#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:50:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179599 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/63/4506367.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_4506367
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(C6 H9 N2)'
_chemical_formula_sum            'C22 H24 N4 O6 S2'
_chemical_formula_weight         504.57
_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                 92.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   39.141(8)
_cell_length_b                   7.2708(15)
_cell_length_c                   7.8823(16)
_cell_measurement_reflns_used    6895
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.13
_cell_volume                     2240.3(8)
_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 0.997
_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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10585
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.9529
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0403
_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)+(0.0621P)²+1.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2338
_reflns_number_total             2551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3004855_si_002.cif
_cod_data_source_block           crystal6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4506367
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 0.336523(8) 0.23249(4) 0.44021(4) 0.02507(14) Uani 1 1 d .
O1 O 0.34625(3) 0.36132(14) 0.57844(13) 0.0322(3) Uani 1 1 d .
O2 O 0.34023(3) 0.04238(15) 0.49529(16) 0.0389(3) Uani 1 1 d .
O3 O 0.35360(3) 0.27542(17) 0.28683(15) 0.0386(3) Uani 1 1 d .
N1 N 0.36898(3) 0.30146(17) 0.92376(15) 0.0278(3) Uani 1 1 d D
H1N1 H 0.3602(5) 0.2008(14) 0.957(2) 0.042 Uiso 1 1 d D
H1N2 H 0.3614(4) 0.3922(16) 0.9810(18) 0.042 Uiso 1 1 d D
H1N3 H 0.3630(5) 0.319(2) 0.8188(11) 0.042 Uiso 1 1 d D
N2 N 0.40939(4) 0.0458(3) 0.7490(2) 0.0583(5) Uani 1 1 d D
H2N1 H 0.3885(3) 0.014(3) 0.756(4) 0.087 Uiso 1 1 d D
H2N2 H 0.4212(5) -0.044(3) 0.714(4) 0.087 Uiso 1 1 d D
C1 C 0.24651(4) 0.34976(19) 0.19257(17) 0.0287(3) Uani 1 1 d .
H1 H 0.2397 0.3873 0.0833 0.034 Uiso 1 1 calc R
C2 C 0.28157(4) 0.3232(2) 0.23522(17) 0.0287(3) Uani 1 1 d .
H2 H 0.2977 0.3433 0.1543 0.034 Uiso 1 1 calc R
C3 C 0.29194(3) 0.26805(17) 0.39535(17) 0.0239(3) Uani 1 1 d .
C4 C 0.26772(3) 0.23647(16) 0.52254(17) 0.0229(3) Uani 1 1 d .
C5 C 0.27751(4) 0.17885(18) 0.69057(17) 0.0267(3) Uani 1 1 d .
H5 H 0.3005 0.1605 0.7211 0.032 Uiso 1 1 calc R
C6 C 0.40630(4) 0.29172(19) 0.95391(18) 0.0278(3) Uani 1 1 d .
C7 C 0.42470(4) 0.1600(2) 0.86733(19) 0.0339(3) Uani 1 1 d .
C8 C 0.46031(4) 0.1550(2) 0.9046(2) 0.0446(4) Uani 1 1 d .
H8 H 0.4735 0.0696 0.8495 0.053 Uiso 1 1 calc R
C9 C 0.47592(5) 0.2725(3) 1.0198(3) 0.0515(5) Uani 1 1 d .
H9 H 0.4995 0.2662 1.0411 0.062 Uiso 1 1 calc R
C10 C 0.45704(5) 0.4007(3) 1.1050(3) 0.0545(5) Uani 1 1 d .
H10 H 0.4677 0.4791 1.1845 0.065 Uiso 1 1 calc R
C11 C 0.42193(4) 0.4104(2) 1.0698(2) 0.0417(4) Uani 1 1 d .
H11 H 0.4090 0.4972 1.1246 0.050 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 114.32(7) . .
O3 S1 O1 111.63(7) . .
O2 S1 O1 111.46(7) . .
O3 S1 C3 107.01(7) . .
O2 S1 C3 106.20(6) . .
O1 S1 C3 105.57(7) . .
C6 N1 H1N1 108.7(12) . .
C6 N1 H1N2 108.7(12) . .
H1N1 N1 H1N2 110.1(12) . .
C6 N1 H1N3 112.4(12) . .
H1N1 N1 H1N3 109.2(12) . .
H1N2 N1 H1N3 107.8(12) . .
C7 N2 H2N1 120.5(18) . .
C7 N2 H2N2 117.4(18) . .
H2N1 N2 H2N2 110.5(16) . .
C5 C1 C2 120.91(13) 7_556 .
C5 C1 H1 119.5 7_556 .
C2 C1 H1 119.5 . .
C3 C2 C1 120.03(13) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C2 C3 C4 121.17(13) . .
C2 C3 S1 117.90(11) . .
C4 C3 S1 120.92(10) . .
C5 C4 C4 118.97(15) . 7_556
C5 C4 C3 122.83(12) . .
C4 C4 C3 118.20(15) 7_556 .
C1 C5 C4 120.72(13) 7_556 .
C1 C5 H5 119.6 7_556 .
C4 C5 H5 119.6 . .
C11 C6 C7 122.06(14) . .
C11 C6 N1 118.79(13) . .
C7 C6 N1 119.13(13) . .
N2 C7 C6 122.13(14) . .
N2 C7 C8 121.46(15) . .
C6 C7 C8 116.38(15) . .
C9 C8 C7 121.72(16) . .
C9 C8 H8 119.1 . .
C7 C8 H8 119.1 . .
C8 C9 C10 120.75(17) . .
C8 C9 H9 119.6 . .
C10 C9 H9 119.6 . .
C9 C10 C11 118.95(17) . .
C9 C10 H10 120.5 . .
C11 C10 H10 120.5 . .
C6 C11 C10 120.14(16) . .
C6 C11 H11 119.9 . .
C10 C11 H11 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4449(12) .
S1 O2 1.4538(11) .
S1 O1 1.4722(11) .
S1 C3 1.7819(14) .
N1 C6 1.4696(18) .
N1 H1N1 0.86(2) .
N1 H1N2 0.86(2) .
N1 H1N3 0.86(2) .
N2 C7 1.365(2) .
N2 H2N1 0.86(2) .
N2 H2N2 0.86(2) .
C1 C5 1.365(2) 7_556
C1 C2 1.409(2) .
C1 H1 0.9300 .
C2 C3 1.3663(19) .
C2 H2 0.9300 .
C3 C4 1.4327(19) .
C4 C5 1.4230(18) .
C4 C4 1.428(3) 7_556
C5 C1 1.365(2) 7_556
C5 H5 0.9300 .
C6 C11 1.377(2) .
C6 C7 1.397(2) .
C7 C8 1.411(2) .
C8 C9 1.368(3) .
C8 H8 0.9300 .
C9 C10 1.384(3) .
C9 H9 0.9300 .
C10 C11 1.390(2) .
C10 H10 0.9300 .
C11 H11 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
N1 H1N1 O2 0.86(2) 1.964(9) 2.811(2) 171.2(15) 6_556
N1 H1N2 O1 0.86(2) 2.049(9) 2.898(2) 168.8(15) 6_566
N1 H1N3 O1 0.86(2) 1.997(9) 2.854(2) 176.5(17) .
N2 H2N1 O3 0.86(2) 2.53(2) 3.222(2) 139(2) 6_556
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 0.0(2) 7_556 .
C1 C2 C3 C4 -0.1(2) . .
C1 C2 C3 S1 178.79(10) . .
O3 S1 C3 C2 0.90(13) . .
O2 S1 C3 C2 -121.61(12) . .
O1 S1 C3 C2 119.93(11) . .
O3 S1 C3 C4 179.80(10) . .
O2 S1 C3 C4 57.29(12) . .
O1 S1 C3 C4 -61.17(12) . .
C2 C3 C4 C5 179.95(13) . .
S1 C3 C4 C5 1.09(18) . .
C2 C3 C4 C4 0.2(2) . 7_556
S1 C3 C4 C4 -178.62(11) . 7_556
C4 C4 C5 C1 -0.2(2) 7_556 7_556
C3 C4 C5 C1 -179.90(12) . 7_556
C11 C6 C7 N2 -178.10(17) . .
N1 C6 C7 N2 3.4(2) . .
C11 C6 C7 C8 -0.1(2) . .
N1 C6 C7 C8 -178.64(13) . .
N2 C7 C8 C9 178.20(19) . .
C6 C7 C8 C9 0.2(3) . .
C7 C8 C9 C10 0.4(3) . .
C8 C9 C10 C11 -1.0(3) . .
C7 C6 C11 C10 -0.5(3) . .
N1 C6 C11 C10 177.99(16) . .
C9 C10 C11 C6 1.1(3) . .
