Synthesis of isomerically pure anti-anthradithiophene derivatives.
Tylleman, Benoît; Vande Velde, Christophe M. L.; Balandier, Jean-Yves; Stas, Sara; Sergeyev, Sergey; Geerts, Yves Henri; Organic letters 13 (2011) 5208–5211; doi:10.1021/ol202089t

data_1502476
_publ_section_title
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 Synthesis of isomerically pure anti-anthradithiophene derivatives.
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_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5208
_journal_page_last               5211
_journal_paper_doi               10.1021/ol202089t
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C30 H40 Br2 O2 S2'
_chemical_formula_sum            'C30 H40 Br2 O2 S2'
_chemical_formula_weight         656.56
_chemical_melting_point          385.5(5)
_chemical_name_systematic
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2,2'-[(2,5-dimethoxy-1,4-phenylene)bis(methylene)]bis(3-bromo-5-hexylthiophene) 
;
_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
_cell_angle_alpha                96.790(10)
_cell_angle_beta                 94.000(10)
_cell_angle_gamma                92.000(10)
_cell_formula_units_Z            1
_cell_length_a                   4.665(2)
_cell_length_b                   7.757(4)
_cell_length_c                   20.266(8)
_cell_measurement_reflns_used    187
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      5.27
_cell_volume                     725.7(6)
_computing_cell_refinement       'APEXII software (Bruker, 2008)'
_computing_data_collection       'APEXII software (Bruker, 2008)'
_computing_data_reduction        'APEXII software (Bruker, 2008)'
_computing_molecular_graphics    'ORTEPIII for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009), WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker Smart 1000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8729
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.89
_diffrn_reflns_theta_min         1.01
_exptl_absorpt_coefficient_mu    2.962
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             338
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_refine_diff_density_max         4.046
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.237
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.295
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0926
_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^)+(0.0523P)^2^+10.3080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.2471
_reflns_number_gt                3334
_reflns_number_total             4234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202089t_si_002.cif
_cod_data_source_block           9a
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '385-386K' was changed to '385.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_cell_volume        725.8(6)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502476