Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-Isomers of Didodecyl[1]benzothieno[3,2-b][1]benzothiophenes
Christian Ruzié; Jolanta Karpinska; Alan R. Kennedy; Yves H. Geerts; Journal of Organic Chemistry 78 (2013) 7741–7748; doi:10.1021/jo401134c

data_4028463
_publ_section_title
;
 Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-Isomers of
 Didodecyl[1]benzothieno[3,2-b][1]benzothiophenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7741
_journal_page_last               7748
_journal_paper_doi               10.1021/jo401134c
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C14 H8 Br2 S2'
_chemical_formula_weight         400.14
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 103.816(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.9821(16)
_cell_length_b                   4.1296(3)
_cell_length_c                   14.4511(11)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.7908
_cell_measurement_theta_min      4.1387
_cell_volume                     1273.88(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4334
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         72.94
_diffrn_reflns_theta_min         6.67
_exptl_absorpt_coefficient_mu    10.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET)
(compiled Nov 25 2010,17:55:46)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0748P)^2^+3.5808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                1174
_reflns_number_total             1252
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo401134c_si_002.cif
_cod_data_source_block           cr760
_cod_original_cell_volume        1273.88(16)
_cod_database_code               4028463