Model for the Enantioselectivity of Asymmetric Intramolecular Alkylations by Bis-Quaternized Cinchona Alkaloid-Derived Catalysts.
He, Cyndi Qixin; Simon, Adam; Lam, Yu-Hong; Brunskill, Andrew P. J.; Yasuda, Nobuyoshi; Tan, Jiajing; Hyde, Alan M.; Sherer, Edward C.; Houk, K. N.; The Journal of organic chemistry 82 (2017) 8645–8650; doi:10.1021/acs.joc.7b01577

data_4032815
_publ_section_title
;
 Model for the Enantioselectivity of Asymmetric Intramolecular Alkylations
 by Bis-Quaternized Cinchona Alkaloid-Derived Catalysts.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8645
_journal_page_last               8650
_journal_paper_doi               10.1021/acs.joc.7b01577
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H33 Br I N3 O4'
_chemical_formula_weight         670.37
_chemical_name_systematic
; 
(1S,2R,4S,5R)-2-((S)-hydroxy(1-methylquinolin-1-ium-4-yl)
methyl)-1-(4-nitrobenzyl)-5-vinylquinuclidin-1-ium 
Iodide Bromide Monohydrate  
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 114.0924(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.2306(4)
_cell_length_b                   9.0943(3)
_cell_length_c                   13.4271(5)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      3.61
_cell_volume                     1363.38(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21276
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.585
_diffrn_reflns_theta_min         3.606
_exptl_absorpt_coefficient_mu    11.249
_exptl_absorpt_correction_T_max  0.324
_exptl_absorpt_correction_T_min  0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.4660
_exptl_transmission_factor_min   0.2109
_refine_diff_density_max         1.958
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.109
_refine_ls_abs_structure_details
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.121(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0831P)^2^+5.8499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4814
_reflns_number_total             4820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01577_si_001.cif
_cod_data_source_block           mdk032
_cod_database_code               4032815
_shelx_estimated_absorpt_t_min   0.165
_shelx_estimated_absorpt_t_max   0.399
_shelxl_version_number           2014-3
_shelx_res_checksum              2479
_shelx_hkl_checksum              87126