#------------------------------------------------------------------------------
#$Date: 2018-01-26 10:17:45 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205709 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020988.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_2020988
loop_
_publ_author_name
'Som, Bozumeh'
'Shue, Jessica R.'
'Smith, Mark D.'
'Shimizu, Linda S.'
_publ_section_title
;
 Temperature-induced pseudopolymorphism of molecular salts from a pyridyl
 bis-urea macrocycle and naphthalene-1,5-disulfonic acid
;
_journal_coeditor_code           FN3249
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              75
_journal_page_last               81
_journal_paper_doi               10.1107/S2053229617017600
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac
'C16 H20 N6 O2 2+, C10 H6 O6 S2 2-, 2C2 H6 O S'
_chemical_formula_moiety
'C16 H20 N6 O2 2+, C10 H6 O6 S2 2-, 2(C2 H6 O S)'
_chemical_formula_sum            'C30 H38 N6 O10 S4'
_chemical_formula_weight         770.90
_chemical_name_systematic
;4,14-Dioxo-3,5,13,15,21,22-hexaazatricyclo[15.3.1.1^7,11^]docosa-1(21),7(22),8,10,17,19-hexaene-21,22-diium naphthalene-1,5-disulfonate dimethyl sulfoxide
disolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                111.3790(10)
_cell_angle_beta                 108.656(2)
_cell_angle_gamma                93.040(2)
_cell_formula_units_Z            1
_cell_length_a                   8.5763(4)
_cell_length_b                   9.7305(5)
_cell_length_c                   11.4194(5)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.29
_cell_volume                     825.08(7)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24789
_diffrn_reflns_theta_full        30.045
_diffrn_reflns_theta_max         30.046
_diffrn_reflns_theta_min         2.290
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.4932
_exptl_absorpt_correction_T_min  0.4742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0424P)²+0.5072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                4044
_reflns_number_total             4807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3249sup1.cif
_cod_data_source_block           js16
_cod_database_code               2020988
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_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_occupancy
O O1 0.81427(12) 0.36129(11) 0.38362(10) 0.01500(19) Uani d 1
N N1 0.87827(14) 0.49577(13) 0.60781(11) 0.0133(2) Uani d 1
H H1 0.965(2) 0.541(2) 0.6072(18) 0.020(4) Uiso d 1
N N2 0.65295(14) 0.29424(13) 0.48400(12) 0.0142(2) Uani d 1
H H2 0.631(3) 0.310(2) 0.555(2) 0.029(5) Uiso d 1
N N3 0.33561(14) 0.32659(12) 0.29475(12) 0.0118(2) Uani d 1
H H3 0.331(3) 0.343(2) 0.373(2) 0.035(6) Uiso d 1
C C1 0.78352(16) 0.38224(14) 0.48736(13) 0.0126(2) Uani d 1
C C2 0.54392(16) 0.17607(15) 0.35676(13) 0.0141(2) Uani d 1
H H2A 0.4676 0.1133 0.3748 0.017 Uiso calc 1
H H2B 0.6133 0.1109 0.3154 0.017 Uiso calc 1
C C3 0.44048(16) 0.23444(14) 0.25748(13) 0.0122(2) Uani d 1
C C4 0.44811(17) 0.19913(15) 0.13154(14) 0.0149(3) Uani d 1
H H4 0.5195 0.1339 0.1030 0.018 Uiso calc 1
C C5 0.35117(17) 0.25905(15) 0.04628(14) 0.0164(3) Uani d 1
H H5 0.3561 0.2347 -0.0408 0.020 Uiso calc 1
C C6 0.24735(17) 0.35428(15) 0.08812(14) 0.0155(3) Uani d 1
H H6 0.1815 0.3965 0.0306 0.019 Uiso calc 1
C C7 0.24068(16) 0.38719(14) 0.21494(13) 0.0125(2) Uani d 1
C C8 0.12751(17) 0.48889(15) 0.26287(13) 0.0144(2) Uani d 1
H H8A 0.1651 0.5899 0.2687 0.017 Uiso calc 1
H H8B 0.0124 0.4498 0.1944 0.017 Uiso calc 1
S S1 0.26651(4) 0.79161(4) 0.12772(3) 0.01500(8) Uani d 1
O O2 0.17885(14) 0.64608(12) 0.02100(11) 0.0253(2) Uani d 1
O O3 0.30892(14) 0.79425(12) 0.26315(11) 0.0223(2) Uani d 1
O O4 0.40943(13) 0.85619(12) 0.10967(11) 0.0199(2) Uani d 1
C C9 0.12016(16) 0.91552(15) 0.11696(14) 0.0142(2) Uani d 1
C C10 0.06926(18) 0.97755(16) 0.22374(14) 0.0172(3) Uani d 1
H H10 0.1103 0.9526 0.2997 0.021 Uiso calc 1
C C11 -0.04363(18) 1.07833(16) 0.22237(14) 0.0174(3) Uani d 1
H H11 -0.0765 1.1215 0.2978 0.021 Uiso calc 1
C C12 -0.10551(17) 1.11383(15) 0.11345(14) 0.0155(3) Uani d 1
H H12 -0.1813 1.1816 0.1137 0.019 Uiso calc 1
C C13 0.05774(16) 0.94970(14) 0.00090(13) 0.0130(2) Uani d 1
S S2 0.23117(4) 0.30337(4) 0.59884(4) 0.01831(9) Uani d 1
O O5 0.36314(14) 0.33789(13) 0.54692(11) 0.0224(2) Uani d 1
C C14 0.2593(2) 0.12976(18) 0.61615(18) 0.0294(4) Uani d 1
H H14A 0.2327 0.0488 0.5268 0.044 Uiso calc 1
H H14B 0.1847 0.1067 0.6587 0.044 Uiso calc 1
H H14C 0.3760 0.1388 0.6725 0.044 Uiso calc 1
C C15 0.3084(2) 0.42181(18) 0.77460(15) 0.0249(3) Uani d 1
H H15A 0.4208 0.4065 0.8179 0.037 Uiso calc 1
H H15B 0.2331 0.3969 0.8160 0.037 Uiso calc 1
H H15C 0.3136 0.5272 0.7866 0.037 Uiso calc 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'
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
C1 N1 H1 . . 114.3(12)
C1 N1 C8 . 2_666 124.68(11)
C8 N1 H1 2_666 . 117.9(12)
C1 N2 H2 . . 120.7(14)
C1 N2 C2 . . 119.73(11)
C2 N2 H2 . . 119.5(14)
C3 N3 H3 . . 116.2(14)
C7 N3 H3 . . 120.8(14)
C7 N3 C3 . . 122.99(12)
O1 C1 N1 . . 121.17(12)
O1 C1 N2 . . 121.08(12)
N2 C1 N1 . . 117.74(12)
N2 C2 H2A . . 108.9
N2 C2 H2B . . 108.9
N2 C2 C3 . . 113.47(11)
H2A C2 H2B . . 107.7
C3 C2 H2A . . 108.9
C3 C2 H2B . . 108.9
N3 C3 C2 . . 118.29(11)
N3 C3 C4 . . 118.70(12)
C4 C3 C2 . . 123.01(12)
C3 C4 H4 . . 120.1
C3 C4 C5 . . 119.83(12)
C5 C4 H4 . . 120.1
C4 C5 H5 . . 120.0
C6 C5 C4 . . 120.00(13)
C6 C5 H5 . . 120.0
C5 C6 H6 . . 120.4
C5 C6 C7 . . 119.13(13)
C7 C6 H6 . . 120.4
N3 C7 C6 . . 119.34(12)
N3 C7 C8 . . 120.20(12)
C6 C7 C8 . . 120.46(12)
N1 C8 C7 2_666 . 114.95(11)
N1 C8 H8A 2_666 . 108.5
N1 C8 H8B 2_666 . 108.5
C7 C8 H8A . . 108.5
C7 C8 H8B . . 108.5
H8A C8 H8B . . 107.5
O2 S1 O3 . . 113.47(7)
O2 S1 O4 . . 113.56(7)
O2 S1 C9 . . 105.79(6)
O3 S1 C9 . . 105.06(6)
O4 S1 O3 . . 112.28(6)
O4 S1 C9 . . 105.75(6)
C10 C9 S1 . . 118.14(11)
C10 C9 C13 . . 120.40(13)
C13 C9 S1 . . 121.46(10)
C9 C10 H10 . . 119.6
C9 C10 C11 . . 120.82(13)
C11 C10 H10 . . 119.6
C10 C11 H11 . . 119.8
C12 C11 C10 . . 120.40(13)
C12 C11 H11 . . 119.8
C11 C12 H12 . . 119.6
C11 C12 C13 . 2_575 120.72(13)
C13 C12 H12 2_575 . 119.6
C9 C13 C13 . 2_575 118.69(15)
C12 C13 C9 2_575 . 122.36(12)
C12 C13 C13 2_575 2_575 118.95(15)
O5 S2 C14 . . 105.65(8)
O5 S2 C15 . . 105.79(7)
C15 S2 C14 . . 97.01(8)
S2 C14 H14A . . 109.5
S2 C14 H14B . . 109.5
S2 C14 H14C . . 109.5
H14A C14 H14B . . 109.5
H14A C14 H14C . . 109.5
H14B C14 H14C . . 109.5
S2 C15 H15A . . 109.5
S2 C15 H15B . . 109.5
S2 C15 H15C . . 109.5
H15A C15 H15B . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.2426(16)
N1 H1 . 0.845(19)
N1 C1 . 1.3618(17)
N1 C8 2_666 1.4465(17)
N2 H2 . 0.85(2)
N2 C1 . 1.3548(17)
N2 C2 . 1.4514(17)
N3 H3 . 0.86(2)
N3 C3 . 1.3587(16)
N3 C7 . 1.3451(17)
C2 H2A . 0.9900
C2 H2B . 0.9900
C2 C3 . 1.5081(18)
C3 C4 . 1.3759(18)
C4 H4 . 0.9500
C4 C5 . 1.388(2)
C5 H5 . 0.9500
C5 C6 . 1.3844(19)
C6 H6 . 0.9500
C6 C7 . 1.3857(18)
C7 C8 . 1.5059(18)
C8 N1 2_666 1.4465(17)
C8 H8A . 0.9900
C8 H8B . 0.9900
S1 O2 . 1.4486(11)
S1 O3 . 1.4611(11)
S1 O4 . 1.4540(11)
S1 C9 . 1.7928(14)
C9 C10 . 1.3688(19)
C9 C13 . 1.4282(19)
C10 H10 . 0.9500
C10 C11 . 1.415(2)
C11 H11 . 0.9500
C11 C12 . 1.363(2)
C12 H12 . 0.9500
C12 C13 2_575 1.4269(18)
C13 C12 2_575 1.4268(18)
C13 C13 2_575 1.430(3)
S2 O5 . 1.5098(11)
S2 C14 . 1.7909(17)
S2 C15 . 1.7825(16)
C14 H14A . 0.9800
C14 H14B . 0.9800
C14 H14C . 0.9800
C15 H15A . 0.9800
C15 H15B . 0.9800
C15 H15C . 0.9800
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 H1 O1 2_766 0.845(19) 2.029(19) 2.8712(15) 174.4(18)
N2 H2 O3 2_666 0.85(2) 2.55(2) 3.2286(16) 136.9(17)
N2 H2 O5 . 0.85(2) 2.30(2) 2.8118(15) 118.4(16)
N3 H3 O5 . 0.86(2) 1.94(2) 2.7733(15) 163(2)
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_4
_geom_torsion
N2 C2 C3 N3 . . -58.65(15)
N2 C2 C3 C4 . . 121.07(13)
N3 C3 C4 C5 . . 0.78(19)
N3 C7 C8 N1 . 2_666 -4.48(18)
C1 N2 C2 C3 . . -67.51(15)
C2 N2 C1 O1 . . -1.74(19)
C2 N2 C1 N1 . . 177.28(11)
C2 C3 C4 C5 . . -178.94(12)
C3 N3 C7 C6 . . 0.62(19)
C3 N3 C7 C8 . . -179.80(12)
C3 C4 C5 C6 . . 0.1(2)
C4 C5 C6 C7 . . -0.7(2)
C5 C6 C7 N3 . . 0.31(19)
C5 C6 C7 C8 . . -179.27(12)
C6 C7 C8 N1 . 2_666 175.10(12)
C7 N3 C3 C2 . . 178.57(11)
C7 N3 C3 C4 . . -1.16(19)
C8 N1 C1 O1 2_666 . -167.63(12)
C8 N1 C1 N2 2_666 . 13.35(19)
S1 C9 C10 C11 . . 178.84(11)
S1 C9 C13 C12 . 2_575 0.98(18)
S1 C9 C13 C13 . 2_575 -179.52(12)
O2 S1 C9 C10 . . 116.33(12)
O2 S1 C9 C13 . . -63.79(12)
O3 S1 C9 C10 . . -3.98(13)
O3 S1 C9 C13 . . 175.90(11)
O4 S1 C9 C10 . . -122.92(11)
O4 S1 C9 C13 . . 56.96(12)
C9 C10 C11 C12 . . 0.9(2)
C10 C9 C13 C12 . 2_575 -179.15(12)
C10 C9 C13 C13 . 2_575 0.4(2)
C10 C11 C12 C13 . 2_575 0.0(2)
C13 C9 C10 C11 . . -1.0(2)

_cod_database_fobs_code 2020988
