#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506371.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_4506371
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, 2(C12 H13 N2 O2 S), H2 O'
_chemical_formula_sum            'C34 H34 N4 O11 S4'
_chemical_formula_weight         802.89
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 126.43(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.300(6)
_cell_length_b                   7.0286(14)
_cell_length_c                   22.237(4)
_cell_measurement_reflns_used    8197
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.07
_cell_volume                     3558.8(18)
_computing_cell_refinement       RAPID-AUTO
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16657
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0468
_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)+(0.0904P)²+3.8013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                2842
_reflns_number_total             4045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3004855_si_002.cif
_cod_data_source_block           crystal10
_cod_original_sg_symbol_Hall     '-C 2yc  '
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               4506371
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.00150(3) 0.67641(10) 0.35601(4) 0.0360(2) Uani 1 1 d .
S2 S 0.24599(3) 0.59667(11) 0.38365(4) 0.0354(2) Uani 1 1 d .
O1 O 0.06477(9) 0.6692(3) 0.39465(12) 0.0443(5) Uani 1 1 d .
O1W O 0.0000 1.1290(4) 0.2500 0.0395(7) Uani 1 2 d SD
H1W H 0.0031(16) 1.061(4) 0.2208(16) 0.059 Uiso 1 1 d D
O2 O -0.02726(10) 0.5120(3) 0.30856(11) 0.0508(6) Uani 1 1 d .
O3 O -0.02378(12) 0.8546(3) 0.31764(15) 0.0600(7) Uani 1 1 d .
O4 O 0.23987(10) 0.7783(3) 0.40833(12) 0.0478(5) Uani 1 1 d .
O5 O 0.19372(8) 0.4893(3) 0.32971(11) 0.0472(6) Uani 1 1 d .
N1 N 0.39910(10) 0.1160(4) 0.65601(13) 0.0361(5) Uani 1 1 d D
H1N1 H 0.3810(11) 0.080(4) 0.6745(15) 0.054 Uiso 1 1 d D
H1N2 H 0.4298(8) 0.179(3) 0.6905(13) 0.054 Uiso 1 1 d D
H1N3 H 0.4116(11) 0.014(3) 0.6479(16) 0.054 Uiso 1 1 d D
N2 N 0.39654(12) 0.6828(4) 0.28340(18) 0.0503(7) Uani 1 1 d D
H2N1 H 0.4109(14) 0.582(3) 0.279(2) 0.076 Uiso 1 1 d D
H2N2 H 0.4220(12) 0.772(3) 0.303(2) 0.076 Uiso 1 1 d D
C1 C -0.05407(15) 0.8054(5) 0.48161(19) 0.0472(8) Uani 1 1 d .
H1 H -0.0745 0.9058 0.4836 0.057 Uiso 1 1 calc R
C2 C -0.04002(14) 0.8118(4) 0.43069(17) 0.0410(7) Uani 1 1 d .
H2 H -0.0504 0.9177 0.4001 0.049 Uiso 1 1 calc R
C3 C -0.01112(12) 0.6631(4) 0.42581(15) 0.0324(6) Uani 1 1 d .
C4 C 0.00694(11) 0.5010(4) 0.47381(14) 0.0307(6) Uani 1 1 d .
C5 C 0.03797(13) 0.3465(4) 0.47192(17) 0.0401(7) Uani 1 1 d .
H5 H 0.0475 0.3485 0.4385 0.048 Uiso 1 1 calc R
C6 C 0.36155(11) 0.2324(4) 0.58915(14) 0.0328(6) Uani 1 1 d .
C7 C 0.32309(13) 0.1442(4) 0.52068(16) 0.0388(7) Uani 1 1 d .
H7 H 0.3215 0.0122 0.5173 0.047 Uiso 1 1 calc R
C8 C 0.28712(13) 0.2540(4) 0.45738(16) 0.0391(6) Uani 1 1 d .
H8 H 0.2611 0.1965 0.4111 0.047 Uiso 1 1 calc R
C9 C 0.29019(11) 0.4504(4) 0.46354(15) 0.0320(6) Uani 1 1 d .
C10 C 0.32832(13) 0.5365(4) 0.53236(16) 0.0427(7) Uani 1 1 d .
H10 H 0.3296 0.6684 0.5361 0.051 Uiso 1 1 calc R
C11 C 0.36454(13) 0.4273(4) 0.59553(16) 0.0410(7) Uani 1 1 d .
H11 H 0.3906 0.4848 0.6418 0.049 Uiso 1 1 calc R
C12 C 0.28735(12) 0.6269(4) 0.34960(15) 0.0339(6) Uani 1 1 d .
C13 C 0.32292(13) 0.7881(4) 0.37033(17) 0.0411(7) Uani 1 1 d .
H13 H 0.3227 0.8817 0.3997 0.049 Uiso 1 1 calc R
C14 C 0.35813(13) 0.8079(5) 0.34717(17) 0.0443(7) Uani 1 1 d .
H14 H 0.3810 0.9167 0.3601 0.053 Uiso 1 1 calc R
C15 C 0.36012(12) 0.6678(4) 0.30482(16) 0.0382(7) Uani 1 1 d .
C16 C 0.32370(13) 0.5073(4) 0.28351(17) 0.0438(7) Uani 1 1 d .
H16 H 0.3238 0.4137 0.2540 0.053 Uiso 1 1 calc R
C17 C 0.28793(13) 0.4878(5) 0.30603(16) 0.0435(7) Uani 1 1 d .
H17 H 0.2641 0.3810 0.2919 0.052 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 113.29(16) . .
O3 S1 O1 112.53(14) . .
O2 S1 O1 111.40(14) . .
O3 S1 C3 105.90(13) . .
O2 S1 C3 105.99(13) . .
O1 S1 C3 107.16(13) . .
O4 S2 O5 118.93(14) . .
O4 S2 C12 108.72(14) . .
O5 S2 C12 108.87(13) . .
O4 S2 C9 107.78(13) . .
O5 S2 C9 107.12(13) . .
C12 S2 C9 104.47(13) . .
C6 N1 H1N1 112(2) . .
C6 N1 H1N2 111(2) . .
H1N1 N1 H1N2 107.2(15) . .
C6 N1 H1N3 113(2) . .
H1N1 N1 H1N3 107(3) . .
H1N2 N1 H1N3 107(3) . .
C15 N2 H2N1 119(3) . .
C15 N2 H2N2 117(3) . .
H2N1 N2 H2N2 111(4) . .
C5 C1 C2 120.6(3) 5_566 .
C5 C1 H1 119.7 5_566 .
C2 C1 H1 119.7 . .
C3 C2 C1 120.4(3) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 120.9(2) . .
C2 C3 S1 117.7(2) . .
C4 C3 S1 121.4(2) . .
C5 C4 C3 122.9(2) . .
C5 C4 C4 119.4(3) . 5_566
C3 C4 C4 117.7(3) . 5_566
C1 C5 C4 120.9(3) 5_566 .
C1 C5 H5 119.5 5_566 .
C4 C5 H5 119.5 . .
C11 C6 C7 121.3(3) . .
C11 C6 N1 119.4(2) . .
C7 C6 N1 119.4(3) . .
C8 C7 C6 119.5(3) . .
C8 C7 H7 120.2 . .
C6 C7 H7 120.2 . .
C7 C8 C9 119.4(3) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
C10 C9 C8 120.5(3) . .
C10 C9 S2 118.6(2) . .
C8 C9 S2 120.9(2) . .
C11 C10 C9 120.2(3) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C6 C11 C10 119.1(3) . .
C6 C11 H11 120.5 . .
C10 C11 H11 120.5 . .
C17 C12 C13 119.8(3) . .
C17 C12 S2 120.5(2) . .
C13 C12 S2 119.5(2) . .
C14 C13 C12 119.9(3) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 120.9(3) . .
C13 C14 H14 119.5 . .
C15 C14 H14 119.5 . .
N2 C15 C14 121.5(3) . .
N2 C15 C16 119.7(3) . .
C14 C15 C16 118.8(3) . .
C17 C16 C15 120.5(3) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C16 C17 C12 120.1(3) . .
C16 C17 H17 120.0 . .
C12 C17 H17 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.444(2) .
S1 O2 1.446(2) .
S1 O1 1.456(2) .
S1 C3 1.790(3) .
S2 O4 1.440(2) .
S2 O5 1.445(2) .
S2 C12 1.744(3) .
S2 C9 1.772(3) .
O1W H1W 0.85(3) .
N1 C6 1.460(3) .
N1 H1N1 0.86(3) .
N1 H1N2 0.86(3) .
N1 H1N3 0.86(3) .
N2 C15 1.372(4) .
N2 H2N1 0.85(4) .
N2 H2N2 0.85(4) .
C1 C5 1.363(4) 5_566
C1 C2 1.406(4) .
C1 H1 0.9300 .
C2 C3 1.371(4) .
C2 H2 0.9300 .
C3 C4 1.432(4) .
C4 C5 1.413(4) .
C4 C4 1.434(5) 5_566
C5 C1 1.363(4) 5_566
C5 H5 0.9300 .
C6 C11 1.375(4) .
C6 C7 1.385(4) .
C7 C8 1.383(4) .
C7 H7 0.9300 .
C8 C9 1.384(4) .
C8 H8 0.9300 .
C9 C10 1.383(4) .
C10 C11 1.379(4) .
C10 H10 0.9300 .
C11 H11 0.9300 .
C12 C17 1.383(4) .
C12 C13 1.399(4) .
C13 C14 1.374(4) .
C13 H13 0.9300 .
C14 C15 1.386(4) .
C14 H14 0.9300 .
C15 C16 1.407(4) .
C16 C17 1.377(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
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 H1W O3 0.85(3) 1.940(15) 2.763(3) 162(4) 2
N1 H1N1 O5 0.86(3) 2.118(14) 2.922(3) 155(3) 7_556
N1 H1N2 O1W 0.86(3) 2.098(11) 2.941(3) 165(3) 7_566
N1 H1N3 O1 0.86(3) 1.933(12) 2.775(3) 163(3) 7_556
N2 H2N1 O3 0.85(4) 2.20(2) 2.991(4) 156(4) 3_545
N2 H2N2 O2 0.85(4) 2.172(19) 2.981(4) 158(4) 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 1.6(5) 5_566 .
C1 C2 C3 C4 -1.9(5) . .
C1 C2 C3 S1 176.6(2) . .
O3 S1 C3 C2 -0.2(3) . .
O2 S1 C3 C2 -120.8(2) . .
O1 S1 C3 C2 120.2(2) . .
O3 S1 C3 C4 178.3(2) . .
O2 S1 C3 C4 57.7(3) . .
O1 S1 C3 C4 -61.3(2) . .
C2 C3 C4 C5 -178.5(3) . .
S1 C3 C4 C5 3.0(4) . .
C2 C3 C4 C4 0.8(5) . 5_566
S1 C3 C4 C4 -177.6(3) . 5_566
C3 C4 C5 C1 -179.7(3) . 5_566
C4 C4 C5 C1 1.0(5) 5_566 5_566
C11 C6 C7 C8 0.3(4) . .
N1 C6 C7 C8 179.4(3) . .
C6 C7 C8 C9 0.0(4) . .
C7 C8 C9 C10 -0.7(4) . .
C7 C8 C9 S2 178.7(2) . .
O4 S2 C9 C10 -23.9(3) . .
O5 S2 C9 C10 -153.0(2) . .
C12 S2 C9 C10 91.6(3) . .
O4 S2 C9 C8 156.6(2) . .
O5 S2 C9 C8 27.5(3) . .
C12 S2 C9 C8 -87.9(2) . .
C8 C9 C10 C11 1.2(5) . .
S2 C9 C10 C11 -178.3(2) . .
C7 C6 C11 C10 0.2(4) . .
N1 C6 C11 C10 -179.0(3) . .
C9 C10 C11 C6 -0.9(5) . .
O4 S2 C12 C17 -164.1(2) . .
O5 S2 C12 C17 -33.1(3) . .
C9 S2 C12 C17 81.1(3) . .
O4 S2 C12 C13 19.8(3) . .
O5 S2 C12 C13 150.7(2) . .
C9 S2 C12 C13 -95.1(2) . .
C17 C12 C13 C14 0.2(4) . .
S2 C12 C13 C14 176.4(2) . .
C12 C13 C14 C15 -1.6(5) . .
C13 C14 C15 N2 -177.8(3) . .
C13 C14 C15 C16 2.3(4) . .
N2 C15 C16 C17 178.4(3) . .
C14 C15 C16 C17 -1.6(5) . .
C15 C16 C17 C12 0.3(5) . .
C13 C12 C17 C16 0.4(4) . .
S2 C12 C17 C16 -175.7(2) . .
