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_7039690
_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         'C2 F3 O2, C12 H16 N'
_chemical_formula_sum            'C14 H16 F3 N O2'
_chemical_formula_weight         287.28
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-03-03
_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                105.666(5)
_cell_angle_beta                 99.952(4)
_cell_angle_gamma                106.901(5)
_cell_formula_units_Z            2
_cell_length_a                   6.3784(3)
_cell_length_b                   9.4630(6)
_cell_length_c                   12.6226(6)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.7330
_cell_measurement_theta_min      1.7920
_cell_volume                     675.27(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'XS (Sheldrick, 2008)'
_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   51.00   86.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  150.0000 35

  2 omega  -14.00   74.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -109.0000  123.0000 88

  3 omega    5.00   46.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000    0.0000 41

  4 omega    3.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -90.0000 95

  5 omega  -41.00   49.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -38.0000  -30.0000 90

  6 omega    9.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000 -120.0000 89

  7 omega   35.00   93.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  -30.0000 58

  8 omega    9.00   98.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   90.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0586424000
_diffrn_orient_matrix_UB_12      0.0426223000
_diffrn_orient_matrix_UB_13      0.0584498000
_diffrn_orient_matrix_UB_21      -0.0036991000
_diffrn_orient_matrix_UB_22      0.0704290000
_diffrn_orient_matrix_UB_23      -0.0084961000
_diffrn_orient_matrix_UB_31      -0.1055527000
_diffrn_orient_matrix_UB_32      -0.0127032000
_diffrn_orient_matrix_UB_33      0.0138312000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8762
_diffrn_reflns_theta_full        28.99
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.39
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.2800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2879
_reflns_number_total             3601
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt01461e2.cif
_cod_data_source_block           7_15srv059
_cod_depositor_comments
'Adding full bibliography for 7039689--7039694.cif.'
_cod_original_cell_volume        675.27(6)
_cod_database_code               7039690
_chemical_oxdiff_formula         'C12 H15 N1'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;