A versatile and efficient synthesis of bithiophene-based dicarboxaldehydes from a common synthon.
Bhuwalka, Achala; Mike, Jared F.; Intemann, Jeremy J.; Ellern, Arkady; Jeffries-El, Malika; Organic & biomolecular chemistry 13 (2015) 9462–9470; doi:10.1039/c5ob01135c

data_7154635
_publ_section_title
;
 A versatile and efficient synthesis of bithiophene-based
 dicarboxaldehydes from a common synthon.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9462
_journal_page_last               9470
_journal_paper_doi               10.1039/c5ob01135c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C11 H4 O3 S2'
_chemical_formula_weight         248.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2013.2-0'
_audit_update_record
;
2013-06-14 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.366(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7349(10)
_cell_length_b                   10.508(3)
_cell_length_c                   12.512(3)
_cell_measurement_reflns_used    2235
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.2583
_cell_measurement_theta_min      2.5376
_cell_volume                     488.0(2)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4982
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.975
_refine_diff_density_min         -0.323
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2355
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0508P)^2^+0.3176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                2238
_reflns_number_total             2355
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01135c2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7154633--7154635.cif.'
_cod_database_code               7154635