The use of organolithium reagents for the synthesis of 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes.
Davidson, Ross; Hsu, Yu-Ting; Batchelor, Thomas; Yufit, Dmitry; Beeby, Andrew; Dalton transactions (Cambridge, England : 2003) 45 (2016) 11496–11507; doi:10.1039/c6dt01461e

data_7039694
_publ_section_title
;
 The use of organolithium reagents for the synthesis of
 4-aryl-2-phenylpyridines and their corresponding iridium(iii) complexes.
;
_journal_issue                   28
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11496
_journal_page_last               11507
_journal_paper_doi               10.1039/c6dt01461e
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C41 H35 Ir N2 O4, C H2 Cl2'
_chemical_formula_sum            'C42 H37 Cl2 Ir N2 O4'
_chemical_formula_weight         896.84
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-14 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                69.040(10)
_cell_angle_beta                 74.260(10)
_cell_angle_gamma                71.550(10)
_cell_formula_units_Z            2
_cell_length_a                   9.3800(6)
_cell_length_b                   14.4932(9)
_cell_length_c                   14.9593(9)
_cell_measurement_reflns_used    7337
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.33
_cell_volume                     1772.6(2)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker SMART CCD 6000'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27616
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.48
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.964
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0698 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.8465.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.856
_refine_diff_density_min         -1.435
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         9378
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0738
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                7579
_reflns_number_total             9378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt01461e2.cif
_cod_data_source_block           Ir3_15srv109
_cod_depositor_comments
'Adding full bibliography for 7039689--7039694.cif.'
_cod_original_cell_volume        1772.57(19)
_cod_database_code               7039694
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C1S \\sim Cl3-C1S \\sim Cl2-C1S
 with sigma of 0.003
3. Others
 Fixed Sof: Cl2(0.5) Cl3(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) H1SD(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C1S(H1SC,H1SD)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C28(H28), C29(H29),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C40(H40)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,H43B,
 H43C)
;