Gold-Catalyzed Cycloisomerization and Diels-Alder Reaction of 1,6-Diyne Esters with Alkenes and Diazenes to Hydronaphthalenes and -cinnolines.
Yan, Jianming; Tay, Guan Liang; Neo, Cuien; Lee, Bo Ra; Chan, Philip Wai Hong; Organic letters 17 (2015) 4176–4179; doi:10.1021/acs.orglett.5b01935

data_1555172
_publ_section_title
;
 Gold-Catalyzed Cycloisomerization and Diels-Alder Reaction of 1,6-Diyne
 Esters with Alkenes and Diazenes to Hydronaphthalenes and -cinnolines.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4176
_journal_page_last               4179
_journal_paper_doi               10.1021/acs.orglett.5b01935
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C34 H30 N2 O6'
_chemical_formula_weight         562.60
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 116.324(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4637(5)
_cell_length_b                   45.4434(19)
_cell_length_c                   12.0124(6)
_cell_measurement_reflns_used    5944
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      19.9455
_cell_measurement_theta_min      2.1753
_cell_volume                     5608.9(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_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      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            51892
_diffrn_reflns_theta_full        25.76
_diffrn_reflns_theta_max         25.76
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         10331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0627P)^2^+2.3651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1555
_reflns_number_gt                6461
_reflns_number_total             10331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01935_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        5608.9(4)
_cod_database_code               1555172