#------------------------------------------------------------------------------
#$Date: 2021-12-14 11:39:55 +0200 (Tue, 14 Dec 2021) $
#$Revision: 271390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/57/1565737.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_1565737
loop_
_publ_author_name
'İbişoğlu, Hanife'
'Erdemir, Eda'
'Atilla, Devrim'
'Zorlu, Yunus'
'Şenkuytu, Elif'
_publ_section_title
;
 Synthesis, characterization and photophysical properties of
 cyclotriphosphazenes including heterocyclic rings
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119120
_journal_paper_doi               10.1016/j.ica.2019.119120
_journal_volume                  498
_journal_year                    2019
_chemical_formula_moiety         'C12 H8 Cl4 N3 O2 P3'
_chemical_formula_sum            'C12 H8 Cl4 N3 O2 P3'
_chemical_formula_weight         460.92
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                87.973(9)
_cell_angle_beta                 85.334(9)
_cell_angle_gamma                76.965(7)
_cell_formula_units_Z            2
_cell_length_a                   8.278(3)
_cell_length_b                   9.383(3)
_cell_length_c                   12.172(4)
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.53
_cell_volume                     917.9(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7513
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.679
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0746P)²+1.2266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1600
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2595
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1.cif
_cod_data_source_block           19gtu052_118z646_0m
_cod_database_code               1565737
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.728
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7550(2) 0.49284(18) 0.54770(12) 0.0839(5) Uani 1 1 d . . . . .
Cl2 Cl 0.90930(15) 0.55206(16) 0.75977(15) 0.0835(5) Uani 1 1 d . . . . .
Cl3 Cl 0.40860(17) 0.21146(16) 0.73492(11) 0.0691(4) Uani 1 1 d . . . . .
Cl4 Cl 0.47021(19) 0.31270(15) 0.96232(10) 0.0701(4) Uani 1 1 d . . . . .
P1 P 0.69616(13) 0.52794(12) 0.70940(10) 0.0471(3) Uani 1 1 d . . . . .
P2 P 0.37048(12) 0.67310(12) 0.75183(9) 0.0423(3) Uani 1 1 d . . . . .
P3 P 0.47161(13) 0.37870(12) 0.80459(9) 0.0440(3) Uani 1 1 d . . . . .
O1 O 0.2621(4) 0.7239(3) 0.6501(2) 0.0491(7) Uani 1 1 d . . . . .
O2 O 0.3009(3) 0.7955(3) 0.8391(2) 0.0452(7) Uani 1 1 d . . . . .
N1 N 0.5609(4) 0.6760(4) 0.7261(3) 0.0499(9) Uani 1 1 d . . . . .
N2 N 0.3307(4) 0.5200(4) 0.7903(3) 0.0545(10) Uani 1 1 d . . . . .
N3 N 0.6571(4) 0.3820(4) 0.7633(4) 0.0614(11) Uani 1 1 d . . . . .
C1 C 0.2223(5) 0.8737(5) 0.6179(3) 0.0454(10) Uani 1 1 d . . . . .
C2 C 0.2971(6) 0.9151(6) 0.5203(4) 0.0603(13) Uani 1 1 d . . . . .
H2 H 0.379369 0.848593 0.480391 0.072 Uiso 1 1 calc R . . . .
C3 C 0.2465(7) 1.0585(7) 0.4832(4) 0.0708(15) Uani 1 1 d . . . . .
H3 H 0.296145 1.088996 0.417997 0.085 Uiso 1 1 calc R . . . .
C4 C 0.1234(7) 1.1564(6) 0.5420(5) 0.0713(15) Uani 1 1 d . . . . .
H4 H 0.088333 1.251484 0.515246 0.086 Uiso 1 1 calc R . . . .
C5 C 0.0522(6) 1.1140(5) 0.6399(4) 0.0599(12) Uani 1 1 d . . . . .
H5 H -0.030169 1.181351 0.678983 0.072 Uiso 1 1 calc R . . . .
C6 C 0.1011(5) 0.9714(5) 0.6823(4) 0.0447(9) Uani 1 1 d . . . . .
C7 C 0.0274(5) 0.9245(5) 0.7882(4) 0.0444(9) Uani 1 1 d . . . . .
C8 C -0.1430(5) 0.9699(5) 0.8192(4) 0.0590(12) Uani 1 1 d . . . . .
H8 H -0.212363 1.029860 0.771760 0.071 Uiso 1 1 calc R . . . .
C9 C -0.2088(6) 0.9267(6) 0.9194(5) 0.0698(14) Uani 1 1 d . . . . .
H9 H -0.322130 0.957077 0.938629 0.084 Uiso 1 1 calc R . . . .
C10 C -0.1080(7) 0.8391(7) 0.9907(5) 0.0701(14) Uani 1 1 d . . . . .
H10 H -0.153991 0.810824 1.057989 0.084 Uiso 1 1 calc R . . . .
C11 C 0.0621(6) 0.7921(6) 0.9639(4) 0.0575(12) Uani 1 1 d . . . . .
H11 H 0.130736 0.732976 1.012123 0.069 Uiso 1 1 calc R . . . .
C12 C 0.1251(5) 0.8362(5) 0.8633(3) 0.0437(9) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
Cl2 P1 Cl1 101.76(9) . .
N1 P1 Cl1 109.81(16) . .
N1 P1 Cl2 109.33(15) . .
N1 P1 N3 118.7(2) . .
N3 P1 Cl1 107.50(19) . .
N3 P1 Cl2 108.36(16) . .
O1 P2 N1 113.19(19) . .
O1 P2 N2 104.79(19) . .
O2 P2 O1 103.89(15) . .
O2 P2 N1 105.47(18) . .
O2 P2 N2 112.3(2) . .
N1 P2 N2 116.65(18) . .
Cl4 P3 Cl3 100.73(7) . .
N2 P3 Cl3 108.76(16) . .
N2 P3 Cl4 109.97(17) . .
N2 P3 N3 119.1(2) . .
N3 P3 Cl3 108.95(18) . .
N3 P3 Cl4 107.76(17) . .
C1 O1 P2 120.0(3) . .
C12 O2 P2 117.9(2) . .
P1 N1 P2 120.2(2) . .
P3 N2 P2 122.2(2) . .
P3 N3 P1 119.2(2) . .
C2 C1 O1 118.1(4) . .
C2 C1 C6 122.8(4) . .
C6 C1 O1 118.9(4) . .
C1 C2 C3 118.3(5) . .
C4 C3 C2 120.7(5) . .
C5 C4 C3 120.3(5) . .
C4 C5 C6 121.4(5) . .
C1 C6 C7 121.4(4) . .
C5 C6 C1 116.6(4) . .
C5 C6 C7 122.1(4) . .
C8 C7 C6 121.7(4) . .
C12 C7 C6 121.3(4) . .
C12 C7 C8 116.9(4) . .
C9 C8 C7 120.7(5) . .
C10 C9 C8 120.4(5) . .
C9 C10 C11 120.9(5) . .
C12 C11 C10 117.7(5) . .
C7 C12 O2 119.1(4) . .
C11 C12 O2 117.5(4) . .
C11 C12 C7 123.3(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 P1 2.009(2) .
Cl2 P1 1.9763(17) .
Cl3 P3 1.9972(17) .
Cl4 P3 1.9963(17) .
P1 N1 1.583(4) .
P1 N3 1.585(4) .
P2 O1 1.584(3) .
P2 O2 1.571(3) .
P2 N1 1.588(4) .
P2 N2 1.591(4) .
P3 N2 1.571(4) .
P3 N3 1.583(4) .
O1 C1 1.418(5) .
O2 C12 1.427(5) .
C1 C2 1.379(6) .
C1 C6 1.403(6) .
C2 C3 1.387(8) .
C3 C4 1.378(8) .
C4 C5 1.372(7) .
C5 C6 1.400(6) .
C6 C7 1.477(6) .
C7 C8 1.402(6) .
C7 C12 1.393(6) .
C8 C9 1.380(8) .
C9 C10 1.372(8) .
C10 C11 1.392(7) .
C11 C12 1.379(6) .
