Gold-catalyzed ring enlargement and cycloisomerization of alkynylamide tethered alkylidenecyclopropanes
Zhang, Jia-hao; Wei, Yin; Shi, Min; Organic Chemistry Frontiers 5 (2018) 2980–; doi:10.1039/C8QO00907D

data_1554451
_publ_section_title
;
 Gold-catalyzed ring enlargement and cycloisomerization of alkynylamide
 tethered alkylidenecyclopropanes
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2980
_journal_paper_doi               10.1039/C8QO00907D
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H23 N O2 S'
_chemical_formula_weight         413.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-08-11 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.519(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1152(14)
_cell_length_b                   14.1577(18)
_cell_length_c                   24.768(3)
_cell_measurement_reflns_used    4586
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      47.909
_cell_measurement_theta_min      4.654
_cell_volume                     4240.3(9)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15242
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.215
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 1862 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       0.00130(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         6780
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.8129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.637
_reflns_Friedel_fraction_max     0.625
_reflns_number_gt                5461
_reflns_number_total             6780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00907d2.cif
_cod_data_source_block           mo_dm16490_0m
_cod_original_cell_volume        4240.2(9)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1554451
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              60522
_shelx_hkl_checksum              33281