DBU-mediated [4 + 1] Annulations of Donor-Acceptor Cyclopropanes with Carbon disulfide or Thiourea for Synthesis of 2-Aminothiophene-3-carboxylates
Su, Zhenjie; Qian, Siran; Xue, Shuwen; Wang, Cunde; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01886J

data_7155861
_publ_section_title
;
 DBU-mediated [4 + 1] Annulations of Donor-Acceptor Cyclopropanes with
 Carbon disulfide or Thiourea for Synthesis of
 2-Aminothiophene-3-carboxylates
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01886J
_journal_year                    2017
_chemical_formula_moiety         '	C20 H15 Br2 N O3 S'
_chemical_formula_sum            'C20 H15 Br2 N O3 S'
_chemical_formula_weight         509.19
_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
_audit_update_record
;
2017-04-20 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                103.86(16)
_cell_angle_beta                 92.63(11)
_cell_angle_gamma                113.20(12)
_cell_formula_units_Z            2
_cell_length_a                   8.24(4)
_cell_length_b                   10.18(6)
_cell_length_c                   13.48(7)
_cell_measurement_reflns_used    3690
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.91
_cell_volume                     997(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13106
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    4.190
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.991
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     440
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0725
_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^)+(0.1532P)^2^+0.8599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2440
_reflns_number_gt                2237
_reflns_number_total             3503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01886j2.cif
_cod_data_source_block           001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        '	C20 H15 Br2 N O3 S'
_cod_database_code               7155861