Preparation of Optically Active cis-Cyclopropane Carboxylates: Cyclopropanation of α-Silyl Stryenes with Aryldiazoacetates and Desilylation of the Resulting Silyl Cyclopropanes.
Su, Yan; Li, Qing-Fang; Zhao, Yu-Ming; Gu, Peiming; Organic letters 18 (2016) 4356–4359; doi:10.1021/acs.orglett.6b02117

data_1555696
_publ_section_title
;
 Preparation of Optically Active cis-Cyclopropane Carboxylates:
 Cyclopropanation of \a-Silyl Stryenes with Aryldiazoacetates and
 Desilylation of the Resulting Silyl Cyclopropanes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4356
_journal_page_last               4359
_journal_paper_doi               10.1021/acs.orglett.6b02117
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H25 Br O2 Si'
_chemical_formula_sum            'C21 H25 Br O2 Si'
_chemical_formula_weight         417.41
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9734(5)
_cell_length_b                   9.5887(8)
_cell_length_c                   24.3831(16)
_cell_measurement_reflns_used    1292
_cell_measurement_temperature    294.29(10)
_cell_measurement_theta_max      21.4920
_cell_measurement_theta_min      4.2430
_cell_volume                     2098.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.29(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   23.00   78.20   1.2000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000  -60.0000 46

  2 omega   -6.00   61.20   1.2000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000 -150.0000 56

  3 omega   -6.00   30.00   1.2000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000   30.0000 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0453084000
_diffrn_orient_matrix_UB_12      0.0582077000
_diffrn_orient_matrix_UB_13      0.0066110000
_diffrn_orient_matrix_UB_21      -0.0646608000
_diffrn_orient_matrix_UB_22      0.0397747000
_diffrn_orient_matrix_UB_23      0.0059174000
_diffrn_orient_matrix_UB_31      0.0029975000
_diffrn_orient_matrix_UB_32      -0.0223243000
_diffrn_orient_matrix_UB_33      0.0277261000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6209
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.342
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0456P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                2753
_reflns_number_total             3963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02117_si_002.cif
_cod_data_source_block           gupm1031
_cod_original_cell_volume        2098.0(2)
_cod_database_code               1555696
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              45725
_shelx_hkl_checksum              76678
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'