Molecular engineering of 3-arylated tetrazo[1,2-<i>b</i>]indazoles: divergent synthesis and structure-property relationships.
Bousfiha, Asmae; Abidi, Oumaima; Lemetayer, Louis; Sood, Navya; Tolbatov, Iogann; Barrois, Fabien; Daher, Ahmad; Cattey, Hélène; Cordier, Marie; Hissler, Muriel; Hierso, Jean-Cyrille; Fleurat-Lessard, Paul; Bouit, Pierre-Antoine; Roger, Julien; Dalton transactions (Cambridge, England : 2003) 53 (2024) 10737–10743; doi:10.1039/d4dt01122h

data_7716258
_publ_section_title
;
 Molecular engineering of 3-arylated tetrazo[1,2-<i>b</i>]indazoles:
 divergent synthesis and structure-property relationships.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10737
_journal_page_last               10743
_journal_paper_doi               10.1039/d4dt01122h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C24 H22 Cl F Ir N5, 1.37(C H2 Cl2)'
_chemical_formula_sum            'C25.37 H24.74 Cl3.74 F Ir N5'
_chemical_formula_weight         743.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-02-13 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.235(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.7718(10)
_cell_length_b                   8.4029(2)
_cell_length_c                   22.5382(7)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.47
_cell_volume                     5287.7(3)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'APEX3 (Bruker, 2020)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            96187
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.589
_diffrn_source                   'X-ray tube'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.461
_exptl_absorpt_correction_T_max  0.0377
_exptl_absorpt_correction_T_min  0.0165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.4377.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark black'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_description       prism
_exptl_crystal_F_000             2892
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of dichloromethane and heptane  by slow evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.049
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     357
_refine_ls_number_reflns         6066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0245P)^2^+17.2203P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5139
_reflns_number_total             6066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01122h2.cif
_cod_data_source_block           3-2FPh-TzIn_IrClCp
_cod_depositor_comments
'Adding full bibliography for 7716255--7716259.cif.'
_cod_database_code               7716258
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.669
_shelx_estimated_absorpt_t_min   0.611
_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. Others
 Fixed Sof: Cl3(0.55) Cl2(0.55) C25(0.55) H25A(0.55) H25B(0.55) Cl2A(0.45)
 Cl3A(0.45) C25A(0.45) H25C(0.45) H25D(0.45) Cl4(0.37) Cl5(0.37) C26(0.37)
 H26A(0.37) H26B(0.37)
3.a Free rotating group:
 Cl4(Cl5,C26)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C25A(H25C,H25D), C26(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C12(H12), C22(H22), C14(H14), C21(H21), C20(H20)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C6(H6A,H6B,H6C),
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              49601
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'