# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_SH-113a
_database_code_depnum_ccdc_archive 'CCDC 1832225'

_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {3e25669c-a5dd-4637-93c0-f600854a2099}
#============================================================================== 
#SH-113a
#==============================================================================
_audit_creation_date             2018-02-13
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
2-(3-methyl-1-phenyl-1H-pyrazol-2-ium-4-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
_chemical_name_common            ?
_chemical_melting_point          458
_chemical_formula_moiety         'C14 H12 F6 N2 O4 S2'
_chemical_formula_sum            'C14 H12 F6 N2 O4 S2'
_chemical_formula_weight         450.38
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
F F 0.0171 0.0103 '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           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'

#==============================================================================
#   CRYSTAL DATA
#==============================================================================


_cell_length_a                   8.4088(5)
_cell_length_b                   17.3980(11)
_cell_length_c                   12.1982(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.3180(10)
_cell_angle_gamma                90
_cell_volume                     1749.85(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2721
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.391
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered conforcal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8458
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3079
_reflns_number_gt                2618
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0383P)²+1.9730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     258
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.0948
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.001

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 0.1496(3) 0.40652(14) 0.3715(2) 0.0222(5) Uani 1 1 d . U . . .
C2 C 0.1237(3) 0.49283(13) 0.3770(2) 0.0225(5) Uani 1 1 d . U . . .
H2A H 0.005775 0.503342 0.358317 0.027 Uiso 1 1 calc R U . . .
H2B H 0.163787 0.510138 0.454788 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2059(3) 0.53989(13) 0.30038(19) 0.0163(5) Uani 1 1 d . U . . .
C4 C 0.3289(3) 0.51862(13) 0.2461(2) 0.0217(5) Uani 1 1 d . U . . .
H4 H 0.378200 0.469297 0.250044 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1725(3) 0.61584(13) 0.2712(2) 0.0198(5) Uani 1 1 d . U . . .
C6 C 0.4892(3) 0.58453(12) 0.11934(19) 0.0150(5) Uani 1 1 d . U . . .
C7 C 0.6403(3) 0.55395(15) 0.1594(2) 0.0257(5) Uani 1 1 d . U . . .
H7 H 0.663471 0.528882 0.229956 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7582(3) 0.56047(15) 0.0948(2) 0.0263(6) Uani 1 1 d . U . . .
H8 H 0.862359 0.538518 0.120254 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7250(3) 0.59861(14) -0.0061(2) 0.0225(5) Uani 1 1 d . U . . .
H9 H 0.807314 0.604753 -0.048735 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5720(3) 0.62783(15) -0.0449(2) 0.0300(6) Uani 1 1 d . U . . .
H10 H 0.549059 0.653532 -0.114911 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4508(3) 0.62021(14) 0.0171(2) 0.0252(5) Uani 1 1 d . U . . .
H11 H 0.344458 0.639108 -0.010444 0.030 Uiso 1 1 calc R U . . .
C12 C 0.0551(4) 0.67016(15) 0.3061(3) 0.0408(8) Uani 1 1 d . U . . .
H12A H 0.082920 0.677720 0.387200 0.061 Uiso 1 1 calc R U . . .
H12B H -0.054714 0.648966 0.285665 0.061 Uiso 1 1 calc R U . . .
H12C H 0.059747 0.719593 0.268307 0.061 Uiso 1 1 calc R U . . .
C13 C -0.1486(3) 0.32897(16) 0.3001(2) 0.0322(6) Uani 1 1 d . U . . .
C14 C 0.4716(3) 0.35788(14) 0.4536(2) 0.0232(5) Uani 1 1 d . U . . .
F1 F -0.22339(19) 0.39179(10) 0.32752(16) 0.0480(5) Uani 1 1 d . U . . .
F2 F -0.24437(18) 0.29512(11) 0.21436(14) 0.0450(5) Uani 1 1 d . U . . .
F3 F -0.12849(18) 0.28121(10) 0.38607(14) 0.0446(5) Uani 1 1 d . U . . .
F4 F 0.56884(17) 0.31819(9) 0.53204(14) 0.0380(4) Uani 1 1 d . U . . .
F5 F 0.52970(18) 0.42859(9) 0.45211(12) 0.0330(4) Uani 1 1 d . U . . .
F6 F 0.47595(17) 0.32589(10) 0.35460(14) 0.0397(4) Uani 1 1 d . U . . .
N1 N 0.3677(2) 0.57804(10) 0.18722(16) 0.0152(4) Uani 1 1 d . U . . .
N2 N 0.2702(2) 0.63702(11) 0.20129(18) 0.0206(4) Uani 1 1 d . U . . .
O1 O -0.0081(2) 0.40903(9) 0.17113(14) 0.0243(4) Uani 1 1 d . U . . .
O2 O 0.1180(2) 0.28546(9) 0.24183(17) 0.0317(5) Uani 1 1 d . U . . .
O3 O 0.2261(2) 0.27860(12) 0.4777(2) 0.0538(7) Uani 1 1 d . U . . .
O4 O 0.2808(2) 0.40273(13) 0.57943(16) 0.0450(6) Uani 1 1 d . U . . .
S1 S 0.04551(7) 0.35728(3) 0.26259(5) 0.02185(17) Uani 1 1 d . U . . .
S2 S 0.26353(7) 0.35899(4) 0.47851(6) 0.02615(18) Uani 1 1 d . U . . .
H2N H 0.291(3) 0.6815(16) 0.179(2) 0.028(7) 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
C1 C2 1.521(3) . ?
C1 S1 1.676(3) . ?
C1 S2 1.678(2) . ?
C2 C3 1.508(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.383(3) . ?
C3 C4 1.384(3) . ?
C4 N1 1.335(3) . ?
C4 H4 0.9500 . ?
C5 N2 1.347(3) . ?
C5 C12 1.488(3) . ?
C6 C11 1.374(3) . ?
C6 C7 1.376(3) . ?
C6 N1 1.440(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 F3 1.323(3) . ?
C13 F2 1.326(3) . ?
C13 F1 1.336(3) . ?
C13 S1 1.846(3) . ?
C14 F5 1.325(3) . ?
C14 F4 1.325(3) . ?
C14 F6 1.337(3) . ?
C14 S2 1.834(2) . ?
N1 N2 1.345(3) . ?
N2 H2N 0.85(3) . ?
O1 S1 1.4356(17) . ?
O2 S1 1.4346(17) . ?
O3 S2 1.433(2) . ?
O4 S2 1.430(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 118.86(18) . . ?
C2 C1 S2 121.15(19) . . ?
S1 C1 S2 119.64(14) . . ?
C3 C2 C1 114.97(19) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C5 C3 C4 105.4(2) . . ?
C5 C3 C2 125.7(2) . . ?
C4 C3 C2 128.9(2) . . ?
N1 C4 C3 109.5(2) . . ?
N1 C4 H4 125.2 . . ?
C3 C4 H4 125.2 . . ?
N2 C5 C3 107.82(19) . . ?
N2 C5 C12 121.9(2) . . ?
C3 C5 C12 130.3(2) . . ?
C11 C6 C7 122.2(2) . . ?
C11 C6 N1 119.4(2) . . ?
C7 C6 N1 118.4(2) . . ?
C6 C7 C8 118.7(2) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 118.1(2) . . ?
C6 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3 C13 F2 108.0(2) . . ?
F3 C13 F1 108.0(2) . . ?
F2 C13 F1 108.5(2) . . ?
F3 C13 S1 112.48(17) . . ?
F2 C13 S1 110.66(19) . . ?
F1 C13 S1 109.04(18) . . ?
F5 C14 F4 108.46(19) . . ?
F5 C14 F6 107.4(2) . . ?
F4 C14 F6 108.24(19) . . ?
F5 C14 S2 111.04(16) . . ?
F4 C14 S2 111.08(17) . . ?
F6 C14 S2 110.52(16) . . ?
C4 N1 N2 107.63(18) . . ?
C4 N1 C6 130.20(19) . . ?
N2 N1 C6 122.16(18) . . ?
N1 N2 C5 109.56(19) . . ?
N1 N2 H2N 119.0(18) . . ?
C5 N2 H2N 129.8(18) . . ?
O2 S1 O1 119.26(11) . . ?
O2 S1 C1 114.29(11) . . ?
O1 S1 C1 109.33(11) . . ?
O2 S1 C13 103.79(12) . . ?
O1 S1 C13 101.62(11) . . ?
C1 S1 C13 106.83(13) . . ?
O4 S2 O3 120.65(14) . . ?
O4 S2 C1 110.70(12) . . ?
O3 S2 C1 112.62(12) . . ?
O4 S2 C14 102.09(12) . . ?
O3 S2 C14 101.79(12) . . ?
C1 S2 C14 107.10(11) . . ?

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
S1 C1 C2 C3 -76.5(2) . . . . ?
S2 C1 C2 C3 110.4(2) . . . . ?
C1 C2 C3 C5 164.6(2) . . . . ?
C1 C2 C3 C4 -16.4(4) . . . . ?
C5 C3 C4 N1 -0.1(3) . . . . ?
C2 C3 C4 N1 -179.4(2) . . . . ?
C4 C3 C5 N2 1.1(3) . . . . ?
C2 C3 C5 N2 -179.6(2) . . . . ?
C4 C3 C5 C12 -178.2(3) . . . . ?
C2 C3 C5 C12 1.0(4) . . . . ?
C11 C6 C7 C8 0.9(4) . . . . ?
N1 C6 C7 C8 -179.6(2) . . . . ?
C6 C7 C8 C9 1.7(4) . . . . ?
C7 C8 C9 C10 -2.5(4) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C7 C6 C11 C10 -2.6(4) . . . . ?
N1 C6 C11 C10 177.9(2) . . . . ?
C9 C10 C11 C6 1.7(4) . . . . ?
C3 C4 N1 N2 -0.9(3) . . . . ?
C3 C4 N1 C6 178.7(2) . . . . ?
C11 C6 N1 C4 136.5(3) . . . . ?
C7 C6 N1 C4 -43.0(4) . . . . ?
C11 C6 N1 N2 -44.0(3) . . . . ?
C7 C6 N1 N2 136.5(2) . . . . ?
C4 N1 N2 C5 1.6(3) . . . . ?
C6 N1 N2 C5 -178.0(2) . . . . ?
C3 C5 N2 N1 -1.7(3) . . . . ?
C12 C5 N2 N1 177.7(2) . . . . ?
C2 C1 S1 O2 157.74(17) . . . . ?
S2 C1 S1 O2 -28.99(18) . . . . ?
C2 C1 S1 O1 21.1(2) . . . . ?
S2 C1 S1 O1 -165.59(13) . . . . ?
C2 C1 S1 C13 -88.08(19) . . . . ?
S2 C1 S1 C13 85.19(16) . . . . ?
F3 C13 S1 O2 56.8(2) . . . . ?
F2 C13 S1 O2 -64.1(2) . . . . ?
F1 C13 S1 O2 176.56(18) . . . . ?
F3 C13 S1 O1 -178.8(2) . . . . ?
F2 C13 S1 O1 60.2(2) . . . . ?
F1 C13 S1 O1 -59.1(2) . . . . ?
F3 C13 S1 C1 -64.3(2) . . . . ?
F2 C13 S1 C1 174.77(17) . . . . ?
F1 C13 S1 C1 55.5(2) . . . . ?
C2 C1 S2 O4 19.5(2) . . . . ?
S1 C1 S2 O4 -153.64(14) . . . . ?
C2 C1 S2 O3 157.87(19) . . . . ?
S1 C1 S2 O3 -15.2(2) . . . . ?
C2 C1 S2 C14 -91.0(2) . . . . ?
S1 C1 S2 C14 95.84(15) . . . . ?
F5 C14 S2 O4 -54.3(2) . . . . ?
F4 C14 S2 O4 66.51(19) . . . . ?
F6 C14 S2 O4 -173.33(17) . . . . ?
F5 C14 S2 O3 -179.55(18) . . . . ?
F4 C14 S2 O3 -58.76(19) . . . . ?
F6 C14 S2 O3 61.4(2) . . . . ?
F5 C14 S2 C1 62.1(2) . . . . ?
F4 C14 S2 C1 -177.13(16) . . . . ?
F6 C14 S2 C1 -57.0(2) . . . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.060



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_HY-1021
_database_code_depnum_ccdc_archive 'CCDC 1833410'
#Added by publCIF



_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
#============================================================================== 
# HY-1021
#==============================================================================
_audit_creation_date             'October 23 2015'
_audit_creation_method           SHELXL-97

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
2-(2,2-bis((trifluoromethyl)sulfonyl)ethyl)-1-(phenylethynyl)-1,5,6,7-tetrahydro-4H-indol-4-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 F6 N O5 S2'
_chemical_formula_sum            'C20 H15 F6 N O5 S2'
_chemical_formula_weight         527.45
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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


_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   12.6441(9)
_cell_length_b                   11.3643(8)
_cell_length_c                   16.2034(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.7510(10)
_cell_angle_gamma                90.00
_cell_volume                     2162.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4443
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.88
_exptl_crystal_description       block
_exptl_crystal_colour            colurless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;
_exptl_special_details           ?

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10342
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3817
_reflns_number_gt                3362
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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. 
;

_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)+(0.0369P)²+1.3932P] 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         3817
_refine_ls_number_parameters     310
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      0.999
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.88725(15) 0.32029(15) 0.58007(12) 0.0156(4) Uani 1 1 d U . .
C2 C 0.83979(15) 0.22897(16) 0.62524(12) 0.0191(4) Uani 1 1 d U . .
H2A H 0.8342 0.2641 0.6794 0.023 Uiso 1 1 calc R . .
H2B H 0.8937 0.1621 0.6440 0.023 Uiso 1 1 calc R . .
C3 C 0.72259(16) 0.18241(16) 0.56613(13) 0.0200(4) Uani 1 1 d U . .
H3A H 0.6946 0.1279 0.6012 0.024 Uiso 1 1 calc R . .
H3B H 0.7301 0.1373 0.5163 0.024 Uiso 1 1 calc R . .
C4 C 0.63481(15) 0.28087(15) 0.52834(12) 0.0174(4) Uani 1 1 d U . .
H4A H 0.5665 0.2496 0.4803 0.021 Uiso 1 1 calc R . .
H4B H 0.6111 0.3132 0.5756 0.021 Uiso 1 1 calc R . .
C5 C 0.68831(14) 0.37485(15) 0.49294(11) 0.0141(4) Uani 1 1 d U . .
C6 C 0.71231(14) 0.53100(15) 0.41316(12) 0.0144(4) Uani 1 1 d U . .
C7 C 0.81743(15) 0.49020(15) 0.46321(12) 0.0151(4) Uani 1 1 d U . .
H7 H 0.8879 0.5208 0.4644 0.018 Uiso 1 1 calc R . .
C8 C 0.80288(14) 0.39230(15) 0.51409(12) 0.0142(4) Uani 1 1 d U . .
C11 C 0.41751(15) 0.47886(15) 0.34475(12) 0.0166(4) Uani 1 1 d U . .
C12 C 0.29856(15) 0.49459(15) 0.29249(12) 0.0159(4) Uani 1 1 d U . .
C13 C 0.21528(16) 0.42878(17) 0.30967(13) 0.0229(4) Uani 1 1 d U . .
H13 H 0.2368 0.3735 0.3570 0.028 Uiso 1 1 calc R . .
C14 C 0.10114(17) 0.44473(18) 0.25714(14) 0.0284(5) Uani 1 1 d U . .
H14 H 0.0447 0.4001 0.2688 0.034 Uiso 1 1 calc R . .
C15 C 0.06900(16) 0.52504(18) 0.18801(13) 0.0263(5) Uani 1 1 d U . .
H15 H -0.0092 0.5344 0.1519 0.032 Uiso 1 1 calc R . .
C16 C 0.15016(16) 0.59147(17) 0.17151(13) 0.0231(4) Uani 1 1 d U . .
H16 H 0.1277 0.6476 0.1247 0.028 Uiso 1 1 calc R . .
C17 C 0.26469(16) 0.57660(17) 0.22316(13) 0.0204(4) Uani 1 1 d U . .
H17 H 0.3204 0.6224 0.2114 0.024 Uiso 1 1 calc R . .
C18 C 0.67259(14) 0.62893(15) 0.34669(12) 0.0150(4) Uani 1 1 d U . .
H18A H 0.6019 0.6637 0.3490 0.018 Uiso 1 1 calc R . .
H18B H 0.6553 0.5974 0.2861 0.018 Uiso 1 1 calc R . .
C19 C 0.76473(15) 0.72451(15) 0.36651(11) 0.0130(4) Uani 1 1 d U . .
C20 C 0.79138(15) 0.69034(16) 0.20048(12) 0.0180(4) Uani 1 1 d U . .
C21 C 0.90542(17) 0.84418(17) 0.52570(13) 0.0250(4) Uani 1 1 d U . .
F1 F 0.83112(9) 0.59416(8) 0.24722(7) 0.0189(2) Uani 1 1 d U . .
F2 F 0.69955(10) 0.66441(10) 0.13062(7) 0.0317(3) Uani 1 1 d U . .
F3 F 0.87012(10) 0.73342(10) 0.17344(8) 0.0306(3) Uani 1 1 d U . .
F4 F 0.94659(10) 0.74304(11) 0.56433(8) 0.0377(3) Uani 1 1 d U . .
F5 F 0.96770(9) 0.88265(10) 0.48142(8) 0.0288(3) Uani 1 1 d U . .
F6 F 0.90778(11) 0.92279(12) 0.58690(8) 0.0405(3) Uani 1 1 d U . .
N1 N 0.63152(12) 0.46000(12) 0.43132(10) 0.0137(3) Uani 1 1 d U . .
C10 C 0.51670(15) 0.46815(15) 0.38736(12) 0.0150(4) Uani 1 1 d U . .
O1 O 0.99001(10) 0.33433(11) 0.59963(9) 0.0220(3) Uani 1 1 d U . .
O2 O 0.63661(10) 0.83502(11) 0.21982(8) 0.0185(3) Uani 1 1 d U . .
O3 O 0.84147(10) 0.89337(10) 0.28893(8) 0.0187(3) Uani 1 1 d U . .
O4 O 0.70119(12) 0.76469(12) 0.50224(9) 0.0250(3) Uani 1 1 d U . .
O5 O 0.71484(12) 0.93765(11) 0.41310(9) 0.0237(3) Uani 1 1 d U . .
S1 S 0.75339(4) 0.80702(4) 0.26787(3) 0.01336(11) Uani 1 1 d U . .
S2 S 0.75461(4) 0.82526(4) 0.45088(3) 0.01704(12) Uani 1 1 d U . .
H19 H 0.8358(18) 0.6938(17) 0.3879(13) 0.020 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
C1 O1 1.228(2) . ?
C1 C8 1.451(2) . ?
C1 C2 1.516(3) . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.535(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C8 1.374(2) . ?
C5 N1 1.385(2) . ?
C6 C7 1.357(2) . ?
C6 N1 1.415(2) . ?
C6 C18 1.500(2) . ?
C7 C8 1.437(2) . ?
C7 H7 0.9500 . ?
C11 C10 1.193(2) . ?
C11 C12 1.438(2) . ?
C12 C17 1.399(3) . ?
C12 C13 1.401(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.537(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 S1 1.8123(17) . ?
C19 S2 1.8237(18) . ?
C19 H19 0.90(2) . ?
C20 F1 1.319(2) . ?
C20 F2 1.320(2) . ?
C20 F3 1.321(2) . ?
C20 S1 1.8895(18) . ?
C21 F4 1.320(2) . ?
C21 F5 1.321(2) . ?
C21 F6 1.327(2) . ?
C21 S2 1.854(2) . ?
N1 C10 1.363(2) . ?
O2 S1 1.4268(13) . ?
O3 S1 1.4277(13) . ?
O4 S2 1.4279(14) . ?
O5 S2 1.4250(13) . ?

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 122.37(17) . . ?
O1 C1 C2 122.31(16) . . ?
C8 C1 C2 115.30(15) . . ?
C1 C2 C3 113.54(15) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C4 112.77(15) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 108.20(15) . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C8 C5 N1 107.22(15) . . ?
C8 C5 C4 126.53(16) . . ?
N1 C5 C4 126.24(15) . . ?
C7 C6 N1 107.67(15) . . ?
C7 C6 C18 132.53(16) . . ?
N1 C6 C18 119.79(15) . . ?
C6 C7 C8 107.60(15) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
C5 C8 C7 108.42(15) . . ?
C5 C8 C1 121.45(16) . . ?
C7 C8 C1 130.10(16) . . ?
C10 C11 C12 178.5(2) . . ?
C17 C12 C13 119.09(17) . . ?
C17 C12 C11 119.86(16) . . ?
C13 C12 C11 121.05(17) . . ?
C14 C13 C12 119.68(18) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.59(19) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.13(18) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.12(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.37(18) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C6 C18 C19 110.37(14) . . ?
C6 C18 H18A 109.6 . . ?
C19 C18 H18A 109.6 . . ?
C6 C18 H18B 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 S1 112.03(12) . . ?
C18 C19 S2 109.99(12) . . ?
S1 C19 S2 109.37(9) . . ?
C18 C19 H19 112.1(13) . . ?
S1 C19 H19 106.2(13) . . ?
S2 C19 H19 106.9(13) . . ?
F1 C20 F2 109.54(15) . . ?
F1 C20 F3 108.90(14) . . ?
F2 C20 F3 109.26(15) . . ?
F1 C20 S1 111.97(12) . . ?
F2 C20 S1 108.73(12) . . ?
F3 C20 S1 108.41(12) . . ?
F4 C21 F5 109.64(17) . . ?
F4 C21 F6 109.64(16) . . ?
F5 C21 F6 109.28(16) . . ?
F4 C21 S2 109.78(13) . . ?
F5 C21 S2 111.03(13) . . ?
F6 C21 S2 107.43(14) . . ?
C10 N1 C5 126.27(14) . . ?
C10 N1 C6 124.31(14) . . ?
C5 N1 C6 109.08(14) . . ?
C11 C10 N1 175.92(19) . . ?
O2 S1 O3 122.35(8) . . ?
O2 S1 C19 108.93(8) . . ?
O3 S1 C19 110.19(8) . . ?
O2 S1 C20 105.93(8) . . ?
O3 S1 C20 106.12(8) . . ?
C19 S1 C20 101.10(8) . . ?
O5 S2 O4 120.97(8) . . ?
O5 S2 C19 110.63(8) . . ?
O4 S2 C19 108.30(8) . . ?
O5 S2 C21 106.89(9) . . ?
O4 S2 C21 105.59(9) . . ?
C19 S2 C21 102.83(9) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_SH-119a
_database_code_depnum_ccdc_archive 'CCDC 1832228'

_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {63cffa51-b0e2-422c-be02-e5615ced5403}
#==============================================================================
# SH-119a
#==============================================================================
_audit_creation_date             2018-02-15
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
2-(2,4-diphenyloxazol-3-ium-5-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide 
;
_chemical_name_common            ?
_chemical_melting_point          479
_chemical_formula_moiety         'C19 H13 F6 N O5 S2, C2 H6 O S'
_chemical_formula_sum            'C21 H19 F6 N O6 S3'
_chemical_formula_weight         591.55
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
F F 0.0171 0.0103 '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           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                   13.0371(9)
_cell_length_b                   14.5605(10)
_cell_length_c                   14.0643(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.6170(10)
_cell_angle_gamma                90
_cell_volume                     2446.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4035
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.139
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            11761
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4313
_reflns_number_gt                3661
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0413P)²+3.1294P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4313
_refine_ls_number_parameters     378
_refine_ls_number_restraints     548
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.329
_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
C1 C 0.6295(2) 0.74750(16) 0.24292(18) 0.0182(3) Uani 1 1 d . U . . .
C2 C 0.7012(2) 0.77344(16) 0.35478(18) 0.0177(4) Uani 1 1 d . U . . .
H2A H 0.780174 0.759630 0.368179 0.021 Uiso 1 1 calc R U . . .
H2B H 0.695494 0.840716 0.361640 0.021 Uiso 1 1 calc R U . . .
C3 C 0.67527(19) 0.72875(16) 0.43746(18) 0.0163(3) Uani 1 1 d . U . . .
C4 C 0.66051(19) 0.76083(16) 0.52095(18) 0.0161(3) Uani 1 1 d . U . . .
C5 C 0.65695(19) 0.60948(16) 0.52498(17) 0.0152(3) Uani 1 1 d . U . . .
C6 C 0.6572(2) 0.85519(16) 0.55661(18) 0.0181(4) Uani 1 1 d . U . . .
C7 C 0.7354(2) 0.91982(17) 0.55433(18) 0.0213(4) Uani 1 1 d . U . . .
H7 H 0.791533 0.902387 0.530909 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7312(2) 1.00952(18) 0.58621(19) 0.0246(4) Uani 1 1 d . U . . .
H8 H 0.783037 1.053746 0.582580 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6515(2) 1.03462(18) 0.62328(19) 0.0253(4) Uani 1 1 d . U . . .
H9 H 0.650078 1.095633 0.646647 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5739(2) 0.97098(17) 0.62637(19) 0.0231(4) Uani 1 1 d . U . . .
H10 H 0.519194 0.988344 0.651655 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5763(2) 0.88173(17) 0.59242(18) 0.0203(4) Uani 1 1 d . U . . .
H11 H 0.522273 0.838440 0.593624 0.024 Uiso 1 1 calc R U . . .
C12 C 0.64834(19) 0.51320(16) 0.54822(18) 0.0171(4) Uani 1 1 d . U . . .
C13 C 0.6569(2) 0.44503(16) 0.48183(18) 0.0186(4) Uani 1 1 d . U . . .
H13 H 0.670536 0.461338 0.422526 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6454(2) 0.35329(17) 0.50295(19) 0.0202(4) Uani 1 1 d . U . . .
H14 H 0.651139 0.306747 0.458008 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6255(2) 0.32958(17) 0.58958(19) 0.0203(4) Uani 1 1 d . U . . .
H15 H 0.617024 0.266818 0.603437 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6179(2) 0.39701(17) 0.65602(19) 0.0200(4) Uani 1 1 d . U . . .
H16 H 0.604975 0.380181 0.715565 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6290(2) 0.48879(17) 0.63609(18) 0.0191(4) Uani 1 1 d . U . . .
H17 H 0.623553 0.534903 0.681630 0.023 Uiso 1 1 calc R U . . .
C18 C 0.6396(2) 0.56961(18) 0.1638(2) 0.0255(4) Uani 1 1 d . U . . .
C19 C 0.5176(2) 0.90972(18) 0.1401(2) 0.0253(4) Uani 1 1 d . U . . .
F1 F 0.52937(14) 0.56316(11) 0.11694(15) 0.0451(5) Uani 1 1 d . U . . .
F2 F 0.68276(16) 0.52024(11) 0.10948(13) 0.0401(4) Uani 1 1 d . U . . .
F3 F 0.67321(15) 0.53157(10) 0.25697(12) 0.0350(4) Uani 1 1 d . U . . .
F4 F 0.56206(17) 0.90836(11) 0.07067(13) 0.0424(4) Uani 1 1 d . U . . .
F5 F 0.41805(14) 0.95076(11) 0.09810(13) 0.0397(4) Uani 1 1 d . U . . .
F6 F 0.58296(13) 0.96103(10) 0.21945(12) 0.0315(4) Uani 1 1 d . U . . .
N1 N 0.64944(16) 0.68346(13) 0.57459(15) 0.0153(3) Uani 1 1 d . U . . .
O1 O 0.67368(13) 0.63317(11) 0.44043(12) 0.0155(3) Uani 1 1 d . U . . .
O2 O 0.80522(16) 0.68080(14) 0.23250(17) 0.0354(5) Uani 1 1 d . U . . .
O3 O 0.64787(19) 0.71714(14) 0.06727(15) 0.0379(5) Uani 1 1 d . U . . .
O4 O 0.43382(16) 0.74791(13) 0.08907(15) 0.0350(5) Uani 1 1 d . U . . .
O5 O 0.45757(15) 0.81239(13) 0.26070(15) 0.0292(4) Uani 1 1 d . U . . .
S1 S 0.68710(5) 0.68980(4) 0.17334(5) 0.02121(16) Uani 1 1 d . U . . .
S2 S 0.50123(5) 0.79308(4) 0.18410(5) 0.01984(16) Uani 1 1 d . U . . .
S1S S 0.60507(9) 0.71513(7) 0.83757(8) 0.0146(2) Uani 0.5559(15) 1 d D U P A 1
O1S O 0.5780(3) 0.6933(2) 0.72389(17) 0.0188(5) Uani 0.5559(15) 1 d D U P A 1
C1S C 0.4855(5) 0.6540(4) 0.8266(4) 0.0191(7) Uani 0.5559(15) 1 d . U P A 1
H1P H 0.419582 0.693694 0.796328 0.029 Uiso 0.5559(15) 1 calc R U P A 1
H1Q H 0.493143 0.633507 0.895489 0.029 Uiso 0.5559(15) 1 calc R U P A 1
H1R H 0.476598 0.600423 0.781749 0.029 Uiso 0.5559(15) 1 calc R U P A 1
C2S C 0.5705(10) 0.8302(3) 0.8493(7) 0.0170(8) Uani 0.5559(15) 1 d D U P A 1
H2P H 0.620167 0.870935 0.831783 0.026 Uiso 0.5559(15) 1 calc R U P A 1
H2Q H 0.579288 0.841938 0.920721 0.026 Uiso 0.5559(15) 1 calc R U P A 1
H2R H 0.492653 0.841665 0.801754 0.026 Uiso 0.5559(15) 1 calc R U P A 1
S1T S 0.53131(11) 0.73477(9) 0.75377(10) 0.0163(3) Uani 0.4441(15) 1 d D U P A
2
O1T O 0.6396(3) 0.6943(3) 0.7543(3) 0.0165(6) Uani 0.4441(15) 1 d D U P A 2
C1T C 0.4925(6) 0.6679(4) 0.8634(5) 0.0157(9) Uani 0.4441(15) 1 d . U P A 2
H1S H 0.524181 0.605849 0.873683 0.024 Uiso 0.4441(15) 1 calc R U P A 2
H1T H 0.411013 0.664146 0.839812 0.024 Uiso 0.4441(15) 1 calc R U P A 2
H1U H 0.523895 0.701852 0.928976 0.024 Uiso 0.4441(15) 1 calc R U P A 2
C2T C 0.5744(13) 0.8292(4) 0.8387(9) 0.0170(9) Uani 0.4441(15) 1 d D U P A 2
H2S H 0.625979 0.808175 0.907545 0.026 Uiso 0.4441(15) 1 calc R U P A 2
H2T H 0.508897 0.857921 0.843899 0.026 Uiso 0.4441(15) 1 calc R U P A 2
H2U H 0.612450 0.873963 0.812096 0.026 Uiso 0.4441(15) 1 calc R U P A 2
H1N H 0.638(2) 0.6844(18) 0.626(2) 0.020 Uiso 1 1 d . 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
C1 C2 1.521(3) . ?
C1 S1 1.678(2) . ?
C1 S2 1.678(2) . ?
C2 C3 1.485(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.347(3) . ?
C3 O1 1.393(3) . ?
C4 N1 1.395(3) . ?
C4 C6 1.469(3) . ?
C5 N1 1.308(3) . ?
C5 O1 1.337(3) . ?
C5 C12 1.454(3) . ?
C6 C11 1.393(4) . ?
C6 C7 1.397(3) . ?
C7 C8 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.397(3) . ?
C12 C17 1.403(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 F1 1.323(3) . ?
C18 F3 1.324(3) . ?
C18 F2 1.328(3) . ?
C18 S1 1.843(3) . ?
C19 F4 1.321(3) . ?
C19 F6 1.329(3) . ?
C19 F5 1.332(3) . ?
C19 S2 1.849(3) . ?
N1 H1N 0.79(3) . ?
O2 S1 1.433(2) . ?
O3 S1 1.4262(19) . ?
O4 S2 1.432(2) . ?
O5 S2 1.4335(19) . ?
S1S O1S 1.526(2) . ?
S1S C1S 1.748(6) . ?
S1S C2S 1.759(4) . ?
C1S H1P 0.9800 . ?
C1S H1Q 0.9800 . ?
C1S H1R 0.9800 . ?
C2S H2P 0.9800 . ?
C2S H2Q 0.9800 . ?
C2S H2R 0.9800 . ?
S1T O1T 1.527(2) . ?
S1T C2T 1.759(5) . ?
S1T C1T 2.050(6) . ?
C1T H1S 0.9800 . ?
C1T H1T 0.9800 . ?
C1T H1U 0.9800 . ?
C2T H2S 0.9800 . ?
C2T H2T 0.9800 . ?
C2T H2U 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
C2 C1 S1 119.65(18) . . ?
C2 C1 S2 119.33(18) . . ?
S1 C1 S2 120.08(15) . . ?
C3 C2 C1 117.6(2) . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C4 C3 O1 108.1(2) . . ?
C4 C3 C2 133.4(2) . . ?
O1 C3 C2 118.2(2) . . ?
C3 C4 N1 105.9(2) . . ?
C3 C4 C6 131.0(2) . . ?
N1 C4 C6 123.2(2) . . ?
N1 C5 O1 109.6(2) . . ?
N1 C5 C12 130.2(2) . . ?
O1 C5 C12 120.2(2) . . ?
C11 C6 C7 119.1(2) . . ?
C11 C6 C4 120.9(2) . . ?
C7 C6 C4 120.0(2) . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C6 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C17 120.0(2) . . ?
C13 C12 C5 120.0(2) . . ?
C17 C12 C5 120.0(2) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
F1 C18 F3 109.0(2) . . ?
F1 C18 F2 107.5(2) . . ?
F3 C18 F2 107.1(2) . . ?
F1 C18 S1 111.71(18) . . ?
F3 C18 S1 110.92(18) . . ?
F2 C18 S1 110.38(18) . . ?
F4 C19 F6 107.8(2) . . ?
F4 C19 F5 108.5(2) . . ?
F6 C19 F5 107.7(2) . . ?
F4 C19 S2 112.16(18) . . ?
F6 C19 S2 110.89(18) . . ?
F5 C19 S2 109.77(18) . . ?
C5 N1 C4 109.3(2) . . ?
C5 N1 H1N 126(2) . . ?
C4 N1 H1N 125(2) . . ?
C5 O1 C3 107.11(17) . . ?
O3 S1 O2 118.98(13) . . ?
O3 S1 C1 114.43(12) . . ?
O2 S1 C1 109.56(12) . . ?
O3 S1 C18 102.71(12) . . ?
O2 S1 C18 101.93(12) . . ?
C1 S1 C18 107.57(12) . . ?
O4 S2 O5 120.77(13) . . ?
O4 S2 C1 113.35(12) . . ?
O5 S2 C1 108.95(12) . . ?
O4 S2 C19 102.69(12) . . ?
O5 S2 C19 101.82(12) . . ?
C1 S2 C19 107.62(12) . . ?
O1S S1S C1S 88.7(2) . . ?
O1S S1S C2S 109.6(3) . . ?
C1S S1S C2S 103.9(5) . . ?
S1S C1S H1P 109.5 . . ?
S1S C1S H1Q 109.5 . . ?
H1P C1S H1Q 109.5 . . ?
S1S C1S H1R 109.5 . . ?
H1P C1S H1R 109.5 . . ?
H1Q C1S H1R 109.5 . . ?
S1S C2S H2P 109.5 . . ?
S1S C2S H2Q 109.5 . . ?
H2P C2S H2Q 109.5 . . ?
S1S C2S H2R 109.5 . . ?
H2P C2S H2R 109.5 . . ?
H2Q C2S H2R 109.5 . . ?
O1T S1T C2T 104.7(5) . . ?
O1T S1T C1T 108.6(2) . . ?
C2T S1T C1T 88.2(5) . . ?
S1T C1T H1S 109.5 . . ?
S1T C1T H1T 109.5 . . ?
H1S C1T H1T 109.5 . . ?
S1T C1T H1U 109.5 . . ?
H1S C1T H1U 109.5 . . ?
H1T C1T H1U 109.5 . . ?
S1T C2T H2S 109.5 . . ?
S1T C2T H2T 109.5 . . ?
H2S C2T H2T 109.5 . . ?
S1T C2T H2U 109.5 . . ?
H2S C2T H2U 109.5 . . ?
H2T C2T H2U 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
S1 C1 C2 C3 -113.2(2) . . . . ?
S2 C1 C2 C3 77.9(3) . . . . ?
C1 C2 C3 C4 -131.5(3) . . . . ?
C1 C2 C3 O1 55.2(3) . . . . ?
O1 C3 C4 N1 -0.2(3) . . . . ?
C2 C3 C4 N1 -174.1(2) . . . . ?
O1 C3 C4 C6 178.8(2) . . . . ?
C2 C3 C4 C6 5.0(5) . . . . ?
C3 C4 C6 C11 136.2(3) . . . . ?
N1 C4 C6 C11 -44.9(3) . . . . ?
C3 C4 C6 C7 -43.4(4) . . . . ?
N1 C4 C6 C7 135.5(2) . . . . ?
C11 C6 C7 C8 -0.8(4) . . . . ?
C4 C6 C7 C8 178.8(2) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C6 0.9(4) . . . . ?
C7 C6 C11 C10 -0.6(4) . . . . ?
C4 C6 C11 C10 179.8(2) . . . . ?
N1 C5 C12 C13 178.6(2) . . . . ?
O1 C5 C12 C13 -0.4(3) . . . . ?
N1 C5 C12 C17 0.0(4) . . . . ?
O1 C5 C12 C17 -179.0(2) . . . . ?
C17 C12 C13 C14 0.5(4) . . . . ?
C5 C12 C13 C14 -178.2(2) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C12 -0.2(4) . . . . ?
C13 C12 C17 C16 -0.4(4) . . . . ?
C5 C12 C17 C16 178.2(2) . . . . ?
O1 C5 N1 C4 0.6(3) . . . . ?
C12 C5 N1 C4 -178.5(2) . . . . ?
C3 C4 N1 C5 -0.2(3) . . . . ?
C6 C4 N1 C5 -179.3(2) . . . . ?
N1 C5 O1 C3 -0.7(2) . . . . ?
C12 C5 O1 C3 178.5(2) . . . . ?
C4 C3 O1 C5 0.6(3) . . . . ?
C2 C3 O1 C5 175.5(2) . . . . ?
C2 C1 S1 O3 -141.86(19) . . . . ?
S2 C1 S1 O3 27.0(2) . . . . ?
C2 C1 S1 O2 -5.3(2) . . . . ?
S2 C1 S1 O2 163.51(15) . . . . ?
C2 C1 S1 C18 104.7(2) . . . . ?
S2 C1 S1 C18 -86.45(17) . . . . ?
F1 C18 S1 O3 -60.5(2) . . . . ?
F3 C18 S1 O3 177.59(18) . . . . ?
F2 C18 S1 O3 59.0(2) . . . . ?
F1 C18 S1 O2 175.74(19) . . . . ?
F3 C18 S1 O2 53.9(2) . . . . ?
F2 C18 S1 O2 -64.7(2) . . . . ?
F1 C18 S1 C1 60.5(2) . . . . ?
F3 C18 S1 C1 -61.3(2) . . . . ?
F2 C18 S1 C1 -179.92(18) . . . . ?
C2 C1 S2 O4 -166.57(18) . . . . ?
S1 C1 S2 O4 24.6(2) . . . . ?
C2 C1 S2 O5 -29.1(2) . . . . ?
S1 C1 S2 O5 162.10(14) . . . . ?
C2 C1 S2 C19 80.6(2) . . . . ?
S1 C1 S2 C19 -88.25(17) . . . . ?
F4 C19 S2 O4 -56.9(2) . . . . ?
F6 C19 S2 O4 -177.47(18) . . . . ?
F5 C19 S2 O4 63.7(2) . . . . ?
F4 C19 S2 O5 177.40(19) . . . . ?
F6 C19 S2 O5 56.9(2) . . . . ?
F5 C19 S2 O5 -62.0(2) . . . . ?
F4 C19 S2 C1 62.9(2) . . . . ?
F6 C19 S2 C1 -57.6(2) . . . . ?
F5 C19 S2 C1 -176.45(18) . . . . ?

_refine_diff_density_max         0.552
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.061



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_SH-112a
_database_code_depnum_ccdc_archive 'CCDC 1832227'

_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {04649364-5b77-4ca1-b4db-ed3bbd00d04c}
#==============================================================================
#SH-112a
#==============================================================================
_audit_creation_date             2018-02-14
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
2-(1-(4-chlorophenyl)-5-hydroxy-3-methyl-1H-pyrazol-2-ium-4-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
_chemical_name_common            ?
_chemical_melting_point          448
_chemical_formula_moiety         'C14 H11 Cl F6 N2 O5 S2'
_chemical_formula_sum            'C14 H11 Cl F6 N2 O5 S2'
_chemical_formula_weight         500.82
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
Cl Cl 0.1484 0.1585 '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'
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           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                   31.442(2)
_cell_length_b                   7.7594(5)
_cell_length_c                   16.3435(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.7400(10)
_cell_angle_gamma                90
_cell_volume                     3985.5(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    4262
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             2016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.486
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered conforcal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            9381
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.296
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3512
_reflns_number_gt                3143
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0380P)²+4.2061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3512
_refine_ls_number_parameters     276
_refine_ls_number_restraints     366
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.007
_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
C1 C 0.66772(5) 0.6474(2) 0.83372(10) 0.0133(4) Uani 1 1 d . U . . .
C2 C 0.68327(6) 0.7758(2) 0.77036(10) 0.0142(4) Uani 1 1 d . U . . .
H2A H 0.680125 0.894100 0.792061 0.017 Uiso 1 1 calc R U . . .
H2B H 0.713922 0.755659 0.761927 0.017 Uiso 1 1 calc R U . . .
C3 C 0.65956(6) 0.7631(2) 0.68900(10) 0.0132(4) Uani 1 1 d . U . . .
C4 C 0.61583(6) 0.7832(2) 0.67389(10) 0.0138(4) Uani 1 1 d . U . . .
C5 C 0.67612(6) 0.7111(2) 0.61518(11) 0.0138(4) Uani 1 1 d . U . . .
C6 C 0.72037(6) 0.6644(3) 0.59510(11) 0.0216(4) Uani 1 1 d . U . . .
H6A H 0.721330 0.631573 0.537279 0.032 Uiso 1 1 calc R U . . .
H6B H 0.729873 0.567252 0.629351 0.032 Uiso 1 1 calc R U . . .
H6C H 0.739114 0.763406 0.605408 0.032 Uiso 1 1 calc R U . . .
C7 C 0.56777(6) 0.7555(2) 0.54655(11) 0.0153(4) Uani 1 1 d . U . . .
C8 C 0.53016(6) 0.6993(3) 0.57944(12) 0.0205(4) Uani 1 1 d . U . . .
H8 H 0.529883 0.654766 0.633570 0.025 Uiso 1 1 calc R U . . .
C9 C 0.49282(6) 0.7090(3) 0.53192(12) 0.0239(4) Uani 1 1 d . U . . .
H9 H 0.466576 0.672435 0.553422 0.029 Uiso 1 1 calc R U . . .
C10 C 0.49431(6) 0.7725(3) 0.45296(12) 0.0216(4) Uani 1 1 d . U . . .
C11 C 0.53193(6) 0.8284(2) 0.42037(12) 0.0218(4) Uani 1 1 d . U . . .
H11 H 0.532260 0.871907 0.366058 0.026 Uiso 1 1 calc R U . . .
C12 C 0.56913(6) 0.8204(2) 0.46775(11) 0.0188(4) Uani 1 1 d . U . . .
H12 H 0.595252 0.858952 0.446474 0.023 Uiso 1 1 calc R U . . .
C13 C 0.67066(6) 0.8181(2) 0.98712(11) 0.0189(4) Uani 1 1 d . U . . .
C14 C 0.63692(7) 0.3334(2) 0.76343(11) 0.0214(4) Uani 1 1 d . U . . .
Cl1 Cl 0.44775(2) 0.78050(7) 0.39266(3) 0.03320(15) Uani 1 1 d . U . . .
F1 F 0.63652(4) 0.38541(15) 0.68590(6) 0.0274(3) Uani 1 1 d . U . . .
F2 F 0.64219(5) 0.16390(16) 0.76349(8) 0.0501(4) Uani 1 1 d . U . . .
F3 F 0.59917(4) 0.3668(2) 0.79317(8) 0.0443(4) Uani 1 1 d . U . . .
F4 F 0.69452(4) 0.94082(15) 0.95478(7) 0.0300(3) Uani 1 1 d . U . . .
F5 F 0.64750(4) 0.88872(14) 1.04477(6) 0.0254(3) Uani 1 1 d . U . . .
F6 F 0.69649(4) 0.70205(15) 1.02226(7) 0.0300(3) Uani 1 1 d . U . . .
N1 N 0.60671(5) 0.74433(19) 0.59440(9) 0.0145(3) Uani 1 1 d . U . . .
N2 N 0.64438(5) 0.70413(19) 0.55879(9) 0.0144(3) Uani 1 1 d . U . . .
O1 O 0.58434(4) 0.83088(17) 0.72054(7) 0.0183(3) Uani 1 1 d . U . . .
H1 H 0.593592 0.844331 0.768876 0.027 Uiso 1 1 calc R U . . .
O2 O 0.71628(4) 0.41944(17) 0.77433(8) 0.0214(3) Uani 1 1 d . U . . .
O3 O 0.67855(4) 0.34447(16) 0.90119(7) 0.0192(3) Uani 1 1 d . U . . .
O4 O 0.61139(4) 0.86144(16) 0.87806(7) 0.0178(3) Uani 1 1 d . U . . .
O5 O 0.61541(4) 0.57933(16) 0.95057(7) 0.0168(3) Uani 1 1 d . U . . .
S1 S 0.68007(2) 0.43801(6) 0.82506(3) 0.01411(12) Uani 1 1 d . U . . .
S2 S 0.63630(2) 0.71495(5) 0.90745(3) 0.01290(12) Uani 1 1 d . U . . .
H2N H 0.6448(6) 0.662(3) 0.5148(13) 0.015 Uiso 1 1 d . 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
C1 C2 1.528(2) . ?
C1 S2 1.6658(18) . ?
C1 S1 1.6775(18) . ?
C2 C3 1.508(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C5 1.388(2) . ?
C3 C4 1.398(2) . ?
C4 O1 1.321(2) . ?
C4 N1 1.356(2) . ?
C5 N2 1.339(2) . ?
C5 C6 1.484(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.385(3) . ?
C7 C8 1.384(3) . ?
C7 N1 1.435(2) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 Cl1 1.7409(18) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 F5 1.327(2) . ?
C13 F6 1.331(2) . ?
C13 F4 1.332(2) . ?
C13 S2 1.8487(19) . ?
C14 F3 1.322(2) . ?
C14 F2 1.326(2) . ?
C14 F1 1.329(2) . ?
C14 S1 1.8521(19) . ?
N1 N2 1.372(2) . ?
N2 H2N 0.79(2) . ?
O1 H1 0.8400 . ?
O2 S1 1.4360(13) . ?
O3 S1 1.4426(13) . ?
O4 S2 1.4538(13) . ?
O5 S2 1.4365(13) . ?

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
C2 C1 S2 119.60(13) . . ?
C2 C1 S1 119.65(13) . . ?
S2 C1 S1 120.64(11) . . ?
C3 C2 C1 113.28(14) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C5 C3 C4 105.75(15) . . ?
C5 C3 C2 126.65(16) . . ?
C4 C3 C2 127.28(16) . . ?
O1 C4 N1 118.35(15) . . ?
O1 C4 C3 132.82(16) . . ?
N1 C4 C3 108.83(16) . . ?
N2 C5 C3 108.59(16) . . ?
N2 C5 C6 121.47(16) . . ?
C3 C5 C6 129.93(16) . . ?
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 . . ?
C12 C7 C8 121.77(17) . . ?
C12 C7 N1 118.63(16) . . ?
C8 C7 N1 119.59(16) . . ?
C7 C8 C9 118.88(18) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 119.25(18) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 121.67(17) . . ?
C11 C10 Cl1 119.04(15) . . ?
C9 C10 Cl1 119.28(15) . . ?
C10 C11 C12 119.26(18) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C11 119.16(18) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
F5 C13 F6 108.29(15) . . ?
F5 C13 F4 108.33(15) . . ?
F6 C13 F4 108.14(15) . . ?
F5 C13 S2 110.95(13) . . ?
F6 C13 S2 110.30(12) . . ?
F4 C13 S2 110.74(12) . . ?
F3 C14 F2 107.93(17) . . ?
F3 C14 F1 107.95(16) . . ?
F2 C14 F1 107.42(15) . . ?
F3 C14 S1 111.42(13) . . ?
F2 C14 S1 110.18(14) . . ?
F1 C14 S1 111.77(13) . . ?
C4 N1 N2 107.27(14) . . ?
C4 N1 C7 131.36(15) . . ?
N2 N1 C7 121.06(14) . . ?
C5 N2 N1 109.51(15) . . ?
C5 N2 H2N 127.6(15) . . ?
N1 N2 H2N 121.3(15) . . ?
C4 O1 H1 109.5 . . ?
O2 S1 O3 119.68(8) . . ?
O2 S1 C1 109.61(8) . . ?
O3 S1 C1 113.62(8) . . ?
O2 S1 C14 102.86(9) . . ?
O3 S1 C14 101.87(8) . . ?
C1 S1 C14 107.62(9) . . ?
O5 S2 O4 119.01(8) . . ?
O5 S2 C1 114.48(8) . . ?
O4 S2 C1 109.42(8) . . ?
O5 S2 C13 103.75(8) . . ?
O4 S2 C13 101.05(8) . . ?
C1 S2 C13 107.40(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
S2 C1 C2 C3 -102.66(16) . . . . ?
S1 C1 C2 C3 73.74(18) . . . . ?
C1 C2 C3 C5 -113.97(19) . . . . ?
C1 C2 C3 C4 58.7(2) . . . . ?
C5 C3 C4 O1 -179.55(18) . . . . ?
C2 C3 C4 O1 6.6(3) . . . . ?
C5 C3 C4 N1 0.2(2) . . . . ?
C2 C3 C4 N1 -173.70(16) . . . . ?
C4 C3 C5 N2 1.3(2) . . . . ?
C2 C3 C5 N2 175.18(16) . . . . ?
C4 C3 C5 C6 -177.51(18) . . . . ?
C2 C3 C5 C6 -3.6(3) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
N1 C7 C8 C9 -179.19(17) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C8 C9 C10 Cl1 178.68(15) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
Cl1 C10 C11 C12 -179.26(15) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
N1 C7 C12 C11 178.63(16) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
O1 C4 N1 N2 178.27(15) . . . . ?
C3 C4 N1 N2 -1.49(19) . . . . ?
O1 C4 N1 C7 4.8(3) . . . . ?
C3 C4 N1 C7 -174.97(17) . . . . ?
C12 C7 N1 C4 137.0(2) . . . . ?
C8 C7 N1 C4 -44.0(3) . . . . ?
C12 C7 N1 N2 -35.7(2) . . . . ?
C8 C7 N1 N2 143.29(17) . . . . ?
C3 C5 N2 N1 -2.2(2) . . . . ?
C6 C5 N2 N1 176.67(16) . . . . ?
C4 N1 N2 C5 2.32(19) . . . . ?
C7 N1 N2 C5 176.61(15) . . . . ?
C2 C1 S1 O2 20.36(16) . . . . ?
S2 C1 S1 O2 -163.29(10) . . . . ?
C2 C1 S1 O3 157.19(12) . . . . ?
S2 C1 S1 O3 -26.45(14) . . . . ?
C2 C1 S1 C14 -90.81(15) . . . . ?
S2 C1 S1 C14 85.55(12) . . . . ?
F3 C14 S1 O2 -167.86(13) . . . . ?
F2 C14 S1 O2 72.37(15) . . . . ?
F1 C14 S1 O2 -46.98(15) . . . . ?
F3 C14 S1 O3 67.61(15) . . . . ?
F2 C14 S1 O3 -52.17(15) . . . . ?
F1 C14 S1 O3 -171.52(13) . . . . ?
F3 C14 S1 C1 -52.16(16) . . . . ?
F2 C14 S1 C1 -171.93(14) . . . . ?
F1 C14 S1 C1 68.71(15) . . . . ?
C2 C1 S2 O5 165.45(12) . . . . ?
S1 C1 S2 O5 -10.91(14) . . . . ?
C2 C1 S2 O4 28.94(16) . . . . ?
S1 C1 S2 O4 -147.42(10) . . . . ?
C2 C1 S2 C13 -79.94(15) . . . . ?
S1 C1 S2 C13 103.70(12) . . . . ?
F5 C13 S2 O5 -63.85(14) . . . . ?
F6 C13 S2 O5 56.14(14) . . . . ?
F4 C13 S2 O5 175.82(12) . . . . ?
F5 C13 S2 O4 59.97(14) . . . . ?
F6 C13 S2 O4 179.96(12) . . . . ?
F4 C13 S2 O4 -60.36(14) . . . . ?
F5 C13 S2 C1 174.56(12) . . . . ?
F6 C13 S2 C1 -65.44(15) . . . . ?
F4 C13 S2 C1 54.23(15) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.053



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_SH-37a
_database_code_depnum_ccdc_archive 'CCDC 1832226'

_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {64cf5533-30fc-4da0-95a4-cf0288596e10}
#============================================================================== 
# SH-37a
#==============================================================================
_audit_creation_date             2017-09-01
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
3-(2,2-Bis((trifluoromethyl)sulfonyl)ethyl)-4-hydroxy-2H-chromen-2-one
;
_chemical_name_common            ?
_chemical_melting_point          560
_chemical_formula_moiety         'C13 H8 F6 O7 S2'
_chemical_formula_sum            'C13 H8 F6 O7 S2'
_chemical_formula_weight         454.31
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
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           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                   5.7308(5)
_cell_length_b                   13.6484(13)
_cell_length_c                   21.184(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.7480(10)
_cell_angle_gamma                90
_cell_volume                     1648.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3992
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.56

_exptl_crystal_description       needle

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.426
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7796
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_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             2904
_reflns_number_gt                2593
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;

_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)+(0.0324P)²+1.5701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2904
_refine_ls_number_parameters     256
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.261
_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
C1 C 0.3235(3) 0.25178(13) 0.26455(9) 0.0134(3) Uani 1 1 d . U . . .
C2 C 0.1884(3) 0.33436(13) 0.25603(9) 0.0132(3) Uani 1 1 d . U . . .
C3 C -0.0228(3) 0.33357(13) 0.21200(9) 0.0135(3) Uani 1 1 d . U . . .
C4 C -0.1760(3) 0.41376(14) 0.20017(9) 0.0150(3) Uani 1 1 d . U . . .
H4 H -0.1404 0.4746 0.2207 0.018 Uiso 1 1 calc R U . . .
C5 C -0.3778(3) 0.40451(14) 0.15894(9) 0.0163(3) Uani 1 1 d . U . . .
H5 H -0.4796 0.4590 0.1509 0.020 Uiso 1 1 calc R U . . .
C6 C -0.4316(3) 0.31481(14) 0.12906(9) 0.0167(3) Uani 1 1 d . U . . .
H6 H -0.5709 0.3087 0.1010 0.020 Uiso 1 1 calc R U . . .
C7 C -0.2844(3) 0.23488(14) 0.13982(9) 0.0160(3) Uani 1 1 d . U . . .
H7 H -0.3219 0.1739 0.1196 0.019 Uiso 1 1 calc R U . . .
C8 C -0.0809(3) 0.24545(14) 0.18071(9) 0.0144(3) Uani 1 1 d . U . . .
C9 C 0.2668(3) 0.16539(14) 0.22801(9) 0.0143(3) Uani 1 1 d . U . . .
C10 C 0.5487(3) 0.25423(14) 0.30782(9) 0.0137(3) Uani 1 1 d . U . . .
H10A H 0.6428 0.3113 0.2965 0.016 Uiso 1 1 calc R U . . .
H10B H 0.6401 0.1943 0.3008 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5095(3) 0.26095(14) 0.37936(9) 0.0140(3) Uani 1 1 d . U . . .
H11 H 0.3631 0.2989 0.3843 0.017 Uiso 1 1 calc R U . . .
C12 C 0.3613(4) 0.14689(15) 0.48799(9) 0.0207(3) Uani 1 1 d . U . . .
C13 C 0.6820(4) 0.45199(15) 0.41229(10) 0.0253(3) Uani 1 1 d . U . . .
F1 F 0.1885(2) 0.08363(10) 0.48904(6) 0.0345(3) Uani 1 1 d . U . . .
F2 F 0.5273(2) 0.12486(9) 0.53354(5) 0.0253(3) Uani 1 1 d . U . . .
F3 F 0.2838(2) 0.23669(9) 0.49668(5) 0.0269(3) Uani 1 1 d . U . . .
F4 F 0.4643(2) 0.46931(9) 0.42507(6) 0.0339(3) Uani 1 1 d . U . . .
F5 F 0.8285(3) 0.50219(10) 0.45228(7) 0.0417(4) Uani 1 1 d . U . . .
F6 F 0.7081(2) 0.47963(9) 0.35356(6) 0.0298(3) Uani 1 1 d . U . . .
O1 O 0.2602(2) 0.41218(10) 0.29047(6) 0.0154(3) Uani 1 1 d . U . . .
O2 O 0.0621(2) 0.16381(9) 0.18867(6) 0.0155(3) Uani 1 1 d . U . . .
O3 O 0.3901(2) 0.09177(9) 0.22817(6) 0.0175(3) Uani 1 1 d . U . . .
O4 O 0.2940(3) 0.09282(10) 0.36746(6) 0.0227(3) Uani 1 1 d . U . . .
O5 O 0.7054(2) 0.09318(10) 0.41831(7) 0.0226(3) Uani 1 1 d . U . . .
O6 O 0.7517(3) 0.30173(11) 0.49005(7) 0.0225(3) Uani 1 1 d . U . . .
O7 O 0.9640(2) 0.30483(11) 0.39298(7) 0.0225(3) Uani 1 1 d . U . . .
S1 S 0.47834(8) 0.13650(3) 0.40811(2) 0.01557(13) Uani 1 1 d . U . . .
S2 S 0.75664(8) 0.31985(4) 0.42395(2) 0.01620(13) Uani 1 1 d . U . . .
H1O H 0.192(4) 0.4656(18) 0.2815(10) 0.019 Uiso 1 1 d . 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
C1 C2 1.369(3) . ?
C1 C9 1.430(3) . ?
C1 C10 1.507(3) . ?
C2 O1 1.330(2) . ?
C2 C3 1.452(3) . ?
C3 C8 1.397(3) . ?
C3 C4 1.410(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 O2 1.384(2) . ?
C9 O3 1.228(2) . ?
C9 O2 1.370(2) . ?
C10 C11 1.557(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 S2 1.8102(19) . ?
C11 S1 1.8192(19) . ?
C11 H11 1.0000 . ?
C12 F1 1.316(2) . ?
C12 F2 1.320(2) . ?
C12 F3 1.323(2) . ?
C12 S1 1.887(2) . ?
C13 F5 1.323(2) . ?
C13 F6 1.323(3) . ?
C13 F4 1.324(3) . ?
C13 S2 1.864(2) . ?
O1 H1O 0.84(2) . ?
O4 S1 1.4250(15) . ?
O5 S1 1.4257(15) . ?
O6 S2 1.4251(15) . ?
O7 S2 1.4285(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 120.84(17) . . ?
C2 C1 C10 120.05(17) . . ?
C9 C1 C10 118.80(16) . . ?
O1 C2 C1 116.43(17) . . ?
O1 C2 C3 123.39(17) . . ?
C1 C2 C3 120.18(17) . . ?
C8 C3 C4 117.99(17) . . ?
C8 C3 C2 117.04(17) . . ?
C4 C3 C2 124.93(17) . . ?
C5 C4 C3 120.51(18) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.88(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.83(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 118.74(18) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
O2 C8 C7 116.27(17) . . ?
O2 C8 C3 121.69(17) . . ?
C7 C8 C3 122.04(18) . . ?
O3 C9 O2 116.50(16) . . ?
O3 C9 C1 125.02(18) . . ?
O2 C9 C1 118.46(16) . . ?
C1 C10 C11 113.27(15) . . ?
C1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 S2 110.63(13) . . ?
C10 C11 S1 107.43(13) . . ?
S2 C11 S1 109.74(10) . . ?
C10 C11 H11 109.7 . . ?
S2 C11 H11 109.7 . . ?
S1 C11 H11 109.7 . . ?
F1 C12 F2 109.06(16) . . ?
F1 C12 F3 109.99(17) . . ?
F2 C12 F3 109.68(17) . . ?
F1 C12 S1 107.55(14) . . ?
F2 C12 S1 110.10(14) . . ?
F3 C12 S1 110.42(13) . . ?
F5 C13 F6 109.29(18) . . ?
F5 C13 F4 109.11(18) . . ?
F6 C13 F4 109.81(17) . . ?
F5 C13 S2 107.09(14) . . ?
F6 C13 S2 110.75(15) . . ?
F4 C13 S2 110.73(15) . . ?
C2 O1 H1O 117.3(15) . . ?
C9 O2 C8 121.50(15) . . ?
O4 S1 O5 121.88(9) . . ?
O4 S1 C11 106.26(8) . . ?
O5 S1 C11 108.63(9) . . ?
O4 S1 C12 105.35(9) . . ?
O5 S1 C12 107.22(9) . . ?
C11 S1 C12 106.60(9) . . ?
O6 S2 O7 121.72(9) . . ?
O6 S2 C11 110.13(9) . . ?
O7 S2 C11 109.88(9) . . ?
O6 S2 C13 105.73(10) . . ?
O7 S2 C13 105.56(10) . . ?
C11 S2 C13 101.74(9) . . ?

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053



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_SH-133
_database_code_depnum_ccdc_archive 'CCDC 1843015'

_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {53d091d5-4cf4-40e6-a7f1-9de94fff2e9d}
#==============================================================================
# SH-133
#==============================================================================
_audit_creation_date             2018-03-30
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
2-(1-phenyl-1H-pyrazol-2-ium-2-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F6 N2 O4 S2'
_chemical_formula_sum            'C13 H10 F6 N2 O4 S2'
_chemical_formula_weight         436.35
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.266(2)
_cell_length_b                   6.0883(9)
_cell_length_c                   18.922(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.123(2)
_cell_angle_gamma                90
_cell_volume                     1639.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    1854
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.131
_exptl_absorpt_coefficient_mu    0.414
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            7671
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.431
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2900
_reflns_number_gt                2376
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;
_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)+(0.0382P)²+0.9851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     244
_refine_ls_number_restraints     330
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      0.971
_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
C1 C 0.68958(17) 0.5702(4) 0.52737(12) 0.0148(5) Uani 1 1 d . U . . .
H1A H 0.631181 0.482766 0.528398 0.018 Uiso 1 1 calc R U . . .
H1B H 0.743398 0.469765 0.537718 0.018 Uiso 1 1 calc R U . . .
C2 C 0.69532(16) 0.6650(4) 0.45456(12) 0.0137(5) Uani 1 1 d . U . . .
C3 C 0.63540(17) 0.9206(4) 0.58488(13) 0.0172(6) Uani 1 1 d . U . . .
H3 H 0.598258 0.977606 0.545391 0.021 Uiso 1 1 calc R U . . .
C4 C 0.64107(18) 1.0077(4) 0.65182(13) 0.0206(6) Uani 1 1 d . U . . .
H4 H 0.609512 1.134294 0.667378 0.025 Uiso 1 1 calc R U . . .
C5 C 0.70198(17) 0.8739(4) 0.69199(13) 0.0192(6) Uani 1 1 d . U . . .
H5 H 0.720296 0.892976 0.740867 0.023 Uiso 1 1 calc R U . . .
C6 C 0.80241(16) 0.5513(4) 0.66973(13) 0.0154(5) Uani 1 1 d . U . . .
C7 C 0.79088(18) 0.4189(4) 0.72777(13) 0.0194(6) Uani 1 1 d . U . . .
H7 H 0.736441 0.430877 0.753630 0.023 Uiso 1 1 calc R U . . .
C8 C 0.8607(2) 0.2684(4) 0.74724(14) 0.0262(7) Uani 1 1 d . U . . .
H8 H 0.855016 0.177700 0.787575 0.031 Uiso 1 1 calc R U . . .
C9 C 0.9392(2) 0.2491(5) 0.70802(15) 0.0292(7) Uani 1 1 d . U . . .
H9 H 0.985896 0.142141 0.720765 0.035 Uiso 1 1 calc R U . . .
C10 C 0.94943(19) 0.3848(5) 0.65074(15) 0.0309(7) Uani 1 1 d . U . . .
H10 H 1.003087 0.371352 0.624089 0.037 Uiso 1 1 calc R U . . .
C11 C 0.88140(17) 0.5410(5) 0.63207(13) 0.0230(6) Uani 1 1 d . U . . .
H11 H 0.889124 0.639205 0.593924 0.028 Uiso 1 1 calc R U . . .
C12 C 0.56841(17) 0.4294(4) 0.36159(13) 0.0176(6) Uani 1 1 d . U . . .
C13 C 0.83213(17) 0.9967(4) 0.44273(14) 0.0202(6) Uani 1 1 d . U . . .
F1 F 0.56294(10) 0.2767(2) 0.41166(7) 0.0223(4) Uani 1 1 d . U . . .
F2 F 0.48509(10) 0.4398(3) 0.32436(8) 0.0282(4) Uani 1 1 d . U . . .
F3 F 0.63219(10) 0.3662(2) 0.31794(7) 0.0236(4) Uani 1 1 d . U . . .
F4 F 0.83430(11) 1.0350(3) 0.51215(8) 0.0306(4) Uani 1 1 d . U . . .
F5 F 0.77053(10) 1.1324(2) 0.41050(8) 0.0289(4) Uani 1 1 d . U . . .
F6 F 0.91666(10) 1.0408(3) 0.42085(8) 0.0292(4) Uani 1 1 d . U . . .
N1 N 0.69036(13) 0.7427(3) 0.58385(10) 0.0141(5) Uani 1 1 d . U . . .
N2 N 0.73085(14) 0.7136(3) 0.65095(10) 0.0147(5) Uani 1 1 d . U . . .
O1 O 0.51837(11) 0.7298(3) 0.44517(9) 0.0176(4) Uani 1 1 d . U . . .
O2 O 0.60809(11) 0.8378(3) 0.34223(9) 0.0180(4) Uani 1 1 d . U . . .
O3 O 0.87163(11) 0.5894(3) 0.46693(9) 0.0196(4) Uani 1 1 d . U . . .
O4 O 0.80137(11) 0.6943(3) 0.34793(8) 0.0181(4) Uani 1 1 d . U . . .
S1 S 0.59642(4) 0.69856(10) 0.40171(3) 0.01379(16) Uani 1 1 d . U . . .
S2 S 0.80190(4) 0.70693(10) 0.42352(3) 0.01485(17) Uani 1 1 d . 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
C1 N1 1.498(3) . ?
C1 C2 1.501(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 S1 1.682(2) . ?
C2 S2 1.688(2) . ?
C3 N1 1.338(3) . ?
C3 C4 1.370(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 N2 1.331(3) . ?
C5 H5 0.9500 . ?
C6 C11 1.377(3) . ?
C6 C7 1.382(3) . ?
C6 N2 1.447(3) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 F3 1.329(3) . ?
C12 F1 1.333(3) . ?
C12 F2 1.339(3) . ?
C12 S1 1.838(3) . ?
C13 F5 1.323(3) . ?
C13 F6 1.330(3) . ?
C13 F4 1.332(3) . ?
C13 S2 1.846(3) . ?
N1 N2 1.368(3) . ?
O1 S1 1.4435(17) . ?
O2 S1 1.4283(18) . ?
O3 S2 1.4348(17) . ?
O4 S2 1.4319(17) . ?

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
N1 C1 C2 112.8(2) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 S1 119.57(18) . . ?
C1 C2 S2 119.16(17) . . ?
S1 C2 S2 120.84(14) . . ?
N1 C3 C4 109.3(2) . . ?
N1 C3 H3 125.3 . . ?
C4 C3 H3 125.3 . . ?
C3 C4 C5 105.9(2) . . ?
C3 C4 H4 127.0 . . ?
C5 C4 H4 127.0 . . ?
N2 C5 C4 108.7(2) . . ?
N2 C5 H5 125.6 . . ?
C4 C5 H5 125.6 . . ?
C11 C6 C7 122.2(2) . . ?
C11 C6 N2 119.6(2) . . ?
C7 C6 N2 118.1(2) . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 118.9(3) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
F3 C12 F1 108.5(2) . . ?
F3 C12 F2 107.96(19) . . ?
F1 C12 F2 108.2(2) . . ?
F3 C12 S1 112.12(17) . . ?
F1 C12 S1 110.50(16) . . ?
F2 C12 S1 109.46(17) . . ?
F5 C13 F6 108.5(2) . . ?
F5 C13 F4 108.2(2) . . ?
F6 C13 F4 108.3(2) . . ?
F5 C13 S2 111.60(16) . . ?
F6 C13 S2 109.64(18) . . ?
F4 C13 S2 110.50(18) . . ?
C3 N1 N2 107.46(19) . . ?
C3 N1 C1 127.13(19) . . ?
N2 N1 C1 123.52(18) . . ?
C5 N2 N1 108.59(19) . . ?
C5 N2 C6 126.9(2) . . ?
N1 N2 C6 124.04(19) . . ?
O2 S1 O1 120.61(10) . . ?
O2 S1 C2 113.60(11) . . ?
O1 S1 C2 109.00(11) . . ?
O2 S1 C12 103.78(11) . . ?
O1 S1 C12 101.47(11) . . ?
C2 S1 C12 106.58(11) . . ?
O4 S2 O3 119.92(11) . . ?
O4 S2 C2 113.53(11) . . ?
O3 S2 C2 109.28(11) . . ?
O4 S2 C13 103.42(11) . . ?
O3 S2 C13 102.78(11) . . ?
C2 S2 C13 106.23(12) . . ?

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
N1 C1 C2 S1 -97.9(2) . . . . ?
N1 C1 C2 S2 89.5(2) . . . . ?
N1 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 N2 -0.3(3) . . . . ?
C11 C6 C7 C8 -1.4(4) . . . . ?
N2 C6 C7 C8 -177.9(2) . . . . ?
C6 C7 C8 C9 -1.4(4) . . . . ?
C7 C8 C9 C10 2.1(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C7 C6 C11 C10 3.4(4) . . . . ?
N2 C6 C11 C10 179.9(2) . . . . ?
C9 C10 C11 C6 -2.6(4) . . . . ?
C4 C3 N1 N2 0.7(3) . . . . ?
C4 C3 N1 C1 165.4(2) . . . . ?
C2 C1 N1 C3 51.2(3) . . . . ?
C2 C1 N1 N2 -146.4(2) . . . . ?
C4 C5 N2 N1 0.8(3) . . . . ?
C4 C5 N2 C6 173.0(2) . . . . ?
C3 N1 N2 C5 -1.0(3) . . . . ?
C1 N1 N2 C5 -166.3(2) . . . . ?
C3 N1 N2 C6 -173.5(2) . . . . ?
C1 N1 N2 C6 21.2(3) . . . . ?
C11 C6 N2 C5 -119.1(3) . . . . ?
C7 C6 N2 C5 57.5(3) . . . . ?
C11 C6 N2 N1 52.0(3) . . . . ?
C7 C6 N2 N1 -131.4(2) . . . . ?
C1 C2 S1 O2 165.27(17) . . . . ?
S2 C2 S1 O2 -22.3(2) . . . . ?
C1 C2 S1 O1 27.7(2) . . . . ?
S2 C2 S1 O1 -159.87(14) . . . . ?
C1 C2 S1 C12 -81.1(2) . . . . ?
S2 C2 S1 C12 91.35(17) . . . . ?
F3 C12 S1 O2 53.80(18) . . . . ?
F1 C12 S1 O2 174.99(16) . . . . ?
F2 C12 S1 O2 -65.98(19) . . . . ?
F3 C12 S1 O1 179.58(16) . . . . ?
F1 C12 S1 O1 -59.23(18) . . . . ?
F2 C12 S1 O1 59.80(18) . . . . ?
F3 C12 S1 C2 -66.39(19) . . . . ?
F1 C12 S1 C2 54.8(2) . . . . ?
F2 C12 S1 C2 173.82(16) . . . . ?
C1 C2 S2 O4 151.68(18) . . . . ?
S1 C2 S2 O4 -20.8(2) . . . . ?
C1 C2 S2 O3 14.9(2) . . . . ?
S1 C2 S2 O3 -157.55(14) . . . . ?
C1 C2 S2 C13 -95.3(2) . . . . ?
S1 C2 S2 C13 92.21(17) . . . . ?
F5 C13 S2 O4 58.8(2) . . . . ?
F6 C13 S2 O4 -61.41(19) . . . . ?
F4 C13 S2 O4 179.28(17) . . . . ?
F5 C13 S2 O3 -175.72(17) . . . . ?
F6 C13 S2 O3 64.03(19) . . . . ?
F4 C13 S2 O3 -55.27(19) . . . . ?
F5 C13 S2 C2 -61.0(2) . . . . ?
F6 C13 S2 C2 178.79(16) . . . . ?
F4 C13 S2 C2 59.5(2) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.066



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_SH-114a
_database_code_depnum_ccdc_archive 'CCDC 1832229'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
#==============================================================================
# SH-114a
#==============================================================================
_audit_creation_date             2018-02-15
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
2-(5-hydroxy-1,3-dimethyl-1H-pyrazol-2-ium-4-yl)-
1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide 
;
_chemical_name_common            ?
_chemical_melting_point          441
_chemical_formula_moiety         'C9 H10 F6 N2 O5 S2'
_chemical_formula_sum            'C9 H10 F6 N2 O5 S2'
_chemical_formula_weight         404.31
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   17.2641(10)
_cell_length_b                   14.8304(8)
_cell_length_c                   23.9088(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6121.5(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    90
_cell_measurement_reflns_used    7817
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block

_exptl_crystal_colour            'pale yellow'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_F_000             3264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.174
_exptl_absorpt_coefficient_mu    0.440
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            28505
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.703
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_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             5403
_reflns_number_gt                4636
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;


_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)+(0.0394P)²+6.9113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5403
_refine_ls_number_parameters     445
_refine_ls_number_restraints     576
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.064
_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
C1 C 0.40318(12) 0.03688(16) 0.39614(10) 0.0155(5) Uani 1 1 d . U . . .
C2 C 0.47072(12) -0.02487(16) 0.41088(9) 0.0157(5) Uani 1 1 d . U . . .
H2A H 0.482505 -0.017369 0.451133 0.019 Uiso 1 1 calc R U . . .
H2B H 0.454015 -0.088071 0.405209 0.019 Uiso 1 1 calc R U . . .
C3 C 0.54389(13) -0.00991(15) 0.37835(10) 0.0158(5) Uani 1 1 d . U . . .
C4 C 0.61439(13) 0.01908(16) 0.39964(10) 0.0183(5) Uani 1 1 d . U . . .
C5 C 0.55683(13) -0.02200(16) 0.32124(10) 0.0172(5) Uani 1 1 d . U . . .
C6 C 0.63589(14) 0.0446(2) 0.45795(10) 0.0263(6) Uani 1 1 d . U . . .
H6A H 0.689557 0.066088 0.458632 0.039 Uiso 1 1 calc R U . . .
H6B H 0.630880 -0.008143 0.482402 0.039 Uiso 1 1 calc R U . . .
H6C H 0.601372 0.092530 0.471144 0.039 Uiso 1 1 calc R U . . .
C7 C 0.67324(14) -0.01763(18) 0.25753(10) 0.0243(6) Uani 1 1 d . U . . .
H7A H 0.687230 -0.081562 0.255165 0.036 Uiso 1 1 calc R U . . .
H7B H 0.720407 0.019136 0.257369 0.036 Uiso 1 1 calc R U . . .
H7C H 0.640907 -0.001369 0.225382 0.036 Uiso 1 1 calc R U . . .
C8 C 0.26405(13) -0.06701(17) 0.39775(10) 0.0216(5) Uani 1 1 d . U . . .
C9 C 0.43825(15) 0.22152(19) 0.37528(15) 0.0376(7) Uani 1 1 d . U . . .
C1B C 0.60217(12) 0.66883(16) 0.39063(10) 0.0159(5) Uani 1 1 d . U . . .
C2B C 0.53909(12) 0.72862(16) 0.41512(10) 0.0171(5) Uani 1 1 d . U . . .
H2B1 H 0.535880 0.717008 0.455832 0.021 Uiso 1 1 calc R U . . .
H2B2 H 0.554525 0.792391 0.410083 0.021 Uiso 1 1 calc R U . . .
C3B C 0.45960(13) 0.71576(15) 0.39008(10) 0.0165(5) Uani 1 1 d . U . . .
C4B C 0.39303(13) 0.68871(15) 0.41756(10) 0.0163(5) Uani 1 1 d . U . . .
C5B C 0.43753(13) 0.72857(16) 0.33446(10) 0.0182(5) Uani 1 1 d . U . . .
C6B C 0.38083(14) 0.66223(19) 0.47719(10) 0.0270(6) Uani 1 1 d . U . . .
H6B1 H 0.325435 0.652845 0.483989 0.040 Uiso 1 1 calc R U . . .
H6B2 H 0.400002 0.710204 0.501745 0.040 Uiso 1 1 calc R U . . .
H6B3 H 0.409046 0.606279 0.484950 0.040 Uiso 1 1 calc R U . . .
C7B C 0.31244(14) 0.72653(18) 0.28073(11) 0.0261(6) Uani 1 1 d . U . . .
H7B1 H 0.297991 0.790411 0.279681 0.039 Uiso 1 1 calc R U . . .
H7B2 H 0.265591 0.689518 0.283719 0.039 Uiso 1 1 calc R U . . .
H7B3 H 0.340329 0.710817 0.246392 0.039 Uiso 1 1 calc R U . . .
C8B C 0.73786(14) 0.77834(17) 0.38256(11) 0.0251(6) Uani 1 1 d . U . . .
C9B C 0.56339(15) 0.48832(19) 0.36340(15) 0.0392(7) Uani 1 1 d . U . . .
F1 F 0.21360(8) -0.10949(11) 0.36486(7) 0.0356(4) Uani 1 1 d . U . . .
F2 F 0.22553(8) -0.01346(10) 0.43214(6) 0.0298(4) Uani 1 1 d . U . . .
F3 F 0.30114(8) -0.12864(10) 0.42810(6) 0.0282(3) Uani 1 1 d . U . . .
F4 F 0.39960(11) 0.22282(13) 0.32742(9) 0.0554(5) Uani 1 1 d . U . . .
F5 F 0.43495(10) 0.30309(11) 0.39811(11) 0.0619(6) Uani 1 1 d . U . . .
F6 F 0.51189(9) 0.20154(11) 0.36457(9) 0.0488(5) Uani 1 1 d . U . . .
F1B F 0.78047(9) 0.82546(12) 0.34654(7) 0.0413(4) Uani 1 1 d . U . . .
F2B F 0.78486(8) 0.72459(11) 0.41146(7) 0.0370(4) Uani 1 1 d . U . . .
F3B F 0.70479(8) 0.83518(10) 0.41825(7) 0.0333(4) Uani 1 1 d . U . . .
F4B F 0.59738(10) 0.49221(13) 0.31387(8) 0.0522(5) Uani 1 1 d . U . . .
F5B F 0.56753(10) 0.40365(11) 0.38219(11) 0.0653(7) Uani 1 1 d . U . . .
F6B F 0.48923(9) 0.51059(12) 0.35752(10) 0.0561(6) Uani 1 1 d . U . . .
N1 N 0.66576(12) 0.02230(15) 0.35792(8) 0.0198(4) Uani 1 1 d . U . . .
N2 N 0.63036(11) -0.00142(13) 0.30909(8) 0.0178(4) Uani 1 1 d . U . . .
N1B N 0.36198(11) 0.70997(14) 0.32882(9) 0.0206(4) Uani 1 1 d . U . . .
N2B N 0.33504(11) 0.68653(14) 0.38041(9) 0.0190(4) Uani 1 1 d . U . . .
O1 O 0.51212(10) -0.04878(13) 0.27939(7) 0.0259(4) Uani 1 1 d . U . . .
H1 H 0.467397 -0.059640 0.291467 0.039 Uiso 1 1 calc R U . . .
O2 O 0.36448(9) -0.07214(11) 0.31877(7) 0.0222(4) Uani 1 1 d . U . . .
O3 O 0.28527(9) 0.06689(11) 0.33088(7) 0.0214(4) Uani 1 1 d . U . . .
O4 O 0.31724(9) 0.17097(12) 0.42978(7) 0.0259(4) Uani 1 1 d . U . . .
O5 O 0.44731(10) 0.14491(12) 0.47175(8) 0.0321(5) Uani 1 1 d . U . . .
O1B O 0.47527(10) 0.75397(13) 0.28871(7) 0.0275(4) Uani 1 1 d . U . . .
H1B H 0.521957 0.763527 0.296623 0.041 Uiso 1 1 calc R U . . .
O2B O 0.62688(9) 0.78178(11) 0.31244(7) 0.0234(4) Uani 1 1 d . U . . .
O3B O 0.71056(9) 0.64514(11) 0.31613(7) 0.0205(4) Uani 1 1 d . U . . .
O4B O 0.69062(10) 0.52961(12) 0.41184(8) 0.0268(4) Uani 1 1 d . U . . .
O5B O 0.56773(11) 0.55171(14) 0.46401(9) 0.0385(5) Uani 1 1 d . U . . .
S1 S 0.33330(3) -0.00199(4) 0.35473(2) 0.01617(14) Uani 1 1 d . U . . .
S2 S 0.39591(3) 0.13992(4) 0.42463(3) 0.02067(15) Uani 1 1 d . U . . .
S1B S 0.66451(3) 0.71132(4) 0.34484(2) 0.01652(14) Uani 1 1 d . U . . .
S2B S 0.61209(3) 0.56239(4) 0.41409(3) 0.02194(15) Uani 1 1 d . U . . .
H1N H 0.7092(17) 0.038(2) 0.3598(12) 0.033 Uiso 1 1 d . U . . .
H2NB H 0.2902(17) 0.674(2) 0.3855(12) 0.033 Uiso 1 1 d . 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
C1 C2 1.524(3) . ?
C1 S1 1.664(2) . ?
C1 S2 1.678(2) . ?
C2 C3 1.500(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.388(3) . ?
C3 C5 1.395(3) . ?
C4 N1 1.336(3) . ?
C4 C6 1.491(3) . ?
C5 O1 1.325(3) . ?
C5 N2 1.338(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N2 1.458(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 F2 1.323(3) . ?
C8 F3 1.331(3) . ?
C8 F1 1.332(3) . ?
C8 S1 1.848(3) . ?
C9 F4 1.325(4) . ?
C9 F5 1.328(3) . ?
C9 F6 1.330(3) . ?
C9 S2 1.842(3) . ?
C1B C2B 1.522(3) . ?
C1B S1B 1.659(2) . ?
C1B S2B 1.684(2) . ?
C2B C3B 1.509(3) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C4B 1.383(3) . ?
C3B C5B 1.396(3) . ?
C4B N2B 1.339(3) . ?
C4B C6B 1.494(3) . ?
C5B O1B 1.328(3) . ?
C5B N1B 1.340(3) . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?
C7B N1B 1.454(3) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B F3B 1.328(3) . ?
C8B F1B 1.331(3) . ?
C8B F2B 1.331(3) . ?
C8B S1B 1.845(3) . ?
C9B F4B 1.323(4) . ?
C9B F6B 1.330(3) . ?
C9B F5B 1.336(3) . ?
C9B S2B 1.839(3) . ?
N1 N2 1.364(3) . ?
N1 H1N 0.78(3) . ?
N1B N2B 1.363(3) . ?
N2B H2NB 0.81(3) . ?
O1 H1 0.8400 . ?
O2 S1 1.4531(17) . ?
O3 S1 1.4339(17) . ?
O4 S2 1.4393(17) . ?
O5 S2 1.4361(18) . ?
O1B H1B 0.8400 . ?
O2B S1B 1.4539(17) . ?
O3B S1B 1.4375(17) . ?
O4B S2B 1.4413(17) . ?
O5B S2B 1.4268(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
C2 C1 S1 118.95(17) . . ?
C2 C1 S2 120.72(16) . . ?
S1 C1 S2 120.19(13) . . ?
C3 C2 C1 115.83(19) . . ?
C3 C2 H2A 108.3 . . ?
C1 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C1 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C4 C3 C5 105.0(2) . . ?
C4 C3 C2 126.5(2) . . ?
C5 C3 C2 128.6(2) . . ?
N1 C4 C3 108.6(2) . . ?
N1 C4 C6 121.6(2) . . ?
C3 C4 C6 129.8(2) . . ?
O1 C5 N2 117.2(2) . . ?
O1 C5 C3 133.2(2) . . ?
N2 C5 C3 109.6(2) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
F2 C8 F3 108.4(2) . . ?
F2 C8 F1 108.80(19) . . ?
F3 C8 F1 108.2(2) . . ?
F2 C8 S1 110.97(17) . . ?
F3 C8 S1 110.51(16) . . ?
F1 C8 S1 109.95(17) . . ?
F4 C9 F5 108.7(2) . . ?
F4 C9 F6 108.6(3) . . ?
F5 C9 F6 108.8(2) . . ?
F4 C9 S2 111.28(19) . . ?
F5 C9 S2 108.5(2) . . ?
F6 C9 S2 110.88(19) . . ?
C2B C1B S1B 119.80(17) . . ?
C2B C1B S2B 119.39(17) . . ?
S1B C1B S2B 120.65(14) . . ?
C3B C2B C1B 115.12(19) . . ?
C3B C2B H2B1 108.5 . . ?
C1B C2B H2B1 108.5 . . ?
C3B C2B H2B2 108.5 . . ?
C1B C2B H2B2 108.5 . . ?
H2B1 C2B H2B2 107.5 . . ?
C4B C3B C5B 105.4(2) . . ?
C4B C3B C2B 127.1(2) . . ?
C5B C3B C2B 127.5(2) . . ?
N2B C4B C3B 108.2(2) . . ?
N2B C4B C6B 121.4(2) . . ?
C3B C4B C6B 130.3(2) . . ?
O1B C5B N1B 116.9(2) . . ?
O1B C5B C3B 133.6(2) . . ?
N1B C5B C3B 109.5(2) . . ?
C4B C6B H6B1 109.5 . . ?
C4B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C4B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
N1B C7B H7B1 109.5 . . ?
N1B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N1B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
F3B C8B F1B 108.7(2) . . ?
F3B C8B F2B 108.0(2) . . ?
F1B C8B F2B 108.3(2) . . ?
F3B C8B S1B 111.15(16) . . ?
F1B C8B S1B 110.24(18) . . ?
F2B C8B S1B 110.46(17) . . ?
F4B C9B F6B 108.8(3) . . ?
F4B C9B F5B 108.6(2) . . ?
F6B C9B F5B 108.7(2) . . ?
F4B C9B S2B 111.17(19) . . ?
F6B C9B S2B 111.2(2) . . ?
F5B C9B S2B 108.4(2) . . ?
C4 N1 N2 109.42(19) . . ?
C4 N1 H1N 127(2) . . ?
N2 N1 H1N 124(2) . . ?
C5 N2 N1 107.35(18) . . ?
C5 N2 C7 128.9(2) . . ?
N1 N2 C7 122.60(19) . . ?
C5B N1B N2B 107.07(19) . . ?
C5B N1B C7B 128.1(2) . . ?
N2B N1B C7B 123.91(19) . . ?
C4B N2B N1B 109.82(19) . . ?
C4B N2B H2NB 129(2) . . ?
N1B N2B H2NB 122(2) . . ?
C5 O1 H1 109.5 . . ?
C5B O1B H1B 109.5 . . ?
O3 S1 O2 119.27(10) . . ?
O3 S1 C1 114.14(11) . . ?
O2 S1 C1 109.37(10) . . ?
O3 S1 C8 102.64(10) . . ?
O2 S1 C8 101.27(11) . . ?
C1 S1 C8 108.58(11) . . ?
O5 S2 O4 119.96(11) . . ?
O5 S2 C1 108.62(11) . . ?
O4 S2 C1 113.38(11) . . ?
O5 S2 C9 102.91(13) . . ?
O4 S2 C9 102.66(12) . . ?
C1 S2 C9 107.99(13) . . ?
O3B S1B O2B 118.92(10) . . ?
O3B S1B C1B 114.48(11) . . ?
O2B S1B C1B 109.55(11) . . ?
O3B S1B C8B 102.79(10) . . ?
O2B S1B C8B 100.36(11) . . ?
C1B S1B C8B 109.10(12) . . ?
O5B S2B O4B 119.91(11) . . ?
O5B S2B C1B 109.15(12) . . ?
O4B S2B C1B 113.53(11) . . ?
O5B S2B C9B 103.87(14) . . ?
O4B S2B C9B 101.77(12) . . ?
C1B S2B C9B 107.08(13) . . ?

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
S1 C1 C2 C3 100.4(2) . . . . ?
S2 C1 C2 C3 -83.8(2) . . . . ?
C1 C2 C3 C4 115.4(3) . . . . ?
C1 C2 C3 C5 -65.0(3) . . . . ?
C5 C3 C4 N1 -1.0(3) . . . . ?
C2 C3 C4 N1 178.7(2) . . . . ?
C5 C3 C4 C6 178.7(3) . . . . ?
C2 C3 C4 C6 -1.6(4) . . . . ?
C4 C3 C5 O1 179.8(3) . . . . ?
C2 C3 C5 O1 0.1(4) . . . . ?
C4 C3 C5 N2 -0.1(3) . . . . ?
C2 C3 C5 N2 -179.8(2) . . . . ?
S1B C1B C2B C3B 102.1(2) . . . . ?
S2B C1B C2B C3B -82.6(2) . . . . ?
C1B C2B C3B C4B 119.2(3) . . . . ?
C1B C2B C3B C5B -60.8(3) . . . . ?
C5B C3B C4B N2B -0.5(3) . . . . ?
C2B C3B C4B N2B 179.5(2) . . . . ?
C5B C3B C4B C6B 177.7(2) . . . . ?
C2B C3B C4B C6B -2.3(4) . . . . ?
C4B C3B C5B O1B -179.9(3) . . . . ?
C2B C3B C5B O1B 0.1(4) . . . . ?
C4B C3B C5B N1B -0.2(3) . . . . ?
C2B C3B C5B N1B 179.8(2) . . . . ?
C3 C4 N1 N2 1.7(3) . . . . ?
C6 C4 N1 N2 -178.0(2) . . . . ?
O1 C5 N2 N1 -178.8(2) . . . . ?
C3 C5 N2 N1 1.1(3) . . . . ?
O1 C5 N2 C7 -11.0(4) . . . . ?
C3 C5 N2 C7 168.9(2) . . . . ?
C4 N1 N2 C5 -1.8(3) . . . . ?
C4 N1 N2 C7 -170.5(2) . . . . ?
O1B C5B N1B N2B -179.4(2) . . . . ?
C3B C5B N1B N2B 0.8(3) . . . . ?
O1B C5B N1B C7B -10.0(4) . . . . ?
C3B C5B N1B C7B 170.2(2) . . . . ?
C3B C4B N2B N1B 1.1(3) . . . . ?
C6B C4B N2B N1B -177.4(2) . . . . ?
C5B N1B N2B C4B -1.2(3) . . . . ?
C7B N1B N2B C4B -171.1(2) . . . . ?
C2 C1 S1 O3 -163.22(16) . . . . ?
S2 C1 S1 O3 20.97(19) . . . . ?
C2 C1 S1 O2 -26.7(2) . . . . ?
S2 C1 S1 O2 157.49(14) . . . . ?
C2 C1 S1 C8 83.0(2) . . . . ?
S2 C1 S1 C8 -92.84(17) . . . . ?
F2 C8 S1 O3 -52.89(18) . . . . ?
F3 C8 S1 O3 -173.14(16) . . . . ?
F1 C8 S1 O3 67.52(19) . . . . ?
F2 C8 S1 O2 -176.65(16) . . . . ?
F3 C8 S1 O2 63.10(18) . . . . ?
F1 C8 S1 O2 -56.23(19) . . . . ?
F2 C8 S1 C1 68.28(19) . . . . ?
F3 C8 S1 C1 -51.97(19) . . . . ?
F1 C8 S1 C1 -171.30(16) . . . . ?
C2 C1 S2 O5 -15.2(2) . . . . ?
S1 C1 S2 O5 160.53(14) . . . . ?
C2 C1 S2 O4 -151.24(18) . . . . ?
S1 C1 S2 O4 24.50(19) . . . . ?
C2 C1 S2 C9 95.7(2) . . . . ?
S1 C1 S2 C9 -88.54(17) . . . . ?
F4 C9 S2 O5 177.1(2) . . . . ?
F5 C9 S2 O5 -63.4(2) . . . . ?
F6 C9 S2 O5 56.1(2) . . . . ?
F4 C9 S2 O4 -57.7(2) . . . . ?
F5 C9 S2 O4 61.8(2) . . . . ?
F6 C9 S2 O4 -178.7(2) . . . . ?
F4 C9 S2 C1 62.3(2) . . . . ?
F5 C9 S2 C1 -178.15(18) . . . . ?
F6 C9 S2 C1 -58.6(2) . . . . ?
C2B C1B S1B O3B -167.67(16) . . . . ?
S2B C1B S1B O3B 17.07(19) . . . . ?
C2B C1B S1B O2B -31.2(2) . . . . ?
S2B C1B S1B O2B 153.58(14) . . . . ?
C2B C1B S1B C8B 77.8(2) . . . . ?
S2B C1B S1B C8B -97.46(16) . . . . ?
F3B C8B S1B O3B -170.77(17) . . . . ?
F1B C8B S1B O3B 68.68(19) . . . . ?
F2B C8B S1B O3B -50.94(19) . . . . ?
F3B C8B S1B O2B 66.16(19) . . . . ?
F1B C8B S1B O2B -54.39(19) . . . . ?
F2B C8B S1B O2B -174.01(17) . . . . ?
F3B C8B S1B C1B -48.9(2) . . . . ?
F1B C8B S1B C1B -169.43(17) . . . . ?
F2B C8B S1B C1B 71.0(2) . . . . ?
C2B C1B S2B O5B -12.8(2) . . . . ?
S1B C1B S2B O5B 162.43(15) . . . . ?
C2B C1B S2B O4B -149.49(17) . . . . ?
S1B C1B S2B O4B 25.8(2) . . . . ?
C2B C1B S2B C9B 99.0(2) . . . . ?
S1B C1B S2B C9B -85.72(17) . . . . ?
F4B C9B S2B O5B 178.76(19) . . . . ?
F6B C9B S2B O5B 57.4(3) . . . . ?
F5B C9B S2B O5B -62.0(2) . . . . ?
F4B C9B S2B O4B -56.1(2) . . . . ?
F6B C9B S2B O4B -177.4(2) . . . . ?
F5B C9B S2B O4B 63.2(2) . . . . ?
F4B C9B S2B C1B 63.3(2) . . . . ?
F6B C9B S2B C1B -58.0(3) . . . . ?
F5B C9B S2B C1B -177.43(18) . . . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_SH-116a
_database_code_depnum_ccdc_archive 'CCDC 1832230'

_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-09-20 downloaded from the CCDC.
;
_publcif_datablock.id            {5b09c1bc-2d17-4d37-b701-5bbe0177b087}

#==============================================================================
# SH-116a
#==============================================================================
_audit_creation_date             2018-02-14
_audit_creation_method           SHELXL-2014

#==============================================================================
#  CHEMICAL DATA
#==============================================================================

_chemical_name_systematic        
;
2-(5-hydroxy-2,3-dimethyl-1-phenyl-1H-pyrazol-2-ium-4-yl)-
1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
;
_chemical_name_common            ?
_chemical_melting_point          354
_chemical_formula_moiety         'C15 H14 F6 N2 O5 S2'
_chemical_formula_sum            'C15 H14 F6 N2 O5 S2'
_chemical_formula_weight         480.40
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_absolute_configuration .

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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   27.2048(18)
_cell_length_b                   18.3507(12)
_cell_length_c                   12.2694(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6125.2(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.28

_exptl_crystal_description       block

_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             2928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_correction_T_min  0.838
_exptl_absorpt_correction_T_max  0.925
_exptl_absorpt_process_details   
;
Crystal Faces plugin in Bruker APEX2 software
;

#==============================================================================
#   EXPERIMENTAL DATA
#==============================================================================

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker TXS fine-focus Turbo X-ray Source'
_diffrn_radiation_monochromator  'Bruker Helios multilayered confocal mirror'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            58829
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.338
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_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             10834
_reflns_number_gt                10264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_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       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_cell_refinement       'APEX2 V2014.11-0 (Bruker AXS Inc.,2014)'
_computing_data_reduction        'SAINT V8.34a (Bruker AXS Inc., 2013)'
_computing_structure_solution    
'SHELXTL XT Intrinsic Phasing (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (A.L.Spek, 2003)'
_computing_publication_material  
;
pubCIF (Westrip, 2010) and enCIFer (Allen et al. 2004)
;


_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)+(0.0412P)²+1.0061P] 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 4669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(15)
_refine_ls_number_reflns         10834
_refine_ls_number_parameters     820
_refine_ls_number_restraints     1099
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0653
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.015
_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
C1 C 0.31090(10) 0.10260(15) 0.3336(2) 0.0189(6) Uani 1 1 d . U . . .
C2 C 0.36548(10) 0.12229(15) 0.3291(2) 0.0193(6) Uani 1 1 d . U . . .
H2A H 0.383373 0.082199 0.292468 0.023 Uiso 1 1 calc R U . . .
H2B H 0.369389 0.166527 0.283744 0.023 Uiso 1 1 calc R U . . .
C3 C 0.38898(10) 0.13589(15) 0.4381(2) 0.0168(6) Uani 1 1 d . U . . .
C4 C 0.42287(10) 0.09358(15) 0.4934(2) 0.0190(6) Uani 1 1 d . U . . .
C5 C 0.38062(10) 0.19556(14) 0.5051(2) 0.0156(6) Uani 1 1 d . U . . .
C6 C 0.44573(12) 0.02290(15) 0.4603(3) 0.0261(7) Uani 1 1 d . U . . .
H6A H 0.481336 0.029250 0.452861 0.039 Uiso 1 1 calc R U . . .
H6B H 0.431890 0.007214 0.390363 0.039 Uiso 1 1 calc R U . . .
H6C H 0.438933 -0.014091 0.515875 0.039 Uiso 1 1 calc R U . . .
C7 C 0.47694(10) 0.11276(16) 0.6587(2) 0.0207(6) Uani 1 1 d . U . . .
H7A H 0.500322 0.081081 0.620667 0.031 Uiso 1 1 calc R U . . .
H7B H 0.466450 0.089310 0.726594 0.031 Uiso 1 1 calc R U . . .
H7C H 0.492742 0.159426 0.675439 0.031 Uiso 1 1 calc R U . . .
C8 C 0.40513(10) 0.23421(15) 0.6925(2) 0.0176(6) Uani 1 1 d . U . . .
C9 C 0.39209(11) 0.20323(17) 0.7902(2) 0.0243(6) Uani 1 1 d . U . . .
H9 H 0.386696 0.152201 0.795452 0.029 Uiso 1 1 calc R U . . .
C10 C 0.38690(12) 0.24731(19) 0.8809(3) 0.0318(7) Uani 1 1 d . U . . .
H10 H 0.378522 0.226356 0.949250 0.038 Uiso 1 1 calc R U . . .
C11 C 0.39389(12) 0.32205(18) 0.8726(3) 0.0319(7) Uani 1 1 d . U . . .
H11 H 0.389827 0.352291 0.934773 0.038 Uiso 1 1 calc R U . . .
C12 C 0.40675(11) 0.35224(17) 0.7736(2) 0.0256(7) Uani 1 1 d . U . . .
H12 H 0.411594 0.403370 0.768058 0.031 Uiso 1 1 calc R U . . .
C13 C 0.41267(10) 0.30876(15) 0.6822(2) 0.0190(6) Uani 1 1 d . U . . .
H13 H 0.421681 0.329440 0.614134 0.023 Uiso 1 1 calc R U . . .
C14 C 0.25870(13) 0.17292(18) 0.1608(3) 0.0315(7) Uani 1 1 d . U . . .
C15 C 0.28355(12) -0.00034(17) 0.4972(3) 0.0281(7) Uani 1 1 d . U . . .
C1B C 0.47734(10) 0.41348(15) 0.3515(2) 0.0189(6) Uani 1 1 d . U . . .
C2B C 0.52940(10) 0.38399(15) 0.3396(2) 0.0197(6) Uani 1 1 d . U . . .
H2B1 H 0.528309 0.338753 0.295685 0.024 Uiso 1 1 calc R U . . .
H2B2 H 0.549412 0.420016 0.299108 0.024 Uiso 1 1 calc R U . . .
C3B C 0.55418(10) 0.36784(15) 0.4462(2) 0.0176(6) Uani 1 1 d . U . . .
C4B C 0.59542(10) 0.40047(15) 0.4922(2) 0.0197(6) Uani 1 1 d . U . . .
C5B C 0.53917(10) 0.31596(14) 0.5214(2) 0.0167(6) Uani 1 1 d . U . . .
C6B C 0.62762(11) 0.45864(16) 0.4463(3) 0.0252(7) Uani 1 1 d . U . . .
H6B1 H 0.638073 0.491478 0.504845 0.038 Uiso 1 1 calc R U . . .
H6B2 H 0.609357 0.486326 0.391271 0.038 Uiso 1 1 calc R U . . .
H6B3 H 0.656601 0.436345 0.412512 0.038 Uiso 1 1 calc R U . . .
C7B C 0.64406(10) 0.38212(16) 0.6675(3) 0.0236(7) Uani 1 1 d . U . . .
H7B1 H 0.662389 0.336637 0.677520 0.035 Uiso 1 1 calc R U . . .
H7B2 H 0.630394 0.397818 0.737574 0.035 Uiso 1 1 calc R U . . .
H7B3 H 0.666187 0.419859 0.639454 0.035 Uiso 1 1 calc R U . . .
C8B C 0.56510(10) 0.27447(15) 0.7065(2) 0.0183(6) Uani 1 1 d . U . . .
C9B C 0.53303(11) 0.29732(16) 0.7868(2) 0.0231(6) Uani 1 1 d . U . . .
H9B H 0.515743 0.342054 0.779828 0.028 Uiso 1 1 calc R U . . .
C10B C 0.52661(12) 0.25371(18) 0.8777(3) 0.0305(7) Uani 1 1 d . U . . .
H10B H 0.504858 0.268510 0.934075 0.037 Uiso 1 1 calc R U . . .
C11B C 0.55206(13) 0.18810(18) 0.8865(3) 0.0327(7) Uani 1 1 d . U . . .
H11B H 0.546942 0.157831 0.948303 0.039 Uiso 1 1 calc R U . . .
C12B C 0.58449(12) 0.16669(19) 0.8068(3) 0.0335(7) Uani 1 1 d . U . . .
H12B H 0.602440 0.122603 0.814789 0.040 Uiso 1 1 calc R U . . .
C13B C 0.59107(12) 0.20950(17) 0.7143(3) 0.0255(7) Uani 1 1 d . U . . .
H13B H 0.612796 0.194661 0.657888 0.031 Uiso 1 1 calc R U . . .
C14B C 0.41694(12) 0.35601(18) 0.1817(3) 0.0298(7) Uani 1 1 d . U . . .
C15B C 0.45904(11) 0.51087(16) 0.5293(3) 0.0269(7) Uani 1 1 d . U . . .
C1C C 0.62388(10) 0.09102(15) 0.3484(2) 0.0213(6) Uani 1 1 d . U . . .
C2C C 0.67450(11) 0.11787(16) 0.3114(2) 0.0239(6) Uani 1 1 d . U . . .
H2C1 H 0.689765 0.080350 0.264304 0.029 Uiso 1 1 calc R U . . .
H2C2 H 0.670352 0.162627 0.267279 0.029 Uiso 1 1 calc R U . . .
C3C C 0.70838(11) 0.13392(15) 0.4054(2) 0.0212(6) Uani 1 1 d . U . . .
C4C C 0.74981(11) 0.09561(16) 0.4380(3) 0.0238(7) Uani 1 1 d . U . . .
C5C C 0.70139(11) 0.18692(15) 0.4843(2) 0.0190(6) Uani 1 1 d . U . . .
C6C C 0.77406(11) 0.03082(17) 0.3878(3) 0.0341(8) Uani 1 1 d . U . . .
H6C1 H 0.808420 0.042450 0.371283 0.051 Uiso 1 1 calc R U . . .
H6C2 H 0.756903 0.017731 0.320311 0.051 Uiso 1 1 calc R U . . .
H6C3 H 0.772763 -0.010244 0.438741 0.051 Uiso 1 1 calc R U . . .
C7C C 0.80725(11) 0.10000(17) 0.6005(3) 0.0258(7) Uani 1 1 d . U . . .
H7C1 H 0.795170 0.062391 0.650481 0.039 Uiso 1 1 calc R U . . .
H7C2 H 0.819935 0.141318 0.642583 0.039 Uiso 1 1 calc R U . . .
H7C3 H 0.833627 0.079792 0.555273 0.039 Uiso 1 1 calc R U . . .
C8C C 0.74338(10) 0.22488(15) 0.6570(2) 0.0205(6) Uani 1 1 d . U . . .
C9C C 0.73010(14) 0.19700(19) 0.7568(3) 0.0361(8) Uani 1 1 d . U . . .
H9C H 0.716502 0.149480 0.762708 0.043 Uiso 1 1 calc R U . . .
C10C C 0.73704(16) 0.2400(2) 0.8486(3) 0.0468(9) Uani 1 1 d . U . . .
H10C H 0.728652 0.221646 0.918555 0.056 Uiso 1 1 calc R U . . .
C11C C 0.75623(14) 0.30959(18) 0.8381(3) 0.0389(8) Uani 1 1 d . U . . .
H11C H 0.761190 0.338552 0.901360 0.047 Uiso 1 1 calc R U . . .
C12C C 0.76809(11) 0.33708(17) 0.7381(3) 0.0260(7) Uani 1 1 d . U . . .
H12C H 0.780912 0.385060 0.732006 0.031 Uiso 1 1 calc R U . . .
C13C C 0.76141(10) 0.29500(16) 0.6455(3) 0.0206(6) Uani 1 1 d . U . . .
H13C H 0.769069 0.313916 0.575496 0.025 Uiso 1 1 calc R U . . .
C14C C 0.62367(12) -0.00139(17) 0.5366(3) 0.0290(7) Uani 1 1 d . U . . .
C15C C 0.54878(16) 0.1453(2) 0.2109(3) 0.0463(10) Uani 1 1 d . U . . .
F1 F 0.22779(8) 0.22698(12) 0.13810(16) 0.0461(5) Uani 1 1 d . U . . .
F2 F 0.30081(8) 0.18573(12) 0.10996(16) 0.0434(5) Uani 1 1 d . U . . .
F3 F 0.23959(9) 0.11163(12) 0.12191(16) 0.0473(6) Uani 1 1 d . U . . .
F4 F 0.24696(7) 0.04044(11) 0.53608(16) 0.0354(5) Uani 1 1 d . U . . .
F5 F 0.27217(8) -0.06993(10) 0.51432(18) 0.0449(5) Uani 1 1 d . U . . .
F6 F 0.32354(7) 0.01479(11) 0.55518(15) 0.0368(5) Uani 1 1 d . U . . .
F1B F 0.45709(7) 0.33534(11) 0.12750(15) 0.0390(5) Uani 1 1 d . U . . .
F2B F 0.38127(7) 0.30850(11) 0.15967(16) 0.0403(5) Uani 1 1 d . U . . .
F3B F 0.40315(8) 0.42063(11) 0.14408(16) 0.0442(5) Uani 1 1 d . U . . .
F4B F 0.41874(7) 0.47646(11) 0.56221(16) 0.0384(5) Uani 1 1 d . U . . .
F5B F 0.45445(8) 0.58073(10) 0.55564(18) 0.0412(5) Uani 1 1 d . U . . .
F6B F 0.49671(8) 0.48390(12) 0.58469(16) 0.0409(5) Uani 1 1 d . U . . .
F1C F 0.51628(10) 0.19841(14) 0.1982(2) 0.0695(8) Uani 1 1 d . U . . .
F2C F 0.52603(10) 0.08204(13) 0.1937(2) 0.0684(8) Uani 1 1 d . U . . .
F3C F 0.58349(11) 0.15299(16) 0.13679(19) 0.0722(8) Uani 1 1 d . U . . .
F4C F 0.59058(8) 0.03809(12) 0.58819(16) 0.0445(5) Uani 1 1 d . U . . .
F5C F 0.61824(9) -0.07032(11) 0.56826(18) 0.0478(5) Uani 1 1 d . U . . .
F6C F 0.66776(8) 0.02043(13) 0.56796(16) 0.0452(5) Uani 1 1 d . U . . .
N1 N 0.43409(9) 0.12539(12) 0.5891(2) 0.0184(5) Uani 1 1 d . U . . .
N2 N 0.40821(9) 0.19031(12) 0.59575(19) 0.0169(5) Uani 1 1 d . U . . .
N1B N 0.60414(8) 0.37027(13) 0.5899(2) 0.0198(5) Uani 1 1 d . U . . .
N2B N 0.56920(8) 0.31701(13) 0.6085(2) 0.0186(5) Uani 1 1 d . U . . .
N1C N 0.76701(9) 0.12463(13) 0.5307(2) 0.0235(6) Uani 1 1 d . U . . .
N2C N 0.73654(9) 0.18136(13) 0.5604(2) 0.0196(5) Uani 1 1 d . U . . .
O1 O 0.35063(7) 0.25250(10) 0.49723(16) 0.0173(4) Uani 1 1 d . U . . .
H1 H 0.332832 0.247880 0.441717 0.026 Uiso 1 1 calc R U . . .
O2 O 0.28998(7) 0.23781(10) 0.33058(17) 0.0248(5) Uani 1 1 d . U . . .
O3 O 0.22075(7) 0.15094(12) 0.35204(19) 0.0285(5) Uani 1 1 d . U . . .
O4 O 0.24641(8) -0.00163(12) 0.3041(2) 0.0321(5) Uani 1 1 d . U . . .
O5 O 0.33489(8) -0.03117(11) 0.32887(19) 0.0305(5) Uani 1 1 d . U . . .
O1B O 0.50225(7) 0.26870(11) 0.52234(16) 0.0200(4) Uani 1 1 d . U . . .
H1B H 0.487469 0.270222 0.462271 0.030 Uiso 1 1 calc R U . . .
O2B O 0.44311(7) 0.28448(10) 0.34943(16) 0.0205(4) Uani 1 1 d . U . . .
O3B O 0.38378(7) 0.38626(11) 0.37331(17) 0.0244(5) Uani 1 1 d . U . . .
O4B O 0.42457(8) 0.53237(11) 0.3365(2) 0.0317(5) Uani 1 1 d . U . . .
O5B O 0.51498(8) 0.53954(11) 0.36594(19) 0.0291(5) Uani 1 1 d . U . . .
O1C O 0.66725(7) 0.23808(10) 0.49765(16) 0.0215(4) Uani 1 1 d . U . . .
H1C H 0.648410 0.238389 0.443410 0.032 Uiso 1 1 calc R U . . .
O2C O 0.59438(8) 0.22213(11) 0.35150(18) 0.0289(5) Uani 1 1 d . U . . .
O3C O 0.53645(8) 0.12718(12) 0.4186(2) 0.0321(5) Uani 1 1 d . U . . .
O4C O 0.56804(8) -0.02343(11) 0.3711(2) 0.0323(5) Uani 1 1 d . U . . .
O5C O 0.65854(8) -0.03738(11) 0.34922(19) 0.0283(5) Uani 1 1 d . U . . .
S1 S 0.26842(3) 0.16664(4) 0.30967(6) 0.02002(16) Uani 1 1 d . U . . .
S2 S 0.29359(3) 0.01530(4) 0.35008(6) 0.02155(16) Uani 1 1 d . U . . .
S1B S 0.42895(2) 0.35957(4) 0.32937(6) 0.01797(15) Uani 1 1 d . U . . .
S2B S 0.46876(3) 0.50230(4) 0.38033(6) 0.02121(16) Uani 1 1 d . U . . .
S1C S 0.57608(3) 0.14770(4) 0.34840(6) 0.02440(17) Uani 1 1 d . U . . .
S2C S 0.61680(3) 0.00384(4) 0.38684(6) 0.02153(16) Uani 1 1 d . 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
C1 C2 1.529(4) . ?
C1 S1 1.674(3) . ?
C1 S2 1.682(3) . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.383(4) . ?
C3 C5 1.388(4) . ?
C4 N1 1.347(4) . ?
C4 C6 1.495(4) . ?
C5 O1 1.329(3) . ?
C5 N2 1.345(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N1 1.463(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.373(4) . ?
C8 C13 1.389(4) . ?
C8 N2 1.437(4) . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 F2 1.326(4) . ?
C14 F3 1.328(4) . ?
C14 F1 1.330(4) . ?
C14 S1 1.849(3) . ?
C15 F6 1.329(4) . ?
C15 F5 1.331(4) . ?
C15 F4 1.334(4) . ?
C15 S2 1.847(4) . ?
C1B C2B 1.523(4) . ?
C1B S1B 1.669(3) . ?
C1B S2B 1.684(3) . ?
C2B C3B 1.501(4) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B C5B 1.388(4) . ?
C3B C4B 1.392(4) . ?
C4B N1B 1.342(4) . ?
C4B C6B 1.492(4) . ?
C5B O1B 1.327(3) . ?
C5B N2B 1.345(4) . ?
C6B H6B1 0.9800 . ?
C6B H6B2 0.9800 . ?
C6B H6B3 0.9800 . ?
C7B N1B 1.460(4) . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B C9B 1.382(4) . ?
C8B C13B 1.389(4) . ?
C8B N2B 1.438(4) . ?
C9B C10B 1.383(4) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.393(5) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.375(5) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.391(5) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B F3B 1.327(4) . ?
C14B F2B 1.332(4) . ?
C14B F1B 1.334(4) . ?
C14B S1B 1.842(3) . ?
C15B F5B 1.328(4) . ?
C15B F4B 1.328(4) . ?
C15B F6B 1.325(4) . ?
C15B S2B 1.854(4) . ?
C1C C2C 1.531(4) . ?
C1C S1C 1.665(3) . ?
C1C S2C 1.679(3) . ?
C2C C3C 1.506(4) . ?
C2C H2C1 0.9900 . ?
C2C H2C2 0.9900 . ?
C3C C5C 1.385(4) . ?
C3C C4C 1.387(4) . ?
C4C N1C 1.340(4) . ?
C4C C6C 1.493(4) . ?
C5C O1C 1.331(3) . ?
C5C N2C 1.340(4) . ?
C6C H6C1 0.9800 . ?
C6C H6C2 0.9800 . ?
C6C H6C3 0.9800 . ?
C7C N1C 1.462(4) . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C C9C 1.375(5) . ?
C8C C13C 1.384(4) . ?
C8C N2C 1.441(4) . ?
C9C C10C 1.388(5) . ?
C9C H9C 0.9500 . ?
C10C C11C 1.386(5) . ?
C10C H10C 0.9500 . ?
C11C C12C 1.365(5) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.385(4) . ?
C12C H12C 0.9500 . ?
C13C H13C 0.9500 . ?
C14C F4C 1.317(4) . ?
C14C F6C 1.322(4) . ?
C14C F5C 1.331(4) . ?
C14C S2C 1.849(4) . ?
C15C F3C 1.319(5) . ?
C15C F1C 1.325(4) . ?
C15C F2C 1.332(5) . ?
C15C S1C 1.843(4) . ?
N1 N2 1.386(3) . ?
N1B N2B 1.382(3) . ?
N1C N2C 1.380(3) . ?
O1 H1 0.8400 . ?
O2 S1 1.455(2) . ?
O3 S1 1.427(2) . ?
O4 S2 1.436(2) . ?
O5 S2 1.434(2) . ?
O1B H1B 0.8400 . ?
O2B S1B 1.452(2) . ?
O3B S1B 1.428(2) . ?
O4B S2B 1.428(2) . ?
O5B S2B 1.442(2) . ?
O1C H1C 0.8400 . ?
O2C S1C 1.454(2) . ?
O3C S1C 1.430(2) . ?
O4C S2C 1.431(2) . ?
O5C S2C 1.441(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 S1 119.9(2) . . ?
C2 C1 S2 120.1(2) . . ?
S1 C1 S2 119.77(16) . . ?
C3 C2 C1 114.9(2) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C5 105.2(3) . . ?
C4 C3 C2 128.8(3) . . ?
C5 C3 C2 126.0(3) . . ?
N1 C4 C3 109.6(2) . . ?
N1 C4 C6 121.3(3) . . ?
C3 C4 C6 129.1(3) . . ?
O1 C5 N2 117.3(2) . . ?
O1 C5 C3 132.7(3) . . ?
N2 C5 C3 110.0(2) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.7(3) . . ?
C9 C8 N2 120.3(3) . . ?
C13 C8 N2 117.9(2) . . ?
C8 C9 C10 119.1(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 118.5(3) . . ?
C12 C13 H13 120.8 . . ?
C8 C13 H13 120.8 . . ?
F2 C14 F3 108.6(3) . . ?
F2 C14 F1 108.4(3) . . ?
F3 C14 F1 108.0(3) . . ?
F2 C14 S1 110.6(2) . . ?
F3 C14 S1 111.0(2) . . ?
F1 C14 S1 110.1(2) . . ?
F6 C15 F5 107.8(3) . . ?
F6 C15 F4 107.6(3) . . ?
F5 C15 F4 107.9(3) . . ?
F6 C15 S2 111.7(2) . . ?
F5 C15 S2 109.8(2) . . ?
F4 C15 S2 111.9(2) . . ?
C2B C1B S1B 120.5(2) . . ?
C2B C1B S2B 119.5(2) . . ?
S1B C1B S2B 119.90(16) . . ?
C3B C2B C1B 113.8(2) . . ?
C3B C2B H2B1 108.8 . . ?
C1B C2B H2B1 108.8 . . ?
C3B C2B H2B2 108.8 . . ?
C1B C2B H2B2 108.8 . . ?
H2B1 C2B H2B2 107.7 . . ?
C5B C3B C4B 105.2(3) . . ?
C5B C3B C2B 125.7(3) . . ?
C4B C3B C2B 129.1(3) . . ?
N1B C4B C3B 109.1(2) . . ?
N1B C4B C6B 122.0(3) . . ?
C3B C4B C6B 128.9(3) . . ?
O1B C5B N2B 117.6(2) . . ?
O1B C5B C3B 132.6(3) . . ?
N2B C5B C3B 109.9(2) . . ?
C4B C6B H6B1 109.5 . . ?
C4B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C4B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
N1B C7B H7B1 109.5 . . ?
N1B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N1B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C9B C8B C13B 122.2(3) . . ?
C9B C8B N2B 118.7(3) . . ?
C13B C8B N2B 119.0(3) . . ?
C8B C9B C10B 118.6(3) . . ?
C8B C9B H9B 120.7 . . ?
C10B C9B H9B 120.7 . . ?
C9B C10B C11B 120.0(3) . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C12B C11B C10B 120.7(3) . . ?
C12B C11B H11B 119.6 . . ?
C10B C11B H11B 119.6 . . ?
C11B C12B C13B 120.1(3) . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C12B C13B C8B 118.4(3) . . ?
C12B C13B H13B 120.8 . . ?
C8B C13B H13B 120.8 . . ?
F3B C14B F2B 108.0(3) . . ?
F3B C14B F1B 108.2(3) . . ?
F2B C14B F1B 108.0(3) . . ?
F3B C14B S1B 111.1(2) . . ?
F2B C14B S1B 110.6(2) . . ?
F1B C14B S1B 110.8(2) . . ?
F5B C15B F4B 107.9(3) . . ?
F5B C15B F6B 108.0(3) . . ?
F4B C15B F6B 107.8(3) . . ?
F5B C15B S2B 109.6(2) . . ?
F4B C15B S2B 112.1(2) . . ?
F6B C15B S2B 111.3(2) . . ?
C2C C1C S1C 120.1(2) . . ?
C2C C1C S2C 119.5(2) . . ?
S1C C1C S2C 120.36(18) . . ?
C3C C2C C1C 112.7(2) . . ?
C3C C2C H2C1 109.0 . . ?
C1C C2C H2C1 109.0 . . ?
C3C C2C H2C2 109.0 . . ?
C1C C2C H2C2 109.0 . . ?
H2C1 C2C H2C2 107.8 . . ?
C5C C3C C4C 105.5(3) . . ?
C5C C3C C2C 126.1(3) . . ?
C4C C3C C2C 128.2(3) . . ?
N1C C4C C3C 109.1(3) . . ?
N1C C4C C6C 120.8(3) . . ?
C3C C4C C6C 130.1(3) . . ?
O1C C5C N2C 117.8(3) . . ?
O1C C5C C3C 132.6(3) . . ?
N2C C5C C3C 109.6(3) . . ?
C4C C6C H6C1 109.5 . . ?
C4C C6C H6C2 109.5 . . ?
H6C1 C6C H6C2 109.5 . . ?
C4C C6C H6C3 109.5 . . ?
H6C1 C6C H6C3 109.5 . . ?
H6C2 C6C H6C3 109.5 . . ?
N1C C7C H7C1 109.5 . . ?
N1C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
N1C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C9C C8C C13C 122.0(3) . . ?
C9C C8C N2C 119.5(3) . . ?
C13C C8C N2C 118.5(3) . . ?
C8C C9C C10C 118.4(3) . . ?
C8C C9C H9C 120.8 . . ?
C10C C9C H9C 120.8 . . ?
C11C C10C C9C 120.0(3) . . ?
C11C C10C H10C 120.0 . . ?
C9C C10C H10C 120.0 . . ?
C12C C11C C10C 120.8(3) . . ?
C12C C11C H11C 119.6 . . ?
C10C C11C H11C 119.6 . . ?
C11C C12C C13C 120.0(3) . . ?
C11C C12C H12C 120.0 . . ?
C13C C12C H12C 120.0 . . ?
C8C C13C C12C 118.8(3) . . ?
C8C C13C H13C 120.6 . . ?
C12C C13C H13C 120.6 . . ?
F4C C14C F6C 108.3(3) . . ?
F4C C14C F5C 107.8(3) . . ?
F6C C14C F5C 107.7(3) . . ?
F4C C14C S2C 112.3(2) . . ?
F6C C14C S2C 111.4(2) . . ?
F5C C14C S2C 109.1(2) . . ?
F3C C15C F1C 108.5(4) . . ?
F3C C15C F2C 108.4(3) . . ?
F1C C15C F2C 108.2(3) . . ?
F3C C15C S1C 109.9(3) . . ?
F1C C15C S1C 111.0(2) . . ?
F2C C15C S1C 110.7(3) . . ?
C4 N1 N2 108.0(2) . . ?
C4 N1 C7 128.4(2) . . ?
N2 N1 C7 120.4(2) . . ?
C5 N2 N1 107.2(2) . . ?
C5 N2 C8 127.6(2) . . ?
N1 N2 C8 124.0(2) . . ?
C4B N1B N2B 108.5(2) . . ?
C4B N1B C7B 130.7(2) . . ?
N2B N1B C7B 120.6(2) . . ?
C5B N2B N1B 107.3(2) . . ?
C5B N2B C8B 127.5(2) . . ?
N1B N2B C8B 125.1(2) . . ?
C4C N1C N2C 108.3(2) . . ?
C4C N1C C7C 129.5(3) . . ?
N2C N1C C7C 121.9(3) . . ?
C5C N2C N1C 107.6(2) . . ?
C5C N2C C8C 128.5(2) . . ?
N1C N2C C8C 123.9(2) . . ?
C5 O1 H1 109.5 . . ?
C5B O1B H1B 109.5 . . ?
C5C O1C H1C 109.5 . . ?
O3 S1 O2 118.92(13) . . ?
O3 S1 C1 114.96(14) . . ?
O2 S1 C1 108.73(13) . . ?
O3 S1 C14 104.03(15) . . ?
O2 S1 C14 100.13(14) . . ?
C1 S1 C14 108.39(14) . . ?
O5 S2 O4 120.02(14) . . ?
O5 S2 C1 108.97(13) . . ?
O4 S2 C1 114.13(14) . . ?
O5 S2 C15 101.58(15) . . ?
O4 S2 C15 102.59(15) . . ?
C1 S2 C15 107.88(14) . . ?
O3B S1B O2B 119.33(12) . . ?
O3B S1B C1B 114.45(13) . . ?
O2B S1B C1B 109.01(13) . . ?
O3B S1B C14B 103.34(14) . . ?
O2B S1B C14B 100.38(14) . . ?
C1B S1B C14B 108.71(15) . . ?
O4B S2B O5B 120.32(13) . . ?
O4B S2B C1B 114.30(14) . . ?
O5B S2B C1B 108.19(13) . . ?
O4B S2B C15B 102.62(15) . . ?
O5B S2B C15B 101.83(14) . . ?
C1B S2B C15B 108.00(14) . . ?
O3C S1C O2C 119.32(13) . . ?
O3C S1C C1C 115.11(14) . . ?
O2C S1C C1C 108.61(14) . . ?
O3C S1C C15C 103.94(18) . . ?
O2C S1C C15C 100.63(16) . . ?
C1C S1C C15C 107.42(16) . . ?
O4C S2C O5C 120.27(13) . . ?
O4C S2C C1C 113.69(14) . . ?
O5C S2C C1C 108.65(13) . . ?
O4C S2C C14C 102.09(15) . . ?
O5C S2C C14C 102.21(14) . . ?
C1C S2C C14C 108.49(14) . . ?

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
S1 C1 C2 C3 99.0(3) . . . . ?
S2 C1 C2 C3 -87.0(3) . . . . ?
C1 C2 C3 C4 109.3(3) . . . . ?
C1 C2 C3 C5 -70.8(4) . . . . ?
C5 C3 C4 N1 0.6(3) . . . . ?
C2 C3 C4 N1 -179.5(3) . . . . ?
C5 C3 C4 C6 -179.6(3) . . . . ?
C2 C3 C4 C6 0.3(5) . . . . ?
C4 C3 C5 O1 -177.0(3) . . . . ?
C2 C3 C5 O1 3.0(5) . . . . ?
C4 C3 C5 N2 0.5(3) . . . . ?
C2 C3 C5 N2 -179.4(2) . . . . ?
C13 C8 C9 C10 -0.8(5) . . . . ?
N2 C8 C9 C10 -176.7(3) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
N2 C8 C13 C12 176.0(3) . . . . ?
S1B C1B C2B C3B -102.7(3) . . . . ?
S2B C1B C2B C3B 80.7(3) . . . . ?
C1B C2B C3B C5B 63.7(4) . . . . ?
C1B C2B C3B C4B -115.3(3) . . . . ?
C5B C3B C4B N1B -0.7(3) . . . . ?
C2B C3B C4B N1B 178.5(3) . . . . ?
C5B C3B C4B C6B 178.2(3) . . . . ?
C2B C3B C4B C6B -2.7(5) . . . . ?
C4B C3B C5B O1B 179.8(3) . . . . ?
C2B C3B C5B O1B 0.7(5) . . . . ?
C4B C3B C5B N2B 0.3(3) . . . . ?
C2B C3B C5B N2B -178.8(3) . . . . ?
C13B C8B C9B C10B -0.2(4) . . . . ?
N2B C8B C9B C10B 175.6(3) . . . . ?
C8B C9B C10B C11B -0.3(4) . . . . ?
C9B C10B C11B C12B 1.4(5) . . . . ?
C10B C11B C12B C13B -2.1(5) . . . . ?
C11B C12B C13B C8B 1.5(5) . . . . ?
C9B C8B C13B C12B -0.4(5) . . . . ?
N2B C8B C13B C12B -176.2(3) . . . . ?
S1C C1C C2C C3C 101.7(3) . . . . ?
S2C C1C C2C C3C -79.3(3) . . . . ?
C1C C2C C3C C5C -63.6(4) . . . . ?
C1C C2C C3C C4C 109.6(3) . . . . ?
C5C C3C C4C N1C -0.7(3) . . . . ?
C2C C3C C4C N1C -174.9(3) . . . . ?
C5C C3C C4C C6C 177.6(3) . . . . ?
C2C C3C C4C C6C 3.3(5) . . . . ?
C4C C3C C5C O1C -178.3(3) . . . . ?
C2C C3C C5C O1C -3.8(5) . . . . ?
C4C C3C C5C N2C 0.1(3) . . . . ?
C2C C3C C5C N2C 174.6(3) . . . . ?
C13C C8C C9C C10C -2.7(5) . . . . ?
N2C C8C C9C C10C 180.0(3) . . . . ?
C8C C9C C10C C11C 1.0(6) . . . . ?
C9C C10C C11C C12C 0.6(6) . . . . ?
C10C C11C C12C C13C -0.6(5) . . . . ?
C9C C8C C13C C12C 2.7(5) . . . . ?
N2C C8C C13C C12C -180.0(3) . . . . ?
C11C C12C C13C C8C -1.0(4) . . . . ?
C3 C4 N1 N2 -1.5(3) . . . . ?
C6 C4 N1 N2 178.7(3) . . . . ?
C3 C4 N1 C7 -160.8(3) . . . . ?
C6 C4 N1 C7 19.3(4) . . . . ?
O1 C5 N2 N1 176.6(2) . . . . ?
C3 C5 N2 N1 -1.4(3) . . . . ?
O1 C5 N2 C8 8.3(4) . . . . ?
C3 C5 N2 C8 -169.7(3) . . . . ?
C4 N1 N2 C5 1.8(3) . . . . ?
C7 N1 N2 C5 163.1(2) . . . . ?
C4 N1 N2 C8 170.6(2) . . . . ?
C7 N1 N2 C8 -28.1(4) . . . . ?
C9 C8 N2 C5 116.0(3) . . . . ?
C13 C8 N2 C5 -60.1(4) . . . . ?
C9 C8 N2 N1 -50.5(4) . . . . ?
C13 C8 N2 N1 133.5(3) . . . . ?
C3B C4B N1B N2B 0.7(3) . . . . ?
C6B C4B N1B N2B -178.2(2) . . . . ?
C3B C4B N1B C7B 176.2(3) . . . . ?
C6B C4B N1B C7B -2.8(5) . . . . ?
O1B C5B N2B N1B -179.5(2) . . . . ?
C3B C5B N2B N1B 0.1(3) . . . . ?
O1B C5B N2B C8B -2.8(4) . . . . ?
C3B C5B N2B C8B 176.8(3) . . . . ?
C4B N1B N2B C5B -0.5(3) . . . . ?
C7B N1B N2B C5B -176.5(2) . . . . ?
C4B N1B N2B C8B -177.3(3) . . . . ?
C7B N1B N2B C8B 6.7(4) . . . . ?
C9B C8B N2B C5B -81.3(4) . . . . ?
C13B C8B N2B C5B 94.7(4) . . . . ?
C9B C8B N2B N1B 94.9(3) . . . . ?
C13B C8B N2B N1B -89.2(3) . . . . ?
C3C C4C N1C N2C 1.0(3) . . . . ?
C6C C4C N1C N2C -177.5(3) . . . . ?
C3C C4C N1C C7C 174.7(3) . . . . ?
C6C C4C N1C C7C -3.7(5) . . . . ?
O1C C5C N2C N1C 179.1(2) . . . . ?
C3C C5C N2C N1C 0.5(3) . . . . ?
O1C C5C N2C C8C -1.0(4) . . . . ?
C3C C5C N2C C8C -179.7(3) . . . . ?
C4C N1C N2C C5C -0.9(3) . . . . ?
C7C N1C N2C C5C -175.2(2) . . . . ?
C4C N1C N2C C8C 179.3(3) . . . . ?
C7C N1C N2C C8C 5.0(4) . . . . ?
C9C C8C N2C C5C 103.1(4) . . . . ?
C13C C8C N2C C5C -74.3(4) . . . . ?
C9C C8C N2C N1C -77.1(4) . . . . ?
C13C C8C N2C N1C 105.5(3) . . . . ?
C2 C1 S1 O3 -158.9(2) . . . . ?
S2 C1 S1 O3 27.2(2) . . . . ?
C2 C1 S1 O2 -22.7(3) . . . . ?
S2 C1 S1 O2 163.30(17) . . . . ?
C2 C1 S1 C14 85.2(3) . . . . ?
S2 C1 S1 C14 -88.7(2) . . . . ?
F2 C14 S1 O3 -178.4(2) . . . . ?
F3 C14 S1 O3 -57.8(3) . . . . ?
F1 C14 S1 O3 61.8(3) . . . . ?
F2 C14 S1 O2 58.1(2) . . . . ?
F3 C14 S1 O2 178.8(2) . . . . ?
F1 C14 S1 O2 -61.7(3) . . . . ?
F2 C14 S1 C1 -55.7(3) . . . . ?
F3 C14 S1 C1 65.0(3) . . . . ?
F1 C14 S1 C1 -175.5(2) . . . . ?
C2 C1 S2 O5 -15.2(3) . . . . ?
S1 C1 S2 O5 158.73(18) . . . . ?
C2 C1 S2 O4 -152.4(2) . . . . ?
S1 C1 S2 O4 21.5(2) . . . . ?
C2 C1 S2 C15 94.3(2) . . . . ?
S1 C1 S2 C15 -91.8(2) . . . . ?
F6 C15 S2 O5 57.1(2) . . . . ?
F5 C15 S2 O5 -62.4(2) . . . . ?
F4 C15 S2 O5 177.8(2) . . . . ?
F6 C15 S2 O4 -178.2(2) . . . . ?
F5 C15 S2 O4 62.3(2) . . . . ?
F4 C15 S2 O4 -57.5(2) . . . . ?
F6 C15 S2 C1 -57.4(3) . . . . ?
F5 C15 S2 C1 -176.9(2) . . . . ?
F4 C15 S2 C1 63.3(2) . . . . ?
C2B C1B S1B O3B 162.4(2) . . . . ?
S2B C1B S1B O3B -21.0(2) . . . . ?
C2B C1B S1B O2B 25.9(3) . . . . ?
S2B C1B S1B O2B -157.53(16) . . . . ?
C2B C1B S1B C14B -82.6(3) . . . . ?
S2B C1B S1B C14B 93.9(2) . . . . ?
F3B C14B S1B O3B 56.4(3) . . . . ?
F2B C14B S1B O3B -63.5(3) . . . . ?
F1B C14B S1B O3B 176.8(2) . . . . ?
F3B C14B S1B O2B -179.8(2) . . . . ?
F2B C14B S1B O2B 60.2(3) . . . . ?
F1B C14B S1B O2B -59.5(2) . . . . ?
F3B C14B S1B C1B -65.5(3) . . . . ?
F2B C14B S1B C1B 174.6(2) . . . . ?
F1B C14B S1B C1B 54.8(3) . . . . ?
C2B C1B S2B O4B 149.2(2) . . . . ?
S1B C1B S2B O4B -27.4(2) . . . . ?
C2B C1B S2B O5B 12.2(3) . . . . ?
S1B C1B S2B O5B -164.40(17) . . . . ?
C2B C1B S2B C15B -97.3(2) . . . . ?
S1B C1B S2B C15B 86.1(2) . . . . ?
F5B C15B S2B O4B -61.8(2) . . . . ?
F4B C15B S2B O4B 58.0(2) . . . . ?
F6B C15B S2B O4B 178.8(2) . . . . ?
F5B C15B S2B O5B 63.3(2) . . . . ?
F4B C15B S2B O5B -176.9(2) . . . . ?
F6B C15B S2B O5B -56.1(2) . . . . ?
F5B C15B S2B C1B 177.1(2) . . . . ?
F4B C15B S2B C1B -63.1(2) . . . . ?
F6B C15B S2B C1B 57.7(2) . . . . ?
C2C C1C S1C O3C -158.4(2) . . . . ?
S2C C1C S1C O3C 22.6(2) . . . . ?
C2C C1C S1C O2C -21.6(3) . . . . ?
S2C C1C S1C O2C 159.40(17) . . . . ?
C2C C1C S1C C15C 86.4(3) . . . . ?
S2C C1C S1C C15C -92.6(2) . . . . ?
F3C C15C S1C O3C -170.9(3) . . . . ?
F1C C15C S1C O3C 69.0(3) . . . . ?
F2C C15C S1C O3C -51.2(3) . . . . ?
F3C C15C S1C O2C 65.0(3) . . . . ?
F1C C15C S1C O2C -55.1(4) . . . . ?
F2C C15C S1C O2C -175.2(3) . . . . ?
F3C C15C S1C C1C -48.5(3) . . . . ?
F1C C15C S1C C1C -168.6(3) . . . . ?
F2C C15C S1C C1C 71.2(3) . . . . ?
C2C C1C S2C O4C -152.7(2) . . . . ?
S1C C1C S2C O4C 26.3(2) . . . . ?
C2C C1C S2C O5C -15.9(3) . . . . ?
S1C C1C S2C O5C 163.07(18) . . . . ?
C2C C1C S2C C14C 94.4(3) . . . . ?
S1C C1C S2C C14C -86.6(2) . . . . ?
F4C C14C S2C O4C -59.7(2) . . . . ?
F6C C14C S2C O4C 178.6(2) . . . . ?
F5C C14C S2C O4C 59.8(2) . . . . ?
F4C C14C S2C O5C 175.2(2) . . . . ?
F6C C14C S2C O5C 53.6(2) . . . . ?
F5C C14C S2C O5C -65.2(2) . . . . ?
F4C C14C S2C C1C 60.6(3) . . . . ?
F6C C14C S2C C1C -61.1(3) . . . . ?
F5C C14C S2C C1C -179.9(2) . . . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.041



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

