An ambient pressure, direct hydrogenation of ketones.
Zhang, Long; Lu, Zhiyao; Rander, Andrew R.; Williams, Travis J.; Chemical communications (Cambridge, England) 59 (2023) 8107–8110; doi:10.1039/d3cc01014g

data_7131783
_publ_section_title
;
 An ambient pressure, direct hydrogenation of ketones.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8107
_journal_page_last               8110
_journal_paper_doi               10.1039/d3cc01014g
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C19 H19 Cl Ir N3 O'
_chemical_formula_sum            'C19 H19 Cl Ir N3 O'
_chemical_formula_weight         533.02
_chemical_name_systematic
'[ 2-((3-mesityl-2H-1l4,3l4-imidazol-1-yl)methyl)pyridine-kappa2 N1 C2)=eta 3 p-cymene] Iridium (I) carbonyl chloride'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-04-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-21 deposited with the CCDC.	2023-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.108(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7180(2)
_cell_length_b                   15.1641(3)
_cell_length_c                   14.4976(3)
_cell_measurement_reflns_used    31218
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      32.3350
_cell_measurement_theta_min      2.6770
_cell_volume                     1841.35(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.899
_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    -19.00  67.00   0.50    4.39    --   -7.34  11.00 -36.00  172
  2  \w    -81.00   5.00   0.50    4.39    --   -7.34 -11.00 150.00  172
  3  \w    -18.00  65.00   0.50    4.39    --   -7.34  38.00 150.00  166
  4  \w    -29.00  25.00   0.50    4.39    --   -7.34  77.00   0.00  108
  5  \w    -14.00  25.00   0.50    4.39    --    7.97  77.00   0.00   78
  6  \w     -7.00  39.00   0.50    4.39    --    7.97 -99.00 120.00   92
  7  \w    -14.00  25.00   0.50    4.39    --    7.97  77.00-120.00   78
  8  \w    -82.00   4.00   0.50    4.39    --   -7.34 -19.00 -30.00  172
  9  \w    -29.00  25.00   0.50    4.39    --   -7.34  77.00  90.00  108
 10  \w    -25.00  14.00   0.50    4.39    --   -7.34 -77.00-150.00   78
 11  \w    -60.00   7.00   0.50    4.39    --   -7.34 -57.00 150.00  134
 12  \w     -7.00  22.00   0.50    4.39    --   -7.34 -99.00  60.00   58
 13  \w    -25.00  30.00   0.50    4.39    --    7.97 -77.00 -90.00  110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0685409000
_diffrn_orient_matrix_UB_12      0.0035271000
_diffrn_orient_matrix_UB_13      -0.0399365000
_diffrn_orient_matrix_UB_21      -0.0484652000
_diffrn_orient_matrix_UB_22      0.0054981000
_diffrn_orient_matrix_UB_23      0.0316043000
_diffrn_orient_matrix_UB_31      0.0110423000
_diffrn_orient_matrix_UB_32      0.0463195000
_diffrn_orient_matrix_UB_33      -0.0007529000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            50998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.409
_diffrn_reflns_theta_min         2.686
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    7.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pinkish pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_description       cube
_exptl_crystal_F_000             1024
_exptl_crystal_recrystallization_method
'prepared from slow liquid diffiusion of dichloromethane and diethyl ether.'
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.058
_refine_diff_density_max         2.646
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0039P)^2^+6.6894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4924
_reflns_number_total             5943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01014g2.cif
_cod_data_source_block           arr-201_auto
_cod_database_code               7131783
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Ir C18 Cl N3 H19'
_chemical_oxdiff_usercomment     'Long's crystal'
_shelx_estimated_absorpt_t_max   0.673
_shelx_estimated_absorpt_t_min   0.361
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C16(H16)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              30772
_shelx_hkl_checksum              52911
_olex2_exptl_crystal_mounting_method 'mounted on a loop'
_olex2_submission_original_sample_id ARR-201
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.851