# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_gdm-CH3SO3
_database_code_depnum_ccdc_archive 'CCDC 2090743'
loop_
_audit_author_name
_audit_author_address
'Craig M. Forsyth'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'guanidinium methanesulfonate'
_chemical_name_common            'guanidinium mesylate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C H3 O3 S, C H6 N3'
_chemical_formula_sum            'C2 H9 N3 O3 S'
_chemical_formula_weight         155.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

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

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

_cell_length_a                   10.343(2)
_cell_length_b                   7.3369(13)
_cell_length_c                   9.8878(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.741(16)
_cell_angle_gamma                90
_cell_volume                     734.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1459
_cell_measurement_theta_min      4.1500
_cell_measurement_theta_max      30.1250

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.390
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.68056
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'OXFORD Gemini Ultra CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_reflns_number            5143
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         30.969
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1157
_reflns_number_gt                966
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+0.1698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1157
_refine_ls_number_parameters     66
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1433
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23083(6) 0.000000 0.45303(6) 0.0268(2) Uani 1 2 d S T P . .
O1 O 0.15138(14) 0.16464(19) 0.42951(13) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.32154(19) 0.000000 0.58659(19) 0.0341(5) Uani 1 2 d S T P . .
N1 N 0.2462(3) 0.500000 0.5729(3) 0.0376(6) Uani 1 2 d S T P . .
N2 N 0.40236(18) 0.3431(2) 0.72672(17) 0.0333(4) Uani 1 1 d . . . . .
C1 C 0.3296(4) 0.000000 0.3281(4) 0.0547(9) Uani 1 2 d DS T P . .
H1A H 0.3845(17) -0.1048(13) 0.337(3) 0.082 Uiso 1 1 d D U . . .
H1B H 0.272(3) 0.000000 0.239(2) 0.082 Uiso 1 2 d DS U P . .
C2 C 0.3504(3) 0.500000 0.6757(2) 0.0289(5) Uani 1 2 d S T P . .
H1N H 0.217(3) 0.405(4) 0.543(3) 0.052(7) Uiso 1 1 d . . . . .
H2N H 0.368(2) 0.246(4) 0.689(2) 0.039(6) Uiso 1 1 d . . . . .
H3N H 0.464(2) 0.346(3) 0.790(2) 0.035(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4529(14) . ?
S1 O1 1.4529(14) 6 ?
S1 O2 1.4560(18) . ?
S1 C1 1.756(3) . ?
N1 C2 1.322(3) . ?
N1 H1N 0.79(3) . ?
N1 H1N 0.79(3) 6_565 ?
N2 C2 1.326(2) . ?
N2 H2N 0.85(3) . ?
N2 H3N 0.80(2) . ?
C1 H1A 0.949(9) . ?
C1 H1B 0.954(10) . ?
C1 H1A 0.949(9) 6 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O1 112.49(12) . 6 ?
O1 S1 O2 112.60(6) . . ?
O1 S1 O2 112.60(6) 6 . ?
O1 S1 C1 106.16(9) . . ?
O1 S1 C1 106.16(9) 6 . ?
O2 S1 C1 106.17(16) . . ?
C2 N1 H1N 118.4(19) . . ?
C2 N1 H1N 118.4(19) . 6_565 ?
H1N N1 H1N 123(4) . 6_565 ?
C2 N2 H2N 117.6(15) . . ?
C2 N2 H3N 118.3(19) . . ?
H2N N2 H3N 124(2) . . ?
S1 C1 H1A 111.1(16) . . ?
S1 C1 H1B 108(3) . . ?
H1A C1 H1B 109.3(17) . . ?
S1 C1 H1A 111.1(16) . 6 ?
H1A C1 H1A 108(2) . 6 ?
H1B C1 H1A 109.3(17) . 6 ?
N1 C2 N2 119.75(12) . . ?
N1 C2 N2 119.76(12) . 6_565 ?
N2 C2 N2 120.5(2) . 6_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.79(3) 2.12(3) 2.9085(19) 169(3) .
N2 H2N O2 0.85(3) 2.07(3) 2.912(2) 169(2) .
N2 H3N O1 0.80(2) 2.13(3) 2.925(2) 168(2) 8

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.091


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fa-CF3COO
_database_code_depnum_ccdc_archive 'CCDC 2090747'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'formamidinium trifluoroacetate'
_chemical_formula_moiety         'C2 F3 O2, C H5 N2'
_chemical_formula_sum            'C3 H5 F3 N2 O2'
_chemical_formula_weight         158.09
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   6.83933(6)
_cell_length_b                   6.83933(6)
_cell_length_c                   25.0216(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1170.42(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10002
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.6270
_cell_measurement_theta_min      6.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.201
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12176
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.059
_diffrn_reflns_theta_min         6.711
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     86.00 145.00   0.50    0.05    --  107.75  77.00  60.00  118
  2  ω     93.00 120.00   0.50    0.05    --  107.75  66.00  56.81   54
  3  ω     96.00 140.00   0.50    0.05    --  107.75  77.00  30.00   88
  4  ω    141.00 166.00   0.50    0.05    --  107.75  77.00  30.00   50
  5  ω     95.00 178.00   0.50    0.05    --  107.75  46.00 -38.00  166
  6  ω    -76.00 -36.00   0.50    0.05    --  -47.64 -38.00  60.00   80
  7  ω    -75.00  25.00   0.50    0.05    --  -47.64  88.00 170.00  200
  8  ω   -120.00 -35.00   0.50    0.05    --  -47.64 -46.00 171.00  170
  9  ω   -103.00 -78.00   0.50    0.05    --  -47.64 -77.00  60.00   50
 10  ω    -72.00 -27.00   0.50    0.05    --  -47.64 -77.00  60.00   90
 11  ω    -21.00  75.00   0.50    0.05    --   47.64 -88.00  54.00  192
 12  ω     46.00  71.00   0.50    0.05    --  107.75 -95.00 -43.00   50
 13  ω     36.00  68.00   0.50    0.05    --  107.75 -45.00 -60.00   64
 14  ω     41.00  70.00   0.50    0.05    --  107.75 -45.00 -30.00   58
 15  ω     36.00  77.00   0.50    0.05    --  107.75 -88.00  54.00   82
 16  ω     48.00  73.00   0.50    0.05    --  107.75 -46.00 171.00   50
 17  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00 120.00   66
 18  ω     36.00  61.00   0.50    0.05    --  107.75 -45.00  90.00   50
 19  ω     37.00  65.00   0.50    0.05    --  107.75 -30.00  30.00   56
 20  ω     33.00  62.00   0.50    0.05    --  107.75 -30.00   0.00   58
 21  ω     33.00  65.00   0.50    0.05    --  107.75 -30.00 -60.00   64
 22  ω     33.00  65.00   0.50    0.05    --  107.75 -30.00-180.00   64
 23  ω    110.00 177.00   0.50    0.05    --  107.75  95.00  66.00  134
 24  ω    129.00 175.00   0.50    0.05    --  107.75  88.00 170.00   92
 25  ω    -24.00  60.00   0.50    0.05    --   47.64 -46.00 171.00  168
 26  ω    -97.00 -65.00   0.50    0.05    --  -86.25 -77.00  60.00   64
 27  ω    -92.00 -66.00   0.50    0.05    --  -86.25 -74.00  81.87   52
 28  ω   -159.00 -73.00   0.50    0.05    --  -86.25 -46.00 171.00  172
 29  ω    -93.00 -68.00   0.50    0.05    --  -86.25 -68.00  63.47   50
 30  ω   -159.00 -79.00   0.50    0.05    --  -86.25 -88.00  54.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0773645000
_diffrn_orient_matrix_UB_12      0.2053861000
_diffrn_orient_matrix_UB_13      -0.0138344000
_diffrn_orient_matrix_UB_21      0.1877236000
_diffrn_orient_matrix_UB_22      0.0418628000
_diffrn_orient_matrix_UB_23      -0.0320636000
_diffrn_orient_matrix_UB_31      -0.0974977000
_diffrn_orient_matrix_UB_32      -0.0824582000
_diffrn_orient_matrix_UB_33      -0.0507147000
_diffrn_oxdiff_digest_frames     
;
01f1838073c9dded57de5dd17e7fcc1f9100118fd35
;
_diffrn_oxdiff_digest_hkl        
;
012df2bb7b0d5c075afbf9eed534fbe4b00dc1
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                1218
_reflns_number_total             1234
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_coef       0.0032(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1234
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.8278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N8-H8B = N8-H8A = N10-H10B = N10-H10A
 0.91 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F 0.3778(3) 0.4075(3) 0.30179(6) 0.0326(5) Uani 1 1 d . . . . .
O5 O 0.4951(3) 0.4000(3) 0.43548(6) 0.0183(4) Uani 1 1 d . . . . .
O4 O 0.5255(3) 0.1554(3) 0.37576(7) 0.0206(4) Uani 1 1 d . . . . .
F7 F 0.3832(4) 0.6391(3) 0.35859(7) 0.0476(6) Uani 1 1 d . . . . .
N8 N 1.0139(3) 0.6648(3) 0.29317(9) 0.0194(5) Uani 1 1 d D . . . .
N10 N 0.9837(4) 0.4080(3) 0.23378(8) 0.0207(5) Uani 1 1 d D . . . .
F6 F 0.6512(3) 0.5279(5) 0.32570(12) 0.0849(12) Uani 1 1 d . . . . .
C3 C 0.5004(4) 0.3276(3) 0.38953(9) 0.0156(5) Uani 1 1 d . . . . .
C9 C 0.9870(3) 0.5944(4) 0.24545(10) 0.0189(5) Uani 1 1 d . . . . .
H9 H 0.968938 0.682864 0.217657 0.023 Uiso 1 1 calc R . . . .
C2 C 0.4789(4) 0.4768(4) 0.34336(9) 0.0237(6) Uani 1 1 d . . . . .
H10A H 0.953(5) 0.377(5) 0.2014(10) 0.033(9) Uiso 1 1 d D . . . .
H10B H 0.986(5) 0.317(4) 0.2586(11) 0.024(8) Uiso 1 1 d D . . . .
H8A H 1.005(5) 0.794(3) 0.2977(14) 0.033(9) Uiso 1 1 d D . . . .
H8B H 1.024(6) 0.581(5) 0.3198(12) 0.045(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.336(3) . ?
O5 C3 1.252(3) . ?
O4 C3 1.239(3) . ?
F7 C2 1.344(3) . ?
N8 C9 1.300(3) . ?
N8 H8A 0.89(2) . ?
N8 H8B 0.88(2) . ?
N10 C9 1.308(3) . ?
N10 H10A 0.86(2) . ?
N10 H10B 0.88(2) . ?
F6 C2 1.306(3) . ?
C3 C2 1.549(3) . ?
C9 H9 0.9300 . ?

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
C9 N8 H8A 118(2) . . ?
C9 N8 H8B 118(3) . . ?
H8A N8 H8B 124(3) . . ?
C9 N10 H10A 117(2) . . ?
C9 N10 H10B 122(2) . . ?
H10A N10 H10B 120(3) . . ?
O5 C3 C2 114.9(2) . . ?
O4 C3 O5 129.5(2) . . ?
O4 C3 C2 115.6(2) . . ?
N8 C9 N10 124.6(2) . . ?
N8 C9 H9 117.7 . . ?
N10 C9 H9 117.7 . . ?
F1 C2 F7 105.2(2) . . ?
F1 C2 C3 113.3(2) . . ?
F7 C2 C3 112.3(2) . . ?
F6 C2 F1 107.4(2) . . ?
F6 C2 F7 108.3(3) . . ?
F6 C2 C3 110.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 O5 0.93 2.39 3.238(3) 151.3 4_564 yes
N10 H10A O5 0.86(2) 2.60(3) 3.064(3) 115(3) 4_554 yes
N10 H10A O4 0.86(2) 2.17(3) 2.937(3) 147(3) 8_665 yes
N10 H10B O5 0.88(2) 2.04(2) 2.920(3) 178(3) 6 yes
N8 H8A O5 0.89(2) 2.13(2) 3.027(3) 175(3) 6_565 yes
N8 H8B O4 0.88(2) 2.11(2) 2.986(3) 170(4) 6 yes

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
O5 C3 C2 F1 -144.0(2) . . . . ?
O5 C3 C2 F7 -25.0(3) . . . . ?
O5 C3 C2 F6 95.8(3) . . . . ?
O4 C3 C2 F1 37.9(3) . . . . ?
O4 C3 C2 F7 156.9(2) . . . . ?
O4 C3 C2 F6 -82.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.732
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fa-Cl
_database_code_depnum_ccdc_archive 'CCDC 2090748'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'formamidine hydrochloride'
_chemical_name_systematic        'formamidinium chloride'
_chemical_formula_moiety         'Cl, C H5 N2'
_chemical_formula_sum            'C H5 Cl N2'
_chemical_formula_weight         80.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.0881(3)
_cell_length_b                   7.7636(4)
_cell_length_c                   8.6548(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.121(4)
_cell_angle_gamma                90
_cell_volume                     396.71(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.8620
_cell_measurement_theta_min      7.4900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.551
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2554
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.421
_diffrn_reflns_theta_min         7.503
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -23.00   0.50    0.13    --  -47.64  38.00-150.00   70
  2  ω    -19.00  23.00   0.50    0.13    --  -47.64  38.00-150.00   84
  3  ω    -44.00 -18.00   0.50    0.13    --  -47.64 118.00 -58.00   52
  4  ω      5.00  75.00   0.50    0.13    --   47.64 -99.00  30.00  140
  5  ω     61.00  86.00   0.50    0.13    --   47.64-160.00  62.00   50
  6  ω     87.00 128.00   0.50    0.51    --  107.75-160.00  62.00   82
  7  ω     60.00 124.00   0.50    0.51    --  107.75 -77.00  30.00  128
  8  ω     71.00 102.00   0.50    0.51    --  107.75 -94.00 -90.00   62
  9  ω     99.00 131.00   0.50    0.51    --  107.75 -77.00-150.00   64
 10  ω     37.00  62.00   0.50    0.13    --   47.64-118.00-145.00   50
 11  ω     35.00 109.00   0.50    0.51    --  107.75-118.00-145.00  148
 12  ω     39.00  64.00   0.50    0.51    --  107.75 -30.00-180.00   50
 13  ω     34.00  65.00   0.50    0.51    --  107.75 -30.00-150.00   62
 14  ω     36.00  65.00   0.50    0.51    --  107.75 -30.00 -90.00   58
 15  ω     33.00  64.00   0.50    0.51    --  107.75 -30.00-120.00   62
 16  ω     38.00  86.00   0.50    0.51    --  107.75 -77.00-150.00   96
 17  ω     33.00  59.00   0.50    0.51    --  107.75 -30.00 -30.00   52
 18  ω     33.00  58.00   0.50    0.51    --  107.75 -30.00   0.00   50
 19  ω     34.00  61.00   0.50    0.51    --  107.75 -30.00  30.00   54
 20  ω     34.00  64.00   0.50    0.51    --  107.75 -30.00  60.00   60
 21  ω     36.00  64.00   0.50    0.51    --  107.75 -30.00  90.00   56
 22  ω     52.00  78.00   0.50    0.51    --  107.75-160.00  62.00   52
 23  ω    -85.00 -58.00   0.50    0.13    --  -47.64-160.00  62.00   54
 24  ω   -104.00 -79.00   0.50    0.51    --  -86.25-118.00-145.00   50
 25  ω    -67.00 -13.00   0.50    0.51    --  -86.25  30.00 150.00  108
 26  ω    108.00 134.00   0.50    0.51    --  107.75 118.00 -58.00   52
 27  ω     91.00 116.00   0.50    0.51    --  107.75 160.00  93.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0723297000
_diffrn_orient_matrix_UB_12      0.0416553000
_diffrn_orient_matrix_UB_13      0.1793141000
_diffrn_orient_matrix_UB_21      0.0195614000
_diffrn_orient_matrix_UB_22      0.1922051000
_diffrn_orient_matrix_UB_23      -0.0391117000
_diffrn_orient_matrix_UB_31      -0.2498471000
_diffrn_orient_matrix_UB_32      0.0271472000
_diffrn_orient_matrix_UB_33      0.0020139000
_diffrn_oxdiff_digest_frames     
;
01a500ed21b7d313f5e2fe3b5e8af3068a0007002f6
;
_diffrn_oxdiff_digest_hkl        
;
01daa3068788a8dee07a727694f10d29542895
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                725
_reflns_number_total             818
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     57
_refine_ls_number_reflns         818
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0968P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1344
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N2-H4 = N1-H2 = N1-H3 = N2-H5
 0.91 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.74877(7) 0.31223(6) 0.52469(7) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.5995(3) 0.5652(3) 0.2275(3) 0.0252(5) Uani 1 1 d D . . . .
N2 N 0.7860(4) 0.7070(3) 0.0646(3) 0.0292(5) Uani 1 1 d D . . . .
C1 C 0.7802(4) 0.5986(3) 0.1774(3) 0.0233(5) Uani 1 1 d . . . . .
H1 H 0.913(6) 0.544(4) 0.225(4) 0.029(8) Uiso 1 1 d . . . . .
H2 H 0.464(3) 0.614(3) 0.182(3) 0.020(6) Uiso 1 1 d D . . . .
H5 H 0.655(4) 0.761(5) 0.019(5) 0.042(9) Uiso 1 1 d D . . . .
H3 H 0.613(5) 0.489(4) 0.308(3) 0.028(8) Uiso 1 1 d D . . . .
H4 H 0.918(5) 0.738(6) 0.044(6) 0.061(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.303(3) . ?
N2 C1 1.296(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 N1 124.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl1 0.92(4) 2.83(4) 3.427(2) 124(2) 3_766 yes
N1 H2 Cl1 0.904(17) 2.48(2) 3.268(2) 147(2) 2_655 yes
N2 H5 Cl1 0.904(19) 2.43(2) 3.261(2) 154(4) 2_655 yes
N1 H3 Cl1 0.900(18) 2.31(2) 3.187(2) 164(3) . yes
N2 H4 Cl1 0.900(19) 2.32(2) 3.218(2) 176(5) 2_755 yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.126
_oxdiff_exptl_absorpt_empirical_full_min 0.514
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fa-C7H7SO3
_database_code_depnum_ccdc_archive 'CCDC 2090746'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'formamidinium tosylate'
_chemical_name_systematic        'formamidinium para-toluenesulfonate'
_chemical_formula_moiety         '2(C7 H7 O3 S), 2(C H5 N2)'
_chemical_formula_sum            'C16 H24 N4 O6 S2'
_chemical_formula_weight         432.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1440(2)
_cell_length_b                   12.8644(6)
_cell_length_c                   13.3576(3)
_cell_angle_alpha                89.604(3)
_cell_angle_beta                 85.602(3)
_cell_angle_gamma                82.341(3)
_cell_volume                     1043.26(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5916
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.3690
_cell_measurement_theta_min      4.8220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20728
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.350
_diffrn_reflns_theta_min         3.467
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00 120.00   0.50    0.05    --   47.64  65.00 178.00  180
  2  ω     25.00 120.00   0.50    0.05    --   47.64  77.00  90.00  190
  3  ω     25.00 120.00   0.50    0.05    --   47.64  77.00   0.00  190
  4  ω     33.00 120.00   0.50    0.05    --   47.64  57.00 -90.00  174
  5  ω     94.00 178.00   0.50    0.14    --  107.75  15.00 120.00  168
  6  ω     90.00 178.00   0.50    0.14    --  107.75  65.00 178.00  176
  7  ω     91.00 178.00   0.50    0.14    --  107.75  61.00 150.00  174
  8  ω     95.00 178.00   0.50    0.14    --  107.75  30.00 -60.00  166
  9  ω    -27.00  60.00   0.50    0.05    --   47.64 -19.00  60.00  174
 10  ω    -24.00  66.00   0.50    0.05    --   47.64 -65.00  42.00  180
 11  ω     95.00 178.00   0.50    0.14    --  107.75 125.00 120.00  166
 12  ω    -65.00  25.00   0.50    0.05    --  -47.64  65.00 178.00  180
 13  ω    -61.00  25.00   0.50    0.05    --  -47.64  38.00  90.00  172
 14  ω   -104.00 -13.00   0.50    0.14    --  -86.25  65.00 178.00  182
 15  ω    -68.00 -11.00   0.50    0.14    --  -86.25  30.00  30.00  114
 16  ω    -78.00 -14.00   0.50    0.14    --  -86.25  45.00   0.00  128
 17  ω   -159.00 -68.00   0.50    0.14    --  -86.25 -65.00  42.00  182
 18  ω   -120.00 -30.00   0.50    0.05    --  -47.64 -65.00  42.00  180
 19  ω     35.00 131.00   0.50    0.14    --  107.75 -77.00 120.00  192
 20  ω     36.00  76.00   0.50    0.14    --  107.75 -45.00 150.00   80
 21  ω     36.00  76.00   0.50    0.14    --  107.75 -45.00  30.00   80
 22  ω     35.00 126.00   0.50    0.14    --  107.75 -65.00  42.00  182
 23  ω     36.00  76.00   0.50    0.14    --  107.75 -45.00 -60.00   80
 24  ω     33.00  66.00   0.50    0.14    --  107.75 -30.00 -90.00   66
 25  ω     33.00  66.00   0.50    0.14    --  107.75 -30.00-150.00   66
 26  ω     36.00  76.00   0.50    0.14    --  107.75 -45.00-180.00   80
 27  ω     33.00  66.00   0.50    0.14    --  107.75 -30.00-180.00   66
 28  ω     33.00 122.00   0.50    0.14    --  107.75 -15.00-180.00  178
 29  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00 -60.00  142
 30  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00 -30.00  142
 31  ω     34.00  95.00   0.50    0.05    --   47.64-125.00-120.00  122
 32  ω     35.00 112.00   0.50    0.14    --  107.75-125.00-150.00  154
 33  ω     35.00 106.00   0.50    0.14    --  107.75-100.00-112.36  142
 34  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00-120.00  142
 35  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00 -90.00  142
 36  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00   0.00  142
 37  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00  60.00  142
 38  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00  30.00  142
 39  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00  90.00  142
 40  ω     35.00 106.00   0.50    0.14    --  107.75 -94.00 120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1204645000
_diffrn_orient_matrix_UB_12      -0.1092060000
_diffrn_orient_matrix_UB_13      -0.0306436000
_diffrn_orient_matrix_UB_21      -0.1420181000
_diffrn_orient_matrix_UB_22      -0.0505315000
_diffrn_orient_matrix_UB_23      0.0818130000
_diffrn_orient_matrix_UB_31      -0.1723498000
_diffrn_orient_matrix_UB_32      -0.0110062000
_diffrn_orient_matrix_UB_33      -0.0758155000
_diffrn_oxdiff_digest_frames     
;
01c411dc968fc3c1a6e9b36a6248a0ae1a05842c208
;
_diffrn_oxdiff_digest_hkl        
;
01e4bc3620460dd672c13ae7e4c35d671b02e7
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3629
_reflns_number_total             4317
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0848P)²+0.3291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C15(H15), C11(H11), C8(H8), C14(H14), C12(H12),
 C7(H7), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S01 S 1.15068(7) 0.83956(4) 0.62318(3) 0.02540(16) Uani 1 1 d . . . . .
S002 S 0.14140(7) 0.83399(4) 0.11819(3) 0.02502(16) Uani 1 1 d . . . . .
O6 O 1.3785(2) 0.84954(12) 0.64243(10) 0.0301(3) Uani 1 1 d . . . . .
O4 O 1.1067(2) 0.87213(13) 0.52089(11) 0.0325(3) Uani 1 1 d . . . . .
O1 O 0.1002(2) 0.85301(13) 0.01274(10) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.3144(2) 0.89246(12) 0.14779(10) 0.0294(3) Uani 1 1 d . . . . .
O2 O -0.0584(3) 0.84817(13) 0.18324(12) 0.0374(4) Uani 1 1 d . . . . .
O5 O 0.9913(3) 0.88971(13) 0.69816(12) 0.0399(4) Uani 1 1 d . . . . .
N2 N -0.3483(3) 0.88618(14) -0.02355(14) 0.0276(4) Uani 1 1 d . . . . .
N4 N 0.6670(3) 0.89131(14) 0.46819(14) 0.0279(4) Uani 1 1 d . . . . .
N1 N -0.5889(3) 0.89778(15) -0.14800(15) 0.0299(4) Uani 1 1 d . . . . .
N3 N 0.4067(3) 0.90356(16) 0.35255(15) 0.0345(4) Uani 1 1 d . . . . .
C10 C 1.1281(3) 0.70393(16) 0.62749(14) 0.0259(4) Uani 1 1 d . . . . .
C1 C -0.3918(3) 0.89048(16) -0.11749(15) 0.0257(4) Uani 1 1 d . . . . .
H1 H -0.274016 0.888170 -0.165878 0.031 Uiso 1 1 calc R . . . .
C2 C 0.6088(3) 0.90048(16) 0.37630(15) 0.0280(4) Uani 1 1 d . . . . .
H2 H 0.718059 0.905088 0.324887 0.034 Uiso 1 1 calc R . . . .
C3 C 0.2521(3) 0.70023(16) 0.12441(14) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.4621(3) 0.66965(17) 0.15427(15) 0.0302(4) Uani 1 1 d . . . . .
H4 H 0.547778 0.719871 0.172349 0.036 Uiso 1 1 calc R . . . .
C15 C 0.9241(3) 0.67118(18) 0.65236(15) 0.0301(4) Uani 1 1 d . . . . .
H15 H 0.801305 0.720141 0.669025 0.036 Uiso 1 1 calc R . . . .
C11 C 1.3107(3) 0.63048(18) 0.60141(16) 0.0326(5) Uani 1 1 d . . . . .
H11 H 1.446903 0.652139 0.583659 0.039 Uiso 1 1 calc R . . . .
C8 C 0.1234(4) 0.62444(18) 0.09789(16) 0.0338(5) Uani 1 1 d . . . . .
H8 H -0.018124 0.644384 0.078308 0.041 Uiso 1 1 calc R . . . .
C13 C 1.0860(4) 0.48986(18) 0.62727(15) 0.0328(5) Uani 1 1 d . . . . .
C14 C 0.9052(4) 0.56522(18) 0.65212(15) 0.0328(5) Uani 1 1 d . . . . .
H14 H 0.768437 0.543705 0.668948 0.039 Uiso 1 1 calc R . . . .
C12 C 1.2879(4) 0.52480(18) 0.60213(16) 0.0351(5) Uani 1 1 d . . . . .
H12 H 1.410774 0.475915 0.585364 0.042 Uiso 1 1 calc R . . . .
C7 C 0.2085(4) 0.51981(19) 0.10107(17) 0.0381(5) Uani 1 1 d . . . . .
H7 H 0.122542 0.469581 0.083279 0.046 Uiso 1 1 calc R . . . .
C5 C 0.5442(4) 0.56412(18) 0.15711(16) 0.0350(5) Uani 1 1 d . . . . .
H5 H 0.685148 0.544094 0.177354 0.042 Uiso 1 1 calc R . . . .
C6 C 0.4192(4) 0.48744(18) 0.13015(16) 0.0359(5) Uani 1 1 d . . . . .
C16 C 1.0633(5) 0.37503(19) 0.62826(18) 0.0429(6) Uani 1 1 d . . . . .
H16A H 1.146645 0.340865 0.679932 0.064 Uiso 1 1 calc GR . . . .
H16B H 1.117906 0.344557 0.564303 0.064 Uiso 1 1 calc GR . . . .
H16C H 0.910997 0.366286 0.641173 0.064 Uiso 1 1 calc GR . . . .
C9 C 0.5089(5) 0.3731(2) 0.13318(19) 0.0481(6) Uani 1 1 d . . . . .
H9A H 0.408509 0.336254 0.173766 0.072 Uiso 1 1 calc GR . . . .
H9B H 0.649128 0.365044 0.161457 0.072 Uiso 1 1 calc GR . . . .
H9C H 0.526285 0.344874 0.066268 0.072 Uiso 1 1 calc GR . . . .
H1A H -0.699(5) 0.896(2) -0.105(2) 0.029(6) Uiso 1 1 d . . . . .
H2A H -0.221(5) 0.881(2) -0.010(2) 0.038(7) Uiso 1 1 d . . . . .
H4A H 0.801(5) 0.892(2) 0.477(2) 0.040(7) Uiso 1 1 d . . . . .
H3A H 0.303(5) 0.899(2) 0.396(2) 0.035(7) Uiso 1 1 d . . . . .
H2B H -0.447(4) 0.8888(18) 0.0244(19) 0.024(6) Uiso 1 1 d . . . . .
H1B H -0.598(5) 0.890(2) -0.208(2) 0.043(8) Uiso 1 1 d . . . . .
H4B H 0.575(5) 0.886(2) 0.521(2) 0.033(7) Uiso 1 1 d . . . . .
H3B H 0.375(5) 0.906(2) 0.291(2) 0.043(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
S01 O6 1.4648(14) . ?
S01 O4 1.4609(15) . ?
S01 O5 1.4383(15) . ?
S01 C10 1.769(2) . ?
S002 O1 1.4634(14) . ?
S002 O3 1.4605(14) . ?
S002 O2 1.4403(15) . ?
S002 C3 1.768(2) . ?
N2 C1 1.302(3) . ?
N2 H2A 0.81(3) . ?
N2 H2B 0.85(3) . ?
N4 C2 1.305(3) . ?
N4 H4A 0.84(3) . ?
N4 H4B 0.88(3) . ?
N1 C1 1.299(3) . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.82(3) . ?
N3 C2 1.301(3) . ?
N3 H3A 0.84(3) . ?
N3 H3B 0.86(3) . ?
C10 C15 1.390(3) . ?
C10 C11 1.391(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 C8 1.398(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.383(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(3) . ?
C13 C14 1.395(3) . ?
C13 C12 1.392(3) . ?
C13 C16 1.502(3) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C9 1.502(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
O6 S01 C10 106.39(9) . . ?
O4 S01 O6 110.66(8) . . ?
O4 S01 C10 105.41(9) . . ?
O5 S01 O6 113.40(9) . . ?
O5 S01 O4 113.35(10) . . ?
O5 S01 C10 106.98(9) . . ?
O1 S002 C3 105.43(9) . . ?
O3 S002 O1 110.89(8) . . ?
O3 S002 C3 105.52(9) . . ?
O2 S002 O1 112.28(9) . . ?
O2 S002 O3 114.81(9) . . ?
O2 S002 C3 107.16(9) . . ?
C1 N2 H2A 119(2) . . ?
C1 N2 H2B 122.9(16) . . ?
H2A N2 H2B 118(2) . . ?
C2 N4 H4A 117.6(19) . . ?
C2 N4 H4B 124.1(17) . . ?
H4A N4 H4B 118(3) . . ?
C1 N1 H1A 119.4(17) . . ?
C1 N1 H1B 117(2) . . ?
H1A N1 H1B 122(3) . . ?
C2 N3 H3A 121.4(19) . . ?
C2 N3 H3B 121.4(19) . . ?
H3A N3 H3B 117(3) . . ?
C15 C10 S01 119.59(16) . . ?
C15 C10 C11 120.0(2) . . ?
C11 C10 S01 120.31(16) . . ?
N2 C1 H1 117.9 . . ?
N1 C1 N2 124.2(2) . . ?
N1 C1 H1 117.9 . . ?
N4 C2 H2 118.2 . . ?
N3 C2 N4 123.7(2) . . ?
N3 C2 H2 118.2 . . ?
C4 C3 S002 121.50(16) . . ?
C4 C3 C8 119.9(2) . . ?
C8 C3 S002 118.62(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C10 C15 H15 120.2 . . ?
C14 C15 C10 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C3 C8 H8 120.3 . . ?
C7 C8 C3 119.3(2) . . ?
C7 C8 H8 120.3 . . ?
C14 C13 C16 121.0(2) . . ?
C12 C13 C14 117.7(2) . . ?
C12 C13 C16 121.3(2) . . ?
C15 C14 C13 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C8 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C6 C7 H7 119.1 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.1(2) . . ?
C7 C6 C9 121.0(2) . . ?
C5 C6 C9 121.0(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
S01 C10 C15 C14 177.66(15) . . . . ?
S01 C10 C11 C12 -177.91(16) . . . . ?
S002 C3 C4 C5 -179.26(15) . . . . ?
S002 C3 C8 C7 179.15(16) . . . . ?
O6 S01 C10 C15 154.11(16) . . . . ?
O6 S01 C10 C11 -29.03(18) . . . . ?
O4 S01 C10 C15 -88.33(17) . . . . ?
O4 S01 C10 C11 88.53(18) . . . . ?
O1 S002 C3 C4 118.30(16) . . . . ?
O1 S002 C3 C8 -61.36(17) . . . . ?
O3 S002 C3 C4 0.89(18) . . . . ?
O3 S002 C3 C8 -178.78(15) . . . . ?
O2 S002 C3 C4 -121.91(17) . . . . ?
O2 S002 C3 C8 58.43(18) . . . . ?
O5 S01 C10 C15 32.60(19) . . . . ?
O5 S01 C10 C11 -150.54(17) . . . . ?
C10 C15 C14 C13 -0.1(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C3 C8 C7 C6 0.1(3) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C4 C5 C6 C9 179.9(2) . . . . ?
C15 C10 C11 C12 -1.1(3) . . . . ?
C11 C10 C15 C14 0.8(3) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C8 C7 C6 C5 0.4(3) . . . . ?
C8 C7 C6 C9 180.0(2) . . . . ?
C14 C13 C12 C11 -0.1(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C16 C13 C14 C15 179.43(19) . . . . ?
C16 C13 C12 C11 -179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.170
_oxdiff_exptl_absorpt_empirical_full_min 0.591
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fa-CH3SO3
_database_code_depnum_ccdc_archive 'CCDC 2090744'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'formamidinium mesylate'
_chemical_name_systematic        'formamidinium methanesulfonate'
_chemical_formula_moiety         'C H3 O3 S, C H5 N2'
_chemical_formula_sum            'C2 H8 N2 O3 S'
_chemical_formula_weight         140.16
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   9.6440(3)
_cell_length_b                   5.3173(2)
_cell_length_c                   11.2997(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     579.45(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4636
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      76.1090
_cell_measurement_theta_min      7.8300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.112
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5410
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.060
_diffrn_reflns_theta_min         7.842
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00 120.00   80
  2  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00  90.00   80
  3  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00  30.00   66
  4  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00 -30.00   80
  5  ω     89.00 178.00   0.50    0.05    --  107.75 134.00 -18.00  178
  6  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00 -90.00   80
  7  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00-120.00   66
  8  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00-150.00   66
  9  ω   -159.00 -73.00   0.50    0.05    --  -86.25 -46.00 142.00  172
 10  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  60.00  188
 11  ω   -119.00 -26.00   0.50    0.05    --  -47.70 -75.00 -25.00  186
 12  ω   -108.00 -13.00   0.50    0.05    --  -86.25  75.00 101.00  190
 13  ω    -94.00 -18.00   0.50    0.05    --  -47.70 135.00 160.00  152
 14  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00-150.00  172
 15  ω   -119.00 -29.00   0.50    0.05    --  -47.70 -77.00-180.00  180
 16  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00 -90.00   92
 17  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00 150.00   92
 18  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00  90.00  142
 19  ω     40.00 119.00   0.50    0.05    --  107.75-135.00  95.00  158
 20  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00 150.00  142
 21  ω     -1.00  81.00   0.50    0.05    --   47.70 -99.00 -90.00  164
 22  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00 -90.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1036653000
_diffrn_orient_matrix_UB_12      0.1774809000
_diffrn_orient_matrix_UB_13      0.0614612000
_diffrn_orient_matrix_UB_21      -0.0812060000
_diffrn_orient_matrix_UB_22      -0.2289846000
_diffrn_orient_matrix_UB_23      0.0466695000
_diffrn_orient_matrix_UB_31      0.0903794000
_diffrn_orient_matrix_UB_32      -0.0020743000
_diffrn_orient_matrix_UB_33      0.1124228000
_diffrn_oxdiff_digest_frames     
;
01882977116440f5be00be9839ff10994c00097d368
;
_diffrn_oxdiff_digest_hkl        
;
012c7ff1f14dd675c5393d74a3bd5a804519e7
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.596
_reflns_Friedel_fraction_full    0.730
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                1014
_reflns_number_total             1023
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.46(4)
_refine_ls_extinction_coef       0.0099(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1023
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0763P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.54(4)
 0.46(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N8-H8A = N8-H8B = N6-H6B = N6-H6A
 0.91 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7)
4.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68629(7) 0.44712(12) 0.59547(10) 0.0160(3) Uani 1 1 d . . . . .
O3 O 0.5524(2) 0.3193(4) 0.5831(3) 0.0198(6) Uani 1 1 d . . . . .
O2 O 0.7341(3) 0.4507(4) 0.7180(3) 0.0227(6) Uani 1 1 d . . . . .
O4 O 0.6847(2) 0.6975(5) 0.5441(3) 0.0237(7) Uani 1 1 d . . . . .
N6 N 0.4527(3) 0.2200(5) 0.3515(3) 0.0210(6) Uani 1 1 d D . . . .
N8 N 0.5808(3) -0.1410(5) 0.3149(3) 0.0224(6) Uani 1 1 d D . . . .
C7 C 0.4979(4) 0.0414(5) 0.2825(3) 0.0213(8) Uani 1 1 d . . . . .
H7 H 0.468879 0.043637 0.204053 0.026 Uiso 1 1 calc R . . . .
C5 C 0.8064(3) 0.2671(6) 0.5149(4) 0.0206(8) Uani 1 1 d . . . . .
H5A H 0.805973 0.097319 0.543755 0.031 Uiso 1 1 calc GR . . . .
H5B H 0.897425 0.337511 0.524252 0.031 Uiso 1 1 calc GR . . . .
H5C H 0.781486 0.268187 0.432643 0.031 Uiso 1 1 calc GR . . . .
H8A H 0.615(5) -0.163(10) 0.386(3) 0.042(14) Uiso 1 1 d D . . . .
H8B H 0.607(6) -0.252(8) 0.259(4) 0.054(17) Uiso 1 1 d D . . . .
H6A H 0.392(4) 0.320(8) 0.315(5) 0.037(12) Uiso 1 1 d D . . . .
H6B H 0.484(5) 0.258(7) 0.425(3) 0.024(11) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.466(2) . ?
S1 O2 1.459(3) . ?
S1 O4 1.452(3) . ?
S1 C5 1.757(4) . ?
N6 C7 1.303(5) . ?
N6 H6A 0.89(2) . ?
N6 H6B 0.90(2) . ?
N8 C7 1.309(5) . ?
N8 H8A 0.87(3) . ?
N8 H8B 0.90(2) . ?
C7 H7 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C5 106.19(14) . . ?
O2 S1 O3 112.03(17) . . ?
O2 S1 C5 106.87(18) . . ?
O4 S1 O3 112.18(14) . . ?
O4 S1 O2 111.74(17) . . ?
O4 S1 C5 107.43(18) . . ?
C7 N6 H6A 112(4) . . ?
C7 N6 H6B 127(3) . . ?
H6A N6 H6B 120(5) . . ?
C7 N8 H8A 126(4) . . ?
C7 N8 H8B 118(4) . . ?
H8A N8 H8B 117(5) . . ?
N6 C7 N8 125.2(4) . . ?
N6 C7 H7 117.4 . . ?
N8 C7 H7 117.4 . . ?
S1 C5 H5A 109.5 . . ?
S1 C5 H5B 109.5 . . ?
S1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 O3 0.93 2.37 2.999(5) 124.4 2_654 yes
N8 H8A O4 0.87(3) 2.05(3) 2.907(5) 167(5) 1_545 yes
N8 H8B O3 0.90(2) 2.54(5) 3.068(4) 118(4) 2_654 yes
N8 H8B O2 0.90(2) 2.25(4) 3.017(4) 143(5) 4_644 yes
N6 H6A O2 0.89(2) 2.04(3) 2.931(4) 174(5) 2_664 yes
N6 H6B O3 0.90(2) 1.94(3) 2.838(5) 177(4) . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.741
_oxdiff_exptl_absorpt_empirical_full_min 0.421
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.54(4)
2 0.46(4)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_aca-CH3SO3
_database_code_depnum_ccdc_archive 'CCDC 2090749'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'acetamidinium mesylate'
_chemical_name_systematic        'acetamidinium methanesulfonate'
_chemical_formula_moiety         '2(C H3 O3 S), 2(C2 H7 N2)'
_chemical_formula_sum            'C6 H20 N4 O6 S2'
_chemical_formula_weight         308.38
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.69460(10)
_cell_length_b                   8.62580(10)
_cell_length_c                   10.37460(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     688.584(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6316
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      77.0060
_cell_measurement_theta_min      4.2410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.183
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6711
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.238
_diffrn_reflns_theta_min         7.716
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     95.00 178.00   0.50    0.05    --  107.75  30.00-180.00  166
  2  ω     94.00 178.00   0.50    0.05    --  107.75  15.00  30.00  168
  3  ω     95.00 139.00   0.50    0.05    --  107.75  45.00  60.00   88
  4  ω     94.00 178.00   0.50    0.05    --  107.75  15.00 120.00  168
  5  ω     95.00 178.00   0.50    0.05    --  107.75 125.00 120.00  166
  6  ω    -63.00  25.00   0.50    0.05    --  -47.70  57.00-120.00  176
  7  ω    -68.00 -11.00   0.50    0.05    --  -86.25  30.00-120.00  114
  8  ω    -68.00 -11.00   0.50    0.05    --  -86.25  30.00 -60.00  114
  9  ω    -78.00 -14.00   0.50    0.05    --  -86.25  45.00   0.00  128
 10  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 -60.00  172
 11  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -90.00  188
 12  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00-180.00  188
 13  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00-180.00  172
 14  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00   0.00  188
 15  ω   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00  30.00  172
 16  ω   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 120.00  188
 17  ω   -159.00 -65.00   0.50    0.05    --  -86.25 -74.00 -21.38  188
 18  ω   -159.00 -63.00   0.50    0.05    --  -86.25 -77.00 -90.00  192
 19  ω   -159.00 -63.00   0.50    0.05    --  -86.25 -77.00-150.00  192
 20  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00-120.00   92
 21  ω   -119.00 -73.00   0.50    0.05    --  -47.70-125.00 120.00   92
 22  ω     35.00 112.00   0.50    0.05    --  107.75-125.00   0.00  154
 23  ω     35.00 112.00   0.50    0.05    --  107.75-125.00-150.00  154
 24  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00-120.00  142
 25  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00 -90.00  142
 26  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00  60.00  142
 27  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00  90.00  142
 28  ω     35.00 106.00   0.50    0.05    --  107.75 -94.00 120.00  142
 29  ω    -24.00  70.00   0.50    0.05    --   47.70 -77.00  60.00  188
 30  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00  60.00   66
 31  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00  90.00   80
 32  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00  90.00   66
 33  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00  30.00   66
 34  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00   0.00   66
 35  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00-150.00   80
 36  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00-120.00   66
 37  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00-150.00   66
 38  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00 -90.00   66
 39  ω     36.00  76.00   0.50    0.05    --  107.75 -45.00 -90.00   80
 40  ω     35.00 124.00   0.50    0.05    --  107.75 -61.00 -30.00  178
 41  ω     33.00 122.00   0.50    0.05    --  107.75 -15.00   0.00  178
 42  ω     33.00  66.00   0.50    0.05    --  107.75 -30.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1326860500
_diffrn_orient_matrix_UB_12      0.0442358500
_diffrn_orient_matrix_UB_13      0.1049605000
_diffrn_orient_matrix_UB_21      -0.0602504000
_diffrn_orient_matrix_UB_22      0.1701132000
_diffrn_orient_matrix_UB_23      -0.0077545000
_diffrn_orient_matrix_UB_31      -0.1372567000
_diffrn_orient_matrix_UB_32      -0.0318697000
_diffrn_orient_matrix_UB_33      0.1047394000
_diffrn_oxdiff_digest_frames     
;
01429401d370cebb233303ce7e7c961415056426308
;
_diffrn_oxdiff_digest_hkl        
;
014459d54a02173c914ee6906b539caaa2752f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                767
_reflns_number_total             767
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 351 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     57
_refine_ls_number_reflns         767
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0232
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.1569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.91 with sigma of 0.02
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H3C(0.5) H2A(0.5) H2B(0.5) H2C(0.5)
4.a Me refined with riding coordinates:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.000000 0.44611(6) 0.26830(5) 0.0114(2) Uani 1 2 d S T P . .
O1 O 0.000000 0.44463(19) 0.4097(2) 0.0176(5) Uani 1 2 d S T P . .
O2 O 0.15810(17) 0.37771(16) 0.21511(15) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.000000 0.6429(3) 0.2222(3) 0.0145(5) Uani 1 2 d S T P . .
H3A H 0.102273 0.692641 0.255340 0.022 Uiso 0.5 1 calc R . . A -1
H3B H -0.000813 0.650140 0.129885 0.022 Uiso 0.5 1 calc R . . A -1
H3C H -0.101459 0.692982 0.256346 0.022 Uiso 0.5 1 calc R . . A -1
N1 N 0.1486(2) 0.1505(2) 0.01277(18) 0.0181(4) Uani 1 1 d D . . . .
C2 C 0.000000 -0.0345(3) -0.1238(3) 0.0201(6) Uani 1 2 d S T P . .
H2A H -0.117626 -0.061931 -0.144546 0.030 Uiso 0.5 1 calc R . . B -1
H2B H 0.059288 -0.002238 -0.200699 0.030 Uiso 0.5 1 calc R . . B -1
H2C H 0.058338 -0.122596 -0.087479 0.030 Uiso 0.5 1 calc R . . B -1
C1 C 0.000000 0.0948(3) -0.0288(3) 0.0151(5) Uani 1 2 d S T P . .
H1A H 0.247(4) 0.111(4) -0.022(3) 0.039(8) Uiso 1 1 d D . . . .
H1B H 0.149(4) 0.229(3) 0.070(3) 0.030(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.467(2) . ?
S1 O2 1.4603(14) 3 ?
S1 O2 1.4603(14) . ?
S1 C3 1.763(3) . ?
N1 C1 1.313(2) . ?
C2 C1 1.488(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C3 106.23(12) . . ?
O2 S1 O1 111.99(7) 3 . ?
O2 S1 O1 111.99(7) . . ?
O2 S1 O2 112.82(12) 3 . ?
O2 S1 C3 106.65(8) 3 . ?
O2 S1 C3 106.65(8) . . ?
N1 C1 N1 121.1(3) . 3 ?
N1 C1 C2 119.44(13) 3 . ?
N1 C1 C2 119.44(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag

N1 H1A O1 0.90(2) 2.13(2) 3.0209(19) 170(3) 6_554 yes
N1 H1B O2 0.90(2) 1.98(2) 2.873(2) 171(3) . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.761
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_aca-C7H7SO3
_database_code_depnum_ccdc_archive 'CCDC 2090751'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'acetamidinium tosylate'
_chemical_name_systematic        'acetamidinium para-toluenesulfonate'
_chemical_formula_moiety         'C7 H7 O3 S, C2 H7 N2'
_chemical_formula_sum            'C9 H14 N2 O3 S'
_chemical_formula_weight         230.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.4723(8)
_cell_length_b                   6.2210(3)
_cell_length_c                   14.2758(7)
_cell_angle_alpha                90
_cell_angle_beta                 115.747(7)
_cell_angle_gamma                90
_cell_volume                     1157.68(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      76.5050
_cell_measurement_theta_min      6.2110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12134
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.932
_diffrn_reflns_theta_min         6.214
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 120.00   0.50    0.06    --   47.64  39.00  72.00  168
  2  ω     95.00 178.00   0.50    0.23    --  107.75  39.00  72.00  166
  3  ω     35.00  70.00   0.50    0.23    --  107.75 -39.00 -81.00   70
  4  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00 -60.00   66
  5  ω     37.00 121.00   0.50    0.23    --  107.75 -15.00 -90.00  168
  6  ω     34.00  95.00   0.50    0.06    --   47.64-125.00-180.00  122
  7  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00-180.00   66
  8  ω     35.00 124.00   0.50    0.23    --  107.75 -61.00-150.00  178
  9  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00 -30.00   66
 10  ω     36.00  76.00   0.50    0.23    --  107.75 -45.00  30.00   80
 11  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00  60.00   66
 12  ω     40.00  66.00   0.50    0.23    --  107.75 -45.00 120.00   52
 13  ω     36.00  76.00   0.50    0.23    --  107.75 -45.00 150.00   80
 14  ω     35.00 106.00   0.50    0.23    --  107.75 -94.00 120.00  142
 15  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00 150.00   66
 16  ω     33.00  62.00   0.50    0.23    --  107.75 -30.00  90.00   58
 17  ω     35.00 106.00   0.50    0.23    --  107.75 -94.00  30.00  142
 18  ω     33.00  66.00   0.50    0.23    --  107.75 -30.00-120.00   66
 19  ω     33.00  58.00   0.50    0.23    --  107.75 -30.00 -90.00   50
 20  ω     35.00 112.00   0.50    0.23    --  107.75-125.00-150.00  154
 21  ω    -25.00  61.00   0.50    0.06    --   47.64 -39.00 -81.00  172
 22  ω    -61.00  25.00   0.50    0.06    --  -47.64  39.00  72.00  172
 23  ω    -62.00  25.00   0.50    0.06    --  -47.64  57.00  60.00  174
 24  ω    -72.00 -13.00   0.50    0.23    --  -86.25  39.00  72.00  118
 25  ω   -120.00 -34.00   0.50    0.06    --  -47.64 -39.00 -81.00  172
 26  ω    -61.00  25.00   0.50    0.06    --  -47.64  38.00-180.00  172
 27  ω   -159.00 -73.00   0.50    0.23    --  -86.25 -39.00 -81.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1021568000
_diffrn_orient_matrix_UB_12      0.1231944000
_diffrn_orient_matrix_UB_13      -0.0530795000
_diffrn_orient_matrix_UB_21      0.0079680000
_diffrn_orient_matrix_UB_22      -0.0082230000
_diffrn_orient_matrix_UB_23      -0.1041238000
_diffrn_orient_matrix_UB_31      -0.0588695000
_diffrn_orient_matrix_UB_32      -0.2146234000
_diffrn_orient_matrix_UB_33      -0.0263852000
_diffrn_oxdiff_digest_frames     
;
0141f9041340572d037923dcf7d7531aa0001681637
;
_diffrn_oxdiff_digest_hkl        
;
01184cbe0895fc9d0a561e9ddc7b43c9ac2018
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2398
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1116P)²+0.4007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2B = N2-H2A = N1-H1B = N1-H1A
 0.91 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.19666(5) 0.73857(10) 0.70570(4) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.19308(15) 0.9653(3) 0.68269(14) 0.0464(5) Uani 1 1 d . . . . .
O3 O 0.14964(14) 0.6941(3) 0.77626(13) 0.0405(4) Uani 1 1 d . . . . .
O1 O 0.15483(15) 0.5996(4) 0.61538(13) 0.0527(5) Uani 1 1 d . . . . .
N2 N 0.1232(2) 0.5058(4) 0.41073(17) 0.0474(6) Uani 1 1 d D . . . .
N1 N 0.1149(2) 0.2516(4) 0.29247(18) 0.0408(5) Uani 1 1 d D . . . .
C3 C 0.32811(19) 0.6693(4) 0.77509(17) 0.0361(5) Uani 1 1 d . . . . .
C8 C 0.3617(2) 0.4660(4) 0.76511(19) 0.0411(6) Uani 1 1 d . . . . .
C4 C 0.3958(2) 0.8196(5) 0.84255(19) 0.0436(6) Uani 1 1 d . . . . .
C1 C 0.10942(19) 0.3074(4) 0.37867(18) 0.0375(6) Uani 1 1 d . . . . .
C2 C 0.0853(2) 0.1418(5) 0.4399(2) 0.0438(6) Uani 1 1 d . . . . .
C7 C 0.4643(2) 0.4123(5) 0.8239(2) 0.0458(6) Uani 1 1 d . . . . .
C6 C 0.5330(2) 0.5595(5) 0.89206(19) 0.0480(7) Uani 1 1 d . . . . .
C5 C 0.4969(3) 0.7626(5) 0.9001(2) 0.0514(8) Uani 1 1 d . . . . .
C9 C 0.6438(3) 0.5021(9) 0.9539(3) 0.0673(11) Uani 1 1 d . . . . .
H4 H 0.369(2) 0.962(5) 0.845(2) 0.043(8) Uiso 1 1 d . . . . .
H8 H 0.315(3) 0.353(6) 0.717(2) 0.050(8) Uiso 1 1 d . . . . .
H7 H 0.489(3) 0.264(5) 0.818(3) 0.047(9) Uiso 1 1 d . . . . .
H9A H 0.670(3) 0.533(7) 1.022(4) 0.089(14) Uiso 1 1 d . . . . .
H9B H 0.656(5) 0.364(12) 0.956(5) 0.13(2) Uiso 1 1 d . . . . .
H9C H 0.690(4) 0.524(8) 0.921(4) 0.098(14) Uiso 1 1 d . . . . .
H5 H 0.544(3) 0.858(6) 0.946(3) 0.057(9) Uiso 1 1 d . . . . .
H2C H 0.021(3) 0.143(7) 0.425(3) 0.073(12) Uiso 1 1 d . . . . .
H2D H 0.094(4) -0.008(8) 0.423(4) 0.096(14) Uiso 1 1 d . . . . .
H2E H 0.129(4) 0.161(9) 0.512(4) 0.112(16) Uiso 1 1 d . . . . .
H1A H 0.112(2) 0.113(3) 0.280(2) 0.043(8) Uiso 1 1 d D . . . .
H1B H 0.135(2) 0.349(4) 0.261(2) 0.042(8) Uiso 1 1 d D . . . .
H2A H 0.138(3) 0.614(4) 0.377(3) 0.061(10) Uiso 1 1 d D . . . .
H2B H 0.117(3) 0.548(6) 0.4683(19) 0.063(10) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.444(2) . ?
S1 O3 1.4662(17) . ?
S1 O1 1.4485(19) . ?
S1 C3 1.774(3) . ?
N2 C1 1.301(4) . ?
N2 H2A 0.905(19) . ?
N2 H2B 0.904(18) . ?
N1 C1 1.314(3) . ?
N1 H1A 0.876(18) . ?
N1 H1B 0.878(18) . ?
C3 C8 1.385(4) . ?
C3 C4 1.393(4) . ?
C8 C7 1.392(4) . ?
C8 H8 1.01(3) . ?
C4 C5 1.378(4) . ?
C4 H4 0.97(3) . ?
C1 C2 1.488(4) . ?
C2 H2C 0.86(4) . ?
C2 H2D 0.99(5) . ?
C2 H2E 0.95(6) . ?
C7 C6 1.391(4) . ?
C7 H7 1.01(3) . ?
C6 C5 1.391(5) . ?
C6 C9 1.500(4) . ?
C5 H5 0.93(4) . ?
C9 H9A 0.89(5) . ?
C9 H9B 0.88(7) . ?
C9 H9C 0.97(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 111.03(11) . . ?
O2 S1 O1 114.87(12) . . ?
O2 S1 C3 106.74(12) . . ?
O3 S1 C3 106.00(11) . . ?
O1 S1 O3 111.09(12) . . ?
O1 S1 C3 106.51(12) . . ?
C1 N2 H2A 124(2) . . ?
C1 N2 H2B 122(2) . . ?
H2A N2 H2B 114(3) . . ?
C1 N1 H1A 116(2) . . ?
C1 N1 H1B 118(2) . . ?
H1A N1 H1B 125(3) . . ?
C8 C3 S1 120.3(2) . . ?
C8 C3 C4 120.7(3) . . ?
C4 C3 S1 119.0(2) . . ?
C3 C8 C7 119.2(3) . . ?
C3 C8 H8 123.1(19) . . ?
C7 C8 H8 117.7(19) . . ?
C3 C4 H4 117.8(18) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 123.1(18) . . ?
N2 C1 N1 121.2(2) . . ?
N2 C1 C2 119.3(2) . . ?
N1 C1 C2 119.5(3) . . ?
C1 C2 H2C 111(3) . . ?
C1 C2 H2D 115(3) . . ?
C1 C2 H2E 110(3) . . ?
H2C C2 H2D 101(4) . . ?
H2C C2 H2E 113(4) . . ?
H2D C2 H2E 107(4) . . ?
C8 C7 H7 120(2) . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119(2) . . ?
C7 C6 C9 120.8(3) . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 C9 120.8(3) . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 122(2) . . ?
C6 C5 H5 117(2) . . ?
C6 C9 H9A 115(3) . . ?
C6 C9 H9B 114(4) . . ?
C6 C9 H9C 118(3) . . ?
H9A C9 H9B 101(4) . . ?
H9A C9 H9C 116(4) . . ?
H9B C9 H9C 89(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O3 0.876(18) 2.00(2) 2.845(3) 163(3) 4_565 yes
N1 H1B O2 0.878(18) 2.025(19) 2.895(3) 170(3) 4_575 yes
N2 H2A O3 0.905(19) 1.93(2) 2.820(3) 166(3) 4_575 yes
N2 H2B O1 0.904(18) 1.95(2) 2.815(3) 159(3) . yes

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 C3 C8 C7 -177.12(18) . . . . ?
S1 C3 C4 C5 177.0(2) . . . . ?
O2 S1 C3 C8 -148.23(19) . . . . ?
O2 S1 C3 C4 34.3(2) . . . . ?
O3 S1 C3 C8 93.3(2) . . . . ?
O3 S1 C3 C4 -84.2(2) . . . . ?
O1 S1 C3 C8 -25.1(2) . . . . ?
O1 S1 C3 C4 157.4(2) . . . . ?
C3 C8 C7 C6 0.0(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?
C8 C7 C6 C9 -179.0(3) . . . . ?
C4 C3 C8 C7 0.3(4) . . . . ?
C7 C6 C5 C4 0.1(4) . . . . ?
C9 C6 C5 C4 178.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.561
_oxdiff_exptl_absorpt_empirical_full_min 0.505
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_fa-cf3so3
_database_code_depnum_ccdc_archive 'CCDC 2090745'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'formamidinium triflate'
_chemical_name_systematic        'formamidinium trifluoromethanesulfonate'
_chemical_formula_moiety         'C F3 O3 S, C H5 N2'
_chemical_formula_sum            'C2 H5 F3 N2 O3 S'
_chemical_formula_weight         194.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2803(3)
_cell_length_b                   6.7118(4)
_cell_length_c                   9.3224(6)
_cell_angle_alpha                89.693(5)
_cell_angle_beta                 71.243(5)
_cell_angle_gamma                83.098(4)
_cell_volume                     369.16(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3673
_cell_measurement_temperature    123.00(12)
_cell_measurement_theta_max      75.1600
_cell_measurement_theta_min      6.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7664
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.225
_diffrn_reflns_theta_min         5.013
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  25.00   0.50    1.00    --  -47.64  38.00 -90.00  172
  2  ω    -61.00  25.00   0.50    1.00    --  -47.64  38.00-180.00  172
  3  ω    -90.00 -16.00   0.50    1.00    --  -47.64 131.00 -42.00  148
  4  ω    -90.00 -16.00   0.50    4.00    --  -86.25 131.00 -42.00  148
  5  ω    -95.00 -20.00   0.50    1.00    --  -47.64 138.00 133.00  150
  6  ω    -95.00 -20.00   0.50    4.00    --  -86.25 138.00 133.00  150
  7  ω   -158.00 -73.00   0.50    4.00    --  -86.25 -45.00 -60.00  170
  8  ω   -120.00 -73.00   0.50    1.00    --  -47.64-125.00 -90.00   94
  9  ω   -120.00 -70.00   0.50    1.00    --  -47.64-131.00-112.00  100
 10  ω   -120.00 -51.00   0.50    1.00    --  -47.64 -77.00 -90.00  138
 11  ω   -120.00 -33.00   0.50    1.00    --  -47.64 -57.00  30.00  174
 12  ω   -120.00 -65.00   0.50    1.00    --  -47.64-138.00  72.00  110
 13  ω     38.00  99.00   0.50    1.00    --   47.64-131.00-112.00  122
 14  ω     38.00 116.00   0.50    4.00    --  107.75-131.00-112.00  156
 15  ω     36.00  76.00   0.50    4.00    --  107.75 -45.00 -90.00   80
 16  ω     94.00 178.00   0.50    4.00    --  107.75  15.00-120.00  168
 17  ω     95.00 178.00   0.50    4.00    --  107.75 125.00  30.00  166
 18  ω     95.00 178.00   0.50    4.00    --  107.75 125.00  90.00  166
 19  ω     95.00 178.00   0.50    4.00    --  107.75  45.00 120.00  166
 20  ω     95.00 178.00   0.50    4.00    --  107.75 125.00 -30.00  166
 21  ω     91.00 178.00   0.50    4.00    --  107.75 131.00 -42.00  174
 22  ω     87.00 175.00   0.50    4.00    --  107.75 138.00 133.00  176
 23  ω     33.00  66.00   0.50    4.00    --  107.75 -30.00   0.00   66
 24  ω     35.00 124.00   0.50    4.00    --  107.75 -61.00 -30.00  178
 25  ω     42.00 103.00   0.50    1.00    --   47.64-138.00  72.00  122
 26  ω     42.00 121.00   0.50    4.00    --  107.75-138.00  72.00  158
 27  ω     35.00 106.00   0.50    4.00    --  107.75 -94.00 120.00  142
 28  ω     36.00  76.00   0.50    4.00    --  107.75 -45.00 120.00   80
 29  ω     33.00  66.00   0.50    4.00    --  107.75 -30.00  90.00   66
 30  ω     33.00  66.00   0.50    4.00    --  107.75 -30.00 120.00   66
 31  ω     35.00 106.00   0.50    4.00    --  107.75 -94.00 150.00  142
 32  ω     35.00 108.00   0.50    4.00    --  107.75-109.00  86.86  146
 33  ω     35.00 112.00   0.50    4.00    --  107.75-125.00 -30.00  154
 34  ω     36.00  76.00   0.50    4.00    --  107.75 -45.00-180.00   80
 35  ω     35.00 106.00   0.50    4.00    --  107.75 -94.00-150.00  142
 36  ω     36.00  76.00   0.50    4.00    --  107.75 -45.00-150.00   80
 37  ω     35.00 124.00   0.50    4.00    --  107.75 -61.00-120.00  178
 38  ω     33.00 122.00   0.50    4.00    --  107.75 -15.00 -60.00  178
 39  ω     35.00 106.00   0.50    4.00    --  107.75 -94.00  90.00  142
 40  ω     33.00  66.00   0.50    4.00    --  107.75 -30.00  30.00   66
 41  ω     35.00 112.00   0.50    4.00    --  107.75-125.00 150.00  154
 42  ω   -120.00 -25.00   0.50    1.00    --  -47.64 -77.00 150.00  190
 43  ω   -159.00 -70.00   0.50    4.00    --  -86.25-131.00-112.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1122560000
_diffrn_orient_matrix_UB_12      -0.2010292000
_diffrn_orient_matrix_UB_13      0.0383205000
_diffrn_orient_matrix_UB_21      0.1060245000
_diffrn_orient_matrix_UB_22      -0.0563698000
_diffrn_orient_matrix_UB_23      -0.1703120000
_diffrn_orient_matrix_UB_31      0.2105618000
_diffrn_orient_matrix_UB_32      0.0996664000
_diffrn_orient_matrix_UB_33      -0.0046757000
_diffrn_oxdiff_digest_frames     
;
01e34f8fa277013b3b7c085d1a2e92b13c0003328e7
;
_diffrn_oxdiff_digest_hkl        
;
018172c30957f547072ddf8d046494f4eff207
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1394
_reflns_number_total             1536
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         1536
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1063P)²+0.6326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.1941
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2A = N2-H2B = N1-H1A = N1-H1B
 0.91 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68977(15) 0.70297(12) 0.79777(10) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.6833(5) 0.4901(4) 0.7833(3) 0.0386(7) Uani 1 1 d . . . . .
O3 O 0.8944(6) 0.7485(4) 0.8210(4) 0.0479(8) Uani 1 1 d . . . . .
F5 F 0.7191(6) 0.9899(5) 0.6073(4) 0.0697(9) Uani 1 1 d . . . . .
F2 F 0.9013(7) 0.7074(6) 0.5066(4) 0.0895(13) Uani 1 1 d . . . . .
O2 O 0.4834(6) 0.8127(5) 0.8919(4) 0.0576(9) Uani 1 1 d . . . . .
N1 N -0.0073(6) 0.1621(5) 0.8401(4) 0.0380(8) Uani 1 1 d D . . . .
F1 F 0.5371(8) 0.7549(6) 0.5714(5) 0.0934(13) Uani 1 1 d . . . . .
N2 N 0.2293(6) 0.4007(5) 0.8209(4) 0.0405(8) Uani 1 1 d D . . . .
C1 C 0.1843(7) 0.2171(6) 0.8352(4) 0.0350(8) Uani 1 1 d . . . . .
H1 H 0.297524 0.118577 0.842370 0.042 Uiso 1 1 calc R . . . .
C2 C 0.7143(9) 0.7928(7) 0.6091(5) 0.0513(11) Uani 1 1 d . . . . .
H2A H 0.377(4) 0.419(6) 0.811(5) 0.029(10) Uiso 1 1 d D . . . .
H2B H 0.129(6) 0.504(5) 0.814(5) 0.035(11) Uiso 1 1 d D . . . .
H1A H -0.028(9) 0.032(4) 0.856(6) 0.045(13) Uiso 1 1 d D . . . .
H1B H -0.118(8) 0.259(7) 0.833(8) 0.08(2) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.442(3) . ?
S1 O3 1.437(3) . ?
S1 O2 1.428(3) . ?
S1 C2 1.821(5) . ?
F5 C2 1.327(6) . ?
F2 C2 1.320(6) . ?
N1 C1 1.287(5) . ?
N1 H1A 0.903(19) . ?
N1 H1B 0.91(2) . ?
F1 C2 1.322(6) . ?
N2 C1 1.294(5) . ?
N2 H2A 0.924(19) . ?
N2 H2B 0.895(19) . ?
C1 H1 0.9300 . ?

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 S1 C2 103.9(2) . . ?
O3 S1 O1 112.71(16) . . ?
O3 S1 C2 103.6(2) . . ?
O2 S1 O1 114.73(19) . . ?
O2 S1 O3 116.3(2) . . ?
O2 S1 C2 103.5(2) . . ?
C1 N1 H1A 119(3) . . ?
C1 N1 H1B 118(4) . . ?
H1A N1 H1B 123(5) . . ?
C1 N2 H2A 116(3) . . ?
C1 N2 H2B 123(3) . . ?
H2A N2 H2B 121(4) . . ?
N1 C1 N2 124.2(4) . . ?
N1 C1 H1 117.9 . . ?
N2 C1 H1 117.9 . . ?
F5 C2 S1 110.0(3) . . ?
F2 C2 S1 111.5(3) . . ?
F2 C2 F5 108.1(4) . . ?
F2 C2 F1 109.2(5) . . ?
F1 C2 S1 110.0(4) . . ?
F1 C2 F5 108.0(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O2 0.93 2.36 3.252(5) 161.6 1_545 yes
N2 H2A O1 0.924(19) 1.97(2) 2.895(4) 173(4) . yes
N2 H2B O3 0.895(19) 2.06(2) 2.948(4) 174(4) 1_455 yes
N1 H1A O3 0.903(19) 2.07(3) 2.933(4) 159(5) 1_445 yes
N1 H1B O1 0.91(2) 2.02(2) 2.919(4) 169(6) 1_455 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C2 F5 179.2(3) . . . . ?
O1 S1 C2 F2 -60.9(4) . . . . ?
O1 S1 C2 F1 60.4(4) . . . . ?
O3 S1 C2 F5 -62.8(4) . . . . ?
O3 S1 C2 F2 57.1(4) . . . . ?
O3 S1 C2 F1 178.4(3) . . . . ?
O2 S1 C2 F5 59.1(4) . . . . ?
O2 S1 C2 F2 179.0(4) . . . . ?
O2 S1 C2 F1 -59.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.582
_oxdiff_exptl_absorpt_empirical_full_min 0.406
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_aca-cf3so3
_database_code_depnum_ccdc_archive 'CCDC 2090750'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'acetamidinium triflate'
_chemical_name_systematic        'acetamidinium trifluoromethanesulfonate'
_chemical_formula_moiety         'C F3 O3 S, C2 H7 N2'
_chemical_formula_sum            'C3 H7 F3 N2 O3 S'
_chemical_formula_weight         208.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5871(5)
_cell_length_b                   11.7652(7)
_cell_length_c                   11.9506(5)
_cell_angle_alpha                74.772(5)
_cell_angle_beta                 77.729(6)
_cell_angle_gamma                77.878(6)
_cell_volume                     861.47(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5997
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      76.4100
_cell_measurement_theta_min      6.0420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17073
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.515
_diffrn_reflns_theta_min         3.888
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     25.00  73.00   0.50    0.05    --   47.64  77.00  90.00   96
  2  ω     25.00 120.00   0.50    0.05    --   47.64  77.00   0.00  190
  3  ω     25.00 120.00   0.50    0.05    --   47.64  77.00 -60.00  190
  4  ω     33.00 120.00   0.50    0.05    --   47.64  57.00 -90.00  174
  5  ω     33.00 120.00   0.50    0.05    --   47.64  55.00-151.00  174
  6  ω    -62.00  25.00   0.50    0.05    --  -47.64  55.00-151.00  174
  7  ω    -94.00 -14.00   0.50    0.19    --  -86.25  55.00-151.00  160
  8  ω    -86.00 -13.00   0.50    0.19    --  -86.25 125.00 -90.00  146
  9  ω     93.00 178.00   0.50    0.19    --  107.75  55.00-151.00  170
 10  ω     95.00 178.00   0.50    0.19    --  107.75 125.00 -90.00  166
 11  ω     95.00 178.00   0.50    0.19    --  107.75 125.00  30.00  166
 12  ω     95.00 178.00   0.50    0.19    --  107.75 125.00 120.00  166
 13  ω     95.00 178.00   0.50    0.19    --  107.75 125.00 150.00  166
 14  ω     33.00 122.00   0.50    0.19    --  107.75 -15.00   0.00  178
 15  ω     36.00  76.00   0.50    0.19    --  107.75 -45.00  60.00   80
 16  ω     35.00  92.00   0.50    0.19    --  107.75 -55.00  65.00  114
 17  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00 120.00   66
 18  ω    -24.00  62.00   0.50    0.05    --   47.64 -55.00  65.00  172
 19  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00 -60.00   66
 20  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00-120.00   66
 21  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00-180.00   66
 22  ω     36.00  76.00   0.50    0.19    --  107.75 -45.00-180.00   80
 23  ω     36.00  76.00   0.50    0.19    --  107.75 -45.00-150.00   80
 24  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00 -90.00   66
 25  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00  60.00   66
 26  ω     33.00  66.00   0.50    0.19    --  107.75 -30.00  90.00   66
 27  ω     34.00  95.00   0.50    0.05    --   47.64-125.00 120.00  122
 28  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00 120.00  142
 29  ω     35.00 112.00   0.50    0.19    --  107.75-125.00  60.00  154
 30  ω     35.00 112.00   0.50    0.19    --  107.75-125.00 -60.00  154
 31  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00 -30.00  142
 32  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00-150.00  142
 33  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00-180.00  142
 34  ω     35.00 112.00   0.50    0.19    --  107.75-125.00-150.00  154
 35  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00 -60.00  142
 36  ω     35.00 106.00   0.50    0.19    --  107.75 -94.00  60.00  142
 37  ω   -120.00 -25.00   0.50    0.05    --  -47.64 -77.00-180.00  190
 38  ω   -120.00 -73.00   0.50    0.05    --  -47.64-125.00-150.00   94
 39  ω   -120.00 -73.00   0.50    0.05    --  -47.64-125.00   0.00   94
 40  ω   -120.00 -73.00   0.50    0.05    --  -47.64-125.00  30.00   94
 41  ω   -159.00 -83.00   0.50    0.19    --  -86.25 -94.00  60.00  152
 42  ω   -159.00 -72.00   0.50    0.19    --  -86.25 -55.00  65.00  174
 43  ω   -120.00 -33.00   0.50    0.05    --  -47.64 -55.00  65.00  174
 44  ω   -120.00 -73.00   0.50    0.05    --  -47.64-125.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0249077000
_diffrn_orient_matrix_UB_12      -0.1288947000
_diffrn_orient_matrix_UB_13      0.0664052000
_diffrn_orient_matrix_UB_21      0.2213463000
_diffrn_orient_matrix_UB_22      -0.0456583000
_diffrn_orient_matrix_UB_23      -0.0611877000
_diffrn_orient_matrix_UB_31      0.0961498000
_diffrn_orient_matrix_UB_32      0.0149632000
_diffrn_orient_matrix_UB_33      0.1010284000
_diffrn_oxdiff_digest_frames     
;
01a172bb8d81acb6f6c6263d031caac35e0580636bf
;
_diffrn_oxdiff_digest_hkl        
;
019eb5871ed0b1d256555ec5f7c52277be4d66
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2974
_reflns_number_total             3582
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1360P)²+0.4324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4-H4B = N4-H4A = N3-H3A = N3-H3B = N1-H1B = N1-H1A = N2-H2B = N2-H2A
 0.91 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C4(H4C,H4D,H4E), C2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S2 S 1.15841(12) 0.28836(7) 1.00740(7) 0.0362(3) Uani 1 1 d . . . . .
S1 S 0.20667(12) 0.78525(6) 0.50131(6) 0.0362(3) Uani 1 1 d . . . . .
O2 O 0.2563(4) 0.8905(2) 0.4130(2) 0.0441(6) Uani 1 1 d . . . . .
O5 O 1.3513(4) 0.2901(2) 1.0440(2) 0.0464(6) Uani 1 1 d . . . . .
O1 O -0.0146(4) 0.7900(2) 0.5472(2) 0.0486(6) Uani 1 1 d . . . . .
O4 O 1.1033(4) 0.3880(2) 0.9120(2) 0.0466(6) Uani 1 1 d . . . . .
O6 O 0.9869(4) 0.2619(2) 1.1006(2) 0.0487(6) Uani 1 1 d . . . . .
O3 O 0.3466(4) 0.7439(2) 0.5863(2) 0.0454(6) Uani 1 1 d . . . . .
F6 F 1.2634(5) 0.0598(2) 1.0216(3) 0.0713(8) Uani 1 1 d . . . . .
N2 N -0.0702(5) 1.0448(3) 0.2844(3) 0.0400(6) Uani 1 1 d D . . . .
N4 N 0.6607(5) 0.4316(3) 0.8919(3) 0.0403(6) Uani 1 1 d D . . . .
F5 F 1.3825(6) 0.1681(3) 0.8559(3) 0.0921(11) Uani 1 1 d . . . . .
N3 N 0.4071(5) 0.5502(3) 0.7905(3) 0.0423(7) Uani 1 1 d D . . . .
F1 F 0.1449(7) 0.6961(3) 0.3367(3) 0.1053(13) Uani 1 1 d . . . . .
N1 N -0.3138(5) 0.9299(3) 0.3941(3) 0.0431(7) Uani 1 1 d D . . . .
F2 F 0.4641(7) 0.6559(3) 0.3685(3) 0.1005(12) Uani 1 1 d . . . . .
F3 F 0.2297(6) 0.5653(2) 0.4902(3) 0.0917(11) Uani 1 1 d . . . . .
F4 F 1.0568(7) 0.1505(3) 0.8975(3) 0.0989(12) Uani 1 1 d . . . . .
C1 C -0.2598(5) 1.0191(3) 0.3088(3) 0.0364(7) Uani 1 1 d . . . . .
C3 C 0.6033(5) 0.5194(3) 0.8056(3) 0.0358(7) Uani 1 1 d . . . . .
C4 C 0.7656(5) 0.5856(3) 0.7244(3) 0.0402(7) Uani 1 1 d . . . . .
H4C H 0.796663 0.642224 0.760811 0.060 Uiso 1 1 calc GR . . . .
H4D H 0.713656 0.627090 0.652824 0.060 Uiso 1 1 calc GR . . . .
H4E H 0.891268 0.530501 0.707083 0.060 Uiso 1 1 calc GR . . . .
C2 C -0.4231(6) 1.0957(3) 0.2393(3) 0.0468(8) Uani 1 1 d . . . . .
H2C H -0.523278 1.142383 0.287503 0.070 Uiso 1 1 calc GR . . . .
H2D H -0.494051 1.045970 0.213910 0.070 Uiso 1 1 calc GR . . . .
H2E H -0.356558 1.147919 0.171869 0.070 Uiso 1 1 calc GR . . . .
C5 C 1.2197(8) 0.1601(4) 0.9412(4) 0.0613(11) Uani 1 1 d . . . . .
C10 C 0.2669(10) 0.6698(4) 0.4187(4) 0.0703(14) Uani 1 1 d . . . . .
H1A H -0.442(4) 0.912(4) 0.407(4) 0.046(11) Uiso 1 1 d D . . . .
H4A H 0.794(3) 0.415(3) 0.902(4) 0.044(11) Uiso 1 1 d D . . . .
H4B H 0.563(5) 0.391(3) 0.940(3) 0.034(9) Uiso 1 1 d D . . . .
H1B H -0.227(5) 0.887(3) 0.442(3) 0.044(10) Uiso 1 1 d D . . . .
H3A H 0.306(6) 0.505(4) 0.833(4) 0.060(13) Uiso 1 1 d D . . . .
H2A H 0.030(5) 1.004(3) 0.327(3) 0.052(11) Uiso 1 1 d D . . . .
H3B H 0.378(9) 0.615(3) 0.732(4) 0.086(17) Uiso 1 1 d D . . . .
H2B H -0.041(7) 1.111(3) 0.230(3) 0.052(12) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S2 O5 1.434(2) . ?
S2 O4 1.449(2) . ?
S2 O6 1.430(3) . ?
S2 C5 1.817(5) . ?
S1 O2 1.446(2) . ?
S1 O1 1.439(3) . ?
S1 O3 1.438(2) . ?
S1 C10 1.814(5) . ?
F6 C5 1.333(5) . ?
N2 C1 1.302(4) . ?
N2 H2A 0.898(19) . ?
N2 H2B 0.901(19) . ?
N4 C3 1.310(4) . ?
N4 H4A 0.886(19) . ?
N4 H4B 0.895(19) . ?
F5 C5 1.313(6) . ?
N3 C3 1.305(4) . ?
N3 H3A 0.914(19) . ?
N3 H3B 0.91(2) . ?
F1 C10 1.331(6) . ?
N1 C1 1.306(4) . ?
N1 H1A 0.882(19) . ?
N1 H1B 0.884(19) . ?
F2 C10 1.305(7) . ?
F3 C10 1.336(6) . ?
F4 C5 1.326(6) . ?
C1 C2 1.496(4) . ?
C3 C4 1.484(5) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?

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
O5 S2 O4 113.73(14) . . ?
O5 S2 C5 103.7(2) . . ?
O4 S2 C5 103.81(19) . . ?
O6 S2 O5 115.32(16) . . ?
O6 S2 O4 114.38(15) . . ?
O6 S2 C5 103.95(19) . . ?
O2 S1 C10 103.3(2) . . ?
O1 S1 O2 113.61(15) . . ?
O1 S1 C10 104.0(2) . . ?
O3 S1 O2 113.72(15) . . ?
O3 S1 O1 116.31(15) . . ?
O3 S1 C10 103.9(2) . . ?
C1 N2 H2A 122(3) . . ?
C1 N2 H2B 120(3) . . ?
H2A N2 H2B 117(4) . . ?
C3 N4 H4A 119(3) . . ?
C3 N4 H4B 119(2) . . ?
H4A N4 H4B 122(4) . . ?
C3 N3 H3A 122(3) . . ?
C3 N3 H3B 117(4) . . ?
H3A N3 H3B 122(5) . . ?
C1 N1 H1A 120(3) . . ?
C1 N1 H1B 122(3) . . ?
H1A N1 H1B 118(4) . . ?
N2 C1 N1 122.1(3) . . ?
N2 C1 C2 119.1(3) . . ?
N1 C1 C2 118.8(3) . . ?
N4 C3 C4 119.0(3) . . ?
N3 C3 N4 121.4(3) . . ?
N3 C3 C4 119.6(3) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C1 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
C1 C2 H2E 109.5 . . ?
H2C C2 H2D 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
F6 C5 S2 110.4(3) . . ?
F5 C5 S2 111.7(3) . . ?
F5 C5 F6 108.1(4) . . ?
F5 C5 F4 108.2(4) . . ?
F4 C5 S2 110.6(4) . . ?
F4 C5 F6 107.6(4) . . ?
F1 C10 S1 110.3(4) . . ?
F1 C10 F3 107.6(5) . . ?
F2 C10 S1 111.7(4) . . ?
F2 C10 F1 109.2(5) . . ?
F2 C10 F3 107.8(4) . . ?
F3 C10 S1 110.1(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.882(19) 2.04(2) 2.917(4) 171(4) 1_455 yes
N4 H4A O4 0.886(19) 2.02(2) 2.903(4) 175(4) . yes
N4 H4B O5 0.895(19) 2.020(19) 2.913(4) 176(3) 1_455 yes
N1 H1B O1 0.884(19) 2.037(19) 2.921(4) 177(4) . yes
N3 H3A O4 0.914(19) 2.04(2) 2.944(4) 172(4) 1_455 yes
N2 H2A O2 0.898(19) 2.04(2) 2.930(4) 171(4) . yes
N3 H3B O3 0.91(2) 2.00(2) 2.901(4) 171(5) . yes
N2 H2B O6 0.901(19) 2.04(2) 2.931(4) 172(4) 1_464 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 C10 F1 -61.9(5) . . . . ?
O2 S1 C10 F2 59.7(4) . . . . ?
O2 S1 C10 F3 179.5(4) . . . . ?
O5 S2 C5 F6 64.1(4) . . . . ?
O5 S2 C5 F5 -56.3(4) . . . . ?
O5 S2 C5 F4 -176.9(3) . . . . ?
O1 S1 C10 F1 57.0(4) . . . . ?
O1 S1 C10 F2 178.6(3) . . . . ?
O1 S1 C10 F3 -61.6(4) . . . . ?
O4 S2 C5 F6 -176.8(3) . . . . ?
O4 S2 C5 F5 62.8(4) . . . . ?
O4 S2 C5 F4 -57.8(4) . . . . ?
O6 S2 C5 F6 -56.9(4) . . . . ?
O6 S2 C5 F5 -177.2(3) . . . . ?
O6 S2 C5 F4 62.1(4) . . . . ?
O3 S1 C10 F1 179.1(4) . . . . ?
O3 S1 C10 F2 -59.2(4) . . . . ?
O3 S1 C10 F3 60.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.477
_oxdiff_exptl_absorpt_empirical_full_min 0.395
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Gd_AuNN2_3
_database_code_depnum_ccdc_archive 'CCDC 2090753'
loop_
_audit_author_name
_audit_author_address
'Shuichi Suzuki'
;Osaka University
Japan
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C23 H40 Au1.5 Cl4 Gd0.5 N6 O6'
_chemical_formula_moiety         'C23 H40 Au1.5 Cl4 Gd0.5 N6 O6'
_chemical_formula_weight         1012.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   18.7386(5)
_cell_length_b                   17.1160(4)
_cell_length_c                   22.0203(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.3600(17)
_cell_angle_gamma                90.0000
_cell_volume                     7004.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22090
_cell_measurement_theta_min      1.94
_cell_measurement_theta_max      30.73
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3892.00
_exptl_absorpt_coefficient_mu    7.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.117
_exptl_absorpt_correction_T_max  0.219

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

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.626
_diffrn_reflns_number            33702
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.690
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7938
_reflns_number_gt                7144
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0890
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7938
_refine_ls_number_parameters     398
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0573P)²+17.6508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         1.98
_refine_diff_density_min         -1.09
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Au Au -2.0133 8.8022
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Gd Gd -0.1653 3.9035
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.67453(2) 0.62749(2) 0.60506(2) 0.03628(7) Uani 1 1 d . . . . .
Au2 Au 0.7500 0.91109(2) 0.5000 0.03867(8) Uani 1 2 d S T P . .
Gd1 Gd 0.7500 0.71594(2) 0.5000 0.03233(8) Uani 1 2 d S T P . .
Cl1 Cl 0.5736(2) 0.2974(3) 0.6972(2) 0.1681(17) Uani 1 1 d D . . . .
Cl2 Cl 0.6365(4) 0.3689(4) 0.59899(19) 0.217(3) Uani 1 1 d D . . . .
Cl3 Cl 0.8441(7) 0.4221(8) 0.8962(7) 0.185(6) Uani 0.5 1 d D . P A 1
Cl4 Cl 0.7456(8) 0.3147(7) 0.8209(7) 0.216(5) Uani 0.5 1 d D . P A 1
Cl5 Cl 0.7652(4) 0.2955(4) 0.9724(7) 0.203(8) Uani 0.5 1 d D . P B 2
Cl6 Cl 0.8192(13) 0.4248(15) 0.8831(8) 0.334(18) Uani 0.5 1 d D . P B 2
O1 O 0.8227(2) 0.6133(3) 0.54154(18) 0.0539(9) Uani 1 1 d . . . . .
O2 O 0.7411(3) 0.4800(3) 0.7003(2) 0.0728(13) Uani 1 1 d . . . . .
O3 O 0.63503(18) 0.7675(2) 0.50388(14) 0.0420(7) Uani 1 1 d . . . . .
O4 O 0.5274(2) 0.6818(2) 0.66875(18) 0.0503(9) Uani 1 1 d . . . . .
O5 O 0.7704(2) 0.7719(2) 0.59653(14) 0.0437(8) Uani 1 1 d . . . . .
O6 O 0.8726(3) 1.0170(2) 0.60018(19) 0.0607(10) Uani 1 1 d . . . . .
N1 N 0.8170(2) 0.5632(2) 0.58513(18) 0.0416(9) Uani 1 1 d . . . . .
N2 N 0.7798(3) 0.5015(3) 0.6598(2) 0.0488(10) Uani 1 1 d . . . . .
N3 N 0.5927(2) 0.7627(2) 0.54680(17) 0.0365(8) Uani 1 1 d . . . . .
N4 N 0.5416(2) 0.7229(2) 0.62318(18) 0.0380(8) Uani 1 1 d . . . . .
N5 N 0.8070(2) 0.8355(2) 0.61452(16) 0.0383(8) Uani 1 1 d . . . . .
N6 N 0.8548(2) 0.9488(2) 0.61684(18) 0.0444(9) Uani 1 1 d . . . . .
C1 C 0.7618(3) 0.5579(3) 0.6170(2) 0.0394(10) Uani 1 1 d . . . . .
C2 C 0.8729(3) 0.5014(4) 0.5987(3) 0.0548(14) Uani 1 1 d . . . . .
C3 C 0.8555(3) 0.4726(4) 0.6618(3) 0.0574(14) Uani 1 1 d . . . . .
C4 C 0.8552(7) 0.4399(6) 0.5486(4) 0.110(4) Uani 1 1 d . . . . .
H4A H 0.8902 0.3971 0.5548 0.132 Uiso 1 1 calc R U . . .
H4B H 0.8067 0.4194 0.5504 0.132 Uiso 1 1 calc R U . . .
H4C H 0.8574 0.4638 0.5084 0.132 Uiso 1 1 calc R U . . .
C5 C 0.9470(5) 0.5335(7) 0.5971(6) 0.114(4) Uani 1 1 d . . . . .
H5A H 0.9825 0.4917 0.6062 0.137 Uiso 1 1 calc R U . . .
H5B H 0.9508 0.5549 0.5564 0.137 Uiso 1 1 calc R U . . .
H5C H 0.9563 0.5750 0.6278 0.137 Uiso 1 1 calc R U . . .
C6 C 0.8609(5) 0.3877(4) 0.6752(4) 0.080(2) Uani 1 1 d . . . . .
H6A H 0.9110 0.3708 0.6762 0.096 Uiso 1 1 calc R U . . .
H6B H 0.8447 0.3774 0.7151 0.096 Uiso 1 1 calc R U . . .
H6C H 0.8305 0.3588 0.6433 0.096 Uiso 1 1 calc R U . . .
C7 C 0.8979(5) 0.5182(6) 0.7151(4) 0.085(2) Uani 1 1 d . . . . .
H7A H 0.8945 0.5744 0.7065 0.102 Uiso 1 1 calc R U . . .
H7B H 0.8777 0.5072 0.7531 0.102 Uiso 1 1 calc R U . . .
H7C H 0.9485 0.5022 0.7197 0.102 Uiso 1 1 calc R U . . .
C8 C 0.5962(2) 0.7074(3) 0.5899(2) 0.0344(9) Uani 1 1 d . . . . .
C9 C 0.5269(3) 0.8125(3) 0.5424(2) 0.0458(11) Uani 1 1 d . . . . .
C10 C 0.5054(3) 0.8003(3) 0.6079(2) 0.0425(11) Uani 1 1 d . . . . .
C11 C 0.4732(3) 0.7754(4) 0.4927(3) 0.0639(16) Uani 1 1 d . . . . .
H11A H 0.4286 0.8059 0.4878 0.077 Uiso 1 1 calc R U . . .
H11B H 0.4937 0.7748 0.4540 0.077 Uiso 1 1 calc R U . . .
H11C H 0.4629 0.7218 0.5046 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5422(4) 0.8951(3) 0.5254(3) 0.0609(16) Uani 1 1 d . . . . .
H12A H 0.4979 0.9260 0.5229 0.073 Uiso 1 1 calc R U . . .
H12B H 0.5784 0.9176 0.5565 0.073 Uiso 1 1 calc R U . . .
H12C H 0.5603 0.8958 0.4856 0.073 Uiso 1 1 calc R U . . .
C13 C 0.4266(4) 0.7956(4) 0.6118(4) 0.0673(18) Uani 1 1 d . . . . .
H13A H 0.4044 0.8466 0.6016 0.081 Uiso 1 1 calc R U . . .
H13B H 0.4048 0.7563 0.5828 0.081 Uiso 1 1 calc R U . . .
H13C H 0.4189 0.7808 0.6534 0.081 Uiso 1 1 calc R U . . .
C14 C 0.5413(4) 0.8582(4) 0.6548(3) 0.0627(16) Uani 1 1 d . . . . .
H14A H 0.5930 0.8606 0.6517 0.075 Uiso 1 1 calc R U . . .
H14B H 0.5200 0.9100 0.6469 0.075 Uiso 1 1 calc R U . . .
H14C H 0.5341 0.8411 0.6961 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8084(3) 0.9005(3) 0.5831(2) 0.0392(10) Uani 1 1 d . . . . .
C16 C 0.8442(3) 0.8387(3) 0.6790(2) 0.0472(12) Uani 1 1 d . . . . .
C17 C 0.8926(3) 0.9111(3) 0.6742(2) 0.0439(11) Uani 1 1 d . . . . .
C18 C 0.8820(5) 0.7626(4) 0.6942(3) 0.080(2) Uani 1 1 d . . . . .
H18A H 0.9064 0.7644 0.7362 0.096 Uiso 1 1 calc R U . . .
H18B H 0.8468 0.7200 0.6903 0.096 Uiso 1 1 calc R U . . .
H18C H 0.9175 0.7537 0.6659 0.096 Uiso 1 1 calc R U . . .
C19 C 0.7845(4) 0.8498(5) 0.7193(3) 0.072(2) Uani 1 1 d . . . . .
H19A H 0.8056 0.8523 0.7623 0.086 Uiso 1 1 calc R U . . .
H19B H 0.7586 0.8984 0.7080 0.086 Uiso 1 1 calc R U . . .
H19C H 0.7510 0.8057 0.7134 0.086 Uiso 1 1 calc R U . . .
C20 C 0.9679(4) 0.8917(4) 0.6607(3) 0.0616(15) Uani 1 1 d . . . . .
H20A H 0.9949 0.8670 0.6967 0.074 Uiso 1 1 calc R U . . .
H20B H 0.9651 0.8559 0.6258 0.074 Uiso 1 1 calc R U . . .
H20C H 0.9924 0.9398 0.6510 0.074 Uiso 1 1 calc R U . . .
C21 C 0.8957(3) 0.9684(4) 0.7275(2) 0.0562(14) Uani 1 1 d . . . . .
H21A H 0.9202 0.9439 0.7646 0.067 Uiso 1 1 calc R U . . .
H21B H 0.9221 1.0153 0.7180 0.067 Uiso 1 1 calc R U . . .
H21C H 0.8466 0.9829 0.7341 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6440(9) 0.3432(13) 0.6751(6) 0.183(8) Uani 1 1 d D . . . .
H22A H 0.6868 0.3092 0.6844 0.219 Uiso 1 1 calc R U . . .
H22B H 0.6530 0.3912 0.7000 0.219 Uiso 1 1 calc R U . . .
C23 C 0.7695(11) 0.4073(10) 0.8442(11) 0.115(8) Uani 0.5 1 d D . P A 1
H23A H 0.7760 0.4379 0.8071 0.138 Uiso 0.5 1 calc R U P A 1
H23B H 0.7281 0.4305 0.8614 0.138 Uiso 0.5 1 calc R U P A 1
C24 C 0.7770(11) 0.3950(10) 0.9476(12) 0.24(3) Uani 0.5 1 d D . P B 2
H24A H 0.7282 0.4182 0.9415 0.289 Uiso 0.5 1 calc R U P B 2
H24B H 0.8033 0.4223 0.9834 0.289 Uiso 0.5 1 calc R U P B 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 C8 2.003(4) . ?
Au1 C1 2.012(5) . ?
Au1 Gd1 3.2376(2) . ?
Au2 C15 2.016(5) . ?
Au2 C15 2.016(5) 2_656 ?
Au2 Gd1 3.3400(4) . ?
Gd1 O5 2.318(3) 2_656 ?
Gd1 O5 2.318(3) . ?
Gd1 O1 2.336(4) . ?
Gd1 O1 2.336(4) 2_656 ?
Gd1 O3 2.340(3) . ?
Gd1 O3 2.340(3) 2_656 ?
Gd1 Au1 3.2376(2) 2_656 ?
Cl1 C22 1.660(12) . ?
Cl2 C22 1.721(13) . ?
Cl3 C23 1.709(15) . ?
Cl4 C23 1.709(16) . ?
Cl5 Cl5 1.41(3) 2_657 ?
Cl5 C24 1.810(15) . ?
Cl6 C24 1.787(18) . ?
O1 N1 1.302(5) . ?
O2 N2 1.275(6) . ?
O3 N3 1.312(5) . ?
O4 N4 1.282(5) . ?
O5 N5 1.321(5) . ?
O6 N6 1.280(6) . ?
N1 C1 1.326(6) . ?
N1 C2 1.492(6) . ?
N2 C1 1.361(6) . ?
N2 C3 1.497(7) . ?
N3 C8 1.336(6) . ?
N3 C9 1.491(6) . ?
N4 C8 1.360(6) . ?
N4 C10 1.506(6) . ?
N5 C15 1.313(6) . ?
N5 C16 1.500(6) . ?
N6 C15 1.351(6) . ?
N6 C17 1.512(6) . ?
C2 C5 1.499(11) . ?
C2 C4 1.531(11) . ?
C2 C3 1.547(8) . ?
C3 C6 1.484(9) . ?
C3 C7 1.544(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C12 1.500(8) . ?
C9 C11 1.525(9) . ?
C9 C10 1.560(7) . ?
C10 C13 1.493(8) . ?
C10 C14 1.524(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C18 1.499(9) . ?
C16 C19 1.527(9) . ?
C16 C17 1.547(8) . ?
C17 C20 1.515(9) . ?
C17 C21 1.525(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 Au1 C1 172.57(19) . . ?
C8 Au1 Gd1 86.51(13) . . ?
C1 Au1 Gd1 87.01(14) . . ?
C15 Au2 C15 169.7(3) . 2_656 ?
C15 Au2 Gd1 84.86(14) . . ?
C15 Au2 Gd1 84.86(14) 2_656 . ?
O5 Gd1 O5 131.23(18) 2_656 . ?
O5 Gd1 O1 133.53(13) 2_656 . ?
O5 Gd1 O1 86.10(14) . . ?
O5 Gd1 O1 86.10(14) 2_656 2_656 ?
O5 Gd1 O1 133.53(13) . 2_656 ?
O1 Gd1 O1 82.5(2) . 2_656 ?
O5 Gd1 O3 80.42(11) 2_656 . ?
O5 Gd1 O3 81.66(13) . . ?
O1 Gd1 O3 139.71(12) . . ?
O1 Gd1 O3 78.71(14) 2_656 . ?
O5 Gd1 O3 81.66(13) 2_656 2_656 ?
O5 Gd1 O3 80.42(11) . 2_656 ?
O1 Gd1 O3 78.71(14) . 2_656 ?
O1 Gd1 O3 139.71(12) 2_656 2_656 ?
O3 Gd1 O3 135.68(18) . 2_656 ?
O5 Gd1 Au1 144.36(9) 2_656 . ?
O5 Gd1 Au1 64.75(8) . . ?
O1 Gd1 Au1 69.82(9) . . ?
O1 Gd1 Au1 69.03(10) 2_656 . ?
O3 Gd1 Au1 70.23(8) . . ?
O3 Gd1 Au1 133.71(8) 2_656 . ?
O5 Gd1 Au1 64.75(8) 2_656 2_656 ?
O5 Gd1 Au1 144.36(9) . 2_656 ?
O1 Gd1 Au1 69.02(10) . 2_656 ?
O1 Gd1 Au1 69.82(9) 2_656 2_656 ?
O3 Gd1 Au1 133.71(8) . 2_656 ?
O3 Gd1 Au1 70.23(8) 2_656 2_656 ?
Au1 Gd1 Au1 124.242(11) . 2_656 ?
O5 Gd1 Au2 65.61(9) 2_656 . ?
O5 Gd1 Au2 65.61(9) . . ?
O1 Gd1 Au2 138.73(12) . . ?
O1 Gd1 Au2 138.73(12) 2_656 . ?
O3 Gd1 Au2 67.84(9) . . ?
O3 Gd1 Au2 67.84(9) 2_656 . ?
Au1 Gd1 Au2 117.879(6) . . ?
Au1 Gd1 Au2 117.880(6) 2_656 . ?
Cl5 Cl5 C24 109.8(8) 2_657 . ?
N1 O1 Gd1 133.2(3) . . ?
N3 O3 Gd1 130.3(3) . . ?
N5 O5 Gd1 129.3(3) . . ?
O1 N1 C1 125.3(4) . . ?
O1 N1 C2 119.6(4) . . ?
C1 N1 C2 114.9(4) . . ?
O2 N2 C1 125.2(4) . . ?
O2 N2 C3 120.4(4) . . ?
C1 N2 C3 113.9(4) . . ?
O3 N3 C8 125.2(4) . . ?
O3 N3 C9 119.2(4) . . ?
C8 N3 C9 114.6(4) . . ?
O4 N4 C8 124.1(4) . . ?
O4 N4 C10 121.8(4) . . ?
C8 N4 C10 113.5(4) . . ?
C15 N5 O5 125.9(4) . . ?
C15 N5 C16 115.4(4) . . ?
O5 N5 C16 118.3(4) . . ?
O6 N6 C15 125.0(4) . . ?
O6 N6 C17 121.1(4) . . ?
C15 N6 C17 113.5(4) . . ?
N1 C1 N2 105.9(4) . . ?
N1 C1 Au1 124.5(3) . . ?
N2 C1 Au1 129.4(4) . . ?
N1 C2 C5 111.3(6) . . ?
N1 C2 C4 105.1(5) . . ?
C5 C2 C4 110.6(8) . . ?
N1 C2 C3 100.5(4) . . ?
C5 C2 C3 116.1(6) . . ?
C4 C2 C3 112.2(6) . . ?
C6 C3 N2 111.7(6) . . ?
C6 C3 C7 109.2(6) . . ?
N2 C3 C7 104.4(5) . . ?
C6 C3 C2 118.3(6) . . ?
N2 C3 C2 100.2(4) . . ?
C7 C3 C2 112.0(6) . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N4 105.8(4) . . ?
N3 C8 Au1 124.8(3) . . ?
N4 C8 Au1 129.0(3) . . ?
N3 C9 C12 111.8(5) . . ?
N3 C9 C11 105.8(5) . . ?
C12 C9 C11 110.0(5) . . ?
N3 C9 C10 99.9(4) . . ?
C12 C9 C10 115.9(5) . . ?
C11 C9 C10 112.5(5) . . ?
C13 C10 N4 111.1(4) . . ?
C13 C10 C14 110.5(5) . . ?
N4 C10 C14 105.9(4) . . ?
C13 C10 C9 115.7(5) . . ?
N4 C10 C9 99.4(4) . . ?
C14 C10 C9 113.4(5) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 N6 106.5(4) . . ?
N5 C15 Au2 120.6(4) . . ?
N6 C15 Au2 132.9(4) . . ?
N5 C16 C18 109.2(4) . . ?
N5 C16 C19 105.5(5) . . ?
C18 C16 C19 109.8(6) . . ?
N5 C16 C17 99.8(4) . . ?
C18 C16 C17 116.5(5) . . ?
C19 C16 C17 114.8(5) . . ?
N6 C17 C20 106.2(4) . . ?
N6 C17 C21 109.6(4) . . ?
C20 C17 C21 110.3(5) . . ?
N6 C17 C16 100.5(4) . . ?
C20 C17 C16 114.0(5) . . ?
C21 C17 C16 115.4(5) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 C22 Cl2 115.9(9) . . ?
Cl1 C22 H22A 108.3 . . ?
Cl2 C22 H22A 108.3 . . ?
Cl1 C22 H22B 108.3 . . ?
Cl2 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
Cl3 C23 Cl4 120.0(13) . . ?
Cl3 C23 H23A 107.3 . . ?
Cl4 C23 H23A 107.3 . . ?
Cl3 C23 H23B 107.3 . . ?
Cl4 C23 H23B 107.3 . . ?
H23A C23 H23B 106.9 . . ?
Cl6 C24 Cl5 126.3(16) . . ?
Cl6 C24 H24A 105.8 . . ?
Cl5 C24 H24A 105.8 . . ?
Cl6 C24 H24B 105.8 . . ?
Cl5 C24 H24B 105.8 . . ?
H24A C24 H24B 106.2 . . ?

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
Gd1 O1 N1 C1 2.5(8) . . . . ?
Gd1 O1 N1 C2 177.3(4) . . . . ?
Gd1 O3 N3 C8 -22.2(6) . . . . ?
Gd1 O3 N3 C9 169.6(3) . . . . ?
Gd1 O5 N5 C15 38.2(7) . . . . ?
Gd1 O5 N5 C16 -149.0(4) . . . . ?
O1 N1 C1 N2 -176.4(5) . . . . ?
C2 N1 C1 N2 8.6(6) . . . . ?
O1 N1 C1 Au1 -0.5(7) . . . . ?
C2 N1 C1 Au1 -175.4(4) . . . . ?
O2 N2 C1 N1 178.7(5) . . . . ?
C3 N2 C1 N1 6.8(6) . . . . ?
O2 N2 C1 Au1 3.0(8) . . . . ?
C3 N2 C1 Au1 -168.9(4) . . . . ?
O1 N1 C2 C5 41.9(8) . . . . ?
C1 N1 C2 C5 -142.8(7) . . . . ?
O1 N1 C2 C4 -77.8(7) . . . . ?
C1 N1 C2 C4 97.4(7) . . . . ?
O1 N1 C2 C3 165.5(5) . . . . ?
C1 N1 C2 C3 -19.2(6) . . . . ?
O2 N2 C3 C6 43.7(8) . . . . ?
C1 N2 C3 C6 -144.0(6) . . . . ?
O2 N2 C3 C7 -74.1(7) . . . . ?
C1 N2 C3 C7 98.1(6) . . . . ?
O2 N2 C3 C2 169.8(5) . . . . ?
C1 N2 C3 C2 -17.9(6) . . . . ?
N1 C2 C3 C6 141.4(6) . . . . ?
C5 C2 C3 C6 -98.4(9) . . . . ?
C4 C2 C3 C6 30.1(9) . . . . ?
N1 C2 C3 N2 19.8(6) . . . . ?
C5 C2 C3 N2 140.1(7) . . . . ?
C4 C2 C3 N2 -91.4(6) . . . . ?
N1 C2 C3 C7 -90.3(6) . . . . ?
C5 C2 C3 C7 29.9(8) . . . . ?
C4 C2 C3 C7 158.4(6) . . . . ?
O3 N3 C8 N4 -178.0(4) . . . . ?
C9 N3 C8 N4 -9.4(5) . . . . ?
O3 N3 C8 Au1 8.1(6) . . . . ?
C9 N3 C8 Au1 176.8(3) . . . . ?
O4 N4 C8 N3 179.5(4) . . . . ?
C10 N4 C8 N3 -9.2(5) . . . . ?
O4 N4 C8 Au1 -7.0(7) . . . . ?
C10 N4 C8 Au1 164.2(3) . . . . ?
O3 N3 C9 C12 -45.0(6) . . . . ?
C8 N3 C9 C12 145.7(5) . . . . ?
O3 N3 C9 C11 74.8(6) . . . . ?
C8 N3 C9 C11 -94.5(5) . . . . ?
O3 N3 C9 C10 -168.2(4) . . . . ?
C8 N3 C9 C10 22.4(5) . . . . ?
O4 N4 C10 C13 -44.1(7) . . . . ?
C8 N4 C10 C13 144.4(5) . . . . ?
O4 N4 C10 C14 75.9(6) . . . . ?
C8 N4 C10 C14 -95.6(5) . . . . ?
O4 N4 C10 C9 -166.4(4) . . . . ?
C8 N4 C10 C9 22.1(5) . . . . ?
N3 C9 C10 C13 -142.7(5) . . . . ?
C12 C9 C10 C13 97.0(6) . . . . ?
C11 C9 C10 C13 -30.9(7) . . . . ?
N3 C9 C10 N4 -23.8(5) . . . . ?
C12 C9 C10 N4 -144.1(5) . . . . ?
C11 C9 C10 N4 88.0(5) . . . . ?
N3 C9 C10 C14 88.1(5) . . . . ?
C12 C9 C10 C14 -32.2(7) . . . . ?
C11 C9 C10 C14 -160.1(5) . . . . ?
O5 N5 C15 N6 -177.1(4) . . . . ?
C16 N5 C15 N6 9.9(6) . . . . ?
O5 N5 C15 Au2 1.2(7) . . . . ?
C16 N5 C15 Au2 -171.8(4) . . . . ?
O6 N6 C15 N5 177.1(5) . . . . ?
C17 N6 C15 N5 4.8(6) . . . . ?
O6 N6 C15 Au2 -0.9(8) . . . . ?
C17 N6 C15 Au2 -173.2(4) . . . . ?
C15 N5 C16 C18 -142.0(6) . . . . ?
O5 N5 C16 C18 44.5(7) . . . . ?
C15 N5 C16 C19 100.1(5) . . . . ?
O5 N5 C16 C19 -73.5(6) . . . . ?
C15 N5 C16 C17 -19.3(6) . . . . ?
O5 N5 C16 C17 167.2(4) . . . . ?
O6 N6 C17 C20 -69.7(6) . . . . ?
C15 N6 C17 C20 102.9(5) . . . . ?
O6 N6 C17 C21 49.4(7) . . . . ?
C15 N6 C17 C21 -137.9(5) . . . . ?
O6 N6 C17 C16 171.3(5) . . . . ?
C15 N6 C17 C16 -16.0(6) . . . . ?
N5 C16 C17 N6 18.7(5) . . . . ?
C18 C16 C17 N6 136.1(5) . . . . ?
C19 C16 C17 N6 -93.6(5) . . . . ?
N5 C16 C17 C20 -94.4(5) . . . . ?
C18 C16 C17 C20 22.9(7) . . . . ?
C19 C16 C17 C20 153.3(5) . . . . ?
N5 C16 C17 C21 136.4(5) . . . . ?
C18 C16 C17 C21 -106.2(6) . . . . ?
C19 C16 C17 C21 24.1(7) . . . . ?
Cl5 Cl5 C24 Cl6 175(2) 2_657 . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_aca-CF3COO
_database_code_depnum_ccdc_archive 'CCDC 2090752'
loop_
_audit_author_name
_audit_author_address
'Samantha Piper'
;Monash University
Australia
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;

_vrf_DIFMX02_sp-aca-tfa          
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The largest resdiual electron density peak is located 
approximately 1.14 A from F5 
;
_vrf_PLAT097_sp-aca-tfa          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.76 eA-3  
RESPONSE: The largest resdiual electron density peak is located 
approximately 1.14 A from F5
;

_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'acetamidinium trifluoroacetate'
_chemical_formula_moiety         '4(C2 F3 O2), 4(C2 H7 N2)'
_chemical_formula_sum            'C16 H28 F12 N8 O8'
_chemical_formula_weight         688.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7077(2)
_cell_length_b                   18.0846(3)
_cell_length_c                   15.5398(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.304(2)
_cell_angle_gamma                90
_cell_volume                     3009.15(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10448
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      75.4160
_cell_measurement_theta_min      3.7250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.81a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.507
_diffrn_reflns_theta_min         3.750
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00 -33.00   0.50    0.34    --  -86.25  96.00 118.00   94
  2  ω   -159.00 -62.00   0.50    0.34    --  -86.25 -79.00-101.00  194
  3  ω   -120.00 -73.00   0.50    0.08    --  -47.95-125.00   0.00   94
  4  ω   -120.00 -73.00   0.50    0.08    --  -47.95-125.00 -90.00   94
  5  ω   -120.00 -73.00   0.50    0.08    --  -47.95-125.00-180.00   94
  6  ω   -120.00 -73.00   0.50    0.08    --  -47.95-125.00 -30.00   94
  7  ω   -120.00 -73.00   0.50    0.08    --  -47.95-125.00  90.00   94
  8  ω     34.00  60.00   0.50    0.34    --  107.75 -30.00 150.00   52
  9  ω     40.00  66.00   0.50    0.34    --  107.75 -30.00 120.00   52
 10  ω     41.00  67.00   0.50    0.34    --  107.75 -45.00  90.00   52
 11  ω     44.00  74.00   0.50    0.34    --  107.75 -45.00  30.00   60
 12  ω     46.00  72.00   0.50    0.34    --  107.75 -45.00 -30.00   52
 13  ω    100.00 126.00   0.50    0.34    --  107.75 -77.00 -90.00   52
 14  ω     94.00 178.00   0.50    0.34    --  107.75  52.00-105.00  168
 15  ω    106.00 178.00   0.50    0.34    --  107.75  96.00 118.00  144
 16  ω     38.00  67.00   0.50    0.34    --  107.75 -77.00 -90.00   58
 17  ω     42.00  68.00   0.50    0.34    --  107.75 -45.00-120.00   52
 18  ω     33.00  62.00   0.50    0.34    --  107.75 -30.00 -90.00   58
 19  ω     36.00  76.00   0.50    0.34    --  107.75 -45.00   0.00   80
 20  ω   -142.00-113.00   0.50    0.34    --  -86.25 -96.00   9.00   58
 21  ω    -45.00  25.00   0.50    0.08    --  -47.95  57.00  30.00  140
 22  ω   -120.00 -95.00   0.50    0.08    --  -47.95-125.00  60.00   50
 23  ω     73.00  99.00   0.50    0.34    --  107.75-125.00  90.00   52
 24  ω     34.00  59.00   0.50    0.34    --  107.75 -30.00  30.00   50
 25  ω    110.00 137.00   0.50    0.34    --  107.75  45.00 -90.00   54
 26  ω     39.00  87.00   0.50    0.34    --  107.75 -77.00 150.00   96
 27  ω     73.00 105.00   0.50    0.34    --  107.75 -94.00 -30.00   64
 28  ω     94.00 128.00   0.50    0.34    --  107.75 -77.00 150.00   68
 29  ω     37.00  63.00   0.50    0.34    --  107.75 -45.00 -90.00   52
 30  ω     60.00  91.00   0.50    0.34    --  107.75 -94.00  60.00   62
 31  ω     43.00  75.00   0.50    0.34    --  107.75 -45.00  60.00   64
 32  ω    146.00 175.00   0.50    0.34    --  107.75  45.00 -90.00   58
 33  ω     35.00  62.00   0.50    0.34    --  107.75 -30.00   0.00   54
 34  ω     45.00  70.00   0.50    0.34    --  107.75 -94.00 120.00   50
 35  ω     63.00 105.00   0.50    0.34    --  107.75 -94.00  90.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0945679000
_diffrn_orient_matrix_UB_12      0.0350882000
_diffrn_orient_matrix_UB_13      -0.0628690000
_diffrn_orient_matrix_UB_21      0.0781870000
_diffrn_orient_matrix_UB_22      0.0714748000
_diffrn_orient_matrix_UB_23      -0.0014762000
_diffrn_orient_matrix_UB_31      0.0751271000
_diffrn_orient_matrix_UB_32      -0.0301851000
_diffrn_orient_matrix_UB_33      -0.0766907000
_diffrn_oxdiff_digest_frames     
;
01d440d5d10fc614eb8096b4b7727ca6c202694ec25
;
_diffrn_oxdiff_digest_hkl        
;
0175262bbc6beff5fdbf99add10575d9362011
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5274
_reflns_number_total             6276
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.81a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     503
_refine_ls_number_reflns         6276
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1171P)²+1.9276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2007
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.926(1)
 0.074(1)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N2-H2B = N2-H2A = N1-H1B = N1-H1A = N3-H3B = N3-H3A = N4-H4A = N4-H4B = N5-
 H5B = N5-H5A = N6-H6A = N6-H6B = N7-H7B = N7-H7A = N8-H8E = N8-H8D
 0.91 with sigma of 0.02
 F3A-C15B \\sim F1B-C15A \\sim F1A-C15B \\sim F2B-C15A \\sim F2A-C15B \\sim
F3B-C15A
 with sigma of 0.01
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(C15A)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C15B)=FVAR(1)
5.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F1A F 0.6661(4) 1.0322(3) 0.1765(4) 0.071(2) Uani 0.629(8) 1 d D . P A 1
F1B F 0.6771(8) 0.9803(11) 0.1921(5) 0.113(7) Uani 0.371(8) 1 d D . P A 2
F2A F 0.6560(8) 0.9683(6) 0.0593(4) 0.087(3) Uani 0.629(8) 1 d D . P A 1
F2B F 0.6593(5) 1.0553(4) 0.0895(6) 0.073(3) Uani 0.371(8) 1 d D . P A 2
F3A F 0.7063(4) 0.9182(3) 0.1763(4) 0.0751(15) Uani 0.629(8) 1 d D . P A 1
F3B F 0.6629(14) 0.9476(8) 0.0659(11) 0.086(5) Uani 0.371(8) 1 d D . P A 2
O1 O 0.90068(18) 1.05672(10) 0.13505(14) 0.0356(4) Uani 1 1 d . . . . .
O2 O 0.91312(18) 0.94322(10) 0.07769(14) 0.0350(4) Uani 1 1 d . . . . .
C15A C 0.7179(13) 0.9958(5) 0.1153(6) 0.033(3) Uani 0.371(8) 1 d D . P A 2
C15B C 0.7164(8) 0.9787(3) 0.1316(4) 0.0345(18) Uani 0.629(8) 1 d D . P A 1
C16 C 0.8581(3) 0.99631(14) 0.11095(17) 0.0297(5) Uani 1 1 d . . . . .
F4 F 0.4970(2) 0.79525(12) 0.24081(14) 0.0561(5) Uani 1 1 d . . . . .
F5 F 0.6291(2) 0.72861(19) 0.17190(13) 0.0765(8) Uani 1 1 d . . . . .
F6 F 0.5146(2) 0.68116(13) 0.26843(16) 0.0649(6) Uani 1 1 d . . . . .
O3 O 0.68299(18) 0.81941(10) 0.35071(12) 0.0327(4) Uani 1 1 d . . . . .
O4 O 0.7552(2) 0.70505(11) 0.32936(13) 0.0396(5) Uani 1 1 d . . . . .
C17 C 0.5808(3) 0.74238(17) 0.24785(19) 0.0386(6) Uani 1 1 d . . . . .
C18 C 0.6833(3) 0.75765(14) 0.31651(16) 0.0298(5) Uani 1 1 d . . . . .
F7 F 1.02475(17) 0.55294(11) 0.14490(19) 0.0606(6) Uani 1 1 d . . . . .
F8 F 1.01027(19) 0.45017(13) 0.07670(15) 0.0564(5) Uani 1 1 d . . . . .
F9 F 1.00731(18) 0.45142(12) 0.21369(14) 0.0513(5) Uani 1 1 d . . . . .
O5 O 0.78152(18) 0.55407(10) 0.11468(15) 0.0360(4) Uani 1 1 d . . . . .
O6 O 0.76759(18) 0.43771(10) 0.16238(15) 0.0380(5) Uani 1 1 d . . . . .
C19 C 0.9684(3) 0.48800(16) 0.1441(2) 0.0348(6) Uani 1 1 d . . . . .
C20 C 0.8245(2) 0.49441(14) 0.14029(17) 0.0286(5) Uani 1 1 d . . . . .
F10 F 0.5184(4) 0.32228(17) 0.5053(3) 0.1192(15) Uani 1 1 d . . . . .
F11 F 0.6107(2) 0.2368(2) 0.58025(14) 0.0917(11) Uani 1 1 d . . . . .
F12 F 0.4655(2) 0.21081(16) 0.49508(15) 0.0661(7) Uani 1 1 d . . . . .
O7 O 0.7300(2) 0.29794(11) 0.41860(14) 0.0429(5) Uani 1 1 d . . . . .
O8 O 0.66289(19) 0.18204(10) 0.39944(13) 0.0358(4) Uani 1 1 d . . . . .
C21 C 0.5638(3) 0.25613(19) 0.5043(2) 0.0448(7) Uani 1 1 d . . . . .
C22 C 0.6618(3) 0.24417(15) 0.43336(17) 0.0309(5) Uani 1 1 d . . . . .
N1 N 0.4905(2) 1.05937(12) 0.39260(17) 0.0322(5) Uani 1 1 d D . . . .
H1A H 0.4071(18) 1.0585(18) 0.386(2) 0.031(8) Uiso 1 1 d D . . . .
H1B H 0.535(4) 1.1008(15) 0.400(3) 0.054(11) Uiso 1 1 d D . . . .
N2 N 0.4983(2) 0.93460(12) 0.36614(16) 0.0311(5) Uani 1 1 d D . . . .
H2A H 0.4143(17) 0.9335(17) 0.360(2) 0.026(7) Uiso 1 1 d D . . . .
H2B H 0.543(3) 0.8948(13) 0.355(2) 0.028(8) Uiso 1 1 d D . . . .
C7 C 0.5531(2) 0.99745(14) 0.38392(17) 0.0288(5) Uani 1 1 d . . . . .
C8 C 0.6912(3) 0.99858(15) 0.3972(2) 0.0353(6) Uani 1 1 d . . . . .
H8A H 0.709969 0.989095 0.456691 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.723359 1.046191 0.381395 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.729101 0.961165 0.362174 0.053 Uiso 1 1 calc GR . . . .
N3 N 0.8382(2) 0.80684(12) 0.00442(15) 0.0300(5) Uani 1 1 d D . . . .
H3A H 0.808(4) 0.806(2) -0.0491(15) 0.047(10) Uiso 1 1 d D . . . .
H3B H 0.856(4) 0.8509(14) 0.030(2) 0.046(10) Uiso 1 1 d D . . . .
N4 N 0.8256(2) 0.68101(12) 0.01214(15) 0.0309(5) Uani 1 1 d D . . . .
H4A H 0.786(3) 0.680(2) -0.0394(16) 0.044(10) Uiso 1 1 d D . . . .
H4B H 0.822(4) 0.6405(16) 0.045(2) 0.057(12) Uiso 1 1 d D . . . .
C9 C 0.8573(2) 0.74489(14) 0.04589(17) 0.0276(5) Uani 1 1 d . . . . .
C10 C 0.9203(3) 0.74659(18) 0.13136(19) 0.0384(6) Uani 1 1 d . . . . .
H10A H 1.008993 0.743282 0.123770 0.058 Uiso 1 1 calc GR . . . .
H10B H 0.892099 0.705574 0.165340 0.058 Uiso 1 1 calc GR . . . .
H10C H 0.900306 0.792007 0.160158 0.058 Uiso 1 1 calc GR . . . .
N5 N 0.8335(2) 0.55800(12) 0.34734(17) 0.0327(5) Uani 1 1 d D . . . .
H5A H 0.9163(18) 0.5606(19) 0.358(2) 0.038(9) Uiso 1 1 d D . . . .
H5B H 0.789(3) 0.5976(15) 0.330(2) 0.041(9) Uiso 1 1 d D . . . .
N6 N 0.8223(2) 0.44273(12) 0.40701(17) 0.0335(5) Uani 1 1 d D . . . .
H6A H 0.9056(18) 0.441(2) 0.415(2) 0.042(9) Uiso 1 1 d D . . . .
H6B H 0.777(3) 0.4023(15) 0.420(3) 0.048(10) Uiso 1 1 d D . . . .
C11 C 0.7685(2) 0.50003(15) 0.37069(18) 0.0305(5) Uani 1 1 d . . . . .
C12 C 0.6307(3) 0.49910(18) 0.3559(2) 0.0406(7) Uani 1 1 d . . . . .
H12A H 0.593886 0.541955 0.381933 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.595771 0.455280 0.380998 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.613708 0.499455 0.295148 0.061 Uiso 1 1 calc GR . . . .
N7 N 0.8076(2) 0.30183(12) 0.24427(15) 0.0305(5) Uani 1 1 d D . . . .
H7A H 0.778(3) 0.3001(19) 0.2990(14) 0.034(8) Uiso 1 1 d D . . . .
H7B H 0.816(4) 0.3446(14) 0.215(2) 0.045(10) Uiso 1 1 d D . . . .
N8 N 0.8128(2) 0.17593(12) 0.23974(16) 0.0316(5) Uani 1 1 d D . . . .
H8D H 0.829(3) 0.1356(15) 0.209(2) 0.044(9) Uiso 1 1 d D . . . .
H8E H 0.773(3) 0.1731(19) 0.2900(15) 0.035(8) Uiso 1 1 d D . . . .
C13 C 0.8360(2) 0.24021(14) 0.20493(17) 0.0278(5) Uani 1 1 d . . . . .
C14 C 0.9005(3) 0.24400(17) 0.12007(19) 0.0385(6) Uani 1 1 d . . . . .
H14A H 0.879511 0.289646 0.091962 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.874135 0.203236 0.084804 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.989177 0.241546 0.128881 0.058 Uiso 1 1 calc GR . . . .


_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
F1A C15B 1.311(6) . ?
F1B C15A 1.303(7) . ?
F2A C15B 1.307(6) . ?
F2B C15A 1.309(7) . ?
F3A C15B 1.301(6) . ?
F3B C15A 1.300(7) . ?
O1 C16 1.241(3) . ?
O2 C16 1.241(3) . ?
C15A C16 1.503(14) . ?
C15B C16 1.584(9) . ?
F4 C17 1.315(4) . ?
F5 C17 1.315(4) . ?
F6 C17 1.354(4) . ?
O3 C18 1.237(3) . ?
O4 C18 1.239(3) . ?
C17 C18 1.552(4) . ?
F7 C19 1.320(3) . ?
F8 C19 1.331(4) . ?
F9 C19 1.332(4) . ?
O5 C20 1.238(3) . ?
O6 C20 1.242(3) . ?
C19 C20 1.546(4) . ?
F10 C21 1.292(5) . ?
F11 C21 1.327(4) . ?
F12 C21 1.341(4) . ?
O7 C22 1.239(3) . ?
O8 C22 1.241(3) . ?
C21 C22 1.541(4) . ?
N1 H1A 0.898(18) . ?
N1 H1B 0.893(19) . ?
N1 C7 1.313(3) . ?
N2 H2A 0.903(18) . ?
N2 H2B 0.884(18) . ?
N2 C7 1.308(3) . ?
C7 C8 1.492(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N3 H3A 0.893(19) . ?
N3 H3B 0.912(19) . ?
N3 C9 1.308(3) . ?
N4 H4A 0.903(19) . ?
N4 H4B 0.898(19) . ?
N4 C9 1.313(3) . ?
C9 C10 1.486(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N5 H5A 0.902(19) . ?
N5 H5B 0.898(18) . ?
N5 C11 1.311(4) . ?
N6 H6A 0.902(19) . ?
N6 H6B 0.902(19) . ?
N6 C11 1.312(4) . ?
C11 C12 1.493(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N7 H7A 0.910(18) . ?
N7 H7B 0.903(18) . ?
N7 C13 1.308(3) . ?
N8 H8D 0.893(18) . ?
N8 H8E 0.894(18) . ?
N8 C13 1.307(3) . ?
C13 C14 1.493(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
F1B C15A F2B 107.1(12) . . ?
F1B C15A C16 112.5(9) . . ?
F2B C15A C16 117.3(9) . . ?
F3B C15A F1B 104.1(14) . . ?
F3B C15A F2B 99.0(10) . . ?
F3B C15A C16 115.3(10) . . ?
F1A C15B C16 110.9(5) . . ?
F2A C15B F1A 111.1(8) . . ?
F2A C15B C16 109.0(6) . . ?
F3A C15B F1A 107.5(6) . . ?
F3A C15B F2A 107.2(7) . . ?
F3A C15B C16 111.1(5) . . ?
O1 C16 C15A 111.0(4) . . ?
O1 C16 C15B 117.8(3) . . ?
O2 C16 O1 129.2(3) . . ?
O2 C16 C15A 119.4(4) . . ?
O2 C16 C15B 112.7(3) . . ?
F4 C17 F6 104.9(3) . . ?
F4 C17 C18 114.1(2) . . ?
F5 C17 F4 109.5(3) . . ?
F5 C17 F6 105.4(3) . . ?
F5 C17 C18 111.8(3) . . ?
F6 C17 C18 110.6(2) . . ?
O3 C18 O4 128.8(3) . . ?
O3 C18 C17 116.9(2) . . ?
O4 C18 C17 114.3(2) . . ?
F7 C19 F8 108.0(3) . . ?
F7 C19 F9 107.1(3) . . ?
F7 C19 C20 112.9(2) . . ?
F8 C19 F9 106.2(2) . . ?
F8 C19 C20 110.4(2) . . ?
F9 C19 C20 112.0(2) . . ?
O5 C20 O6 128.8(3) . . ?
O5 C20 C19 116.5(2) . . ?
O6 C20 C19 114.7(2) . . ?
F10 C21 F11 111.9(4) . . ?
F10 C21 F12 105.8(3) . . ?
F10 C21 C22 113.4(3) . . ?
F11 C21 F12 103.1(3) . . ?
F11 C21 C22 110.1(3) . . ?
F12 C21 C22 112.0(3) . . ?
O7 C22 O8 128.7(3) . . ?
O7 C22 C21 115.3(3) . . ?
O8 C22 C21 116.0(2) . . ?
H1A N1 H1B 124(3) . . ?
C7 N1 H1A 119(2) . . ?
C7 N1 H1B 117(3) . . ?
H2A N2 H2B 120(3) . . ?
C7 N2 H2A 119(2) . . ?
C7 N2 H2B 120(2) . . ?
N1 C7 C8 118.7(2) . . ?
N2 C7 N1 122.3(2) . . ?
N2 C7 C8 119.0(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H3A N3 H3B 120(4) . . ?
C9 N3 H3A 120(3) . . ?
C9 N3 H3B 120(3) . . ?
H4A N4 H4B 118(4) . . ?
C9 N4 H4A 120(2) . . ?
C9 N4 H4B 120(3) . . ?
N3 C9 N4 121.2(2) . . ?
N3 C9 C10 119.4(2) . . ?
N4 C9 C10 119.4(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H5A N5 H5B 122(3) . . ?
C11 N5 H5A 121(2) . . ?
C11 N5 H5B 116(2) . . ?
H6A N6 H6B 118(3) . . ?
C11 N6 H6A 121(2) . . ?
C11 N6 H6B 120(3) . . ?
N5 C11 N6 121.2(2) . . ?
N5 C11 C12 119.5(3) . . ?
N6 C11 C12 119.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H7A N7 H7B 123(3) . . ?
C13 N7 H7A 119(2) . . ?
C13 N7 H7B 118(2) . . ?
H8D N8 H8E 122(3) . . ?
C13 N8 H8D 118(2) . . ?
C13 N8 H8E 120(2) . . ?
N7 C13 C14 118.9(2) . . ?
N8 C13 N7 121.3(2) . . ?
N8 C13 C14 119.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O5 0.898(18) 2.021(19) 2.916(3) 174(3) 2_655 yes
N1 H1B O8 0.893(19) 2.01(2) 2.887(3) 166(4) 1_565 yes
N2 H2A O6 0.903(18) 1.979(19) 2.879(3) 174(3) 2_655 yes
N2 H2B O3 0.884(18) 2.02(2) 2.884(3) 164(3) . yes
N3 H3A O4 0.893(19) 1.98(2) 2.865(3) 173(4) 4_575 yes
N3 H3B O2 0.912(19) 1.923(19) 2.831(3) 173(4) . yes
N4 H4A O3 0.903(19) 2.03(2) 2.930(3) 174(4) 4_575 yes
N4 H4B O5 0.898(19) 1.95(2) 2.835(3) 170(4) . yes
N5 H5A O1 0.902(19) 1.96(2) 2.858(3) 171(3) 2_745 yes
N5 H5B O4 0.898(18) 1.98(2) 2.802(3) 152(3) . yes
N6 H6A O2 0.902(19) 1.944(19) 2.842(3) 174(4) 2_745 yes
N6 H6B O7 0.902(19) 1.95(2) 2.805(3) 157(4) . yes
N7 H7A O7 0.910(18) 1.931(19) 2.839(3) 175(3) . yes
N7 H7B O6 0.903(18) 1.94(2) 2.799(3) 158(4) . yes
N8 H8D O1 0.893(18) 1.98(2) 2.863(3) 168(3) 1_545 yes
N8 H8E O8 0.894(18) 2.08(2) 2.965(3) 170(3) . yes

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
F1A C15B C16 O1 -3.0(7) . . . . ?
F1A C15B C16 O2 171.8(5) . . . . ?
F1B C15A C16 O1 -83.4(11) . . . . ?
F1B C15A C16 O2 103.6(11) . . . . ?
F2A C15B C16 O1 119.6(6) . . . . ?
F2A C15B C16 O2 -65.6(7) . . . . ?
F2B C15A C16 O1 41.5(9) . . . . ?
F2B C15A C16 O2 -131.5(8) . . . . ?
F3A C15B C16 O1 -122.5(5) . . . . ?
F3A C15B C16 O2 52.3(6) . . . . ?
F3B C15A C16 O1 157.5(10) . . . . ?
F3B C15A C16 O2 -15.5(12) . . . . ?
F4 C17 C18 O3 -6.7(4) . . . . ?
F4 C17 C18 O4 173.3(3) . . . . ?
F5 C17 C18 O3 118.2(3) . . . . ?
F5 C17 C18 O4 -61.8(4) . . . . ?
F6 C17 C18 O3 -124.7(3) . . . . ?
F6 C17 C18 O4 55.3(3) . . . . ?
F7 C19 C20 O5 19.5(4) . . . . ?
F7 C19 C20 O6 -161.6(3) . . . . ?
F8 C19 C20 O5 -101.4(3) . . . . ?
F8 C19 C20 O6 77.5(3) . . . . ?
F9 C19 C20 O5 140.5(3) . . . . ?
F9 C19 C20 O6 -40.6(3) . . . . ?
F10 C21 C22 O7 36.0(5) . . . . ?
F10 C21 C22 O8 -144.8(4) . . . . ?
F11 C21 C22 O7 -90.3(4) . . . . ?
F11 C21 C22 O8 88.9(4) . . . . ?
F12 C21 C22 O7 155.6(3) . . . . ?
F12 C21 C22 O8 -25.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.116
_oxdiff_exptl_absorpt_empirical_full_min 0.870
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.926(1)
2 0.074(1)

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
