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_1513126
_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         'C23 H29 N O2'
_chemical_formula_sum            'C23 H29 N O2'
_chemical_formula_weight         351.47
_chemical_name_common            Pasha
_chemical_name_systematic
;
 Chiral-(R)-substituted cyclopropane
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6721(4)
_cell_length_b                   19.6189(11)
_cell_length_c                   21.5843(11)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      49.89
_cell_measurement_theta_min      2.45
_cell_volume                     4095.7(4)
_computing_cell_refinement       'Bruker SAINT v8.30C'
_computing_data_collection       'Bruker APEX2 v2012.4.3'
_computing_data_reduction        'Bruker SAINT v8.30C'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'D8 goniostat with Bruker APEXII'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'Si-<111> channel cut crystal'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.2399
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30096
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        48.068
_diffrn_reflns_theta_max         50.003
_diffrn_reflns_theta_min         2.447
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  0.2
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.7499
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2013)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details
;
 Flack x determined using 2747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         7776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1321P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1828
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                6920
_reflns_number_total             7776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol4027792_si_003.cif
_cod_data_source_block           ASpek-11
_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               1513126
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.993
_chemical_absolute_configuration_at_c6 R
_chemical_absolute_configuration_at_c7 S
_chemical_absolute_configuration_at_c8 R
_chemical_absolute_configuration_at_c29 R
_chemical_absolute_configuration_at_c30 S
_chemical_absolute_configuration_at_c31 R
_shelxl_version_number           2013-3
_shelx_res_checksum              95534
_shelx_hkl_checksum              66080