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_4028130
_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
;
2,9-dibutyl-3,8-bis(4-methoxyphenyl)naphtho[1,2-b:8,7-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 01:19:06 2012'
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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                81.463(4)
_cell_angle_beta                 87.681(5)
_cell_angle_gamma                84.909(5)
_cell_formula_units_Z            2
_cell_length_a                   9.5250(10)
_cell_length_b                   11.5200(10)
_cell_length_c                   13.5910(10)
_cell_measurement_reflns_used    5577
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.0118
_cell_measurement_theta_min      4.6585
_cell_volume                     1468.4(2)
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
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_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
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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
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_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 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -72.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574   77.0000  -90.0000 95

  2 omega -110.00  -16.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -77.0000  150.0000 94

  3 omega  -13.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.1574  -37.0000  -30.0000 78

  4 omega -108.00  -81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -120.0000 27

  5 omega  -57.00  -25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -120.0000 32

  6 omega -118.00  -90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 28

  7 omega   36.00   75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000  -60.0000 39

  8 omega   75.00  152.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000 -150.0000 77

  9 omega   34.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -45.0000  -90.0000 33

 10 omega   70.00  156.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  150.0000 86

 11 omega   37.00  124.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -77.0000 -120.0000 87

 12 omega   74.00  172.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  125.0000 -150.0000 98

 13 omega   96.00  165.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   45.0000  120.0000 69

 14 omega   81.00  112.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  125.0000  150.0000 31

 15 omega  133.00  169.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  125.0000  150.0000 36

 16 omega   58.00  130.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000  -77.0000   90.0000 72

 17 omega   91.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -130.0000   91.0000 31

 18 omega   30.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000 -130.0000   91.0000 47

 19 omega -117.00  -24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -37.0000  -60.0000 93

 20 omega -117.00  -24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -37.0000 -150.0000 93

 21 omega -117.00  -66.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574 -138.0000   21.0000 51

 22 omega -118.00  -16.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.1574  -77.0000   60.0000 102

 23 omega   70.00  143.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   77.0000  -90.0000 73

 24 omega   64.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   15.0000   30.0000 113

;
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16531
_diffrn_reflns_theta_full        72.16
_diffrn_reflns_theta_max         72.16
_diffrn_reflns_theta_min         4.66
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  0.9502
_exptl_absorpt_correction_T_min  0.9086
_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            pale-yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0587P)^2^+0.4446P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                4004
_reflns_number_total             5625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400205j_si_004.cif
_cod_data_source_block           exp_760
_cod_database_code               4028130