Design, synthesis and antimycobacterial activity of Imidazo[1,5-a]quinolines and their Zinc-complexes
Marner, Michael; Kulhanek, Niclas; Eichberg, Johanna; Hardes, Kornelia; Dal-Molin, Michael; Rybniker, Jan; Kirchner, Michael; Schäberle, Till; Goettlich, Richard; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D4MD00086B

data_7248304
_publ_section_title
;
 Design, synthesis and antimycobacterial activity of
 Imidazo[1,5-a]quinolines and their Zinc-complexes
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00086B
_journal_year                    2024
_chemical_formula_sum            'C93 H72 Cl12 Fe4 N12'
_chemical_formula_weight         2006.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-25 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.910(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.6450(18)
_cell_length_b                   20.687(3)
_cell_length_c                   15.733(2)
_cell_measurement_reflns_used    7400
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.53
_cell_volume                     4323.1(10)
_computing_cell_refinement       'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            93776
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_min         1.874
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2(Sheldrick, 2016)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2044
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.116
_refine_diff_density_max         1.916
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.074(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1140
_refine_ls_number_reflns         21460
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0702P)^2^+5.0057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.945
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                20140
_reflns_number_total             21460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00086b2.cif
_cod_data_source_block           DC22177_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7248304
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.647
_shelx_estimated_absorpt_t_max   0.884
_shelx_res_checksum              45174