Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct Arylation.
Nitti, Andrea; Signorile, Marco; Boiocchi, Massimo; Bianchi, Gabriele; Po, Riccardo; Pasini, Dario; The Journal of organic chemistry 81 (2016) 11035–11042; doi:10.1021/acs.joc.6b01922

data_4037290
_publ_contact_author
;
  Dario Pasini
  Dipartimento di Chimica 
  University of Pavia
  via Taramelli 12, I-27100 Pavia, ITALY
;
_publ_section_title
;
 Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct
 Arylation.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11035
_journal_page_last               11042
_journal_paper_doi               10.1021/acs.joc.6b01922
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C15 H12 Br2 N2 O2 S'
_chemical_formula_sum            'C15 H12 Br2 N2 O2 S'
_chemical_formula_weight         444.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.99(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.534(4)
_cell_length_b                   8.2908(12)
_cell_length_c                   16.250(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      6
_cell_volume                     3147.1(14)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'MERCURY (Macrae et al.2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'profiled omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1197
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.744
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.292
_exptl_absorpt_correction_T_max  0.708
_exptl_absorpt_correction_T_min  0.288
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_crystal_colour            ORANGE
_exptl_crystal_density_diffrn    1.875
_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.697
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.1087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0279P)^2^+48.9035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3540
_reflns_number_total             5532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01922_si_002.cif
_cod_data_source_block           17
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'PSI-SCAN' was
changed to 'psi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_moiety     '2(C15 H12 Br2 N2 O2 S)'
_cod_original_formula_sum        'C30 H24 Br4 N4 O4 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     888.26
_cod_database_code               4037290
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              19948
_shelx_hkl_checksum              12510