Iridium-catalyzed asymmetric hydrogenation of 2-pyridyl cyclic imines: a highly enantioselective approach to nicotine derivatives.
Guo, Cui; Sun, Dong-Wei; Yang, Shuang; Mao, Shen-Jie; Xu, Xiao-Hua; Zhu, Shou-Fei; Zhou, Qi-Lin; Journal of the American Chemical Society 137 (2015) 90–93; doi:10.1021/ja511422q

data_4123334
_publ_section_title
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 Iridium-catalyzed asymmetric hydrogenation of 2-pyridyl cyclic imines: a
 highly enantioselective approach to nicotine derivatives.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              90
_journal_page_last               93
_journal_paper_doi               10.1021/ja511422q
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H12 B F24, C62 H76 Ir N O P'
_chemical_formula_sum            'C94 H88 B F24 Ir N O P'
_chemical_formula_weight         1937.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.496(4)
_cell_length_b                   21.323(4)
_cell_length_c                   21.734(4)
_cell_measurement_reflns_used    46208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     9035(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  SCX-mini
_diffrn_measurement_method       '\ w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1122
_diffrn_reflns_av_sigmaI/netI    0.1131
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            92542
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_exptl_absorpt_coefficient_mu    1.591
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3920
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         2.496
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    construct
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1367
_refine_ls_number_reflns         20641
_refine_ls_number_restraints     3022
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+3.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                13725
_reflns_number_total             20641
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja511422q_si_003.cif
_cod_data_source_block           x
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
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_cod_database_code               4123334