Diastereoselective Synthesis of 1,3-Diyne-Tethered Trifluoromethyl-Cyclopropanes through Sulfur Ylides-Mediated Cyclopropanation/ DBU-Mediated Epimerization Sequence.
Chen, Guo-Shu; Yan, Xiaoxue; Chen, Shujie; Mao, Xiang-Yu; Li, Zhao-Dong; Liu, Yunlin; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00162

data_4038283
_publ_section_title
;
 Diastereoselective Synthesis of 1,3-Diyne-Tethered
 Trifluoromethyl-Cyclopropanes through Sulfur Ylides-Mediated
 Cyclopropanation/ DBU-Mediated Epimerization Sequence.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00162
_journal_year                    2020
_chemical_formula_moiety         'C15 H8 Br F3 O'
_chemical_formula_sum            'C15 H8 Br F3 O'
_chemical_formula_weight         341.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.070(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.9012(13)
_cell_length_b                   5.7981(3)
_cell_length_c                   26.3242(16)
_cell_measurement_reflns_used    3856
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.8440
_cell_measurement_theta_min      3.1770
_cell_volume                     2742.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.450
_diffrn_reflns_theta_min         2.267
_exptl_absorpt_coefficient_mu    3.023
_exptl_absorpt_correction_T_max  0.717
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0252P)^2^+0.7728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             3791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00162_si_001.cif
_cod_data_source_block           exp_1990
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038283
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C2(H2)
2.d :
 C15(H15)
;
_shelx_res_checksum              38648
_shelx_hkl_checksum              85074
_olex2_submission_special_instructions 'No special instructions were received'