The Carbocation-Catalyzed Intermolecular Formal [2 + 2 + 1] Cycloaddition of Ynamides with Quinoxaline N-Oxides
Jin, Hongming; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.; ACS Catalysis  (2019) 11663–; doi:10.1021/acscatal.9b03911

data_4516240
_publ_section_title
;
 The Carbocation-Catalyzed Intermolecular Formal [2 + 2 + 1] Cycloaddition
 of Ynamides with Quinoxaline N-Oxides
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              11663
_journal_paper_doi               10.1021/acscatal.9b03911
_journal_year                    2019
_chemical_formula_sum            'C36 H36 N2 O5 S2'
_chemical_formula_weight         640.79
_chemical_name_common            '6b in manuscript'
_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-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_a                   10.1824(19)
_cell_length_b                   12.255(2)
_cell_length_c                   25.931(5)
_cell_measurement_reflns_used    1885
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.25
_cell_measurement_theta_min      2.29
_cell_volume                     3235.8(10)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
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_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
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_diffrn_reflns_limit_k_min       -12
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_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        21.486
_diffrn_reflns_theta_max         21.486
_diffrn_reflns_theta_min         1.571
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_correction_T_min  0.7717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). <i>SADABS</i>. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       plate
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_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0392P)^2^+2.0030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1193
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_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2752
_reflns_number_total             3722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03911_si_002.cif
_cod_data_source_block           jih10
_cod_database_code               4516240
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              72360
_shelx_hkl_checksum              99091