Highly potent extranuclear-targeted luminescent iridium(iii) antitumor agents containing benzimidazole-based ligands with a handle for functionalization.
Yellol, Jyoti; Pérez, Sergio A; Yellol, Gorakh; Zajac, Juraj; Donaire, Antonio; Vigueras, Gloria; Novohradsky, Vojtech; Janiak, Christoph; Brabec, Viktor; Ruiz, José; Chemical communications (Cambridge, England) 52 (2016) 14165–14168; doi:10.1039/c6cc07909a

data_7125255
_publ_section_title
;
 Highly potent extranuclear-targeted luminescent iridium(iii) antitumor
 agents containing benzimidazole-based ligands with a handle for
 functionalization.
;
_journal_issue                   98
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14165
_journal_page_last               14168
_journal_paper_doi               10.1039/c6cc07909a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C35 H29.50 Ir N7 O2, F6 P, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C35.5 H30.5 Cl F6 Ir N7 O2 P'
_chemical_formula_weight         959.79
_chemical_name_systematic
'bis(1-phenyl-1H-pyrazole-\k^2^N,C)-{methyl 1-butyl-2-(pyridin-2-yl)-1H-benzo[d]imidazole-5-carboxylate-\k^2^N,N'}iridium(III) hexafluorophosphate dichloromethane solvate'
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-06 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.7896(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.4157(10)
_cell_length_b                   16.5559(7)
_cell_length_c                   23.3462(9)
_cell_measurement_reflns_used    9344
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.64
_cell_volume                     8635.2(6)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            260552
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.049
_diffrn_reflns_theta_min         1.988
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.254
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       prism
_exptl_crystal_F_000             3772
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.160
_platon_squeeze_details
;
Possible disordered solvent residues in what would be
otherwise voids were tried to remove with the option
SQUEEZE by Platon.
In two voids of 735 \%A^3^ each, in the unit cell, 176 electrons
each, were removed.
Total potential solvent accessible void volume per unit cell
is 1468.2 \%A^3^ (17%) with a total electron count/cell of 358.
The total electron count for the potential solvent molecules is:
hexane = 48,
CH2Cl2 = 48.
The structure has Z = 8.
Thus, a half-occupied CH2Cl2 or hexane molecule with Z = 8 would
give 24 x 8 = 192 electrons per void in the unit cell.
With two voids of the same electron count, overall the approximate
 equivalent of a full hexane or CH2Cl2 molecule could be present 
per formula unit.
;
_refine_diff_density_max         1.645
_refine_diff_density_min         -2.134
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     676
_refine_ls_number_reflns         8538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+58.2454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8151
_reflns_number_total             8538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc07909a2.cif
_cod_data_source_block           gy200c_sq
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C35.50 H30.50 Cl F6 Ir N7 O2 P'
_cod_database_code               7125255
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.577
_shelx_estimated_absorpt_t_max   0.624
_shelx_res_checksum              20112
_solvent_exptl_crystal_recrystallization_method 'methylene chloride, hexane'