Rhodium-catalyzed [2+2+2] cycloaddition of 1,6-diynes with isothiocyanates and carbon disulfide.
Tanaka, Ken; Wada, Azusa; Noguchi, Keiichi; Organic letters 8 (2006) 907–909; doi:10.1021/ol053044r

data_1556115
_publ_section_title
;
 Rhodium-catalyzed [2+2+2] cycloaddition of 1,6-diynes with
 isothiocyanates and carbon disulfide.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              907
_journal_page_last               909
_journal_paper_doi               10.1021/ol053044r
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H19 N O2 S'
_chemical_formula_sum            'C22 H19 N O2 S'
_chemical_formula_weight         361.44
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.834(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9578(3)
_cell_length_b                   20.7251(9)
_cell_length_c                   11.7791(5)
_cell_measurement_reflns_used    32850
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.0
_cell_volume                     1815.66(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics
'ORTEP-3 for Windows Ver. 1.076 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34272
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_min         4.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881.  3167 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.002(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0277P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                6022
_reflns_number_total             6592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol053044rsi20051215_055705.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 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_database_code               1556115