# 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_1_1
_database_code_depnum_ccdc_archive 'CCDC 1575419'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H5 O6 S, C6 H13 N4'
_chemical_formula_sum            'C13 H18 N4 O6 S'
_chemical_formula_weight         358.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5803(7)
_cell_length_b                   10.4110(10)
_cell_length_c                   19.476(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.922(3)
_cell_angle_gamma                90
_cell_volume                     1522.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9076
_cell_measurement_temperature    222(2)
_cell_measurement_theta_max      28.207
_cell_measurement_theta_min      3.345
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhomboic
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34677
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_min         2.772
_diffrn_ambient_temperature      222.38
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3092
_reflns_number_total             3765
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3765
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+0.8086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33618(5) 0.84644(4) 0.17579(2) 0.02610(12) Uani 1 1 d . . . . .
N1 N 0.99841(17) 0.93261(13) 0.28358(7) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.09240(15) 0.98725(13) -0.13975(6) 0.0353(3) Uani 1 1 d . . . . .
O4 O 0.52411(14) 0.83588(12) 0.16564(6) 0.0330(3) Uani 1 1 d . . . . .
O1 O 0.33732(16) 1.04396(15) -0.06900(7) 0.0454(4) Uani 1 1 d . . . . .
O6 O 0.28415(16) 0.74302(13) 0.21860(6) 0.0385(3) Uani 1 1 d . . . . .
O3 O -0.11150(17) 0.80656(14) -0.09749(7) 0.0406(3) Uani 1 1 d . . . . .
C2 C 0.14517(19) 0.89762(15) -0.02647(8) 0.0255(3) Uani 1 1 d . . . . .
C7 C 0.24893(19) 0.90350(16) 0.03850(8) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.3459 0.9605 0.0458 0.031 Uiso 1 1 calc R . . . .
N2 N 1.05887(18) 0.93252(15) 0.40884(7) 0.0327(3) Uani 1 1 d . . . . .
C6 C 0.21025(19) 0.82595(15) 0.09240(8) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.1877(2) 0.97977(16) -0.08386(8) 0.0289(3) Uani 1 1 d . . . . .
N3 N 0.77912(18) 1.01963(15) 0.34992(7) 0.0352(3) Uani 1 1 d . . . . .
O5 O 0.29230(17) 0.97267(12) 0.19952(6) 0.0399(3) Uani 1 1 d . . . . .
C9 C 0.8561(2) 1.03428(17) 0.28675(8) 0.0313(3) Uani 1 1 d . . . . .
H9A H 0.9088 1.1200 0.2852 0.038 Uiso 1 1 calc R . . . .
H9B H 0.7632 1.0254 0.2467 0.038 Uiso 1 1 calc R . . . .
N4 N 0.83423(19) 0.78890(16) 0.34870(8) 0.0391(4) Uani 1 1 d . . . . .
C3 C -0.0010(2) 0.81359(16) -0.03659(8) 0.0293(3) Uani 1 1 d . . . . .
C4 C -0.0354(2) 0.73346(17) 0.01717(9) 0.0347(4) Uani 1 1 d . . . . .
H4 H -0.1299 0.6743 0.0098 0.042 Uiso 1 1 calc R . . . .
C5 C 0.0682(2) 0.74007(16) 0.08148(9) 0.0313(3) Uani 1 1 d . . . . .
H5 H 0.0426 0.6866 0.1177 0.038 Uiso 1 1 calc R . . . .
C8 C 1.1404(2) 0.94620(17) 0.34637(8) 0.0295(3) Uani 1 1 d . . . . .
H8A H 1.2320 0.8801 0.3451 0.035 Uiso 1 1 calc R . . . .
H8B H 1.1976 1.0306 0.3458 0.035 Uiso 1 1 calc R . . . .
C11 C 0.9210(2) 1.03204(19) 0.40942(9) 0.0391(4) Uani 1 1 d . . . . .
H11A H 0.9761 1.1170 0.4083 0.047 Uiso 1 1 calc R . . . .
H11B H 0.8685 1.0254 0.4525 0.047 Uiso 1 1 calc R . . . .
C12 C 0.7004(2) 0.8907(2) 0.35091(10) 0.0438(5) Uani 1 1 d . . . . .
H12A H 0.6073 0.8814 0.3110 0.053 Uiso 1 1 calc R . . . .
H12B H 0.6445 0.8809 0.3931 0.053 Uiso 1 1 calc R . . . .
C13 C 0.9744(2) 0.80541(19) 0.40862(9) 0.0399(4) Uani 1 1 d . . . . .
H13A H 0.9222 0.7944 0.4516 0.048 Uiso 1 1 calc R . . . .
H13B H 1.0653 0.7388 0.4073 0.048 Uiso 1 1 calc R . . . .
C10 C 0.9136(2) 0.80051(17) 0.28552(9) 0.0359(4) Uani 1 1 d . . . . .
H10A H 0.8222 0.7895 0.2452 0.043 Uiso 1 1 calc R . . . .
H10B H 1.0042 0.7338 0.2840 0.043 Uiso 1 1 calc R . . . .
H1 H 1.046(3) 0.943(2) 0.2434(11) 0.042(5) Uiso 1 1 d . . . . .
H3 H -0.077(3) 0.870(3) -0.1249(14) 0.074(8) Uiso 1 1 d . . . . .
H1A H 0.371(4) 1.086(3) -0.1051(16) 0.084(9) 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 O4 1.4690(12) . ?
S1 O6 1.4493(12) . ?
S1 C6 1.7796(15) . ?
S1 O5 1.4470(13) . ?
N1 C9 1.519(2) . ?
N1 C8 1.5204(19) . ?
N1 C10 1.521(2) . ?
N1 H1 0.91(2) . ?
O2 C1 1.2231(19) . ?
O1 C1 1.314(2) . ?
O1 H1A 0.89(3) . ?
O3 C3 1.3565(19) . ?
O3 H3 0.91(3) . ?
C2 C7 1.396(2) . ?
C2 C1 1.478(2) . ?
C2 C3 1.404(2) . ?
C7 H7 0.9400 . ?
C7 C6 1.387(2) . ?
N2 C8 1.446(2) . ?
N2 C11 1.473(2) . ?
N2 C13 1.470(2) . ?
C6 C5 1.393(2) . ?
N3 C9 1.441(2) . ?
N3 C11 1.474(2) . ?
N3 C12 1.470(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
N4 C12 1.472(3) . ?
N4 C13 1.476(2) . ?
N4 C10 1.447(2) . ?
C3 C4 1.391(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.385(2) . ?
C5 H5 0.9400 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 C6 106.05(7) . . ?
O6 S1 O4 111.57(7) . . ?
O6 S1 C6 106.36(7) . . ?
O5 S1 O4 112.38(8) . . ?
O5 S1 O6 113.46(8) . . ?
O5 S1 C6 106.40(7) . . ?
C9 N1 C8 109.31(12) . . ?
C9 N1 C10 108.92(13) . . ?
C9 N1 H1 108.5(13) . . ?
C8 N1 C10 108.61(12) . . ?
C8 N1 H1 111.1(13) . . ?
C10 N1 H1 110.4(13) . . ?
C1 O1 H1A 113.8(19) . . ?
C3 O3 H3 106.4(17) . . ?
C7 C2 C1 120.38(14) . . ?
C7 C2 C3 119.31(14) . . ?
C3 C2 C1 120.31(14) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.59(14) . . ?
C6 C7 H7 119.7 . . ?
C8 N2 C11 108.87(13) . . ?
C8 N2 C13 108.83(14) . . ?
C13 N2 C11 108.92(14) . . ?
C7 C6 S1 118.56(12) . . ?
C7 C6 C5 119.83(14) . . ?
C5 C6 S1 121.49(12) . . ?
O2 C1 O1 123.34(15) . . ?
O2 C1 C2 123.12(15) . . ?
O1 C1 C2 113.54(13) . . ?
C9 N3 C11 108.96(13) . . ?
C9 N3 C12 108.71(14) . . ?
C12 N3 C11 108.86(14) . . ?
N1 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
N3 C9 N1 109.54(13) . . ?
N3 C9 H9A 109.8 . . ?
N3 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C12 N4 C13 108.49(15) . . ?
C10 N4 C12 109.50(14) . . ?
C10 N4 C13 108.90(13) . . ?
O3 C3 C2 122.44(15) . . ?
O3 C3 C4 117.93(15) . . ?
C4 C3 C2 119.63(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.58(15) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.99(15) . . ?
C4 C5 H5 120.0 . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N2 C8 N1 109.28(12) . . ?
N2 C8 H8A 109.8 . . ?
N2 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C11 N3 111.96(14) . . ?
N2 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
N3 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 N4 111.98(14) . . ?
N3 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
N4 C12 H12A 109.2 . . ?
N4 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 N4 111.89(14) . . ?
N2 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
N4 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N1 C10 H10A 109.9 . . ?
N1 C10 H10B 109.9 . . ?
N4 C10 N1 108.86(14) . . ?
N4 C10 H10A 109.9 . . ?
N4 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C6 C5 C4 175.13(13) . . . . ?
O4 S1 C6 C7 -53.65(14) . . . . ?
O4 S1 C6 C5 130.34(13) . . . . ?
O6 S1 C6 C7 -172.53(12) . . . . ?
O6 S1 C6 C5 11.46(15) . . . . ?
O3 C3 C4 C5 -177.28(16) . . . . ?
C2 C7 C6 S1 -175.18(12) . . . . ?
C2 C7 C6 C5 0.9(2) . . . . ?
C2 C3 C4 C5 3.0(3) . . . . ?
C7 C2 C1 O2 -173.12(15) . . . . ?
C7 C2 C1 O1 6.8(2) . . . . ?
C7 C2 C3 O3 177.39(15) . . . . ?
C7 C2 C3 C4 -2.9(2) . . . . ?
C7 C6 C5 C4 -0.8(2) . . . . ?
C1 C2 C7 C6 -179.57(14) . . . . ?
C1 C2 C3 O3 -2.1(2) . . . . ?
C1 C2 C3 C4 177.64(15) . . . . ?
O5 S1 C6 C7 66.20(14) . . . . ?
O5 S1 C6 C5 -109.81(14) . . . . ?
C9 N1 C8 N2 58.67(16) . . . . ?
C9 N1 C10 N4 -58.92(16) . . . . ?
C9 N3 C11 N2 -61.03(19) . . . . ?
C9 N3 C12 N4 60.64(18) . . . . ?
C3 C2 C7 C6 1.0(2) . . . . ?
C3 C2 C1 O2 6.3(2) . . . . ?
C3 C2 C1 O1 -173.75(15) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C8 N1 C9 N3 -58.67(17) . . . . ?
C8 N1 C10 N4 60.04(17) . . . . ?
C8 N2 C11 N3 61.13(18) . . . . ?
C8 N2 C13 N4 -60.73(18) . . . . ?
C11 N2 C8 N1 -59.02(17) . . . . ?
C11 N2 C13 N4 57.83(18) . . . . ?
C11 N3 C9 N1 58.86(18) . . . . ?
C11 N3 C12 N4 -57.93(18) . . . . ?
C12 N3 C9 N1 -59.65(17) . . . . ?
C12 N3 C11 N2 57.38(18) . . . . ?
C12 N4 C13 N2 -58.10(19) . . . . ?
C12 N4 C10 N1 58.73(17) . . . . ?
C13 N2 C8 N1 59.57(17) . . . . ?
C13 N2 C11 N3 -57.41(18) . . . . ?
C13 N4 C12 N3 58.15(18) . . . . ?
C13 N4 C10 N1 -59.75(18) . . . . ?
C10 N1 C9 N3 59.85(17) . . . . ?
C10 N1 C8 N2 -60.05(17) . . . . ?
C10 N4 C12 N3 -60.58(19) . . . . ?
C10 N4 C13 N2 61.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1575420'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H5 O6 S, C6 H13 N4, H2 O'
_chemical_formula_sum            'C13 H20 N4 O7 S'
_chemical_formula_weight         376.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.0591(11)
_cell_length_b                   6.7221(5)
_cell_length_c                   16.0418(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1623.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      28.323
_cell_measurement_theta_min      3.286
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needlelike
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14178
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         3.286
_diffrn_ambient_temperature      172.53
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2017
_reflns_number_total             2151
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+0.8541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H10B(0.5) H10A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C10(H10B,H10A), C11(H11B,H11A)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87780(2) 0.2500 0.26234(2) 0.01949(12) Uani 1 2 d S T P . .
O1 O 0.90373(8) 0.2500 0.65740(7) 0.0254(3) Uani 1 2 d S T P . .
O2 O 0.78489(8) 0.2500 0.57428(7) 0.0262(3) Uani 1 2 d S T P . .
O3 O 1.06133(8) 0.2500 0.58781(8) 0.0265(3) Uani 1 2 d S T P . .
C6 C 0.88297(10) 0.2500 0.43216(10) 0.0169(3) Uani 1 2 d S T P . .
H6 H 0.8200 0.2500 0.4289 0.020 Uiso 1 2 calc RS T P . .
O4 O 0.78337(8) 0.2500 0.28028(8) 0.0289(3) Uani 1 2 d S T P . .
C1 C 0.92427(10) 0.2500 0.51032(10) 0.0165(3) Uani 1 2 d S T P . .
C7 C 0.87077(10) 0.2500 0.58718(10) 0.0183(3) Uani 1 2 d S T P . .
C4 C 1.02548(11) 0.2500 0.36470(10) 0.0207(3) Uani 1 2 d S T P . .
H4 H 1.0597 0.2500 0.3150 0.025 Uiso 1 2 calc RS T P . .
O5 O 0.90809(6) 0.07044(15) 0.21932(5) 0.0289(2) Uani 1 1 d . . . . .
C2 C 1.01729(10) 0.2500 0.51455(10) 0.0187(3) Uani 1 2 d S T P . .
C3 C 1.06742(10) 0.2500 0.44096(11) 0.0214(3) Uani 1 2 d S T P . .
H3A H 1.1304 0.2500 0.4437 0.026 Uiso 1 2 calc RS T P . .
C5 C 0.93225(10) 0.2500 0.35999(10) 0.0173(3) Uani 1 2 d S T P . .
N2 N 0.33455(9) 0.2500 0.66900(9) 0.0197(3) Uani 1 2 d S T P . .
N1 N 0.42906(6) 0.06856(15) 0.57412(6) 0.0202(2) Uani 1 1 d . . . . .
C9 C 0.39155(8) 0.06596(18) 0.65682(7) 0.0216(2) Uani 1 1 d . . . . .
H9A H 0.4397 0.0637 0.6988 0.026 Uiso 1 1 calc R . . . .
H9B H 0.3549 -0.0551 0.6643 0.026 Uiso 1 1 calc R . . . .
N3 N 0.30063(10) 0.2500 0.52138(9) 0.0256(3) Uani 1 2 d S T P . .
C8 C 0.35703(8) 0.0730(2) 0.51193(7) 0.0257(3) Uani 1 1 d . . . . .
H8A H 0.3831 0.0719 0.4553 0.031 Uiso 1 1 calc R . . . .
H8B H 0.3201 -0.0479 0.5181 0.031 Uiso 1 1 calc R . . . .
C10 C 0.26164(10) 0.2500 0.60366(11) 0.0266(4) Uani 1 2 d S T P . .
H10B H 0.2238 0.1307 0.6107 0.032 Uiso 0.5 1 calc R . . . .
H10A H 0.2238 0.3693 0.6107 0.032 Uiso 0.5 1 calc R . . . .
C11 C 0.48241(10) 0.2500 0.56393(10) 0.0201(3) Uani 1 2 d S T P . .
H11B H 0.5309 0.2500 0.6056 0.024 Uiso 1 2 calc RS T P . .
H11A H 0.5097 0.2500 0.5078 0.024 Uiso 1 2 calc RS T P . .
OW O 0.69674(8) 0.2500 0.70922(8) 0.0229(3) Uani 1 2 d S T P . .
H2A H 0.3152(17) 0.2500 0.7187(15) 0.036(6) Uiso 1 2 d S T P . .
HW H 0.6654(12) 0.148(3) 0.7137(11) 0.045(5) Uiso 1 1 d . . . . .
H3 H 1.0210(19) 0.2500 0.6248(18) 0.052(8) Uiso 1 2 d S T P . .
H2 H 0.7569(18) 0.2500 0.6237(19) 0.055(8) Uiso 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4508(12) . ?
S1 O5 1.4633(9) . ?
S1 O5 1.4632(9) 7_565 ?
S1 C5 1.7681(16) . ?
O1 C7 1.2310(19) . ?
O2 C7 1.3096(19) . ?
O2 H2 0.90(3) . ?
O3 C2 1.3495(19) . ?
O3 H3 0.85(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.400(2) . ?
C6 C5 1.375(2) . ?
C1 C7 1.473(2) . ?
C1 C2 1.403(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.377(2) . ?
C4 C5 1.406(2) . ?
C2 C3 1.401(2) . ?
C3 H3A 0.9500 . ?
N2 C9 1.5183(14) 7_565 ?
N2 C9 1.5184(14) . ?
N2 C10 1.518(2) . ?
N2 H2A 0.85(2) . ?
N1 C9 1.4419(13) . ?
N1 C8 1.4741(15) . ?
N1 C11 1.4696(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N3 C8 1.4697(15) . ?
N3 C8 1.4697(15) 7_565 ?
N3 C10 1.445(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 N1 1.4696(13) 7_565 ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
OW HW 0.833(18) . ?

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 O5 113.52(4) . 7_565 ?
O4 S1 O5 113.52(4) . . ?
O4 S1 C5 106.19(7) . . ?
O5 S1 O5 111.16(8) 7_565 . ?
O5 S1 C5 105.85(5) . . ?
O5 S1 C5 105.85(5) 7_565 . ?
C7 O2 H2 108.9(18) . . ?
C2 O3 H3 104.9(19) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C1 120.96(14) . . ?
C6 C1 C7 120.46(14) . . ?
C6 C1 C2 119.15(14) . . ?
C2 C1 C7 120.39(14) . . ?
O1 C7 O2 122.88(15) . . ?
O1 C7 C1 123.05(14) . . ?
O2 C7 C1 114.07(13) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.39(15) . . ?
C5 C4 H4 119.8 . . ?
O3 C2 C1 122.21(15) . . ?
O3 C2 C3 117.97(14) . . ?
C3 C2 C1 119.83(14) . . ?
C4 C3 C2 120.09(14) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C6 C5 S1 119.71(12) . . ?
C6 C5 C4 119.58(15) . . ?
C4 C5 S1 120.71(12) . . ?
C9 N2 C9 109.13(12) 7_565 . ?
C9 N2 H2A 108.4(9) 7_565 . ?
C9 N2 H2A 108.4(9) . . ?
C10 N2 C9 108.67(8) . . ?
C10 N2 C9 108.67(8) . 7_565 ?
C10 N2 H2A 113.6(17) . . ?
C9 N1 C8 109.55(9) . . ?
C9 N1 C11 109.06(10) . . ?
C11 N1 C8 108.07(10) . . ?
N2 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
N1 C9 N2 109.27(9) . . ?
N1 C9 H9A 109.8 . . ?
N1 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C8 N3 C8 108.11(13) . 7_565 ?
C10 N3 C8 109.22(9) . . ?
C10 N3 C8 109.22(9) . 7_565 ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N3 C8 N1 111.82(10) . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N2 C10 H10B 109.7 . . ?
N2 C10 H10A 109.7 . . ?
N3 C10 N2 109.69(13) . . ?
N3 C10 H10B 109.7 . . ?
N3 C10 H10A 109.7 . . ?
H10B C10 H10A 108.2 . . ?
N1 C11 N1 112.18(12) 7_565 . ?
N1 C11 H11B 109.2 7_565 . ?
N1 C11 H11B 109.2 . . ?
N1 C11 H11A 109.2 7_565 . ?
N1 C11 H11A 109.2 . . ?
H11B C11 H11A 107.9 . . ?

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
O3 C2 C3 C4 180.000(0) . . . . ?
C6 C1 C7 O1 180.000(0) . . . . ?
C6 C1 C7 O2 0.000(0) . . . . ?
C6 C1 C2 O3 180.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
O4 S1 C5 C6 0.000(0) . . . . ?
O4 S1 C5 C4 180.000(0) . . . . ?
C1 C6 C5 S1 180.000(0) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C7 C1 C2 O3 0.000(0) . . . . ?
C7 C1 C2 C3 180.000(0) . . . . ?
O5 S1 C5 C6 -120.96(4) . . . . ?
O5 S1 C5 C6 120.96(4) 7_565 . . . ?
O5 S1 C5 C4 59.04(4) . . . . ?
O5 S1 C5 C4 -59.04(4) 7_565 . . . ?
C2 C1 C7 O1 0.000(0) . . . . ?
C2 C1 C7 O2 180.000(0) . . . . ?
C3 C4 C5 S1 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C5 C6 C1 C7 180.000(0) . . . . ?
C5 C6 C1 C2 0.000(0) . . . . ?
C5 C4 C3 C2 0.000(0) . . . . ?
C9 N2 C9 N1 -59.11(14) 7_565 . . . ?
C9 N2 C10 N3 59.32(8) 7_565 . . . ?
C9 N2 C10 N3 -59.32(8) . . . . ?
C9 N1 C8 N3 60.12(13) . . . . ?
C9 N1 C11 N1 -60.59(15) . . . 7_565 ?
C8 N1 C9 N2 -59.18(12) . . . . ?
C8 N1 C11 N1 58.43(15) . . . 7_565 ?
C8 N3 C8 N1 58.98(16) 7_565 . . . ?
C8 N3 C10 N2 -59.02(8) 7_565 . . . ?
C8 N3 C10 N2 59.02(8) . . . . ?
C10 N2 C9 N1 59.23(12) . . . . ?
C10 N3 C8 N1 -59.75(13) . . . . ?
C11 N1 C9 N2 58.92(12) . . . . ?
C11 N1 C8 N3 -58.60(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_2
_database_code_depnum_ccdc_archive 'CCDC 1575421'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 O6 S, 2(C6 H13 N4)'
_chemical_formula_sum            'C19 H30 N8 O6 S'
_chemical_formula_weight         498.57
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.8939(7)
_cell_length_b                   12.2771(9)
_cell_length_c                   16.6849(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2231.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    222(2)
_cell_measurement_theta_max      28.257
_cell_measurement_theta_min      2.952
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12193
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.952
_diffrn_ambient_temperature      222.14
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4463
_reflns_number_total             5461
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+2.4291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B), C10(H10A,
 H10B), C9(H9A,H9B), C16(H16A,H16B), C13(H13A,H13B), C18(H18A,H18B), C11(H11A,
 H11B), C8(H8A,H8B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3A), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.14073(10) 0.34854(9) 0.01993(7) 0.0317(3) Uani 1 1 d . . . . .
O3 O 0.8369(4) 0.7451(2) 0.0345(2) 0.0397(9) Uani 1 1 d . . . . .
C1 C 0.8484(4) 0.5503(3) 0.0313(2) 0.0215(8) Uani 1 1 d . . . . .
C5 C 1.0482(4) 0.4670(3) 0.0225(2) 0.0229(8) Uani 1 1 d . . . . .
O1 O 0.6650(3) 0.4470(2) 0.03443(18) 0.0311(7) Uani 1 1 d . . . . .
C2 C 0.9044(4) 0.6537(3) 0.0297(2) 0.0241(8) Uani 1 1 d . . . . .
N4 N 0.6322(4) 0.3291(3) 0.2885(2) 0.0309(8) Uani 1 1 d . . . . .
O2 O 0.6512(3) 0.6261(3) 0.0496(2) 0.0462(9) Uani 1 1 d . . . . .
C6 C 0.9226(4) 0.4581(3) 0.0273(2) 0.0209(8) Uani 1 1 d . . . . .
H6 H 0.8862 0.3887 0.0279 0.025 Uiso 1 1 calc R . . . .
O4 O 1.0556(3) 0.2594(2) 0.00228(19) 0.0331(7) Uani 1 1 d . . . . .
N3 N 0.4394(4) 0.4191(3) 0.2565(2) 0.0320(9) Uani 1 1 d . . . . .
N1 N 0.5526(3) 0.3250(3) 0.1535(2) 0.0267(8) Uani 1 1 d . . . . .
N5 N 0.0357(3) 0.0697(3) 0.1081(2) 0.0245(7) Uani 1 1 d . . . . .
C3 C 1.0307(4) 0.6619(3) 0.0241(3) 0.0314(9) Uani 1 1 d . . . . .
H3A H 1.0678 0.7310 0.0225 0.038 Uiso 1 1 calc R . . . .
O5 O 1.1934(3) 0.3373(3) 0.0995(2) 0.0504(10) Uani 1 1 d . . . . .
C7 C 0.7117(4) 0.5401(3) 0.0391(2) 0.0254(9) Uani 1 1 d . . . . .
C14 C -0.0440(4) -0.0310(4) 0.1056(3) 0.0342(10) Uani 1 1 d . . . . .
H14A H -0.1194 -0.0157 0.0756 0.041 Uiso 1 1 calc R . . . .
H14B H -0.0002 -0.0901 0.0784 0.041 Uiso 1 1 calc R . . . .
C12 C 0.5518(4) 0.4223(4) 0.3044(3) 0.0340(11) Uani 1 1 d . . . . .
H12A H 0.5300 0.4230 0.3614 0.041 Uiso 1 1 calc R . . . .
H12B H 0.5964 0.4897 0.2926 0.041 Uiso 1 1 calc R . . . .
C15 C -0.0354(4) 0.1605(3) 0.1494(2) 0.0280(9) Uani 1 1 d . . . . .
H15A H 0.0151 0.2264 0.1520 0.034 Uiso 1 1 calc R . . . .
H15B H -0.1097 0.1774 0.1187 0.034 Uiso 1 1 calc R . . . .
N7 N -0.0683(3) 0.1260(3) 0.2292(2) 0.0289(8) Uani 1 1 d . . . . .
C17 C -0.1420(5) 0.0258(4) 0.2249(3) 0.0378(11) Uani 1 1 d . . . . .
H17A H -0.1655 0.0036 0.2792 0.045 Uiso 1 1 calc R . . . .
H17B H -0.2173 0.0402 0.1946 0.045 Uiso 1 1 calc R . . . .
C4 C 1.1029(4) 0.5698(3) 0.0209(3) 0.0311(10) Uani 1 1 d . . . . .
H4 H 1.1888 0.5762 0.0177 0.037 Uiso 1 1 calc R . . . .
C10 C 0.6662(4) 0.3306(4) 0.2045(3) 0.0290(9) Uani 1 1 d . . . . .
H10A H 0.7195 0.2684 0.1925 0.035 Uiso 1 1 calc R . . . .
H10B H 0.7116 0.3976 0.1924 0.035 Uiso 1 1 calc R . . . .
C9 C 0.4719(4) 0.4218(4) 0.1724(3) 0.0334(10) Uani 1 1 d . . . . .
H9A H 0.5158 0.4895 0.1602 0.040 Uiso 1 1 calc R . . . .
H9B H 0.3975 0.4193 0.1394 0.040 Uiso 1 1 calc R . . . .
N8 N 0.1166(4) 0.0155(3) 0.2359(2) 0.0349(9) Uani 1 1 d . . . . .
N2 N 0.4505(4) 0.2211(3) 0.2569(2) 0.0371(10) Uani 1 1 d . . . . .
C16 C 0.1500(4) 0.0471(4) 0.1557(3) 0.0315(10) Uani 1 1 d . . . . .
H16A H 0.1970 -0.0114 0.1301 0.038 Uiso 1 1 calc R . . . .
H16B H 0.2016 0.1125 0.1574 0.038 Uiso 1 1 calc R . . . .
C13 C 0.5633(5) 0.2286(4) 0.3050(3) 0.0393(12) Uani 1 1 d . . . . .
H13A H 0.5418 0.2262 0.3620 0.047 Uiso 1 1 calc R . . . .
H13B H 0.6156 0.1656 0.2934 0.047 Uiso 1 1 calc R . . . .
C18 C 0.0450(5) 0.1016(4) 0.2733(3) 0.0384(12) Uani 1 1 d . . . . .
H18A H 0.0951 0.1678 0.2765 0.046 Uiso 1 1 calc R . . . .
H18B H 0.0240 0.0797 0.3281 0.046 Uiso 1 1 calc R . . . .
C11 C 0.3735(5) 0.3168(4) 0.2741(3) 0.0403(12) Uani 1 1 d . . . . .
H11A H 0.3494 0.3159 0.3307 0.048 Uiso 1 1 calc R . . . .
H11B H 0.2987 0.3133 0.2416 0.048 Uiso 1 1 calc R . . . .
N6 N -0.0737(4) -0.0629(3) 0.1862(3) 0.0369(9) Uani 1 1 d . . . . .
C8 C 0.4827(5) 0.2222(4) 0.1727(3) 0.0368(11) Uani 1 1 d . . . . .
H8A H 0.4081 0.2187 0.1401 0.044 Uiso 1 1 calc R . . . .
H8B H 0.5334 0.1585 0.1601 0.044 Uiso 1 1 calc R . . . .
C19 C 0.0393(5) -0.0822(4) 0.2315(3) 0.0438(13) Uani 1 1 d . . . . .
H19A H 0.0857 -0.1411 0.2058 0.053 Uiso 1 1 calc R . . . .
H19B H 0.0183 -0.1058 0.2859 0.053 Uiso 1 1 calc R . . . .
O6 O 1.2265(4) 0.3648(3) -0.0450(3) 0.0680(14) Uani 1 1 d . . . . .
H5 H 0.053(4) 0.090(3) 0.061(3) 0.022(11) Uiso 1 1 d . . . . .
H1 H 0.570(5) 0.327(5) 0.106(3) 0.050(17) Uiso 1 1 d . . . . .
H3 H 0.765(8) 0.724(6) 0.036(5) 0.10(3) 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 C5 1.769(4) . ?
S1 O4 1.464(3) . ?
S1 O5 1.453(4) . ?
S1 O6 1.444(4) . ?
O3 C2 1.344(5) . ?
O3 H3 0.82(8) . ?
C1 C2 1.409(5) . ?
C1 C6 1.393(5) . ?
C1 C7 1.500(6) . ?
C5 C6 1.375(6) . ?
C5 C4 1.396(6) . ?
O1 C7 1.254(5) . ?
C2 C3 1.383(6) . ?
N4 C12 1.464(6) . ?
N4 C10 1.451(5) . ?
N4 C13 1.471(6) . ?
O2 C7 1.256(5) . ?
C6 H6 0.9400 . ?
N3 C12 1.463(6) . ?
N3 C9 1.448(6) . ?
N3 C11 1.476(6) . ?
N1 C10 1.503(5) . ?
N1 C9 1.511(6) . ?
N1 C8 1.508(6) . ?
N1 H1 0.81(6) . ?
N5 C14 1.511(6) . ?
N5 C15 1.522(5) . ?
N5 C16 1.503(5) . ?
N5 H5 0.84(5) . ?
C3 H3A 0.9400 . ?
C3 C4 1.378(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 N6 1.439(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 N7 1.443(5) . ?
N7 C17 1.470(6) . ?
N7 C18 1.468(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 N6 1.469(6) . ?
C4 H4 0.9400 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
N8 C16 1.439(6) . ?
N8 C18 1.455(6) . ?
N8 C19 1.468(6) . ?
N2 C13 1.471(7) . ?
N2 C11 1.472(6) . ?
N2 C8 1.448(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
N6 C19 1.464(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 C5 104.98(18) . . ?
O5 S1 C5 106.3(2) . . ?
O5 S1 O4 111.3(2) . . ?
O6 S1 C5 105.9(2) . . ?
O6 S1 O4 111.2(2) . . ?
O6 S1 O5 116.3(3) . . ?
C2 O3 H3 105(5) . . ?
C2 C1 C7 120.4(4) . . ?
C6 C1 C2 118.7(4) . . ?
C6 C1 C7 120.8(3) . . ?
C6 C5 S1 120.2(3) . . ?
C6 C5 C4 119.8(4) . . ?
C4 C5 S1 120.0(3) . . ?
O3 C2 C1 120.9(4) . . ?
O3 C2 C3 119.2(4) . . ?
C3 C2 C1 119.8(4) . . ?
C12 N4 C13 108.4(4) . . ?
C10 N4 C12 108.5(3) . . ?
C10 N4 C13 108.8(4) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C12 N3 C11 108.7(4) . . ?
C9 N3 C12 108.9(4) . . ?
C9 N3 C11 109.4(4) . . ?
C10 N1 C9 109.0(3) . . ?
C10 N1 C8 109.5(4) . . ?
C10 N1 H1 111(4) . . ?
C9 N1 H1 109(4) . . ?
C8 N1 C9 108.7(3) . . ?
C8 N1 H1 110(4) . . ?
C14 N5 C15 108.6(3) . . ?
C14 N5 H5 110(3) . . ?
C15 N5 H5 108(3) . . ?
C16 N5 C14 109.9(3) . . ?
C16 N5 C15 108.6(3) . . ?
C16 N5 H5 111(3) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3A 119.6 . . ?
O1 C7 C1 118.2(4) . . ?
O1 C7 O2 124.2(4) . . ?
O2 C7 C1 117.6(4) . . ?
N5 C14 H14A 109.9 . . ?
N5 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
N6 C14 N5 109.0(3) . . ?
N6 C14 H14A 109.9 . . ?
N6 C14 H14B 109.9 . . ?
N4 C12 H12A 109.1 . . ?
N4 C12 H12B 109.1 . . ?
N3 C12 N4 112.4(4) . . ?
N3 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
N5 C15 H15A 109.8 . . ?
N5 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N7 C15 N5 109.2(3) . . ?
N7 C15 H15A 109.8 . . ?
N7 C15 H15B 109.8 . . ?
C15 N7 C17 109.6(3) . . ?
C15 N7 C18 108.3(3) . . ?
C18 N7 C17 108.2(4) . . ?
N7 C17 H17A 109.3 . . ?
N7 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N6 C17 N7 111.4(4) . . ?
N6 C17 H17A 109.3 . . ?
N6 C17 H17B 109.3 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
N4 C10 N1 109.7(3) . . ?
N4 C10 H10A 109.7 . . ?
N4 C10 H10B 109.7 . . ?
N1 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C9 N1 109.0(4) . . ?
N3 C9 H9A 109.9 . . ?
N3 C9 H9B 109.9 . . ?
N1 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C16 N8 C18 109.8(4) . . ?
C16 N8 C19 108.6(4) . . ?
C18 N8 C19 107.9(4) . . ?
C13 N2 C11 108.6(4) . . ?
C8 N2 C13 109.0(4) . . ?
C8 N2 C11 108.6(4) . . ?
N5 C16 H16A 109.8 . . ?
N5 C16 H16B 109.8 . . ?
N8 C16 N5 109.3(4) . . ?
N8 C16 H16A 109.8 . . ?
N8 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N4 C13 N2 112.1(4) . . ?
N4 C13 H13A 109.2 . . ?
N4 C13 H13B 109.2 . . ?
N2 C13 H13A 109.2 . . ?
N2 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N7 C18 H18A 109.1 . . ?
N7 C18 H18B 109.1 . . ?
N8 C18 N7 112.6(4) . . ?
N8 C18 H18A 109.1 . . ?
N8 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N2 C11 N3 111.3(4) . . ?
N2 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C14 N6 C17 108.9(4) . . ?
C14 N6 C19 109.7(4) . . ?
C19 N6 C17 108.7(4) . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
N2 C8 N1 109.7(4) . . ?
N2 C8 H8A 109.7 . . ?
N2 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N8 C19 H19A 109.2 . . ?
N8 C19 H19B 109.2 . . ?
N6 C19 N8 112.1(4) . . ?
N6 C19 H19A 109.2 . . ?
N6 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?

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
S1 C5 C6 C1 178.5(3) . . . . ?
S1 C5 C4 C3 -179.1(3) . . . . ?
O3 C2 C3 C4 178.5(4) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C1 C7 O1 174.9(4) . . . . ?
C2 C1 C7 O2 -4.8(6) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C6 C1 C2 O3 -179.0(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C6 C1 C7 O1 -6.6(6) . . . . ?
C6 C1 C7 O2 173.8(4) . . . . ?
C6 C5 C4 C3 0.0(7) . . . . ?
O4 S1 C5 C6 14.7(4) . . . . ?
O4 S1 C5 C4 -166.3(4) . . . . ?
N5 C14 N6 C17 61.0(5) . . . . ?
N5 C14 N6 C19 -57.7(5) . . . . ?
N5 C15 N7 C17 -58.3(4) . . . . ?
N5 C15 N7 C18 59.6(4) . . . . ?
O5 S1 C5 C6 -103.3(4) . . . . ?
O5 S1 C5 C4 75.7(4) . . . . ?
C7 C1 C2 O3 -0.5(6) . . . . ?
C7 C1 C2 C3 178.6(4) . . . . ?
C7 C1 C6 C5 -178.1(4) . . . . ?
C14 N5 C15 N7 59.0(4) . . . . ?
C14 N5 C16 N8 -59.4(5) . . . . ?
C14 N6 C19 N8 60.4(5) . . . . ?
C12 N4 C10 N1 -58.9(4) . . . . ?
C12 N4 C13 N2 57.6(5) . . . . ?
C12 N3 C9 N1 59.2(5) . . . . ?
C12 N3 C11 N2 -58.1(5) . . . . ?
C15 N5 C14 N6 -60.5(4) . . . . ?
C15 N5 C16 N8 59.3(4) . . . . ?
C15 N7 C17 N6 60.1(5) . . . . ?
C15 N7 C18 N8 -60.1(5) . . . . ?
N7 C17 N6 C14 -61.3(5) . . . . ?
N7 C17 N6 C19 58.1(5) . . . . ?
C17 N7 C18 N8 58.7(5) . . . . ?
C17 N6 C19 N8 -58.5(5) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C10 N4 C12 N3 60.2(5) . . . . ?
C10 N4 C13 N2 -60.2(5) . . . . ?
C10 N1 C9 N3 -59.7(4) . . . . ?
C10 N1 C8 N2 58.7(5) . . . . ?
C9 N3 C12 N4 -60.7(5) . . . . ?
C9 N3 C11 N2 60.7(5) . . . . ?
C9 N1 C10 N4 59.7(4) . . . . ?
C9 N1 C8 N2 -60.2(5) . . . . ?
C16 N5 C14 N6 58.2(4) . . . . ?
C16 N5 C15 N7 -60.5(4) . . . . ?
C16 N8 C18 N7 59.7(5) . . . . ?
C16 N8 C19 N6 -60.7(5) . . . . ?
C13 N4 C12 N3 -57.8(5) . . . . ?
C13 N4 C10 N1 58.9(5) . . . . ?
C13 N2 C11 N3 58.1(5) . . . . ?
C13 N2 C8 N1 -58.3(5) . . . . ?
C18 N7 C17 N6 -57.8(5) . . . . ?
C18 N8 C16 N5 -58.5(5) . . . . ?
C18 N8 C19 N6 58.3(5) . . . . ?
C11 N3 C12 N4 58.3(5) . . . . ?
C11 N3 C9 N1 -59.5(5) . . . . ?
C11 N2 C13 N4 -58.1(5) . . . . ?
C11 N2 C8 N1 59.9(5) . . . . ?
C8 N1 C10 N4 -59.0(4) . . . . ?
C8 N1 C9 N3 59.6(5) . . . . ?
C8 N2 C13 N4 60.1(5) . . . . ?
C8 N2 C11 N3 -60.4(5) . . . . ?
C19 N8 C16 N5 59.3(5) . . . . ?
C19 N8 C18 N7 -58.5(5) . . . . ?
O6 S1 C5 C6 132.4(4) . . . . ?
O6 S1 C5 C4 -48.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_new_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1575422'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H4 O6 S, 2(C6 H13 N4), H2 O'
_chemical_formula_sum            'C19 H32 N8 O7 S'
_chemical_formula_weight         516.58
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2433(14)
_cell_length_b                   35.039(9)
_cell_length_c                   10.477(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.424(9)
_cell_angle_gamma                90
_cell_volume                     2285.1(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9644
_cell_measurement_temperature    172(2)
_cell_measurement_theta_max      28.267
_cell_measurement_theta_min      3.324
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            89711
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      172.13
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5209
_reflns_number_total             5674
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0381P)²+1.6615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36872(5) 0.07415(2) 0.80756(3) 0.01413(9) Uani 1 1 d . . . . .
O1 O 0.0655(2) 0.21118(3) 0.64973(12) 0.0281(3) Uani 1 1 d . . . . .
O2 O 0.2506(2) 0.22761(3) 0.48384(12) 0.0297(3) Uani 1 1 d . . . . .
O3 O 0.5958(2) 0.19491(3) 0.44893(11) 0.0249(2) Uani 1 1 d . . . . .
O4 O 0.4175(2) 0.03886(3) 0.74336(11) 0.0241(2) Uani 1 1 d . . . . .
O5 O 0.5004(2) 0.07905(3) 0.92778(10) 0.0243(2) Uani 1 1 d . . . . .
O6 O 0.13996(19) 0.07913(3) 0.82255(14) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.3550(2) 0.17143(4) 0.59830(13) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.5476(2) 0.16876(4) 0.53703(13) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.6905(2) 0.13861(4) 0.56621(14) 0.0190(3) Uani 1 1 d . . . . .
H3A H 0.8236 0.1375 0.5281 0.023 Uiso 1 1 calc R . . . .
C4 C 0.6371(2) 0.11055(4) 0.65054(14) 0.0169(3) Uani 1 1 d . . . . .
H4A H 0.7349 0.0903 0.6714 0.020 Uiso 1 1 calc R . . . .
C5 C 0.4391(2) 0.11168(4) 0.70573(13) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.3013(2) 0.14225(4) 0.68125(13) 0.0138(3) Uani 1 1 d . . . . .
H6 H 0.1697 0.1434 0.7210 0.017 Uiso 1 1 calc R . . . .
C7 C 0.2112(2) 0.20545(4) 0.57591(15) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.0425(2) 0.08555(4) 0.34826(12) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.40159(19) 0.06479(3) 0.30037(12) 0.0163(2) Uani 1 1 d . . . . .
N3 N 0.18381(19) 0.02459(3) 0.43076(11) 0.0154(2) Uani 1 1 d . . . . .
N4 N 0.08559(19) 0.03245(3) 0.20456(11) 0.0145(2) Uani 1 1 d . . . . .
C15 C 0.2639(2) 0.09748(4) 0.32790(15) 0.0188(3) Uani 1 1 d . . . . .
H15A H 0.2605 0.1157 0.2555 0.023 Uiso 1 1 calc R . . . .
H15B H 0.3262 0.1108 0.4054 0.023 Uiso 1 1 calc R . . . .
C16 C 0.4024(2) 0.03784(4) 0.40885(13) 0.0167(3) Uani 1 1 d . . . . .
H16A H 0.4931 0.0156 0.3913 0.020 Uiso 1 1 calc R . . . .
H16B H 0.4662 0.0505 0.4873 0.020 Uiso 1 1 calc R . . . .
C17 C 0.0502(2) 0.05808(4) 0.45520(14) 0.0185(3) Uani 1 1 d . . . . .
H17A H 0.1089 0.0709 0.5345 0.022 Uiso 1 1 calc R . . . .
H17B H -0.0975 0.0495 0.4686 0.022 Uiso 1 1 calc R . . . .
C18 C -0.0490(2) 0.06693(4) 0.23376(14) 0.0183(3) Uani 1 1 d . . . . .
H18A H -0.0536 0.0850 0.1609 0.022 Uiso 1 1 calc R . . . .
H18B H -0.1979 0.0588 0.2460 0.022 Uiso 1 1 calc R . . . .
C19 C 0.3132(2) 0.04574(4) 0.18560(13) 0.0171(3) Uani 1 1 d . . . . .
H19A H 0.4038 0.0235 0.1670 0.021 Uiso 1 1 calc R . . . .
H19B H 0.3113 0.0635 0.1120 0.021 Uiso 1 1 calc R . . . .
C20 C 0.0930(2) 0.00513(4) 0.31737(13) 0.0162(3) Uani 1 1 d . . . . .
H20A H -0.0539 -0.0038 0.3310 0.019 Uiso 1 1 calc R . . . .
H20B H 0.1819 -0.0174 0.2996 0.019 Uiso 1 1 calc R . . . .
N5 N 0.8762(2) 0.22305(4) 0.08847(12) 0.0184(2) Uani 1 1 d . . . . .
N6 N 0.7454(2) 0.18275(4) -0.08916(13) 0.0233(3) Uani 1 1 d . . . . .
N7 N 0.9151(2) 0.15447(4) 0.10587(13) 0.0217(3) Uani 1 1 d . . . . .
N8 N 0.5599(2) 0.18370(4) 0.10775(12) 0.0191(3) Uani 1 1 d . . . . .
C21 C 0.8456(3) 0.21885(4) -0.05595(14) 0.0238(3) Uani 1 1 d . . . . .
H21A H 0.7545 0.2399 -0.0923 0.029 Uiso 1 1 calc R . . . .
H21B H 0.9866 0.2204 -0.0928 0.029 Uiso 1 1 calc R . . . .
C22 C 0.8835(3) 0.15206(4) -0.03501(16) 0.0246(3) Uani 1 1 d . . . . .
H22A H 1.0249 0.1535 -0.0715 0.030 Uiso 1 1 calc R . . . .
H22B H 0.8181 0.1271 -0.0594 0.030 Uiso 1 1 calc R . . . .
C23 C 1.0146(2) 0.19056(5) 0.14156(16) 0.0222(3) Uani 1 1 d . . . . .
H23A H 1.1581 0.1921 0.1077 0.027 Uiso 1 1 calc R . . . .
H23B H 1.0337 0.1926 0.2360 0.027 Uiso 1 1 calc R . . . .
C24 C 0.5370(3) 0.18053(5) -0.03303(16) 0.0257(3) Uani 1 1 d . . . . .
H24A H 0.4672 0.1559 -0.0573 0.031 Uiso 1 1 calc R . . . .
H24B H 0.4428 0.2013 -0.0685 0.031 Uiso 1 1 calc R . . . .
C25 C 0.7016(3) 0.15276(4) 0.15786(16) 0.0227(3) Uani 1 1 d . . . . .
H25A H 0.6337 0.1279 0.1353 0.027 Uiso 1 1 calc R . . . .
H25B H 0.7196 0.1545 0.2524 0.027 Uiso 1 1 calc R . . . .
C26 C 0.6593(2) 0.21994(4) 0.14265(14) 0.0194(3) Uani 1 1 d . . . . .
H26A H 0.6770 0.2222 0.2371 0.023 Uiso 1 1 calc R . . . .
H26B H 0.5656 0.2410 0.1092 0.023 Uiso 1 1 calc R . . . .
O1W O 0.8734(2) 0.03493(3) 0.95690(10) 0.0218(2) Uani 1 1 d . . . . .
H4 H 0.032(3) 0.0217(6) 0.132(2) 0.027(5) Uiso 1 1 d . . . . .
H1WA H 0.963(4) 0.0498(7) 0.919(2) 0.038(6) Uiso 1 1 d . . . . .
H5 H 0.942(4) 0.2475(7) 0.109(2) 0.038(6) Uiso 1 1 d . . . . .
H1WB H 0.752(4) 0.0473(7) 0.949(2) 0.044(7) Uiso 1 1 d . . . . .
H3 H 0.473(5) 0.2104(8) 0.445(3) 0.062(8) 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 O4 1.4513(11) . ?
S1 O5 1.4602(12) . ?
S1 O6 1.4593(12) . ?
S1 C5 1.7701(14) . ?
O1 C7 1.2549(19) . ?
O2 C7 1.2767(19) . ?
O3 C2 1.3509(17) . ?
O3 H3 0.94(3) . ?
C1 C2 1.409(2) . ?
C1 C6 1.3992(19) . ?
C1 C7 1.4999(19) . ?
C2 C3 1.401(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.380(2) . ?
C4 H4A 0.9500 . ?
C4 C5 1.4053(19) . ?
C5 C6 1.3852(19) . ?
C6 H6 0.9500 . ?
N1 C15 1.4750(19) . ?
N1 C17 1.4749(19) . ?
N1 C18 1.4440(19) . ?
N2 C15 1.4741(18) . ?
N2 C16 1.4774(18) . ?
N2 C19 1.4470(18) . ?
N3 C16 1.4760(18) . ?
N3 C17 1.4738(19) . ?
N3 C20 1.4470(18) . ?
N4 C18 1.5164(18) . ?
N4 C19 1.5228(18) . ?
N4 C20 1.5187(18) . ?
N4 H4 0.89(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
N5 C21 1.518(2) . ?
N5 C23 1.509(2) . ?
N5 C26 1.5121(19) . ?
N5 H5 0.97(2) . ?
N6 C21 1.442(2) . ?
N6 C22 1.465(2) . ?
N6 C24 1.471(2) . ?
N7 C22 1.476(2) . ?
N7 C23 1.446(2) . ?
N7 C25 1.479(2) . ?
N8 C24 1.475(2) . ?
N8 C25 1.470(2) . ?
N8 C26 1.4477(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
O1W H1WA 0.88(3) . ?
O1W H1WB 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O5 112.07(7) . . ?
O4 S1 O6 113.20(8) . . ?
O4 S1 C5 106.44(7) . . ?
O5 S1 C5 106.44(7) . . ?
O6 S1 O5 112.56(8) . . ?
O6 S1 C5 105.46(7) . . ?
C2 O3 H3 101.7(18) . . ?
C2 C1 C7 120.19(13) . . ?
C6 C1 C2 119.22(12) . . ?
C6 C1 C7 120.59(13) . . ?
O3 C2 C1 120.61(13) . . ?
O3 C2 C3 119.24(13) . . ?
C3 C2 C1 120.14(13) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 C2 119.70(13) . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 H4A 119.8 . . ?
C3 C4 C5 120.47(13) . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 S1 119.62(10) . . ?
C6 C5 S1 120.43(10) . . ?
C6 C5 C4 119.94(13) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.33(13) . . ?
C5 C6 H6 119.8 . . ?
O1 C7 O2 124.01(14) . . ?
O1 C7 C1 118.96(13) . . ?
O2 C7 C1 116.99(13) . . ?
C17 N1 C15 108.60(11) . . ?
C18 N1 C15 108.85(12) . . ?
C18 N1 C17 108.90(12) . . ?
C15 N2 C16 108.28(11) . . ?
C19 N2 C15 109.29(11) . . ?
C19 N2 C16 108.83(11) . . ?
C17 N3 C16 108.61(11) . . ?
C20 N3 C16 109.21(11) . . ?
C20 N3 C17 109.06(11) . . ?
C18 N4 C19 108.66(11) . . ?
C18 N4 C20 109.22(11) . . ?
C18 N4 H4 109.4(13) . . ?
C19 N4 H4 108.2(13) . . ?
C20 N4 C19 108.76(11) . . ?
C20 N4 H4 112.5(13) . . ?
N1 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
N2 C15 N1 112.03(11) . . ?
N2 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 H16A 109.2 . . ?
N2 C16 H16B 109.2 . . ?
N3 C16 N2 111.86(11) . . ?
N3 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N1 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
N3 C17 N1 111.91(11) . . ?
N3 C17 H17A 109.2 . . ?
N3 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
N1 C18 N4 109.73(11) . . ?
N1 C18 H18A 109.7 . . ?
N1 C18 H18B 109.7 . . ?
N4 C18 H18A 109.7 . . ?
N4 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N2 C19 N4 109.43(11) . . ?
N2 C19 H19A 109.8 . . ?
N2 C19 H19B 109.8 . . ?
N4 C19 H19A 109.8 . . ?
N4 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
N3 C20 N4 109.17(11) . . ?
N3 C20 H20A 109.8 . . ?
N3 C20 H20B 109.8 . . ?
N4 C20 H20A 109.8 . . ?
N4 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C21 N5 H5 108.9(13) . . ?
C23 N5 C21 108.59(12) . . ?
C23 N5 C26 108.12(11) . . ?
C23 N5 H5 111.3(14) . . ?
C26 N5 C21 108.64(12) . . ?
C26 N5 H5 111.2(13) . . ?
C21 N6 C22 108.60(13) . . ?
C21 N6 C24 109.31(13) . . ?
C22 N6 C24 108.60(13) . . ?
C22 N7 C25 108.15(13) . . ?
C23 N7 C22 109.27(12) . . ?
C23 N7 C25 108.77(12) . . ?
C25 N8 C24 108.12(12) . . ?
C26 N8 C24 108.98(12) . . ?
C26 N8 C25 108.80(12) . . ?
N5 C21 H21A 109.6 . . ?
N5 C21 H21B 109.6 . . ?
N6 C21 N5 110.17(12) . . ?
N6 C21 H21A 109.6 . . ?
N6 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
N6 C22 N7 111.97(12) . . ?
N6 C22 H22A 109.2 . . ?
N6 C22 H22B 109.2 . . ?
N7 C22 H22A 109.2 . . ?
N7 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N5 C23 H23A 109.7 . . ?
N5 C23 H23B 109.7 . . ?
N7 C23 N5 110.01(12) . . ?
N7 C23 H23A 109.7 . . ?
N7 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
N6 C24 N8 112.03(12) . . ?
N6 C24 H24A 109.2 . . ?
N6 C24 H24B 109.2 . . ?
N8 C24 H24A 109.2 . . ?
N8 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N7 C25 H25A 109.2 . . ?
N7 C25 H25B 109.2 . . ?
N8 C25 N7 111.89(12) . . ?
N8 C25 H25A 109.2 . . ?
N8 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
N5 C26 H26A 109.6 . . ?
N5 C26 H26B 109.6 . . ?
N8 C26 N5 110.32(11) . . ?
N8 C26 H26A 109.6 . . ?
N8 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
H1WA O1W H1WB 104(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
S1 C5 C6 C1 -178.46(10) . . . . ?
O3 C2 C3 C4 -176.28(13) . . . . ?
O4 S1 C5 C4 -46.17(13) . . . . ?
O4 S1 C5 C6 134.47(11) . . . . ?
O5 S1 C5 C4 73.53(12) . . . . ?
O5 S1 C5 C6 -105.83(12) . . . . ?
O6 S1 C5 C4 -166.69(12) . . . . ?
O6 S1 C5 C6 13.95(13) . . . . ?
C1 C2 C3 C4 3.1(2) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C2 C1 C7 O1 -165.62(14) . . . . ?
C2 C1 C7 O2 12.2(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 S1 176.95(11) . . . . ?
C3 C4 C5 C6 -3.7(2) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C6 C1 C2 O3 174.81(13) . . . . ?
C6 C1 C2 C3 -4.6(2) . . . . ?
C6 C1 C7 O1 13.6(2) . . . . ?
C6 C1 C7 O2 -168.57(14) . . . . ?
C7 C1 C2 O3 -6.0(2) . . . . ?
C7 C1 C2 C3 174.61(13) . . . . ?
C7 C1 C6 C5 -177.27(13) . . . . ?
C15 N1 C17 N3 -57.87(15) . . . . ?
C15 N1 C18 N4 59.49(15) . . . . ?
C15 N2 C16 N3 58.30(15) . . . . ?
C15 N2 C19 N4 -58.73(14) . . . . ?
C16 N2 C15 N1 -58.30(15) . . . . ?
C16 N2 C19 N4 59.32(14) . . . . ?
C16 N3 C17 N1 57.98(15) . . . . ?
C16 N3 C20 N4 -59.38(14) . . . . ?
C17 N1 C15 N2 58.18(15) . . . . ?
C17 N1 C18 N4 -58.75(15) . . . . ?
C17 N3 C16 N2 -58.27(14) . . . . ?
C17 N3 C20 N4 59.17(14) . . . . ?
C18 N1 C15 N2 -60.25(15) . . . . ?
C18 N1 C17 N3 60.53(15) . . . . ?
C18 N4 C19 N2 59.02(14) . . . . ?
C18 N4 C20 N3 -58.88(14) . . . . ?
C19 N2 C15 N1 60.10(15) . . . . ?
C19 N2 C16 N3 -60.39(14) . . . . ?
C19 N4 C18 N1 -59.61(14) . . . . ?
C19 N4 C20 N3 59.56(14) . . . . ?
C20 N3 C16 N2 60.56(15) . . . . ?
C20 N3 C17 N1 -60.95(15) . . . . ?
C20 N4 C18 N1 58.89(14) . . . . ?
C20 N4 C19 N2 -59.77(14) . . . . ?
C21 N5 C23 N7 -58.11(15) . . . . ?
C21 N5 C26 N8 58.33(15) . . . . ?
C21 N6 C22 N7 60.51(16) . . . . ?
C21 N6 C24 N8 -59.94(17) . . . . ?
C22 N6 C21 N5 -59.62(16) . . . . ?
C22 N6 C24 N8 58.39(17) . . . . ?
C22 N7 C23 N5 58.26(15) . . . . ?
C22 N7 C25 N8 -58.47(16) . . . . ?
C23 N5 C21 N6 59.07(16) . . . . ?
C23 N5 C26 N8 -59.34(15) . . . . ?
C23 N7 C22 N6 -60.05(16) . . . . ?
C23 N7 C25 N8 60.10(17) . . . . ?
C24 N6 C21 N5 58.71(17) . . . . ?
C24 N6 C22 N7 -58.27(16) . . . . ?
C24 N8 C25 N7 58.54(16) . . . . ?
C24 N8 C26 N5 -58.59(15) . . . . ?
C25 N7 C22 N6 58.20(16) . . . . ?
C25 N7 C23 N5 -59.60(16) . . . . ?
C25 N8 C24 N6 -58.43(17) . . . . ?
C25 N8 C26 N5 59.09(15) . . . . ?
C26 N5 C21 N6 -58.30(16) . . . . ?
C26 N5 C23 N7 59.59(15) . . . . ?
C26 N8 C24 N6 59.68(17) . . . . ?
C26 N8 C25 N7 -59.68(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
