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_7157983
_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         'C41 H43 Cl N2 P Ru, Cl'
_chemical_formula_sum            'C41 H43 Cl2 N2 P Ru'
_chemical_formula_weight         766.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-03-19 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                85.671(3)
_cell_angle_beta                 78.534(3)
_cell_angle_gamma                67.010(3)
_cell_formula_units_Z            2
_cell_length_a                   10.0105(3)
_cell_length_b                   11.3092(4)
_cell_length_c                   19.0850(7)
_cell_measurement_reflns_used    11478
_cell_measurement_temperature    282.72(10)
_cell_measurement_theta_max      66.8900
_cell_measurement_theta_min      4.2050
_cell_volume                     1949.31(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      air
_diffrn_ambient_temperature      282.72(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   16.00  115.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   38.0000  -90.0000 99

  2 omega   64.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -90.0000 35

  3 omega   78.00  126.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -120.0000 48

  4 omega  123.00  151.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -120.0000 28

  5 omega  123.00  150.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  -90.0000 27

  6 omega  122.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 32

  7 omega  120.00  171.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 51

  8 omega  112.00  138.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000  -60.0000 26

  9 omega  114.00  167.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000   60.0000 53

 10 omega  120.00  146.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000  150.0000 26

 11 omega  117.00  153.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 36

 12 omega   73.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000   60.0000 38

 13 omega   62.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -30.0000 35

 14 omega   72.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000  -60.0000 34

 15 omega   65.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000 -180.0000 41

 16 omega   27.00   53.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -111.2419 26

 17 omega   45.00   70.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -88.0000 -150.9619 25

 18 omega   64.00  123.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -150.8211 59

 19 omega   98.00  130.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -111.2419 32

 20 omega   81.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000    2.0079 27

 21 omega   63.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -20.9206 26

 22 omega   35.00   74.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 39

 23 omega   57.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000   86.6200 53

 24 omega   80.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  162.6949 26

 25 omega   42.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  150.0000 26

 26 omega   37.00   62.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000  162.6949 25

 27 omega   20.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   55.4295 88

 28 omega   33.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  150.0000 66

 29 omega   68.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  120.0000 25

 30 omega   20.00  115.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000  150.0000 95

 31 omega   21.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000    2.0079 42

 32 omega   31.00   88.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000   60.0000 57

 33 omega    9.00   45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  -20.9206 36

 34 omega   23.00   50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000 -120.0000 27

 35 omega   12.00   78.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -120.0000 66

 36 omega   34.00   78.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000 -120.0000 44

 37 omega   19.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000 -150.0000 70

 38 omega   11.00   36.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -150.8211 25

 39 omega  -15.00   80.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -99.0000   30.0000 95

 40 omega   10.00   76.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  120.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0495842000
_diffrn_orient_matrix_UB_12      -0.0603701000
_diffrn_orient_matrix_UB_13      -0.0752199000
_diffrn_orient_matrix_UB_21      -0.1489079000
_diffrn_orient_matrix_UB_22      0.0894392000
_diffrn_orient_matrix_UB_23      -0.0196655000
_diffrn_orient_matrix_UB_31      0.0655646000
_diffrn_orient_matrix_UB_32      0.1012560000
_diffrn_orient_matrix_UB_33      -0.0271883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22685
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.090
_diffrn_reflns_theta_max         67.090
_diffrn_reflns_theta_min         4.247
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.541
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.4621P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6356
_reflns_number_total             6911
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00362c2.cif
_cod_data_source_block           exp_9819
_cod_depositor_comments
'Adding full bibliography for 7157983--7157985.cif.'
_cod_database_code               7157983
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.628
_shelx_estimated_absorpt_t_min   0.476
_reflns_odcompleteness_completeness 99.28
_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:
 C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C25(H25), C9(H9), C8(H8), C1(H1), C17(H17), C19(H19),
 C11(H11), C33(H33), C20(H20), C21(H21), C28(H28), C2(H2), C18(H18), C12(H12),
 C26(H26), C31(H31), C15(H15), C27(H27), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C35(H35A,H35B,H35C), C41(H41A,H41B,H41C), C40(H40A,H40B,
 H40C), C39(H39A,H39B,H39C), C36(H36A,H36B,H36C)
;
_olex2_submission_special_instructions 'No special instructions were received'