Cyclic phosphazene derivatives combined with two different forms of the phenol-pyrazole group: synthesis, spectroscopic and crystallographic characterization and stereochemical properties
Mutlu Balcı, Ceylan; Palabıyık, Duygu; Beşli, Serap; New Journal of Chemistry 49 (2025) 9583–9599; doi:10.1039/D5NJ01321F

data_7063815
_publ_section_title
;
 Cyclic phosphazene derivatives combined with two different forms of the
 phenol-pyrazole group: synthesis, spectroscopic and crystallographic
 characterization and stereochemical properties
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9583
_journal_page_last               9599
_journal_paper_doi               10.1039/D5NJ01321F
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C36 H26 N11 O4 P3 [+ solvent]'
_chemical_formula_sum            'C36 H26 N11 O4 P3'
_chemical_formula_weight         769.59
_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     iterative
_audit_creation_date             2022-03-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2025-03-03 deposited with the CCDC.	2025-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                97.720(2)
_cell_angle_beta                 104.312(2)
_cell_angle_gamma                92.798(2)
_cell_formula_units_Z            4
_cell_length_a                   12.4130(11)
_cell_length_b                   14.0903(12)
_cell_length_c                   23.476(2)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    173.01
_cell_measurement_theta_max      22.31
_cell_measurement_theta_min      2.24
_cell_volume                     3928.1(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            59955
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.464
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1006 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8890.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.189
_refine_diff_density_max         0.741
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     978
_refine_ls_number_reflns         13814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0734
_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/[\s^2^(Fo^2^)+(0.0721P)^2^+8.3360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1710
_refine_ls_wR_factor_ref         0.1913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8680
_reflns_number_total             13814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj01321f2.cif
_cod_data_source_block           21gtu40_321_cpy_01_4t_0m
_cod_depositor_comments
'Adding full bibliography for 7063812--7063815.cif.'
_cod_database_code               7063815
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28),
 C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C1(H1), C2(H2), C5(H5),
 C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C55(H55), C56(H56), C59(H59), C60(H60), C61(H61), C62(H62), C64(H64),
  C65(H65), C68(H68), C69(H69), C70(H70), C71(H71), C37(H37), C38(H38),
 C41(H41), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C50(H50), C51(H51),
  C52(H52), C53(H53)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O7(H7A), O8(H8A)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 250 electrons were 
found in a volume of 716\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[CH3CH2CH2CH2CH2CH2CH3] per Unit Cell 
which account for 232 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              4052
_shelx_hkl_checksum              65134
_shelx_fab_checksum              90875
_olex2_submission_special_instructions 'No special instructions were received'