One-pot dual catalysis for the hydrogenation of heteroarenes and arenes
Chatterjee, Basujit; Kalsi, Deepti; Kaithal, Akash; Bordet, Alexis; Leitner, Walter; Gunanathan, Chidambaram; Catalysis Science & Technology 10 (2020) 5163–5170; doi:10.1039/D0CY00928H

data_1558540
_publ_section_title
;
 One-pot dual catalysis for the hydrogenation of heteroarenes and arenes
;
_journal_issue                   15
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              5163
_journal_page_last               5170
_journal_paper_doi               10.1039/D0CY00928H
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 Cl2 N Ru'
_chemical_formula_sum            'C19 H21 Cl2 N Ru'
_chemical_formula_weight         435.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-24
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-06-23 deposited with the CCDC.	2020-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1672(3)
_cell_length_b                   13.7037(5)
_cell_length_c                   17.9697(8)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.71
_cell_volume                     1764.93(13)
_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_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7724
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         4.115
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0426 after correction.
The Ratio of minimum to maximum transmission is 0.8495.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0186P)^2^+0.6734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0463
_refine_ls_wR_factor_ref         0.0477
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2039
_reflns_number_total             2199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cy00928h2.cif
_cod_data_source_block           cg_bc_520_3_0m
_cod_depositor_comments
;Adding full bibliography for 1558540.cif.

 Adding full bibliography for 1558540.cif.
;
_cod_database_code               1558540
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.46(7) 0.54(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'