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_4516239
_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            'C33.5 H31.5 Cl4.5 N2 O5 S2'
_chemical_formula_weight         765.75
_chemical_name_common            '3a in manuscript'
_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_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 114.326(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.081(3)
_cell_length_b                   10.5270(8)
_cell_length_c                   22.0782(18)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      19.82
_cell_measurement_theta_min      2.57
_cell_volume                     7217.8(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30608
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.906
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  0.9350
_exptl_absorpt_correction_T_min  0.7885
_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    1.409
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             3160
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         6394
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+17.5142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3963
_reflns_number_total             6394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03911_si_001.cif
_cod_data_source_block           jih4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C33.50 H31.50 Cl4.50 N2 O5 S2'
_cod_database_code               4516239
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.926
_shelx_res_checksum              81833
_shelx_hkl_checksum              76293