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_1512577
_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            'C16 H16 N2 O5 S'
_chemical_formula_weight         348.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.685(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.7900(9)
_cell_length_b                   15.132(2)
_cell_length_c                   6.9300(5)
_cell_measurement_reflns_used    5413
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      1.2
_cell_volume                     1540.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT  A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7555
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.121
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0873
_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^)+(0.0512P)^2^+11.6375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2206
_refine_ls_wR_factor_ref         0.2268
_reflns_number_gt                2276
_reflns_number_total             2685
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol402469v_si_002.cif
_cod_data_source_block           13octc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1512577