#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:48:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180519 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/88/7218839.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_7218839
loop_
_publ_author_name
'Li, Ya-Nan'
'Huo, Li-Hua'
'Yu, Yi-Zhe'
'Ge, Fa-Yuan'
'Deng, Zhao-Peng'
'Zhu, Zhi-Biao'
'Gao, Shan'
_publ_section_title
;
 Influence of solvents and assembly on the supramolecular patterns and
 luminescent properties of organic salts comprising
 4,4’-dihydroxybiphenyl-3,3’-disulfonate and
 triphenylmethanaminium
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12338G
_journal_year                    2014
_chemical_formula_moiety         'C12 H8 O8 S2, 2(C19 H18 N), 2(H2 O), H2 O'
_chemical_formula_sum            'C50 H50 N2 O11 S2'
_chemical_formula_weight         919.04
_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                 103.679(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.0976(12)
_cell_length_b                   12.9962(4)
_cell_length_c                   13.9750(8)
_cell_measurement_reflns_used    1890
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.47
_cell_volume                     4781.9(4)
_computing_cell_refinement
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis Pro (Agilent, 2013)
;
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.1954
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8515
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.9581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis Pro (Agilent, 2013)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5476
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0852P)²+6.2570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1906
_reflns_number_gt                3677
_reflns_number_total             5476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12338g2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7218839
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46286(3) 0.65582(5) 0.01555(6) 0.0420(2) Uani 1 1 d . . .
O1 O 0.48616(10) 0.62485(18) 0.11389(19) 0.0749(7) Uani 1 1 d . . .
O1W O 0.43872(10) 0.48262(19) 0.27638(16) 0.0638(6) Uani 1 1 d D . .
H1W H 0.4608(12) 0.531(2) 0.289(3) 0.096 Uiso 1 1 d D . .
H2W H 0.4468(14) 0.437(2) 0.322(2) 0.096 Uiso 1 1 d D . .
O2 O 0.49445(9) 0.64396(15) -0.0541(2) 0.0658(7) Uani 1 1 d . . .
O3 O 0.41344(7) 0.60587(14) -0.02082(17) 0.0527(5) Uani 1 1 d . . .
O4 O 0.36591(8) 0.76277(16) 0.0487(2) 0.0627(7) Uani 1 1 d D . .
H4O H 0.3703(16) 0.7043(16) 0.025(3) 0.094 Uiso 1 1 d D . .
N1 N 0.41121(8) 0.41795(16) 0.08343(17) 0.0372(5) Uani 1 1 d D . .
H1N1 H 0.4116(10) 0.4744(12) 0.0501(15) 0.056 Uiso 1 1 d D . .
H1N2 H 0.4182(10) 0.4367(18) 0.1453(8) 0.056 Uiso 1 1 d D . .
H1N3 H 0.4362(8) 0.3807(16) 0.0755(17) 0.056 Uiso 1 1 d D . .
C1 C 0.36091(10) 0.36077(19) 0.05609(19) 0.0375(6) Uani 1 1 d . . .
C2 C 0.35697(15) 0.2917(2) 0.1423(2) 0.0565(8) Uani 1 1 d . . .
C3 C 0.31130(19) 0.2855(4) 0.1724(3) 0.0937(15) Uani 1 1 d . . .
H3A H 0.2840 0.3272 0.1433 0.112 Uiso 1 1 calc R . .
C4 C 0.3071(4) 0.2168(6) 0.2459(5) 0.0977(15) Uani 1 1 d . . .
H4A H 0.2767 0.2128 0.2658 0.188 Uiso 1 1 calc R . .
C5 C 0.3463(5) 0.1554(6) 0.2894(5) 0.0837(6) Uani 1 1 d . . .
H5A H 0.3428 0.1088 0.3378 0.226 Uiso 1 1 calc R . .
C6 C 0.3906(4) 0.1623(4) 0.2617(4) 0.0815(5) Uani 1 1 d . . .
H6A H 0.4177 0.1210 0.2927 0.175 Uiso 1 1 calc R . .
C7 C 0.3970(2) 0.2310(3) 0.1868(3) 0.0864(13) Uani 1 1 d . . .
H7A H 0.4278 0.2347 0.1683 0.104 Uiso 1 1 calc R . .
C8 C 0.35995(10) 0.2956(2) -0.03574(19) 0.0389(6) Uani 1 1 d . . .
C9 C 0.38401(13) 0.3283(3) -0.1074(2) 0.0566(8) Uani 1 1 d . . .
H9A H 0.4018 0.3901 -0.0991 0.068 Uiso 1 1 calc R . .
C10 C 0.38199(16) 0.2703(3) -0.1914(3) 0.0738(11) Uani 1 1 d . . .
H10A H 0.3989 0.2925 -0.2383 0.089 Uiso 1 1 calc R . .
C11 C 0.35506(16) 0.1798(3) -0.2052(3) 0.0745(11) Uani 1 1 d . . .
H11A H 0.3534 0.1411 -0.2618 0.089 Uiso 1 1 calc R . .
C12 C 0.33074(16) 0.1467(3) -0.1356(3) 0.0717(10) Uani 1 1 d . . .
H12A H 0.3126 0.0854 -0.1451 0.086 Uiso 1 1 calc R . .
C13 C 0.33290(13) 0.2037(2) -0.0511(2) 0.0546(8) Uani 1 1 d . . .
H13A H 0.3162 0.1805 -0.0044 0.065 Uiso 1 1 calc R . .
C14 C 0.31974(10) 0.4445(2) 0.0367(2) 0.0459(7) Uani 1 1 d . . .
C15 C 0.31957(12) 0.5197(3) 0.1075(3) 0.0690(10) Uani 1 1 d . . .
H15A H 0.3442 0.5182 0.1664 0.083 Uiso 1 1 calc R . .
C16 C 0.28331(15) 0.5967(3) 0.0915(4) 0.0925(15) Uani 1 1 d . . .
H16A H 0.2840 0.6466 0.1394 0.111 Uiso 1 1 calc R . .
C17 C 0.24713(16) 0.5997(3) 0.0071(5) 0.1015(17) Uani 1 1 d . . .
H17A H 0.2229 0.6518 -0.0036 0.122 Uiso 1 1 calc R . .
C18 C 0.24617(16) 0.5266(4) -0.0625(4) 0.0968(15) Uani 1 1 d . . .
H18A H 0.2207 0.5281 -0.1202 0.116 Uiso 1 1 calc R . .
C19 C 0.28288(13) 0.4491(3) -0.0488(3) 0.0680(10) Uani 1 1 d . . .
H19A H 0.2822 0.4006 -0.0980 0.082 Uiso 1 1 calc R . .
C20 C 0.44963(10) 0.78852(18) 0.0177(2) 0.0378(6) Uani 1 1 d . . .
C21 C 0.40420(11) 0.8251(2) 0.0362(2) 0.0465(7) Uani 1 1 d . . .
C22 C 0.39742(12) 0.9302(2) 0.0410(3) 0.0629(10) Uani 1 1 d . . .
H22A H 0.3676 0.9558 0.0539 0.075 Uiso 1 1 calc R . .
C23 C 0.43430(12) 0.9974(2) 0.0269(3) 0.0577(9) Uani 1 1 d . . .
H23A H 0.4286 1.0678 0.0304 0.069 Uiso 1 1 calc R . .
C24 C 0.48006(10) 0.96389(19) 0.0075(2) 0.0419(6) Uani 1 1 d . . .
C25 C 0.48653(10) 0.85748(19) 0.0040(2) 0.0411(6) Uani 1 1 d . . .
H25A H 0.5166 0.8319 -0.0080 0.049 Uiso 1 1 calc R . .
O2W O 0.5000 -0.0947(19) 0.2500 0.209(7) Uani 0.50 2 d SP A 1
O2W' O 0.5000 0.0572(19) 0.2500 0.209(7) Uani 0.50 2 d SP 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
_geom_angle_site_symmetry_3
O1 S1 O2 114.81(16) .
O1 S1 O3 111.62(14) .
O2 S1 O3 110.88(14) .
O1 S1 C20 107.73(14) .
O2 S1 C20 105.70(12) .
O3 S1 C20 105.43(12) .
H1W O1W H2W 108.0(16) .
C21 O4 H4O 108(3) .
C1 N1 H1N1 113.7(18) .
C1 N1 H1N2 110.9(18) .
H1N1 N1 H1N2 105.5(14) .
C1 N1 H1N3 112.3(19) .
H1N1 N1 H1N3 107.2(14) .
H1N2 N1 H1N3 106.9(14) .
N1 C1 C2 108.4(2) .
N1 C1 C8 108.5(2) .
C2 C1 C8 110.2(2) .
N1 C1 C14 105.6(2) .
C2 C1 C14 111.9(2) .
C8 C1 C14 112.1(2) .
C7 C2 C3 119.6(4) .
C7 C2 C1 120.1(3) .
C3 C2 C1 120.2(3) .
C4 C3 C2 119.5(6) .
C4 C3 H3A 120.2 .
C2 C3 H3A 120.2 .
C5 C4 C3 121.2(8) .
C5 C4 H4A 119.4 .
C3 C4 H4A 119.4 .
C6 C5 C4 119.4(6) .
C6 C5 H5A 120.3 .
C4 C5 H5A 120.3 .
C5 C6 C7 121.8(7) .
C5 C6 H6A 119.1 .
C7 C6 H6A 119.1 .
C2 C7 C6 118.5(6) .
C2 C7 H7A 120.8 .
C6 C7 H7A 120.8 .
C9 C8 C13 118.2(3) .
C9 C8 C1 121.2(2) .
C13 C8 C1 120.5(2) .
C10 C9 C8 121.0(3) .
C10 C9 H9A 119.5 .
C8 C9 H9A 119.5 .
C11 C10 C9 119.9(3) .
C11 C10 H10A 120.0 .
C9 C10 H10A 120.0 .
C12 C11 C10 119.9(3) .
C12 C11 H11A 120.0 .
C10 C11 H11A 120.0 .
C11 C12 C13 120.6(3) .
C11 C12 H12A 119.7 .
C13 C12 H12A 119.7 .
C12 C13 C8 120.4(3) .
C12 C13 H13A 119.8 .
C8 C13 H13A 119.8 .
C19 C14 C15 117.8(3) .
C19 C14 C1 122.4(3) .
C15 C14 C1 119.8(3) .
C16 C15 C14 121.0(4) .
C16 C15 H15A 119.5 .
C14 C15 H15A 119.5 .
C17 C16 C15 120.4(4) .
C17 C16 H16A 119.8 .
C15 C16 H16A 119.8 .
C16 C17 C18 119.7(4) .
C16 C17 H17A 120.2 .
C18 C17 H17A 120.2 .
C17 C18 C19 121.0(4) .
C17 C18 H18A 119.5 .
C19 C18 H18A 119.5 .
C14 C19 C18 120.1(4) .
C14 C19 H19A 120.0 .
C18 C19 H19A 120.0 .
C25 C20 C21 120.0(2) .
C25 C20 S1 118.20(19) .
C21 C20 S1 121.80(19) .
O4 C21 C22 117.9(2) .
O4 C21 C20 123.5(2) .
C22 C21 C20 118.5(2) .
C23 C22 C21 120.7(3) .
C23 C22 H22A 119.6 .
C21 C22 H22A 119.6 .
C22 C23 C24 122.4(3) .
C22 C23 H23A 118.8 .
C24 C23 H23A 118.8 .
C25 C24 C23 116.1(2) .
C25 C24 C24 121.3(3) 5_675
C23 C24 C24 122.6(3) 5_675
C20 C25 C24 122.2(2) .
C20 C25 H25A 118.9 .
C24 C25 H25A 118.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.428(2) .
S1 O2 1.448(2) .
S1 O3 1.467(2) .
S1 C20 1.763(2) .
O1W H1W 0.85(3) .
O1W H2W 0.85(3) .
O4 C21 1.360(3) .
O4 H4O 0.85(3) .
N1 C1 1.520(3) .
N1 H1N1 0.87(3) .
N1 H1N2 0.87(3) .
N1 H1N3 0.86(3) .
C1 C2 1.527(4) .
C1 C8 1.533(4) .
C1 C14 1.536(4) .
C2 C7 1.366(6) .
C2 C3 1.400(6) .
C3 C4 1.387(7) .
C3 H3A 0.9300 .
C4 C5 1.353(13) .
C4 H4A 0.9300 .
C5 C6 1.348(13) .
C5 H5A 0.9300 .
C6 C7 1.417(7) .
C6 H6A 0.9300 .
C7 H7A 0.9300 .
C8 C9 1.385(4) .
C8 C13 1.391(4) .
C9 C10 1.385(5) .
C9 H9A 0.9300 .
C10 C11 1.373(5) .
C10 H10A 0.9300 .
C11 C12 1.367(5) .
C11 H11A 0.9300 .
C12 C13 1.383(5) .
C12 H12A 0.9300 .
C13 H13A 0.9300 .
C14 C19 1.365(5) .
C14 C15 1.392(4) .
C15 C16 1.383(5) .
C15 H15A 0.9300 .
C16 C17 1.344(7) .
C16 H16A 0.9300 .
C17 C18 1.355(7) .
C17 H17A 0.9300 .
C18 C19 1.397(5) .
C18 H18A 0.9300 .
C19 H19A 0.9300 .
C20 C25 1.390(3) .
C20 C21 1.399(4) .
C21 C22 1.382(4) .
C22 C23 1.376(4) .
C22 H22A 0.9300 .
C23 C24 1.400(4) .
C23 H23A 0.9300 .
C24 C25 1.396(3) .
C24 C24 1.484(5) 5_675
C25 H25A 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 O1 0.85(3) 2.12(2) 2.904(3) 153(3) 2_655
O1W H2W O2 0.85(3) 2.176(18) 2.985(3) 158(3) 6_566
O4 H4O O3 0.85(3) 1.94(2) 2.712(3) 150(4) .
N1 H1N1 O3 0.87(3) 1.981(10) 2.852(3) 178(2) .
N1 H1N2 O1W 0.87(3) 1.882(11) 2.754(3) 175(3) .
N1 H1N3 O2 0.86(3) 1.997(16) 2.801(3) 155(2) 5_665
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
N1 C1 C2 C7 -47.1(4) . .
C8 C1 C2 C7 71.5(4) . .
C14 C1 C2 C7 -163.1(3) . .
N1 C1 C2 C3 136.8(3) . .
C8 C1 C2 C3 -104.6(3) . .
C14 C1 C2 C3 20.8(4) . .
C7 C2 C3 C4 -1.0(6) . .
C1 C2 C3 C4 175.2(4) . .
C2 C3 C4 C5 0.0(9) . .
C3 C4 C5 C6 1.1(12) . .
C4 C5 C6 C7 -1.3(11) . .
C3 C2 C7 C6 0.8(6) . .
C1 C2 C7 C6 -175.4(3) . .
C5 C6 C7 C2 0.3(8) . .
N1 C1 C8 C9 -33.0(3) . .
C2 C1 C8 C9 -151.5(3) . .
C14 C1 C8 C9 83.2(3) . .
N1 C1 C8 C13 149.8(3) . .
C2 C1 C8 C13 31.3(4) . .
C14 C1 C8 C13 -94.0(3) . .
C13 C8 C9 C10 -1.2(5) . .
C1 C8 C9 C10 -178.4(3) . .
C8 C9 C10 C11 1.2(6) . .
C9 C10 C11 C12 -0.7(6) . .
C10 C11 C12 C13 0.1(6) . .
C11 C12 C13 C8 -0.1(6) . .
C9 C8 C13 C12 0.6(5) . .
C1 C8 C13 C12 177.9(3) . .
N1 C1 C14 C19 126.3(3) . .
C2 C1 C14 C19 -116.0(3) . .
C8 C1 C14 C19 8.4(4) . .
N1 C1 C14 C15 -53.1(3) . .
C2 C1 C14 C15 64.6(3) . .
C8 C1 C14 C15 -171.1(3) . .
C19 C14 C15 C16 -0.2(5) . .
C1 C14 C15 C16 179.2(3) . .
C14 C15 C16 C17 0.5(6) . .
C15 C16 C17 C18 0.3(7) . .
C16 C17 C18 C19 -1.4(7) . .
C15 C14 C19 C18 -0.9(5) . .
C1 C14 C19 C18 179.7(3) . .
C17 C18 C19 C14 1.7(7) . .
O1 S1 C20 C25 90.2(3) . .
O2 S1 C20 C25 -33.0(3) . .
O3 S1 C20 C25 -150.5(2) . .
O1 S1 C20 C21 -87.6(3) . .
O2 S1 C20 C21 149.2(3) . .
O3 S1 C20 C21 31.7(3) . .
C25 C20 C21 O4 178.8(3) . .
S1 C20 C21 O4 -3.4(4) . .
C25 C20 C21 C22 -0.5(5) . .
S1 C20 C21 C22 177.2(3) . .
O4 C21 C22 C23 -178.7(3) . .
C20 C21 C22 C23 0.7(6) . .
C21 C22 C23 C24 -0.2(6) . .
C22 C23 C24 C25 -0.5(5) . .
C22 C23 C24 C24 -179.9(4) . 5_675
C21 C20 C25 C24 -0.2(5) . .
S1 C20 C25 C24 -178.0(2) . .
C23 C24 C25 C20 0.7(5) . .
C24 C24 C25 C20 -179.9(3) 5_675 .
