# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_is_mha60
_database_code_depnum_ccdc_archive 'CCDC 1914143'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;

_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_publcif_datablock.id            {fa114a63-126e-4870-b3f2-316102250e96}
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
'N-(Phenyl-6-deoxy-2,3,4-tri-O-methyl-β-D-glucopyranosid-6-yl)-pyridinium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N O5 +, C F3 O3 S -'
_chemical_formula_sum            'C21 H26 F3 N O8 S'
_chemical_formula_weight         509.49

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'
F F 0.0171 0.0103 '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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.1908(4)
_cell_length_b                   15.8291(8)
_cell_length_c                   20.6394(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2349.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3926
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      23.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.208
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33895
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6841
_reflns_number_gt                4103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups),
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) =
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles
 of all methyl groups were allowed to refine.

 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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.0638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6841
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.7795(4) 0.42133(15) 0.31722(13) 0.0343(6) Uani 1 1 d . . . . .
O1 O 0.5145(3) 0.46987(11) 0.40507(10) 0.0319(5) Uani 1 1 d . . . . .
O2 O 0.2792(3) 0.40575(12) 0.46049(10) 0.0372(5) Uani 1 1 d . . . . .
O3 O 0.5587(3) 0.67541(13) 0.32851(13) 0.0499(7) Uani 1 1 d . . . . .
O4 O 0.3205(4) 0.70437(14) 0.43761(13) 0.0569(8) Uani 1 1 d . . . . .
O5 O 0.0624(3) 0.55617(14) 0.44899(12) 0.0432(6) Uani 1 1 d . . . . .
C1 C 0.5569(4) 0.52756(16) 0.35451(15) 0.0312(7) Uani 1 1 d . . . . .
H1 H 0.4730 0.5167 0.3168 0.037 Uiso 1 1 calc R U . . .
C2 C 0.5256(5) 0.61722(18) 0.37924(17) 0.0378(8) Uani 1 1 d . . . . .
H2 H 0.6128 0.6290 0.4159 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3258(5) 0.62668(17) 0.40253(16) 0.0356(8) Uani 1 1 d . . . . .
H3 H 0.2422 0.6314 0.3640 0.043 Uiso 1 1 calc R U . . .
C4 C 0.2603(4) 0.55350(18) 0.44441(16) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.3149 0.5593 0.4887 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3186(5) 0.46870(17) 0.41563(15) 0.0320(7) Uani 1 1 d . . . . .
H5 H 0.2512 0.4579 0.3741 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7569(5) 0.51149(18) 0.33464(16) 0.0382(7) Uani 1 1 d . . . . .
H6A H 0.7894 0.5475 0.2971 0.046 Uiso 1 1 calc R U . . .
H6B H 0.8414 0.5260 0.3708 0.046 Uiso 1 1 calc R U . . .
C7 C 0.8667(5) 0.3686(2) 0.35852(17) 0.0419(8) Uani 1 1 d . . . . .
H7 H 0.9168 0.3900 0.3978 0.050 Uiso 1 1 calc R U . . .
C8 C 0.8836(5) 0.2850(2) 0.3444(2) 0.0503(10) Uani 1 1 d . . . . .
H8 H 0.9485 0.2482 0.3728 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8048(6) 0.2543(2) 0.2880(2) 0.0572(11) Uani 1 1 d . . . . .
H9 H 0.8123 0.1958 0.2780 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7162(6) 0.3084(2) 0.24671(18) 0.0524(9) Uani 1 1 d . . . . .
H10 H 0.6635 0.2878 0.2076 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7036(5) 0.3925(2) 0.26193(16) 0.0423(8) Uani 1 1 d . . . . .
H11 H 0.6414 0.4303 0.2335 0.051 Uiso 1 1 calc R U . . .
C12 C 0.7131(7) 0.7293(3) 0.3380(3) 0.0940(18) Uani 1 1 d . . . . .
H12A H 0.8281 0.6961 0.3359 0.141 Uiso 1 1 calc R U . . .
H12B H 0.7036 0.7564 0.3805 0.141 Uiso 1 1 calc R U . . .
H12C H 0.7148 0.7726 0.3041 0.141 Uiso 1 1 calc R U . . .
C13 C 0.1546(6) 0.7504(2) 0.4342(2) 0.0625(12) Uani 1 1 d . . . . .
H13A H 0.0585 0.7218 0.4597 0.094 Uiso 1 1 calc R U . . .
H13B H 0.1143 0.7544 0.3890 0.094 Uiso 1 1 calc R U . . .
H13C H 0.1749 0.8073 0.4516 0.094 Uiso 1 1 calc R U . . .
C14 C -0.0108(6) 0.5446(3) 0.5121(2) 0.0614(11) Uani 1 1 d . . . . .
H14A H 0.0218 0.5932 0.5392 0.092 Uiso 1 1 calc R U . . .
H14B H 0.0415 0.4931 0.5311 0.092 Uiso 1 1 calc R U . . .
H14C H -0.1465 0.5394 0.5097 0.092 Uiso 1 1 calc R U . . .
C15 C 0.2881(5) 0.32180(18) 0.43988(15) 0.0339(7) Uani 1 1 d . . . . .
C16 C 0.2177(5) 0.2633(2) 0.48360(17) 0.0405(8) Uani 1 1 d . . . . .
H16 H 0.1670 0.2815 0.5238 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2223(5) 0.1789(2) 0.46812(18) 0.0483(9) Uani 1 1 d . . . . .
H17 H 0.1744 0.1385 0.4978 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2955(5) 0.15226(19) 0.40994(18) 0.0462(9) Uani 1 1 d . . . . .
H18 H 0.2994 0.0937 0.3998 0.055 Uiso 1 1 calc R U . . .
C19 C 0.3632(5) 0.2106(2) 0.36647(18) 0.0428(8) Uani 1 1 d . . . . .
H19 H 0.4124 0.1921 0.3262 0.051 Uiso 1 1 calc R U . . .
C20 C 0.3601(5) 0.29596(19) 0.38098(15) 0.0371(8) Uani 1 1 d . . . . .
H20 H 0.4067 0.3362 0.3509 0.045 Uiso 1 1 calc R U . . .
S1 S 1.20714(13) 0.49052(5) 0.21549(4) 0.0417(2) Uani 1 1 d . . . . .
O7 O 1.3909(4) 0.5099(2) 0.19341(14) 0.0776(9) Uani 1 1 d . . . . .
O8 O 1.1853(4) 0.41154(15) 0.24736(12) 0.0587(7) Uani 1 1 d . . . . .
O9 O 1.1138(5) 0.55812(16) 0.24722(14) 0.0718(9) Uani 1 1 d . . . . .
C21 C 1.0800(6) 0.4781(2) 0.14015(19) 0.0523(9) Uani 1 1 d . . . . .
F1 F 1.1380(5) 0.41126(16) 0.10745(11) 0.0864(9) Uani 1 1 d . . . . .
F2 F 1.1012(3) 0.54551(15) 0.10245(11) 0.0698(7) Uani 1 1 d . . . . .
F3 F 0.8991(4) 0.46806(19) 0.15095(13) 0.0918(9) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C11 1.345(4) . ?
N1 C7 1.348(4) . ?
N1 C6 1.481(4) . ?
O1 C1 1.420(3) . ?
O1 C5 1.426(4) . ?
O2 C5 1.389(3) . ?
O2 C15 1.397(4) . ?
O3 C12 1.413(5) . ?
O3 C2 1.415(4) . ?
O4 C13 1.400(5) . ?
O4 C3 1.428(3) . ?
O5 C14 1.417(4) . ?
O5 C4 1.427(4) . ?
C1 C6 1.517(5) . ?
C1 C2 1.525(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.523(5) . ?
C2 H2 1.0000 . ?
C3 C4 1.520(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.527(4) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.361(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.383(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.375(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
S1 O8 1.422(2) . ?
S1 O9 1.423(3) . ?
S1 O7 1.431(3) . ?
S1 C21 1.815(4) . ?
C21 F1 1.322(4) . ?
C21 F3 1.329(5) . ?
C21 F2 1.330(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C7 121.0(3) . . ?
C11 N1 C6 119.3(3) . . ?
C7 N1 C6 119.6(3) . . ?
C1 O1 C5 109.4(2) . . ?
C5 O2 C15 118.0(2) . . ?
C12 O3 C2 115.0(3) . . ?
C13 O4 C3 116.5(3) . . ?
C14 O5 C4 115.3(3) . . ?
O1 C1 C6 107.1(2) . . ?
O1 C1 C2 108.7(2) . . ?
C6 C1 C2 112.7(2) . . ?
O1 C1 H1 109.4 . . ?
C6 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
O3 C2 C3 109.2(3) . . ?
O3 C2 C1 109.5(3) . . ?
C3 C2 C1 109.6(2) . . ?
O3 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
O4 C3 C4 111.1(3) . . ?
O4 C3 C2 105.7(2) . . ?
C4 C3 C2 113.4(3) . . ?
O4 C3 H3 108.9 . . ?
C4 C3 H3 108.9 . . ?
C2 C3 H3 108.9 . . ?
O5 C4 C3 108.9(3) . . ?
O5 C4 C5 109.0(2) . . ?
C3 C4 C5 111.3(2) . . ?
O5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
O2 C5 O1 108.2(2) . . ?
O2 C5 C4 108.4(2) . . ?
O1 C5 C4 108.6(2) . . ?
O2 C5 H5 110.5 . . ?
O1 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
N1 C6 C1 109.3(2) . . ?
N1 C6 H6A 109.8 . . ?
C1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N1 C7 C8 120.5(3) . . ?
N1 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
N1 C11 C10 119.8(3) . . ?
N1 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.7(3) . . ?
C20 C15 O2 124.5(3) . . ?
C16 C15 O2 114.8(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.0(3) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O8 S1 O9 113.34(16) . . ?
O8 S1 O7 115.98(19) . . ?
O9 S1 O7 114.9(2) . . ?
O8 S1 C21 104.20(17) . . ?
O9 S1 C21 103.8(2) . . ?
O7 S1 C21 102.46(17) . . ?
F1 C21 F3 107.4(4) . . ?
F1 C21 F2 107.9(3) . . ?
F3 C21 F2 107.8(3) . . ?
F1 C21 S1 111.4(3) . . ?
F3 C21 S1 111.2(3) . . ?
F2 C21 S1 110.9(3) . . ?

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
C5 O1 C1 C6 -167.0(2) . . . . ?
C5 O1 C1 C2 71.0(3) . . . . ?
C12 O3 C2 C3 125.7(4) . . . . ?
C12 O3 C2 C1 -114.2(4) . . . . ?
O1 C1 C2 O3 -177.2(2) . . . . ?
C6 C1 C2 O3 64.2(3) . . . . ?
O1 C1 C2 C3 -57.5(3) . . . . ?
C6 C1 C2 C3 -176.1(3) . . . . ?
C13 O4 C3 C4 -90.1(4) . . . . ?
C13 O4 C3 C2 146.6(3) . . . . ?
O3 C2 C3 O4 -72.8(3) . . . . ?
C1 C2 C3 O4 167.3(2) . . . . ?
O3 C2 C3 C4 165.4(2) . . . . ?
C1 C2 C3 C4 45.4(4) . . . . ?
C14 O5 C4 C3 -134.4(3) . . . . ?
C14 O5 C4 C5 104.0(3) . . . . ?
O4 C3 C4 O5 76.8(3) . . . . ?
C2 C3 C4 O5 -164.4(3) . . . . ?
O4 C3 C4 C5 -163.0(3) . . . . ?
C2 C3 C4 C5 -44.2(4) . . . . ?
C15 O2 C5 O1 -74.3(3) . . . . ?
C15 O2 C5 C4 168.0(3) . . . . ?
C1 O1 C5 O2 174.0(2) . . . . ?
C1 O1 C5 C4 -68.5(3) . . . . ?
O5 C4 C5 O2 -68.5(3) . . . . ?
C3 C4 C5 O2 171.3(3) . . . . ?
O5 C4 C5 O1 174.1(2) . . . . ?
C3 C4 C5 O1 54.0(3) . . . . ?
C11 N1 C6 C1 71.6(4) . . . . ?
C7 N1 C6 C1 -104.9(3) . . . . ?
O1 C1 C6 N1 55.1(3) . . . . ?
C2 C1 C6 N1 174.7(2) . . . . ?
C11 N1 C7 C8 1.5(5) . . . . ?
C6 N1 C7 C8 177.9(3) . . . . ?
N1 C7 C8 C9 -2.0(5) . . . . ?
C7 C8 C9 C10 1.8(6) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C7 N1 C11 C10 -0.7(5) . . . . ?
C6 N1 C11 C10 -177.1(3) . . . . ?
C9 C10 C11 N1 0.4(6) . . . . ?
C5 O2 C15 C20 10.2(5) . . . . ?
C5 O2 C15 C16 -169.7(3) . . . . ?
C20 C15 C16 C17 0.8(5) . . . . ?
O2 C15 C16 C17 -179.2(3) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C16 C15 C20 C19 -0.8(5) . . . . ?
O2 C15 C20 C19 179.2(3) . . . . ?
C18 C19 C20 C15 0.1(5) . . . . ?
O8 S1 C21 F1 -54.7(3) . . . . ?
O9 S1 C21 F1 -173.5(3) . . . . ?
O7 S1 C21 F1 66.6(3) . . . . ?
O8 S1 C21 F3 65.2(3) . . . . ?
O9 S1 C21 F3 -53.7(3) . . . . ?
O7 S1 C21 F3 -173.6(3) . . . . ?
O8 S1 C21 F2 -174.9(3) . . . . ?
O9 S1 C21 F2 66.3(3) . . . . ?
O7 S1 C21 F2 -53.6(3) . . . . ?

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_is_mhB61
_database_code_depnum_ccdc_archive 'CCDC 1916778'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

_chemical_name_systematic        
'N-(1,4-anhydro-5-deoxy-2,3-O-isopropyliden-D-ribitol-5-yl)-pyridinium mesylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N O3 +, C H3 O3 S -, 0.5 (H2 O)'
_chemical_formula_sum            'C14 H22 N O6.50 S'
_chemical_formula_weight         340.38

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   16.0965(11)
_cell_length_b                   8.7488(6)
_cell_length_c                   13.4481(9)
_cell_angle_alpha                90
_cell_angle_beta                 121.558(3)
_cell_angle_gamma                90
_cell_volume                     1613.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7182
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      31.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex II CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13005
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         31.975
_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 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4965
_reflns_number_gt                4616
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_max     0.771
_reflns_Friedel_fraction_full    0.931

_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 Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model,
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups),
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) =
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles
 of all methyl groups were allowed to refine.

 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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.3986P] 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_abs_structure_details 
;
 Flack x determined using 1760 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4965
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
C1 C 0.18670(14) 0.5459(2) 0.25760(17) 0.0148(4) Uani 1 1 d . . . . .
H1 H 0.1717 0.4501 0.2857 0.018 Uiso 1 1 calc R U . . .
C2 C 0.29411(15) 0.7478(3) 0.33461(19) 0.0224(4) Uani 1 1 d . . . . .
H2A H 0.2961 0.7841 0.2661 0.027 Uiso 1 1 calc R U . . .
H2B H 0.3536 0.7834 0.4065 0.027 Uiso 1 1 calc R U . . .
C3 C 0.20368(16) 0.8056(3) 0.32999(18) 0.0182(4) Uani 1 1 d . . . . .
H3 H 0.1821 0.9081 0.2920 0.022 Uiso 1 1 calc R U . . .
C4 C 0.12726(15) 0.6790(2) 0.26431(19) 0.0155(4) Uani 1 1 d . . . . .
H4 H 0.0742 0.7132 0.1852 0.019 Uiso 1 1 calc R U . . .
C5 C 0.13115(14) 0.7483(3) 0.43392(16) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.06098(17) 0.8790(3) 0.40802(19) 0.0212(4) Uani 1 1 d . . . . .
H6A H 0.0481 0.9319 0.3371 0.032 Uiso 1 1 calc R U . . .
H6B H 0.0897 0.9508 0.4736 0.032 Uiso 1 1 calc R U . . .
H6C H -0.0003 0.8388 0.3966 0.032 Uiso 1 1 calc R U . . .
C7 C 0.15737(19) 0.6622(3) 0.5438(2) 0.0280(5) Uani 1 1 d . . . . .
H7A H 0.1877 0.7323 0.6105 0.042 Uiso 1 1 calc R U . . .
H7B H 0.2032 0.5799 0.5562 0.042 Uiso 1 1 calc R U . . .
H7C H 0.0982 0.6184 0.5361 0.042 Uiso 1 1 calc R U . . .
C8 C 0.16394(15) 0.5217(2) 0.13295(18) 0.0158(4) Uani 1 1 d . . . . .
H8A H 0.0929 0.5079 0.0794 0.019 Uiso 1 1 calc R U . . .
H8B H 0.1844 0.6127 0.1073 0.019 Uiso 1 1 calc R U . . .
C9 C 0.17805(14) 0.2454(3) 0.12278(17) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.1173 0.2365 0.1181 0.021 Uiso 1 1 calc R U . . .
C10 C 0.22719(19) 0.1160(2) 0.1236(2) 0.0218(5) Uani 1 1 d . . . . .
H10 H 0.2006 0.0177 0.1200 0.026 Uiso 1 1 calc R U . . .
C11 C 0.31580(19) 0.1300(3) 0.1298(2) 0.0244(5) Uani 1 1 d . . . . .
H11 H 0.3509 0.0418 0.1314 0.029 Uiso 1 1 calc R U . . .
C12 C 0.35190(16) 0.2749(3) 0.1337(2) 0.0243(5) Uani 1 1 d . . . . .
H12 H 0.4118 0.2868 0.1365 0.029 Uiso 1 1 calc R U . . .
C13 C 0.30114(16) 0.4019(3) 0.1334(2) 0.0189(4) Uani 1 1 d . . . . .
H13 H 0.3262 0.5013 0.1367 0.023 Uiso 1 1 calc R U . . .
N1 N 0.21623(13) 0.3848(2) 0.12854(15) 0.0139(3) Uani 1 1 d . . . . .
O1 O 0.28719(11) 0.58393(19) 0.33377(13) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.09103(11) 0.64224(19) 0.33810(13) 0.0208(3) Uani 1 1 d . . . . .
O3 O 0.21894(11) 0.80144(19) 0.44457(13) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.02201(16) 0.2828(3) 0.33006(18) 0.0216(4) Uani 1 1 d . . . . .
H14A H -0.0005 0.2095 0.3661 0.032 Uiso 1 1 calc R U . . .
H14B H 0.0092 0.3870 0.3453 0.032 Uiso 1 1 calc R U . . .
H14C H 0.0922 0.2696 0.3632 0.032 Uiso 1 1 calc R U . . .
S1 S -0.04099(3) 0.25100(6) 0.17756(4) 0.01507(11) Uani 1 1 d . . . . .
O4 O -0.14432(10) 0.2557(2) 0.13776(12) 0.0194(3) Uani 1 1 d . . . . .
O5 O -0.00969(13) 0.10059(18) 0.16213(14) 0.0249(4) Uani 1 1 d . . . . .
O6 O -0.01286(12) 0.37415(19) 0.12790(14) 0.0225(3) Uani 1 1 d . . . . .
O7 O 0.0000 -0.0920(3) 0.0000 0.0408(7) Uani 1 2 d S T P . .
H7 H -0.010(3) -0.032(5) 0.043(3) 0.057(11) Uiso 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
C1 O1 1.429(3) . ?
C1 C8 1.532(3) . ?
C1 C4 1.539(3) . ?
C1 H1 1.0000 . ?
C2 O1 1.438(3) . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.428(2) . ?
C3 C4 1.544(3) . ?
C3 H3 1.0000 . ?
C4 O2 1.426(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.422(2) . ?
C5 O2 1.438(3) . ?
C5 C7 1.509(3) . ?
C5 C6 1.514(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.482(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.350(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 N1 1.342(3) . ?
C13 H13 0.9500 . ?
C14 S1 1.771(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1 O4 1.4570(14) . ?
S1 O6 1.4588(16) . ?
S1 O5 1.4621(16) . ?
O7 H7 0.85(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8 110.45(16) . . ?
O1 C1 C4 106.68(16) . . ?
C8 C1 C4 111.65(16) . . ?
O1 C1 H1 109.3 . . ?
C8 C1 H1 109.3 . . ?
C4 C1 H1 109.3 . . ?
O1 C2 C3 105.33(16) . . ?
O1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
O1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
O3 C3 C2 109.21(18) . . ?
O3 C3 C4 103.58(16) . . ?
C2 C3 C4 104.20(17) . . ?
O3 C3 H3 113.0 . . ?
C2 C3 H3 113.0 . . ?
C4 C3 H3 113.0 . . ?
O2 C4 C1 111.31(16) . . ?
O2 C4 C3 104.89(16) . . ?
C1 C4 C3 104.05(16) . . ?
O2 C4 H4 112.0 . . ?
C1 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
O3 C5 O2 104.94(14) . . ?
O3 C5 C7 108.11(17) . . ?
O2 C5 C7 108.62(19) . . ?
O3 C5 C6 111.05(19) . . ?
O2 C5 C6 110.49(17) . . ?
C7 C5 C6 113.27(17) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C1 109.88(16) . . ?
N1 C8 H8A 109.7 . . ?
C1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C1 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C10 119.99(17) . . ?
N1 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N1 C13 C12 119.8(2) . . ?
N1 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 N1 C9 121.67(18) . . ?
C13 N1 C8 119.55(17) . . ?
C9 N1 C8 118.76(16) . . ?
C1 O1 C2 106.96(15) . . ?
C4 O2 C5 108.82(15) . . ?
C5 O3 C3 107.39(15) . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 S1 O6 112.28(10) . . ?
O4 S1 O5 112.65(11) . . ?
O6 S1 O5 112.78(10) . . ?
O4 S1 C14 105.83(10) . . ?
O6 S1 C14 106.69(10) . . ?
O5 S1 C14 105.96(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 C2 C3 O3 81.48(19) . . . . ?
O1 C2 C3 C4 -28.7(2) . . . . ?
O1 C1 C4 O2 -101.05(18) . . . . ?
C8 C1 C4 O2 138.20(17) . . . . ?
O1 C1 C4 C3 11.4(2) . . . . ?
C8 C1 C4 C3 -109.34(18) . . . . ?
O3 C3 C4 O2 13.2(2) . . . . ?
C2 C3 C4 O2 127.39(17) . . . . ?
O3 C3 C4 C1 -103.86(18) . . . . ?
C2 C3 C4 C1 10.4(2) . . . . ?
O1 C1 C8 N1 66.2(2) . . . . ?
C4 C1 C8 N1 -175.26(16) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 N1 -0.5(3) . . . . ?
C12 C13 N1 C9 -0.6(3) . . . . ?
C12 C13 N1 C8 177.62(19) . . . . ?
C10 C9 N1 C13 1.0(3) . . . . ?
C10 C9 N1 C8 -177.2(2) . . . . ?
C1 C8 N1 C13 -97.7(2) . . . . ?
C1 C8 N1 C9 80.6(2) . . . . ?
C8 C1 O1 C2 91.15(18) . . . . ?
C4 C1 O1 C2 -30.4(2) . . . . ?
C3 C2 O1 C1 37.4(2) . . . . ?
C1 C4 O2 C5 118.60(18) . . . . ?
C3 C4 O2 C5 6.7(2) . . . . ?
O3 C5 O2 C4 -24.3(2) . . . . ?
C7 C5 O2 C4 -139.72(18) . . . . ?
C6 C5 O2 C4 95.47(19) . . . . ?
O2 C5 O3 C3 33.3(2) . . . . ?
C7 C5 O3 C3 149.10(19) . . . . ?
C6 C5 O3 C3 -86.1(2) . . . . ?
C2 C3 O3 C5 -139.16(19) . . . . ?
C4 C3 O3 C5 -28.6(2) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.060

#==============================================================================

# SHELX FILES

_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_is_mha131
_database_code_depnum_ccdc_archive 'CCDC 1916780'
loop_
_audit_author_name
_audit_author_address
'A. Villinger'
;University of Rostock
Germany
;

_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
'N-(Methyl-6-deoxy-2,3,4-tri-O-ethyl-β-D-glucopyranosid-6-yl)-pyridinium trifluoromethanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H30 N O5 +, C F3 O3 S -'
_chemical_formula_sum            'C19 H30 F3 N O8 S'
_chemical_formula_weight         489.50

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'
F F 0.0171 0.0103 '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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   15.5061(9)
_cell_length_b                   6.3564(4)
_cell_length_c                   24.1497(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.865(3)
_cell_angle_gamma                90
_cell_volume                     2337.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9648
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      32.37

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23163
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.576
_diffrn_reflns_theta_max         32.499
_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 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7523
_reflns_number_gt                6827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_max     0.754
_reflns_Friedel_fraction_full    0.956

_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 Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups),
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) =
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles
 of all methyl groups were allowed to refine.

 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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+1.0577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7523
_refine_ls_number_parameters     293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
N1 N 0.51371(12) 0.9683(3) 0.14883(7) 0.0204(3) Uani 1 1 d . . . . .
O1 O 0.49049(10) 0.6489(3) 0.23078(6) 0.0213(3) Uani 1 1 d . . . . .
O2 O 0.40588(11) 0.3728(3) 0.24832(7) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.44654(11) 0.4668(3) 0.36658(7) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.61325(11) 0.6817(3) 0.39602(6) 0.0259(3) Uani 1 1 d . . . . .
O5 O 0.62244(10) 1.0349(2) 0.31999(7) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.43955(14) 0.5651(3) 0.26917(9) 0.0201(4) Uani 1 1 d . . . . .
H1 H 0.3907 0.6637 0.2729 0.024 Uiso 1 1 calc R U . . .
C2 C 0.49834(14) 0.5286(3) 0.32652(9) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.5418 0.4153 0.3231 0.024 Uiso 1 1 calc R U . . .
C3 C 0.54688(15) 0.7281(3) 0.34820(9) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.5043 0.8301 0.3595 0.024 Uiso 1 1 calc R U . . .
C4 C 0.59110(13) 0.8298(3) 0.30367(8) 0.0193(4) Uani 1 1 d . . . . .
H4 H 0.6414 0.7400 0.2976 0.023 Uiso 1 1 calc R U . . .
C5 C 0.52529(12) 0.8506(4) 0.24800(8) 0.0189(3) Uani 1 1 d . . . . .
H5 H 0.4769 0.9492 0.2526 0.023 Uiso 1 1 calc R U . . .
C6 C 0.32847(17) 0.3918(5) 0.20578(12) 0.0366(6) Uani 1 1 d . . . . .
H6A H 0.2829 0.4655 0.2213 0.055 Uiso 1 1 calc R U . . .
H6B H 0.3074 0.2513 0.1931 0.055 Uiso 1 1 calc R U . . .
H6C H 0.3421 0.4715 0.1738 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4491(2) 0.2474(4) 0.37808(14) 0.0440(8) Uani 1 1 d . . . . .
H7A H 0.5109 0.1999 0.3879 0.053 Uiso 1 1 calc R U . . .
H7B H 0.4203 0.1695 0.3441 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4036(2) 0.2026(5) 0.42544(14) 0.0433(7) Uani 1 1 d . . . . .
H8A H 0.4273 0.2937 0.4575 0.065 Uiso 1 1 calc R U . . .
H8B H 0.4127 0.0550 0.4367 0.065 Uiso 1 1 calc R U . . .
H8C H 0.3406 0.2296 0.4135 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5945(3) 0.7433(7) 0.44836(11) 0.0612(11) Uani 1 1 d . . . . .
H9A H 0.5392 0.6764 0.4541 0.073 Uiso 1 1 calc R U . . .
H9B H 0.5867 0.8978 0.4490 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6669(2) 0.6803(7) 0.49396(12) 0.0509(8) Uani 1 1 d . . . . .
H10A H 0.6731 0.5268 0.4941 0.076 Uiso 1 1 calc R U . . .
H10B H 0.6542 0.7268 0.5303 0.076 Uiso 1 1 calc R U . . .
H10C H 0.7217 0.7452 0.4879 0.076 Uiso 1 1 calc R U . . .
C11 C 0.71410(16) 1.0499(4) 0.34271(11) 0.0305(5) Uani 1 1 d . . . . .
H11A H 0.7478 0.9624 0.3203 0.037 Uiso 1 1 calc R U . . .
H11B H 0.7262 0.9985 0.3821 0.037 Uiso 1 1 calc R U . . .
C12 C 0.74108(19) 1.2761(5) 0.34080(14) 0.0392(6) Uani 1 1 d . . . . .
H12A H 0.7275 1.3267 0.3018 0.059 Uiso 1 1 calc R U . . .
H12B H 0.8043 1.2886 0.3552 0.059 Uiso 1 1 calc R U . . .
H12C H 0.7091 1.3606 0.3642 0.059 Uiso 1 1 calc R U . . .
C13 C 0.57324(15) 0.9319(4) 0.20323(9) 0.0246(4) Uani 1 1 d . . . . .
H13A H 0.6032 1.0653 0.2164 0.030 Uiso 1 1 calc R U . . .
H13B H 0.6188 0.8288 0.1978 0.030 Uiso 1 1 calc R U . . .
C14 C 0.47706(16) 1.1586(4) 0.13718(10) 0.0268(4) Uani 1 1 d . . . . .
H14 H 0.4872 1.2674 0.1646 0.032 Uiso 1 1 calc R U . . .
C15 C 0.42478(18) 1.1954(4) 0.08530(11) 0.0317(5) Uani 1 1 d . . . . .
H15 H 0.3987 1.3297 0.0769 0.038 Uiso 1 1 calc R U . . .
C16 C 0.41049(16) 1.0380(5) 0.04580(10) 0.0311(5) Uani 1 1 d . . . . .
H16 H 0.3757 1.0630 0.0096 0.037 Uiso 1 1 calc R U . . .
C17 C 0.44739(17) 0.8423(5) 0.05937(10) 0.0322(5) Uani 1 1 d . . . . .
H17 H 0.4372 0.7304 0.0329 0.039 Uiso 1 1 calc R U . . .
C18 C 0.49909(16) 0.8113(4) 0.11163(9) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.5245 0.6771 0.1213 0.032 Uiso 1 1 calc R U . . .
S1 S 0.20519(4) 0.84340(9) 0.13100(2) 0.02572(12) Uani 1 1 d . . . . .
O6 O 0.17897(14) 0.6311(3) 0.11431(10) 0.0413(5) Uani 1 1 d . . . . .
O7 O 0.15054(14) 0.9453(4) 0.16500(8) 0.0395(5) Uani 1 1 d . . . . .
O8 O 0.29783(12) 0.8799(3) 0.14789(8) 0.0365(4) Uani 1 1 d . . . . .
F1 F 0.09039(11) 0.9649(3) 0.04310(7) 0.0398(4) Uani 1 1 d . . . . .
F2 F 0.19532(15) 1.1876(3) 0.06966(8) 0.0517(5) Uani 1 1 d . . . . .
F3 F 0.21924(12) 0.9073(3) 0.02538(7) 0.0467(5) Uani 1 1 d . . . . .
C19 C 0.17696(18) 0.9829(4) 0.06423(11) 0.0294(5) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.333(3) . ?
N1 C14 1.344(3) . ?
N1 C13 1.475(3) . ?
O1 C5 1.422(3) . ?
O1 C1 1.429(3) . ?
O2 C1 1.386(3) . ?
O2 C6 1.430(3) . ?
O3 C7 1.421(3) . ?
O3 C2 1.424(3) . ?
O4 C9 1.405(3) . ?
O4 C3 1.425(3) . ?
O5 C4 1.421(3) . ?
O5 C11 1.427(3) . ?
C1 C2 1.525(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.517(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.533(3) . ?
C4 H4 1.0000 . ?
C5 C13 1.514(3) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.481(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.472(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.500(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
S1 O8 1.4362(19) . ?
S1 O7 1.440(2) . ?
S1 O6 1.445(2) . ?
S1 C19 1.820(3) . ?
F1 C19 1.348(3) . ?
F2 C19 1.333(3) . ?
F3 C19 1.332(3) . ?

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
C18 N1 C14 121.4(2) . . ?
C18 N1 C13 118.8(2) . . ?
C14 N1 C13 119.8(2) . . ?
C5 O1 C1 111.84(15) . . ?
C1 O2 C6 113.22(19) . . ?
C7 O3 C2 113.88(18) . . ?
C9 O4 C3 115.5(2) . . ?
C4 O5 C11 115.56(17) . . ?
O2 C1 O1 108.02(16) . . ?
O2 C1 C2 108.38(17) . . ?
O1 C1 C2 109.68(17) . . ?
O2 C1 H1 110.2 . . ?
O1 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
O3 C2 C3 107.63(16) . . ?
O3 C2 C1 109.98(17) . . ?
C3 C2 C1 111.04(17) . . ?
O3 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
O4 C3 C2 110.01(17) . . ?
O4 C3 C4 107.90(17) . . ?
C2 C3 C4 111.77(17) . . ?
O4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C4 C3 H3 109.0 . . ?
O5 C4 C3 111.66(16) . . ?
O5 C4 C5 107.48(17) . . ?
C3 C4 C5 109.99(16) . . ?
O5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
O1 C5 C13 108.01(17) . . ?
O1 C5 C4 109.38(17) . . ?
C13 C5 C4 108.69(16) . . ?
O1 C5 H5 110.2 . . ?
C13 C5 H5 110.2 . . ?
C4 C5 H5 110.2 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C8 109.9(2) . . ?
O3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C10 109.8(3) . . ?
O4 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O4 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 C12 108.4(2) . . ?
O5 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
O5 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C5 112.37(17) . . ?
N1 C13 H13A 109.1 . . ?
C5 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C5 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N1 C14 C15 119.8(2) . . ?
N1 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N1 C18 C17 120.4(2) . . ?
N1 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
O8 S1 O7 115.46(13) . . ?
O8 S1 O6 116.35(13) . . ?
O7 S1 O6 114.47(13) . . ?
O8 S1 C19 103.51(12) . . ?
O7 S1 C19 102.52(12) . . ?
O6 S1 C19 101.55(13) . . ?
F3 C19 F2 107.3(2) . . ?
F3 C19 F1 106.9(2) . . ?
F2 C19 F1 107.4(2) . . ?
F3 C19 S1 112.34(19) . . ?
F2 C19 S1 112.17(18) . . ?
F1 C19 S1 110.49(17) . . ?

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
C6 O2 C1 O1 -81.6(2) . . . . ?
C6 O2 C1 C2 159.63(19) . . . . ?
C5 O1 C1 O2 178.01(16) . . . . ?
C5 O1 C1 C2 -64.1(2) . . . . ?
C7 O3 C2 C3 -136.9(2) . . . . ?
C7 O3 C2 C1 102.0(3) . . . . ?
O2 C1 C2 O3 -68.5(2) . . . . ?
O1 C1 C2 O3 173.74(16) . . . . ?
O2 C1 C2 C3 172.44(17) . . . . ?
O1 C1 C2 C3 54.7(2) . . . . ?
C9 O4 C3 C2 -105.3(3) . . . . ?
C9 O4 C3 C4 132.6(3) . . . . ?
O3 C2 C3 O4 70.6(2) . . . . ?
C1 C2 C3 O4 -168.99(16) . . . . ?
O3 C2 C3 C4 -169.56(16) . . . . ?
C1 C2 C3 C4 -49.1(2) . . . . ?
C11 O5 C4 C3 100.0(2) . . . . ?
C11 O5 C4 C5 -139.28(19) . . . . ?
O4 C3 C4 O5 -69.8(2) . . . . ?
C2 C3 C4 O5 169.11(16) . . . . ?
O4 C3 C4 C5 170.94(17) . . . . ?
C2 C3 C4 C5 49.9(2) . . . . ?
C1 O1 C5 C13 -176.61(17) . . . . ?
C1 O1 C5 C4 65.3(2) . . . . ?
O5 C4 C5 O1 -178.53(15) . . . . ?
C3 C4 C5 O1 -56.8(2) . . . . ?
O5 C4 C5 C13 63.7(2) . . . . ?
C3 C4 C5 C13 -174.48(18) . . . . ?
C2 O3 C7 C8 172.4(2) . . . . ?
C3 O4 C9 C10 178.2(3) . . . . ?
C4 O5 C11 C12 162.7(2) . . . . ?
C18 N1 C13 C5 -89.9(2) . . . . ?
C14 N1 C13 C5 91.6(2) . . . . ?
O1 C5 C13 N1 64.7(2) . . . . ?
C4 C5 C13 N1 -176.73(19) . . . . ?
C18 N1 C14 C15 -1.5(3) . . . . ?
C13 N1 C14 C15 176.9(2) . . . . ?
N1 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C14 N1 C18 C17 1.7(3) . . . . ?
C13 N1 C18 C17 -176.8(2) . . . . ?
C16 C17 C18 N1 -0.2(4) . . . . ?
O8 S1 C19 F3 61.5(2) . . . . ?
O7 S1 C19 F3 -178.09(19) . . . . ?
O6 S1 C19 F3 -59.5(2) . . . . ?
O8 S1 C19 F2 -59.5(2) . . . . ?
O7 S1 C19 F2 60.9(2) . . . . ?
O6 S1 C19 F2 179.5(2) . . . . ?
O8 S1 C19 F1 -179.28(17) . . . . ?
O7 S1 C19 F1 -58.9(2) . . . . ?
O6 S1 C19 F1 59.7(2) . . . . ?

_refine_diff_density_max         0.617
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

