#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/81/4028129.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4028129
loop_
_publ_author_name
'Caterina Viglianisi'
'Lucia Becucci'
'Cristina Faggi'
'Sara Piantini'
'Piero Procacci'
'Stefano Menichetti'
_publ_contact_author_address
;Dipartimento Chimica "U. Schiff"
Università 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       'ω 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/[σ²(Fo²)+(0.0553P)²+0.1106P] where P=(Fo²+2Fc²)/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
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.49504(14) 0.19059(9) 0.60987(6) 0.0238(2) Uani 1 1 d .
Cl1 Cl 0.50405(14) 0.70356(9) 0.79514(6) 0.0288(2) Uani 1 1 d .
C1 C -0.0797(5) 0.4548(4) 0.4487(2) 0.0214(6) Uani 1 1 d .
C2 C -0.0560(6) 0.2804(4) 0.3973(2) 0.0231(6) Uani 1 1 d .
H2 H -0.1604 0.2232 0.3310 0.028 Uiso 1 1 calc R
C3 C 0.1133(6) 0.1952(4) 0.4416(2) 0.0240(6) Uani 1 1 d .
H3 H 0.1259 0.0813 0.4064 0.029 Uiso 1 1 calc R
C4 C 0.2711(5) 0.2830(4) 0.5426(2) 0.0227(6) Uani 1 1 d .
C5 C 0.2598(5) 0.4535(3) 0.5974(2) 0.0211(6) Uani 1 1 d .
C6 C 0.4454(5) 0.5038(3) 0.6971(2) 0.0216(6) Uani 1 1 d .
C7 C 0.5849(5) 0.3792(4) 0.7144(2) 0.0229(6) Uani 1 1 d .
C8 C 0.7885(6) 0.3938(4) 0.8102(2) 0.0250(6) Uani 1 1 d .
H8A H 0.7099 0.4101 0.8791 0.030 Uiso 1 1 calc R
H8B H 0.9251 0.5010 0.8123 0.030 Uiso 1 1 calc R
C9 C 0.9116(6) 0.2321(4) 0.8058(2) 0.0246(6) Uani 1 1 d .
H9A H 1.0022 0.2204 0.7400 0.030 Uiso 1 1 calc R
H9B H 0.7753 0.1232 0.7992 0.030 Uiso 1 1 calc R
C10 C 1.1030(6) 0.2493(4) 0.9090(2) 0.0277(7) Uani 1 1 d .
H10A H 1.0123 0.2591 0.9749 0.033 Uiso 1 1 calc R
H10B H 1.2387 0.3587 0.9162 0.033 Uiso 1 1 calc R
C11 C 1.2268(6) 0.0864(4) 0.9021(3) 0.0335(7) Uani 1 1 d .
H11A H 1.3457 0.1011 0.9681 0.050 Uiso 1 1 calc R
H11B H 1.3194 0.0778 0.8377 0.050 Uiso 1 1 calc R
H11C H 1.0930 -0.0218 0.8961 0.050 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 S1 C4 91.68(13) . .
C2 C1 C1 119.7(3) . 2_566
C2 C1 C5 122.7(2) . 2_566
C1 C1 C5 117.6(3) 2_566 2_566
C3 C2 C1 122.2(2) . .
C3 C2 H2 118.9 . .
C1 C2 H2 118.9 . .
C2 C3 C4 118.6(3) . .
C2 C3 H3 120.7 . .
C4 C3 H3 120.7 . .
C5 C4 C3 122.5(3) . .
C5 C4 S1 113.5(2) . .
C3 C4 S1 123.9(2) . .
C4 C5 C1 119.4(2) . 2_566
C4 C5 C6 108.6(2) . .
C1 C5 C6 132.1(2) 2_566 .
C7 C6 C5 115.4(2) . .
C7 C6 Cl1 118.0(2) . .
C5 C6 Cl1 126.6(2) . .
C6 C7 C8 127.2(2) . .
C6 C7 S1 110.8(2) . .
C8 C7 S1 122.0(2) . .
C7 C8 C9 114.9(2) . .
C7 C8 H8A 108.5 . .
C9 C8 H8A 108.5 . .
C7 C8 H8B 108.5 . .
C9 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
C8 C9 C10 112.4(2) . .
C8 C9 H9A 109.1 . .
C10 C9 H9A 109.1 . .
C8 C9 H9B 109.1 . .
C10 C9 H9B 109.1 . .
H9A C9 H9B 107.9 . .
C9 C10 C11 111.5(2) . .
C9 C10 H10A 109.3 . .
C11 C10 H10A 109.3 . .
C9 C10 H10B 109.3 . .
C11 C10 H10B 109.3 . .
H10A C10 H10B 108.0 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.722(3) .
S1 C4 1.731(3) .
Cl1 C6 1.740(3) .
C1 C2 1.423(4) .
C1 C1 1.437(5) 2_566
C1 C5 1.437(4) 2_566
C2 C3 1.351(4) .
C2 H2 0.9300 .
C3 C4 1.416(4) .
C3 H3 0.9300 .
C4 C5 1.389(4) .
C5 C1 1.437(4) 2_566
C5 C6 1.449(4) .
C6 C7 1.365(4) .
C7 C8 1.502(4) .
C8 C9 1.521(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.525(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.530(4) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 71658188
