Asymmetric C(sp)–H Addition of Terminal Alkynes to Cyclopropenes by a Chiral Gadolinium Catalyst
Teng, Huai-Long; Ma, Yuanhong; Zhan, Gu; Nishiura, Masayoshi; Hou, Zhaomin; ACS Catalysis 8 (2018) 4705–; doi:10.1021/acscatal.8b01189

data_4515576
_publ_section_title
;
 Asymmetric C(sp)--H Addition of Terminal Alkynes to Cyclopropenes by a
 Chiral Gadolinium Catalyst
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              4705
_journal_paper_doi               10.1021/acscatal.8b01189
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 Cl O'
_chemical_formula_sum            'C19 H17 Cl O'
_chemical_formula_weight         296.77
_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
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6120(9)
_cell_length_b                   7.5305(14)
_cell_length_c                   37.033(6)
_cell_measurement_reflns_used    278
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1565.1(5)
_computing_cell_refinement       'Bruker SMART APEX3 v2016.1-0'
_computing_data_collection       'Bruker SMART APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SMART APEX3 v2016.1-0'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8Quest with CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            13675
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.068
_diffrn_reflns_theta_max         25.068
_diffrn_reflns_theta_min         1.100
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.650
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0736P)^2^+0.3497P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2540
_reflns_number_total             2750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b01189_si_002.cif
_cod_data_source_block           3g
_cod_original_cell_volume        1565.0(5)
_cod_database_code               4515576
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.942
_shelx_res_checksum              8156
_shelx_hkl_checksum              25911