Reaction of Cyclic α-Oxoketene Dithioacetals with Methylene Isocyanides: A Novel Pyrrole Annulation–Ring-Expansion Domino Process
Yugandar, Somaraju; Misra, Nimesh C.; Parameshwarappa, Gangajji; Panda, Kausik; Ila, Hiriyakkanavar; Organic Letters 15 (2013) 5250–; doi:10.1021/ol402469v

data_1512581
_publ_section_title
;
 Reaction of Cyclic \a-Oxoketene Dithioacetals with Methylene Isocyanides:
 A Novel Pyrrole Annulation--Ring-Expansion Domino Process
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5250
_journal_paper_doi               10.1021/ol402469v
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C24 H16 Cl N O S2'
_chemical_formula_weight         433.96
_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                94.482(2)
_cell_angle_beta                 95.013(2)
_cell_angle_gamma                105.512(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6132(3)
_cell_length_b                   11.2387(4)
_cell_length_c                   12.7129(4)
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6
_cell_measurement_theta_min      1.9
_cell_volume                     1038.26(7)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II, (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0671
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9388
_diffrn_reflns_theta_full        32.8.58
_diffrn_reflns_theta_max         23.58
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.000
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.005(3)
_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   0.879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.879
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0549P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                1594
_reflns_number_total             2265
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol402469v_si_002.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:
'__diffrn_measurement_device_type' tag replaced with
'_diffrn_measurement_device_type'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_cell_volume        1038.26(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C6 H4 Cl0.25 N0.25 O0.25 S0.50'
_cod_database_code               1512581