Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines.
Pradhan, Subham; Thiyagarajan, Subramanian; Gunanathan, Chidambaram; Organic & biomolecular chemistry 19 (2021) 7147–7151; doi:10.1039/d1ob01218e

data_7158234
_publ_section_title
;
 Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7147
_journal_page_last               7151
_journal_paper_doi               10.1039/d1ob01218e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C20 H26 N2'
_chemical_formula_sum            'C20 H26 N2'
_chemical_formula_weight         294.43
_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
_audit_creation_date             2021-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                94.559(2)
_cell_angle_beta                 102.195(2)
_cell_angle_gamma                117.627(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2530(2)
_cell_length_b                   8.2551(2)
_cell_length_c                   14.7902(2)
_cell_measurement_reflns_used    11061
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.2840
_cell_measurement_theta_min      6.1670
_cell_volume                     854.10(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -100.00 -15.00   0.50    0.25    --  -38.50 143.00  37.00  170
  2  \w    -88.00  -8.00   0.50    0.25    --  -38.50 127.00-132.00  160
  3  \w     29.00 102.00   0.50    0.25    --   49.31-127.00 152.00  146
  4  \w     38.00 114.00   0.50    0.98    --  102.63-127.00 152.00  152
  5  \w     39.00 126.00   0.50    0.98    --  102.63-143.00 -17.00  174
  6  \w     87.00 166.00   0.50    0.98    --  102.63 143.00  37.00  158
  7  \w     96.00 167.00   0.50    0.98    --  102.63 127.00-132.00  142
  8  \w    -42.00  28.00   0.50    0.25    --  -38.50  38.00 -30.00  140
  9  \w   -105.00 -35.00   0.50    0.25    --  -38.50 -38.00 150.00  140
 10  \w     38.00 112.00   0.50    0.25    --   49.31  57.00 150.00  148
 11  \w    -20.00  55.00   0.50    0.25    --   49.31 -19.00 -30.00  150
 12  \w     46.00 116.00   0.50    0.25    --   49.31  38.00-150.00  140
 13  \w     37.00 111.00   0.50    0.25    --   49.31-143.00 -17.00  148
 14  \w     98.00 167.00   0.50    0.98    --  102.63  45.00-120.00  138
 15  \w     38.00 107.00   0.50    0.98    --  102.63 -45.00 120.00  138
 16  \w     34.00 107.00   0.50    0.98    --  102.63 -94.00-120.00  146
 17  \w     97.00 168.00   0.50    0.98    --  102.63 125.00   0.00  142
 18  \w     34.00 107.00   0.50    0.98    --  102.63 -94.00  30.00  146
 19  \w     34.00 107.00   0.50    0.98    --  102.63 -94.00  60.00  146
 20  \w     34.00 111.00   0.50    0.98    --  102.63 -15.00   0.00  154
 21  \w     90.00 165.00   0.50    0.98    --  102.63  61.00 120.00  150
 22  \w     97.00 168.00   0.50    0.98    --  102.63 125.00  90.00  142
 23  \w     35.00 106.00   0.50    0.98    --  102.63 -30.00 120.00  142
 24  \w     38.00 126.00   0.50    0.98    --  102.63 -77.00  60.00  176
 25  \w     97.00 168.00   0.50    0.98    --  102.63 125.00  60.00  142
 26  \w     34.00 107.00   0.50    0.98    --  102.63 -94.00 150.00  146
 27  \w     40.00 116.00   0.50    0.98    --  102.63 -61.00 -90.00  152
 28  \w    103.00 167.00   0.50    0.98    --  102.63  77.00  90.00  128
 29  \w    103.00 167.00   0.50    0.98    --  102.63  77.00-180.00  128
 30  \w     35.00 106.00   0.50    0.98    --  102.63 -30.00 -60.00  142
 31  \w     95.00 171.00   0.50    0.98    --  102.63  15.00-180.00  152
 32  \w     38.00  84.00   0.50    0.25    --   49.31  57.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0970961000
_diffrn_orient_matrix_UB_12      0.0535737000
_diffrn_orient_matrix_UB_13      0.1071653000
_diffrn_orient_matrix_UB_21      -0.1687264000
_diffrn_orient_matrix_UB_22      0.0176423000
_diffrn_orient_matrix_UB_23      0.0182242000
_diffrn_orient_matrix_UB_31      -0.1014688000
_diffrn_orient_matrix_UB_32      -0.2076810000
_diffrn_orient_matrix_UB_33      0.0060804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        61.473
_diffrn_reflns_theta_max         61.473
_diffrn_reflns_theta_min         6.182
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+0.7656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2553
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01218e2.cif
_cod_data_source_block           cg-sp-61
_cod_depositor_comments
'Adding full bibliography for 7158232--7158234.cif.'
_cod_database_code               7158234
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C40 H52 N4 '
_diffrn_oxdiff_digest_frames
;
016c4ba5fcc49094a53c880df09b4a5ea00006526e7
;
_diffrn_oxdiff_digest_hkl
;
01cb71a589637cb813e2eb3653d6bae788a79b
;
_reflns_odcompleteness_completeness 99.87
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C5(H5), C15(H15), C13(H13), C3(H3), C10(H10)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              81701
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.448