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_7062128
_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         '2(C25 H17 N7), 2(C3 H7 N O)'
_chemical_formula_sum            'C56 H48 N16 O2'
_chemical_formula_weight         977.10
_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                103.400(3)
_cell_angle_beta                 106.838(3)
_cell_angle_gamma                112.929(3)
_cell_formula_units_Z            1
_cell_length_a                   10.5322(4)
_cell_length_b                   11.0246(4)
_cell_length_c                   12.4797(4)
_cell_measurement_reflns_used    18876
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.69
_cell_measurement_theta_min      4.02
_cell_volume                     1175.70(9)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22892
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.639
_diffrn_reflns_theta_min         4.021
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_correction_T_min  0.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0032(5)
_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   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0743P)^2^+0.4152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3509
_reflns_number_total             4438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04774h2.cif
_cod_data_source_block           13503dmf
_cod_depositor_comments
'Adding full bibliography for 7062127--7062133.cif.'
_cod_original_cell_volume        1175.70(8)
_cod_database_code               7062128
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.864
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained planarity
 O1, C26, N1AA, C27, C28
 with sigma of 0.1
 O1A, C26A, N8A, C27A, C28A
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(C26) = Uanis(C26A)
Uanis(N1AA) = Uanis(N8A)
Uanis(C27) = Uanis(C27A)
Uanis(C28) = Uanis(C28A)
4. Rigid body (RIGU) restrains
 O1, C26, N1AA, C27, C28, O1A, C26A, N8A, C27A, C28A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1A, C26A, N8A, C27A, C28A} sigma for 1-2: 0.01, 1-3: 0.04
as in
{O1, C26, N1AA, C27, C28}
6. Others
 Sof(O1A)=Sof(C26A)=Sof(H26A)=Sof(N8A)=Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=
 Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(O1)=Sof(C26)=Sof(H26)=Sof(N1AA)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
7.a Me refined with riding coordinates:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C27A(H27D,H27E,H27F), C28A(H28D,
 H28E,H28F)
7.b Aromatic/amide H refined with riding coordinates:
 N10(H10), N7(H7), C18(H18), C17(H17), C16(H16), C15(H15), C11(H11), C9(H9),
 C3(H3), C4(H4), C5(H5), C6(H6), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C26A(H26A)
;
_shelx_res_checksum              84702
_olex2_submission_special_instructions 'No special instructions were received'