Ruthenium(II) complexes with N-heterocyclic carbene-phosphine ligands for the <i>N</i>-alkylation of amines with alcohols.
Huang, Ming; Li, Yinwu; Lan, Xiao-Bing; Liu, Jiahao; Zhao, Cunyuan; Liu, Yan; Ke, Zhuofeng; Organic & biomolecular chemistry 19 (2021) 3451–3461; doi:10.1039/d1ob00362c

data_7157985
_publ_section_title
;
 Ruthenium(II) complexes with N-heterocyclic carbene-phosphine ligands for
 the <i>N</i>-alkylation of amines with alcohols.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3451
_journal_page_last               3461
_journal_paper_doi               10.1039/d1ob00362c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         '0.13(C33 H35 Cl N2 P Ru), 0.06(F6 P)'
_chemical_formula_sum            'C H Cl F N P Ru'
_chemical_formula_weight         213.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2019-04-23 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.0420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            62
_cell_length_a                   12.9079(2)
_cell_length_b                   14.7545(2)
_cell_length_c                   35.0697(4)
_cell_measurement_reflns_used    9164
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.0840
_cell_measurement_theta_min      4.5430
_cell_volume                     6653.17(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_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   -128.00 -39.00   1.00    1.00    --  -41.14   0.00 120.00   89
  2  \w    -98.00 -72.00   1.00    1.00    --  -41.14 -38.00  30.00   26
  3  \w    -66.00 -18.00   1.00    1.00    --  -41.14 -38.00  30.00   48
  4  \w     30.00  86.00   1.00    1.00    --   41.14-125.00-150.00   56
  5  \w      1.00  45.00   1.00    1.00    --   41.14 -57.00-150.00   44
  6  \w     39.00 124.00   1.00    2.00    --  107.79 -30.00-150.00   85
  7  \w     36.00 101.00   1.00    2.00    --  107.79 -30.00 -60.00   65
  8  \w     79.00 150.00   1.00    2.00    --  107.79  61.00  60.00   71
  9  \w     40.00 100.00   1.00    2.00    --  107.79-125.00 120.00   60
 10  \w     48.00 118.00   1.00    2.00    --  107.79-125.00-150.00   70
 11  \w    128.00 177.00   1.00    2.00    --  107.79 125.00   0.00   49
 12  \w     38.00  85.00   1.00    2.00    --  107.79 -94.00 -30.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0030580000
_diffrn_orient_matrix_UB_12      0.1036955000
_diffrn_orient_matrix_UB_13      -0.0054764000
_diffrn_orient_matrix_UB_21      -0.1118228000
_diffrn_orient_matrix_UB_22      -0.0069884000
_diffrn_orient_matrix_UB_23      -0.0190840000
_diffrn_orient_matrix_UB_31      -0.0428801000
_diffrn_orient_matrix_UB_32      0.0109014000
_diffrn_orient_matrix_UB_33      0.0393407000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.359
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    37.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    3.304
_exptl_crystal_description       block
_exptl_crystal_F_000             6138
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.999
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+6.2924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6173
_reflns_number_total             6569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00362c2.cif
_cod_data_source_block           19041902_sq
_cod_depositor_comments
'Adding full bibliography for 7157983--7157985.cif.'
_cod_database_code               7157985
_chemical_oxdiff_formula         'C H Cl N P Ru F'
_chemical_oxdiff_usercomment     2019.4.19-RU-1
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Ternary CH refined with riding coordinates:
 C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C28(H28), C18(H18), C3(H3), C12(H12), C2(H2), C26(H26), C9(H9),
 C6(H6), C16(H16), C25(H25), C29(H29), C8(H8), C20(H20), C7(H7), C19(H19),
 C21(H21), C13(H13), C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,
 H33C)
;
_shelx_fab_checksum              76832
_shelx_shelxl_version_number     2014/7
_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 8.159
_oxdiff_exptl_absorpt_empirical_full_min 0.629