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_7157984
_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         'C38 H37 Cl N2 P Ru, F6 P'
_chemical_formula_sum            'C38 H37 Cl F6 N2 P2 Ru'
_chemical_formula_weight         834.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-25 deposited with the CCDC.	2021-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.44120(10)
_cell_length_b                   11.3932(2)
_cell_length_c                   29.2341(3)
_cell_measurement_reflns_used    8900
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.0390
_cell_measurement_theta_min      4.1180
_cell_volume                     3477.65(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -89.00 -29.00   1.00    1.00    --  -41.14 125.00  30.00   60
  2  \w   -110.00 -30.00   1.00    1.00    --  -41.14 -38.00  60.00   80
  3  \w    -26.00   0.00   1.00    1.00    --   41.14 -57.00  30.00   26
  4  \w     37.00  63.00   1.00    2.93    --  107.79 -61.00-150.00   26
  5  \w     37.00  66.00   1.00    2.93    --  107.79 -61.00-180.00   29
  6  \w     86.00 135.00   1.00    2.93    --  107.79 -61.00-150.00   49
  7  \w     29.00  94.00   1.00    2.93    --  107.79 -94.00 -90.00   65
  8  \w     32.00 140.00   1.00    2.93    --  107.79 -77.00   0.00  108
  9  \w   -113.00 -73.00   1.00    1.00    --  -41.14 -38.00  30.00   40
 10  \w     27.00  57.00   1.00    1.00    --   41.14-125.00-180.00   30
 11  \w    132.00 178.00   1.00    2.93    --  107.79  30.00-150.00   46
 12  \w     29.00  55.00   1.00    2.93    --  107.79 -94.00  90.00   26
 13  \w     82.00 110.00   1.00    2.93    --  107.79 -94.00  90.00   28
 14  \w     82.00 110.00   1.00    2.93    --  107.79-125.00   0.00   28
 15  \w     78.00 104.00   1.00    2.93    --  107.79-125.00-120.00   26
 16  \w     89.00 115.00   1.00    2.93    --  107.79  30.00-150.00   26
;
_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      0.0759533000
_diffrn_orient_matrix_UB_12      0.0373189000
_diffrn_orient_matrix_UB_13      0.0427706000
_diffrn_orient_matrix_UB_21      -0.0611751000
_diffrn_orient_matrix_UB_22      0.1228992000
_diffrn_orient_matrix_UB_23      -0.0024196000
_diffrn_orient_matrix_UB_31      -0.1107345000
_diffrn_orient_matrix_UB_32      -0.0423154000
_diffrn_orient_matrix_UB_33      0.0306735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14160
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.204
_diffrn_reflns_theta_min         4.165
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91972
_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    1.593
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.505(10)
_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     455
_refine_ls_number_reflns         6846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0487P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                6617
_reflns_number_total             6846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00362c2.cif
_cod_data_source_block           19042408
_cod_depositor_comments
;
Adding full bibliography for 7157983--7157985.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         85.55
_cod_original_formula_moiety         '0.1(C38 H37 Cl N2 P Ru), 0.1(F6 P)'
_cod_original_formula_units_Z            39
_cod_original_formula_sum        'C3.90 H3.79 Cl0.10 F0.62 N0.21 P0.21 Ru0.10'
_cod_database_code               7157984
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N  Cl Ru F'
_chemical_oxdiff_usercomment     2019.4.22-rU-2
_shelx_estimated_absorpt_t_max   0.596
_shelx_estimated_absorpt_t_min   0.206
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.495(10)
 0.505(10)
2. 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
3.a Ternary CH refined with riding coordinates:
 C36(H36)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C9(H9), C19(H19), C20(H20), C18(H18), C24(H24), C2(H2), C11(H11),
 C3(H3), C12(H12), C13(H13), C31(H31), C27(H27), C5(H5), C14(H14), C25(H25),
 C32(H32), C21(H21), C22(H22), C7(H7), C34(H34), C6(H6), C35(H35), C26(H26),
 C8(H8)
3.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C)
;
_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 1.156
_oxdiff_exptl_absorpt_empirical_full_min 0.891