Stacking patterns of thieno[3,2-b]thiophenes functionalized by sequential palladium-catalyzed Suzuki and Heck cross-coupling reactions.
Nguyen, Hien; Nguyen Bich, Ngan; Dang, Tung T.; Van Meervelt, Luc; Acta crystallographica. Section C, Structural chemistry 70 (2014) 895–899; doi:10.1107/S2053229614018683

data_2311822
_publ_section_title
;
 Stacking patterns of thieno[3,2-b]thiophenes functionalized by sequential
 palladium-catalyzed Suzuki and Heck cross-coupling reactions.
;
_journal_coeditor_code           LG3143
_journal_issue                   'Pt 9'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              895
_journal_page_last               899
_journal_paper_doi               10.1107/S2053229614018683
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C25 H16 Br2 S2'
_chemical_formula_moiety         'C25 H16 Br2 S2'
_chemical_formula_sum            'C25 H16 Br2 S2'
_chemical_formula_weight         540.32
_chemical_name_systematic
3,6-Dibromo-5-(4-methylstyryl)-2-(naphthalen-1-yl)thieno[3,2-<i>b</i>]thiophene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                106.464(9)
_cell_angle_beta                 94.945(7)
_cell_angle_gamma                93.016(7)
_cell_formula_units_Z            2
_cell_length_a                   4.1522(3)
_cell_length_b                   13.2861(14)
_cell_length_c                   19.6117(18)
_cell_measurement_reflns_used    11208
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.9730
_cell_measurement_theta_min      3.1790
_cell_volume                     1030.32(17)
_computing_cell_refinement
;
(CrysAlisPro; Agilent, 2012)
;
_computing_data_collection
;
(CrysAlisPro; Agilent, 2012)
;
_computing_data_reduction
;
(CrysAlisPro; Agilent, 2012)
;
_computing_molecular_graphics    'Olex2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material  'Olex2 (Dolomanov <i>et al.</i>, 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Agilent SuperNova diffractometer (Single source at offset, Eos detector)
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20862
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    4.146
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.486
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0279
_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^)+(0.0365P)^2^+0.8570P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0742
_reflns_number_gt                3705
_reflns_number_total             4207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lg3143sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        1030.32(16)
_cod_database_code               2311822