Regioselective Electrophilic Access to Naphtho[1,2-b:8,7-b']- and -[1,2-b:5,6-b']dithiophenes
Caterina Viglianisi; Lucia Becucci; Cristina Faggi; Sara Piantini; Piero Procacci; Stefano Menichetti; Journal of Organic Chemistry 78 (2013) 3496–3502; doi:10.1021/jo400205j

data_4028131
_publ_contact_author_address
;Dipartimento Chimica "U. Schiff"
Universit\`a Firenze
Via della Lastruccia 13
50019  Sesto Fiorentino
Firenze
;
_publ_contact_author_email       cristina.@unifi.it
_publ_contact_author_name        'Dr. Cristina Faggi'
_publ_section_title
;
 Regioselective Electrophilic Access to Naphtho[1,2-b:8,7-b']- and
 -[1,2-b:5,6-b']dithiophenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3496
_journal_page_last               3502
_journal_paper_doi               10.1021/jo400205j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C36 H36 O2 S2'
_chemical_formula_sum            'C36 H36 O2 S2'
_chemical_formula_weight         564.77
_chemical_name_systematic
;
2,7-dibutyl-1,6-bis(4-methoxyphenyl)naphtho[1,2-b:5,6-b']dithiophene
;
_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_date
;
'Thu Nov 15 18:19:58 2012'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_cell_angle_alpha                98.344(3)
_cell_angle_beta                 90.870(3)
_cell_angle_gamma                91.061(3)
_cell_formula_units_Z            4
_cell_length_a                   10.6890(10)
_cell_length_b                   14.4040(10)
_cell_length_c                   19.0760(10)
_cell_measurement_reflns_used    9366
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.5335
_cell_measurement_theta_min      4.1339
_cell_volume                     2905.0(4)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -45.00   12.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824   37.0000 -120.0000 57

  2 omega -121.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824    0.0000 -150.0000 141

  3 omega  -98.00  -34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  125.0000   30.0000 64

  4 omega   47.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824   37.0000  -90.0000 27

  5 omega -104.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000  -60.0000 84

  6 omega -120.00  -28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -120.0000 92

  7 omega  -96.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000    0.0000 77

  8 omega -114.00  -78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000   60.0000 36

  9 omega   84.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   15.0000  150.0000 90

 10 omega   83.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  125.0000 -150.0000 77

 11 omega   83.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   77.0000    0.0000 82

 12 omega   30.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  150.0000 30

 13 omega   30.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  120.0000 29

 14 omega   40.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -90.0000 30

 15 omega   26.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -77.0000  120.0000 101

 16 omega   28.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000 -150.0000 39

;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23272
_diffrn_reflns_theta_full        70.66
_diffrn_reflns_theta_max         70.66
_diffrn_reflns_theta_min         4.14
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.901
_exptl_absorpt_correction_T_max  0.9446
_exptl_absorpt_correction_T_min  0.8838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.363
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         10632
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0593P)^2^+2.6063P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                7904
_reflns_number_total             10632
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400205j_si_005.cif
_cod_data_source_block           exp_763
_cod_database_code               4028131