#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/62/1506201.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_1506201
loop_
_publ_author_name
'Wong, Ken-Tsung'
'Chao, Teng-Chih'
'Chi, Liang-Chen'
'Chu, Ying-Ying'
'Balaiah, Akula'
'Chiu, Shih-Feng'
'Liu, Yi-Hung'
'Wang, Yu'
_publ_section_title
;
 Syntheses and structures of novel heteroarene-fused coplanar
 pi-conjugated chromophores.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5033
_journal_page_last               5036
_journal_paper_doi               10.1021/ol061791y
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C46 H38 Cl4 S2'
_chemical_formula_weight         796.68
_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                107.4040(10)
_cell_angle_beta                 109.7960(10)
_cell_angle_gamma                99.0340(10)
_cell_formula_units_Z            1
_cell_length_a                   10.3765(2)
_cell_length_b                   10.4444(2)
_cell_length_c                   10.7639(2)
_cell_measurement_reflns_used    22261
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1003.08(4)
_computing_cell_refinement       'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_data_collection       'COLLECT (Nonius BV)'
_computing_data_reduction        'HKL Denzo & Scalepack (Otwinowski & Minor)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_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  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8709
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995) 
;
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.176(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0555
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1037P)²+0.3452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1789
_reflns_number_gt                3728
_reflns_number_total             4549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061791ysi20060720_074111.cif
_cod_data_source_block           ic11988
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1003.08(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506201
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55977(6) 0.09889(5) 0.32005(6) 0.0465(2) Uani 1 1 d . . .
C1 C 0.60697(19) 0.47258(19) 0.4500(2) 0.0358(4) Uani 1 1 d . . .
H1A H 0.6769 0.4538 0.4174 0.043 Uiso 1 1 calc R . .
C2 C 0.50344(19) 0.36438(19) 0.44257(19) 0.0342(4) Uani 1 1 d . . .
C3 C 0.39719(19) 0.39109(19) 0.4925(2) 0.0340(4) Uani 1 1 d . . .
C4 C 0.29416(19) 0.25361(18) 0.4685(2) 0.0347(4) Uani 1 1 d . . .
C5 C 0.3591(2) 0.14743(19) 0.3990(2) 0.0366(4) Uani 1 1 d . . .
C6 C 0.3321(2) -0.0006(2) 0.3485(2) 0.0449(5) Uani 1 1 d . . .
H6A H 0.2558 -0.0624 0.3467 0.054 Uiso 1 1 calc R . .
C7 C 0.4324(3) -0.0399(2) 0.3030(2) 0.0489(5) Uani 1 1 d . . .
H7A H 0.4321 -0.1327 0.2663 0.059 Uiso 1 1 calc R . .
C8 C 0.4772(2) 0.21340(19) 0.3884(2) 0.0364(4) Uani 1 1 d . . .
C9 C 0.14305(19) 0.24444(19) 0.3700(2) 0.0367(4) Uani 1 1 d . . .
C10 C 0.0554(2) 0.3052(2) 0.4274(2) 0.0443(5) Uani 1 1 d . . .
H10A H 0.0862 0.3454 0.5259 0.053 Uiso 1 1 calc R . .
C11 C -0.0769(2) 0.3067(3) 0.3397(3) 0.0526(5) Uani 1 1 d . . .
H11A H -0.1332 0.3482 0.3808 0.063 Uiso 1 1 calc R . .
C12 C -0.1277(2) 0.2482(3) 0.1927(3) 0.0549(6) Uani 1 1 d . . .
C13 C -0.0408(3) 0.1867(3) 0.1358(3) 0.0596(6) Uani 1 1 d . . .
H13A H -0.0721 0.1460 0.0373 0.072 Uiso 1 1 calc R . .
C14 C 0.0924(2) 0.1844(3) 0.2232(2) 0.0494(5) Uani 1 1 d . . .
H14A H 0.1481 0.1418 0.1820 0.059 Uiso 1 1 calc R . .
C15 C -0.2714(3) 0.2528(4) 0.0992(4) 0.0832(10) Uani 1 1 d . . .
H15A H -0.2891 0.2073 0.0008 0.125 Uiso 1 1 calc R . .
H15B H -0.2718 0.3485 0.1184 0.125 Uiso 1 1 calc R . .
H15C H -0.3446 0.2055 0.1190 0.125 Uiso 1 1 calc R . .
C16 C 0.29671(19) 0.23848(19) 0.6070(2) 0.0348(4) Uani 1 1 d . . .
C17 C 0.2024(2) 0.1212(2) 0.5979(2) 0.0424(5) Uani 1 1 d . . .
H17A H 0.1380 0.0559 0.5086 0.051 Uiso 1 1 calc R . .
C18 C 0.2031(2) 0.1003(2) 0.7190(2) 0.0474(5) Uani 1 1 d . . .
H18A H 0.1396 0.0211 0.7098 0.057 Uiso 1 1 calc R . .
C19 C 0.2969(3) 0.1957(2) 0.8539(2) 0.0497(5) Uani 1 1 d . . .
C20 C 0.3911(3) 0.3107(2) 0.8628(2) 0.0530(6) Uani 1 1 d . . .
H20A H 0.4565 0.3749 0.9522 0.064 Uiso 1 1 calc R . .
C21 C 0.3909(2) 0.3331(2) 0.7418(2) 0.0451(5) Uani 1 1 d . . .
H21A H 0.4547 0.4125 0.7515 0.054 Uiso 1 1 calc R . .
C22 C 0.2964(4) 0.1747(4) 0.9867(3) 0.0789(9) Uani 1 1 d . . .
H22A H 0.3686 0.2505 1.0695 0.118 Uiso 1 1 calc R . .
H22B H 0.3160 0.0877 0.9860 0.118 Uiso 1 1 calc R . .
H22C H 0.2044 0.1726 0.9889 0.118 Uiso 1 1 calc R . .
Cl1 Cl 0.9977(4) 0.3391(5) 0.7625(4) 0.1031(11) Uani 0.50 1 d P A 1
Cl2 Cl 0.7514(5) 0.4200(5) 0.8139(6) 0.1137(12) Uani 0.50 1 d P A 1
C23 C 0.8424(13) 0.3959(13) 0.7107(11) 0.118(5) Uani 0.50 1 d P A 1
H23A H 0.8702 0.4838 0.7000 0.141 Uiso 0.50 1 calc PR A 1
H23B H 0.7764 0.3283 0.6168 0.141 Uiso 0.50 1 calc PR A 1
Cl1' Cl 0.9593(7) 0.3318(6) 0.7455(9) 0.207(3) Uani 0.50 1 d P B 2
Cl2' Cl 0.7955(5) 0.4533(8) 0.8643(8) 0.179(3) Uani 0.50 1 d P B 2
C23' C 0.8959(12) 0.4630(13) 0.7896(16) 0.117(4) Uani 0.50 1 d P B 2
H23D H 0.9764 0.5459 0.8512 0.140 Uiso 0.50 1 calc PR B 2
H23E H 0.8456 0.4779 0.7034 0.140 Uiso 0.50 1 calc PR B 2
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'
Cl Cl 0.1484 0.1585 '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
C8 S1 C7 90.46(10) .
C3 C1 C2 118.18(16) 2_666
C3 C1 H1A 120.9 2_666
C2 C1 H1A 120.9 .
C1 C2 C3 121.63(16) .
C1 C2 C8 131.91(16) .
C3 C2 C8 106.46(16) .
C1 C3 C2 120.19(17) 2_666
C1 C3 C4 128.55(16) 2_666
C2 C3 C4 111.22(15) .
C5 C4 C9 113.92(15) .
C5 C4 C16 109.31(14) .
C9 C4 C16 111.14(14) .
C5 C4 C3 100.10(14) .
C9 C4 C3 108.07(14) .
C16 C4 C3 113.95(15) .
C8 C5 C6 112.56(17) .
C8 C5 C4 110.83(16) .
C6 C5 C4 136.54(18) .
C7 C6 C5 111.07(19) .
C7 C6 H6A 124.5 .
C5 C6 H6A 124.5 .
C6 C7 S1 113.36(16) .
C6 C7 H7A 123.3 .
S1 C7 H7A 123.3 .
C5 C8 C2 111.36(16) .
C5 C8 S1 112.55(14) .
C2 C8 S1 136.06(15) .
C14 C9 C10 117.72(18) .
C14 C9 C4 122.02(17) .
C10 C9 C4 120.14(17) .
C11 C10 C9 120.8(2) .
C11 C10 H10A 119.6 .
C9 C10 H10A 119.6 .
C12 C11 C10 121.8(2) .
C12 C11 H11A 119.1 .
C10 C11 H11A 119.1 .
C11 C12 C13 117.2(2) .
C11 C12 C15 120.9(3) .
C13 C12 C15 121.9(2) .
C12 C13 C14 121.4(2) .
C12 C13 H13A 119.3 .
C14 C13 H13A 119.3 .
C9 C14 C13 121.0(2) .
C9 C14 H14A 119.5 .
C13 C14 H14A 119.5 .
C12 C15 H15A 109.5 .
C12 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C12 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C21 C16 C17 117.54(18) .
C21 C16 C4 123.51(17) .
C17 C16 C4 118.92(16) .
C18 C17 C16 121.31(19) .
C18 C17 H17A 119.3 .
C16 C17 H17A 119.3 .
C17 C18 C19 121.0(2) .
C17 C18 H18A 119.5 .
C19 C18 H18A 119.5 .
C20 C19 C18 117.68(19) .
C20 C19 C22 121.0(2) .
C18 C19 C22 121.3(2) .
C19 C20 C21 121.8(2) .
C19 C20 H20A 119.1 .
C21 C20 H20A 119.1 .
C16 C21 C20 120.67(19) .
C16 C21 H21A 119.7 .
C20 C21 H21A 119.7 .
C19 C22 H22A 109.5 .
C19 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C19 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
Cl2 C23 Cl1 119.7(5) .
Cl2 C23 H23A 107.4 .
Cl1 C23 H23A 107.4 .
Cl2 C23 H23B 107.4 .
Cl1 C23 H23B 107.4 .
H23A C23 H23B 106.9 .
Cl2' C23' Cl1' 118.2(7) .
Cl2' C23' H23D 107.8 .
Cl1' C23' H23D 107.8 .
Cl2' C23' H23E 107.8 .
Cl1' C23' H23E 107.8 .
H23D C23' H23E 107.1 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C8 1.7109(19) .
S1 C7 1.720(2) .
C1 C3 1.386(2) 2_666
C1 C2 1.394(2) .
C1 H1A 0.9300 .
C2 C3 1.411(2) .
C2 C8 1.452(2) .
C3 C1 1.386(2) 2_666
C3 C4 1.543(2) .
C4 C5 1.524(2) .
C4 C9 1.535(3) .
C4 C16 1.537(3) .
C5 C8 1.366(3) .
C5 C6 1.422(3) .
C6 C7 1.361(3) .
C6 H6A 0.9300 .
C7 H7A 0.9300 .
C9 C14 1.382(3) .
C9 C10 1.393(3) .
C10 C11 1.383(3) .
C10 H10A 0.9300 .
C11 C12 1.383(4) .
C11 H11A 0.9300 .
C12 C13 1.386(4) .
C12 C15 1.507(3) .
C13 C14 1.392(3) .
C13 H13A 0.9300 .
C14 H14A 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C21 1.384(3) .
C16 C17 1.398(3) .
C17 C18 1.382(3) .
C17 H17A 0.9300 .
C18 C19 1.386(3) .
C18 H18A 0.9300 .
C19 C20 1.381(3) .
C19 C22 1.511(3) .
C20 C21 1.390(3) .
C20 H20A 0.9300 .
C21 H21A 0.9300 .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
Cl1 C23 1.775(13) .
Cl2 C23 1.675(17) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
Cl1' C23' 1.625(14) .
Cl2' C23' 1.525(13) .
C23' H23D 0.9700 .
C23' H23E 0.9700 .
