#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506369.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_4506369
loop_
_publ_author_name
'Deng, Zhao-Peng'
'Huo, Li-Hua'
'Zhao, Hui'
'Gao, Shan'
_publ_section_title
;
 A Co-Crystal Strategy to Tune the Supramolecular Patterns and Luminescent
 Properties: Ten Well-Designed Salts Assembled by Arenedisulfonic Acid
 with Diverse Diamines
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3342
_journal_paper_doi               10.1021/cg3004855
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C10 H6 O6 S2, C7 H12 N2, 3(H2 O)'
_chemical_formula_sum            'C17 H24 N2 O9 S2'
_chemical_formula_weight         464.50
_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                 118.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.383(3)
_cell_length_b                   12.706(3)
_cell_length_c                   13.944(3)
_cell_measurement_reflns_used    10949
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.21
_cell_volume                     2086.7(10)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       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  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20046
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_correction_T_min  0.9270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0569
_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)+(0.1143P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.1930
_reflns_number_gt                3219
_reflns_number_total             4761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3004855_si_002.cif
_cod_data_source_block           crystal8
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4506369
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 0.57277(5) 0.72740(5) 0.41213(6) 0.0409(2) Uani 1 1 d .
S2 S -0.01294(6) 0.23153(6) 0.02869(7) 0.0533(3) Uani 1 1 d .
O1W O 0.4205(2) 0.5633(3) 0.0740(2) 0.0929(10) Uani 1 1 d D
H1W1 H 0.392(4) 0.545(5) 0.0071(15) 0.139 Uiso 1 1 d D
H1W2 H 0.4921(12) 0.551(5) 0.104(3) 0.139 Uiso 1 1 d D
O1 O 0.45716(16) 0.76738(15) 0.34963(17) 0.0527(6) Uani 1 1 d .
O2 O 0.63129(18) 0.77651(16) 0.51792(18) 0.0586(6) Uani 1 1 d .
O2W O 0.1609(2) 0.9927(2) 0.1636(3) 0.0927(10) Uani 1 1 d D
H2W1 H 0.134(4) 1.041(3) 0.115(3) 0.139 Uiso 1 1 d D
H2W2 H 0.112(3) 0.944(3) 0.149(4) 0.139 Uiso 1 1 d D
O3 O 0.6346(2) 0.73228(19) 0.3518(2) 0.0701(7) Uani 1 1 d .
O3W O 0.3635(2) 0.9667(2) 0.3530(2) 0.0715(7) Uani 1 1 d D
H3W1 H 0.305(3) 0.986(3) 0.296(2) 0.107 Uiso 1 1 d D
H3W2 H 0.387(3) 0.9073(19) 0.343(3) 0.107 Uiso 1 1 d D
O4 O -0.13595(17) 0.22881(17) -0.0221(2) 0.0640(7) Uani 1 1 d .
O5 O 0.03652(18) 0.22816(19) 0.1465(2) 0.0685(7) Uani 1 1 d .
O6 O 0.0330(2) 0.15200(18) -0.0130(3) 0.0857(9) Uani 1 1 d .
N1 N 0.3074(2) 0.6466(2) 0.1748(2) 0.0557(7) Uani 1 1 d D
H1N1 H 0.346(2) 0.624(3) 0.143(2) 0.084 Uiso 1 1 d D
H1N2 H 0.2522(18) 0.684(2) 0.1262(19) 0.084 Uiso 1 1 d D
H1N3 H 0.353(2) 0.691(2) 0.224(2) 0.084 Uiso 1 1 d D
N2 N 0.2581(2) 0.2869(2) 0.2679(2) 0.0484(6) Uani 1 1 d D
H2N1 H 0.296(2) 0.277(3) 0.2330(19) 0.073 Uiso 1 1 d D
H2N2 H 0.296(2) 0.259(2) 0.3317(12) 0.073 Uiso 1 1 d D
H2N3 H 0.1950(14) 0.253(2) 0.234(2) 0.073 Uiso 1 1 d D
C1 C 0.6022(2) 0.5205(2) 0.3885(2) 0.0475(7) Uani 1 1 d .
H1 H 0.6375 0.5448 0.3491 0.057 Uiso 1 1 calc R
C2 C 0.5585(2) 0.5906(2) 0.4326(2) 0.0374(6) Uani 1 1 d .
C3 C 0.50356(19) 0.55551(19) 0.49334(19) 0.0330(5) Uani 1 1 d .
C4 C 0.4567(2) 0.6253(2) 0.5405(2) 0.0420(6) Uani 1 1 d .
H4 H 0.4608 0.6975 0.5321 0.050 Uiso 1 1 calc R
C5 C 0.4056(3) 0.5879(2) 0.5980(3) 0.0511(7) Uani 1 1 d .
H5 H 0.3756 0.6350 0.6287 0.061 Uiso 1 1 calc R
C6 C 0.0941(3) 0.3552(2) -0.0513(3) 0.0557(8) Uani 1 1 d .
H6 H 0.1219 0.2917 -0.0622 0.067 Uiso 1 1 calc R
C7 C 0.0255(2) 0.3552(2) -0.0044(2) 0.0437(7) Uani 1 1 d .
C8 C -0.01545(19) 0.4520(2) 0.0167(2) 0.0391(6) Uani 1 1 d .
C9 C -0.0848(2) 0.4574(2) 0.0678(3) 0.0497(7) Uani 1 1 d .
H9 H -0.1041 0.3958 0.0911 0.060 Uiso 1 1 calc R
C10 C -0.1236(3) 0.5508(3) 0.0835(3) 0.0604(8) Uani 1 1 d .
H10 H -0.1704 0.5524 0.1159 0.072 Uiso 1 1 calc R
C11 C 0.2045(2) 0.6119(3) 0.2801(3) 0.0592(9) Uani 1 1 d .
C12 C 0.2623(2) 0.5733(2) 0.2260(2) 0.0483(7) Uani 1 1 d .
C13 C 0.2823(2) 0.4679(2) 0.2213(2) 0.0435(6) Uani 1 1 d .
H13 H 0.3221 0.4435 0.1863 0.052 Uiso 1 1 calc R
C14 C 0.2405(2) 0.3996(2) 0.2709(2) 0.0450(7) Uani 1 1 d .
C15 C 0.1817(3) 0.4343(3) 0.3238(3) 0.0597(8) Uani 1 1 d .
H15 H 0.1544 0.3865 0.3563 0.072 Uiso 1 1 calc R
C16 C 0.1645(3) 0.5388(3) 0.3277(3) 0.0665(9) Uani 1 1 d .
H16 H 0.1249 0.5623 0.3631 0.080 Uiso 1 1 calc R
C17 C 0.1855(3) 0.7252(3) 0.2908(3) 0.0715(10) Uani 1 1 d .
H17A H 0.1157 0.7339 0.2936 0.107 Uiso 1 1 calc R
H17B H 0.1813 0.7628 0.2293 0.107 Uiso 1 1 calc R
H17C H 0.2472 0.7523 0.3565 0.107 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 S1 O2 113.38(15) . .
O3 S1 O1 112.19(15) . .
O2 S1 O1 111.52(14) . .
O3 S1 C2 105.73(13) . .
O2 S1 C2 107.76(12) . .
O1 S1 C2 105.68(12) . .
O6 S2 O5 112.52(17) . .
O6 S2 O4 112.91(17) . .
O5 S2 O4 110.71(16) . .
O6 S2 C7 106.42(15) . .
O5 S2 C7 106.67(13) . .
O4 S2 C7 107.16(12) . .
H1W1 O1W H1W2 107(4) . .
H2W1 O2W H2W2 110(5) . .
H3W1 O3W H3W2 111(4) . .
C12 N1 H1N1 121(2) . .
C12 N1 H1N2 109(2) . .
H1N1 N1 H1N2 105.5(15) . .
C12 N1 H1N3 109(2) . .
H1N1 N1 H1N3 105(3) . .
H1N2 N1 H1N3 106.2(15) . .
C14 N2 H2N1 107(2) . .
C14 N2 H2N2 113(2) . .
H2N1 N2 H2N2 108.3(15) . .
C14 N2 H2N3 113(2) . .
H2N1 N2 H2N3 107.8(15) . .
H2N2 N2 H2N3 107.4(15) . .
C2 C1 C5 120.4(3) . 3_666
C2 C1 H1 119.8 . .
C5 C1 H1 119.8 3_666 .
C1 C2 C3 121.0(2) . .
C1 C2 S1 117.5(2) . .
C3 C2 S1 121.5(2) . .
C4 C3 C2 123.0(2) . .
C4 C3 C3 119.0(3) . 3_666
C2 C3 C3 117.9(3) . 3_666
C5 C4 C3 120.8(3) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C1 120.8(3) . 3_666
C4 C5 H5 119.6 . .
C1 C5 H5 119.6 3_666 .
C7 C6 C10 120.9(3) . 3_565
C7 C6 H6 119.5 . .
C10 C6 H6 119.5 3_565 .
C6 C7 C8 120.8(2) . .
C6 C7 S2 118.0(2) . .
C8 C7 S2 121.2(2) . .
C9 C8 C7 123.5(2) . .
C9 C8 C8 118.8(3) . 3_565
C7 C8 C8 117.7(3) . 3_565
C10 C9 C8 121.2(3) . .
C10 C9 H9 119.4 . .
C8 C9 H9 119.4 . .
C9 C10 C6 120.6(3) . 3_565
C9 C10 H10 119.7 . .
C6 C10 H10 119.7 3_565 .
C16 C11 C12 117.4(3) . .
C16 C11 C17 118.5(3) . .
C12 C11 C17 124.1(4) . .
C13 C12 C11 122.5(3) . .
C13 C12 N1 117.5(3) . .
C11 C12 N1 120.0(3) . .
C12 C13 C14 117.0(3) . .
C12 C13 H13 121.5 . .
C14 C13 H13 121.5 . .
C15 C14 C13 122.4(3) . .
C15 C14 N2 118.0(3) . .
C13 C14 N2 119.6(2) . .
C16 C15 C14 119.0(4) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
C15 C16 C11 121.7(3) . .
C15 C16 H16 119.1 . .
C11 C16 H16 119.1 . .
C11 C17 H17A 109.5 . .
C11 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C11 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.434(2) .
S1 O2 1.443(2) .
S1 O1 1.460(2) .
S1 C2 1.786(3) .
S2 O6 1.441(3) .
S2 O5 1.451(3) .
S2 O4 1.451(2) .
S2 C7 1.781(3) .
O1W H1W1 0.86(4) .
O1W H1W2 0.86(4) .
O2W H2W1 0.85(4) .
O2W H2W2 0.85(4) .
O3W H3W1 0.85(4) .
O3W H3W2 0.85(4) .
N1 C12 1.466(4) .
N1 H1N1 0.87(4) .
N1 H1N2 0.87(4) .
N1 H1N3 0.87(4) .
N2 C14 1.456(4) .
N2 H2N1 0.86(3) .
N2 H2N2 0.86(3) .
N2 H2N3 0.86(3) .
C1 C2 1.362(4) .
C1 C5 1.402(4) 3_666
C1 H1 0.9300 .
C2 C3 1.431(4) .
C3 C4 1.416(4) .
C3 C3 1.432(5) 3_666
C4 C5 1.363(4) .
C4 H4 0.9300 .
C5 C1 1.402(4) 3_666
C5 H5 0.9300 .
C6 C7 1.356(4) .
C6 C10 1.397(4) 3_565
C6 H6 0.9300 .
C7 C8 1.434(4) .
C8 C9 1.415(4) .
C8 C8 1.434(5) 3_565
C9 C10 1.354(5) .
C9 H9 0.9300 .
C10 C6 1.397(4) 3_565
C10 H10 0.9300 .
C11 C16 1.388(5) .
C11 C12 1.401(4) .
C11 C17 1.482(5) .
C12 C13 1.373(4) .
C13 C14 1.383(4) .
C13 H13 0.9300 .
C14 C15 1.381(4) .
C15 C16 1.354(5) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W1 O3W 0.86(4) 2.00(2) 2.826(4) 162(5) 4_575
O1W H1W2 O3W 0.86(4) 2.04(3) 2.846(4) 157(5) 2_645
O2W H2W1 O6 0.85(4) 2.175(15) 3.014(4) 169(5) 1_565
O2W H2W2 O6 0.85(4) 2.31(3) 3.058(4) 146(4) 3_565
O3W H3W1 O2W 0.85(4) 1.938(16) 2.764(4) 165(4) .
O3W H3W2 O1 0.85(4) 1.994(12) 2.837(3) 170(4) .
N1 H1N1 O1W 0.87(4) 1.849(10) 2.722(4) 175(3) .
N1 H1N2 O4 0.87(4) 1.903(11) 2.769(3) 177(3) 3_565
N1 H1N3 O1 0.87(4) 1.909(11) 2.770(3) 169(3) .
N2 H2N1 O3 0.86(3) 1.909(13) 2.758(3) 169(3) 2_645
N2 H2N2 O2 0.86(3) 1.900(10) 2.749(3) 168(3) 3_666
N2 H2N3 O5 0.86(3) 1.904(13) 2.729(3) 159(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 C1 C2 C3 -0.1(4) 3_666 .
C5 C1 C2 S1 179.7(2) 3_666 .
O3 S1 C2 C1 -1.6(3) . .
O2 S1 C2 C1 -123.2(2) . .
O1 S1 C2 C1 117.5(2) . .
O3 S1 C2 C3 178.1(2) . .
O2 S1 C2 C3 56.6(2) . .
O1 S1 C2 C3 -62.8(2) . .
C1 C2 C3 C4 -179.9(3) . .
S1 C2 C3 C4 0.4(3) . .
C1 C2 C3 C3 0.2(4) . 3_666
S1 C2 C3 C3 -179.5(2) . 3_666
C2 C3 C4 C5 -179.7(3) . .
C3 C3 C4 C5 0.1(4) 3_666 .
C3 C4 C5 C1 -0.3(4) . 3_666
C10 C6 C7 C8 -2.1(5) 3_565 .
C10 C6 C7 S2 177.3(3) 3_565 .
O6 S2 C7 C6 -5.0(3) . .
O5 S2 C7 C6 115.3(3) . .
O4 S2 C7 C6 -126.1(3) . .
O6 S2 C7 C8 174.4(2) . .
O5 S2 C7 C8 -65.3(2) . .
O4 S2 C7 C8 53.3(3) . .
C6 C7 C8 C9 -178.3(3) . .
S2 C7 C8 C9 2.2(4) . .
C6 C7 C8 C8 2.1(4) . 3_565
S2 C7 C8 C8 -177.3(2) . 3_565
C7 C8 C9 C10 -178.3(3) . .
C8 C8 C9 C10 1.3(5) 3_565 .
C8 C9 C10 C6 -1.3(5) . 3_565
C16 C11 C12 C13 -1.6(4) . .
C17 C11 C12 C13 177.4(3) . .
C16 C11 C12 N1 -179.5(3) . .
C17 C11 C12 N1 -0.6(4) . .
C11 C12 C13 C14 1.3(4) . .
N1 C12 C13 C14 179.3(2) . .
C12 C13 C14 C15 -0.4(4) . .
C12 C13 C14 N2 179.5(2) . .
C13 C14 C15 C16 -0.2(5) . .
N2 C14 C15 C16 179.9(3) . .
C14 C15 C16 C11 -0.1(5) . .
C12 C11 C16 C15 0.9(5) . .
C17 C11 C16 C15 -178.1(3) . .
