#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/81/7058127.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_7058127
loop_
_publ_author_name
'Vedernikov, Artem I.'
'Lobova, Natalia A.'
'Kuzmina, Lyudmila G.'
'Fomina, Marina V.'
'Strelenko, Yuri A.'
'Howard, Judith A. K.'
'Gromov, Sergey P.'
_publ_section_title
;
 Self-assembly of cucurbiturils and cyclodextrins to supramolecular
 millstones with naphthalene derivatives capable of translocations in the
 host cavities
;
_journal_issue                   9
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3673
_journal_page_last               3689
_journal_paper_doi               10.1039/C8NJ04685A
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C18 H17 N O3 S, 0.5(C6 H6), 2(H2 O)'
_chemical_formula_sum            'C21 H24 N O5 S'
_chemical_formula_weight         402.47
_chemical_name_systematic
'3-[4-(2-naphthyl)pyridinium-1-yl]propane-1-sulfonate,benzene and water solvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                72.9840(10)
_cell_angle_beta                 84.0570(10)
_cell_angle_gamma                65.7620(10)
_cell_formula_units_Z            2
_cell_length_a                   8.2091(3)
_cell_length_b                   9.6979(4)
_cell_length_c                   13.7643(5)
_cell_measurement_reflns_used    2906
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.004
_cell_measurement_theta_min      2.396
_cell_volume                     955.28(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART-6K'
_diffrn_measurement_method       /W
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8150
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         1.547
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_description       block
_exptl_crystal_F_000             426
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeCN-DMSO-benzene'
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0597P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             4975
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj04685a2.cif
_cod_data_source_block           pp
_cod_database_code               7058127
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.930
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
S1 S 0.29377(3) 0.28016(3) 1.09831(2) 0.01872(9) Uani 1 1 d
O1 O 0.28633(12) 0.43870(10) 1.07951(7) 0.02622(19) Uani 1 1 d
O2 O 0.47477(11) 0.16535(10) 1.09086(7) 0.02480(18) Uani 1 1 d
O3 O 0.20864(13) 0.23136(12) 1.19211(7) 0.0320(2) Uani 1 1 d
N1 N 0.10713(12) 0.24072(10) 0.80400(7) 0.01773(18) Uani 1 1 d
C1 C 0.25525(15) 0.18001(13) 0.75124(9) 0.0212(2) Uani 1 1 d
C2 C 0.29021(15) 0.27130(13) 0.66154(9) 0.0219(2) Uani 1 1 d
C3 C 0.17439(14) 0.42899(12) 0.62259(8) 0.0178(2) Uani 1 1 d
C4 C 0.02346(15) 0.48737(12) 0.68006(8) 0.0199(2) Uani 1 1 d
C5 C -0.00768(15) 0.39205(13) 0.76925(8) 0.0200(2) Uani 1 1 d
C6 C 0.20874(15) 0.52834(12) 0.52562(8) 0.0190(2) Uani 1 1 d
C7 C 0.10995(17) 0.69462(13) 0.49734(9) 0.0250(2) Uani 1 1 d
C8 C 0.13565(17) 0.78703(13) 0.40599(9) 0.0248(2) Uani 1 1 d
C9 C 0.26257(15) 0.72002(13) 0.33673(8) 0.0204(2) Uani 1 1 d
C10 C 0.29003(16) 0.81219(14) 0.24053(9) 0.0239(2) Uani 1 1 d
C11 C 0.40805(17) 0.74219(14) 0.17394(9) 0.0256(2) Uani 1 1 d
C12 C 0.50758(17) 0.57765(14) 0.20109(9) 0.0258(2) Uani 1 1 d
C13 C 0.48812(17) 0.48616(14) 0.29503(9) 0.0238(2) Uani 1 1 d
C14 C 0.36389(15) 0.55495(12) 0.36426(8) 0.0192(2) Uani 1 1 d
C15 C 0.33415(15) 0.46217(12) 0.45952(8) 0.0194(2) Uani 1 1 d
C16 C 0.07637(15) 0.14248(13) 0.90343(8) 0.0199(2) Uani 1 1 d
C17 C 0.19327(15) 0.13102(12) 0.98738(8) 0.0188(2) Uani 1 1 d
C18 C 0.16702(15) 0.29146(12) 0.99648(8) 0.0188(2) Uani 1 1 d
C1S C 0.64011(18) 0.04332(15) 0.45895(11) 0.0306(3) Uani 1 1 d
C2S C 0.49515(19) 0.08067(14) 0.39787(10) 0.0297(3) Uani 1 1 d
C3S C 0.35575(18) 0.03721(14) 0.43861(11) 0.0297(3) Uani 1 1 d
O1W O 0.25360(13) 0.72686(12) 0.93991(8) 0.0325(2) Uani 1 1 d
O2W O -0.10417(17) 0.17789(15) 1.25865(10) 0.0467(3) Uani 1 1 d
H1A H 0.328(2) 0.0789(19) 0.7805(13) 0.031(4) Uiso 1 1 d
H2A H 0.406(2) 0.2225(19) 0.6312(13) 0.033(4) Uiso 1 1 d
H4A H -0.065(2) 0.5919(19) 0.6578(13) 0.030(4) Uiso 1 1 d
H5A H -0.109(2) 0.4314(19) 0.8085(13) 0.032(4) Uiso 1 1 d
H7A H 0.023(2) 0.7427(18) 0.5444(13) 0.032(4) Uiso 1 1 d
H8A H 0.067(2) 0.902(2) 0.3861(13) 0.038(5) Uiso 1 1 d
H10A H 0.228(2) 0.9200(19) 0.2266(12) 0.025(4) Uiso 1 1 d
H11A H 0.421(3) 0.803(2) 0.1074(14) 0.041(5) Uiso 1 1 d
H12A H 0.591(2) 0.5263(19) 0.1553(13) 0.035(4) Uiso 1 1 d
H13A H 0.558(2) 0.376(2) 0.3136(13) 0.035(4) Uiso 1 1 d
H15A H 0.3992(18) 0.3525(16) 0.4725(10) 0.015(3) Uiso 1 1 d
H16A H -0.0467(19) 0.1915(16) 0.9168(11) 0.018(3) Uiso 1 1 d
H16B H 0.100(2) 0.0447(17) 0.8949(12) 0.023(4) Uiso 1 1 d
H17A H 0.317(2) 0.0721(16) 0.9754(12) 0.022(3) Uiso 1 1 d
H17B H 0.158(2) 0.0739(18) 1.0493(12) 0.028(4) Uiso 1 1 d
H18A H 0.205(2) 0.3506(17) 0.9379(12) 0.022(3) Uiso 1 1 d
H18B H 0.045(2) 0.3514(18) 1.0070(12) 0.027(4) Uiso 1 1 d
H1SA H 0.733(2) 0.071(2) 0.4299(13) 0.036(4) Uiso 1 1 d
H2SA H 0.496(2) 0.137(2) 0.3242(14) 0.039(5) Uiso 1 1 d
H3SA H 0.259(2) 0.063(2) 0.3965(14) 0.038(4) Uiso 1 1 d
H1WA H 0.347(3) 0.744(2) 0.9331(14) 0.038(5) Uiso 1 1 d
H1WB H 0.286(3) 0.638(2) 0.9759(16) 0.045(5) Uiso 1 1 d
H2WA H -0.155(3) 0.217(3) 1.195(2) 0.069(7) Uiso 1 1 d
H2WB H -0.014(3) 0.197(2) 1.2436(16) 0.052(6) Uiso 1 1 d
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
O3 S1 O1 112.82(6) .
O3 S1 O2 112.56(6) .
O1 S1 O2 112.38(5) .
O3 S1 C18 107.21(5) .
O1 S1 C18 104.86(5) .
O2 S1 C18 106.35(5) .
C5 N1 C1 120.32(9) .
C5 N1 C16 119.89(9) .
C1 N1 C16 119.71(9) .
N1 C1 C2 120.53(10) .
C1 C2 C3 121.04(10) .
C2 C3 C4 116.53(10) .
C2 C3 C6 121.77(10) .
C4 C3 C6 121.70(9) .
C5 C4 C3 120.77(10) .
N1 C5 C4 120.81(10) .
C15 C6 C7 118.58(10) .
C15 C6 C3 120.83(9) .
C7 C6 C3 120.58(10) .
C8 C7 C6 121.08(11) .
C7 C8 C9 120.85(10) .
C10 C9 C14 118.91(10) .
C10 C9 C8 122.26(10) .
C14 C9 C8 118.83(10) .
C11 C10 C9 120.48(11) .
C10 C11 C12 120.51(11) .
C13 C12 C11 120.25(11) .
C12 C13 C14 120.37(11) .
C13 C14 C15 121.53(10) .
C13 C14 C9 119.42(10) .
C15 C14 C9 119.02(10) .
C6 C15 C14 121.64(10) .
N1 C16 C17 111.18(8) .
C18 C17 C16 112.67(9) .
C17 C18 S1 113.26(7) .
C2S C1S C3S 119.63(12) 2_656
C3S C2S C1S 120.10(12) .
C2S C3S C1S 120.26(13) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O3 1.4513(9) .
S1 O1 1.4587(9) .
S1 O2 1.4611(8) .
S1 C18 1.7827(11) .
N1 C5 1.3482(14) .
N1 C1 1.3536(14) .
N1 C16 1.4857(13) .
C1 C2 1.3733(15) .
C2 C3 1.4007(15) .
C3 C4 1.4016(15) .
C3 C6 1.4771(14) .
C4 C5 1.3755(15) .
C6 C15 1.3801(15) .
C6 C7 1.4261(15) .
C7 C8 1.3673(16) .
C8 C9 1.4205(16) .
C9 C10 1.4192(15) .
C9 C14 1.4196(15) .
C10 C11 1.3711(18) .
C11 C12 1.4132(17) .
C12 C13 1.3737(16) .
C13 C14 1.4161(16) .
C14 C15 1.4184(14) .
C16 C17 1.5282(15) .
C17 C18 1.5220(15) .
C1S C2S 1.389(2) .
C1S C3S 1.3938(19) 2_656
C2S C3S 1.388(2) .
C3S C1S 1.3938(19) 2_656
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 H1WB O1 0.80(2) 2.04(2) 2.8145(14) 162(2) .
O1W H1WA O2 0.84(2) 1.95(2) 2.7756(13) 167.1(17) 2_667
O2W H2WB O3 0.83(2) 2.01(2) 2.8337(15) 173(2) .
O2W H2WA O1W 0.92(3) 1.93(3) 2.8485(17) 173(2) 2_567
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139179102
