#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:05:35 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179651 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/04/4510461.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_4510461
loop_
_publ_author_name
'Li, Ya-Nan'
'Huo, Li-Hua'
'Deng, Zhao-Peng'
'Zou, Xin'
'Zhu, Zhi-Biao'
'Zhao, Hui'
'Gao, Shan'
_publ_section_title
;
 Solvent Effect on the Supramolecular Patterns and Luminescent Properties
 of Organic Salts Comprising Naphthalene-1,5-disulfonic Acid and
 Triphenylmethylamine
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2381
_journal_paper_doi               10.1021/cg5001057
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C19 H18 N, 0.5(C10 H6 O6 S2), 2(H2 O)'
_chemical_formula_sum            'C24 H25 N O5 S'
_chemical_formula_weight         439.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.557(7)
_cell_angle_beta                 94.862(6)
_cell_angle_gamma                97.117(6)
_cell_formula_units_Z            2
_cell_length_a                   8.8813(7)
_cell_length_b                   10.3007(7)
_cell_length_c                   13.0949(11)
_cell_measurement_reflns_used    2057
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.29
_cell_volume                     1117.07(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6671
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0435
_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)+(0.0559P)²+0.1726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                3927
_reflns_number_total             5099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5001057_si_002.cif
_cod_data_source_block           10
_cod_depositor_comments
'Adding full bibliography for 4510452--4510462.cif.'
_cod_original_cell_volume        1117.08(14)
_cod_database_code               4510461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.16339(5) 0.84347(4) 0.61420(4) 0.03414(13) Uani 1 1 d .
O1 O 0.12784(19) 0.87733(14) 0.51648(12) 0.0586(4) Uani 1 1 d .
O1W O 0.20446(14) 1.00624(14) 0.37160(11) 0.0427(3) Uani 1 1 d GD
H1W1 H 0.172(2) 0.970(2) 0.4181(14) 0.064 Uiso 1 1 d D
H1W2 H 0.1278(17) 1.032(2) 0.3438(16) 0.064 Uiso 1 1 d D
O2W O 0.53593(16) 0.81964(15) 0.49696(11) 0.0478(3) Uani 1 1 d GD
H2W1 H 0.6188(14) 0.863(2) 0.5374(15) 0.072 Uiso 1 1 d D
H2W2 H 0.4643(17) 0.821(2) 0.5365(15) 0.072 Uiso 1 1 d D
O2 O 0.05649(14) 0.88301(12) 0.69116(10) 0.0440(3) Uani 1 1 d .
O3 O 0.32293(14) 0.89280(12) 0.66189(12) 0.0504(4) Uani 1 1 d .
N1 N 0.53781(15) 1.13175(14) 0.69695(11) 0.0309(3) Uani 1 1 d D
H1N1 H 0.4719(15) 1.0602(14) 0.6940(14) 0.046 Uiso 1 1 d D
H1N2 H 0.6259(11) 1.1045(18) 0.6911(14) 0.046 Uiso 1 1 d D
H1N3 H 0.5124(17) 1.1498(18) 0.6372(11) 0.046 Uiso 1 1 d D
C1 C 0.2631(2) 0.45748(18) 0.55701(16) 0.0412(4) Uani 1 1 d .
H1A H 0.3497 0.4198 0.5699 0.049 Uiso 1 1 calc R
C2 C 0.27055(19) 0.60197(17) 0.59110(15) 0.0382(4) Uani 1 1 d .
H2A H 0.3615 0.6592 0.6274 0.046 Uiso 1 1 calc R
C3 C 0.14521(18) 0.65928(16) 0.57140(13) 0.0297(3) Uani 1 1 d .
C4 C 0.00350(17) 0.57350(15) 0.51652(12) 0.0273(3) Uani 1 1 d .
C5 C -0.13062(19) 0.62800(17) 0.49473(14) 0.0342(4) Uani 1 1 d .
H5A H -0.1275 0.7236 0.5162 0.041 Uiso 1 1 calc R
C6 C 0.53671(16) 1.25323(15) 0.80074(12) 0.0263(3) Uani 1 1 d .
C7 C 0.63212(17) 1.22851(17) 0.89338(13) 0.0320(4) Uani 1 1 d .
C8 C 0.6288(3) 1.0960(2) 0.89910(19) 0.0581(6) Uani 1 1 d .
H8A H 0.5718 1.0204 0.8441 0.070 Uiso 1 1 calc R
C9 C 0.7099(3) 1.0758(3) 0.9863(2) 0.0787(8) Uani 1 1 d .
H9A H 0.7082 0.9863 0.9886 0.094 Uiso 1 1 calc R
C10 C 0.7933(3) 1.1863(3) 1.0698(2) 0.0723(7) Uani 1 1 d .
H10A H 0.8472 1.1719 1.1282 0.087 Uiso 1 1 calc R
C11 C 0.7955(2) 1.3169(3) 1.06532(17) 0.0603(6) Uani 1 1 d .
H11A H 0.8503 1.3921 1.1217 0.072 Uiso 1 1 calc R
C12 C 0.7167(2) 1.3389(2) 0.97755(14) 0.0427(4) Uani 1 1 d .
H12A H 0.7207 1.4286 0.9753 0.051 Uiso 1 1 calc R
C13 C 0.60630(17) 1.38559(16) 0.78044(12) 0.0283(3) Uani 1 1 d .
C14 C 0.7444(2) 1.3893(2) 0.73776(15) 0.0410(4) Uani 1 1 d .
H14A H 0.7901 1.3100 0.7177 0.049 Uiso 1 1 calc R
C15 C 0.8144(3) 1.5095(2) 0.72484(17) 0.0559(6) Uani 1 1 d .
H15A H 0.9081 1.5112 0.6982 0.067 Uiso 1 1 calc R
C16 C 0.7462(3) 1.6266(2) 0.75114(17) 0.0583(6) Uani 1 1 d .
H16A H 0.7929 1.7071 0.7415 0.070 Uiso 1 1 calc R
C17 C 0.6081(3) 1.62392(19) 0.79192(16) 0.0505(5) Uani 1 1 d .
H17A H 0.5613 1.7027 0.8095 0.061 Uiso 1 1 calc R
C18 C 0.5385(2) 1.50397(17) 0.80687(14) 0.0386(4) Uani 1 1 d .
H18A H 0.4458 1.5032 0.8348 0.046 Uiso 1 1 calc R
C19 C 0.36843(17) 1.25245(15) 0.81845(13) 0.0277(3) Uani 1 1 d .
C20 C 0.3206(2) 1.2587(2) 0.91741(14) 0.0400(4) Uani 1 1 d .
H20A H 0.3916 1.2628 0.9752 0.048 Uiso 1 1 calc R
C21 C 0.1676(2) 1.2590(2) 0.93105(16) 0.0527(5) Uani 1 1 d .
H21A H 0.1366 1.2636 0.9980 0.063 Uiso 1 1 calc R
C22 C 0.0616(2) 1.2525(2) 0.84630(17) 0.0530(5) Uani 1 1 d .
H22A H -0.0411 1.2518 0.8556 0.064 Uiso 1 1 calc R
C23 C 0.10752(19) 1.2469(2) 0.74761(16) 0.0445(4) Uani 1 1 d .
H23A H 0.0359 1.2431 0.6902 0.053 Uiso 1 1 calc R
C24 C 0.25937(18) 1.24696(18) 0.73349(14) 0.0355(4) Uani 1 1 d .
H24A H 0.2895 1.2433 0.6665 0.043 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
O2 S1 O1 112.88(9) . .
O2 S1 O3 113.41(8) . .
O1 S1 O3 112.32(9) . .
O2 S1 C3 106.97(7) . .
O1 S1 C3 105.82(8) . .
O3 S1 C3 104.64(7) . .
H1W1 O1W H1W2 107.2(13) . .
H2W1 O2W H2W2 108.8(14) . .
C6 N1 H1N1 111.0(12) . .
C6 N1 H1N2 113.3(13) . .
H1N1 N1 H1N2 106.9(12) . .
C6 N1 H1N3 113.6(12) . .
H1N1 N1 H1N3 105.4(11) . .
H1N2 N1 H1N3 106.0(12) . .
C5 C1 C2 120.65(15) 2_566 .
C5 C1 H1A 119.7 2_566 .
C2 C1 H1A 119.7 . .
C3 C2 C1 120.51(15) . .
C3 C2 H2A 119.7 . .
C1 C2 H2A 119.7 . .
C2 C3 C4 120.84(14) . .
C2 C3 S1 118.28(12) . .
C4 C3 S1 120.87(12) . .
C5 C4 C4 118.74(17) . 2_566
C5 C4 C3 123.04(14) . .
C4 C4 C3 118.22(17) 2_566 .
C1 C5 C4 121.02(15) 2_566 .
C1 C5 H5A 119.5 2_566 .
C4 C5 H5A 119.5 . .
C7 C6 N1 107.99(12) . .
C7 C6 C19 111.86(12) . .
N1 C6 C19 105.74(12) . .
C7 C6 C13 111.56(12) . .
N1 C6 C13 107.07(12) . .
C19 C6 C13 112.24(12) . .
C12 C7 C8 118.25(17) . .
C12 C7 C6 120.76(15) . .
C8 C7 C6 120.87(16) . .
C9 C8 C7 120.3(2) . .
C9 C8 H8A 119.8 . .
C7 C8 H8A 119.8 . .
C10 C9 C8 121.0(2) . .
C10 C9 H9A 119.5 . .
C8 C9 H9A 119.5 . .
C11 C10 C9 119.0(2) . .
C11 C10 H10A 120.5 . .
C9 C10 H10A 120.5 . .
C10 C11 C12 120.8(2) . .
C10 C11 H11A 119.6 . .
C12 C11 H11A 119.6 . .
C7 C12 C11 120.65(19) . .
C7 C12 H12A 119.7 . .
C11 C12 H12A 119.7 . .
C18 C13 C14 118.48(15) . .
C18 C13 C6 122.02(14) . .
C14 C13 C6 119.46(14) . .
C15 C14 C13 120.76(18) . .
C15 C14 H14A 119.6 . .
C13 C14 H14A 119.6 . .
C16 C15 C14 120.4(2) . .
C16 C15 H15A 119.8 . .
C14 C15 H15A 119.8 . .
C15 C16 C17 119.52(18) . .
C15 C16 H16A 120.2 . .
C17 C16 H16A 120.2 . .
C16 C17 C18 120.29(19) . .
C16 C17 H17A 119.9 . .
C18 C17 H17A 119.9 . .
C13 C18 C17 120.54(18) . .
C13 C18 H18A 119.7 . .
C17 C18 H18A 119.7 . .
C20 C19 C24 118.41(15) . .
C20 C19 C6 121.86(14) . .
C24 C19 C6 119.72(14) . .
C19 C20 C21 120.45(17) . .
C19 C20 H20A 119.8 . .
C21 C20 H20A 119.8 . .
C22 C21 C20 120.37(18) . .
C22 C21 H21A 119.8 . .
C20 C21 H21A 119.8 . .
C21 C22 C23 119.85(17) . .
C21 C22 H22A 120.1 . .
C23 C22 H22A 120.1 . .
C22 C23 C24 120.13(17) . .
C22 C23 H23A 119.9 . .
C24 C23 H23A 119.9 . .
C23 C24 C19 120.80(16) . .
C23 C24 H24A 119.6 . .
C19 C24 H24A 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4421(13) .
S1 O1 1.4497(14) .
S1 O3 1.4579(13) .
S1 C3 1.7809(16) .
O1W H1W1 0.86(9) .
O1W H1W2 0.86(9) .
O2W H2W1 0.85(9) .
O2W H2W2 0.85(9) .
N1 C6 1.5285(19) .
N1 H1N1 0.87(8) .
N1 H1N2 0.87(8) .
N1 H1N3 0.87(8) .
C1 C5 1.359(2) 2_566
C1 C2 1.402(2) .
C1 H1A 0.9300 .
C2 C3 1.366(2) .
C2 H2A 0.9300 .
C3 C4 1.431(2) .
C4 C5 1.423(2) .
C4 C4 1.428(3) 2_566
C5 C1 1.359(2) 2_566
C5 H5A 0.9300 .
C6 C7 1.526(2) .
C6 C19 1.531(2) .
C6 C13 1.537(2) .
C7 C12 1.386(2) .
C7 C8 1.387(3) .
C8 C9 1.384(3) .
C8 H8A 0.9300 .
C9 C10 1.379(4) .
C9 H9A 0.9300 .
C10 C11 1.362(4) .
C10 H10A 0.9300 .
C11 C12 1.390(3) .
C11 H11A 0.9300 .
C12 H12A 0.9300 .
C13 C18 1.385(2) .
C13 C14 1.391(2) .
C14 C15 1.381(3) .
C14 H14A 0.9300 .
C15 C16 1.376(3) .
C15 H15A 0.9300 .
C16 C17 1.379(3) .
C16 H16A 0.9300 .
C17 C18 1.390(2) .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
C19 C20 1.382(2) .
C19 C24 1.394(2) .
C20 C21 1.386(2) .
C20 H20A 0.9300 .
C21 C22 1.372(3) .
C21 H21A 0.9300 .
C22 C23 1.374(3) .
C22 H22A 0.9300 .
C23 C24 1.377(2) .
C23 H23A 0.9300 .
C24 H24A 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 H1W1 O1 0.86(9) 1.871(9) 2.7248(18) 171(2) .
O1W H1W2 O2 0.86(9) 2.032(11) 2.8770(18) 169(2) 2_576
O2W H2W1 O1W 0.85(9) 1.958(10) 2.7987(19) 169(2) 2_676
O2W H2W2 O3 0.85(9) 2.150(12) 2.970(2) 161(2) .
N1 H1N1 O3 0.87(8) 1.944(9) 2.8070(18) 170.6(16) .
N1 H1N2 O1W 0.87(8) 2.070(11) 2.8996(18) 160.6(17) 2_676
N1 H1N3 O2W 0.87(8) 1.905(9) 2.781(2) 176.5(17) 2_676
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 -1.0(3) 2_566 .
C1 C2 C3 C4 0.5(3) . .
C1 C2 C3 S1 -178.66(14) . .
O2 S1 C3 C2 -119.19(15) . .
O1 S1 C3 C2 120.22(15) . .
O3 S1 C3 C2 1.41(16) . .
O2 S1 C3 C4 61.61(15) . .
O1 S1 C3 C4 -58.98(15) . .
O3 S1 C3 C4 -177.79(13) . .
C2 C3 C4 C5 179.54(16) . .
S1 C3 C4 C5 -1.3(2) . .
C2 C3 C4 C4 0.3(3) . 2_566
S1 C3 C4 C4 179.51(15) . 2_566
C4 C4 C5 C1 -0.3(3) 2_566 2_566
C3 C4 C5 C1 -179.53(16) . 2_566
N1 C6 C7 C12 146.70(15) . .
C19 C6 C7 C12 -97.35(18) . .
C13 C6 C7 C12 29.3(2) . .
N1 C6 C7 C8 -37.4(2) . .
C19 C6 C7 C8 78.5(2) . .
C13 C6 C7 C8 -154.81(17) . .
C12 C7 C8 C9 -0.8(3) . .
C6 C7 C8 C9 -176.8(2) . .
C7 C8 C9 C10 1.1(4) . .
C8 C9 C10 C11 -0.3(4) . .
C9 C10 C11 C12 -0.8(4) . .
C8 C7 C12 C11 -0.2(3) . .
C6 C7 C12 C11 175.80(16) . .
C10 C11 C12 C7 1.0(3) . .
C7 C6 C13 C18 -108.96(17) . .
N1 C6 C13 C18 133.09(15) . .
C19 C6 C13 C18 17.5(2) . .
C7 C6 C13 C14 68.73(18) . .
N1 C6 C13 C14 -49.22(18) . .
C19 C6 C13 C14 -164.82(14) . .
C18 C13 C14 C15 1.7(3) . .
C6 C13 C14 C15 -176.02(17) . .
C13 C14 C15 C16 -1.9(3) . .
C14 C15 C16 C17 0.8(3) . .
C15 C16 C17 C18 0.3(3) . .
C14 C13 C18 C17 -0.6(3) . .
C6 C13 C18 C17 177.11(16) . .
C16 C17 C18 C13 -0.4(3) . .
C7 C6 C19 C20 12.9(2) . .
N1 C6 C19 C20 130.25(16) . .
C13 C6 C19 C20 -113.35(17) . .
C7 C6 C19 C24 -167.85(14) . .
N1 C6 C19 C24 -50.54(18) . .
C13 C6 C19 C24 65.86(18) . .
C24 C19 C20 C21 0.2(3) . .
C6 C19 C20 C21 179.46(17) . .
C19 C20 C21 C22 0.2(3) . .
C20 C21 C22 C23 -0.6(3) . .
C21 C22 C23 C24 0.4(3) . .
C22 C23 C24 C19 0.1(3) . .
C20 C19 C24 C23 -0.4(3) . .
C6 C19 C24 C23 -179.64(15) . .
