# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1THF
_database_code_depnum_ccdc_archive 'CCDC 1036224'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '4-phenylpyridinium pamoate THF solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, 2(C11 H10 N), C4 H8 O'
_chemical_formula_sum            'C49 H42 N2 O7'
_chemical_formula_weight         770.84

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'

_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                   26.859(5)
_cell_length_b                   10.5583(19)
_cell_length_c                   15.311(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.508(2)
_cell_angle_gamma                90
_cell_volume                     3778.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1763
_cell_measurement_theta_min      2.671
_cell_measurement_theta_max      25.362

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1624
_exptl_transmission_factor_min   0.9277
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focused sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10792
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3853
_reflns_number_gt                2724
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_computing_publication_material  
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_refine_special_details          
;
The THF molecule has been modelled with half occupancy as it 
is on a special position
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+1.4719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3853
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.23935(5) 0.66742(13) 0.85920(10) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.26162(7) 0.56264(15) 0.68505(12) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.19957(8) 0.59019(18) 0.82204(14) 0.0210(4) Uani 1 1 d . . . . .
O2 O 0.19579(5) 0.50191(13) 0.76059(10) 0.0255(3) Uani 1 1 d . . . . .
C2 C 0.15197(8) 0.59741(17) 0.84693(14) 0.0200(4) Uani 1 1 d . . . . .
O3 O 0.09222(6) 0.45360(13) 0.71374(10) 0.0245(3) Uani 1 1 d . . . . .
C3 C 0.09933(8) 0.53071(17) 0.79023(13) 0.0198(4) Uani 1 1 d . . . . .
O4 O 0.43791(14) 0.4792(3) 0.2614(2) 0.0445(8) Uani 0.5 1 d . . P A -1
C4 C 0.05495(7) 0.54190(17) 0.81122(13) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.06374(7) 0.61477(17) 0.89582(13) 0.0191(4) Uani 1 1 d . . . . .
C6 C 0.02253(8) 0.62313(18) 0.92837(14) 0.0221(4) Uani 1 1 d . . . . .
H6 H -0.0130 0.5804 0.8917 0.026 Uiso 1 1 calc R U . . .
C7 C 0.03341(8) 0.69192(19) 1.01178(14) 0.0257(5) Uani 1 1 d . . . . .
H7 H 0.0051 0.6964 1.0318 0.031 Uiso 1 1 calc R U . . .
C8 C 0.08547(8) 0.75590(19) 1.06833(15) 0.0268(5) Uani 1 1 d . . . . .
H8 H 0.0921 0.8041 1.1255 0.032 Uiso 1 1 calc R U . . .
C9 C 0.12637(8) 0.74833(18) 1.04050(14) 0.0248(4) Uani 1 1 d . . . . .
H9 H 0.1619 0.7904 1.0795 0.030 Uiso 1 1 calc R U . . .
C10 C 0.11695(8) 0.67907(17) 0.95475(14) 0.0204(4) Uani 1 1 d . . . . .
C11 C 0.15948(8) 0.66957(17) 0.92680(13) 0.0207(4) Uani 1 1 d . . . . .
H11 H 0.1944 0.7145 0.9644 0.025 Uiso 1 1 calc R U . . .
C12 C 0.0000 0.4662(2) 0.7500 0.0207(6) Uani 1 2 d S T P . .
H12B H 0.0055 0.4106 0.7034 0.025 Uiso 0.5 1 calc R U P . .
H12A H -0.0055 0.4106 0.7966 0.025 Uiso 0.5 1 calc R U P . .
C13 C 0.27356(9) 0.4750(2) 0.63498(16) 0.0332(5) Uani 1 1 d . . . . .
H13 H 0.2637 0.3890 0.6368 0.040 Uiso 1 1 calc R U . . .
C14 C 0.29996(9) 0.5079(2) 0.58107(16) 0.0327(5) Uani 1 1 d . . . . .
H14 H 0.3081 0.4445 0.5459 0.039 Uiso 1 1 calc R U . . .
C15 C 0.31495(8) 0.63324(18) 0.57718(14) 0.0214(4) Uani 1 1 d . . . . .
C16 C 0.34135(8) 0.67078(18) 0.51562(14) 0.0225(4) Uani 1 1 d . . . . .
C17 C 0.34535(11) 0.5856(2) 0.45044(19) 0.0454(7) Uani 1 1 d . . . . .
H17 H 0.3317 0.5016 0.4462 0.054 Uiso 1 1 calc R U . . .
C18 C 0.36886(11) 0.6206(2) 0.39153(18) 0.0456(7) Uani 1 1 d . . . . .
H18 H 0.3721 0.5599 0.3488 0.055 Uiso 1 1 calc R U . . .
C19 C 0.38756(8) 0.74214(19) 0.39429(15) 0.0283(5) Uani 1 1 d . . . . .
H19 H 0.4033 0.7663 0.3532 0.034 Uiso 1 1 calc R U . . .
C20 C 0.38327(9) 0.8283(2) 0.45715(16) 0.0325(5) Uani 1 1 d . . . . .
H20 H 0.3959 0.9129 0.4594 0.039 Uiso 1 1 calc R U . . .
C21 C 0.36059(8) 0.79301(19) 0.51753(15) 0.0298(5) Uani 1 1 d . . . . .
H21 H 0.3582 0.8538 0.5611 0.036 Uiso 1 1 calc R U . . .
C22 C 0.30257(8) 0.72052(19) 0.63193(15) 0.0269(5) Uani 1 1 d . . . . .
H22 H 0.3128 0.8069 0.6330 0.032 Uiso 1 1 calc R U . . .
C23 C 0.27590(8) 0.68341(19) 0.68427(15) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.2674 0.7446 0.7206 0.033 Uiso 1 1 calc R U . . .
C24 C 0.4679(4) 0.5903(8) 0.2658(7) 0.065(2) Uani 0.5 1 d . . P A -1
H24A H 0.4899 0.6210 0.3358 0.078 Uiso 0.5 1 calc R U P A -1
H24B H 0.4409 0.6576 0.2242 0.078 Uiso 0.5 1 calc R U P A -1
C25 C 0.5070(5) 0.5576(8) 0.2270(10) 0.088(3) Uani 0.5 1 d . . P A -1
H25A H 0.5462 0.5878 0.2735 0.106 Uiso 0.5 1 calc R U P A -1
H25B H 0.4937 0.5970 0.1604 0.106 Uiso 0.5 1 calc R U P A -1
C26 C 0.5060(4) 0.4172(8) 0.2188(8) 0.056(2) Uani 0.5 1 d . . P A -1
H26A H 0.5453 0.3821 0.2510 0.067 Uiso 0.5 1 calc R U P A -1
H26B H 0.4851 0.3897 0.1478 0.067 Uiso 0.5 1 calc R U P A -1
H3O H 0.1277(11) 0.458(2) 0.7151(19) 0.064(8) Uiso 1 1 d . . . . .
H1N H 0.2402(11) 0.536(2) 0.7249(18) 0.064(8) Uiso 1 1 d . . . . .
C27 C 0.4750(3) 0.3772(7) 0.2741(7) 0.0461(17) Uani 0.5 1 d . . P A -1
H27B H 0.4531 0.2983 0.2451 0.055 Uiso 0.5 1 calc R U P A -1
H27A H 0.5024 0.3629 0.3461 0.055 Uiso 0.5 1 calc R U P A -1


_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
O1 C1 1.238(2) . ?
N1 C23 1.333(2) . ?
N1 C13 1.338(2) . ?
N1 H1N 1.06(2) . ?
C1 O2 1.292(2) . ?
C1 C2 1.505(2) . ?
C2 C11 1.369(3) . ?
C2 C3 1.428(2) . ?
O3 C3 1.360(2) . ?
O3 H3O 0.94(3) . ?
C3 C4 1.384(2) . ?
O4 C24 1.406(10) . ?
O4 C27 1.415(9) . ?
C4 C5 1.423(3) . ?
C4 C12 1.527(2) . ?
C5 C6 1.423(2) . ?
C5 C10 1.431(2) . ?
C6 C7 1.370(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.407(2) . ?
C11 H11 0.9500 . ?
C12 C4 1.527(2) 2_556 ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.372(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C22 1.392(3) . ?
C15 C16 1.485(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.480(9) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.487(12) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.511(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27B 0.9900 . ?
C27 H27A 0.9900 . ?

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
C23 N1 C13 120.36(17) . . ?
C23 N1 H1N 120.1(14) . . ?
C13 N1 H1N 119.5(14) . . ?
O1 C1 O2 123.38(16) . . ?
O1 C1 C2 119.93(17) . . ?
O2 C1 C2 116.68(16) . . ?
C11 C2 C3 118.93(16) . . ?
C11 C2 C1 118.99(16) . . ?
C3 C2 C1 122.09(16) . . ?
C3 O3 H3O 104.0(16) . . ?
O3 C3 C4 118.64(16) . . ?
O3 C3 C2 119.71(15) . . ?
C4 C3 C2 121.66(17) . . ?
C24 O4 C27 106.3(4) . . ?
C3 C4 C5 118.81(16) . . ?
C3 C4 C12 119.69(15) . . ?
C5 C4 C12 121.23(14) . . ?
C4 C5 C6 122.92(17) . . ?
C4 C5 C10 119.80(16) . . ?
C6 C5 C10 117.22(16) . . ?
C7 C6 C5 120.92(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.38(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.40(18) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.22(18) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.27(17) . . ?
C11 C10 C5 118.86(17) . . ?
C9 C10 C5 119.85(16) . . ?
C2 C11 C10 121.80(17) . . ?
C2 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C4 C12 C4 116.9(2) 2_556 . ?
C4 C12 H12B 108.1 2_556 . ?
C4 C12 H12B 108.1 . . ?
C4 C12 H12A 108.1 2_556 . ?
C4 C12 H12A 108.1 . . ?
H12B C12 H12A 107.3 . . ?
N1 C13 C14 120.68(19) . . ?
N1 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.84(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C22 C15 C14 116.32(17) . . ?
C22 C15 C16 122.40(17) . . ?
C14 C15 C16 121.26(17) . . ?
C21 C16 C17 117.34(18) . . ?
C21 C16 C15 121.67(17) . . ?
C17 C16 C15 120.93(17) . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.14(19) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.46(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 121.25(18) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C15 120.81(18) . . ?
C23 C22 H22 119.6 . . ?
C15 C22 H22 119.6 . . ?
N1 C23 C22 120.98(18) . . ?
N1 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
O4 C24 C25 106.8(6) . . ?
O4 C24 H24A 110.4 . . ?
C25 C24 H24A 110.4 . . ?
O4 C24 H24B 110.4 . . ?
C25 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C24 C25 C26 106.3(6) . . ?
C24 C25 H25A 110.5 . . ?
C26 C25 H25A 110.5 . . ?
C24 C25 H25B 110.5 . . ?
C26 C25 H25B 110.5 . . ?
H25A C25 H25B 108.7 . . ?
C25 C26 C27 102.8(5) . . ?
C25 C26 H26A 111.2 . . ?
C27 C26 H26A 111.2 . . ?
C25 C26 H26B 111.2 . . ?
C27 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
O4 C27 C26 104.8(5) . . ?
O4 C27 H27B 110.8 . . ?
C26 C27 H27B 110.8 . . ?
O4 C27 H27A 110.8 . . ?
C26 C27 H27A 110.8 . . ?
H27B C27 H27A 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -14.7(3) . . . . ?
O2 C1 C2 C11 166.01(16) . . . . ?
O1 C1 C2 C3 165.69(17) . . . . ?
O2 C1 C2 C3 -13.6(3) . . . . ?
C11 C2 C3 O3 -176.74(16) . . . . ?
C1 C2 C3 O3 2.9(3) . . . . ?
C11 C2 C3 C4 3.0(3) . . . . ?
C1 C2 C3 C4 -177.40(16) . . . . ?
O3 C3 C4 C5 175.29(15) . . . . ?
C2 C3 C4 C5 -4.5(3) . . . . ?
O3 C3 C4 C12 1.2(2) . . . . ?
C2 C3 C4 C12 -178.57(16) . . . . ?
C3 C4 C5 C6 -174.58(17) . . . . ?
C12 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C10 2.6(3) . . . . ?
C12 C4 C5 C10 176.64(16) . . . . ?
C4 C5 C6 C7 178.35(17) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C11 -179.02(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C4 C5 C10 C11 0.6(3) . . . . ?
C6 C5 C10 C11 177.95(16) . . . . ?
C4 C5 C10 C9 -178.11(17) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
C3 C2 C11 C10 0.4(3) . . . . ?
C1 C2 C11 C10 -179.22(16) . . . . ?
C9 C10 C11 C2 176.57(17) . . . . ?
C5 C10 C11 C2 -2.1(3) . . . . ?
C3 C4 C12 C4 -117.73(17) . . . 2_556 ?
C5 C4 C12 C4 68.30(15) . . . 2_556 ?
C23 N1 C13 C14 -0.8(3) . . . . ?
N1 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C22 1.1(3) . . . . ?
C13 C14 C15 C16 -177.42(19) . . . . ?
C22 C15 C16 C21 6.8(3) . . . . ?
C14 C15 C16 C21 -174.7(2) . . . . ?
C22 C15 C16 C17 -170.3(2) . . . . ?
C14 C15 C16 C17 8.1(3) . . . . ?
C21 C16 C17 C18 1.5(4) . . . . ?
C15 C16 C17 C18 178.7(2) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C17 C16 C21 C20 -0.4(3) . . . . ?
C15 C16 C21 C20 -177.66(19) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C14 C15 C22 C23 -1.5(3) . . . . ?
C16 C15 C22 C23 177.05(18) . . . . ?
C13 N1 C23 C22 0.5(3) . . . . ?
C15 C22 C23 N1 0.7(3) . . . . ?
C27 O4 C24 C25 30.1(7) . . . . ?
O4 C24 C25 C26 -10.7(9) . . . . ?
C24 C25 C26 C27 -11.1(9) . . . . ?
C24 O4 C27 C26 -37.2(7) . . . . ?
C25 C26 C27 O4 29.1(8) . . . . ?

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
O3 H3O O2 0.94(3) 1.67(3) 2.5588(18) 155(2) .
N1 H1N O2 1.06(2) 1.58(3) 2.625(2) 167(2) .

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_1Dioxane
_database_code_depnum_ccdc_archive 'CCDC 1036225'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'4-phenylpyridinium pamoate 1,4-dioxane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, 2(C11 H10 N), C4 H8 O2'
_chemical_formula_sum            'C49 H42 N2 O8'
_chemical_formula_weight         786.84

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'

_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                   26.804(4)
_cell_length_b                   10.6999(16)
_cell_length_c                   15.194(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.868(2)
_cell_angle_gamma                90
_cell_volume                     3778.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1759
_cell_measurement_theta_min      2.690
_cell_measurement_theta_max      21.867

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   0.9186
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11690
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.752
_diffrn_reflns_theta_max         28.237
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4376
_reflns_number_gt                2757
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_computing_publication_material  
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_refine_special_details          
;
Half of the 1,4-dioxane molecule has been modelled at f
ull occupancy since the second half is generated through
symmetry
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4376
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O 0.23960(5) 0.66664(12) 0.85925(10) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.26292(7) 0.55820(15) 0.68642(12) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.20002(8) 0.58872(17) 0.82276(14) 0.0226(4) Uani 1 1 d . . . . .
O2 O 0.19668(5) 0.49949(12) 0.76291(10) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.15254(8) 0.59612(16) 0.84839(14) 0.0213(4) Uani 1 1 d . . . . .
O3 O 0.09301(6) 0.45123(12) 0.71551(10) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.09986(8) 0.52923(16) 0.79166(14) 0.0208(4) Uani 1 1 d . . . . .
O4 O 0.44790(6) 0.48817(13) 0.25243(11) 0.0397(4) Uani 1 1 d . . . . .
C4 C 0.05515(7) 0.54008(16) 0.81214(14) 0.0199(4) Uani 1 1 d . . . . .
C5 C 0.06391(8) 0.61316(16) 0.89691(13) 0.0198(4) Uani 1 1 d . . . . .
C6 C 0.02283(8) 0.62124(16) 0.92993(14) 0.0219(4) Uani 1 1 d . . . . .
H9 H -0.0127 0.5779 0.8935 0.026 Uiso 1 1 calc R U . . .
C7 C 0.03353(8) 0.69042(17) 1.01329(14) 0.0260(4) Uani 1 1 d . . . . .
H13 H 0.0053 0.6940 1.0337 0.031 Uiso 1 1 calc R U . . .
C8 C 0.08541(8) 0.75628(18) 1.06941(14) 0.0267(4) Uani 1 1 d . . . . .
H19 H 0.0918 0.8053 1.1263 0.032 Uiso 1 1 calc R U . . .
C9 C 0.12639(8) 0.74910(17) 1.04146(14) 0.0254(4) Uani 1 1 d . . . . .
H11 H 0.1618 0.7921 1.0802 0.030 Uiso 1 1 calc R U . . .
C10 C 0.11706(8) 0.67869(16) 0.95575(14) 0.0215(4) Uani 1 1 d . . . . .
C11 C 0.15987(8) 0.66929(17) 0.92773(14) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.1946 0.7150 0.9650 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0000 0.4660(2) 0.7500 0.0208(6) Uani 1 2 d S T P . .
H12B H -0.0055 0.4112 0.7970 0.025 Uiso 0.5 1 calc R U P . .
H12A H 0.0055 0.4112 0.7030 0.025 Uiso 0.5 1 calc R U P . .
C13 C 0.27692(9) 0.47207(19) 0.63867(16) 0.0339(5) Uani 1 1 d . . . . .
H1 H 0.2680 0.3867 0.6414 0.041 Uiso 1 1 calc R U . . .
C14 C 0.30396(9) 0.50545(19) 0.58598(16) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.3142 0.4427 0.5536 0.042 Uiso 1 1 calc R U . . .
C15 C 0.31667(8) 0.63028(17) 0.57909(14) 0.0230(4) Uani 1 1 d . . . . .
C16 C 0.34317(8) 0.66891(17) 0.51780(14) 0.0240(4) Uani 1 1 d . . . . .
C17 C 0.34999(11) 0.5843(2) 0.45530(18) 0.0432(6) Uani 1 1 d . . . . .
H17 H 0.3389 0.4997 0.4539 0.052 Uiso 1 1 calc R U . . .
C18 C 0.37267(11) 0.6208(2) 0.39499(18) 0.0442(6) Uani 1 1 d . . . . .
H18 H 0.3772 0.5610 0.3533 0.053 Uiso 1 1 calc R U . . .
C19 C 0.38857(8) 0.74203(19) 0.39505(15) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.4037 0.7669 0.3530 0.036 Uiso 1 1 calc R U . . .
C20 C 0.38251(9) 0.8279(2) 0.45662(16) 0.0352(5) Uani 1 1 d . . . . .
H20 H 0.3937 0.9123 0.4574 0.042 Uiso 1 1 calc R U . . .
C21 C 0.36011(9) 0.79143(19) 0.51737(16) 0.0338(5) Uani 1 1 d . . . . .
H21 H 0.3562 0.8515 0.5596 0.041 Uiso 1 1 calc R U . . .
C22 C 0.30212(8) 0.71637(18) 0.63150(15) 0.0285(5) Uani 1 1 d . . . . .
H22 H 0.3109 0.8023 0.6309 0.034 Uiso 1 1 calc R U . . .
C23 C 0.27540(8) 0.67878(18) 0.68372(15) 0.0292(5) Uani 1 1 d . . . . .
H23 H 0.2656 0.7390 0.7185 0.035 Uiso 1 1 calc R U . . .
C24 C 0.48275(11) 0.59732(18) 0.27672(18) 0.0423(6) Uani 1 1 d . . . . .
H24A H 0.5092 0.6010 0.3510 0.051 Uiso 1 1 calc R U . . .
H24B H 0.4579 0.6724 0.2565 0.051 Uiso 1 1 calc R U . . .
C25 C 0.48308(10) 0.37990(18) 0.27730(18) 0.0368(5) Uani 1 1 d . . . . .
H25B H 0.4586 0.3043 0.2583 0.044 Uiso 1 1 calc R U . . .
H25A H 0.5099 0.3774 0.3515 0.044 Uiso 1 1 calc R U . . .
H3O H 0.1300(11) 0.458(2) 0.7202(19) 0.069(8) Uiso 1 1 d . . . . .
H1N H 0.2423(11) 0.530(3) 0.729(2) 0.079(8) 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
O1 C1 1.242(2) . ?
N1 C13 1.337(2) . ?
N1 C23 1.339(2) . ?
N1 H1N 1.09(3) . ?
C1 O2 1.291(2) . ?
C1 C2 1.507(2) . ?
C2 C11 1.367(3) . ?
C2 C3 1.427(2) . ?
O3 C3 1.363(2) . ?
O3 H3O 0.96(3) . ?
C3 C4 1.385(2) . ?
O4 C25 1.421(2) . ?
O4 C24 1.424(2) . ?
C4 C5 1.423(2) . ?
C4 C12 1.521(2) . ?
C5 C6 1.422(2) . ?
C5 C10 1.433(2) . ?
C6 C7 1.368(3) . ?
C6 H9 0.9500 . ?
C7 C8 1.406(3) . ?
C7 H13 0.9500 . ?
C8 C9 1.363(3) . ?
C8 H19 0.9500 . ?
C9 C10 1.415(3) . ?
C9 H11 0.9500 . ?
C10 C11 1.412(2) . ?
C11 H12 0.9500 . ?
C12 C4 1.521(2) 2_556 ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.368(3) . ?
C13 H1 0.9500 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C22 1.394(2) . ?
C15 C16 1.484(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.388(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(3) . ?
C19 H2 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.368(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C24 1.504(4) 2_655 ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C25 1.503(4) 2_655 ?
C25 H25B 0.9900 . ?
C25 H25A 0.9900 . ?

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
C13 N1 C23 120.38(17) . . ?
C13 N1 H1N 119.6(14) . . ?
C23 N1 H1N 120.0(14) . . ?
O1 C1 O2 123.72(17) . . ?
O1 C1 C2 119.54(17) . . ?
O2 C1 C2 116.74(16) . . ?
C11 C2 C3 118.95(16) . . ?
C11 C2 C1 119.28(17) . . ?
C3 C2 C1 121.77(16) . . ?
C3 O3 H3O 101.1(15) . . ?
O3 C3 C4 118.44(16) . . ?
O3 C3 C2 119.62(15) . . ?
C4 C3 C2 121.93(17) . . ?
C25 O4 C24 109.69(16) . . ?
C3 C4 C5 118.58(16) . . ?
C3 C4 C12 119.94(15) . . ?
C5 C4 C12 121.29(14) . . ?
C6 C5 C4 123.04(17) . . ?
C6 C5 C10 117.03(16) . . ?
C4 C5 C10 119.89(16) . . ?
C7 C6 C5 121.15(17) . . ?
C7 C6 H9 119.4 . . ?
C5 C6 H9 119.4 . . ?
C6 C7 C8 121.37(17) . . ?
C6 C7 H13 119.3 . . ?
C8 C7 H13 119.3 . . ?
C9 C8 C7 119.34(18) . . ?
C9 C8 H19 120.3 . . ?
C7 C8 H19 120.3 . . ?
C8 C9 C10 121.09(18) . . ?
C8 C9 H11 119.5 . . ?
C10 C9 H11 119.5 . . ?
C11 C10 C9 121.18(17) . . ?
C11 C10 C5 118.81(17) . . ?
C9 C10 C5 120.00(16) . . ?
C2 C11 C10 121.68(17) . . ?
C2 C11 H12 119.2 . . ?
C10 C11 H12 119.2 . . ?
C4 C12 C4 117.2(2) . 2_556 ?
C4 C12 H12B 108.0 . . ?
C4 C12 H12B 108.0 2_556 . ?
C4 C12 H12A 108.0 . . ?
C4 C12 H12A 108.0 2_556 . ?
H12B C12 H12A 107.2 . . ?
N1 C13 C14 120.74(19) . . ?
N1 C13 H1 119.6 . . ?
C14 C13 H1 119.6 . . ?
C13 C14 C15 120.94(19) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C22 C15 C14 116.19(17) . . ?
C22 C15 C16 122.14(17) . . ?
C14 C15 C16 121.66(17) . . ?
C17 C16 C21 117.24(18) . . ?
C17 C16 C15 121.00(17) . . ?
C21 C16 C15 121.72(17) . . ?
C18 C17 C16 121.32(19) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 119.48(19) . . ?
C18 C19 H2 120.3 . . ?
C20 C19 H2 120.3 . . ?
C19 C20 C21 120.09(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 121.39(18) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C23 C22 C15 120.89(18) . . ?
C23 C22 H22 119.6 . . ?
C15 C22 H22 119.6 . . ?
N1 C23 C22 120.82(18) . . ?
N1 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O4 C24 C24 111.11(15) . 2_655 ?
O4 C24 H24A 109.4 . . ?
C24 C24 H24A 109.4 2_655 . ?
O4 C24 H24B 109.4 . . ?
C24 C24 H24B 109.4 2_655 . ?
H24A C24 H24B 108.0 . . ?
O4 C25 C25 110.86(15) . 2_655 ?
O4 C25 H25B 109.5 . . ?
C25 C25 H25B 109.5 2_655 . ?
O4 C25 H25A 109.5 . . ?
C25 C25 H25A 109.5 2_655 . ?
H25B C25 H25A 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -14.5(3) . . . . ?
O2 C1 C2 C11 165.48(17) . . . . ?
O1 C1 C2 C3 165.18(17) . . . . ?
O2 C1 C2 C3 -14.9(3) . . . . ?
C11 C2 C3 O3 -176.84(16) . . . . ?
C1 C2 C3 O3 3.5(3) . . . . ?
C11 C2 C3 C4 2.6(3) . . . . ?
C1 C2 C3 C4 -177.11(16) . . . . ?
O3 C3 C4 C5 174.81(15) . . . . ?
C2 C3 C4 C5 -4.6(3) . . . . ?
O3 C3 C4 C12 -0.1(2) . . . . ?
C2 C3 C4 C12 -179.54(16) . . . . ?
C3 C4 C5 C6 -174.19(16) . . . . ?
C12 C4 C5 C6 0.7(3) . . . . ?
C3 C4 C5 C10 3.2(3) . . . . ?
C12 C4 C5 C10 178.07(16) . . . . ?
C4 C5 C6 C7 178.50(17) . . . . ?
C10 C5 C6 C7 1.0(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C9 C10 C11 -178.84(17) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C11 177.68(16) . . . . ?
C4 C5 C10 C11 0.1(3) . . . . ?
C6 C5 C10 C9 -1.0(2) . . . . ?
C4 C5 C10 C9 -178.55(17) . . . . ?
C3 C2 C11 C10 1.0(3) . . . . ?
C1 C2 C11 C10 -179.34(16) . . . . ?
C9 C10 C11 C2 176.41(18) . . . . ?
C5 C10 C11 C2 -2.3(3) . . . . ?
C3 C4 C12 C4 -117.69(17) . . . 2_556 ?
C5 C4 C12 C4 67.50(15) . . . 2_556 ?
C23 N1 C13 C14 -0.3(3) . . . . ?
N1 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C22 2.2(3) . . . . ?
C13 C14 C15 C16 -176.71(19) . . . . ?
C22 C15 C16 C17 -171.0(2) . . . . ?
C14 C15 C16 C17 7.8(3) . . . . ?
C22 C15 C16 C21 6.5(3) . . . . ?
C14 C15 C16 C21 -174.7(2) . . . . ?
C21 C16 C17 C18 -0.1(4) . . . . ?
C15 C16 C17 C18 177.5(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C16 -0.2(3) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
C15 C16 C21 C20 -177.17(19) . . . . ?
C14 C15 C22 C23 -1.8(3) . . . . ?
C16 C15 C22 C23 177.06(18) . . . . ?
C13 N1 C23 C22 0.6(3) . . . . ?
C15 C22 C23 N1 0.5(3) . . . . ?
C25 O4 C24 C24 56.7(3) . . . 2_655 ?
C24 O4 C25 C25 -57.3(3) . . . 2_655 ?

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
O3 H3O O2 0.96(3) 1.63(3) 2.5523(18) 159(2) .
N1 H1N O2 1.09(3) 1.58(3) 2.637(2) 164(2) .

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_1DMSO
_database_code_depnum_ccdc_archive 'CCDC 1036226'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-phenylpyridinium pamoate DMSO solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C23 H14 O6, 2(C11 H10 N), 0.4(S2), 0.2(S), O, 2(C)'
_chemical_formula_sum            'C47 H34 N2 O7 S'
_chemical_formula_weight         770.82

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      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                   27.277(10)
_cell_length_b                   10.398(4)
_cell_length_c                   15.424(6)
_cell_angle_alpha                90
_cell_angle_beta                 119.020(4)
_cell_angle_gamma                90
_cell_volume                     3825(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1748
_cell_measurement_theta_min      2.366
_cell_measurement_theta_max      24.656

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             1608
_exptl_transmission_factor_min   0.8900
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8405
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.707
_diffrn_reflns_theta_max         24.689
_diffrn_reflns_theta_full        24.689
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3246
_reflns_number_gt                2291
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_computing_publication_material  
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_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)+(0.0890P)²+3.4970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3246
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.45887(10) 0.5612(3) 0.2636(2) 0.0652(7) Uani 0.4 1 d . . P A 1
O1 O 0.23742(7) 0.67052(18) 0.85832(14) 0.0327(5) Uani 1 1 d . . . . .
N1 N 0.25681(9) 0.5730(2) 0.67993(16) 0.0312(6) Uani 1 1 d D . . . .
C1 C 0.19649(10) 0.5972(3) 0.8183(2) 0.0291(6) Uani 1 1 d . . . . .
O2 O 0.19134(7) 0.51135(18) 0.75415(14) 0.0336(5) Uani 1 1 d . . . . .
C2 C 0.14983(10) 0.6062(2) 0.84369(19) 0.0271(6) Uani 1 1 d . . . . .
O3 O 0.08999(8) 0.46395(18) 0.71057(14) 0.0334(5) Uani 1 1 d . . . . .
C3 C 0.09761(10) 0.5398(2) 0.78765(19) 0.0272(6) Uani 1 1 d . . . . .
O4 O 0.4166(3) 0.4645(7) 0.2498(4) 0.0895(19) Uani 0.5 1 d . . P . .
C4 C 0.05414(10) 0.5515(2) 0.81034(19) 0.0262(6) Uani 1 1 d . . . . .
C5 C 0.06362(10) 0.6237(3) 0.8948(2) 0.0285(6) Uani 1 1 d . . . . .
C6 C 0.02348(11) 0.6322(3) 0.9284(2) 0.0323(7) Uani 1 1 d . . . . .
H6 H -0.0119 0.5913 0.8915 0.039 Uiso 1 1 calc R U . . .
C7 C 0.03486(12) 0.6984(3) 1.0131(2) 0.0396(7) Uani 1 1 d . . . . .
H7 H 0.0072 0.7026 1.0336 0.048 Uiso 1 1 calc R U . . .
C8 C 0.08699(12) 0.7604(3) 1.0702(2) 0.0395(7) Uani 1 1 d . . . . .
H8 H 0.0943 0.8064 1.1285 0.047 Uiso 1 1 calc R U . . .
C9 C 0.12673(11) 0.7533(3) 1.0405(2) 0.0358(7) Uani 1 1 d . . . . .
H9 H 0.1620 0.7939 1.0794 0.043 Uiso 1 1 calc R U . . .
C10 C 0.11659(10) 0.6874(3) 0.9536(2) 0.0291(6) Uani 1 1 d . . . . .
C11 C 0.15781(10) 0.6771(3) 0.92394(19) 0.0284(6) Uani 1 1 d . . . . .
H11 H 0.1924 0.7210 0.9611 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0000 0.4755(3) 0.7500 0.0278(8) Uani 1 2 d S T P . .
H12B H 0.0055 0.4190 0.7037 0.033 Uiso 0.5 1 calc R U P . .
H12A H -0.0055 0.4190 0.7963 0.033 Uiso 0.5 1 calc R U P . .
C13 C 0.26359(13) 0.4850(3) 0.6240(2) 0.0433(8) Uani 1 1 d . . . . .
H13 H 0.2501 0.4001 0.6217 0.052 Uiso 1 1 calc R U . . .
C14 C 0.28962(13) 0.5144(3) 0.5698(2) 0.0401(7) Uani 1 1 d . . . . .
H14 H 0.2934 0.4502 0.5296 0.048 Uiso 1 1 calc R U . . .
C15 C 0.31071(10) 0.6381(2) 0.57303(19) 0.0264(6) Uani 1 1 d . . . . .
C16 C 0.33738(10) 0.6728(2) 0.51290(19) 0.0270(6) Uani 1 1 d . . . . .
C17 C 0.33386(12) 0.5920(3) 0.4378(2) 0.0396(7) Uani 1 1 d . . . . .
H17 H 0.3140 0.5130 0.4256 0.048 Uiso 1 1 calc R U . . .
C18 C 0.35849(13) 0.6240(3) 0.3810(2) 0.0413(8) Uani 1 1 d . . . . .
H18 H 0.3559 0.5667 0.3310 0.050 Uiso 1 1 calc R U . . .
C19 C 0.38686(11) 0.7388(3) 0.3965(2) 0.0337(7) Uani 1 1 d . . . . .
H19 H 0.4042 0.7606 0.3579 0.040 Uiso 1 1 calc R U . . .
C20 C 0.38980(12) 0.8213(3) 0.4683(2) 0.0397(7) Uani 1 1 d . . . . .
H20 H 0.4084 0.9016 0.4780 0.048 Uiso 1 1 calc R U . . .
C21 C 0.36601(11) 0.7888(3) 0.5266(2) 0.0362(7) Uani 1 1 d . . . . .
H21 H 0.3692 0.8464 0.5769 0.043 Uiso 1 1 calc R U . . .
C22 C 0.30344(11) 0.7259(3) 0.6335(2) 0.0331(7) Uani 1 1 d . . . . .
H22 H 0.3173 0.8110 0.6389 0.040 Uiso 1 1 calc R U . . .
C23 C 0.27642(11) 0.6915(3) 0.6858(2) 0.0341(7) Uani 1 1 d . . . . .
H23 H 0.2717 0.7533 0.7266 0.041 Uiso 1 1 calc R U . . .
C24 C 0.5222(7) 0.5106(14) 0.3687(11) 0.107(7) Uani 0.5 1 d . . P . .
H3O H 0.131(2) 0.470(5) 0.715(4) 0.123(17) Uiso 1 1 d . . . . .
C25 C 0.4818(7) 0.516(2) 0.1733(12) 0.138(9) Uani 0.5 1 d . . P . .
S2 S 0.4794(5) 0.4199(11) 0.2644(9) 0.077(3) Uani 0.1 1 d . . P A -1
H1N H 0.2319(14) 0.550(4) 0.712(3) 0.088(13) Uiso 1 1 d 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 O4 1.466(6) . ?
S1 C25 1.503(19) 2_655 ?
S1 S2 1.570(12) . ?
S1 C24 1.781(14) . ?
S1 C25 1.84(2) . ?
S1 S1 2.475(5) 2_655 ?
O1 C1 1.241(3) . ?
N1 C23 1.329(4) . ?
N1 C13 1.330(4) . ?
N1 H1N 1.040(19) . ?
C1 O2 1.289(3) . ?
C1 C2 1.505(4) . ?
C2 C11 1.364(4) . ?
C2 C3 1.435(4) . ?
O3 C3 1.356(3) . ?
O3 H3O 1.08(5) . ?
C3 C4 1.395(4) . ?
O4 S2 1.683(14) . ?
C4 C5 1.414(4) . ?
C4 C12 1.529(3) . ?
C5 C6 1.424(4) . ?
C5 C10 1.442(4) . ?
C6 C7 1.371(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.414(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.408(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.409(4) . ?
C11 H11 0.9500 . ?
C12 C4 1.529(3) 2_556 ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.400(4) . ?
C14 H14 0.9500 . ?
C15 C22 1.386(4) . ?
C15 C16 1.475(4) . ?
C16 C21 1.396(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 0.60(3) 2_655 ?
C24 S2 1.736(17) . ?
C25 C24 0.60(3) 2_655 ?
C25 S1 1.503(18) 2_655 ?
C25 S2 1.753(19) . ?

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
O4 S1 C25 114.0(10) . 2_655 ?
O4 S1 S2 67.2(5) . . ?
C25 S1 S2 55.7(10) 2_655 . ?
O4 S1 C24 106.1(7) . . ?
C25 S1 C24 18.9(10) 2_655 . ?
S2 S1 C24 62.1(6) . . ?
O4 S1 C25 104.4(8) . . ?
C25 S1 C25 75.9(8) 2_655 . ?
S2 S1 C25 61.2(8) . . ?
C24 S1 C25 94.5(9) . . ?
O4 S1 S1 133.6(3) . 2_655 ?
C25 S1 S1 47.9(8) 2_655 2_655 ?
S2 S1 S1 69.6(4) . 2_655 ?
C24 S1 S1 66.1(7) . 2_655 ?
C25 S1 S1 37.2(6) . 2_655 ?
C23 N1 C13 120.3(3) . . ?
C23 N1 H1N 121(2) . . ?
C13 N1 H1N 119(2) . . ?
O1 C1 O2 123.0(2) . . ?
O1 C1 C2 120.2(2) . . ?
O2 C1 C2 116.9(2) . . ?
C11 C2 C3 118.8(2) . . ?
C11 C2 C1 119.1(2) . . ?
C3 C2 C1 122.1(2) . . ?
C3 O3 H3O 101(3) . . ?
O3 C3 C4 118.9(2) . . ?
O3 C3 C2 119.6(2) . . ?
C4 C3 C2 121.5(2) . . ?
S1 O4 S2 59.3(5) . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 C12 119.3(2) . . ?
C5 C4 C12 121.7(2) . . ?
C4 C5 C6 122.7(2) . . ?
C4 C5 C10 120.2(2) . . ?
C6 C5 C10 117.0(2) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.6(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 C5 119.8(2) . . ?
C11 C10 C5 118.3(2) . . ?
C2 C11 C10 122.3(2) . . ?
C2 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C4 C12 C4 117.8(3) 2_556 . ?
C4 C12 H12B 107.9 2_556 . ?
C4 C12 H12B 107.9 . . ?
C4 C12 H12A 107.9 2_556 . ?
C4 C12 H12A 107.9 . . ?
H12B C12 H12A 107.2 . . ?
N1 C13 C14 121.3(3) . . ?
N1 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C22 C15 C14 116.0(3) . . ?
C22 C15 C16 122.5(2) . . ?
C14 C15 C16 121.5(2) . . ?
C21 C16 C17 117.0(3) . . ?
C21 C16 C15 121.8(2) . . ?
C17 C16 C15 121.2(2) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C23 C22 C15 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C15 C22 H22 119.5 . . ?
N1 C23 C22 120.8(3) . . ?
N1 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 S2 51(3) 2_655 . ?
C25 C24 S1 54(3) 2_655 . ?
S2 C24 S1 53.0(6) . . ?
C24 C25 S1 107(3) 2_655 2_655 ?
C24 C25 S2 138(4) 2_655 . ?
S1 C25 S2 96.0(9) 2_655 . ?
C24 C25 S1 152(4) 2_655 . ?
S1 C25 S1 94.9(11) 2_655 . ?
S2 C25 S1 51.7(6) . . ?
S1 S2 O4 53.4(5) . . ?
S1 S2 C24 64.9(6) . . ?
O4 S2 C24 99.1(9) . . ?
S1 S2 C25 67.1(9) . . ?
O4 S2 C25 99.6(9) . . ?
C24 S2 C25 99.4(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -12.7(4) . . . . ?
O2 C1 C2 C11 167.5(2) . . . . ?
O1 C1 C2 C3 169.0(2) . . . . ?
O2 C1 C2 C3 -10.8(3) . . . . ?
C11 C2 C3 O3 -176.8(2) . . . . ?
C1 C2 C3 O3 1.5(4) . . . . ?
C11 C2 C3 C4 3.3(4) . . . . ?
C1 C2 C3 C4 -178.4(2) . . . . ?
C25 S1 O4 S2 -31.1(8) 2_655 . . . ?
C24 S1 O4 S2 -49.4(7) . . . . ?
C25 S1 O4 S2 49.7(8) . . . . ?
S1 S1 O4 S2 22.7(6) 2_655 . . . ?
O3 C3 C4 C5 175.8(2) . . . . ?
C2 C3 C4 C5 -4.3(4) . . . . ?
O3 C3 C4 C12 1.9(3) . . . . ?
C2 C3 C4 C12 -178.3(2) . . . . ?
C3 C4 C5 C6 -174.7(2) . . . . ?
C12 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 C10 2.2(4) . . . . ?
C12 C4 C5 C10 176.0(2) . . . . ?
C4 C5 C6 C7 177.1(3) . . . . ?
C10 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 -178.4(3) . . . . ?
C8 C9 C10 C5 -1.0(4) . . . . ?
C4 C5 C10 C9 -176.6(2) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
C4 C5 C10 C11 0.8(4) . . . . ?
C6 C5 C10 C11 177.9(2) . . . . ?
C3 C2 C11 C10 -0.1(4) . . . . ?
C1 C2 C11 C10 -178.4(2) . . . . ?
C9 C10 C11 C2 175.5(3) . . . . ?
C5 C10 C11 C2 -1.9(4) . . . . ?
C3 C4 C12 C4 -117.1(2) . . . 2_556 ?
C5 C4 C12 C4 69.2(2) . . . 2_556 ?
C23 N1 C13 C14 -1.4(4) . . . . ?
N1 C13 C14 C15 1.0(5) . . . . ?
C13 C14 C15 C22 0.0(4) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C22 C15 C16 C21 11.9(4) . . . . ?
C14 C15 C16 C21 -170.1(3) . . . . ?
C22 C15 C16 C17 -166.5(3) . . . . ?
C14 C15 C16 C17 11.5(4) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?
C15 C16 C17 C18 179.7(3) . . . . ?
C16 C17 C18 C19 -0.9(5) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 C21 1.8(4) . . . . ?
C19 C20 C21 C16 -1.4(5) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C15 C16 C21 C20 -178.6(3) . . . . ?
C14 C15 C22 C23 -0.6(4) . . . . ?
C16 C15 C22 C23 177.5(2) . . . . ?
C13 N1 C23 C22 0.7(4) . . . . ?
C15 C22 C23 N1 0.3(4) . . . . ?
O4 S1 C24 C25 118(4) . . . 2_655 ?
S2 S1 C24 C25 65(4) . . . 2_655 ?
C25 S1 C24 C25 11(4) . . . 2_655 ?
S1 S1 C24 C25 -14(4) 2_655 . . 2_655 ?
O4 S1 C24 S2 52.4(7) . . . . ?
C25 S1 C24 S2 -65(4) 2_655 . . . ?
C25 S1 C24 S2 -53.9(9) . . . . ?
S1 S1 C24 S2 -78.7(6) 2_655 . . . ?
O4 S1 C25 C24 69(8) . . . 2_655 ?
C25 S1 C25 C24 -179(8) 2_655 . . 2_655 ?
S2 S1 C25 C24 122(9) . . . 2_655 ?
C24 S1 C25 C24 177(9) . . . 2_655 ?
S1 S1 C25 C24 -144(9) 2_655 . . 2_655 ?
O4 S1 C25 S1 -147.1(8) . . . 2_655 ?
C25 S1 C25 S1 -35.5(17) 2_655 . . 2_655 ?
S2 S1 C25 S1 -93.8(10) . . . 2_655 ?
C24 S1 C25 S1 -39.2(8) . . . 2_655 ?
O4 S1 C25 S2 -53.3(7) . . . . ?
C25 S1 C25 S2 58.3(11) 2_655 . . . ?
C24 S1 C25 S2 54.6(8) . . . . ?
S1 S1 C25 S2 93.8(10) 2_655 . . . ?
C25 S1 S2 O4 145.2(10) 2_655 . . . ?
C24 S1 S2 O4 124.3(9) . . . . ?
C25 S1 S2 O4 -122.6(8) . . . . ?
S1 S1 S2 O4 -162.6(5) 2_655 . . . ?
O4 S1 S2 C24 -124.3(9) . . . . ?
C25 S1 S2 C24 20.9(14) 2_655 . . . ?
C25 S1 S2 C24 113.1(12) . . . . ?
S1 S1 S2 C24 73.0(8) 2_655 . . . ?
O4 S1 S2 C25 122.6(8) . . . . ?
C25 S1 S2 C25 -92.3(13) 2_655 . . . ?
C24 S1 S2 C25 -113.1(12) . . . . ?
S1 S1 S2 C25 -40.1(7) 2_655 . . . ?
S1 O4 S2 C24 49.3(7) . . . . ?
S1 O4 S2 C25 -51.9(9) . . . . ?
C25 C24 S2 S1 -70(3) 2_655 . . . ?
C25 C24 S2 O4 -112(4) 2_655 . . . ?
S1 C24 S2 O4 -42.2(6) . . . . ?
C25 C24 S2 C25 -11(4) 2_655 . . . ?
S1 C24 S2 C25 59.1(11) . . . . ?
C24 C25 S2 S1 -144(6) 2_655 . . . ?
S1 C25 S2 S1 91.5(12) 2_655 . . . ?
C24 C25 S2 O4 -100(6) 2_655 . . . ?
S1 C25 S2 O4 134.9(10) 2_655 . . . ?
S1 C25 S2 O4 43.3(5) . . . . ?
C24 C25 S2 C24 159(5) 2_655 . . . ?
S1 C25 S2 C24 33.9(14) 2_655 . . . ?
S1 C25 S2 C24 -57.6(9) . . . . ?

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
O3 H3O O2 1.08(5) 1.52(5) 2.556(3) 158(4) .
N1 H1N O2 1.040(19) 1.587(19) 2.626(3) 176(4) .

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_1Acetone
_database_code_depnum_ccdc_archive 'CCDC 1036227'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            '4-phenylpyridinium pamoate acetone solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 O6, 2(C11 H10 N), C3 H6 O'
_chemical_formula_sum            'C48 H40 N2 O7'
_chemical_formula_weight         756.82

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'

_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                   27.121(6)
_cell_length_b                   10.418(2)
_cell_length_c                   15.424(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.915(3)
_cell_angle_gamma                90
_cell_volume                     3814.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    877
_cell_measurement_theta_min      2.654
_cell_measurement_theta_max      19.693

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1592
_exptl_transmission_factor_min   0.8605
_exptl_transmission_factor_max   0.9563
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10909
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3884
_reflns_number_gt                2090
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_computing_publication_material  
'X-seed (Barbour, 2003; Atwood & Barbour, 2001)'
_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)+(0.0516P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
O1 O 0.23822(7) 0.66963(17) 0.85943(13) 0.0327(6) Uani 1 1 d . . . . .
N1 N 0.25785(9) 0.5706(2) 0.68097(16) 0.0306(7) Uani 1 1 d . . . . .
C1 C 0.19742(11) 0.5951(3) 0.81980(19) 0.0288(8) Uani 1 1 d . . . . .
O2 O 0.19290(7) 0.50843(17) 0.75652(13) 0.0324(6) Uani 1 1 d . . . . .
C2 C 0.15057(10) 0.6032(2) 0.84526(18) 0.0252(7) Uani 1 1 d . . . . .
O3 O 0.09071(7) 0.46153(17) 0.71144(13) 0.0325(6) Uani 1 1 d . . . . .
C3 C 0.09790(10) 0.5378(2) 0.78829(18) 0.0269(7) Uani 1 1 d . . . . .
O4 O 0.4208(2) 0.4920(7) 0.2452(4) 0.107(2) Uani 0.5 1 d . . P A -1
C4 C 0.05403(10) 0.5486(2) 0.81008(19) 0.0265(7) Uani 1 1 d . . . . .
C5 C 0.06340(10) 0.6213(2) 0.89514(18) 0.0279(8) Uani 1 1 d . . . . .
C6 C 0.02288(11) 0.6296(3) 0.92857(19) 0.0304(8) Uani 1 1 d . . . . .
H6 H -0.0125 0.5882 0.8919 0.036 Uiso 1 1 calc R U . . .
C7 C 0.03395(11) 0.6960(3) 1.0124(2) 0.0356(8) Uani 1 1 d . . . . .
H7 H 0.0060 0.7008 1.0326 0.043 Uiso 1 1 calc R U . . .
C8 C 0.08610(11) 0.7575(3) 1.06932(19) 0.0354(8) Uani 1 1 d . . . . .
H8 H 0.0932 0.8035 1.1274 0.042 Uiso 1 1 calc R U . . .
C9 C 0.12637(11) 0.7509(3) 1.04093(19) 0.0334(8) Uani 1 1 d . . . . .
H9 H 0.1616 0.7921 1.0798 0.040 Uiso 1 1 calc R U . . .
C10 C 0.11646(10) 0.6837(2) 0.95441(18) 0.0270(8) Uani 1 1 d . . . . .
C11 C 0.15821(10) 0.6736(2) 0.92511(18) 0.0282(7) Uani 1 1 d . . . . .
H11 H 0.1929 0.7176 0.9625 0.034 Uiso 1 1 calc R U . . .
C12 C 0.0000 0.4734(3) 0.7500 0.0298(10) Uani 1 2 d S T P . .
H12A H -0.0056 0.4170 0.7961 0.036 Uiso 0.5 1 calc R U P . .
H12B H 0.0056 0.4170 0.7039 0.036 Uiso 0.5 1 calc R U P . .
C13 C 0.26660(12) 0.4819(3) 0.6274(2) 0.0391(9) Uani 1 1 d . . . . .
H13 H 0.2543 0.3963 0.6266 0.047 Uiso 1 1 calc R U . . .
C14 C 0.29303(11) 0.5125(3) 0.5736(2) 0.0367(8) Uani 1 1 d . . . . .
H14 H 0.2989 0.4477 0.5362 0.044 Uiso 1 1 calc R U . . .
C15 C 0.31142(10) 0.6373(2) 0.57301(18) 0.0270(7) Uani 1 1 d . . . . .
C16 C 0.33798(10) 0.6728(2) 0.51200(18) 0.0275(7) Uani 1 1 d . . . . .
C17 C 0.33593(12) 0.5900(3) 0.4394(2) 0.0387(8) Uani 1 1 d . . . . .
H17 H 0.3174 0.5096 0.4292 0.046 Uiso 1 1 calc R U . . .
C18 C 0.36032(12) 0.6226(3) 0.3816(2) 0.0400(9) Uani 1 1 d . . . . .
H18 H 0.3592 0.5639 0.3336 0.048 Uiso 1 1 calc R U . . .
C19 C 0.38625(10) 0.7403(3) 0.3938(2) 0.0345(8) Uani 1 1 d . . . . .
H19 H 0.4030 0.7631 0.3542 0.041 Uiso 1 1 calc R U . . .
C20 C 0.38763(11) 0.8245(3) 0.4639(2) 0.0382(8) Uani 1 1 d . . . . .
H20 H 0.4048 0.9062 0.4718 0.046 Uiso 1 1 calc R U . . .
C21 C 0.36440(11) 0.7913(3) 0.5226(2) 0.0352(8) Uani 1 1 d . . . . .
H21 H 0.3663 0.8500 0.5713 0.042 Uiso 1 1 calc R U . . .
C22 C 0.30233(11) 0.7256(3) 0.63143(19) 0.0331(8) Uani 1 1 d . . . . .
H22 H 0.3150 0.8115 0.6351 0.040 Uiso 1 1 calc R U . . .
C23 C 0.27555(11) 0.6911(3) 0.6837(2) 0.0339(8) Uani 1 1 d . . . . .
H23 H 0.2694 0.7536 0.7224 0.041 Uiso 1 1 calc R U . . .
C24 C 0.4882(7) 0.5327(18) 0.1899(8) 0.164(8) Uani 0.5 1 d . . P A -1
H24A H 0.4563 0.5587 0.1265 0.245 Uiso 0.5 1 calc R U P A -1
H24B H 0.5064 0.4570 0.1799 0.245 Uiso 0.5 1 calc R U P A -1
H24C H 0.5155 0.6032 0.2164 0.245 Uiso 0.5 1 calc R U P A -1
C25 C 0.4676(3) 0.5010(9) 0.2617(6) 0.067(2) Uani 0.5 1 d . . P A -1
C26 C 0.5152(5) 0.4964(11) 0.3661(6) 0.088(4) Uani 0.5 1 d . . P A -1
H26A H 0.5000 0.4949 0.4121 0.132 Uiso 0.5 1 calc R U P A -1
H26C H 0.5390 0.5725 0.3790 0.132 Uiso 0.5 1 calc R U P A -1
H26B H 0.5377 0.4190 0.3752 0.132 Uiso 0.5 1 calc R U P A -1
H3O H 0.1238(12) 0.467(3) 0.7091(19) 0.047(9) Uiso 1 1 d . . . . .
H1N H 0.2341(13) 0.541(3) 0.721(2) 0.068(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
O1 C1 1.244(3) . ?
N1 C13 1.335(3) . ?
N1 C23 1.338(3) . ?
N1 H1N 1.13(3) . ?
C1 O2 1.291(3) . ?
C1 C2 1.503(3) . ?
C2 C11 1.361(3) . ?
C2 C3 1.436(3) . ?
O3 C3 1.361(3) . ?
O3 H3O 0.92(3) . ?
C3 C4 1.388(3) . ?
O4 C25 1.173(8) . ?
C4 C5 1.427(3) . ?
C4 C12 1.519(3) . ?
C5 C6 1.424(3) . ?
C5 C10 1.434(3) . ?
C6 C7 1.365(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.361(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.412(3) . ?
C11 H11 0.9500 . ?
C12 C4 1.519(3) 2_556 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.371(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C22 1.390(3) . ?
C15 C16 1.482(3) . ?
C16 C17 1.393(4) . ?
C16 C21 1.397(3) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.368(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.498(13) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.500(11) . ?
C26 H26A 0.9800 . ?
C26 H26C 0.9800 . ?
C26 H26B 0.9800 . ?

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
C13 N1 C23 120.1(2) . . ?
C13 N1 H1N 117.8(15) . . ?
C23 N1 H1N 122.1(15) . . ?
O1 C1 O2 123.0(2) . . ?
O1 C1 C2 120.0(2) . . ?
O2 C1 C2 117.0(2) . . ?
C11 C2 C3 118.7(2) . . ?
C11 C2 C1 119.3(2) . . ?
C3 C2 C1 122.0(2) . . ?
C3 O3 H3O 105.6(17) . . ?
O3 C3 C4 118.7(2) . . ?
O3 C3 C2 119.4(2) . . ?
C4 C3 C2 121.9(2) . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C12 119.8(2) . . ?
C5 C4 C12 121.7(2) . . ?
C6 C5 C4 122.6(2) . . ?
C6 C5 C10 117.0(2) . . ?
C4 C5 C10 120.3(2) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 C5 118.4(2) . . ?
C9 C10 C5 120.0(2) . . ?
C2 C11 C10 122.4(2) . . ?
C2 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C4 C12 C4 117.9(3) . 2_556 ?
C4 C12 H12A 107.8 . . ?
C4 C12 H12A 107.8 2_556 . ?
C4 C12 H12B 107.8 . . ?
C4 C12 H12B 107.8 2_556 . ?
H12A C12 H12B 107.2 . . ?
N1 C13 C14 121.0(3) . . ?
N1 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C22 C15 C14 115.9(2) . . ?
C22 C15 C16 122.7(2) . . ?
C14 C15 C16 121.4(2) . . ?
C17 C16 C21 117.3(3) . . ?
C17 C16 C15 120.9(2) . . ?
C21 C16 C15 121.7(2) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
C23 C22 C15 121.3(3) . . ?
C23 C22 H22 119.4 . . ?
C15 C22 H22 119.4 . . ?
N1 C23 C22 120.8(3) . . ?
N1 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 C24 127.5(10) . . ?
O4 C25 C26 120.7(8) . . ?
C24 C25 C26 111.5(11) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26C C26 H26B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -13.0(3) . . . . ?
O2 C1 C2 C11 166.8(2) . . . . ?
O1 C1 C2 C3 167.5(2) . . . . ?
O2 C1 C2 C3 -12.7(3) . . . . ?
C11 C2 C3 O3 -176.5(2) . . . . ?
C1 C2 C3 O3 3.0(4) . . . . ?
C11 C2 C3 C4 2.5(4) . . . . ?
C1 C2 C3 C4 -178.0(2) . . . . ?
O3 C3 C4 C5 175.5(2) . . . . ?
C2 C3 C4 C5 -3.6(4) . . . . ?
O3 C3 C4 C12 1.5(3) . . . . ?
C2 C3 C4 C12 -177.6(2) . . . . ?
C3 C4 C5 C6 -174.7(2) . . . . ?
C12 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C10 1.5(4) . . . . ?
C12 C4 C5 C10 175.5(2) . . . . ?
C4 C5 C6 C7 177.5(2) . . . . ?
C10 C5 C6 C7 1.1(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -178.6(3) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?
C6 C5 C10 C11 177.9(2) . . . . ?
C4 C5 C10 C11 1.4(4) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C4 C5 C10 C9 -177.3(2) . . . . ?
C3 C2 C11 C10 0.7(4) . . . . ?
C1 C2 C11 C10 -178.9(2) . . . . ?
C9 C10 C11 C2 176.2(2) . . . . ?
C5 C10 C11 C2 -2.6(4) . . . . ?
C3 C4 C12 C4 -117.0(2) . . . 2_556 ?
C5 C4 C12 C4 69.1(2) . . . 2_556 ?
C23 N1 C13 C14 -0.8(4) . . . . ?
N1 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C22 1.4(4) . . . . ?
C13 C14 C15 C16 -177.5(2) . . . . ?
C22 C15 C16 C17 -166.5(3) . . . . ?
C14 C15 C16 C17 12.3(4) . . . . ?
C22 C15 C16 C21 11.4(4) . . . . ?
C14 C15 C16 C21 -169.7(2) . . . . ?
C21 C16 C17 C18 1.6(4) . . . . ?
C15 C16 C17 C18 179.6(2) . . . . ?
C16 C17 C18 C19 -1.5(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 1.1(4) . . . . ?
C19 C20 C21 C16 -1.1(4) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C15 C16 C21 C20 -178.3(2) . . . . ?
C14 C15 C22 C23 -1.7(4) . . . . ?
C16 C15 C22 C23 177.2(2) . . . . ?
C13 N1 C23 C22 0.5(4) . . . . ?
C15 C22 C23 N1 0.8(4) . . . . ?

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
O3 H3O O2 0.92(3) 1.70(3) 2.557(2) 153(2) .
N1 H1N O1 1.13(3) 2.48(3) 3.216(3) 121.5(19) .

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_1DMF
_database_code_depnum_ccdc_archive 'CCDC 1036228'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '4-phenylpyridinium pamoate DMF solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'C23 H14 O6, 2(C11 H10 N), 0.881(C N), 0.882(C H O), 0.118(O),0'
_chemical_formula_sum            'C47.65 H40.17 N2.88 O7'
_chemical_formula_weight         765.07

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        C2/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_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.355(7)
_cell_length_b                   10.464(3)
_cell_length_c                   15.401(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.512(3)
_cell_angle_gamma                90.00
_cell_volume                     3836.5(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    2578
_cell_measurement_theta_min      2.356
_cell_measurement_theta_max      26.315

_exptl_crystal_description       shard
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.93
_exptl_crystal_size_mid          0.84
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1611
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_process_details   'symmetry-related measurements'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9837
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         26.44
_reflns_number_total             3918
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

Numerous attempts were made to model the disordered DMF in this structure, 
but the model did not converge, despite repeated cycles of refinement. 
It is clear from the NMR results that there is DMF in the channels 
of this material.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0558P)²+10.0257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3918
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.381
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23699(8) 0.67328(19) 0.86049(15) 0.0308(5) Uani 1 1 d . . .
N1 N 0.25662(9) 0.5739(2) 0.68273(17) 0.0281(5) Uani 1 1 d . . .
C1 C 0.19627(11) 0.5997(3) 0.8198(2) 0.0261(6) Uani 1 1 d . . .
O2 O 0.19120(8) 0.51292(19) 0.75657(14) 0.0298(5) Uani 1 1 d . . .
N2 N 0.5000 0.5123(4) 0.2500 0.0521(13) Uani 0.881(6) 2 d SP . .
C2 C 0.14947(10) 0.6078(3) 0.8452(2) 0.0247(6) Uani 1 1 d . . .
O3 O 0.08999(8) 0.46405(19) 0.71178(14) 0.0297(5) Uani 1 1 d . . .
C3 C 0.09751(10) 0.5413(3) 0.78874(19) 0.0241(6) Uani 1 1 d . . .
O4 O 0.4129(2) 0.5106(6) 0.2551(4) 0.0566(17) Uani 0.441(3) 1 d P A -1
C5 C 0.06326(11) 0.6246(3) 0.8957(2) 0.0248(6) Uani 1 1 d . . .
C6 C 0.02314(11) 0.6326(3) 0.9292(2) 0.0287(6) Uani 1 1 d . . .
H6 H -0.0120 0.5906 0.8926 0.034 Uiso 1 1 calc R . .
C7 C 0.03463(12) 0.7000(3) 1.0133(2) 0.0362(7) Uani 1 1 d . . .
H7 H 0.0071 0.7041 1.0339 0.043 Uiso 1 1 calc R . .
C8 C 0.08641(13) 0.7634(3) 1.0703(2) 0.0420(8) Uani 1 1 d . . .
H8 H 0.0936 0.8100 1.1284 0.050 Uiso 1 1 calc R . .
C9 C 0.12599(12) 0.7571(3) 1.0412(2) 0.0364(7) Uani 1 1 d . . .
H9 H 0.1610 0.7992 1.0797 0.044 Uiso 1 1 calc R . .
C10 C 0.11585(11) 0.6887(3) 0.9544(2) 0.0282(6) Uani 1 1 d . . .
C11 C 0.15738(11) 0.6800(3) 0.9254(2) 0.0269(6) Uani 1 1 d . . .
H11 H 0.1917 0.7253 0.9624 0.032 Uiso 1 1 calc R . .
C12 C 0.0000 0.4756(4) 0.7500 0.0262(8) Uani 1 2 d S . .
H12A H 0.0053 0.4195 0.7035 0.031 Uiso 0.50 1 calc PR . .
H12B H -0.0053 0.4195 0.7965 0.031 Uiso 0.50 1 calc PR . .
H1N H 0.2321(13) 0.551(3) 0.716(2) 0.045(9) Uiso 1 1 d . . .
H3O H 0.1243(16) 0.461(4) 0.710(3) 0.056(11) Uiso 1 1 d . . .
C13 C 0.26327(14) 0.4863(3) 0.6258(2) 0.0410(8) Uani 1 1 d . . .
H13 H 0.2496 0.4020 0.6225 0.049 Uiso 1 1 calc R . .
C14 C 0.28965(13) 0.5165(3) 0.5720(2) 0.0378(7) Uani 1 1 d . . .
H14 H 0.2936 0.4535 0.5315 0.045 Uiso 1 1 calc R . .
C15 C 0.31047(11) 0.6389(3) 0.5767(2) 0.0262(6) Uani 1 1 d . . .
C16 C 0.33752(11) 0.6741(3) 0.5164(2) 0.0286(6) Uani 1 1 d . . .
C17 C 0.33483(19) 0.5921(4) 0.4426(3) 0.0663(13) Uani 1 1 d . . .
H17 H 0.3158 0.5127 0.4312 0.080 Uiso 1 1 calc R . .
C18 C 0.35942(19) 0.6246(4) 0.3854(3) 0.0659(13) Uani 1 1 d . . .
H18 H 0.3575 0.5674 0.3360 0.079 Uiso 1 1 calc R . .
C19 C 0.38662(12) 0.7402(3) 0.4006(2) 0.0347(7) Uani 1 1 d . . .
H19 H 0.4050 0.7611 0.3639 0.042 Uiso 1 1 calc R . .
C20 C 0.38704(12) 0.8247(3) 0.4689(2) 0.0341(7) Uani 1 1 d . . .
H20 H 0.4040 0.9062 0.4768 0.041 Uiso 1 1 calc R . .
C21 C 0.36280(12) 0.7920(3) 0.5264(2) 0.0312(6) Uani 1 1 d . . .
H21 H 0.3635 0.8515 0.5736 0.037 Uiso 1 1 calc R . .
C22 C 0.30243(13) 0.7266(3) 0.6362(2) 0.0378(7) Uani 1 1 d . . .
H22 H 0.3157 0.8116 0.6412 0.045 Uiso 1 1 calc R . .
C23 C 0.27553(13) 0.6921(3) 0.6880(2) 0.0346(7) Uani 1 1 d . . .
H23 H 0.2704 0.7537 0.7282 0.042 Uiso 1 1 calc R . .
C24 C 0.5369(10) 0.5670(18) 0.2346(19) 0.079(8) Uani 0.441(3) 1 d P A -1
H24A H 0.5292 0.5480 0.1667 0.118 Uiso 0.441(3) 1 calc PR A -1
H24B H 0.5743 0.5353 0.2827 0.118 Uiso 0.441(3) 1 calc PR A -1
H24C H 0.5353 0.6596 0.2425 0.118 Uiso 0.441(3) 1 calc PR A -1
C4 C 0.05414(10) 0.5518(3) 0.8108(2) 0.0237(6) Uani 1 1 d . . .
C25 C 0.4521(9) 0.560(2) 0.245(2) 0.081(8) Uani 0.441(3) 1 d P A -1
H25 H 0.4471 0.6488 0.2304 0.097 Uiso 0.441(3) 1 calc PR A -1
C26 C 0.5000 0.3723(8) 0.2500 0.144(5) Uani 0.881(6) 2 d SP A .
H26A H 0.5105 0.3411 0.3170 0.216 Uiso 0.441(3) 1 calc PR . .
H26B H 0.5271 0.3411 0.2307 0.216 Uiso 0.441(3) 1 calc PR . .
H26C H 0.4624 0.3411 0.2023 0.216 Uiso 0.441(3) 1 calc PR . .
O5 O 0.5220(10) 0.488(2) 0.3753(18) 0.013(6) Uiso 0.059(3) 1 d P A 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
O1 C1 1.240(3) . ?
N1 C23 1.328(4) . ?
N1 C13 1.341(4) . ?
N1 H1N 1.05(3) . ?
C1 O2 1.288(3) . ?
C1 C2 1.514(3) . ?
N2 C24 1.28(2) . ?
N2 C24 1.28(2) 2_655 ?
N2 C25 1.367(19) . ?
N2 C25 1.367(19) 2_655 ?
N2 C26 1.464(10) . ?
N2 O5 1.73(2) 2_655 ?
N2 O5 1.73(2) . ?
C2 C11 1.371(4) . ?
C2 C3 1.430(4) . ?
O3 C3 1.364(3) . ?
O3 H3O 0.95(4) . ?
C3 C4 1.390(3) . ?
O4 C25 1.27(3) . ?
C5 C4 1.425(4) . ?
C5 C6 1.427(4) . ?
C5 C10 1.434(4) . ?
C6 C7 1.369(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.412(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.363(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.414(4) . ?
C11 H11 0.9500 . ?
C12 C4 1.529(3) 2_556 ?
C12 C4 1.530(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C22 1.389(4) . ?
C15 C16 1.491(4) . ?
C16 C21 1.385(4) . ?
C16 C17 1.397(4) . ?
C17 C18 1.388(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9863 . ?
C26 H26B 0.9863 . ?
C26 H26C 0.9863 . ?

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
C23 N1 C13 120.2(2) . . ?
C23 N1 H1N 120.1(18) . . ?
C13 N1 H1N 119.3(19) . . ?
O1 C1 O2 123.7(2) . . ?
O1 C1 C2 119.9(3) . . ?
O2 C1 C2 116.4(2) . . ?
C24 N2 C24 127(2) . 2_655 ?
C24 N2 C25 130.3(8) . . ?
C24 N2 C25 13(2) 2_655 . ?
C24 N2 C25 13(2) . 2_655 ?
C24 N2 C25 130.3(8) 2_655 2_655 ?
C25 N2 C25 137(2) . 2_655 ?
C24 N2 C26 116.6(10) . . ?
C24 N2 C26 116.6(10) 2_655 . ?
C25 N2 C26 111.4(11) . . ?
C25 N2 C26 111.4(11) 2_655 . ?
C24 N2 O5 74.4(14) . 2_655 ?
C24 N2 O5 113.5(14) 2_655 2_655 ?
C25 N2 O5 101.0(14) . 2_655 ?
C25 N2 O5 85.1(14) 2_655 2_655 ?
C26 N2 O5 81.6(9) . 2_655 ?
C24 N2 O5 113.5(14) . . ?
C24 N2 O5 74.4(14) 2_655 . ?
C25 N2 O5 85.1(14) . . ?
C25 N2 O5 101.0(14) 2_655 . ?
C26 N2 O5 81.6(9) . . ?
O5 N2 O5 163.2(17) 2_655 . ?
C11 C2 C3 119.0(2) . . ?
C11 C2 C1 119.0(2) . . ?
C3 C2 C1 122.0(2) . . ?
C3 O3 H3O 108(2) . . ?
O3 C3 C4 118.5(2) . . ?
O3 C3 C2 119.7(2) . . ?
C4 C3 C2 121.7(2) . . ?
C4 C5 C6 123.0(2) . . ?
C4 C5 C10 119.8(2) . . ?
C6 C5 C10 117.1(2) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.1(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 C5 118.9(3) . . ?
C9 C10 C5 120.0(2) . . ?
C2 C11 C10 121.7(3) . . ?
C2 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C4 C12 C4 117.2(3) 2_556 . ?
C4 C12 H12A 108.0 2_556 . ?
C4 C12 H12A 108.0 . . ?
C4 C12 H12B 108.0 2_556 . ?
C4 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
N1 C13 C14 121.1(3) . . ?
N1 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C22 116.7(3) . . ?
C14 C15 C16 120.8(2) . . ?
C22 C15 C16 122.4(3) . . ?
C21 C16 C17 117.4(3) . . ?
C21 C16 C15 121.6(2) . . ?
C17 C16 C15 120.8(3) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.8(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 121.3(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C15 120.9(3) . . ?
C23 C22 H22 119.5 . . ?
C15 C22 H22 119.5 . . ?
N1 C23 C22 120.9(3) . . ?
N1 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 C12 119.7(2) . . ?
C5 C4 C12 121.3(2) . . ?
O4 C25 N2 133.6(17) . . ?
O4 C25 H25 113.2 . . ?
N2 C25 H25 113.2 . . ?
N2 C26 H26A 110.1 . . ?
N2 C26 H26B 110.1 . . ?
H26A C26 H26B 108.8 . . ?
N2 C26 H26C 110.1 . . ?
H26A C26 H26C 108.8 . . ?
H26B C26 H26C 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C11 -11.7(4) . . . . ?
O2 C1 C2 C11 167.3(2) . . . . ?
O1 C1 C2 C3 169.1(2) . . . . ?
O2 C1 C2 C3 -11.9(4) . . . . ?
C11 C2 C3 O3 -176.8(2) . . . . ?
C1 C2 C3 O3 2.4(4) . . . . ?
C11 C2 C3 C4 2.5(4) . . . . ?
C1 C2 C3 C4 -178.3(2) . . . . ?
C4 C5 C6 C7 177.5(3) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C8 C9 C10 C11 -178.7(3) . . . . ?
C8 C9 C10 C5 -0.1(5) . . . . ?
C4 C5 C10 C11 1.2(4) . . . . ?
C6 C5 C10 C11 178.2(3) . . . . ?
C4 C5 C10 C9 -177.5(3) . . . . ?
C6 C5 C10 C9 -0.5(4) . . . . ?
C3 C2 C11 C10 0.9(4) . . . . ?
C1 C2 C11 C10 -178.3(2) . . . . ?
C9 C10 C11 C2 176.0(3) . . . . ?
C5 C10 C11 C2 -2.7(4) . . . . ?
C23 N1 C13 C14 0.0(5) . . . . ?
N1 C13 C14 C15 0.7(5) . . . . ?
C13 C14 C15 C22 -0.9(5) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 C21 -174.4(3) . . . . ?
C22 C15 C16 C21 8.6(4) . . . . ?
C14 C15 C16 C17 10.1(5) . . . . ?
C22 C15 C16 C17 -166.9(4) . . . . ?
C21 C16 C17 C18 3.7(6) . . . . ?
C15 C16 C17 C18 179.4(4) . . . . ?
C16 C17 C18 C19 -0.7(7) . . . . ?
C17 C18 C19 C20 -2.9(6) . . . . ?
C18 C19 C20 C21 3.4(5) . . . . ?
C17 C16 C21 C20 -3.2(5) . . . . ?
C15 C16 C21 C20 -178.9(3) . . . . ?
C19 C20 C21 C16 -0.2(5) . . . . ?
C14 C15 C22 C23 0.5(5) . . . . ?
C16 C15 C22 C23 177.6(3) . . . . ?
C13 N1 C23 C22 -0.4(5) . . . . ?
C15 C22 C23 N1 0.1(5) . . . . ?
O3 C3 C4 C5 175.3(2) . . . . ?
C2 C3 C4 C5 -4.0(4) . . . . ?
O3 C3 C4 C12 1.0(4) . . . . ?
C2 C3 C4 C12 -178.3(2) . . . . ?
C6 C5 C4 C3 -174.7(3) . . . . ?
C10 C5 C4 C3 2.1(4) . . . . ?
C6 C5 C4 C12 -0.5(4) . . . . ?
C10 C5 C4 C12 176.3(2) . . . . ?
C4 C12 C4 C3 -117.1(2) 2_556 . . . ?
C4 C12 C4 C5 68.8(2) 2_556 . . . ?
C24 N2 C25 O4 176.7(14) . . . . ?
C24 N2 C25 O4 -103(9) 2_655 . . . ?
C25 N2 C25 O4 -167(3) 2_655 . . . ?
C26 N2 C25 O4 13(3) . . . . ?
O5 N2 C25 O4 98(3) 2_655 . . . ?
O5 N2 C25 O4 -66(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 1.05(3) 1.58(3) 2.628(3) 175(3) .
O3 H3O O2 0.95(4) 1.69(4) 2.554(3) 149(3) .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_S1
_database_code_depnum_ccdc_archive 'CCDC 1036229'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '4-phenylpyridinium pamoate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C11 H10 N'
_chemical_formula_sum            'C34 H25 N O6'
_chemical_formula_weight         543.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7618(7)
_cell_length_b                   17.3278(16)
_cell_length_c                   18.8269(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.8670(10)
_cell_angle_gamma                90
_cell_volume                     2494.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3254
_cell_measurement_theta_min      2.351
_cell_measurement_theta_max      27.962

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.9448
_exptl_transmission_factor_max   1.0000
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.177
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15561
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.608
_diffrn_reflns_theta_max         28.297
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5752
_reflns_number_gt                4117
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'

_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)+(0.0510P)²+0.1107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5752
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O -0.11050(13) 0.39610(6) 0.35067(6) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.13976(16) 0.08153(7) 0.02228(7) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.04845(19) 0.40385(8) 0.33491(8) 0.0189(3) Uani 1 1 d . . . . .
O2 O 0.12054(14) 0.46660(6) 0.33240(6) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.12996(19) 0.32994(8) 0.31900(8) 0.0174(3) Uani 1 1 d . . . . .
O3 O 0.38304(14) 0.39683(6) 0.29030(6) 0.0216(2) Uani 1 1 d . . . . .
C3 C 0.29609(19) 0.32913(8) 0.29608(8) 0.0175(3) Uani 1 1 d . . . . .
O4 O 0.68986(14) 0.04519(6) 0.00392(6) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.37222(18) 0.26081(8) 0.27892(8) 0.0172(3) Uani 1 1 d . . . . .
O5 O 0.75924(13) 0.02216(6) 0.12209(6) 0.0223(2) Uani 1 1 d . . . . .
C5 C 0.29102(19) 0.18960(8) 0.29320(8) 0.0170(3) Uani 1 1 d . . . . .
O6 O 0.71088(13) 0.12725(6) 0.21123(6) 0.0223(3) Uani 1 1 d . . . . .
C6 C 0.3721(2) 0.11664(8) 0.28849(8) 0.0208(3) Uani 1 1 d . . . . .
H6 H 0.4835 0.1141 0.2742 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2922(2) 0.05028(8) 0.30419(8) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.3515 0.0025 0.3028 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1229(2) 0.05107(8) 0.32258(8) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.0666 0.0041 0.3311 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0418(2) 0.11976(8) 0.32797(8) 0.0201(3) Uani 1 1 d . . . . .
H9 H -0.0716 0.1205 0.3405 0.024 Uiso 1 1 calc R U . . .
C10 C 0.12381(19) 0.19021(8) 0.31523(8) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.04575(19) 0.26142(8) 0.32556(8) 0.0175(3) Uani 1 1 d . . . . .
H11 H -0.0684 0.2622 0.3374 0.021 Uiso 1 1 calc R U . . .
C12 C 0.54179(18) 0.26136(8) 0.24808(8) 0.0187(3) Uani 1 1 d . . . . .
H12A H 0.6289 0.2290 0.2792 0.022 Uiso 1 1 calc R U . . .
H12B H 0.5877 0.3148 0.2503 0.022 Uiso 1 1 calc R U . . .
C13 C 0.68814(19) 0.06315(8) 0.06810(9) 0.0200(3) Uani 1 1 d . . . . .
C14 C 0.59991(18) 0.13705(8) 0.08379(8) 0.0176(3) Uani 1 1 d . . . . .
C15 C 0.61087(18) 0.16543(8) 0.15574(8) 0.0174(3) Uani 1 1 d . . . . .
C16 C 0.52498(18) 0.23244(8) 0.17056(8) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.43129(18) 0.27532(8) 0.11161(8) 0.0163(3) Uani 1 1 d . . . . .
C18 C 0.34663(18) 0.34661(8) 0.12068(8) 0.0185(3) Uani 1 1 d . . . . .
H18 H 0.3523 0.3672 0.1678 0.022 Uiso 1 1 calc R U . . .
C19 C 0.25750(19) 0.38596(8) 0.06312(8) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.2026 0.4334 0.0710 0.025 Uiso 1 1 calc R U . . .
C20 C 0.24520(19) 0.35768(9) -0.00773(8) 0.0221(3) Uani 1 1 d . . . . .
H20 H 0.1818 0.3854 -0.0473 0.027 Uiso 1 1 calc R U . . .
C21 C 0.32608(19) 0.28973(8) -0.01844(8) 0.0211(3) Uani 1 1 d . . . . .
H21 H 0.3185 0.2704 -0.0661 0.025 Uiso 1 1 calc R U . . .
C22 C 0.42088(18) 0.24755(8) 0.03974(8) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.50668(19) 0.17765(8) 0.02790(8) 0.0188(3) Uani 1 1 d . . . . .
H23 H 0.4991 0.1587 -0.0199 0.023 Uiso 1 1 calc R U . . .
C24 C 0.04928(19) 0.12194(8) -0.03256(9) 0.0235(3) Uani 1 1 d . . . . .
H24 H 0.0442 0.1042 -0.0806 0.028 Uiso 1 1 calc R U . . .
C25 C -0.03610(19) 0.18868(9) -0.02002(8) 0.0213(3) Uani 1 1 d . . . . .
H25 H -0.0999 0.2164 -0.0595 0.026 Uiso 1 1 calc R U . . .
C26 C -0.03051(18) 0.21654(8) 0.05024(8) 0.0168(3) Uani 1 1 d . . . . .
C27 C -0.11349(18) 0.29064(8) 0.06502(8) 0.0170(3) Uani 1 1 d . . . . .
C28 C -0.19167(19) 0.33872(9) 0.00915(9) 0.0229(3) Uani 1 1 d . . . . .
H28 H -0.1972 0.3225 -0.0394 0.028 Uiso 1 1 calc R U . . .
C29 C -0.2614(2) 0.40965(9) 0.02324(9) 0.0269(4) Uani 1 1 d . . . . .
H29 H -0.3145 0.4414 -0.0156 0.032 Uiso 1 1 calc R U . . .
H6O H 0.741(3) 0.0805(12) 0.1869(11) 0.055(6) Uiso 1 1 d . . . . .
H3O H 0.314(3) 0.4342(11) 0.3054(11) 0.051(6) Uiso 1 1 d . . . . .
H1N H 0.206(3) 0.0298(12) 0.0129(11) 0.061(6) Uiso 1 1 d . . . . .
H1O H -0.159(3) 0.4491(14) 0.3619(13) 0.085(8) Uiso 1 1 d . . . . .
C30 C -0.25399(19) 0.43428(8) 0.09338(9) 0.0241(4) Uani 1 1 d . . . . .
H30 H -0.2999 0.4833 0.1030 0.029 Uiso 1 1 calc R U . . .
C31 C -0.1795(2) 0.38740(9) 0.14952(9) 0.0238(3) Uani 1 1 d . . . . .
H31 H -0.1756 0.4039 0.1979 0.029 Uiso 1 1 calc R U . . .
C32 C -0.11021(19) 0.31609(9) 0.13574(8) 0.0209(3) Uani 1 1 d . . . . .
H32 H -0.0599 0.2842 0.1749 0.025 Uiso 1 1 calc R U . . .
C33 C 0.06371(19) 0.17188(8) 0.10563(8) 0.0204(3) Uani 1 1 d . . . . .
H33 H 0.0702 0.1877 0.1543 0.024 Uiso 1 1 calc R U . . .
C34 C 0.1470(2) 0.10533(8) 0.09049(9) 0.0226(3) Uani 1 1 d . . . . .
H34 H 0.2105 0.0759 0.1288 0.027 Uiso 1 1 calc R U . . .


_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
O1 C1 1.3242(17) . ?
O1 H1O 1.03(2) . ?
N1 C34 1.341(2) . ?
N1 C24 1.3421(19) . ?
N1 H1N 1.06(2) . ?
C1 O2 1.2275(17) . ?
C1 C2 1.482(2) . ?
C2 C11 1.371(2) . ?
C2 C3 1.428(2) . ?
O3 C3 1.3670(16) . ?
O3 H3O 0.91(2) . ?
C3 C4 1.386(2) . ?
O4 C13 1.2499(18) . ?
C4 C5 1.4318(19) . ?
C4 C12 1.5269(19) . ?
O5 C13 1.2846(18) . ?
C5 C6 1.4216(19) . ?
C5 C10 1.429(2) . ?
O6 C15 1.3615(17) . ?
O6 H6O 0.98(2) . ?
C6 C7 1.362(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.415(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.358(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.416(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4028(19) . ?
C11 H11 0.9500 . ?
C12 C16 1.527(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.505(2) . ?
C14 C23 1.366(2) . ?
C14 C15 1.430(2) . ?
C15 C16 1.3908(19) . ?
C16 C17 1.427(2) . ?
C17 C18 1.4231(19) . ?
C17 C22 1.425(2) . ?
C18 C19 1.364(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.409(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.365(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.414(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.4182(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(2) . ?
C25 H25 0.9500 . ?
C26 C33 1.400(2) . ?
C26 C27 1.484(2) . ?
C27 C28 1.396(2) . ?
C27 C32 1.399(2) . ?
C28 C29 1.387(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.376(2) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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 O1 H1O 110.0(13) . . ?
C34 N1 C24 120.46(13) . . ?
C34 N1 H1N 118.4(11) . . ?
C24 N1 H1N 121.1(11) . . ?
O2 C1 O1 123.14(13) . . ?
O2 C1 C2 123.00(13) . . ?
O1 C1 C2 113.84(12) . . ?
C11 C2 C3 119.20(13) . . ?
C11 C2 C1 120.24(13) . . ?
C3 C2 C1 120.56(13) . . ?
C3 O3 H3O 105.1(12) . . ?
O3 C3 C4 118.58(13) . . ?
O3 C3 C2 119.95(12) . . ?
C4 C3 C2 121.46(13) . . ?
C3 C4 C5 118.25(13) . . ?
C3 C4 C12 120.88(13) . . ?
C5 C4 C12 120.84(12) . . ?
C6 C5 C10 117.28(13) . . ?
C6 C5 C4 122.75(13) . . ?
C10 C5 C4 119.95(12) . . ?
C15 O6 H6O 101.1(12) . . ?
C7 C6 C5 120.96(14) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.39(14) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 119.22(14) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.03(14) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 121.17(13) . . ?
C11 C10 C5 118.83(13) . . ?
C9 C10 C5 119.98(13) . . ?
C2 C11 C10 121.69(14) . . ?
C2 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C4 C12 C16 115.04(12) . . ?
C4 C12 H12A 108.5 . . ?
C16 C12 H12A 108.5 . . ?
C4 C12 H12B 108.5 . . ?
C16 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
O4 C13 O5 123.58(13) . . ?
O4 C13 C14 118.82(14) . . ?
O5 C13 C14 117.60(13) . . ?
C23 C14 C15 119.37(13) . . ?
C23 C14 C13 119.07(13) . . ?
C15 C14 C13 121.56(13) . . ?
O6 C15 C16 118.80(13) . . ?
O6 C15 C14 119.56(13) . . ?
C16 C15 C14 121.63(13) . . ?
C15 C16 C17 118.47(13) . . ?
C15 C16 C12 120.01(13) . . ?
C17 C16 C12 121.41(12) . . ?
C18 C17 C22 117.05(13) . . ?
C18 C17 C16 122.88(13) . . ?
C22 C17 C16 120.07(13) . . ?
C19 C18 C17 121.35(14) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.41(14) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 118.78(14) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 121.52(14) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 121.05(14) . . ?
C21 C22 C17 119.88(13) . . ?
C23 C22 C17 119.07(13) . . ?
C14 C23 C22 121.33(14) . . ?
C14 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
N1 C24 C25 120.76(15) . . ?
N1 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C24 C25 C26 120.97(14) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C33 C26 C25 116.12(13) . . ?
C33 C26 C27 121.78(13) . . ?
C25 C26 C27 122.06(13) . . ?
C28 C27 C32 117.62(14) . . ?
C28 C27 C26 121.43(13) . . ?
C32 C27 C26 120.91(13) . . ?
C29 C28 C27 121.21(15) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 120.24(15) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 119.65(14) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.37(15) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.90(15) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
C34 C33 C26 120.88(15) . . ?
C34 C33 H33 119.6 . . ?
C26 C33 H33 119.6 . . ?
N1 C34 C33 120.81(15) . . ?
N1 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C11 177.36(14) . . . . ?
O1 C1 C2 C11 -3.9(2) . . . . ?
O2 C1 C2 C3 -3.2(2) . . . . ?
O1 C1 C2 C3 175.54(12) . . . . ?
C11 C2 C3 O3 -179.01(13) . . . . ?
C1 C2 C3 O3 1.5(2) . . . . ?
C11 C2 C3 C4 1.4(2) . . . . ?
C1 C2 C3 C4 -178.10(13) . . . . ?
O3 C3 C4 C5 172.69(13) . . . . ?
C2 C3 C4 C5 -7.7(2) . . . . ?
O3 C3 C4 C12 -5.2(2) . . . . ?
C2 C3 C4 C12 174.46(13) . . . . ?
C3 C4 C5 C6 -169.77(14) . . . . ?
C12 C4 C5 C6 8.1(2) . . . . ?
C3 C4 C5 C10 8.4(2) . . . . ?
C12 C4 C5 C10 -173.78(13) . . . . ?
C10 C5 C6 C7 0.2(2) . . . . ?
C4 C5 C6 C7 178.41(14) . . . . ?
C5 C6 C7 C8 2.9(2) . . . . ?
C6 C7 C8 C9 -3.1(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 C11 -175.57(14) . . . . ?
C8 C9 C10 C5 2.8(2) . . . . ?
C6 C5 C10 C11 175.40(13) . . . . ?
C4 C5 C10 C11 -2.8(2) . . . . ?
C6 C5 C10 C9 -3.0(2) . . . . ?
C4 C5 C10 C9 178.73(13) . . . . ?
C3 C2 C11 C10 4.5(2) . . . . ?
C1 C2 C11 C10 -176.01(13) . . . . ?
C9 C10 C11 C2 174.71(14) . . . . ?
C5 C10 C11 C2 -3.7(2) . . . . ?
C3 C4 C12 C16 -113.96(15) . . . . ?
C5 C4 C12 C16 68.23(17) . . . . ?
O4 C13 C14 C23 7.7(2) . . . . ?
O5 C13 C14 C23 -172.87(12) . . . . ?
O4 C13 C14 C15 -172.58(13) . . . . ?
O5 C13 C14 C15 6.8(2) . . . . ?
C23 C14 C15 O6 -176.70(12) . . . . ?
C13 C14 C15 O6 3.6(2) . . . . ?
C23 C14 C15 C16 1.7(2) . . . . ?
C13 C14 C15 C16 -177.98(12) . . . . ?
O6 C15 C16 C17 175.31(12) . . . . ?
C14 C15 C16 C17 -3.1(2) . . . . ?
O6 C15 C16 C12 -0.83(19) . . . . ?
C14 C15 C16 C12 -179.27(12) . . . . ?
C4 C12 C16 C15 -115.15(15) . . . . ?
C4 C12 C16 C17 68.83(17) . . . . ?
C15 C16 C17 C18 -176.70(13) . . . . ?
C12 C16 C17 C18 -0.6(2) . . . . ?
C15 C16 C17 C22 2.7(2) . . . . ?
C12 C16 C17 C22 178.76(12) . . . . ?
C22 C17 C18 C19 0.9(2) . . . . ?
C16 C17 C18 C19 -179.72(13) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C23 -179.00(14) . . . . ?
C20 C21 C22 C17 0.9(2) . . . . ?
C18 C17 C22 C21 -1.37(19) . . . . ?
C16 C17 C22 C21 179.22(12) . . . . ?
C18 C17 C22 C23 178.55(12) . . . . ?
C16 C17 C22 C23 -0.9(2) . . . . ?
C15 C14 C23 C22 0.2(2) . . . . ?
C13 C14 C23 C22 179.91(12) . . . . ?
C21 C22 C23 C14 179.33(13) . . . . ?
C17 C22 C23 C14 -0.6(2) . . . . ?
C34 N1 C24 C25 0.6(2) . . . . ?
N1 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 C33 -1.0(2) . . . . ?
C24 C25 C26 C27 176.64(13) . . . . ?
C33 C26 C27 C28 173.30(13) . . . . ?
C25 C26 C27 C28 -4.2(2) . . . . ?
C33 C26 C27 C32 -4.3(2) . . . . ?
C25 C26 C27 C32 178.20(13) . . . . ?
C32 C27 C28 C29 0.9(2) . . . . ?
C26 C27 C28 C29 -176.78(13) . . . . ?
C27 C28 C29 C30 0.3(2) . . . . ?
C28 C29 C30 C31 -1.1(2) . . . . ?
C29 C30 C31 C32 0.8(2) . . . . ?
C30 C31 C32 C27 0.4(2) . . . . ?
C28 C27 C32 C31 -1.2(2) . . . . ?
C26 C27 C32 C31 176.48(13) . . . . ?
C25 C26 C33 C34 0.9(2) . . . . ?
C27 C26 C33 C34 -176.71(13) . . . . ?
C24 N1 C34 C33 -0.7(2) . . . . ?
C26 C33 C34 N1 -0.1(2) . . . . ?

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
O6 H6O O5 0.98(2) 1.61(2) 2.5473(15) 159.1(18) .
O3 H3O O2 0.91(2) 1.76(2) 2.6066(15) 152.7(17) .
N1 H1N O4 1.06(2) 1.59(2) 2.6528(16) 176.9(18) 3_655
O1 H1O O5 1.03(2) 1.54(2) 2.5632(14) 171(2) 2

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_S2
_database_code_depnum_ccdc_archive 'CCDC 1036230'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '4-phenylpyridinium pamoate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 O6, C11 H10 N'
_chemical_formula_sum            'C34 H25 N O6'
_chemical_formula_weight         543.55

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'

_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                   11.0358(19)
_cell_length_b                   13.172(2)
_cell_length_c                   17.721(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.056(2)
_cell_angle_gamma                90
_cell_volume                     2528.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      2.435
_cell_measurement_theta_max      28.101

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.9011
_exptl_transmission_factor_max   0.9798
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'symmetry-related measurements'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13893
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.880
_diffrn_reflns_theta_max         28.263
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5802
_reflns_number_gt                4475
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_publication_material  
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'

_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)+(0.0513P)²+0.2972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Direct
_atom_sites_solution_secondary   Difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5802
_refine_ls_number_parameters     386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
O1 O 0.38711(9) 0.87663(8) 0.14468(6) 0.0197(2) Uani 1 1 d . . . . .
N1 N 0.43263(11) 0.10545(9) 0.09732(7) 0.0190(3) Uani 1 1 d . . . . .
C1 C 0.50359(13) 0.86364(10) 0.14160(8) 0.0161(3) Uani 1 1 d . . . . .
O2 O 0.54287(9) 0.86292(8) 0.08114(6) 0.0235(3) Uani 1 1 d . . . . .
C2 C 0.58580(13) 0.84897(10) 0.21795(8) 0.0144(3) Uani 1 1 d . . . . .
O3 O 0.76021(10) 0.81339(8) 0.15740(6) 0.0205(2) Uani 1 1 d . . . . .
C3 C 0.71188(13) 0.82100(10) 0.22225(8) 0.0146(3) Uani 1 1 d . . . . .
O4 O 1.22649(9) 0.44041(8) 0.49813(6) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.78768(12) 0.79914(10) 0.29262(8) 0.0144(3) Uani 1 1 d . . . . .
O5 O 1.23679(9) 0.60834(8) 0.51771(6) 0.0217(2) Uani 1 1 d . . . . .
C5 C 0.74087(13) 0.81499(10) 0.36102(8) 0.0150(3) Uani 1 1 d . . . . .
O6 O 1.10183(9) 0.72672(8) 0.42558(6) 0.0205(2) Uani 1 1 d . . . . .
C6 C 0.81493(13) 0.80152(10) 0.43568(8) 0.0175(3) Uani 1 1 d . . . . .
H6 H 0.8986 0.7810 0.4404 0.021 Uiso 1 1 calc R U . . .
C7 C 0.76776(14) 0.81755(11) 0.50058(8) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.8191 0.8078 0.5496 0.025 Uiso 1 1 calc R U . . .
C8 C 0.64389(14) 0.84835(11) 0.49596(8) 0.0217(3) Uani 1 1 d . . . . .
H8 H 0.6121 0.8586 0.5415 0.026 Uiso 1 1 calc R U . . .
C9 C 0.57023(14) 0.86335(11) 0.42565(8) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.4872 0.8846 0.4226 0.024 Uiso 1 1 calc R U . . .
C10 C 0.61614(13) 0.84754(10) 0.35698(8) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.54012(13) 0.86127(10) 0.28406(8) 0.0161(3) Uani 1 1 d . . . . .
H11 H 0.4559 0.8793 0.2807 0.019 Uiso 1 1 calc R U . . .
C12 C 0.91996(12) 0.76493(11) 0.29477(8) 0.0166(3) Uani 1 1 d . . . . .
H12A H 0.9759 0.8132 0.3273 0.020 Uiso 1 1 calc R U . . .
H12B H 0.9370 0.7697 0.2420 0.020 Uiso 1 1 calc R U . . .
C13 C 1.18816(13) 0.52810(11) 0.48336(8) 0.0181(3) Uani 1 1 d . . . . .
C14 C 1.07970(12) 0.54429(11) 0.41817(8) 0.0167(3) Uani 1 1 d . . . . .
C15 C 1.04374(12) 0.64355(11) 0.38959(8) 0.0158(3) Uani 1 1 d . . . . .
C16 C 0.95245(12) 0.65809(11) 0.32464(8) 0.0155(3) Uani 1 1 d . . . . .
C17 C 0.89646(12) 0.57020(11) 0.28522(8) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.81484(13) 0.57643(12) 0.21238(8) 0.0183(3) Uani 1 1 d . . . . .
H18 H 0.7957 0.6409 0.1891 0.022 Uiso 1 1 calc R U . . .
C19 C 0.76379(13) 0.49057(12) 0.17562(8) 0.0221(3) Uani 1 1 d . . . . .
H19 H 0.7124 0.4963 0.1262 0.027 Uiso 1 1 calc R U . . .
C20 C 0.78606(13) 0.39386(12) 0.20972(9) 0.0224(3) Uani 1 1 d . . . . .
H20 H 0.7478 0.3353 0.1844 0.027 Uiso 1 1 calc R U . . .
C21 C 0.86334(13) 0.38552(11) 0.27956(9) 0.0207(3) Uani 1 1 d . . . . .
H21 H 0.8768 0.3208 0.3033 0.025 Uiso 1 1 calc R U . . .
C22 C 0.92372(13) 0.47157(11) 0.31720(8) 0.0172(3) Uani 1 1 d . . . . .
C23 C 1.01700(13) 0.46161(11) 0.38366(8) 0.0179(3) Uani 1 1 d . . . . .
H23 H 1.0367 0.3961 0.4049 0.022 Uiso 1 1 calc R U . . .
C24 C 0.39619(13) 0.09795(11) 0.16480(8) 0.0187(3) Uani 1 1 d . . . . .
H24 H 0.3110 0.0901 0.1659 0.022 Uiso 1 1 calc R U . . .
C25 C 0.48082(13) 0.10150(10) 0.23243(8) 0.0173(3) Uani 1 1 d . . . . .
H25 H 0.4539 0.0970 0.2801 0.021 Uiso 1 1 calc R U . . .
C26 C 0.60676(13) 0.11176(10) 0.23143(8) 0.0151(3) Uani 1 1 d . . . . .
C27 C 0.70064(13) 0.10615(10) 0.30369(8) 0.0162(3) Uani 1 1 d . . . . .
C28 C 0.66917(14) 0.13004(11) 0.37444(8) 0.0207(3) Uani 1 1 d . . . . .
H28 H 0.5877 0.1520 0.3762 0.025 Uiso 1 1 calc R U . . .
C29 C 0.75595(16) 0.12196(12) 0.44210(9) 0.0261(4) Uani 1 1 d . . . . .
H29 H 0.7336 0.1383 0.4898 0.031 Uiso 1 1 calc R U . . .
C30 C 0.87469(15) 0.09019(12) 0.44028(9) 0.0290(4) Uani 1 1 d . . . . .
H30 H 0.9341 0.0853 0.4866 0.035 Uiso 1 1 calc R U . . .
H1N H 0.3660(18) 0.0949(14) 0.0519(11) 0.046(6) Uiso 1 1 d . . . . .
H6O H 1.1593(18) 0.6979(15) 0.4693(12) 0.051(6) Uiso 1 1 d . . . . .
H3O H 0.702(2) 0.8338(16) 0.1191(12) 0.056(6) Uiso 1 1 d . . . . .
H1O H 0.335(2) 0.8868(16) 0.0876(13) 0.064(7) Uiso 1 1 d . . . . .
C31 C 0.90677(15) 0.06567(12) 0.37104(9) 0.0270(4) Uani 1 1 d . . . . .
H31 H 0.9883 0.0433 0.3700 0.032 Uiso 1 1 calc R U . . .
C32 C 0.82074(13) 0.07346(11) 0.30265(9) 0.0211(3) Uani 1 1 d . . . . .
H32 H 0.8437 0.0565 0.2552 0.025 Uiso 1 1 calc R U . . .
C33 C 0.63995(13) 0.12333(11) 0.15978(8) 0.0180(3) Uani 1 1 d . . . . .
H33 H 0.7240 0.1341 0.1568 0.022 Uiso 1 1 calc R U . . .
C34 C 0.55152(13) 0.11926(11) 0.09328(8) 0.0196(3) Uani 1 1 d . . . . .
H34 H 0.5749 0.1262 0.0447 0.023 Uiso 1 1 calc R U . . .


_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
O1 C1 1.3083(17) . ?
O1 H1O 1.07(2) . ?
N1 C24 1.3363(19) . ?
N1 C34 1.3401(19) . ?
N1 H1N 0.990(19) . ?
C1 O2 1.2306(17) . ?
C1 C2 1.4900(18) . ?
C2 C11 1.3708(19) . ?
C2 C3 1.4273(19) . ?
O3 C3 1.3600(16) . ?
O3 H3O 0.89(2) . ?
C3 C4 1.3920(18) . ?
O4 C13 1.2407(17) . ?
C4 C5 1.4212(19) . ?
C4 C12 1.5212(19) . ?
O5 C13 1.2847(17) . ?
C5 C6 1.4266(18) . ?
C5 C10 1.430(2) . ?
O6 C15 1.3642(16) . ?
O6 H6O 0.98(2) . ?
C6 C7 1.367(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.413(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.365(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.420(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.4108(19) . ?
C11 H11 0.9500 . ?
C12 C16 1.5221(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5107(19) . ?
C14 C23 1.370(2) . ?
C14 C15 1.431(2) . ?
C15 C16 1.3898(19) . ?
C16 C17 1.4299(19) . ?
C17 C22 1.426(2) . ?
C17 C18 1.4277(19) . ?
C18 C19 1.371(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.411(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.366(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.4139(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.371(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(2) . ?
C25 H25 0.9500 . ?
C26 C33 1.3955(19) . ?
C26 C27 1.4865(19) . ?
C27 C32 1.397(2) . ?
C27 C28 1.399(2) . ?
C28 C29 1.388(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.3794(19) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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 O1 H1O 109.3(11) . . ?
C24 N1 C34 121.56(13) . . ?
C24 N1 H1N 114.4(11) . . ?
C34 N1 H1N 123.9(11) . . ?
O2 C1 O1 123.38(13) . . ?
O2 C1 C2 122.33(13) . . ?
O1 C1 C2 114.28(12) . . ?
C11 C2 C3 119.97(12) . . ?
C11 C2 C1 120.06(13) . . ?
C3 C2 C1 119.97(12) . . ?
C3 O3 H3O 106.2(13) . . ?
O3 C3 C4 118.43(13) . . ?
O3 C3 C2 120.68(12) . . ?
C4 C3 C2 120.89(13) . . ?
C3 C4 C5 118.65(13) . . ?
C3 C4 C12 119.51(12) . . ?
C5 C4 C12 121.75(12) . . ?
C4 C5 C6 122.37(13) . . ?
C4 C5 C10 120.33(12) . . ?
C6 C5 C10 117.28(13) . . ?
C15 O6 H6O 103.5(12) . . ?
C7 C6 C5 121.22(14) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 121.06(13) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.64(14) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.86(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.25(13) . . ?
C11 C10 C5 118.80(13) . . ?
C9 C10 C5 119.93(13) . . ?
C2 C11 C10 121.06(13) . . ?
C2 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C4 C12 C16 116.33(11) . . ?
C4 C12 H12A 108.2 . . ?
C16 C12 H12A 108.2 . . ?
C4 C12 H12B 108.2 . . ?
C16 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
O4 C13 O5 124.86(13) . . ?
O4 C13 C14 118.74(13) . . ?
O5 C13 C14 116.35(12) . . ?
C23 C14 C15 119.11(13) . . ?
C23 C14 C13 119.17(13) . . ?
C15 C14 C13 121.67(12) . . ?
O6 C15 C16 118.52(13) . . ?
O6 C15 C14 119.66(12) . . ?
C16 C15 C14 121.80(13) . . ?
C15 C16 C17 118.02(13) . . ?
C15 C16 C12 120.03(12) . . ?
C17 C16 C12 121.86(12) . . ?
C22 C17 C18 117.39(13) . . ?
C22 C17 C16 120.33(12) . . ?
C18 C17 C16 122.26(13) . . ?
C19 C18 C17 120.84(14) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.28(14) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 119.20(14) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 121.21(14) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 121.33(13) . . ?
C23 C22 C17 118.68(13) . . ?
C21 C22 C17 119.86(13) . . ?
C14 C23 C22 121.52(13) . . ?
C14 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
N1 C24 C25 120.53(13) . . ?
N1 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.24(13) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C33 C26 C25 117.16(13) . . ?
C33 C26 C27 121.86(13) . . ?
C25 C26 C27 120.93(13) . . ?
C32 C27 C28 118.69(13) . . ?
C32 C27 C26 120.68(13) . . ?
C28 C27 C26 120.59(13) . . ?
C29 C28 C27 120.54(15) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C30 C29 C28 120.23(15) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C31 C30 C29 119.87(14) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.56(15) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C27 120.11(15) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C34 C33 C26 120.45(14) . . ?
C34 C33 H33 119.8 . . ?
C26 C33 H33 119.8 . . ?
N1 C34 C33 119.95(14) . . ?
N1 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C11 172.95(13) . . . . ?
O1 C1 C2 C11 -7.41(19) . . . . ?
O2 C1 C2 C3 -7.7(2) . . . . ?
O1 C1 C2 C3 171.91(12) . . . . ?
C11 C2 C3 O3 -176.73(12) . . . . ?
C1 C2 C3 O3 3.96(19) . . . . ?
C11 C2 C3 C4 4.4(2) . . . . ?
C1 C2 C3 C4 -174.91(12) . . . . ?
O3 C3 C4 C5 174.89(12) . . . . ?
C2 C3 C4 C5 -6.2(2) . . . . ?
O3 C3 C4 C12 -1.65(19) . . . . ?
C2 C3 C4 C12 177.24(12) . . . . ?
C3 C4 C5 C6 -175.43(13) . . . . ?
C12 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C10 3.3(2) . . . . ?
C12 C4 C5 C10 179.76(12) . . . . ?
C4 C5 C6 C7 179.80(13) . . . . ?
C10 C5 C6 C7 1.0(2) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 -0.6(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 178.97(13) . . . . ?
C8 C9 C10 C5 0.3(2) . . . . ?
C4 C5 C10 C11 1.43(19) . . . . ?
C6 C5 C10 C11 -179.77(12) . . . . ?
C4 C5 C10 C9 -179.89(13) . . . . ?
C6 C5 C10 C9 -1.09(19) . . . . ?
C3 C2 C11 C10 0.5(2) . . . . ?
C1 C2 C11 C10 179.85(12) . . . . ?
C9 C10 C11 C2 177.98(13) . . . . ?
C5 C10 C11 C2 -3.4(2) . . . . ?
C3 C4 C12 C16 -116.28(14) . . . . ?
C5 C4 C12 C16 67.29(17) . . . . ?
O4 C13 C14 C23 8.2(2) . . . . ?
O5 C13 C14 C23 -174.33(13) . . . . ?
O4 C13 C14 C15 -169.37(13) . . . . ?
O5 C13 C14 C15 8.1(2) . . . . ?
C23 C14 C15 O6 177.11(13) . . . . ?
C13 C14 C15 O6 -5.3(2) . . . . ?
C23 C14 C15 C16 -4.4(2) . . . . ?
C13 C14 C15 C16 173.18(13) . . . . ?
O6 C15 C16 C17 176.98(12) . . . . ?
C14 C15 C16 C17 -1.6(2) . . . . ?
O6 C15 C16 C12 0.5(2) . . . . ?
C14 C15 C16 C12 -178.05(12) . . . . ?
C4 C12 C16 C15 -119.26(14) . . . . ?
C4 C12 C16 C17 64.38(17) . . . . ?
C15 C16 C17 C22 7.24(19) . . . . ?
C12 C16 C17 C22 -176.33(13) . . . . ?
C15 C16 C17 C18 -171.02(13) . . . . ?
C12 C16 C17 C18 5.4(2) . . . . ?
C22 C17 C18 C19 0.9(2) . . . . ?
C16 C17 C18 C19 179.21(13) . . . . ?
C17 C18 C19 C20 2.6(2) . . . . ?
C18 C19 C20 C21 -2.2(2) . . . . ?
C19 C20 C21 C22 -1.7(2) . . . . ?
C20 C21 C22 C23 -170.71(14) . . . . ?
C20 C21 C22 C17 5.1(2) . . . . ?
C18 C17 C22 C23 171.30(12) . . . . ?
C16 C17 C22 C23 -7.0(2) . . . . ?
C18 C17 C22 C21 -4.7(2) . . . . ?
C16 C17 C22 C21 176.99(13) . . . . ?
C15 C14 C23 C22 4.6(2) . . . . ?
C13 C14 C23 C22 -172.99(13) . . . . ?
C21 C22 C23 C14 176.89(13) . . . . ?
C17 C22 C23 C14 1.0(2) . . . . ?
C34 N1 C24 C25 -1.8(2) . . . . ?
N1 C24 C25 C26 -0.8(2) . . . . ?
C24 C25 C26 C33 3.2(2) . . . . ?
C24 C25 C26 C27 -174.29(13) . . . . ?
C33 C26 C27 C32 -24.8(2) . . . . ?
C25 C26 C27 C32 152.58(14) . . . . ?
C33 C26 C27 C28 157.47(13) . . . . ?
C25 C26 C27 C28 -25.1(2) . . . . ?
C32 C27 C28 C29 0.4(2) . . . . ?
C26 C27 C28 C29 178.13(13) . . . . ?
C27 C28 C29 C30 0.0(2) . . . . ?
C28 C29 C30 C31 -0.5(2) . . . . ?
C29 C30 C31 C32 0.6(2) . . . . ?
C30 C31 C32 C27 -0.1(2) . . . . ?
C28 C27 C32 C31 -0.4(2) . . . . ?
C26 C27 C32 C31 -178.08(13) . . . . ?
C25 C26 C33 C34 -3.3(2) . . . . ?
C27 C26 C33 C34 174.23(13) . . . . ?
C24 N1 C34 C33 1.7(2) . . . . ?
C26 C33 C34 N1 0.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O4 0.990(19) 1.712(19) 2.6638(16) 159.8(17) 4_465
O6 H6O O5 0.98(2) 1.61(2) 2.5264(14) 155.0(18) .
O3 H3O O2 0.89(2) 1.79(2) 2.6003(15) 150.5(19) .
O1 H1O O5 1.07(2) 1.48(2) 2.5342(14) 165.4(19) 4_475

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

