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_4128999
_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            'C32 H57 Li2 N6 O2 P'
_chemical_formula_weight         602.68
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.958(6)
_cell_length_b                   15.579(7)
_cell_length_c                   30.593(10)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      19.87
_cell_measurement_theta_min      2.31
_cell_volume                     7129(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.1334
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15848
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        23.254
_diffrn_reflns_theta_max         23.254
_diffrn_reflns_theta_min         1.331
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7450
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_process_details   Multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1890 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.452
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.452
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0863
_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^)+0.8832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                6264
_reflns_number_total             9954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08659_si_005.cif
_cod_data_source_block           Complex_1r_lithiated
_cod_depositor_comments
;

2020-06-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C64 H114 Li4 N12 O4 P2'
_cod_original_formula_weight         1205.37
_cod_original_formula_units_Z            4
_cod_database_code               4128999
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   sadabs
_shelx_res_checksum              7995
_shelx_hkl_checksum              51233