#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/30/2003085.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003085
loop_
_publ_author_name
'Krebs, Frederik C.'
'Laursen, Bo W.'
'Johannsen, Ib'
'Faldt, André'
'Bechgaard, Klaus'
'Jacobsen, Claus S.'
'Thorup, Niels'
'Boubekeur, Kamal'
_publ_section_title
;
 The geometry and structural properties of the
 4,8,12-trioxa-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene system
 in the cationic state. Structures of a planar organic cation with
 various monovalent and divalent anions
;
_journal_coden_ASTM              ASBSDK
_journal_issue                   3
_journal_name_full
;
 Acta Crystallographica, Section B: Structural Science
;
_journal_page_first              410
_journal_page_last               423
_journal_paper_doi               10.1107/S0108768198016140
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '2(C19 H9 O3), O6 S2'
_chemical_formula_sum            'C38 H18 O12 S2'
_chemical_formula_weight         730.64
_chemical_name_systematic
;
 Bis(4,8,12-trioxa-4,8,12,12c-tetrahydro-dibenzo[cd,mn]pyrenium)
dithionate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.91(3)
_cell_angle_beta                 102.37(3)
_cell_angle_gamma                108.61(3)
_cell_formula_units_Z            1
_cell_length_a                   8.6300(17)
_cell_length_b                   8.9680(18)
_cell_length_c                   9.876(2)
_cell_measurement_temperature    120(2)
_cell_volume                     689.8(3)
_computing_cell_refinement       'SAINT Siemens'
_computing_data_collection       'SMART Siemens'
_computing_data_reduction        'SAINT Siemens'
_computing_molecular_graphics    'SHELXTL (Sheldrick)'
_computing_publication_material  'XCIF (Sheldrick)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'omega scan, frame data integration'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5953
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.500
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0629P)²+0.1004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2452
_reflns_number_total             2779
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            os0007.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.1004P] 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^)+(0.0629P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3'.

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

2019-10-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C19 H9 O6 S'
_cod_original_formula_weight         365.32
_cod_original_formula_moiety         'C19 H9 O3,O3 S'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        689.8(2)
_cod_database_code               2003085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 -0.09095(4) -0.08812(4) 0.03601(4) 0.01374(12) Uani d . 1 . . S
O7 -0.25338(14) -0.07534(14) -0.02557(13) 0.0254(3) Uani d . 1 . . O
O8 -0.03366(15) -0.03780(14) 0.18974(12) 0.0286(3) Uani d . 1 . . O
O9 -0.08044(15) -0.24187(13) -0.01992(13) 0.0255(3) Uani d . 1 . . O
O1 -0.37974(13) -0.38610(12) 0.14184(11) 0.0171(2) Uani d . 1 . . O
O2 -0.49125(14) -0.83946(12) 0.36618(11) 0.0189(2) Uani d . 1 . . O
O3 -0.82405(13) -0.49878(13) 0.37918(12) 0.0189(2) Uani d . 1 . . O
C1 -0.56952(18) -0.57924(17) 0.28984(15) 0.0147(3) Uani d . 1 . . C
C2 -0.43809(19) -0.61505(17) 0.25103(15) 0.0153(3) Uani d . 1 . . C
C3 -0.34140(19) -0.51602(17) 0.17734(15) 0.0163(3) Uani d . 1 . . C
C4 -0.20936(19) -0.54894(19) 0.13989(16) 0.0197(3) Uani d . 1 . . C
H4 -0.1429 -0.4833 0.0929 0.024 Uiso calc . 1 . . H
C5 -0.17824(19) -0.6845(2) 0.17483(17) 0.0215(3) Uani d . 1 . . C
H5 -0.0911 -0.7092 0.1475 0.026 Uiso calc . 1 . . H
C6 -0.2710(2) -0.78490(18) 0.24865(17) 0.0208(3) Uani d . 1 . . C
H6 -0.2462 -0.8739 0.2703 0.025 Uiso calc . 1 . . H
C7 -0.39998(19) -0.74797(17) 0.28820(16) 0.0171(3) Uani d . 1 . . C
C8 -0.66195(19) -0.67269(17) 0.36837(15) 0.0160(3) Uani d . 1 . . C
C9 -0.61880(19) -0.80211(17) 0.40795(16) 0.0172(3) Uani d . 1 . . C
C10 -0.7001(2) -0.88712(18) 0.49493(17) 0.0215(3) Uani d . 1 . . C
H10 -0.6737 -0.9734 0.5219 0.026 Uiso calc . 1 . . H
C11 -0.8226(2) -0.84029(18) 0.54116(16) 0.0219(3) Uani d . 1 . . C
H11 -0.8761 -0.8964 0.6009 0.026 Uiso calc . 1 . . H
C12 -0.8691(2) -0.71312(19) 0.50226(16) 0.0208(3) Uani d . 1 . . C
H12 -0.9524 -0.6857 0.5342 0.025 Uiso calc . 1 . . H
C13 -0.78726(19) -0.62956(17) 0.41471(16) 0.0171(3) Uani d . 1 . . C
C14 -0.60521(18) -0.44509(17) 0.25648(15) 0.0151(3) Uani d . 1 . . C
C15 -0.73563(19) -0.40754(17) 0.29924(16) 0.0167(3) Uani d . 1 . . C
C16 -0.7746(2) -0.27802(18) 0.26240(17) 0.0199(3) Uani d . 1 . . C
H16 -0.8625 -0.2527 0.2877 0.024 Uiso calc . 1 . . H
C17 -0.6775(2) -0.18627(17) 0.18595(16) 0.0199(3) Uani d . 1 . . C
H17 -0.7042 -0.0997 0.1600 0.024 Uiso calc . 1 . . H
C18 -0.5433(2) -0.21684(17) 0.14640(16) 0.0184(3) Uani d . 1 . . C
H18 -0.4794 -0.1508 0.0981 0.022 Uiso calc . 1 . . H
C19 -0.50842(18) -0.34897(17) 0.18146(15) 0.0157(3) Uani d . 1 . . C
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'
O O 0.0106 0.0060 '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_site_symmetry_3
_geom_angle
O8 S1 O7 . 113.75(8)
O8 S1 O9 . 114.14(8)
O7 S1 O9 . 113.22(8)
O8 S1 S1 2 104.55(6)
O7 S1 S1 2 104.83(5)
O9 S1 S1 2 105.05(5)
C19 O1 C3 . 120.65(12)
C9 O2 C7 . 120.69(11)
C13 O3 C15 . 120.29(12)
C2 C1 C14 . 120.15(13)
C2 C1 C8 . 120.18(13)
C14 C1 C8 . 119.60(14)
C1 C2 C3 . 119.63(13)
C1 C2 C7 . 119.85(14)
C3 C2 C7 . 120.50(14)
C4 C3 O1 . 119.84(13)
C4 C3 C2 . 120.21(14)
O1 C3 C2 . 119.95(13)
C3 C4 C5 . 117.75(14)
C4 C5 C6 . 123.56(14)
C7 C6 C5 . 117.89(14)
C6 C7 O2 . 120.26(13)
C6 C7 C2 . 120.04(14)
O2 C7 C2 . 119.70(13)
C1 C8 C13 . 119.76(13)
C1 C8 C9 . 119.11(14)
C13 C8 C9 . 120.98(14)
O2 C9 C10 . 119.94(13)
O2 C9 C8 . 120.42(13)
C10 C9 C8 . 119.57(14)
C9 C10 C11 . 118.29(14)
C10 C11 C12 . 123.30(14)
C13 C12 C11 . 117.78(14)
O3 C13 C12 . 119.52(14)
O3 C13 C8 . 120.34(13)
C12 C13 C8 . 120.07(14)
C1 C14 C15 . 119.74(13)
C1 C14 C19 . 119.28(14)
C15 C14 C19 . 120.97(13)
C16 C15 O3 . 120.03(14)
C16 C15 C14 . 119.77(14)
O3 C15 C14 . 120.20(13)
C15 C16 C17 . 117.79(14)
C18 C17 C16 . 123.82(13)
C19 C18 C17 . 117.62(14)
O1 C19 C18 . 119.72(13)
O1 C19 C14 . 120.31(13)
C18 C19 C14 . 119.96(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O8 . 1.4493(12)
S1 O7 . 1.4507(12)
S1 O9 . 1.4512(12)
S1 S1 2 2.1616(10)
O1 C19 . 1.3724(18)
O1 C3 . 1.3779(18)
O2 C9 . 1.3733(19)
O2 C7 . 1.3813(18)
O3 C13 . 1.3793(18)
O3 C15 . 1.3829(18)
C1 C2 . 1.386(2)
C1 C14 . 1.397(2)
C1 C8 . 1.399(2)
C2 C3 . 1.407(2)
C2 C7 . 1.408(2)
C3 C4 . 1.374(2)
C4 C5 . 1.397(2)
C5 C6 . 1.398(2)
C6 C7 . 1.374(2)
C8 C13 . 1.400(2)
C8 C9 . 1.406(2)
C9 C10 . 1.381(2)
C10 C11 . 1.393(2)
C11 C12 . 1.399(2)
C12 C13 . 1.382(2)
C14 C15 . 1.402(2)
C14 C19 . 1.404(2)
C15 C16 . 1.381(2)
C16 C17 . 1.397(2)
C17 C18 . 1.391(2)
C18 C19 . 1.382(2)
