# Supplementary Material (ESI) for Perkin Transactions

# This journal is © The Royal Society of Chemistry 1999

# CCDC Number: 207/359



data_compound1 

 

_audit_creation_method            SHELXL 

_chemical_name_systematic 

; 

 3,3'''''-bis(butylthio)-2,2':5,,2'':5'',2''':5''',2'''':5'''',2'''''-

 -sexithiophene

; 



_chemical_name_common             ? 

_chemical_formula_moiety          'C32 H30 S8' 

_chemical_formula_structural      ? 

_chemical_formula_analytical      ? 

_chemical_formula_sum             'C32 H30 S8' 

_chemical_formula_weight          671.04 

_chemical_melting_point           '385-387'

_chemical_compound_source         'synthesis'

 

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' 

 

_symmetry_cell_setting            Monoclinic

_symmetry_space_group_name_H-M    P2(1)/a

 

loop_ 

 _symmetry_equiv_pos_as_xyz 

 'x, y, z' 

 '-x+1/2, y+1/2, -z' 

 '-x, -y, -z' 

 'x-1/2, -y-1/2, z' 

 

_cell_length_a                    13.684(2) 

_cell_length_b                    5.8270(10) 

_cell_length_c                    20.132(3) 

_cell_angle_alpha                 90.00(2) 

_cell_angle_beta                  91.76(2) 

_cell_angle_gamma                 90.00(2) 

_cell_volume                      1604.5(4) 

_cell_formula_units_Z             2 

_cell_measurement_temperature     293(2) 

_cell_measurement_reflns_used     30

_cell_measurement_theta_min       5

_cell_measurement_theta_max       16 

 

_exptl_crystal_description        'tranparent prisms'

_exptl_crystal_colour             orange

_exptl_crystal_size_max           0.28

_exptl_crystal_size_mid           0.20

_exptl_crystal_size_min           0.15

_exptl_crystal_density_meas       ? 

_exptl_crystal_density_diffrn     1.389 

_exptl_crystal_density_method     ? 

_exptl_crystal_F_000              700 

_exptl_absorpt_coefficient_mu     0.579 

_exptl_absorpt_correction_type    'based on empirical psi scan' 

_exptl_absorpt_correction_T_min   0.7766

_exptl_absorpt_correction_T_max   1.0000

 

_exptl_special_details 

; 

 ? 

; 

 

_diffrn_ambient_temperature       293(2) 

_diffrn_radiation_wavelength      0.71069 

_diffrn_radiation_type            MoK\a 

_diffrn_radiation_source          'rotating anode : 52 KV, 120 mA' 

_diffrn_radiation_monochromator   graphite 

_diffrn_measurement_device        'Siemens P4RA-M18X diffractometer'

_diffrn_measurement_method        'theta-two(theta) scan'

_diffrn_standards_number          3

_diffrn_standards_interval_count  200 

_diffrn_standards_interval_time   ? 

_diffrn_standards_decay_%         -1.2 

_diffrn_reflns_number             4116 

_diffrn_reflns_av_R_equivalents   0.0327 

_diffrn_reflns_av_sigmaI/netI     0.0539 

_diffrn_reflns_limit_h_min        -16 

_diffrn_reflns_limit_h_max        16 

_diffrn_reflns_limit_k_min        -1 

_diffrn_reflns_limit_k_max        7 

_diffrn_reflns_limit_l_min        -1 

_diffrn_reflns_limit_l_max        24 

_diffrn_reflns_theta_min          2.02 

_diffrn_reflns_theta_max          25.97 

_reflns_number_total              3140 

_reflns_number_observed           1677 

_reflns_observed_criterion        >2sigma(I) 

 

_computing_data_collection        'Siemens XSCANS'

_computing_cell_refinement        'Siemens XSCANS'

_computing_data_reduction         'Siemens XSCANS'

_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 

_computing_structure_refinement   'SHELXL-93 (Sheldrick, 1993)' 

_computing_molecular_graphics     'ORTEP (Johnson, 1965)'

_computing_publication_material   ? 

 

_refine_special_details 

; 

 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ 

 or flagged by the user for potential systematic errors.  Weighted R-factors 

 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R 

 are based on F, with F set to zero for negative F^2^. The observed criterion 

 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is 

 not relevant to the choice of reflections for refinement.  R-factors based 

 on F^2^ are statistically about twice as large as those based on F, and R- 

 factors based on ALL data will be even larger. 

; 

 

_refine_ls_structure_factor_coef  Fsqd  

_refine_ls_matrix_type            full 

_refine_ls_weighting_scheme 

 'calc w=1/[\s^2^(Fo^2^)+(0.1044P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 

_atom_sites_solution_primary      direct 

_atom_sites_solution_secondary    difmap 

_atom_sites_solution_hydrogens    geom 

_refine_ls_hydrogen_treatment     ? 

_refine_ls_extinction_method      none 

_refine_ls_extinction_coef        ? 

_refine_ls_number_reflns          3140 

_refine_ls_number_parameters      181 

_refine_ls_number_restraints      0 

_refine_ls_R_factor_all           0.1109 

_refine_ls_R_factor_obs           0.0540 

_refine_ls_wR_factor_all          0.1759 

_refine_ls_wR_factor_obs          0.1482 

_refine_ls_goodness_of_fit_all    0.979 

_refine_ls_goodness_of_fit_obs    1.152 

_refine_ls_restrained_S_all       0.979 

_refine_ls_restrained_S_obs       1.152 

_refine_ls_shift/esd_max          0.000 

_refine_ls_shift/esd_mean         0.000 

 

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 

S1A S 0.60649(8) -0.1910(2) 0.27476(7) 0.0807(4) Uani 1 d . . 

C2A C 0.5038(3) -0.0217(7) 0.2651(2) 0.0569(10) Uani 1 d . . 

C3A C 0.5175(3) 0.1442(8) 0.2185(2) 0.0718(12) Uani 1 d . . 

C4A C 0.6130(4) 0.1299(10) 0.1912(3) 0.095(2) Uani 1 d . . 

H4A H 0.6359(4) 0.2291(10) 0.1590(3) 0.114 Uiso 1 calc R . 

C5A C 0.6655(3) -0.0438(11) 0.2178(3) 0.098(2) Uani 1 d . . 

H5A H 0.7288(3) -0.0783(11) 0.2055(3) 0.117 Uiso 1 calc R . 

S2A S 0.42663(10) 0.3431(2) 0.19529(7) 0.0972(5) Uani 1 d . . 

C6A C 0.4768(4) 0.5031(11) 0.1286(2) 0.099(2) Uani 1 d . . 

H6A1 H 0.5347(4) 0.5858(11) 0.1439(2) 0.119 Uiso 1 calc R . 

H6A2 H 0.4946(4) 0.4011(11) 0.0929(2) 0.119 Uiso 1 calc R . 

C7A C 0.3955(5) 0.6752(12) 0.1038(3) 0.131(2) Uani 1 d . . 

H7A1 H 0.3376(5) 0.5883(12) 0.0906(3) 0.157 Uiso 1 calc R . 

H7A2 H 0.3783(5) 0.7729(12) 0.1407(3) 0.157 Uiso 1 calc R . 

C8A C 0.4218(8) 0.8162(18) 0.0500(5) 0.197(4) Uani 1 d . . 

H8A1 H 0.4384(8) 0.7222(18) 0.0123(5) 0.237 Uiso 1 calc R . 

H8A2 H 0.4782(8) 0.9090(18) 0.0626(5) 0.237 Uiso 1 calc R . 

C9A C 0.3334(8) 0.9729(18) 0.0314(6) 0.256(7) Uani 1 d . . 

H9A1 H 0.3499(8) 1.0702(18) -0.0050(6) 0.307 Uiso 1 calc R . 

H9A2 H 0.3177(8) 1.0658(18) 0.0690(6) 0.307 Uiso 1 calc R . 

H9A3 H 0.2781(8) 0.8796(18) 0.0188(6) 0.307 Uiso 1 calc R . 

S1B S 0.32862(7) 0.1259(2) 0.31965(6) 0.0621(3) Uani 1 d . . 

C2B C 0.4224(2) -0.0667(7) 0.3078(2) 0.0534(9) Uani 1 d . . 

C3B C 0.4120(3) -0.2520(7) 0.3472(2) 0.0635(10) Uani 1 d . . 

H3B H 0.4553(3) -0.3751(7) 0.3479(2) 0.076 Uiso 1 calc R . 

C4B C 0.3299(3) -0.2415(7) 0.3870(2) 0.0632(10) Uani 1 d . . 

H4B H 0.3131(3) -0.3578(7) 0.4161(2) 0.076 Uiso 1 calc R . 

C5B C 0.2774(3) -0.0461(7) 0.3789(2) 0.0527(9) Uani 1 d . . 

S1C S 0.13377(7) -0.1598(2) 0.46596(5) 0.0570(3) Uani 1 d . . 

C2C C 0.1885(3) 0.0234(6) 0.4103(2) 0.0509(9) Uani 1 d . . 

C3C C 0.1345(3) 0.2169(7) 0.4023(2) 0.0623(10) Uani 1 d . . 

H3C H 0.1520(3) 0.3359(7) 0.3743(2) 0.075 Uiso 1 calc R . 

C4C C 0.0502(3) 0.2218(7) 0.4400(2) 0.0591(10) Uani 1 d . . 

H4C H 0.0064(3) 0.3439(7) 0.4394(2) 0.071 Uiso 1 calc R . 

C5C C 0.0386(2) 0.0297(6) 0.4776(2) 0.0494(9) Uani 1 d . . 

 

loop_ 

 _atom_site_aniso_label 

 _atom_site_aniso_U_11 

 _atom_site_aniso_U_22 

 _atom_site_aniso_U_33 

 _atom_site_aniso_U_23 

 _atom_site_aniso_U_13 

 _atom_site_aniso_U_12 

S1A 0.0562(6) 0.0880(9) 0.0980(9) -0.0090(7) 0.0017(6) 0.0141(6) 

C2A 0.050(2) 0.059(2) 0.061(2) -0.006(2) 0.000(2) 0.000(2) 

C3A 0.064(3) 0.073(3) 0.079(3) -0.007(2) 0.011(2) 0.000(2) 

C4A 0.077(3) 0.101(4) 0.110(4) 0.001(3) 0.032(3) -0.013(3) 

C5A 0.056(3) 0.116(5) 0.123(4) -0.018(4) 0.019(3) 0.003(3) 

S2A 0.0939(9) 0.0873(10) 0.1123(11) 0.0363(8) 0.0353(8) 0.0170(7) 

C6A 0.119(4) 0.094(4) 0.086(4) 0.013(3) 0.019(3) -0.012(4) 

C7A 0.154(6) 0.129(6) 0.110(5) 0.058(4) 0.027(4) -0.006(5) 

C8A 0.256(11) 0.177(10) 0.161(8) 0.016(7) 0.035(8) -0.009(9) 

C9A 0.289(13) 0.124(8) 0.344(15) 0.018(9) -0.173(12) 0.047(9) 

S1B 0.0594(6) 0.0456(6) 0.0824(7) 0.0122(5) 0.0170(5) 0.0060(4) 

C2B 0.050(2) 0.051(2) 0.059(2) -0.008(2) -0.004(2) -0.001(2) 

C3B 0.063(2) 0.049(2) 0.079(3) 0.001(2) -0.001(2) 0.010(2) 

C4B 0.066(2) 0.050(2) 0.074(3) 0.011(2) 0.005(2) 0.005(2) 

C5B 0.050(2) 0.047(2) 0.061(2) 0.003(2) 0.000(2) -0.001(2) 

S1C 0.0640(6) 0.0391(5) 0.0684(6) 0.0079(5) 0.0105(5) 0.0032(4) 

C2C 0.054(2) 0.042(2) 0.056(2) 0.003(2) 0.003(2) -0.004(2) 

C3C 0.068(2) 0.043(2) 0.076(3) 0.016(2) 0.014(2) -0.002(2) 

C4C 0.063(2) 0.040(2) 0.075(3) 0.009(2) 0.007(2) 0.004(2) 

C5C 0.050(2) 0.041(2) 0.057(2) -0.002(2) 0.003(2) -0.001(2) 

 

_geom_special_details 

; 

 All esds (except the esd in the dihedral angle between two l.s. planes) 

 are estimated using the full covariance matrix.  The cell esds are taken 

 into account individually in the estimation of esds in distances, angles 

 and torsion angles; correlations between esds in cell parameters are only 

 used when they are defined by crystal symmetry.  An approximate (isotropic) 

 treatment of cell esds is used for estimating esds involving l.s. planes. 

; 

 

loop_ 

 _geom_bond_atom_site_label_1 

 _geom_bond_atom_site_label_2 

 _geom_bond_distance 

 _geom_bond_site_symmetry_2 

 _geom_bond_publ_flag 

S1A C5A 1.662(6) . ? 

S1A C2A 1.723(4) . ? 

C2A C3A 1.364(6) . ? 

C2A C2B 1.451(5) . ? 

C3A C4A 1.436(6) . ? 

C3A S2A 1.752(5) . ? 

C4A C5A 1.342(7) . ? 

S2A C6A 1.789(5) . ? 

C6A C7A 1.568(8) . ? 

C7A C8A 1.414(9) . ? 

C8A C9A 1.551(12) . ? 

S1B C5B 1.723(4) . ? 

S1B C2B 1.727(4) . ? 

C2B C3B 1.350(6) . ? 

C3B C4B 1.400(6) . ? 

C4B C5B 1.354(5) . ? 

C5B C2C 1.446(5) . ? 

S1C C5C 1.729(4) . ? 

S1C C2C 1.734(4) . ? 

C2C C3C 1.354(5) . ? 

C3C C4C 1.401(5) . ? 

C4C C5C 1.363(5) . ? 

C5C C5C 1.453(6) 3_556 ? 

 

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 

 _geom_angle_publ_flag 

C5A S1A C2A 92.2(2) . . ? 

C3A C2A C2B 131.3(4) . . ? 

C3A C2A S1A 110.8(3) . . ? 

C2B C2A S1A 117.9(3) . . ? 

C2A C3A C4A 111.5(4) . . ? 

C2A C3A S2A 122.7(3) . . ? 

C4A C3A S2A 125.7(4) . . ? 

C5A C4A C3A 112.0(5) . . ? 

C4A C5A S1A 113.5(4) . . ? 

C3A S2A C6A 105.0(2) . . ? 

C7A C6A S2A 106.7(4) . . ? 

C8A C7A C6A 114.9(7) . . ? 

C7A C8A C9A 108.2(9) . . ? 

C5B S1B C2B 92.1(2) . . ? 

C3B C2B C2A 126.1(4) . . ? 

C3B C2B S1B 110.3(3) . . ? 

C2A C2B S1B 123.4(3) . . ? 

C2B C3B C4B 113.7(4) . . ? 

C5B C4B C3B 113.6(4) . . ? 

C4B C5B C2C 129.3(4) . . ? 

C4B C5B S1B 110.3(3) . . ? 

C2C C5B S1B 120.4(3) . . ? 

C5C S1C C2C 92.1(2) . . ? 

C3C C2C C5B 130.1(3) . . ? 

C3C C2C S1C 110.2(3) . . ? 

C5B C2C S1C 119.7(3) . . ? 

C2C C3C C4C 114.1(3) . . ? 

C5C C4C C3C 113.3(3) . . ? 

C4C C5C C5C 129.8(4) . 3_556 ? 

C4C C5C S1C 110.4(3) . . ? 

C5C C5C S1C 119.8(4) 3_556 . ? 

 

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_1 

 _geom_torsion_site_symmetry_2 

 _geom_torsion_site_symmetry_3 

 _geom_torsion_site_symmetry_4 

 _geom_torsion_publ_flag 

 C5A S1A C2A C3A -0.2(4) . . . . ? 

 C5A S1A C2A C2B -177.1(3) . . . . ? 

 C2B C2A C3A C4A 176.3(4) . . . . ? 

 S1A C2A C3A C4A -0.1(5) . . . . ? 

 C2B C2A C3A S2A -4.8(7) . . . . ? 

 S1A C2A C3A S2A 178.8(2) . . . . ? 

 C2A C3A C4A C5A 0.4(6) . . . . ? 

 S2A C3A C4A C5A -178.4(4) . . . . ? 

 C3A C4A C5A S1A -0.6(6) . . . . ? 

 C2A S1A C5A C4A 0.4(5) . . . . ? 

 C2A C3A S2A C6A -175.0(4) . . . . ? 

 C4A C3A S2A C6A 3.7(5) . . . . ? 

 C3A S2A C6A C7A 177.2(4) . . . . ? 

 S2A C6A C7A C8A -179.3(6) . . . . ? 

 C6A C7A C8A C9A 179.4(7) . . . . ? 

 C3A C2A C2B C3B 172.1(4) . . . . ? 

 S1A C2A C2B C3B -11.7(5) . . . . ? 

 C3A C2A C2B S1B -13.0(6) . . . . ? 

 S1A C2A C2B S1B 163.2(2) . . . . ? 

 C5B S1B C2B C3B 0.8(3) . . . . ? 

 C5B S1B C2B C2A -174.8(3) . . . . ? 

 C2A C2B C3B C4B 175.3(4) . . . . ? 

 S1B C2B C3B C4B -0.2(5) . . . . ? 

 C2B C3B C4B C5B -0.8(5) . . . . ? 

 C3B C4B C5B C2C 179.1(4) . . . . ? 

 C3B C4B C5B S1B 1.4(5) . . . . ? 

 C2B S1B C5B C4B -1.3(3) . . . . ? 

 C2B S1B C5B C2C -179.2(3) . . . . ? 

 C4B C5B C2C C3C -179.3(4) . . . . ? 

 S1B C5B C2C C3C -1.8(6) . . . . ? 

 C4B C5B C2C S1C -1.5(6) . . . . ? 

 S1B C5B C2C S1C 176.0(2) . . . . ? 

 C5C S1C C2C C3C -0.1(3) . . . . ? 

 C5C S1C C2C C5B -178.3(3) . . . . ? 

 C5B C2C C3C C4C 178.0(4) . . . . ? 

 S1C C2C C3C C4C 0.1(4) . . . . ? 

 C2C C3C C4C C5C 0.0(5) . . . . ? 

 C3C C4C C5C C5C -179.7(5) . . . 3_556 ? 

 C3C C4C C5C S1C 0.0(4) . . . . ? 

 C2C S1C C5C C4C 0.1(3) . . . . ? 

 C2C S1C C5C C5C 179.8(4) . . . 3_556 ? 

 

_refine_diff_density_max    0.407 

_refine_diff_density_min   -0.321 

_refine_diff_density_rms    0.070 

#END