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#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/62/7056206.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_7056206
loop_
_publ_author_name
'Elmas, Gamze'
'Okumuş, Aytuğ'
'Sevinç, Pelin'
'Kılıç, Zeynel'
'Açık, Leyla'
'Atalan, Mustafa'
'Turk, Mustafa'
'Deniz, Gökberk'
'Hökelek, Tuncer'
_publ_section_title
;
 Phosphorus-nitrogen compounds. Part 37. Syntheses and structural
 characterizations, biological activities of mono and
 bis(4-fluorobenzyl)spirocyclotetraphosphazenes
;
_journal_issue                   13
_journal_name_full               'New J. Chem.'
_journal_page_first              5818
_journal_page_last               5835
_journal_paper_doi               10.1039/C7NJ00478H
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C20 H26 Cl4 F2 N8 P4'
_chemical_formula_sum            'C20 H26 Cl4 F2 N8 P4'
_chemical_formula_weight         682.17
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-02-03 deposited with the CCDC.
2017-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                75.382(3)
_cell_angle_beta                 71.148(3)
_cell_angle_gamma                87.868(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5886(2)
_cell_length_b                   9.2505(3)
_cell_length_c                   9.5924(3)
_cell_measurement_reflns_used    5449
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.28
_cell_volume                     697.06(4)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10863
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2005'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0425
_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)+(0.0621P)²+0.1989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2523
_reflns_number_total             2850
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c7nj00478h2.cif
_cod_data_source_block           Compound_7
_cod_database_code               7056206
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
P1 P 0.15724(6) 0.32594(5) 0.43112(6) 0.01630(17) Uani 1 1 d .
P2 P 0.13593(6) 0.54732(5) 0.61628(6) 0.01682(17) Uani 1 1 d .
Cl1 Cl 0.17160(8) 0.48780(6) 0.82120(7) 0.0348(2) Uani 1 1 d .
Cl2 Cl 0.35021(7) 0.66603(7) 0.48825(8) 0.0395(2) Uani 1 1 d .
F1 F 0.29143(18) -0.08374(18) 1.13869(17) 0.0419(4) Uani 1 1 d .
N1 N 0.1253(2) 0.40188(18) 0.5684(2) 0.0191(4) Uani 1 1 d .
N2 N -0.0049(2) 0.6595(2) 0.6329(2) 0.0257(4) Uani 1 1 d .
N3 N 0.2028(2) 0.15079(18) 0.4761(2) 0.0197(4) Uani 1 1 d .
N4 N 0.3352(2) 0.38127(19) 0.2953(2) 0.0218(4) Uani 1 1 d .
C1 C 0.2521(3) -0.0543(3) 1.0068(3) 0.0273(5) Uani 1 1 d .
C2 C 0.1465(3) -0.1547(2) 0.9932(3) 0.0279(5) Uani 1 1 d .
H2 H 0.1044 -0.2407 1.0705 0.033 Uiso 1 1 calc R
C3 C 0.1053(3) -0.1237(2) 0.8614(3) 0.0244(5) Uani 1 1 d .
H3 H 0.0354 -0.1906 0.8495 0.029 Uiso 1 1 calc R
C4 C 0.1664(2) 0.0064(2) 0.7456(3) 0.0198(5) Uani 1 1 d .
C5 C 0.2734(3) 0.1036(2) 0.7647(3) 0.0228(5) Uani 1 1 d .
H5 H 0.3159 0.1903 0.6885 0.027 Uiso 1 1 calc R
C6 C 0.3177(3) 0.0728(3) 0.8959(3) 0.0271(5) Uani 1 1 d .
H6 H 0.3903 0.1372 0.9078 0.033 Uiso 1 1 calc R
C7 C 0.1059(3) 0.0394(2) 0.6098(3) 0.0230(5) Uani 1 1 d .
H7A H 0.1014 -0.0532 0.5809 0.028 Uiso 1 1 calc R
H7B H -0.0058 0.0723 0.6412 0.028 Uiso 1 1 calc R
C8 C 0.3677(3) 0.1212(2) 0.3841(3) 0.0247(5) Uani 1 1 d .
H8A H 0.3661 0.0278 0.3559 0.030 Uiso 1 1 calc R
H8B H 0.4449 0.1155 0.4398 0.030 Uiso 1 1 calc R
C9 C 0.4155(3) 0.2519(3) 0.2437(3) 0.0283(5) Uani 1 1 d .
H9A H 0.5341 0.2697 0.2032 0.034 Uiso 1 1 calc R
H9B H 0.3770 0.2326 0.1652 0.034 Uiso 1 1 calc R
C10 C 0.3455(3) 0.5191(3) 0.1784(3) 0.0348(6) Uani 1 1 d .
H10A H 0.2747 0.5900 0.2224 0.052 Uiso 1 1 calc R
H10B H 0.3116 0.4987 0.0989 0.052 Uiso 1 1 calc R
H10C H 0.4570 0.5597 0.1367 0.052 Uiso 1 1 calc R
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 P1 N2 112.07(9) . 2_566
N1 P1 N3 112.27(9) . .
N1 P1 N4 113.26(9) . .
N2 P1 N3 110.27(9) 2_566 .
N2 P1 N4 112.74(10) 2_566 .
N3 P1 N4 95.12(9) . .
Cl1 P2 Cl2 100.08(4) . .
N1 P2 Cl1 106.97(7) . .
N1 P2 Cl2 111.09(7) . .
N1 P2 N2 122.78(9) . .
N2 P2 Cl1 105.67(8) . .
N2 P2 Cl2 107.73(8) . .
P2 N1 P1 146.41(13) . .
P2 N2 P1 129.33(11) . 2_566
C7 N3 P1 124.43(14) . .
C7 N3 C8 121.45(16) . .
C8 N3 P1 113.24(14) . .
C9 N4 P1 109.83(14) . .
C10 N4 P1 119.08(15) . .
C10 N4 C9 116.83(18) . .
F1 C1 C2 118.2(2) . .
C6 C1 F1 118.9(2) . .
C6 C1 C2 123.0(2) . .
C1 C2 C3 118.0(2) . .
C1 C2 H2 121.0 . .
C3 C2 H2 121.0 . .
C2 C3 C4 121.3(2) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C4 C7 118.52(18) . .
C5 C4 C3 118.4(2) . .
C5 C4 C7 123.0(2) . .
C4 C5 H5 119.5 . .
C6 C5 C4 121.0(2) . .
C6 C5 H5 119.5 . .
C1 C6 C5 118.4(2) . .
C1 C6 H6 120.8 . .
C5 C6 H6 120.8 . .
N3 C7 C4 116.24(17) . .
N3 C7 H7A 108.2 . .
N3 C7 H7B 108.2 . .
C4 C7 H7A 108.2 . .
C4 C7 H7B 108.2 . .
H7A C7 H7B 107.4 . .
N3 C8 C9 105.32(16) . .
N3 C8 H8A 110.7 . .
N3 C8 H8B 110.7 . .
C9 C8 H8A 110.7 . .
C9 C8 H8B 110.7 . .
H8A C8 H8B 108.8 . .
N4 C9 C8 105.49(18) . .
N4 C9 H9A 110.6 . .
N4 C9 H9B 110.6 . .
C8 C9 H9A 110.6 . .
C8 C9 H9B 110.6 . .
H9A C9 H9B 108.8 . .
N4 C10 H10A 109.5 . .
N4 C10 H10B 109.5 . .
N4 C10 H10C 109.5 . .
H10A C10 H10B 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
_geom_bond_site_symmetry_2
P1 N1 1.5884(17) .
P1 N2 1.6037(18) 2_566
P1 N3 1.6351(16) .
P1 N4 1.6527(18) .
P2 Cl1 2.0226(8) .
P2 Cl2 2.0273(8) .
P2 N1 1.5418(16) .
P2 N2 1.5592(17) .
F1 C1 1.372(3) .
N2 P1 1.6037(18) 2_566
N3 C7 1.451(3) .
N3 C8 1.465(3) .
N4 C9 1.472(3) .
N4 C10 1.454(3) .
C1 C2 1.379(3) .
C1 C6 1.365(3) .
C2 H2 0.9300 .
C3 C2 1.380(3) .
C3 C4 1.397(3) .
C3 H3 0.9300 .
C4 C7 1.512(3) .
C5 C4 1.393(3) .
C5 C6 1.389(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.517(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
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
N2 P1 N1 P2 -86.2(2) 2_566 .
N3 P1 N1 P2 149.0(2) . .
N4 P1 N1 P2 42.7(2) . .
N1 P1 N3 C7 51.57(18) . .
N1 P1 N3 C8 -117.81(16) . .
N2 P1 N3 C7 -74.17(18) 2_566 .
N2 P1 N3 C8 116.44(16) 2_566 .
N4 P1 N3 C7 169.29(17) . .
N4 P1 N3 C8 -0.10(16) . .
N1 P1 N4 C9 137.32(15) . .
N1 P1 N4 C10 -84.14(19) . .
N2 P1 N4 C9 -94.10(16) 2_566 .
N2 P1 N4 C10 44.4(2) 2_566 .
N3 P1 N4 C9 20.41(16) . .
N3 P1 N4 C10 158.95(18) . .
Cl1 P2 N1 P1 -150.00(19) . .
Cl2 P2 N1 P1 -41.7(2) . .
N2 P2 N1 P1 87.8(2) . .
Cl1 P2 N2 P1 -139.54(15) . 2_566
Cl2 P2 N2 P1 114.17(15) . 2_566
N1 P2 N2 P1 -16.8(2) . 2_566
P1 N3 C7 C4 -98.7(2) . .
C8 N3 C7 C4 69.8(2) . .
P1 N3 C8 C9 -19.1(2) . .
C7 N3 C8 C9 171.15(18) . .
P1 N4 C9 C8 -33.6(2) . .
C10 N4 C9 C8 -173.1(2) . .
C6 C1 C2 C3 -0.5(3) . .
F1 C1 C2 C3 179.06(18) . .
F1 C1 C6 C5 -178.23(18) . .
C2 C1 C6 C5 1.3(3) . .
C4 C3 C2 C1 -0.8(3) . .
C2 C3 C4 C5 1.3(3) . .
C2 C3 C4 C7 -175.31(19) . .
C3 C4 C7 N3 -163.96(17) . .
C5 C4 C7 N3 19.6(3) . .
C6 C5 C4 C3 -0.4(3) . .
C6 C5 C4 C7 176.00(19) . .
C4 C5 C6 C1 -0.8(3) . .
N3 C8 C9 N4 32.0(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139177859
