# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mds189_1
_database_code_depnum_ccdc_archive 'CCDC 2364251'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_mds189_1            
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.909 Why?
RESPONSE: Miscommunication problem with the data collection
;
# Added during the CSD deposition process: Thursday 20 June 2024 07:42 PM
# end Validation Reply Form

_chemical_name_systematic        
'guanidinium cyclohexanemonosulfonate 2-bromopropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H9 F O, 2[C6 H11 O3 S], 2[C H6 N3]'
_chemical_formula_sum            'C23 H43 N6 O7 S2 F1'
_chemical_formula_iupac          ?
_chemical_formula_weight         598.73

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   17.2223(4)
_cell_length_b                   7.28010(10)
_cell_length_c                   12.1354(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1521.54(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4842
_cell_measurement_theta_min      3.7220
_cell_measurement_theta_max      74.2590
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_T_max  0.869

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω shutterless scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            8001
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_theta_min         4.46
_diffrn_reflns_theta_max         76.66
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.909
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15

_refine_special_details          SQUEEZE,SQUEEZE

_reflns_number_total             1576
_reflns_number_gt                1446
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1161
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_number_reflns         1576
_refine_ls_number_parameters     73
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.4256P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.362
_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 0.0181 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'

_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.33217(3) 0.250000 0.59388(4) 0.02545(19) Uani d T P S 1 . .
O O1 0.30209(9) 0.250000 0.70684(11) 0.0281(3) Uani d T P S 1 . .
O O2 0.31040(6) 0.08340(14) 0.53381(8) 0.0304(3) Uani d . . . 1 . .
C C1 0.43556(13) 0.250000 0.60313(16) 0.0276(5) Uani d T P S 1 . .
H H1 0.456880 0.250000 0.526479 0.033000 Uiso calc U P R 1 . .
C C009 0.58125(15) 0.250000 0.7305(2) 0.0441(6) Uani d T P S 1 . .
H H00A 0.638709 0.250001 0.732739 0.053000 Uiso calc U P R 1 . .
H H00B 0.561918 0.249999 0.807359 0.053000 Uiso calc U P R 1 . .
N N1 0.74667(9) 0.40785(18) 0.18788(11) 0.0409(4) Uani d . . . 1 . .
H H1A 0.736423 0.512406 0.221230 0.049000 Uiso calc U . R 1 . .
H H1B 0.766356 0.408088 0.120958 0.049000 Uiso calc U . R 1 . .
N N2 0.70282(12) 0.250000 0.33924(15) 0.0336(4) Uani d T P S 1 . .
H H2A 0.692604 0.354679 0.372479 0.040000 Uiso calc U P R 0.5 . .
H H2B 0.693357 0.145321 0.372925 0.040000 Uiso calc U P R 0.5 . .
C C4 0.73247(13) 0.250000 0.23844(19) 0.0323(5) Uani d T P S 1 . .
C C2 0.46446(9) 0.4236(2) 0.66106(13) 0.0348(4) Uani d . . . 1 . .
H H2C 0.448086 0.533072 0.618608 0.042000 Uiso calc U . R 1 . .
H H2D 0.440902 0.431542 0.735318 0.042000 Uiso calc U . R 1 . .
C C3 0.55277(10) 0.4220(3) 0.67151(15) 0.0428(4) Uani d . . . 1 . .
H H3A 0.576251 0.427603 0.597119 0.051000 Uiso calc U . R 1 . .
H H3B 0.569788 0.532030 0.712917 0.051000 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.4639(10) ?
S1 O2 7_565 1.4639(10) ?
S1 O1 . 1.4655(14) ?
S1 C1 . 1.784(2) ?
C1 C2 7_565 1.5295(19) ?
C1 C2 . 1.5295(19) ?
C1 H1 . 1.000000 ?
C009 C3 7_565 1.524(2) ?
C009 C3 . 1.524(2) ?
C009 H00A . 0.990000 ?
C009 H00B . 0.990000 ?
N1 C4 . 1.3255(17) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C4 . 1.326(3) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
C2 C3 . 1.526(2) ?
C2 H2C . 0.990000 ?
C2 H2D . 0.990000 ?
C3 H3A . 0.990000 ?
C3 H3B . 0.990000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O2 . 7_565 111.89(8) ?
O2 S1 O1 . . 112.04(5) ?
O2 S1 O1 7_565 . 112.04(5) ?
O2 S1 C1 . . 106.67(6) ?
O2 S1 C1 7_565 . 106.67(6) ?
O1 S1 C1 . . 107.09(9) ?
C2 C1 C2 7_565 . 111.44(18) ?
C2 C1 S1 7_565 . 110.71(11) ?
C2 C1 S1 . . 110.72(11) ?
C2 C1 H1 7_565 . 107.900000 ?
C2 C1 H1 . . 107.900000 ?
S1 C1 H1 . . 107.900000 ?
C3 C009 C3 7_565 . 110.5(2) ?
C3 C009 H00A 7_565 . 109.500000 ?
C3 C009 H00A . . 109.500000 ?
C3 C009 H00B 7_565 . 109.500000 ?
C3 C009 H00B . . 109.500000 ?
H00A C009 H00B . . 108.100000 ?
C4 N1 H1A . . 120.000000 ?
C4 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C4 N2 H2A . . 120.000000 ?
C4 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
N2 C4 N1 . . 119.89(10) ?
N2 C4 N1 . 7_565 119.89(10) ?
N1 C4 N1 . 7_565 120.2(2) ?
C3 C2 C1 . . 110.87(15) ?
C3 C2 H2C . . 109.500000 ?
C1 C2 H2C . . 109.500000 ?
C3 C2 H2D . . 109.500000 ?
C1 C2 H2D . . 109.500000 ?
H2C C2 H2D . . 108.100000 ?
C009 C3 C2 . . 111.47(16) ?
C009 C3 H3A . . 109.300000 ?
C2 C3 H3A . . 109.300000 ?
C009 C3 H3B . . 109.300000 ?
C2 C3 H3B . . 109.300000 ?
H3A C3 H3B . . 108.000000 ?



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol ethanol'
####################################################################### 
# 
# 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_23mdw6d
_database_code_depnum_ccdc_archive 'CCDC 2364254'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium 1,5-naphthalenedisulfonate 2-fluoropropiophenone'
_chemical_name_common            23mdw6d
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 F N6 O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         558.60

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_H-M_alt        'P n n m'
_space_group_name_Hall           '-P 2 2n'
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                   7.9767(8)
_cell_length_b                   21.0642(19)
_cell_length_c                   7.4827(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1257.3(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2257
_cell_measurement_theta_min      2.7305
_cell_measurement_theta_max      23.2675
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              Incoatec
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12389
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_special_details          
;
;

_reflns_number_total             1206
_reflns_number_gt                986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0843
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2150
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         1206
_refine_ls_number_parameters     140
_refine_ls_number_restraints     66
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²+6.6182P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.773
_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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (Brakdenburg 2014)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 -0.1874(2) 0.35398(8) 1.000000 0.0302(5) Uani d T P S 1 A .
O O1 -0.2858(4) 0.36416(14) 0.8386(5) 0.0374(9) Uani d . . . 1 . .
O O2 -0.1049(6) 0.2923(2) 1.000000 0.0342(12) Uani d T P S 1 . .
N N1 -0.1986(8) 0.3083(3) 0.500000 0.0443(17) Uani d T P S 1 . .
H H1A -0.229993 0.325505 0.601844 0.053000 Uiso calc U P R 0.5 . .
H H1B -0.228518 0.325879 0.398156 0.053000 Uiso calc U P R 0.5 . .
N N2 -0.0620(5) 0.23014(17) 0.6533(6) 0.0333(10) Uani d . . . 1 . .
H H2A -0.093643 0.247435 0.754863 0.040000 Uiso calc U . R 1 . .
H H2B -0.000674 0.195422 0.653711 0.040000 Uiso calc U . R 1 . .
C C1 -0.0276(8) 0.4123(3) 1.000000 0.0277(15) Uani d T P S 1 . .
C C2 0.1335(10) 0.3915(4) 1.0270(19) 0.026(3) Uani d U P . 0.5 A -1
H H2 0.155504 0.347318 1.037317 0.031000 Uiso calc U P R 0.5 A -1
C C3 0.2653(11) 0.4350(4) 1.0395(11) 0.028(3) Uani d U P . 0.5 A -1
H H3 0.376953 0.420216 1.054710 0.034000 Uiso calc U P R 0.5 A -1
C C4 0.2340(10) 0.4988(4) 1.0300(15) 0.025(3) Uani d U P . 0.5 A -1
H H4 0.323979 0.527931 1.043537 0.030000 Uiso calc U P R 0.5 A -1
C C5 0.0689(8) 0.5222(3) 1.000000 0.0265(15) Uani d T P S 1 . .
C C6 -0.1067(9) 0.2563(3) 0.500000 0.0327(16) Uani d T P S 1 . .
O O3 0.486(2) 0.3905(7) 0.544(3) 0.075(7) Uani d U P D 0.25 B -1
F F1 0.177(3) 0.3930(11) 0.450(6) 0.199(16) Uani d U P D 0.25 B -1
C C7 0.5555(19) 0.4995(6) 0.498(4) 0.070(3) Uani d . P DG 0.25 B -1
C C8 0.726(2) 0.4920(6) 0.468(3) 0.070(3) Uani d . P DG 0.25 B -1
H H8 0.771998 0.450690 0.452457 0.084000 Uiso calc U P R 0.25 B -1
C C9 0.8304(17) 0.5448(8) 0.462(3) 0.070(3) Uani d . P DG 0.25 B -1
H H9 0.947190 0.539706 0.441387 0.084000 Uiso calc U P R 0.25 B -1
C C10 0.764(2) 0.6052(6) 0.485(4) 0.070(3) Uani d . P DG 0.25 B -1
H H10 0.834780 0.641364 0.480622 0.084000 Uiso calc U P R 0.25 B -1
C C11 0.593(2) 0.6127(5) 0.515(5) 0.070(3) Uani d . P DG 0.25 B -1
H H11 0.547179 0.654007 0.530926 0.084000 Uiso calc U P R 0.25 B -1
C C12 0.4887(17) 0.5599(8) 0.522(4) 0.070(3) Uani d . P DG 0.25 B -1
H H12 0.371984 0.564991 0.541996 0.084000 Uiso calc U P R 0.25 B -1
C C13 0.444(2) 0.4422(8) 0.497(7) 0.085(8) Uani d U P D 0.25 B -1
C C14 0.263(3) 0.4505(12) 0.438(4) 0.130(18) Uani d U P D 0.25 B -1
H H14 0.254957 0.469439 0.315507 0.156000 Uiso calc U P R 0.25 B -1
C C15 0.181(3) 0.4937(13) 0.582(4) 0.084(9) Uani d U P D 0.25 B -1
H H15A 0.241930 0.534076 0.588847 0.125000 Uiso calc U P R 0.25 B -1
H H15B 0.186092 0.472439 0.698807 0.125000 Uiso calc U P R 0.25 B -1
H H15C 0.063876 0.501795 0.550693 0.125000 Uiso calc U P R 0.25 B -1


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.456(4) ?
S1 O1 6_557 1.456(4) ?
S1 O2 . 1.457(5) ?
S1 C1 . 1.769(7) ?
N1 C6 . 1.318(9) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C6 . 1.321(5) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
C1 C2 . 1.373(10) ?
C1 C5 5_567 1.420(8) ?
C2 C3 . 1.398(11) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.368(11) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.424(10) ?
C4 H4 . 0.950000 ?
C5 C5 5_567 1.442(13) ?
O3 C13 . 1.19(2) ?
F1 C14 . 1.397(19) ?
C7 C8 . 1.390000 ?
C7 C12 . 1.390000 ?
C7 C13 . 1.498(10) ?
C8 C9 . 1.390000 ?
C8 H8 . 0.950000 ?
C9 C10 . 1.390000 ?
C9 H9 . 0.950000 ?
C10 C11 . 1.390000 ?
C10 H10 . 0.950000 ?
C11 C12 . 1.390000 ?
C11 H11 . 0.950000 ?
C12 H12 . 0.950000 ?
C13 C14 . 1.522(10) ?
C14 C15 . 1.558(19) ?
C14 H14 . 1.000000 ?
C15 H15A . 0.980000 ?
C15 H15B . 0.980000 ?
C15 H15C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O1 . 6_557 112.0(3) ?
O1 S1 O2 . . 112.02(17) ?
O1 S1 O2 6_557 . 112.02(17) ?
O1 S1 C1 . . 106.63(18) ?
O1 S1 C1 6_557 . 106.63(18) ?
O2 S1 C1 . . 107.1(3) ?
C6 N1 H1A . . 120.000000 ?
C6 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C6 N2 H2A . . 120.000000 ?
C6 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C2 C1 C5 . 5_567 121.8(6) ?
C2 C1 S1 . . 116.9(5) ?
C5 C1 S1 5_567 . 120.5(5) ?
C1 C2 C3 . . 120.4(7) ?
C1 C2 H2 . . 119.800000 ?
C3 C2 H2 . . 119.800000 ?
C4 C3 C2 . . 120.2(8) ?
C4 C3 H3 . . 119.900000 ?
C2 C3 H3 . . 119.900000 ?
C3 C4 C5 . . 121.1(7) ?
C3 C4 H4 . . 119.400000 ?
C5 C4 H4 . . 119.400000 ?
C1 C5 C4 5_567 . 123.4(6) ?
C1 C5 C5 5_567 5_567 116.9(7) ?
C4 C5 C5 . 5_567 118.8(7) ?
N1 C6 N2 . . 119.8(3) ?
N1 C6 N2 . 6_556 119.8(3) ?
N2 C6 N2 . 6_556 120.4(6) ?
C8 C7 C12 . . 120.000000 ?
C8 C7 C13 . . 119.2(13) ?
C12 C7 C13 . . 120.7(13) ?
C9 C8 C7 . . 120.000000 ?
C9 C8 H8 . . 120.000000 ?
C7 C8 H8 . . 120.000000 ?
C8 C9 C10 . . 120.000000 ?
C8 C9 H9 . . 120.000000 ?
C10 C9 H9 . . 120.000000 ?
C11 C10 C9 . . 120.000000 ?
C11 C10 H10 . . 120.000000 ?
C9 C10 H10 . . 120.000000 ?
C12 C11 C10 . . 120.000000 ?
C12 C11 H11 . . 120.000000 ?
C10 C11 H11 . . 120.000000 ?
C11 C12 C7 . . 120.000000 ?
C11 C12 H12 . . 120.000000 ?
C7 C12 H12 . . 120.000000 ?
O3 C13 C7 . . 124.7(16) ?
O3 C13 C14 . . 117.1(14) ?
C7 C13 C14 . . 118.1(18) ?
F1 C14 C13 . . 110.5(16) ?
F1 C14 C15 . . 104.7(18) ?
C13 C14 C15 . . 105.2(15) ?
F1 C14 H14 . . 112.000000 ?
C13 C14 H14 . . 112.000000 ?
C15 C14 H14 . . 112.000000 ?
C14 C15 H15A . . 109.500000 ?
C14 C15 H15B . . 109.500000 ?
H15A C15 H15B . . 109.500000 ?
C14 C15 H15C . . 109.500000 ?
H15A C15 H15C . . 109.500000 ?
H15B C15 H15C . . 109.500000 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol ethanol'
####################################################################### 
# 
# 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_24mdw38d
_database_code_depnum_ccdc_archive 'CCDC 2364256'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium 1,5-naphthalenedisulfonate 2-chloropropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Cl N6 O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         575.05

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6588(5)
_cell_length_b                   20.9928(11)
_cell_length_c                   8.0310(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.117(4)
_cell_angle_gamma                90
_cell_volume                     1291.22(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5853
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.47
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600

_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              Incoatec
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            12933
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             3239
_reflns_number_gt                2767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.1588
_refine_ls_wR_factor_gt          0.3972
_refine_ls_wR_factor_ref         0.4046
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.131
_refine_ls_number_reflns         3239
_refine_ls_number_parameters     222
_refine_ls_number_restraints     240
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1832P)²+6.9779P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.012
_refine_diff_density_max         1.474
_refine_diff_density_min         -0.936
_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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5000(7) 0.7090(2) 0.4113(7) 0.0510(12) Uani d . . . 1.000000 . .
O O2 0.3437(7) 0.6392(2) 0.2241(6) 0.0499(12) Uani d . . . 1.000000 . .
O O3 0.6573(7) 0.6391(2) 0.2230(6) 0.0484(12) Uani d . . . 1.000000 . .
S S1 0.4996(2) 0.64843(6) 0.3234(2) 0.0434(5) Uani d . . . 1.000000 . .
C C5 0.5003(11) 0.5885(3) 0.4797(8) 0.0482(16) Uani d U . D 1.000000 . .
C C1 0.4999(10) 0.4773(3) 0.5662(7) 0.0461(16) Uani d U . D 1.000000 . .
C C4A 0.541(4) 0.6071(8) 0.6383(16) 0.047(5) Uani d U P D 0.49(3) A 1
H H4A 0.562833 0.650768 0.661907 0.057000 Uiso calc U P R 0.49(3) A 1
C C3A 0.551(4) 0.5615(7) 0.7667(16) 0.046(4) Uani d U P D 0.49(3) A 1
H H3A 0.566269 0.574981 0.878690 0.056000 Uiso calc U P R 0.49(3) A 1
C C2A 0.539(3) 0.4982(7) 0.7312(17) 0.042(4) Uani d U P D 0.49(3) A 1
H H2A 0.556960 0.467728 0.817007 0.051000 Uiso calc U P R 0.49(3) A 1
C C4B 0.462(4) 0.6072(7) 0.6388(16) 0.049(5) Uani d U P D 0.51(3) A 2
H H4B 0.443087 0.650925 0.662573 0.059000 Uiso calc U P R 0.51(3) A 2
C C3B 0.451(4) 0.5617(6) 0.7677(15) 0.049(4) Uani d U P D 0.51(3) A 2
H H3B 0.437269 0.575295 0.879656 0.059000 Uiso calc U P R 0.51(3) A 2
C C2B 0.461(3) 0.4983(7) 0.7318(15) 0.043(4) Uani d U P D 0.51(3) A 2
H H2B 0.442398 0.467839 0.817292 0.052000 Uiso calc U P R 0.51(3) A 2
N N1 0.6503(8) 0.7339(2) 0.9499(7) 0.0444(13) Uani d . . . 1.000000 . .
H H1AN 0.651956 0.698955 1.010287 0.053000 Uiso calc U . R 1.000000 . .
H H1BN 0.749002 0.751921 0.919446 0.053000 Uiso calc U . R 1.000000 . .
N N2 0.3515(8) 0.7334(2) 0.9488(7) 0.0432(13) Uani d . . . 1.000000 . .
H H2AN 0.351631 0.698380 1.009258 0.052000 Uiso calc U . R 1.000000 . .
H H2BN 0.251997 0.750733 0.918153 0.052000 Uiso calc U . R 1.000000 . .
N N3 0.4994(9) 0.8121(3) 0.8110(7) 0.0500(14) Uani d . . . 1.000000 . .
H H3AN 0.399966 0.829194 0.778971 0.060000 Uiso calc U . R 1.000000 . .
H H3BN 0.598965 0.829641 0.781386 0.060000 Uiso calc U . R 1.000000 . .
C C6 0.4993(9) 0.7595(3) 0.9047(7) 0.0397(14) Uani d . . . 1.000000 . .
C C4G 0.987(4) 0.5586(7) 0.0119(12) 0.126(8) Uani d U P DG 0.500000 B -1
H H4G 0.979721 0.559943 0.129929 0.152000 Uiso calc U P R 0.500000 B -1
C C1G 0.987(3) 0.6149(5) -0.0791(14) 0.105(8) Uani d U P G 0.500000 B -1
H H1G 0.979712 0.654734 -0.023370 0.126000 Uiso calc U P R 0.500000 B -1
C C6G 0.999(4) 0.6130(5) -0.2518(14) 0.125(9) Uani d U P G 0.500000 B -1
H H6G 0.998621 0.651471 -0.314020 0.150000 Uiso calc U P R 0.500000 B -1
C C2G 1.010(5) 0.5547(7) -0.3334(13) 0.162(10) Uani d U P G 0.500000 B -1
H H2G 1.017539 0.553417 -0.451372 0.194000 Uiso calc U P R 0.500000 B -1
C C3G 1.010(4) 0.4984(5) -0.242(2) 0.171(10) Uani d U P DG 0.500000 B -1
H H3G 1.017548 0.458625 -0.298076 0.206000 Uiso calc U P R 0.500000 B -1
C C5G 0.999(4) 0.5004(5) -0.070(2) 0.136(8) Uani d U P DG 0.500000 B -1
C C7G 0.991(4) 0.4434(7) 0.042(2) 0.181(7) Uani d U P D 0.500000 B -1
C C8G 1.044(4) 0.4482(9) 0.222(2) 0.181(7) Uani d U P D 0.500000 B -1
H H8G 1.167641 0.463118 0.226349 0.218000 Uiso calc U P R 0.500000 B -1
Cl Cl1 1.038(4) 0.3687(7) 0.287(3) 0.370(16) Uani d U P D 0.500000 B -1
C C9G 0.940(6) 0.4852(12) 0.351(4) 0.181(7) Uani d U P D 0.500000 B -1
H H9GA 0.815316 0.475747 0.337965 0.272000 Uiso calc U P R 0.500000 B -1
H H9GB 0.959486 0.530920 0.335869 0.272000 Uiso calc U P R 0.500000 B -1
H H9GC 0.978151 0.472564 0.462881 0.272000 Uiso calc U P R 0.500000 B -1
O O1G 0.954(5) 0.3918(7) -0.008(3) 0.252(16) Uani d U P D 0.500000 B -1


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 S1 . 1.455(5) ?
O2 S1 . 1.447(5) ?
O3 S1 . 1.467(5) ?
S1 C5 . 1.777(6) ?
C5 C4A . 1.368(14) ?
C5 C4B . 1.368(14) ?
C5 C1 3_666 1.432(8) ?
C1 C1 3_666 1.427(10) ?
C1 C2A . 1.427(14) ?
C1 C2B . 1.432(13) ?
C4A C3A . 1.409(15) ?
C4A H4A . 0.950000 ?
C3A C2A . 1.362(15) ?
C3A H3A . 0.950000 ?
C2A H2A . 0.950000 ?
C4B C3B . 1.410(14) ?
C4B H4B . 0.950000 ?
C3B C2B . 1.364(14) ?
C3B H3B . 0.950000 ?
C2B H2B . 0.950000 ?
N1 C6 . 1.325(9) ?
N1 H1AN . 0.880000 ?
N1 H1BN . 0.880000 ?
N2 C6 . 1.307(8) ?
N2 H2AN . 0.880000 ?
N2 H2BN . 0.880000 ?
N3 C6 . 1.336(7) ?
N3 H3AN . 0.880000 ?
N3 H3BN . 0.880000 ?
C4G C1G . 1.390000 ?
C4G C5G . 1.390000 ?
C4G H4G . 0.950000 ?
C1G C6G . 1.390000 ?
C1G H1G . 0.950000 ?
C6G C2G . 1.390000 ?
C6G H6G . 0.950000 ?
C2G C3G . 1.390000 ?
C2G H2G . 0.950000 ?
C3G C5G . 1.390000 ?
C3G H3G . 0.950000 ?
C5G C7G . 1.495(9) ?
C7G O1G . 1.188(16) ?
C7G C8G . 1.502(10) ?
C8G C9G . 1.523(10) ?
C8G Cl1 . 1.752(17) ?
C8G H8G . 1.000000 ?
C9G H9GA . 0.980000 ?
C9G H9GB . 0.980000 ?
C9G H9GC . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 112.7(3) ?
O2 S1 O3 . . 111.0(3) ?
O1 S1 O3 . . 112.5(3) ?
O2 S1 C5 . . 107.2(3) ?
O1 S1 C5 . . 106.0(3) ?
O3 S1 C5 . . 107.0(3) ?
C4A C5 C1 . 3_666 121.0(8) ?
C4B C5 C1 . 3_666 121.1(8) ?
C4A C5 S1 . . 117.2(8) ?
C4B C5 S1 . . 117.2(7) ?
C1 C5 S1 3_666 . 120.1(5) ?
C1 C1 C2A 3_666 . 119.1(9) ?
C1 C1 C5 3_666 3_666 116.9(7) ?
C2A C1 C5 . 3_666 122.4(8) ?
C1 C1 C2B 3_666 . 119.2(9) ?
C5 C1 C2B 3_666 . 122.4(8) ?
C5 C4A C3A . . 119.9(12) ?
C5 C4A H4A . . 120.000000 ?
C3A C4A H4A . . 120.000000 ?
C2A C3A C4A . . 120.4(12) ?
C2A C3A H3A . . 119.800000 ?
C4A C3A H3A . . 119.800000 ?
C3A C2A C1 . . 120.5(12) ?
C3A C2A H2A . . 119.700000 ?
C1 C2A H2A . . 119.800000 ?
C5 C4B C3B . . 120.4(12) ?
C5 C4B H4B . . 119.800000 ?
C3B C4B H4B . . 119.800000 ?
C2B C3B C4B . . 120.1(11) ?
C2B C3B H3B . . 119.900000 ?
C4B C3B H3B . . 119.900000 ?
C3B C2B C1 . . 120.5(11) ?
C3B C2B H2B . . 119.700000 ?
C1 C2B H2B . . 119.700000 ?
C6 N1 H1AN . . 120.000000 ?
C6 N1 H1BN . . 120.000000 ?
H1AN N1 H1BN . . 120.000000 ?
C6 N2 H2AN . . 120.000000 ?
C6 N2 H2BN . . 120.000000 ?
H2AN N2 H2BN . . 120.000000 ?
C6 N3 H3AN . . 120.000000 ?
C6 N3 H3BN . . 120.000000 ?
H3AN N3 H3BN . . 120.000000 ?
N2 C6 N1 . . 120.8(5) ?
N2 C6 N3 . . 120.1(6) ?
N1 C6 N3 . . 119.1(6) ?
C1G C4G C5G . . 120.000000 ?
C1G C4G H4G . . 120.000000 ?
C5G C4G H4G . . 120.000000 ?
C4G C1G C6G . . 120.000000 ?
C4G C1G H1G . . 120.000000 ?
C6G C1G H1G . . 120.000000 ?
C1G C6G C2G . . 120.000000 ?
C1G C6G H6G . . 120.000000 ?
C2G C6G H6G . . 120.000000 ?
C3G C2G C6G . . 120.000000 ?
C3G C2G H2G . . 120.000000 ?
C6G C2G H2G . . 120.000000 ?
C5G C3G C2G . . 120.000000 ?
C5G C3G H3G . . 120.000000 ?
C2G C3G H3G . . 120.000000 ?
C3G C5G C4G . . 120.000000 ?
C3G C5G C7G . . 125.2(10) ?
C4G C5G C7G . . 114.8(10) ?
O1G C7G C5G . . 122.6(11) ?
O1G C7G C8G . . 116.6(11) ?
C5G C7G C8G . . 120.6(12) ?
C7G C8G C9G . . 124.(2) ?
C7G C8G Cl1 . . 102.5(14) ?
C9G C8G Cl1 . . 105.4(16) ?
C7G C8G H8G . . 108.200000 ?
C9G C8G H8G . . 108.000000 ?
Cl1 C8G H8G . . 108.200000 ?
C8G C9G H9GA . . 109.400000 ?
C8G C9G H9GB . . 109.500000 ?
H9GA C9G H9GB . . 109.500000 ?
C8G C9G H9GC . . 109.600000 ?
H9GA C9G H9GC . . 109.500000 ?
H9GB C9G H9GC . . 109.500000 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol ethanol'
####################################################################### 
# 
# 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_23mdw66d
_database_code_depnum_ccdc_archive 'CCDC 2364255'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            AD-II-143-A1
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Br N6 O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         619.51
_chemical_absolute_configuration rmad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7603(6)
_cell_length_b                   21.0415(17)
_cell_length_c                   7.9327(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.550(4)
_cell_angle_gamma                90
_cell_volume                     1277.37(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9797
_cell_measurement_theta_min      2.6048
_cell_measurement_theta_max      28.4399
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636

_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              Incoatec
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            3339
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_special_details          'Refined as a 2-component inversion twin.,Twin'

_reflns_number_total             3339
_reflns_number_gt                3217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     ?
_reflns_Friedel_fraction_full    ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1269
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_refine_ls_number_reflns         3339
_refine_ls_number_parameters     336
_refine_ls_number_restraints     7
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+2.0625P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.602
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(3)

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Diamond (Brakdenburg 2014)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.19302(8) 0.29445(6) 0.35982(7) 0.02694(16) Uani d . . . 1 . .
O O006 0.1048(5) 0.2176(2) 0.7507(5) 0.0182(8) Uani d . . . 1 . .
C C13 0.2553(7) 0.3798(2) 0.7302(7) 0.0187(10) Uani d . . D 1 . .
H H13 0.314738 0.377109 0.635001 0.022000 Uiso calc U . R 1 . .
C C14 0.2479(7) 0.4373(2) 0.8150(7) 0.0223(11) Uani d . . D 1 . .
H H14 0.302243 0.473852 0.776994 0.027000 Uiso calc U . R 1 . .
C C15 0.1618(8) 0.4417(3) 0.9546(7) 0.0251(12) Uani d . . D 1 . .
H H15 0.158976 0.480943 1.013445 0.030000 Uiso calc U . R 1 . .
C C16 0.0801(8) 0.3885(2) 1.0073(7) 0.0247(12) Uani d . . D 1 . .
H H16 0.019048 0.391492 1.101338 0.030000 Uiso calc U . R 1 . .
C C17 0.0868(7) 0.3305(2) 0.9235(6) 0.0179(10) Uani d . . D 1 . .
H H17 0.031165 0.294130 0.960703 0.021000 Uiso calc U . R 1 . .
C C18 0.1755(6) 0.3261(2) 0.7848(6) 0.0158(10) Uani d . . D 1 . .
C C19 0.1847(6) 0.2621(3) 0.7065(7) 0.0131(9) Uani d . . . 1 . .
C C20 0.3006(7) 0.2518(3) 0.5728(7) 0.0172(10) Uani d . . . 1 . .
H H20 0.416668 0.271868 0.614060 0.021000 Uiso calc U . R 1 . .
C C21 0.3309(5) 0.1788(2) 0.5335(6) 0.0080(8) Uani d . . . 1 . .
H H21A 0.369884 0.156148 0.640975 0.012000 Uiso calc U . R 1 . .
H H21B 0.420245 0.175236 0.460007 0.012000 Uiso calc U . R 1 . .
H H21C 0.221291 0.160180 0.475312 0.012000 Uiso calc U . R 1 . .
S S1 0.69560(16) 0.17048(6) 0.07203(17) 0.0143(2) Uani d . . . 1 . .
S S2 0.67464(15) 0.46736(6) 0.42273(17) 0.0138(2) Uani d . . . 1 . .
O O1 0.8361(5) 0.18162(19) -0.0256(5) 0.0170(8) Uani d . . . 1 . .
O O2 0.5238(5) 0.1768(2) -0.0341(5) 0.0194(8) Uani d . . . 1 . .
O O3 0.7161(5) 0.11016(19) 0.1648(5) 0.0189(8) Uani d . . . 1 . .
O O4 0.6471(5) 0.52731(19) 0.3308(6) 0.0199(8) Uani d . . . 1 . .
O O5 0.8487(5) 0.4635(2) 0.5283(5) 0.0184(8) Uani d . . . 1 . .
O O6 0.5364(5) 0.45392(19) 0.5222(5) 0.0167(7) Uani d . . . 1 . .
C C1 0.7094(6) 0.2304(2) 0.2299(6) 0.0116(9) Uani d . . . 1 . .
C C2 0.7417(7) 0.2128(3) 0.3979(7) 0.0143(10) Uani d . . . 1 . .
H H2 0.757834 0.169205 0.427081 0.017000 Uiso calc U . R 1 . .
C C3 0.7513(7) 0.2584(3) 0.5275(7) 0.0146(10) Uani d . . . 1 . .
H H3 0.774421 0.245379 0.643765 0.018000 Uiso calc U . R 1 . .
C C4 0.7277(7) 0.3216(3) 0.4884(7) 0.0134(9) Uani d . . . 1 . .
H H4 0.733629 0.352007 0.577710 0.016000 Uiso calc U . R 1 . .
C C5 0.6942(6) 0.3420(2) 0.3138(7) 0.0114(9) Uani d . . . 1 . .
C C6 0.6689(6) 0.4068(2) 0.2660(7) 0.0128(9) Uani d . . . 1 . .
C C7 0.6429(7) 0.4250(3) 0.0980(7) 0.0172(10) Uani d . . . 1 . .
H H7 0.627487 0.468707 0.069131 0.021000 Uiso calc U . R 1 . .
C C8 0.6389(7) 0.3799(3) -0.0301(7) 0.0188(11) Uani d . . . 1 . .
H H8 0.622920 0.393164 -0.146167 0.023000 Uiso calc U . R 1 . .
C C9 0.6576(7) 0.3163(3) 0.0083(7) 0.0159(10) Uani d . . . 1 . .
H H9 0.651485 0.285943 -0.081143 0.019000 Uiso calc U . R 1 . .
C C10 0.6864(5) 0.2956(3) 0.1827(6) 0.0102(8) Uani d . . . 1 . .
N N1 0.7975(6) 0.6405(2) 0.9299(6) 0.0167(9) Uani d . . . 1 . .
H H1A 0.899325 0.659560 0.955825 0.020000 Uiso calc U . R 1 . .
H H1B 0.705114 0.656309 0.966036 0.020000 Uiso calc U . R 1 . .
N N2 0.6285(6) 0.5589(2) 0.7988(6) 0.0190(9) Uani d . . . 1 . .
H H2A 0.618661 0.523819 0.737534 0.023000 Uiso calc U . R 1 . .
H H2B 0.536517 0.574871 0.835110 0.023000 Uiso calc U . R 1 . .
N N3 0.9208(6) 0.5635(2) 0.7814(7) 0.0191(9) Uani d . . . 1 . .
H H3A 1.023213 0.582283 0.806659 0.023000 Uiso calc U . R 1 . .
H H3B 0.909990 0.528618 0.719543 0.023000 Uiso calc U . R 1 . .
C C11 0.7831(7) 0.5879(3) 0.8366(7) 0.0142(9) Uani d . . . 1 . .
N N4 0.1711(6) 0.4956(2) 0.4056(7) 0.0175(9) Uani d . . . 1 . .
H H4A 0.274201 0.477138 0.424898 0.021000 Uiso calc U . R 1 . .
H H4B 0.078639 0.475516 0.429318 0.021000 Uiso calc U . R 1 . .
N N5 -0.0002(6) 0.5822(2) 0.3107(7) 0.0206(10) Uani d . . . 1 . .
H H5A -0.010397 0.620769 0.267472 0.025000 Uiso calc U . R 1 . .
H H5B -0.092934 0.562193 0.334312 0.025000 Uiso calc U . R 1 . .
N N6 0.2941(6) 0.5846(2) 0.3045(6) 0.0174(9) Uani d . . . 1 . .
H H6A 0.283114 0.623148 0.261247 0.021000 Uiso calc U . R 1 . .
H H6B 0.397322 0.566181 0.323898 0.021000 Uiso calc U . R 1 . .
C C12 0.1550(7) 0.5541(3) 0.3404(6) 0.0146(9) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C20 . 1.973(6) ?
O006 C19 . 1.207(7) ?
C13 C14 . 1.390(4) ?
C13 C18 . 1.390(4) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.388(5) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.386(5) ?
C15 H15 . 0.950000 ?
C16 C17 . 1.394(4) ?
C16 H16 . 0.950000 ?
C17 C18 . 1.394(4) ?
C17 H17 . 0.950000 ?
C18 C19 . 1.490(7) ?
C19 C20 . 1.515(7) ?
C20 C21 . 1.591(7) ?
C20 H20 . 1.000000 ?
C21 H21A . 0.980000 ?
C21 H21B . 0.980000 ?
C21 H21C . 0.980000 ?
S1 O1 . 1.457(4) ?
S1 O2 . 1.460(4) ?
S1 O3 . 1.463(4) ?
S1 C1 . 1.767(5) ?
S2 O4 . 1.455(4) ?
S2 O6 . 1.461(4) ?
S2 O5 . 1.469(4) ?
S2 C6 . 1.777(5) ?
C1 C2 . 1.366(7) ?
C1 C10 . 1.425(7) ?
C2 C3 . 1.398(7) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.371(7) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.433(7) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.419(7) ?
C5 C10 . 1.421(7) ?
C6 C7 . 1.369(8) ?
C7 C8 . 1.387(8) ?
C7 H7 . 0.950000 ?
C8 C9 . 1.376(8) ?
C8 H8 . 0.950000 ?
C9 C10 . 1.432(7) ?
C9 H9 . 0.950000 ?
N1 C11 . 1.326(7) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C11 . 1.334(7) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
N3 C11 . 1.323(7) ?
N3 H3A . 0.880000 ?
N3 H3B . 0.880000 ?
N4 C12 . 1.333(7) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C12 . 1.327(7) ?
N5 H5A . 0.880000 ?
N5 H5B . 0.880000 ?
N6 C12 . 1.326(7) ?
N6 H6A . 0.880000 ?
N6 H6B . 0.880000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 C13 C18 . . 120.0(5) ?
C14 C13 H13 . . 120.000000 ?
C18 C13 H13 . . 120.000000 ?
C15 C14 C13 . . 120.5(5) ?
C15 C14 H14 . . 119.700000 ?
C13 C14 H14 . . 119.700000 ?
C16 C15 C14 . . 119.4(5) ?
C16 C15 H15 . . 120.300000 ?
C14 C15 H15 . . 120.300000 ?
C15 C16 C17 . . 120.5(5) ?
C15 C16 H16 . . 119.700000 ?
C17 C16 H16 . . 119.700000 ?
C18 C17 C16 . . 119.8(5) ?
C18 C17 H17 . . 120.100000 ?
C16 C17 H17 . . 120.100000 ?
C13 C18 C17 . . 119.7(5) ?
C13 C18 C19 . . 123.3(4) ?
C17 C18 C19 . . 116.9(4) ?
O006 C19 C18 . . 121.2(5) ?
O006 C19 C20 . . 119.0(5) ?
C18 C19 C20 . . 119.8(4) ?
C19 C20 C21 . . 113.6(4) ?
C19 C20 Br1 . . 108.5(4) ?
C21 C20 Br1 . . 109.1(3) ?
C19 C20 H20 . . 108.500000 ?
C21 C20 H20 . . 108.500000 ?
Br1 C20 H20 . . 108.500000 ?
C20 C21 H21A . . 109.500000 ?
C20 C21 H21B . . 109.500000 ?
H21A C21 H21B . . 109.500000 ?
C20 C21 H21C . . 109.500000 ?
H21A C21 H21C . . 109.500000 ?
H21B C21 H21C . . 109.500000 ?
O1 S1 O2 . . 111.8(2) ?
O1 S1 O3 . . 112.2(2) ?
O2 S1 O3 . . 112.4(2) ?
O1 S1 C1 . . 107.4(2) ?
O2 S1 C1 . . 106.6(2) ?
O3 S1 C1 . . 105.9(2) ?
O4 S2 O6 . . 112.2(2) ?
O4 S2 O5 . . 112.2(3) ?
O6 S2 O5 . . 111.7(2) ?
O4 S2 C6 . . 106.7(2) ?
O6 S2 C6 . . 107.7(2) ?
O5 S2 C6 . . 105.9(2) ?
C2 C1 C10 . . 120.7(5) ?
C2 C1 S1 . . 118.6(4) ?
C10 C1 S1 . . 120.7(4) ?
C1 C2 C3 . . 120.7(5) ?
C1 C2 H2 . . 119.600000 ?
C3 C2 H2 . . 119.600000 ?
C4 C3 C2 . . 120.6(5) ?
C4 C3 H3 . . 119.700000 ?
C2 C3 H3 . . 119.700000 ?
C3 C4 C5 . . 120.4(5) ?
C3 C4 H4 . . 119.800000 ?
C5 C4 H4 . . 119.800000 ?
C6 C5 C10 . . 118.5(5) ?
C6 C5 C4 . . 122.8(5) ?
C10 C5 C4 . . 118.7(5) ?
C7 C6 C5 . . 121.4(5) ?
C7 C6 S2 . . 117.5(4) ?
C5 C6 S2 . . 121.0(4) ?
C6 C7 C8 . . 120.2(5) ?
C6 C7 H7 . . 119.900000 ?
C8 C7 H7 . . 119.900000 ?
C9 C8 C7 . . 121.0(5) ?
C9 C8 H8 . . 119.500000 ?
C7 C8 H8 . . 119.500000 ?
C8 C9 C10 . . 120.3(5) ?
C8 C9 H9 . . 119.900000 ?
C10 C9 H9 . . 119.900000 ?
C5 C10 C1 . . 118.8(4) ?
C5 C10 C9 . . 118.6(5) ?
C1 C10 C9 . . 122.6(5) ?
C11 N1 H1A . . 120.000000 ?
C11 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C11 N2 H2A . . 120.000000 ?
C11 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C11 N3 H3A . . 120.000000 ?
C11 N3 H3B . . 120.000000 ?
H3A N3 H3B . . 120.000000 ?
N3 C11 N1 . . 120.7(5) ?
N3 C11 N2 . . 119.6(5) ?
N1 C11 N2 . . 119.7(5) ?
C12 N4 H4A . . 120.000000 ?
C12 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C12 N5 H5A . . 120.000000 ?
C12 N5 H5B . . 120.000000 ?
H5A N5 H5B . . 120.000000 ?
C12 N6 H6A . . 120.000000 ?
C12 N6 H6B . . 120.000000 ?
H6A N6 H6B . . 120.000000 ?
N6 C12 N5 . . 119.6(5) ?
N6 C12 N4 . . 120.1(5) ?
N5 C12 N4 . . 120.2(5) ?

####################################################################### 
# 
# 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_23mdw94d_Hunter
_database_code_depnum_ccdc_archive 'CCDC 2364252'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-09-13 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium cyclohexanemonosulfonate 2-bromopropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H9 Br O, 4(C6 H11 O3 S), 4(C H6 N3)'
_chemical_formula_sum            'C37 H77 Br N12 O13 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         1106.25
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   17.4620(7)
_cell_length_b                   8.6851(3)
_cell_length_c                   19.0810(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.365(2)
_cell_angle_gamma                90
_cell_volume                     2855.24(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      4.70
_cell_measurement_theta_max      74.45
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.29
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172

_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_T_max  0.7538

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            64513
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         74.80
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             11250
_reflns_number_gt                9625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_max     0.922
_reflns_Friedel_fraction_full    0.943

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.1263
_refine_ls_wR_factor_gt          0.3445
_refine_ls_wR_factor_ref         0.3666
_refine_ls_goodness_of_fit_ref   1.588
_refine_ls_restrained_S_all      1.593
_refine_ls_number_reflns         11250
_refine_ls_number_parameters     593
_refine_ls_number_restraints     101
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.075
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.316
_refine_diff_density_min         -1.497
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3586 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(4)

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S3 0.70619(14) 0.3029(3) 0.28507(11) 0.0447(6) Uani d . . . 1 . .
O O7 0.6870(5) 0.3315(10) 0.3558(3) 0.0508(17) Uani d . . . 1 . .
O O8 0.6388(4) 0.3224(10) 0.2287(4) 0.0474(16) Uani d . . . 1 . .
O O9 0.7715(4) 0.3951(10) 0.2703(3) 0.0523(18) Uani d . . . 1 . .
C C13 0.7341(6) 0.1059(15) 0.2825(5) 0.050(2) Uani d . . . 1 . .
H H13 0.691224 0.041405 0.295724 0.061000 Uiso calc U . R 1 . .
C C14 0.8078(8) 0.0766(17) 0.3375(6) 0.060(3) Uani d . . . 1 . .
H H14A 0.797890 0.102503 0.385743 0.072000 Uiso calc U . R 1 . .
H H14B 0.850881 0.142040 0.326801 0.072000 Uiso calc U . R 1 . .
C C15 0.8301(9) -0.0959(19) 0.3341(7) 0.070(4) Uani d . . . 1 . .
H H15A 0.878671 -0.114977 0.367631 0.084000 Uiso calc U . R 1 . .
H H15B 0.788719 -0.159722 0.349173 0.084000 Uiso calc U . R 1 . .
C C16 0.8410(11) -0.142(2) 0.2626(8) 0.080(4) Uani d . . . 1 . .
H H16A 0.854761 -0.252982 0.262900 0.096000 Uiso calc U . R 1 . .
H H16B 0.884630 -0.083298 0.248639 0.096000 Uiso calc U . R 1 . .
C C17 0.7678(11) -0.1149(18) 0.2080(8) 0.074(4) Uani d . . . 1 . .
H H17A 0.724434 -0.177133 0.220426 0.089000 Uiso calc U . R 1 . .
H H17B 0.777061 -0.146639 0.160288 0.089000 Uiso calc U . R 1 . .
C C18 0.7464(8) 0.0590(16) 0.2075(6) 0.060(3) Uani d . . . 1 . .
H H18A 0.788648 0.121082 0.192881 0.072000 Uiso calc U . R 1 . .
H H18B 0.698344 0.077736 0.173151 0.072000 Uiso calc U . R 1 . .
S S1 0.42056(16) 1.2361(3) 0.53354(12) 0.0445(6) Uani d . . . 1 . .
O O1 0.3620(5) 1.2887(9) 0.4754(4) 0.0465(16) Uani d . . . 1 . .
O O2 0.4983(5) 1.2678(10) 0.5227(4) 0.0523(18) Uani d . . . 1 . .
O O3 0.4062(5) 1.2946(10) 0.6020(4) 0.0510(18) Uani d . . . 1 . .
C C1 0.4107(13) 1.0330(18) 0.5376(9) 0.086(5) Uani d . . . 1 . .
H H1 0.357531 1.015978 0.549197 0.103000 Uiso calc U . R 1 . .
C C2 0.4103(13) 0.951(2) 0.4665(11) 0.089(5) Uani d . . . 1 . .
H H2A 0.368244 0.992131 0.430223 0.107000 Uiso calc U . R 1 . .
H H2B 0.460437 0.966461 0.449626 0.107000 Uiso calc U . R 1 . .
C C3 0.3972(16) 0.782(3) 0.479(2) 0.142(13) Uani d . . . 1 . .
H H3A 0.345105 0.769691 0.492270 0.170000 Uiso calc U . R 1 . .
H H3B 0.396992 0.726580 0.433564 0.170000 Uiso calc U . R 1 . .
C C4 0.454(2) 0.708(2) 0.5335(18) 0.128(10) Uani d . . . 1 . .
H H4A 0.506734 0.720909 0.521801 0.153000 Uiso calc U . R 1 . .
H H4B 0.442849 0.595982 0.534624 0.153000 Uiso calc U . R 1 . .
C C5 0.4502(16) 0.780(2) 0.6082(16) 0.114(8) Uani d . . . 1 . .
H H5A 0.489505 0.731964 0.644904 0.137000 Uiso calc U . R 1 . .
H H5B 0.398253 0.763579 0.621327 0.137000 Uiso calc U . R 1 . .
C C6 0.4674(15) 0.962(2) 0.6024(10) 0.100(6) Uani d . . . 1 . .
H H6A 0.459683 1.014707 0.646860 0.119000 Uiso calc U . R 1 . .
H H6B 0.521851 0.978355 0.595759 0.119000 Uiso calc U . R 1 . .
S S2 0.07485(13) 0.7251(3) 0.40117(11) 0.0432(6) Uani d . . . 1 . .
O O4 0.0076(4) 0.6926(9) 0.3472(4) 0.0463(16) Uani d . . . 1 . .
O O5 0.1443(5) 0.6361(10) 0.3891(4) 0.0520(17) Uani d . . . 1 . .
O O6 0.0574(4) 0.7041(9) 0.4733(4) 0.0475(17) Uani d . . . 1 . .
C C7 0.0954(6) 0.9256(15) 0.3933(6) 0.049(2) Uani d . . . 1 . .
H H7 0.048769 0.985769 0.401370 0.059000 Uiso calc U . R 1 . .
C C8 0.1124(8) 0.9632(17) 0.3181(6) 0.063(3) Uani d . . . 1 . .
H H8A 0.157280 0.901714 0.308396 0.076000 Uiso calc U . R 1 . .
H H8B 0.066894 0.935844 0.282199 0.076000 Uiso calc U . R 1 . .
C C9 0.1299(10) 1.131(2) 0.3129(8) 0.077(4) Uani d . . . 1 . .
H H9C 0.143439 1.152363 0.265439 0.093000 Uiso calc U . R 1 . .
H H9D 0.082634 1.190903 0.317248 0.093000 Uiso calc U . R 1 . .
C C10 0.1930(12) 1.182(2) 0.3669(10) 0.083(4) Uani d . . . 1 . .
H H10A 0.198084 1.295723 0.363918 0.100000 Uiso calc U . R 1 . .
H H10B 0.242154 1.135772 0.357908 0.100000 Uiso calc U . R 1 . .
C C11 0.1789(9) 1.1370(18) 0.4446(8) 0.069(3) Uani d . . . 1 . .
H H11A 0.225518 1.163283 0.479401 0.083000 Uiso calc U . R 1 . .
H H11B 0.134656 1.196952 0.456774 0.083000 Uiso calc U . R 1 . .
C C12 0.1622(7) 0.9690(17) 0.4494(7) 0.062(3) Uani d . . . 1 . .
H H12A 0.149465 0.945051 0.496932 0.074000 Uiso calc U . R 1 . .
H H12B 0.208647 0.908731 0.443013 0.074000 Uiso calc U . R 1 . .
S S4 0.77934(15) 0.7108(3) 0.63924(12) 0.0467(6) Uani d . . . 1 . .
O O10 0.7692(4) 0.6843(10) 0.7129(3) 0.0476(17) Uani d . . . 1 . .
O O11 0.7395(6) 0.5914(13) 0.5911(4) 0.067(2) Uani d . . . 1 . .
O O12 0.8600(5) 0.7234(10) 0.6314(4) 0.0531(18) Uani d . . . 1 . .
C C19 0.7302(10) 0.8832(18) 0.6099(8) 0.072(4) Uani d . . . 1 . .
H H19 0.675452 0.872637 0.618366 0.086000 Uiso calc U . R 1 . .
C C20 0.7630(13) 1.013(3) 0.6494(9) 0.089(5) Uani d . . . 1 . .
H H20A 0.817514 1.027564 0.642523 0.107000 Uiso calc U . R 1 . .
H H20B 0.762456 0.996780 0.700675 0.107000 Uiso calc U . R 1 . .
C C21 0.7152(15) 1.158(2) 0.6240(12) 0.100(6) Uani d . . . 1 . .
H H21A 0.661094 1.145249 0.632174 0.121000 Uiso calc U . R 1 . .
H H21B 0.737532 1.249107 0.651481 0.121000 Uiso calc U . R 1 . .
C C22 0.7160(15) 1.185(2) 0.5451(11) 0.093(6) Uani d . . . 1 . .
H H22A 0.686007 1.279184 0.529314 0.111000 Uiso calc U . R 1 . .
H H22B 0.770085 1.200668 0.537009 0.111000 Uiso calc U . R 1 . .
C C23 0.6808(12) 1.048(3) 0.5026(9) 0.090(5) Uani d . . . 1 . .
H H23A 0.682233 1.064141 0.451515 0.108000 Uiso calc U . R 1 . .
H H23B 0.626014 1.034829 0.508903 0.108000 Uiso calc U . R 1 . .
C C24 0.7276(12) 0.904(2) 0.5289(8) 0.082(5) Uani d . . . 1 . .
H H24A 0.781066 0.913872 0.518477 0.098000 Uiso calc U . R 1 . .
H H24B 0.703460 0.812365 0.503542 0.098000 Uiso calc U . R 1 . .
N N7 0.2825(6) 0.4829(12) 0.6319(4) 0.052(2) Uani d . . . 1 . .
H H7A 0.276232 0.505392 0.675578 0.063000 Uiso calc U . R 1 . .
H H7B 0.321559 0.424573 0.624426 0.063000 Uiso calc U . R 1 . .
N N8 0.1744(6) 0.6239(11) 0.5876(4) 0.049(2) Uani d . . . 1 . .
H H8C 0.167495 0.647312 0.631022 0.059000 Uiso calc U . R 1 . .
H H8D 0.142044 0.658881 0.550910 0.059000 Uiso calc U . R 1 . .
N N9 0.2421(5) 0.5007(11) 0.5117(4) 0.0463(19) Uani d . . . 1 . .
H H9A 0.280768 0.441221 0.504286 0.056000 Uiso calc U . R 1 . .
H H9B 0.209247 0.536496 0.475477 0.056000 Uiso calc U . R 1 . .
C C27 0.2333(6) 0.5365(12) 0.5777(5) 0.045(2) Uani d . . . 1 . .
N N10 0.8798(6) 0.5198(12) 0.3860(4) 0.051(2) Uani d . . . 1 . .
H H10C 0.925507 0.549786 0.377355 0.061000 Uiso calc U . R 1 . .
H H10D 0.849608 0.463182 0.354639 0.061000 Uiso calc U . R 1 . .
N N11 0.9010(6) 0.6449(13) 0.4940(4) 0.052(2) Uani d . . . 1 . .
H H11C 0.885519 0.671173 0.533944 0.062000 Uiso calc U . R 1 . .
H H11D 0.946662 0.675176 0.485346 0.062000 Uiso calc U . R 1 . .
N N12 0.7875(6) 0.5139(12) 0.4590(4) 0.050(2) Uani d . . . 1 . .
H H12C 0.771264 0.539326 0.498750 0.061000 Uiso calc U . R 1 . .
H H12D 0.758001 0.457392 0.427157 0.061000 Uiso calc U . R 1 . .
C C28 0.8560(6) 0.5605(12) 0.4472(4) 0.043(2) Uani d . . . 1 . .
N N4 0.5986(6) 0.4695(11) 0.6257(4) 0.0487(19) Uani d . . . 1 . .
H H4C 0.561564 0.441783 0.591058 0.058000 Uiso calc U . R 1 . .
H H4D 0.639487 0.519417 0.616137 0.058000 Uiso calc U . R 1 . .
N N5 0.6480(6) 0.4795(13) 0.7444(5) 0.054(2) Uani d . . . 1 . .
H H5C 0.644592 0.459167 0.788945 0.065000 Uiso calc U . R 1 . .
H H5D 0.688612 0.529372 0.734019 0.065000 Uiso calc U . R 1 . .
N N6 0.5329(6) 0.3627(14) 0.7077(5) 0.056(2) Uani d . . . 1 . .
H H6C 0.528886 0.341732 0.752059 0.067000 Uiso calc U . R 1 . .
H H6D 0.496076 0.333798 0.673077 0.067000 Uiso calc U . R 1 . .
C C26 0.5926(7) 0.4356(13) 0.6934(5) 0.048(2) Uani d . . . 1 . .
C C25 0.4671(7) 0.2998(16) 0.3212(5) 0.055(3) Uani d . . . 1 . .
N N1 0.4816(6) 0.3086(14) 0.2545(5) 0.056(2) Uani d . . . 1 . .
H H1A 0.529847 0.312025 0.246540 0.067000 Uiso calc U . R 1 . .
H H1B 0.442954 0.310870 0.218610 0.067000 Uiso calc U . R 1 . .
N N2 0.5248(6) 0.2963(15) 0.3754(5) 0.061(3) Uani d . . . 1 . .
H H2C 0.573131 0.299687 0.367764 0.073000 Uiso calc U . R 1 . .
H H2D 0.514917 0.290485 0.419097 0.073000 Uiso calc U . R 1 . .
N N3 0.3932(6) 0.2935(15) 0.3321(5) 0.062(3) Uani d . . . 1 . .
H H3C 0.382781 0.286997 0.375654 0.075000 Uiso calc U . R 1 . .
H H3D 0.355057 0.295914 0.295777 0.075000 Uiso calc U . R 1 . .
O O13 0.5593(14) 0.970(2) 0.2580(15) 0.177(9) Uani d U . D 1 . .
C C29 0.5335(11) 0.6906(13) 0.1207(11) 0.143(8) Uani d U . G 1 . .
H H29 0.553774 0.603306 0.147490 0.172000 Uiso calc U . R 1 . .
C C30 0.5126(13) 0.6793(16) 0.0474(11) 0.146(8) Uani d U . G 1 . .
H H30 0.518463 0.584383 0.024128 0.175000 Uiso calc U . R 1 . .
C C31 0.4829(12) 0.807(2) 0.0081(9) 0.152(8) Uani d U . G 1 . .
H H31 0.468614 0.799339 -0.041949 0.182000 Uiso calc U . R 1 . .
C C32 0.4743(12) 0.9460(18) 0.0422(10) 0.155(9) Uani d U . G 1 . .
H H32 0.454076 1.033219 0.015335 0.186000 Uiso calc U . R 1 . .
C C33 0.4953(12) 0.9572(13) 0.1154(11) 0.143(8) Uani d U . G 1 . .
H H33 0.489387 1.052145 0.138697 0.172000 Uiso calc U . R 1 . .
C C34 0.5249(10) 0.8295(16) 0.1547(9) 0.119(5) Uani d U . DG 1 . .
C C35 0.5438(14) 0.848(2) 0.2348(13) 0.145(7) Uani d U . D 1 . .
C C36 0.5311(15) 0.720(4) 0.287(2) 0.189(10) Uani d U . D 1 . .
H H36 0.551211 0.624261 0.267336 0.227000 Uiso calc U . R 1 . .
C C37 0.584(2) 0.746(4) 0.3587(17) 0.149(7) Uani d U . D 1 . .
H H37A 0.637397 0.714710 0.354727 0.224000 Uiso calc U . R 1 . .
H H37B 0.565695 0.684938 0.395613 0.224000 Uiso calc U . R 1 . .
H H37C 0.583967 0.855516 0.371246 0.224000 Uiso calc U . R 1 . .
Br Br1 0.4180(5) 0.6917(8) 0.2748(6) 0.247(4) Uani d U . D 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S3 O9 . 1.457(7) ?
S3 O7 . 1.463(6) ?
S3 O8 . 1.468(7) ?
S3 C13 . 1.783(13) ?
C13 C18 . 1.536(14) ?
C13 C14 . 1.545(16) ?
C13 H13 . 1.000000 ?
C14 C15 . 1.55(2) ?
C14 H14A . 0.990000 ?
C14 H14B . 0.990000 ?
C15 C16 . 1.464(19) ?
C15 H15A . 0.990000 ?
C15 H15B . 0.990000 ?
C16 C17 . 1.53(2) ?
C16 H16A . 0.990000 ?
C16 H16B . 0.990000 ?
C17 C18 . 1.556(19) ?
C17 H17A . 0.990000 ?
C17 H17B . 0.990000 ?
C18 H18A . 0.990000 ?
C18 H18B . 0.990000 ?
S1 O2 . 1.433(9) ?
S1 O1 . 1.455(8) ?
S1 O3 . 1.461(7) ?
S1 C1 . 1.776(16) ?
C1 C2 . 1.53(3) ?
C1 C6 . 1.58(3) ?
C1 H1 . 1.000000 ?
C2 C3 . 1.51(3) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 C4 . 1.46(4) ?
C3 H3A . 0.990000 ?
C3 H3B . 0.990000 ?
C4 C5 . 1.57(4) ?
C4 H4A . 0.990000 ?
C4 H4B . 0.990000 ?
C5 C6 . 1.62(3) ?
C5 H5A . 0.990000 ?
C5 H5B . 0.990000 ?
C6 H6A . 0.990000 ?
C6 H6B . 0.990000 ?
S2 O4 . 1.457(8) ?
S2 O6 . 1.469(7) ?
S2 O5 . 1.488(8) ?
S2 C7 . 1.789(13) ?
C7 C12 . 1.498(15) ?
C7 C8 . 1.547(15) ?
C7 H7 . 1.000000 ?
C8 C9 . 1.50(2) ?
C8 H8A . 0.990000 ?
C8 H8B . 0.990000 ?
C9 C10 . 1.45(3) ?
C9 H9C . 0.990000 ?
C9 H9D . 0.990000 ?
C10 C11 . 1.59(2) ?
C10 H10A . 0.990000 ?
C10 H10B . 0.990000 ?
C11 C12 . 1.49(2) ?
C11 H11A . 0.990000 ?
C11 H11B . 0.990000 ?
C12 H12A . 0.990000 ?
C12 H12B . 0.990000 ?
S4 O12 . 1.445(9) ?
S4 O10 . 1.463(6) ?
S4 O11 . 1.482(10) ?
S4 C19 . 1.770(14) ?
C19 C20 . 1.43(3) ?
C19 C24 . 1.549(19) ?
C19 H19 . 1.000000 ?
C20 C21 . 1.54(3) ?
C20 H20A . 0.990000 ?
C20 H20B . 0.990000 ?
C21 C22 . 1.52(3) ?
C21 H21A . 0.990000 ?
C21 H21B . 0.990000 ?
C22 C23 . 1.52(3) ?
C22 H22A . 0.990000 ?
C22 H22B . 0.990000 ?
C23 C24 . 1.53(3) ?
C23 H23A . 0.990000 ?
C23 H23B . 0.990000 ?
C24 H24A . 0.990000 ?
C24 H24B . 0.990000 ?
N7 C27 . 1.318(14) ?
N7 H7A . 0.880000 ?
N7 H7B . 0.880000 ?
N8 C27 . 1.315(14) ?
N8 H8C . 0.880000 ?
N8 H8D . 0.880000 ?
N9 C27 . 1.329(12) ?
N9 H9A . 0.880000 ?
N9 H9B . 0.880000 ?
N10 C28 . 1.349(12) ?
N10 H10C . 0.880000 ?
N10 H10D . 0.880000 ?
N11 C28 . 1.312(14) ?
N11 H11C . 0.880000 ?
N11 H11D . 0.880000 ?
N12 C28 . 1.317(14) ?
N12 H12C . 0.880000 ?
N12 H12D . 0.880000 ?
N4 C26 . 1.345(13) ?
N4 H4C . 0.880000 ?
N4 H4D . 0.880000 ?
N5 C26 . 1.312(15) ?
N5 H5C . 0.880000 ?
N5 H5D . 0.880000 ?
N6 C26 . 1.286(16) ?
N6 H6C . 0.880000 ?
N6 H6D . 0.880000 ?
C25 N2 . 1.321(15) ?
C25 N1 . 1.341(13) ?
C25 N3 . 1.341(16) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 H2C . 0.880000 ?
N2 H2D . 0.880000 ?
N3 H3C . 0.880000 ?
N3 H3D . 0.880000 ?
O13 C35 . 1.16(2) ?
C29 C30 . 1.390000 ?
C29 C34 . 1.390000 ?
C29 H29 . 0.950000 ?
C30 C31 . 1.390000 ?
C30 H30 . 0.950000 ?
C31 C32 . 1.390000 ?
C31 H31 . 0.950000 ?
C32 C33 . 1.390000 ?
C32 H32 . 0.950000 ?
C33 C34 . 1.390000 ?
C33 H33 . 0.950000 ?
C34 C35 . 1.52(2) ?
C35 C36 . 1.54(3) ?
C36 C37 . 1.54(3) ?
C36 Br1 . 1.96(2) ?
C36 H36 . 1.000000 ?
C37 H37A . 0.980000 ?
C37 H37B . 0.980000 ?
C37 H37C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O9 S3 O7 . . 112.9(4) ?
O9 S3 O8 . . 110.7(4) ?
O7 S3 O8 . . 112.3(4) ?
O9 S3 C13 . . 107.2(5) ?
O7 S3 C13 . . 107.1(5) ?
O8 S3 C13 . . 106.2(5) ?
C18 C13 C14 . . 111.3(10) ?
C18 C13 S3 . . 111.2(8) ?
C14 C13 S3 . . 109.9(9) ?
C18 C13 H13 . . 108.100000 ?
C14 C13 H13 . . 108.100000 ?
S3 C13 H13 . . 108.100000 ?
C13 C14 C15 . . 108.5(11) ?
C13 C14 H14A . . 110.000000 ?
C15 C14 H14A . . 110.000000 ?
C13 C14 H14B . . 110.000000 ?
C15 C14 H14B . . 110.000000 ?
H14A C14 H14B . . 108.400000 ?
C16 C15 C14 . . 112.1(12) ?
C16 C15 H15A . . 109.200000 ?
C14 C15 H15A . . 109.200000 ?
C16 C15 H15B . . 109.200000 ?
C14 C15 H15B . . 109.200000 ?
H15A C15 H15B . . 107.900000 ?
C15 C16 C17 . . 111.7(13) ?
C15 C16 H16A . . 109.300000 ?
C17 C16 H16A . . 109.300000 ?
C15 C16 H16B . . 109.300000 ?
C17 C16 H16B . . 109.300000 ?
H16A C16 H16B . . 107.900000 ?
C16 C17 C18 . . 109.2(13) ?
C16 C17 H17A . . 109.800000 ?
C18 C17 H17A . . 109.800000 ?
C16 C17 H17B . . 109.800000 ?
C18 C17 H17B . . 109.800000 ?
H17A C17 H17B . . 108.300000 ?
C13 C18 C17 . . 108.7(10) ?
C13 C18 H18A . . 109.900000 ?
C17 C18 H18A . . 109.900000 ?
C13 C18 H18B . . 109.900000 ?
C17 C18 H18B . . 109.900000 ?
H18A C18 H18B . . 108.300000 ?
O2 S1 O1 . . 113.2(5) ?
O2 S1 O3 . . 111.5(5) ?
O1 S1 O3 . . 111.8(5) ?
O2 S1 C1 . . 107.3(8) ?
O1 S1 C1 . . 106.5(8) ?
O3 S1 C1 . . 105.9(6) ?
C2 C1 C6 . . 115.2(14) ?
C2 C1 S1 . . 114.2(11) ?
C6 C1 S1 . . 111.6(16) ?
C2 C1 H1 . . 104.800000 ?
C6 C1 H1 . . 104.800000 ?
S1 C1 H1 . . 104.800000 ?
C3 C2 C1 . . 107.(2) ?
C3 C2 H2A . . 110.300000 ?
C1 C2 H2A . . 110.300000 ?
C3 C2 H2B . . 110.300000 ?
C1 C2 H2B . . 110.300000 ?
H2A C2 H2B . . 108.600000 ?
C4 C3 C2 . . 116.(2) ?
C4 C3 H3A . . 108.300000 ?
C2 C3 H3A . . 108.300000 ?
C4 C3 H3B . . 108.300000 ?
C2 C3 H3B . . 108.300000 ?
H3A C3 H3B . . 107.400000 ?
C3 C4 C5 . . 110.(2) ?
C3 C4 H4A . . 109.600000 ?
C5 C4 H4A . . 109.600000 ?
C3 C4 H4B . . 109.600000 ?
C5 C4 H4B . . 109.600000 ?
H4A C4 H4B . . 108.100000 ?
C4 C5 C6 . . 107.2(19) ?
C4 C5 H5A . . 110.300000 ?
C6 C5 H5A . . 110.300000 ?
C4 C5 H5B . . 110.300000 ?
C6 C5 H5B . . 110.300000 ?
H5A C5 H5B . . 108.500000 ?
C1 C6 C5 . . 110.(2) ?
C1 C6 H6A . . 109.800000 ?
C5 C6 H6A . . 109.800000 ?
C1 C6 H6B . . 109.800000 ?
C5 C6 H6B . . 109.800000 ?
H6A C6 H6B . . 108.200000 ?
O4 S2 O6 . . 111.8(4) ?
O4 S2 O5 . . 111.9(5) ?
O6 S2 O5 . . 112.3(4) ?
O4 S2 C7 . . 106.2(5) ?
O6 S2 C7 . . 105.9(5) ?
O5 S2 C7 . . 108.3(5) ?
C12 C7 C8 . . 111.4(10) ?
C12 C7 S2 . . 109.2(9) ?
C8 C7 S2 . . 110.8(9) ?
C12 C7 H7 . . 108.500000 ?
C8 C7 H7 . . 108.500000 ?
S2 C7 H7 . . 108.500000 ?
C9 C8 C7 . . 109.8(12) ?
C9 C8 H8A . . 109.700000 ?
C7 C8 H8A . . 109.700000 ?
C9 C8 H8B . . 109.700000 ?
C7 C8 H8B . . 109.700000 ?
H8A C8 H8B . . 108.200000 ?
C10 C9 C8 . . 113.1(14) ?
C10 C9 H9C . . 109.000000 ?
C8 C9 H9C . . 109.000000 ?
C10 C9 H9D . . 109.000000 ?
C8 C9 H9D . . 109.000000 ?
H9C C9 H9D . . 107.800000 ?
C9 C10 C11 . . 111.8(13) ?
C9 C10 H10A . . 109.300000 ?
C11 C10 H10A . . 109.300000 ?
C9 C10 H10B . . 109.300000 ?
C11 C10 H10B . . 109.300000 ?
H10A C10 H10B . . 107.900000 ?
C12 C11 C10 . . 111.2(12) ?
C12 C11 H11A . . 109.400000 ?
C10 C11 H11A . . 109.400000 ?
C12 C11 H11B . . 109.400000 ?
C10 C11 H11B . . 109.400000 ?
H11A C11 H11B . . 108.000000 ?
C11 C12 C7 . . 109.8(12) ?
C11 C12 H12A . . 109.700000 ?
C7 C12 H12A . . 109.700000 ?
C11 C12 H12B . . 109.700000 ?
C7 C12 H12B . . 109.700000 ?
H12A C12 H12B . . 108.200000 ?
O12 S4 O10 . . 112.6(4) ?
O12 S4 O11 . . 110.8(5) ?
O10 S4 O11 . . 111.6(5) ?
O12 S4 C19 . . 109.5(7) ?
O10 S4 C19 . . 108.0(6) ?
O11 S4 C19 . . 103.9(8) ?
C20 C19 C24 . . 112.3(14) ?
C20 C19 S4 . . 111.8(13) ?
C24 C19 S4 . . 110.5(10) ?
C20 C19 H19 . . 107.400000 ?
C24 C19 H19 . . 107.300000 ?
S4 C19 H19 . . 107.400000 ?
C19 C20 C21 . . 109.3(17) ?
C19 C20 H20A . . 109.800000 ?
C21 C20 H20A . . 109.800000 ?
C19 C20 H20B . . 109.800000 ?
C21 C20 H20B . . 109.800000 ?
H20A C20 H20B . . 108.300000 ?
C22 C21 C20 . . 110.1(16) ?
C22 C21 H21A . . 109.600000 ?
C20 C21 H21A . . 109.600000 ?
C22 C21 H21B . . 109.600000 ?
C20 C21 H21B . . 109.600000 ?
H21A C21 H21B . . 108.200000 ?
C23 C22 C21 . . 109.9(15) ?
C23 C22 H22A . . 109.700000 ?
C21 C22 H22A . . 109.700000 ?
C23 C22 H22B . . 109.700000 ?
C21 C22 H22B . . 109.700000 ?
H22A C22 H22B . . 108.200000 ?
C22 C23 C24 . . 108.6(17) ?
C22 C23 H23A . . 110.000000 ?
C24 C23 H23A . . 110.000000 ?
C22 C23 H23B . . 110.000000 ?
C24 C23 H23B . . 110.000000 ?
H23A C23 H23B . . 108.400000 ?
C23 C24 C19 . . 110.5(12) ?
C23 C24 H24A . . 109.500000 ?
C19 C24 H24A . . 109.500000 ?
C23 C24 H24B . . 109.600000 ?
C19 C24 H24B . . 109.600000 ?
H24A C24 H24B . . 108.100000 ?
C27 N7 H7A . . 120.000000 ?
C27 N7 H7B . . 120.000000 ?
H7A N7 H7B . . 120.000000 ?
C27 N8 H8C . . 120.000000 ?
C27 N8 H8D . . 120.000000 ?
H8C N8 H8D . . 120.000000 ?
C27 N9 H9A . . 120.000000 ?
C27 N9 H9B . . 120.000000 ?
H9A N9 H9B . . 120.000000 ?
N7 C27 N8 . . 121.0(9) ?
N7 C27 N9 . . 120.0(9) ?
N8 C27 N9 . . 119.0(9) ?
C28 N10 H10C . . 120.000000 ?
C28 N10 H10D . . 120.000000 ?
H10C N10 H10D . . 120.000000 ?
C28 N11 H11C . . 120.000000 ?
C28 N11 H11D . . 120.000000 ?
H11C N11 H11D . . 120.000000 ?
C28 N12 H12C . . 120.000000 ?
C28 N12 H12D . . 120.000000 ?
H12C N12 H12D . . 120.000000 ?
N11 C28 N12 . . 121.0(8) ?
N11 C28 N10 . . 120.1(9) ?
N12 C28 N10 . . 118.9(9) ?
C26 N4 H4C . . 120.000000 ?
C26 N4 H4D . . 120.000000 ?
H4C N4 H4D . . 120.000000 ?
C26 N5 H5C . . 120.000000 ?
C26 N5 H5D . . 120.000000 ?
H5C N5 H5D . . 120.000000 ?
C26 N6 H6C . . 120.000000 ?
C26 N6 H6D . . 120.000000 ?
H6C N6 H6D . . 120.000000 ?
N6 C26 N5 . . 120.8(9) ?
N6 C26 N4 . . 120.2(10) ?
N5 C26 N4 . . 119.0(11) ?
N2 C25 N1 . . 120.4(11) ?
N2 C25 N3 . . 120.6(9) ?
N1 C25 N3 . . 119.0(10) ?
C25 N1 H1A . . 120.000000 ?
C25 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C25 N2 H2C . . 120.000000 ?
C25 N2 H2D . . 120.000000 ?
H2C N2 H2D . . 120.000000 ?
C25 N3 H3C . . 120.000000 ?
C25 N3 H3D . . 120.000000 ?
H3C N3 H3D . . 120.000000 ?
C30 C29 C34 . . 120.000000 ?
C30 C29 H29 . . 120.000000 ?
C34 C29 H29 . . 120.000000 ?
C31 C30 C29 . . 120.000000 ?
C31 C30 H30 . . 120.000000 ?
C29 C30 H30 . . 120.000000 ?
C30 C31 C32 . . 120.000000 ?
C30 C31 H31 . . 120.000000 ?
C32 C31 H31 . . 120.000000 ?
C33 C32 C31 . . 120.000000 ?
C33 C32 H32 . . 120.000000 ?
C31 C32 H32 . . 120.000000 ?
C32 C33 C34 . . 120.000000 ?
C32 C33 H33 . . 120.000000 ?
C34 C33 H33 . . 120.000000 ?
C33 C34 C29 . . 120.000000 ?
C33 C34 C35 . . 117.2(13) ?
C29 C34 C35 . . 122.8(13) ?
O13 C35 C34 . . 119.(2) ?
O13 C35 C36 . . 117.(3) ?
C34 C35 C36 . . 123.(2) ?
C37 C36 C35 . . 110.(2) ?
C37 C36 Br1 . . 125.(3) ?
C35 C36 Br1 . . 105.1(17) ?
C37 C36 H36 . . 105.000000 ?
C35 C36 H36 . . 105.000000 ?
Br1 C36 H36 . . 105.000000 ?
C36 C37 H37A . . 109.500000 ?
C36 C37 H37B . . 109.500000 ?
H37A C37 H37B . . 109.500000 ?
C36 C37 H37C . . 109.500000 ?
H37A C37 H37C . . 109.500000 ?
H37B C37 H37C . . 109.500000 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol, ethanol'
####################################################################### 
# 
# 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_23mdw65d
_database_code_depnum_ccdc_archive 'CCDC 2364258'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium 4,4?-biphenyldisulfonate 2-fluoropropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 F N6 O7 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         584.64

_chemical_melting_point          ?

_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                   7.3252(5)
_cell_length_b                   12.7523(9)
_cell_length_c                   30.161(2)
_cell_angle_alpha                96.337(4)
_cell_angle_beta                 94.485(4)
_cell_angle_gamma                93.536(4)
_cell_volume                     2784.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.31
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224

_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   Incoatec
_diffrn_source_type              'microfocus sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       " 'three-circle diffractometer'"
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            50789
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40

_refine_special_details          
;
;

_reflns_number_total             13848
_reflns_number_gt                9939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.1468
_refine_ls_wR_factor_gt          0.2969
_refine_ls_wR_factor_ref         0.3125
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.141
_refine_ls_number_reflns         13848
_refine_ls_number_parameters     669
_refine_ls_number_restraints     249
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+33.4676P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.887
_refine_diff_density_min         -0.928
_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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C44 0.3728(9) 0.5618(10) 0.6956(3) 0.111(7) Uani d U . D 1 . .
H H44A 0.390379 0.637862 0.705452 0.167000 Uiso calc U . R 1 . .
H H44B 0.341822 0.523992 0.720831 0.167000 Uiso calc U . R 1 . .
H H44C 0.272843 0.548662 0.671638 0.167000 Uiso calc U . R 1 . .
C C43 0.5469(11) 0.5234(9) 0.6783(4) 0.122(3) Uani d U . D 1 . .
H H43 0.570068 0.458692 0.693192 0.147000 Uiso calc U . R 1 . .
F F1 0.522(2) 0.4905(17) 0.6356(5) 0.274(10) Uani d U . D 1 . .
O O13 0.7835(14) 0.6539(8) 0.6750(4) 0.139(4) Uani d U . D 1 . .
C C41 0.6964(9) 0.6063(7) 0.6992(3) 0.122(3) Uani d U . D 1 . .
C C35 0.7835(17) 0.6394(11) 0.8424(3) 0.169(8) Uani d U . G 1 . .
H H35 0.804879 0.644530 0.874048 0.203000 Uiso calc U . R 1 . .
C C36 0.8773(13) 0.7098(9) 0.8187(4) 0.158(7) Uani d U . G 1 . .
H H36 0.962864 0.763033 0.834138 0.190000 Uiso calc U . R 1 . .
C C37 0.8461(11) 0.7023(8) 0.7723(4) 0.129(5) Uani d U . DG 1 . .
H H37 0.910193 0.750456 0.756143 0.155000 Uiso calc U . R 1 . .
C C38 0.7209(11) 0.6245(8) 0.7497(3) 0.122(3) Uani d U . DG 1 . .
C C39 0.6271(11) 0.5541(7) 0.7734(3) 0.129(5) Uani d U . DG 1 . .
H H39 0.541551 0.500872 0.757965 0.154000 Uiso calc U . R 1 . .
C C40 0.6584(16) 0.5616(9) 0.8198(3) 0.159(7) Uani d U . G 1 . .
H H40 0.594219 0.513447 0.835961 0.191000 Uiso calc U . R 1 . .
C C46 0.0679(12) 0.0352(10) 0.8126(4) 0.161(6) Uani d U . D 1 . .
H H46 0.106706 -0.035962 0.801285 0.193000 Uiso calc U . R 1 . .
C C45 -0.1130(13) 0.0561(14) 0.7895(5) 0.146(9) Uani d U . D 1 . .
H H45A -0.091734 0.099181 0.765185 0.220000 Uiso calc U . R 1 . .
H H45B -0.186204 0.093979 0.811049 0.220000 Uiso calc U . R 1 . .
H H45C -0.179148 -0.011242 0.777176 0.220000 Uiso calc U . R 1 . .
O O14 0.2966(15) 0.1720(8) 0.8329(3) 0.121(4) Uani d U . D 1 . .
C C42 0.2033(11) 0.1234(9) 0.8019(3) 0.113(4) Uani d U . D 1 . .
F F2 0.042(2) 0.0409(18) 0.8571(4) 0.271(10) Uani d U . D 1 . .
C C29 0.1727(17) 0.0503(9) 0.6765(3) 0.152(7) Uani d U . G 1 . .
H H29 0.115113 -0.004266 0.655043 0.182000 Uiso calc U . R 1 . .
C C30 0.1443(12) 0.0503(6) 0.7215(4) 0.124(5) Uani d U . DG 1 . .
H H30 0.067346 -0.004298 0.730852 0.149000 Uiso calc U . R 1 . .
C C31 0.2286(11) 0.1302(7) 0.7529(2) 0.102(4) Uani d U . DG 1 . .
C C32 0.3413(12) 0.2101(7) 0.7392(3) 0.125(5) Uani d U . DG 1 . .
H H32 0.398896 0.264744 0.760617 0.150000 Uiso calc U . R 1 . .
C C33 0.3697(14) 0.2102(10) 0.6942(4) 0.146(6) Uani d U . G 1 . .
H H33 0.446664 0.264778 0.684809 0.175000 Uiso calc U . R 1 . .
C C34 0.2854(17) 0.1303(11) 0.6628(3) 0.153(7) Uani d U . G 1 . .
H H34 0.304775 0.130274 0.632021 0.184000 Uiso calc U . R 1 . .
S S1 0.42572(19) 0.81798(11) 0.57374(5) 0.0152(3) Uani d . . . 1 . .
S S2 0.4844(2) 0.87824(11) 0.92784(5) 0.0164(3) Uani d . . . 1 . .
O O1 0.5927(5) 0.8734(3) 0.56257(14) 0.0158(8) Uani d . . . 1 . .
O O2 0.2580(6) 0.8657(3) 0.55803(15) 0.0184(9) Uani d . . . 1 . .
O O3 0.4175(6) 0.7045(3) 0.55950(14) 0.0180(9) Uani d . . . 1 . .
O O4 0.6588(6) 0.9390(3) 0.94279(14) 0.0196(9) Uani d . . . 1 . .
O O5 0.3259(6) 0.9341(3) 0.94218(15) 0.0223(9) Uani d . . . 1 . .
O O6 0.4797(6) 0.7699(3) 0.93983(15) 0.0196(9) Uani d . . . 1 . .
C C1 0.4302(9) 0.8304(5) 0.6323(2) 0.0216(13) Uani d . . . 1 . .
C C2 0.2860(9) 0.7850(6) 0.6531(2) 0.0273(14) Uani d . . . 1 . .
H H2 0.183827 0.748458 0.635335 0.033000 Uiso calc U . R 1 . .
C C3 0.2908(9) 0.7926(6) 0.6987(2) 0.0273(14) Uani d . . . 1 . .
H H3 0.193203 0.759384 0.712227 0.033000 Uiso calc U . R 1 . .
C C4 0.4354(9) 0.8481(5) 0.7259(2) 0.0240(13) Uani d . . . 1 . .
C C5 0.5783(9) 0.8945(5) 0.7051(2) 0.0216(13) Uani d . . . 1 . .
H H5 0.679174 0.931887 0.722982 0.026000 Uiso calc U . R 1 . .
C C6 0.5764(8) 0.8872(5) 0.6588(2) 0.0211(12) Uani d . . . 1 . .
H H6 0.673648 0.920518 0.645267 0.025000 Uiso calc U . R 1 . .
C C7 0.4401(9) 0.8556(5) 0.7751(2) 0.0216(13) Uani d . . . 1 . .
C C8 0.3727(10) 0.7709(5) 0.7965(2) 0.0253(14) Uani d . . . 1 . .
H H8 0.317816 0.708383 0.779234 0.030000 Uiso calc U . R 1 . .
C C9 0.3864(9) 0.7786(5) 0.8427(2) 0.0212(12) Uani d . . . 1 . .
H H9 0.339345 0.721110 0.856958 0.025000 Uiso calc U . R 1 . .
C C10 0.4668(9) 0.8682(5) 0.8688(2) 0.0193(12) Uani d . . . 1 . .
C C11 0.5359(9) 0.9541(5) 0.8482(2) 0.0216(13) Uani d . . . 1 . .
H H11 0.590998 1.016168 0.865711 0.026000 Uiso calc U . R 1 . .
C C12 0.5219(9) 0.9466(5) 0.8011(2) 0.0203(12) Uani d . . . 1 . .
H H12 0.568697 1.004038 0.786834 0.024000 Uiso calc U . R 1 . .
S S3 0.92990(19) 0.31483(11) 0.57127(5) 0.0145(3) Uani d . . . 1 . .
S S4 0.9903(2) 0.38234(11) 0.92570(5) 0.0154(3) Uani d . . . 1 . .
O O7 1.0992(5) 0.3718(3) 0.56085(14) 0.0175(9) Uani d . . . 1 . .
O O8 0.7662(6) 0.3643(3) 0.55552(14) 0.0184(9) Uani d . . . 1 . .
O O9 0.9218(6) 0.2019(3) 0.55603(15) 0.0182(9) Uani d . . . 1 . .
O O10 0.8300(6) 0.4367(3) 0.93931(15) 0.0203(9) Uani d . . . 1 . .
O O11 1.1626(6) 0.4418(3) 0.94268(15) 0.0185(9) Uani d . . . 1 . .
O O12 0.9847(6) 0.2731(3) 0.93597(14) 0.0175(9) Uani d . . . 1 . .
C C13 0.9342(8) 0.3272(5) 0.63053(19) 0.0153(11) Uani d . . . 1 . .
C C14 0.8623(8) 0.2451(5) 0.6520(2) 0.0191(12) Uani d . . . 1 . .
H H14 0.811276 0.181453 0.634976 0.023000 Uiso calc U . R 1 . .
C C15 0.8650(9) 0.2564(5) 0.6984(2) 0.0245(14) Uani d . . . 1 . .
H H15 0.814446 0.200495 0.713044 0.029000 Uiso calc U . R 1 . .
C C16 0.9413(8) 0.3490(5) 0.7235(2) 0.0202(13) Uani d . . . 1 . .
C C17 1.0106(8) 0.4309(5) 0.7012(2) 0.0186(12) Uani d . . . 1 . .
H H17 1.061156 0.494946 0.717929 0.022000 Uiso calc U . R 1 . .
C C18 1.0068(8) 0.4201(5) 0.6553(2) 0.0185(12) Uani d . . . 1 . .
H H18 1.054240 0.476686 0.640547 0.022000 Uiso calc U . R 1 . .
C C19 0.9544(9) 0.3595(5) 0.7733(2) 0.0209(13) Uani d . . . 1 . .
C C20 0.8174(9) 0.3090(6) 0.7956(2) 0.0270(14) Uani d . . . 1 . .
H H20 0.717668 0.268382 0.778543 0.032000 Uiso calc U . R 1 . .
C C21 0.8263(10) 0.3178(6) 0.8419(2) 0.0285(15) Uani d . . . 1 . .
H H21 0.731443 0.285762 0.856719 0.034000 Uiso calc U . R 1 . .
C C22 0.9770(8) 0.3747(5) 0.8665(2) 0.0182(12) Uani d . . . 1 . .
C C23 1.1113(9) 0.4244(5) 0.8452(2) 0.0219(13) Uani d . . . 1 . .
H H23 1.212567 0.463768 0.862235 0.026000 Uiso calc U . R 1 . .
C C24 1.0984(9) 0.4170(5) 0.7991(2) 0.0232(13) Uani d . . . 1 . .
H H24 1.190955 0.452265 0.784674 0.028000 Uiso calc U . R 1 . .
N N1 0.9073(7) 0.7467(4) 0.54769(17) 0.0180(10) Uani d . . . 1 . .
H H1A 0.804649 0.779127 0.547418 0.022000 Uiso calc U . R 1 . .
H H1B 1.013635 0.783769 0.549710 0.022000 Uiso calc U . R 1 . .
N N2 1.0562(7) 0.5925(4) 0.54645(18) 0.0191(10) Uani d . . . 1 . .
H H2A 1.163107 0.629091 0.549166 0.023000 Uiso calc U . R 1 . .
H H2B 1.051379 0.523029 0.544676 0.023000 Uiso calc U . R 1 . .
N N3 0.7416(7) 0.5862(4) 0.54199(19) 0.0211(11) Uani d . . . 1 . .
H H3A 0.638891 0.618544 0.541716 0.025000 Uiso calc U . R 1 . .
H H3B 0.738170 0.516792 0.540231 0.025000 Uiso calc U . R 1 . .
C C25 0.9018(8) 0.6422(4) 0.54504(19) 0.0150(11) Uani d . . . 1 . .
N N4 0.4116(7) 0.2460(4) 0.54350(18) 0.0190(10) Uani d . . . 1 . .
H H4A 0.309306 0.278816 0.543110 0.023000 Uiso calc U . R 1 . .
H H4B 0.518069 0.282513 0.544495 0.023000 Uiso calc U . R 1 . .
N N5 0.5598(7) 0.0916(4) 0.54394(18) 0.0180(10) Uani d . . . 1 . .
H H5A 0.666626 0.127971 0.545429 0.022000 Uiso calc U . R 1 . .
H H5B 0.554995 0.022377 0.543331 0.022000 Uiso calc U . R 1 . .
N N6 0.2445(7) 0.0857(4) 0.5411(2) 0.0235(12) Uani d . . . 1 . .
H H6A 0.141824 0.118139 0.540695 0.028000 Uiso calc U . R 1 . .
H H6B 0.241031 0.016502 0.540499 0.028000 Uiso calc U . R 1 . .
C C26 0.4052(8) 0.1415(4) 0.54260(19) 0.0144(11) Uani d . . . 1 . .
N N7 0.4888(7) 0.3225(4) 0.95178(19) 0.0218(11) Uani d . . . 1 . .
H H7A 0.594756 0.357813 0.950295 0.026000 Uiso calc U . R 1 . .
H H7B 0.387353 0.355948 0.952352 0.026000 Uiso calc U . R 1 . .
N N8 0.6339(7) 0.1687(4) 0.95232(18) 0.0197(11) Uani d . . . 1 . .
H H8A 0.630530 0.099887 0.953182 0.024000 Uiso calc U . R 1 . .
H H8B 0.739360 0.204654 0.950870 0.024000 Uiso calc U . R 1 . .
N N9 0.3227(7) 0.1650(4) 0.95535(19) 0.0220(11) Uani d . . . 1 . .
H H9A 0.317820 0.096143 0.956229 0.026000 Uiso calc U . R 1 . .
H H9B 0.221510 0.198684 0.955914 0.026000 Uiso calc U . R 1 . .
C C27 0.4819(8) 0.2177(5) 0.9532(2) 0.0178(12) Uani d . . . 1 . .
N N10 1.1321(7) 0.6704(4) 0.95724(18) 0.0194(11) Uani d . . . 1 . .
H H10A 1.129103 0.601240 0.956858 0.023000 Uiso calc U . R 1 . .
H H10B 1.237737 0.707182 0.957069 0.023000 Uiso calc U . R 1 . .
N N11 0.8170(7) 0.6650(4) 0.95833(18) 0.0205(11) Uani d . . . 1 . .
H H11A 0.714425 0.697452 0.958187 0.025000 Uiso calc U . R 1 . .
H H11B 0.813887 0.596007 0.958648 0.025000 Uiso calc U . R 1 . .
N N12 0.9839(7) 0.8238(4) 0.95760(19) 0.0220(11) Uani d . . . 1 . .
H H12A 0.882493 0.857340 0.957450 0.026000 Uiso calc U . R 1 . .
H H12B 1.090741 0.859225 0.957434 0.026000 Uiso calc U . R 1 . .
C C28 0.9758(8) 0.7199(5) 0.95808(19) 0.0162(11) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C44 C43 . 1.504(5) ?
C44 H44A . 0.980000 ?
C44 H44B . 0.980000 ?
C44 H44C . 0.980000 ?
C43 F1 . 1.304(13) ?
C43 C41 . 1.522(5) ?
C43 H43 . 1.000000 ?
O13 C41 . 1.197(5) ?
C41 C38 . 1.509(5) ?
C35 C36 . 1.390000 ?
C35 C40 . 1.390000 ?
C35 H35 . 0.950000 ?
C36 C37 . 1.390000 ?
C36 H36 . 0.950000 ?
C37 C38 . 1.390000 ?
C37 H37 . 0.950000 ?
C38 C39 . 1.390000 ?
C39 C40 . 1.390000 ?
C39 H39 . 0.950000 ?
C40 H40 . 0.950000 ?
C46 F2 . 1.365(5) ?
C46 C45 . 1.501(5) ?
C46 C42 . 1.531(5) ?
C46 H46 . 1.000000 ?
C45 H45A . 0.980000 ?
C45 H45B . 0.980000 ?
C45 H45C . 0.980000 ?
O14 C42 . 1.201(5) ?
C42 C31 . 1.518(5) ?
C29 C30 . 1.390000 ?
C29 C34 . 1.390000 ?
C29 H29 . 0.950000 ?
C30 C31 . 1.390000 ?
C30 H30 . 0.950000 ?
C31 C32 . 1.390000 ?
C32 C33 . 1.390000 ?
C32 H32 . 0.950000 ?
C33 C34 . 1.390000 ?
C33 H33 . 0.950000 ?
C34 H34 . 0.950000 ?
S1 O1 . 1.456(4) ?
S1 O3 . 1.460(4) ?
S1 O2 . 1.472(4) ?
S1 C1 . 1.754(7) ?
S2 O4 . 1.465(5) ?
S2 O6 . 1.465(4) ?
S2 O5 . 1.468(4) ?
S2 C10 . 1.765(6) ?
C1 C6 . 1.397(9) ?
C1 C2 . 1.397(9) ?
C2 C3 . 1.367(9) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.392(9) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.396(9) ?
C4 C7 . 1.473(9) ?
C5 C6 . 1.387(9) ?
C5 H5 . 0.950000 ?
C6 H6 . 0.950000 ?
C7 C12 . 1.400(9) ?
C7 C8 . 1.402(9) ?
C8 C9 . 1.384(9) ?
C8 H8 . 0.950000 ?
C9 C10 . 1.384(9) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.406(8) ?
C11 C12 . 1.407(8) ?
C11 H11 . 0.950000 ?
C12 H12 . 0.950000 ?
S3 O9 . 1.459(4) ?
S3 O8 . 1.460(4) ?
S3 O7 . 1.471(4) ?
S3 C13 . 1.775(6) ?
S4 O11 . 1.458(4) ?
S4 O12 . 1.460(4) ?
S4 O10 . 1.464(4) ?
S4 C22 . 1.772(6) ?
C13 C18 . 1.382(8) ?
C13 C14 . 1.388(8) ?
C14 C15 . 1.390(9) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.392(9) ?
C15 H15 . 0.950000 ?
C16 C17 . 1.395(9) ?
C16 C19 . 1.486(9) ?
C17 C18 . 1.374(8) ?
C17 H17 . 0.950000 ?
C18 H18 . 0.950000 ?
C19 C24 . 1.380(9) ?
C19 C20 . 1.413(9) ?
C20 C21 . 1.386(10) ?
C20 H20 . 0.950000 ?
C21 C22 . 1.396(9) ?
C21 H21 . 0.950000 ?
C22 C23 . 1.376(9) ?
C23 C24 . 1.380(9) ?
C23 H23 . 0.950000 ?
C24 H24 . 0.950000 ?
N1 C25 . 1.324(7) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C25 . 1.330(7) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
N3 C25 . 1.326(8) ?
N3 H3A . 0.880000 ?
N3 H3B . 0.880000 ?
N4 C26 . 1.328(7) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C26 . 1.333(7) ?
N5 H5A . 0.880000 ?
N5 H5B . 0.880000 ?
N6 C26 . 1.332(8) ?
N6 H6A . 0.880000 ?
N6 H6B . 0.880000 ?
N7 C27 . 1.339(8) ?
N7 H7A . 0.880000 ?
N7 H7B . 0.880000 ?
N8 C27 . 1.311(7) ?
N8 H8A . 0.880000 ?
N8 H8B . 0.880000 ?
N9 C27 . 1.320(8) ?
N9 H9A . 0.880000 ?
N9 H9B . 0.880000 ?
N10 C28 . 1.342(7) ?
N10 H10A . 0.880000 ?
N10 H10B . 0.880000 ?
N11 C28 . 1.321(8) ?
N11 H11A . 0.880000 ?
N11 H11B . 0.880000 ?
N12 C28 . 1.324(8) ?
N12 H12A . 0.880000 ?
N12 H12B . 0.880000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C43 C44 H44A . . 109.500000 ?
C43 C44 H44B . . 109.500000 ?
H44A C44 H44B . . 109.500000 ?
C43 C44 H44C . . 109.500000 ?
H44A C44 H44C . . 109.500000 ?
H44B C44 H44C . . 109.500000 ?
F1 C43 C44 . . 110.7(10) ?
F1 C43 C41 . . 124.4(13) ?
C44 C43 C41 . . 104.6(4) ?
F1 C43 H43 . . 105.200000 ?
C44 C43 H43 . . 105.200000 ?
C41 C43 H43 . . 105.200000 ?
O13 C41 C38 . . 124.5(7) ?
O13 C41 C43 . . 118.5(8) ?
C38 C41 C43 . . 117.0(5) ?
C36 C35 C40 . . 120.000000 ?
C36 C35 H35 . . 120.000000 ?
C40 C35 H35 . . 120.000000 ?
C37 C36 C35 . . 120.000000 ?
C37 C36 H36 . . 120.000000 ?
C35 C36 H36 . . 120.000000 ?
C36 C37 C38 . . 120.000000 ?
C36 C37 H37 . . 120.000000 ?
C38 C37 H37 . . 120.000000 ?
C37 C38 C39 . . 120.000000 ?
C37 C38 C41 . . 121.8(6) ?
C39 C38 C41 . . 117.9(6) ?
C40 C39 C38 . . 120.000000 ?
C40 C39 H39 . . 120.000000 ?
C38 C39 H39 . . 120.000000 ?
C39 C40 C35 . . 120.000000 ?
C39 C40 H40 . . 120.000000 ?
C35 C40 H40 . . 120.000000 ?
F2 C46 C45 . . 105.9(5) ?
F2 C46 C42 . . 112.6(13) ?
C45 C46 C42 . . 105.1(4) ?
F2 C46 H46 . . 111.000000 ?
C45 C46 H46 . . 111.000000 ?
C42 C46 H46 . . 111.000000 ?
C46 C45 H45A . . 109.500000 ?
C46 C45 H45B . . 109.500000 ?
H45A C45 H45B . . 109.500000 ?
C46 C45 H45C . . 109.500000 ?
H45A C45 H45C . . 109.500000 ?
H45B C45 H45C . . 109.500000 ?
O14 C42 C31 . . 125.3(7) ?
O14 C42 C46 . . 117.2(8) ?
C31 C42 C46 . . 116.8(5) ?
C30 C29 C34 . . 120.000000 ?
C30 C29 H29 . . 120.000000 ?
C34 C29 H29 . . 120.000000 ?
C29 C30 C31 . . 120.000000 ?
C29 C30 H30 . . 120.000000 ?
C31 C30 H30 . . 120.000000 ?
C30 C31 C32 . . 120.000000 ?
C30 C31 C42 . . 118.2(6) ?
C32 C31 C42 . . 121.7(6) ?
C33 C32 C31 . . 120.000000 ?
C33 C32 H32 . . 120.000000 ?
C31 C32 H32 . . 120.000000 ?
C32 C33 C34 . . 120.000000 ?
C32 C33 H33 . . 120.000000 ?
C34 C33 H33 . . 120.000000 ?
C33 C34 C29 . . 120.000000 ?
C33 C34 H34 . . 120.000000 ?
C29 C34 H34 . . 120.000000 ?
O1 S1 O3 . . 112.7(2) ?
O1 S1 O2 . . 112.8(2) ?
O3 S1 O2 . . 111.9(3) ?
O1 S1 C1 . . 107.2(3) ?
O3 S1 C1 . . 105.6(3) ?
O2 S1 C1 . . 106.0(3) ?
O4 S2 O6 . . 112.9(3) ?
O4 S2 O5 . . 112.2(3) ?
O6 S2 O5 . . 112.2(3) ?
O4 S2 C10 . . 105.9(3) ?
O6 S2 C10 . . 106.6(3) ?
O5 S2 C10 . . 106.3(3) ?
C6 C1 C2 . . 119.2(6) ?
C6 C1 S1 . . 120.5(5) ?
C2 C1 S1 . . 120.3(5) ?
C3 C2 C1 . . 120.5(6) ?
C3 C2 H2 . . 119.800000 ?
C1 C2 H2 . . 119.800000 ?
C2 C3 C4 . . 121.5(6) ?
C2 C3 H3 . . 119.200000 ?
C4 C3 H3 . . 119.200000 ?
C3 C4 C5 . . 117.8(6) ?
C3 C4 C7 . . 121.2(6) ?
C5 C4 C7 . . 120.9(6) ?
C6 C5 C4 . . 121.5(6) ?
C6 C5 H5 . . 119.200000 ?
C4 C5 H5 . . 119.200000 ?
C5 C6 C1 . . 119.5(6) ?
C5 C6 H6 . . 120.300000 ?
C1 C6 H6 . . 120.300000 ?
C12 C7 C8 . . 119.2(6) ?
C12 C7 C4 . . 119.7(6) ?
C8 C7 C4 . . 121.0(6) ?
C9 C8 C7 . . 119.7(6) ?
C9 C8 H8 . . 120.200000 ?
C7 C8 H8 . . 120.200000 ?
C8 C9 C10 . . 121.7(6) ?
C8 C9 H9 . . 119.200000 ?
C10 C9 H9 . . 119.200000 ?
C9 C10 C11 . . 119.8(6) ?
C9 C10 S2 . . 121.7(5) ?
C11 C10 S2 . . 118.5(5) ?
C10 C11 C12 . . 118.7(6) ?
C10 C11 H11 . . 120.600000 ?
C12 C11 H11 . . 120.600000 ?
C7 C12 C11 . . 121.0(6) ?
C7 C12 H12 . . 119.500000 ?
C11 C12 H12 . . 119.500000 ?
O9 S3 O8 . . 112.4(3) ?
O9 S3 O7 . . 112.9(2) ?
O8 S3 O7 . . 111.8(2) ?
O9 S3 C13 . . 106.7(3) ?
O8 S3 C13 . . 106.2(3) ?
O7 S3 C13 . . 106.3(3) ?
O11 S4 O12 . . 112.6(2) ?
O11 S4 O10 . . 112.4(3) ?
O12 S4 O10 . . 112.6(3) ?
O11 S4 C22 . . 107.2(3) ?
O12 S4 C22 . . 105.6(3) ?
O10 S4 C22 . . 105.9(3) ?
C18 C13 C14 . . 120.0(6) ?
C18 C13 S3 . . 119.5(5) ?
C14 C13 S3 . . 120.5(5) ?
C13 C14 C15 . . 119.8(6) ?
C13 C14 H14 . . 120.100000 ?
C15 C14 H14 . . 120.100000 ?
C14 C15 C16 . . 120.4(6) ?
C14 C15 H15 . . 119.800000 ?
C16 C15 H15 . . 119.800000 ?
C15 C16 C17 . . 118.7(6) ?
C15 C16 C19 . . 120.8(6) ?
C17 C16 C19 . . 120.4(6) ?
C18 C17 C16 . . 120.9(6) ?
C18 C17 H17 . . 119.500000 ?
C16 C17 H17 . . 119.500000 ?
C17 C18 C13 . . 120.1(6) ?
C17 C18 H18 . . 119.900000 ?
C13 C18 H18 . . 119.900000 ?
C24 C19 C20 . . 117.9(6) ?
C24 C19 C16 . . 122.2(6) ?
C20 C19 C16 . . 120.0(6) ?
C21 C20 C19 . . 121.1(6) ?
C21 C20 H20 . . 119.500000 ?
C19 C20 H20 . . 119.500000 ?
C20 C21 C22 . . 118.8(6) ?
C20 C21 H21 . . 120.600000 ?
C22 C21 H21 . . 120.600000 ?
C23 C22 C21 . . 120.7(6) ?
C23 C22 S4 . . 120.8(5) ?
C21 C22 S4 . . 118.5(5) ?
C22 C23 C24 . . 119.7(6) ?
C22 C23 H23 . . 120.100000 ?
C24 C23 H23 . . 120.100000 ?
C23 C24 C19 . . 121.7(6) ?
C23 C24 H24 . . 119.100000 ?
C19 C24 H24 . . 119.100000 ?
C25 N1 H1A . . 120.000000 ?
C25 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C25 N2 H2A . . 120.000000 ?
C25 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C25 N3 H3A . . 120.000000 ?
C25 N3 H3B . . 120.000000 ?
H3A N3 H3B . . 120.000000 ?
N1 C25 N3 . . 120.1(5) ?
N1 C25 N2 . . 120.5(5) ?
N3 C25 N2 . . 119.4(5) ?
C26 N4 H4A . . 120.000000 ?
C26 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C26 N5 H5A . . 120.000000 ?
C26 N5 H5B . . 120.000000 ?
H5A N5 H5B . . 120.000000 ?
C26 N6 H6A . . 120.000000 ?
C26 N6 H6B . . 120.000000 ?
H6A N6 H6B . . 120.000000 ?
N4 C26 N6 . . 120.4(5) ?
N4 C26 N5 . . 120.3(5) ?
N6 C26 N5 . . 119.4(5) ?
C27 N7 H7A . . 120.000000 ?
C27 N7 H7B . . 120.000000 ?
H7A N7 H7B . . 120.000000 ?
C27 N8 H8A . . 120.000000 ?
C27 N8 H8B . . 120.000000 ?
H8A N8 H8B . . 120.000000 ?
C27 N9 H9A . . 120.000000 ?
C27 N9 H9B . . 120.000000 ?
H9A N9 H9B . . 120.000000 ?
N8 C27 N9 . . 120.7(6) ?
N8 C27 N7 . . 119.5(6) ?
N9 C27 N7 . . 119.8(5) ?
C28 N10 H10A . . 120.000000 ?
C28 N10 H10B . . 120.000000 ?
H10A N10 H10B . . 120.000000 ?
C28 N11 H11A . . 120.000000 ?
C28 N11 H11B . . 120.000000 ?
H11A N11 H11B . . 120.000000 ?
C28 N12 H12A . . 120.000000 ?
C28 N12 H12B . . 120.000000 ?
H12A N12 H12B . . 120.000000 ?
N11 C28 N12 . . 121.1(5) ?
N11 C28 N10 . . 120.2(5) ?
N12 C28 N10 . . 118.7(6) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol ethanol'
####################################################################### 
# 
# 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_23mdw67d
_database_code_depnum_ccdc_archive 'CCDC 2364257'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium 4,4?-biphenyldisulfonate 2-bromopropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H33 Br N6 O9 S2'
_chemical_formula_iupac          ?
_chemical_formula_weight         681.58
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   31.674(3)
_cell_length_b                   11.6225(12)
_cell_length_c                   8.2592(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.032(6)
_cell_angle_gamma                90
_cell_volume                     2984.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3017
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      22.83
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408

_exptl_absorpt_coefficient_mu    1.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   Incoatec
_diffrn_source_type              'microfocus sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       'Bruker D8 SMART APEXII'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21396
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.1323
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          'Refined as a 2-component inversion twin.,Twin'

_reflns_number_total             7077
_reflns_number_gt                4459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.862
_reflns_Friedel_fraction_full    0.875

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0831
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.1996
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         7077
_refine_ls_number_parameters     463
_refine_ls_number_restraints     661
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+15.6818P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.059
_refine_diff_density_min         -1.169
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.33(3)

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.44555(10) 0.2728(2) 0.1550(3) 0.0689(10) Uani d U P D 0.707(6) A 1
C C22A 0.4586(5) 0.4045(14) 0.3047(17) 0.023(2) Uani d U P D 0.707(6) A 1
H H22A 0.465875 0.374573 0.420158 0.028000 Uiso calc U P R 0.707(6) A 1
C C21A 0.4199(5) 0.4842(14) 0.2921(18) 0.023(2) Uani d U P D 0.707(6) A 1
H H21A 0.426492 0.545432 0.374652 0.035000 Uiso calc U P R 0.707(6) A 1
H H21B 0.395040 0.440109 0.312064 0.035000 Uiso calc U P R 0.707(6) A 1
H H21C 0.413358 0.518228 0.181616 0.035000 Uiso calc U P R 0.707(6) A 1
C C23A 0.4988(5) 0.4586(15) 0.263(2) 0.033(3) Uani d U P D 0.707(6) A 1
O O7A 0.4953(4) 0.5414(13) 0.1755(16) 0.054(4) Uani d U P D 0.707(6) A 1
C C18A 0.5430(3) 0.4085(11) 0.3283(17) 0.033(3) Uani d U P DG 0.707(6) A 1
C C15A 0.5779(4) 0.4775(11) 0.314(2) 0.072(6) Uani d U P DG 0.707(6) A 1
H H15A 0.573437 0.548788 0.256463 0.086000 Uiso calc U P R 0.707(6) A 1
C C16A 0.6194(3) 0.4423(14) 0.382(2) 0.094(5) Uani d U P DG 0.707(6) A 1
H H16A 0.643295 0.489454 0.372164 0.112000 Uiso calc U P R 0.707(6) A 1
C C17A 0.6260(3) 0.3380(15) 0.466(2) 0.094(5) Uani d U P DG 0.707(6) A 1
H H17A 0.654391 0.313944 0.512691 0.112000 Uiso calc U P R 0.707(6) A 1
C C19A 0.5911(5) 0.2690(10) 0.4805(19) 0.063(5) Uani d U P DG 0.707(6) A 1
H H19A 0.595630 0.197766 0.537517 0.076000 Uiso calc U P R 0.707(6) A 1
C C20A 0.5496(4) 0.3043(9) 0.4117(17) 0.048(4) Uani d U P DG 0.707(6) A 1
H H20A 0.525771 0.257098 0.421816 0.057000 Uiso calc U P R 0.707(6) A 1
Br Br1B 0.4744(4) 0.2006(8) 0.2329(16) 0.132(6) Uani d U P D 0.293(6) A 2
C C22B 0.4776(11) 0.359(2) 0.314(4) 0.034(6) Uani d U P D 0.293(6) A 2
H H22B 0.488812 0.354444 0.435265 0.041000 Uiso calc U P R 0.293(6) A 2
C C21B 0.4360(11) 0.437(3) 0.291(4) 0.023(2) Uani d U P D 0.293(6) A 2
H H21D 0.440591 0.499273 0.372465 0.035000 Uiso calc U P R 0.293(6) A 2
H H21E 0.411448 0.389978 0.308008 0.035000 Uiso calc U P R 0.293(6) A 2
H H21F 0.430182 0.469210 0.179841 0.035000 Uiso calc U P R 0.293(6) A 2
C C23B 0.5136(9) 0.410(3) 0.239(4) 0.037(6) Uani d U P D 0.293(6) A 2
O O7B 0.5038(10) 0.445(3) 0.101(3) 0.054(4) Uani d U P D 0.293(6) A 2
C C18B 0.5605(7) 0.406(3) 0.321(4) 0.033(3) Uani d U P DG 0.293(6) A 2
C C15B 0.5855(9) 0.492(3) 0.271(4) 0.072(6) Uani d U P DG 0.293(6) A 2
H H15B 0.574038 0.538051 0.177358 0.086000 Uiso calc U P R 0.293(6) A 2
C C16B 0.6271(9) 0.511(3) 0.356(5) 0.094(5) Uani d U P DG 0.293(6) A 2
H H16B 0.644167 0.569987 0.321379 0.112000 Uiso calc U P R 0.293(6) A 2
C C17B 0.6438(7) 0.444(4) 0.492(4) 0.069(9) Uani d U P DG 0.293(6) A 2
H H17B 0.672311 0.456708 0.550925 0.082000 Uiso calc U P R 0.293(6) A 2
C C19B 0.6189(10) 0.357(3) 0.543(4) 0.078(10) Uani d U P DG 0.293(6) A 2
H H19B 0.630326 0.311492 0.636451 0.094000 Uiso calc U P R 0.293(6) A 2
C C20B 0.5772(10) 0.339(3) 0.458(4) 0.072(10) Uani d U P DG 0.293(6) A 2
H H20B 0.560196 0.279555 0.492432 0.087000 Uiso calc U P R 0.293(6) A 2
S S1 0.69383(8) 0.1573(2) 1.0360(2) 0.0148(5) Uani d . . . 1.000000 . .
S S2 0.36381(8) 0.1527(2) 0.4714(2) 0.0138(5) Uani d . . . 1.000000 . .
O O1 0.7169(2) 0.1154(6) 0.9103(8) 0.0173(15) Uani d . . . 1.000000 . .
O O2 0.7019(2) 0.0868(6) 1.1820(8) 0.0165(15) Uani d . . . 1.000000 . .
O O3 0.7014(2) 0.2798(6) 1.0754(9) 0.0222(17) Uani d . . . 1.000000 . .
O O4 0.3581(2) 0.0788(6) 0.3245(9) 0.0206(17) Uani d . . . 1.000000 . .
O O5 0.3380(2) 0.1169(6) 0.5911(9) 0.0213(16) Uani d . . . 1.000000 . .
O O6 0.3575(2) 0.2734(6) 0.4328(8) 0.0201(16) Uani d . . . 1.000000 . .
C C1 0.6379(3) 0.1437(8) 0.9529(13) 0.018(2) Uani d U . D 1.000000 . .
C C4 0.5509(3) 0.1308(8) 0.8160(11) 0.0144(17) Uani d U . D 1.000000 . .
C C5A 0.5645(7) 0.1982(18) 0.955(2) 0.020(4) Uani d U P D 0.46(2) B 1
H H5A 0.544253 0.238840 1.004039 0.024000 Uiso calc U P R 0.46(2) B 1
C C6A 0.6086(6) 0.2053(19) 1.021(3) 0.019(4) Uani d U P D 0.46(2) B 1
H H6A 0.618280 0.253293 1.113505 0.022000 Uiso calc U P R 0.46(2) B 1
C C2A 0.6247(7) 0.074(2) 0.817(3) 0.020(6) Uani d U P D 0.46(2) B 1
H H2A 0.645066 0.032403 0.769597 0.023000 Uiso calc U P R 0.46(2) B 1
C C3A 0.5802(6) 0.0670(18) 0.749(3) 0.0144(17) Uani d U P D 0.46(2) B 1
H H3A 0.570419 0.017994 0.657593 0.017000 Uiso calc U P R 0.46(2) B 1
C C5B 0.5669(6) 0.2266(15) 0.904(2) 0.020(4) Uani d U P D 0.54(2) B 2
H H5B 0.548035 0.287127 0.921380 0.024000 Uiso calc U P R 0.54(2) B 2
C C6B 0.6107(6) 0.2348(15) 0.969(3) 0.019(4) Uani d U P D 0.54(2) B 2
H H6B 0.622050 0.302944 1.024358 0.022000 Uiso calc U P R 0.54(2) B 2
C C2B 0.6222(6) 0.0492(15) 0.859(3) 0.012(5) Uani d U P D 0.54(2) B 2
H H2B 0.641481 -0.009341 0.838470 0.015000 Uiso calc U P R 0.54(2) B 2
C C3B 0.5777(5) 0.0389(15) 0.794(2) 0.0144(17) Uani d U P D 0.54(2) B 2
H H3B 0.566324 -0.028464 0.736411 0.017000 Uiso calc U P R 0.54(2) B 2
C C7 0.5044(3) 0.1282(8) 0.7349(11) 0.0150(19) Uani d U . D 1.000000 . .
C C10 0.4177(3) 0.1401(9) 0.5732(13) 0.018(2) Uani d U . D 1.000000 . .
C C8A 0.4889(5) 0.0675(13) 0.589(2) 0.016(4) Uani d U P D 0.561(17) C 1
H H8A 0.508596 0.021583 0.543419 0.020000 Uiso calc U P R 0.561(17) C 1
C C9A 0.4466(5) 0.0708(15) 0.507(2) 0.016(4) Uani d U P D 0.561(17) C 1
H H9A 0.437304 0.027606 0.409088 0.019000 Uiso calc U P R 0.561(17) C 1
C C11A 0.4320(5) 0.1956(16) 0.721(2) 0.020(4) Uani d U P D 0.561(17) C 1
H H11A 0.412311 0.237491 0.771803 0.024000 Uiso calc U P R 0.561(17) C 1
C C12A 0.4743(5) 0.1908(14) 0.795(2) 0.015(3) Uani d U P D 0.561(17) C 1
H H12A 0.483275 0.233428 0.893524 0.018000 Uiso calc U P R 0.561(17) C 1
C C8B 0.4845(6) 0.0366(17) 0.645(3) 0.018(5) Uani d U P D 0.439(17) C 2
H H8B 0.500476 -0.031658 0.637126 0.022000 Uiso calc U P R 0.439(17) C 2
C C9B 0.4422(6) 0.0417(17) 0.567(3) 0.020(6) Uani d U P D 0.439(17) C 2
H H9B 0.429443 -0.023487 0.507709 0.024000 Uiso calc U P R 0.439(17) C 2
C C11B 0.4374(7) 0.2359(18) 0.663(3) 0.025(5) Uani d U P D 0.439(17) C 2
H H11B 0.421387 0.304306 0.669983 0.030000 Uiso calc U P R 0.439(17) C 2
C C12B 0.4796(6) 0.2294(16) 0.740(3) 0.015(3) Uani d U P D 0.439(17) C 2
H H12B 0.492675 0.294414 0.799314 0.018000 Uiso calc U P R 0.439(17) C 2
O O8 0.3026(2) 0.4620(7) 0.4340(10) 0.0229(17) Uani d . . D 1.000000 . .
H H1 0.318(3) 0.405(7) 0.415(15) 0.034000 Uiso d U . D 1.000000 . .
H H1E 0.2779(17) 0.430(9) 0.415(15) 0.034000 Uiso d U . D 1.000000 . .
O O9 0.7562(2) 0.5317(6) 0.5778(12) 0.029(2) Uani d . . D 1.000000 . .
H H1D 0.741(3) 0.591(6) 0.588(16) 0.043000 Uiso d U . D 1.000000 . .
H H1C 0.7830(10) 0.543(11) 0.582(17) 0.043000 Uiso d U . D 1.000000 . .
N N4 0.7187(3) 0.1438(7) 0.5378(11) 0.0194(19) Uani d . . . 1.000000 . .
H H4A 0.716373 0.101754 0.624257 0.023000 Uiso calc U . R 1.000000 . .
H H4B 0.712479 0.113810 0.438220 0.023000 Uiso calc U . R 1.000000 . .
N N5 0.7351(3) 0.3162(7) 0.4259(10) 0.0182(19) Uani d . . . 1.000000 . .
H H5C 0.743593 0.388319 0.437945 0.022000 Uiso calc U . R 1.000000 . .
H H5D 0.728805 0.285640 0.326690 0.022000 Uiso calc U . R 1.000000 . .
N N6 0.7413(3) 0.3012(7) 0.7035(10) 0.0208(19) Uani d . . . 1.000000 . .
H H6C 0.749713 0.373427 0.712949 0.025000 Uiso calc U . R 1.000000 . .
H H6D 0.739243 0.261148 0.792095 0.025000 Uiso calc U . R 1.000000 . .
C C14 0.7317(3) 0.2534(9) 0.5577(13) 0.018(2) Uani d . . . 1.000000 . .
N N1 0.3242(3) 0.6937(8) 0.3045(10) 0.023(2) Uani d . . . 1.000000 . .
H H1A 0.315927 0.621367 0.292815 0.027000 Uiso calc U . R 1.000000 . .
H H1B 0.326353 0.735020 0.217174 0.027000 Uiso calc U . R 1.000000 . .
N N2 0.3300(3) 0.6769(8) 0.5830(11) 0.022(2) Uani d . . . 1.000000 . .
H H2C 0.336080 0.706821 0.682682 0.026000 Uiso calc U . R 1.000000 . .
H H2D 0.321691 0.604776 0.569639 0.026000 Uiso calc U . R 1.000000 . .
N N3 0.3459(3) 0.8490(7) 0.4717(10) 0.0192(19) Uani d . . . 1.000000 . .
H H3C 0.352067 0.879725 0.570817 0.023000 Uiso calc U . R 1.000000 . .
H H3D 0.348104 0.890491 0.384591 0.023000 Uiso calc U . R 1.000000 . .
C C13 0.3334(3) 0.7403(8) 0.4538(12) 0.017(2) Uani d . . . 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C22A . 1.962(15) ?
C22A C23A . 1.519(18) ?
C22A C21A . 1.52(2) ?
C22A H22A . 1.000000 ?
C21A H21A . 0.980000 ?
C21A H21B . 0.980000 ?
C21A H21C . 0.980000 ?
C23A O7A . 1.19(2) ?
C23A C18A . 1.52(2) ?
C18A C15A . 1.390000 ?
C18A C20A . 1.390000 ?
C15A C16A . 1.390000 ?
C15A H15A . 0.950000 ?
C16A C17A . 1.390000 ?
C16A H16A . 0.950000 ?
C17A C19A . 1.390000 ?
C17A H17A . 0.950000 ?
C19A C20A . 1.390000 ?
C19A H19A . 0.950000 ?
C20A H20A . 0.950000 ?
Br1B C22B . 1.96(3) ?
C22B C23B . 1.52(3) ?
C22B C21B . 1.58(3) ?
C22B H22B . 1.000000 ?
C21B H21D . 0.980000 ?
C21B H21E . 0.980000 ?
C21B H21F . 0.980000 ?
C23B O7B . 1.20(3) ?
C23B C18B . 1.51(3) ?
C18B C15B . 1.390000 ?
C18B C20B . 1.390000 ?
C15B C16B . 1.390000 ?
C15B H15B . 0.950000 ?
C16B C17B . 1.390000 ?
C16B H16B . 0.950000 ?
C17B C19B . 1.390000 ?
C17B H17B . 0.950000 ?
C19B C20B . 1.390000 ?
C19B H19B . 0.950000 ?
C20B H20B . 0.950000 ?
S1 O2 . 1.439(7) ?
S1 O1 . 1.463(7) ?
S1 O3 . 1.470(7) ?
S1 C1 . 1.781(11) ?
S2 O6 . 1.444(7) ?
S2 O5 . 1.459(7) ?
S2 O4 . 1.470(7) ?
S2 C10 . 1.759(11) ?
C1 C6A . 1.37(2) ?
C1 C2B . 1.380(18) ?
C1 C2A . 1.38(2) ?
C1 C6B . 1.386(18) ?
C4 C5B . 1.373(18) ?
C4 C3A . 1.382(18) ?
C4 C5A . 1.39(2) ?
C4 C3B . 1.397(16) ?
C4 C7 . 1.497(11) ?
C5A C6A . 1.40(2) ?
C5A H5A . 0.950000 ?
C6A H6A . 0.950000 ?
C2A C3A . 1.42(2) ?
C2A H2A . 0.950000 ?
C3A H3A . 0.950000 ?
C5B C6B . 1.392(19) ?
C5B H5B . 0.950000 ?
C6B H6B . 0.950000 ?
C2B C3B . 1.416(19) ?
C2B H2B . 0.950000 ?
C3B H3B . 0.950000 ?
C7 C12A . 1.367(16) ?
C7 C8B . 1.38(2) ?
C7 C8A . 1.404(18) ?
C7 C12B . 1.420(19) ?
C10 C11A . 1.380(18) ?
C10 C9B . 1.388(19) ?
C10 C9A . 1.405(17) ?
C10 C11B . 1.42(2) ?
C8A C9A . 1.380(19) ?
C8A H8A . 0.950000 ?
C9A H9A . 0.950000 ?
C11A C12A . 1.36(2) ?
C11A H11A . 0.950000 ?
C12A H12A . 0.950000 ?
C8B C9B . 1.37(2) ?
C8B H8B . 0.950000 ?
C9B H9B . 0.950000 ?
C11B C12B . 1.37(2) ?
C11B H11B . 0.950000 ?
C12B H12B . 0.950000 ?
O8 H1 . 0.846(15) ?
O8 H1E . 0.852(14) ?
O9 H1D . 0.849(14) ?
O9 H1C . 0.851(15) ?
N4 C14 . 1.339(13) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C14 . 1.332(12) ?
N5 H5C . 0.880000 ?
N5 H5D . 0.880000 ?
N6 C14 . 1.308(13) ?
N6 H6C . 0.880000 ?
N6 H6D . 0.880000 ?
N1 C13 . 1.327(12) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C13 . 1.319(13) ?
N2 H2C . 0.880000 ?
N2 H2D . 0.880000 ?
N3 C13 . 1.323(12) ?
N3 H3C . 0.880000 ?
N3 H3D . 0.880000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23A C22A C21A . . 115.6(13) ?
C23A C22A Br1A . . 105.3(10) ?
C21A C22A Br1A . . 111.2(10) ?
C23A C22A H22A . . 108.200000 ?
C21A C22A H22A . . 108.200000 ?
Br1A C22A H22A . . 108.200000 ?
C22A C21A H21A . . 109.500000 ?
C22A C21A H21B . . 109.500000 ?
H21A C21A H21B . . 109.500000 ?
C22A C21A H21C . . 109.500000 ?
H21A C21A H21C . . 109.500000 ?
H21B C21A H21C . . 109.500000 ?
O7A C23A C18A . . 119.8(14) ?
O7A C23A C22A . . 119.1(16) ?
C18A C23A C22A . . 121.1(14) ?
C15A C18A C20A . . 120.000000 ?
C15A C18A C23A . . 116.2(10) ?
C20A C18A C23A . . 123.5(10) ?
C16A C15A C18A . . 120.000000 ?
C16A C15A H15A . . 120.000000 ?
C18A C15A H15A . . 120.000000 ?
C15A C16A C17A . . 120.000000 ?
C15A C16A H16A . . 120.000000 ?
C17A C16A H16A . . 120.000000 ?
C16A C17A C19A . . 120.000000 ?
C16A C17A H17A . . 120.000000 ?
C19A C17A H17A . . 120.000000 ?
C20A C19A C17A . . 120.000000 ?
C20A C19A H19A . . 120.000000 ?
C17A C19A H19A . . 120.000000 ?
C19A C20A C18A . . 120.000000 ?
C19A C20A H20A . . 120.000000 ?
C18A C20A H20A . . 120.000000 ?
C23B C22B C21B . . 114.(3) ?
C23B C22B Br1B . . 103.(2) ?
C21B C22B Br1B . . 121.(2) ?
C23B C22B H22B . . 106.100000 ?
C21B C22B H22B . . 106.100000 ?
Br1B C22B H22B . . 106.100000 ?
C22B C21B H21D . . 109.500000 ?
C22B C21B H21E . . 109.500000 ?
H21D C21B H21E . . 109.500000 ?
C22B C21B H21F . . 109.500000 ?
H21D C21B H21F . . 109.500000 ?
H21E C21B H21F . . 109.500000 ?
O7B C23B C18B . . 120.(3) ?
O7B C23B C22B . . 116.(3) ?
C18B C23B C22B . . 124.(3) ?
C15B C18B C20B . . 120.000000 ?
C15B C18B C23B . . 114.(2) ?
C20B C18B C23B . . 125.(2) ?
C18B C15B C16B . . 120.000000 ?
C18B C15B H15B . . 120.000000 ?
C16B C15B H15B . . 120.000000 ?
C17B C16B C15B . . 120.000000 ?
C17B C16B H16B . . 120.000000 ?
C15B C16B H16B . . 120.000000 ?
C16B C17B C19B . . 120.000000 ?
C16B C17B H17B . . 120.000000 ?
C19B C17B H17B . . 120.000000 ?
C20B C19B C17B . . 120.000000 ?
C20B C19B H19B . . 120.000000 ?
C17B C19B H19B . . 120.000000 ?
C19B C20B C18B . . 120.000000 ?
C19B C20B H20B . . 120.000000 ?
C18B C20B H20B . . 120.000000 ?
O2 S1 O1 . . 111.9(4) ?
O2 S1 O3 . . 111.7(4) ?
O1 S1 O3 . . 113.4(4) ?
O2 S1 C1 . . 106.0(5) ?
O1 S1 C1 . . 107.0(5) ?
O3 S1 C1 . . 106.3(4) ?
O6 S2 O5 . . 110.8(4) ?
O6 S2 O4 . . 113.3(4) ?
O5 S2 O4 . . 113.3(4) ?
O6 S2 C10 . . 105.5(5) ?
O5 S2 C10 . . 105.7(5) ?
O4 S2 C10 . . 107.5(5) ?
C6A C1 C2A . . 120.9(15) ?
C2B C1 C6B . . 120.0(13) ?
C6A C1 S1 . . 119.8(11) ?
C2B C1 S1 . . 120.7(10) ?
C2A C1 S1 . . 119.2(11) ?
C6B C1 S1 . . 119.0(10) ?
C3A C4 C5A . . 120.5(14) ?
C5B C4 C3B . . 121.3(13) ?
C5B C4 C7 . . 119.0(11) ?
C3A C4 C7 . . 119.2(11) ?
C5A C4 C7 . . 120.3(12) ?
C3B C4 C7 . . 119.7(11) ?
C4 C5A C6A . . 119.0(18) ?
C4 C5A H5A . . 120.500000 ?
C6A C5A H5A . . 120.500000 ?
C1 C6A C5A . . 120.7(18) ?
C1 C6A H6A . . 119.700000 ?
C5A C6A H6A . . 119.700000 ?
C1 C2A C3A . . 118.6(18) ?
C1 C2A H2A . . 120.700000 ?
C3A C2A H2A . . 120.700000 ?
C4 C3A C2A . . 120.2(16) ?
C4 C3A H3A . . 119.900000 ?
C2A C3A H3A . . 119.900000 ?
C4 C5B C6B . . 119.8(15) ?
C4 C5B H5B . . 120.100000 ?
C6B C5B H5B . . 120.100000 ?
C1 C6B C5B . . 120.2(15) ?
C1 C6B H6B . . 119.900000 ?
C5B C6B H6B . . 119.900000 ?
C1 C2B C3B . . 120.3(15) ?
C1 C2B H2B . . 119.800000 ?
C3B C2B H2B . . 119.800000 ?
C4 C3B C2B . . 118.1(14) ?
C4 C3B H3B . . 121.000000 ?
C2B C3B H3B . . 121.000000 ?
C12A C7 C8A . . 115.1(12) ?
C8B C7 C12B . . 117.2(13) ?
C12A C7 C4 . . 121.6(10) ?
C8B C7 C4 . . 124.5(12) ?
C8A C7 C4 . . 123.2(10) ?
C12B C7 C4 . . 118.2(11) ?
C11A C10 C9A . . 119.0(13) ?
C9B C10 C11B . . 118.3(14) ?
C11A C10 S2 . . 120.6(10) ?
C9B C10 S2 . . 123.4(11) ?
C9A C10 S2 . . 120.5(10) ?
C11B C10 S2 . . 118.3(10) ?
C9A C8A C7 . . 123.6(14) ?
C9A C8A H8A . . 118.200000 ?
C7 C8A H8A . . 118.200000 ?
C8A C9A C10 . . 118.0(14) ?
C8A C9A H9A . . 121.000000 ?
C10 C9A H9A . . 121.000000 ?
C12A C11A C10 . . 120.4(14) ?
C12A C11A H11A . . 119.800000 ?
C10 C11A H11A . . 119.800000 ?
C11A C12A C7 . . 123.8(14) ?
C11A C12A H12A . . 118.100000 ?
C7 C12A H12A . . 118.100000 ?
C9B C8B C7 . . 121.6(17) ?
C9B C8B H8B . . 119.200000 ?
C7 C8B H8B . . 119.200000 ?
C8B C9B C10 . . 121.4(18) ?
C8B C9B H9B . . 119.300000 ?
C10 C9B H9B . . 119.300000 ?
C12B C11B C10 . . 119.5(16) ?
C12B C11B H11B . . 120.200000 ?
C10 C11B H11B . . 120.200000 ?
C11B C12B C7 . . 121.9(16) ?
C11B C12B H12B . . 119.000000 ?
C7 C12B H12B . . 119.000000 ?
H1 O8 H1E . . 99.(10) ?
H1D O9 H1C . . 116.(10) ?
C14 N4 H4A . . 120.000000 ?
C14 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C14 N5 H5C . . 120.000000 ?
C14 N5 H5D . . 120.000000 ?
H5C N5 H5D . . 120.000000 ?
C14 N6 H6C . . 120.000000 ?
C14 N6 H6D . . 120.000000 ?
H6C N6 H6D . . 120.000000 ?
N6 C14 N5 . . 118.6(9) ?
N6 C14 N4 . . 121.9(9) ?
N5 C14 N4 . . 119.5(10) ?
C13 N1 H1A . . 120.000000 ?
C13 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C13 N2 H2C . . 120.000000 ?
C13 N2 H2D . . 120.000000 ?
H2C N2 H2D . . 120.000000 ?
C13 N3 H3C . . 120.000000 ?
C13 N3 H3D . . 120.000000 ?
H3C N3 H3D . . 120.000000 ?
N2 C13 N3 . . 120.8(9) ?
N2 C13 N1 . . 119.1(10) ?
N3 C13 N1 . . 120.2(9) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol ethanol'
####################################################################### 
# 
# 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_147d_hunter
_database_code_depnum_ccdc_archive 'CCDC 2364253'
loop_
_audit_author_name
_audit_author_address
'Alexander Shtukenberg'
;New York University
United States of America
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_chemical_name_systematic        
'guanidinium cyclohexanemonosulfonate 2-chloropropiophenone'
_chemical_name_common            ?
_chemical_formula_moiety         '4(C6 H11 O3 S), C9 H9 Cl O, 4(C H6 N3)'
_chemical_formula_sum            'C37 H77 Cl N12 O13 S4'
_chemical_formula_iupac          ?
_chemical_formula_weight         1061.80
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   17.5076(8)
_cell_length_b                   8.6683(4)
_cell_length_c                   19.0441(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.021(3)
_cell_angle_gamma                90
_cell_volume                     2854.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9377
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      74.67
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_max          0.35
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136

_exptl_absorpt_coefficient_mu    2.489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 with PHOTON III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            144528
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         75.13
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             11470
_reflns_number_gt                10700
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.977

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_gt          0.2305
_refine_ls_wR_factor_ref         0.2368
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         11470
_refine_ls_number_parameters     703
_refine_ls_number_restraints     485
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1555P)²+2.7825P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.457
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 4742 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)

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'
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'

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2019 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.66912(9) 0.3057(2) 0.62851(8) 0.0468(4) Uani d . . . 1.000000 . .
O O1 0.6888(3) 0.3320(7) 0.5575(2) 0.0521(12) Uani d . . . 1.000000 . .
O O2 0.6043(3) 0.3995(7) 0.6422(3) 0.0567(13) Uani d . . . 1.000000 . .
O O3 0.7360(3) 0.3241(6) 0.6842(2) 0.0490(11) Uani d . . . 1.000000 . .
C C5 0.6279(5) 0.0620(11) 0.7064(4) 0.0585(18) Uani d . . . 1.000000 . .
H H5C 0.676831 0.077037 0.739535 0.070000 Uiso calc U . R 1.000000 . .
H H5D 0.587673 0.127512 0.722503 0.070000 Uiso calc U . R 1.000000 . .
C C6 0.6035(6) -0.1082(13) 0.7066(5) 0.076(3) Uani d . . . 1.000000 . .
H H6C 0.646582 -0.174042 0.696292 0.091000 Uiso calc U . R 1.000000 . .
H H6D 0.592124 -0.136097 0.754268 0.091000 Uiso calc U . R 1.000000 . .
C C7 0.5331(6) -0.1379(14) 0.6519(5) 0.077(3) Uani d . . . 1.000000 . .
H H7C 0.520342 -0.249185 0.652126 0.093000 Uiso calc U . R 1.000000 . .
H H7D 0.488742 -0.080288 0.665435 0.093000 Uiso calc U . R 1.000000 . .
C C8 0.5434(6) -0.0922(14) 0.5790(5) 0.076(3) Uani d . . . 1.000000 . .
H H8C 0.494587 -0.109241 0.545954 0.091000 Uiso calc U . R 1.000000 . .
H H8D 0.584005 -0.157050 0.563039 0.091000 Uiso calc U . R 1.000000 . .
C C9 0.5669(5) 0.0798(13) 0.5770(4) 0.066(2) Uani d . . . 1.000000 . .
H H9C 0.576613 0.106921 0.528664 0.079000 Uiso calc U . R 1.000000 . .
H H9D 0.524165 0.145461 0.588302 0.079000 Uiso calc U . R 1.000000 . .
C C10 0.6390(5) 0.1089(10) 0.6303(4) 0.0529(16) Uani d . . . 1.000000 . .
H H10 0.681262 0.043387 0.616530 0.063000 Uiso calc U . R 1.000000 . .
O O11 0.5173(3) 0.7209(7) 0.2827(3) 0.0558(13) Uani d . . . 1.000000 . .
O O12 0.6083(3) 0.6815(6) 0.2006(3) 0.0510(11) Uani d . . . 1.000000 . .
O O13 0.6412(4) 0.6085(11) 0.3235(3) 0.086(2) Uani d . . . 1.000000 . .
S S2 0.59779(10) 0.7158(2) 0.27358(9) 0.0500(4) Uani d . . D 1.000000 . .
C C32A 0.6615(17) 1.162(2) 0.2897(12) 0.100(6) Uani d U P D 0.566(15) A 1
H H32C 0.714613 1.150003 0.278695 0.120000 Uiso calc U P R 0.566(15) A 1
H H32D 0.638363 1.253791 0.263904 0.120000 Uiso calc U P R 0.566(15) A 1
C C33A 0.6497(10) 0.8836(19) 0.3054(8) 0.051(3) Uani d U P D 0.566(15) A 1
H H33A 0.704411 0.872312 0.297062 0.062000 Uiso calc U P R 0.566(15) A 1
C C34A 0.6132(12) 1.017(2) 0.2613(11) 0.072(4) Uani d U P D 0.566(15) A 1
H H34C 0.558393 1.029296 0.267311 0.086000 Uiso calc U P R 0.566(15) A 1
H H34D 0.615687 0.999899 0.210294 0.086000 Uiso calc U P R 0.566(15) A 1
C C35A 0.6662(17) 1.189(3) 0.3693(14) 0.092(6) Uani d U P D 0.566(15) A 1
H H35C 0.700180 1.279008 0.383530 0.110000 Uiso calc U P R 0.566(15) A 1
H H35D 0.614047 1.213743 0.380112 0.110000 Uiso calc U P R 0.566(15) A 1
C C36A 0.6969(12) 1.053(2) 0.4101(9) 0.081(5) Uani d U P D 0.566(15) A 1
H H36A 0.695017 1.069907 0.461224 0.097000 Uiso calc U P R 0.566(15) A 1
H H36B 0.751630 1.037041 0.404526 0.097000 Uiso calc U P R 0.566(15) A 1
C C37A 0.6497(10) 0.905(2) 0.3849(7) 0.062(4) Uani d U P D 0.566(15) A 1
H H37A 0.673187 0.813843 0.411169 0.074000 Uiso calc U P R 0.566(15) A 1
H H37B 0.595921 0.915677 0.394325 0.074000 Uiso calc U P R 0.566(15) A 1
C C32B 0.600(2) 1.187(3) 0.2250(18) 0.109(8) Uani d U P D 0.434(15) A 2
H H32A 0.654959 1.196123 0.217927 0.130000 Uiso calc U P R 0.434(15) A 2
H H32B 0.568624 1.249068 0.187585 0.130000 Uiso calc U P R 0.434(15) A 2
C C33B 0.6222(13) 0.923(2) 0.2774(12) 0.059(5) Uani d U P D 0.434(15) A 2
H H33B 0.677928 0.932713 0.272154 0.071000 Uiso calc U P R 0.434(15) A 2
C C34B 0.5748(16) 1.012(2) 0.2156(14) 0.081(6) Uani d U P D 0.434(15) A 2
H H34A 0.518799 1.001803 0.217206 0.097000 Uiso calc U P R 0.434(15) A 2
H H34B 0.585421 0.972136 0.169466 0.097000 Uiso calc U P R 0.434(15) A 2
C C35B 0.592(2) 1.254(3) 0.2966(17) 0.116(8) Uani d U P D 0.434(15) A 2
H H35A 0.611422 1.361248 0.299520 0.139000 Uiso calc U P R 0.434(15) A 2
H H35B 0.536935 1.255330 0.302046 0.139000 Uiso calc U P R 0.434(15) A 2
C C36B 0.636(3) 1.162(4) 0.355(2) 0.108(9) Uani d U P D 0.434(15) A 2
H H36C 0.626370 1.203907 0.401258 0.130000 Uiso calc U P R 0.434(15) A 2
H H36D 0.692245 1.172321 0.353477 0.130000 Uiso calc U P R 0.434(15) A 2
C C37B 0.6134(19) 0.986(3) 0.3503(13) 0.087(6) Uani d U P D 0.434(15) A 2
H H37C 0.647155 0.927939 0.387653 0.105000 Uiso calc U P R 0.434(15) A 2
H H37D 0.559245 0.974067 0.358289 0.105000 Uiso calc U P R 0.434(15) A 2
S S3 0.30134(8) 0.7249(2) 0.51234(8) 0.0412(4) Uani d . . . 1.000000 . .
O O4 0.3186(3) 0.7014(6) 0.4402(3) 0.0494(11) Uani d . . . 1.000000 . .
O O5 0.2326(3) 0.6398(7) 0.5249(3) 0.0520(11) Uani d . . . 1.000000 . .
O O6 0.3681(3) 0.6919(6) 0.5661(2) 0.0460(11) Uani d . . . 1.000000 . .
C C17 0.2801(4) 0.9251(8) 0.5192(4) 0.0456(14) Uani d . . . 1.000000 . .
H H17 0.326768 0.984276 0.510435 0.055000 Uiso calc U . R 1.000000 . .
C C18 0.2652(5) 0.9652(10) 0.5939(4) 0.0590(18) Uani d . . . 1.000000 . .
H H18A 0.311161 0.938379 0.629062 0.071000 Uiso calc U . R 1.000000 . .
H H18B 0.220764 0.904583 0.605212 0.071000 Uiso calc U . R 1.000000 . .
C C19 0.2479(6) 1.1385(12) 0.5987(5) 0.073(2) Uani d . . . 1.000000 . .
H H19A 0.234664 1.162209 0.646236 0.087000 Uiso calc U . R 1.000000 . .
H H19B 0.294529 1.198617 0.592818 0.087000 Uiso calc U . R 1.000000 . .
C C20 0.1818(6) 1.1852(12) 0.5424(6) 0.074(2) Uani d . . . 1.000000 . .
H H20A 0.174063 1.298124 0.544655 0.089000 Uiso calc U . R 1.000000 . .
H H20B 0.133872 1.134101 0.551691 0.089000 Uiso calc U . R 1.000000 . .
C C22 0.2140(5) 0.9709(10) 0.4626(4) 0.0571(18) Uani d . . . 1.000000 . .
H H22A 0.167451 0.910023 0.468225 0.069000 Uiso calc U . R 1.000000 . .
H H22B 0.227402 0.948639 0.415081 0.069000 Uiso calc U . R 1.000000 . .
C C25 0.1968(5) 1.1420(12) 0.4686(5) 0.069(2) Uani d . . . 1.000000 . .
H H25A 0.241183 1.202497 0.457121 0.083000 Uiso calc U . R 1.000000 . .
H H25B 0.150903 1.168972 0.433414 0.083000 Uiso calc U . R 1.000000 . .
O O7 0.3771(3) 0.7328(7) 0.8931(3) 0.0532(12) Uani d . . . 1.000000 . .
O O8 0.4706(3) 0.7080(7) 0.8131(3) 0.0507(12) Uani d . . . 1.000000 . .
O O9 0.5136(3) 0.7069(5) 0.9401(3) 0.0461(10) Uani d . . . 1.000000 . .
S S4 0.45591(9) 0.76361(18) 0.88240(8) 0.0425(4) Uani d . . D 1.000000 . .
C C11A 0.4712(6) 0.9694(11) 0.8795(6) 0.057(2) Uani d U P D 0.822(12) B 1
H H11C 0.525010 0.987488 0.869833 0.068000 Uiso calc U P R 0.822(12) B 1
C C12A 0.4154(8) 1.0418(13) 0.8193(6) 0.073(3) Uani d U P D 0.822(12) B 1
H H12C 0.361687 1.021200 0.826850 0.087000 Uiso calc U P R 0.822(12) B 1
H H12D 0.422807 0.993566 0.773764 0.087000 Uiso calc U P R 0.822(12) B 1
C C13A 0.4278(10) 1.2182(15) 0.8148(10) 0.094(4) Uani d U P D 0.822(12) B 1
H H13A 0.478684 1.239160 0.800417 0.113000 Uiso calc U P R 0.822(12) B 1
H H13B 0.387247 1.263044 0.778444 0.113000 Uiso calc U P R 0.822(12) B 1
C C14A 0.4242(10) 1.2934(14) 0.8870(11) 0.100(5) Uani d U P D 0.822(12) B 1
H H14A 0.439487 1.403098 0.885220 0.120000 Uiso calc U P R 0.822(12) B 1
H H14B 0.370343 1.289740 0.896764 0.120000 Uiso calc U P R 0.822(12) B 1
C C15A 0.4769(11) 1.2135(14) 0.9468(11) 0.102(5) Uani d U P D 0.822(12) B 1
H H15C 0.531245 1.232400 0.940907 0.122000 Uiso calc U P R 0.822(12) B 1
H H15D 0.468909 1.260356 0.992547 0.122000 Uiso calc U P R 0.822(12) B 1
C C16A 0.4642(7) 1.0421(12) 0.9507(7) 0.069(3) Uani d U P D 0.822(12) B 1
H H16C 0.412203 1.021385 0.962755 0.082000 Uiso calc U P R 0.822(12) B 1
H H16D 0.503121 0.996645 0.988292 0.082000 Uiso calc U P R 0.822(12) B 1
C C11B 0.429(2) 0.962(3) 0.877(2) 0.055(8) Uani d U P D 0.178(12) B 2
H H11D 0.411104 0.991683 0.922761 0.066000 Uiso calc U P R 0.178(12) B 2
C C12B 0.364(2) 0.993(4) 0.817(2) 0.058(8) Uani d U P D 0.178(12) B 2
H H12E 0.314602 0.950511 0.828710 0.070000 Uiso calc U P R 0.178(12) B 2
H H12F 0.374345 0.940157 0.773087 0.070000 Uiso calc U P R 0.178(12) B 2
C C13B 0.355(3) 1.168(4) 0.803(3) 0.078(9) Uani d U P D 0.178(12) B 2
H H13C 0.377084 1.196101 0.759965 0.094000 Uiso calc U P R 0.178(12) B 2
H H13D 0.299553 1.196901 0.795085 0.094000 Uiso calc U P R 0.178(12) B 2
C C14B 0.397(4) 1.255(7) 0.867(4) 0.112(12) Uani d U P D 0.178(12) B 2
H H14C 0.387871 1.367649 0.861622 0.134000 Uiso calc U P R 0.178(12) B 2
H H14D 0.378651 1.221152 0.911270 0.134000 Uiso calc U P R 0.178(12) B 2
C C15B 0.484(3) 1.222(4) 0.873(5) 0.106(11) Uani d U P D 0.178(12) B 2
H H15A 0.503288 1.273049 0.832473 0.127000 Uiso calc U P R 0.178(12) B 2
H H15B 0.511260 1.266429 0.917199 0.127000 Uiso calc U P R 0.178(12) B 2
C C16B 0.502(2) 1.053(4) 0.871(4) 0.081(10) Uani d U P D 0.178(12) B 2
H H16A 0.543538 1.026530 0.910944 0.097000 Uiso calc U P R 0.178(12) B 2
H H16B 0.520830 1.026466 0.825901 0.097000 Uiso calc U P R 0.178(12) B 2
O O10A 0.3225(11) 1.0233(17) 0.1515(11) 0.293(15) Uani d . . D 1.000000 . .
C C21A 0.3452(7) 1.3142(9) 0.2868(7) 0.138(5) Uani d U . G 1.000000 . .
H H21A 0.328343 1.403056 0.259499 0.166000 Uiso calc U . R 1.000000 . .
C C24A 0.3675(8) 1.3265(11) 0.3599(7) 0.148(6) Uani d U . G 1.000000 . .
H H24A 0.365770 1.423772 0.382597 0.177000 Uiso calc U . R 1.000000 . .
C C26A 0.3922(8) 1.1965(16) 0.3998(6) 0.161(6) Uani d U . G 1.000000 . .
H H26A 0.407387 1.204915 0.449802 0.194000 Uiso calc U . R 1.000000 . .
C C27A 0.3947(8) 1.0542(13) 0.3666(7) 0.190(8) Uani d U . G 1.000000 . .
H H27A 0.411578 0.965340 0.393910 0.228000 Uiso calc U . R 1.000000 . .
C C28A 0.3725(7) 1.0419(9) 0.2935(8) 0.159(6) Uani d U . DG 1.000000 . .
H H28A 0.374152 0.944621 0.270813 0.191000 Uiso calc U . R 1.000000 . .
C C29A 0.3477(6) 1.1719(11) 0.2536(6) 0.121(4) Uani d U . DG 1.000000 . .
C C30A 0.3271(8) 1.1515(19) 0.1739(11) 0.141(5) Uani d U . D 1.000000 . .
C C23A 0.268(2) 1.238(3) 0.0512(15) 0.193(10) Uani d U . . 1.000000 . .
H H23A 0.279183 1.309411 0.014179 0.289000 Uiso calc U . R 1.000000 . .
H H23B 0.213097 1.243649 0.055300 0.289000 Uiso calc U . R 1.000000 . .
H H23C 0.281003 1.132586 0.038543 0.289000 Uiso calc U . R 1.000000 . .
C C31A 0.3233(17) 1.288(2) 0.1320(17) 0.206(11) Uani d U . D 1.000000 . .
H H31A 0.306758 1.383670 0.154930 0.247000 Uiso calc U . R 1.000000 . .
Cl Cl1A 0.419(2) 1.284(4) 0.119(2) 0.63(3) Uani d . . D 1.000000 . .
N N1 0.8946(4) 0.3151(10) 0.6609(3) 0.0642(19) Uani d . . . 1.000000 . .
H H1A 0.933017 0.316547 0.696774 0.077000 Uiso calc U . R 1.000000 . .
H H1B 0.846519 0.318311 0.668905 0.077000 Uiso calc U . R 1.000000 . .
N N2 0.9821(4) 0.3035(11) 0.5832(4) 0.067(2) Uani d . . . 1.000000 . .
H H2A 1.020217 0.304965 0.619326 0.080000 Uiso calc U . R 1.000000 . .
H H2B 0.992357 0.298945 0.539426 0.080000 Uiso calc U . R 1.000000 . .
N N3 0.8514(4) 0.3075(10) 0.5402(3) 0.0624(18) Uani d . . . 1.000000 . .
H H3A 0.861260 0.303868 0.496358 0.075000 Uiso calc U . R 1.000000 . .
H H3B 0.803258 0.310662 0.548187 0.075000 Uiso calc U . R 1.000000 . .
C C1 0.9094(4) 0.3082(11) 0.5946(4) 0.0547(17) Uani d . . . 1.000000 . .
N N4 0.5900(4) 0.5181(9) 0.4548(3) 0.0578(16) Uani d . . . 1.000000 . .
H H4A 0.619052 0.460342 0.486396 0.069000 Uiso calc U . R 1.000000 . .
H H4B 0.606727 0.544926 0.415351 0.069000 Uiso calc U . R 1.000000 . .
N N5 0.4971(4) 0.5230(8) 0.5265(3) 0.0533(14) Uani d . . . 1.000000 . .
H H5A 0.526572 0.465217 0.557705 0.064000 Uiso calc U . R 1.000000 . .
H H5B 0.451414 0.553284 0.534946 0.064000 Uiso calc U . R 1.000000 . .
N N6 0.4758(4) 0.6477(9) 0.4188(3) 0.0578(16) Uani d . . . 1.000000 . .
H H6A 0.491248 0.672625 0.378462 0.069000 Uiso calc U . R 1.000000 . .
H H6B 0.430204 0.677886 0.427352 0.069000 Uiso calc U . R 1.000000 . .
C C2 0.5215(4) 0.5644(9) 0.4667(3) 0.0503(15) Uani d . . . 1.000000 . .
N N7 0.6333(3) 0.4961(7) 0.9034(3) 0.0445(12) Uani d . . . 1.000000 . .
H H7A 0.666324 0.461154 0.939583 0.053000 Uiso calc U . R 1.000000 . .
H H7B 0.593916 0.553261 0.911091 0.053000 Uiso calc U . R 1.000000 . .
N N8 0.7022(3) 0.3767(7) 0.8260(3) 0.0464(12) Uani d . . . 1.000000 . .
H H8A 0.708890 0.353454 0.782419 0.056000 Uiso calc U . R 1.000000 . .
H H8B 0.735014 0.342620 0.862466 0.056000 Uiso calc U . R 1.000000 . .
N N9 0.5928(4) 0.5146(8) 0.7820(3) 0.0516(14) Uani d . . . 1.000000 . .
H H9A 0.598996 0.492092 0.738221 0.062000 Uiso calc U . R 1.000000 . .
H H9B 0.553431 0.571805 0.789771 0.062000 Uiso calc U . R 1.000000 . .
C C4 0.6431(4) 0.4621(7) 0.8367(3) 0.0404(12) Uani d . . . 1.000000 . .
N N10 0.2295(4) 0.5195(8) 0.6702(3) 0.0513(13) Uani d . . . 1.000000 . .
H H10A 0.232771 0.542650 0.625797 0.062000 Uiso calc U . R 1.000000 . .
H H10B 0.189667 0.466655 0.680226 0.062000 Uiso calc U . R 1.000000 . .
N N11 0.3444(4) 0.6432(9) 0.7075(3) 0.0550(14) Uani d . . . 1.000000 . .
H H11A 0.348376 0.667100 0.663337 0.066000 Uiso calc U . R 1.000000 . .
H H11B 0.380581 0.672078 0.742447 0.066000 Uiso calc U . R 1.000000 . .
N N12 0.2780(4) 0.5305(7) 0.7888(3) 0.0478(12) Uani d . . . 1.000000 . .
H H12A 0.237529 0.479208 0.798550 0.057000 Uiso calc U . R 1.000000 . .
H H12B 0.314386 0.559852 0.823368 0.057000 Uiso calc U . R 1.000000 . .
C C3 0.2840(4) 0.5636(8) 0.7215(4) 0.0453(14) Uani d . . . 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.453(5) ?
S1 O3 . 1.460(5) ?
S1 O1 . 1.466(5) ?
S1 C10 . 1.788(9) ?
C5 C6 . 1.536(14) ?
C5 C10 . 1.546(10) ?
C5 H5C . 0.990000 ?
C5 H5D . 0.990000 ?
C6 C7 . 1.505(14) ?
C6 H6C . 0.990000 ?
C6 H6D . 0.990000 ?
C7 C8 . 1.484(13) ?
C7 H7C . 0.990000 ?
C7 H7D . 0.990000 ?
C8 C9 . 1.548(15) ?
C8 H8C . 0.990000 ?
C8 H8D . 0.990000 ?
C9 C10 . 1.513(11) ?
C9 H9C . 0.990000 ?
C9 H9D . 0.990000 ?
C10 H10 . 1.000000 ?
O11 S2 . 1.448(6) ?
O12 S2 . 1.461(5) ?
O13 S2 . 1.456(7) ?
S2 C33A . 1.770(13) ?
S2 C33B . 1.85(2) ?
C32A C35A . 1.52(3) ?
C32A C34A . 1.56(2) ?
C32A H32C . 0.990000 ?
C32A H32D . 0.990000 ?
C33A C34A . 1.51(2) ?
C33A C37A . 1.525(17) ?
C33A H33A . 1.000000 ?
C34A H34C . 0.990000 ?
C34A H34D . 0.990000 ?
C35A C36A . 1.47(4) ?
C35A H35C . 0.990000 ?
C35A H35D . 0.990000 ?
C36A C37A . 1.56(2) ?
C36A H36A . 0.990000 ?
C36A H36B . 0.990000 ?
C37A H37A . 0.990000 ?
C37A H37B . 0.990000 ?
C32B C35B . 1.51(3) ?
C32B C34B . 1.58(3) ?
C32B H32A . 0.990000 ?
C32B H32B . 0.990000 ?
C33B C37B . 1.52(2) ?
C33B C34B . 1.54(3) ?
C33B H33B . 1.000000 ?
C34B H34A . 0.990000 ?
C34B H34B . 0.990000 ?
C35B C36B . 1.48(4) ?
C35B H35A . 0.990000 ?
C35B H35B . 0.990000 ?
C36B C37B . 1.57(3) ?
C36B H36C . 0.990000 ?
C36B H36D . 0.990000 ?
C37B H37C . 0.990000 ?
C37B H37D . 0.990000 ?
S3 O6 . 1.456(5) ?
S3 O5 . 1.464(5) ?
S3 O4 . 1.466(5) ?
S3 C17 . 1.783(7) ?
C17 C22 . 1.506(10) ?
C17 C18 . 1.527(10) ?
C17 H17 . 1.000000 ?
C18 C19 . 1.538(12) ?
C18 H18A . 0.990000 ?
C18 H18B . 0.990000 ?
C19 C20 . 1.504(14) ?
C19 H19A . 0.990000 ?
C19 H19B . 0.990000 ?
C20 C25 . 1.516(14) ?
C20 H20A . 0.990000 ?
C20 H20B . 0.990000 ?
C22 C25 . 1.521(13) ?
C22 H22A . 0.990000 ?
C22 H22B . 0.990000 ?
C25 H25A . 0.990000 ?
C25 H25B . 0.990000 ?
O7 S4 . 1.451(6) ?
O8 S4 . 1.466(5) ?
O9 S4 . 1.456(5) ?
S4 C11B . 1.78(2) ?
S4 C11A . 1.806(10) ?
C11A C16A . 1.517(15) ?
C11A C12A . 1.519(15) ?
C11A H11C . 1.000000 ?
C12A C13A . 1.549(17) ?
C12A H12C . 0.990000 ?
C12A H12D . 0.990000 ?
C13A C14A . 1.53(3) ?
C13A H13A . 0.990000 ?
C13A H13B . 0.990000 ?
C14A C15A . 1.52(2) ?
C14A H14A . 0.990000 ?
C14A H14B . 0.990000 ?
C15A C16A . 1.505(16) ?
C15A H15C . 0.990000 ?
C15A H15D . 0.990000 ?
C16A H16C . 0.990000 ?
C16A H16D . 0.990000 ?
C11B C12B . 1.51(3) ?
C11B C16B . 1.53(3) ?
C11B H11D . 1.000000 ?
C12B C13B . 1.55(3) ?
C12B H12E . 0.990000 ?
C12B H12F . 0.990000 ?
C13B C14B . 1.53(4) ?
C13B H13C . 0.990000 ?
C13B H13D . 0.990000 ?
C14B C15B . 1.53(4) ?
C14B H14C . 0.990000 ?
C14B H14D . 0.990000 ?
C15B C16B . 1.50(3) ?
C15B H15A . 0.990000 ?
C15B H15B . 0.990000 ?
C16B H16A . 0.990000 ?
C16B H16B . 0.990000 ?
O10A C30A . 1.19(2) ?
C21A C24A . 1.390000 ?
C21A C29A . 1.390000 ?
C21A H21A . 0.950000 ?
C24A C26A . 1.390000 ?
C24A H24A . 0.950000 ?
C26A C27A . 1.390000 ?
C26A H26A . 0.950000 ?
C27A C28A . 1.390000 ?
C27A H27A . 0.950000 ?
C28A C29A . 1.390000 ?
C28A H28A . 0.950000 ?
C29A C30A . 1.515(19) ?
C30A C31A . 1.42(3) ?
C23A C31A . 1.74(4) ?
C23A H23A . 0.980000 ?
C23A H23B . 0.980000 ?
C23A H23C . 0.980000 ?
C31A Cl1A . 1.73(2) ?
C31A H31A . 1.000000 ?
N1 C1 . 1.328(10) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C1 . 1.326(9) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
N3 C1 . 1.332(10) ?
N3 H3A . 0.880000 ?
N3 H3B . 0.880000 ?
N4 C2 . 1.318(9) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C2 . 1.326(9) ?
N5 H5A . 0.880000 ?
N5 H5B . 0.880000 ?
N6 C2 . 1.328(9) ?
N6 H6A . 0.880000 ?
N6 H6B . 0.880000 ?
N7 C4 . 1.342(8) ?
N7 H7A . 0.880000 ?
N7 H7B . 0.880000 ?
N8 C4 . 1.314(9) ?
N8 H8A . 0.880000 ?
N8 H8B . 0.880000 ?
N9 C4 . 1.334(9) ?
N9 H9A . 0.880000 ?
N9 H9B . 0.880000 ?
N10 C3 . 1.310(9) ?
N10 H10A . 0.880000 ?
N10 H10B . 0.880000 ?
N11 C3 . 1.324(10) ?
N11 H11A . 0.880000 ?
N11 H11B . 0.880000 ?
N12 C3 . 1.334(9) ?
N12 H12A . 0.880000 ?
N12 H12B . 0.880000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . 111.6(3) ?
O2 S1 O1 . . 112.5(3) ?
O3 S1 O1 . . 112.0(3) ?
O2 S1 C10 . . 106.8(4) ?
O3 S1 C10 . . 107.2(3) ?
O1 S1 C10 . . 106.2(3) ?
C6 C5 C10 . . 109.3(7) ?
C6 C5 H5C . . 109.800000 ?
C10 C5 H5C . . 109.800000 ?
C6 C5 H5D . . 109.800000 ?
C10 C5 H5D . . 109.800000 ?
H5C C5 H5D . . 108.300000 ?
C7 C6 C5 . . 111.2(9) ?
C7 C6 H6C . . 109.400000 ?
C5 C6 H6C . . 109.400000 ?
C7 C6 H6D . . 109.400000 ?
C5 C6 H6D . . 109.400000 ?
H6C C6 H6D . . 108.000000 ?
C8 C7 C6 . . 113.2(8) ?
C8 C7 H7C . . 108.900000 ?
C6 C7 H7C . . 108.900000 ?
C8 C7 H7D . . 108.900000 ?
C6 C7 H7D . . 108.900000 ?
H7C C7 H7D . . 107.700000 ?
C7 C8 C9 . . 110.6(8) ?
C7 C8 H8C . . 109.500000 ?
C9 C8 H8C . . 109.500000 ?
C7 C8 H8D . . 109.500000 ?
C9 C8 H8D . . 109.500000 ?
H8C C8 H8D . . 108.100000 ?
C10 C9 C8 . . 109.9(8) ?
C10 C9 H9C . . 109.700000 ?
C8 C9 H9C . . 109.700000 ?
C10 C9 H9D . . 109.700000 ?
C8 C9 H9D . . 109.700000 ?
H9C C9 H9D . . 108.200000 ?
C9 C10 C5 . . 111.8(7) ?
C9 C10 S1 . . 111.4(6) ?
C5 C10 S1 . . 110.5(5) ?
C9 C10 H10 . . 107.700000 ?
C5 C10 H10 . . 107.700000 ?
S1 C10 H10 . . 107.700000 ?
O11 S2 O13 . . 111.0(4) ?
O11 S2 O12 . . 113.0(3) ?
O13 S2 O12 . . 111.1(3) ?
O11 S2 C33A . . 113.0(6) ?
O13 S2 C33A . . 96.5(8) ?
O12 S2 C33A . . 111.0(5) ?
O11 S2 C33B . . 100.9(7) ?
O13 S2 C33B . . 120.2(9) ?
O12 S2 C33B . . 99.9(7) ?
C35A C32A C34A . . 114.4(15) ?
C35A C32A H32C . . 108.700000 ?
C34A C32A H32C . . 108.700000 ?
C35A C32A H32D . . 108.700000 ?
C34A C32A H32D . . 108.700000 ?
H32C C32A H32D . . 107.600000 ?
C34A C33A C37A . . 113.1(14) ?
C34A C33A S2 . . 106.7(12) ?
C37A C33A S2 . . 111.1(9) ?
C34A C33A H33A . . 108.600000 ?
C37A C33A H33A . . 108.600000 ?
S2 C33A H33A . . 108.600000 ?
C33A C34A C32A . . 105.3(18) ?
C33A C34A H34C . . 110.700000 ?
C32A C34A H34C . . 110.700000 ?
C33A C34A H34D . . 110.700000 ?
C32A C34A H34D . . 110.700000 ?
H34C C34A H34D . . 108.800000 ?
C36A C35A C32A . . 110.9(18) ?
C36A C35A H35C . . 109.500000 ?
C32A C35A H35C . . 109.500000 ?
C36A C35A H35D . . 109.500000 ?
C32A C35A H35D . . 109.500000 ?
H35C C35A H35D . . 108.000000 ?
C35A C36A C37A . . 111.5(17) ?
C35A C36A H36A . . 109.300000 ?
C37A C36A H36A . . 109.300000 ?
C35A C36A H36B . . 109.300000 ?
C37A C36A H36B . . 109.300000 ?
H36A C36A H36B . . 108.000000 ?
C33A C37A C36A . . 108.9(12) ?
C33A C37A H37A . . 109.900000 ?
C36A C37A H37A . . 109.900000 ?
C33A C37A H37B . . 109.900000 ?
C36A C37A H37B . . 109.900000 ?
H37A C37A H37B . . 108.300000 ?
C35B C32B C34B . . 114.(2) ?
C35B C32B H32A . . 108.800000 ?
C34B C32B H32A . . 108.800000 ?
C35B C32B H32B . . 108.800000 ?
C34B C32B H32B . . 108.800000 ?
H32A C32B H32B . . 107.700000 ?
C37B C33B C34B . . 113.(2) ?
C37B C33B S2 . . 109.3(15) ?
C34B C33B S2 . . 111.5(14) ?
C37B C33B H33B . . 107.500000 ?
C34B C33B H33B . . 107.500000 ?
S2 C33B H33B . . 107.500000 ?
C33B C34B C32B . . 107.(2) ?
C33B C34B H34A . . 110.400000 ?
C32B C34B H34A . . 110.400000 ?
C33B C34B H34B . . 110.400000 ?
C32B C34B H34B . . 110.400000 ?
H34A C34B H34B . . 108.600000 ?
C36B C35B C32B . . 111.(3) ?
C36B C35B H35A . . 109.400000 ?
C32B C35B H35A . . 109.400000 ?
C36B C35B H35B . . 109.400000 ?
C32B C35B H35B . . 109.400000 ?
H35A C35B H35B . . 108.000000 ?
C35B C36B C37B . . 112.(2) ?
C35B C36B H36C . . 109.200000 ?
C37B C36B H36C . . 109.200000 ?
C35B C36B H36D . . 109.200000 ?
C37B C36B H36D . . 109.200000 ?
H36C C36B H36D . . 107.900000 ?
C33B C37B C36B . . 110.(2) ?
C33B C37B H37C . . 109.700000 ?
C36B C37B H37C . . 109.700000 ?
C33B C37B H37D . . 109.700000 ?
C36B C37B H37D . . 109.700000 ?
H37C C37B H37D . . 108.200000 ?
O6 S3 O5 . . 112.1(3) ?
O6 S3 O4 . . 111.8(3) ?
O5 S3 O4 . . 112.3(3) ?
O6 S3 C17 . . 107.0(3) ?
O5 S3 C17 . . 107.0(3) ?
O4 S3 C17 . . 106.3(3) ?
C22 C17 C18 . . 112.4(6) ?
C22 C17 S3 . . 110.5(5) ?
C18 C17 S3 . . 111.0(5) ?
C22 C17 H17 . . 107.600000 ?
C18 C17 H17 . . 107.600000 ?
S3 C17 H17 . . 107.600000 ?
C17 C18 C19 . . 110.0(7) ?
C17 C18 H18A . . 109.700000 ?
C19 C18 H18A . . 109.700000 ?
C17 C18 H18B . . 109.700000 ?
C19 C18 H18B . . 109.700000 ?
H18A C18 H18B . . 108.200000 ?
C20 C19 C18 . . 110.9(8) ?
C20 C19 H19A . . 109.500000 ?
C18 C19 H19A . . 109.500000 ?
C20 C19 H19B . . 109.500000 ?
C18 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 108.000000 ?
C19 C20 C25 . . 111.7(7) ?
C19 C20 H20A . . 109.300000 ?
C25 C20 H20A . . 109.300000 ?
C19 C20 H20B . . 109.300000 ?
C25 C20 H20B . . 109.300000 ?
H20A C20 H20B . . 107.900000 ?
C17 C22 C25 . . 110.0(7) ?
C17 C22 H22A . . 109.600000 ?
C25 C22 H22A . . 109.700000 ?
C17 C22 H22B . . 109.700000 ?
C25 C22 H22B . . 109.700000 ?
H22A C22 H22B . . 108.200000 ?
C20 C25 C22 . . 112.0(8) ?
C20 C25 H25A . . 109.200000 ?
C22 C25 H25A . . 109.200000 ?
C20 C25 H25B . . 109.200000 ?
C22 C25 H25B . . 109.200000 ?
H25A C25 H25B . . 107.900000 ?
O7 S4 O9 . . 113.2(3) ?
O7 S4 O8 . . 111.8(3) ?
O9 S4 O8 . . 111.7(3) ?
O7 S4 C11B . . 86.3(13) ?
O9 S4 C11B . . 121.0(12) ?
O8 S4 C11B . . 110.5(13) ?
O7 S4 C11A . . 109.6(4) ?
O9 S4 C11A . . 105.5(4) ?
O8 S4 C11A . . 104.4(4) ?
C16A C11A C12A . . 111.7(8) ?
C16A C11A S4 . . 110.5(7) ?
C12A C11A S4 . . 110.5(8) ?
C16A C11A H11C . . 108.000000 ?
C12A C11A H11C . . 108.000000 ?
S4 C11A H11C . . 108.000000 ?
C11A C12A C13A . . 111.8(13) ?
C11A C12A H12C . . 109.300000 ?
C13A C12A H12C . . 109.300000 ?
C11A C12A H12D . . 109.300000 ?
C13A C12A H12D . . 109.300000 ?
H12C C12A H12D . . 107.900000 ?
C14A C13A C12A . . 110.2(12) ?
C14A C13A H13A . . 109.600000 ?
C12A C13A H13A . . 109.600000 ?
C14A C13A H13B . . 109.600000 ?
C12A C13A H13B . . 109.600000 ?
H13A C13A H13B . . 108.100000 ?
C15A C14A C13A . . 112.0(12) ?
C15A C14A H14A . . 109.200000 ?
C13A C14A H14A . . 109.200000 ?
C15A C14A H14B . . 109.200000 ?
C13A C14A H14B . . 109.200000 ?
H14A C14A H14B . . 107.900000 ?
C16A C15A C14A . . 114.2(13) ?
C16A C15A H15C . . 108.700000 ?
C14A C15A H15C . . 108.700000 ?
C16A C15A H15D . . 108.700000 ?
C14A C15A H15D . . 108.700000 ?
H15C C15A H15D . . 107.600000 ?
C15A C16A C11A . . 109.5(12) ?
C15A C16A H16C . . 109.800000 ?
C11A C16A H16C . . 109.800000 ?
C15A C16A H16D . . 109.800000 ?
C11A C16A H16D . . 109.800000 ?
H16C C16A H16D . . 108.200000 ?
C12B C11B C16B . . 113.(3) ?
C12B C11B S4 . . 112.(2) ?
C16B C11B S4 . . 106.(2) ?
C12B C11B H11D . . 108.400000 ?
C16B C11B H11D . . 108.400000 ?
S4 C11B H11D . . 108.400000 ?
C11B C12B C13B . . 110.(3) ?
C11B C12B H12E . . 109.700000 ?
C13B C12B H12E . . 109.700000 ?
C11B C12B H12F . . 109.700000 ?
C13B C12B H12F . . 109.700000 ?
H12E C12B H12F . . 108.200000 ?
C14B C13B C12B . . 109.(3) ?
C14B C13B H13C . . 109.800000 ?
C12B C13B H13C . . 109.800000 ?
C14B C13B H13D . . 109.800000 ?
C12B C13B H13D . . 109.800000 ?
H13C C13B H13D . . 108.300000 ?
C15B C14B C13B . . 108.(4) ?
C15B C14B H14C . . 110.100000 ?
C13B C14B H14C . . 110.200000 ?
C15B C14B H14D . . 110.100000 ?
C13B C14B H14D . . 110.100000 ?
H14C C14B H14D . . 108.400000 ?
C16B C15B C14B . . 114.(3) ?
C16B C15B H15A . . 108.800000 ?
C14B C15B H15A . . 108.800000 ?
C16B C15B H15B . . 108.800000 ?
C14B C15B H15B . . 108.800000 ?
H15A C15B H15B . . 107.700000 ?
C15B C16B C11B . . 108.(3) ?
C15B C16B H16A . . 110.100000 ?
C11B C16B H16A . . 110.100000 ?
C15B C16B H16B . . 110.100000 ?
C11B C16B H16B . . 110.100000 ?
H16A C16B H16B . . 108.400000 ?
C24A C21A C29A . . 120.000000 ?
C24A C21A H21A . . 120.000000 ?
C29A C21A H21A . . 120.000000 ?
C26A C24A C21A . . 120.000000 ?
C26A C24A H24A . . 120.000000 ?
C21A C24A H24A . . 120.000000 ?
C24A C26A C27A . . 120.000000 ?
C24A C26A H26A . . 120.000000 ?
C27A C26A H26A . . 120.000000 ?
C26A C27A C28A . . 120.000000 ?
C26A C27A H27A . . 120.000000 ?
C28A C27A H27A . . 120.000000 ?
C29A C28A C27A . . 120.000000 ?
C29A C28A H28A . . 120.000000 ?
C27A C28A H28A . . 120.000000 ?
C28A C29A C21A . . 120.000000 ?
C28A C29A C30A . . 117.3(10) ?
C21A C29A C30A . . 122.7(10) ?
O10A C30A C31A . . 126.(2) ?
O10A C30A C29A . . 117.4(18) ?
C31A C30A C29A . . 116.6(17) ?
C31A C23A H23A . . 109.500000 ?
C31A C23A H23B . . 109.500000 ?
H23A C23A H23B . . 109.500000 ?
C31A C23A H23C . . 109.500000 ?
H23A C23A H23C . . 109.500000 ?
H23B C23A H23C . . 109.500000 ?
C30A C31A Cl1A . . 95.7(16) ?
C30A C31A C23A . . 105.0(18) ?
Cl1A C31A C23A . . 106.(2) ?
C30A C31A H31A . . 115.800000 ?
Cl1A C31A H31A . . 115.800000 ?
C23A C31A H31A . . 115.800000 ?
C1 N1 H1A . . 120.000000 ?
C1 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C1 N2 H2A . . 120.000000 ?
C1 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C1 N3 H3A . . 120.000000 ?
C1 N3 H3B . . 120.000000 ?
H3A N3 H3B . . 120.000000 ?
N2 C1 N1 . . 119.5(7) ?
N2 C1 N3 . . 120.4(7) ?
N1 C1 N3 . . 120.1(7) ?
C2 N4 H4A . . 120.000000 ?
C2 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C2 N5 H5A . . 120.000000 ?
C2 N5 H5B . . 120.000000 ?
H5A N5 H5B . . 120.000000 ?
C2 N6 H6A . . 120.000000 ?
C2 N6 H6B . . 120.000000 ?
H6A N6 H6B . . 120.000000 ?
N4 C2 N5 . . 119.3(6) ?
N4 C2 N6 . . 120.9(6) ?
N5 C2 N6 . . 119.8(6) ?
C4 N7 H7A . . 120.000000 ?
C4 N7 H7B . . 120.000000 ?
H7A N7 H7B . . 120.000000 ?
C4 N8 H8A . . 120.000000 ?
C4 N8 H8B . . 120.000000 ?
H8A N8 H8B . . 120.000000 ?
C4 N9 H9A . . 120.000000 ?
C4 N9 H9B . . 120.000000 ?
H9A N9 H9B . . 120.000000 ?
N8 C4 N9 . . 120.7(6) ?
N8 C4 N7 . . 119.4(6) ?
N9 C4 N7 . . 119.9(6) ?
C3 N10 H10A . . 120.000000 ?
C3 N10 H10B . . 120.000000 ?
H10A N10 H10B . . 120.000000 ?
C3 N11 H11A . . 120.000000 ?
C3 N11 H11B . . 120.000000 ?
H11A N11 H11B . . 120.000000 ?
C3 N12 H12A . . 120.000000 ?
C3 N12 H12B . . 120.000000 ?
H12A N12 H12B . . 120.000000 ?
N10 C3 N11 . . 120.9(6) ?
N10 C3 N12 . . 119.6(6) ?
N11 C3 N12 . . 119.4(6) ?

