A phosphine-mediated stereocontrolled synthesis of Z-enediynes by a vicinal dialkynylation of ethynylphosphonium salts
Kyle D. Reichl; Alexander T. Radosevich; Chem.Commun. 50 (2014) 9302–; doi:10.1039/C4cc03415E

data_7115448
_publ_section_title
;
 A phosphine-mediated stereocontrolled synthesis of Z-enediynes by a
 vicinal dialkynylation of ethynylphosphonium salts
;
_journal_name_full               Chem.Commun.
_journal_page_first              9302
_journal_paper_doi               10.1039/C4cc03415E
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C27 H22'
_chemical_formula_sum            'C27 H22'
_chemical_formula_weight         346.45
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.887(6)
_cell_length_b                   14.683(4)
_cell_length_c                   7.344(2)
_cell_measurement_reflns_used    981
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.540
_cell_measurement_theta_min      2.774
_cell_volume                     2036.6(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_sigmaI/netI    0.1220
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15340
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.2507
_refine_ls_R_factor_gt           0.1146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0911P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2584
_reflns_number_gt                1965
_reflns_number_total             4859
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03415e2.cif
_cod_data_source_block           kor2o
_cod_original_cell_volume        2036.8(11)
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7115448