Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined Quaternary Centers.
Picazo, Elias; Anthony, Sarah M.; Giroud, Maude; Simon, Adam; Miller, Margeaux A.; Houk, K. N.; Garg, Neil K.; Journal of the American Chemical Society 140 (2018) 7605–7610; doi:10.1021/jacs.8b02875

data_4132305
_publ_section_title
;
 Arynes and Cyclic Alkynes as Synthetic Building Blocks for Stereodefined
 Quaternary Centers.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7605
_journal_page_last               7610
_journal_paper_doi               10.1021/jacs.8b02875
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H25 N O S'
_chemical_formula_sum            'C21 H25 N O S'
_chemical_formula_weight         339.48
_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   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1114(2)
_cell_length_b                   9.3977(2)
_cell_length_c                   21.5596(5)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.10
_cell_measurement_theta_min      4.10
_cell_volume                     1846.07(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17507
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.125
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    1.593
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       platelet
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 1337 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.030(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0219
_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^)+(0.0379P)^2^+0.0315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0582
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.956
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                3251
_reflns_number_total             3394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b02875_si_002.cif
_cod_data_source_block           garg1708s_a
_cod_database_code               4132305
_shelx_estimated_absorpt_t_min   0.741
_shelx_estimated_absorpt_t_max   0.939
_shelxl_version_number           2014/6
_shelx_res_checksum              68177
_shelx_hkl_checksum              5063