An umpolung approach to the hydroboration of pyridines: a novel and efficient synthesis of N-H 1,4-dihydropyridines
Yang, Huan; Zhang, Li; Zhou, Fei-Yu; Jiao, Lei; Chemical Science 11 (2020) 742–747; doi:10.1039/C9SC05627K

data_1557131
_publ_section_title
;
 An umpolung approach to the hydroboration of pyridines: a novel and
 efficient synthesis of N-H 1,4-dihydropyridines
;
_journal_issue                   3
_journal_name_full               'Chemical Science'
_journal_page_first              742
_journal_page_last               747
_journal_paper_doi               10.1039/C9SC05627K
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C6 H5 D N2'
_chemical_formula_sum            'C6 H5 D N2'
_chemical_formula_weight         107.13
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-21 deposited with the CCDC.	2019-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.0431(2)
_cell_length_b                   13.3857(4)
_cell_length_c                   14.3592(4)
_cell_measurement_reflns_used    1163
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.5170
_cell_measurement_theta_min      6.1600
_cell_volume                     1161.53(6)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.967
_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    -40.00 -10.00   1.00    1.00    --  -40.81 -77.00  90.00   30
  2  \w   -116.00 -91.00   1.00    1.00    --  -40.81 -77.00  90.00   25
  3  \w     17.00  54.00   1.00    1.00    --   40.81 -38.00-120.00   37
  4  \w    -30.00  67.00   1.00    1.00    --   40.81 -57.00 150.00   97
  5  \w     38.00 117.00   1.00    2.00    --  111.58-125.00 -60.00   79
  6  \w    114.00 144.00   1.00    2.00    --  111.58  45.00-150.00   30
  7  \w     97.00 178.00   1.00    2.00    --  111.58  45.00 -30.00   81
  8  \w     52.00  98.00   1.00    2.00    --  111.58 -61.00  60.00   46
;
_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      -0.0145307000
_diffrn_orient_matrix_UB_12      0.0800564000
_diffrn_orient_matrix_UB_13      0.0767866000
_diffrn_orient_matrix_UB_21      0.0047642000
_diffrn_orient_matrix_UB_22      0.0826628000
_diffrn_orient_matrix_UB_23      -0.0746946000
_diffrn_orient_matrix_UB_31      -0.2544434000
_diffrn_orient_matrix_UB_32      -0.0029920000
_diffrn_orient_matrix_UB_33      -0.0057283000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2497
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.697
_diffrn_reflns_theta_min         6.164
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61230
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0923P)^2^+0.0614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                976
_reflns_number_total             1181
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc05627k2.cif
_cod_data_source_block           exp_2511
_cod_depositor_comments          'Adding full bibliography for 1557131.cif.'
_cod_database_code               1557131
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5)
;
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.627