# 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
_database_code_depnum_ccdc_archive 'CCDC 1816606'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C53 H80 N22 O12 S5'
_chemical_formula_weight         1377.69

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   40.012(8)
_cell_length_b                   16.186(3)
_cell_length_c                   10.282(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.64(3)
_cell_angle_gamma                90
_cell_volume                     6646(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    8512
_cell_measurement_theta_min      1.9809
_cell_measurement_theta_max      27.8744

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             2912
_exptl_transmission_factor_min   0.5951
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.249
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33058
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7928
_reflns_number_gt                6308
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7928
_refine_ls_number_parameters     452
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20070(2) 0.27854(2) 0.55326(3) 0.02027(11) Uani 1 1 d . . . . .
S2 S 0.10106(2) 0.22106(2) 0.65369(4) 0.02027(11) Uani 1 1 d . . . . .
S3 S 0.000000 0.28934(3) 0.750000 0.02028(13) Uani 1 2 d S T P . .
O1 O 0.21535(3) 0.95680(7) 0.53340(11) 0.0321(3) Uani 1 1 d . . . . .
O2 O 0.20189(3) 0.55994(7) 0.34163(11) 0.0367(3) Uani 1 1 d . . . . .
O3 O 0.13719(3) 0.97559(7) 0.63718(11) 0.0371(3) Uani 1 1 d . . . . .
O4 O 0.12346(3) 0.53974(7) 0.65312(11) 0.0293(3) Uani 1 1 d . . . . .
O5 O 0.03876(3) 0.96883(7) 0.70294(11) 0.0367(3) Uani 1 1 d . . . . .
O6 O 0.04679(3) 0.53206(7) 0.73394(11) 0.0332(3) Uani 1 1 d . . . . .
N1 N 0.21116(3) 0.82166(8) 0.58494(12) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.20587(3) 0.65406(8) 0.50411(12) 0.0210(3) Uani 1 1 d . . . . .
N3 N 0.12718(3) 0.84061(8) 0.59701(12) 0.0218(3) Uani 1 1 d . . . . .
N4 N 0.12504(3) 0.67675(7) 0.69315(12) 0.0197(3) Uani 1 1 d . . . . .
N5 N 0.04244(3) 0.83420(8) 0.75744(12) 0.0218(3) Uani 1 1 d . . . . .
N6 N 0.04099(3) 0.66645(7) 0.67910(12) 0.0210(3) Uani 1 1 d . . . . .
N7 N 0.23044(3) 0.13175(8) 0.57045(13) 0.0244(3) Uani 1 1 d D . . . .
H7A H 0.2485(3) 0.1565(8) 0.5428(16) 0.029 Uiso 1 1 d D U . . .
H7B H 0.2306(4) 0.0768(5) 0.5662(15) 0.029 Uiso 1 1 d D U . . .
N8 N 0.17414(3) 0.13149(8) 0.59254(15) 0.0298(3) Uani 1 1 d D . . . .
H8A H 0.1727(4) 0.0770(5) 0.6010(17) 0.036 Uiso 1 1 d D U . . .
H8B H 0.1545(3) 0.1585(8) 0.5983(16) 0.036 Uiso 1 1 d D U . . .
N9 N 0.13234(3) 0.36448(8) 0.69471(14) 0.0255(3) Uani 1 1 d D . . . .
H9A H 0.1324(4) 0.4192(5) 0.6919(16) 0.031 Uiso 1 1 d D U . . .
H9B H 0.1504(3) 0.3392(8) 0.6684(16) 0.031 Uiso 1 1 d D U . . .
N10 N 0.07536(3) 0.36989(8) 0.68618(15) 0.0299(3) Uani 1 1 d D . . . .
H10A H 0.0747(4) 0.4242(5) 0.6973(17) 0.036 Uiso 1 1 d D U . . .
H10B H 0.0558(3) 0.3444(9) 0.6921(17) 0.036 Uiso 1 1 d D U . . .
N11 N 0.02842(3) 0.14140(8) 0.74588(14) 0.0279(3) Uani 1 1 d D . . . .
H11A H 0.0468(3) 0.1682(8) 0.7275(16) 0.033 Uiso 1 1 d D U . . .
H11B H 0.0295(4) 0.0862(5) 0.7406(16) 0.033 Uiso 1 1 d D U . . .
C1 C 0.21648(4) 0.92350(11) 0.76156(16) 0.0335(4) Uani 1 1 d . . . . .
H1A H 0.217355 0.983580 0.773041 0.050 Uiso 1 1 calc R U . . .
H1B H 0.236776 0.898593 0.803071 0.050 Uiso 1 1 calc R U . . .
H1C H 0.196777 0.901502 0.801770 0.050 Uiso 1 1 calc R U . . .
C2 C 0.21421(4) 0.90332(10) 0.61883(16) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.20962(4) 0.79837(9) 0.45178(14) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.210431 0.840241 0.387311 0.027 Uiso 1 1 calc R U . . .
C4 C 0.20710(4) 0.72031(9) 0.41418(14) 0.0221(3) Uani 1 1 d . . . . .
H4 H 0.206078 0.708173 0.323620 0.026 Uiso 1 1 calc R U . . .
C5 C 0.20766(4) 0.67714(10) 0.63687(14) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.207124 0.635092 0.701169 0.027 Uiso 1 1 calc R U . . .
C6 C 0.21009(4) 0.75563(10) 0.67534(15) 0.0235(3) Uani 1 1 d . . . . .
H6 H 0.211125 0.767741 0.765913 0.028 Uiso 1 1 calc R U . . .
C7 C 0.20376(4) 0.57378(9) 0.45879(15) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.20396(4) 0.50645(10) 0.55877(15) 0.0291(4) Uani 1 1 d . . . . .
H8D H 0.204218 0.452613 0.515248 0.044 Uiso 1 1 calc R U . . .
H8E H 0.183858 0.510839 0.608044 0.044 Uiso 1 1 calc R U . . .
H8C H 0.223933 0.511849 0.618446 0.044 Uiso 1 1 calc R U . . .
C9 C 0.13077(5) 0.93644(10) 0.41214(16) 0.0376(4) Uani 1 1 d . . . . .
H9D H 0.134746 0.995233 0.396416 0.056 Uiso 1 1 calc R U . . .
H9E H 0.108712 0.920859 0.372833 0.056 Uiso 1 1 calc R U . . .
H9C H 0.148095 0.903556 0.373102 0.056 Uiso 1 1 calc R U . . .
C10 C 0.13192(4) 0.92059(10) 0.55640(16) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.12372(4) 0.77159(9) 0.51286(15) 0.0215(3) Uani 1 1 d . . . . .
H11 H 0.121986 0.780345 0.421324 0.026 Uiso 1 1 calc R U . . .
C12 C 0.12283(4) 0.69480(9) 0.55838(14) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.120629 0.650379 0.498054 0.026 Uiso 1 1 calc R U . . .
C13 C 0.12698(4) 0.74592(10) 0.77744(14) 0.0228(3) Uani 1 1 d . . . . .
H13 H 0.127452 0.737304 0.868931 0.027 Uiso 1 1 calc R U . . .
C14 C 0.12814(4) 0.82268(9) 0.73187(14) 0.0229(3) Uani 1 1 d . . . . .
H14 H 0.129677 0.867189 0.792183 0.027 Uiso 1 1 calc R U . . .
C15 C 0.12533(4) 0.59600(9) 0.73416(15) 0.0227(3) Uani 1 1 d . . . . .
C16 C 0.12770(4) 0.58033(10) 0.87813(15) 0.0299(4) Uani 1 1 d . . . . .
H16A H 0.129646 0.520801 0.894296 0.045 Uiso 1 1 calc R U . . .
H16B H 0.107548 0.601431 0.916194 0.045 Uiso 1 1 calc R U . . .
H16C H 0.147470 0.608501 0.918014 0.045 Uiso 1 1 calc R U . . .
C17 C 0.04678(5) 0.93852(10) 0.93140(16) 0.0370(4) Uani 1 1 d . . . . .
H17A H 0.047791 0.998736 0.940697 0.056 Uiso 1 1 calc R U . . .
H17B H 0.067594 0.914113 0.969328 0.056 Uiso 1 1 calc R U . . .
H17C H 0.027783 0.917130 0.976782 0.056 Uiso 1 1 calc R U . . .
C18 C 0.04245(4) 0.91641(10) 0.78952(16) 0.0265(4) Uani 1 1 d . . . . .
C19 C 0.03864(4) 0.81029(9) 0.62479(14) 0.0225(3) Uani 1 1 d . . . . .
H19 H 0.036533 0.852042 0.559845 0.027 Uiso 1 1 calc R U . . .
C20 C 0.03793(4) 0.73152(9) 0.58784(15) 0.0217(3) Uani 1 1 d . . . . .
H20 H 0.035284 0.718747 0.497593 0.026 Uiso 1 1 calc R U . . .
C21 C 0.04441(4) 0.69001(9) 0.81146(14) 0.0219(3) Uani 1 1 d . . . . .
H21 H 0.046233 0.648159 0.876304 0.026 Uiso 1 1 calc R U . . .
C22 C 0.04518(4) 0.76872(9) 0.84857(15) 0.0230(3) Uani 1 1 d . . . . .
H22 H 0.047636 0.781338 0.938907 0.028 Uiso 1 1 calc R U . . .
C23 C 0.04271(4) 0.58388(9) 0.64712(16) 0.0243(3) Uani 1 1 d . . . . .
C24 C 0.04013(5) 0.56144(10) 0.50514(16) 0.0335(4) Uani 1 1 d . . . . .
H24A H 0.041480 0.501289 0.495939 0.050 Uiso 1 1 calc R U . . .
H24B H 0.058530 0.587346 0.461592 0.050 Uiso 1 1 calc R U . . .
H24C H 0.018686 0.581034 0.465220 0.050 Uiso 1 1 calc R U . . .
C25 C 0.20184(3) 0.17349(9) 0.57271(13) 0.0192(3) Uani 1 1 d . . . . .
C26 C 0.10310(4) 0.32541(9) 0.67951(14) 0.0198(3) Uani 1 1 d . . . . .
C27 C 0.000000 0.18368(13) 0.750000 0.0200(4) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C25 1.7124(16) . ?
S2 C26 1.7109(16) . ?
S3 C27 1.710(2) . ?
O1 C2 1.2362(19) . ?
O2 C7 1.2229(18) . ?
O3 C10 1.2267(19) . ?
O4 C15 1.2335(18) . ?
O5 C18 1.2318(19) . ?
O6 C23 1.2282(18) . ?
N1 C2 1.3704(19) . ?
N1 C3 1.4177(18) . ?
N1 C6 1.4189(19) . ?
N2 C7 1.3812(19) . ?
N2 C5 1.4126(19) . ?
N2 C4 1.4188(18) . ?
N3 C10 1.3771(19) . ?
N3 C11 1.4144(18) . ?
N3 C14 1.4148(18) . ?
N4 C15 1.3731(18) . ?
N4 C12 1.4134(18) . ?
N4 C13 1.4150(18) . ?
N5 C18 1.3709(19) . ?
N5 C22 1.4143(18) . ?
N5 C19 1.4166(18) . ?
N6 C23 1.3792(18) . ?
N6 C20 1.4108(18) . ?
N6 C21 1.4116(18) . ?
N7 C25 1.3306(18) . ?
N7 H7A 0.889(8) . ?
N7 H7B 0.890(8) . ?
N8 C25 1.3267(19) . ?
N8 H8A 0.889(8) . ?
N8 H8B 0.903(8) . ?
N9 C26 1.3303(19) . ?
N9 H9A 0.886(8) . ?
N9 H9B 0.888(8) . ?
N10 C26 1.3284(19) . ?
N10 H10A 0.887(8) . ?
N10 H10B 0.891(8) . ?
N11 C27 1.3302(17) . ?
N11 H11A 0.883(8) . ?
N11 H11B 0.896(8) . ?
C1 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.323(2) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.332(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.498(2) . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.503(2) . ?
C9 H9D 0.9800 . ?
C9 H9E 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.329(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.330(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.499(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.501(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.330(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.330(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.501(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C2 N1 C3 119.99(13) . . ?
C2 N1 C6 124.46(13) . . ?
C3 N1 C6 115.54(13) . . ?
C7 N2 C5 124.96(13) . . ?
C7 N2 C4 119.67(13) . . ?
C5 N2 C4 115.35(12) . . ?
C10 N3 C11 124.55(13) . . ?
C10 N3 C14 119.63(13) . . ?
C11 N3 C14 115.66(12) . . ?
C15 N4 C12 119.78(13) . . ?
C15 N4 C13 124.47(13) . . ?
C12 N4 C13 115.75(12) . . ?
C18 N5 C22 124.69(13) . . ?
C18 N5 C19 119.68(13) . . ?
C22 N5 C19 115.61(12) . . ?
C23 N6 C20 124.65(13) . . ?
C23 N6 C21 119.24(12) . . ?
C20 N6 C21 116.01(12) . . ?
C25 N7 H7A 119.7(10) . . ?
C25 N7 H7B 121.1(10) . . ?
H7A N7 H7B 115.2(11) . . ?
C25 N8 H8A 125.8(10) . . ?
C25 N8 H8B 120.0(10) . . ?
H8A N8 H8B 114.2(11) . . ?
C26 N9 H9A 118.3(10) . . ?
C26 N9 H9B 118.2(10) . . ?
H9A N9 H9B 116.6(11) . . ?
C26 N10 H10A 125.1(10) . . ?
C26 N10 H10B 119.6(10) . . ?
H10A N10 H10B 114.7(12) . . ?
C27 N11 H11A 118.6(10) . . ?
C27 N11 H11B 124.0(10) . . ?
H11A N11 H11B 115.7(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 120.10(14) . . ?
O1 C2 C1 122.67(15) . . ?
N1 C2 C1 117.23(14) . . ?
C4 C3 N1 122.27(14) . . ?
C4 C3 H3 118.9 . . ?
N1 C3 H3 118.9 . . ?
C3 C4 N2 122.44(14) . . ?
C3 C4 H4 118.8 . . ?
N2 C4 H4 118.8 . . ?
C6 C5 N2 122.50(14) . . ?
C6 C5 H5 118.8 . . ?
N2 C5 H5 118.8 . . ?
C5 C6 N1 121.90(14) . . ?
C5 C6 H6 119.0 . . ?
N1 C6 H6 119.0 . . ?
O2 C7 N2 120.22(14) . . ?
O2 C7 C8 122.69(15) . . ?
N2 C7 C8 117.09(14) . . ?
C7 C8 H8D 109.5 . . ?
C7 C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8D C8 H8C 109.5 . . ?
H8E C8 H8C 109.5 . . ?
C10 C9 H9D 109.5 . . ?
C10 C9 H9E 109.5 . . ?
H9D C9 H9E 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9D C9 H9C 109.5 . . ?
H9E C9 H9C 109.5 . . ?
O3 C10 N3 119.87(15) . . ?
O3 C10 C9 122.51(15) . . ?
N3 C10 C9 117.61(14) . . ?
C12 C11 N3 121.80(14) . . ?
C12 C11 H11 119.1 . . ?
N3 C11 H11 119.1 . . ?
C11 C12 N4 122.48(14) . . ?
C11 C12 H12 118.8 . . ?
N4 C12 H12 118.8 . . ?
C14 C13 N4 121.69(14) . . ?
C14 C13 H13 119.2 . . ?
N4 C13 H13 119.2 . . ?
C13 C14 N3 122.52(14) . . ?
C13 C14 H14 118.7 . . ?
N3 C14 H14 118.7 . . ?
O4 C15 N4 119.76(14) . . ?
O4 C15 C16 122.65(14) . . ?
N4 C15 C16 117.59(13) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 N5 119.76(15) . . ?
O5 C18 C17 122.63(15) . . ?
N5 C18 C17 117.61(14) . . ?
C20 C19 N5 122.40(14) . . ?
C20 C19 H19 118.8 . . ?
N5 C19 H19 118.8 . . ?
C19 C20 N6 121.76(14) . . ?
C19 C20 H20 119.1 . . ?
N6 C20 H20 119.1 . . ?
C22 C21 N6 122.31(14) . . ?
C22 C21 H21 118.8 . . ?
N6 C21 H21 118.8 . . ?
C21 C22 N5 121.90(14) . . ?
C21 C22 H22 119.0 . . ?
N5 C22 H22 119.0 . . ?
O6 C23 N6 119.66(15) . . ?
O6 C23 C24 122.63(14) . . ?
N6 C23 C24 117.70(14) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N8 C25 N7 118.05(14) . . ?
N8 C25 S1 120.70(11) . . ?
N7 C25 S1 121.24(11) . . ?
N10 C26 N9 117.89(14) . . ?
N10 C26 S2 120.75(12) . . ?
N9 C26 S2 121.36(11) . . ?
N11 C27 N11 118.1(2) 2_556 . ?
N11 C27 S3 120.96(10) 2_556 . ?
N11 C27 S3 120.96(10) . . ?

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
C3 N1 C2 O1 0.6(2) . . . . ?
C6 N1 C2 O1 179.11(13) . . . . ?
C3 N1 C2 C1 -178.66(12) . . . . ?
C6 N1 C2 C1 -0.1(2) . . . . ?
C2 N1 C3 C4 179.14(14) . . . . ?
C6 N1 C3 C4 0.5(2) . . . . ?
N1 C3 C4 N2 -0.2(2) . . . . ?
C7 N2 C4 C3 -178.97(14) . . . . ?
C5 N2 C4 C3 -0.3(2) . . . . ?
C7 N2 C5 C6 179.14(14) . . . . ?
C4 N2 C5 C6 0.5(2) . . . . ?
N2 C5 C6 N1 -0.3(2) . . . . ?
C2 N1 C6 C5 -178.83(14) . . . . ?
C3 N1 C6 C5 -0.2(2) . . . . ?
C5 N2 C7 O2 179.09(13) . . . . ?
C4 N2 C7 O2 -2.3(2) . . . . ?
C5 N2 C7 C8 -1.0(2) . . . . ?
C4 N2 C7 C8 177.57(12) . . . . ?
C11 N3 C10 O3 -174.49(14) . . . . ?
C14 N3 C10 O3 0.6(2) . . . . ?
C11 N3 C10 C9 4.8(2) . . . . ?
C14 N3 C10 C9 179.83(13) . . . . ?
C10 N3 C11 C12 172.59(15) . . . . ?
C14 N3 C11 C12 -2.7(2) . . . . ?
N3 C11 C12 N4 0.4(2) . . . . ?
C15 N4 C12 C11 -177.39(14) . . . . ?
C13 N4 C12 C11 2.4(2) . . . . ?
C15 N4 C13 C14 176.84(14) . . . . ?
C12 N4 C13 C14 -2.9(2) . . . . ?
N4 C13 C14 N3 0.7(2) . . . . ?
C10 N3 C14 C13 -173.39(15) . . . . ?
C11 N3 C14 C13 2.1(2) . . . . ?
C12 N4 C15 O4 -0.4(2) . . . . ?
C13 N4 C15 O4 179.86(13) . . . . ?
C12 N4 C15 C16 -179.99(12) . . . . ?
C13 N4 C15 C16 0.3(2) . . . . ?
C22 N5 C18 O5 -177.49(14) . . . . ?
C19 N5 C18 O5 0.9(2) . . . . ?
C22 N5 C18 C17 2.0(2) . . . . ?
C19 N5 C18 C17 -179.60(13) . . . . ?
C18 N5 C19 C20 -178.96(14) . . . . ?
C22 N5 C19 C20 -0.5(2) . . . . ?
N5 C19 C20 N6 -0.1(2) . . . . ?
C23 N6 C20 C19 -175.42(14) . . . . ?
C21 N6 C20 C19 0.8(2) . . . . ?
C23 N6 C21 C22 175.54(14) . . . . ?
C20 N6 C21 C22 -0.9(2) . . . . ?
N6 C21 C22 N5 0.3(2) . . . . ?
C18 N5 C22 C21 178.78(15) . . . . ?
C19 N5 C22 C21 0.4(2) . . . . ?
C20 N6 C23 O6 176.93(13) . . . . ?
C21 N6 C23 O6 0.8(2) . . . . ?
C20 N6 C23 C24 -1.9(2) . . . . ?
C21 N6 C23 C24 -177.98(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7A S1 0.889(8) 2.543(9) 3.4297(15) 175.5(14) 7_556 yes
N7 H7B O1 0.890(8) 2.057(9) 2.9153(18) 161.5(14) 1_545 yes
N11 H11B O5 0.896(8) 1.979(9) 2.8622(18) 168.3(14) 1_545 yes
N8 H8A O3 0.889(8) 2.217(12) 2.9749(18) 142.9(13) 1_545 yes
N8 H8B S2 0.903(8) 2.466(9) 3.3589(15) 169.7(14) . yes
N9 H9A O4 0.886(8) 2.018(9) 2.8874(18) 166.4(15) . yes
N9 H9B S1 0.888(8) 2.592(9) 3.4695(16) 169.9(14) . yes
N10 H10A O6 0.887(8) 2.120(12) 2.9171(18) 149.3(13) . yes
N10 H10B S3 0.891(8) 2.510(9) 3.3873(15) 168.4(15) . yes
N11 H11A S2 0.883(8) 2.498(9) 3.3702(15) 169.8(14) . yes

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.059

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1816610'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N4 O4'
_chemical_formula_weight         388.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   7.9117(16)
_cell_length_b                   9.6617(19)
_cell_length_c                   12.132(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.67(3)
_cell_angle_gamma                90
_cell_volume                     924.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    2508
_cell_measurement_theta_min      2.6986
_cell_measurement_theta_max      28.1179

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   0.5956
_exptl_transmission_factor_max   0.7451
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9285
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.583
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2214
_reflns_number_gt                1626
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47283(11) 1.15530(9) 0.05621(7) 0.0195(2) Uani 1 1 d . . . . .
O2 O 0.07294(11) 0.63140(10) 0.14930(7) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.20701(12) 1.07292(11) 0.06861(8) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.07529(13) 0.81655(11) 0.03620(8) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.18455(15) 1.03419(13) -0.04673(10) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.288269 1.050178 -0.086907 0.018 Uiso 1 1 calc R U . . .
C2 C 0.10839(15) 0.88604(13) -0.06584(10) 0.0148(3) Uani 1 1 d . . . . .
H2 H 0.173897 0.827782 -0.115545 0.018 Uiso 1 1 calc R U . . .
C3 C -0.02001(15) 0.90117(13) 0.10752(10) 0.0150(3) Uani 1 1 d . . . . .
H3 H -0.042112 0.853571 0.178113 0.018 Uiso 1 1 calc R U . . .
C4 C 0.05644(15) 1.04949(13) 0.12635(10) 0.0150(3) Uani 1 1 d . . . . .
H4 H 0.072258 1.075407 0.206329 0.018 Uiso 1 1 calc R U . . .
C5 C 0.35300(15) 1.13525(13) 0.11205(10) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.35961(16) 1.17810(14) 0.23272(10) 0.0198(3) Uani 1 1 d . . . . .
H6A H 0.347750 1.094729 0.278900 0.024 Uiso 1 1 calc R U . . .
H6B H 0.262590 1.239965 0.243543 0.024 Uiso 1 1 calc R U . . .
C7 C 0.52371(16) 1.25218(16) 0.27128(11) 0.0252(3) Uani 1 1 d . . . . .
H7A H 0.620142 1.190621 0.262517 0.038 Uiso 1 1 calc R U . . .
H7B H 0.521472 1.277756 0.349317 0.038 Uiso 1 1 calc R U . . .
H7C H 0.535135 1.335847 0.226831 0.038 Uiso 1 1 calc R U . . .
C8 C 0.11636(15) 0.68286(13) 0.06342(10) 0.0153(3) Uani 1 1 d . . . . .
C9 C 0.21708(15) 0.60195(13) -0.01570(10) 0.0176(3) Uani 1 1 d . . . . .
H9A H 0.315892 0.657623 -0.034288 0.021 Uiso 1 1 calc R U . . .
H9B H 0.145207 0.584631 -0.084993 0.021 Uiso 1 1 calc R U . . .
C10 C 0.27894(17) 0.46411(14) 0.03371(11) 0.0227(3) Uani 1 1 d . . . . .
H10A H 0.357062 0.481127 0.099210 0.034 Uiso 1 1 calc R U . . .
H10B H 0.337778 0.412383 -0.021173 0.034 Uiso 1 1 calc R U . . .
H10C H 0.181738 0.410233 0.054862 0.034 Uiso 1 1 calc R U . . .


_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
O1 C5 1.2248(15) . ?
O2 C8 1.2284(15) . ?
N1 C5 1.3695(16) . ?
N1 C1 1.4454(15) . ?
N1 C4 1.4481(15) . ?
N2 C8 1.3659(16) . ?
N2 C3 1.4463(15) . ?
N2 C2 1.4508(14) . ?
C1 C2 1.5629(17) . ?
C1 C3 1.5723(17) 3_575 ?
C1 H1 1.0000 . ?
C2 C4 1.5720(17) 3_575 ?
C2 H2 1.0000 . ?
C3 C4 1.5649(18) . ?
C3 H3 1.0000 . ?
C4 H4 1.0000 . ?
C5 C6 1.5182(17) . ?
C6 C7 1.5224(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5141(17) . ?
C9 C10 1.5246(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C5 N1 C1 121.31(10) . . ?
C5 N1 C4 125.73(10) . . ?
C1 N1 C4 112.76(10) . . ?
C8 N2 C3 121.01(10) . . ?
C8 N2 C2 126.02(10) . . ?
C3 N2 C2 112.83(10) . . ?
N1 C1 C2 113.34(10) . . ?
N1 C1 C3 112.52(10) . 3_575 ?
C2 C1 C3 89.98(9) . 3_575 ?
N1 C1 H1 113.0 . . ?
C2 C1 H1 113.0 . . ?
C3 C1 H1 113.0 3_575 . ?
N2 C2 C1 113.04(10) . . ?
N2 C2 C4 112.41(9) . 3_575 ?
C1 C2 C4 90.09(9) . 3_575 ?
N2 C2 H2 113.1 . . ?
C1 C2 H2 113.1 . . ?
C4 C2 H2 113.1 3_575 . ?
N2 C3 C4 113.01(9) . . ?
N2 C3 C1 113.33(9) . 3_575 ?
C4 C3 C1 90.01(9) . 3_575 ?
N2 C3 H3 112.9 . . ?
C4 C3 H3 112.9 . . ?
C1 C3 H3 112.9 3_575 . ?
N1 C4 C3 113.32(10) . . ?
N1 C4 C2 113.33(10) . 3_575 ?
C3 C4 C2 89.92(9) . 3_575 ?
N1 C4 H4 112.8 . . ?
C3 C4 H4 112.8 . . ?
C2 C4 H4 112.8 3_575 . ?
O1 C5 N1 121.55(11) . . ?
O1 C5 C6 121.53(11) . . ?
N1 C5 C6 116.92(10) . . ?
C5 C6 C7 112.71(11) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N2 120.69(11) . . ?
O2 C8 C9 121.79(12) . . ?
N2 C8 C9 117.52(10) . . ?
C8 C9 C10 111.74(10) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 135.22(11) . . . . ?
C4 N1 C1 C2 -49.75(13) . . . . ?
C5 N1 C1 C3 -124.49(12) . . . 3_575 ?
C4 N1 C1 C3 50.54(13) . . . 3_575 ?
C8 N2 C2 C1 -134.18(12) . . . . ?
C3 N2 C2 C1 50.03(13) . . . . ?
C8 N2 C2 C4 125.61(12) . . . 3_575 ?
C3 N2 C2 C4 -50.18(13) . . . 3_575 ?
N1 C1 C2 N2 -0.02(14) . . . . ?
C3 C1 C2 N2 -114.67(10) 3_575 . . . ?
N1 C1 C2 C4 114.50(10) . . . 3_575 ?
C3 C1 C2 C4 -0.15(8) 3_575 . . 3_575 ?
C8 N2 C3 C4 133.98(12) . . . . ?
C2 N2 C3 C4 -50.00(13) . . . . ?
C8 N2 C3 C1 -125.46(12) . . . 3_575 ?
C2 N2 C3 C1 50.56(13) . . . 3_575 ?
C5 N1 C4 C3 -135.48(12) . . . . ?
C1 N1 C4 C3 49.75(13) . . . . ?
C5 N1 C4 C2 123.90(13) . . . 3_575 ?
C1 N1 C4 C2 -50.86(14) . . . 3_575 ?
N2 C3 C4 N1 0.13(14) . . . . ?
C1 C3 C4 N1 -115.36(10) 3_575 . . . ?
N2 C3 C4 C2 115.63(10) . . . 3_575 ?
C1 C3 C4 C2 0.15(8) 3_575 . . 3_575 ?
C1 N1 C5 O1 -3.13(18) . . . . ?
C4 N1 C5 O1 -177.48(11) . . . . ?
C1 N1 C5 C6 176.99(11) . . . . ?
C4 N1 C5 C6 2.65(18) . . . . ?
O1 C5 C6 C7 2.76(18) . . . . ?
N1 C5 C6 C7 -177.36(11) . . . . ?
C3 N2 C8 O2 0.08(17) . . . . ?
C2 N2 C8 O2 -175.39(11) . . . . ?
C3 N2 C8 C9 -179.71(10) . . . . ?
C2 N2 C8 C9 4.82(17) . . . . ?
O2 C8 C9 C10 -9.33(17) . . . . ?
N2 C8 C9 C10 170.46(11) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.051

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1816608'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N4 O2 S'
_chemical_formula_weight         270.35

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.5271(17)
_cell_length_b                   11.207(2)
_cell_length_c                   15.059(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1439.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3981
_cell_measurement_theta_min      2.2653
_cell_measurement_theta_max      27.8346

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   0.5956
_exptl_transmission_factor_max   0.7451
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14417
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         27.860
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3425
_reflns_number_gt                2507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.93811(7) 0.25812(7) 0.46472(4) 0.0584(2) Uani 1 1 d . . . . .
O1 O 0.2592(3) 0.1593(2) 0.77881(15) 0.0947(9) Uani 1 1 d . . . . .
O2 O 0.3306(3) 0.3187(2) 1.19878(14) 0.0880(8) Uani 1 1 d . . . . .
N1 N 1.0704(3) 0.1982(2) 0.61717(16) 0.0539(6) Uani 1 1 d . . . . .
H1A H 1.072(3) 0.172(3) 0.672(2) 0.065 Uiso 1 1 d . U . . .
H1B H 1.158(4) 0.214(3) 0.5911(19) 0.065 Uiso 1 1 d . U . . .
N2 N 0.8048(3) 0.1848(2) 0.61316(16) 0.0551(6) Uani 1 1 d . . . . .
H2A H 0.803(3) 0.169(3) 0.669(2) 0.066 Uiso 1 1 d . U . . .
H2B H 0.712(4) 0.195(3) 0.589(2) 0.066 Uiso 1 1 d . U . . .
N3 N 0.3955(3) 0.1722(2) 0.90751(14) 0.0544(6) Uani 1 1 d . . . . .
N4 N 0.4199(3) 0.3043(2) 1.05864(13) 0.0491(5) Uani 1 1 d . . . . .
C1 C 0.9378(3) 0.2112(2) 0.57157(16) 0.0422(5) Uani 1 1 d . . . . .
C2 C 0.2787(4) -0.0194(3) 0.8632(2) 0.0760(10) Uani 1 1 d . . . . .
H2C H 0.216338 -0.052436 0.816180 0.114 Uiso 1 1 calc R U . . .
H2D H 0.223573 -0.027332 0.918509 0.114 Uiso 1 1 calc R U . . .
H2E H 0.376626 -0.061442 0.866722 0.114 Uiso 1 1 calc R U . . .
C3 C 0.3092(4) 0.1098(3) 0.84498(19) 0.0652(9) Uani 1 1 d . . . . .
C4 C 0.4360(4) 0.2947(3) 0.89998(17) 0.0581(7) Uani 1 1 d . . . . .
C5 C 0.4482(4) 0.3574(3) 0.97421(18) 0.0575(7) Uani 1 1 d . . . . .
H5 H 0.475787 0.437611 0.971148 0.069 Uiso 1 1 calc R U . . .
C6 C 0.4534(3) 0.1793(2) 1.06277(16) 0.0494(6) Uani 1 1 d . . . . .
C7 C 0.4412(4) 0.1174(3) 0.98811(16) 0.0530(6) Uani 1 1 d . . . . .
H7 H 0.463337 0.036144 0.988703 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4819(5) 0.3468(4) 0.8114(2) 0.0941(13) Uani 1 1 d . . . . .
H8A H 0.518772 0.426935 0.819675 0.141 Uiso 1 1 calc R U . . .
H8B H 0.392426 0.347264 0.772735 0.141 Uiso 1 1 calc R U . . .
H8C H 0.563635 0.299280 0.785519 0.141 Uiso 1 1 calc R U . . .
C9 C 0.5155(4) 0.1238(3) 1.14656(19) 0.0694(9) Uani 1 1 d . . . . .
H9A H 0.430706 0.111502 1.187490 0.104 Uiso 1 1 calc R U . . .
H9B H 0.591791 0.175983 1.172843 0.104 Uiso 1 1 calc R U . . .
H9C H 0.563596 0.048628 1.132851 0.104 Uiso 1 1 calc R U . . .
C10 C 0.3587(3) 0.3678(3) 1.12779(19) 0.0587(7) Uani 1 1 d . . . . .
C11 C 0.3264(4) 0.4976(3) 1.1145(2) 0.0781(10) Uani 1 1 d . . . . .
H11A H 0.278173 0.529658 1.166925 0.117 Uiso 1 1 calc R U . . .
H11B H 0.257112 0.507721 1.064806 0.117 Uiso 1 1 calc R U . . .
H11C H 0.423062 0.538740 1.103203 0.117 Uiso 1 1 calc R U . . .


_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 C1 1.693(3) . ?
O1 C3 1.218(4) . ?
O2 C10 1.226(3) . ?
N1 C1 1.331(3) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.86(3) . ?
N2 C1 1.329(3) . ?
N2 H2A 0.86(3) . ?
N2 H2B 0.88(3) . ?
N3 C3 1.384(4) . ?
N3 C7 1.415(3) . ?
N3 C4 1.420(4) . ?
N4 C10 1.365(4) . ?
N4 C5 1.425(3) . ?
N4 C6 1.430(3) . ?
C2 C3 1.497(5) . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9600 . ?
C4 C5 1.325(4) . ?
C4 C8 1.507(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.325(4) . ?
C6 C9 1.503(4) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.493(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 122(2) . . ?
C1 N1 H1B 119(2) . . ?
H1A N1 H1B 119(3) . . ?
C1 N2 H2A 121(2) . . ?
C1 N2 H2B 123(2) . . ?
H2A N2 H2B 115(3) . . ?
C3 N3 C7 120.7(3) . . ?
C3 N3 C4 124.3(3) . . ?
C7 N3 C4 114.9(2) . . ?
C10 N4 C5 121.8(3) . . ?
C10 N4 C6 123.6(2) . . ?
C5 N4 C6 114.5(2) . . ?
N2 C1 N1 117.3(2) . . ?
N2 C1 S1 121.2(2) . . ?
N1 C1 S1 121.51(19) . . ?
C3 C2 H2C 109.5 . . ?
C3 C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C3 C2 H2E 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O1 C3 N3 120.8(3) . . ?
O1 C3 C2 122.0(3) . . ?
N3 C3 C2 117.1(3) . . ?
C5 C4 N3 117.7(2) . . ?
C5 C4 C8 121.4(3) . . ?
N3 C4 C8 120.5(3) . . ?
C4 C5 N4 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
N4 C5 H5 119.4 . . ?
C7 C6 N4 117.4(2) . . ?
C7 C6 C9 121.5(3) . . ?
N4 C6 C9 120.8(2) . . ?
C6 C7 N3 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
N3 C7 H7 119.3 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N4 120.3(3) . . ?
O2 C10 C11 121.2(3) . . ?
N4 C10 C11 118.4(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N3 C3 O1 174.2(3) . . . . ?
C4 N3 C3 O1 -1.6(5) . . . . ?
C7 N3 C3 C2 -4.9(4) . . . . ?
C4 N3 C3 C2 179.3(3) . . . . ?
C3 N3 C4 C5 148.2(3) . . . . ?
C7 N3 C4 C5 -27.8(4) . . . . ?
C3 N3 C4 C8 -38.8(4) . . . . ?
C7 N3 C4 C8 145.2(3) . . . . ?
N3 C4 C5 N4 -0.7(4) . . . . ?
C8 C4 C5 N4 -173.6(3) . . . . ?
C10 N4 C5 C4 -148.2(3) . . . . ?
C6 N4 C5 C4 28.9(4) . . . . ?
C10 N4 C6 C7 149.3(3) . . . . ?
C5 N4 C6 C7 -27.7(4) . . . . ?
C10 N4 C6 C9 -36.8(4) . . . . ?
C5 N4 C6 C9 146.3(3) . . . . ?
N4 C6 C7 N3 -0.6(5) . . . . ?
C9 C6 C7 N3 -174.5(3) . . . . ?
C3 N3 C7 C6 -147.2(3) . . . . ?
C4 N3 C7 C6 29.0(4) . . . . ?
C5 N4 C10 O2 177.5(3) . . . . ?
C6 N4 C10 O2 0.8(5) . . . . ?
C5 N4 C10 C11 -2.2(4) . . . . ?
C6 N4 C10 C11 -178.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.88(3) 2.27(3) 2.951(3) 134(3) 1_655 yes
N1 H1B S1 0.86(3) 2.55(3) 3.404(3) 170(3) 4_556 yes
N2 H2A O2 0.86(3) 2.00(3) 2.841(3) 163(3) 4_557 yes
N2 H2B S1 0.88(3) 2.53(3) 3.400(3) 173(3) 4_456 yes
C8 H8B O1 0.96 2.40 2.874(5) 110.4 . yes
C8 H8C O2 0.96 2.64 3.508(5) 150.0 4_557 yes
C9 H9B O1 0.96 2.44 3.389(4) 168.0 4_557 yes

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1816609'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 N4 O4'
_chemical_formula_weight         332.36

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'

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

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

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

_cell_length_a                   12.177(2)
_cell_length_b                   10.283(2)
_cell_length_c                   24.918(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3120.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6882
_cell_measurement_theta_min      2.1425
_cell_measurement_theta_max      27.9624

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   0.5951
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19157
_diffrn_reflns_av_unetI/netI     0.1093
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             5155
_reflns_number_gt                3964
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.877
_reflns_Friedel_fraction_full    0.876

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5155
_refine_ls_number_parameters     442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.1908
_refine_ls_wR_factor_gt          0.1818
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6833(4) 0.3024(4) 0.0089(2) 0.0261(12) Uani 1 1 d . . . . .
O2 O 0.2283(4) 0.7252(5) -0.0158(2) 0.0311(13) Uani 1 1 d . . . . .
O3 O 0.3142(4) 0.7519(4) 0.1113(2) 0.0244(12) Uani 1 1 d . . . . .
O4 O 0.7057(4) 0.2619(5) 0.15999(18) 0.0249(12) Uani 1 1 d . . . . .
O5 O 0.4112(4) 0.2524(4) 0.26432(19) 0.0217(11) Uani 1 1 d . . . . .
O6 O 0.0198(4) -0.2394(4) 0.21618(19) 0.0229(11) Uani 1 1 d . . . . .
O7 O 0.0419(4) -0.1988(4) 0.3691(2) 0.0260(11) Uani 1 1 d . . . . .
O8 O 0.4931(4) 0.2275(5) 0.3943(2) 0.0307(13) Uani 1 1 d . . . . .
N1 N 0.5171(4) 0.3981(5) 0.0145(2) 0.0155(12) Uani 1 1 d . . . . .
N2 N 0.3902(4) 0.6299(5) 0.0063(2) 0.0177(13) Uani 1 1 d . . . . .
N3 N 0.4066(4) 0.5648(5) 0.1180(2) 0.0160(12) Uani 1 1 d . . . . .
N4 N 0.6080(4) 0.4265(5) 0.1214(2) 0.0157(12) Uani 1 1 d . . . . .
N5 N 0.3164(4) 0.0631(5) 0.2577(2) 0.0158(11) Uani 1 1 d . . . . .
N6 N 0.1127(4) -0.0758(5) 0.2551(2) 0.0160(12) Uani 1 1 d . . . . .
N7 N 0.2077(4) -0.1023(5) 0.3624(2) 0.0183(12) Uani 1 1 d . . . . .
N8 N 0.3348(4) 0.1311(5) 0.3688(2) 0.0201(13) Uani 1 1 d . . . . .
C1 C 0.5266(6) 0.1642(6) -0.0028(3) 0.0296(17) Uani 1 1 d . . . . .
H1A H 0.500179 0.161338 -0.039938 0.044 Uiso 1 1 calc R U . . .
H1B H 0.464397 0.154120 0.021788 0.044 Uiso 1 1 calc R U . . .
H1C H 0.579167 0.093389 0.003056 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5818(6) 0.2920(7) 0.0074(3) 0.0224(16) Uani 1 1 d . . . . .
C3 C 0.5733(5) 0.5201(6) 0.0260(3) 0.0179(14) Uani 1 1 d . . . . .
H3 H 0.637055 0.536565 0.001698 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4951(5) 0.6391(6) 0.0309(3) 0.0159(14) Uani 1 1 d . . . . .
H4 H 0.533509 0.719514 0.018416 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3448(5) 0.5041(6) 0.0016(3) 0.0230(15) Uani 1 1 d . . . . .
H5 H 0.268253 0.497135 -0.005118 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4018(5) 0.3959(6) 0.0059(3) 0.0195(15) Uani 1 1 d . . . . .
H6 H 0.365083 0.314632 0.003306 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3261(6) 0.7377(7) -0.0040(3) 0.0233(17) Uani 1 1 d . . . . .
C8 C 0.3817(6) 0.8681(6) 0.0003(3) 0.0276(18) Uani 1 1 d . . . . .
H8A H 0.331204 0.936334 -0.011769 0.041 Uiso 1 1 calc R U . . .
H8B H 0.447633 0.868813 -0.022308 0.041 Uiso 1 1 calc R U . . .
H8C H 0.402527 0.884119 0.037684 0.041 Uiso 1 1 calc R U . . .
C9 C 0.2123(5) 0.5709(7) 0.1444(3) 0.0243(16) Uani 1 1 d . . . . .
H9A H 0.152170 0.634030 0.146643 0.036 Uiso 1 1 calc R U . . .
H9B H 0.227026 0.535204 0.180159 0.036 Uiso 1 1 calc R U . . .
H9C H 0.191453 0.500235 0.120040 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3125(5) 0.6362(6) 0.1238(3) 0.0183(15) Uani 1 1 d . . . . .
C11 C 0.5025(5) 0.6286(6) 0.0941(3) 0.0149(14) Uani 1 1 d . . . . .
H11 H 0.521141 0.713081 0.111757 0.018 Uiso 1 1 calc R U . . .
C12 C 0.6026(5) 0.5386(6) 0.0872(2) 0.0142(13) Uani 1 1 d . . . . .
H12 H 0.671776 0.590340 0.090701 0.017 Uiso 1 1 calc R U . . .
C13 C 0.5100(5) 0.3735(6) 0.1401(3) 0.0164(14) Uani 1 1 d . . . . .
H13 H 0.510804 0.288561 0.155057 0.020 Uiso 1 1 calc R U . . .
C14 C 0.4157(5) 0.4374(6) 0.1376(3) 0.0189(14) Uani 1 1 d . . . . .
H14 H 0.351088 0.394922 0.149780 0.023 Uiso 1 1 calc R U . . .
C15 C 0.7059(5) 0.3617(6) 0.1320(3) 0.0166(15) Uani 1 1 d . . . . .
C16 C 0.8091(5) 0.4169(6) 0.1101(3) 0.0188(15) Uani 1 1 d . . . . .
H16A H 0.871234 0.362110 0.120806 0.028 Uiso 1 1 calc R U . . .
H16B H 0.819665 0.505031 0.124124 0.028 Uiso 1 1 calc R U . . .
H16C H 0.804714 0.420000 0.070833 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5110(5) 0.0696(6) 0.2313(3) 0.0262(17) Uani 1 1 d . . . . .
H17A H 0.571704 0.131834 0.228735 0.039 Uiso 1 1 calc R U . . .
H17B H 0.495364 0.033642 0.195705 0.039 Uiso 1 1 calc R U . . .
H17C H 0.531477 -0.001050 0.255774 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4099(5) 0.1378(6) 0.2525(3) 0.0183(15) Uani 1 1 d . . . . .
C19 C 0.3064(5) -0.0641(6) 0.2385(3) 0.0170(14) Uani 1 1 d . . . . .
H19 H 0.370658 -0.107636 0.226505 0.020 Uiso 1 1 calc R U . . .
C20 C 0.2123(5) -0.1264(6) 0.2363(3) 0.0193(15) Uani 1 1 d . . . . .
H20 H 0.211777 -0.211053 0.221097 0.023 Uiso 1 1 calc R U . . .
C21 C 0.1206(5) 0.0381(6) 0.2895(3) 0.0185(15) Uani 1 1 d . . . . .
H21 H 0.051774 0.090674 0.286448 0.022 Uiso 1 1 calc R U . . .
C22 C 0.2216(5) 0.1274(6) 0.2813(3) 0.0166(15) Uani 1 1 d . . . . .
H22 H 0.203110 0.211662 0.263388 0.020 Uiso 1 1 calc R U . . .
C23 C 0.0178(5) -0.1405(7) 0.2436(3) 0.0183(15) Uani 1 1 d . . . . .
C24 C -0.0861(5) -0.0844(7) 0.2668(3) 0.0224(16) Uani 1 1 d . . . . .
H24A H -0.148430 -0.139887 0.256988 0.034 Uiso 1 1 calc R U . . .
H24B H -0.097669 0.003239 0.252428 0.034 Uiso 1 1 calc R U . . .
H24C H -0.079876 -0.080212 0.305936 0.034 Uiso 1 1 calc R U . . .
C25 C 0.1965(6) -0.3337(7) 0.3832(3) 0.0291(18) Uani 1 1 d . . . . .
H25A H 0.141022 -0.401284 0.389014 0.044 Uiso 1 1 calc R U . . .
H25B H 0.241760 -0.324599 0.415467 0.044 Uiso 1 1 calc R U . . .
H25C H 0.243183 -0.358106 0.352753 0.044 Uiso 1 1 calc R U . . .
C26 C 0.1417(5) -0.2092(6) 0.3715(3) 0.0169(14) Uani 1 1 d . . . . .
C27 C 0.1514(5) 0.0206(5) 0.3502(2) 0.0157(13) Uani 1 1 d . . . . .
H27 H 0.088107 0.037850 0.374804 0.019 Uiso 1 1 calc R U . . .
C28 C 0.2270(5) 0.1380(6) 0.3440(3) 0.0169(14) Uani 1 1 d . . . . .
H28 H 0.188130 0.218525 0.356147 0.020 Uiso 1 1 calc R U . . .
C29 C 0.3811(5) 0.0062(6) 0.3735(3) 0.0198(14) Uani 1 1 d . . . . .
H29 H 0.458012 -0.001627 0.379019 0.024 Uiso 1 1 calc R U . . .
C30 C 0.3211(5) -0.1000(6) 0.3705(3) 0.0200(15) Uani 1 1 d . . . . .
H30 H 0.357753 -0.181121 0.374023 0.024 Uiso 1 1 calc R U . . .
C31 C 0.3984(6) 0.2368(7) 0.3803(3) 0.0222(16) Uani 1 1 d . . . . .
C32 C 0.3430(6) 0.3680(6) 0.3760(3) 0.0252(17) Uani 1 1 d . . . . .
H32A H 0.285651 0.374907 0.403493 0.038 Uiso 1 1 calc R U . . .
H32B H 0.309933 0.377236 0.340382 0.038 Uiso 1 1 calc R U . . .
H32C H 0.397446 0.436938 0.381476 0.038 Uiso 1 1 calc R U . . .


_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
O1 C2 1.241(8) . ?
O2 C7 1.234(9) . ?
O3 C10 1.230(8) . ?
O4 C15 1.240(8) . ?
O5 C18 1.215(8) . ?
O6 C23 1.226(8) . ?
O7 C26 1.222(7) . ?
O8 C31 1.209(8) . ?
N1 C2 1.357(8) . ?
N1 C6 1.420(7) . ?
N1 C3 1.458(8) . ?
N2 C7 1.380(9) . ?
N2 C5 1.411(8) . ?
N2 C4 1.420(8) . ?
N3 C10 1.368(8) . ?
N3 C14 1.403(8) . ?
N3 C11 1.466(8) . ?
N4 C13 1.391(8) . ?
N4 C15 1.392(8) . ?
N4 C12 1.434(7) . ?
N5 C18 1.380(8) . ?
N5 C19 1.399(8) . ?
N5 C22 1.454(8) . ?
N6 C23 1.363(8) . ?
N6 C20 1.399(8) . ?
N6 C21 1.455(8) . ?
N7 C26 1.381(8) . ?
N7 C30 1.395(7) . ?
N7 C27 1.470(7) . ?
N8 C31 1.365(9) . ?
N8 C29 1.407(7) . ?
N8 C28 1.453(8) . ?
C1 C2 1.499(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.554(8) . ?
C3 C12 1.578(9) . ?
C3 H3 1.0000 . ?
C4 C11 1.581(9) . ?
C4 H4 1.0000 . ?
C5 C6 1.316(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.507(10) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.485(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.540(8) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.325(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.483(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.512(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 C20 1.314(9) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.549(9) . ?
C21 C27 1.570(9) . ?
C21 H21 1.0000 . ?
C22 C28 1.569(9) . ?
C22 H22 1.0000 . ?
C23 C24 1.505(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.472(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C27 C28 1.526(8) . ?
C27 H27 1.0000 . ?
C28 H28 1.0000 . ?
C29 C30 1.316(8) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.513(9) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C2 N1 C6 122.8(5) . . ?
C2 N1 C3 116.4(5) . . ?
C6 N1 C3 120.5(5) . . ?
C7 N2 C5 119.9(6) . . ?
C7 N2 C4 122.4(5) . . ?
C5 N2 C4 116.7(5) . . ?
C10 N3 C14 122.1(5) . . ?
C10 N3 C11 118.0(5) . . ?
C14 N3 C11 119.7(5) . . ?
C13 N4 C15 118.9(5) . . ?
C13 N4 C12 118.3(5) . . ?
C15 N4 C12 122.5(5) . . ?
C18 N5 C19 124.1(5) . . ?
C18 N5 C22 116.1(5) . . ?
C19 N5 C22 119.6(5) . . ?
C23 N6 C20 118.9(6) . . ?
C23 N6 C21 124.9(5) . . ?
C20 N6 C21 116.0(5) . . ?
C26 N7 C30 124.5(5) . . ?
C26 N7 C27 116.5(5) . . ?
C30 N7 C27 118.5(5) . . ?
C31 N8 C29 118.8(6) . . ?
C31 N8 C28 124.3(5) . . ?
C29 N8 C28 116.2(5) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 120.4(6) . . ?
O1 C2 C1 121.8(6) . . ?
N1 C2 C1 117.8(6) . . ?
N1 C3 C4 113.9(5) . . ?
N1 C3 C12 113.6(5) . . ?
C4 C3 C12 88.2(5) . . ?
N1 C3 H3 113.0 . . ?
C4 C3 H3 113.0 . . ?
C12 C3 H3 113.0 . . ?
N2 C4 C3 117.7(5) . . ?
N2 C4 C11 118.5(5) . . ?
C3 C4 C11 89.4(5) . . ?
N2 C4 H4 109.9 . . ?
C3 C4 H4 109.9 . . ?
C11 C4 H4 109.9 . . ?
C6 C5 N2 124.1(6) . . ?
C6 C5 H5 117.9 . . ?
N2 C5 H5 117.9 . . ?
C5 C6 N1 121.3(6) . . ?
C5 C6 H6 119.3 . . ?
N1 C6 H6 119.3 . . ?
O2 C7 N2 120.5(6) . . ?
O2 C7 C8 122.9(6) . . ?
N2 C7 C8 116.6(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N3 118.6(6) . . ?
O3 C10 C9 122.6(6) . . ?
N3 C10 C9 118.8(6) . . ?
N3 C11 C12 114.1(5) . . ?
N3 C11 C4 112.9(5) . . ?
C12 C11 C4 88.6(5) . . ?
N3 C11 H11 113.0 . . ?
C12 C11 H11 113.0 . . ?
C4 C11 H11 113.0 . . ?
N4 C12 C11 116.9(5) . . ?
N4 C12 C3 119.1(5) . . ?
C11 C12 C3 90.0(4) . . ?
N4 C12 H12 109.8 . . ?
C11 C12 H12 109.8 . . ?
C3 C12 H12 109.8 . . ?
C14 C13 N4 122.2(6) . . ?
C14 C13 H13 118.9 . . ?
N4 C13 H13 118.9 . . ?
C13 C14 N3 123.3(6) . . ?
C13 C14 H14 118.4 . . ?
N3 C14 H14 118.4 . . ?
O4 C15 N4 120.1(6) . . ?
O4 C15 C16 121.7(6) . . ?
N4 C15 C16 118.2(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 N5 121.8(6) . . ?
O5 C18 C17 121.7(6) . . ?
N5 C18 C17 116.5(6) . . ?
C20 C19 N5 123.1(6) . . ?
C20 C19 H19 118.4 . . ?
N5 C19 H19 118.4 . . ?
C19 C20 N6 124.1(6) . . ?
C19 C20 H20 117.9 . . ?
N6 C20 H20 117.9 . . ?
N6 C21 C22 116.9(5) . . ?
N6 C21 C27 119.4(5) . . ?
C22 C21 C27 90.3(5) . . ?
N6 C21 H21 109.6 . . ?
C22 C21 H21 109.6 . . ?
C27 C21 H21 109.6 . . ?
N5 C22 C21 114.5(5) . . ?
N5 C22 C28 113.6(5) . . ?
C21 C22 C28 86.7(5) . . ?
N5 C22 H22 113.2 . . ?
C21 C22 H22 113.2 . . ?
C28 C22 H22 113.2 . . ?
O6 C23 N6 120.3(6) . . ?
O6 C23 C24 123.2(6) . . ?
N6 C23 C24 116.5(6) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O7 C26 N7 120.1(6) . . ?
O7 C26 C25 122.5(6) . . ?
N7 C26 C25 117.4(6) . . ?
N7 C27 C28 114.8(5) . . ?
N7 C27 C21 114.2(5) . . ?
C28 C27 C21 87.4(5) . . ?
N7 C27 H27 112.7 . . ?
C28 C27 H27 112.7 . . ?
C21 C27 H27 112.7 . . ?
N8 C28 C27 117.6(5) . . ?
N8 C28 C22 117.2(5) . . ?
C27 C28 C22 91.2(5) . . ?
N8 C28 H28 109.8 . . ?
C27 C28 H28 109.8 . . ?
C22 C28 H28 109.8 . . ?
C30 C29 N8 122.0(6) . . ?
C30 C29 H29 119.0 . . ?
N8 C29 H29 119.0 . . ?
C29 C30 N7 124.8(6) . . ?
C29 C30 H30 117.6 . . ?
N7 C30 H30 117.6 . . ?
O8 C31 N8 122.7(6) . . ?
O8 C31 C32 121.1(6) . . ?
N8 C31 C32 116.2(6) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 O1 171.1(6) . . . . ?
C3 N1 C2 O1 -2.7(9) . . . . ?
C6 N1 C2 C1 -8.2(10) . . . . ?
C3 N1 C2 C1 178.1(6) . . . . ?
C2 N1 C3 C4 177.1(6) . . . . ?
C6 N1 C3 C4 3.2(8) . . . . ?
C2 N1 C3 C12 -83.9(7) . . . . ?
C6 N1 C3 C12 102.2(6) . . . . ?
C7 N2 C4 C3 -162.9(6) . . . . ?
C5 N2 C4 C3 28.4(8) . . . . ?
C7 N2 C4 C11 91.3(8) . . . . ?
C5 N2 C4 C11 -77.3(8) . . . . ?
N1 C3 C4 N2 -21.6(8) . . . . ?
C12 C3 C4 N2 -136.7(6) . . . . ?
N1 C3 C4 C11 100.7(6) . . . . ?
C12 C3 C4 C11 -14.5(5) . . . . ?
C7 N2 C5 C6 173.7(7) . . . . ?
C4 N2 C5 C6 -17.4(10) . . . . ?
N2 C5 C6 N1 -1.8(11) . . . . ?
C2 N1 C6 C5 -165.0(7) . . . . ?
C3 N1 C6 C5 8.5(9) . . . . ?
C5 N2 C7 O2 2.2(10) . . . . ?
C4 N2 C7 O2 -166.2(6) . . . . ?
C5 N2 C7 C8 -178.2(6) . . . . ?
C4 N2 C7 C8 13.4(10) . . . . ?
C14 N3 C10 O3 171.6(6) . . . . ?
C11 N3 C10 O3 -3.6(9) . . . . ?
C14 N3 C10 C9 -8.9(9) . . . . ?
C11 N3 C10 C9 175.9(6) . . . . ?
C10 N3 C11 C12 -177.6(5) . . . . ?
C14 N3 C11 C12 7.0(8) . . . . ?
C10 N3 C11 C4 -78.5(7) . . . . ?
C14 N3 C11 C4 106.1(7) . . . . ?
N2 C4 C11 N3 20.7(8) . . . . ?
C3 C4 C11 N3 -100.8(5) . . . . ?
N2 C4 C11 C12 136.3(5) . . . . ?
C3 C4 C11 C12 14.8(5) . . . . ?
C13 N4 C12 C11 27.7(8) . . . . ?
C15 N4 C12 C11 -158.9(5) . . . . ?
C13 N4 C12 C3 -78.8(7) . . . . ?
C15 N4 C12 C3 94.5(7) . . . . ?
N3 C11 C12 N4 -23.2(7) . . . . ?
C4 C11 C12 N4 -137.7(5) . . . . ?
N3 C11 C12 C3 99.9(6) . . . . ?
C4 C11 C12 C3 -14.6(5) . . . . ?
N1 C3 C12 N4 20.7(8) . . . . ?
C4 C3 C12 N4 136.1(5) . . . . ?
N1 C3 C12 C11 -100.5(5) . . . . ?
C4 C3 C12 C11 14.9(5) . . . . ?
C15 N4 C13 C14 171.1(6) . . . . ?
C12 N4 C13 C14 -15.3(9) . . . . ?
N4 C13 C14 N3 -2.3(11) . . . . ?
C10 N3 C14 C13 -169.3(7) . . . . ?
C11 N3 C14 C13 5.9(10) . . . . ?
C13 N4 C15 O4 -3.6(9) . . . . ?
C12 N4 C15 O4 -177.0(6) . . . . ?
C13 N4 C15 C16 177.8(6) . . . . ?
C12 N4 C15 C16 4.4(9) . . . . ?
C19 N5 C18 O5 171.5(6) . . . . ?
C22 N5 C18 O5 -3.8(9) . . . . ?
C19 N5 C18 C17 -8.4(9) . . . . ?
C22 N5 C18 C17 176.3(6) . . . . ?
C18 N5 C19 C20 -169.1(7) . . . . ?
C22 N5 C19 C20 6.0(10) . . . . ?
N5 C19 C20 N6 -3.1(11) . . . . ?
C23 N6 C20 C19 170.4(7) . . . . ?
C21 N6 C20 C19 -14.5(10) . . . . ?
C23 N6 C21 C22 -157.6(6) . . . . ?
C20 N6 C21 C22 27.6(8) . . . . ?
C23 N6 C21 C27 95.4(8) . . . . ?
C20 N6 C21 C27 -79.4(7) . . . . ?
C18 N5 C22 C21 -176.6(5) . . . . ?
C19 N5 C22 C21 7.9(8) . . . . ?
C18 N5 C22 C28 -79.1(7) . . . . ?
C19 N5 C22 C28 105.4(6) . . . . ?
N6 C21 C22 N5 -24.5(8) . . . . ?
C27 C21 C22 N5 99.2(6) . . . . ?
N6 C21 C22 C28 -139.0(6) . . . . ?
C27 C21 C22 C28 -15.4(4) . . . . ?
C20 N6 C23 O6 -1.9(10) . . . . ?
C21 N6 C23 O6 -176.5(6) . . . . ?
C20 N6 C23 C24 177.5(6) . . . . ?
C21 N6 C23 C24 2.9(9) . . . . ?
C30 N7 C26 O7 171.9(6) . . . . ?
C27 N7 C26 O7 0.2(9) . . . . ?
C30 N7 C26 C25 -9.0(10) . . . . ?
C27 N7 C26 C25 179.3(6) . . . . ?
C26 N7 C27 C28 176.2(5) . . . . ?
C30 N7 C27 C28 4.0(8) . . . . ?
C26 N7 C27 C21 -85.0(7) . . . . ?
C30 N7 C27 C21 102.8(6) . . . . ?
N6 C21 C27 N7 21.1(8) . . . . ?
C22 C21 C27 N7 -100.3(5) . . . . ?
N6 C21 C27 C28 137.3(5) . . . . ?
C22 C21 C27 C28 15.8(5) . . . . ?
C31 N8 C28 C27 -160.4(6) . . . . ?
C29 N8 C28 C27 29.2(8) . . . . ?
C31 N8 C28 C22 92.4(8) . . . . ?
C29 N8 C28 C22 -78.0(7) . . . . ?
N7 C27 C28 N8 -21.9(8) . . . . ?
C21 C27 C28 N8 -137.4(6) . . . . ?
N7 C27 C28 C22 99.9(6) . . . . ?
C21 C27 C28 C22 -15.6(5) . . . . ?
N5 C22 C28 N8 22.6(8) . . . . ?
C21 C22 C28 N8 138.0(5) . . . . ?
N5 C22 C28 C27 -99.5(5) . . . . ?
C21 C22 C28 C27 15.8(5) . . . . ?
C31 N8 C29 C30 170.3(6) . . . . ?
C28 N8 C29 C30 -18.9(10) . . . . ?
N8 C29 C30 N7 0.1(11) . . . . ?
C26 N7 C30 C29 -164.2(7) . . . . ?
C27 N7 C30 C29 7.4(10) . . . . ?
C29 N8 C31 O8 0.1(10) . . . . ?
C28 N8 C31 O8 -170.0(7) . . . . ?
C29 N8 C31 C32 -178.3(6) . . . . ?
C28 N8 C31 C32 11.6(10) . . . . ?

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.100

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1816607'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N4 O2 S'
_chemical_formula_weight         270.35

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.286(3)
_cell_length_b                   10.958(2)
_cell_length_c                   16.735(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.88(3)
_cell_angle_gamma                90
_cell_volume                     2801.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5236
_cell_measurement_theta_min      2.2219
_cell_measurement_theta_max      27.8824

_exptl_crystal_description       Orthorhombic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   0.5950
_exptl_transmission_factor_max   0.7453
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28188
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.333
_diffrn_reflns_theta_max         27.928
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6684
_reflns_number_gt                4224
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0752P)²] 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-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0137(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6684
_refine_ls_number_parameters     358
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74472(3) 0.20141(6) 0.04866(4) 0.05159(19) Uani 1 1 d . . . . .
S2 S 0.80875(3) 0.29680(6) 0.29814(4) 0.04887(19) Uani 1 1 d . . . . .
O1 O 0.06609(10) 0.27192(17) 0.40068(11) 0.0650(5) Uani 1 1 d . . . . .
O2 O 0.45882(9) 0.33673(15) 0.33746(11) 0.0579(5) Uani 1 1 d . . . . .
O3 O 0.08674(10) 0.27677(16) 0.11898(12) 0.0639(5) Uani 1 1 d . . . . .
O4 O 0.48427(9) 0.33416(15) 0.13063(11) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.16476(10) 0.22291(15) 0.30712(11) 0.0416(4) Uani 1 1 d . . . . .
N2 N 0.33640(10) 0.25089(15) 0.28056(11) 0.0423(4) Uani 1 1 d . . . . .
N3 N 0.20628(10) 0.23535(15) 0.04701(11) 0.0427(4) Uani 1 1 d . . . . .
N4 N 0.38064(10) 0.26532(16) 0.04191(11) 0.0436(4) Uani 1 1 d . . . . .
N5 N 0.89826(12) 0.2503(2) 0.11860(12) 0.0535(5) Uani 1 1 d D . . . .
H5A H 0.9566(6) 0.262(2) 0.1232(13) 0.064 Uiso 1 1 d D U . . .
H5B H 0.8711(12) 0.253(2) 0.1651(9) 0.064 Uiso 1 1 d D U . . .
N6 N 0.89811(11) 0.23050(19) -0.01640(11) 0.0505(5) Uani 1 1 d D . . . .
H6A H 0.8718(11) 0.220(2) -0.0643(8) 0.061 Uiso 1 1 d D U . . .
H6B H 0.9570(6) 0.241(2) -0.0190(12) 0.061 Uiso 1 1 d D U . . .
N7 N 0.65255(12) 0.3402(2) 0.35473(13) 0.0597(6) Uani 1 1 d D . . . .
H7A H 0.5940(6) 0.338(2) 0.3521(13) 0.072 Uiso 1 1 d D U . . .
H7B H 0.6776(12) 0.340(2) 0.4034(8) 0.072 Uiso 1 1 d D U . . .
N8 N 0.65690(12) 0.31584(19) 0.21985(12) 0.0510(5) Uani 1 1 d D . . . .
H8A H 0.5998(6) 0.325(2) 0.2127(12) 0.061 Uiso 1 1 d D U . . .
H8B H 0.6879(11) 0.300(2) 0.1768(9) 0.061 Uiso 1 1 d D U . . .
C1 C 0.05273(18) 0.0737(3) 0.3431(2) 0.0884(10) Uani 1 1 d . . . . .
H1A H 0.004318 0.066564 0.377915 0.133 Uiso 1 1 calc R U . . .
H1B H 0.095171 0.011622 0.356110 0.133 Uiso 1 1 calc R U . . .
H1C H 0.032254 0.063955 0.288630 0.133 Uiso 1 1 calc R U . . .
C2 C 0.09413(14) 0.1972(2) 0.35351(15) 0.0523(6) Uani 1 1 d . . . . .
C3 C 0.20851(14) 0.13218(19) 0.26500(14) 0.0488(5) Uani 1 1 d . . . . .
H3 H 0.178648 0.062905 0.247145 0.059 Uiso 1 1 calc R U . . .
C4 C 0.29202(14) 0.14567(19) 0.25089(14) 0.0487(6) Uani 1 1 d . . . . .
H4 H 0.321584 0.087158 0.221910 0.058 Uiso 1 1 calc R U . . .
C5 C 0.28262(12) 0.35894(17) 0.28313(13) 0.0386(5) Uani 1 1 d . . . . .
C6 C 0.19786(12) 0.34486(18) 0.29743(13) 0.0391(5) Uani 1 1 d . . . . .
C7 C 0.13246(14) 0.4466(2) 0.29258(16) 0.0574(6) Uani 1 1 d . . . . .
H7D H 0.122433 0.476807 0.345340 0.086 Uiso 1 1 calc R U . . .
H7E H 0.078448 0.416883 0.269029 0.086 Uiso 1 1 calc R U . . .
H7C H 0.154587 0.511294 0.260259 0.086 Uiso 1 1 calc R U . . .
C8 C 0.32322(14) 0.47716(19) 0.25876(15) 0.0548(6) Uani 1 1 d . . . . .
H8D H 0.281441 0.523597 0.227310 0.082 Uiso 1 1 calc R U . . .
H8E H 0.373628 0.460867 0.227719 0.082 Uiso 1 1 calc R U . . .
H8C H 0.340606 0.522750 0.305624 0.082 Uiso 1 1 calc R U . . .
C9 C 0.42200(14) 0.2472(2) 0.30756(14) 0.0478(6) Uani 1 1 d . . . . .
C10 C 0.46836(15) 0.1276(2) 0.30025(18) 0.0690(8) Uani 1 1 d . . . . .
H10A H 0.527677 0.135829 0.320186 0.103 Uiso 1 1 calc R U . . .
H10B H 0.468152 0.103422 0.245103 0.103 Uiso 1 1 calc R U . . .
H10C H 0.438993 0.066767 0.330776 0.103 Uiso 1 1 calc R U . . .
C11 C 0.09896(15) 0.0742(2) 0.06897(17) 0.0615(7) Uani 1 1 d . . . . .
H11A H 0.045898 0.061520 0.096961 0.092 Uiso 1 1 calc R U . . .
H11B H 0.143272 0.019332 0.089392 0.092 Uiso 1 1 calc R U . . .
H11C H 0.088381 0.059005 0.012980 0.092 Uiso 1 1 calc R U . . .
C12 C 0.12906(13) 0.2029(2) 0.08074(15) 0.0473(6) Uani 1 1 d . . . . .
C13 C 0.25610(14) 0.1506(2) 0.00403(15) 0.0500(6) Uani 1 1 d . . . . .
H13 H 0.228884 0.085009 -0.021789 0.060 Uiso 1 1 calc R U . . .
C14 C 0.34101(14) 0.1653(2) 0.00086(14) 0.0504(6) Uani 1 1 d . . . . .
H14 H 0.374709 0.111041 -0.027806 0.060 Uiso 1 1 calc R U . . .
C15 C 0.32699(13) 0.37236(19) 0.04518(14) 0.0441(5) Uani 1 1 d . . . . .
C16 C 0.24028(13) 0.35815(19) 0.04829(14) 0.0433(5) Uani 1 1 d . . . . .
C17 C 0.17718(14) 0.4630(2) 0.04214(19) 0.0702(8) Uani 1 1 d . . . . .
H17A H 0.166972 0.494181 0.094619 0.105 Uiso 1 1 calc R U . . .
H17B H 0.122880 0.435464 0.017949 0.105 Uiso 1 1 calc R U . . .
H17C H 0.201344 0.526285 0.009925 0.105 Uiso 1 1 calc R U . . .
C18 C 0.37130(15) 0.4928(2) 0.03148(18) 0.0674(8) Uani 1 1 d . . . . .
H18A H 0.338605 0.538159 -0.008485 0.101 Uiso 1 1 calc R U . . .
H18B H 0.429518 0.478832 0.013687 0.101 Uiso 1 1 calc R U . . .
H18C H 0.374043 0.538414 0.080494 0.101 Uiso 1 1 calc R U . . .
C19 C 0.45872(13) 0.2551(2) 0.08369(15) 0.0472(5) Uani 1 1 d . . . . .
C20 C 0.51154(15) 0.1420(2) 0.06887(18) 0.0676(8) Uani 1 1 d . . . . .
H20A H 0.567079 0.148024 0.097082 0.101 Uiso 1 1 calc R U . . .
H20B H 0.520697 0.134028 0.012631 0.101 Uiso 1 1 calc R U . . .
H20C H 0.480566 0.071851 0.087423 0.101 Uiso 1 1 calc R U . . .
C21 C 0.85419(13) 0.22945(17) 0.05009(13) 0.0384(5) Uani 1 1 d . . . . .
C22 C 0.69912(13) 0.31774(18) 0.29050(14) 0.0412(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C21 1.701(2) . ?
S2 C22 1.692(2) . ?
O1 C2 1.224(3) . ?
O2 C9 1.229(3) . ?
O3 C12 1.229(3) . ?
O4 C19 1.225(3) . ?
N1 C2 1.379(3) . ?
N1 C3 1.401(3) . ?
N1 C6 1.440(3) . ?
N2 C9 1.371(3) . ?
N2 C4 1.419(3) . ?
N2 C5 1.443(2) . ?
N3 C12 1.372(3) . ?
N3 C13 1.413(3) . ?
N3 C16 1.442(3) . ?
N4 C19 1.368(3) . ?
N4 C14 1.419(3) . ?
N4 C15 1.433(3) . ?
N5 C21 1.330(3) . ?
N5 H5A 0.901(9) . ?
N5 H5B 0.895(9) . ?
N6 C21 1.318(3) . ?
N6 H6A 0.892(9) . ?
N6 H6B 0.909(9) . ?
N7 C22 1.331(3) . ?
N7 H7A 0.894(9) . ?
N7 H7B 0.888(9) . ?
N8 C22 1.328(3) . ?
N8 H8A 0.883(9) . ?
N8 H8B 0.893(9) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.314(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.334(3) . ?
C5 C8 1.499(3) . ?
C6 C7 1.498(3) . ?
C7 H7D 0.9600 . ?
C7 H7E 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8D 0.9600 . ?
C8 H8E 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.497(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.495(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.311(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.337(3) . ?
C15 C18 1.505(3) . ?
C16 C17 1.501(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.504(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 122.25(19) . . ?
C2 N1 C6 122.50(18) . . ?
C3 N1 C6 115.24(17) . . ?
C9 N2 C4 122.10(17) . . ?
C9 N2 C5 123.58(17) . . ?
C4 N2 C5 114.26(16) . . ?
C12 N3 C13 121.65(18) . . ?
C12 N3 C16 123.38(18) . . ?
C13 N3 C16 114.88(17) . . ?
C19 N4 C14 122.38(18) . . ?
C19 N4 C15 122.58(18) . . ?
C14 N4 C15 114.52(17) . . ?
C21 N5 H5A 124.6(14) . . ?
C21 N5 H5B 121.2(14) . . ?
H5A N5 H5B 114.2(14) . . ?
C21 N6 H6A 122.0(13) . . ?
C21 N6 H6B 125.0(13) . . ?
H6A N6 H6B 113.0(14) . . ?
C22 N7 H7A 121.1(14) . . ?
C22 N7 H7B 121.0(15) . . ?
H7A N7 H7B 116.4(15) . . ?
C22 N8 H8A 124.7(14) . . ?
C22 N8 H8B 117.8(14) . . ?
H8A N8 H8B 117.4(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 121.6(2) . . ?
O1 C2 C1 121.5(2) . . ?
N1 C2 C1 117.0(2) . . ?
C4 C3 N1 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
N1 C3 H3 120.2 . . ?
C3 C4 N2 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
N2 C4 H4 120.5 . . ?
C6 C5 N2 117.91(18) . . ?
C6 C5 C8 124.19(18) . . ?
N2 C5 C8 117.37(17) . . ?
C5 C6 N1 118.32(17) . . ?
C5 C6 C7 123.68(19) . . ?
N1 C6 C7 117.41(17) . . ?
C6 C7 H7D 109.5 . . ?
C6 C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7D C7 H7C 109.5 . . ?
H7E C7 H7C 109.5 . . ?
C5 C8 H8D 109.5 . . ?
C5 C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8D C8 H8C 109.5 . . ?
H8E C8 H8C 109.5 . . ?
O2 C9 N2 122.0(2) . . ?
O2 C9 C10 121.4(2) . . ?
N2 C9 C10 116.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N3 121.2(2) . . ?
O3 C12 C11 121.7(2) . . ?
N3 C12 C11 117.1(2) . . ?
C14 C13 N3 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
N3 C13 H13 120.3 . . ?
C13 C14 N4 118.9(2) . . ?
C13 C14 H14 120.6 . . ?
N4 C14 H14 120.6 . . ?
C16 C15 N4 118.38(18) . . ?
C16 C15 C18 124.04(19) . . ?
N4 C15 C18 116.82(18) . . ?
C15 C16 N3 117.72(18) . . ?
C15 C16 C17 122.9(2) . . ?
N3 C16 C17 118.84(17) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 N4 121.6(2) . . ?
O4 C19 C20 121.8(2) . . ?
N4 C19 C20 116.6(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N6 C21 N5 117.94(18) . . ?
N6 C21 S1 121.18(17) . . ?
N5 C21 S1 120.88(16) . . ?
N8 C22 N7 117.67(19) . . ?
N8 C22 S2 121.07(17) . . ?
N7 C22 S2 121.23(17) . . ?

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
C3 N1 C2 O1 167.1(2) . . . . ?
C6 N1 C2 O1 -14.0(3) . . . . ?
C3 N1 C2 C1 -13.4(3) . . . . ?
C6 N1 C2 C1 165.6(2) . . . . ?
C2 N1 C3 C4 -151.1(2) . . . . ?
C6 N1 C3 C4 29.9(3) . . . . ?
N1 C3 C4 N2 1.5(3) . . . . ?
C9 N2 C4 C3 144.4(2) . . . . ?
C5 N2 C4 C3 -32.9(3) . . . . ?
C9 N2 C5 C6 -144.7(2) . . . . ?
C4 N2 C5 C6 32.5(3) . . . . ?
C9 N2 C5 C8 43.3(3) . . . . ?
C4 N2 C5 C8 -139.5(2) . . . . ?
N2 C5 C6 N1 -1.7(3) . . . . ?
C8 C5 C6 N1 169.7(2) . . . . ?
N2 C5 C6 C7 -172.8(2) . . . . ?
C8 C5 C6 C7 -1.3(4) . . . . ?
C2 N1 C6 C5 151.5(2) . . . . ?
C3 N1 C6 C5 -29.5(3) . . . . ?
C2 N1 C6 C7 -36.9(3) . . . . ?
C3 N1 C6 C7 142.1(2) . . . . ?
C4 N2 C9 O2 -175.8(2) . . . . ?
C5 N2 C9 O2 1.2(3) . . . . ?
C4 N2 C9 C10 3.2(3) . . . . ?
C5 N2 C9 C10 -179.9(2) . . . . ?
C13 N3 C12 O3 179.0(2) . . . . ?
C16 N3 C12 O3 -4.8(3) . . . . ?
C13 N3 C12 C11 -1.0(3) . . . . ?
C16 N3 C12 C11 175.3(2) . . . . ?
C12 N3 C13 C14 -152.4(2) . . . . ?
C16 N3 C13 C14 31.0(3) . . . . ?
N3 C13 C14 N4 0.9(3) . . . . ?
C19 N4 C14 C13 139.1(2) . . . . ?
C15 N4 C14 C13 -32.7(3) . . . . ?
C19 N4 C15 C16 -139.5(2) . . . . ?
C14 N4 C15 C16 32.3(3) . . . . ?
C19 N4 C15 C18 50.1(3) . . . . ?
C14 N4 C15 C18 -138.1(2) . . . . ?
N4 C15 C16 N3 -0.8(3) . . . . ?
C18 C15 C16 N3 168.8(2) . . . . ?
N4 C15 C16 C17 -172.6(2) . . . . ?
C18 C15 C16 C17 -2.9(4) . . . . ?
C12 N3 C16 C15 152.8(2) . . . . ?
C13 N3 C16 C15 -30.7(3) . . . . ?
C12 N3 C16 C17 -35.1(3) . . . . ?
C13 N3 C16 C17 141.4(2) . . . . ?
C14 N4 C19 O4 -166.2(2) . . . . ?
C15 N4 C19 O4 5.0(3) . . . . ?
C14 N4 C19 C20 13.9(3) . . . . ?
C15 N4 C19 C20 -174.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5A O3 0.901(9) 1.999(9) 2.895(2) 172(2) 1_655 yes
N6 H6A S2 0.892(9) 2.474(10) 3.363(2) 175.0(19) 4_565 yes
N6 H6B O1 0.909(9) 2.181(16) 2.959(2) 143.1(17) 4_665 yes
N7 H7B S1 0.888(9) 2.647(11) 3.525(2) 170(2) 4_566 yes
N5 H5B S2 0.895(9) 2.497(11) 3.381(2) 170(2) . yes
N8 H8A O4 0.883(9) 2.203(15) 2.995(2) 149.2(18) . yes
N7 H7A O2 0.894(9) 2.074(9) 2.966(2) 176(2) . yes
N8 H8B S1 0.893(9) 2.576(12) 3.440(2) 163.1(19) . yes

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049

