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_4028128
_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         'C11 H11 Cl S'
_chemical_formula_sum            'C11 H11 Cl S'
_chemical_formula_weight         210.71
_chemical_name_systematic
;
2,7-dibutyl-1,6-dichloronaphtho[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
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_audit_creation_date
;
'Fri Mar 09 11:41:45 2012'
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Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_cell_angle_alpha                90.861(6)
_cell_angle_beta                 89.656(6)
_cell_angle_gamma                98.724(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9460(10)
_cell_length_b                   7.7200(10)
_cell_length_c                   9.0570(10)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    100(2)
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_cell_volume                     479.99(11)
_computing_cell_refinement
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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_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_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.966
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_diffrn_measurement_details
;
  1 omega  -19.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.4688   77.0000   30.0000 31

  2 omega  -63.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.4688  179.0000  -30.0000 31

  3 omega   43.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.4688   77.0000   30.0000 28

  4 omega  -76.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.4688  179.0000  150.0000 41

  5 omega -107.00  -16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -77.8666   77.0000  120.0000 91

  6 omega -111.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -77.8666  125.0000  120.0000 105

  7 omega   68.00  138.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041   77.0000    0.0000 70

  8 omega   31.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -37.0000    0.0000 25

  9 omega   16.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -37.0000  -90.0000 55

 10 omega    9.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -37.0000 -150.0000 61

 11 omega   64.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041   37.0000  120.0000 78

 12 omega   55.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -77.0000  -90.0000 46

 13 omega   22.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -77.0000 -150.0000 62

;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Cu) x-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2478
_diffrn_reflns_theta_full        61.76
_diffrn_reflns_theta_max         61.76
_diffrn_reflns_theta_min         6.45
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.086
_exptl_absorpt_correction_T_max  0.8585
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0444P)^2^+0.1539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0741
_reflns_number_gt                1315
_reflns_number_total             1442
_reflns_threshold_expression     >2sigma(I)
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