#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:58:18 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179945 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/40/7024007.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_7024007
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           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 94.079(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6100(4)
_cell_length_b                   14.0284(4)
_cell_length_c                   13.3930(7)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    120.(2)
_cell_measurement_theta_max      28.2354
_cell_measurement_theta_min      2.7806
_cell_volume                     1613.57(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15864
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.78
_diffrn_source                   ImuS
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.235
_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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0221
_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)+(0.0331P)²+0.5934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0550
_refine_ls_wR_factor_ref         0.0565
_reflns_number_gt                3815
_reflns_number_total             3980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt52461b.txt
_cod_data_source_block           SB3a
_cod_database_code               7024007
loop_
_space_group_symop_operation_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'
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 P3 0.74643(5) 0.10714(3) 0.80062(4) 0.01539(10) Uani d . 1
P P2 0.74001(5) -0.05038(3) 0.68069(4) 0.01530(10) Uani d . 1
P P1 0.78928(6) 0.12553(3) 0.60027(4) 0.01592(10) Uani d . 1
Cl Cl1 0.61748(6) 0.17954(4) 0.50663(4) 0.02688(11) Uani d . 1
Cl Cl2 0.87096(6) -0.16728(4) 0.68400(4) 0.02625(11) Uani d . 1
Cl Cl3 0.89874(6) 0.14543(4) 0.91214(4) 0.02579(11) Uani d . 1
N N2 0.7540(2) -0.00505(11) 0.78959(12) 0.0170(3) Uani d . 1
N N1 0.7810(2) 0.01286(11) 0.58924(12) 0.0182(3) Uani d . 1
N N3 0.7740(2) 0.17092(12) 0.70720(13) 0.0204(3) Uani d . 1
O O1 0.93916(17) 0.16890(11) 0.56041(11) 0.0242(3) Uani d . 1
O O3 0.58496(17) 0.13851(10) 0.83983(12) 0.0224(3) Uani d . 1
O O2 0.56858(16) -0.08961(11) 0.65719(10) 0.0209(3) Uani d . 1
C C1 0.9985(3) 0.13939(19) 0.4675(2) 0.0361(6) Uani d . 1
H H1A 1.0045 0.0697 0.4655 0.054 Uiso calc R 1
H H1B 1.1026 0.1664 0.4623 0.054 Uiso calc R 1
H H1C 0.9288 0.1621 0.4115 0.054 Uiso calc R 1
C C6 0.4808(2) -0.12664(15) 0.73534(15) 0.0200(4) Uani d . 1
H H6A 0.5345 -0.1118 0.8013 0.024 Uiso calc R 1
H H6B 0.4721 -0.1968 0.729 0.024 Uiso calc R 1
C C3 0.3317(2) 0.07118(15) 0.85083(16) 0.0221(4) Uani d . 1
C C5 0.3199(2) -0.08224(16) 0.72783(15) 0.0226(4) Uani d . 1
C C2 0.4963(2) 0.07617(15) 0.89837(15) 0.0209(4) Uani d . 1
H H2A 0.4956 0.1006 0.9677 0.025 Uiso calc R 1
H H2B 0.5436 0.0118 0.9008 0.025 Uiso calc R 1
C C4 0.2974(2) 0.02657(16) 0.74487(16) 0.0231(4) Uani d . 1
F F3 0.38188(16) 0.07444(9) 0.67978(9) 0.0288(3) Uani d . 1
F F6 0.23542(16) -0.12825(9) 0.79522(10) 0.0295(3) Uani d . 1
F F2 0.24655(15) 0.02252(10) 0.91568(10) 0.0304(3) Uani d . 1
F F4 0.14546(16) 0.04442(11) 0.71991(12) 0.0378(3) Uani d . 1
F F5 0.25233(15) -0.09986(11) 0.63549(10) 0.0316(3) Uani d . 1
F F1 0.27397(16) 0.16072(9) 0.84441(11) 0.0308(3) Uani d . 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
N3 P3 N2 118.86(9)
N3 P3 O3 107.00(9)
N2 P3 O3 110.52(8)
N3 P3 Cl3 108.38(7)
N2 P3 Cl3 108.00(7)
O3 P3 Cl3 102.91(6)
N1 P2 O2 107.37(8)
N1 P2 N2 118.87(9)
O2 P2 N2 109.28(8)
N1 P2 Cl2 108.92(7)
O2 P2 Cl2 103.68(6)
N2 P2 Cl2 107.68(6)
O1 P1 N3 106.13(9)
O1 P1 N1 112.96(9)
N3 P1 N1 118.61(9)
O1 P1 Cl1 103.26(6)
N3 P1 Cl1 107.90(7)
N1 P1 Cl1 106.84(7)
P3 N2 P2 118.89(10)
P2 N1 P1 120.00(10)
P3 N3 P1 121.29(11)
C1 O1 P1 122.59(15)
C2 O3 P3 121.81(13)
C6 O2 P2 120.88(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 C6 C5 109.26(17)
O2 C6 H6A 109.8
C5 C6 H6A 109.8
O2 C6 H6B 109.8
C5 C6 H6B 109.8
H6A C6 H6B 108.3
F1 C3 F2 107.14(16)
F1 C3 C2 108.24(18)
F2 C3 C2 106.62(17)
F1 C3 C4 105.66(17)
F2 C3 C4 107.69(17)
C2 C3 C4 120.82(17)
F5 C5 F6 107.70(16)
F5 C5 C6 108.52(17)
F6 C5 C6 106.87(17)
F5 C5 C4 105.26(18)
F6 C5 C4 106.82(16)
C6 C5 C4 121.07(17)
O3 C2 C3 108.53(17)
O3 C2 H2A 110.0
C3 C2 H2A 110.0
O3 C2 H2B 110.0
C3 C2 H2B 110.0
H2A C2 H2B 108.4
F4 C4 F3 107.72(17)
F4 C4 C5 105.91(17)
F3 C4 C5 108.28(17)
F4 C4 C3 105.56(17)
F3 C4 C3 108.14(16)
C5 C4 C3 120.59(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P3 N3 1.5700(18)
P3 N2 1.5825(17)
P3 O3 1.5831(15)
P3 Cl3 1.9901(7)
P2 N1 1.5726(17)
P2 O2 1.5857(15)
P2 N2 1.5879(16)
P2 Cl2 1.9888(7)
P1 O1 1.5552(15)
P1 N3 1.5812(18)
P1 N1 1.5887(16)
P1 Cl1 2.0177(7)
O1 C1 1.439(3)
O3 C2 1.431(2)
O2 C6 1.431(2)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C6 C5 1.515(3)
C6 H6A 0.99
C6 H6B 0.99
C3 F1 1.351(2)
C3 F2 1.360(2)
C3 C2 1.514(3)
C3 C4 1.560(3)
C5 F5 1.352(2)
C5 F6 1.362(2)
C5 C4 1.558(3)
C2 H2A 0.99
C2 H2B 0.99
C4 F4 1.350(3)
C4 F3 1.353(2)
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
N3 P3 N2 P2 -17.56(16)
O3 P3 N2 P2 106.68(12)
Cl3 P3 N2 P2 -141.45(9)
N1 P2 N2 P3 22.48(16)
O2 P2 N2 P3 -101.16(12)
Cl2 P2 N2 P3 146.85(9)
O2 P2 N1 P1 107.58(12)
N2 P2 N1 P1 -17.00(16)
Cl2 P2 N1 P1 -140.76(10)
O1 P1 N1 P2 131.71(11)
N3 P1 N1 P2 6.63(17)
Cl1 P1 N1 P2 -115.43(11)
N2 P3 N3 P1 7.29(18)
O3 P3 N3 P1 -118.66(13)
Cl3 P3 N3 P1 130.99(11)
O1 P1 N3 P3 -130.09(13)
N1 P1 N3 P3 -1.75(18)
Cl1 P1 N3 P3 119.78(12)
N3 P1 O1 C1 175.34(18)
N1 P1 O1 C1 43.7(2)
Cl1 P1 O1 C1 -71.28(18)
N3 P3 O3 C2 156.97(15)
N2 P3 O3 C2 26.17(17)
Cl3 P3 O3 C2 -88.94(15)
N1 P2 O2 C6 -162.31(15)
N2 P2 O2 C6 -32.11(18)
Cl2 P2 O2 C6 82.49(15)
P2 O2 C6 C5 131.29(15)
O2 C6 C5 F5 56.7(2)
O2 C6 C5 F6 172.55(15)
O2 C6 C5 C4 -65.1(2)
P3 O3 C2 C3 -128.21(16)
F1 C3 C2 O3 -56.7(2)
F2 C3 C2 O3 -171.67(15)
C4 C3 C2 O3 65.1(2)
F5 C5 C4 F4 48.8(2)
F6 C5 C4 F4 -65.5(2)
C6 C5 C4 F4 172.06(18)
F5 C5 C4 F3 -66.5(2)
F6 C5 C4 F3 179.17(16)
C6 C5 C4 F3 56.8(2)
F5 C5 C4 C3 168.30(17)
F6 C5 C4 C3 54.0(2)
C6 C5 C4 C3 -68.4(2)
F1 C3 C4 F4 -49.20(19)
F2 C3 C4 F4 65.0(2)
C2 C3 C4 F4 -172.28(18)
F1 C3 C4 F3 65.9(2)
F2 C3 C4 F3 -179.89(17)
C2 C3 C4 F3 -57.2(2)
F1 C3 C4 C5 -168.89(17)
F2 C3 C4 C5 -54.6(2)
C2 C3 C4 C5 68.0(3)
