Stereoselective synthesis of beta-(chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: application to the synthesis of a masked triyne.
Simpkins, Simon M. E.; Kariuki, Benson M.; Aricó, Caterina S; Cox, Liam R.; Organic letters 5 (2003) 3971–3974; doi:10.1021/ol035536e

data_1556108
_publ_section_title
;
 Stereoselective synthesis of beta-(chloro)vinylsilanes using a regio- and
 (E)-stereoselective bis-stannylation of unsymmetrically substituted
 butadiynes: application to the synthesis of a masked triyne.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              3971
_journal_page_last               3974
_journal_paper_doi               10.1021/ol035536e
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C24 H31 Cl O1 Si2, 0.3(C2 H6 O)'
_chemical_formula_sum            'C24.6 H32.8 Cl O1.3 Si2'
_chemical_formula_weight         440.94
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I 41/a :2'
_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            16
_cell_length_a                   33.3269(11)
_cell_length_b                   33.3269(11)
_cell_length_c                   9.8038(3)
_cell_measurement_reflns_used    1609
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.82
_cell_measurement_theta_min      2.65
_cell_volume                     10888.9(6)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.864
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD diffractometer'
_diffrn_measurement_method       'CCD slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1415
_diffrn_reflns_av_sigmaI/netI    0.1887
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20574
_diffrn_reflns_theta_full        70.82
_diffrn_reflns_theta_max         70.82
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    2.176
_exptl_absorpt_correction_T_max  0.8805
_exptl_absorpt_correction_T_min  0.8118
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS in SAINTPLUS'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3773
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4528
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.2038
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.2114
_reflns_number_gt                1613
_reflns_number_total             4528
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035536esi20030813_113715.cif
_cod_data_source_block           smes412
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Tetragonal' was changed to
'tetragonal' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

 Corrected the value of the '_refine_diff_density_rms' data item
 by removing an ASCII start of heading (SOH) symbol.

 Antanas Vaitkus,
 2019-12-11
;
_cod_original_sg_symbol_H-M      I41/a
_cod_original_formula_sum        'C24.60 H32.80 Cl O1.30 Si2'
_cod_database_code               1556108