Aromatic alkyne insertion into six-membered cyclometalated pyridine complexes of iridium: different insertion modes and structurally novel products
Chu, Xiaodan; Zhang, Shaowei; Wang, Zhuo; Li, Tongyu; Zhu, Bolin; RSC Advances 8 (2018) 7164–; doi:10.1039/C7RA13547E

data_7230162
_publ_section_title
;
 Aromatic alkyne insertion into six-membered cyclometalated pyridine
 complexes of iridium: different insertion modes and structurally novel
 products
;
_journal_issue                   13
_journal_name_full               'RSC Advances'
_journal_page_first              7164
_journal_paper_doi               10.1039/C7RA13547E
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C37 H33 Cl Ir N O2, H2 O'
_chemical_formula_sum            'C37 H35 Cl Ir N O3'
_chemical_formula_weight         769.31
_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   mixed
_audit_creation_date             2017-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-12-06 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.702(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2945(2)
_cell_length_b                   24.4790(7)
_cell_length_c                   15.6644(4)
_cell_measurement_reflns_used    7453
_cell_measurement_temperature    151.0(3)
_cell_measurement_theta_max      73.6540
_cell_measurement_theta_min      4.5840
_cell_volume                     3114.41(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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      151.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -114.00 -13.00   1.00    1.00    --  -41.49 -57.00  30.00  101
  2  \w    -33.00  66.00   1.00    1.00    --   41.49 -38.00-180.00   99
  3  \w     17.00 116.00   1.00    1.00    --   41.49  38.00  30.00   99
  4  \w      1.00  82.00   1.00    1.00    --   41.49 -99.00-120.00   81
  5  \w     35.00 136.00   1.00    3.65    --  107.08 -61.00 150.00  101
  6  \w     25.00 109.00   1.00    3.65    --  107.08 -95.00  90.00   84
  7  \w     33.00 118.00   1.00    3.65    --  107.08-119.00 -46.00   85
  8  \w     25.00 109.00   1.00    3.65    --  107.08 -95.00 150.00   84
  9  \w     54.00 178.00   1.00    3.65    --  107.08  15.00-120.00  124
 10  \w   -118.00 -77.00   1.00    1.00    --  -41.49 -77.00 -90.00   41
 11  \w   -118.00 -93.00   1.00    1.00    --  -41.49 -77.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0261505000
_diffrn_orient_matrix_UB_12      0.0622822000
_diffrn_orient_matrix_UB_13      -0.0070923000
_diffrn_orient_matrix_UB_21      -0.0290142000
_diffrn_orient_matrix_UB_22      -0.0040941000
_diffrn_orient_matrix_UB_23      -0.1001018000
_diffrn_orient_matrix_UB_31      -0.1855633000
_diffrn_orient_matrix_UB_32      -0.0081672000
_diffrn_orient_matrix_UB_33      -0.0041269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15453
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.611
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.641
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.183
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0242P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0667
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4623
_reflns_number_total             5547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra13547e2.cif
_cod_data_source_block           a170606a
_cod_original_cell_volume        3114.40(16)
_cod_database_code               7230162
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21),
 C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-06-06
_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 2.628
_oxdiff_exptl_absorpt_empirical_full_min 0.649