# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_crystal_1p
_database_code_depnum_ccdc_archive 'CCDC 1504953'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H14 N2 O8 S2'
_chemical_formula_sum            'C12 H14 N2 O8 S2'
_chemical_formula_weight         378.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6740(4)
_cell_length_b                   9.2402(4)
_cell_length_c                   9.7072(4)
_cell_angle_alpha                94.987(2)
_cell_angle_beta                 109.996(2)
_cell_angle_gamma                90.045(2)
_cell_volume                     727.97(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    5096
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      29.62

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.022
_diffrn_reflns_number            10417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.966
_reflns_number_total             2875
_reflns_number_gt                2449
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2875
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.066

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23558(6) 0.20175(5) 0.83023(5) 0.01821(15) Uani 1 1 d . . .
S2 S 0.20240(6) 0.70723(5) 0.78436(5) 0.01841(15) Uani 1 1 d . . .
O1 O 0.11634(17) 0.23952(16) 0.90194(16) 0.0232(3) Uani 1 1 d . . .
O2 O 0.37729(18) 0.32085(17) 0.88769(17) 0.0245(3) Uani 1 1 d . . .
O3 O 0.32124(19) 0.07194(16) 0.88369(18) 0.0290(4) Uani 1 1 d . . .
O4 O 0.16829(19) 0.20172(18) 0.67335(16) 0.0310(4) Uani 1 1 d . . .
O5 O 0.11354(18) 0.74210(16) 0.88520(16) 0.0254(3) Uani 1 1 d . . .
O6 O 0.11576(17) 0.74878(16) 0.63862(16) 0.0240(3) Uani 1 1 d . . .
O7 O 0.36928(17) 0.79594(18) 0.84559(17) 0.0245(3) Uani 1 1 d . . .
O8 O 0.25290(19) 0.55838(16) 0.78255(19) 0.0320(4) Uani 1 1 d . . .
N1 N 0.8680(2) -0.06536(18) 0.75880(18) 0.0200(4) Uani 1 1 d . . .
H1A H 0.9425 -0.1278 0.8 0.024 Uiso 1 1 calc R . .
N2 N 0.1246(2) 0.57863(18) 0.23085(19) 0.0200(4) Uani 1 1 d . . .
H2A H 0.0523 0.6418 0.1873 0.024 Uiso 1 1 calc R . .
C1 C 0.7714(3) -0.0109(2) 0.8316(2) 0.0233(4) Uani 1 1 d . . .
H1 H 0.7852 -0.0392 0.9268 0.028 Uiso 1 1 calc R . .
C2 C 0.6534(3) 0.0849(2) 0.7702(2) 0.0223(4) Uani 1 1 d . . .
H2 H 0.5851 0.1227 0.8222 0.027 Uiso 1 1 calc R . .
C3 C 0.6332(2) 0.1275(2) 0.6297(2) 0.0191(4) Uani 1 1 d . . .
C4 C 0.7378(2) 0.0686(2) 0.5581(2) 0.0207(4) Uani 1 1 d . . .
H4 H 0.7278 0.0954 0.4632 0.025 Uiso 1 1 calc R . .
C5 C 0.8540(2) -0.0272(2) 0.6243(2) 0.0203(4) Uani 1 1 d . . .
H5 H 0.9247 -0.0667 0.5756 0.024 Uiso 1 1 calc R . .
C6 C 0.5044(2) 0.2294(2) 0.5648(2) 0.0204(4) Uani 1 1 d . . .
H6 H 0.4358 0.2609 0.619 0.025 Uiso 1 1 calc R . .
C7 C 0.4775(2) 0.2805(2) 0.4344(2) 0.0207(4) Uani 1 1 d . . .
H7 H 0.5463 0.2478 0.3809 0.025 Uiso 1 1 calc R . .
C8 C 0.3510(2) 0.3829(2) 0.3669(2) 0.0187(4) Uani 1 1 d . . .
C9 C 0.3381(2) 0.4236(2) 0.2275(2) 0.0204(4) Uani 1 1 d . . .
H9 H 0.4087 0.3836 0.1788 0.024 Uiso 1 1 calc R . .
C10 C 0.2236(2) 0.5213(2) 0.1621(2) 0.0216(4) Uani 1 1 d . . .
H10 H 0.2143 0.5485 0.0675 0.026 Uiso 1 1 calc R . .
C11 C 0.1324(2) 0.5427(2) 0.3641(2) 0.0203(4) Uani 1 1 d . . .
H11 H 0.0604 0.5854 0.4099 0.024 Uiso 1 1 calc R . .
C12 C 0.2438(2) 0.4447(2) 0.4341(2) 0.0204(4) Uani 1 1 d . . .
H12 H 0.2485 0.4187 0.5279 0.025 Uiso 1 1 calc R . .
H2B H 0.341(4) 0.396(4) 0.857(3) 0.056(10) Uiso 1 1 d . . .
H7A H 0.353(3) 0.880(3) 0.855(3) 0.036(8) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4324(16) . ?
S1 O3 1.4513(15) . ?
S1 O1 1.4583(14) . ?
S1 O2 1.5670(15) . ?
S2 O6 1.4427(15) . ?
S2 O8 1.4443(16) . ?
S2 O5 1.4553(15) . ?
S2 O7 1.5638(15) . ?
O2 H2B 0.80(3) . ?
O7 H7A 0.79(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.347(3) . ?
N1 H1A 0.88 . ?
N2 C10 1.340(3) . ?
N2 C11 1.343(3) . ?
N2 H2A 0.88 . ?
C1 C2 1.365(3) . ?
C1 H1 0.95 . ?
C2 C3 1.405(3) . ?
C2 H2 0.95 . ?
C3 C4 1.403(3) . ?
C3 C6 1.468(3) . ?
C4 C5 1.367(3) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 C7 1.335(3) . ?
C6 H6 0.95 . ?
C7 C8 1.465(3) . ?
C7 H7 0.95 . ?
C8 C12 1.403(3) . ?
C8 C9 1.403(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.369(3) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?

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
O4 S1 O3 115.42(10) . . ?
O4 S1 O1 112.81(9) . . ?
O3 S1 O1 111.15(9) . . ?
O4 S1 O2 107.35(9) . . ?
O3 S1 O2 101.88(9) . . ?
O1 S1 O2 107.24(9) . . ?
O6 S2 O8 112.41(9) . . ?
O6 S2 O5 112.28(9) . . ?
O8 S2 O5 113.34(9) . . ?
O6 S2 O7 107.55(9) . . ?
O8 S2 O7 103.06(9) . . ?
O5 S2 O7 107.49(9) . . ?
S1 O2 H2B 108(2) . . ?
S2 O7 H7A 110(2) . . ?
C1 N1 C5 121.82(17) . . ?
C1 N1 H1A 119.1 . . ?
C5 N1 H1A 119.1 . . ?
C10 N2 C11 122.02(17) . . ?
C10 N2 H2A 119 . . ?
C11 N2 H2A 119 . . ?
N1 C1 C2 120.55(18) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 119.82(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 117.65(18) . . ?
C4 C3 C6 123.34(18) . . ?
C2 C3 C6 119.01(18) . . ?
C5 C4 C3 120.28(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 119.88(18) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C3 124.11(19) . . ?
C7 C6 H6 117.9 . . ?
C3 C6 H6 117.9 . . ?
C6 C7 C8 125.56(19) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C12 C8 C9 117.93(18) . . ?
C12 C8 C7 124.01(18) . . ?
C9 C8 C7 118.04(18) . . ?
C10 C9 C8 119.78(18) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 120.28(18) . . ?
N2 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N2 C11 C12 120.12(18) . . ?
N2 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C8 119.87(18) . . ?
C11 C12 H12 120.1 . . ?
C8 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.7(3) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C6 179.32(19) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C6 C3 C4 C5 -179.21(19) . . . . ?
C1 N1 C5 C4 -0.6(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C4 C3 C6 C7 -2.6(3) . . . . ?
C2 C3 C6 C7 177.9(2) . . . . ?
C3 C6 C7 C8 -179.59(18) . . . . ?
C6 C7 C8 C12 2.2(3) . . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C12 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -178.69(18) . . . . ?
C11 N2 C10 C9 -0.5(3) . . . . ?
C8 C9 C10 N2 0.4(3) . . . . ?
C10 N2 C11 C12 0.0(3) . . . . ?
N2 C11 C12 C8 0.6(3) . . . . ?
C9 C8 C12 C11 -0.7(3) . . . . ?
C7 C8 C12 C11 178.11(18) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

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

data_crystal_1
_database_code_depnum_ccdc_archive 'CCDC 939268'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H14 N2 O8 S2'
_chemical_formula_sum            'C12 H14 N2 O8 S2'
_chemical_formula_weight         378.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6748(4)
_cell_length_b                   9.2418(4)
_cell_length_c                   9.7123(5)
_cell_angle_alpha                95.073(2)
_cell_angle_beta                 110.088(2)
_cell_angle_gamma                90.128(2)
_cell_volume                     727.97(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    5527
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.35

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_T_max  0.959

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_number            10313
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.959
_reflns_number_total             2871
_reflns_number_gt                2521
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0414P)²+0.5826P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_restrained_S_all      1.03
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.23604(5) 0.20210(5) 0.83102(5) 0.01550(13) Uani 1 1 d . . .
S2 S 0.20206(5) 0.70754(5) 0.78347(5) 0.01553(13) Uani 1 1 d . . .
O1 O 0.11628(15) 0.23948(14) 0.90218(14) 0.0208(3) Uani 1 1 d . . .
O2 O 0.37783(16) 0.32220(15) 0.88893(15) 0.0217(3) Uani 1 1 d . . .
O3 O 0.32189(16) 0.07246(14) 0.88441(16) 0.0248(3) Uani 1 1 d . . .
O4 O 0.16909(17) 0.20155(16) 0.67366(14) 0.0269(3) Uani 1 1 d . . .
O5 O 0.11348(16) 0.74206(15) 0.88476(14) 0.0224(3) Uani 1 1 d . . .
O6 O 0.11528(15) 0.74942(14) 0.63801(14) 0.0207(3) Uani 1 1 d . . .
O7 O 0.36946(15) 0.79626(15) 0.84510(15) 0.0217(3) Uani 1 1 d . . .
O8 O 0.25282(17) 0.55842(14) 0.78136(16) 0.0272(3) Uani 1 1 d . . .
N1 N 0.86820(18) -0.06483(16) 0.75888(16) 0.0175(3) Uani 1 1 d . . .
H1A H 0.9431 -0.1268 0.8001 0.021 Uiso 1 1 calc R . .
N2 N 0.12437(17) 0.57858(16) 0.23064(16) 0.0174(3) Uani 1 1 d . . .
H2A H 0.052 0.6415 0.1871 0.021 Uiso 1 1 calc R . .
C1 C 0.7717(2) -0.0111(2) 0.8320(2) 0.0208(4) Uani 1 1 d . . .
H1 H 0.7854 -0.0397 0.927 0.025 Uiso 1 1 calc R . .
C2 C 0.6532(2) 0.0849(2) 0.7699(2) 0.0199(4) Uani 1 1 d . . .
H2 H 0.5848 0.1226 0.8218 0.024 Uiso 1 1 calc R . .
C3 C 0.6330(2) 0.12740(19) 0.62990(19) 0.0168(4) Uani 1 1 d . . .
C4 C 0.7375(2) 0.06913(19) 0.55829(19) 0.0177(4) Uani 1 1 d . . .
H4 H 0.7276 0.0962 0.4636 0.021 Uiso 1 1 calc R . .
C5 C 0.8541(2) -0.02690(19) 0.6246(2) 0.0181(4) Uani 1 1 d . . .
H5 H 0.9246 -0.0665 0.5758 0.022 Uiso 1 1 calc R . .
C6 C 0.5040(2) 0.22953(19) 0.5649(2) 0.0174(4) Uani 1 1 d . . .
H6 H 0.4355 0.2612 0.6189 0.021 Uiso 1 1 calc R . .
C7 C 0.4776(2) 0.28029(19) 0.4346(2) 0.0177(4) Uani 1 1 d . . .
H7 H 0.5463 0.2474 0.3811 0.021 Uiso 1 1 calc R . .
C8 C 0.3507(2) 0.38299(19) 0.36691(19) 0.0159(4) Uani 1 1 d . . .
C9 C 0.3380(2) 0.42378(19) 0.22746(19) 0.0179(4) Uani 1 1 d . . .
H9 H 0.4086 0.3839 0.1789 0.022 Uiso 1 1 calc R . .
C10 C 0.2232(2) 0.5214(2) 0.1618(2) 0.0191(4) Uani 1 1 d . . .
H10 H 0.2139 0.5486 0.0672 0.023 Uiso 1 1 calc R . .
C11 C 0.1322(2) 0.5429(2) 0.36409(19) 0.0178(4) Uani 1 1 d . . .
H11 H 0.0606 0.5858 0.41 0.021 Uiso 1 1 calc R . .
C12 C 0.2437(2) 0.4443(2) 0.43415(19) 0.0177(4) Uani 1 1 d . . .
H12 H 0.2481 0.4179 0.5277 0.021 Uiso 1 1 calc R . .
H2B H 0.340(3) 0.402(3) 0.858(3) 0.044(8) Uiso 1 1 d . . .
H7A H 0.352(3) 0.885(3) 0.857(3) 0.044(8) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4360(14) . ?
S1 O3 1.4517(13) . ?
S1 O1 1.4591(12) . ?
S1 O2 1.5715(13) . ?
S2 O6 1.4422(13) . ?
S2 O8 1.4483(14) . ?
S2 O5 1.4576(13) . ?
S2 O7 1.5653(13) . ?
O2 H2B 0.84(3) . ?
O7 H7A 0.84(3) . ?
N1 C1 1.342(2) . ?
N1 C5 1.345(2) . ?
N1 H1A 0.88 . ?
N2 C10 1.340(2) . ?
N2 C11 1.345(2) . ?
N2 H2A 0.88 . ?
C1 C2 1.371(3) . ?
C1 H1 0.95 . ?
C2 C3 1.402(2) . ?
C2 H2 0.95 . ?
C3 C4 1.401(2) . ?
C3 C6 1.472(2) . ?
C4 C5 1.372(2) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 C7 1.335(3) . ?
C6 H6 0.95 . ?
C7 C8 1.470(2) . ?
C7 H7 0.95 . ?
C8 C12 1.401(2) . ?
C8 C9 1.406(2) . ?
C9 C10 1.372(2) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.374(2) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?

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
O4 S1 O3 115.20(8) . . ?
O4 S1 O1 112.88(8) . . ?
O3 S1 O1 111.23(8) . . ?
O4 S1 O2 107.27(8) . . ?
O3 S1 O2 102.02(8) . . ?
O1 S1 O2 107.26(8) . . ?
O6 S2 O8 112.57(8) . . ?
O6 S2 O5 112.34(7) . . ?
O8 S2 O5 113.29(8) . . ?
O6 S2 O7 107.53(8) . . ?
O8 S2 O7 102.87(8) . . ?
O5 S2 O7 107.50(8) . . ?
S1 O2 H2B 108.8(18) . . ?
S2 O7 H7A 109.4(18) . . ?
C1 N1 C5 122.08(15) . . ?
C1 N1 H1A 119 . . ?
C5 N1 H1A 119 . . ?
C10 N2 C11 122.14(15) . . ?
C10 N2 H2A 118.9 . . ?
C11 N2 H2A 118.9 . . ?
N1 C1 C2 120.16(16) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C1 C2 C3 119.97(16) . . ?
C1 C2 H2 120 . . ?
C3 C2 H2 120 . . ?
C4 C3 C2 117.78(16) . . ?
C4 C3 C6 123.21(16) . . ?
C2 C3 C6 119.01(16) . . ?
C5 C4 C3 120.18(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 119.83(16) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C3 123.90(17) . . ?
C7 C6 H6 118.1 . . ?
C3 C6 H6 118.1 . . ?
C6 C7 C8 125.32(17) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C12 C8 C9 118.11(16) . . ?
C12 C8 C7 123.91(16) . . ?
C9 C8 C7 117.97(15) . . ?
C10 C9 C8 119.78(16) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 120.16(16) . . ?
N2 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
N2 C11 C12 120.11(16) . . ?
N2 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C8 119.70(16) . . ?
C11 C12 H12 120.1 . . ?
C8 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.4(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C6 179.43(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C6 C3 C4 C5 -179.26(17) . . . . ?
C1 N1 C5 C4 -0.3(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C4 C3 C6 C7 -2.4(3) . . . . ?
C2 C3 C6 C7 177.93(18) . . . . ?
C3 C6 C7 C8 -179.56(16) . . . . ?
C6 C7 C8 C12 2.0(3) . . . . ?
C6 C7 C8 C9 -179.06(18) . . . . ?
C12 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 -178.81(16) . . . . ?
C11 N2 C10 C9 -0.4(3) . . . . ?
C8 C9 C10 N2 0.5(3) . . . . ?
C10 N2 C11 C12 -0.3(3) . . . . ?
N2 C11 C12 C8 1.0(3) . . . . ?
C9 C8 C12 C11 -0.9(3) . . . . ?
C7 C8 C12 C11 178.02(16) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

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

data_crystal_1_php
_database_code_depnum_ccdc_archive 'CCDC 1504955'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_date             2016-08-06T00:15:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'S4  O18  N5  C30  H34'
_chemical_formula_sum            'C60 H74 N10 O36 S8'
_chemical_formula_weight         1767.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8660(3)
_cell_length_b                   11.0557(3)
_cell_length_c                   16.8860(5)
_cell_angle_alpha                80.416(2)
_cell_angle_beta                 88.478(3)
_cell_angle_gamma                86.132(2)
_cell_volume                     1811.79(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      31.59
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.62
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   multi-scan
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_T_min  0.4791
_exptl_absorpt_correction_T_max  0.7534

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_measurement_device_type  'Bruker Prospector'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_number            61739
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             7381
_reflns_number_gt                5515
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+1.8643P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_number_reflns         7381
_refine_ls_number_parameters     571
_refine_ls_number_restraints     8
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S4 S 1.23976(6) 0.16996(5) 0.96635(3) 0.01776(14) Uani 1 1 d . . . . .
S1 S 1.30615(6) 0.12314(6) 0.37997(3) 0.01995(14) Uani 1 1 d . . . . .
S2 S 1.15755(6) 0.24488(6) 0.59698(3) 0.01996(14) Uani 1 1 d . . . . .
S3 S 0.92681(6) 0.41155(5) 0.79103(3) 0.01798(14) Uani 1 1 d . . . . .
O005 O 1.36574(16) 0.09696(16) 0.98415(10) 0.0229(4) Uani 1 1 d . . . . .
O15 O 1.12077(16) 0.09924(15) 0.98933(10) 0.0208(4) Uani 1 1 d . . . . .
O13 O 1.24169(18) 0.20070(17) 0.87221(10) 0.0234(4) Uani 1 1 d . . . . .
O8 O 1.28790(17) 0.17890(17) 0.58232(10) 0.0270(4) Uani 1 1 d . . . . .
O12 O 0.80172(17) 0.35098(16) 0.78034(11) 0.0250(4) Uani 1 1 d . . . . .
O2 O 1.26158(17) 0.25192(16) 0.36313(10) 0.0254(4) Uani 1 1 d . . . . .
O2W O -0.45599(18) 1.10555(18) 0.84513(12) 0.0276(4) Uani 1 1 d DG . . . .
O7 O 1.13512(18) 0.35963(16) 0.54299(10) 0.0268(4) Uani 1 1 d . . . . .
O1 O 1.39365(17) 0.10182(18) 0.45737(10) 0.0284(4) Uani 1 1 d . . . . .
H1 H 1.3506 0.1315 0.494 0.043 Uiso 1 1 calc R U . . .
O14 O 1.23052(18) 0.28488(15) 0.99684(10) 0.0256(4) Uani 1 1 d . . . . .
O3 O 1.19233(17) 0.04424(16) 0.39646(11) 0.0283(4) Uani 1 1 d . . . . .
O9 O 1.0018(2) 0.43409(19) 0.71133(11) 0.0295(4) Uani 1 1 d D . . . .
O4 O 1.39870(18) 0.08400(18) 0.32028(11) 0.0310(4) Uani 1 1 d . . . . .
O10 O 1.01532(18) 0.32906(19) 0.84681(10) 0.0321(5) Uani 1 1 d . . . . .
O1W O 1.6198(2) -0.0374(2) 0.26581(12) 0.0319(4) Uani 1 1 d DG . . . .
O11 O 0.89500(19) 0.52869(16) 0.81679(11) 0.0321(4) Uani 1 1 d . . . . .
O5 O 1.1677(2) 0.27132(19) 0.68173(10) 0.0364(5) Uani 1 1 d . . . . .
O6 O 1.04721(18) 0.16394(16) 0.59458(12) 0.0334(5) Uani 1 1 d . . . . .
N4 N -0.2067(2) 0.99885(19) 0.82291(12) 0.0216(4) Uani 1 1 d . . . . .
N2 N 0.0510(2) 0.82927(19) 0.59777(11) 0.0211(4) Uani 1 1 d . . . . .
H2A H -0.0265 0.8732 0.5994 0.025 Uiso 1 1 calc R U . . .
N3 N 0.5682(2) 0.48087(19) 0.79437(11) 0.0201(4) Uani 1 1 d . . . . .
H3A H 0.6459 0.437 0.7935 0.024 Uiso 1 1 calc R U . . .
N1 N 0.8022(2) 0.28006(19) 0.60350(12) 0.0214(4) Uani 1 1 d . . . . .
N5 N 0.8781(2) 0.2266(2) 1.00305(12) 0.0245(5) Uani 1 1 d . . . . .
C8 C 0.2928(2) 0.6921(2) 0.59399(13) 0.0178(5) Uani 1 1 d . . . . .
C14 C 0.4481(2) 0.6749(2) 0.78160(13) 0.0204(5) Uani 1 1 d . . . . .
H14B H 0.4489 0.762 0.7716 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3298(2) 0.4903(2) 0.81225(13) 0.0203(5) Uani 1 1 d . . . . .
H16B H 0.2482 0.4492 0.8235 0.024 Uiso 1 1 calc R U . . .
C2 C 0.6902(2) 0.4772(2) 0.58351(13) 0.0188(5) Uani 1 1 d . . . . .
H2B H 0.6935 0.5638 0.569 0.023 Uiso 1 1 calc R U . . .
C20 C 0.0375(2) 0.8720(2) 0.80261(13) 0.0192(5) Uani 1 1 d . . . . .
C15 C 0.3250(2) 0.6183(2) 0.79804(13) 0.0183(5) Uani 1 1 d . . . . .
C19 C 0.1717(2) 0.8073(2) 0.79505(13) 0.0199(5) Uani 1 1 d . . . . .
H19B H 0.2485 0.8553 0.7851 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5671(2) 0.4258(2) 0.60664(13) 0.0186(5) Uani 1 1 d . . . . .
C7 C 0.4234(2) 0.6217(2) 0.59297(14) 0.0205(5) Uani 1 1 d . . . . .
H7B H 0.5028 0.6659 0.5815 0.025 Uiso 1 1 calc R U . . .
C1 C 0.8064(2) 0.4023(2) 0.58179(13) 0.0206(5) Uani 1 1 d . . . . .
H1B H 0.8902 0.437 0.5652 0.025 Uiso 1 1 calc R U . . .
C12 C 0.1691(2) 0.6356(2) 0.60681(14) 0.0205(5) Uani 1 1 d . . . . .
H12B H 0.1683 0.5486 0.6141 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5680(2) 0.6034(2) 0.77998(13) 0.0207(5) Uani 1 1 d . . . . .
H13B H 0.6512 0.6417 0.7685 0.025 Uiso 1 1 calc R U . . .
C17 C 0.4523(2) 0.4229(2) 0.81015(13) 0.0204(5) Uani 1 1 d . . . . .
H17B H 0.4549 0.3356 0.8198 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1921(2) 0.6855(2) 0.80134(13) 0.0200(5) Uani 1 1 d . . . . .
H18B H 0.1142 0.6385 0.8085 0.024 Uiso 1 1 calc R U . . .
C27 C 0.6434(3) 0.3720(2) 1.00360(13) 0.0234(5) Uani 1 1 d . . . . .
C6 C 0.4379(2) 0.4987(2) 0.60726(14) 0.0200(5) Uani 1 1 d . . . . .
H6B H 0.3579 0.4554 0.6187 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6871(3) 0.2270(2) 0.62744(15) 0.0239(5) Uani 1 1 d . . . . .
H5B H 0.6877 0.1404 0.6431 0.029 Uiso 1 1 calc R U . . .
C23 C -0.2033(3) 0.8778(2) 0.82502(14) 0.0218(5) Uani 1 1 d . . . . .
H23B H -0.2853 0.8367 0.8335 0.026 Uiso 1 1 calc R U . . .
C26 C 0.7694(3) 0.4221(3) 1.00026(14) 0.0257(6) Uani 1 1 d . . . . .
C11 C 0.0496(2) 0.7059(2) 0.60879(14) 0.0222(5) Uani 1 1 d . . . . .
H11B H -0.034 0.6676 0.6179 0.027 Uiso 1 1 calc R U . . .
C24 C -0.0829(3) 0.8111(2) 0.81504(14) 0.0229(5) Uani 1 1 d . . . . .
H24B H -0.0816 0.7248 0.8166 0.027 Uiso 1 1 calc R U . . .
C25 C 0.8852(3) 0.3473(3) 1.00046(14) 0.0264(6) Uani 1 1 d . . . . .
H25B H 0.9713 0.3813 0.9987 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2884(2) 0.8211(2) 0.58220(14) 0.0218(5) Uani 1 1 d . . . . .
H9B H 0.3701 0.8624 0.5727 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1665(3) 0.8875(2) 0.58443(14) 0.0232(5) Uani 1 1 d . . . . .
H10B H 0.1636 0.9747 0.5765 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5677(3) 0.2982(2) 0.62937(14) 0.0228(5) Uani 1 1 d . . . . .
H4B H 0.4856 0.2608 0.6462 0.027 Uiso 1 1 calc R U . . .
C21 C 0.0292(3) 0.9994(2) 0.80015(15) 0.0247(5) Uani 1 1 d . . . . .
H21B H 0.1091 1.0436 0.7914 0.03 Uiso 1 1 calc R U . . .
C28 C 0.6405(3) 0.2456(3) 1.00736(15) 0.0271(6) Uani 1 1 d . . . . .
H28B H 0.556 0.2084 1.0103 0.032 Uiso 1 1 calc R U . . .
C29 C 0.7600(3) 0.1748(2) 1.00680(15) 0.0271(6) Uani 1 1 d . . . . .
H29B H 0.7583 0.0885 1.0091 0.033 Uiso 1 1 calc R U . . .
C22 C -0.0936(3) 1.0605(2) 0.81038(16) 0.0277(6) Uani 1 1 d . . . . .
H22B H -0.0988 1.147 0.8086 0.033 Uiso 1 1 calc R U . . .
C30A C 0.5076(3) 0.4396(3) 1.00358(16) 0.0198(12) Uani 0.856(13) 1 d . . P A 2
C30B C 0.5693(18) 0.5000(15) 0.9973(8) 0.008(6) Uiso 0.144(13) 1 d . . P A 1
H4A H -0.289(3) 1.039(3) 0.8328(18) 0.043(9) Uiso 1 1 d . . . . .
H1A H 0.886(3) 0.230(3) 0.6038(18) 0.048(9) Uiso 1 1 d . . . . .
H5A H 0.954(4) 0.179(3) 1.0006(19) 0.053(10) Uiso 1 1 d . . . . .
H30A H 0.419(3) 0.400(3) 1.0081(16) 0.032(8) Uiso 1 1 d . . . . .
H26B H 0.769(3) 0.501(3) 0.9993(18) 0.038(8) Uiso 1 1 d . . . . .
H1W2 H -0.490(3) 1.088(3) 0.8887(12) 0.045(10) Uiso 1 1 d D . . . .
H2W2 H -0.511(3) 1.085(3) 0.8142(16) 0.052(11) Uiso 1 1 d D . . . .
H1W1 H 1.562(3) -0.003(3) 0.289(2) 0.062(13) Uiso 1 1 d D . . . .
H2W1 H 1.662(4) -0.085(3) 0.297(2) 0.097(17) Uiso 1 1 d D . . . .
H13 H 1.169(4) 0.243(4) 0.860(2) 0.069(13) Uiso 1 1 d . . . . .
H9 H 1.053(5) 0.379(4) 0.705(3) 0.13(2) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S4 O14 1.4447(17) . ?
S4 O005 1.4458(17) . ?
S4 O15 1.4624(17) . ?
S4 O13 1.5692(17) . ?
S1 O4 1.4421(18) . ?
S1 O2 1.4452(18) . ?
S1 O3 1.4609(18) . ?
S1 O1 1.5617(17) . ?
S2 O7 1.4413(18) . ?
S2 O6 1.4605(19) . ?
S2 O8 1.4710(18) . ?
S2 O5 1.5148(18) . ?
S3 O11 1.4457(18) . ?
S3 O10 1.4600(18) . ?
S3 O12 1.4723(17) . ?
S3 O9 1.5102(18) . ?
O13 H13 0.84(4) . ?
O2W H1W2 0.799(17) . ?
O2W H2W2 0.833(18) . ?
O1 H1 0.84 . ?
O9 H9 0.780(14) . ?
O1W H1W1 0.794(18) . ?
O1W H2W1 0.791(19) . ?
N4 C23 1.331(3) . ?
N4 C22 1.340(3) . ?
N4 H4A 0.92(3) . ?
N2 C10 1.342(3) . ?
N2 C11 1.347(3) . ?
N2 H2A 0.88 . ?
N3 C13 1.336(3) . ?
N3 C17 1.348(3) . ?
N3 H3A 0.88 . ?
N1 C5 1.336(3) . ?
N1 C1 1.344(3) . ?
N1 H1A 0.96(3) . ?
N5 C29 1.328(3) . ?
N5 C25 1.334(3) . ?
N5 H5A 0.89(4) . ?
C8 C12 1.403(3) . ?
C8 C9 1.405(3) . ?
C8 C7 1.461(3) . ?
C14 C13 1.380(3) . ?
C14 C15 1.404(3) . ?
C14 H14B 0.95 . ?
C16 C17 1.379(3) . ?
C16 C15 1.393(3) . ?
C16 H16B 0.95 . ?
C2 C1 1.371(3) . ?
C2 C3 1.394(3) . ?
C2 H2B 0.95 . ?
C20 C24 1.399(3) . ?
C20 C21 1.399(3) . ?
C20 C19 1.474(3) . ?
C15 C18 1.467(3) . ?
C19 C18 1.335(3) . ?
C19 H19B 0.95 . ?
C3 C4 1.398(3) . ?
C3 C6 1.462(3) . ?
C7 C6 1.339(3) . ?
C7 H7B 0.95 . ?
C1 H1B 0.95 . ?
C12 C11 1.370(3) . ?
C12 H12B 0.95 . ?
C13 H13B 0.95 . ?
C17 H17B 0.95 . ?
C18 H18B 0.95 . ?
C27 C26 1.391(4) . ?
C27 C28 1.391(4) . ?
C27 C30A 1.489(4) . ?
C27 C30B 1.537(16) . ?
C6 H6B 0.95 . ?
C5 C4 1.374(3) . ?
C5 H5B 0.95 . ?
C23 C24 1.377(3) . ?
C23 H23B 0.95 . ?
C26 C25 1.364(4) . ?
C26 H26B 0.87(3) . ?
C11 H11B 0.95 . ?
C24 H24B 0.95 . ?
C25 H25B 0.95 . ?
C9 C10 1.369(3) . ?
C9 H9B 0.95 . ?
C10 H10B 0.95 . ?
C4 H4B 0.95 . ?
C21 C22 1.368(4) . ?
C21 H21B 0.95 . ?
C28 C29 1.371(4) . ?
C28 H28B 0.95 . ?
C29 H29B 0.95 . ?
C22 H22B 0.95 . ?
C30A C30A 1.320(7) 2_667 ?
C30A H30A 0.99(3) . ?
C30B C30B 1.37(4) 2_667 ?

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
O14 S4 O005 114.37(10) . . ?
O14 S4 O15 111.79(10) . . ?
O005 S4 O15 112.26(10) . . ?
O14 S4 O13 107.77(10) . . ?
O005 S4 O13 103.32(10) . . ?
O15 S4 O13 106.57(10) . . ?
O4 S1 O2 113.89(11) . . ?
O4 S1 O3 111.92(11) . . ?
O2 S1 O3 112.17(10) . . ?
O4 S1 O1 103.16(11) . . ?
O2 S1 O1 108.00(10) . . ?
O3 S1 O1 106.98(11) . . ?
O7 S2 O6 111.85(11) . . ?
O7 S2 O8 113.18(11) . . ?
O6 S2 O8 109.40(11) . . ?
O7 S2 O5 108.83(11) . . ?
O6 S2 O5 108.78(12) . . ?
O8 S2 O5 104.46(10) . . ?
O11 S3 O10 112.59(11) . . ?
O11 S3 O12 110.70(10) . . ?
O10 S3 O12 109.38(11) . . ?
O11 S3 O9 108.36(12) . . ?
O10 S3 O9 107.12(11) . . ?
O12 S3 O9 108.55(11) . . ?
S4 O13 H13 106(3) . . ?
H1W2 O2W H2W2 104(3) . . ?
S1 O1 H1 109.5 . . ?
S3 O9 H9 112(4) . . ?
H1W1 O1W H2W1 109(3) . . ?
C23 N4 C22 121.4(2) . . ?
C23 N4 H4A 118(2) . . ?
C22 N4 H4A 121(2) . . ?
C10 N2 C11 122.2(2) . . ?
C10 N2 H2A 118.9 . . ?
C11 N2 H2A 118.9 . . ?
C13 N3 C17 121.6(2) . . ?
C13 N3 H3A 119.2 . . ?
C17 N3 H3A 119.2 . . ?
C5 N1 C1 122.1(2) . . ?
C5 N1 H1A 119.2(19) . . ?
C1 N1 H1A 119(2) . . ?
C29 N5 C25 121.9(2) . . ?
C29 N5 H5A 118(2) . . ?
C25 N5 H5A 120(2) . . ?
C12 C8 C9 117.7(2) . . ?
C12 C8 C7 122.4(2) . . ?
C9 C8 C7 119.8(2) . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14B 120.2 . . ?
C15 C14 H14B 120.2 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16B 119.8 . . ?
C15 C16 H16B 119.8 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2B 120.1 . . ?
C3 C2 H2B 120.1 . . ?
C24 C20 C21 117.8(2) . . ?
C24 C20 C19 122.9(2) . . ?
C21 C20 C19 119.2(2) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 C18 118.2(2) . . ?
C14 C15 C18 124.1(2) . . ?
C18 C19 C20 124.2(2) . . ?
C18 C19 H19B 117.9 . . ?
C20 C19 H19B 117.9 . . ?
C2 C3 C4 118.1(2) . . ?
C2 C3 C6 123.1(2) . . ?
C4 C3 C6 118.7(2) . . ?
C6 C7 C8 124.0(2) . . ?
C6 C7 H7B 118 . . ?
C8 C7 H7B 118 . . ?
N1 C1 C2 120.2(2) . . ?
N1 C1 H1B 119.9 . . ?
C2 C1 H1B 119.9 . . ?
C11 C12 C8 120.1(2) . . ?
C11 C12 H12B 120 . . ?
C8 C12 H12B 120 . . ?
N3 C13 C14 120.7(2) . . ?
N3 C13 H13B 119.7 . . ?
C14 C13 H13B 119.7 . . ?
N3 C17 C16 119.9(2) . . ?
N3 C17 H17B 120 . . ?
C16 C17 H17B 120 . . ?
C19 C18 C15 125.3(2) . . ?
C19 C18 H18B 117.4 . . ?
C15 C18 H18B 117.4 . . ?
C26 C27 C28 118.1(2) . . ?
C26 C27 C30A 126.9(3) . . ?
C28 C27 C30A 115.0(2) . . ?
C26 C27 C30B 91.4(7) . . ?
C28 C27 C30B 150.4(7) . . ?
C7 C6 C3 125.2(2) . . ?
C7 C6 H6B 117.4 . . ?
C3 C6 H6B 117.4 . . ?
N1 C5 C4 119.8(2) . . ?
N1 C5 H5B 120.1 . . ?
C4 C5 H5B 120.1 . . ?
N4 C23 C24 121.0(2) . . ?
N4 C23 H23B 119.5 . . ?
C24 C23 H23B 119.5 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26B 123(2) . . ?
C27 C26 H26B 117(2) . . ?
N2 C11 C12 119.9(2) . . ?
N2 C11 H11B 120.1 . . ?
C12 C11 H11B 120.1 . . ?
C23 C24 C20 119.3(2) . . ?
C23 C24 H24B 120.4 . . ?
C20 C24 H24B 120.4 . . ?
N5 C25 C26 120.3(2) . . ?
N5 C25 H25B 119.8 . . ?
C26 C25 H25B 119.8 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9B 119.9 . . ?
C8 C9 H9B 119.9 . . ?
N2 C10 C9 120.0(2) . . ?
N2 C10 H10B 120 . . ?
C9 C10 H10B 120 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4B 120 . . ?
C3 C4 H4B 120 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21B 119.9 . . ?
C20 C21 H21B 119.9 . . ?
C29 C28 C27 119.7(2) . . ?
C29 C28 H28B 120.1 . . ?
C27 C28 H28B 120.1 . . ?
N5 C29 C28 120.1(2) . . ?
N5 C29 H29B 119.9 . . ?
C28 C29 H29B 119.9 . . ?
N4 C22 C21 120.3(2) . . ?
N4 C22 H22B 119.8 . . ?
C21 C22 H22B 119.8 . . ?
C30A C30A C27 122.6(3) 2_667 . ?
C30A C30A H30A 112.7(17) 2_667 . ?
C27 C30A H30A 124.7(17) . . ?
C30B C30B C27 114.8(18) 2_667 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C16 C15 C14 0.1(3) . . . . ?
C17 C16 C15 C18 -179.7(2) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C13 C14 C15 C18 179.9(2) . . . . ?
C24 C20 C19 C18 -1.8(4) . . . . ?
C21 C20 C19 C18 175.9(2) . . . . ?
C1 C2 C3 C4 1.6(3) . . . . ?
C1 C2 C3 C6 -177.7(2) . . . . ?
C12 C8 C7 C6 -2.9(4) . . . . ?
C9 C8 C7 C6 176.8(2) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
C3 C2 C1 N1 -1.1(3) . . . . ?
C9 C8 C12 C11 -1.0(3) . . . . ?
C7 C8 C12 C11 178.7(2) . . . . ?
C17 N3 C13 C14 0.6(3) . . . . ?
C15 C14 C13 N3 -0.4(3) . . . . ?
C13 N3 C17 C16 -0.5(3) . . . . ?
C15 C16 C17 N3 0.1(3) . . . . ?
C20 C19 C18 C15 -176.8(2) . . . . ?
C16 C15 C18 C19 174.8(2) . . . . ?
C14 C15 C18 C19 -5.1(4) . . . . ?
C8 C7 C6 C3 180.0(2) . . . . ?
C2 C3 C6 C7 -6.1(4) . . . . ?
C4 C3 C6 C7 174.6(2) . . . . ?
C1 N1 C5 C4 0.8(4) . . . . ?
C22 N4 C23 C24 0.6(4) . . . . ?
C28 C27 C26 C25 0.2(3) . . . . ?
C30A C27 C26 C25 -179.7(2) . . . . ?
C30B C27 C26 C25 -177.5(5) . . . . ?
C10 N2 C11 C12 0.2(3) . . . . ?
C8 C12 C11 N2 0.5(3) . . . . ?
N4 C23 C24 C20 0.1(3) . . . . ?
C21 C20 C24 C23 -0.6(3) . . . . ?
C19 C20 C24 C23 177.1(2) . . . . ?
C29 N5 C25 C26 -1.1(4) . . . . ?
C27 C26 C25 N5 0.7(4) . . . . ?
C12 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C10 -178.9(2) . . . . ?
C11 N2 C10 C9 -0.4(3) . . . . ?
C8 C9 C10 N2 -0.1(3) . . . . ?
N1 C5 C4 C3 -0.3(4) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C6 C3 C4 C5 178.4(2) . . . . ?
C24 C20 C21 C22 0.5(4) . . . . ?
C19 C20 C21 C22 -177.3(2) . . . . ?
C26 C27 C28 C29 -0.7(3) . . . . ?
C30A C27 C28 C29 179.3(2) . . . . ?
C30B C27 C28 C29 174.6(10) . . . . ?
C25 N5 C29 C28 0.6(4) . . . . ?
C27 C28 C29 N5 0.3(4) . . . . ?
C23 N4 C22 C21 -0.6(4) . . . . ?
C20 C21 C22 N4 0.1(4) . . . . ?
C26 C27 C30A C30A 3.3(5) . . . 2_667 ?
C28 C27 C30A C30A -176.7(3) . . . 2_667 ?
C26 C27 C30B C30B -176.3(14) . . . 2_667 ?
C28 C27 C30B C30B 8(2) . . . 2_667 ?


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

data_crystal_2_ph
_database_code_depnum_ccdc_archive 'CCDC 1504958'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_date             2016-08-06T03:12:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'S4  O18  N5  C30  H37'
_chemical_formula_sum            'C60 H74 N10 O36 S8'
_chemical_formula_weight         1767.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8533(5)
_cell_length_b                   11.0612(6)
_cell_length_c                   16.9145(9)
_cell_angle_alpha                80.528(2)
_cell_angle_beta                 88.607(3)
_cell_angle_gamma                86.101(2)
_cell_volume                     1814.00(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.23
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   multi-scan
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_T_min  0.4635
_exptl_absorpt_correction_T_max  0.7625

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Prospector'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_number            24941
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_reflns_Friedel_coverage         0
_reflns_number_total             7260
_reflns_number_gt                5665
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+1.5663P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7260
_refine_ls_number_parameters     564
_refine_ls_number_restraints     12
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      5.534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.067

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 -0.24045(5) 0.83023(5) 0.03312(3) 0.01667(14) Uani 1 1 d . . . . .
S4 S -0.30737(6) 0.87783(5) 0.62054(4) 0.02028(14) Uani 1 1 d . . . . .
S2 S 0.07135(6) 0.58859(5) 0.20904(3) 0.01740(14) Uani 1 1 d . . . . .
S3 S -0.15848(6) 0.75576(6) 0.40340(4) 0.02046(14) Uani 1 1 d . . . . .
O3 O -0.12144(15) 0.90063(14) 0.01078(10) 0.0191(4) Uani 1 1 d . . . . .
O2 O -0.36655(15) 0.90419(15) 0.01533(10) 0.0225(4) Uani 1 1 d . . . . .
O1 O -0.24318(18) 0.79905(16) 0.12693(10) 0.0235(4) Uani 1 1 d . . . . .
O7 O 0.19606(16) 0.64932(15) 0.21885(11) 0.0257(4) Uani 1 1 d . . . . .
O4 O -0.23174(17) 0.71588(15) 0.00218(11) 0.0258(4) Uani 1 1 d . . . . .
O2W O 1.45435(18) -0.10542(17) 0.15432(12) 0.0278(4) Uani 1 1 d D . . . .
O15 O -0.26289(17) 0.74913(15) 0.63773(11) 0.0264(4) Uani 1 1 d . . . . .
O11 O -0.13542(18) 0.64082(16) 0.45660(10) 0.0281(4) Uani 1 1 d . . . . .
O14 O -0.19363(16) 0.95606(15) 0.60417(12) 0.0295(4) Uani 1 1 d . . . . .
O12 O -0.28848(16) 0.82252(17) 0.41836(11) 0.0293(4) Uani 1 1 d . . . . .
O5 O -0.00341(18) 0.56800(17) 0.28849(10) 0.0315(4) Uani 1 1 d . . . . .
O8 O 0.10347(19) 0.47101(16) 0.18398(12) 0.0339(5) Uani 1 1 d . . . . .
O6 O -0.01766(17) 0.67018(19) 0.15333(10) 0.0348(5) Uani 1 1 d . . . . .
O1W O -0.6201(2) 1.03856(19) 0.73551(13) 0.0337(5) Uani 1 1 d D . . . .
O16 O -0.39999(18) 0.91701(18) 0.68025(11) 0.0335(4) Uani 1 1 d . . . . .
O10 O -0.04756(17) 0.83604(16) 0.40548(13) 0.0343(5) Uani 1 1 d . . . . .
O9 O -0.1708(2) 0.7299(2) 0.31873(11) 0.0380(5) Uani 1 1 d D . . . .
N4 N 1.2055(2) 0.00136(18) 0.17698(12) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.9498(2) 0.17158(18) 0.40174(12) 0.0221(4) Uani 1 1 d . . . . .
H2 H 1.0275 0.1278 0.4002 0.027 Uiso 1 1 calc DR U . . .
N5 N 0.1211(2) 0.77250(19) -0.00281(12) 0.0229(5) Uani 1 1 d . . . . .
N1 N 0.1978(2) 0.71864(19) 0.39655(12) 0.0226(5) Uani 1 1 d D . . . .
C8 C 0.7083(2) 0.3074(2) 0.40641(13) 0.0187(5) Uani 1 1 d . . . . .
C16 C 0.5505(2) 0.3258(2) 0.21816(14) 0.0200(5) Uani 1 1 d . . . . .
H16B H 0.5501 0.2388 0.2283 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6728(2) 0.3823(2) 0.20171(13) 0.0180(5) Uani 1 1 d . . . . .
C4 C 0.3097(2) 0.5217(2) 0.41627(14) 0.0202(5) Uani 1 1 d . . . . .
H4B H 0.3066 0.4351 0.4304 0.024 Uiso 1 1 calc R U . . .
C19 C 0.8267(2) 0.1928(2) 0.20461(14) 0.0194(5) Uani 1 1 d . . . . .
H19B H 0.7499 0.1448 0.2146 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4326(2) 0.5742(2) 0.39371(14) 0.0190(5) Uani 1 1 d . . . . .
C27 C 0.3565(2) 0.6284(2) -0.00350(14) 0.0215(5) Uani 1 1 d . . . . .
C9 C 0.8318(2) 0.3640(2) 0.39299(14) 0.0214(5) Uani 1 1 d . . . . .
H9B H 0.8325 0.4509 0.3857 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4303(2) 0.3969(2) 0.21957(14) 0.0193(5) Uani 1 1 d . . . . .
H17B H 0.347 0.3586 0.2309 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6681(2) 0.5103(2) 0.18731(14) 0.0210(5) Uani 1 1 d . . . . .
H14B H 0.7498 0.5512 0.1761 0.025 Uiso 1 1 calc R U . . .
C20 C 0.9614(2) 0.1282(2) 0.19700(13) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.5628(2) 0.5009(2) 0.39289(14) 0.0206(5) Uani 1 1 d . . . . .
H6B H 0.6429 0.5439 0.3812 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5457(2) 0.5777(2) 0.18934(14) 0.0204(5) Uani 1 1 d . . . . .
H13B H 0.543 0.6649 0.1797 0.025 Uiso 1 1 calc R U . . .
C22 C 1.2024(2) 0.1225(2) 0.17533(14) 0.0224(5) Uani 1 1 d . . . . .
H22B H 1.2844 0.1635 0.167 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1933(2) 0.5972(2) 0.41769(14) 0.0209(5) Uani 1 1 d . . . . .
H5B H 0.1092 0.5628 0.4338 0.025 Uiso 1 1 calc R U . . .
C18 C 0.8066(2) 0.3146(2) 0.19825(13) 0.0189(5) Uani 1 1 d . . . . .
H18B H 0.8846 0.3614 0.1909 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5767(2) 0.3783(2) 0.40732(14) 0.0220(5) Uani 1 1 d . . . . .
H7B H 0.497 0.3344 0.4188 0.026 Uiso 1 1 calc R U . . .
C21 C 1.0821(2) 0.1886(2) 0.18547(14) 0.0216(5) Uani 1 1 d . . . . .
H21B H 1.0809 0.2748 0.1847 0.026 Uiso 1 1 calc R U . . .
C29 C 0.1144(2) 0.6527(2) -0.00010(15) 0.0242(5) Uani 1 1 d . . . . .
H29B H 0.0282 0.6186 0.002 0.029 Uiso 1 1 calc R U . . .
C10 C 0.9513(2) 0.2941(2) 0.39045(15) 0.0223(5) Uani 1 1 d . . . . .
H10B H 1.0349 0.3323 0.3807 0.027 Uiso 1 1 calc R U . . .
C28 C 0.2311(3) 0.5772(2) -0.00030(15) 0.0250(5) Uani 1 1 d . . . . .
H28B H 0.2262 0.4912 0.0017 0.03 Uiso 1 1 calc R U . . .
C24 C 0.9690(3) 0.0014(2) 0.19885(15) 0.0252(5) Uani 1 1 d . . . . .
H24B H 0.8889 -0.0424 0.207 0.03 Uiso 1 1 calc R U . . .
C11 C 0.8350(2) 0.1126(2) 0.41533(15) 0.0234(5) Uani 1 1 d . . . . .
H11B H 0.8381 0.0255 0.423 0.028 Uiso 1 1 calc R U . . .
C26 C 0.3587(2) 0.7543(2) -0.00746(15) 0.0243(5) Uani 1 1 d . . . . .
H26B H 0.4431 0.7918 -0.0111 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7128(2) 0.1795(2) 0.41797(14) 0.0213(5) Uani 1 1 d . . . . .
H12B H 0.631 0.1384 0.4277 0.026 Uiso 1 1 calc R U . . .
C25 C 0.2390(3) 0.8248(2) -0.00619(15) 0.0250(5) Uani 1 1 d . . . . .
H25B H 0.2404 0.9109 -0.0077 0.03 Uiso 1 1 calc R U . . .
C1 C 0.3125(3) 0.7721(2) 0.37297(16) 0.0257(6) Uani 1 1 d . . . . .
H1B H 0.3116 0.8588 0.3578 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4319(2) 0.7013(2) 0.37077(15) 0.0236(5) Uani 1 1 d . . . . .
H2B H 0.5139 0.7387 0.3537 0.028 Uiso 1 1 calc R U . . .
C23 C 1.0929(3) -0.0603(2) 0.18880(16) 0.0272(6) Uani 1 1 d . . . . .
H23B H 1.0981 -0.1467 0.1903 0.033 Uiso 1 1 calc R U . . .
C30A C 0.4923(3) 0.5606(3) -0.00340(16) 0.0175(12) Uani 0.846(13) 1 d . . P A 2
O13 O -0.39446(16) 0.89857(17) 0.54331(10) 0.0293(4) Uani 1 1 d . . . . .
H13A H -0.3501 0.8709 0.5064 0.044 Uiso 1 1 calc R U . . .
C30B C 0.4340(19) 0.4973(16) 0.0043(8) 0.012(6) Uiso 0.154(13) 1 d . . P A 1
N3 N 0.4301(2) 0.51989(18) 0.20499(12) 0.0189(4) Uani 1 1 d . . . . .
H1A H -0.179(4) 0.757(3) 0.139(2) 0.053(11) Uiso 1 1 d . . . . .
H4 H 1.283(3) -0.037(3) 0.1697(16) 0.030(7) Uiso 1 1 d . . . . .
H5 H 0.044(4) 0.823(3) 0.004(2) 0.059(10) Uiso 1 1 d . . . . .
H1 H 0.115(4) 0.774(3) 0.396(2) 0.061(10) Uiso 1 1 d . . . . .
H3 H 0.348(4) 0.562(3) 0.209(2) 0.060(10) Uiso 1 1 d . . . . .
H30A H 0.580(3) 0.602(3) -0.0119(17) 0.039(8) Uiso 1 1 d . . . . .
H1W2 H 1.487(3) -0.082(3) 0.1101(12) 0.061(12) Uiso 1 1 d D . . . .
H2W2 H 1.512(3) -0.082(3) 0.1848(16) 0.054(11) Uiso 1 1 d D . . . .
H1W1 H -0.561(3) 1.011(3) 0.7090(18) 0.065(13) Uiso 1 1 d D . . . .
H2W1 H -0.662(4) 1.090(3) 0.706(2) 0.093(16) Uiso 1 1 d D . . . .
H9A H -0.111(5) 0.684(5) 0.302(4) 0.17(3) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4429(17) . ?
S1 O2 1.4501(16) . ?
S1 O3 1.4595(16) . ?
S1 O1 1.5673(18) . ?
S4 O16 1.4444(18) . ?
S4 O15 1.4451(17) . ?
S4 O14 1.4558(18) . ?
S4 O13 1.5570(18) . ?
S2 O8 1.4458(18) . ?
S2 O6 1.4575(18) . ?
S2 O7 1.4655(17) . ?
S2 O5 1.5081(18) . ?
S3 O11 1.4393(18) . ?
S3 O10 1.4589(18) . ?
S3 O12 1.4722(17) . ?
S3 O9 1.515(2) . ?
O1 H1A 0.77(3) . ?
O2W H1W2 0.817(18) . ?
O2W H2W2 0.858(17) . ?
O1W H1W1 0.803(14) . ?
O1W H2W1 0.797(14) . ?
O9 H9A 0.82(2) . ?
N4 C22 1.334(3) . ?
N4 C23 1.336(3) . ?
N4 H4 0.87(3) . ?
N2 C10 1.338(3) . ?
N2 C11 1.340(3) . ?
N2 H2 0.88 . ?
N5 C29 1.325(3) . ?
N5 C25 1.328(3) . ?
N5 H5 0.93(4) . ?
N1 C1 1.333(3) . ?
N1 C5 1.336(3) . ?
N1 H1 0.99(4) . ?
C8 C12 1.394(3) . ?
C8 C9 1.403(3) . ?
C8 C7 1.470(3) . ?
C16 C17 1.379(3) . ?
C16 C15 1.396(3) . ?
C16 H16B 0.95 . ?
C15 C14 1.395(3) . ?
C15 C18 1.476(3) . ?
C4 C5 1.374(3) . ?
C4 C3 1.397(3) . ?
C4 H4B 0.95 . ?
C19 C18 1.336(3) . ?
C19 C20 1.477(3) . ?
C19 H19B 0.95 . ?
C3 C2 1.395(3) . ?
C3 C6 1.471(3) . ?
C27 C26 1.384(4) . ?
C27 C28 1.390(4) . ?
C27 C30A 1.489(3) . ?
C27 C30B 1.580(17) . ?
C9 C10 1.367(3) . ?
C9 H9B 0.95 . ?
C17 N3 1.342(3) . ?
C17 H17B 0.95 . ?
C14 C13 1.377(3) . ?
C14 H14B 0.95 . ?
C20 C24 1.395(3) . ?
C20 C21 1.397(3) . ?
C6 C7 1.336(3) . ?
C6 H6B 0.95 . ?
C13 N3 1.343(3) . ?
C13 H13B 0.95 . ?
C22 C21 1.372(3) . ?
C22 H22B 0.95 . ?
C5 H5B 0.95 . ?
C18 H18B 0.95 . ?
C7 H7B 0.95 . ?
C21 H21B 0.95 . ?
C29 C28 1.375(3) . ?
C29 H29B 0.95 . ?
C10 H10B 0.95 . ?
C28 H28B 0.95 . ?
C24 C23 1.378(3) . ?
C24 H24B 0.95 . ?
C11 C12 1.373(3) . ?
C11 H11B 0.95 . ?
C26 C25 1.370(3) . ?
C26 H26B 0.95 . ?
C12 H12B 0.95 . ?
C25 H25B 0.95 . ?
C1 C2 1.371(3) . ?
C1 H1B 0.95 . ?
C2 H2B 0.95 . ?
C23 H23B 0.95 . ?
C30A C30A 1.325(7) 2_665 ?
C30A H30A 1.00(3) . ?
O13 H13A 0.84 . ?
C30B C30B 1.31(4) 2_665 ?
N3 H3 0.91(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O2 114.42(10) . . ?
O4 S1 O3 111.94(10) . . ?
O2 S1 O3 112.02(9) . . ?
O4 S1 O1 107.85(10) . . ?
O2 S1 O1 103.12(10) . . ?
O3 S1 O1 106.73(10) . . ?
O16 S4 O15 113.54(11) . . ?
O16 S4 O14 112.07(11) . . ?
O15 S4 O14 112.13(10) . . ?
O16 S4 O13 103.45(10) . . ?
O15 S4 O13 108.01(11) . . ?
O14 S4 O13 106.95(11) . . ?
O8 S2 O6 112.74(12) . . ?
O8 S2 O7 110.53(10) . . ?
O6 S2 O7 109.24(11) . . ?
O8 S2 O5 108.73(11) . . ?
O6 S2 O5 106.78(10) . . ?
O7 S2 O5 108.69(11) . . ?
O11 S3 O10 111.85(11) . . ?
O11 S3 O12 113.66(11) . . ?
O10 S3 O12 109.33(11) . . ?
O11 S3 O9 108.73(12) . . ?
O10 S3 O9 108.85(12) . . ?
O12 S3 O9 104.04(11) . . ?
S1 O1 H1A 107(3) . . ?
H1W2 O2W H2W2 101(3) . . ?
H1W1 O1W H2W1 106(3) . . ?
S3 O9 H9A 118(4) . . ?
C22 N4 C23 121.7(2) . . ?
C22 N4 H4 118.1(19) . . ?
C23 N4 H4 120.2(19) . . ?
C10 N2 C11 122.8(2) . . ?
C10 N2 H2 118.6 . . ?
C11 N2 H2 118.6 . . ?
C29 N5 C25 122.1(2) . . ?
C29 N5 H5 121(2) . . ?
C25 N5 H5 116(2) . . ?
C1 N1 C5 122.6(2) . . ?
C1 N1 H1 116(2) . . ?
C5 N1 H1 121(2) . . ?
C12 C8 C9 117.8(2) . . ?
C12 C8 C7 119.9(2) . . ?
C9 C8 C7 122.3(2) . . ?
C17 C16 C15 119.7(2) . . ?
C17 C16 H16B 120.2 . . ?
C15 C16 H16B 120.2 . . ?
C14 C15 C16 118.0(2) . . ?
C14 C15 C18 118.0(2) . . ?
C16 C15 C18 123.9(2) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4B 120.5 . . ?
C3 C4 H4B 120.5 . . ?
C18 C19 C20 123.8(2) . . ?
C18 C19 H19B 118.1 . . ?
C20 C19 H19B 118.1 . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 C6 118.7(2) . . ?
C4 C3 C6 122.7(2) . . ?
C26 C27 C28 118.5(2) . . ?
C26 C27 C30A 115.4(2) . . ?
C28 C27 C30A 126.2(2) . . ?
C26 C27 C30B 150.1(7) . . ?
C28 C27 C30B 91.3(7) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9B 120 . . ?
C8 C9 H9B 120 . . ?
N3 C17 C16 120.4(2) . . ?
N3 C17 H17B 119.8 . . ?
C16 C17 H17B 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14B 119.9 . . ?
C15 C14 H14B 119.9 . . ?
C24 C20 C21 118.0(2) . . ?
C24 C20 C19 118.8(2) . . ?
C21 C20 C19 123.1(2) . . ?
C7 C6 C3 124.9(2) . . ?
C7 C6 H6B 117.5 . . ?
C3 C6 H6B 117.5 . . ?
N3 C13 C14 119.9(2) . . ?
N3 C13 H13B 120.1 . . ?
C14 C13 H13B 120.1 . . ?
N4 C22 C21 120.8(2) . . ?
N4 C22 H22B 119.6 . . ?
C21 C22 H22B 119.6 . . ?
N1 C5 C4 120.3(2) . . ?
N1 C5 H5B 119.8 . . ?
C4 C5 H5B 119.8 . . ?
C19 C18 C15 125.2(2) . . ?
C19 C18 H18B 117.4 . . ?
C15 C18 H18B 117.4 . . ?
C6 C7 C8 123.7(2) . . ?
C6 C7 H7B 118.1 . . ?
C8 C7 H7B 118.1 . . ?
C22 C21 C20 119.5(2) . . ?
C22 C21 H21B 120.3 . . ?
C20 C21 H21B 120.3 . . ?
N5 C29 C28 120.6(2) . . ?
N5 C29 H29B 119.7 . . ?
C28 C29 H29B 119.7 . . ?
N2 C10 C9 119.6(2) . . ?
N2 C10 H10B 120.2 . . ?
C9 C10 H10B 120.2 . . ?
C29 C28 C27 119.0(2) . . ?
C29 C28 H28B 120.5 . . ?
C27 C28 H28B 120.5 . . ?
C23 C24 C20 120.0(2) . . ?
C23 C24 H24B 120 . . ?
C20 C24 H24B 120 . . ?
N2 C11 C12 119.3(2) . . ?
N2 C11 H11B 120.3 . . ?
C12 C11 H11B 120.3 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26B 120.1 . . ?
C27 C26 H26B 120.1 . . ?
C11 C12 C8 120.3(2) . . ?
C11 C12 H12B 119.8 . . ?
C8 C12 H12B 119.8 . . ?
N5 C25 C26 120.0(2) . . ?
N5 C25 H25B 120 . . ?
C26 C25 H25B 120 . . ?
N1 C1 C2 119.6(2) . . ?
N1 C1 H1B 120.2 . . ?
C2 C1 H1B 120.2 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2B 120.1 . . ?
C3 C2 H2B 120.1 . . ?
N4 C23 C24 120.0(2) . . ?
N4 C23 H23B 120 . . ?
C24 C23 H23B 120 . . ?
C30A C30A C27 122.8(3) 2_665 . ?
C30A C30A H30A 113.5(17) 2_665 . ?
C27 C30A H30A 123.6(17) . . ?
S4 O13 H13A 109.5 . . ?
C30B C30B C27 112.7(19) 2_665 . ?
C17 N3 C13 121.7(2) . . ?
C17 N3 H3 116(2) . . ?
C13 N3 H3 122(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C16 C15 C14 0.1(3) . . . . ?
C17 C16 C15 C18 -179.6(2) . . . . ?
C5 C4 C3 C2 -2.2(3) . . . . ?
C5 C4 C3 C6 178.1(2) . . . . ?
C12 C8 C9 C10 0.9(3) . . . . ?
C7 C8 C9 C10 -178.1(2) . . . . ?
C15 C16 C17 N3 0.2(3) . . . . ?
C16 C15 C14 C13 -0.1(3) . . . . ?
C18 C15 C14 C13 179.6(2) . . . . ?
C18 C19 C20 C24 -175.3(2) . . . . ?
C18 C19 C20 C21 2.6(4) . . . . ?
C2 C3 C6 C7 -174.6(2) . . . . ?
C4 C3 C6 C7 5.2(4) . . . . ?
C15 C14 C13 N3 -0.2(4) . . . . ?
C23 N4 C22 C21 -0.3(4) . . . . ?
C1 N1 C5 C4 0.4(4) . . . . ?
C3 C4 C5 N1 1.1(3) . . . . ?
C20 C19 C18 C15 176.9(2) . . . . ?
C14 C15 C18 C19 -174.7(2) . . . . ?
C16 C15 C18 C19 5.0(4) . . . . ?
C3 C6 C7 C8 -179.7(2) . . . . ?
C12 C8 C7 C6 -176.6(2) . . . . ?
C9 C8 C7 C6 2.4(4) . . . . ?
N4 C22 C21 C20 -0.5(4) . . . . ?
C24 C20 C21 C22 0.9(3) . . . . ?
C19 C20 C21 C22 -177.0(2) . . . . ?
C25 N5 C29 C28 0.3(4) . . . . ?
C11 N2 C10 C9 0.3(4) . . . . ?
C8 C9 C10 N2 -0.8(4) . . . . ?
N5 C29 C28 C27 -0.1(4) . . . . ?
C26 C27 C28 C29 -0.9(4) . . . . ?
C30A C27 C28 C29 179.4(2) . . . . ?
C30B C27 C28 C29 176.3(5) . . . . ?
C21 C20 C24 C23 -0.5(4) . . . . ?
C19 C20 C24 C23 177.5(2) . . . . ?
C10 N2 C11 C12 0.0(4) . . . . ?
C28 C27 C26 C25 1.6(4) . . . . ?
C30A C27 C26 C25 -178.6(2) . . . . ?
C30B C27 C26 C25 -172.6(11) . . . . ?
N2 C11 C12 C8 0.2(4) . . . . ?
C9 C8 C12 C11 -0.6(3) . . . . ?
C7 C8 C12 C11 178.5(2) . . . . ?
C29 N5 C25 C26 0.4(4) . . . . ?
C27 C26 C25 N5 -1.4(4) . . . . ?
C5 N1 C1 C2 -0.7(4) . . . . ?
N1 C1 C2 C3 -0.4(4) . . . . ?
C4 C3 C2 C1 1.9(4) . . . . ?
C6 C3 C2 C1 -178.3(2) . . . . ?
C22 N4 C23 C24 0.7(4) . . . . ?
C20 C24 C23 N4 -0.3(4) . . . . ?
C26 C27 C30A C30A 177.2(3) . . . 2_665 ?
C28 C27 C30A C30A -3.0(5) . . . 2_665 ?
C26 C27 C30B C30B -12(2) . . . 2_665 ?
C28 C27 C30B C30B 173.4(15) . . . 2_665 ?
C16 C17 N3 C13 -0.6(3) . . . . ?
C14 C13 N3 C17 0.6(3) . . . . ?


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

data_crystal_1_ph
_database_code_depnum_ccdc_archive 'CCDC 1504954'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_date             2016-08-06T01:42:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'S4  O18  N5  C30  H34'
_chemical_formula_sum            'C60 H74 N10 O36 S8'
_chemical_formula_weight         1767.77

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8602(5)
_cell_length_b                   11.0507(6)
_cell_length_c                   16.8724(9)
_cell_angle_alpha                80.390(2)
_cell_angle_beta                 88.453(4)
_cell_angle_gamma                86.193(2)
_cell_volume                     1808.42(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7200
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      26.09
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_T_max  0.7584

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_number            25393
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_reflns_Friedel_coverage         0
_reflns_number_total             7224
_reflns_number_gt                5042
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+0.8069P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7224
_refine_ls_number_parameters     567
_refine_ls_number_restraints     5
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.083

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S4 S -0.23953(7) 0.82991(6) 0.03383(4) 0.01766(17) Uani 1 1 d . . . . .
S1 S -0.30539(7) 0.87646(6) 0.61966(4) 0.01894(18) Uani 1 1 d . . . . .
S2 S -0.15769(7) 0.75481(6) 0.40291(4) 0.01913(18) Uani 1 1 d . . . . .
S3 S 0.07377(7) 0.58825(6) 0.20892(4) 0.01759(18) Uani 1 1 d . . . . .
O14 O -0.36585(19) 0.90291(18) 0.01600(12) 0.0223(5) Uani 1 1 d . . . . .
O16 O -0.12093(19) 0.90100(17) 0.01046(12) 0.0206(4) Uani 1 1 d . . . . .
O3 O -0.2612(2) 0.74796(18) 0.63628(12) 0.0252(5) Uani 1 1 d . . . . .
O11 O 0.19881(19) 0.64910(18) 0.21961(12) 0.0234(5) Uani 1 1 d . . . . .
O13 O -0.2414(2) 0.79924(19) 0.12797(12) 0.0234(5) Uani 1 1 d . . . . .
O6 O -0.2881(2) 0.82065(19) 0.41734(12) 0.0253(5) Uani 1 1 d . . . . .
O7 O -0.1351(2) 0.63989(18) 0.45702(12) 0.0261(5) Uani 1 1 d . . . . .
O2 O -0.1919(2) 0.95547(18) 0.60297(13) 0.0263(5) Uani 1 1 d . . . . .
O1 O -0.3930(2) 0.8981(2) 0.54227(12) 0.0261(5) Uani 1 1 d . . . . .
H1A H -0.3461 0.8777 0.5038 0.039 Uiso 1 1 calc R U . . .
O2W O 1.4562(2) -0.1058(2) 0.15524(16) 0.0264(5) Uani 1 1 d G . . . .
O15 O -0.2307(2) 0.71465(18) 0.00358(13) 0.0254(5) Uani 1 1 d . . . . .
O1W O -0.6195(3) 1.0365(2) 0.73362(14) 0.0291(5) Uani 1 1 d G . . . .
O12 O -0.0011(2) 0.56604(19) 0.28862(12) 0.0281(5) Uani 1 1 d . . . . .
O4 O -0.3976(2) 0.9155(2) 0.67974(13) 0.0301(5) Uani 1 1 d . . . . .
O10 O 0.1054(2) 0.47079(18) 0.18323(13) 0.0313(5) Uani 1 1 d . . . . .
O9 O -0.0150(2) 0.6710(2) 0.15329(12) 0.0310(5) Uani 1 1 d . . . . .
O8 O -0.0472(2) 0.83600(18) 0.40522(15) 0.0317(5) Uani 1 1 d . . . . .
N2 N 0.9486(2) 0.1709(2) 0.40250(14) 0.0197(5) Uani 1 1 d . . . . .
H2 H 1.0262 0.127 0.4009 0.024 Uiso 1 1 calc R U . . .
O5 O -0.1677(2) 0.7286(2) 0.31792(12) 0.0355(6) Uani 1 1 d . . . . .
H5A H -0.1053 0.6766 0.3094 0.053 Uiso 1 1 calc R U . . .
N3 N 0.4327(2) 0.5189(2) 0.20560(13) 0.0187(5) Uani 1 1 d . . . . .
H3 H 0.3549 0.5627 0.2062 0.022 Uiso 1 1 calc R U . . .
N4 N 1.2068(3) 0.0008(2) 0.17725(14) 0.0206(6) Uani 1 1 d . . . . .
N1 N 0.1981(2) 0.7202(2) 0.39627(14) 0.0198(5) Uani 1 1 d D . . . .
N5 N 0.1222(3) 0.7734(2) -0.00310(15) 0.0250(6) Uani 1 1 d . . . . .
C3 C 0.4327(3) 0.5745(3) 0.39301(16) 0.0173(6) Uani 1 1 d . . . . .
C15 C 0.6754(3) 0.3814(3) 0.20185(16) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.3093(3) 0.5232(3) 0.41669(16) 0.0174(6) Uani 1 1 d . . . . .
H2B H 0.3059 0.4366 0.4317 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7065(3) 0.3081(2) 0.40589(16) 0.0171(6) Uani 1 1 d . . . . .
C7 C 0.5767(3) 0.3791(3) 0.40669(16) 0.0173(6) Uani 1 1 d . . . . .
H7B H 0.4971 0.3348 0.4181 0.021 Uiso 1 1 calc R U . . .
C14 C 0.5520(3) 0.3250(3) 0.21858(17) 0.0192(6) Uani 1 1 d . . . . .
H14B H 0.5511 0.2379 0.2286 0.023 Uiso 1 1 calc R U . . .
C12 C 0.8306(3) 0.3644(3) 0.39323(17) 0.0191(6) Uani 1 1 d . . . . .
H12B H 0.8317 0.4515 0.3858 0.023 Uiso 1 1 calc R U . . .
C13 C 0.4332(3) 0.3957(3) 0.22040(16) 0.0192(6) Uani 1 1 d . . . . .
H13B H 0.35 0.3572 0.2323 0.023 Uiso 1 1 calc R U . . .
C16 C 0.6696(3) 0.5099(3) 0.18784(16) 0.0192(6) Uani 1 1 d . . . . .
H16B H 0.751 0.5514 0.1767 0.023 Uiso 1 1 calc R U . . .
C1 C 0.1932(3) 0.5983(3) 0.41818(16) 0.0189(6) Uani 1 1 d . . . . .
H1B H 0.1092 0.564 0.4348 0.023 Uiso 1 1 calc R U . . .
C24 C 1.0833(3) 0.1882(3) 0.18513(17) 0.0222(7) Uani 1 1 d . . . . .
H24B H 1.0822 0.2745 0.1838 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5613(3) 0.5017(2) 0.39258(16) 0.0181(6) Uani 1 1 d . . . . .
H6B H 0.6413 0.5453 0.3813 0.022 Uiso 1 1 calc R U . . .
C17 C 0.5475(3) 0.5765(3) 0.18998(16) 0.0197(6) Uani 1 1 d . . . . .
H17B H 0.5447 0.6639 0.1803 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3132(3) 0.7731(3) 0.37230(17) 0.0221(7) Uani 1 1 d . . . . .
H5B H 0.3127 0.8598 0.3567 0.026 Uiso 1 1 calc R U . . .
C19 C 0.8287(3) 0.1924(3) 0.20534(17) 0.0202(6) Uani 1 1 d . . . . .
H19B H 0.7521 0.1441 0.2158 0.024 Uiso 1 1 calc R U . . .
C11 C 0.9495(3) 0.2944(3) 0.39158(17) 0.0216(6) Uani 1 1 d . . . . .
H11B H 1.0332 0.3328 0.3827 0.026 Uiso 1 1 calc R U . . .
C27 C 0.3563(3) 0.6282(3) -0.00336(16) 0.0221(7) Uani 1 1 d . . . . .
C20 C 0.9628(3) 0.1279(3) 0.19752(16) 0.0194(6) Uani 1 1 d . . . . .
C18 C 0.8077(3) 0.3143(3) 0.19871(16) 0.0195(6) Uani 1 1 d . . . . .
H18B H 0.8856 0.3615 0.1913 0.023 Uiso 1 1 calc R U . . .
C23 C 1.2028(3) 0.1226(3) 0.17492(17) 0.0221(7) Uani 1 1 d . . . . .
H23B H 1.2846 0.1641 0.166 0.026 Uiso 1 1 calc R U . . .
C26 C 0.2303(3) 0.5776(3) -0.00040(18) 0.0259(7) Uani 1 1 d . . . . .
C10 C 0.8327(3) 0.1128(3) 0.41575(17) 0.0214(6) Uani 1 1 d . . . . .
H10B H 0.8354 0.0255 0.4237 0.026 Uiso 1 1 calc R U . . .
C25 C 0.1149(3) 0.6530(3) -0.00043(18) 0.0261(7) Uani 1 1 d . . . . .
H25B H 0.0286 0.6192 0.0015 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7106(3) 0.1790(3) 0.41777(17) 0.0202(6) Uani 1 1 d . . . . .
H9B H 0.6288 0.1378 0.4272 0.024 Uiso 1 1 calc R U . . .
C21 C 0.9711(3) 0.0004(3) 0.20026(18) 0.0249(7) Uani 1 1 d . . . . .
H21B H 0.8913 -0.0439 0.2094 0.03 Uiso 1 1 calc R U . . .
C4 C 0.4323(3) 0.7021(3) 0.37027(17) 0.0198(6) Uani 1 1 d . . . . .
H4B H 0.5145 0.7396 0.3534 0.024 Uiso 1 1 calc R U . . .
C28 C 0.3595(3) 0.7550(3) -0.00763(17) 0.0266(7) Uani 1 1 d . . . . .
H28B H 0.4439 0.7924 -0.0111 0.032 Uiso 1 1 calc R U . . .
C29 C 0.2400(3) 0.8254(3) -0.00673(18) 0.0267(7) Uani 1 1 d . . . . .
H29B H 0.2416 0.9117 -0.0087 0.032 Uiso 1 1 calc R U . . .
C22 C 1.0941(3) -0.0606(3) 0.18985(19) 0.0279(7) Uani 1 1 d . . . . .
H22B H 1.0991 -0.1472 0.1916 0.033 Uiso 1 1 calc R U . . .
C30A C 0.4920(4) 0.5601(4) -0.0032(2) 0.0185(16) Uani 0.836(17) 1 d . . P A 1
C30B C 0.432(3) 0.4988(19) 0.0025(10) 0.014(8) Uiso 0.164(17) 1 d . . P A 2
H5 H 0.048(4) 0.824(4) 0.002(2) 0.054(12) Uiso 1 1 d . . . . .
H1 H 0.122(2) 0.770(3) 0.396(2) 0.037(10) Uiso 1 1 d D . . . .
H4 H 1.286(4) -0.035(3) 0.169(2) 0.033(10) Uiso 1 1 d . . . . .
H30A H 0.578(3) 0.602(2) -0.0072(16) 0.012(7) Uiso 1 1 d . . . . .
H1W2 H 1.498(4) -0.086(3) 0.110(2) 0.044(12) Uiso 1 1 d D . . . .
H2W2 H 1.517(4) -0.086(4) 0.186(2) 0.051(12) Uiso 1 1 d D . . . .
H1W1 H -0.562(4) 1.000(4) 0.713(2) 0.048(14) Uiso 1 1 d D . . . .
H2W1 H -0.654(4) 1.089(4) 0.700(3) 0.078(17) Uiso 1 1 d D . . . .
H13A H -0.169(4) 0.746(4) 0.138(3) 0.069(14) Uiso 1 1 d . . . . .
H26B H 0.233(3) 0.492(3) 0.001(2) 0.036(9) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S4 O15 1.446(2) . ?
S4 O14 1.449(2) . ?
S4 O16 1.461(2) . ?
S4 O13 1.568(2) . ?
S1 O3 1.441(2) . ?
S1 O4 1.444(2) . ?
S1 O2 1.458(2) . ?
S1 O1 1.561(2) . ?
S2 O7 1.443(2) . ?
S2 O8 1.462(2) . ?
S2 O6 1.470(2) . ?
S2 O5 1.516(2) . ?
S3 O10 1.448(2) . ?
S3 O9 1.462(2) . ?
S3 O11 1.472(2) . ?
S3 O12 1.508(2) . ?
O13 H13A 0.89(4) . ?
O1 H1A 0.84 . ?
O2W H1W2 0.85(4) . ?
O2W H2W2 0.87(4) . ?
O1W H1W1 0.79(4) . ?
O1W H2W1 0.80(4) . ?
N2 C10 1.344(4) . ?
N2 C11 1.347(4) . ?
N2 H2 0.88 . ?
O5 H5A 0.84 . ?
N3 C17 1.334(4) . ?
N3 C13 1.343(3) . ?
N3 H3 0.88 . ?
N4 C22 1.335(4) . ?
N4 C23 1.338(4) . ?
N4 H4 0.87(3) . ?
N1 C5 1.333(4) . ?
N1 C1 1.340(4) . ?
N1 H1 0.899(18) . ?
N5 C29 1.325(4) . ?
N5 C25 1.330(4) . ?
N5 H5 0.90(4) . ?
C3 C2 1.397(4) . ?
C3 C4 1.398(4) . ?
C3 C6 1.456(4) . ?
C15 C16 1.397(4) . ?
C15 C14 1.404(4) . ?
C15 C18 1.461(4) . ?
C2 C1 1.372(4) . ?
C2 H2B 0.95 . ?
C8 C12 1.405(4) . ?
C8 C9 1.405(4) . ?
C8 C7 1.457(4) . ?
C7 C6 1.335(4) . ?
C7 H7B 0.95 . ?
C14 C13 1.367(4) . ?
C14 H14B 0.95 . ?
C12 C11 1.364(4) . ?
C12 H12B 0.95 . ?
C13 H13B 0.95 . ?
C16 C17 1.372(4) . ?
C16 H16B 0.95 . ?
C1 H1B 0.95 . ?
C24 C23 1.364(4) . ?
C24 C20 1.394(4) . ?
C24 H24B 0.95 . ?
C6 H6B 0.95 . ?
C17 H17B 0.95 . ?
C5 C4 1.371(4) . ?
C5 H5B 0.95 . ?
C19 C18 1.335(4) . ?
C19 C20 1.473(4) . ?
C19 H19B 0.95 . ?
C11 H11B 0.95 . ?
C27 C26 1.393(4) . ?
C27 C28 1.394(4) . ?
C27 C30A 1.491(5) . ?
C27 C30B 1.56(2) . ?
C20 C21 1.399(4) . ?
C18 H18B 0.95 . ?
C23 H23B 0.95 . ?
C26 C25 1.365(4) . ?
C26 H26B 0.94(3) . ?
C10 C9 1.369(4) . ?
C10 H10B 0.95 . ?
C25 H25B 0.95 . ?
C9 H9B 0.95 . ?
C21 C22 1.369(4) . ?
C21 H21B 0.95 . ?
C4 H4B 0.95 . ?
C28 C29 1.369(4) . ?
C28 H28B 0.95 . ?
C29 H29B 0.95 . ?
C22 H22B 0.95 . ?
C30A C30A 1.314(9) 2_665 ?
C30A H30A 0.99(3) . ?
C30B C30B 1.34(5) 2_665 ?

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
O15 S4 O14 114.27(12) . . ?
O15 S4 O16 112.02(12) . . ?
O14 S4 O16 112.08(12) . . ?
O15 S4 O13 107.62(12) . . ?
O14 S4 O13 103.34(12) . . ?
O16 S4 O13 106.75(12) . . ?
O3 S1 O4 113.88(13) . . ?
O3 S1 O2 112.34(12) . . ?
O4 S1 O2 111.80(13) . . ?
O3 S1 O1 108.00(12) . . ?
O4 S1 O1 103.33(12) . . ?
O2 S1 O1 106.76(12) . . ?
O7 S2 O8 111.83(13) . . ?
O7 S2 O6 113.33(13) . . ?
O8 S2 O6 109.46(12) . . ?
O7 S2 O5 108.94(13) . . ?
O8 S2 O5 108.64(14) . . ?
O6 S2 O5 104.29(12) . . ?
O10 S3 O9 112.80(13) . . ?
O10 S3 O11 110.85(12) . . ?
O9 S3 O11 109.31(13) . . ?
O10 S3 O12 108.42(13) . . ?
O9 S3 O12 106.87(12) . . ?
O11 S3 O12 108.42(12) . . ?
S4 O13 H13A 102(3) . . ?
S1 O1 H1A 109.5 . . ?
H1W2 O2W H2W2 98(3) . . ?
H1W1 O1W H2W1 108(4) . . ?
C10 N2 C11 121.9(3) . . ?
C10 N2 H2 119.1 . . ?
C11 N2 H2 119.1 . . ?
S2 O5 H5A 109.5 . . ?
C17 N3 C13 121.5(2) . . ?
C17 N3 H3 119.3 . . ?
C13 N3 H3 119.3 . . ?
C22 N4 C23 121.1(3) . . ?
C22 N4 H4 122(2) . . ?
C23 N4 H4 116(2) . . ?
C5 N1 C1 122.4(3) . . ?
C5 N1 H1 117(2) . . ?
C1 N1 H1 120(2) . . ?
C29 N5 C25 122.1(3) . . ?
C29 N5 H5 115(2) . . ?
C25 N5 H5 123(2) . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 C6 123.1(3) . . ?
C4 C3 C6 118.8(3) . . ?
C16 C15 C14 117.2(3) . . ?
C16 C15 C18 118.7(3) . . ?
C14 C15 C18 124.1(3) . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2B 120.2 . . ?
C3 C2 H2B 120.2 . . ?
C12 C8 C9 117.7(3) . . ?
C12 C8 C7 122.1(2) . . ?
C9 C8 C7 120.1(3) . . ?
C6 C7 C8 124.8(3) . . ?
C6 C7 H7B 117.6 . . ?
C8 C7 H7B 117.6 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14B 120.1 . . ?
C15 C14 H14B 120.1 . . ?
C11 C12 C8 120.1(3) . . ?
C11 C12 H12B 119.9 . . ?
C8 C12 H12B 119.9 . . ?
N3 C13 C14 120.8(3) . . ?
N3 C13 H13B 119.6 . . ?
C14 C13 H13B 119.6 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16B 119.7 . . ?
C15 C16 H16B 119.7 . . ?
N1 C1 C2 120.0(3) . . ?
N1 C1 H1B 120 . . ?
C2 C1 H1B 120 . . ?
C23 C24 C20 119.7(3) . . ?
C23 C24 H24B 120.2 . . ?
C20 C24 H24B 120.2 . . ?
C7 C6 C3 125.8(3) . . ?
C7 C6 H6B 117.1 . . ?
C3 C6 H6B 117.1 . . ?
N3 C17 C16 120.1(3) . . ?
N3 C17 H17B 119.9 . . ?
C16 C17 H17B 119.9 . . ?
N1 C5 C4 119.9(3) . . ?
N1 C5 H5B 120.1 . . ?
C4 C5 H5B 120.1 . . ?
C18 C19 C20 124.4(3) . . ?
C18 C19 H19B 117.8 . . ?
C20 C19 H19B 117.8 . . ?
N2 C11 C12 120.2(3) . . ?
N2 C11 H11B 119.9 . . ?
C12 C11 H11B 119.9 . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 C30A 126.5(3) . . ?
C28 C27 C30A 115.2(3) . . ?
C26 C27 C30B 91.5(9) . . ?
C28 C27 C30B 150.1(10) . . ?
C24 C20 C21 117.6(3) . . ?
C24 C20 C19 123.2(3) . . ?
C21 C20 C19 119.2(3) . . ?
C19 C18 C15 125.7(3) . . ?
C19 C18 H18B 117.2 . . ?
C15 C18 H18B 117.2 . . ?
N4 C23 C24 121.1(3) . . ?
N4 C23 H23B 119.4 . . ?
C24 C23 H23B 119.4 . . ?
C25 C26 C27 119.1(3) . . ?
C25 C26 H26B 126(2) . . ?
C27 C26 H26B 115(2) . . ?
N2 C10 C9 120.2(3) . . ?
N2 C10 H10B 119.9 . . ?
C9 C10 H10B 119.9 . . ?
N5 C25 C26 120.7(3) . . ?
N5 C25 H25B 119.7 . . ?
C26 C25 H25B 119.7 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9B 120 . . ?
C8 C9 H9B 120 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21B 119.9 . . ?
C20 C21 H21B 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4B 120 . . ?
C3 C4 H4B 120 . . ?
C29 C28 C27 119.5(3) . . ?
C29 C28 H28B 120.2 . . ?
C27 C28 H28B 120.2 . . ?
N5 C29 C28 120.2(3) . . ?
N5 C29 H29B 119.9 . . ?
C28 C29 H29B 119.9 . . ?
N4 C22 C21 120.4(3) . . ?
N4 C22 H22B 119.8 . . ?
C21 C22 H22B 119.8 . . ?
C30A C30A C27 123.3(5) 2_665 . ?
C30A C30A H30A 114.0(16) 2_665 . ?
C27 C30A H30A 122.7(16) . . ?
C30B C30B C27 114(2) 2_665 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 -1.0(4) . . . . ?
C6 C3 C2 C1 177.7(3) . . . . ?
C12 C8 C7 C6 2.9(4) . . . . ?
C9 C8 C7 C6 -176.9(3) . . . . ?
C16 C15 C14 C13 0.2(4) . . . . ?
C18 C15 C14 C13 179.8(3) . . . . ?
C9 C8 C12 C11 1.0(4) . . . . ?
C7 C8 C12 C11 -178.9(3) . . . . ?
C17 N3 C13 C14 -1.1(4) . . . . ?
C15 C14 C13 N3 0.6(4) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C18 C15 C16 C17 179.8(3) . . . . ?
C5 N1 C1 C2 0.2(4) . . . . ?
C3 C2 C1 N1 0.6(4) . . . . ?
C8 C7 C6 C3 180.0(3) . . . . ?
C2 C3 C6 C7 6.8(4) . . . . ?
C4 C3 C6 C7 -174.6(3) . . . . ?
C13 N3 C17 C16 0.8(4) . . . . ?
C15 C16 C17 N3 0.0(4) . . . . ?
C1 N1 C5 C4 -0.7(4) . . . . ?
C10 N2 C11 C12 -0.4(4) . . . . ?
C8 C12 C11 N2 -0.4(4) . . . . ?
C23 C24 C20 C21 1.1(4) . . . . ?
C23 C24 C20 C19 -177.1(3) . . . . ?
C18 C19 C20 C24 2.4(5) . . . . ?
C18 C19 C20 C21 -175.7(3) . . . . ?
C20 C19 C18 C15 176.5(3) . . . . ?
C16 C15 C18 C19 -175.2(3) . . . . ?
C14 C15 C18 C19 5.1(5) . . . . ?
C22 N4 C23 C24 -0.2(4) . . . . ?
C20 C24 C23 N4 -0.6(4) . . . . ?
C28 C27 C26 C25 -1.1(4) . . . . ?
C30A C27 C26 C25 179.5(3) . . . . ?
C30B C27 C26 C25 177.5(7) . . . . ?
C11 N2 C10 C9 0.6(4) . . . . ?
C29 N5 C25 C26 0.8(4) . . . . ?
C27 C26 C25 N5 -0.1(4) . . . . ?
N2 C10 C9 C8 0.1(4) . . . . ?
C12 C8 C9 C10 -0.8(4) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C24 C20 C21 C22 -0.9(4) . . . . ?
C19 C20 C21 C22 177.3(3) . . . . ?
N1 C5 C4 C3 0.3(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C6 C3 C4 C5 -178.2(3) . . . . ?
C26 C27 C28 C29 1.7(4) . . . . ?
C30A C27 C28 C29 -178.9(3) . . . . ?
C30B C27 C28 C29 -175.4(13) . . . . ?
C25 N5 C29 C28 -0.2(5) . . . . ?
C27 C28 C29 N5 -1.1(4) . . . . ?
C23 N4 C22 C21 0.4(4) . . . . ?
C20 C21 C22 N4 0.2(5) . . . . ?
C26 C27 C30A C30A -2.8(6) . . . 2_665 ?
C28 C27 C30A C30A 177.7(4) . . . 2_665 ?
C26 C27 C30B C30B 176.5(18) . . . 2_665 ?
C28 C27 C30B C30B -6(3) . . . 2_665 ?


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

data_crystal_2
_database_code_depnum_ccdc_archive 'CCDC 1504956'
_audit_update_record             
;
2016-09-19 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'S2  O8  N2  C12  H14'
_chemical_formula_sum            'C12 H14 N2 O8 S2'
_chemical_formula_weight         378.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.6670(2)
_cell_length_b                   9.2424(3)
_cell_length_c                   9.7010(3)
_cell_angle_alpha                95.062(2)
_cell_angle_beta                 110.090(2)
_cell_angle_gamma                90.142(2)
_cell_volume                     726.51(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2958
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      26.4

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.416
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Prospector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20962
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.500
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2958
_reflns_number_gt                2713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Apex 2'
_computing_cell_refinement       'Bruker Apex 2'
_computing_data_reduction        'Bruker Apex 2'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0336P)²+0.5168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0072(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.73600(4) 0.20212(3) 0.83102(4) 0.01188(11) Uani 1 1 d . . . . .
S2 S 0.70203(4) 0.70761(3) 0.78351(4) 0.01192(11) Uani 1 1 d . . . . .
O2 O 0.61513(13) 0.74938(11) 0.63787(11) 0.0172(2) Uani 1 1 d . . . . .
O1 O 0.86950(12) 0.79644(11) 0.84509(12) 0.0183(2) Uani 1 1 d . . . . .
H1A H 0.8517 0.8852 0.8562 0.027 Uiso 1 1 calc R U . . .
O5 O 0.87772(13) 0.32230(11) 0.88906(12) 0.0183(2) Uani 1 1 d . . . . .
H2A H 0.8418 0.4015 0.8569 0.027 Uiso 1 1 calc R U . . .
O7 O 0.61623(13) 0.23958(11) 0.90237(12) 0.0180(2) Uani 1 1 d . . . . .
O3 O 0.61337(13) 0.74208(12) 0.88478(12) 0.0194(2) Uani 1 1 d . . . . .
O8 O 0.82180(14) 0.07247(11) 0.88437(13) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.75282(14) 0.55826(11) 0.78141(13) 0.0237(3) Uani 1 1 d . . . . .
O6 O 0.66861(14) 0.20155(12) 0.67341(12) 0.0231(3) Uani 1 1 d . . . . .
N2 N -0.36809(15) 1.06487(13) 0.24121(14) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.37551(15) 0.42136(12) 0.76928(14) 0.0142(3) Uani 1 1 d . . . . .
C11 C -0.35423(17) 1.02703(15) 0.37513(16) 0.0147(3) Uani 1 1 d . . . . .
H11C H -0.4249 1.0667 0.4238 0.018 Uiso 1 1 calc R U . . .
C8 C -0.13306(17) 0.87246(14) 0.37005(16) 0.0135(3) Uani 1 1 d . . . . .
C3 C 0.14934(17) 0.61701(14) 0.63323(16) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.25602(17) 0.55573(15) 0.56581(16) 0.0146(3) Uani 1 1 d . . . . .
H2C H 0.2513 0.5820 0.4720 0.018 Uiso 1 1 calc R U . . .
C1 C 0.36794(17) 0.45702(15) 0.63617(16) 0.0150(3) Uani 1 1 d . . . . .
H1C H 0.4398 0.4142 0.5903 0.018 Uiso 1 1 calc R U . . .
C4 C 0.16193(18) 0.57654(15) 0.77244(16) 0.0148(3) Uani 1 1 d . . . . .
H4C H 0.0914 0.6167 0.8210 0.018 Uiso 1 1 calc R U . . .
C7 C -0.00369(17) 0.77081(15) 0.43501(16) 0.0143(3) Uani 1 1 d . . . . .
H7C H 0.0655 0.7397 0.3813 0.017 Uiso 1 1 calc R U . . .
C12 C -0.23745(17) 0.93074(15) 0.44184(16) 0.0147(3) Uani 1 1 d . . . . .
H12C H -0.2276 0.9037 0.5367 0.018 Uiso 1 1 calc R U . . .
C9 C -0.15296(18) 0.91486(15) 0.23009(16) 0.0166(3) Uani 1 1 d . . . . .
H9C H -0.0844 0.8772 0.1782 0.020 Uiso 1 1 calc R U . . .
C6 C 0.02206(17) 0.71962(15) 0.56561(16) 0.0141(3) Uani 1 1 d . . . . .
H6C H -0.0472 0.7520 0.6188 0.017 Uiso 1 1 calc R U . . .
C5 C 0.27675(18) 0.47853(15) 0.83842(16) 0.0159(3) Uani 1 1 d . . . . .
H5C H 0.2861 0.4513 0.9331 0.019 Uiso 1 1 calc R U . . .
C10 C -0.27195(19) 1.01115(16) 0.16786(16) 0.0172(3) Uani 1 1 d . . . . .
H1OC H -0.2860 1.0396 0.0727 0.021 Uiso 1 1 calc R U . . .
H1B H 0.446(3) 0.361(2) 0.812(2) 0.027(5) Uiso 1 1 d . . . . .
H2B H -0.443(3) 1.126(2) 0.203(2) 0.028(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O6 1.4366(11) . ?
S1 O8 1.4513(10) . ?
S1 O7 1.4593(10) . ?
S1 O5 1.5708(10) . ?
S2 O2 1.4419(11) . ?
S2 O4 1.4504(10) . ?
S2 O3 1.4566(11) . ?
S2 O1 1.5651(10) . ?
O1 H1A 0.8400 . ?
O5 H2A 0.8400 . ?
N2 C10 1.3395(19) . ?
N2 C11 1.3408(19) . ?
N2 H2B 0.87(2) . ?
N1 C5 1.3401(19) . ?
N1 C1 1.3406(19) . ?
N1 H1B 0.85(2) . ?
C11 C12 1.375(2) . ?
C11 H11C 0.9500 . ?
C8 C9 1.400(2) . ?
C8 C12 1.401(2) . ?
C8 C7 1.4701(19) . ?
C3 C2 1.399(2) . ?
C3 C4 1.401(2) . ?
C3 C6 1.4712(19) . ?
C2 C1 1.378(2) . ?
C2 H2C 0.9500 . ?
C1 H1C 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4C 0.9500 . ?
C7 C6 1.338(2) . ?
C7 H7C 0.9500 . ?
C12 H12C 0.9500 . ?
C9 C10 1.375(2) . ?
C9 H9C 0.9500 . ?
C6 H6C 0.9500 . ?
C5 H5C 0.9500 . ?
C10 H1OC 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 O8 115.21(7) . . ?
O6 S1 O7 112.81(7) . . ?
O8 S1 O7 111.24(6) . . ?
O6 S1 O5 107.39(6) . . ?
O8 S1 O5 102.10(6) . . ?
O7 S1 O5 107.13(6) . . ?
O2 S2 O4 112.54(7) . . ?
O2 S2 O3 112.31(6) . . ?
O4 S2 O3 113.27(7) . . ?
O2 S2 O1 107.52(6) . . ?
O4 S2 O1 102.94(6) . . ?
O3 S2 O1 107.52(6) . . ?
S2 O1 H1A 109.5 . . ?
S1 O5 H2A 109.5 . . ?
C10 N2 C11 122.21(12) . . ?
C10 N2 H2B 120.7(13) . . ?
C11 N2 H2B 117.0(13) . . ?
C5 N1 C1 122.26(12) . . ?
C5 N1 H1B 118.9(14) . . ?
C1 N1 H1B 118.8(13) . . ?
N2 C11 C12 119.87(13) . . ?
N2 C11 H11C 120.1 . . ?
C12 C11 H11C 120.1 . . ?
C9 C8 C12 117.89(13) . . ?
C9 C8 C7 118.84(13) . . ?
C12 C8 C7 123.27(13) . . ?
C2 C3 C4 118.26(13) . . ?
C2 C3 C6 123.96(13) . . ?
C4 C3 C6 117.77(13) . . ?
C1 C2 C3 119.65(13) . . ?
C1 C2 H2C 120.2 . . ?
C3 C2 H2C 120.2 . . ?
N1 C1 C2 120.04(13) . . ?
N1 C1 H1C 120.0 . . ?
C2 C1 H1C 120.0 . . ?
C5 C4 C3 119.77(13) . . ?
C5 C4 H4C 120.1 . . ?
C3 C4 H4C 120.1 . . ?
C6 C7 C8 123.64(13) . . ?
C6 C7 H7C 118.2 . . ?
C8 C7 H7C 118.2 . . ?
C11 C12 C8 120.05(13) . . ?
C11 C12 H12C 120.0 . . ?
C8 C12 H12C 120.0 . . ?
C10 C9 C8 119.85(13) . . ?
C10 C9 H9C 120.1 . . ?
C8 C9 H9C 120.1 . . ?
C7 C6 C3 125.05(13) . . ?
C7 C6 H6C 117.5 . . ?
C3 C6 H6C 117.5 . . ?
N1 C5 C4 120.02(13) . . ?
N1 C5 H5C 120.0 . . ?
C4 C5 H5C 120.0 . . ?
N2 C10 C9 120.12(13) . . ?
N2 C10 H1OC 119.9 . . ?
C9 C10 H1OC 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C11 C12 0.4(2) . . . . ?
C4 C3 C2 C1 0.8(2) . . . . ?
C6 C3 C2 C1 -177.97(13) . . . . ?
C5 N1 C1 C2 0.1(2) . . . . ?
C3 C2 C1 N1 -0.7(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C6 C3 C4 C5 178.61(13) . . . . ?
C9 C8 C7 C6 -177.66(14) . . . . ?
C12 C8 C7 C6 3.0(2) . . . . ?
N2 C11 C12 C8 0.1(2) . . . . ?
C9 C8 C12 C11 -0.4(2) . . . . ?
C7 C8 C12 C11 179.02(13) . . . . ?
C12 C8 C9 C10 0.2(2) . . . . ?
C7 C8 C9 C10 -179.26(13) . . . . ?
C8 C7 C6 C3 179.48(12) . . . . ?
C2 C3 C6 C7 -2.5(2) . . . . ?
C4 C3 C6 C7 178.71(14) . . . . ?
C1 N1 C5 C4 0.5(2) . . . . ?
C3 C4 C5 N1 -0.4(2) . . . . ?
C11 N2 C10 C9 -0.7(2) . . . . ?
C8 C9 C10 N2 0.3(2) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.051

