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_7062393
_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         'C17 H20 Cl2 F3 N O Ru'
_chemical_formula_sum            'C17 H20 Cl2 F3 N O Ru'
_chemical_formula_weight         483.31
_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             2019-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-01 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                81.364(5)
_cell_angle_beta                 89.730(5)
_cell_angle_gamma                70.383(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8494(5)
_cell_length_b                   9.0853(5)
_cell_length_c                   14.9436(9)
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      28.6690
_cell_measurement_theta_min      2.6560
_cell_volume                     991.26(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.850
_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    -68.00  29.20   0.30    5.00    --   29.89  54.00 -30.00  324
  2  \w     20.00  47.00   0.30    5.00    --   29.89  54.00 150.00   90
  3  \w     72.00  99.00   0.30    5.00    --   29.89  54.00 150.00   90
  4  \w    -69.00 115.20   0.30    5.00    --   29.89  54.00-150.00  614
;
_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      0.0111732000
_diffrn_orient_matrix_UB_12      0.0126368000
_diffrn_orient_matrix_UB_13      -0.0473395000
_diffrn_orient_matrix_UB_21      0.0720303000
_diffrn_orient_matrix_UB_22      0.0279520000
_diffrn_orient_matrix_UB_23      0.0076791000
_diffrn_orient_matrix_UB_31      0.0625455000
_diffrn_orient_matrix_UB_32      -0.0781265000
_diffrn_orient_matrix_UB_33      0.0032360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.745
_diffrn_reflns_theta_min         2.758
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.29
_refine_diff_density_max         2.401
_refine_diff_density_min         -1.810
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.0011(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.274
_refine_ls_shift/su_mean         0.015
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1134P)^2^+0.6075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.2261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4424
_reflns_number_total             6212
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00210a2.cif
_cod_data_source_block           bp_06_rt
_cod_depositor_comments
'Adding full bibliography for 7062393--7062394.cif.'
_cod_database_code               7062393
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{C7A, C7B}
3. Uiso/Uaniso restraints and constraints
Uiso(C7A) = Uiso(C7B)
Uiso(F1A) = Uiso(F1B)
Uiso(F2A) = Uiso(F2B)
Uiso(F3B) = Uiso(F3A)
4. Others
 Sof(F2B)=Sof(C7B)=Sof(F1B)=Sof(F3B)=1-FVAR(1)
 Sof(F3A)=Sof(F1A)=Sof(C7A)=Sof(F2A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C6(H6), C11(H11), C8(H8), C10(H10), C2(H2), C5(H5), C3(H3)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.718