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_7158232
_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         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37
_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                80.613(3)
_cell_angle_beta                 85.440(3)
_cell_angle_gamma                89.520(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2951(2)
_cell_length_b                   7.8493(3)
_cell_length_c                   16.3441(5)
_cell_measurement_reflns_used    7407
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1210
_cell_measurement_theta_min      5.4840
_cell_volume                     794.25(5)
_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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_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    -99.00 -14.00   0.50    0.88    --  -38.50 141.00-114.00  170
  2  \w    -90.00  -8.00   0.50    0.88    --  -38.50 129.00  73.00  164
  3  \w     36.00 110.00   0.50    0.88    --   49.31-141.00-172.00  148
  4  \w     30.00 103.00   0.50    0.88    --   49.31-129.00  -0.00  146
  5  \w     39.00 115.00   0.50    3.49    --  102.63-129.00  -0.00  152
  6  \w     95.00 167.00   0.50    3.49    --  102.63 129.00  73.00  144
  7  \w     39.00 124.00   0.50    3.49    --  102.63-141.00-172.00  170
  8  \w     88.00 166.00   0.50    3.49    --  102.63 141.00-114.00  156
  9  \w   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00   0.00  140
 10  \w   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00-180.00  140
 11  \w    -42.00  28.00   0.50    0.88    --  -38.50  38.00-180.00  140
 12  \w    -42.00  28.00   0.50    0.88    --  -38.50  38.00 -60.00  140
 13  \w     40.00 116.00   0.50    3.49    --  102.63 -61.00 150.00  152
 14  \w     99.00 171.00   0.50    3.49    --  102.63  30.00 -90.00  144
 15  \w     38.00 107.00   0.50    3.49    --  102.63 -45.00 -30.00  138
 16  \w    103.00 167.00   0.50    3.49    --  102.63  77.00 -30.00  128
 17  \w     38.00 107.00   0.50    3.49    --  102.63 -45.00-180.00  138
 18  \w     35.00 106.00   0.50    3.49    --  102.63 -30.00 120.00  142
 19  \w     98.00 167.00   0.50    3.49    --  102.63  45.00  90.00  138
 20  \w     34.00 107.00   0.50    3.49    --  102.63 -94.00 150.00  146
 21  \w     38.00 126.00   0.50    3.49    --  102.63 -77.00 -30.00  176
 22  \w     95.00 171.00   0.50    3.49    --  102.63  15.00-180.00  152
 23  \w     38.00 107.00   0.50    3.49    --  102.63 -45.00-120.00  138
 24  \w     40.00 116.00   0.50    3.49    --  102.63 -61.00   0.00  152
 25  \w     38.00 112.00   0.50    3.49    --  102.63-125.00 -90.00  148
 26  \w     34.00 107.00   0.50    3.49    --  102.63 -94.00 -30.00  146
 27  \w     90.00 165.00   0.50    3.49    --  102.63  61.00 150.00  150
 28  \w    103.00 167.00   0.50    3.49    --  102.63  77.00-120.00  128
 29  \w     38.00 112.00   0.50    3.49    --  102.63-125.00 120.00  148
 30  \w     99.00 171.00   0.50    3.49    --  102.63  30.00  30.00  144
 31  \w   -101.00 -27.00   0.50    0.88    --  -38.50 -57.00 -90.00  148
 32  \w     38.00 112.00   0.50    0.88    --   49.31  57.00 120.00  148
;
_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      0.1437773000
_diffrn_orient_matrix_UB_12      -0.0233417000
_diffrn_orient_matrix_UB_13      -0.0781336000
_diffrn_orient_matrix_UB_21      -0.1601905000
_diffrn_orient_matrix_UB_22      0.1022336000
_diffrn_orient_matrix_UB_23      -0.0553316000
_diffrn_orient_matrix_UB_31      0.1180669000
_diffrn_orient_matrix_UB_32      0.1690570000
_diffrn_orient_matrix_UB_33      0.0042933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12051
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.831
_diffrn_reflns_theta_min         5.504
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73382
_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    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0020(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0752P)^2^+0.1820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2845
_reflns_number_total             3191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01218e2.cif
_cod_data_source_block           cg-sp-96
_cod_depositor_comments
'Adding full bibliography for 7158232--7158234.cif.'
_cod_database_code               7158232
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C38 H46 N2 O4 '
_diffrn_oxdiff_digest_frames
;
0199e80f5b6b5c2dcd3f935e022fa7c17b00033e592
;
_diffrn_oxdiff_digest_hkl
;
018773a3b8a7fda95d06f2129fb964651562f5
;
_reflns_odcompleteness_completeness 99.82
_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), C21(H21A,H21B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C15(H15), C10(H10), C12(H12), C16(H16), C5(H5), C13(H13), C3(H3),
 C6(H6), C2(H2)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              96039
_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 3.276
_oxdiff_exptl_absorpt_empirical_full_min 0.645