Cyclometalation via Carbon‒Fluorine Bond Activation Induced by Silver Particles
Thomas, Hayden P.; Wang, Yue-Ming; Lorenzini, Fabio; Coles, Simon J.; Horton, Peter N.; Marr, Andrew C.; Saunders, Graham C.; Organometallics  (2017) –; doi:10.1021/acs.organomet.6b00872

data_4087067
_publ_section_title
;
 Cyclometalation via Carbon--Fluorine Bond Activation Induced by Silver
 Particles
;
_journal_name_full               Organometallics
_journal_paper_doi               10.1021/acs.organomet.6b00872
_journal_year                    2017
_chemical_formula_moiety         'C21 H22 Cl F4 Ir N2, C1 H2 Cl2'
_chemical_formula_sum            'C22 H24 Cl3 F4 Ir N2'
_chemical_formula_weight         690.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.252(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1891(8)
_cell_length_b                   15.6168(11)
_cell_length_c                   14.3860(10)
_cell_measurement_reflns_used    20902
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.3
_cell_volume                     2373.2(3)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 3.1 b27
;
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Image plate'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            'Rigaku Curved Fujifilm '
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle quarter \c goniometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       'profile data from oscillation \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    '0.3 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.1617
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32257
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.009
_diffrn_source                   'Sealed X-Ray tube'
_diffrn_source_current           40
_diffrn_source_power             2
_diffrn_source_size              '12mm x 0.4 mm long fine-focus'
_diffrn_source_target            Mo
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    6.008
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_description       Blade
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.040
_refine_diff_density_max         2.436
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5430
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0344P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3584
_reflns_number_total             5430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om6b00872_si_002.cif
_cod_data_source_block           2014ncs0413
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4087067
_shelx_estimated_absorpt_t_max   0.795
_shelx_estimated_absorpt_t_min   0.102
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.052) H3(0.049) H4A(0.037) H4B(0.037) H11A(0.059) H11B(0.059)
 H11C(0.059) H26A(0.061) H26B(0.061) H26C(0.061) H27A(0.063) H27B(0.063)
 H27C(0.063) H28A(0.06) H28B(0.06) H28C(0.06) H29A(0.058) H29B(0.058)
 H29C(0.058) H30A(0.057) H30B(0.057) H30C(0.057) H31A(0.072) H31B(0.072)
 H36A(0.091) H36B(0.091)
 Fixed X: H2(0.1501) H3(0.1698) H4A(0.462) H4B(0.3531) H11A(0.3351)
 H11B(0.3415) H11C(0.4665) H26A(0.6584) H26B(0.8077) H26C(0.7547) H27A(0.9116)
 H27B(1.0026) H27C(0.9595) H28A(0.8966) H28B(0.9231) H28C(0.7981) H29A(0.6269)
 H29B(0.6601) H29C(0.5266) H30A(0.464) H30B(0.5658) H30C(0.5312) H31A(0.9074)
 H31B(0.9331) H36A(0.9222) H36B(0.8262)
 Fixed Y: H2(0.4114) H3(0.2757) H4A(0.234) H4B(0.1737) H11A(0.4732)
 H11B(0.5323) H11C(0.4855) H26A(0.5769) H26B(0.5852) H26C(0.5226) H27A(0.4107)
 H27B(0.4277) H27C(0.3322) H28A(0.2436) H28B(0.2886) H28C(0.2323) H29A(0.2954)
 H29B(0.3866) H29C(0.372) H30A(0.4943) H30B(0.5555) H30C(0.5685) H31A(0.3128)
 H31B(0.2721) H36A(0.2455) H36B(0.2793)
 Fixed Z: H2(0.7069) H3(0.6251) H4A(0.6183) H4B(0.6318) H11A(0.8873)
 H11B(0.7982) H11C(0.8672) H26A(0.8728) H26B(0.8945) H26C(0.9599) H27A(0.9919)
 H27B(0.9283) H27C(0.942) H28A(0.8075) H28B(0.7163) H28C(0.6987) H29A(0.5768)
 H29B(0.5408) H29C(0.5567) H30A(0.6422) H30B(0.6197) H30C(0.7182) H31A(0.5186)
 H31B(0.4247) H36A(0.4262) H36B(0.3234)
;
_shelx_res_checksum              42955
_shelx_hkl_checksum              19947
_shelx_shelxl_version_number     2014/7