Synthesis, Properties, Crystal Structures, and Semiconductor Characteristics of Naphtho[1,2-b:5,6-b']dithiophene and -diselenophene Derivatives
Shoji Shinamura; Eigo Miyazaki; Kazuo Takimiya; Journal of Organic Chemistry 75 (2010) 1228–1234; doi:10.1021/jo902545a

data_4025241
_publ_section_title
;
 Synthesis, Properties, Crystal Structures, and Semiconductor
 Characteristics of Naphtho[1,2-b:5,6-b']dithiophene and -diselenophene
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1228
_journal_page_last               1234
_journal_paper_doi               10.1021/jo902545a
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C14 H8 Se2'
_chemical_formula_sum            'C14 H8 Se2'
_chemical_formula_weight         334.12
_chemical_name_common            NDS
_chemical_name_systematic
; 
 NDS 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.542(4)
_cell_length_b                   9.100(6)
_cell_length_c                   19.268(12)
_cell_measurement_reflns_used    2483
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1147.1(13)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.71
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1302
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.48
_diffrn_standards_number         8048
_exptl_absorpt_coefficient_mu    6.412
_exptl_absorpt_correction_T_max  0.726
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1500
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.723
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.723
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0229P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0797
_reflns_number_gt                700
_reflns_number_total             1302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902545a_si_001_2.cif
_cod_data_source_block           NDS
_cod_original_cell_volume        1147.0(12)
_cod_database_code               4025241