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_4028129
_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-3,8-dichloronaphtho[2,1-b:6,5-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 13:35:40 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                99.618(7)
_cell_angle_beta                 94.426(7)
_cell_angle_gamma                102.384(8)
_cell_formula_units_Z            2
_cell_length_a                   5.2910(10)
_cell_length_b                   7.7140(10)
_cell_length_c                   12.2390(10)
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.2182
_cell_measurement_theta_min      5.9757
_cell_volume                     477.73(12)
_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 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
  1 omega -114.00  -75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824 -125.0000  120.0000 39

  2 omega   46.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824   37.0000 -180.0000 43

  3 omega  -25.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -37.0000  -60.0000 87

  4 omega   24.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824   37.0000  120.0000 73

  5 omega -120.00  -73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000  120.0000 47

  6 omega  -76.00  -24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   45.0000 -120.0000 52

  7 omega -117.00  -72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 45

  8 omega -151.00  -75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000   90.0000 76

  9 omega -148.00  -68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000   30.0000 80

 10 omega  -53.00  -19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  125.0000 -180.0000 34

 11 omega   35.00  119.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -77.0000 -120.0000 84

 12 omega  105.00  154.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  125.0000  -90.0000 49

 13 omega   37.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -15.0000 -150.0000 96

 14 omega   28.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -77.0000    0.0000 94

;
_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  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3252
_diffrn_reflns_theta_full        70.84
_diffrn_reflns_theta_max         70.84
_diffrn_reflns_theta_min         5.98
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.110
_exptl_absorpt_correction_T_max  0.8579
_exptl_absorpt_correction_T_min  0.6816
_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            light-yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0553P)^2^+0.1106P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                1357
_reflns_number_total             1722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400205j_si_003.cif
_cod_data_source_block           exp_762
_cod_database_code               4028129