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_7039692
_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         'C40 H28 Ir N3 O2, 2(C H4 O)'
_chemical_formula_sum            'C42 H36 Ir N3 O4'
_chemical_formula_weight         838.94
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-12
_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                102.782(4)
_cell_angle_beta                 108.667(4)
_cell_angle_gamma                107.287(4)
_cell_formula_units_Z            2
_cell_length_a                   11.2366(4)
_cell_length_b                   12.7646(6)
_cell_length_c                   13.7741(6)
_cell_measurement_reflns_used    4617
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.7340
_cell_measurement_theta_min      1.8190
_cell_volume                     1674.30(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -88.00  -10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  131.0000  128.0000 78

  2 omega   38.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -131.0000   57.0000 49

  3 omega   81.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000   90.0000 25

  4 omega  -37.00   50.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000 -120.0000 87

  5 omega   10.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  120.0000 88

  6 omega   70.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -60.0000 27

  7 omega   -1.00  102.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   19.0000   60.0000 103

  8 omega    9.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000 -120.0000 52
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0098980000
_diffrn_orient_matrix_UB_12      0.0583141000
_diffrn_orient_matrix_UB_13      0.0028377000
_diffrn_orient_matrix_UB_21      -0.0318821000
_diffrn_orient_matrix_UB_22      -0.0192293000
_diffrn_orient_matrix_UB_23      -0.0579146000
_diffrn_orient_matrix_UB_31      -0.0645130000
_diffrn_orient_matrix_UB_32      -0.0094066000
_diffrn_orient_matrix_UB_33      0.0019900000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.1079
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18500
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    4.037
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.559
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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)
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.957
_refine_diff_density_min         -1.811
_refine_diff_density_rms         0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         8900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0380P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1132
_reflns_number_gt                7089
_reflns_number_total             8900
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt01461e2.cif
_cod_data_source_block           Ir1_15srv040
_cod_depositor_comments
'Adding full bibliography for 7039689--7039694.cif.'
_cod_original_cell_volume        1674.30(12)
_cod_database_code               7039692
_chemical_oxdiff_formula         'C40 H28 N3 O2 Ir1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{C2SA, O2SA}
{O2S, C2S}
3. Uiso/Uaniso restraints and constraints
Uiso(C2SA) = Uiso(O2SA)
Uiso(O2S) = Uiso(C2S)
4. Others
 Fixed Sof: C2SA(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5) O2S(0.5) H2S(0.5)
 O2SA(0.5) H2SD(0.5) C2S(0.5) H2SE(0.5) H2SF(0.5) H2SG(0.5)
5.a 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), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36),
 C37(H37), C42(H42), C43(H43), C44(H44), C45(H45)
5.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2SA(H2SA,H2SB,H2SC), C2S(H2SE,H2SF,H2SG)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2S(H2S), O2SA(H2SD)
;