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#$Date: 2021-12-15 11:55:55 +0200 (Wed, 15 Dec 2021) $
#$Revision: 271444 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/57/1565778.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_1565778
loop_
_publ_author_name
'Yenilmez Çiftçi, Gönül'
'Tanrıverdi Eçik, Esra'
'Goler, Omer'
'Yuksel, Fatma'
'Duygulu, Ercan'
'Donbaloglu, Fadime'
'Turhal, Gulseren'
'Demiroglu-Zergeroglu, Asuman'
_publ_section_title
;
 Thiazole substituted dispiromonoansa and monospiro cyclotriphosphazenes:
 Design, synthesis and biological activity
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119158
_journal_paper_doi               10.1016/j.ica.2019.119158
_journal_volume                  498
_journal_year                    2019
_chemical_formula_moiety         'C26 H34 N9 O2 P3 S2'
_chemical_formula_sum            'C26 H34 N9 O2 P3 S2'
_chemical_formula_weight         661.65
_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   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                79.634(6)
_cell_angle_beta                 85.067(7)
_cell_angle_gamma                71.749(7)
_cell_formula_units_Z            2
_cell_length_a                   10.0646(10)
_cell_length_b                   10.5825(10)
_cell_length_c                   15.2015(13)
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.27
_cell_volume                     1511.8(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      299.47
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13197
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.362
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5218
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0405P)²+0.8194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3679
_reflns_number_total             5218
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2019-498-119158.cif
_cod_data_source_block           18gtu128_omg_06_0m
_cod_database_code               1565778
_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   0.956
_shelx_estimated_absorpt_t_min   0.950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4-N4
 0.89 with sigma of 0.02
 H6-N6
 0.89 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C18(H18), C20(H20), C21(H21), C26(H26)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
;
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
S1 S 0.24269(10) 0.69090(9) 0.88334(6) 0.0511(3) Uani 1 1 d . . . . .
S2 S 0.51231(12) -0.22706(12) 0.55309(8) 0.0677(3) Uani 1 1 d . . . . .
P1 P 1.00658(9) 0.15574(8) 0.85430(5) 0.0322(2) Uani 1 1 d . . . . .
P2 P 0.92851(9) 0.23027(8) 0.67495(5) 0.0339(2) Uani 1 1 d . . . . .
P3 P 0.76880(9) 0.12058(8) 0.80233(6) 0.0335(2) Uani 1 1 d . . . . .
O1 O 0.6082(2) 0.1576(2) 0.83632(15) 0.0424(6) Uani 1 1 d . . . . .
O2 O 0.7934(2) -0.0348(2) 0.79815(14) 0.0353(5) Uani 1 1 d . . . . .
N1 N 1.0407(3) 0.1898(2) 0.74970(16) 0.0328(6) Uani 1 1 d . . . . .
N2 N 0.7806(3) 0.2056(3) 0.70848(17) 0.0373(7) Uani 1 1 d . . . . .
N3 N 0.8625(3) 0.1230(3) 0.87950(16) 0.0355(6) Uani 1 1 d . . . . .
N4 N 1.1343(3) 0.0233(3) 0.89568(19) 0.0450(8) Uani 1 1 d D . . . .
H4 H 1.114(3) -0.018(3) 0.9445(15) 0.036(10) Uiso 1 1 d D . . . .
N5 N 1.0112(3) 0.2750(3) 0.90967(17) 0.0412(7) Uani 1 1 d . . . . .
N6 N 0.9889(3) 0.1446(3) 0.59182(18) 0.0420(7) Uani 1 1 d D . . . .
H6 H 1.077(2) 0.133(3) 0.581(2) 0.034(9) Uiso 1 1 d D . . . .
N7 N 0.9005(3) 0.3907(3) 0.62855(17) 0.0436(7) Uani 1 1 d . . . . .
N8 N 0.3195(3) 0.6127(3) 0.73042(19) 0.0464(7) Uani 1 1 d . . . . .
N9 N 0.7157(3) -0.1273(3) 0.5072(2) 0.0513(8) Uani 1 1 d . . . . .
C1 C 1.2655(4) 0.0474(5) 0.9087(3) 0.0699(13) Uani 1 1 d . . . . .
H1A H 1.3027 0.0809 0.8514 0.084 Uiso 1 1 calc R . . . .
H1B H 1.3330 -0.0368 0.9333 0.084 Uiso 1 1 calc R . . . .
C2 C 1.2446(5) 0.1475(5) 0.9707(3) 0.0799(15) Uani 1 1 d . . . . .
H2A H 1.3344 0.1577 0.9807 0.096 Uiso 1 1 calc R . . . .
H2B H 1.2072 0.1138 1.0279 0.096 Uiso 1 1 calc R . . . .
C3 C 1.1463(5) 0.2829(4) 0.9337(3) 0.0673(12) Uani 1 1 d . . . . .
H3A H 1.1301 0.3423 0.9778 0.081 Uiso 1 1 calc R . . . .
H3B H 1.1901 0.3221 0.8810 0.081 Uiso 1 1 calc R . . . .
C4 C 0.8982(4) 0.4025(4) 0.9006(2) 0.0558(11) Uani 1 1 d . . . . .
H4A H 0.8736 0.4269 0.9598 0.067 Uiso 1 1 calc R . . . .
H4B H 0.8170 0.3875 0.8795 0.067 Uiso 1 1 calc R . . . .
C5 C 0.9259(5) 0.5232(4) 0.8388(3) 0.0690(13) Uani 1 1 d . . . . .
H5A H 0.8424 0.6001 0.8389 0.083 Uiso 1 1 calc R . . . .
H5B H 1.0003 0.5451 0.8633 0.083 Uiso 1 1 calc R . . . .
C6 C 0.9662(5) 0.5032(4) 0.7427(2) 0.0599(11) Uani 1 1 d . . . . .
H6A H 1.0469 0.4236 0.7423 0.072 Uiso 1 1 calc R . . . .
H6B H 0.9936 0.5800 0.7113 0.072 Uiso 1 1 calc R . . . .
C7 C 0.8483(4) 0.4870(4) 0.6917(3) 0.0588(11) Uani 1 1 d . . . . .
H7A H 0.7831 0.4567 0.7345 0.071 Uiso 1 1 calc R . . . .
H7B H 0.7978 0.5742 0.6591 0.071 Uiso 1 1 calc R . . . .
C8 C 0.8231(4) 0.4302(4) 0.5442(2) 0.0597(11) Uani 1 1 d . . . . .
H8A H 0.8174 0.5228 0.5192 0.072 Uiso 1 1 calc R . . . .
H8B H 0.7284 0.4259 0.5573 0.072 Uiso 1 1 calc R . . . .
C9 C 0.8922(5) 0.3405(4) 0.4758(2) 0.0642(12) Uani 1 1 d . . . . .
H9A H 0.8372 0.3693 0.4225 0.077 Uiso 1 1 calc R . . . .
H9B H 0.9843 0.3500 0.4594 0.077 Uiso 1 1 calc R . . . .
C10 C 0.9063(4) 0.1957(4) 0.5106(2) 0.0545(10) Uani 1 1 d . . . . .
H10A H 0.8138 0.1856 0.5237 0.065 Uiso 1 1 calc R . . . .
H10B H 0.9508 0.1421 0.4647 0.065 Uiso 1 1 calc R . . . .
C11 C 0.5309(3) 0.2862(3) 0.8489(2) 0.0375(8) Uani 1 1 d . . . . .
C12 C 0.5022(4) 0.3104(3) 0.9364(2) 0.0479(9) Uani 1 1 d . . . . .
H12 H 0.5434 0.2438 0.9833 0.057 Uiso 1 1 calc R . . . .
C13 C 0.4136(4) 0.4319(4) 0.9541(2) 0.0517(10) Uani 1 1 d . . . . .
H13 H 0.3936 0.4481 1.0127 0.062 Uiso 1 1 calc R . . . .
C14 C 0.3547(3) 0.5296(3) 0.8829(2) 0.0397(8) Uani 1 1 d . . . . .
C15 C 0.2422(4) 0.7134(3) 0.7670(2) 0.0449(9) Uani 1 1 d . . . . .
C16 C 0.1587(4) 0.8428(4) 0.7161(3) 0.0635(12) Uani 1 1 d . . . . .
H16A H 0.0619 0.8464 0.7192 0.095 Uiso 1 1 calc GR . . . .
H16B H 0.1914 0.8497 0.6547 0.095 Uiso 1 1 calc GR . . . .
H16C H 0.1686 0.9162 0.7412 0.095 Uiso 1 1 calc GR . . . .
C17 C 0.3853(3) 0.5060(3) 0.7954(2) 0.0378(8) Uani 1 1 d . . . . .
C18 C 0.4750(3) 0.3821(3) 0.7779(2) 0.0416(8) Uani 1 1 d . . . . .
H18 H 0.4960 0.3653 0.7195 0.050 Uiso 1 1 calc R . . . .
C19 C 0.7201(3) -0.0768(3) 0.7407(2) 0.0350(8) Uani 1 1 d . . . . .
C20 C 0.6147(4) -0.1271(4) 0.7778(2) 0.0500(9) Uani 1 1 d . . . . .
H20 H 0.5911 -0.1278 0.8384 0.060 Uiso 1 1 calc R . . . .
C21 C 0.5433(4) -0.1766(4) 0.7260(3) 0.0615(11) Uani 1 1 d . . . . .
H21 H 0.4721 -0.2118 0.7509 0.074 Uiso 1 1 calc R . . . .
C22 C 0.5797(4) -0.1730(4) 0.6356(3) 0.0482(9) Uani 1 1 d . . . . .
C23 C 0.6317(4) -0.1783(4) 0.4763(3) 0.0557(10) Uani 1 1 d . . . . .
C24 C 0.6352(5) -0.1987(5) 0.3816(3) 0.0794(14) Uani 1 1 d . . . . .
H24A H 0.6710 -0.2933 0.3786 0.119 Uiso 1 1 calc GR . . . .
H24B H 0.6946 -0.1525 0.3461 0.119 Uiso 1 1 calc GR . . . .
H24C H 0.5422 -0.1635 0.3592 0.119 Uiso 1 1 calc GR . . . .
C25 C 0.6880(3) -0.1233(3) 0.5982(2) 0.0395(8) Uani 1 1 d . . . . .
C26 C 0.7592(3) -0.0731(3) 0.6516(2) 0.0395(8) Uani 1 1 d . . . . .
H26 H 0.8310 -0.0382 0.6276 0.047 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'
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'
S S 0.1246 0.1234 '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
C14 S1 C15 88.92(16) . .
C23 S2 C22 89.45(18) . .
N1 P1 N4 107.38(14) . .
N1 P1 N5 112.62(14) . .
N3 P1 N1 115.56(14) . .
N3 P1 N4 108.04(15) . .
N3 P1 N5 108.36(14) . .
N4 P1 N5 104.17(15) . .
N1 P2 N2 114.82(13) . .
N1 P2 N6 110.56(14) . .
N1 P2 N7 110.17(15) . .
N2 P2 N6 106.89(15) . .
N2 P2 N7 109.23(14) . .
N6 P2 N7 104.63(14) . .
O2 P3 O1 97.90(12) . .
N2 P3 O1 109.42(13) . .
N2 P3 O2 112.92(13) . .
N2 P3 N3 119.00(14) . .
N3 P3 O1 109.49(13) . .
N3 P3 O2 106.02(13) . .
C11 O1 P3 122.41(19) . .
C19 O2 P3 122.42(19) . .
P2 N1 P1 124.18(16) . .
P3 N2 P2 119.25(16) . .
P3 N3 P1 119.26(15) . .
C1 N4 P1 116.3(3) . .
C3 N5 P1 119.9(3) . .
C4 N5 P1 119.7(2) . .
C4 N5 C3 114.9(3) . .
C10 N6 P2 114.6(2) . .
C7 N7 P2 114.2(2) . .
C7 N7 C8 113.8(3) . .
C8 N7 P2 114.4(2) . .
C15 N8 C17 110.5(3) . .
C23 N9 C25 110.4(3) . .
N4 C1 C2 111.1(4) . .
C1 C2 C3 111.9(3) . .
N5 C3 C2 112.8(3) . .
N5 C4 C5 117.4(3) . .
C6 C5 C4 115.4(3) . .
C5 C6 C7 113.7(4) . .
N7 C7 C6 112.9(3) . .
N7 C8 C9 112.3(3) . .
C10 C9 C8 111.9(3) . .
N6 C10 C9 112.4(3) . .
O1 C11 C12 117.5(3) . .
C18 C11 O1 120.6(3) . .
C18 C11 C12 121.6(3) . .
C13 C12 C11 120.5(3) . .
C12 C13 C14 118.5(3) . .
C13 C14 S1 129.4(3) . .
C13 C14 C17 120.8(3) . .
C17 C14 S1 109.7(2) . .
N8 C15 S1 115.9(3) . .
N8 C15 C16 123.9(3) . .
C16 C15 S1 120.2(3) . .
N8 C17 C18 124.8(3) . .
C14 C17 N8 114.9(3) . .
C14 C17 C18 120.3(3) . .
C11 C18 C17 118.1(3) . .
C20 C19 O2 117.3(3) . .
C20 C19 C26 122.3(3) . .
C26 C19 O2 120.3(3) . .
C19 C20 C21 120.3(3) . .
C20 C21 C22 118.5(3) . .
C21 C22 S2 130.1(3) . .
C21 C22 C25 121.1(3) . .
C25 C22 S2 108.8(3) . .
N9 C23 S2 115.9(3) . .
N9 C23 C24 123.9(4) . .
C24 C23 S2 120.1(3) . .
N9 C25 C26 124.9(3) . .
C22 C25 N9 115.4(3) . .
C22 C25 C26 119.7(3) . .
C19 C26 C25 118.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C14 1.727(3) .
S1 C15 1.741(4) .
S2 C22 1.735(4) .
S2 C23 1.733(4) .
P1 N1 1.598(2) .
P1 N3 1.594(3) .
P1 N4 1.645(3) .
P1 N5 1.652(3) .
P2 N1 1.579(3) .
P2 N2 1.615(3) .
P2 N6 1.650(3) .
P2 N7 1.662(3) .
P3 O1 1.602(2) .
P3 O2 1.596(2) .
P3 N2 1.560(3) .
P3 N3 1.576(3) .
O1 C11 1.378(4) .
O2 C19 1.400(4) .
N4 C1 1.457(5) .
N5 C3 1.469(5) .
N5 C4 1.461(4) .
N6 C10 1.470(4) .
N7 C7 1.472(4) .
N7 C8 1.483(4) .
N8 C15 1.292(4) .
N8 C17 1.390(4) .
N9 C23 1.293(5) .
N9 C25 1.393(4) .
C1 C2 1.496(6) .
C2 C3 1.506(6) .
C4 C5 1.529(5) .
C5 C6 1.516(5) .
C6 C7 1.540(5) .
C8 C9 1.511(5) .
C9 C10 1.494(5) .
C11 C12 1.389(5) .
C11 C18 1.365(5) .
C12 C13 1.373(5) .
C13 C14 1.384(5) .
C14 C17 1.388(4) .
C15 C16 1.481(5) .
C17 C18 1.396(4) .
C19 C20 1.368(5) .
C19 C26 1.374(4) .
C20 C21 1.377(5) .
C21 C22 1.387(5) .
C22 C25 1.390(5) .
C23 C24 1.490(5) .
C25 C26 1.396(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6 N9 0.864(17) 2.37(2) 3.183(4) 157(3) 2_756
C2 H2B O2 0.97 2.63 3.531(5) 155.2 2_757
C4 H4A S1 0.97 2.82 3.561(4) 133.4 2_667
C4 H4B N3 0.97 2.69 3.164(4) 110.5 .
C6 H6A N1 0.97 2.48 3.147(5) 126.0 .
