Pyridyl-benzimidazole derivatives decorated with phenylazo substituents and their low-spin iron(ii) complexes: a study of the synthesis, structure and photoisomerization
Orvoš, Jakub; Fischer, Róbert; Brachňaková, Barbora; Pavlik, Ján; Moncoľ, Ján; Šagátová, Alexandra; Fronc, Marek; Kožíšek, Jozef; Routaboul, Lucie; Bousseksou, Azzedine; Šalitroš, Ivan; New Journal of Chemistry 47 (2023) 1488–1497; doi:10.1039/D2NJ04774H

data_7062132
_publ_section_title
;
 Pyridyl-benzimidazole derivatives decorated with phenylazo substituents
 and their low-spin iron(ii) complexes: a study of the synthesis,
 structure and photoisomerization
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1488
_journal_page_last               1497
_journal_paper_doi               10.1039/D2NJ04774H
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety
'C50 H34 Fe N14, 1.75(C F3 O3 S), 0.75(C2 H6 O), C H3 N O2'
_chemical_formula_sum            'C54.25 H41.5 F5.25 Fe N15 O8 S1.75'
_chemical_formula_weight         1243.23
_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
_audit_creation_date             2022-06-07
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-10 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                76.494(2)
_cell_angle_beta                 87.725(3)
_cell_angle_gamma                82.131(2)
_cell_formula_units_Z            2
_cell_length_a                   13.2426(4)
_cell_length_b                   14.0283(4)
_cell_length_c                   15.6093(5)
_cell_measurement_reflns_used    29798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.06
_cell_measurement_theta_min      2.91
_cell_volume                     2792.93(15)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            99703
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.666
_diffrn_reflns_theta_min         2.912
_exptl_absorpt_coefficient_mu    3.526
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270.
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Finally a spherical absorption correction was done within STOE LANA.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1274
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     882
_refine_ls_number_reflns         10546
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.1720
_refine_ls_R_factor_gt           0.0853
_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^)+(0.1655P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2278
_refine_ls_wR_factor_ref         0.2766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4994
_reflns_number_total             10546
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04774h2.cif
_cod_data_source_block           bb199
_cod_depositor_comments
'Adding full bibliography for 7062127--7062133.cif.'
_cod_original_formula_sum        'C54.25 H41.50 F5.25 Fe N15 O8 S1.75'
_cod_database_code               7062132
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.569
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F5T-C2T
 1.35 with sigma of 0.003
 F4T-C2T
 1.35 with sigma of 0.003
 F6T-C2T
 1.35 with sigma of 0.003
 F6T-F4T
 2.35 with sigma of 0.003
 F6T-F5T
 2.35 with sigma of 0.003
 F5T-F4T
 2.35 with sigma of 0.003
 O1T-S1T
 1.45 with sigma of 0.003
 O2T-S1T
 1.45 with sigma of 0.003
 O3T-S1T
 1.45 with sigma of 0.003
 O1T-O2T
 2.45 with sigma of 0.003
 O1T-O3T
 2.45 with sigma of 0.003
 O2T-O3T
 2.45 with sigma of 0.003
3. Rigid bond restraints
 F5T, F4T, C2T, F6T, O1T, O3T, O2T, S1T, F2T, F3T, F1T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
F5T \\sim F4T \\sim C2T \\sim F6T \\sim O1T \\sim O3T \\sim O2T \\sim S1T \\sim
F2T \\sim F3T \\sim F1T: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
5. Others
 Fixed Sof: S1T(0.5) S2T(0.75) S3T(0.5) F1T(0.5) F2T(0.5) F3T(0.5) F4T(0.75)
 F5T(0.75) F6T(0.75) F7T(0.5) F8T(0.5) F9T(0.5) O1E(0.5) H1E(0.5) O1T(0.5)
 O2E(0.25) H2E(0.25) O2T(0.5) O3T(0.5) O4T(0.75) O5T(0.75) O6T(0.75) O7T(0.5)
 O8T(0.5) O9T(0.5) C1E(0.5) H1EA(0.5) H1EB(0.5) C1T(0.5) C2E(0.5) H2EA(0.5)
 H2EB(0.5) H2EC(0.5) C2T(0.75) C3E(0.25) H3EA(0.25) H3EB(0.25) C3T(0.5)
 C4E(0.25) H4EA(0.25) H4EB(0.25) H4EC(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C1E(H1EA,H1EB), C3E(H3EA,H3EB)
6.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N10(H10), N11(H11), N14(H14), C1AA(H1AA), C3(H3), C5(H5), C6(H6),
 C9(H9), C11(H11A), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31), C34(H34),
  C36(H36), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46), C47(H47),
 C48(H48), C49(H49), C50(H50)
6.c Idealised Me refined as rotating group:
 C1N(H1NA,H1NB,H1NC), C2E(H2EA,H2EB,H2EC), C4E(H4EA,H4EB,H4EC)
6.d Idealised tetrahedral OH refined as rotating group:
 O1E(H1E), O2E(H2E)
;
_shelx_res_checksum              34203
_olex2_submission_special_instructions 'No special instructions were received'