Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective Cycloisomerization Using Palladium-Catalyzed Alkyne-Alkyne Coupling.
Trost, Barry M.; Masters, James T.; Le Vaillant, Franck; Lumb, Jean-Philip; The Journal of organic chemistry 81 (2016) 10023–10028; doi:10.1021/acs.joc.6b01920

data_4037286
_publ_section_title
;
 Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective
 Cycloisomerization Using Palladium-Catalyzed Alkyne-Alkyne Coupling.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10023
_journal_page_last               10028
_journal_paper_doi               10.1021/acs.joc.6b01920
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C19 H24 O4'
_chemical_formula_sum            'C19 H24 O4'
_chemical_formula_weight         316.38
_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
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.983(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7733(11)
_cell_length_b                   14.7716(19)
_cell_length_c                   13.7797(18)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    120(2)
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_cell_measurement_theta_min      2.47
_cell_volume                     1707.9(4)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX-II v2014-5.0'
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_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.198
_diffrn_reflns_theta_min         2.071
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0344P)^2^+0.6499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3041
_reflns_number_total             3788
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01920_si_001.cif
_cod_data_source_block           su1425
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037286
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              98508
_shelx_hkl_checksum              45111