Diastereoselective Ring Opening of Fully-Substituted Cyclopropanes via Intramolecular Friedel–Crafts Alkylation
Marek, Ilan; Lanke, Veeranjaneyulu; Zhang, Fa-Guang; Kaushansky, Alexander; Chemical Science  (2019) –; doi:10.1039/C9SC03832A

data_1552266
_publ_section_title
;
 Diastereoselective Ring Opening of Fully-Substituted Cyclopropanes via
 Intramolecular Friedel--Crafts Alkylation
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC03832A
_journal_year                    2019
_chemical_formula_moiety         'C27 H37 F O2 Si'
_chemical_formula_sum            'C27 H37 F O2 Si'
_chemical_formula_weight         440.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-01 deposited with the CCDC.    2019-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.127(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3821(15)
_cell_length_b                   12.1651(12)
_cell_length_c                   16.6919(18)
_cell_measurement_temperature    296(2)
_cell_volume                     2656.7(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2010
_diffrn_reflns_av_unetI/netI     0.1374
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15337
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.103
_diffrn_reflns_theta_max         25.103
_diffrn_reflns_theta_min         1.556
_exptl_absorpt_coefficient_mu    0.114
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0721
_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^)+(0.0781P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2246
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc03832a2.cif
_cod_data_source_block           marek153b
_cod_database_code               1552266
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.976
_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:
 C5(H5A,H5B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C13(H13), C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C16(H16A,
 H16B,H16C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              99338
_olex2_submission_special_instructions 'No special instructions were received'