Biguanide Iridium(III) Complexes with Potent Antimicrobial Activity.
Chen, Feng; Moat, John; McFeely, Daniel; Clarkson, Guy; Hands-Portman, Ian J; Furner-Pardoe, Jessica P; Harrison, Freya; Dowson, Christopher G.; Sadler, Peter J.; Journal of medicinal chemistry 61 (2018) 7330–7344; doi:10.1021/acs.jmedchem.8b00906

data_1553263
_publ_section_title
;
 Biguanide Iridium(III) Complexes with Potent Antimicrobial Activity.
;
_journal_issue                   16
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              7330
_journal_page_last               7344
_journal_paper_doi               10.1021/acs.jmedchem.8b00906
_journal_volume                  61
_journal_year                    2018
_chemical_formula_moiety         'C18 H23 Cl Ir N5, 0.75(C H4 O)'
_chemical_formula_sum            'C18.75 H26 Cl Ir N5 O0.75'
_chemical_formula_weight         561.09
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.78544(6)
_cell_length_b                   14.43434(11)
_cell_length_c                   23.04719(13)
_cell_measurement_reflns_used    20430
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.8120
_cell_measurement_theta_min      3.7280
_cell_volume                     3920.67(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -95.00   3.00   1.00    1.00    --  -41.46 125.00 -90.00   98
  2  \w    -70.00  32.00   1.00    1.00    --  -41.46  57.00-120.00  102
  3  \w     32.00 109.00   1.00    4.00    --  114.00 -95.00-180.00   77
  4  \w     38.00 147.00   1.00    4.00    --  114.00 -77.00-120.00  109
  5  \w     86.00 178.00   1.00    4.00    --  114.00  30.00 -30.00   92
  6  \w     38.00 116.00   1.00    4.00    --  114.00-111.00  90.00   78
  7  \w     38.00 142.00   1.00    4.00    --  114.00 -30.00 -60.00  104
  8  \w     85.00 178.00   1.00    4.00    --  114.00  61.00 -90.00   93
  9  \w   -114.00 -13.00   1.00    1.00    --  -41.46 -57.00-150.00  101
 10  \w   -114.00 -13.00   1.00    1.00    --  -41.46 -57.00  90.00  101
 11  \w     61.00 175.00   1.00    4.00    --  114.00  15.00 120.00  114
 12  \w     86.00 178.00   1.00    4.00    --  114.00  30.00-150.00   92
 13  \w     88.00 178.00   1.00    4.00    --  114.00  45.00 150.00   90
 14  \w     81.00 178.00   1.00    4.00    --  114.00  77.00   0.00   97
 15  \w   -118.00  -9.00   1.00    1.00    --  -41.46 -77.00 -30.00  109
 16  \w     -4.00  82.00   1.00    1.00    --   41.46 -99.00  90.00   86
 17  \w     85.00 178.00   1.00    4.00    --  114.00  61.00-120.00   93
 18  \w     81.00 122.00   1.00    4.00    --  114.00  77.00 -30.00   41
 19  \w     81.00 178.00   1.00    4.00    --  114.00  77.00  60.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0210477000
_diffrn_orient_matrix_UB_12      0.0405035000
_diffrn_orient_matrix_UB_13      0.0609098000
_diffrn_orient_matrix_UB_21      0.1263653000
_diffrn_orient_matrix_UB_22      0.0134538000
_diffrn_orient_matrix_UB_23      -0.0149135000
_diffrn_orient_matrix_UB_31      -0.0260039000
_diffrn_orient_matrix_UB_32      0.0977968000
_diffrn_orient_matrix_UB_33      -0.0231878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            40117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.154
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.576
_exptl_absorpt_correction_T_max  0.325
_exptl_absorpt_correction_T_min  0.098
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_description       block
_exptl_crystal_F_000             2188
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.157
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.000039(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+1.0554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0611
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3912
_reflns_number_total             4185
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm8b00906_si_003.cif
_cod_data_source_block           fc9
_cod_database_code               1553263
_chemical_oxdiff_formula         'C19 H27 Cl O Ir'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
The methanol solvent was modeled at 0.75 occupancy.
The NHs were located in a difference map and given Uiiso 1.5 times 
the Uequiv of the parent nitrogen. They were refined with a DFIX 
restraint to give them similar N-H bond lengths. 
The OH was placed at a calculated position.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All N(H,H) groups, All O(H) groups
2. Restrained distances
 N10-H10 = N11-H11B = N11-H11A = N12-H12
 0.88 with sigma of 0.008
3. Others
 Fixed Sof: C24(0.75) H24A(0.75) H24B(0.75) H24C(0.75) O23(0.75) H23(0.75)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
4.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C)
4.c Idealised tetrahedral OH refined as rotating group:
 O23(H23)
;
_shelx_res_checksum              77010
_shelx_hkl_checksum              51699
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.763