Gold-Catalyzed Tandem 1,3-Migration/Double Cyclopropanation of 1-Ene-4,n-diyne Esters to Tetracyclodecene and Tetracycloundecene Derivatives.
Chen, Cuili; Zou, Yongzhen; Chen, Xianxiao; Zhang, Xiaoxiang; Rao, Weidong; Chan, Philip Wai Hong; Organic letters 18 (2016) 4730–4733; doi:10.1021/acs.orglett.6b02404

data_1555758
_publ_section_title
;
 Gold-Catalyzed Tandem 1,3-Migration/Double Cyclopropanation of
 1-Ene-4,n-diyne Esters to Tetracyclodecene and Tetracycloundecene
 Derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4730
_journal_page_last               4733
_journal_paper_doi               10.1021/acs.orglett.6b02404
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C25 H23 N O4'
_chemical_formula_weight         401.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.9069(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.1296(3)
_cell_length_b                   15.4679(6)
_cell_length_c                   33.0511(14)
_cell_measurement_reflns_used    5871
_cell_measurement_temperature    376.(2)
_cell_measurement_theta_max      26.8992
_cell_measurement_theta_min      2.7053
_cell_volume                     4140.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      376.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            27141
_diffrn_reflns_theta_full        27.12
_diffrn_reflns_theta_max         27.12
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         9144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0818P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1491
_reflns_number_gt                6561
_reflns_number_total             9144
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02404_si_002.cif
_cod_data_source_block           I
_cod_database_code               1555758
_shelx_res_checksum              35687
_shelx_hkl_checksum              97877