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_1502477
_publ_section_title
;
 Synthesis of isomerically pure anti-anthradithiophene derivatives.
;
_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 H32 O2 S2'
_chemical_formula_sum            'C30 H32 O2 S2'
_chemical_formula_weight         488.68
_chemical_melting_point          520.0(10)
_chemical_name_systematic
;
2,8-dihexylanthra[2,3-b:6,7-b']dithiophene-5,11-dione
;
_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                83.044(3)
_cell_angle_beta                 87.215(3)
_cell_angle_gamma                77.447(3)
_cell_formula_units_Z            1
_cell_length_a                   6.5606(12)
_cell_length_b                   7.3288(13)
_cell_length_c                   13.452(2)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.86
_cell_volume                     626.52(19)
_computing_cell_refinement       Bruker
_computing_data_collection       Bruker
_computing_data_reduction        Bruker
_computing_molecular_graphics    'ORTEP (Farrugia, 1997), Mercury'
_computing_publication_material  'WinGX (Farrugia, 1999), PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type
'Bruker Smart APEX area detector diffractometer'
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7286
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.90
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3687
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0583P)^2^+0.3685P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                2890
_reflns_number_total             3687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202089t_si_003.cif
_cod_data_source_block           12a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '519-521K' was changed to '520.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        626.53(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502477