#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:09:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178771 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/25/4102505.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_4102505
loop_
_publ_author_name
'Eric L. Dane'
'Sarah B. King'
'Timothy M. Swager'
_publ_section_title
;
 Conjugated Polymers That Respond to Oxidation with Increased Emission
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7758
_journal_page_last               7768
_journal_paper_doi               10.1021/ja1019063
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C24 H36 I2 S4'
_chemical_formula_weight         706.57
_chemical_name_systematic
; 
 ? 
;
_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_method           SHELXL-97
_cell_angle_alpha                61.8790(10)
_cell_angle_beta                 75.5560(10)
_cell_angle_gamma                76.3020(10)
_cell_formula_units_Z            2
_cell_length_a                   9.9066(7)
_cell_length_b                   12.6542(9)
_cell_length_c                   13.0668(9)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.44
_cell_volume                     1385.32(17)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34253
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  0.6980
_exptl_absorpt_correction_T_min  0.4248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         7713
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0230P)²+0.9402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0526
_reflns_number_gt                7054
_reflns_number_total             7713
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1019063_si_004.cif
_cod_data_source_block           09318
_cod_original_cell_volume        1385.33(17)
_cod_database_code               4102505
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
I1 I 0.275010(12) 0.283797(11) 0.606126(11) 0.01791(4) Uani 1 1 d .
S1 S 0.61178(4) 0.23014(4) 0.66114(4) 0.01397(8) Uani 1 1 d .
S2 S 0.80712(4) 0.41268(4) 0.56182(4) 0.01386(8) Uani 1 1 d .
C1 C 0.79926(18) 0.25103(16) 0.61214(16) 0.0129(3) Uani 1 1 d D
C8 C 0.87862(19) 0.17920(16) 0.71706(16) 0.0145(3) Uani 1 1 d D
H8A H 0.9768 0.1971 0.6909 0.017 Uiso 1 1 calc R
H8B H 0.8348 0.2079 0.7780 0.017 Uiso 1 1 calc R
C9 C 0.8815(2) 0.04237(17) 0.77279(17) 0.0177(4) Uani 1 1 d D
H9A H 0.7838 0.0232 0.7989 0.021 Uiso 1 1 calc R
H9B H 0.9280 0.0121 0.7134 0.021 Uiso 1 1 calc R
C10 C 0.9600(2) -0.02148(19) 0.87761(19) 0.0250(4) Uani 1 1 d D
H10A H 1.0566 0.0002 0.8516 0.030 Uiso 1 1 calc R
H10B H 0.9118 0.0076 0.9376 0.030 Uiso 1 1 calc R
C11 C 0.9685(3) -0.1585(2) 0.9332(2) 0.0362(6) Uani 1 1 d D
H11A H 0.8734 -0.1805 0.9568 0.054 Uiso 1 1 calc R
H11B H 1.0152 -0.1946 1.0025 0.054 Uiso 1 1 calc R
H11C H 1.0226 -0.1886 0.8761 0.054 Uiso 1 1 calc R
C12 C 0.85588(18) 0.21621(17) 0.51002(16) 0.0145(3) Uani 1 1 d D
H12A H 0.8321 0.1349 0.5349 0.017 Uiso 1 1 calc R
H12B H 0.8061 0.2739 0.4433 0.017 Uiso 1 1 calc R
C13 C 1.01404(18) 0.21416(17) 0.46628(16) 0.0160(3) Uani 1 1 d D
H13A H 1.0416 0.2916 0.4498 0.019 Uiso 1 1 calc R
H13B H 1.0655 0.1481 0.5283 0.019 Uiso 1 1 calc R
C14 C 1.0547(2) 0.1952(2) 0.35501(18) 0.0217(4) Uani 1 1 d D
H14A H 1.0082 0.2646 0.2919 0.026 Uiso 1 1 calc R
H14B H 1.0190 0.1215 0.3702 0.026 Uiso 1 1 calc R
C15 C 1.2135(2) 0.1821(2) 0.3122(2) 0.0271(4) Uani 1 1 d D
H15A H 1.2504 0.2536 0.2993 0.041 Uiso 1 1 calc R
H15B H 1.2323 0.1750 0.2383 0.041 Uiso 1 1 calc R
H15C H 1.2597 0.1096 0.3715 0.041 Uiso 1 1 calc R
C2 C 0.54663(18) 0.37804(16) 0.56871(16) 0.0130(3) Uani 1 1 d .
C3 C 0.40890(18) 0.41373(16) 0.54424(16) 0.0133(3) Uani 1 1 d .
C4 C 0.36172(17) 0.53452(16) 0.47680(16) 0.0132(3) Uani 1 1 d .
I2 I 0.092434(11) 0.544551(10) 1.216585(10) 0.01333(3) Uani 1 1 d .
S3 S 0.32104(5) 0.47633(5) 1.00721(4) 0.01838(9) Uani 1 1 d .
S4 S 0.24401(5) 0.43831(5) 0.82092(4) 0.01968(10) Uani 1 1 d .
C21 C 0.38900(18) 0.46666(18) 0.86644(16) 0.0164(4) Uani 1 1 d D
C28 C 0.44301(19) 0.58514(18) 0.77082(18) 0.0191(4) Uani 1 1 d D
H28A H 0.5303 0.5913 0.7905 0.023 Uiso 1 1 calc R
H28B H 0.4686 0.5794 0.6952 0.023 Uiso 1 1 calc R
C29 C 0.3422(2) 0.70171(19) 0.75283(18) 0.0214(4) Uani 1 1 d D
H29A H 0.3200 0.7112 0.8265 0.026 Uiso 1 1 calc R
H29B H 0.2532 0.6960 0.7354 0.026 Uiso 1 1 calc R
C30 C 0.4032(2) 0.8128(2) 0.6530(2) 0.0302(5) Uani 1 1 d D
H30A H 0.4198 0.8054 0.5786 0.036 Uiso 1 1 calc R
H30B H 0.4952 0.8153 0.6681 0.036 Uiso 1 1 calc R
C31 C 0.3072(3) 0.9309(2) 0.6390(2) 0.0346(5) Uani 1 1 d D
H31A H 0.2186 0.9317 0.6179 0.052 Uiso 1 1 calc R
H31B H 0.3537 0.9993 0.5768 0.052 Uiso 1 1 calc R
H31C H 0.2878 0.9375 0.7132 0.052 Uiso 1 1 calc R
C32 C 0.50983(19) 0.36044(17) 0.88594(17) 0.0170(4) Uani 1 1 d D
H32A H 0.5452 0.3551 0.8104 0.020 Uiso 1 1 calc R
H32B H 0.5876 0.3799 0.9064 0.020 Uiso 1 1 calc R
C33 C 0.4755(2) 0.23593(19) 0.9803(2) 0.0248(4) Uani 1 1 d D
H33A H 0.4247 0.2428 1.0529 0.030 Uiso 1 1 calc R
H33B H 0.4125 0.2076 0.9532 0.030 Uiso 1 1 calc R
C34 C 0.6071(2) 0.1430(2) 1.00809(19) 0.0257(4) Uani 1 1 d D
H34A H 0.6748 0.1759 1.0260 0.031 Uiso 1 1 calc R
H34B H 0.6518 0.1294 0.9378 0.031 Uiso 1 1 calc R
C35 C 0.5763(3) 0.0221(2) 1.1117(2) 0.0360(5) Uani 1 1 d D
H35A H 0.5402 0.0336 1.1833 0.054 Uiso 1 1 calc R
H35B H 0.6630 -0.0358 1.1221 0.054 Uiso 1 1 calc R
H35C H 0.5058 -0.0091 1.0963 0.054 Uiso 1 1 calc R
C22 C 0.14145(18) 0.49311(16) 1.00443(16) 0.0137(3) Uani 1 1 d .
C23 C 0.03617(18) 0.51768(16) 1.08696(15) 0.0131(3) Uani 1 1 d .
C24 C -0.10511(18) 0.52528(16) 1.08254(15) 0.0131(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C2 S1 C1 95.68(8) . .
C4 S2 C1 96.05(8) 2_666 .
C8 C1 C12 114.46(14) . .
C8 C1 S2 107.16(11) . .
C12 C1 S2 110.36(12) . .
C8 C1 S1 109.54(12) . .
C12 C1 S1 108.10(11) . .
S2 C1 S1 106.98(9) . .
C9 C8 C1 115.00(14) . .
C9 C8 H8A 108.5 . .
C1 C8 H8A 108.5 . .
C9 C8 H8B 108.5 . .
C1 C8 H8B 108.5 . .
H8A C8 H8B 107.5 . .
C10 C9 C8 111.46(15) . .
C10 C9 H9A 109.3 . .
C8 C9 H9A 109.3 . .
C10 C9 H9B 109.3 . .
C8 C9 H9B 109.3 . .
H9A C9 H9B 108.0 . .
C11 C10 C9 112.85(18) . .
C11 C10 H10A 109.0 . .
C9 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C9 C10 H10B 109.0 . .
H10A C10 H10B 107.8 . .
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 . .
C13 C12 C1 115.81(14) . .
C13 C12 H12A 108.3 . .
C1 C12 H12A 108.3 . .
C13 C12 H12B 108.3 . .
C1 C12 H12B 108.3 . .
H12A C12 H12B 107.4 . .
C14 C13 C12 110.97(15) . .
C14 C13 H13A 109.4 . .
C12 C13 H13A 109.4 . .
C14 C13 H13B 109.4 . .
C12 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
C13 C14 C15 113.50(16) . .
C13 C14 H14A 108.9 . .
C15 C14 H14A 108.9 . .
C13 C14 H14B 108.9 . .
C15 C14 H14B 108.9 . .
H14A C14 H14B 107.7 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C3 C2 C4 119.54(16) . 2_666
C3 C2 S1 123.78(14) . .
C4 C2 S1 116.58(13) 2_666 .
C4 C3 C2 120.47(16) . .
C4 C3 I1 119.80(12) . .
C2 C3 I1 119.72(13) . .
C3 C4 C2 119.99(15) . 2_666
C3 C4 S2 123.78(13) . 2_666
C2 C4 S2 116.18(13) 2_666 2_666
C22 S3 C21 97.90(8) . .
C24 S4 C21 97.63(8) 2_567 .
C32 C21 C28 109.84(15) . .
C32 C21 S3 108.39(13) . .
C28 C21 S3 110.91(13) . .
C32 C21 S4 109.89(12) . .
C28 C21 S4 109.68(13) . .
S3 C21 S4 108.09(9) . .
C29 C28 C21 116.51(16) . .
C29 C28 H28A 108.2 . .
C21 C28 H28A 108.2 . .
C29 C28 H28B 108.2 . .
C21 C28 H28B 108.2 . .
H28A C28 H28B 107.3 . .
C28 C29 C30 112.32(17) . .
C28 C29 H29A 109.1 . .
C30 C29 H29A 109.1 . .
C28 C29 H29B 109.1 . .
C30 C29 H29B 109.1 . .
H29A C29 H29B 107.9 . .
C29 C30 C31 112.9(2) . .
C29 C30 H30A 109.0 . .
C31 C30 H30A 109.0 . .
C29 C30 H30B 109.0 . .
C31 C30 H30B 109.0 . .
H30A C30 H30B 107.8 . .
C30 C31 H31A 109.5 . .
C30 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
C30 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
C33 C32 C21 116.87(16) . .
C33 C32 H32A 108.1 . .
C21 C32 H32A 108.1 . .
C33 C32 H32B 108.1 . .
C21 C32 H32B 108.1 . .
H32A C32 H32B 107.3 . .
C34 C33 C32 112.29(16) . .
C34 C33 H33A 109.1 . .
C32 C33 H33A 109.1 . .
C34 C33 H33B 109.1 . .
C32 C33 H33B 109.1 . .
H33A C33 H33B 107.9 . .
C33 C34 C35 112.93(19) . .
C33 C34 H34A 109.0 . .
C35 C34 H34A 109.0 . .
C33 C34 H34B 109.0 . .
C35 C34 H34B 109.0 . .
H34A C34 H34B 107.8 . .
C34 C35 H35A 109.5 . .
C34 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
C34 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C23 C22 C24 119.94(15) . 2_567
C23 C22 S3 123.08(13) . .
C24 C22 S3 116.91(13) 2_567 .
C24 C23 C22 120.23(15) . .
C24 C23 I2 120.35(12) . .
C22 C23 I2 119.42(12) . .
C23 C24 C22 119.83(15) . 2_567
C23 C24 S4 123.15(13) . 2_567
C22 C24 S4 116.99(13) 2_567 2_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C3 2.0883(17) .
S1 C2 1.7503(18) .
S1 C1 1.8464(18) .
S2 C4 1.7530(17) 2_666
S2 C1 1.8452(18) .
C1 C8 1.533(2) .
C1 C12 1.534(2) .
C8 C9 1.526(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.524(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.521(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 C13 1.527(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.525(3) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.530(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C2 C3 1.399(2) .
C2 C4 1.410(2) 2_666
C3 C4 1.389(3) .
C4 C2 1.410(2) 2_666
C4 S2 1.7530(17) 2_666
I2 C23 2.0974(17) .
S3 C22 1.7486(17) .
S3 C21 1.8458(18) .
S4 C24 1.7546(18) 2_567
S4 C21 1.8485(18) .
C21 C32 1.540(3) .
C21 C28 1.541(3) .
C28 C29 1.524(3) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 C30 1.524(3) .
C29 H29A 0.9900 .
C29 H29B 0.9900 .
C30 C31 1.525(3) .
C30 H30A 0.9900 .
C30 H30B 0.9900 .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 C33 1.527(3) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.523(3) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.527(3) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 H35A 0.9800 .
C35 H35B 0.9800 .
C35 H35C 0.9800 .
C22 C23 1.396(2) .
C22 C24 1.403(2) 2_567
C23 C24 1.394(2) .
C24 C22 1.403(2) 2_567
C24 S4 1.7546(18) 2_567
