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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2012777'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H12 N6 O4 S'
_chemical_formula_weight         216.24

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

_space_group_crystal_system      cubic
_space_group_IT_number           212
_space_group_name_H-M_alt        'P 43 3 2'
_space_group_name_Hall           'P 4acd 2ab 3'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'y+3/4, -x+3/4, z+1/4'
'-y+3/4, x+1/4, z+3/4'
'x+1/4, z+3/4, -y+3/4'
'-x+3/4, z+1/4, y+3/4'
'-x+1/4, -z+1/4, -y+1/4'
'x+3/4, -z+3/4, y+1/4'
'z+1/4, y+3/4, -x+3/4'
'z+3/4, -y+3/4, x+1/4'
'-z+3/4, y+1/4, x+3/4'
'-z+1/4, -y+1/4, -x+1/4'

_cell_length_a                   17.8273(6)
_cell_length_b                   17.8273(6)
_cell_length_c                   17.8273(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5665.7(6)
_cell_formula_units_Z            20
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9304
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             2280
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.286
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9706
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            131432
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1952
_reflns_number_gt                1900
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+3.6256P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1952
_refine_ls_number_parameters     131
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44481(4) 0.44481(4) 0.44481(4) 0.0154(3) Uani 1 3 d S T P . .
S2 S 0.29748(4) 0.04748(4) 0.375000 0.0157(3) Uani 1 2 d S T P . .
O1 O 0.28141(13) -0.00453(13) 0.31210(13) 0.0203(5) Uani 1 1 d . . . . .
O2 O 0.37575(12) 0.03741(12) 0.40058(13) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.48507(13) 0.42638(12) 0.37455(13) 0.0198(5) Uani 1 1 d . . . . .
O4 O 0.49290(12) 0.49290(12) 0.49290(12) 0.0181(8) Uani 1 3 d S T P . .
N1 N 0.125000 -0.07272(16) 0.32272(16) 0.0252(9) Uani 1 2 d S T P . .
H1A H 0.090095 -0.072720 0.287815 0.030 Uiso 0.5 1 calc R U P . .
H1B H 0.159905 -0.037815 0.322720 0.030 Uiso 0.5 1 calc R U P . .
N2 N 0.35108(17) -0.14890(17) 0.31965(19) 0.0275(7) Uani 1 1 d D . . . .
H2A H 0.336(3) -0.1027(19) 0.319(3) 0.033(12) Uiso 1 1 d D . . . .
H2B H 0.331(3) -0.186(3) 0.299(3) 0.052(15) Uiso 1 1 d D . . . .
N3 N 0.44375(19) -0.11121(18) 0.4008(2) 0.0315(7) Uani 1 1 d D . . . .
H3A H 0.416(2) -0.076(2) 0.411(3) 0.043(14) Uiso 1 1 d D . . . .
H3B H 0.486(2) -0.115(3) 0.424(3) 0.044(14) Uiso 1 1 d D . . . .
N4 N 0.4407(2) -0.23303(18) 0.3580(2) 0.0349(8) Uani 1 1 d D . . . .
H4A H 0.471(2) -0.248(3) 0.396(2) 0.042 Uiso 1 1 d D U . . .
H4B H 0.425(3) -0.265(3) 0.326(2) 0.042 Uiso 1 1 d D U . . .
N5 N 0.48353(19) 0.14913(18) 0.3496(2) 0.0314(8) Uani 1 1 d . . . . .
H5A H 0.525(3) 0.143(3) 0.332(3) 0.038(13) Uiso 1 1 d . . . . .
H5B H 0.448(3) 0.115(3) 0.350(3) 0.042(13) Uiso 1 1 d . . . . .
N6 N 0.51994(17) 0.26994(17) 0.375000 0.0325(11) Uani 1 2 d S T P . .
H6A H 0.565206 0.259581 0.358254 0.039 Uiso 0.5 1 calc R U P . .
H6B H 0.509582 0.315206 0.391746 0.039 Uiso 0.5 1 calc R U P . .
C1 C 0.125000 -0.125000 0.375000 0.0206(15) Uani 1 6 d S T P . .
C2 C 0.4114(2) -0.16444(19) 0.3599(2) 0.0250(7) Uani 1 1 d . . . . .
C3 C 0.46774(19) 0.21774(19) 0.375000 0.0262(11) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.480(2) . ?
S1 O3 1.481(2) 9 ?
S1 O3 1.481(2) 5 ?
S1 O4 1.485(4) . ?
S2 O2 1.479(2) . ?
S2 O2 1.479(2) 13_545 ?
S2 O1 1.483(2) . ?
S2 O1 1.483(2) 13_545 ?
N1 C1 1.318(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C2 1.323(5) . ?
N2 H2A 0.87(3) . ?
N2 H2B 0.84(3) . ?
N3 C2 1.328(5) . ?
N3 H3A 0.82(3) . ?
N3 H3B 0.86(3) . ?
N4 C2 1.330(4) . ?
N4 H4A 0.90(3) . ?
N4 H4B 0.85(3) . ?
N5 C3 1.334(4) . ?
N5 H5A 0.82(6) . ?
N5 H5B 0.88(6) . ?
N6 C3 1.316(7) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O3 109.27(10) . 9 ?
O3 S1 O3 109.27(10) . 5 ?
O3 S1 O3 109.27(10) 9 5 ?
O3 S1 O4 109.68(10) . . ?
O3 S1 O4 109.67(10) 9 . ?
O3 S1 O4 109.67(10) 5 . ?
O2 S2 O2 108.92(19) . 13_545 ?
O2 S2 O1 109.84(12) . . ?
O2 S2 O1 109.47(13) 13_545 . ?
O2 S2 O1 109.47(13) . 13_545 ?
O2 S2 O1 109.85(12) 13_545 13_545 ?
O1 S2 O1 109.3(2) . 13_545 ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C2 N2 H2A 117(3) . . ?
C2 N2 H2B 115(4) . . ?
H2A N2 H2B 128(5) . . ?
C2 N3 H3A 114(3) . . ?
C2 N3 H3B 125(3) . . ?
H3A N3 H3B 119(5) . . ?
C2 N4 H4A 119(3) . . ?
C2 N4 H4B 120(4) . . ?
H4A N4 H4B 121(5) . . ?
C3 N5 H5A 116(4) . . ?
C3 N5 H5B 119(3) . . ?
H5A N5 H5B 124(5) . . ?
C3 N6 H6A 120.0 . . ?
C3 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N1 C1 N1 120.0 10_545 7 ?
N1 C1 N1 120.0 10_545 . ?
N1 C1 N1 120.0 7 . ?
N2 C2 N3 120.1(3) . . ?
N2 C2 N4 119.9(3) . . ?
N3 C2 N4 120.1(3) . . ?
N6 C3 N5 119.9(2) . . ?
N6 C3 N5 119.9(2) . 13_545 ?
N5 C3 N5 120.1(5) . 13_545 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.88 2.25 3.048(3) 150.0 19
N1 H1B O1 0.88 2.25 3.048(3) 150.0 .
N2 H2A O1 0.87(3) 2.01(3) 2.861(4) 169(4) .
N2 H2B O4 0.84(3) 2.09(4) 2.898(3) 164(6) 16_544
N3 H3A O2 0.82(3) 2.15(4) 2.914(4) 154(5) .
N3 H3B O2 0.86(3) 2.14(3) 2.995(4) 171(5) 8_645
N4 H4B O3 0.85(3) 2.12(3) 2.961(4) 168(5) 23_544
N5 H5A O3 0.82(6) 2.21(5) 2.972(4) 155(5) 21_545
N5 H5B O2 0.88(6) 2.10(5) 2.913(4) 154(5) .
N6 H6B O3 0.88 2.05 2.857(3) 151.6 .
N6 H6A O3 0.88 2.05 2.857(3) 151.6 13_545

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2012783'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H38 N8 O10 S2'
_chemical_formula_weight         638.72

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.1728(4)
_cell_length_b                   11.1002(7)
_cell_length_c                   19.3610(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.265(2)
_cell_angle_gamma                90
_cell_volume                     1516.84(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9674
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.28

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.377
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.240
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9480
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46918
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6243
_reflns_number_gt                5761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.3302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6243
_refine_ls_number_parameters     440
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78971(9) 0.20140(6) 0.55934(3) 0.01994(16) Uani 1 1 d . . . . .
S2 S -0.18884(9) 0.49011(6) 0.07294(4) 0.02101(16) Uani 1 1 d . . . . .
O1 O -0.0783(3) 0.2178(2) 0.28317(12) 0.0400(6) Uani 1 1 d . . . . .
O2 O 0.5180(3) 0.6082(2) 0.18293(11) 0.0281(5) Uani 1 1 d D . . . .
H2B H 0.537(9) 0.555(5) 0.150(3) 0.12(2) Uiso 1 1 d D . . . .
O3 O 0.8284(3) 0.18918(19) 0.48641(10) 0.0247(4) Uani 1 1 d . . . . .
O4 O 0.7687(3) 0.33094(19) 0.57294(11) 0.0246(5) Uani 1 1 d . . . . .
O5 O 0.6116(3) 0.13797(19) 0.56410(11) 0.0265(5) Uani 1 1 d . . . . .
O6 O 0.9482(3) 0.1507(2) 0.60901(11) 0.0277(5) Uani 1 1 d . . . . .
O7 O -0.3671(3) 0.4323(2) 0.08404(11) 0.0294(5) Uani 1 1 d . . . . .
O8 O -0.2267(3) 0.6076(2) 0.03921(13) 0.0385(6) Uani 1 1 d . . . . .
O9 O -0.0626(4) 0.5044(2) 0.14058(12) 0.0454(6) Uani 1 1 d . . . . .
O10 O -0.0967(4) 0.4128(2) 0.02768(15) 0.0485(7) Uani 1 1 d . . . . .
N1 N 0.6519(4) 0.3509(2) 0.39280(13) 0.0248(6) Uani 1 1 d . . . . .
H1A H 0.711(5) 0.302(4) 0.425(2) 0.042(11) Uiso 1 1 d . . . . .
N2 N 0.1093(3) 0.7085(2) 0.18261(12) 0.0226(5) Uani 1 1 d . . . . .
H2A H 0.061(5) 0.643(3) 0.1597(17) 0.025(9) Uiso 1 1 d . . . . .
N3 N 0.0984(4) 0.4425(3) 0.53773(17) 0.0330(7) Uani 1 1 d . . . . .
H3A H 0.105(5) 0.518(4) 0.5307(19) 0.029(9) Uiso 1 1 d . . . . .
H3B H 0.000(5) 0.411(3) 0.5537(18) 0.033(9) Uiso 1 1 d . . . . .
N4 N 0.4134(4) 0.4337(3) 0.52940(17) 0.0320(6) Uani 1 1 d . . . . .
H4A H 0.528(6) 0.398(4) 0.547(2) 0.050(11) Uiso 1 1 d . . . . .
H4B H 0.397(5) 0.494(4) 0.5064(18) 0.026(9) Uiso 1 1 d . . . . .
N5 N 0.2745(4) 0.2727(3) 0.57427(15) 0.0303(6) Uani 1 1 d . . . . .
H5A H 0.375(7) 0.229(4) 0.576(2) 0.053(12) Uiso 1 1 d . . . . .
H5B H 0.181(6) 0.245(4) 0.585(2) 0.039(11) Uiso 1 1 d . . . . .
N6 N -0.0756(4) 0.1597(3) 0.04264(15) 0.0289(6) Uani 1 1 d . . . . .
H6A H -0.069(5) 0.238(4) 0.0478(18) 0.024(9) Uiso 1 1 d . . . . .
H6B H 0.009(6) 0.134(4) 0.031(2) 0.038(12) Uiso 1 1 d . . . . .
N7 N -0.2682(4) 0.0084(3) -0.01082(15) 0.0314(6) Uani 1 1 d . . . . .
H7A H -0.367(6) -0.018(4) -0.0271(19) 0.038(10) Uiso 1 1 d . . . . .
H7B H -0.175(6) -0.025(4) -0.0175(19) 0.035(10) Uiso 1 1 d . . . . .
N8 N -0.3983(4) 0.1846(3) 0.02092(14) 0.0272(6) Uani 1 1 d . . . . .
H8A H -0.498(6) 0.163(3) 0.001(2) 0.032(10) Uiso 1 1 d . . . . .
H8B H -0.382(5) 0.257(4) 0.0422(19) 0.031(9) Uiso 1 1 d . . . . .
C1 C 0.3828(5) 0.2230(3) 0.39141(17) 0.0356(8) Uani 1 1 d . . . . .
H1 H 0.450946 0.177945 0.429394 0.043 Uiso 1 1 calc R U . . .
C2 C 0.2009(5) 0.1926(4) 0.36326(18) 0.0401(8) Uani 1 1 d . . . . .
H2 H 0.141459 0.126679 0.381920 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1010(4) 0.2592(3) 0.30631(16) 0.0300(7) Uani 1 1 d . . . . .
C4 C 0.1818(4) 0.3554(3) 0.27861(16) 0.0250(6) Uani 1 1 d . . . . .
H4 H 0.112468 0.398644 0.240055 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3705(4) 0.3904(3) 0.30787(14) 0.0216(6) Uani 1 1 d . . . . .
C6 C 0.4687(4) 0.3214(3) 0.36395(15) 0.0253(6) Uani 1 1 d . . . . .
C7 C 0.7406(4) 0.4440(3) 0.37101(15) 0.0249(6) Uani 1 1 d . . . . .
H7 H 0.866367 0.462806 0.393112 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6500(4) 0.5142(3) 0.31589(15) 0.0235(6) Uani 1 1 d . . . . .
H8 H 0.714648 0.581061 0.300573 0.028 Uiso 1 1 calc R U . . .
C9 C 0.4679(4) 0.4887(3) 0.28294(13) 0.0203(5) Uani 1 1 d . . . . .
C10 C -0.1819(5) 0.2711(4) 0.22061(17) 0.0360(8) Uani 1 1 d . . . . .
H10A H -0.187106 0.358604 0.226665 0.054 Uiso 1 1 calc R U . . .
H10B H -0.310914 0.238465 0.211358 0.054 Uiso 1 1 calc R U . . .
H10C H -0.118679 0.252658 0.180978 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3775(4) 0.5626(3) 0.21897(15) 0.0211(6) Uani 1 1 d . . . . .
H11 H 0.289797 0.509470 0.186398 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2628(4) 0.6680(3) 0.24222(14) 0.0204(6) Uani 1 1 d . . . . .
H12 H 0.199669 0.638304 0.281036 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3786(4) 0.7806(3) 0.26892(15) 0.0235(6) Uani 1 1 d . . . . .
H13A H 0.500052 0.780673 0.251326 0.028 Uiso 1 1 calc R U . . .
H13B H 0.407186 0.780354 0.320865 0.028 Uiso 1 1 calc R U . . .
C14 C 0.2629(4) 0.8939(3) 0.24255(17) 0.0301(7) Uani 1 1 d . . . . .
H14 H 0.324591 0.966994 0.266721 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2509(5) 0.9061(3) 0.16282(17) 0.0317(7) Uani 1 1 d . . . . .
H15 H 0.149248 0.966152 0.145676 0.038 Uiso 1 1 calc R U . . .
C16 C 0.1852(4) 0.7839(3) 0.12983(16) 0.0283(7) Uani 1 1 d . . . . .
H16A H 0.085348 0.796469 0.088048 0.034 Uiso 1 1 calc R U . . .
H16B H 0.292969 0.742112 0.114675 0.034 Uiso 1 1 calc R U . . .
C17 C -0.0375(4) 0.7782(3) 0.21237(18) 0.0320(7) Uani 1 1 d . . . . .
H17A H -0.102693 0.724680 0.241350 0.038 Uiso 1 1 calc R U . . .
H17B H -0.133283 0.811303 0.173859 0.038 Uiso 1 1 calc R U . . .
C18 C 0.0618(5) 0.8813(3) 0.25757(17) 0.0344(8) Uani 1 1 d . . . . .
H18A H -0.008737 0.957428 0.246156 0.041 Uiso 1 1 calc R U . . .
H18B H 0.066018 0.863440 0.307926 0.041 Uiso 1 1 calc R U . . .
C19 C 0.4280(6) 0.9469(4) 0.1378(2) 0.0524(11) Uani 1 1 d . . . . .
H19 H 0.427051 0.937744 0.088971 0.063 Uiso 1 1 calc R U . . .
C20 C 0.5794(6) 0.9920(5) 0.1733(3) 0.0623(12) Uani 1 1 d . . . . .
H20A H 0.590117 1.003715 0.222411 0.075 Uiso 1 1 calc R U . . .
H20B H 0.681181 1.013942 0.150407 0.075 Uiso 1 1 calc R U . . .
C21 C 0.2617(4) 0.3830(3) 0.54745(16) 0.0261(7) Uani 1 1 d . . . . .
C22 C -0.2493(4) 0.1178(3) 0.01645(15) 0.0239(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O6 1.464(2) . ?
S1 O4 1.474(2) . ?
S1 O5 1.476(2) . ?
S1 O3 1.493(2) . ?
S2 O8 1.462(2) . ?
S2 O9 1.462(2) . ?
S2 O10 1.465(2) . ?
S2 O7 1.480(2) . ?
O1 C3 1.364(4) . ?
O1 C10 1.431(4) . ?
O2 C11 1.417(3) . ?
O2 H2B 0.90(3) . ?
N1 C7 1.322(4) . ?
N1 C6 1.372(4) . ?
N1 H1A 0.87(4) . ?
N2 C16 1.497(4) . ?
N2 C17 1.502(4) . ?
N2 C12 1.514(3) . ?
N2 H2A 0.89(4) . ?
N3 C21 1.328(4) . ?
N3 H3A 0.86(4) . ?
N3 H3B 0.89(4) . ?
N4 C21 1.326(4) . ?
N4 H4A 0.92(4) . ?
N4 H4B 0.80(4) . ?
N5 C21 1.327(4) . ?
N5 H5A 0.87(5) . ?
N5 H5B 0.80(4) . ?
N6 C22 1.342(4) . ?
N6 H6A 0.88(4) . ?
N6 H6B 0.75(4) . ?
N7 C22 1.322(4) . ?
N7 H7A 0.78(4) . ?
N7 H7B 0.80(4) . ?
N8 C22 1.316(4) . ?
N8 H8A 0.78(4) . ?
N8 H8B 0.90(4) . ?
C1 C2 1.364(5) . ?
C1 C6 1.404(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.412(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(4) . ?
C4 C5 1.424(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(4) . ?
C5 C9 1.426(4) . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C11 1.530(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.543(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.538(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.542(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C18 1.527(5) . ?
C14 C15 1.537(5) . ?
C14 H14 1.0000 . ?
C15 C19 1.508(5) . ?
C15 C16 1.537(5) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.536(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.279(6) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9500 . ?
C20 H20B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 S1 O4 110.49(13) . . ?
O6 S1 O5 110.78(13) . . ?
O4 S1 O5 109.68(12) . . ?
O6 S1 O3 109.43(12) . . ?
O4 S1 O3 107.44(12) . . ?
O5 S1 O3 108.95(12) . . ?
O8 S2 O9 109.83(15) . . ?
O8 S2 O10 108.84(16) . . ?
O9 S2 O10 109.02(17) . . ?
O8 S2 O7 110.78(13) . . ?
O9 S2 O7 109.28(14) . . ?
O10 S2 O7 109.05(14) . . ?
C3 O1 C10 117.1(3) . . ?
C11 O2 H2B 109(4) . . ?
C7 N1 C6 122.5(3) . . ?
C7 N1 H1A 121(3) . . ?
C6 N1 H1A 117(3) . . ?
C16 N2 C17 109.8(2) . . ?
C16 N2 C12 112.5(2) . . ?
C17 N2 C12 109.0(2) . . ?
C16 N2 H2A 106(2) . . ?
C17 N2 H2A 112(2) . . ?
C12 N2 H2A 108(2) . . ?
C21 N3 H3A 116(2) . . ?
C21 N3 H3B 119(2) . . ?
H3A N3 H3B 121(3) . . ?
C21 N4 H4A 116(3) . . ?
C21 N4 H4B 117(2) . . ?
H4A N4 H4B 126(3) . . ?
C21 N5 H5A 122(3) . . ?
C21 N5 H5B 117(3) . . ?
H5A N5 H5B 121(4) . . ?
C22 N6 H6A 114(2) . . ?
C22 N6 H6B 120(3) . . ?
H6A N6 H6B 113(4) . . ?
C22 N7 H7A 122(3) . . ?
C22 N7 H7B 118(3) . . ?
H7A N7 H7B 119(4) . . ?
C22 N8 H8A 119(3) . . ?
C22 N8 H8B 119(2) . . ?
H8A N8 H8B 122(4) . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
O1 C3 C4 125.1(3) . . ?
O1 C3 C2 113.4(3) . . ?
C4 C3 C2 121.5(3) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C9 117.9(3) . . ?
C4 C5 C9 124.2(3) . . ?
N1 C6 C1 119.0(3) . . ?
N1 C6 C5 119.7(3) . . ?
C1 C6 C5 121.4(3) . . ?
N1 C7 C8 119.9(3) . . ?
N1 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C5 118.8(3) . . ?
C8 C9 C11 119.7(3) . . ?
C5 C9 C11 121.4(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C9 110.7(2) . . ?
O2 C11 C12 109.6(2) . . ?
C9 C11 C12 110.0(2) . . ?
O2 C11 H11 108.8 . . ?
C9 C11 H11 108.8 . . ?
C12 C11 H11 108.8 . . ?
N2 C12 C13 106.9(2) . . ?
N2 C12 C11 110.8(2) . . ?
C13 C12 C11 115.5(2) . . ?
N2 C12 H12 107.8 . . ?
C13 C12 H12 107.8 . . ?
C11 C12 H12 107.8 . . ?
C12 C13 C14 108.9(2) . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C18 C14 C15 108.3(3) . . ?
C18 C14 C13 109.5(3) . . ?
C15 C14 C13 109.6(3) . . ?
C18 C14 H14 109.8 . . ?
C15 C14 H14 109.8 . . ?
C13 C14 H14 109.8 . . ?
C19 C15 C14 116.7(3) . . ?
C19 C15 C16 110.2(3) . . ?
C14 C15 C16 107.3(3) . . ?
C19 C15 H15 107.4 . . ?
C14 C15 H15 107.4 . . ?
C16 C15 H15 107.4 . . ?
N2 C16 C15 109.4(3) . . ?
N2 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N2 C17 C18 108.5(2) . . ?
N2 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
N2 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C14 C18 C17 108.5(3) . . ?
C14 C18 H18A 110.0 . . ?
C17 C18 H18A 110.0 . . ?
C14 C18 H18B 110.0 . . ?
C17 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C20 C19 C15 129.0(4) . . ?
C20 C19 H19 115.5 . . ?
C15 C19 H19 115.5 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
N4 C21 N5 119.5(3) . . ?
N4 C21 N3 119.7(3) . . ?
N5 C21 N3 120.8(3) . . ?
N8 C22 N7 121.1(3) . . ?
N8 C22 N6 119.3(3) . . ?
N7 C22 N6 119.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2B O7 0.90(3) 2.07(3) 2.952(3) 169(6) 1_655
N1 H1A O3 0.87(4) 1.83(4) 2.701(3) 175(4) .
N2 H2A O9 0.89(4) 1.78(4) 2.637(4) 161(3) .
N3 H3A O3 0.86(4) 2.00(4) 2.843(4) 169(3) 2_656
N3 H3B O4 0.89(4) 1.98(4) 2.858(4) 171(3) 1_455
N4 H4A O4 0.92(4) 1.86(4) 2.782(3) 174(4) .
N4 H4B O5 0.80(4) 2.09(4) 2.887(4) 170(3) 2_656
N5 H5A O5 0.87(5) 2.02(5) 2.879(4) 171(4) .
N5 H5B O6 0.80(4) 2.09(4) 2.885(4) 172(4) 1_455
N6 H6A O10 0.88(4) 1.98(4) 2.825(4) 162(3) .
N6 H6B O8 0.75(4) 2.26(4) 2.962(4) 158(4) 2_545
N7 H7A O7 0.78(4) 2.10(4) 2.871(4) 171(4) 2_445
N7 H7B O10 0.80(4) 2.11(4) 2.896(4) 170(4) 2_545
N8 H8A O8 0.78(4) 2.08(4) 2.865(4) 173(4) 2_445
N8 H8B O7 0.90(4) 2.11(4) 3.002(4) 174(3) .
C4 H4 O9 0.95 2.41 3.359(4) 178.7 .
C7 H7 O6 0.95 2.48 3.176(4) 130.3 2_756
C16 H16B O2 0.99 2.41 3.112(4) 127.5 .
C18 H18B O4 0.99 2.43 3.337(4) 152.9 2_656

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.047


# start Validation Reply Form
_vrf_PLAT601_1                   
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        205 Ang**3
RESPONSE: These are the natural pores formed in the guanidinium sulfate
structure, and contain no solvent molecules.  All electron density of 
significance is modeled by the guanidinium sulfate framework (max diff
peak is 0.74 e-/A^3).
;
# end Validation Reply Form
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2012782'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H34 N10 O8 S2'
_chemical_formula_weight         474.58

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

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   10.8776(4)
_cell_length_b                   10.8776(4)
_cell_length_c                   20.4184(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2415.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.398
_exptl_crystal_size_min          0.351
_exptl_absorpt_coefficient_mu    0.272
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9539
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22103
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4984
_reflns_number_gt                4821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.0990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2222 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4984
_refine_ls_number_parameters     341
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0620
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28959(5) 0.18611(4) 0.56428(2) 0.01636(12) Uani 1 1 d . . . . .
S2 S 0.73104(5) 0.26227(4) 0.29477(2) 0.01722(12) Uani 1 1 d . . . . .
O1 O 0.34664(14) 0.08283(14) 0.60106(7) 0.0239(3) Uani 1 1 d . . . . .
O2 O 0.32017(15) 0.17112(14) 0.49443(7) 0.0217(3) Uani 1 1 d . . . . .
O3 O 0.15567(14) 0.18178(14) 0.57386(8) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.33980(14) 0.30386(14) 0.58829(8) 0.0245(3) Uani 1 1 d . . . . .
O5 O 0.86557(13) 0.24646(14) 0.29364(8) 0.0217(3) Uani 1 1 d . . . . .
O6 O 0.70217(14) 0.39549(13) 0.30123(7) 0.0215(3) Uani 1 1 d . . . . .
O7 O 0.67803(16) 0.19566(14) 0.35064(9) 0.0300(4) Uani 1 1 d . . . . .
O8 O 0.67830(15) 0.21760(16) 0.23274(9) 0.0303(4) Uani 1 1 d . . . . .
N1 N 0.51915(19) 0.07505(18) 0.69692(10) 0.0258(4) Uani 1 1 d . . . . .
H1 H 0.461(2) 0.083(2) 0.6683(12) 0.017(6) Uiso 1 1 d . . . . .
N2 N 0.9542(2) 0.0058(2) 0.34202(11) 0.0304(5) Uani 1 1 d . . . . .
H2A H 1.016(3) -0.029(3) 0.3273(14) 0.031(7) Uiso 1 1 d . . . . .
H2B H 0.933(3) 0.068(3) 0.3291(15) 0.032(8) Uiso 1 1 d . . . . .
N3 N 0.7979(2) 0.0006(2) 0.41816(10) 0.0279(5) Uani 1 1 d . . . . .
H3A H 0.766(2) -0.033(3) 0.4504(13) 0.023(7) Uiso 1 1 d . . . . .
H3B H 0.764(3) 0.055(3) 0.4014(14) 0.027(7) Uiso 1 1 d . . . . .
N4 N 0.9376(2) -0.15618(19) 0.41333(11) 0.0293(5) Uani 1 1 d . . . . .
H4A H 0.999(3) -0.188(3) 0.3963(14) 0.028(7) Uiso 1 1 d . . . . .
H4B H 0.884(3) -0.200(3) 0.4368(14) 0.029(7) Uiso 1 1 d . . . . .
N5 N 0.63407(18) 0.4838(2) 0.42921(10) 0.0243(4) Uani 1 1 d . . . . .
H5A H 0.659(2) 0.456(3) 0.3956(15) 0.025(7) Uiso 1 1 d . . . . .
H5B H 0.670(3) 0.541(3) 0.4456(14) 0.027(7) Uiso 1 1 d . . . . .
N6 N 0.5117(2) 0.31295(19) 0.43719(10) 0.0264(4) Uani 1 1 d . . . . .
H6A H 0.460(3) 0.278(3) 0.4543(14) 0.025(7) Uiso 1 1 d . . . . .
H6B H 0.552(3) 0.281(3) 0.4054(15) 0.031(7) Uiso 1 1 d . . . . .
N7 N 0.50453(19) 0.4612(2) 0.51728(10) 0.0259(4) Uani 1 1 d . . . . .
H7A H 0.461(3) 0.418(3) 0.5392(14) 0.030(7) Uiso 1 1 d . . . . .
H7B H 0.524(2) 0.535(3) 0.5317(13) 0.026(7) Uiso 1 1 d . . . . .
N8 N 0.0595(2) 0.3245(2) 0.67937(11) 0.0302(5) Uani 1 1 d . . . . .
H8A H -0.006(3) 0.308(3) 0.6956(13) 0.026(7) Uiso 1 1 d . . . . .
H8B H 0.093(3) 0.286(3) 0.6500(13) 0.024(7) Uiso 1 1 d . . . . .
N9 N 0.2241(2) 0.4577(2) 0.68045(10) 0.0279(5) Uani 1 1 d . . . . .
H9A H 0.264(3) 0.512(3) 0.6997(15) 0.038(8) Uiso 1 1 d . . . . .
H9B H 0.261(2) 0.406(2) 0.6529(14) 0.022(6) Uiso 1 1 d . . . . .
N10 N 0.0671(2) 0.4803(2) 0.75482(11) 0.0392(6) Uani 1 1 d . . . . .
H10A H 0.012(3) 0.439(3) 0.7790(16) 0.040(8) Uiso 1 1 d . . . . .
H10B H 0.109(4) 0.535(4) 0.769(2) 0.078(13) Uiso 1 1 d . . . . .
C1 C 0.6064(3) 0.1778(3) 0.68447(14) 0.0396(6) Uani 1 1 d . . . . .
H1A H 0.676373 0.170779 0.715243 0.048 Uiso 1 1 calc R U . . .
H1B H 0.564254 0.256689 0.693548 0.048 Uiso 1 1 calc R U . . .
C2 C 0.6557(3) 0.1802(3) 0.61486(16) 0.0434(7) Uani 1 1 d . . . . .
H2C H 0.709899 0.109445 0.607967 0.065 Uiso 1 1 calc R U . . .
H2D H 0.702001 0.256355 0.607810 0.065 Uiso 1 1 calc R U . . .
H2E H 0.586932 0.176411 0.583908 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4612(3) 0.0838(2) 0.76443(12) 0.0348(6) Uani 1 1 d . . . . .
H3C H 0.423277 0.003818 0.775608 0.042 Uiso 1 1 calc R U . . .
H3D H 0.526322 0.100732 0.797113 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3660(3) 0.1819(3) 0.76846(14) 0.0440(7) Uani 1 1 d . . . . .
H4C H 0.403001 0.261360 0.757291 0.066 Uiso 1 1 calc R U . . .
H4D H 0.333012 0.185347 0.813085 0.066 Uiso 1 1 calc R U . . .
H4E H 0.299390 0.163624 0.737664 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5736(2) -0.0506(2) 0.68596(14) 0.0324(6) Uani 1 1 d . . . . .
H5C H 0.507648 -0.112757 0.690480 0.039 Uiso 1 1 calc R U . . .
H5D H 0.605003 -0.055231 0.640520 0.039 Uiso 1 1 calc R U . . .
C6 C 0.6759(4) -0.0827(4) 0.7320(2) 0.0663(11) Uani 1 1 d . . . . .
H6C H 0.740073 -0.019675 0.729509 0.099 Uiso 1 1 calc R U . . .
H6D H 0.710518 -0.162660 0.719880 0.099 Uiso 1 1 calc R U . . .
H6E H 0.643885 -0.086716 0.776854 0.099 Uiso 1 1 calc R U . . .
C7 C 0.8962(2) -0.0497(2) 0.39080(10) 0.0225(5) Uani 1 1 d . . . . .
C8 C 0.55089(19) 0.4181(2) 0.46167(10) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.1180(2) 0.4193(2) 0.70534(11) 0.0236(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4705(15) . ?
S1 O2 1.4735(16) . ?
S1 O4 1.4762(16) . ?
S1 O1 1.4871(15) . ?
S2 O7 1.4693(16) . ?
S2 O8 1.4729(18) . ?
S2 O5 1.4736(15) . ?
S2 O6 1.4885(14) . ?
N1 C1 1.488(3) . ?
N1 C5 1.507(3) . ?
N1 C3 1.519(3) . ?
N1 H1 0.87(3) . ?
N2 C7 1.324(3) . ?
N2 H2A 0.83(3) . ?
N2 H2B 0.76(3) . ?
N3 C7 1.325(3) . ?
N3 H3A 0.83(3) . ?
N3 H3B 0.78(3) . ?
N4 C7 1.325(3) . ?
N4 H4A 0.83(3) . ?
N4 H4B 0.89(3) . ?
N5 C8 1.330(3) . ?
N5 H5A 0.80(3) . ?
N5 H5B 0.80(3) . ?
N6 C8 1.319(3) . ?
N6 H6A 0.76(3) . ?
N6 H6B 0.86(3) . ?
N7 C8 1.328(3) . ?
N7 H7A 0.80(3) . ?
N7 H7B 0.88(3) . ?
N8 C9 1.323(3) . ?
N8 H8A 0.81(3) . ?
N8 H8B 0.82(3) . ?
N9 C9 1.329(3) . ?
N9 H9A 0.84(3) . ?
N9 H9B 0.89(3) . ?
N10 C9 1.330(3) . ?
N10 H10A 0.90(3) . ?
N10 H10B 0.80(5) . ?
C1 C2 1.519(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C3 C4 1.489(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4C 0.9800 . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C5 C6 1.498(4) . ?
C5 H5C 0.9900 . ?
C5 H5D 0.9900 . ?
C6 H6C 0.9800 . ?
C6 H6D 0.9800 . ?
C6 H6E 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 110.42(9) . . ?
O3 S1 O4 110.50(9) . . ?
O2 S1 O4 109.51(9) . . ?
O3 S1 O1 108.79(9) . . ?
O2 S1 O1 108.12(9) . . ?
O4 S1 O1 109.47(10) . . ?
O7 S2 O8 110.62(11) . . ?
O7 S2 O5 110.14(10) . . ?
O8 S2 O5 109.56(9) . . ?
O7 S2 O6 109.17(9) . . ?
O8 S2 O6 108.38(9) . . ?
O5 S2 O6 108.93(9) . . ?
C1 N1 C5 113.9(2) . . ?
C1 N1 C3 111.85(19) . . ?
C5 N1 C3 110.78(19) . . ?
C1 N1 H1 105.8(16) . . ?
C5 N1 H1 106.4(16) . . ?
C3 N1 H1 107.6(16) . . ?
C7 N2 H2A 117(2) . . ?
C7 N2 H2B 121(2) . . ?
H2A N2 H2B 122(3) . . ?
C7 N3 H3A 119.4(18) . . ?
C7 N3 H3B 121(2) . . ?
H3A N3 H3B 119(3) . . ?
C7 N4 H4A 120(2) . . ?
C7 N4 H4B 115.6(18) . . ?
H4A N4 H4B 122(3) . . ?
C8 N5 H5A 117(2) . . ?
C8 N5 H5B 122(2) . . ?
H5A N5 H5B 119(3) . . ?
C8 N6 H6A 120(2) . . ?
C8 N6 H6B 118.2(19) . . ?
H6A N6 H6B 122(3) . . ?
C8 N7 H7A 120(2) . . ?
C8 N7 H7B 120.9(17) . . ?
H7A N7 H7B 119(3) . . ?
C9 N8 H8A 116(2) . . ?
C9 N8 H8B 118.6(19) . . ?
H8A N8 H8B 125(3) . . ?
C9 N9 H9A 120(2) . . ?
C9 N9 H9B 115.7(17) . . ?
H9A N9 H9B 121(3) . . ?
C9 N10 H10A 117(2) . . ?
C9 N10 H10B 114(3) . . ?
H10A N10 H10B 123(4) . . ?
N1 C1 C2 113.4(2) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C1 C2 H2E 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
C4 C3 N1 112.6(2) . . ?
C4 C3 H3C 109.1 . . ?
N1 C3 H3C 109.1 . . ?
C4 C3 H3D 109.1 . . ?
N1 C3 H3D 109.1 . . ?
H3C C3 H3D 107.8 . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C6 C5 N1 114.2(2) . . ?
C6 C5 H5C 108.7 . . ?
N1 C5 H5C 108.7 . . ?
C6 C5 H5D 108.7 . . ?
N1 C5 H5D 108.7 . . ?
H5C C5 H5D 107.6 . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6D 109.5 . . ?
H6C C6 H6D 109.5 . . ?
C5 C6 H6E 109.5 . . ?
H6C C6 H6E 109.5 . . ?
H6D C6 H6E 109.5 . . ?
N2 C7 N3 120.9(2) . . ?
N2 C7 N4 119.8(2) . . ?
N3 C7 N4 119.3(2) . . ?
N6 C8 N7 120.5(2) . . ?
N6 C8 N5 119.8(2) . . ?
N7 C8 N5 119.6(2) . . ?
N8 C9 N9 120.6(2) . . ?
N8 C9 N10 119.6(2) . . ?
N9 C9 N10 119.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.87(3) 1.85(3) 2.713(2) 172(2) .
N2 H2A O3 0.83(3) 2.27(3) 3.058(3) 159(3) 4_654
N2 H2B O5 0.76(3) 2.20(3) 2.960(3) 178(3) .
N3 H3A O5 0.83(3) 2.20(3) 2.993(3) 158(2) 3_645
N3 H3B O7 0.78(3) 2.07(3) 2.847(3) 176(3) .
N4 H4A O1 0.83(3) 2.16(3) 2.899(3) 149(3) 4_654
N4 H4A O3 0.83(3) 2.50(3) 3.223(3) 146(3) 4_654
N4 H4B O5 0.89(3) 2.70(3) 3.339(3) 129(2) 3_645
N4 H4B O8 0.89(3) 1.96(3) 2.846(3) 170(3) 3_645
N5 H5A O6 0.80(3) 2.09(3) 2.881(3) 172(3) .
N5 H5B O8 0.80(3) 2.08(3) 2.876(3) 173(3) 3_655
N6 H6A O2 0.76(3) 2.08(3) 2.844(3) 175(3) .
N6 H6B O7 0.86(3) 1.99(3) 2.833(3) 165(3) .
N7 H7A O4 0.80(3) 2.07(3) 2.871(3) 175(3) .
N7 H7B O6 0.88(3) 2.05(3) 2.921(3) 167(3) 3_655
N8 H8A O2 0.81(3) 2.06(3) 2.839(3) 163(3) 3
N8 H8B O3 0.82(3) 2.04(3) 2.854(3) 173(3) .
N9 H9A O6 0.84(3) 2.33(3) 3.046(3) 144(3) 2_665
N9 H9B O4 0.89(3) 1.93(3) 2.815(3) 176(2) .
N10 H10A O1 0.90(3) 2.06(3) 2.939(3) 166(3) 3
N10 H10A O2 0.90(3) 2.48(3) 3.129(3) 130(3) 3
N10 H10B O5 0.80(5) 2.45(5) 3.162(3) 149(4) 2_665
N10 H10B O6 0.80(5) 2.28(5) 3.004(3) 149(4) 2_665

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.050

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 2012781'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H87 N34 O26.50 S6'
_chemical_formula_weight         1432.60

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   26.0251(8)
_cell_length_b                   22.0693(6)
_cell_length_c                   12.5545(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7210.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9917
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             3036
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.141
_exptl_absorpt_coefficient_mu    0.278
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59324
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.024
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             13979
_reflns_number_gt                11583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0764P)²+3.9769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4541 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         13979
_refine_ls_number_parameters     945
_refine_ls_number_restraints     188
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70952(4) -0.09410(5) 0.63023(10) 0.0192(2) Uani 1 1 d . . . . .
S2 S 0.71437(4) 0.57358(5) 0.63796(10) 0.0184(2) Uani 1 1 d . . . . .
S3 S 0.72006(4) 0.24383(5) 0.63968(11) 0.0231(3) Uani 1 1 d . . . . .
S4 S 0.54763(5) 0.24328(5) 1.11136(11) 0.0279(3) Uani 1 1 d . . . . .
S5 S 0.53787(5) 0.57503(6) 1.08995(12) 0.0334(3) Uani 1 1 d D . . . .
S6 S 0.54227(4) -0.08646(5) 0.12137(11) 0.0246(3) Uani 1 1 d D . . . .
O1 O 0.70822(12) -0.09352(14) 0.7476(3) 0.0250(7) Uani 1 1 d . . . . .
O2 O 0.65688(13) -0.09611(16) 0.5881(3) 0.0299(8) Uani 1 1 d . . . . .
O3 O 0.73786(12) -0.14811(14) 0.5918(3) 0.0245(7) Uani 1 1 d . . . . .
O4 O 0.73614(12) -0.03953(14) 0.5903(3) 0.0246(7) Uani 1 1 d . . . . .
O5 O 0.73458(13) 0.52004(14) 0.5807(3) 0.0263(7) Uani 1 1 d . . . . .
O6 O 0.73573(15) 0.57483(15) 0.7460(3) 0.0329(8) Uani 1 1 d . . . . .
O7 O 0.73183(11) 0.62916(13) 0.5804(3) 0.0223(7) Uani 1 1 d . . . . .
O8 O 0.65828(12) 0.57290(15) 0.6412(3) 0.0349(8) Uani 1 1 d . . . . .
O9 O 0.74536(13) 0.29785(14) 0.5929(3) 0.0262(7) Uani 1 1 d . . . . .
O10 O 0.74482(13) 0.18902(15) 0.5953(3) 0.0295(8) Uani 1 1 d . . . . .
O11 O 0.7263(2) 0.24408(16) 0.7557(3) 0.0518(13) Uani 1 1 d . . . . .
O12 O 0.66615(16) 0.24412(19) 0.6119(5) 0.0633(16) Uani 1 1 d . . . . .
O13 O 0.52141(12) 0.18864(15) 1.0696(3) 0.0328(8) Uani 1 1 d . . . . .
O14 O 0.60198(13) 0.24186(15) 1.0769(3) 0.0343(9) Uani 1 1 d . . . . .
O15 O 0.52299(13) 0.29784(15) 1.0683(3) 0.0350(9) Uani 1 1 d . . . . .
O16 O 0.54439(14) 0.24320(16) 1.2282(3) 0.0354(9) Uani 1 1 d . . . . .
O17 O 0.51792(14) 0.52048(16) 1.1406(3) 0.0372(8) Uani 1 1 d . . . . .
O18A O 0.49904(19) 0.5920(2) 1.0070(4) 0.0325(14) Uani 0.714(7) 1 d D . P A 1
O19A O 0.5329(2) 0.6235(2) 1.1773(4) 0.0359(14) Uani 0.714(7) 1 d D . P A 1
O20A O 0.5883(2) 0.5735(2) 1.0522(5) 0.0366(15) Uani 0.714(7) 1 d D . P A 1
O18B O 0.5932(4) 0.5780(5) 1.1382(10) 0.023(3) Uani 0.286(7) 1 d D . P A 2
O19B O 0.5566(5) 0.5427(5) 0.9789(9) 0.033(3) Uani 0.286(7) 1 d D . P A 2
O20B O 0.5204(4) 0.6308(5) 1.0579(11) 0.035(4) Uani 0.286(7) 1 d D . P A 2
O21 O 0.5139(2) -0.0387(3) 0.1753(4) 0.0766(17) Uani 1 1 d . . . . .
O22A O 0.5498(3) -0.0611(4) 0.0167(5) 0.081(3) Uani 0.676(8) 1 d D U P B 1
O23A O 0.5183(3) -0.1443(3) 0.1120(13) 0.107(4) Uani 0.676(8) 1 d D U P B 1
O24A O 0.5925(2) -0.0918(3) 0.1725(5) 0.0365(16) Uani 0.676(8) 1 d D U P B 1
O22B O 0.5918(4) -0.0818(7) 0.0656(11) 0.052(4) Uani 0.324(8) 1 d D U P B 2
O23B O 0.5061(6) -0.1211(10) 0.0572(10) 0.065(5) Uani 0.324(8) 1 d D U P B 2
O24B O 0.5505(6) -0.1284(6) 0.2111(12) 0.069(4) Uani 0.324(8) 1 d D U P B 2
N1 N 0.72812(19) -0.26026(18) 0.7069(4) 0.0353(11) Uani 1 1 d . . . . .
H1A H 0.7278 -0.2950 0.6726 0.042 Uiso 1 1 calc R U . . .
H1B H 0.7246 -0.2261 0.6716 0.042 Uiso 1 1 calc R U . . .
N2 N 0.73481(17) -0.20694(18) 0.8635(4) 0.0336(10) Uani 1 1 d . . . . .
H2A H 0.7389 -0.2063 0.9331 0.040 Uiso 1 1 calc R U . . .
H2B H 0.7313 -0.1728 0.8282 0.040 Uiso 1 1 calc R U . . .
N3 N 0.73926(17) -0.31083(18) 0.8646(3) 0.0328(10) Uani 1 1 d . . . . .
H3A H 0.7433 -0.3104 0.9341 0.039 Uiso 1 1 calc R U . . .
H3B H 0.7387 -0.3455 0.8300 0.039 Uiso 1 1 calc R U . . .
N4 N 0.52176(17) -0.0100(2) 0.3982(4) 0.0439(12) Uani 1 1 d . . . . .
H4A H 0.5175 -0.0189 0.3305 0.053 Uiso 1 1 calc R U . . .
H4B H 0.4994 0.0134 0.4309 0.053 Uiso 1 1 calc R U . . .
N5 N 0.56766(17) -0.0192(2) 0.5536(4) 0.0389(11) Uani 1 1 d . . . . .
H5A H 0.5939 -0.0343 0.5887 0.047 Uiso 1 1 calc R U . . .
H5B H 0.5453 0.0042 0.5865 0.047 Uiso 1 1 calc R U . . .
N6 N 0.59525(18) -0.0664(2) 0.4024(4) 0.0381(11) Uani 1 1 d . . . . .
H6A H 0.5912 -0.0755 0.3347 0.046 Uiso 1 1 calc R U . . .
H6B H 0.6218 -0.0807 0.4378 0.046 Uiso 1 1 calc R U . . .
N7 N 0.72712(19) 0.07481(19) 0.6967(3) 0.0356(11) Uani 1 1 d . . . . .
H7A H 0.7214 0.0407 0.6623 0.043 Uiso 1 1 calc R U . . .
H7B H 0.7260 0.1096 0.6624 0.043 Uiso 1 1 calc R U . . .
N8 N 0.74592(17) 0.12553(18) 0.8520(3) 0.0333(10) Uani 1 1 d . . . . .
H8A H 0.7448 0.1604 0.8182 0.040 Uiso 1 1 calc R U . . .
H8B H 0.7527 0.1246 0.9207 0.040 Uiso 1 1 calc R U . . .
N9 N 0.73902(18) 0.02189(18) 0.8513(4) 0.0357(11) Uani 1 1 d . . . . .
H9A H 0.7334 -0.0124 0.8175 0.043 Uiso 1 1 calc R U . . .
H9B H 0.7459 0.0216 0.9200 0.043 Uiso 1 1 calc R U . . .
N10 N 0.93261(16) 0.24250(19) 0.6183(4) 0.0386(12) Uani 1 1 d . . . . .
H10A H 0.9496 0.2081 0.6161 0.046 Uiso 1 1 calc R U . . .
H10B H 0.9494 0.2770 0.6217 0.046 Uiso 1 1 calc R U . . .
N11 N 0.85653(16) 0.29438(19) 0.6199(4) 0.0392(12) Uani 1 1 d . . . . .
H11A H 0.8734 0.3289 0.6234 0.047 Uiso 1 1 calc R U . . .
H11B H 0.8227 0.2943 0.6186 0.047 Uiso 1 1 calc R U . . .
N12 N 0.85724(17) 0.1901(2) 0.6113(4) 0.0383(12) Uani 1 1 d . . . . .
H12A H 0.8745 0.1558 0.6091 0.046 Uiso 1 1 calc R U . . .
H12B H 0.8234 0.1896 0.6100 0.046 Uiso 1 1 calc R U . . .
N13 N 0.57279(16) -0.1605(2) -0.3135(4) 0.0344(10) Uani 1 1 d . . . . .
H13A H 0.6016 -0.1519 -0.3468 0.041 Uiso 1 1 calc R U . . .
H13B H 0.5485 -0.1810 -0.3465 0.041 Uiso 1 1 calc R U . . .
N14 N 0.52188(17) -0.1548(2) -0.1641(4) 0.0405(12) Uani 1 1 d . . . . .
H14A H 0.4974 -0.1746 -0.1975 0.049 Uiso 1 1 calc R U . . .
H14B H 0.5173 -0.1430 -0.0978 0.049 Uiso 1 1 calc R U . . .
N15 N 0.60224(17) -0.1117(2) -0.1629(4) 0.0419(12) Uani 1 1 d . . . . .
H15A H 0.6312 -0.1029 -0.1955 0.050 Uiso 1 1 calc R U . . .
H15B H 0.5973 -0.1001 -0.0966 0.050 Uiso 1 1 calc R U . . .
N16 N 0.61311(18) 0.2157(2) 0.8457(4) 0.0463(13) Uani 1 1 d . . . . .
H16A H 0.6412 0.2277 0.8129 0.056 Uiso 1 1 calc R U . . .
H16B H 0.6096 0.2218 0.9146 0.056 Uiso 1 1 calc R U . . .
N17 N 0.5807(2) 0.1788(3) 0.6873(5) 0.0579(15) Uani 1 1 d . . . . .
H17A H 0.6086 0.1906 0.6536 0.069 Uiso 1 1 calc R U . . .
H17B H 0.5559 0.1606 0.6521 0.069 Uiso 1 1 calc R U . . .
N18 N 0.5331(2) 0.1721(3) 0.8419(5) 0.0597(16) Uani 1 1 d . . . . .
H18A H 0.5078 0.1550 0.8064 0.072 Uiso 1 1 calc R U . . .
H18B H 0.5301 0.1784 0.9108 0.072 Uiso 1 1 calc R U . . .
N19 N 0.74414(18) 0.40964(18) 0.7016(3) 0.0337(10) Uani 1 1 d . . . . .
H19A H 0.7414 0.4442 0.6671 0.040 Uiso 1 1 calc R U . . .
H19B H 0.7416 0.3751 0.6668 0.040 Uiso 1 1 calc R U . . .
N20 N 0.75594(17) 0.46153(18) 0.8579(3) 0.0321(10) Uani 1 1 d . . . . .
H20A H 0.7532 0.4960 0.8232 0.039 Uiso 1 1 calc R U . . .
H20B H 0.7612 0.4616 0.9271 0.039 Uiso 1 1 calc R U . . .
N21 N 0.75720(17) 0.35715(18) 0.8565(3) 0.0336(10) Uani 1 1 d . . . . .
H21A H 0.7632 0.3567 0.9255 0.040 Uiso 1 1 calc R U . . .
H21B H 0.7546 0.3228 0.8212 0.040 Uiso 1 1 calc R U . . .
N22 N 0.59806(17) 0.6147(2) 0.8218(4) 0.0421(12) Uani 1 1 d . . . . .
H22A H 0.5930 0.6012 0.8869 0.051 Uiso 1 1 calc R U . . .
H22B H 0.6267 0.6060 0.7880 0.051 Uiso 1 1 calc R U . . .
N23 N 0.57007(16) 0.6691(2) 0.6763(4) 0.0360(10) Uani 1 1 d . . . . .
H23A H 0.5466 0.6915 0.6448 0.043 Uiso 1 1 calc R U . . .
H23B H 0.5988 0.6602 0.6428 0.043 Uiso 1 1 calc R U . . .
N24 N 0.51892(16) 0.6618(2) 0.8247(4) 0.0382(11) Uani 1 1 d . . . . .
H24A H 0.4954 0.6842 0.7934 0.046 Uiso 1 1 calc R U . . .
H24B H 0.5137 0.6482 0.8897 0.046 Uiso 1 1 calc R U . . .
N25 N 0.65295(16) 0.1265(2) 1.0952(4) 0.0394(12) Uani 1 1 d . . . . .
H25A H 0.6868 0.1259 1.0932 0.047 Uiso 1 1 calc R U . . .
H25B H 0.6364 0.1611 1.0907 0.047 Uiso 1 1 calc R U . . .
N26 N 0.65136(16) 0.0228(2) 1.1118(4) 0.0448(14) Uani 1 1 d . . . . .
H26A H 0.6851 0.0214 1.1099 0.054 Uiso 1 1 calc R U . . .
H26B H 0.6335 -0.0109 1.1182 0.054 Uiso 1 1 calc R U . . .
N27 N 0.57587(17) 0.0768(2) 1.1064(5) 0.0466(15) Uani 1 1 d . . . . .
H27A H 0.5594 0.1115 1.1010 0.056 Uiso 1 1 calc R U . . .
H27B H 0.5585 0.0428 1.1129 0.056 Uiso 1 1 calc R U . . .
N28 N 0.65106(16) 0.36015(18) 1.0782(4) 0.0343(10) Uani 1 1 d . . . . .
H28A H 0.6848 0.3606 1.0748 0.041 Uiso 1 1 calc R U . . .
H28B H 0.6344 0.3256 1.0738 0.041 Uiso 1 1 calc R U . . .
N29 N 0.57434(17) 0.4107(2) 1.0956(5) 0.0423(13) Uani 1 1 d . . . . .
H29A H 0.5576 0.3761 1.0915 0.051 Uiso 1 1 calc R U . . .
H29B H 0.5573 0.4448 1.1035 0.051 Uiso 1 1 calc R U . . .
N30 N 0.65021(17) 0.46383(19) 1.0968(4) 0.0393(12) Uani 1 1 d . . . . .
H30A H 0.6840 0.4647 1.0935 0.047 Uiso 1 1 calc R U . . .
H30B H 0.6328 0.4977 1.1046 0.047 Uiso 1 1 calc R U . . .
N31 N 0.47269(18) 0.4886(2) 0.8697(4) 0.0415(12) Uani 1 1 d . . . . .
H31A H 0.4916 0.5153 0.9041 0.050 Uiso 1 1 calc R U . . .
H31B H 0.4768 0.4836 0.8006 0.050 Uiso 1 1 calc R U . . .
N32 N 0.43242(17) 0.4641(2) 1.0248(4) 0.0373(11) Uani 1 1 d . . . . .
H32A H 0.4514 0.4908 1.0590 0.045 Uiso 1 1 calc R U . . .
H32B H 0.4095 0.4425 1.0597 0.045 Uiso 1 1 calc R U . . .
N33 N 0.4101(2) 0.4160(2) 0.8699(4) 0.0481(13) Uani 1 1 d . . . . .
H33A H 0.4142 0.4107 0.8010 0.058 Uiso 1 1 calc R U . . .
H33B H 0.3872 0.3944 0.9048 0.058 Uiso 1 1 calc R U . . .
C1 C 0.73399(19) -0.2594(2) 0.8120(4) 0.0256(10) Uani 1 1 d . . . . .
C2 C 0.56167(19) -0.0315(2) 0.4506(4) 0.0304(11) Uani 1 1 d . . . . .
C3 C 0.7373(2) 0.0738(2) 0.7991(4) 0.0289(11) Uani 1 1 d . . . . .
C4 C 0.88213(19) 0.2423(2) 0.6164(4) 0.0305(12) Uani 1 1 d . . . . .
C5 C 0.56588(19) -0.1427(2) -0.2137(4) 0.0317(11) Uani 1 1 d . . . . .
C6 C 0.5761(2) 0.1884(3) 0.7912(5) 0.0459(15) Uani 1 1 d . . . . .
C7 C 0.75211(19) 0.4095(2) 0.8058(4) 0.0269(11) Uani 1 1 d . . . . .
C8 C 0.56214(19) 0.6486(2) 0.7741(4) 0.0304(11) Uani 1 1 d . . . . .
C9 C 0.6273(2) 0.0757(2) 1.1048(5) 0.0356(14) Uani 1 1 d . . . . .
C10 C 0.6255(2) 0.4113(2) 1.0900(5) 0.0321(12) Uani 1 1 d . . . . .
C11 C 0.4384(2) 0.4563(2) 0.9213(4) 0.0320(12) Uani 1 1 d . . . . .
O25 O 0.64155(12) 0.67829(15) 0.4911(3) 0.0298(8) Uani 1 1 d . . . . .
H25 H 0.6702 0.6656 0.5122 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6475(2) 0.7369(3) 0.4459(6) 0.0497(16) Uani 1 1 d . . . . .
H17C H 0.6717 0.7353 0.3850 0.060 Uiso 1 1 calc R U . . .
H17D H 0.6614 0.7654 0.4996 0.060 Uiso 1 1 calc R U . . .
C18 C 0.5954(3) 0.7582(3) 0.4087(6) 0.0561(19) Uani 1 1 d . . . . .
H18C H 0.5813 0.7288 0.3581 0.084 Uiso 1 1 calc R U . . .
H18D H 0.5988 0.7977 0.3738 0.084 Uiso 1 1 calc R U . . .
H18E H 0.5723 0.7618 0.4700 0.084 Uiso 1 1 calc R U . . .
C19A C 0.5885(8) 0.3718(9) 0.8137(14) 0.064(4) Uani 0.503(9) 1 d . U P C 3
H19C H 0.6183 0.3475 0.8373 0.077 Uiso 0.503(9) 1 calc R U P C 3
H19D H 0.5612 0.3674 0.8682 0.077 Uiso 0.503(9) 1 calc R U P C 3
C20A C 0.6041(8) 0.4373(9) 0.8078(15) 0.059(5) Uani 0.503(9) 1 d . U P C 3
H20C H 0.6344 0.4413 0.7620 0.089 Uiso 0.503(9) 1 calc R U P C 3
H20D H 0.6123 0.4520 0.8795 0.089 Uiso 0.503(9) 1 calc R U P C 3
H20E H 0.5758 0.4612 0.7782 0.089 Uiso 0.503(9) 1 calc R U P C 3
O26A O 0.5697(8) 0.3472(8) 0.7131(11) 0.044(3) Uani 0.503(9) 1 d . U P C 3
H26C H 0.5377 0.3522 0.7092 0.065 Uiso 0.503(9) 1 calc R U P C 3
C12A C 0.5984(9) 0.3215(14) 0.4392(17) 0.058(4) Uani 0.503(9) 1 d D U P C 3
H12C H 0.5689 0.2963 0.4387 0.069 Uiso 0.503(9) 1 calc R U P C 3
N34A N 0.6150(4) 0.3616(5) 0.5308(9) 0.046(3) Uani 0.503(9) 1 d . U P C 3
H34A H 0.6072 0.3511 0.5965 0.055 Uiso 0.503(9) 1 calc R U P C 3
C13A C 0.6405(5) 0.4112(6) 0.5140(10) 0.045(3) Uani 0.503(9) 1 d D U P C 3
H13C H 0.6435 0.4404 0.5692 0.054 Uiso 0.503(9) 1 calc R U P C 3
C14A C 0.6629(6) 0.4218(8) 0.4186(10) 0.063(4) Uani 0.503(9) 1 d D U P C 3
H14C H 0.6802 0.4589 0.4051 0.075 Uiso 0.503(9) 1 calc R U P C 3
C15A C 0.6603(8) 0.3783(7) 0.3427(16) 0.064(4) Uani 0.503(9) 1 d D U P C 3
H15C H 0.6782 0.3838 0.2775 0.077 Uiso 0.503(9) 1 calc R U P C 3
C16A C 0.6325(7) 0.3273(8) 0.3581(17) 0.056(4) Uani 0.503(9) 1 d D U P C 3
H16C H 0.6369 0.2943 0.3103 0.068 Uiso 0.503(9) 1 calc R U P C 3
C19B C 0.6278(14) 0.3482(12) 0.357(2) 0.106(7) Uani 0.497(9) 1 d D U P C 4
H19E H 0.6482 0.3187 0.3153 0.127 Uiso 0.497(9) 1 calc R U P C 4
H19F H 0.5961 0.3568 0.3160 0.127 Uiso 0.497(9) 1 calc R U P C 4
C20B C 0.6569(13) 0.4037(13) 0.366(3) 0.110(8) Uani 0.497(9) 1 d . U P C 4
H20F H 0.6480 0.4308 0.3071 0.166 Uiso 0.497(9) 1 calc R U P C 4
H20G H 0.6937 0.3944 0.3632 0.166 Uiso 0.497(9) 1 calc R U P C 4
H20H H 0.6489 0.4234 0.4339 0.166 Uiso 0.497(9) 1 calc R U P C 4
O26B O 0.6136(7) 0.3205(12) 0.4571(16) 0.102(7) Uani 0.497(9) 1 d D U P C 4
H26D H 0.5973 0.2883 0.4453 0.153 Uiso 0.497(9) 1 calc R U P C 4
C16B C 0.566(2) 0.338(2) 0.728(3) 0.089(7) Uani 0.497(9) 1 d D U P C 4
H16D H 0.5513 0.2993 0.7146 0.107 Uiso 0.497(9) 1 calc R U P C 4
C12B C 0.5604(9) 0.3661(11) 0.8198(19) 0.088(5) Uani 0.497(9) 1 d D U P C 4
H12D H 0.5392 0.3493 0.8739 0.106 Uiso 0.497(9) 1 calc R U P C 4
C13B C 0.5847(9) 0.4179(11) 0.8356(19) 0.087(5) Uani 0.497(9) 1 d D U P C 4
H13D H 0.5825 0.4349 0.9049 0.104 Uiso 0.497(9) 1 calc R U P C 4
C14B C 0.6118(10) 0.4484(12) 0.7643(14) 0.083(5) Uani 0.497(9) 1 d D U P C 4
H14D H 0.6252 0.4872 0.7817 0.099 Uiso 0.497(9) 1 calc R U P C 4
C15B C 0.6203(7) 0.4250(8) 0.6688(15) 0.083(5) Uani 0.497(9) 1 d D U P C 4
H15D H 0.6418 0.4449 0.6187 0.100 Uiso 0.497(9) 1 calc R U P C 4
N34B N 0.5970(6) 0.3713(7) 0.6447(14) 0.085(4) Uani 0.497(9) 1 d . U P C 4
H34B H 0.6002 0.3559 0.5803 0.102 Uiso 0.497(9) 1 calc R U P C 4
C21 C 0.6212(5) 0.1360(8) 1.3792(11) 0.066(3) Uani 0.5 1 d . U P . .
H21C H 0.5930 0.1133 1.3445 0.079 Uiso 0.5 1 calc R U P . .
H21D H 0.6425 0.1530 1.3212 0.079 Uiso 0.5 1 calc R U P . .
C22 C 0.6493(5) 0.0965(7) 1.4282(13) 0.062(4) Uani 0.5 1 d . U P . .
H22C H 0.6787 0.1170 1.4613 0.092 Uiso 0.5 1 calc R U P . .
H22D H 0.6617 0.0663 1.3771 0.092 Uiso 0.5 1 calc R U P . .
H22E H 0.6288 0.0764 1.4834 0.092 Uiso 0.5 1 calc R U P . .
O27 O 0.5995(4) 0.1833(6) 1.4299(10) 0.087(3) Uani 0.5 1 d . U P . .
H27 H 0.5721 0.1929 1.3990 0.130 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.469(3) . ?
S1 O1 1.474(4) . ?
S1 O4 1.477(3) . ?
S1 O3 1.483(3) . ?
S2 O8 1.460(3) . ?
S2 O6 1.467(4) . ?
S2 O5 1.480(3) . ?
S2 O7 1.494(3) . ?
S3 O12 1.446(4) . ?
S3 O11 1.466(4) . ?
S3 O10 1.480(3) . ?
S3 O9 1.483(3) . ?
S4 O15 1.467(4) . ?
S4 O16 1.470(4) . ?
S4 O14 1.479(4) . ?
S4 O13 1.482(4) . ?
S5 O20B 1.372(11) . ?
S5 O20A 1.395(5) . ?
S5 O17 1.457(4) . ?
S5 O18A 1.499(5) . ?
S5 O19A 1.538(5) . ?
S5 O18B 1.564(10) . ?
S5 O19B 1.640(11) . ?
S6 O23A 1.427(8) . ?
S6 O22A 1.441(7) . ?
S6 O21 1.455(5) . ?
S6 O23B 1.457(11) . ?
S6 O24A 1.461(5) . ?
S6 O22B 1.469(11) . ?
S6 O24B 1.474(12) . ?
N1 C1 1.328(7) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.326(6) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C1 1.321(6) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C2 1.319(7) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 C2 1.330(7) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 C2 1.312(7) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N7 C3 1.312(7) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 C3 1.340(6) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N9 C3 1.321(6) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N10 C4 1.314(7) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N11 C4 1.328(6) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N12 C4 1.324(6) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 C5 1.325(7) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N14 C5 1.331(7) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N15 C5 1.330(7) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N16 C6 1.327(8) . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
N17 C6 1.327(8) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N18 C6 1.337(7) . ?
N18 H18A 0.8800 . ?
N18 H18B 0.8800 . ?
N19 C7 1.325(7) . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
N20 C7 1.324(6) . ?
N20 H20A 0.8800 . ?
N20 H20B 0.8800 . ?
N21 C7 1.327(6) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?
N22 C8 1.337(7) . ?
N22 H22A 0.8800 . ?
N22 H22B 0.8800 . ?
N23 C8 1.325(7) . ?
N23 H23A 0.8800 . ?
N23 H23B 0.8800 . ?
N24 C8 1.324(6) . ?
N24 H24A 0.8800 . ?
N24 H24B 0.8800 . ?
N25 C9 1.310(7) . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N26 C9 1.328(7) . ?
N26 H26A 0.8800 . ?
N26 H26B 0.8800 . ?
N27 C9 1.339(7) . ?
N27 H27A 0.8800 . ?
N27 H27B 0.8800 . ?
N28 C10 1.319(6) . ?
N28 H28A 0.8800 . ?
N28 H28B 0.8800 . ?
N29 C10 1.333(7) . ?
N29 H29A 0.8800 . ?
N29 H29B 0.8800 . ?
N30 C10 1.329(7) . ?
N30 H30A 0.8800 . ?
N30 H30B 0.8800 . ?
N31 C11 1.313(7) . ?
N31 H31A 0.8800 . ?
N31 H31B 0.8800 . ?
N32 C11 1.321(7) . ?
N32 H32A 0.8800 . ?
N32 H32B 0.8800 . ?
N33 C11 1.324(7) . ?
N33 H33A 0.8800 . ?
N33 H33B 0.8800 . ?
O25 C17 1.422(6) . ?
O25 H25 0.8400 . ?
C17 C18 1.507(9) . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C19A O26A 1.46(2) . ?
C19A C20A 1.50(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20C 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
O26A H26C 0.8400 . ?
C12A C16A 1.356(14) . ?
C12A N34A 1.51(3) . ?
C12A H12C 0.9500 . ?
N34A C13A 1.298(15) . ?
N34A H34A 0.8800 . ?
C13A C14A 1.352(13) . ?
C13A H13C 0.9500 . ?
C14A C15A 1.354(14) . ?
C14A H14C 0.9500 . ?
C15A C16A 1.352(14) . ?
C15A H15C 0.9500 . ?
C16A H16C 0.9500 . ?
C19B C20B 1.44(4) . ?
C19B O26B 1.45(2) . ?
C19B H19E 0.9900 . ?
C19B H19F 0.9900 . ?
C20B H20F 0.9800 . ?
C20B H20G 0.9800 . ?
C20B H20H 0.9800 . ?
O26B H26D 0.8400 . ?
C16B C12B 1.318(19) . ?
C16B N34B 1.51(4) . ?
C16B H16D 0.9500 . ?
C12B C13B 1.322(18) . ?
C12B H12D 0.9500 . ?
C13B C14B 1.324(18) . ?
C13B H13D 0.9500 . ?
C14B C15B 1.325(17) . ?
C14B H14D 0.9500 . ?
C15B N34B 1.36(2) . ?
C15B H15D 0.9500 . ?
N34B H34B 0.8800 . ?
C21 C22 1.29(2) . ?
C21 O27 1.347(18) . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C22 H22C 0.9800 . ?
C22 H22D 0.9800 . ?
C22 H22E 0.9800 . ?
O27 H27 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 109.8(2) . . ?
O2 S1 O4 109.9(2) . . ?
O1 S1 O4 110.05(19) . . ?
O2 S1 O3 108.8(2) . . ?
O1 S1 O3 110.13(19) . . ?
O4 S1 O3 108.16(19) . . ?
O8 S2 O6 110.7(2) . . ?
O8 S2 O5 111.1(2) . . ?
O6 S2 O5 109.2(2) . . ?
O8 S2 O7 109.03(19) . . ?
O6 S2 O7 108.5(2) . . ?
O5 S2 O7 108.20(19) . . ?
O12 S3 O11 110.3(3) . . ?
O12 S3 O10 109.6(3) . . ?
O11 S3 O10 109.2(2) . . ?
O12 S3 O9 109.4(2) . . ?
O11 S3 O9 110.0(2) . . ?
O10 S3 O9 108.3(2) . . ?
O15 S4 O16 110.1(2) . . ?
O15 S4 O14 109.1(2) . . ?
O16 S4 O14 110.3(2) . . ?
O15 S4 O13 109.6(2) . . ?
O16 S4 O13 109.0(2) . . ?
O14 S4 O13 108.6(2) . . ?
O20B S5 O17 138.7(5) . . ?
O20A S5 O17 117.6(3) . . ?
O20A S5 O18A 113.8(3) . . ?
O17 S5 O18A 105.6(3) . . ?
O20A S5 O19A 109.8(3) . . ?
O17 S5 O19A 103.5(3) . . ?
O18A S5 O19A 105.4(3) . . ?
O20B S5 O18B 112.4(7) . . ?
O17 S5 O18B 101.2(4) . . ?
O20B S5 O19B 103.8(7) . . ?
O17 S5 O19B 96.7(5) . . ?
O18B S5 O19B 94.2(6) . . ?
O23A S6 O22A 109.4(8) . . ?
O23A S6 O21 117.7(5) . . ?
O22A S6 O21 102.2(4) . . ?
O21 S6 O23B 108.0(8) . . ?
O23A S6 O24A 110.8(4) . . ?
O22A S6 O24A 108.1(4) . . ?
O21 S6 O24A 108.0(3) . . ?
O21 S6 O22B 128.0(6) . . ?
O23B S6 O22B 109.9(7) . . ?
O21 S6 O24B 100.0(7) . . ?
O23B S6 O24B 100.8(10) . . ?
O22B S6 O24B 106.3(9) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C3 N8 H8A 120.0 . . ?
C3 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C3 N9 H9A 120.0 . . ?
C3 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C4 N11 H11A 120.0 . . ?
C4 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C4 N12 H12A 120.0 . . ?
C4 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C5 N14 H14A 120.0 . . ?
C5 N14 H14B 120.0 . . ?
H14A N14 H14B 120.0 . . ?
C5 N15 H15A 120.0 . . ?
C5 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C6 N16 H16A 120.0 . . ?
C6 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
C6 N17 H17A 120.0 . . ?
C6 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C6 N18 H18A 120.0 . . ?
C6 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
C7 N19 H19A 120.0 . . ?
C7 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C7 N20 H20A 120.0 . . ?
C7 N20 H20B 120.0 . . ?
H20A N20 H20B 120.0 . . ?
C7 N21 H21A 120.0 . . ?
C7 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
C8 N22 H22A 120.0 . . ?
C8 N22 H22B 120.0 . . ?
H22A N22 H22B 120.0 . . ?
C8 N23 H23A 120.0 . . ?
C8 N23 H23B 120.0 . . ?
H23A N23 H23B 120.0 . . ?
C8 N24 H24A 120.0 . . ?
C8 N24 H24B 120.0 . . ?
H24A N24 H24B 120.0 . . ?
C9 N25 H25A 120.0 . . ?
C9 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
C9 N26 H26A 120.0 . . ?
C9 N26 H26B 120.0 . . ?
H26A N26 H26B 120.0 . . ?
C9 N27 H27A 120.0 . . ?
C9 N27 H27B 120.0 . . ?
H27A N27 H27B 120.0 . . ?
C10 N28 H28A 120.0 . . ?
C10 N28 H28B 120.0 . . ?
H28A N28 H28B 120.0 . . ?
C10 N29 H29A 120.0 . . ?
C10 N29 H29B 120.0 . . ?
H29A N29 H29B 120.0 . . ?
C10 N30 H30A 120.0 . . ?
C10 N30 H30B 120.0 . . ?
H30A N30 H30B 120.0 . . ?
C11 N31 H31A 120.0 . . ?
C11 N31 H31B 120.0 . . ?
H31A N31 H31B 120.0 . . ?
C11 N32 H32A 120.0 . . ?
C11 N32 H32B 120.0 . . ?
H32A N32 H32B 120.0 . . ?
C11 N33 H33A 120.0 . . ?
C11 N33 H33B 120.0 . . ?
H33A N33 H33B 120.0 . . ?
N3 C1 N2 120.3(5) . . ?
N3 C1 N1 119.7(4) . . ?
N2 C1 N1 120.0(4) . . ?
N6 C2 N4 120.4(5) . . ?
N6 C2 N5 119.4(5) . . ?
N4 C2 N5 120.2(5) . . ?
N7 C3 N9 120.5(5) . . ?
N7 C3 N8 120.4(5) . . ?
N9 C3 N8 119.1(5) . . ?
N10 C4 N12 119.5(5) . . ?
N10 C4 N11 119.9(5) . . ?
N12 C4 N11 120.6(5) . . ?
N13 C5 N15 120.6(5) . . ?
N13 C5 N14 120.0(5) . . ?
N15 C5 N14 119.4(5) . . ?
N17 C6 N16 120.9(5) . . ?
N17 C6 N18 120.1(6) . . ?
N16 C6 N18 119.0(6) . . ?
N20 C7 N19 119.9(4) . . ?
N20 C7 N21 120.7(5) . . ?
N19 C7 N21 119.4(5) . . ?
N24 C8 N23 120.1(5) . . ?
N24 C8 N22 120.2(5) . . ?
N23 C8 N22 119.7(5) . . ?
N25 C9 N26 121.2(5) . . ?
N25 C9 N27 119.7(5) . . ?
N26 C9 N27 119.1(5) . . ?
N28 C10 N30 120.6(5) . . ?
N28 C10 N29 120.1(5) . . ?
N30 C10 N29 119.3(5) . . ?
N31 C11 N32 119.7(5) . . ?
N31 C11 N33 120.3(5) . . ?
N32 C11 N33 120.0(5) . . ?
C17 O25 H25 109.5 . . ?
O25 C17 C18 108.0(5) . . ?
O25 C17 H17C 110.1 . . ?
C18 C17 H17C 110.1 . . ?
O25 C17 H17D 110.1 . . ?
C18 C17 H17D 110.1 . . ?
H17C C17 H17D 108.4 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18C C18 H18D 109.5 . . ?
C17 C18 H18E 109.5 . . ?
H18C C18 H18E 109.5 . . ?
H18D C18 H18E 109.5 . . ?
O26A C19A C20A 113.9(15) . . ?
O26A C19A H19C 108.8 . . ?
C20A C19A H19C 108.8 . . ?
O26A C19A H19D 108.8 . . ?
C20A C19A H19D 108.8 . . ?
H19C C19A H19D 107.7 . . ?
C19A C20A H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
H20C C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20C C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A O26A H26C 109.5 . . ?
C16A C12A N34A 109.2(18) . . ?
C16A C12A H12C 125.4 . . ?
N34A C12A H12C 125.4 . . ?
C13A N34A C12A 121.0(13) . . ?
C13A N34A H34A 119.5 . . ?
C12A N34A H34A 119.5 . . ?
N34A C13A C14A 120.7(12) . . ?
N34A C13A H13C 119.7 . . ?
C14A C13A H13C 119.7 . . ?
C13A C14A C15A 118.6(15) . . ?
C13A C14A H14C 120.7 . . ?
C15A C14A H14C 120.7 . . ?
C16A C15A C14A 121.1(18) . . ?
C16A C15A H15C 119.5 . . ?
C14A C15A H15C 119.5 . . ?
C15A C16A C12A 122.4(19) . . ?
C15A C16A H16C 118.8 . . ?
C12A C16A H16C 118.8 . . ?
C20B C19B O26B 115(3) . . ?
C20B C19B H19E 108.5 . . ?
O26B C19B H19E 108.5 . . ?
C20B C19B H19F 108.5 . . ?
O26B C19B H19F 108.5 . . ?
H19E C19B H19F 107.5 . . ?
C19B C20B H20F 109.5 . . ?
C19B C20B H20G 109.5 . . ?
H20F C20B H20G 109.5 . . ?
C19B C20B H20H 109.5 . . ?
H20F C20B H20H 109.5 . . ?
H20G C20B H20H 109.5 . . ?
C19B O26B H26D 109.5 . . ?
C12B C16B N34B 116(3) . . ?
C12B C16B H16D 122.1 . . ?
N34B C16B H16D 122.1 . . ?
C16B C12B C13B 119(3) . . ?
C16B C12B H12D 120.5 . . ?
C13B C12B H12D 120.5 . . ?
C12B C13B C14B 126(2) . . ?
C12B C13B H13D 116.8 . . ?
C14B C13B H13D 116.8 . . ?
C13B C14B C15B 120(2) . . ?
C13B C14B H14D 119.9 . . ?
C15B C14B H14D 119.9 . . ?
C14B C15B N34B 118(2) . . ?
C14B C15B H15D 121.1 . . ?
N34B C15B H15D 121.1 . . ?
C15B N34B C16B 120(2) . . ?
C15B N34B H34B 119.8 . . ?
C16B N34B H34B 119.8 . . ?
C22 C21 O27 122.2(14) . . ?
C22 C21 H21C 106.8 . . ?
O27 C21 H21C 106.8 . . ?
C22 C21 H21D 106.8 . . ?
O27 C21 H21D 106.8 . . ?
H21C C21 H21D 106.6 . . ?
C21 C22 H22C 109.5 . . ?
C21 C22 H22D 109.5 . . ?
H22C C22 H22D 109.5 . . ?
C21 C22 H22E 109.5 . . ?
H22C C22 H22E 109.5 . . ?
H22D C22 H22E 109.5 . . ?
C21 O27 H27 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O7 0.88 2.04 2.914(5) 173.5 1_545
N1 H1B O3 0.88 2.02 2.878(5) 164.2 .
N2 H2A O9 0.88 2.05 2.927(5) 175.0 4_645
N2 H2B O1 0.88 2.11 2.977(5) 169.4 .
N3 H3A O10 0.88 2.05 2.926(5) 178.0 4_645
N3 H3B O6 0.88 2.05 2.931(5) 178.1 1_545
N4 H4A O21 0.88 2.00 2.876(7) 175.5 .
N4 H4B O22A 0.88 1.98 2.854(8) 174.5 2_655
N5 H5A O2 0.88 2.13 2.909(5) 147.0 .
N5 H5B O21 0.88 2.05 2.910(6) 166.0 2_655
N6 H6A O24A 0.88 2.07 2.940(7) 171.5 .
N6 H6A O24B 0.88 2.21 2.999(18) 148.8 .
N6 H6B O2 0.88 2.12 2.905(6) 147.5 .
N7 H7A O4 0.88 2.02 2.865(5) 159.2 .
N7 H7B O10 0.88 2.01 2.862(5) 163.6 .
N8 H8A O11 0.88 2.06 2.927(6) 167.0 .
N8 H8B O7 0.88 2.05 2.926(5) 175.8 4_645
N9 H9A O1 0.88 2.10 2.971(5) 170.9 .
N9 H9B O5 0.88 2.08 2.960(5) 177.4 4_645
N10 H10A O19A 0.88 2.07 2.872(7) 151.5 4_644
N10 H10A O20B 0.88 2.01 2.855(14) 159.7 4_644
N10 H10B O23A 0.88 1.93 2.807(8) 172.5 4_655
N10 H10B O24B 0.88 2.37 3.110(16) 141.9 4_655
N11 H11A O24A 0.88 2.06 2.916(7) 165.1 4_655
N11 H11A O22B 0.88 2.29 3.121(16) 158.0 4_655
N11 H11A O24B 0.88 2.45 3.174(16) 139.2 4_655
N11 H11B O9 0.88 2.04 2.914(5) 171.6 .
N12 H12A O20A 0.88 2.18 3.030(7) 162.4 4_644
N12 H12A O18B 0.88 1.95 2.811(11) 166.6 4_644
N12 H12B O10 0.88 2.05 2.933(5) 175.9 .
N13 H13A O2 0.88 2.06 2.887(6) 155.8 1_554
N13 H13B O13 0.88 2.11 2.924(5) 153.6 2_653
N14 H14A O16 0.88 2.08 2.934(6) 162.4 2_653
N14 H14B O22A 0.88 2.46 3.155(10) 136.4 .
N14 H14B O23B 0.88 2.03 2.905(12) 176.5 .
N15 H15A O1 0.88 2.14 3.005(6) 168.6 1_554
N15 H15B O22A 0.88 2.07 2.863(9) 149.0 .
N15 H15B O22B 0.88 2.08 2.957(14) 172.6 .
N16 H16A O11 0.88 2.36 3.216(7) 165.9 .
N16 H16B O14 0.88 2.10 2.975(7) 176.5 .
N17 H17A O12 0.88 1.98 2.815(7) 158.3 .
N17 H17B O23A 0.88 2.03 2.847(11) 154.9 2_655
N17 H17B O23B 0.88 2.19 3.064(15) 175.9 2_655
N18 H18B O13 0.88 2.02 2.897(7) 176.9 .
N18 H18A O23A 0.88 2.54 3.239(16) 136.5 2_655
N18 H18A O24B 0.88 2.02 2.891(16) 170.7 2_655
N19 H19A O5 0.88 2.00 2.881(5) 176.6 .
N19 H19B O9 0.88 1.94 2.820(5) 172.7 .
N20 H20A O6 0.88 2.04 2.916(5) 171.8 .
N20 H20B O4 0.88 2.05 2.926(5) 172.9 4_655
N21 H21A O3 0.88 2.09 2.958(5) 168.8 4_655
N21 H21B O11 0.88 2.06 2.911(6) 162.8 .
N22 H22A O20A 0.88 2.17 3.044(8) 173.6 .
N22 H22A O19B 0.88 1.98 2.754(13) 146.8 .
N22 H22B O8 0.88 2.15 2.906(6) 144.4 .
N23 H23A O15 0.88 2.06 2.870(6) 151.9 2_664
N23 H23B O8 0.88 2.47 3.157(6) 135.1 .
N23 H23B O25 0.88 2.24 2.985(6) 142.1 .
N24 H24A O16 0.88 2.08 2.929(6) 163.3 2_664
N24 H24B O18A 0.88 1.96 2.807(7) 160.3 .
N24 H24B O20B 0.88 2.15 3.006(14) 163.2 .
N25 H25A O7 0.88 2.13 3.005(5) 176.2 4_645
N25 H25B O14 0.88 2.00 2.881(6) 177.0 .
N26 H26A O5 0.88 2.12 2.994(5) 171.5 4_645
N26 H26B O24A 0.88 2.19 3.053(7) 167.1 1_556
N26 H26B O22B 0.88 2.02 2.840(13) 155.4 1_556
N27 H27A O13 0.88 2.01 2.884(6) 173.1 .
N27 H27B O21 0.88 2.28 3.137(8) 165.1 1_556
N27 H27B O22A 0.88 2.60 3.315(11) 138.9 1_556
N28 H28A O3 0.88 2.03 2.901(5) 169.3 4_655
N28 H28B O14 0.88 2.03 2.906(5) 173.0 .
N29 H29A O15 0.88 1.97 2.847(6) 174.4 .
N29 H29B O17 0.88 2.01 2.889(6) 173.0 .
N30 H30A O4 0.88 2.08 2.960(5) 175.8 4_655
N30 H30B O20A 0.88 2.14 2.960(7) 155.4 .
N30 H30B O18B 0.88 2.09 2.969(12) 174.7 .
N31 H31A O18A 0.88 2.14 2.940(7) 151.3 .
N31 H31A O19B 0.88 2.03 2.841(13) 153.2 .
N31 H31B O17 0.88 2.02 2.894(6) 174.4 2_664
N32 H32A O17 0.88 2.12 2.935(6) 154.4 .
N32 H32B O8 0.88 2.07 2.894(6) 156.0 2_665
N33 H33A O19A 0.88 2.21 2.969(8) 144.3 2_664
N33 H33A O18B 0.88 2.07 2.914(14) 160.9 2_664
N33 H33B O25 0.88 2.07 2.906(6) 157.3 2_665
O25 H25 O7 0.84 1.99 2.820(4) 170.9 .
N34A H34A O26A 0.88 1.76 2.595(18) 156.8 .
O26B H26D O27 0.84 2.33 3.07(3) 147.7 1_554
N34B H34B O26B 0.88 1.77 2.64(3) 172.8 .
O27 H27 O16 0.84 2.52 3.197(14) 138.5 .

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2012779'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H26 N10 O9 S2'
_chemical_formula_weight         470.51

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

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

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

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

_cell_length_a                   12.3826(9)
_cell_length_b                   11.1225(7)
_cell_length_c                   7.7723(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.385(2)
_cell_angle_gamma                90
_cell_volume                     1045.53(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      30.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    0.318
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11289
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         28.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2640
_reflns_number_gt                2585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2640
_refine_ls_number_parameters     179
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0554
_refine_ls_wR_factor_gt          0.0550
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69412(3) 0.28175(3) 0.81959(4) 0.01361(10) Uani 1 1 d . . . . .
O1 O 0.59700(9) 0.28405(13) 0.90141(14) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.79111(10) 0.33293(11) 0.94168(16) 0.0194(3) Uani 1 1 d . . . . .
O3 O 0.67009(10) 0.35480(11) 0.65497(16) 0.0188(3) Uani 1 1 d . . . . .
O4 O 0.71675(11) 0.15657(11) 0.77348(16) 0.0191(3) Uani 1 1 d . . . . .
N1 N 1.000000 0.20416(19) 1.000000 0.0216(4) Uani 1 2 d S T P . .
H1A H 1.062621 0.243717 1.032308 0.026 Uiso 0.5 1 calc R U P . .
H1B H 0.937379 0.243717 0.967692 0.026 Uiso 0.5 1 calc R U P . .
N2 N 0.90561(14) 0.02546(16) 0.9513(2) 0.0247(3) Uani 1 1 d . . . . .
H2A H 0.846(2) 0.065(3) 0.909(3) 0.029(7) Uiso 1 1 d . . . . .
H2B H 0.904(2) -0.043(3) 0.972(4) 0.040(8) Uiso 1 1 d . . . . .
N3 N 0.63837(14) 0.07597(15) 0.1384(2) 0.0217(3) Uani 1 1 d . . . . .
H3A H 0.610(2) 0.119(3) 0.050(4) 0.033(7) Uiso 1 1 d . . . . .
H3B H 0.664(2) 0.009(3) 0.120(3) 0.030(7) Uiso 1 1 d . . . . .
N4 N 0.73461(13) 0.07598(15) 0.4279(2) 0.0199(3) Uani 1 1 d . . . . .
H4A H 0.735(2) 0.099(2) 0.527(4) 0.023(6) Uiso 1 1 d . . . . .
H4B H 0.763(2) 0.011(2) 0.405(3) 0.021(6) Uiso 1 1 d . . . . .
N5 N 0.61933(14) 0.23328(15) 0.3216(2) 0.0220(3) Uani 1 1 d . . . . .
H5A H 0.638(2) 0.271(3) 0.422(3) 0.034(6) Uiso 1 1 d . . . . .
H5B H 0.569(2) 0.256(3) 0.251(4) 0.034(7) Uiso 1 1 d . . . . .
N6 N 0.500000 0.7302(2) 0.500000 0.0248(5) Uani 1 2 d S T P . .
H6 H 0.500000 0.648(4) 0.500000 0.030 Uiso 1 2 d S U P . .
C1 C 1.000000 0.0850(2) 1.000000 0.0178(4) Uani 1 2 d S T P . .
C2 C 0.66374(14) 0.12793(15) 0.2960(2) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.56874(15) 0.7883(2) 0.6300(2) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.616592 0.744092 0.719780 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5700(2) 0.9109(2) 0.6335(3) 0.0389(6) Uani 1 1 d . . . . .
H4 H 0.618032 0.952986 0.725560 0.047 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.9726(3) 0.500000 0.0457(10) Uani 1 2 d S T P . .
H5 H 0.500001 1.058001 0.499998 0.055 Uiso 1 2 calc R U P . .
O5W O 0.5060(8) 0.4947(2) 0.4666(7) 0.0329(15) Uani 0.5 1 d D . P A -1
H5C H 0.461(5) 0.446(5) 0.389(7) 0.044(17) Uiso 0.5 1 d D . P B -1
H5D H 0.558(4) 0.452(5) 0.541(7) 0.032(15) Uiso 0.5 1 d D . P C -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4758(12) . ?
S1 O1 1.4764(11) . ?
S1 O4 1.4794(13) . ?
S1 O3 1.4908(12) . ?
N1 C1 1.325(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.326(2) . ?
N2 H2A 0.86(3) . ?
N2 H2B 0.78(3) . ?
N3 C2 1.330(2) . ?
N3 H3A 0.85(3) . ?
N3 H3B 0.83(3) . ?
N4 C2 1.330(2) . ?
N4 H4A 0.81(3) . ?
N4 H4B 0.84(3) . ?
N5 C2 1.327(2) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.78(3) . ?
N6 C3 1.339(2) . ?
N6 C3 1.339(2) 2_656 ?
N6 H6 0.91(4) . ?
C3 C4 1.364(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
O5W H5C 0.91(3) . ?
O5W H5D 0.90(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 110.00(7) . . ?
O2 S1 O4 110.40(7) . . ?
O1 S1 O4 109.56(8) . . ?
O2 S1 O3 109.07(7) . . ?
O1 S1 O3 109.21(7) . . ?
O4 S1 O3 108.57(7) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 119.0(18) . . ?
C1 N2 H2B 119(2) . . ?
H2A N2 H2B 122(3) . . ?
C2 N3 H3A 118.7(19) . . ?
C2 N3 H3B 121.4(18) . . ?
H3A N3 H3B 118(2) . . ?
C2 N4 H4A 117.6(18) . . ?
C2 N4 H4B 117.0(15) . . ?
H4A N4 H4B 123(2) . . ?
C2 N5 H5A 121.0(19) . . ?
C2 N5 H5B 118(2) . . ?
H5A N5 H5B 120(3) . . ?
C3 N6 C3 122.3(3) . 2_656 ?
C3 N6 H6 118.84(14) . . ?
C3 N6 H6 118.84(14) 2_656 . ?
N1 C1 N2 119.96(13) . 2_757 ?
N1 C1 N2 119.96(13) . . ?
N2 C1 N2 120.1(3) 2_757 . ?
N5 C2 N3 119.87(16) . . ?
N5 C2 N4 119.63(16) . . ?
N3 C2 N4 120.50(16) . . ?
N6 C3 C4 120.0(2) . . ?
N6 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C4 120.5(3) . 2_656 ?
C4 C5 H5 119.8 . . ?
C4 C5 H5 119.8 2_656 . ?
H5C O5W H5D 111(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.88 2.04 2.9059(17) 169.2 2_757
N1 H1B O2 0.88 2.04 2.9059(17) 169.2 .
N2 H2A O4 0.86(3) 2.00(3) 2.849(2) 171(2) .
N2 H2B O1 0.78(3) 2.17(3) 2.922(2) 165(3) 4_647
N3 H3A O1 0.85(3) 2.16(3) 2.934(2) 152(3) 1_554
N3 H3B O2 0.83(3) 2.12(3) 2.948(2) 173(3) 4_646
N4 H4A O4 0.81(3) 2.07(3) 2.885(2) 174(2) .
N4 H4B O3 0.84(3) 2.02(3) 2.861(2) 178(2) 4_646
N5 H5A O3 0.88(3) 2.00(3) 2.870(2) 176(2) .
N5 H5B O1 0.78(3) 2.16(3) 2.917(2) 163(3) 2_656
N6 H6 O5W 0.91(4) 1.73(4) 2.635(4) 170.5(3) .
N6 H6 O5W 0.91(4) 1.73(4) 2.635(4) 170.5(3) 2_656
O5W H5C O3 0.91(3) 1.89(4) 2.681(9) 145(6) 2_656
O5W H5D O3 0.90(3) 1.83(3) 2.723(8) 169(6) .

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2012780'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H28 N10 O9 S2'
_chemical_formula_weight         484.53

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   7.4737(6)
_cell_length_b                   11.8491(11)
_cell_length_c                   13.0179(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.723(3)
_cell_angle_gamma                90
_cell_volume                     1150.39(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9516
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25166
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4270
_reflns_number_gt                3983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4270
_refine_ls_number_parameters     352
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25000(9) 0.66909(5) 0.09326(6) 0.01511(17) Uani 1 1 d . . . . .
S2 S 0.68700(9) 0.59698(6) 0.61680(6) 0.01891(18) Uani 1 1 d . . . . .
O1 O 0.0847(3) 0.71376(16) 0.03804(16) 0.0183(5) Uani 1 1 d . . . . .
O2 O 0.4055(3) 0.71343(17) 0.03999(17) 0.0202(5) Uani 1 1 d . . . . .
O3 O 0.2600(3) 0.70544(18) 0.20055(16) 0.0236(5) Uani 1 1 d . . . . .
O4 O 0.2499(3) 0.54419(17) 0.08539(16) 0.0201(5) Uani 1 1 d . . . . .
O5 O 0.5283(3) 0.64847(17) 0.56049(16) 0.0235(5) Uani 1 1 d . . . . .
O6 O 0.7063(3) 0.64756(18) 0.72096(16) 0.0239(5) Uani 1 1 d . . . . .
O7 O 0.6583(3) 0.47419(18) 0.62390(18) 0.0282(5) Uani 1 1 d . . . . .
O8 O 0.8489(3) 0.6202(2) 0.56203(16) 0.0283(5) Uani 1 1 d . . . . .
N1 N 0.7475(4) 0.6086(2) 0.0651(2) 0.0252(6) Uani 1 1 d D . . . .
H1A H 0.653(5) 0.641(3) 0.063(3) 0.034(11) Uiso 1 1 d D . . . .
H1B H 0.849(5) 0.641(3) 0.063(3) 0.040(12) Uiso 1 1 d D . . . .
N2 N 0.8987(4) 0.4495(3) 0.0184(2) 0.0226(6) Uani 1 1 d . . . . .
H2A H 0.993(6) 0.484(3) 0.035(3) 0.034(11) Uiso 1 1 d . . . . .
H2B H 0.899(5) 0.380(4) 0.001(3) 0.039(11) Uiso 1 1 d . . . . .
N3 N 0.5908(4) 0.4483(3) 0.0175(2) 0.0256(7) Uani 1 1 d . . . . .
H3A H 0.503(5) 0.475(3) 0.031(3) 0.012(9) Uiso 1 1 d . . . . .
H3B H 0.589(5) 0.380(3) -0.008(3) 0.024(9) Uiso 1 1 d . . . . .
N4 N 0.3282(4) 0.4024(3) 0.2713(2) 0.0263(6) Uani 1 1 d . . . . .
H4A H 0.293(5) 0.445(3) 0.224(3) 0.023(10) Uiso 1 1 d . . . . .
H4B H 0.317(5) 0.339(4) 0.273(3) 0.032(12) Uiso 1 1 d . . . . .
N5 N 0.4494(4) 0.3912(3) 0.4378(2) 0.0298(7) Uani 1 1 d . . . . .
H5A H 0.493(5) 0.423(3) 0.486(3) 0.023(10) Uiso 1 1 d . . . . .
H5B H 0.452(5) 0.317(4) 0.435(3) 0.041(12) Uiso 1 1 d . . . . .
N6 N 0.3931(4) 0.5646(2) 0.3634(3) 0.0289(7) Uani 1 1 d . . . . .
H6A H 0.354(4) 0.597(3) 0.314(3) 0.020(9) Uiso 1 1 d . . . . .
H6B H 0.435(4) 0.592(3) 0.418(3) 0.019(8) Uiso 1 1 d . . . . .
N7 N 1.0612(4) 0.6744(3) 0.8168(2) 0.0252(6) Uani 1 1 d . . . . .
H7A H 1.072(5) 0.677(3) 0.879(3) 0.027(10) Uiso 1 1 d . . . . .
H7B H 0.963(5) 0.666(3) 0.786(3) 0.016(8) Uiso 1 1 d . . . . .
N8 N 1.3683(4) 0.6668(3) 0.8179(2) 0.0278(6) Uani 1 1 d . . . . .
H8A H 1.464(6) 0.655(3) 0.790(3) 0.032(10) Uiso 1 1 d . . . . .
H8B H 1.378(5) 0.677(4) 0.883(4) 0.040(11) Uiso 1 1 d . . . . .
N9 N 1.1970(4) 0.6438(3) 0.6660(2) 0.0283(7) Uani 1 1 d . . . . .
H9A H 1.288(6) 0.643(3) 0.633(3) 0.031(10) Uiso 1 1 d . . . . .
H9B H 1.088(5) 0.640(3) 0.634(3) 0.030(10) Uiso 1 1 d . . . . .
N10 N 0.9782(4) 0.3706(2) 0.6705(2) 0.0296(7) Uani 1 1 d D . . . .
H10 H 0.863(4) 0.392(4) 0.649(3) 0.064(14) Uiso 1 1 d D . . . .
C1 C 0.7454(4) 0.5023(2) 0.0340(2) 0.0193(6) Uani 1 1 d . . . . .
C2 C 0.3890(4) 0.4534(3) 0.3577(2) 0.0233(7) Uani 1 1 d . . . . .
C3 C 1.2096(4) 0.6615(3) 0.7666(2) 0.0220(7) Uani 1 1 d . . . . .
C4 C 1.0276(5) 0.3956(3) 0.7681(3) 0.0294(8) Uani 1 1 d . . . . .
H4 H 0.943742 0.430051 0.810119 0.035 Uiso 1 1 calc R U . . .
C5 C 1.1952(5) 0.3728(3) 0.8083(3) 0.0342(8) Uani 1 1 d . . . . .
H5 H 1.231066 0.393737 0.876990 0.041 Uiso 1 1 calc R U . . .
C6 C 1.3143(5) 0.3180(4) 0.7470(3) 0.0440(10) Uani 1 1 d . . . . .
H6 H 1.433263 0.301302 0.772754 0.053 Uiso 1 1 calc R U . . .
C7 C 1.2545(5) 0.2883(3) 0.6471(3) 0.0411(10) Uani 1 1 d . . . . .
H7 H 1.331118 0.247479 0.605028 0.049 Uiso 1 1 calc R U . . .
C8 C 1.0884(6) 0.3171(3) 0.6098(3) 0.0409(9) Uani 1 1 d . . . . .
H8 H 1.049758 0.299604 0.540686 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8829(6) 0.4780(4) 0.3155(3) 0.0498(11) Uani 1 1 d . . . . .
H9C H 0.754670 0.495919 0.311745 0.075 Uiso 1 1 calc R U . . .
H9D H 0.903701 0.412932 0.271286 0.075 Uiso 1 1 calc R U . . .
H9E H 0.950184 0.543098 0.292156 0.075 Uiso 1 1 calc R U . . .
O9 O 0.9405(5) 0.4521(3) 0.4175(2) 0.0618(9) Uani 1 1 d D . . . .
H9F H 0.935(9) 0.513(4) 0.455(4) 0.10(2) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.459(2) . ?
S1 O4 1.483(2) . ?
S1 O1 1.486(2) . ?
S1 O2 1.488(2) . ?
S2 O8 1.470(2) . ?
S2 O7 1.474(2) . ?
S2 O6 1.481(2) . ?
S2 O5 1.484(2) . ?
N1 C1 1.323(4) . ?
N1 H1A 0.80(3) . ?
N1 H1B 0.86(3) . ?
N2 C1 1.333(4) . ?
N2 H2A 0.83(4) . ?
N2 H2B 0.85(5) . ?
N3 C1 1.326(4) . ?
N3 H3A 0.76(4) . ?
N3 H3B 0.88(4) . ?
N4 C2 1.331(4) . ?
N4 H4A 0.83(4) . ?
N4 H4B 0.75(5) . ?
N5 C2 1.332(4) . ?
N5 H5A 0.79(4) . ?
N5 H5B 0.87(5) . ?
N6 C2 1.320(4) . ?
N6 H6A 0.80(4) . ?
N6 H6B 0.83(4) . ?
N7 C3 1.332(4) . ?
N7 H7A 0.81(4) . ?
N7 H7B 0.82(4) . ?
N8 C3 1.325(4) . ?
N8 H8A 0.84(4) . ?
N8 H8B 0.86(4) . ?
N9 C3 1.323(4) . ?
N9 H9A 0.82(4) . ?
N9 H9B 0.89(4) . ?
N10 C4 1.333(4) . ?
N10 C8 1.338(5) . ?
N10 H10 0.92(3) . ?
C4 C5 1.353(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.347(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 O9 1.404(5) . ?
C9 H9C 0.9800 . ?
C9 H9D 0.9800 . ?
C9 H9E 0.9800 . ?
O9 H9F 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 111.12(13) . . ?
O3 S1 O1 110.31(12) . . ?
O4 S1 O1 108.99(12) . . ?
O3 S1 O2 110.43(13) . . ?
O4 S1 O2 108.48(12) . . ?
O1 S1 O2 107.40(12) . . ?
O8 S2 O7 110.05(14) . . ?
O8 S2 O6 109.54(13) . . ?
O7 S2 O6 110.35(13) . . ?
O8 S2 O5 109.88(13) . . ?
O7 S2 O5 108.76(13) . . ?
O6 S2 O5 108.23(12) . . ?
C1 N1 H1A 117(3) . . ?
C1 N1 H1B 114(3) . . ?
H1A N1 H1B 124(4) . . ?
C1 N2 H2A 117(3) . . ?
C1 N2 H2B 121(3) . . ?
H2A N2 H2B 121(4) . . ?
C1 N3 H3A 121(3) . . ?
C1 N3 H3B 120(2) . . ?
H3A N3 H3B 119(3) . . ?
C2 N4 H4A 116(3) . . ?
C2 N4 H4B 118(3) . . ?
H4A N4 H4B 126(4) . . ?
C2 N5 H5A 118(3) . . ?
C2 N5 H5B 122(3) . . ?
H5A N5 H5B 120(4) . . ?
C2 N6 H6A 116(3) . . ?
C2 N6 H6B 117(3) . . ?
H6A N6 H6B 127(4) . . ?
C3 N7 H7A 118(3) . . ?
C3 N7 H7B 120(2) . . ?
H7A N7 H7B 122(4) . . ?
C3 N8 H8A 123(3) . . ?
C3 N8 H8B 122(3) . . ?
H8A N8 H8B 116(4) . . ?
C3 N9 H9A 120(3) . . ?
C3 N9 H9B 118(2) . . ?
H9A N9 H9B 121(4) . . ?
C4 N10 C8 121.7(3) . . ?
C4 N10 H10 115(3) . . ?
C8 N10 H10 123(3) . . ?
N1 C1 N3 120.1(3) . . ?
N1 C1 N2 120.0(3) . . ?
N3 C1 N2 119.9(3) . . ?
N6 C2 N4 120.4(3) . . ?
N6 C2 N5 120.2(3) . . ?
N4 C2 N5 119.4(3) . . ?
N9 C3 N8 120.7(3) . . ?
N9 C3 N7 119.7(3) . . ?
N8 C3 N7 119.6(3) . . ?
N10 C4 C5 121.0(3) . . ?
N10 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
N10 C8 C7 119.7(4) . . ?
N10 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O9 C9 H9C 109.5 . . ?
O9 C9 H9D 109.5 . . ?
H9C C9 H9D 109.5 . . ?
O9 C9 H9E 109.5 . . ?
H9C C9 H9E 109.5 . . ?
H9D C9 H9E 109.5 . . ?
C9 O9 H9F 109(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.80(3) 2.04(3) 2.841(3) 173(4) .
N1 H1B O1 0.86(3) 2.00(3) 2.854(3) 173(4) 1_655
N2 H2A O4 0.83(4) 2.11(4) 2.934(4) 171(4) 1_655
N2 H2B O1 0.85(5) 2.04(5) 2.893(4) 177(4) 2_645
N3 H3A O4 0.76(4) 2.22(4) 2.976(4) 175(3) .
N3 H3B O2 0.88(4) 2.02(4) 2.882(4) 169(3) 2_645
N4 H4A O4 0.83(4) 2.16(4) 2.973(4) 168(3) .
N4 H4B O6 0.75(5) 2.28(5) 3.032(4) 178(4) 2_646
N5 H5A O7 0.79(4) 2.20(4) 2.963(4) 166(4) .
N5 H5B O5 0.87(5) 2.01(5) 2.881(4) 175(4) 2_646
N6 H6A O3 0.80(4) 2.04(4) 2.827(4) 170(4) .
N6 H6B O5 0.83(4) 2.04(4) 2.874(4) 175(3) .
N7 H7A O1 0.81(4) 2.11(4) 2.912(4) 169(4) 1_656
N7 H7B O6 0.82(4) 2.06(4) 2.875(4) 175(3) .
N8 H8A O6 0.84(4) 2.07(4) 2.905(4) 172(4) 1_655
N8 H8B O2 0.86(4) 2.08(5) 2.938(4) 176(4) 1_656
N9 H9A O5 0.82(4) 2.09(4) 2.909(4) 176(4) 1_655
N9 H9B O8 0.89(4) 1.98(4) 2.868(4) 176(3) .
N10 H10 O7 0.92(3) 1.83(3) 2.721(4) 163(4) .
O9 H9F O8 0.87(3) 2.02(4) 2.853(4) 159(6) .

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2012778'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H24 N10 O8 S2'
_chemical_formula_weight         452.49

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

_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_H-M_alt        'R 3 2 :H'
_space_group_name_Hall           'R 3 2"'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   10.0469(10)
_cell_length_b                   10.0469(10)
_cell_length_c                   17.3180(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1513.9(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9557
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             714
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    0.322
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11748
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.620
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             774
_reflns_number_gt                755
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+1.0330P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 302 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         774
_refine_ls_number_parameters     54
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.333333 0.666667 0.48990(4) 0.0207(2) Uani 1 3 d S T P . .
O1 O 0.333333 0.666667 0.57549(11) 0.0243(5) Uani 1 3 d S T P . .
O2 O 0.30903(18) 0.51728(18) 0.46168(8) 0.0289(4) Uani 1 1 d . . . . .
N1 N 0.7902(3) 0.666667 0.666667 0.0269(6) Uani 1 2 d S T P . .
H1A H 0.800691 0.600077 0.638079 0.032 Uiso 0.5 1 calc R U P . .
H1B H 0.867281 0.733256 0.695255 0.032 Uiso 0.5 1 calc R U P . .
N2 N 0.5413(2) 0.5664(2) 0.62362(12) 0.0285(4) Uani 1 1 d . . . . .
H2A H 0.553(3) 0.505(3) 0.5967(14) 0.034 Uiso 1 1 d . U . . .
H2B H 0.477(3) 0.588(3) 0.6132(14) 0.034 Uiso 1 1 d . U . . .
C1 C 0.6582(3) 0.666667 0.666667 0.0228(6) Uani 1 2 d S T P . .
C2 C 0.0809(6) 0.1573(4) 0.50013(13) 0.0713(9) Uani 0.8333 1 d . . P . .
N3 N 0.0809(6) 0.1573(4) 0.50013(13) 0.0713(9) Uani 0.1667 1 d D . P . .
H3 H 0.137(6) 0.262(3) 0.501(2) 0.089(13) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4781(15) . ?
S1 O2 1.4781(15) 3_565 ?
S1 O2 1.4781(16) 2_665 ?
S1 O1 1.482(2) . ?
N1 C1 1.327(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.329(3) . ?
N2 H2A 0.83(3) . ?
N2 H2B 0.79(3) . ?
C2 C2 1.328(9) 4_556 ?
C2 C2 1.409(10) 6_556 ?
C2 H3 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O2 109.63(6) . 3_565 ?
O2 S1 O2 109.63(6) . 2_665 ?
O2 S1 O2 109.63(6) 3_565 2_665 ?
O2 S1 O1 109.31(6) . . ?
O2 S1 O1 109.31(6) 3_565 . ?
O2 S1 O1 109.31(6) 2_665 . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 H2A 118.6(19) . . ?
C1 N2 H2B 117(2) . . ?
H2A N2 H2B 121(3) . . ?
N1 C1 N2 120.29(14) . . ?
N1 C1 N2 120.30(14) . 11_566 ?
N2 C1 N2 119.4(3) . 11_566 ?
C2 C2 C2 119.999(5) 4_556 6_556 ?
C2 C2 H3 118(4) 4_556 . ?
C2 C2 H3 122(4) 6_556 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.88 2.07 2.8957(17) 156.3 5_666
N1 H1B O2 0.88 2.07 2.8957(17) 156.3 7
N2 H2A O2 0.83(3) 2.08(3) 2.881(3) 163(3) 4_556
N2 H2B O1 0.79(3) 2.07(3) 2.860(2) 172(3) .

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.047

