#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/45/2234559.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_2234559
loop_
_publ_author_name
'Teerawatananond, Thapong'
'Kerdsamut, Chiaranan'
'Kokpol, Sirirat'
'Muangsin, Nongnuj'
_publ_section_title
;
 9,10-Dioxoanthracene-1,4-diyl bis(4-methylbenzenesulfonate)
;
_journal_coeditor_code           CV5268
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1423
_journal_page_last               o1424
_journal_paper_doi               10.1107/S1600536812015814
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C28 H20 O8 S2'
_chemical_formula_moiety         'C28 H20 O8 S2'
_chemical_formula_sum            'C28 H20 O8 S2'
_chemical_formula_weight         548.56
_chemical_name_common            1,4-Bis(tosyloxy)anthraquinone
_chemical_name_systematic
;
9,10-Dioxoanthracene-1,4-diyl bis(4-methylbenzenesulfonate)
;
_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                111.1220(10)
_cell_angle_beta                 90.9610(10)
_cell_angle_gamma                107.1900(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6796(2)
_cell_length_b                   10.9426(3)
_cell_length_c                   13.1833(4)
_cell_measurement_pressure       101.325
_cell_measurement_reflns_used    3943
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.59
_cell_volume                     1232.41(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12983
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 3
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9481
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow--orange
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5616
_refine_ls_number_restraints     346
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.3809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                3997
_reflns_number_total             5616
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5268.cif
_cod_data_source_block           I
_cod_database_code               2234559
_cod_database_fobs_code          2234559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
C C1 0.0724(2) -0.3607(2) 0.30321(17) 0.0455(5) Uani d U 1 1
C C2 0.2026(2) -0.2898(2) 0.37289(19) 0.0540(5) Uani d U 1 1
H H2 0.2612 -0.3377 0.3859 0.065 Uiso calc R 1 1
C C3 0.2451(2) -0.1479(2) 0.42300(19) 0.0526(5) Uani d U 1 1
H H3 0.3337 -0.0992 0.4688 0.063 Uiso calc R 1 1
C C4 0.1559(2) -0.07826(19) 0.40504(16) 0.0410(4) Uani d U 1 1
C C4A 0.0214(2) -0.14744(19) 0.33781(15) 0.0381(4) Uani d U 1 1
C C5 -0.3343(2) -0.0885(3) 0.2748(2) 0.0572(6) Uani d U 1 1
H H5 -0.3097 0.0060 0.3157 0.069 Uiso calc R 1 1
C C5A -0.2305(2) -0.1552(2) 0.26945(16) 0.0441(4) Uani d U 1 1
C C6 -0.4726(3) -0.1623(3) 0.2197(2) 0.0700(7) Uani d U 1 1
H H6 -0.5425 -0.1183 0.2251 0.084 Uiso calc R 1 1
C C7 -0.5085(3) -0.3014(3) 0.1565(2) 0.0713(7) Uani d U 1 1
H H7 -0.6016 -0.3501 0.1173 0.086 Uiso calc R 1 1
C C8 -0.4074(3) -0.3691(3) 0.1510(2) 0.0616(6) Uani d U 1 1
H H8 -0.4325 -0.4632 0.1084 0.074 Uiso calc R 1 1
C C8A -0.2675(2) -0.2962(2) 0.20916(17) 0.0457(5) Uani d U 1 1
C C9 -0.1623(2) -0.3716(2) 0.20721(17) 0.0465(5) Uani d U 1 1
C C9A -0.0210(2) -0.29290(19) 0.28346(16) 0.0404(4) Uani d U 1 1
C C10 -0.0799(2) -0.0713(2) 0.32586(16) 0.0426(4) Uani d U 1 1
C C11 -0.0130(2) -0.7359(2) 0.09847(17) 0.0465(5) Uani d U 1 1
C C12 -0.0189(3) -0.8400(2) 0.13582(17) 0.0508(5) Uani d U 1 1
H H12 0.0487 -0.8251 0.1935 0.061 Uiso calc R 1 1
C C13 -0.1266(3) -0.9662(2) 0.08608(19) 0.0571(6) Uani d U 1 1
H H13 -0.1306 -1.0367 0.1107 0.068 Uiso calc R 1 1
C C14 -0.2286(3) -0.9906(2) 0.00061(19) 0.0575(6) Uani d U 1 1
C C15 -0.2168(3) -0.8849(3) -0.0367(2) 0.0693(7) Uani d U 1 1
H H15 -0.2822 -0.9008 -0.0961 0.083 Uiso calc R 1 1
C C16 -0.1114(3) -0.7576(2) 0.0115(2) 0.0619(6) Uani d U 1 1
H H16 -0.1063 -0.6875 -0.0139 0.074 Uiso calc R 1 1
C C17 -0.3479(3) -1.1281(3) -0.0518(2) 0.0844(9) Uani d U 1 1
H H17A -0.3392 -1.1883 -0.0159 0.127 Uiso calc R 1 1
H H17B -0.3392 -1.1692 -0.1282 0.127 Uiso calc R 1 1
H H17C -0.4413 -1.1144 -0.0447 0.127 Uiso calc R 1 1
C C18 0.3179(2) 0.32113(19) 0.50215(16) 0.0406(4) Uani d U 1 1
C C19 0.4237(2) 0.4068(2) 0.59098(17) 0.0491(5) Uani d U 1 1
H H19 0.4989 0.3777 0.6082 0.059 Uiso calc R 1 1
C C20 0.4172(3) 0.5357(2) 0.65400(19) 0.0552(5) Uani d U 1 1
H H20 0.4894 0.5940 0.7133 0.066 Uiso calc R 1 1
C C21 0.3059(2) 0.5800(2) 0.6309(2) 0.0533(5) Uani d U 1 1
C C22 0.2026(3) 0.4927(2) 0.5408(2) 0.0627(6) Uani d U 1 1
H H22 0.1280 0.5223 0.5234 0.075 Uiso calc R 1 1
C C23 0.2062(2) 0.3635(2) 0.4759(2) 0.0568(6) Uani d U 1 1
H H23 0.1350 0.3061 0.4158 0.068 Uiso calc R 1 1
C C24 0.2962(3) 0.7192(2) 0.7032(3) 0.0808(9) Uani d U 1 1
H H24A 0.3768 0.7652 0.7615 0.121 Uiso calc R 1 1
H H24B 0.2062 0.7065 0.7337 0.121 Uiso calc R 1 1
H H24C 0.2995 0.7744 0.6603 0.121 Uiso calc R 1 1
O O1 -0.19121(19) -0.49172(16) 0.14755(15) 0.0704(5) Uani d U 1 1
O O2 -0.04323(17) 0.05362(15) 0.36092(15) 0.0641(4) Uani d U 1 1
O O3 0.03027(16) -0.50532(13) 0.25827(12) 0.0530(4) Uani d U 1 1
O O4 0.14116(19) -0.49740(17) 0.09439(14) 0.0711(5) Uani d U 1 1
O O5 0.24035(19) -0.58494(17) 0.21518(16) 0.0765(5) Uani d U 1 1
O O6 0.19989(14) 0.06504(13) 0.46365(11) 0.0434(3) Uani d U 1 1
O O7 0.2846(2) 0.12386(17) 0.30826(13) 0.0737(5) Uani d U 1 1
O O8 0.46239(17) 0.14656(16) 0.45212(16) 0.0697(5) Uani d U 1 1
S S1 0.32770(6) 0.15885(5) 0.42096(4) 0.04743(15) Uani d U 1 1
S S2 0.11835(6) -0.57384(5) 0.16304(5) 0.05089(16) Uani d U 1 1
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
C2 C1 O3 117.61(18)
C2 C1 C9A 122.05(18)
O3 C1 C9A 120.18(18)
C3 C2 C1 119.6(2)
C3 C2 H2 120.2
C1 C2 H2 120.2
C2 C3 C4 119.7(2)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C4A 122.00(18)
C3 C4 O6 117.29(17)
C4A C4 O6 120.54(17)
C4 C4A C9A 118.59(17)
C4 C4A C10 121.41(17)
C9A C4A C10 119.96(17)
C6 C5 C5A 119.9(2)
C6 C5 H5 120.0
C5A C5 H5 120.0
C8A C5A C5 120.04(19)
C8A C5A C10 121.30(18)
C5 C5A C10 118.63(19)
C5 C6 C7 120.3(2)
C5 C6 H6 119.8
C7 C6 H6 119.8
C6 C7 C8 120.4(2)
C6 C7 H7 119.8
C8 C7 H7 119.8
C7 C8 C8A 119.9(2)
C7 C8 H8 120.0
C8A C8 H8 120.0
C5A C8A C8 119.3(2)
C5A C8A C9 121.30(18)
C8 C8A C9 119.3(2)
O1 C9 C8A 120.74(19)
O1 C9 C9A 122.00(19)
C8A C9 C9A 117.25(17)
C1 C9A C4A 117.97(17)
C1 C9A C9 121.38(17)
C4A C9A C9 120.65(17)
O2 C10 C5A 119.98(18)
O2 C10 C4A 122.49(18)
C5A C10 C4A 117.53(17)
C12 C11 C16 121.1(2)
C12 C11 S2 119.64(17)
C16 C11 S2 119.27(17)
C13 C12 C11 118.8(2)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 121.7(2)
C12 C13 H13 119.2
C14 C13 H13 119.2
C13 C14 C15 117.8(2)
C13 C14 C17 121.2(2)
C15 C14 C17 120.9(2)
C16 C15 C14 122.0(2)
C16 C15 H15 119.0
C14 C15 H15 119.0
C15 C16 C11 118.5(2)
C15 C16 H16 120.7
C11 C16 H16 120.7
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C23 120.68(19)
C19 C18 S1 119.46(16)
C23 C18 S1 119.85(16)
C20 C19 C18 119.4(2)
C20 C19 H19 120.3
C18 C19 H19 120.3
C21 C20 C19 121.2(2)
C21 C20 H20 119.4
C19 C20 H20 119.4
C20 C21 C22 118.0(2)
C20 C21 C24 120.9(2)
C22 C21 C24 121.1(2)
C23 C22 C21 122.2(2)
C23 C22 H22 118.9
C21 C22 H22 118.9
C22 C23 C18 118.4(2)
C22 C23 H23 120.8
C18 C23 H23 120.8
C21 C24 H24A 109.5
C21 C24 H24B 109.5
H24A C24 H24B 109.5
C21 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C1 O3 S2 116.74(12)
C4 O6 S1 116.91(11)
O7 S1 O8 118.31(12)
O7 S1 O6 107.69(9)
O8 S1 O6 108.43(9)
O7 S1 C18 111.86(11)
O8 S1 C18 109.96(10)
O6 S1 C18 98.69(8)
O5 S2 O4 119.21(12)
O5 S2 O3 107.16(10)
O4 S2 O3 107.48(10)
O5 S2 C11 110.58(10)
O4 S2 C11 111.42(11)
O3 S2 C11 98.85(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.379(3)
C1 O3 1.399(2)
C1 C9A 1.401(3)
C2 C3 1.375(3)
C2 H2 0.9300
C3 C4 1.376(3)
C3 H3 0.9300
C4 C4A 1.396(3)
C4 O6 1.399(2)
C4A C9A 1.413(3)
C4A C10 1.500(3)
C5 C6 1.370(3)
C5 C5A 1.395(3)
C5 H5 0.9300
C5A C8A 1.385(3)
C5A C10 1.484(3)
C6 C7 1.376(4)
C6 H6 0.9300
C7 C8 1.380(4)
C7 H7 0.9300
C8 C8A 1.394(3)
C8 H8 0.9300
C8A C9 1.484(3)
C9 O1 1.206(2)
C9 C9A 1.502(3)
C10 O2 1.209(2)
C11 C12 1.383(3)
C11 C16 1.383(3)
C11 S2 1.740(2)
C12 C13 1.377(3)
C12 H12 0.9300
C13 C14 1.381(3)
C13 H13 0.9300
C14 C15 1.387(4)
C14 C17 1.507(3)
C15 C16 1.373(3)
C15 H15 0.9300
C16 H16 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.379(3)
C18 C23 1.380(3)
C18 S1 1.744(2)
C19 C20 1.376(3)
C19 H19 0.9300
C20 C21 1.375(3)
C20 H20 0.9300
C21 C22 1.378(3)
C21 C24 1.510(3)
C22 C23 1.375(3)
C22 H22 0.9300
C23 H23 0.9300
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
O3 S2 1.6126(15)
O4 S2 1.4180(17)
O5 S2 1.4140(18)
O6 S1 1.6094(14)
O7 S1 1.4153(18)
O8 S1 1.4185(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7 O4 1_455 0.93 2.48 3.333(3) 153.0
C3 H3 O8 2_656 0.93 2.49 3.245(3) 139.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 340346
