A novel anionic domino process for the synthesis of o-cyanoaryl-methylthio/alkyl/aryl/heteroaryl acetylenes.
Kumar, Sarvesh; Peruncheralathan, Saravanan; Ila, Hiriyakkanavar; Junjappa, Hiriyakkanavar; Organic letters 10 (2008) 965–968; doi:10.1021/ol800029c

data_1504567
_publ_section_title
;
 A novel anionic domino process for the synthesis of
 o-cyanoaryl-methylthio/alkyl/aryl/heteroaryl acetylenes.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              965
_journal_page_last               968
_journal_paper_doi               10.1021/ol800029c
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C13 H14 Br N O2 S2'
_chemical_formula_sum            'C13 H14 Br N O2 S2'
_chemical_formula_weight         360.28
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.110(5)
_cell_angle_beta                 80.871(5)
_cell_angle_gamma                64.089(5)
_cell_formula_units_Z            2
_cell_length_a                   8.575(5)
_cell_length_b                   9.110(5)
_cell_length_c                   11.133(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.04
_cell_volume                     757.9(7)
_computing_cell_refinement       SAINT6.45(Bruker2003)
_computing_data_collection       SMART5.628(Bruker2003)
_computing_data_reduction        SAINT6.45(Bruker2003)
_computing_molecular_graphics    Diamond2.1
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick,1997)'
_computing_structure_solution    SHELXS-97(Sheldrick,1990)
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  BrukerSMARTAPEX
_diffrn_measurement_method       /w-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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2132
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         23.18
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        <0.05
_exptl_absorpt_coefficient_mu    2.984
_exptl_absorpt_correction_T_max  0.7963
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS2.10(Bruker2003)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0879P)^2^+0.8706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1401
_reflns_number_gt                1509
_reflns_number_total             1974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800029c-file003.cif
_cod_data_source_block           Compound1a.CIF
_cod_depositor_comments
;
 Removing the _chemical_melting_point data item since it contained the
 _chemical_formula_sum data item value and not the melting temperature.

 Antanas Vaitkus,
 2017-09-27

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        758.0(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504567