#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229212.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_2229212
loop_
_publ_author_name
'Jia, Jia'
_publ_section_title
;
 Bis(1,10-phenanthrolin-1-ium)
 9,10-dioxo-9,10-dihydroanthracene-1,5-disulfonate hexahydrate
;
_journal_coeditor_code           SI2318
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o250
_journal_paper_doi               10.1107/S1600536810053456
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C12 H9 N2 +, C14 H6 O8 S2 2-, 6H2 O'
_chemical_formula_moiety         '2(C12 H9 N2 +), C14 H6 O8 S2 2-, 6(H2 O)'
_chemical_formula_sum            'C38 H36 N4 O14 S2'
_chemical_formula_weight         836.83
_chemical_name_systematic
;
Bis(1,10-phenanthrolin-1-ium) 9,10-dioxo-9,10-dihydroanthracene-1,5-disulfonate
hexahydrate
;
_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                111.5910(10)
_cell_angle_beta                 98.8480(10)
_cell_angle_gamma                111.2340(10)
_cell_formula_units_Z            1
_cell_length_a                   10.0439(6)
_cell_length_b                   10.1978(6)
_cell_length_c                   11.1070(6)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.41
_cell_volume                     930.34(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt,
1999)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0087
_diffrn_reflns_av_sigmaI/netI    0.0171
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5035
_diffrn_reflns_theta_full        25.65
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.781957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.389
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+1.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                2964
_reflns_number_total             3499
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            si2318.cif
_cod_data_source_block           I
_cod_database_code               2229212
_cod_database_fobs_code          2229212
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_disorder_assembly
_atom_site_disorder_group
N N1 0.7261(2) 0.6318(3) 0.6490(2) 0.0508(5) Uani d . 1 . .
H H1A 0.777(3) 0.583(3) 0.616(3) 0.061 Uiso d . 1 . .
N N2 0.7525(2) 0.5796(3) 0.3953(2) 0.0529(5) Uani d . 1 . .
C C1 0.6554(3) 0.6801(3) 0.5725(3) 0.0473(6) Uani d . 1 . .
C C2 0.7199(3) 0.6540(3) 0.7734(3) 0.0614(7) Uani d . 1 . .
H H2A 0.7702 0.6189 0.8220 0.074 Uiso calc R 1 . .
C C3 0.6388(4) 0.7293(4) 0.8305(3) 0.0678(8) Uani d . 1 . .
H H3A 0.6351 0.7461 0.9179 0.081 Uiso calc R 1 . .
C C4 0.5642(3) 0.7788(3) 0.7575(3) 0.0654(8) Uani d . 1 . .
H H4A 0.5086 0.8285 0.7953 0.078 Uiso calc R 1 . .
C C5 0.5701(3) 0.7558(3) 0.6260(3) 0.0547(7) Uani d . 1 . .
C C6 0.4937(3) 0.8035(3) 0.5441(4) 0.0657(8) Uani d . 1 . .
H H6 0.4366 0.8533 0.5779 0.079 Uiso calc R 1 . .
C C7 0.5030(3) 0.7776(3) 0.4189(4) 0.0661(8) Uani d . 1 . .
H H7 0.4522 0.8101 0.3678 0.079 Uiso calc R 1 . .
C C8 0.5896(3) 0.7008(3) 0.3618(3) 0.0536(7) Uani d . 1 . .
C C9 0.6022(3) 0.6695(3) 0.2310(3) 0.0643(8) Uani d . 1 . .
H H9A 0.5532 0.6992 0.1756 0.077 Uiso calc R 1 . .
C C10 0.6866(4) 0.5954(4) 0.1856(3) 0.0652(8) Uani d . 1 . .
H H10A 0.6953 0.5735 0.0990 0.078 Uiso calc R 1 . .
C C11 0.7599(3) 0.5531(4) 0.2714(3) 0.0610(7) Uani d . 1 . .
H H11A 0.8174 0.5030 0.2392 0.073 Uiso calc R 1 . .
C C12 0.6670(3) 0.6521(3) 0.4392(3) 0.0469(6) Uani d . 1 . .
S S1 0.78814(8) 0.11641(9) 0.22241(7) 0.05292(19) Uani d . 1 . .
O O1 0.6380(2) 0.0104(3) 0.2065(3) 0.0829(7) Uani d . 1 . .
O O2 0.8478(2) 0.2720(2) 0.3366(2) 0.0633(5) Uani d . 1 . .
O O3 0.8023(3) 0.1250(4) 0.0977(2) 0.1002(9) Uani d . 1 . .
O O4 0.7954(2) 0.1068(3) 0.4845(2) 0.0661(6) Uani d . 1 . .
C C13 0.9069(3) 0.0280(3) 0.2540(2) 0.0395(5) Uani d . 1 . .
C C14 0.9501(2) 0.0149(3) 0.3743(2) 0.0346(5) Uani d . 1 . .
C C15 0.8932(3) 0.0643(3) 0.4908(2) 0.0383(5) Uani d . 1 . .
C C16 1.0474(2) -0.0535(3) 0.3832(2) 0.0365(5) Uani d . 1 . .
C C17 1.0957(3) -0.1127(3) 0.2735(3) 0.0506(6) Uani d . 1 . .
H H17 1.1599 -0.1583 0.2805 0.061 Uiso calc R 1 . .
C C18 1.0489(3) -0.1042(4) 0.1554(3) 0.0602(8) Uani d . 1 . .
H H18 1.0788 -0.1465 0.0812 0.072 Uiso calc R 1 . .
C C19 0.9570(3) -0.0324(3) 0.1471(3) 0.0524(6) Uani d . 1 . .
H H19 0.9281 -0.0245 0.0674 0.063 Uiso calc R 1 . .
O O5 0.8925(2) 0.4707(2) 0.6231(2) 0.0661(6) Uani d . 1 . .
H H5A 0.9758 0.5440 0.6439 0.099 Uiso d R 1 . .
H H5B 0.8657 0.3892 0.5524 0.099 Uiso d R 1 . .
O O6 0.6538(3) 0.2203(3) 0.9409(3) 0.1278(13) Uani d . 1 . .
H H6A 0.6893 0.1913 0.9919 0.192 Uiso d R 1 . .
H H6B 0.5678 0.1470 0.9015 0.192 Uiso d R 1 . .
O O7 0.8515(4) 0.4711(3) 0.9125(3) 0.1289(12) Uani d . 1 . .
H H7A 0.7860 0.3911 0.9080 0.193 Uiso d R 1 . .
H H7B 0.9314 0.4878 0.9619 0.193 Uiso d PR 0.50 A 1
H H7C 0.8613 0.4715 0.8406 0.193 Uiso d PR 0.50 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'
N N 0.0061 0.0033 '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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C1 . . 123.0(3) ?
C2 N1 H1A . . 117.5(19) ?
C1 N1 H1A . . 119.5(19) ?
C11 N2 C12 . . 116.6(2) ?
N1 C1 C5 . . 118.8(3) ?
N1 C1 C12 . . 120.0(2) ?
C5 C1 C12 . . 121.2(2) ?
N1 C2 C3 . . 120.1(3) ?
N1 C2 H2A . . 119.9 ?
C3 C2 H2A . . 119.9 ?
C4 C3 C2 . . 119.3(3) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
C3 C4 C5 . . 121.0(3) ?
C3 C4 H4A . . 119.5 ?
C5 C4 H4A . . 119.5 ?
C4 C5 C1 . . 117.7(3) ?
C4 C5 C6 . . 123.7(3) ?
C1 C5 C6 . . 118.6(3) ?
C7 C6 C5 . . 121.0(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C6 C7 C8 . . 121.6(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C12 . . 116.7(3) ?
C9 C8 C7 . . 124.0(3) ?
C12 C8 C7 . . 119.3(3) ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9A . . 120.1 ?
C8 C9 H9A . . 120.1 ?
C9 C10 C11 . . 118.9(3) ?
C9 C10 H10A . . 120.5 ?
C11 C10 H10A . . 120.5 ?
N2 C11 C10 . . 124.1(3) ?
N2 C11 H11A . . 117.9 ?
C10 C11 H11A . . 117.9 ?
N2 C12 C8 . . 123.9(3) ?
N2 C12 C1 . . 117.7(2) ?
C8 C12 C1 . . 118.4(2) ?
O1 S1 O2 . . 113.37(14) ?
O1 S1 O3 . . 113.36(17) ?
O2 S1 O3 . . 111.51(15) ?
O1 S1 C13 . . 106.06(12) ?
O2 S1 C13 . . 108.18(11) ?
O3 S1 C13 . . 103.59(12) ?
C19 C13 C14 . . 119.0(2) ?
C19 C13 S1 . . 114.84(18) ?
C14 C13 S1 . . 126.17(18) ?
C16 C14 C13 . . 118.6(2) ?
C16 C14 C15 . . 117.95(19) ?
C13 C14 C15 . . 123.4(2) ?
O4 C15 C14 . . 122.0(2) ?
O4 C15 C16 . 2_756 118.9(2) ?
C14 C15 C16 . 2_756 119.07(19) ?
C17 C16 C14 . . 120.7(2) ?
C17 C16 C15 . 2_756 116.5(2) ?
C14 C16 C15 . 2_756 122.7(2) ?
C18 C17 C16 . . 120.1(2) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 119.7(2) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C18 C19 C13 . . 121.8(2) ?
C18 C19 H19 . . 119.1 ?
C13 C19 H19 . . 119.1 ?
H5A O5 H5B . . 117.0 ?
H6A O6 H6B . . 100.6 ?
H7A O7 H7B . . 106.1 ?
H7A O7 H7C . . 118.2 ?
H7B O7 H7C . . 109.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.330(4) ?
N1 C1 . 1.359(3) ?
N1 H1A . 0.87(3) ?
N2 C11 . 1.320(4) ?
N2 C12 . 1.359(3) ?
C1 C5 . 1.408(4) ?
C1 C12 . 1.433(4) ?
C2 C3 . 1.382(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.364(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.406(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.427(4) ?
C6 C7 . 1.341(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.439(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.405(4) ?
C8 C12 . 1.406(3) ?
C9 C10 . 1.363(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.398(4) ?
C10 H10A . 0.9300 ?
C11 H11A . 0.9300 ?
S1 O1 . 1.439(2) ?
S1 O2 . 1.443(2) ?
S1 O3 . 1.445(2) ?
S1 C13 . 1.801(2) ?
O4 C15 . 1.211(3) ?
C13 C19 . 1.384(3) ?
C13 C14 . 1.409(3) ?
C14 C16 . 1.402(3) ?
C14 C15 . 1.487(3) ?
C15 C16 2_756 1.494(3) ?
C16 C17 . 1.391(3) ?
C16 C15 2_756 1.494(3) ?
C17 C18 . 1.369(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.381(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
O5 H5A . 0.8200 ?
O5 H5B . 0.8200 ?
O6 H6A . 0.8201 ?
O6 H6B . 0.8200 ?
O7 H7A . 0.8199 ?
O7 H7B . 0.8200 ?
O7 H7C . 0.8200 ?
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
N1 H1A O5 . 0.87(3) 1.91(3) 2.713(3) 153(3)
O5 H5A O2 2_766 0.82 1.97 2.776(3) 168
O5 H5B O2 . 0.82 2.19 2.931(3) 150
O5 H5B O4 . 0.82 2.48 3.131(3) 138
O6 H6A O3 1_556 0.82 1.96 2.775(3) 170
O6 H6B O1 2_656 0.82 1.92 2.739(3) 172
O7 H7A O6 . 0.82 1.97 2.774(4) 167
O7 H7B O7 2_767 0.82 2.20 3.021(6) 178
O7 H7C O5 . 0.82 2.48 3.301(4) 179
C2 H2A O7 . 0.93 2.39 3.300(4) 167
C4 H4A O1 2_666 0.93 2.58 3.418(4) 151
C6 H6 O4 2_666 0.93 2.54 3.350(3) 145
C18 H18 O3 2_755 0.93 2.51 3.357(4) 152
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C5 . . . . -0.7(4) ?
C2 N1 C1 C12 . . . . 180.0(2) ?
C1 N1 C2 C3 . . . . 0.0(4) ?
N1 C2 C3 C4 . . . . 0.7(4) ?
C2 C3 C4 C5 . . . . -0.7(4) ?
C3 C4 C5 C1 . . . . 0.0(4) ?
C3 C4 C5 C6 . . . . 179.5(3) ?
N1 C1 C5 C4 . . . . 0.7(4) ?
C12 C1 C5 C4 . . . . 180.0(2) ?
N1 C1 C5 C6 . . . . -178.8(2) ?
C12 C1 C5 C6 . . . . 0.5(4) ?
C4 C5 C6 C7 . . . . -179.7(3) ?
C1 C5 C6 C7 . . . . -0.2(4) ?
C5 C6 C7 C8 . . . . 0.1(5) ?
C6 C7 C8 C9 . . . . 179.4(3) ?
C6 C7 C8 C12 . . . . -0.3(4) ?
C12 C8 C9 C10 . . . . 0.0(4) ?
C7 C8 C9 C10 . . . . -179.7(3) ?
C8 C9 C10 C11 . . . . -0.4(4) ?
C12 N2 C11 C10 . . . . 0.3(4) ?
C9 C10 C11 N2 . . . . 0.3(5) ?
C11 N2 C12 C8 . . . . -0.8(4) ?
C11 N2 C12 C1 . . . . 179.1(2) ?
C9 C8 C12 N2 . . . . 0.7(4) ?
C7 C8 C12 N2 . . . . -179.6(2) ?
C9 C8 C12 C1 . . . . -179.2(2) ?
C7 C8 C12 C1 . . . . 0.5(4) ?
N1 C1 C12 N2 . . . . -1.3(3) ?
C5 C1 C12 N2 . . . . 179.5(2) ?
N1 C1 C12 C8 . . . . 178.7(2) ?
C5 C1 C12 C8 . . . . -0.6(4) ?
O1 S1 C13 C19 . . . . 109.1(2) ?
O2 S1 C13 C19 . . . . -129.0(2) ?
O3 S1 C13 C19 . . . . -10.6(2) ?
O1 S1 C13 C14 . . . . -70.5(2) ?
O2 S1 C13 C14 . . . . 51.5(2) ?
O3 S1 C13 C14 . . . . 169.9(2) ?
C19 C13 C14 C16 . . . . 2.4(3) ?
S1 C13 C14 C16 . . . . -178.08(17) ?
C19 C13 C14 C15 . . . . -175.1(2) ?
S1 C13 C14 C15 . . . . 4.4(3) ?
C16 C14 C15 O4 . . . . -171.1(2) ?
C13 C14 C15 O4 . . . . 6.4(4) ?
C16 C14 C15 C16 . . . 2_756 5.7(3) ?
C13 C14 C15 C16 . . . 2_756 -176.7(2) ?
C13 C14 C16 C17 . . . . -2.4(3) ?
C15 C14 C16 C17 . . . . 175.3(2) ?
C13 C14 C16 C15 . . . 2_756 176.4(2) ?
C15 C14 C16 C15 . . . 2_756 -5.9(4) ?
C14 C16 C17 C18 . . . . 0.3(4) ?
C15 C16 C17 C18 2_756 . . . -178.6(2) ?
C16 C17 C18 C19 . . . . 1.8(4) ?
C17 C18 C19 C13 . . . . -1.8(5) ?
C14 C13 C19 C18 . . . . -0.4(4) ?
S1 C13 C19 C18 . . . . -179.9(2) ?
