# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ii
_database_code_depnum_ccdc_archive 'CCDC 1867412'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1-methyl-4-(2-naphthyl)pyridinium iodide, benzene solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C16 H14 N), 2(I), C6 H6, 0.5(C6 H6), 0.5(C6 H6)'
_chemical_formula_sum            'C22 H20 I N'
_chemical_formula_weight         425.29

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9470(8)
_cell_length_b                   19.1821(10)
_cell_length_c                   14.0976(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.2390(10)
_cell_angle_gamma                90
_cell_volume                     3714.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.590
_cell_measurement_theta_max      27.444

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.726
_shelx_estimated_absorpt_T_min   0.450
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4502
_exptl_absorpt_correction_T_max  0.9342
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40387
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.590
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9859
_reflns_number_gt                7285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²+1.7184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9859
_refine_ls_number_parameters     637
_refine_ls_number_restraints     264
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.34984(2) 0.36874(2) 0.63627(2) 0.04933(6) Uani 1 1 d . . . . .
I2 I 0.87965(2) 0.01584(2) 0.60117(2) 0.04989(6) Uani 1 1 d . . . . .
N1 N 0.55552(14) 0.21030(11) 0.59336(15) 0.0409(5) Uani 1 1 d . . . . .
C1 C 0.58510(19) 0.27652(14) 0.6098(2) 0.0467(6) Uani 1 1 d . . . . .
H1A H 0.5385 0.3125 0.5989 0.056 Uiso 1 1 calc R U . . .
C2 C 0.68089(19) 0.29317(14) 0.6417(2) 0.0429(6) Uani 1 1 d . . . . .
H2A H 0.7001 0.3407 0.6532 0.051 Uiso 1 1 calc R U . . .
C3 C 0.75131(17) 0.24201(12) 0.65790(16) 0.0342(5) Uani 1 1 d . . . . .
C4 C 0.71732(18) 0.17349(14) 0.6403(2) 0.0464(6) Uani 1 1 d . . . . .
H4A H 0.7622 0.1363 0.6506 0.056 Uiso 1 1 calc R U . . .
C5 C 0.62089(19) 0.15933(14) 0.6087(2) 0.0477(6) Uani 1 1 d . . . . .
H5A H 0.5994 0.1123 0.5972 0.057 Uiso 1 1 calc R U . . .
C6 C 0.92583(17) 0.20959(14) 0.72257(18) 0.0401(6) Uani 1 1 d . . . . .
H6A H 0.9073 0.1620 0.7197 0.048 Uiso 1 1 calc R U . . .
C7 C 0.85500(17) 0.25985(13) 0.69261(17) 0.0357(5) Uani 1 1 d . . . . .
C8 C 0.8845(2) 0.33061(15) 0.6969(2) 0.0553(7) Uani 1 1 d . . . . .
H8A H 0.8365 0.3662 0.6754 0.066 Uiso 1 1 calc R U . . .
C9 C 0.9799(2) 0.34819(16) 0.7311(3) 0.0661(9) Uani 1 1 d . . . . .
H9A H 0.9975 0.3960 0.7339 0.079 Uiso 1 1 calc R U . . .
C10 C 1.05332(19) 0.29717(16) 0.76239(19) 0.0492(7) Uani 1 1 d . . . . .
C11 C 1.1534(2) 0.3140(2) 0.7960(2) 0.0677(9) Uani 1 1 d . . . . .
H11A H 1.1730 0.3613 0.7989 0.081 Uiso 1 1 calc R U . . .
C12 C 1.2215(2) 0.2626(2) 0.8241(2) 0.0683(10) Uani 1 1 d . . . . .
H12A H 1.2883 0.2744 0.8454 0.082 Uiso 1 1 calc R U . . .
C13 C 1.1950(2) 0.1930(2) 0.8223(2) 0.0677(9) Uani 1 1 d . . . . .
H13A H 1.2436 0.1578 0.8447 0.081 Uiso 1 1 calc R U . . .
C14 C 1.0987(2) 0.17529(18) 0.7882(2) 0.0618(8) Uani 1 1 d . . . . .
H14A H 1.0809 0.1275 0.7852 0.074 Uiso 1 1 calc R U . . .
C15 C 1.02583(18) 0.22663(15) 0.75769(18) 0.0431(6) Uani 1 1 d . . . . .
C16 C 0.45087(19) 0.19280(17) 0.5557(2) 0.0569(8) Uani 1 1 d . . . . .
H16A H 0.4142 0.2340 0.5605 0.085 Uiso 1 1 calc R U . . .
H16B H 0.4415 0.1552 0.5980 0.085 Uiso 1 1 calc R U . . .
H16C H 0.4276 0.1775 0.4836 0.085 Uiso 1 1 calc R U . . .
N1' N 1.11400(14) 0.19108(11) 0.53895(15) 0.0374(5) Uani 1 1 d . . . . .
C1' C 1.10131(19) 0.25924(14) 0.5372(2) 0.0460(6) Uani 1 1 d . . . . .
H1'A H 1.1582 0.2873 0.5651 0.055 Uiso 0.671(4) 1 calc R U P A 1
H1'B H 1.1520 0.2925 0.5506 0.055 Uiso 0.329(4) 1 calc R U P A 2
C5' C 1.0366(2) 0.14903(16) 0.5064(3) 0.0677(9) Uani 1 1 d . . . . .
H5'A H 1.0428 0.0999 0.5024 0.081 Uiso 0.671(4) 1 calc R U P A 1
H5'B H 1.0509 0.1008 0.5191 0.081 Uiso 0.329(4) 1 calc R U P A 2
C2' C 1.0164(6) 0.2921(5) 0.4998(7) 0.0454(18) Uani 0.671(4) 1 d . U P A 1
H2'A H 1.0146 0.3414 0.4938 0.054 Uiso 0.671(4) 1 calc R U P A 1
C3' C 0.9302(6) 0.2546(3) 0.4695(6) 0.0317(13) Uani 0.671(4) 1 d . U P A 1
C4' C 0.9424(7) 0.1824(5) 0.4773(8) 0.058(2) Uani 0.671(4) 1 d . U P A 1
H4'A H 0.8866 0.1539 0.4631 0.069 Uiso 0.671(4) 1 calc R U P A 1
C6' C 0.7502(3) 0.2516(2) 0.4074(3) 0.0353(9) Uani 0.671(4) 1 d . U P A 1
H6'A H 0.7532 0.2021 0.4105 0.042 Uiso 0.671(4) 1 calc R U P A 1
C7' C 0.8344(3) 0.2889(3) 0.4334(3) 0.0334(9) Uani 0.671(4) 1 d . U P A 1
C8' C 0.8282(3) 0.3629(2) 0.4268(3) 0.0436(10) Uani 0.671(4) 1 d . U P A 1
H8'A H 0.8860 0.3895 0.4433 0.052 Uiso 0.671(4) 1 calc R U P A 1
C9' C 0.7411(3) 0.3963(2) 0.3972(3) 0.0488(11) Uani 0.671(4) 1 d . U P A 1
H9'A H 0.7387 0.4458 0.3931 0.059 Uiso 0.671(4) 1 calc R U P A 1
C10' C 0.6549(4) 0.3582(3) 0.3727(4) 0.0404(11) Uani 0.671(4) 1 d . U P A 1
C11' C 0.5611(6) 0.3918(3) 0.3441(6) 0.0525(17) Uani 0.671(4) 1 d . U P A 1
H11B H 0.5563 0.4412 0.3411 0.063 Uiso 0.671(4) 1 calc R U P A 1
C12' C 0.4808(9) 0.3525(5) 0.3216(11) 0.049(2) Uani 0.671(4) 1 d . U P A 1
H12B H 0.4199 0.3752 0.3048 0.059 Uiso 0.671(4) 1 calc R U P A 1
C13' C 0.4833(4) 0.2812(3) 0.3220(5) 0.0503(14) Uani 0.671(4) 1 d . U P A 1
H13B H 0.4247 0.2553 0.3035 0.060 Uiso 0.671(4) 1 calc R U P A 1
C14' C 0.5705(3) 0.2472(3) 0.3491(3) 0.0438(10) Uani 0.671(4) 1 d . U P A 1
H14B H 0.5723 0.1977 0.3499 0.053 Uiso 0.671(4) 1 calc R U P A 1
C15' C 0.6574(4) 0.2854(3) 0.3756(4) 0.0335(11) Uani 0.671(4) 1 d . U P A 1
C16' C 1.2157(11) 0.1599(9) 0.5765(12) 0.061(4) Uani 0.671(4) 1 d . U P A 1
H16D H 1.2236 0.1255 0.6307 0.091 Uiso 0.671(4) 1 calc R U P A 1
H16E H 1.2642 0.1970 0.6043 0.091 Uiso 0.671(4) 1 calc R U P A 1
H16F H 1.2247 0.1371 0.5187 0.091 Uiso 0.671(4) 1 calc R U P A 1
C2" C 0.9970(12) 0.2775(8) 0.5113(13) 0.034(3) Uani 0.329(4) 1 d . U P A 2
H2"A H 0.9806 0.3237 0.5230 0.041 Uiso 0.329(4) 1 calc R U P A 2
C3" C 0.9242(10) 0.2286(6) 0.4707(11) 0.023(2) Uani 0.329(4) 1 d . U P A 2
C4" C 0.9502(15) 0.1631(9) 0.4627(14) 0.041(3) Uani 0.329(4) 1 d . U P A 2
H4"A H 0.9037 0.1290 0.4249 0.050 Uiso 0.329(4) 1 calc R U P A 2
C6" C 0.7894(6) 0.3155(5) 0.4143(6) 0.0313(18) Uani 0.329(4) 1 d . U P A 2
H6"A H 0.8365 0.3510 0.4240 0.038 Uiso 0.329(4) 1 calc R U P A 2
C7" C 0.8176(6) 0.2481(5) 0.4338(5) 0.0265(15) Uani 0.329(4) 1 d . U P A 2
C8" C 0.7457(5) 0.1956(4) 0.4202(5) 0.0333(17) Uani 0.329(4) 1 d . U P A 2
H8"A H 0.7652 0.1484 0.4354 0.040 Uiso 0.329(4) 1 calc R U P A 2
C9" C 0.6499(5) 0.2124(4) 0.3858(6) 0.0393(19) Uani 0.329(4) 1 d . U P A 2
H9"A H 0.6036 0.1762 0.3754 0.047 Uiso 0.329(4) 1 calc R U P A 2
C10" C 0.6177(7) 0.2799(6) 0.3654(8) 0.029(2) Uani 0.329(4) 1 d . U P A 2
C11" C 0.5182(7) 0.3014(6) 0.3304(8) 0.041(2) Uani 0.329(4) 1 d . U P A 2
H11C H 0.4693 0.2668 0.3179 0.050 Uiso 0.329(4) 1 calc R U P A 2
C12" C 0.490(2) 0.3718(10) 0.314(2) 0.043(5) Uani 0.329(4) 1 d . U P A 2
H12C H 0.4237 0.3854 0.2912 0.051 Uiso 0.329(4) 1 calc R U P A 2
C13" C 0.5633(10) 0.4205(6) 0.3317(11) 0.041(3) Uani 0.329(4) 1 d . U P A 2
H13C H 0.5462 0.4685 0.3235 0.049 Uiso 0.329(4) 1 calc R U P A 2
C14" C 0.6580(6) 0.4030(6) 0.3602(7) 0.048(2) Uani 0.329(4) 1 d . U P A 2
H14C H 0.7049 0.4383 0.3679 0.057 Uiso 0.329(4) 1 calc R U P A 2
C15" C 0.6879(7) 0.3329(7) 0.3787(7) 0.038(2) Uani 0.329(4) 1 d . U P A 2
C16" C 1.207(2) 0.1637(16) 0.5766(18) 0.046(6) Uani 0.329(4) 1 d . U P A 2
H16G H 1.2517 0.1978 0.5683 0.069 Uiso 0.329(4) 1 calc R U P A 2
H16H H 1.2072 0.1211 0.5384 0.069 Uiso 0.329(4) 1 calc R U P A 2
H16I H 1.2266 0.1526 0.6500 0.069 Uiso 0.329(4) 1 calc R U P A 2
C1S C -0.0054(3) 0.5148(2) 0.5930(3) 0.0747(10) Uani 1 1 d . . . . .
H1SA H -0.0086 0.5252 0.6574 0.090 Uiso 1 1 calc R U . B 1
C2S C 0.0727(5) 0.4750(7) 0.5909(5) 0.0514(18) Uani 0.77(3) 1 d . U P C 1
H2SA H 0.1214 0.4581 0.6532 0.062 Uiso 0.77(3) 1 calc R U P C 1
C3S C 0.0777(7) 0.4607(6) 0.4972(7) 0.0552(19) Uani 0.77(3) 1 d . U P C 1
H3SA H 0.1303 0.4342 0.4945 0.066 Uiso 0.77(3) 1 calc R U P C 1
C2'S C 0.0857(13) 0.5024(14) 0.5883(15) 0.039(4) Uani 0.23(3) 1 d . U P C 2
H2'B H 0.1437 0.5068 0.6488 0.046 Uiso 0.23(3) 1 calc R U P C 2
C3'S C 0.091(2) 0.4844(16) 0.500(2) 0.048(5) Uani 0.23(3) 1 d . U P C 2
H3'A H 0.1513 0.4711 0.4982 0.057 Uiso 0.23(3) 1 calc R U P C 2
C4S C 0.4110(3) 0.47477(16) -0.0666(3) 0.0655(9) Uani 1 1 d . . . . .
H4SA H 0.3497 0.4574 -0.1126 0.079 Uiso 1 1 calc R U . . .
C5S C 0.4226(3) 0.49824(17) 0.0296(3) 0.0656(9) Uani 1 1 d . . . . .
H5SA H 0.3694 0.4971 0.0503 0.079 Uiso 1 1 calc R U . . .
C6S C 0.5120(3) 0.52353(17) 0.0961(3) 0.0676(9) Uani 1 1 d . . . . .
H6SA H 0.5201 0.5398 0.1627 0.081 Uiso 1 1 calc R U . . .
C7S C 0.2098(9) 0.5203(6) 0.2111(10) 0.047(2) Uani 0.51(2) 1 d . U P D 1
H7SA H 0.1489 0.5158 0.1543 0.056 Uiso 0.51(2) 1 calc R U P D 1
C8S C 0.2877(10) 0.5475(7) 0.1953(10) 0.044(2) Uani 0.51(2) 1 d . U P D 1
H8SA H 0.2813 0.5638 0.1293 0.053 Uiso 0.51(2) 1 calc R U P D 1
C9S C 0.3775(14) 0.5504(12) 0.2812(16) 0.049(4) Uani 0.51(2) 1 d . U P D 1
H9SA H 0.4334 0.5676 0.2726 0.059 Uiso 0.51(2) 1 calc R U P D 1
C10S C 0.3854(14) 0.5286(11) 0.3773(15) 0.048(4) Uani 0.51(2) 1 d . U P D 1
H10A H 0.4466 0.5305 0.4341 0.058 Uiso 0.51(2) 1 calc R U P D 1
C11S C 0.3056(15) 0.5043(8) 0.3913(13) 0.066(4) Uani 0.51(2) 1 d . U P D 1
H11D H 0.3103 0.4909 0.4580 0.079 Uiso 0.51(2) 1 calc R U P D 1
C12S C 0.2184(12) 0.4995(6) 0.3074(15) 0.065(3) Uani 0.51(2) 1 d . U P D 1
H12D H 0.1630 0.4815 0.3163 0.077 Uiso 0.51(2) 1 calc R U P D 1
C7D C 0.2713(12) 0.5266(8) 0.2033(10) 0.052(3) Uani 0.49(2) 1 d . U P D 2
H7DA H 0.2482 0.5316 0.1305 0.062 Uiso 0.49(2) 1 calc R U P D 2
C8D C 0.3627(16) 0.5445(13) 0.2605(15) 0.055(5) Uani 0.49(2) 1 d . U P D 2
H8DA H 0.4018 0.5644 0.2282 0.066 Uiso 0.49(2) 1 calc R U P D 2
C9D C 0.4013(14) 0.5348(12) 0.3647(18) 0.042(3) Uani 0.49(2) 1 d . U P D 2
H9DA H 0.4667 0.5474 0.4061 0.050 Uiso 0.49(2) 1 calc R U P D 2
C10D C 0.3399(10) 0.5051(8) 0.4084(11) 0.041(2) Uani 0.49(2) 1 d . U P D 2
H10B H 0.3650 0.4956 0.4803 0.050 Uiso 0.49(2) 1 calc R U P D 2
C11D C 0.2437(10) 0.4897(7) 0.3480(13) 0.053(3) Uani 0.49(2) 1 d . U P D 2
H11E H 0.2024 0.4711 0.3785 0.063 Uiso 0.49(2) 1 calc R U P D 2
C12D C 0.2090(9) 0.5014(8) 0.2444(14) 0.062(3) Uani 0.49(2) 1 d . U P D 2
H12E H 0.1428 0.4923 0.2016 0.074 Uiso 0.49(2) 1 calc R U P D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.335(3) . ?
N1 C5 1.338(3) . ?
N1 C16 1.478(3) . ?
C1 C2 1.359(4) . ?
C2 C3 1.390(3) . ?
C3 C4 1.396(3) . ?
C3 C7 1.470(3) . ?
C4 C5 1.358(4) . ?
C6 C7 1.370(3) . ?
C6 C15 1.415(3) . ?
C7 C8 1.421(4) . ?
C8 C9 1.355(4) . ?
C9 C10 1.405(4) . ?
C10 C15 1.408(4) . ?
C10 C11 1.417(4) . ?
C11 C12 1.359(5) . ?
C12 C13 1.389(5) . ?
C13 C14 1.368(4) . ?
C14 C15 1.404(4) . ?
N1' C1' 1.320(3) . ?
N1' C5' 1.335(3) . ?
N1' C16" 1.38(3) . ?
N1' C16' 1.521(16) . ?
C1' C2' 1.325(9) . ?
C1' C2" 1.496(16) . ?
C5' C4" 1.22(2) . ?
C5' C4' 1.452(10) . ?
C2' C3' 1.388(9) . ?
C3' C4' 1.395(9) . ?
C3' C7' 1.472(9) . ?
C6' C7' 1.366(6) . ?
C6' C15' 1.433(7) . ?
C7' C8' 1.422(6) . ?
C8' C9' 1.361(5) . ?
C9' C10' 1.402(6) . ?
C10' C15' 1.397(8) . ?
C10' C11' 1.448(10) . ?
C11' C12' 1.345(13) . ?
C12' C13' 1.369(11) . ?
C13' C14' 1.370(7) . ?
C14' C15' 1.407(6) . ?
C2" C3" 1.379(17) . ?
C3" C4" 1.332(16) . ?
C3" C7" 1.516(16) . ?
C6" C7" 1.353(11) . ?
C6" C15" 1.437(13) . ?
C7" C8" 1.430(11) . ?
C8" C9" 1.356(10) . ?
C9" C10" 1.371(14) . ?
C10" C15" 1.418(14) . ?
C10" C11" 1.431(14) . ?
C11" C12" 1.41(2) . ?
C12" C13" 1.38(2) . ?
C13" C14" 1.352(17) . ?
C14" C15" 1.409(13) . ?
C1S C3S 1.386(9) 3_566 ?
C1S C2S 1.404(7) . ?
C1S C2'S 1.409(19) . ?
C1S C3'S 1.42(3) 3_566 ?
C2S C3S 1.379(11) . ?
C3S C1S 1.386(9) 3_566 ?
C2'S C3'S 1.33(4) . ?
C3'S C1S 1.42(3) 3_566 ?
C4S C6S 1.370(5) 3_665 ?
C4S C5S 1.373(5) . ?
C5S C6S 1.383(5) . ?
C6S C4S 1.370(5) 3_665 ?
C7S C8S 1.371(14) . ?
C7S C12S 1.372(13) . ?
C8S C9S 1.41(2) . ?
C9S C10S 1.38(3) . ?
C10S C11S 1.37(2) . ?
C11S C12S 1.375(15) . ?
C7D C8D 1.33(2) . ?
C7D C12D 1.364(16) . ?
C8D C9D 1.36(3) . ?
C9D C10D 1.41(2) . ?
C10D C11D 1.382(13) . ?
C11D C12D 1.363(15) . ?

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
_geom_angle_publ_flag
C1 N1 C5 119.8(2) . . ?
C1 N1 C16 120.6(2) . . ?
C5 N1 C16 119.6(2) . . ?
N1 C1 C2 121.0(2) . . ?
C1 C2 C3 121.3(2) . . ?
C2 C3 C4 115.9(2) . . ?
C2 C3 C7 121.4(2) . . ?
C4 C3 C7 122.7(2) . . ?
C5 C4 C3 120.8(2) . . ?
N1 C5 C4 121.3(2) . . ?
C7 C6 C15 121.8(2) . . ?
C6 C7 C8 118.0(2) . . ?
C6 C7 C3 121.6(2) . . ?
C8 C7 C3 120.4(2) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C9 C10 121.3(3) . . ?
C9 C10 C15 118.5(2) . . ?
C9 C10 C11 122.5(3) . . ?
C15 C10 C11 119.0(3) . . ?
C12 C11 C10 120.1(3) . . ?
C11 C12 C13 121.1(3) . . ?
C14 C13 C12 119.9(3) . . ?
C13 C14 C15 121.0(3) . . ?
C14 C15 C10 118.9(3) . . ?
C14 C15 C6 122.0(3) . . ?
C10 C15 C6 119.1(2) . . ?
C1' N1' C5' 119.6(2) . . ?
C1' N1' C16" 120.1(12) . . ?
C5' N1' C16" 120.3(12) . . ?
C1' N1' C16' 120.8(7) . . ?
C5' N1' C16' 119.6(7) . . ?
N1' C1' C2' 125.9(4) . . ?
N1' C1' C2" 111.4(6) . . ?
C4" C5' N1' 129.8(9) . . ?
N1' C5' C4' 116.3(4) . . ?
C1' C2' C3' 120.2(7) . . ?
C2' C3' C4' 114.4(8) . . ?
C2' C3' C7' 122.2(6) . . ?
C4' C3' C7' 123.4(7) . . ?
C3' C4' C5' 122.8(8) . . ?
C7' C6' C15' 121.5(5) . . ?
C6' C7' C8' 118.4(4) . . ?
C6' C7' C3' 121.7(5) . . ?
C8' C7' C3' 119.9(4) . . ?
C9' C8' C7' 121.3(4) . . ?
C8' C9' C10' 120.3(4) . . ?
C15' C10' C9' 120.2(6) . . ?
C15' C10' C11' 117.8(5) . . ?
C9' C10' C11' 122.1(6) . . ?
C12' C11' C10' 119.4(7) . . ?
C11' C12' C13' 122.6(10) . . ?
C12' C13' C14' 119.9(7) . . ?
C13' C14' C15' 120.2(5) . . ?
C10' C15' C14' 120.0(5) . . ?
C10' C15' C6' 118.3(5) . . ?
C14' C15' C6' 121.7(5) . . ?
C3" C2" C1' 121.1(13) . . ?
C4" C3" C2" 118.0(16) . . ?
C4" C3" C7" 120.4(14) . . ?
C2" C3" C7" 121.6(11) . . ?
C5' C4" C3" 116.8(16) . . ?
C7" C6" C15" 119.6(8) . . ?
C6" C7" C8" 119.2(7) . . ?
C6" C7" C3" 120.5(9) . . ?
C8" C7" C3" 120.4(8) . . ?
C9" C8" C7" 120.8(7) . . ?
C8" C9" C10" 122.2(8) . . ?
C9" C10" C15" 117.9(9) . . ?
C9" C10" C11" 125.1(10) . . ?
C15" C10" C11" 117.0(9) . . ?
C12" C11" C10" 122.4(14) . . ?
C13" C12" C11" 117(2) . . ?
C14" C13" C12" 123.1(15) . . ?
C13" C14" C15" 120.7(10) . . ?
C14" C15" C10" 119.7(9) . . ?
C14" C15" C6" 120.0(9) . . ?
C10" C15" C6" 120.3(10) . . ?
C3S C1S C2S 121.3(5) 3_566 . ?
C2'S C1S C3'S 119.5(15) . 3_566 ?
C3S C2S C1S 119.2(5) . . ?
C2S C3S C1S 119.6(7) . 3_566 ?
C3'S C2'S C1S 120.2(17) . . ?
C2'S C3'S C1S 120(2) . 3_566 ?
C6S C4S C5S 119.9(3) 3_665 . ?
C4S C5S C6S 119.8(3) . . ?
C4S C6S C5S 120.3(3) 3_665 . ?
C8S C7S C12S 121.2(12) . . ?
C7S C8S C9S 117.2(14) . . ?
C10S C9S C8S 121.1(17) . . ?
C11S C10S C9S 120.3(16) . . ?
C10S C11S C12S 118.9(15) . . ?
C7S C12S C11S 121.3(13) . . ?
C8D C7D C12D 123.0(14) . . ?
C7D C8D C9D 121.0(19) . . ?
C8D C9D C10D 117.0(17) . . ?
C11D C10D C9D 121.0(15) . . ?
C12D C11D C10D 119.2(13) . . ?
C11D C12D C7D 118.6(11) . . ?

_refine_diff_density_max         1.114
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN-benzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bb
_database_code_depnum_ccdc_archive 'CCDC 1867416'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'3-[4-(2-naphthyl)pyridinium-1-yl]propane-1-sulfonate,water solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 N O3 S, 4(H2 O)'
_chemical_formula_sum            'C18 H25 N O7 S'
_chemical_formula_weight         399.45

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1522(8)
_cell_length_b                   9.6335(10)
_cell_length_c                   13.8091(14)
_cell_angle_alpha                73.187(2)
_cell_angle_beta                 82.605(2)
_cell_angle_gamma                66.352(2)
_cell_volume                     950.86(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2605
_cell_measurement_theta_min      2.391
_cell_measurement_theta_max      30.358

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10493
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5016
_reflns_number_gt                3622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0646P)²+0.1077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5016
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.72071(6) 0.71906(5) -0.09538(3) 0.01850(12) Uani 1 1 d . . . . .
O11 O 0.53932(17) 0.83432(15) -0.09065(10) 0.0254(3) Uani 1 1 d . . . . .
O12 O 0.72626(18) 0.56095(15) -0.07817(10) 0.0265(3) Uani 1 1 d . . . . .
O13 O 0.81624(19) 0.76596(18) -0.18758(10) 0.0311(3) Uani 1 1 d . . . . .
N1 N 0.88806(19) 0.76867(17) 0.19955(11) 0.0186(3) Uani 1 1 d . . . . .
C1 C 0.7409(3) 0.8308(2) 0.25470(14) 0.0241(4) Uani 1 1 d . . . . .
C2 C 0.7034(3) 0.7407(2) 0.34486(14) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.8152(2) 0.5823(2) 0.38100(13) 0.0220(4) Uani 1 1 d . . . . .
C4 C 0.9663(3) 0.5239(2) 0.32197(14) 0.0239(4) Uani 1 1 d . . . . .
C5 C 1.0002(2) 0.6178(2) 0.23299(14) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.6621(3) 0.5446(2) 0.54774(14) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.7792(3) 0.4799(2) 0.47713(14) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.8671(3) 0.3137(2) 0.49813(16) 0.0321(5) Uani 1 1 d . . . . .
C9 C 0.8387(3) 0.2189(2) 0.58783(16) 0.0328(5) Uani 1 1 d . . . . .
C10 C 0.7217(3) 0.2838(2) 0.66231(14) 0.0254(4) Uani 1 1 d . . . . .
C11 C 0.6942(3) 0.1872(3) 0.75794(15) 0.0283(4) Uani 1 1 d . . . . .
C12 C 0.5848(3) 0.2549(2) 0.82898(14) 0.0271(4) Uani 1 1 d . . . . .
C13 C 0.4969(3) 0.4196(3) 0.80878(15) 0.0301(4) Uani 1 1 d . . . . .
C14 C 0.5186(3) 0.5144(2) 0.71687(16) 0.0299(4) Uani 1 1 d . . . . .
C15 C 0.6318(2) 0.4483(2) 0.64281(14) 0.0230(4) Uani 1 1 d . . . . .
C16 C 0.9231(3) 0.8651(2) 0.09983(13) 0.0209(4) Uani 1 1 d . . . . .
C17 C 0.8098(2) 0.8726(2) 0.01720(13) 0.0195(3) Uani 1 1 d . . . . .
C18 C 0.8381(2) 0.7116(2) 0.00726(13) 0.0186(3) Uani 1 1 d . . . . .
O3W O 0.6889(3) 0.8895(3) -0.38841(14) 0.0586(6) Uani 1 1 d . . . . .
O1W O 0.2645(2) 0.7251(2) -0.05531(12) 0.0308(3) Uani 1 1 d . . . . .
O2W O 1.1235(2) 0.8439(2) -0.24895(13) 0.0455(4) Uani 1 1 d . . . . .
O4W O 0.3450(2) 0.9202(2) -0.41251(15) 0.0458(5) Uani 1 1 d . . . . .
H1WA H 0.363(4) 0.741(3) -0.0604(19) 0.042(7) Uiso 1 1 d . . . . .
H1WB H 0.287(4) 0.637(3) -0.021(2) 0.051(9) Uiso 1 1 d . . . . .
H2WA H 1.031(4) 0.815(3) -0.237(2) 0.066(9) Uiso 1 1 d . . . . .
H2WB H 1.183(4) 0.795(4) -0.192(3) 0.062(9) Uiso 1 1 d . . . . .
H3WA H 0.566(5) 0.912(4) -0.385(3) 0.090(12) Uiso 1 1 d . . . . .
H3WB H 0.716(4) 0.860(3) -0.328(2) 0.063(9) Uiso 1 1 d . . . . .
H4WA H 0.268(4) 0.909(4) -0.373(3) 0.064(10) Uiso 1 1 d . . . . .
H4WB H 0.305(4) 0.983(4) -0.468(3) 0.068(10) Uiso 1 1 d . . . . .
H1A H 0.668(3) 0.933(3) 0.2256(16) 0.026(6) Uiso 1 1 d . . . . .
H2A H 0.595(3) 0.789(3) 0.3801(17) 0.033(6) Uiso 1 1 d . . . . .
H4A H 1.049(3) 0.422(2) 0.3415(16) 0.023(5) Uiso 1 1 d . . . . .
H5A H 1.101(3) 0.578(2) 0.1939(16) 0.021(5) Uiso 1 1 d . . . . .
H6A H 0.605(3) 0.665(2) 0.5397(14) 0.016(5) Uiso 1 1 d . . . . .
H8A H 0.954(3) 0.268(3) 0.4466(19) 0.042(7) Uiso 1 1 d . . . . .
H9A H 0.902(3) 0.102(3) 0.6035(18) 0.039(6) Uiso 1 1 d . . . . .
H11A H 0.745(3) 0.080(2) 0.7685(15) 0.020(5) Uiso 1 1 d . . . . .
H12A H 0.564(3) 0.197(3) 0.8937(19) 0.041(7) Uiso 1 1 d . . . . .
H13A H 0.427(3) 0.464(3) 0.8623(19) 0.039(7) Uiso 1 1 d . . . . .
H14A H 0.468(3) 0.629(3) 0.6973(19) 0.048(7) Uiso 1 1 d . . . . .
H16A H 0.897(3) 0.966(3) 0.1083(17) 0.031(6) Uiso 1 1 d . . . . .
H16B H 1.053(3) 0.818(2) 0.0874(16) 0.024(5) Uiso 1 1 d . . . . .
H17A H 0.685(3) 0.927(3) 0.0299(17) 0.029(6) Uiso 1 1 d . . . . .
H17B H 0.843(3) 0.932(2) -0.0450(17) 0.028(6) Uiso 1 1 d . . . . .
H18A H 0.952(3) 0.656(3) -0.0062(17) 0.029(6) Uiso 1 1 d . . . . .
H18B H 0.797(3) 0.654(2) 0.0638(16) 0.021(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O12 1.4548(14) . ?
S1 O11 1.4573(13) . ?
S1 O13 1.4580(14) . ?
S1 C18 1.7790(18) . ?
N1 C5 1.347(2) . ?
N1 C1 1.353(2) . ?
N1 C16 1.487(2) . ?
C1 C2 1.374(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.396(3) . ?
C3 C7 1.482(3) . ?
C4 C5 1.369(3) . ?
C6 C7 1.373(3) . ?
C6 C15 1.429(3) . ?
C7 C8 1.423(3) . ?
C8 C9 1.365(3) . ?
C9 C10 1.414(3) . ?
C10 C15 1.411(3) . ?
C10 C11 1.429(3) . ?
C11 C12 1.364(3) . ?
C12 C13 1.411(3) . ?
C13 C14 1.370(3) . ?
C14 C15 1.402(3) . ?
C16 C17 1.526(2) . ?
C17 C18 1.518(2) . ?

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
_geom_angle_publ_flag
O12 S1 O11 112.65(8) . . ?
O12 S1 O13 112.59(8) . . ?
O11 S1 O13 112.29(8) . . ?
O12 S1 C18 105.41(8) . . ?
O11 S1 C18 106.62(8) . . ?
O13 S1 C18 106.66(8) . . ?
C5 N1 C1 120.24(16) . . ?
C5 N1 C16 119.68(15) . . ?
C1 N1 C16 120.04(15) . . ?
N1 C1 C2 120.45(18) . . ?
C1 C2 C3 120.86(18) . . ?
C4 C3 C2 116.61(17) . . ?
C4 C3 C7 120.56(17) . . ?
C2 C3 C7 122.83(17) . . ?
C5 C4 C3 120.85(18) . . ?
N1 C5 C4 120.97(17) . . ?
C7 C6 C15 121.13(18) . . ?
C6 C7 C8 119.15(18) . . ?
C6 C7 C3 120.27(17) . . ?
C8 C7 C3 120.57(17) . . ?
C9 C8 C7 120.88(18) . . ?
C8 C9 C10 120.68(19) . . ?
C15 C10 C9 119.44(18) . . ?
C15 C10 C11 118.89(17) . . ?
C9 C10 C11 121.66(18) . . ?
C12 C11 C10 119.77(19) . . ?
C11 C12 C13 120.75(18) . . ?
C14 C13 C12 120.48(19) . . ?
C13 C14 C15 120.06(19) . . ?
C14 C15 C10 120.04(17) . . ?
C14 C15 C6 121.25(17) . . ?
C10 C15 C6 118.70(17) . . ?
N1 C16 C17 111.32(14) . . ?
C18 C17 C16 112.97(15) . . ?
C17 C18 S1 113.38(12) . . ?

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 H1WA O11 0.87(3) 1.93(3) 2.771(2) 164(2) .
O1W H1WB O12 0.81(3) 2.03(3) 2.815(2) 165(3) 2_665
O2W H2WA O13 0.88(3) 1.98(3) 2.855(2) 169(3) .
O2W H2WB O1W 0.88(3) 1.92(3) 2.783(2) 166(3) 1_655
O3W H3WA O4W 0.93(4) 1.86(4) 2.752(3) 160(3) .
O3W H3WB O13 0.83(3) 2.01(3) 2.833(2) 171(3) .
O4W H4WA O2W 0.80(3) 2.04(3) 2.821(3) 165(3) 1_455
O4W H4WB O3W 0.83(3) 2.02(3) 2.805(3) 158(3) 2_674

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa
_database_code_depnum_ccdc_archive 'CCDC 1867417'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'complex between 3-[4-(2-naphthyl)pyridinium-1-yl]propane-1-sulfonateand cucurbit[8]uril, water solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C18 H17 N O3 S), C48 H48 N32 O16, 28.5(H2 O)'
_chemical_formula_sum            'C84 H139 N34 O50.50 S2'
_chemical_formula_weight         2497.40

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.460(15)
_cell_length_b                   15.020(15)
_cell_length_c                   15.044(15)
_cell_angle_alpha                67.677(16)
_cell_angle_beta                 76.564(17)
_cell_angle_gamma                71.319(17)
_cell_volume                     2840(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    2682
_cell_measurement_theta_min      2.232
_cell_measurement_theta_max      21.736

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1317
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20983
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.966
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             14240
_reflns_number_gt                6237
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1397P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14240
_refine_ls_number_parameters     846
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.1751
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2613
_refine_ls_wR_factor_gt          0.2236
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.916
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86235(8) -0.28817(9) 0.86545(9) 0.0544(3) Uani 1 1 d . . . . .
O11 O 0.8548(3) -0.2717(3) 0.9567(2) 0.0698(10) Uani 1 1 d . . . . .
O12 O 0.7669(2) -0.2805(3) 0.8430(3) 0.0687(9) Uani 1 1 d . . . . .
O13 O 0.9347(3) -0.3806(3) 0.8612(3) 0.0810(11) Uani 1 1 d . . . . .
N17 N 0.7502(3) 0.0532(3) 0.8140(3) 0.0597(10) Uani 1 1 d . . . . .
C25 C 0.7881(4) 0.1315(4) 0.7553(4) 0.0724(15) Uani 1 1 d . . . . .
H25A H 0.8564 0.1216 0.7379 0.087 Uiso 1 1 calc R U . . .
C26 C 0.7269(5) 0.2236(4) 0.7221(4) 0.0699(14) Uani 1 1 d . . . . .
H26A H 0.7515 0.2791 0.6836 0.084 Uiso 1 1 calc R U . A 1
C28 C 0.5913(4) 0.1583(4) 0.8110(4) 0.0691(15) Uani 1 1 d . . . . .
H28A H 0.5248 0.1651 0.8372 0.083 Uiso 1 1 calc R U . B 1
C29 C 0.6537(4) 0.0666(4) 0.8431(4) 0.0637(13) Uani 1 1 d . . . . .
H29A H 0.6289 0.0125 0.8859 0.076 Uiso 1 1 calc R U . . .
C27 C 0.6136(13) 0.2334(15) 0.7509(15) 0.044(4) Uani 0.492(7) 1 d . U P C 1
C30 C 0.5553(4) 0.4208(4) 0.6753(5) 0.064(3) Uani 0.492(7) 1 d G U P C 1
H30A H 0.6118 0.4272 0.6906 0.076 Uiso 0.492(7) 1 calc R U P C 1
C31 C 0.5381(5) 0.3273(4) 0.7039(5) 0.053(3) Uani 0.492(7) 1 d G U P C 1
C32 C 0.4547(5) 0.3177(4) 0.6813(5) 0.071(3) Uani 0.492(7) 1 d G U P C 1
H32A H 0.4430 0.2545 0.7007 0.085 Uiso 0.492(7) 1 calc R U P C 1
C33 C 0.3884(4) 0.4016(5) 0.6300(5) 0.077(4) Uani 0.492(7) 1 d G U P C 1
H33A H 0.3319 0.3952 0.6147 0.093 Uiso 0.492(7) 1 calc R U P C 1
C34 C 0.4056(4) 0.4951(4) 0.6014(4) 0.067(4) Uani 0.492(7) 1 d G U P C 1
C35 C 0.4891(4) 0.5046(4) 0.6240(4) 0.075(4) Uani 0.492(7) 1 d G U P C 1
C36 C 0.5063(6) 0.5981(4) 0.5954(6) 0.089(4) Uani 0.492(7) 1 d G U P C 1
H36A H 0.5627 0.6046 0.6107 0.107 Uiso 0.492(7) 1 calc R U P C 1
C37 C 0.4400(7) 0.6820(4) 0.5441(6) 0.101(5) Uani 0.492(7) 1 d G U P C 1
H37A H 0.4517 0.7452 0.5247 0.121 Uiso 0.492(7) 1 calc R U P C 1
C38 C 0.3565(6) 0.6724(4) 0.5215(6) 0.082(4) Uani 0.492(7) 1 d G U P C 1
H38A H 0.3117 0.7291 0.4868 0.098 Uiso 0.492(7) 1 calc R U P C 1
C39 C 0.3393(5) 0.5790(5) 0.5501(5) 0.089(5) Uani 0.492(7) 1 d G U P C 1
H39A H 0.2829 0.5725 0.5349 0.107 Uiso 0.492(7) 1 calc R U P C 1
C27' C 0.6395(13) 0.2478(16) 0.7442(17) 0.052(5) Uani 0.508(7) 1 d . U P C 2
C30' C 0.4846(4) 0.3617(3) 0.6774(4) 0.050(3) Uani 0.508(7) 1 d G U P C 2
H30B H 0.4606 0.3065 0.6890 0.060 Uiso 0.508(7) 1 calc R U P C 2
C31' C 0.5728(4) 0.3478(3) 0.7091(4) 0.043(2) Uani 0.508(7) 1 d G U P C 2
C32' C 0.6083(4) 0.4294(4) 0.6920(4) 0.056(3) Uani 0.508(7) 1 d G U P C 2
H32B H 0.6679 0.4200 0.7134 0.068 Uiso 0.508(7) 1 calc R U P C 2
C33' C 0.5556(4) 0.5248(4) 0.6433(4) 0.067(3) Uani 0.508(7) 1 d G U P C 2
H33B H 0.5796 0.5799 0.6318 0.080 Uiso 0.508(7) 1 calc R U P C 2
C34' C 0.4675(3) 0.5386(3) 0.6116(3) 0.058(3) Uani 0.508(7) 1 d G U P C 2
C35' C 0.4320(3) 0.4570(3) 0.6287(3) 0.052(3) Uani 0.508(7) 1 d G U P C 2
C36' C 0.3438(3) 0.4709(4) 0.5970(4) 0.072(3) Uani 0.508(7) 1 d G U P C 2
H36B H 0.3198 0.4157 0.6086 0.086 Uiso 0.508(7) 1 calc R U P C 2
C37' C 0.2912(4) 0.5662(5) 0.5483(5) 0.082(4) Uani 0.508(7) 1 d G U P C 2
H37B H 0.2316 0.5756 0.5269 0.098 Uiso 0.508(7) 1 calc R U P C 2
C38' C 0.3267(4) 0.6478(4) 0.5313(5) 0.071(4) Uani 0.508(7) 1 d G U P C 2
H38B H 0.2910 0.7123 0.4983 0.085 Uiso 0.508(7) 1 calc R U P C 2
C39' C 0.4148(5) 0.6340(3) 0.5629(5) 0.072(3) Uani 0.508(7) 1 d G U P C 2
H39B H 0.4388 0.6891 0.5514 0.086 Uiso 0.508(7) 1 calc R U P C 2
C40 C 0.8157(4) -0.0493(4) 0.8400(4) 0.0665(14) Uani 1 1 d . . . . .
H40A H 0.7853 -0.0926 0.8986 0.080 Uiso 1 1 calc R U . . .
H40B H 0.8786 -0.0487 0.8534 0.080 Uiso 1 1 calc R U . . .
C41 C 0.8333(4) -0.0892(4) 0.7575(3) 0.0609(13) Uani 1 1 d . . . . .
H41A H 0.8576 -0.0419 0.6981 0.073 Uiso 1 1 calc R U . . .
H41B H 0.7705 -0.0939 0.7479 0.073 Uiso 1 1 calc R U . . .
C42 C 0.9068(3) -0.1913(3) 0.7741(3) 0.0558(12) Uani 1 1 d . . . . .
H42A H 0.9670 -0.1888 0.7914 0.067 Uiso 1 1 calc R U . . .
H42B H 0.9242 -0.2063 0.7134 0.067 Uiso 1 1 calc R U . . .
O1 O 0.2627(2) 0.4622(2) 0.2409(2) 0.0504(7) Uani 1 1 d . . . . .
O2 O 0.1136(2) 0.49744(19) 0.46482(19) 0.0453(7) Uani 1 1 d . . . . .
O3 O 0.0889(2) 0.64380(19) 0.63758(19) 0.0457(7) Uani 1 1 d . . . . .
O4 O 0.24539(19) 0.81215(19) 0.65688(19) 0.0435(7) Uani 1 1 d . . . . .
O5 O 0.54129(19) 0.09398(19) 0.4837(2) 0.0451(7) Uani 1 1 d . . . . .
O6 O 0.3762(2) 0.1228(2) 0.7182(2) 0.0513(8) Uani 1 1 d . . . . .
O7 O 0.36655(19) 0.2640(2) 0.88793(19) 0.0448(7) Uani 1 1 d . . . . .
O8 O 0.52020(19) 0.4355(2) 0.90964(19) 0.0460(7) Uani 1 1 d . . . . .
N1 N 0.3917(2) 0.3266(2) 0.2352(2) 0.0355(7) Uani 1 1 d . . . . .
N2 N 0.2694(2) 0.3049(2) 0.3521(2) 0.0349(7) Uani 1 1 d . . . . .
N3 N 0.1679(2) 0.3273(2) 0.4982(2) 0.0348(7) Uani 1 1 d . . . . .
N4 N 0.1210(2) 0.3850(2) 0.6212(2) 0.0337(7) Uani 1 1 d . . . . .
N5 N 0.1106(2) 0.4763(2) 0.7263(2) 0.0333(7) Uani 1 1 d . . . . .
N6 N 0.1584(2) 0.5701(2) 0.7802(2) 0.0320(7) Uani 1 1 d . . . . .
N7 N 0.2517(2) 0.6701(2) 0.7932(2) 0.0328(7) Uani 1 1 d . . . . .
N8 N 0.3624(2) 0.7567(2) 0.7607(2) 0.0355(7) Uani 1 1 d . . . . .
N9 N 0.5011(2) 0.1753(2) 0.3295(2) 0.0352(7) Uani 1 1 d . . . . .
N10 N 0.3803(2) 0.1604(2) 0.4506(2) 0.0317(7) Uani 1 1 d . . . . .
N11 N 0.2776(2) 0.1820(2) 0.5972(2) 0.0352(7) Uani 1 1 d . . . . .
N12 N 0.2227(2) 0.2329(2) 0.7232(2) 0.0369(7) Uani 1 1 d . . . . .
N13 N 0.2209(2) 0.3272(2) 0.8223(2) 0.0321(7) Uani 1 1 d . . . . .
N14 N 0.2667(2) 0.4221(2) 0.8785(2) 0.0338(7) Uani 1 1 d . . . . .
N15 N 0.3582(2) 0.5233(2) 0.8954(2) 0.0352(7) Uani 1 1 d . . . . .
N16 N 0.4704(2) 0.6080(2) 0.8576(2) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.3039(3) 0.3736(3) 0.2724(3) 0.0360(8) Uani 1 1 d . . . . .
C2 C 0.1709(3) 0.3278(3) 0.4023(3) 0.0383(9) Uani 1 1 d . . . . .
H2A H 0.1343 0.3936 0.3642 0.046 Uiso 1 1 calc R U . . .
H2B H 0.1373 0.2790 0.4059 0.046 Uiso 1 1 calc R U . . .
C3 C 0.1328(3) 0.4118(3) 0.5222(3) 0.0331(8) Uani 1 1 d . . . . .
C4 C 0.0585(3) 0.4527(3) 0.6708(3) 0.0362(8) Uani 1 1 d . . . . .
H4A H 0.0271 0.5146 0.6230 0.043 Uiso 1 1 calc R U . . .
H4B H 0.0063 0.4230 0.7144 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1168(3) 0.5712(3) 0.7070(3) 0.0335(8) Uani 1 1 d . . . . .
C6 C 0.1551(2) 0.6609(3) 0.7942(3) 0.0339(8) Uani 1 1 d . . . . .
H6A H 0.1158 0.6628 0.8563 0.041 Uiso 1 1 calc R U . . .
H6B H 0.1225 0.7178 0.7428 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2834(3) 0.7519(3) 0.7290(3) 0.0340(8) Uani 1 1 d . . . . .
C8 C 0.3998(3) 0.8434(3) 0.7201(3) 0.0379(9) Uani 1 1 d . . . . .
H8A H 0.3988 0.8681 0.7720 0.046 Uiso 1 1 calc R U . . .
H8B H 0.3563 0.8956 0.6743 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4788(3) 0.1395(2) 0.4270(3) 0.0326(8) Uani 1 1 d . . . . .
C10 C 0.3338(3) 0.1130(3) 0.5460(3) 0.0350(8) Uani 1 1 d . . . . .
H10A H 0.2899 0.0784 0.5395 0.042 Uiso 1 1 calc R U . . .
H10B H 0.3847 0.0628 0.5848 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2998(3) 0.1740(3) 0.6834(3) 0.0361(8) Uani 1 1 d . . . . .
C12 C 0.2146(3) 0.2348(3) 0.8204(3) 0.0387(9) Uani 1 1 d . . . . .
H12A H 0.1515 0.2223 0.8560 0.046 Uiso 1 1 calc R U . . .
H12B H 0.2671 0.1808 0.8538 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2927(3) 0.3305(3) 0.8658(2) 0.0343(8) Uani 1 1 d . . . . .
C14 C 0.3166(3) 0.4387(3) 0.9415(3) 0.0363(8) Uani 1 1 d . . . . .
H14A H 0.2699 0.4486 0.9977 0.044 Uiso 1 1 calc R U . . .
H14B H 0.3694 0.3790 0.9652 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4560(3) 0.5134(3) 0.8892(2) 0.0348(8) Uani 1 1 d . . . . .
C16 C 0.5621(3) 0.6250(3) 0.8599(3) 0.0411(9) Uani 1 1 d . . . . .
H16A H 0.6073 0.5610 0.8898 0.049 Uiso 1 1 calc R U . . .
H16B H 0.5503 0.6664 0.9005 0.049 Uiso 1 1 calc R U . . .
C17 C 0.4132(2) 0.2197(3) 0.2810(2) 0.0307(8) Uani 1 1 d . . . . .
H17A H 0.4136 0.1860 0.2356 0.037 Uiso 1 1 calc R U . . .
C18 C 0.3294(3) 0.2052(3) 0.3651(2) 0.0326(8) Uani 1 1 d . . . . .
H18A H 0.2924 0.1616 0.3617 0.039 Uiso 1 1 calc R U . . .
C19 C 0.1775(2) 0.2380(3) 0.5816(2) 0.0308(8) Uani 1 1 d . . . . .
H19A H 0.1376 0.1954 0.5818 0.037 Uiso 1 1 calc R U . . .
C20 C 0.1407(3) 0.2779(3) 0.6676(3) 0.0328(8) Uani 1 1 d . . . . .
H20A H 0.0806 0.2578 0.7058 0.039 Uiso 1 1 calc R U . . .
C21 C 0.1346(2) 0.4094(3) 0.8218(2) 0.0304(8) Uani 1 1 d . . . . .
H21A H 0.0770 0.3866 0.8637 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1678(2) 0.4755(3) 0.8597(2) 0.0297(8) Uani 1 1 d . . . . .
H22A H 0.1254 0.4841 0.9194 0.036 Uiso 1 1 calc R U . . .
C23 C 0.2999(3) 0.6260(3) 0.8785(2) 0.0323(8) Uani 1 1 d . . . . .
H23A H 0.2532 0.6336 0.9364 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3782(3) 0.6836(3) 0.8558(3) 0.0338(8) Uani 1 1 d . . . . .
H24A H 0.3700 0.7158 0.9046 0.041 Uiso 1 1 calc R U . . .
O1W O 0.6021(3) 0.8388(3) 0.9224(3) 0.0837(11) Uani 1 1 d . . . . .
O2W O 0.9404(3) 0.2950(3) 0.5940(3) 0.0791(11) Uani 1 1 d . . . . .
O3W O 0.8767(3) 0.4501(3) 0.9021(3) 0.0777(11) Uani 1 1 d . . . . .
O4W O 0.7607(3) 0.0750(3) 0.5351(3) 0.0798(11) Uani 1 1 d . . . . .
O5W O 0.9770(3) 0.2561(3) 0.9938(3) 0.0880(12) Uani 1 1 d . . . . .
O6W O 0.5926(3) 0.0189(3) 0.6671(3) 0.0854(12) Uani 1 1 d . . . . .
O7W O 0.1486(3) 0.8507(3) 0.8683(3) 0.0968(13) Uani 1 1 d . . . . .
O8W O 0.0922(3) 0.8250(3) 0.5011(3) 0.0921(13) Uani 1 1 d . . . . .
O9W O 0.4193(4) 0.9711(4) 0.8970(4) 0.131(2) Uani 1 1 d . . . . .
O10W O 0.1058(3) 0.0837(3) 0.5156(4) 0.1119(16) Uani 1 1 d . . . . .
O11W O 0.7163(3) 0.3140(3) 0.9139(3) 0.0897(12) Uani 1 1 d . . . . .
O12W O 0.8948(11) 0.2978(18) 0.7945(12) 0.091(6) Uani 0.53(3) 1 d . . P D 1
O13W O 0.8586(12) 0.3500(12) 0.7484(18) 0.101(5) Uani 0.47(3) 1 d . . P D 2
O14W O 0.2703(5) 0.8816(4) 0.9725(5) 0.1018(19) Uani 0.75 1 d . . P . .
O15W O 0.0566(7) 1.0155(6) 0.7230(5) 0.098(3) Uani 0.5 1 d . . P . .
O16W O 1.0077(6) 0.1164(6) 0.8550(6) 0.091(2) Uani 0.5 1 d . . P . .
O17W O 0.1010(8) 1.0069(7) 1.0118(7) 0.110(3) Uani 0.5 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O12 1.455(4) . ?
S1 O11 1.459(4) . ?
S1 O13 1.460(4) . ?
S1 C42 1.757(5) . ?
N17 C29 1.336(6) . ?
N17 C25 1.364(7) . ?
N17 C40 1.484(6) . ?
C25 C26 1.357(7) . ?
C26 C27' 1.202(18) . ?
C26 C27 1.569(17) . ?
C28 C27 1.230(19) . ?
C28 C29 1.359(7) . ?
C28 C27' 1.597(19) . ?
C27 C31 1.52(2) . ?
C30 C31 1.3900 . ?
C30 C35 1.3900 . ?
C31 C32 1.3900 . ?
C32 C33 1.3900 . ?
C33 C34 1.3900 . ?
C34 C35 1.3900 . ?
C34 C39 1.3900 . ?
C35 C36 1.3900 . ?
C36 C37 1.3900 . ?
C37 C38 1.3900 . ?
C38 C39 1.3900 . ?
C27' C31' 1.47(2) . ?
C30' C31' 1.3900 . ?
C30' C35' 1.3900 . ?
C31' C32' 1.3900 . ?
C32' C33' 1.3900 . ?
C33' C34' 1.3900 . ?
C34' C35' 1.3900 . ?
C34' C39' 1.3900 . ?
C35' C36' 1.3900 . ?
C36' C37' 1.3900 . ?
C37' C38' 1.3900 . ?
C38' C39' 1.3900 . ?
C40 C41 1.511(7) . ?
C41 C42 1.527(6) . ?
O1 C1 1.222(5) . ?
O2 C3 1.231(4) . ?
O3 C5 1.221(4) . ?
O4 C7 1.229(4) . ?
O5 C9 1.237(4) . ?
O6 C11 1.226(4) . ?
O7 C13 1.216(4) . ?
O8 C15 1.221(4) . ?
N1 C1 1.349(5) . ?
N1 C17 1.445(5) . ?
N1 C16 1.449(5) 2_666 ?
N2 C1 1.365(5) . ?
N2 C18 1.435(5) . ?
N2 C2 1.450(5) . ?
N3 C3 1.360(5) . ?
N3 C2 1.431(5) . ?
N3 C19 1.442(5) . ?
N4 C3 1.372(5) . ?
N4 C4 1.444(5) . ?
N4 C20 1.449(5) . ?
N5 C5 1.372(5) . ?
N5 C4 1.442(5) . ?
N5 C21 1.450(4) . ?
N6 C5 1.364(5) . ?
N6 C6 1.440(5) . ?
N6 C22 1.459(4) . ?
N7 C7 1.380(5) . ?
N7 C23 1.430(4) . ?
N7 C6 1.444(5) . ?
N8 C7 1.367(5) . ?
N8 C8 1.433(5) . ?
N8 C24 1.450(5) . ?
N9 C9 1.356(5) . ?
N9 C8 1.447(5) 2_666 ?
N9 C17 1.453(4) . ?
N10 C9 1.348(5) . ?
N10 C10 1.450(5) . ?
N10 C18 1.453(5) . ?
N11 C11 1.360(5) . ?
N11 C19 1.444(4) . ?
N11 C10 1.450(4) . ?
N12 C11 1.359(5) . ?
N12 C20 1.443(5) . ?
N12 C12 1.450(5) . ?
N13 C13 1.371(5) . ?
N13 C12 1.431(5) . ?
N13 C21 1.447(4) . ?
N14 C13 1.381(5) . ?
N14 C22 1.431(4) . ?
N14 C14 1.447(5) . ?
N15 C15 1.358(5) . ?
N15 C14 1.444(5) . ?
N15 C23 1.457(5) . ?
N16 C15 1.384(5) . ?
N16 C16 1.439(5) . ?
N16 C24 1.446(5) . ?
C8 N9 1.447(5) 2_666 ?
C16 N1 1.449(5) 2_666 ?
C17 C18 1.537(5) . ?
C19 C20 1.542(5) . ?
C21 C22 1.551(5) . ?
C23 C24 1.539(5) . ?

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
_geom_angle_publ_flag
O12 S1 O11 112.1(2) . . ?
O12 S1 O13 112.6(2) . . ?
O11 S1 O13 112.3(2) . . ?
O12 S1 C42 106.6(2) . . ?
O11 S1 C42 106.5(2) . . ?
O13 S1 C42 106.1(2) . . ?
C29 N17 C25 120.9(4) . . ?
C29 N17 C40 119.2(4) . . ?
C25 N17 C40 119.8(5) . . ?
C26 C25 N17 120.0(5) . . ?
C27' C26 C25 126.8(11) . . ?
C25 C26 C27 117.1(9) . . ?
C27 C28 C29 126.3(10) . . ?
C29 C28 C27' 117.1(8) . . ?
N17 C29 C28 120.0(5) . . ?
C28 C27 C31 123.2(13) . . ?
C28 C27 C26 115.1(14) . . ?
C31 C27 C26 121.7(13) . . ?
C31 C30 C35 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 C27 118.4(8) . . ?
C30 C31 C27 121.4(8) . . ?
C31 C32 C33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 C39 120.0 . . ?
C35 C34 C39 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 C30 120.0 . . ?
C36 C35 C30 120.0 . . ?
C37 C36 C35 120.0 . . ?
C36 C37 C38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C38 C39 C34 120.0 . . ?
C26 C27' C31' 127.1(16) . . ?
C26 C27' C28 114.9(15) . . ?
C31' C27' C28 117.7(12) . . ?
C31' C30' C35' 120.0 . . ?
C30' C31' C32' 120.0 . . ?
C30' C31' C27' 121.3(8) . . ?
C32' C31' C27' 117.7(8) . . ?
C33' C32' C31' 120.0 . . ?
C34' C33' C32' 120.0 . . ?
C33' C34' C35' 120.0 . . ?
C33' C34' C39' 120.0 . . ?
C35' C34' C39' 120.0 . . ?
C36' C35' C34' 120.0 . . ?
C36' C35' C30' 120.0 . . ?
C34' C35' C30' 120.0 . . ?
C35' C36' C37' 120.0 . . ?
C38' C37' C36' 120.0 . . ?
C39' C38' C37' 120.0 . . ?
C38' C39' C34' 120.0 . . ?
N17 C40 C41 109.8(4) . . ?
C40 C41 C42 113.6(4) . . ?
C41 C42 S1 113.6(3) . . ?
C1 N1 C17 112.3(3) . . ?
C1 N1 C16 120.8(3) . 2_666 ?
C17 N1 C16 123.3(3) . 2_666 ?
C1 N2 C18 112.9(3) . . ?
C1 N2 C2 122.2(3) . . ?
C18 N2 C2 123.2(3) . . ?
C3 N3 C2 122.3(3) . . ?
C3 N3 C19 112.8(3) . . ?
C2 N3 C19 123.2(3) . . ?
C3 N4 C4 121.6(3) . . ?
C3 N4 C20 112.0(3) . . ?
C4 N4 C20 121.6(3) . . ?
C5 N5 C4 122.5(3) . . ?
C5 N5 C21 113.5(3) . . ?
C4 N5 C21 121.6(3) . . ?
C5 N6 C6 121.5(3) . . ?
C5 N6 C22 112.1(3) . . ?
C6 N6 C22 122.0(3) . . ?
C7 N7 C23 111.8(3) . . ?
C7 N7 C6 120.8(3) . . ?
C23 N7 C6 121.7(3) . . ?
C7 N8 C8 121.5(3) . . ?
C7 N8 C24 111.1(3) . . ?
C8 N8 C24 124.1(3) . . ?
C9 N9 C8 123.5(3) . 2_666 ?
C9 N9 C17 111.7(3) . . ?
C8 N9 C17 124.1(3) 2_666 . ?
C9 N10 C10 122.3(3) . . ?
C9 N10 C18 111.7(3) . . ?
C10 N10 C18 122.7(3) . . ?
C11 N11 C19 112.7(3) . . ?
C11 N11 C10 121.8(3) . . ?
C19 N11 C10 121.9(3) . . ?
C11 N12 C20 113.0(3) . . ?
C11 N12 C12 123.6(3) . . ?
C20 N12 C12 122.2(3) . . ?
C13 N13 C12 121.0(3) . . ?
C13 N13 C21 111.7(3) . . ?
C12 N13 C21 121.4(3) . . ?
C13 N14 C22 111.7(3) . . ?
C13 N14 C14 120.2(3) . . ?
C22 N14 C14 123.0(3) . . ?
C15 N15 C14 121.6(3) . . ?
C15 N15 C23 112.8(3) . . ?
C14 N15 C23 123.3(3) . . ?
C15 N16 C16 122.6(3) . . ?
C15 N16 C24 111.8(3) . . ?
C16 N16 C24 122.3(3) . . ?
O1 C1 N1 126.2(4) . . ?
O1 C1 N2 126.0(4) . . ?
N1 C1 N2 107.9(3) . . ?
N3 C2 N2 114.1(3) . . ?
O2 C3 N3 125.8(3) . . ?
O2 C3 N4 126.0(3) . . ?
N3 C3 N4 108.2(3) . . ?
N5 C4 N4 113.3(3) . . ?
O3 C5 N6 126.3(4) . . ?
O3 C5 N5 126.1(3) . . ?
N6 C5 N5 107.6(3) . . ?
N6 C6 N7 112.6(3) . . ?
O4 C7 N8 125.5(3) . . ?
O4 C7 N7 125.9(3) . . ?
N8 C7 N7 108.6(3) . . ?
N8 C8 N9 113.1(3) . 2_666 ?
O5 C9 N10 126.6(3) . . ?
O5 C9 N9 123.8(3) . . ?
N10 C9 N9 109.6(3) . . ?
N11 C10 N10 113.6(3) . . ?
O6 C11 N12 126.6(3) . . ?
O6 C11 N11 125.7(3) . . ?
N12 C11 N11 107.7(3) . . ?
N13 C12 N12 113.3(3) . . ?
O7 C13 N13 125.3(4) . . ?
O7 C13 N14 126.6(3) . . ?
N13 C13 N14 108.1(3) . . ?
N15 C14 N14 113.9(3) . . ?
O8 C15 N15 126.6(4) . . ?
O8 C15 N16 125.5(3) . . ?
N15 C15 N16 107.9(3) . . ?
N16 C16 N1 113.3(3) . 2_666 ?
N1 C17 N9 114.9(3) . . ?
N1 C17 C18 103.4(3) . . ?
N9 C17 C18 103.3(3) . . ?
N2 C18 N10 114.7(3) . . ?
N2 C18 C17 102.9(3) . . ?
N10 C18 C17 103.4(3) . . ?
N3 C19 N11 114.9(3) . . ?
N3 C19 C20 103.3(3) . . ?
N11 C19 C20 103.1(3) . . ?
N12 C20 N4 115.3(3) . . ?
N12 C20 C19 102.9(3) . . ?
N4 C20 C19 103.4(3) . . ?
N13 C21 N5 115.0(3) . . ?
N13 C21 C22 103.2(3) . . ?
N5 C21 C22 102.2(3) . . ?
N14 C22 N6 114.8(3) . . ?
N14 C22 C21 104.0(3) . . ?
N6 C22 C21 103.9(3) . . ?
N7 C23 N15 115.2(3) . . ?
N7 C23 C24 103.7(3) . . ?
N15 C23 C24 103.0(3) . . ?
N16 C24 N8 114.1(3) . . ?
N16 C24 C23 103.9(3) . . ?
N8 C24 C23 104.1(3) . . ?

_refine_diff_density_max         0.900
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.085


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cc
_database_code_depnum_ccdc_archive 'CCDC 1867414'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1-butyl-4-(2-naphthyl)pyridinium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N, I'
_chemical_formula_sum            'C19 H20 I N'
_chemical_formula_weight         389.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   15.871(6)
_cell_length_b                   15.739(8)
_cell_length_c                   15.215(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.826(4)
_cell_angle_gamma                90
_cell_volume                     3756(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2513
_cell_measurement_theta_min      2.395
_cell_measurement_theta_max      26.101

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.700
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7495
_exptl_absorpt_correction_T_max  0.8760
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17490
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4103
_reflns_number_gt                1889
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+35.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     446
_refine_ls_number_restraints     384
_refine_ls_R_factor_all          0.2212
_refine_ls_R_factor_gt           0.1318
_refine_ls_wR_factor_ref         0.4247
_refine_ls_wR_factor_gt          0.3853
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.46008(11) 0.19187(13) -0.57248(14) 0.0893(7) Uani 0.5 1 d . . P A 1
I2 I 0.43439(14) 0.15582(14) -0.5035(2) 0.0954(9) Uani 0.42 1 d . . P B 2
I3 I 0.4812(14) 0.1489(14) -0.3410(17) 0.087(6) Uani 0.04 1 d . U P C 3
I4 I 0.448(2) -0.025(2) -0.375(2) 0.060(8) Uani 0.02 1 d . U P D 4
I5 I 0.480(2) -0.0251(17) -0.306(3) 0.055(7) Uani 0.02 1 d . U P E 5
N1 N 0.205(2) 0.2141(16) 0.2812(11) 0.040(15) Uani 0.3 1 d DG U P F 1
C1 C 0.2671(19) 0.165(2) 0.2497(15) 0.052(11) Uani 0.3 1 d G U P F 1
H1A H 0.3139 0.1438 0.2899 0.063 Uiso 0.3 1 calc R U P F 1
C2 C 0.2606(19) 0.148(2) 0.1593(17) 0.057(9) Uani 0.3 1 d G U P F 1
H2A H 0.3030 0.1147 0.1378 0.068 Uiso 0.3 1 calc R U P F 1
C3 C 0.1920(19) 0.1795(18) 0.1004(11) 0.053(9) Uani 0.3 1 d DG U P F 1
C4 C 0.1300(17) 0.228(2) 0.1319(17) 0.052(10) Uani 0.3 1 d G U P F 1
H4A H 0.0831 0.2497 0.0917 0.062 Uiso 0.3 1 calc R U P F 1
C5 C 0.137(2) 0.2455(18) 0.2223(19) 0.11(2) Uani 0.3 1 d G U P F 1
H5A H 0.0941 0.2788 0.2438 0.131 Uiso 0.3 1 calc R U P F 1
C6 C 0.2540(10) 0.1148(12) -0.0321(8) 0.054(10) Uani 0.3 1 d G U P F 1
H6A H 0.3018 0.0948 0.0079 0.065 Uiso 0.3 1 calc R U P F 1
C7 C 0.1895(11) 0.1594(11) 0.0000(8) 0.031(5) Uani 0.3 1 d DG U P F 1
C8 C 0.1197(11) 0.1887(12) -0.0585(10) 0.050(7) Uani 0.3 1 d G U P F 1
H8A H 0.0756 0.2191 -0.0366 0.060 Uiso 0.3 1 calc R U P F 1
C9 C 0.1144(10) 0.1735(13) -0.1492(10) 0.074(10) Uani 0.3 1 d G U P F 1
H9A H 0.0667 0.1936 -0.1892 0.089 Uiso 0.3 1 calc R U P F 1
C10 C 0.1789(9) 0.1290(10) -0.1813(8) 0.06(2) Uani 0.3 1 d G U P F 1
C15 C 0.2487(8) 0.0997(9) -0.1228(9) 0.043(7) Uani 0.3 1 d G U P F 1
C14 C 0.3133(10) 0.0552(12) -0.1549(13) 0.060(10) Uani 0.3 1 d G U P F 1
H14A H 0.3610 0.0351 -0.1149 0.072 Uiso 0.3 1 calc R U P F 1
C13 C 0.3080(13) 0.0400(14) -0.2456(13) 0.058(8) Uani 0.3 1 d G U P F 1
H13A H 0.3521 0.0096 -0.2676 0.070 Uiso 0.3 1 calc R U P F 1
C12 C 0.2381(15) 0.0694(15) -0.3042(10) 0.054(11) Uani 0.3 1 d G U P F 1
H12A H 0.2345 0.0590 -0.3661 0.065 Uiso 0.3 1 calc R U P F 1
C11 C 0.1736(13) 0.1139(15) -0.2720(8) 0.068(10) Uani 0.3 1 d G U P F 1
H11A H 0.1259 0.1339 -0.3120 0.082 Uiso 0.3 1 calc R U P F 1
C16 C 0.2084(16) 0.2286(13) 0.383(3) 0.066(7) Uani 0.55(6) 1 d D U P F 1
H16A H 0.2678 0.2401 0.4104 0.079 Uiso 0.55(6) 1 calc R U P F 1
H16B H 0.1731 0.2785 0.3926 0.079 Uiso 0.55(6) 1 calc R U P F 1
C17 C 0.1754(14) 0.1509(14) 0.424(2) 0.066(7) Uani 0.55(6) 1 d D U P F 1
H17A H 0.1741 0.1625 0.4876 0.079 Uiso 0.55(6) 1 calc R U P F 1
H17B H 0.2157 0.1035 0.4204 0.079 Uiso 0.55(6) 1 calc R U P F 1
C18 C 0.0876(15) 0.1233(15) 0.381(3) 0.071(8) Uani 0.55(6) 1 d D U P F 1
H18A H 0.0911 0.1008 0.3209 0.085 Uiso 0.55(6) 1 calc R U P F 1
H18B H 0.0496 0.1734 0.3740 0.085 Uiso 0.55(6) 1 calc R U P F 1
C19 C 0.049(2) 0.056(2) 0.433(3) 0.088(10) Uani 0.55(6) 1 d D U P F 1
H19A H -0.0029 0.0337 0.3975 0.132 Uiso 0.55(6) 1 calc R U P F 1
H19B H 0.0343 0.0814 0.4880 0.132 Uiso 0.55(6) 1 calc R U P F 1
H19C H 0.0899 0.0100 0.4486 0.132 Uiso 0.55(6) 1 calc R U P F 1
N1' N 0.2060(13) 0.2052(13) 0.2472(12) 0.047(6) Uani 0.40(2) 1 d DG U P F 2
C1' C 0.1436(11) 0.2298(12) 0.1775(15) 0.044(7) Uani 0.40(2) 1 d G U P F 2
H1'A H 0.0965 0.2629 0.1891 0.053 Uiso 0.40(2) 1 calc R U P F 2
C2' C 0.1501(11) 0.2058(13) 0.0909(13) 0.056(7) Uani 0.40(2) 1 d G U P F 2
H2'A H 0.1075 0.2226 0.0433 0.067 Uiso 0.40(2) 1 calc R U P F 2
C3' C 0.2191(13) 0.1573(14) 0.0740(12) 0.050(7) Uani 0.40(2) 1 d DG U P F 2
C4' C 0.2815(13) 0.1328(17) 0.1437(15) 0.091(12) Uani 0.40(2) 1 d G U P F 2
H4'A H 0.3286 0.0997 0.1322 0.109 Uiso 0.40(2) 1 calc R U P F 2
C5' C 0.2749(13) 0.1568(17) 0.2303(13) 0.071(11) Uani 0.40(2) 1 d G U P F 2
H5'A H 0.3175 0.1400 0.2780 0.086 Uiso 0.40(2) 1 calc R U P F 2
C6' C 0.1651(11) 0.1452(13) -0.0892(12) 0.085(10) Uani 0.40(2) 1 d G U P F 2
H6'A H 0.1147 0.1727 -0.0773 0.102 Uiso 0.40(2) 1 calc R U P F 2
C7' C 0.2307(13) 0.1277(13) -0.0200(11) 0.048(7) Uani 0.40(2) 1 d DG U P F 2
C8' C 0.3044(11) 0.0876(13) -0.0375(13) 0.074(9) Uani 0.40(2) 1 d G U P F 2
H8'A H 0.3492 0.0755 0.0098 0.089 Uiso 0.40(2) 1 calc R U P F 2
C9' C 0.3125(9) 0.0651(12) -0.1241(14) 0.064(9) Uani 0.40(2) 1 d G U P F 2
H9'A H 0.3629 0.0376 -0.1361 0.077 Uiso 0.40(2) 1 calc R U P F 2
C10' C 0.2469(9) 0.0826(8) -0.1933(12) 0.063(8) Uani 0.40(2) 1 d G U P F 2
C15' C 0.1732(9) 0.1227(9) -0.1759(11) 0.048(12) Uani 0.40(2) 1 d G U P F 2
C14' C 0.1076(11) 0.1403(14) -0.2450(12) 0.091(11) Uani 0.40(2) 1 d G U P F 2
H14B H 0.0573 0.1677 -0.2331 0.109 Uiso 0.40(2) 1 calc R U P F 2
C13' C 0.1157(13) 0.1178(15) -0.3317(12) 0.092(10) Uani 0.40(2) 1 d G U P F 2
H13B H 0.0709 0.1298 -0.3790 0.110 Uiso 0.40(2) 1 calc R U P F 2
C12' C 0.1894(14) 0.0777(13) -0.3492(12) 0.070(8) Uani 0.40(2) 1 d G U P F 2
H12B H 0.1949 0.0623 -0.4084 0.084 Uiso 0.40(2) 1 calc R U P F 2
C11' C 0.2550(11) 0.0601(12) -0.2800(13) 0.063(9) Uani 0.40(2) 1 d G U P F 2
H11B H 0.3054 0.0327 -0.2919 0.075 Uiso 0.40(2) 1 calc R U P F 2
C16' C 0.1975(16) 0.2224(14) 0.345(3) 0.051(8) Uani 0.45(6) 1 d D U P F 2
H16C H 0.2542 0.2364 0.3791 0.062 Uiso 0.45(6) 1 calc R U P F 2
H16D H 0.1595 0.2718 0.3489 0.062 Uiso 0.45(6) 1 calc R U P F 2
C17' C 0.1616(14) 0.1460(17) 0.387(3) 0.065(9) Uani 0.45(6) 1 d D U P F 2
H17C H 0.2012 0.0976 0.3851 0.078 Uiso 0.45(6) 1 calc R U P F 2
H17D H 0.1588 0.1586 0.4500 0.078 Uiso 0.45(6) 1 calc R U P F 2
C18' C 0.0741(14) 0.1197(15) 0.342(3) 0.054(8) Uani 0.45(6) 1 d D U P F 2
H18C H 0.0794 0.0939 0.2835 0.064 Uiso 0.45(6) 1 calc R U P F 2
H18D H 0.0382 0.1711 0.3303 0.064 Uiso 0.45(6) 1 calc R U P F 2
C19' C 0.0295(19) 0.0574(19) 0.395(3) 0.064(9) Uani 0.45(6) 1 d D U P F 2
H19D H -0.0193 0.0324 0.3560 0.096 Uiso 0.45(6) 1 calc R U P F 2
H19E H 0.0096 0.0870 0.4442 0.096 Uiso 0.45(6) 1 calc R U P F 2
H19F H 0.0694 0.0123 0.4179 0.096 Uiso 0.45(6) 1 calc R U P F 2
N1" N 0.2152(18) 0.2153(15) 0.2848(13) 0.06(2) Uani 0.30(2) 1 d DG U P F 3
C1" C 0.1487(14) 0.2314(15) 0.2161(17) 0.030(7) Uani 0.30(2) 1 d G U P F 3
H1"A H 0.0979 0.2576 0.2284 0.036 Uiso 0.30(2) 1 calc R U P F 3
C2" C 0.1566(15) 0.2091(17) 0.1293(15) 0.041(8) Uani 0.30(2) 1 d G U P F 3
H2"A H 0.1112 0.2201 0.0823 0.050 Uiso 0.30(2) 1 calc R U P F 3
C3" C 0.2310(19) 0.1707(18) 0.1113(14) 0.060(11) Uani 0.30(2) 1 d DG U P F 3
C4" C 0.2974(16) 0.1546(17) 0.1801(18) 0.057(10) Uani 0.30(2) 1 d G U P F 3
H4"A H 0.3483 0.1284 0.1677 0.069 Uiso 0.30(2) 1 calc R U P F 3
C5" C 0.2895(16) 0.1769(17) 0.2668(15) 0.049(9) Uani 0.30(2) 1 d G U P F 3
H5"A H 0.3350 0.1659 0.3138 0.058 Uiso 0.30(2) 1 calc R U P F 3
C6" C 0.1782(13) 0.1530(14) -0.0545(14) 0.050(9) Uani 0.30(2) 1 d G U P F 3
H6"A H 0.1286 0.1839 -0.0463 0.060 Uiso 0.30(2) 1 calc R U P F 3
C7" C 0.2397(14) 0.1340(14) 0.0181(13) 0.042(8) Uani 0.30(2) 1 d DG U P F 3
C8" C 0.3123(13) 0.0888(15) 0.0061(15) 0.060(9) Uani 0.30(2) 1 d G U P F 3
H8"A H 0.3542 0.0757 0.0558 0.073 Uiso 0.30(2) 1 calc R U P F 3
C9" C 0.3235(12) 0.0626(16) -0.0786(17) 0.080(13) Uani 0.30(2) 1 d G U P F 3
H9"A H 0.3731 0.0318 -0.0868 0.096 Uiso 0.30(2) 1 calc R U P F 3
C10" C 0.2620(12) 0.0817(12) -0.1513(14) 0.053(10) Uani 0.30(2) 1 d G U P F 3
C15" C 0.1894(12) 0.1269(12) -0.1393(13) 0.061(10) Uani 0.30(2) 1 d G U P F 3
C14" C 0.1280(15) 0.1460(19) -0.2119(15) 0.079(12) Uani 0.30(2) 1 d G U P F 3
H14C H 0.0784 0.1769 -0.2037 0.095 Uiso 0.30(2) 1 calc R U P F 3
C13" C 0.139(2) 0.120(2) -0.2966(14) 0.103(17) Uani 0.30(2) 1 d G U P F 3
H13C H 0.0972 0.1329 -0.3463 0.124 Uiso 0.30(2) 1 calc R U P F 3
C12" C 0.212(2) 0.075(2) -0.3087(14) 0.076(14) Uani 0.30(2) 1 d G U P F 3
H12C H 0.2195 0.0568 -0.3666 0.091 Uiso 0.30(2) 1 calc R U P F 3
C11" C 0.2732(18) 0.0556(19) -0.2360(16) 0.12(2) Uani 0.30(2) 1 d G U P F 3
H11C H 0.3228 0.0247 -0.2442 0.139 Uiso 0.30(2) 1 calc R U P F 3


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I3 I3 2.74(5) 2_654 ?
I5 I5 1.72(8) 2_654 ?
N1 C1 1.3900 . ?
N1 C5 1.3900 . ?
N1 C16 1.55(4) . ?
C1 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C7 1.555(17) . ?
C4 C5 1.3900 . ?
C6 C7 1.3900 . ?
C6 C15 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C10 C15 1.3900 . ?
C10 C11 1.3900 . ?
C15 C14 1.3900 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C11 1.3900 . ?
C16 C17 1.506(17) . ?
C17 C18 1.509(18) . ?
C18 C19 1.509(17) . ?
N1' C1' 1.3900 . ?
N1' C5' 1.3900 . ?
N1' C16' 1.54(4) . ?
C1' C2' 1.3900 . ?
C2' C3' 1.3900 . ?
C3' C4' 1.3900 . ?
C3' C7' 1.543(17) . ?
C4' C5' 1.3900 . ?
C6' C7' 1.3900 . ?
C6' C15' 1.3900 . ?
C7' C8' 1.3900 . ?
C8' C9' 1.3900 . ?
C9' C10' 1.3900 . ?
C10' C15' 1.3900 . ?
C10' C11' 1.3900 . ?
C15' C14' 1.3900 . ?
C14' C13' 1.3900 . ?
C13' C12' 1.3900 . ?
C12' C11' 1.3900 . ?
C16' C17' 1.509(17) . ?
C17' C18' 1.508(18) . ?
C18' C19' 1.511(17) . ?
N1" C1" 1.3900 . ?
N1" C5" 1.3900 . ?
C1" C2" 1.3900 . ?
C2" C3" 1.3900 . ?
C3" C4" 1.3900 . ?
C3" C7" 1.557(17) . ?
C4" C5" 1.3900 . ?
C6" C7" 1.3900 . ?
C6" C15" 1.3900 . ?
C7" C8" 1.3900 . ?
C8" C9" 1.3900 . ?
C9" C10" 1.3900 . ?
C10" C15" 1.3900 . ?
C10" C11" 1.3900 . ?
C15" C14" 1.3900 . ?
C14" C13" 1.3900 . ?
C13" C12" 1.3900 . ?
C12" C11" 1.3900 . ?

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
_geom_angle_publ_flag
C1 N1 C5 120.0 . . ?
C1 N1 C16 120(2) . . ?
C5 N1 C16 119(2) . . ?
C2 C1 N1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C7 123(2) . . ?
C2 C3 C7 117(2) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 N1 120.0 . . ?
C7 C6 C15 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 C3 117.4(15) . . ?
C6 C7 C3 122.6(15) . . ?
C9 C8 C7 120.0 . . ?
C8 C9 C10 120.0 . . ?
C15 C10 C9 120.0 . . ?
C15 C10 C11 120.0 . . ?
C9 C10 C11 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 C6 120.0 . . ?
C10 C15 C6 120.0 . . ?
C15 C14 C13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C11 C12 C13 120.0 . . ?
C12 C11 C10 120.0 . . ?
C17 C16 N1 109.6(16) . . ?
C16 C17 C18 114.2(17) . . ?
C17 C18 C19 113.4(18) . . ?
C1' N1' C5' 120.0 . . ?
C1' N1' C16' 122.1(16) . . ?
C5' N1' C16' 117.6(16) . . ?
C2' C1' N1' 120.0 . . ?
C3' C2' C1' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' C7' 123.2(14) . . ?
C4' C3' C7' 116.8(14) . . ?
C5' C4' C3' 120.0 . . ?
C4' C5' N1' 120.0 . . ?
C7' C6' C15' 120.0 . . ?
C8' C7' C6' 120.0 . . ?
C8' C7' C3' 122.6(13) . . ?
C6' C7' C3' 117.4(13) . . ?
C7' C8' C9' 120.0 . . ?
C8' C9' C10' 120.0 . . ?
C15' C10' C9' 120.0 . . ?
C15' C10' C11' 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C14' C15' C10' 120.0 . . ?
C14' C15' C6' 120.0 . . ?
C10' C15' C6' 120.0 . . ?
C13' C14' C15' 120.0 . . ?
C14' C13' C12' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C12' C11' C10' 120.0 . . ?
C17' C16' N1' 111.0(16) . . ?
C18' C17' C16' 114.2(18) . . ?
C17' C18' C19' 114.2(18) . . ?
C1" N1" C5" 120.0 . . ?
C2" C1" N1" 120.0 . . ?
C1" C2" C3" 120.0 . . ?
C2" C3" C4" 120.0 . . ?
C2" C3" C7" 122.5(19) . . ?
C4" C3" C7" 117.0(19) . . ?
C5" C4" C3" 120.0 . . ?
C4" C5" N1" 120.0 . . ?
C7" C6" C15" 120.0 . . ?
C6" C7" C8" 120.0 . . ?
C6" C7" C3" 119.7(16) . . ?
C8" C7" C3" 120.1(16) . . ?
C7" C8" C9" 120.0 . . ?
C8" C9" C10" 120.0 . . ?
C15" C10" C9" 120.0 . . ?
C15" C10" C11" 120.0 . . ?
C9" C10" C11" 120.0 . . ?
C10" C15" C14" 120.0 . . ?
C10" C15" C6" 120.0 . . ?
C14" C15" C6" 120.0 . . ?
C13" C14" C15" 120.0 . . ?
C14" C13" C12" 120.0 . . ?
C11" C12" C13" 120.0 . . ?
C12" C11" C10" 120.0 . . ?

_refine_diff_density_max         1.417
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.126


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pp
_database_code_depnum_ccdc_archive 'CCDC 1867415'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'3-[4-(2-naphthyl)pyridinium-1-yl]propane-1-sulfonate,benzene and water solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_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

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2091(3)
_cell_length_b                   9.6979(4)
_cell_length_c                   13.7643(5)
_cell_angle_alpha                72.9840(10)
_cell_angle_beta                 84.0570(10)
_cell_angle_gamma                65.7620(10)
_cell_volume                     955.28(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2906
_cell_measurement_theta_min      2.396
_cell_measurement_theta_max      30.004

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             426
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.203
_shelx_estimated_absorpt_T_min   0.895
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART-6K'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8150
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.547
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4975
_reflns_number_gt                4365
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4975
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN-DMSO-benzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nn
_database_code_depnum_ccdc_archive 'CCDC 1867413'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1-butyl-4-(2-naphthyl)pyridinium iodide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C19 H20 N), 2(I)'
_chemical_formula_sum            'C19 H20 I N'
_chemical_formula_weight         389.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8562(3)
_cell_length_b                   14.2979(3)
_cell_length_c                   15.3748(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.969(2)
_cell_angle_gamma                90
_cell_volume                     3396.71(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13070
_cell_measurement_theta_min      3.154
_cell_measurement_theta_max      28.838

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.880
_shelx_estimated_absorpt_T_min   0.520
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5202
_exptl_absorpt_correction_T_max  0.9119
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46072
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8351
_reflns_number_gt                6927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.7094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8351
_refine_ls_number_parameters     539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.45627(2) 0.56566(2) 0.30779(2) 0.01970(5) Uani 1 1 d . . . . .
I2 I 0.82540(2) 0.64447(2) 0.40423(2) 0.02277(5) Uani 1 1 d . . . . .
N1 N 0.29171(12) 0.26814(13) 0.36836(13) 0.0163(4) Uani 1 1 d . . . . .
C1 C 0.33178(17) 0.32054(17) 0.43830(18) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.41947(16) 0.33441(17) 0.45593(17) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.46989(15) 0.29303(16) 0.40257(16) 0.0164(5) Uani 1 1 d . . . . .
C4 C 0.42640(16) 0.23626(17) 0.33259(17) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.33817(17) 0.22588(17) 0.31639(17) 0.0196(5) Uani 1 1 d . . . . .
C6 C 0.56415(15) 0.30980(16) 0.41849(15) 0.0152(5) Uani 1 1 d . . . . .
C7 C 0.60047(16) 0.39276(16) 0.46319(16) 0.0174(5) Uani 1 1 d . . . . .
C8 C 0.68705(16) 0.41039(16) 0.47615(16) 0.0174(5) Uani 1 1 d . . . . .
C9 C 0.74336(15) 0.34694(16) 0.44687(15) 0.0164(5) Uani 1 1 d . . . . .
C10 C 0.83368(16) 0.36420(18) 0.45879(17) 0.0200(5) Uani 1 1 d . . . . .
C11 C 0.88535(17) 0.30193(19) 0.42830(18) 0.0238(6) Uani 1 1 d . . . . .
C12 C 0.85023(17) 0.21946(19) 0.38387(18) 0.0252(6) Uani 1 1 d . . . . .
C13 C 0.76403(17) 0.20046(18) 0.37146(17) 0.0224(6) Uani 1 1 d . . . . .
C14 C 0.70825(15) 0.26379(16) 0.40246(15) 0.0162(5) Uani 1 1 d . . . . .
C15 C 0.61781(16) 0.24730(17) 0.38922(16) 0.0171(5) Uani 1 1 d . . . . .
C16 C 0.19677(16) 0.25273(18) 0.35172(18) 0.0187(5) Uani 1 1 d . . . . .
C17 C 0.17594(16) 0.16667(17) 0.40025(18) 0.0171(5) Uani 1 1 d . . . . .
C18 C 0.07883(16) 0.15605(18) 0.39049(19) 0.0212(5) Uani 1 1 d . . . . .
C19 C 0.05708(19) 0.07384(19) 0.4438(2) 0.0244(6) Uani 1 1 d . . . . .
N2 N 0.60747(13) 0.35690(13) 0.18255(13) 0.0169(4) Uani 1 1 d . . . . .
C1' C 0.65318(16) 0.42500(16) 0.23328(16) 0.0175(5) Uani 1 1 d . . . . .
C2' C 0.74053(16) 0.43309(17) 0.24155(16) 0.0175(5) Uani 1 1 d . . . . .
C3' C 0.78573(16) 0.37165(15) 0.19744(15) 0.0150(5) Uani 1 1 d . . . . .
C4' C 0.73613(17) 0.30112(17) 0.14669(17) 0.0212(5) Uani 1 1 d . . . . .
C5' C 0.64866(17) 0.29527(17) 0.14030(17) 0.0204(5) Uani 1 1 d . . . . .
C6' C 0.87958(16) 0.38074(16) 0.20261(16) 0.0159(5) Uani 1 1 d . . . . .
C7' C 0.92131(17) 0.32231(17) 0.15017(18) 0.0215(5) Uani 1 1 d . . . . .
C8' C 1.00702(17) 0.33266(18) 0.15096(18) 0.0224(6) Uani 1 1 d . . . . .
C9' C 1.05746(16) 0.40243(17) 0.20365(16) 0.0194(5) Uani 1 1 d . . . . .
C10' C 1.14619(17) 0.41793(18) 0.20328(18) 0.0228(6) Uani 1 1 d . . . . .
C11' C 1.19184(18) 0.48573(19) 0.25526(19) 0.0266(6) Uani 1 1 d . . . . .
C12' C 1.15236(19) 0.5423(2) 0.30972(19) 0.0302(7) Uani 1 1 d . . . . .
C13' C 1.06722(18) 0.5299(2) 0.31160(18) 0.0267(6) Uani 1 1 d . . . . .
C14' C 1.01740(16) 0.45955(17) 0.25808(16) 0.0183(5) Uani 1 1 d . . . . .
C15' C 0.92898(16) 0.44701(17) 0.25679(16) 0.0183(5) Uani 1 1 d . . . . .
C16' C 0.51172(16) 0.35363(18) 0.16846(18) 0.0193(5) Uani 1 1 d . . . . .
C17' C 0.46981(17) 0.41828(19) 0.09273(18) 0.0221(6) Uani 1 1 d . . . . .
C18' C 0.37179(17) 0.42202(19) 0.0814(2) 0.0251(6) Uani 1 1 d . . . . .
C19' C 0.3308(2) 0.4951(2) 0.0130(2) 0.0325(7) Uani 1 1 d . . . . .
H1A H 0.2983(16) 0.3431(16) 0.4745(16) 0.015(7) Uiso 1 1 d . . . . .
H2A H 0.4436(17) 0.3663(17) 0.5037(18) 0.020(7) Uiso 1 1 d . . . . .
H4A H 0.4542(17) 0.2056(18) 0.2950(17) 0.025(7) Uiso 1 1 d . . . . .
H5A H 0.3099(16) 0.1911(17) 0.2704(17) 0.017(7) Uiso 1 1 d . . . . .
H7A H 0.5639(17) 0.4363(17) 0.4847(16) 0.019(7) Uiso 1 1 d . . . . .
H8A H 0.7104(15) 0.4656(16) 0.5056(15) 0.011(6) Uiso 1 1 d . . . . .
H10A H 0.8549(16) 0.4199(16) 0.4886(16) 0.013(6) Uiso 1 1 d . . . . .
H11A H 0.9445(17) 0.3135(17) 0.4383(16) 0.020(7) Uiso 1 1 d . . . . .
H12A H 0.8840(17) 0.1762(18) 0.3597(17) 0.023(7) Uiso 1 1 d . . . . .
H13A H 0.7384(19) 0.1470(19) 0.3384(19) 0.035(8) Uiso 1 1 d . . . . .
H15A H 0.5975(16) 0.1926(17) 0.3595(16) 0.016(6) Uiso 1 1 d . . . . .
H16A H 0.1738(16) 0.3093(17) 0.3724(16) 0.015(6) Uiso 1 1 d . . . . .
H16B H 0.1766(16) 0.2466(16) 0.2874(17) 0.018(7) Uiso 1 1 d . . . . .
H17A H 0.1991(16) 0.1107(17) 0.3759(16) 0.015(6) Uiso 1 1 d . . . . .
H17B H 0.2013(16) 0.1709(16) 0.4608(17) 0.017(7) Uiso 1 1 d . . . . .
H18A H 0.0485(17) 0.1496(16) 0.3264(18) 0.022(7) Uiso 1 1 d . . . . .
H18B H 0.0584(16) 0.2139(18) 0.4109(16) 0.022(7) Uiso 1 1 d . . . . .
H19A H 0.0773(16) 0.0160(18) 0.4242(16) 0.019(7) Uiso 1 1 d . . . . .
H19B H -0.0064(19) 0.0661(18) 0.4340(18) 0.029(8) Uiso 1 1 d . . . . .
H19C H 0.0801(19) 0.0806(18) 0.506(2) 0.032(8) Uiso 1 1 d . . . . .
H1'A H 0.6213(16) 0.4629(17) 0.2618(16) 0.015(6) Uiso 1 1 d . . . . .
H2'A H 0.7680(16) 0.4773(17) 0.2765(17) 0.019(7) Uiso 1 1 d . . . . .
H4'A H 0.7595(17) 0.2560(18) 0.1159(18) 0.027(7) Uiso 1 1 d . . . . .
H5'A H 0.6168(16) 0.2491(17) 0.1092(16) 0.017(7) Uiso 1 1 d . . . . .
H7'A H 0.8887(16) 0.2775(17) 0.1128(16) 0.015(6) Uiso 1 1 d . . . . .
H8'A H 1.0331(17) 0.2942(18) 0.1164(17) 0.023(7) Uiso 1 1 d . . . . .
H10B H 1.1723(17) 0.3781(18) 0.1674(17) 0.021(7) Uiso 1 1 d . . . . .
H11B H 1.2490(18) 0.4944(18) 0.2549(17) 0.025(7) Uiso 1 1 d . . . . .
H12B H 1.1835(19) 0.588(2) 0.3427(19) 0.036(9) Uiso 1 1 d . . . . .
H13B H 1.0412(17) 0.5680(17) 0.3473(18) 0.022(7) Uiso 1 1 d . . . . .
H15B H 0.9037(16) 0.4866(17) 0.2916(16) 0.017(7) Uiso 1 1 d . . . . .
H16C H 0.4975(16) 0.3737(16) 0.2213(17) 0.013(6) Uiso 1 1 d . . . . .
H16D H 0.4953(16) 0.2878(17) 0.1576(16) 0.017(6) Uiso 1 1 d . . . . .
H17C H 0.4950(17) 0.4799(18) 0.1074(17) 0.023(7) Uiso 1 1 d . . . . .
H17D H 0.4864(15) 0.3989(16) 0.0369(17) 0.014(6) Uiso 1 1 d . . . . .
H18C H 0.3612(17) 0.4350(16) 0.1356(18) 0.019(7) Uiso 1 1 d . . . . .
H18D H 0.3476(18) 0.3598(19) 0.0639(18) 0.030(8) Uiso 1 1 d . . . . .
H19D H 0.3528(19) 0.559(2) 0.0277(18) 0.033(8) Uiso 1 1 d . . . . .
H19E H 0.269(2) 0.5009(19) 0.0064(18) 0.035(8) Uiso 1 1 d . . . . .
H19F H 0.339(2) 0.479(2) -0.049(2) 0.051(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.345(3) . ?
N1 C1 1.347(3) . ?
N1 C16 1.486(3) . ?
C1 C2 1.370(3) . ?
C2 C3 1.399(3) . ?
C3 C4 1.400(3) . ?
C3 C6 1.479(3) . ?
C4 C5 1.373(3) . ?
C6 C15 1.377(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.366(3) . ?
C8 C9 1.416(3) . ?
C9 C14 1.421(3) . ?
C9 C10 1.424(3) . ?
C10 C11 1.362(4) . ?
C11 C12 1.413(4) . ?
C12 C13 1.364(4) . ?
C13 C14 1.421(3) . ?
C14 C15 1.422(3) . ?
C16 C17 1.513(3) . ?
C17 C18 1.521(3) . ?
C18 C19 1.516(4) . ?
N2 C5' 1.347(3) . ?
N2 C1' 1.352(3) . ?
N2 C16' 1.485(3) . ?
C1' C2' 1.367(3) . ?
C2' C3' 1.401(3) . ?
C3' C4' 1.403(3) . ?
C3' C6' 1.478(3) . ?
C4' C5' 1.371(4) . ?
C6' C15' 1.383(3) . ?
C6' C7' 1.423(3) . ?
C7' C8' 1.364(4) . ?
C8' C9' 1.414(4) . ?
C9' C14' 1.418(3) . ?
C9' C10' 1.426(3) . ?
C10' C11' 1.357(4) . ?
C11' C12' 1.408(4) . ?
C12' C13' 1.368(4) . ?
C13' C14' 1.422(4) . ?
C14' C15' 1.409(3) . ?
C16' C17' 1.518(4) . ?
C17' C18' 1.526(4) . ?
C18' C19' 1.521(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
_geom_angle_publ_flag
C5 N1 C1 120.1(2) . . ?
C5 N1 C16 120.0(2) . . ?
C1 N1 C16 119.9(2) . . ?
N1 C1 C2 121.0(2) . . ?
C1 C2 C3 120.7(2) . . ?
C2 C3 C4 116.6(2) . . ?
C2 C3 C6 121.6(2) . . ?
C4 C3 C6 121.8(2) . . ?
C5 C4 C3 120.6(2) . . ?
N1 C5 C4 121.0(2) . . ?
C15 C6 C7 119.0(2) . . ?
C15 C6 C3 121.1(2) . . ?
C7 C6 C3 119.9(2) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C8 C9 121.4(2) . . ?
C8 C9 C14 118.8(2) . . ?
C8 C9 C10 122.4(2) . . ?
C14 C9 C10 118.8(2) . . ?
C11 C10 C9 120.5(2) . . ?
C10 C11 C12 120.6(2) . . ?
C13 C12 C11 120.5(3) . . ?
C12 C13 C14 120.4(2) . . ?
C13 C14 C9 119.2(2) . . ?
C13 C14 C15 122.0(2) . . ?
C9 C14 C15 118.8(2) . . ?
C6 C15 C14 121.5(2) . . ?
N1 C16 C17 111.1(2) . . ?
C16 C17 C18 111.1(2) . . ?
C19 C18 C17 111.8(2) . . ?
C5' N2 C1' 119.6(2) . . ?
C5' N2 C16' 120.0(2) . . ?
C1' N2 C16' 120.3(2) . . ?
N2 C1' C2' 121.0(2) . . ?
C1' C2' C3' 121.3(2) . . ?
C2' C3' C4' 115.9(2) . . ?
C2' C3' C6' 122.5(2) . . ?
C4' C3' C6' 121.7(2) . . ?
C5' C4' C3' 121.0(2) . . ?
N2 C5' C4' 121.2(2) . . ?
C15' C6' C7' 118.1(2) . . ?
C15' C6' C3' 121.3(2) . . ?
C7' C6' C3' 120.6(2) . . ?
C8' C7' C6' 121.3(2) . . ?
C7' C8' C9' 121.0(2) . . ?
C8' C9' C14' 118.3(2) . . ?
C8' C9' C10' 122.6(2) . . ?
C14' C9' C10' 119.1(2) . . ?
C11' C10' C9' 120.3(3) . . ?
C10' C11' C12' 120.7(3) . . ?
C13' C12' C11' 120.8(3) . . ?
C12' C13' C14' 120.1(3) . . ?
C15' C14' C9' 119.6(2) . . ?
C15' C14' C13' 121.3(2) . . ?
C9' C14' C13' 119.0(2) . . ?
C6' C15' C14' 121.5(2) . . ?
N2 C16' C17' 110.5(2) . . ?
C16' C17' C18' 111.6(2) . . ?
C19' C18' C17' 111.6(2) . . ?

_refine_diff_density_max         1.354
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.102


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN-benzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dd
_database_code_depnum_ccdc_archive 'CCDC 1867418'
_audit_update_record             
;
2018-09-13 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'complex between 3-[4-(2-naphthyl)pyridinium-1-yl]propane-1-sulfonateand cucurbit[8]uril, water solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C18 H17 N O3 S), C48 H48 N32 O16, 15.7(H2 O)'
_chemical_formula_sum            'C84 H113.40 N34 O37.70 S2'
_chemical_formula_weight         2266.80

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   38.5719(14)
_cell_length_b                   38.5719(14)
_cell_length_c                   14.8762(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     22133(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2956
_cell_measurement_theta_min      2.248
_cell_measurement_theta_max      20.974

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             9512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       /W
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            119809
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.094
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             14726
_reflns_number_gt                7228
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         14726
_refine_ls_number_parameters     918
_refine_ls_number_restraints     354
_refine_ls_R_factor_all          0.1936
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.3502
_refine_ls_wR_factor_gt          0.3069
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38787(3) 0.57888(3) 0.04001(8) 0.0490(3) Uani 1 1 d . . . . .
O11 O 0.37345(9) 0.55922(12) -0.0322(2) 0.0659(11) Uani 1 1 d . . . . .
O12 O 0.36458(11) 0.58043(12) 0.1163(3) 0.0743(12) Uani 1 1 d . . . . .
O13 O 0.39827(13) 0.61229(12) 0.0105(3) 0.0859(14) Uani 1 1 d . . . . .
N1' N 0.43679(19) 0.52298(19) 0.2631(6) 0.051(2) Uani 0.522(6) 1 d G U P A 1
C1' C 0.4696(2) 0.5093(2) 0.2474(4) 0.045(3) Uani 0.522(6) 1 d G U P A 1
H1'A H 0.4741 0.4970 0.1933 0.054 Uiso 0.522(6) 1 calc R U P A 1
C2' C 0.49570(17) 0.5136(3) 0.3107(6) 0.050(3) Uani 0.522(6) 1 d G U P A 1
H2'A H 0.5181 0.5043 0.3000 0.060 Uiso 0.522(6) 1 calc R U P A 1
C3' C 0.4891(2) 0.5316(3) 0.3898(6) 0.052(5) Uani 0.522(6) 1 d G U P A 1
C4' C 0.4563(3) 0.5453(3) 0.4055(6) 0.085(5) Uani 0.522(6) 1 d G U P A 1
H4'A H 0.4517 0.5576 0.4595 0.102 Uiso 0.522(6) 1 calc R U P A 1
C5' C 0.4301(2) 0.5410(2) 0.3421(7) 0.085(4) Uani 0.522(6) 1 d G U P A 1
H5'A H 0.4077 0.5504 0.3529 0.101 Uiso 0.522(6) 1 calc R U P A 1
C6' C 0.51869(15) 0.55703(17) 0.5312(4) 0.071(3) Uani 0.522(6) 1 d G U P A 1
H6'A H 0.4982 0.5700 0.5428 0.086 Uiso 0.522(6) 1 calc R U P A 1
C7' C 0.52113(18) 0.53693(19) 0.4539(4) 0.055(3) Uani 0.522(6) 1 d G U P A 1
C8' C 0.5511(2) 0.51797(19) 0.4369(4) 0.078(4) Uani 0.522(6) 1 d G U P A 1
H8'A H 0.5527 0.5042 0.3841 0.093 Uiso 0.522(6) 1 calc R U P A 1
C9' C 0.57857(17) 0.51912(19) 0.4972(4) 0.097(5) Uani 0.522(6) 1 d G U P A 1
H9'A H 0.5990 0.5062 0.4856 0.116 Uiso 0.522(6) 1 calc R U P A 1
C10' C 0.57614(13) 0.53923(15) 0.5745(4) 0.074(4) Uani 0.522(6) 1 d G U P A 1
C15' C 0.54620(14) 0.55818(13) 0.5915(4) 0.055(3) Uani 0.522(6) 1 d G U P A 1
C14' C 0.5438(2) 0.57829(19) 0.6687(4) 0.119(7) Uani 0.522(6) 1 d G U P A 1
H14C H 0.5233 0.5912 0.6804 0.142 Uiso 0.522(6) 1 calc R U P A 1
C13' C 0.5713(2) 0.5794(2) 0.7290(4) 0.080(4) Uani 0.522(6) 1 d G U P A 1
H13A H 0.5696 0.5932 0.7819 0.096 Uiso 0.522(6) 1 calc R U P A 1
C12' C 0.6012(2) 0.5605(2) 0.7120(5) 0.060(3) Uani 0.522(6) 1 d G U P A 1
H12C H 0.6200 0.5613 0.7533 0.072 Uiso 0.522(6) 1 calc R U P A 1
C11' C 0.60364(15) 0.5404(2) 0.6348(5) 0.095(5) Uani 0.522(6) 1 d G U P A 1
H11A H 0.6241 0.5274 0.6232 0.114 Uiso 0.522(6) 1 calc R U P A 1
C16' C 0.4110(4) 0.5161(4) 0.1909(9) 0.092(4) Uani 0.522(6) 1 d D U P A 1
H16C H 0.3917 0.5330 0.1958 0.111 Uiso 0.522(6) 1 calc R U P A 1
H16D H 0.4013 0.4926 0.1986 0.111 Uiso 0.522(6) 1 calc R U P A 1
C17' C 0.4284(5) 0.5193(3) 0.0942(11) 0.100(6) Uani 0.522(6) 1 d D U P A 1
H17B H 0.4529 0.5117 0.0954 0.120 Uiso 0.522(6) 1 calc R U P A 1
H17C H 0.4156 0.5055 0.0490 0.120 Uiso 0.522(6) 1 calc R U P A 1
N1" N 0.4578(3) 0.5132(3) 0.2384(5) 0.063(4) Uani 0.478(6) 1 d G U P A 2
C1" C 0.4415(2) 0.5361(3) 0.2968(6) 0.053(3) Uani 0.478(6) 1 d G U P A 2
H1"A H 0.4187 0.5439 0.2845 0.064 Uiso 0.478(6) 1 calc R U P A 2
C2" C 0.4587(2) 0.5476(3) 0.3735(6) 0.053(3) Uani 0.478(6) 1 d G U P A 2
H2"A H 0.4476 0.5632 0.4134 0.063 Uiso 0.478(6) 1 calc R U P A 2
C3" C 0.4921(3) 0.5361(4) 0.3916(6) 0.040(4) Uani 0.478(6) 1 d G U P A 2
C4" C 0.5084(2) 0.5132(3) 0.3331(8) 0.078(5) Uani 0.478(6) 1 d G U P A 2
H4"A H 0.5313 0.5054 0.3455 0.094 Uiso 0.478(6) 1 calc R U P A 2
C5" C 0.4913(3) 0.5017(2) 0.2565(7) 0.075(4) Uani 0.478(6) 1 d G U P A 2
H5"A H 0.5024 0.4861 0.2165 0.090 Uiso 0.478(6) 1 calc R U P A 2
C6" C 0.54340(17) 0.53893(19) 0.4959(4) 0.072(4) Uani 0.478(6) 1 d G U P A 2
H6"A H 0.5568 0.5272 0.4517 0.086 Uiso 0.478(6) 1 calc R U P A 2
C7" C 0.50870(18) 0.54631(18) 0.4796(4) 0.043(3) Uani 0.478(6) 1 d G U P A 2
C8" C 0.48911(15) 0.56344(19) 0.5443(5) 0.067(3) Uani 0.478(6) 1 d G U P A 2
H8"A H 0.4654 0.5685 0.5331 0.081 Uiso 0.478(6) 1 calc R U P A 2
C9" C 0.50424(17) 0.5732(2) 0.6252(5) 0.094(5) Uani 0.478(6) 1 d G U P A 2
H9"A H 0.4909 0.5849 0.6694 0.112 Uiso 0.478(6) 1 calc R U P A 2
C10" C 0.53895(16) 0.56583(15) 0.6415(4) 0.087(5) Uani 0.478(6) 1 d G U P A 2
C15" C 0.55853(13) 0.54869(16) 0.5769(4) 0.069(4) Uani 0.478(6) 1 d G U P A 2
C14" C 0.59324(14) 0.5413(2) 0.5932(6) 0.144(10) Uani 0.478(6) 1 d G U P A 2
H14D H 0.6066 0.5296 0.5490 0.172 Uiso 0.478(6) 1 calc R U P A 2
C13" C 0.60837(16) 0.5511(3) 0.6741(7) 0.069(4) Uani 0.478(6) 1 d G U P A 2
H13B H 0.6321 0.5460 0.6852 0.083 Uiso 0.478(6) 1 calc R U P A 2
C12" C 0.5888(2) 0.5682(3) 0.7387(6) 0.078(5) Uani 0.478(6) 1 d G U P A 2
H12D H 0.5991 0.5749 0.7941 0.093 Uiso 0.478(6) 1 calc R U P A 2
C11" C 0.5541(2) 0.5756(2) 0.7225(5) 0.090(5) Uani 0.478(6) 1 d G U P A 2
H11B H 0.5407 0.5873 0.7666 0.108 Uiso 0.478(6) 1 calc R U P A 2
C16" C 0.4453(3) 0.4989(3) 0.1498(9) 0.070(4) Uani 0.478(6) 1 d D U P A 2
H16E H 0.4381 0.4745 0.1577 0.083 Uiso 0.478(6) 1 calc R U P A 2
H16F H 0.4644 0.4996 0.1054 0.083 Uiso 0.478(6) 1 calc R U P A 2
C17" C 0.4138(3) 0.5206(2) 0.1136(8) 0.037(3) Uani 0.478(6) 1 d D U P A 2
H17D H 0.3970 0.5241 0.1629 0.044 Uiso 0.478(6) 1 calc R U P A 2
H17E H 0.4021 0.5073 0.0654 0.044 Uiso 0.478(6) 1 calc R U P A 2
C18' C 0.42560(13) 0.55738(13) 0.0752(3) 0.0531(13) Uani 1 1 d D . . . .
H18B H 0.4434 0.5625 0.0291 0.064 Uiso 0.522(6) 1 calc R U P A 1
H18C H 0.4332 0.5693 0.1307 0.064 Uiso 0.522(6) 1 calc R U P A 1
H18D H 0.4417 0.5543 0.0239 0.064 Uiso 0.478(6) 1 calc R U P A 2
H18E H 0.4375 0.5709 0.1224 0.064 Uiso 0.478(6) 1 calc R U P A 2
O1 O 0.61254(7) 0.59164(7) 0.43180(19) 0.0368(7) Uani 1 1 d . . . . .
O2 O 0.65331(9) 0.49827(8) 0.4270(2) 0.0492(8) Uani 1 1 d . . . . .
O3 O 0.62644(9) 0.41909(8) 0.5556(2) 0.0484(8) Uani 1 1 d . . . . .
O4 O 0.56289(8) 0.39250(9) 0.7450(2) 0.0457(8) Uani 1 1 d . . . . .
O5 O 0.50740(7) 0.55611(8) 0.1272(2) 0.0387(7) Uani 1 1 d . . . . .
O6 O 0.54124(8) 0.45867(7) 0.1518(2) 0.0475(8) Uani 1 1 d . . . . .
O7 O 0.52528(8) 0.36786(9) 0.2637(2) 0.0481(8) Uani 1 1 d . . . . .
O8 O 0.45985(7) 0.34880(8) 0.4443(2) 0.0389(7) Uani 1 1 d . . . . .
N1 N 0.57314(8) 0.61343(8) 0.3292(2) 0.0277(7) Uani 1 1 d . . . . .
N2 N 0.60698(8) 0.56956(8) 0.2882(2) 0.0304(7) Uani 1 1 d . . . . .
N3 N 0.63070(8) 0.51152(8) 0.2876(2) 0.0330(8) Uani 1 1 d . . . . .
N4 N 0.63713(9) 0.45636(8) 0.3253(2) 0.0353(8) Uani 1 1 d . . . . .
N5 N 0.62305(9) 0.40406(8) 0.4058(2) 0.0321(7) Uani 1 1 d . . . . .
N6 N 0.59546(9) 0.37173(9) 0.5061(2) 0.0349(8) Uani 1 1 d . . . . .
N7 N 0.55323(9) 0.35797(10) 0.6205(2) 0.0360(8) Uani 1 1 d . . . . .
N8 N 0.51076(9) 0.36492(9) 0.7190(2) 0.0345(8) Uani 1 1 d . . . . .
N9 N 0.53306(8) 0.60072(8) 0.2065(2) 0.0309(7) Uani 1 1 d . . . . .
N10 N 0.56467(9) 0.55435(8) 0.1735(2) 0.0326(7) Uani 1 1 d . . . . .
N11 N 0.58683(9) 0.49585(9) 0.1770(2) 0.0361(8) Uani 1 1 d . . . . .
N12 N 0.59170(8) 0.44068(8) 0.2196(2) 0.0296(7) Uani 1 1 d . . . . .
N13 N 0.58125(8) 0.38545(9) 0.2911(2) 0.0312(7) Uani 1 1 d . . . . .
N14 N 0.55526(8) 0.35140(9) 0.3907(2) 0.0325(7) Uani 1 1 d . . . . .
N15 N 0.51329(8) 0.33674(9) 0.5060(2) 0.0331(7) Uani 1 1 d . . . . .
N16 N 0.47026(8) 0.35177(8) 0.5973(2) 0.0301(7) Uani 1 1 d . . . . .
C1 C 0.59894(10) 0.59151(9) 0.3575(3) 0.0282(8) Uani 1 1 d . . . . .
C2 C 0.63842(11) 0.54830(10) 0.2899(3) 0.0377(10) Uani 1 1 d . . . . .
H2A H 0.6531 0.5543 0.2376 0.045 Uiso 1 1 calc R U . . .
H2B H 0.6517 0.5536 0.3451 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64165(10) 0.48976(10) 0.3545(3) 0.0340(9) Uani 1 1 d . . . . .
C4 C 0.65022(11) 0.42672(10) 0.3732(3) 0.0369(10) Uani 1 1 d . . . . .
H4A H 0.6642 0.4348 0.4249 0.044 Uiso 1 1 calc R U . . .
H4B H 0.6657 0.4134 0.3329 0.044 Uiso 1 1 calc R U . . .
C5 C 0.61607(10) 0.40010(11) 0.4956(3) 0.0349(9) Uani 1 1 d . . . . .
C6 C 0.58941(11) 0.35627(13) 0.5932(3) 0.0405(10) Uani 1 1 d . . . . .
H6A H 0.6038 0.3683 0.6385 0.049 Uiso 1 1 calc R U . . .
H6B H 0.5968 0.3317 0.5915 0.049 Uiso 1 1 calc R U . . .
C7 C 0.54439(11) 0.37379(11) 0.7000(3) 0.0354(9) Uani 1 1 d . . . . .
C8 C 0.49449(11) 0.37415(11) 0.8038(3) 0.0344(9) Uani 1 1 d . . . . .
H8A H 0.4850 0.3529 0.8319 0.041 Uiso 1 1 calc R U . . .
H8B H 0.5123 0.3837 0.8447 0.041 Uiso 1 1 calc R U . . .
C9 C 0.53212(10) 0.56925(10) 0.1647(3) 0.0303(8) Uani 1 1 d . . . . .
C10 C 0.57440(12) 0.52406(10) 0.1217(3) 0.0380(10) Uani 1 1 d . . . . .
H10A H 0.5541 0.5160 0.0868 0.046 Uiso 1 1 calc R U . . .
H10B H 0.5928 0.5306 0.0784 0.046 Uiso 1 1 calc R U . . .
C11 C 0.57043(10) 0.46433(10) 0.1798(3) 0.0311(8) Uani 1 1 d . . . . .
C12 C 0.58643(10) 0.40369(9) 0.2085(3) 0.0307(8) Uani 1 1 d . . . . .
H12A H 0.5660 0.4000 0.1695 0.037 Uiso 1 1 calc R U . . .
H12B H 0.6068 0.3938 0.1775 0.037 Uiso 1 1 calc R U . . .
C13 C 0.55127(10) 0.36839(11) 0.3108(3) 0.0352(9) Uani 1 1 d . . . . .
C14 C 0.53042(11) 0.32606(11) 0.4239(3) 0.0372(9) Uani 1 1 d . . . . .
H14A H 0.5127 0.3219 0.3771 0.045 Uiso 1 1 calc R U . . .
H14B H 0.5426 0.3039 0.4349 0.045 Uiso 1 1 calc R U . . .
C15 C 0.47907(10) 0.34628(10) 0.5086(3) 0.0320(9) Uani 1 1 d . . . . .
C16 C 0.43456(10) 0.35480(10) 0.6226(3) 0.0315(8) Uani 1 1 d . . . . .
H16A H 0.4282 0.3348 0.6608 0.038 Uiso 1 1 calc R U . . .
H16B H 0.4200 0.3538 0.5677 0.038 Uiso 1 1 calc R U . . .
C17 C 0.56773(10) 0.61061(10) 0.2330(3) 0.0293(8) Uani 1 1 d . . . . .
H17A H 0.5754 0.6321 0.2011 0.035 Uiso 1 1 calc R U . . .
C18 C 0.58998(10) 0.57915(9) 0.2060(3) 0.0278(8) Uani 1 1 d . . . . .
H18A H 0.6071 0.5854 0.1582 0.033 Uiso 1 1 calc R U . . .
C19 C 0.62268(10) 0.49338(10) 0.2047(3) 0.0316(8) Uani 1 1 d . . . . .
H19A H 0.6390 0.4997 0.1551 0.038 Uiso 1 1 calc R U . . .
C20 C 0.62645(9) 0.45470(10) 0.2333(3) 0.0296(8) Uani 1 1 d . . . . .
H20A H 0.6440 0.4424 0.1954 0.035 Uiso 1 1 calc R U . . .
C21 C 0.60925(10) 0.37572(10) 0.3527(3) 0.0291(8) Uani 1 1 d . . . . .
H21A H 0.6281 0.3628 0.3208 0.035 Uiso 1 1 calc R U . . .
C22 C 0.59082(10) 0.35264(10) 0.4224(3) 0.0296(8) Uani 1 1 d . . . . .
H22A H 0.6014 0.3290 0.4255 0.036 Uiso 1 1 calc R U . . .
C23 C 0.52795(10) 0.33217(10) 0.5945(3) 0.0338(9) Uani 1 1 d . . . . .
H23A H 0.5372 0.3082 0.6026 0.041 Uiso 1 1 calc R U . . .
C24 C 0.49746(11) 0.33917(10) 0.6577(3) 0.0345(9) Uani 1 1 d . . . . .
H24A H 0.4901 0.3177 0.6901 0.041 Uiso 1 1 calc R U . . .
O1W O 0.5000 0.2500 0.4647(4) 0.0834(19) Uani 1 2 d S TU P . .
O2W O 0.3553(3) 0.6867(2) 0.2557(6) 0.095(3) Uani 0.5 1 d . U P . .
O3W O 0.44741(19) 0.6611(2) 0.0655(6) 0.076(3) Uani 0.5 1 d . U P . .
O4W O 0.3390(3) 0.6216(2) 0.2578(5) 0.084(3) Uani 0.5 1 d . U P . .
O5W O 0.6912(3) 0.5091(4) 0.7332(8) 0.084(4) Uani 0.35 1 d . U P . .
O6W O 0.48098(15) 0.4523(2) 0.0561(4) 0.095(2) Uani 0.75 1 d . U P B 1
O7W O 0.5185(2) 0.3017(3) 0.1715(7) 0.065(3) Uani 0.5 1 d . U P C 1
O8W O 0.4501(3) 0.7590(2) 0.2497(6) 0.084(3) Uani 0.5 1 d . U P D 1
O9W O 0.4275(3) 0.6936(2) 0.2252(7) 0.082(3) Uani 0.4 1 d . U P E 1
O10W O 0.6678(6) 0.5377(4) 0.8927(12) 0.087(5) Uani 0.25 1 d . U P F 1
O11W O 0.7513(2) 0.54533(19) 0.4485(6) 0.070(2) Uani 0.5 1 d . U P G 1
O12W O 0.3135(2) 0.5186(2) -0.0223(7) 0.085(3) Uani 0.5 1 d . U P H 1
O13W O 0.7043(2) 0.5085(4) 0.5465(6) 0.088(4) Uani 0.4 1 d . U P I 1
O14W O 0.7113(4) 0.5430(3) 0.4761(14) 0.080(5) Uani 0.25 1 d . U P J 2
O15W O 0.2700(4) 0.5063(4) -0.0259(11) 0.068(4) Uani 0.25 1 d . U P K 2
O16W O 0.4204(7) 0.7302(6) 0.2626(14) 0.054(6) Uani 0.15 1 d . U P L 2
O17W O 0.6426(6) 0.5375(7) 0.955(2) 0.067(7) Uani 0.15 1 d . U P M 2
O18W O 0.4905(6) 0.4120(7) 0.111(2) 0.076(8) Uani 0.15 1 d . U P N 2
O19W O 0.5003(4) 0.3096(4) 0.1853(9) 0.068(4) Uani 0.35 1 d . U P O 2
O20W O 0.5000 0.7500 0.1250 0.065(10) Uani 0.2 4 d S TU P . .
O21W O 0.3538(6) 0.5536(6) 0.2826(12) 0.082(6) Uani 0.2 1 d . U P . .
O22W O 0.6674(5) 0.4827(5) 0.6216(14) 0.043(5) Uani 0.15 1 d . U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O13 1.419(5) . ?
S1 O11 1.428(4) . ?
S1 O12 1.448(4) . ?
S1 C18' 1.755(5) . ?
N1' C1' 1.3900 . ?
N1' C5' 1.3900 . ?
N1' C16' 1.486(13) . ?
C1' C2' 1.3900 . ?
C2' C3' 1.3900 . ?
C3' C4' 1.3900 . ?
C3' C7' 1.575(8) . ?
C4' C5' 1.3900 . ?
C6' C7' 1.3900 . ?
C6' C15' 1.3900 . ?
C7' C8' 1.3900 . ?
C8' C9' 1.3900 . ?
C9' C10' 1.3900 . ?
C10' C15' 1.3900 . ?
C10' C11' 1.3900 . ?
C15' C14' 1.3900 . ?
C14' C13' 1.3900 . ?
C13' C12' 1.3900 . ?
C12' C11' 1.3900 . ?
C16' C17' 1.592(14) . ?
C17' C18' 1.501(13) . ?
N1" C1" 1.3900 . ?
N1" C5" 1.3900 . ?
N1" C16" 1.508(15) . ?
C1" C2" 1.3900 . ?
C2" C3" 1.3900 . ?
C3" C4" 1.3900 . ?
C3" C7" 1.509(8) . ?
C4" C5" 1.3900 . ?
C6" C7" 1.3900 . ?
C6" C15" 1.3900 . ?
C7" C8" 1.3900 . ?
C8" C9" 1.3900 . ?
C9" C10" 1.3900 . ?
C10" C15" 1.3900 . ?
C10" C11" 1.3900 . ?
C15" C14" 1.3900 . ?
C14" C13" 1.3900 . ?
C13" C12" 1.3900 . ?
C12" C11" 1.3900 . ?
C16" C17" 1.567(12) . ?
C17" C18' 1.597(10) . ?
O1 C1 1.224(5) . ?
O2 C3 1.214(5) . ?
O3 C5 1.222(5) . ?
O4 C7 1.216(5) . ?
O5 C9 1.216(5) . ?
O6 C11 1.220(5) . ?
O7 C13 1.223(5) . ?
O8 C15 1.215(5) . ?
N1 C1 1.372(5) . ?
N1 C16 1.451(5) 9_666 ?
N1 C17 1.451(5) . ?
N2 C1 1.370(5) . ?
N2 C18 1.436(5) . ?
N2 C2 1.464(5) . ?
N3 C3 1.368(5) . ?
N3 C2 1.450(5) . ?
N3 C19 1.451(5) . ?
N4 C3 1.371(5) . ?
N4 C20 1.431(5) . ?
N4 C4 1.439(5) . ?
N5 C5 1.371(5) . ?
N5 C4 1.448(5) . ?
N5 C21 1.450(5) . ?
N6 C5 1.362(5) . ?
N6 C6 1.445(6) . ?
N6 C22 1.457(5) . ?
N7 C7 1.373(5) . ?
N7 C23 1.446(5) . ?
N7 C6 1.455(5) . ?
N8 C7 1.371(5) . ?
N8 C24 1.442(5) . ?
N8 C8 1.453(5) . ?
N9 C9 1.365(5) . ?
N9 C17 1.445(5) . ?
N9 C8 1.447(5) 9_666 ?
N10 C9 1.387(5) . ?
N10 C10 1.449(5) . ?
N10 C18 1.450(5) . ?
N11 C11 1.371(5) . ?
N11 C19 1.446(5) . ?
N11 C10 1.446(5) . ?
N12 C11 1.362(5) . ?
N12 C12 1.451(5) . ?
N12 C20 1.460(5) . ?
N13 C13 1.363(5) . ?
N13 C12 1.429(5) . ?
N13 C21 1.465(5) . ?
N14 C13 1.366(6) . ?
N14 C22 1.451(5) . ?
N14 C14 1.455(5) . ?
N15 C15 1.370(5) . ?
N15 C23 1.444(5) . ?
N15 C14 1.448(5) . ?
N16 C15 1.378(5) . ?
N16 C16 1.432(5) . ?
N16 C24 1.465(5) . ?
C8 N9 1.447(5) 9_666 ?
C16 N1 1.450(5) 9_666 ?
C17 C18 1.540(5) . ?
C19 C20 1.558(5) . ?
C21 C22 1.541(6) . ?
C23 C24 1.530(6) . ?

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
_geom_angle_publ_flag
O13 S1 O11 111.1(3) . . ?
O13 S1 O12 112.3(3) . . ?
O11 S1 O12 111.7(3) . . ?
O13 S1 C18' 106.7(3) . . ?
O11 S1 C18' 107.2(2) . . ?
O12 S1 C18' 107.5(3) . . ?
C1' N1' C5' 120.0 . . ?
C1' N1' C16' 114.8(9) . . ?
C5' N1' C16' 125.2(9) . . ?
C2' C1' N1' 120.0 . . ?
C1' C2' C3' 120.0 . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' C7' 115.6(7) . . ?
C4' C3' C7' 124.3(7) . . ?
C5' C4' C3' 120.0 . . ?
C4' C5' N1' 120.0 . . ?
C7' C6' C15' 120.0 . . ?
C6' C7' C8' 120.0 . . ?
C6' C7' C3' 121.3(6) . . ?
C8' C7' C3' 118.3(6) . . ?
C9' C8' C7' 120.0 . . ?
C8' C9' C10' 120.0 . . ?
C9' C10' C15' 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C15' C10' C11' 120.0 . . ?
C14' C15' C10' 120.0 . . ?
C14' C15' C6' 120.0 . . ?
C10' C15' C6' 120.0 . . ?
C15' C14' C13' 120.0 . . ?
C12' C13' C14' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C12' C11' C10' 120.0 . . ?
N1' C16' C17' 110.9(11) . . ?
C18' C17' C16' 102.4(9) . . ?
C1" N1" C5" 120.0 . . ?
C1" N1" C16" 129.3(9) . . ?
C5" N1" C16" 110.6(9) . . ?
N1" C1" C2" 120.0 . . ?
C1" C2" C3" 120.0 . . ?
C4" C3" C2" 120.0 . . ?
C4" C3" C7" 121.2(7) . . ?
C2" C3" C7" 118.6(7) . . ?
C3" C4" C5" 120.0 . . ?
C4" C5" N1" 120.0 . . ?
C7" C6" C15" 120.0 . . ?
C6" C7" C8" 120.0 . . ?
C6" C7" C3" 120.4(6) . . ?
C8" C7" C3" 119.6(6) . . ?
C9" C8" C7" 120.0 . . ?
C10" C9" C8" 120.0 . . ?
C15" C10" C9" 120.0 . . ?
C15" C10" C11" 120.0 . . ?
C9" C10" C11" 120.0 . . ?
C10" C15" C14" 120.0 . . ?
C10" C15" C6" 120.0 . . ?
C14" C15" C6" 120.0 . . ?
C13" C14" C15" 120.0 . . ?
C12" C13" C14" 120.0 . . ?
C13" C12" C11" 120.0 . . ?
C12" C11" C10" 120.0 . . ?
N1" C16" C17" 110.8(10) . . ?
C16" C17" C18' 112.2(8) . . ?
C17' C18' S1 125.4(8) . . ?
C17" C18' S1 107.0(4) . . ?
C1 N1 C16 121.2(3) . 9_666 ?
C1 N1 C17 111.1(3) . . ?
C16 N1 C17 121.4(3) 9_666 . ?
C1 N2 C18 112.2(3) . . ?
C1 N2 C2 121.4(3) . . ?
C18 N2 C2 122.5(3) . . ?
C3 N3 C2 121.3(3) . . ?
C3 N3 C19 112.8(3) . . ?
C2 N3 C19 122.4(3) . . ?
C3 N4 C20 112.5(3) . . ?
C3 N4 C4 123.0(3) . . ?
C20 N4 C4 122.6(3) . . ?
C5 N5 C4 122.4(3) . . ?
C5 N5 C21 112.0(3) . . ?
C4 N5 C21 122.6(3) . . ?
C5 N6 C6 121.9(4) . . ?
C5 N6 C22 112.3(3) . . ?
C6 N6 C22 122.5(3) . . ?
C7 N7 C23 111.7(3) . . ?
C7 N7 C6 119.9(3) . . ?
C23 N7 C6 122.7(3) . . ?
C7 N8 C24 112.2(3) . . ?
C7 N8 C8 121.7(3) . . ?
C24 N8 C8 124.3(3) . . ?
C9 N9 C17 112.6(3) . . ?
C9 N9 C8 121.9(3) . 9_666 ?
C17 N9 C8 122.1(3) . 9_666 ?
C9 N10 C10 121.2(3) . . ?
C9 N10 C18 111.6(3) . . ?
C10 N10 C18 122.3(3) . . ?
C11 N11 C19 112.0(3) . . ?
C11 N11 C10 122.1(3) . . ?
C19 N11 C10 121.9(4) . . ?
C11 N12 C12 121.7(3) . . ?
C11 N12 C20 111.4(3) . . ?
C12 N12 C20 120.6(3) . . ?
C13 N13 C12 122.8(3) . . ?
C13 N13 C21 111.6(3) . . ?
C12 N13 C21 124.1(3) . . ?
C13 N14 C22 111.9(3) . . ?
C13 N14 C14 122.9(3) . . ?
C22 N14 C14 122.3(3) . . ?
C15 N15 C23 112.6(3) . . ?
C15 N15 C14 122.7(3) . . ?
C23 N15 C14 123.7(3) . . ?
C15 N16 C16 120.1(3) . . ?
C15 N16 C24 111.1(3) . . ?
C16 N16 C24 123.7(3) . . ?
O1 C1 N2 125.9(4) . . ?
O1 C1 N1 125.8(4) . . ?
N2 C1 N1 108.4(3) . . ?
N3 C2 N2 112.2(3) . . ?
O2 C3 N3 126.5(4) . . ?
O2 C3 N4 125.7(4) . . ?
N3 C3 N4 107.9(3) . . ?
N4 C4 N5 113.0(3) . . ?
O3 C5 N6 126.1(4) . . ?
O3 C5 N5 125.5(4) . . ?
N6 C5 N5 108.4(3) . . ?
N6 C6 N7 112.8(3) . . ?
O4 C7 N8 126.2(4) . . ?
O4 C7 N7 126.3(4) . . ?
N8 C7 N7 107.5(3) . . ?
N9 C8 N8 112.9(3) 9_666 . ?
O5 C9 N9 127.0(4) . . ?
O5 C9 N10 125.5(4) . . ?
N9 C9 N10 107.5(3) . . ?
N11 C10 N10 113.0(3) . . ?
O6 C11 N12 125.8(4) . . ?
O6 C11 N11 125.0(4) . . ?
N12 C11 N11 109.2(3) . . ?
N13 C12 N12 114.0(3) . . ?
O7 C13 N13 125.5(4) . . ?
O7 C13 N14 125.7(4) . . ?
N13 C13 N14 108.8(3) . . ?
N15 C14 N14 113.3(3) . . ?
O8 C15 N15 125.9(4) . . ?
O8 C15 N16 126.2(4) . . ?
N15 C15 N16 107.8(3) . . ?
N16 C16 N1 113.3(3) . 9_666 ?
N9 C17 N1 114.9(3) . . ?
N9 C17 C18 103.7(3) . . ?
N1 C17 C18 103.7(3) . . ?
N2 C18 N10 114.9(3) . . ?
N2 C18 C17 103.6(3) . . ?
N10 C18 C17 103.4(3) . . ?
N11 C19 N3 114.5(3) . . ?
N11 C19 C20 103.3(3) . . ?
N3 C19 C20 102.1(3) . . ?
N4 C20 N12 114.5(3) . . ?
N4 C20 C19 104.2(3) . . ?
N12 C20 C19 103.4(3) . . ?
N5 C21 N13 114.7(3) . . ?
N5 C21 C22 103.8(3) . . ?
N13 C21 C22 103.2(3) . . ?
N14 C22 N6 114.2(3) . . ?
N14 C22 C21 103.7(3) . . ?
N6 C22 C21 103.1(3) . . ?
N15 C23 N7 115.1(3) . . ?
N15 C23 C24 103.8(3) . . ?
N7 C23 C24 103.4(3) . . ?
N8 C24 N16 114.5(3) . . ?
N8 C24 C23 103.7(3) . . ?
N16 C24 C23 103.4(3) . . ?

_refine_diff_density_max         1.269
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.137


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
