Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors.
Kutateladze, Dennis A.; Strassfeld, Daniel A.; Jacobsen, Eric N.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02665

data_4134608
_publ_section_title
;
 Enantioselective Tail-to-Head Cyclizations Catalyzed by
 Dual-Hydrogen-Bond Donors.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02665
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H17 F3'
_chemical_formula_weight         266.25
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.4157(17)
_cell_angle_beta                 90.3788(19)
_cell_angle_gamma                90.853(2)
_cell_formula_units_Z            4
_cell_length_a                   7.9199(2)
_cell_length_b                   11.2795(3)
_cell_length_c                   14.9844(4)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      3.24
_cell_volume                     1338.00(6)
_computing_cell_refinement       'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27812
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        66.959
_diffrn_reflns_theta_max         66.959
_diffrn_reflns_theta_min         2.950
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.8402
_exptl_absorpt_correction_T_min  0.7568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 2599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.20(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     807
_refine_ls_number_reflns         8000
_refine_ls_number_restraints     1378
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0511
_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^)+(0.0685P)^2^+0.6233P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_full    0.723
_reflns_Friedel_fraction_max     0.723
_reflns_number_gt                6944
_reflns_number_total             8000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02665_si_002.cif
_cod_data_source_block           DAS-I
_cod_database_code               4134608
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              27318
_shelx_hkl_checksum              12741