Synthesis of polycyclic sultams via a palladium-catalyzed reaction of 1-bromo-2-(cyclopropylidenemethyl)benzenes with 2-alkynylbenzenesulfonamides
Gong, Xinxing; Li, Guangming; Wu, Jie; Organic Chemistry Frontiers 4 (2017) 14–; doi:10.1039/C6QO00480F

data_1553545
_publ_section_title
;
 Synthesis of polycyclic sultams via a palladium-catalyzed reaction of
 1-bromo-2-(cyclopropylidenemethyl)benzenes with
 2-alkynylbenzenesulfonamides
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              14
_journal_paper_doi               10.1039/C6QO00480F
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C25 H21 N O2 S'
_chemical_formula_weight         399.49
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1m2c24
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-07-10 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.922(6)
_cell_length_b                   33.922(6)
_cell_length_c                   11.008(2)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      2.40
_cell_volume                     10970(3)
_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      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1586
_diffrn_reflns_av_unetI/netI     0.1223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26825
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         1.201
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_description       block
_exptl_crystal_F_000             3780
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1143 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.31(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.976
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3251
_reflns_number_total             5552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00480f2.cif
_cod_data_source_block           mo_60511c
_cod_original_cell_volume        10970(5)
_cod_database_code               1553545
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.909
_shelx_estimated_absorpt_t_max   0.984
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              7170
_shelx_hkl_checksum              56910