Enantioselective Alkylation of 2-Alkylpyridines Controlled by Organolithium Aggregation.
Gladfelder, Joshua J.; Ghosh, Santanu; Podunavac, Maša; Cook, Andrew W.; Ma, Yun; Woltornist, Ryan A.; Keresztes, Ivan; Hayton, Trevor W.; Collum, David B.; Zakarian, Armen; Journal of the American Chemical Society 141 (2019) 15024–15028; doi:10.1021/jacs.9b08659

data_4128998
_publ_section_title
;
 Enantioselective Alkylation of 2-Alkylpyridines Controlled by
 Organolithium Aggregation.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15024
_journal_page_last               15028
_journal_paper_doi               10.1021/jacs.9b08659
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H53 Li2 N6 O P'
_chemical_formula_weight         558.63
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.770(6)
_cell_length_b                   10.980(6)
_cell_length_c                   28.973(17)
_cell_measurement_reflns_used    919
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.33
_cell_volume                     3426(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.2742
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6710
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        24.164
_diffrn_reflns_theta_max         24.164
_diffrn_reflns_theta_min         1.406
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.3861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5228
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.2208
_refine_ls_R_factor_gt           0.0886
_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^)+0.6465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1725
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2314
_reflns_number_total             5228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08659_si_005.cif
_cod_data_source_block           Complex_1c_Lithiated
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4128998
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              56513
_shelx_hkl_checksum              36325