N-coordinated Ru(ii) catalyzed solvent free N-alkylation of primary amines with alcohols through borrowing hydrogen strategy
Patel, Bhavya; Ranjan, Rishi; Chauhan, Nimesh R.; Mukhopadhyay, Suman; Choudhury, Angshuman Roy; Vyas, Komal M.; New Journal of Chemistry 47 (2023) 8305–8317; doi:10.1039/D3NJ00210A

data_7062394
_publ_section_title
;
 N-coordinated Ru(ii) catalyzed solvent free N-alkylation of primary
 amines with alcohols through borrowing hydrogen strategy
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8305
_journal_page_last               8317
_journal_paper_doi               10.1039/D3NJ00210A
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C20 H20 Cl N O2 Ru'
_chemical_formula_sum            'C20 H20 Cl N O2 Ru'
_chemical_formula_weight         442.89
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-04 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.668(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8285(5)
_cell_length_b                   17.5067(5)
_cell_length_c                   10.5960(5)
_cell_measurement_reflns_used    4048
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      28.5650
_cell_measurement_theta_min      3.1360
_cell_volume                     1779.01(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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      298.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.919
_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    -69.00 118.20   0.30   10.00    --   29.89  54.00-150.00  624
  2  \w    -57.00 108.00   0.30   10.00    --   29.89  54.00  90.00  550
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0622688000
_diffrn_orient_matrix_UB_12      0.0073249000
_diffrn_orient_matrix_UB_13      0.0044750000
_diffrn_orient_matrix_UB_21      -0.0344621000
_diffrn_orient_matrix_UB_22      -0.0291011000
_diffrn_orient_matrix_UB_23      -0.0509806000
_diffrn_orient_matrix_UB_31      0.0200807000
_diffrn_orient_matrix_UB_32      -0.0272331000
_diffrn_orient_matrix_UB_33      0.0556177000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15820
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.792
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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    1.654
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         1.769
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         6065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0428P)^2^+0.5905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             6065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00210a2.cif
_cod_data_source_block           bp07
_cod_depositor_comments
'Adding full bibliography for 7062393--7062394.cif.'
_cod_original_cell_volume        1779.01(15)
_cod_database_code               7062394
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), C14(H14), C2(H2), C8(H8), C13(H13), C7(H7), C5(H5),
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c)
;
_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 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.881