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_7115446
_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         '2(C34 H26 P, B F4)'
_chemical_formula_sum            'C34 H26 B F4 P'
_chemical_formula_weight         552.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c 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            8
_cell_length_a                   20.732(3)
_cell_length_b                   19.775(3)
_cell_length_c                   13.7739(19)
_cell_measurement_reflns_used    6504
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.735
_cell_measurement_theta_min      2.283
_cell_volume                     5647.0(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'XSHELL, 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_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31645
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.9756
_exptl_absorpt_correction_T_min  0.9589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         11499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0540
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                8569
_reflns_number_total             11499
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03415e2.cif
_cod_data_source_block           kor8o
_cod_original_cell_volume        5646.9(13)
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7115446