Dual Control of the Selectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes en Route to Densely Functionalized, Chirally Rich Cyclopropyl Derivatives
Ryabchuk, Pavel; Edwards, Andrew; Gerasimchuk, Nikolay; Rubina, Marina; Rubin, Michael; Organic Letters 15 (2013) 6010–; doi:10.1021/ol4027792

data_1513125
_publ_section_title
;
 Dual Control of the Selectivity in the Formal Nucleophilic Substitution
 of Bromocyclopropanes en Route to Densely Functionalized, Chirally Rich
 Cyclopropyl Derivatives
;
_journal_issue                   23
_journal_name_full               'Organic Letters'
_journal_page_first              6010
_journal_paper_doi               10.1021/ol4027792
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C19 H23 N2 O, C12 H12 Br O2'
_chemical_formula_sum            'C31 H35 Br N2 O3'
_chemical_formula_weight         563.52
_chemical_name_common            'Cinchonine salt'
_chemical_name_systematic
; 
 Cinchonine, M.Rubin sample #4 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   '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                   9.9583(8)
_cell_length_b                   11.9802(9)
_cell_length_c                   22.9491(17)
_cell_measurement_reflns_used    143
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      54.69
_cell_measurement_theta_min      2.17
_cell_volume                     2737.9(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX2 CCD area detector'
_diffrn_measurement_method       '4 omega scans; full sphere'
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            35390
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0309P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                5536
_reflns_number_total             6518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4027792_si_002.cif
_cod_data_source_block           first-inv
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1513125
_chemical_absolute_configuration_n2 S
_chemical_absolute_configuration_c10 R
_chemical_absolute_configuration_c11 S
_chemical_absolute_configuration_c13 S
_chemical_absolute_configuration_c17 R
_chemical_absolute_configuration_c27 S
_chemical_absolute_configuration_c30 R