585(2)
P1 N1 1.586(3)
P2 O3 1.575(3)
P2 N1 1.582(3)
P2 N2 1.586(3)
P2 O4 1.591(2)
P3 O6 1.571(2)
P3 N3 1.581(3)
P3 N2 1.583(3)
P3 O5 1.585(2)
O1 C1 1.445(4)
O2 C2 1.452(5)
O3 C3 1.441(4)
O4 C4 1.428(4)
O5 C9 1.429(4)
O6 C10 1.450(4)
F1 C5 1.342(5)
F2 C5 1.347(5)
F3 C6 1.354(4)
F4 C6 1.355(5)
F5 C7 1.354(5)
F6 C7 1.361(5)
F7 C8 1.364(5)
F8 C8 1.349(5)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C2 H2A 0.98
C2 H2B 0.98
C2 H2C 0.98
C3 H3A 0.98
C3 H3B 0.98
C3 H3C 0.98
C4 C5 1.524(6)
C4 H4A 0.99
C4 H4B 0.99
C5 C6 1.589(6)
C6 C7 1.539(6)
C7 C8 1.567(6)
C8 C9 1.501(5)
C9 H9A 0.99
C9 H9B 0.99
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
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
O3 P2 N1 P1 133.12(19)
N2 P2 N1 P1 5.6(3)
O4 P2 N1 P1 -120.3(2)
O1 P1 N1 P2 129.8(2)
N3 P1 N1 P2 7.5(3)
O2 P1 N1 P2 -117.7(2)
O6 P3 N2 P2 139.02(19)
N3 P3 N2 P2 10.8(3)
O5 P3 N2 P2 -111.1(2)
O3 P2 N2 P3 -143.58(19)
N1 P2 N2 P3 -15.2(3)
O4 P2 N2 P3 108.0(2)
O6 P3 N3 P1 -124.0(2)
N2 P3 N3 P1 3.3(3)
O5 P3 N3 P1 128.4(2)
O1 P1 N3 P3 -137.3(2)
O2 P1 N3 P3 109.9(2)
N1 P1 N3 P3 -12.2(3)
N3 P1 O1 C1 -174.0(3)
O2 P1 O1 C1 -56.5(3)
N1 P1 O1 C1 56.3(3)
O1 P1 O2 C2 -66.3(3)
N3 P1 O2 C2 47.0(3)
N1 P1 O2 C2 176.6(3)
N1 P2 O3 C3 -67.3(3)
N2 P2 O3 C3 64.4(3)
O4 P2 O3 C3 -178.6(3)
O3 P2 O4 C4 -64.4(3)
N1 P2 O4 C4 -179.8(2)
N2 P2 O4 C4 50.8(3)
O6 P3 O5 C9 53.3(3)
N3 P3 O5 C9 169.4(3)
N2 P3 O5 C9 -62.7(3)
N3 P3 O6 C10 67.9(3)
N2 P3 O6 C10 -63.1(3)
O5 P3 O6 C10 179.2(3)
P2 O4 C4 C5 -129.4(3)
O4 C4 C5 F1 -57.4(4)
O4 C4 C5 F2 -173.3(3)
O4 C4 C5 C6 61.3(5)
F1 C5 C6 F3 73.8(4)
F2 C5 C6 F3 -173.1(3)
C4 C5 C6 F3 -48.3(5)
F1 C5 C6 F4 -42.9(4)
F2 C5 C6 F4 70.1(4)
C4 C5 C6 F4 -165.1(3)
F1 C5 C6 C7 -162.7(3)
F2 C5 C6 C7 -49.6(5)
C4 C5 C6 C7 75.2(5)
F3 C6 C7 F5 -157.4(3)
F4 C6 C7 F5 -41.5(5)
C5 C6 C7 F5 79.8(4)
F3 C6 C7 F6 88.8(4)
F4 C6 C7 F6 -155.3(3)
C5 C6 C7 F6 -34.0(5)
F3 C6 C7 C8 -35.3(5)
F4 C6 C7 C8 80.6(4)
C5 C6 C7 C8 -158.1(3)
F5 C7 C8 F8 84.1(4)
F6 C7 C8 F8 -159.4(3)
C6 C7 C8 F8 -36.4(5)
F5 C7 C8 F7 -30.3(4)
F6 C7 C8 F7 86.2(4)
C6 C7 C8 F7 -150.8(3)
F5 C7 C8 C9 -146.4(4)
F6 C7 C8 C9 -29.9(5)
C6 C7 C8 C9 93.1(4)
P3 O5 C9 C8 129.5(3)
F8 C8 C9 O5 50.0(4)
F7 C8 C9 O5 166.0(3)
C7 C8 C9 O5 -79.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139160913
