#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/65/4116547.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_4116547
loop_
_publ_author_name
'Giovanna Barbarella'
'Massimo Zambianchi'
'Luciano Antolini'
'Paolo Ostoja'
'Piera Maccagnani'
'Alessandro Bongini'
'Elisabeth A. Marseglia'
'Emilio Tedesco'
'Giuseppe Gigli'
'Roberto Cingolani'
_publ_section_title
;
 Solid-State Conformation, Molecular Packing, and Electrical and Optical
 Properties of Processable β-Methylated Sexithiophenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8920
_journal_page_last               8926
_journal_paper_doi               10.1021/ja9916512
_journal_volume                  121
_journal_year                    1999
_chemical_compound_source        synthesis
_chemical_formula_sum            'C28 H22 S6'
_chemical_formula_weight         550.82
_chemical_name_systematic
; 
 4',3'',4''',3''''-tetramethyl-2,2':5,2'':5'',2''':5''',2'''':5'''',2'''''.-
 sexithiophene (triclinic form)
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                99.47(2)
_cell_angle_beta                 91.62(2)
_cell_angle_gamma                107.08(2)
_cell_formula_units_Z            1
_cell_length_a                   7.595(2)
_cell_length_b                   7.680(2)
_cell_length_c                   11.438(3)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      4.5
_cell_volume                     627.0(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4RA-M18X diffractometer'
_diffrn_measurement_method       'theta-two(theta) scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode : 52 KV, 100 mA'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            3047
_diffrn_reflns_theta_max         26.93
_diffrn_reflns_theta_min         1.81
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            orange-yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       'transparent prisms'
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.053
_refine_ls_goodness_of_fit_obs   1.072
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.178
_refine_ls_restrained_S_obs      1.075
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_obs          0.0388
_refine_ls_shift/esd_max         -0.003
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0468P)²+0.2496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1165
_refine_ls_wR_factor_obs         0.0957
_reflns_number_observed          2034
_reflns_number_total             2460
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja9916512_3.cif
_cod_data_source_block           Compound2T
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.2496P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.2496P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'difmap and geom' was changed
to 'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        626.9(3)
_cod_database_code               4116547
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C2A C 0.2484(3) 0.1854(3) 0.2910(2) 0.0434(5) Uani 1 d D .
S1A S 0.1254(2) 0.0570(2) 0.16406(9) 0.0622(4) Uani 0.790(3) d P 1
C3A C 0.4377(8) 0.2483(10) 0.2726(5) 0.0538(15) Uani 0.790(3) d P 1
C4A C 0.4765(7) 0.1793(8) 0.1556(4) 0.0619(13) Uani 0.790(3) d P 1
C5A C 0.3205(7) 0.0782(7) 0.0902(4) 0.0621(15) Uani 0.790(3) d P 1
S1A* S 0.4793(5) 0.2562(12) 0.2792(9) 0.067(2) Uiso 0.210(3) d PD 2
C3A* C 0.1565(28) 0.0898(37) 0.1835(11) 0.067(2) Uiso 0.210(3) d PD 2
H3A* H 0.0282(28) 0.0555(37) 0.1730(11) 0.075(5) Uiso 0.210(3) calc PR 2
C4A* C 0.2609(33) 0.0445(40) 0.0891(24) 0.067(2) Uiso 0.210(3) d PD 2
H4A* H 0.2227(33) -0.0302(40) 0.0147(24) 0.075(5) Uiso 0.210(3) calc PR 2
C5A* C 0.4264(43) 0.1381(41) 0.1371(13) 0.067(2) Uiso 0.210(3) d PD 2
H5A* H 0.5241(43) 0.1406(41) 0.0895(13) 0.075(5) Uiso 0.210(3) calc PR 2
S1B S 0.28577(8) 0.29897(9) 0.53534(5) 0.0435(2) Uani 1 d . .
C2B C 0.1609(3) 0.2244(3) 0.3990(2) 0.0393(5) Uani 1 d . .
C3B C -0.0220(3) 0.2032(3) 0.4123(2) 0.0429(5) Uani 1 d . .
C4B C -0.0647(3) 0.2460(3) 0.5313(2) 0.0387(5) Uani 1 d . .
C5B C 0.0905(3) 0.3019(3) 0.6103(2) 0.0353(5) Uani 1 d . .
C6B C -0.2591(4) 0.2262(5) 0.5617(3) 0.0531(7) Uani 1 d . .
S1C S -0.05652(8) 0.44983(10) 0.80719(5) 0.0467(2) Uani 1 d . .
C2C C 0.1070(3) 0.3585(3) 0.7396(2) 0.0360(5) Uani 1 d . .
C3C C 0.2358(3) 0.3490(3) 0.8240(2) 0.0381(5) Uani 1 d . .
C4C C 0.1963(3) 0.4109(3) 0.9411(2) 0.0404(5) Uani 1 d . .
C5C C 0.0418(3) 0.4672(3) 0.9479(2) 0.0384(5) Uani 1 d . .
C6C C 0.3975(4) 0.2772(5) 0.8001(2) 0.0559(7) Uani 1 d . .
H3A H 0.5465(58) 0.3275(61) 0.3509(40) 0.075(5) Uiso 0.790(3) d P .
H4A H 0.5761(63) 0.2023(64) 0.1335(39) 0.075(5) Uiso 0.790(3) d P .
H5A H 0.3070(58) 0.0299(59) 0.0081(39) 0.075(5) Uiso 0.790(3) d P .
H3B H -0.1274(44) 0.1653(44) 0.3430(27) 0.075(5) Uiso 1 d . .
H6B1 H -0.2830(44) 0.1727(45) 0.6279(30) 0.072(4) Uiso 1 d . .
H6B2 H -0.3314(46) 0.1709(46) 0.4993(31) 0.072(4) Uiso 1 d . .
H6B3 H -0.2827(45) 0.3453(48) 0.5773(29) 0.072(4) Uiso 1 d . .
H4C H 0.2701(45) 0.4079(45) 1.0045(29) 0.075(5) Uiso 1 d . .
H6C1 H 0.4551(46) 0.2725(46) 0.8644(31) 0.072(4) Uiso 1 d . .
H6C2 H 0.3720(45) 0.1672(48) 0.7435(31) 0.072(4) Uiso 1 d . .
H6C3 H 0.5025(46) 0.3732(46) 0.7725(28) 0.072(4) Uiso 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
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
C3A C2A C2B 127.5(3) . .
C3A C2A S1A 110.4(3) . .
C2B C2A S1A 122.0(2) . .
C3A* C2A S1A* 110.6(10) . .
C2B C2A S1A* 124.3(4) . .
C2A S1A C5A 91.9(2) . .
C2A C3A C4A 112.6(5) . .
C2A C3A H3A 120.9(20) . .
C4A C3A H3A 125.8(20) . .
C5A C4A C3A 110.6(4) . .
C5A C4A H4A 125.9(33) . .
C3A C4A H4A 123.5(34) . .
C4A C5A S1A 114.4(3) . .
C4A C5A H5A 127.1(26) . .
S1A C5A H5A 118.2(26) . .
C2A S1A* C5A* 85.1(11) . .
C2A C3A* C4A* 118.7(20) . .
C2A C3A* H3A* 120.7(10) . .
C4A* C3A* H3A* 120.7(13) . .
C5A* C4A* C3A* 99.4(23) . .
C5A* C4A* H4A* 130.3(14) . .
C3A* C4A* H4A* 130.3(13) . .
C4A* C5A* S1A* 125.7(22) . .
C4A* C5A* H5A* 117.2(14) . .
S1A* C5A* H5A* 117.2(11) . .
C2B S1B C5B 92.71(12) . .
C3B C2B C2A 128.4(2) . .
C3B C2B S1B 110.1(2) . .
C2A C2B S1B 121.4(2) . .
C2B C3B C4B 114.6(2) . .
C2B C3B H3B 125.8(17) . .
C4B C3B H3B 119.5(17) . .
C5B C4B C3B 112.0(2) . .
C5B C4B C6B 126.5(2) . .
C3B C4B C6B 121.4(2) . .
C4B C5B C2C 129.5(2) . .
C4B C5B S1B 110.5(2) . .
C2C C5B S1B 120.0(2) . .
C4B C6B H6B1 110.6(21) . .
C4B C6B H6B2 108.2(22) . .
H6B1 C6B H6B2 115.9(30) . .
C4B C6B H6B3 111.7(20) . .
H6B1 C6B H6B3 108.2(28) . .
H6B2 C6B H6B3 102.0(28) . .
C5C S1C C2C 92.73(11) . .
C3C C2C C5B 130.1(2) . .
C3C C2C S1C 110.4(2) . .
C5B C2C S1C 119.4(2) . .
C2C C3C C4C 112.0(2) . .
C2C C3C C6C 126.1(2) . .
C4C C3C C6C 121.9(2) . .
C5C C4C C3C 114.7(2) . .
C5C C4C H4C 125.3(20) . .
C3C C4C H4C 120.0(20) . .
C4C C5C C5C 129.4(3) . 2_567
C4C C5C S1C 110.1(2) . .
C5C C5C S1C 120.5(2) 2_567 .
C3C C6C H6C1 112.1(22) . .
C3C C6C H6C2 115.3(21) . .
H6C1 C6C H6C2 112.9(30) . .
C3C C6C H6C3 111.0(18) . .
H6C1 C6C H6C3 96.6(27) . .
H6C2 C6C H6C3 107.4(26) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2A C3A* 1.375(2) .
C2A C3A 1.410(6) .
C2A C2B 1.449(3) .
C2A S1A 1.692(3) .
C2A S1A* 1.693(2) .
S1A C5A 1.706(4) .
C3A C4A 1.428(6) .
C3A H3A 1.16(5) .
C4A C5A 1.336(7) .
C4A H4A 0.78(4) .
C5A H5A 0.94(4) .
S1A* C5A* 1.700(2) .
C3A* C4A* 1.4149(14) .
C3A* H3A* 0.93 .
C4A* C5A* 1.30(4) .
C4A* H4A* 0.93 .
C4A* H5A 1.00(5) .
C5A* H5A* 0.93 .
C5A* H4A 1.10(5) .
S1B C2B 1.721(3) .
S1B C5B 1.738(2) .
C2B C3B 1.366(3) .
C3B C4B 1.416(3) .
C3B H3B 1.05(3) .
C4B C5B 1.380(3) .
C4B C6B 1.496(3) .
C5B C2C 1.462(3) .
C6B H6B1 0.92(3) .
C6B H6B2 0.86(3) .
C6B H6B3 0.97(3) .
S1C C5C 1.723(2) .
S1C C2C 1.738(2) .
C2C C3C 1.381(3) .
C3C C4C 1.416(3) .
C3C C6C 1.501(3) .
C4C C5C 1.365(3) .
C4C H4C 0.91(3) .
C5C C5C 1.453(4) 2_567
C6C H6C1 0.86(3) .
C6C H6C2 0.94(4) .
C6C H6C3 1.01(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C3A C2A S1A C5A 2.2(4) .
C2B C2A S1A C5A -179.6(3) .
C2B C2A C3A C4A 178.6(4) .
S1A C2A C3A C4A -3.3(6) .
C2A C3A C4A C5A 2.9(8) .
C3A C4A C5A S1A -1.2(7) .
C2A S1A C5A C4A -0.6(5) .
C3A* C2A S1A* C5A* -3.7(19) .
S1A* C2A C3A* C4A* 8.2(30) .
C2A C3A* C4A* C5A* -8.2(38) .
C3A* C4A* C5A* S1A* 5.3(42) .
C2A S1A* C5A* C4A* -1.3(34) .
C3A C2A C2B C3B 163.2(4) .
S1A C2A C2B C3B -14.7(4) .
S1A* C2A C2B C3B 167.1(4) .
C3A* C2A C2B S1B 165.5(16) .
C3A C2A C2B S1B -19.9(5) .
S1A C2A C2B S1B 162.3(2) .
S1A* C2A C2B S1B -15.9(5) .
C5B S1B C2B C3B -0.1(2) .
C5B S1B C2B C2A -177.6(2) .
C2A C2B C3B C4B 177.2(2) .
S1B C2B C3B C4B 0.0(3) .
C2B C3B C4B C5B 0.2(3) .
C2B C3B C4B C6B -178.7(2) .
C3B C4B C5B C2C 179.7(2) .
C6B C4B C5B C2C -1.4(4) .
C3B C4B C5B S1B -0.3(3) .
C6B C4B C5B S1B 178.5(2) .
C2B S1B C5B C4B 0.3(2) .
C2B S1B C5B C2C -179.8(2) .
C4B C5B C2C C3C 152.9(3) .
S1B C5B C2C C3C -27.1(4) .
C4B C5B C2C S1C -25.8(3) .
S1B C5B C2C S1C 154.32(14) .
C5C S1C C2C C3C -2.1(2) .
C5C S1C C2C C5B 176.8(2) .
C5B C2C C3C C4C -177.1(2) .
S1C C2C C3C C4C 1.6(3) .
C5B C2C C3C C6C 1.0(4) .
S1C C2C C3C C6C 179.7(2) .
C2C C3C C4C C5C -0.1(3) .
C6C C3C C4C C5C -178.3(3) .
C3C C4C C5C C5C 178.0(3) 2_567
C3C C4C C5C S1C -1.5(3) .
C2C S1C C5C C4C 2.0(2) .
C2C S1C C5C C5C -177.5(3) 2_567
