#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/48/1504828.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_1504828
loop_
_publ_author_name
'Li, Xiaochuan'
'Ma, Yuzhen'
'Wang, Bingcai'
'Li, Gongan'
_publ_section_title
;
 "Lock and key control" of photochromic reactivity by
 controlling the oxidation/reduction state.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              3639
_journal_page_last               3642
_journal_paper_doi               10.1021/ol8013655
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C18 H14 S3'
_chemical_formula_weight         326.47
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.8370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4475(10)
_cell_length_b                   8.2843(8)
_cell_length_c                   19.3730(19)
_cell_measurement_reflns_used    4860
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.46
_cell_volume                     1628.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0131
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10481
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.8806
_exptl_absorpt_correction_T_min  0.8438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     167
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.6122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2581
_reflns_number_total             2965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8013655-file002.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504828
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.65109(6) 0.30045(10) 0.17995(4) 0.0803(2) Uani 1 1 d U
S2 S 1.05179(5) 0.16871(6) 0.07419(3) 0.05356(16) Uani 1 1 d U
S3 S 0.66478(5) 0.05939(7) 0.00361(3) 0.06059(17) Uani 1 1 d U
C1 C 0.5273(3) 0.4405(4) 0.15303(19) 0.1006(11) Uani 1 1 d U
H1 H 0.4522 0.4457 0.1707 0.121 Uiso 1 1 calc R
C2 C 0.5518(2) 0.5408(4) 0.10382(19) 0.0917(9) Uani 1 1 d U
H2 H 0.4944 0.6232 0.0836 0.110 Uiso 1 1 calc R
C3 C 0.6733(2) 0.5110(3) 0.08485(13) 0.0651(6) Uani 1 1 d U
C4 C 0.73861(18) 0.3835(2) 0.12267(10) 0.0486(4) Uani 1 1 d U
C5 C 0.7231(3) 0.6059(3) 0.03516(16) 0.0850(8) Uani 1 1 d U
H5A H 0.7740 0.6941 0.0596 0.128 Uiso 1 1 calc R
H5B H 0.6507 0.6473 -0.0008 0.128 Uiso 1 1 calc R
H5C H 0.7778 0.5398 0.0133 0.128 Uiso 1 1 calc R
C6 C 0.86753(17) 0.31574(19) 0.11909(9) 0.0410(4) Uani 1 1 d U
C7 C 0.98524(17) 0.3286(2) 0.17602(9) 0.0431(4) Uani 1 1 d U
C8 C 1.0030(2) 0.4060(2) 0.24199(10) 0.0567(5) Uani 1 1 d U
H8 H 0.9326 0.4581 0.2542 0.068 Uiso 1 1 calc R
C9 C 1.1248(2) 0.4045(3) 0.28847(12) 0.0688(6) Uani 1 1 d U
H9 H 1.1365 0.4560 0.3322 0.083 Uiso 1 1 calc R
C10 C 1.2313(2) 0.3267(3) 0.27110(13) 0.0706(6) Uani 1 1 d U
H10 H 1.3126 0.3257 0.3037 0.085 Uiso 1 1 calc R
C11 C 1.2180(2) 0.2513(3) 0.20647(12) 0.0605(5) Uani 1 1 d U
H11 H 1.2894 0.2006 0.1948 0.073 Uiso 1 1 calc R
C12 C 1.09424(18) 0.2532(2) 0.15884(10) 0.0466(4) Uani 1 1 d U
C13 C 0.88884(17) 0.2343(2) 0.06173(9) 0.0417(4) Uani 1 1 d U
C14 C 0.79232(17) 0.1856(2) -0.00358(9) 0.0429(4) Uani 1 1 d U
C15 C 0.79114(19) 0.2152(2) -0.07336(10) 0.0503(4) Uani 1 1 d U
C16 C 0.6855(2) 0.1329(3) -0.11968(10) 0.0598(5) Uani 1 1 d U
H16 H 0.6696 0.1394 -0.1689 0.072 Uiso 1 1 calc R
C17 C 0.6104(2) 0.0448(3) -0.08653(11) 0.0636(5) Uani 1 1 d U
H17 H 0.5382 -0.0164 -0.1097 0.076 Uiso 1 1 calc R
C18 C 0.8880(3) 0.3210(3) -0.09788(13) 0.0793(7) Uani 1 1 d U
H18A H 0.9252 0.3970 -0.0612 0.119 Uiso 1 1 calc R
H18B H 0.8438 0.3781 -0.1400 0.119 Uiso 1 1 calc R
H18C H 0.9569 0.2556 -0.1082 0.119 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 90.65(15)
C12 S2 C13 91.46(8)
C17 S3 C14 91.99(10)
C2 C1 S1 112.2(2)
C2 C1 H1 123.9
S1 C1 H1 123.9
C1 C2 C3 114.2(3)
C1 C2 H2 122.9
C3 C2 H2 122.9
C4 C3 C2 110.9(3)
C4 C3 C5 124.6(2)
C2 C3 C5 124.5(2)
C3 C4 C6 127.68(19)
C3 C4 S1 112.03(15)
C6 C4 S1 120.29(14)
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C13 C6 C7 112.53(15)
C13 C6 C4 123.73(16)
C7 C6 C4 123.74(15)
C8 C7 C12 118.74(17)
C8 C7 C6 129.17(17)
C12 C7 C6 112.08(15)
C9 C8 C7 119.6(2)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C10 120.9(2)
C8 C9 H9 119.5
C10 C9 H9 119.5
C11 C10 C9 121.1(2)
C11 C10 H10 119.5
C9 C10 H10 119.5
C10 C11 C12 118.2(2)
C10 C11 H11 120.9
C12 C11 H11 120.9
C11 C12 C7 121.48(18)
C11 C12 S2 127.22(16)
C7 C12 S2 111.30(13)
C6 C13 C14 128.62(16)
C6 C13 S2 112.63(13)
C14 C13 S2 118.52(12)
C15 C14 C13 129.83(17)
C15 C14 S3 111.30(14)
C13 C14 S3 118.68(13)
C14 C15 C16 111.05(18)
C14 C15 C18 124.73(19)
C16 C15 C18 124.21(19)
C17 C16 C15 114.45(18)
C17 C16 H16 122.8
C15 C16 H16 122.8
C16 C17 S3 111.21(16)
C16 C17 H17 124.4
S3 C17 H17 124.4
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.723(3)
S1 C4 1.740(2)
S2 C12 1.7401(19)
S2 C13 1.7479(18)
S3 C17 1.706(2)
S3 C14 1.7252(18)
C1 C2 1.335(4)
C1 H1 0.9300
C2 C3 1.425(3)
C2 H2 0.9300
C3 C4 1.371(3)
C3 C5 1.434(4)
C4 C6 1.476(2)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 C13 1.363(2)
C6 C7 1.446(2)
C7 C8 1.402(3)
C7 C12 1.407(3)
C8 C9 1.372(3)
C8 H8 0.9300
C9 C10 1.395(3)
C9 H9 0.9300
C10 C11 1.376(3)
C10 H10 0.9300
C11 C12 1.397(3)
C11 H11 0.9300
C13 C14 1.473(2)
C14 C15 1.371(2)
C15 C16 1.420(3)
C15 C18 1.499(3)
C16 C17 1.342(3)
C16 H16 0.9300
C17 H17 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C4 S1 C1 C2 0.5(2)
S1 C1 C2 C3 -0.2(3)
C1 C2 C3 C4 -0.3(3)
C1 C2 C3 C5 -177.7(2)
C2 C3 C4 C6 -179.40(19)
C5 C3 C4 C6 -1.9(3)
C2 C3 C4 S1 0.6(2)
C5 C3 C4 S1 178.11(19)
C1 S1 C4 C3 -0.65(17)
C1 S1 C4 C6 179.37(16)
C3 C4 C6 C13 -69.0(3)
S1 C4 C6 C13 111.02(18)
C3 C4 C6 C7 111.0(2)
S1 C4 C6 C7 -69.1(2)
C13 C6 C7 C8 178.31(18)
C4 C6 C7 C8 -1.6(3)
C13 C6 C7 C12 -0.2(2)
C4 C6 C7 C12 179.83(16)
C12 C7 C8 C9 -1.0(3)
C6 C7 C8 C9 -179.49(19)
C7 C8 C9 C10 -0.1(3)
C8 C9 C10 C11 1.0(4)
C9 C10 C11 C12 -0.7(3)
C10 C11 C12 C7 -0.4(3)
C10 C11 C12 S2 179.52(17)
C8 C7 C12 C11 1.3(3)
C6 C7 C12 C11 -179.97(17)
C8 C7 C12 S2 -178.66(14)
C6 C7 C12 S2 0.05(19)
C13 S2 C12 C11 -179.87(18)
C13 S2 C12 C7 0.10(14)
C7 C6 C13 C14 174.61(16)
C4 C6 C13 C14 -5.4(3)
C7 C6 C13 S2 0.31(19)
C4 C6 C13 S2 -179.75(14)
C12 S2 C13 C6 -0.24(14)
C12 S2 C13 C14 -175.17(14)
C6 C13 C14 C15 125.8(2)
S2 C13 C14 C15 -60.2(2)
C6 C13 C14 S3 -59.7(2)
S2 C13 C14 S3 114.28(13)
C17 S3 C14 C15 0.46(15)
C17 S3 C14 C13 -175.02(15)
C13 C14 C15 C16 174.57(17)
S3 C14 C15 C16 -0.3(2)
C13 C14 C15 C18 -5.6(3)
S3 C14 C15 C18 179.53(18)
C14 C15 C16 C17 -0.1(3)
C18 C15 C16 C17 -179.9(2)
C15 C16 C17 S3 0.5(2)
C14 S3 C17 C16 -0.53(18)
