# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1823979'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N4 O5 S'
_chemical_formula_sum            'C18 H20 N4 O5 S'
_chemical_formula_weight         404.44

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1334(13)
_cell_length_b                   9.0145(15)
_cell_length_c                   14.731(2)
_cell_angle_alpha                94.156(5)
_cell_angle_beta                 102.111(4)
_cell_angle_gamma                102.813(5)
_cell_volume                     1021.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2751
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9308
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             4507
_reflns_number_gt                2315
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1800P)²+1.4713P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4507
_refine_ls_number_parameters     255
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1910
_refine_ls_R_factor_gt           0.1093
_refine_ls_wR_factor_ref         0.3491
_refine_ls_wR_factor_gt          0.3032
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.5403(8) 0.5771(7) 0.7534(4) 0.0619(17) Uani 1 1 d . . . . .
H1 H 0.4945 0.6226 0.7025 0.074 Uiso 1 1 calc R U . . .
C2 C 0.5902(11) 0.6580(9) 0.8388(5) 0.085(2) Uani 1 1 d . . . . .
H2 H 0.5765 0.7576 0.8461 0.103 Uiso 1 1 calc R U . . .
C3 C 0.6628(9) 0.5945(8) 0.9173(4) 0.0706(18) Uani 1 1 d . . . . .
C4 C 0.7865(14) 0.6241(13) 1.0812(5) 0.117(3) Uani 1 1 d . . . . .
H4A H 0.7026 0.5387 1.0927 0.175 Uiso 1 1 calc R U . . .
H4B H 0.8217 0.7014 1.1346 0.175 Uiso 1 1 calc R U . . .
H4C H 0.8857 0.5904 1.0706 0.175 Uiso 1 1 calc R U . . .
C5 C 0.6801(9) 0.4482(8) 0.9059(4) 0.0660(18) Uani 1 1 d . . . . .
H5 H 0.7281 0.4040 0.9569 0.079 Uiso 1 1 calc R U . . .
C6 C 0.6248(7) 0.3648(7) 0.8164(4) 0.0532(14) Uani 1 1 d . . . . .
H6 H 0.6352 0.2642 0.8088 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5552(6) 0.4280(6) 0.7393(3) 0.0425(12) Uani 1 1 d . . . . .
C8 C 0.5000(6) 0.3429(6) 0.6410(3) 0.0405(12) Uani 1 1 d . . . . .
H8 H 0.5404 0.4130 0.5981 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5668(6) 0.2022(6) 0.6295(3) 0.0404(12) Uani 1 1 d . . . . .
C10 C 0.7446(7) 0.2139(7) 0.6306(4) 0.0480(13) Uani 1 1 d . . . . .
C11 C 0.4522(6) 0.0644(6) 0.6224(3) 0.0434(12) Uani 1 1 d . . . . .
C12 C 0.2981(6) 0.2845(6) 0.6084(3) 0.0424(12) Uani 1 1 d . . . . .
H12 H 0.2433 0.3421 0.6472 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2339(6) 0.3020(6) 0.5058(3) 0.0414(12) Uani 1 1 d . . . . .
C14 C -0.0313(7) 0.3317(6) 0.3963(4) 0.0460(13) Uani 1 1 d . . . . .
C15 C -0.0367(9) 0.3782(9) 0.2369(4) 0.074(2) Uani 1 1 d . . . . .
H15A H 0.0334 0.4638 0.2151 0.088 Uiso 1 1 calc R U . . .
H15B H -0.1451 0.4036 0.2407 0.088 Uiso 1 1 calc R U . . .
C16 C -0.0736(13) 0.2418(14) 0.1684(6) 0.110(3) Uani 1 1 d . . . . .
C17 C 0.006(2) 0.0310(19) 0.1200(9) 0.200(4) Uani 1 1 d D U . . .
H17A H -0.1013 -0.0477 0.0987 0.240 Uiso 1 1 calc R U . . .
H17B H 0.0232 0.0885 0.0682 0.240 Uiso 1 1 calc R U . . .
C18 C 0.148(2) -0.0423(19) 0.1452(11) 0.212(5) Uani 1 1 d D U . . .
H18A H 0.2529 0.0344 0.1718 0.318 Uiso 1 1 calc R U . . .
H18B H 0.1604 -0.0987 0.0903 0.318 Uiso 1 1 calc R U . . .
H18C H 0.1236 -0.1111 0.1901 0.318 Uiso 1 1 calc R U . . .
N1 N 0.8878(6) 0.2278(7) 0.6334(4) 0.0753(16) Uani 1 1 d . . . . .
N2 N 0.4797(6) -0.0768(6) 0.6168(4) 0.0632(14) Uani 1 1 d . . . . .
H2A H 0.5819 -0.0887 0.6175 0.076 Uiso 1 1 calc R U . . .
H2B H 0.3951 -0.1555 0.6125 0.076 Uiso 1 1 calc R U . . .
N3 N 0.0647(5) 0.3084(5) 0.4819(3) 0.0438(10) Uani 1 1 d . . . . .
H3 H 0.0095 0.2964 0.5257 0.053 Uiso 1 1 calc R U . . .
N4 N 0.0525(6) 0.3594(6) 0.3294(3) 0.0637(14) Uani 1 1 d . . . . .
H4 H 0.1622 0.3663 0.3411 0.076 Uiso 1 1 calc R U . . .
O1 O 0.7119(9) 0.6862(7) 1.0010(3) 0.111(2) Uani 1 1 d . . . . .
O2 O 0.3279(5) 0.3114(6) 0.4506(3) 0.0662(12) Uani 1 1 d . . . . .
O3 O -0.1838(5) 0.3300(5) 0.3895(3) 0.0698(13) Uani 1 1 d . . . . .
O4 O -0.1510(13) 0.2463(10) 0.0872(4) 0.172(4) Uani 1 1 d . . . . .
O5 O -0.0116(14) 0.1342(11) 0.1964(5) 0.181(3) Uani 1 1 d D U . . .
S1 S 0.24207(16) 0.08192(18) 0.62399(11) 0.0558(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
C1 C2 1.341(9) . ?
C1 C7 1.381(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.405(9) . ?
C2 H2 0.9300 . ?
C3 C5 1.359(9) . ?
C3 O1 1.365(8) . ?
C4 O1 1.422(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.401(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.517(7) . ?
C8 C9 1.498(7) . ?
C8 C12 1.566(6) . ?
C8 H8 0.9800 . ?
C9 C11 1.359(7) . ?
C9 C10 1.423(7) . ?
C10 N1 1.135(6) . ?
C11 N2 1.340(7) . ?
C11 S1 1.755(5) . ?
C12 C13 1.524(7) . ?
C12 S1 1.825(5) . ?
C12 H12 0.9800 . ?
C13 O2 1.222(6) . ?
C13 N3 1.362(6) . ?
C14 O3 1.220(6) . ?
C14 N4 1.319(7) . ?
C14 N3 1.393(6) . ?
C15 N4 1.444(7) . ?
C15 C16 1.467(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O4 1.236(9) . ?
C16 O5 1.246(11) . ?
C17 C18 1.448(13) . ?
C17 O5 1.459(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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 C1 C7 121.7(5) . . ?
C2 C1 H1 119.2 . . ?
C7 C1 H1 119.2 . . ?
C1 C2 C3 121.0(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C5 C3 O1 124.2(6) . . ?
C5 C3 C2 119.0(6) . . ?
O1 C3 C2 116.8(6) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 119.2(5) . . ?
C3 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.7(6) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C1 117.5(5) . . ?
C6 C7 C8 123.0(5) . . ?
C1 C7 C8 119.5(4) . . ?
C9 C8 C7 114.6(4) . . ?
C9 C8 C12 104.7(4) . . ?
C7 C8 C12 111.6(4) . . ?
C9 C8 H8 108.5 . . ?
C7 C8 H8 108.5 . . ?
C12 C8 H8 108.5 . . ?
C11 C9 C10 122.0(5) . . ?
C11 C9 C8 117.1(4) . . ?
C10 C9 C8 120.9(4) . . ?
N1 C10 C9 177.8(7) . . ?
N2 C11 C9 129.2(5) . . ?
N2 C11 S1 117.9(4) . . ?
C9 C11 S1 112.9(4) . . ?
C13 C12 C8 111.4(4) . . ?
C13 C12 S1 109.2(4) . . ?
C8 C12 S1 107.5(3) . . ?
C13 C12 H12 109.6 . . ?
C8 C12 H12 109.6 . . ?
S1 C12 H12 109.6 . . ?
O2 C13 N3 123.4(4) . . ?
O2 C13 C12 122.4(4) . . ?
N3 C13 C12 114.1(4) . . ?
O3 C14 N4 124.9(5) . . ?
O3 C14 N3 118.1(5) . . ?
N4 C14 N3 116.9(4) . . ?
N4 C15 C16 113.7(6) . . ?
N4 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O4 C16 O5 125.5(9) . . ?
O4 C16 C15 118.5(9) . . ?
O5 C16 C15 115.8(7) . . ?
C18 C17 O5 113.8(10) . . ?
C18 C17 H17A 108.8 . . ?
O5 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
O5 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 128.9(4) . . ?
C13 N3 H3 115.5 . . ?
C14 N3 H3 115.5 . . ?
C14 N4 C15 121.2(5) . . ?
C14 N4 H4 119.4 . . ?
C15 N4 H4 119.4 . . ?
C3 O1 C4 117.6(6) . . ?
C16 O5 C17 112.6(9) . . ?
C11 S1 C12 91.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.86 2.50 3.119(7) 129.6 2_656
N2 H2B O3 0.86 2.05 2.906(6) 174.4 2_556
N3 H3 N1 0.86 2.10 2.949(7) 169.3 1_455
N4 H4 O2 0.86 2.04 2.693(6) 132.1 .

_refine_diff_density_max         1.547
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.137

####################################################################### 
# 
# 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_1b_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1848361'
_audit_update_record             
;
2018-06-10 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N4 O4 S2'
_chemical_formula_sum            'C15 H16 N4 O4 S2'
_chemical_formula_weight         380.44

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2173(8)
_cell_length_b                   8.3786(9)
_cell_length_c                   14.5475(15)
_cell_angle_alpha                92.588(4)
_cell_angle_beta                 103.511(3)
_cell_angle_gamma                103.084(3)
_cell_volume                     943.49(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6719
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.308
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14655
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.509
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_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 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4334
_reflns_number_gt                3297
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1287P)²+0.7299P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4334
_refine_ls_number_parameters     221
_refine_ls_number_restraints     80
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2222
_refine_ls_wR_factor_gt          0.2050
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1462(6) 0.0293(7) -0.4179(3) 0.0771(12) Uani 1 1 d . U . . .
H1 H -0.1885 0.0359 -0.4824 0.092 Uiso 1 1 calc R U . . .
C2 C -0.1027(7) -0.1017(7) -0.3839(3) 0.0818(13) Uani 1 1 d . U . . .
H2 H -0.1107 -0.1952 -0.4234 0.098 Uiso 1 1 calc R U . . .
C3 C -0.0408(5) -0.0925(5) -0.2804(2) 0.050 Uani 1 1 d . U . . .
H3 H -0.0077 -0.1744 -0.2447 0.060 Uiso 1 1 calc R U . . .
C4 C -0.0426(4) 0.0744(4) -0.2451(2) 0.0393(6) Uani 1 1 d . U . . .
C5 C 0.2108(3) 0.2081(3) -0.10659(18) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.2680 0.1468 -0.1427 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0126(3) 0.1464(3) -0.14264(19) 0.0323(6) Uani 1 1 d . . . . .
H6 H -0.0285 0.0617 -0.1035 0.039 Uiso 1 1 calc R U . . .
C7 C -0.0563(3) 0.2940(4) -0.12620(19) 0.0340(6) Uani 1 1 d . . . . .
C8 C -0.2278(4) 0.2788(4) -0.1213(2) 0.0398(7) Uani 1 1 d . . . . .
C9 C 0.0562(3) 0.4428(4) -0.11984(19) 0.0344(6) Uani 1 1 d . . . . .
C10 C 0.2711(3) 0.1935(3) -0.00076(19) 0.0318(6) Uani 1 1 d . . . . .
C11 C 0.5303(4) 0.1628(3) 0.1189(2) 0.0382(6) Uani 1 1 d . . . . .
C12 C 0.5288(6) 0.1247(5) 0.2828(3) 0.0632(10) Uani 1 1 d . U . . .
H12A H 0.6144 0.0636 0.2788 0.076 Uiso 1 1 calc R U . . .
H12B H 0.4421 0.0552 0.3084 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6128(8) 0.2700(7) 0.3507(3) 0.0901(14) Uani 1 1 d . U . . .
C14 C 0.6646(13) 0.5597(9) 0.3882(5) 0.150(3) Uani 1 1 d . U . . .
H14A H 0.6688 0.5401 0.4538 0.180 Uiso 1 1 calc R U . . .
H14B H 0.7819 0.5960 0.3819 0.180 Uiso 1 1 calc R U . . .
C15 C 0.5755(15) 0.6773(10) 0.3624(6) 0.171(4) Uani 1 1 d . U . . .
H15A H 0.5806 0.7026 0.2993 0.256 Uiso 1 1 calc R U . . .
H15B H 0.6262 0.7752 0.4060 0.256 Uiso 1 1 calc R U . . .
H15C H 0.4573 0.6366 0.3640 0.256 Uiso 1 1 calc R U . . .
N1 N -0.3679(4) 0.2620(5) -0.1166(2) 0.0604(8) Uani 1 1 d . . . . .
N2 N 0.0299(4) 0.5938(3) -0.1124(2) 0.0485(7) Uani 1 1 d . . . . .
H2A H -0.0707 0.6061 -0.1110 0.058 Uiso 1 1 calc R U . . .
H2B H 0.1134 0.6787 -0.1089 0.058 Uiso 1 1 calc R U . . .
N3 N 0.4379(3) 0.1843(3) 0.02835(17) 0.0366(5) Uani 1 1 d . . . . .
H3A H 0.4946 0.1930 -0.0147 0.044 Uiso 1 1 calc R U . . .
N4 N 0.4468(4) 0.1510(4) 0.18748(19) 0.0474(7) Uani 1 1 d . . . . .
H4 H 0.3416 0.1592 0.1747 0.057 Uiso 1 1 calc R U . . .
O1 O 0.1766(3) 0.1887(3) 0.05304(14) 0.0445(5) Uani 1 1 d . . . . .
O2 O 0.6793(3) 0.1533(3) 0.12943(18) 0.0544(6) Uani 1 1 d . . . . .
O3 O 0.7050(10) 0.2646(7) 0.4244(3) 0.198(3) Uani 1 1 d . U . . .
O4 O 0.5712(7) 0.4037(5) 0.3230(3) 0.1108(13) Uani 1 1 d . U . . .
S1 S -0.11828(16) 0.18257(15) -0.33441(7) 0.0718(4) Uani 1 1 d . U . . .
S2 S 0.26395(8) 0.42626(9) -0.12469(5) 0.0382(2) 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
C1 C2 1.312(7) . ?
C1 S1 1.665(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.465(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.472(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.507(4) . ?
C4 S1 1.697(3) . ?
C5 C10 1.523(4) . ?
C5 C6 1.546(3) . ?
C5 S2 1.826(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.504(4) . ?
C6 H6 0.9800 . ?
C7 C9 1.358(4) . ?
C7 C8 1.405(4) . ?
C8 N1 1.147(4) . ?
C9 N2 1.335(4) . ?
C9 S2 1.761(3) . ?
C10 O1 1.220(3) . ?
C10 N3 1.358(3) . ?
C11 O2 1.219(4) . ?
C11 N4 1.332(4) . ?
C11 N3 1.400(4) . ?
C12 N4 1.443(4) . ?
C12 C13 1.458(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.169(6) . ?
C13 O4 1.297(6) . ?
C14 C15 1.370(11) . ?
C14 O4 1.513(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8600 . ?
N4 H4 0.8600 . ?

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 C1 S1 113.5(3) . . ?
C2 C1 H1 123.2 . . ?
S1 C1 H1 123.2 . . ?
C1 C2 C3 116.2(4) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 105.0(3) . . ?
C2 C3 H3 127.5 . . ?
C4 C3 H3 127.5 . . ?
C3 C4 C6 125.9(3) . . ?
C3 C4 S1 112.2(2) . . ?
C6 C4 S1 121.9(2) . . ?
C10 C5 C6 111.4(2) . . ?
C10 C5 S2 108.03(18) . . ?
C6 C5 S2 106.54(18) . . ?
C10 C5 H5 110.3 . . ?
C6 C5 H5 110.3 . . ?
S2 C5 H5 110.3 . . ?
C7 C6 C4 112.8(2) . . ?
C7 C6 C5 105.0(2) . . ?
C4 C6 C5 112.3(2) . . ?
C7 C6 H6 108.9 . . ?
C4 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
C9 C7 C8 122.3(3) . . ?
C9 C7 C6 115.6(2) . . ?
C8 C7 C6 122.1(3) . . ?
N1 C8 C7 178.1(4) . . ?
N2 C9 C7 129.5(3) . . ?
N2 C9 S2 117.6(2) . . ?
C7 C9 S2 112.9(2) . . ?
O1 C10 N3 122.9(3) . . ?
O1 C10 C5 122.7(2) . . ?
N3 C10 C5 114.4(2) . . ?
O2 C11 N4 124.6(3) . . ?
O2 C11 N3 118.4(3) . . ?
N4 C11 N3 117.1(3) . . ?
N4 C12 C13 117.4(4) . . ?
N4 C12 H12A 107.9 . . ?
C13 C12 H12A 107.9 . . ?
N4 C12 H12B 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
O3 C13 O4 123.4(6) . . ?
O3 C13 C12 122.7(5) . . ?
O4 C13 C12 113.9(4) . . ?
C15 C14 O4 107.6(7) . . ?
C15 C14 H14A 110.2 . . ?
O4 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
O4 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N2 H2A 120.0 . . ?
C9 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C10 N3 C11 128.8(3) . . ?
C10 N3 H3A 115.6 . . ?
C11 N3 H3A 115.6 . . ?
C11 N4 C12 121.5(3) . . ?
C11 N4 H4 119.2 . . ?
C12 N4 H4 119.2 . . ?
C13 O4 C14 115.7(5) . . ?
C1 S1 C4 93.0(2) . . ?
C9 S2 C5 91.15(12) . . ?

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
N2 H2A O1 0.86 2.31 2.981(3) 135.6 2_565
N2 H2B O2 0.86 2.04 2.880(4) 165.3 2_665
N3 H3A N1 0.86 2.09 2.940(4) 168.9 1_655
N4 H4 O1 0.86 2.02 2.683(3) 132.6 .

_refine_diff_density_max         0.864
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1823985'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N4 O5 S'
_chemical_formula_sum            'C25 H24 N4 O5 S'
_chemical_formula_weight         492.54

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

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

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

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

_cell_length_a                   19.0354(9)
_cell_length_b                   9.4928(4)
_cell_length_c                   14.2722(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.6311(16)
_cell_angle_gamma                90
_cell_volume                     2429.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12525
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         25.997
_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 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4633
_reflns_number_gt                3839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.949

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.4021P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1450 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4633
_refine_ls_number_parameters     318
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.104
_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
C1 C 0.2066(2) 1.0082(4) 0.7387(2) 0.0429(8) Uani 1 1 d . . . . .
H1 H 0.1606 1.0414 0.7384 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2406(2) 0.8974(5) 0.8002(3) 0.0518(9) Uani 1 1 d . . . . .
H2 H 0.2175 0.8573 0.8418 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3081(2) 0.8461(4) 0.8005(3) 0.0545(11) Uani 1 1 d . . . . .
C4 C 0.4120(3) 0.6984(6) 0.8835(5) 0.0978(14) Uani 1 1 d . U . . .
H4A H 0.4170 0.6544 0.8255 0.147 Uiso 1 1 calc R U . . .
H4B H 0.4273 0.6338 0.9384 0.147 Uiso 1 1 calc R U . . .
H4C H 0.4428 0.7811 0.8996 0.147 Uiso 1 1 calc R U . . .
C5 C 0.3425(2) 0.9048(4) 0.7386(3) 0.0570(10) Uani 1 1 d . . . . .
H5 H 0.3875 0.8690 0.7370 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3088(2) 1.0180(4) 0.6789(3) 0.0461(9) Uani 1 1 d . . . . .
H6 H 0.3327 1.0595 0.6388 0.055 Uiso 1 1 calc R U . . .
C7 C 0.24154(19) 1.0702(4) 0.6771(2) 0.0357(8) Uani 1 1 d . . . . .
C8 C 0.14220(19) 1.2096(3) 0.5425(2) 0.0372(8) Uani 1 1 d . . . . .
C9 C 0.20830(19) 1.1982(3) 0.6200(2) 0.0351(7) Uani 1 1 d . . . . .
C10 C 0.24333(19) 1.3313(3) 0.6459(2) 0.0377(8) Uani 1 1 d . . . . .
C11 C 0.3137(2) 1.3543(4) 0.7215(3) 0.0444(9) Uani 1 1 d . . . . .
C12 C 0.2035(2) 1.4427(3) 0.5901(2) 0.0382(8) Uani 1 1 d . . . . .
C13 C 0.0915(2) 1.1062(4) 0.4768(3) 0.0403(8) Uani 1 1 d . . . . .
C14 C 0.08080(19) 0.8478(4) 0.4392(2) 0.0380(8) Uani 1 1 d . . . . .
C15 C -0.0544(2) 0.4148(4) 0.2638(3) 0.0613(11) Uani 1 1 d . . . . .
H15 H -0.0066 0.4108 0.3102 0.074 Uiso 1 1 calc R U . . .
C16 C -0.0823(3) 0.2990(5) 0.2038(4) 0.0753(14) Uani 1 1 d . . . . .
H16 H -0.0536 0.2179 0.2106 0.090 Uiso 1 1 calc R U . . .
C17 C -0.1517(3) 0.3045(5) 0.1351(4) 0.0759(14) Uani 1 1 d . . . . .
H17 H -0.1700 0.2283 0.0930 0.091 Uiso 1 1 calc R U . . .
C18 C -0.1945(3) 0.4216(6) 0.1277(4) 0.0760(15) Uani 1 1 d . . . . .
H18 H -0.2425 0.4244 0.0816 0.091 Uiso 1 1 calc R U . . .
C19 C -0.1669(2) 0.5359(5) 0.1884(3) 0.0579(10) Uani 1 1 d . . . . .
H19 H -0.1969 0.6149 0.1833 0.070 Uiso 1 1 calc R U . . .
C20 C -0.0957(2) 0.5354(4) 0.2565(3) 0.0444(9) Uani 1 1 d . . . . .
C21 C -0.0645(2) 0.6617(4) 0.3211(3) 0.0488(9) Uani 1 1 d . . . . .
H21A H -0.0401 0.6293 0.3887 0.059 Uiso 1 1 calc R U . . .
H21B H -0.1058 0.7215 0.3214 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0086(2) 0.7518(4) 0.2900(2) 0.0391(8) Uani 1 1 d . . . . .
H22 H 0.0329 0.6917 0.2886 0.047 Uiso 1 1 calc R U . . .
C23 C -0.0450(2) 0.8154(4) 0.1876(3) 0.0409(8) Uani 1 1 d . . . . .
C24 C -0.0957(3) 0.7589(5) 0.0170(3) 0.0674(8) Uani 1 1 d . U . . .
H24A H -0.0689 0.8242 -0.0110 0.081 Uiso 1 1 calc R U . . .
H24B H -0.1417 0.8033 0.0166 0.081 Uiso 1 1 calc R U . . .
C25 C -0.1120(4) 0.6260(6) -0.0419(3) 0.0904(13) Uani 1 1 d . U . . .
H25A H -0.0660 0.5802 -0.0373 0.136 Uiso 1 1 calc R U . . .
H25B H -0.1392 0.6474 -0.1102 0.136 Uiso 1 1 calc R U . . .
H25C H -0.1413 0.5649 -0.0161 0.136 Uiso 1 1 calc R U . . .
N1 N 0.37020(19) 1.3784(5) 0.7801(3) 0.0661(9) Uani 1 1 d . . . . .
N2 N 0.22427(19) 1.5790(3) 0.5994(3) 0.0538(9) Uani 1 1 d . . . . .
H2A H 0.2658 1.6035 0.6433 0.065 Uiso 1 1 calc R U . . .
H2B H 0.1960 1.6415 0.5615 0.065 Uiso 1 1 calc R U . . .
N3 N 0.11096(17) 0.9662(3) 0.4972(2) 0.0425(7) Uani 1 1 d . . . . .
H3 H 0.1460 0.9499 0.5526 0.051 Uiso 1 1 calc R U . . .
N4 N 0.02074(15) 0.8665(3) 0.35918(19) 0.0420(7) Uani 1 1 d . . . . .
H4 H -0.0009 0.9473 0.3483 0.050 Uiso 1 1 calc R U . . .
O1 O 0.33703(18) 0.7366(4) 0.8645(3) 0.0911(11) Uani 1 1 d . U . . .
O2 O 0.03860(16) 1.1426(3) 0.4070(2) 0.0605(8) Uani 1 1 d . . . . .
O3 O 0.11127(16) 0.7344(3) 0.46422(19) 0.0564(7) Uani 1 1 d . . . . .
O4 O -0.06906(17) 0.9331(3) 0.1734(2) 0.0610(8) Uani 1 1 d . . . . .
O5 O -0.05049(16) 0.7213(3) 0.11775(17) 0.0586(7) Uani 1 1 d . U . . .
S1 S 0.12121(5) 1.38468(9) 0.50527(6) 0.0435(2) 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
C1 C2 1.383(5) . ?
C1 C7 1.398(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 O1 1.371(4) . ?
C3 C5 1.380(6) . ?
C4 O1 1.407(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.388(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.482(5) . ?
C8 C9 1.373(5) . ?
C8 C13 1.471(5) . ?
C8 S1 1.750(3) . ?
C9 C10 1.419(5) . ?
C10 C12 1.386(5) . ?
C10 C11 1.427(5) . ?
C11 N1 1.141(5) . ?
C12 N2 1.346(5) . ?
C12 S1 1.717(3) . ?
C13 O2 1.205(4) . ?
C13 N3 1.384(5) . ?
C14 O3 1.218(4) . ?
C14 N4 1.329(4) . ?
C14 N3 1.400(4) . ?
C15 C20 1.372(6) . ?
C15 C16 1.385(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.356(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.507(5) . ?
C21 C22 1.541(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.449(4) . ?
C22 C23 1.517(5) . ?
C22 H22 0.9800 . ?
C23 O4 1.199(4) . ?
C23 O5 1.317(4) . ?
C24 O5 1.450(5) . ?
C24 C25 1.490(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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 C1 C7 119.9(3) . . ?
C2 C1 H1 120.0 . . ?
C7 C1 H1 120.0 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O1 C3 C2 115.8(4) . . ?
O1 C3 C5 124.2(4) . . ?
C2 C3 C5 120.0(3) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 119.0(4) . . ?
C3 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C1 118.5(3) . . ?
C6 C7 C9 122.2(3) . . ?
C1 C7 C9 119.1(3) . . ?
C9 C8 C13 133.5(3) . . ?
C9 C8 S1 111.9(2) . . ?
C13 C8 S1 114.0(2) . . ?
C8 C9 C10 111.3(3) . . ?
C8 C9 C7 127.9(3) . . ?
C10 C9 C7 120.7(3) . . ?
C12 C10 C9 114.3(3) . . ?
C12 C10 C11 120.8(3) . . ?
C9 C10 C11 125.0(3) . . ?
N1 C11 C10 176.9(4) . . ?
N2 C12 C10 126.2(3) . . ?
N2 C12 S1 123.1(3) . . ?
C10 C12 S1 110.7(2) . . ?
O2 C13 N3 122.6(3) . . ?
O2 C13 C8 121.5(3) . . ?
N3 C13 C8 115.8(3) . . ?
O3 C14 N4 123.9(3) . . ?
O3 C14 N3 118.4(3) . . ?
N4 C14 N3 117.7(3) . . ?
C20 C15 C16 121.6(4) . . ?
C20 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 119.6(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C15 C20 C19 117.3(4) . . ?
C15 C20 C21 121.3(3) . . ?
C19 C20 C21 121.4(4) . . ?
C20 C21 C22 115.7(3) . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21B 108.4 . . ?
C22 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
N4 C22 C23 107.7(3) . . ?
N4 C22 C21 111.5(3) . . ?
C23 C22 C21 111.2(3) . . ?
N4 C22 H22 108.8 . . ?
C23 C22 H22 108.8 . . ?
C21 C22 H22 108.8 . . ?
O4 C23 O5 125.2(3) . . ?
O4 C23 C22 123.9(3) . . ?
O5 C23 C22 110.7(3) . . ?
O5 C24 C25 107.0(4) . . ?
O5 C24 H24A 110.3 . . ?
C25 C24 H24A 110.3 . . ?
O5 C24 H24B 110.3 . . ?
C25 C24 H24B 110.3 . . ?
H24A C24 H24B 108.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 128.2(3) . . ?
C13 N3 H3 115.9 . . ?
C14 N3 H3 115.9 . . ?
C14 N4 C22 120.6(3) . . ?
C14 N4 H4 119.7 . . ?
C22 N4 H4 119.7 . . ?
C3 O1 C4 118.5(4) . . ?
C23 O5 C24 116.9(3) . . ?
C12 S1 C8 91.68(16) . . ?

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
N2 H2B O3 0.86 1.95 2.782(4) 162.5 1_565
N4 H4 O2 0.86 2.07 2.701(4) 129.8 .

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.042

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

data_2j
_database_code_depnum_ccdc_archive 'CCDC 1823983'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N4 O5 S'
_chemical_formula_sum            'C19 H22 N4 O5 S'
_chemical_formula_weight         418.46

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'
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                   8.1029(9)
_cell_length_b                   31.573(3)
_cell_length_c                   8.6015(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.122(3)
_cell_angle_gamma                90
_cell_volume                     2159.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5977
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.42

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21304
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4949
_reflns_number_gt                2942
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0832P)²+1.8823P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4949
_refine_ls_number_parameters     265
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2226
_refine_ls_wR_factor_gt          0.1948
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5910(6) 0.62239(13) 0.4553(5) 0.0676(12) Uani 1 1 d . . . . .
H1 H 0.5905 0.6006 0.3825 0.081 Uiso 1 1 calc R U . . .
C2 C 0.6030(8) 0.66327(14) 0.4076(5) 0.0885(17) Uani 1 1 d . . . . .
H2 H 0.6090 0.6688 0.3026 0.106 Uiso 1 1 calc R U . . .
C3 C 0.6062(7) 0.69618(13) 0.5106(5) 0.0735(13) Uani 1 1 d . . . . .
C4 C 0.6540(12) 0.76928(17) 0.5657(7) 0.155(4) Uani 1 1 d . . . . .
H4A H 0.5566 0.7741 0.6115 0.233 Uiso 1 1 calc R U . . .
H4B H 0.6806 0.7946 0.5139 0.233 Uiso 1 1 calc R U . . .
H4C H 0.7474 0.7616 0.6476 0.233 Uiso 1 1 calc R U . . .
C5 C 0.5861(8) 0.68765(13) 0.6620(5) 0.0849(16) Uani 1 1 d . . . . .
H5 H 0.5809 0.7097 0.7327 0.102 Uiso 1 1 calc R U . . .
C6 C 0.5736(6) 0.64628(13) 0.7089(5) 0.0729(13) Uani 1 1 d . . . . .
H6 H 0.5605 0.6409 0.8121 0.088 Uiso 1 1 calc R U . . .
C7 C 0.5799(4) 0.61268(10) 0.6085(4) 0.0426(8) Uani 1 1 d . . . . .
C8 C 0.7569(4) 0.54967(10) 0.7158(4) 0.0400(8) Uani 1 1 d . . . . .
H8 H 0.8365 0.5656 0.6657 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5781(4) 0.56711(10) 0.6603(4) 0.0388(7) Uani 1 1 d . . . . .
H9 H 0.5211 0.5501 0.5706 0.047 Uiso 1 1 calc R U . . .
C10 C 0.4912(4) 0.56024(10) 0.7987(4) 0.0419(8) Uani 1 1 d . . . . .
C11 C 0.3154(4) 0.56027(12) 0.7787(5) 0.0533(9) Uani 1 1 d . . . . .
C12 C 0.5947(4) 0.55577(10) 0.9416(4) 0.0445(8) Uani 1 1 d . . . . .
C13 C 0.7719(4) 0.50307(11) 0.6851(4) 0.0412(8) Uani 1 1 d . . . . .
C14 C 0.9969(5) 0.45028(12) 0.6730(4) 0.0507(9) Uani 1 1 d . . . . .
C15 C 0.9067(9) 0.34866(18) 0.5695(8) 0.124(2) Uani 1 1 d . . . . .
H15A H 0.7871 0.3481 0.5328 0.187 Uiso 1 1 calc R U . . .
H15B H 0.9468 0.3204 0.5941 0.187 Uiso 1 1 calc R U . . .
H15C H 0.9598 0.3602 0.4883 0.187 Uiso 1 1 calc R U . . .
C16 C 0.9476(7) 0.37537(14) 0.7137(7) 0.0860(15) Uani 1 1 d . . . . .
H16 H 1.0699 0.3756 0.7495 0.103 Uiso 1 1 calc R U . . .
C17 C 0.8655(9) 0.36013(19) 0.8538(8) 0.1034(19) Uani 1 1 d . . . . .
N1 N 0.1722(4) 0.56032(13) 0.7576(5) 0.0839(12) Uani 1 1 d . . . . .
N2 N 0.5556(4) 0.55222(11) 1.0850(4) 0.0649(9) Uani 1 1 d . . . . .
H2A H 0.4520 0.5526 1.0949 0.078 Uiso 1 1 calc R U . . .
H2B H 0.6340 0.5495 1.1674 0.078 Uiso 1 1 calc R U . . .
N3 N 0.9303(3) 0.49073(9) 0.6720(3) 0.0454(7) Uani 1 1 d . . . . .
H3 H 0.9984 0.5110 0.6617 0.054 Uiso 1 1 calc R U . . .
N4 N 0.8914(4) 0.41851(10) 0.6808(4) 0.0648(9) Uani 1 1 d . . . . .
H4 H 0.7854 0.4238 0.6657 0.078 Uiso 1 1 calc R U . . .
O1 O 0.6208(7) 0.73623(10) 0.4544(4) 0.1229(16) Uani 1 1 d . . . . .
O2 O 0.6550(3) 0.47849(8) 0.6759(3) 0.0568(7) Uani 1 1 d . . . . .
O3 O 1.1453(4) 0.44577(9) 0.6680(4) 0.0714(8) Uani 1 1 d . . . . .
O4 O 0.7429(7) 0.37519(18) 0.8834(6) 0.1449(18) Uani 1 1 d . . . . .
O5 O 0.9388(9) 0.3272(2) 0.9161(9) 0.208(3) Uani 1 1 d D . . . .
C18 C 0.836(2) 0.3009(7) 1.0213(19) 0.332(11) Uani 1 1 d D . . . .
H18A H 0.7245 0.3125 1.0186 0.398 Uiso 1 1 calc R U . . .
H18B H 0.8275 0.2712 0.9924 0.398 Uiso 1 1 calc R U . . .
C19 C 0.934(2) 0.3072(8) 1.1545(17) 0.379(14) Uani 1 1 d D . . . .
H19A H 1.0445 0.2967 1.1498 0.569 Uiso 1 1 calc R U . . .
H19B H 0.8919 0.2926 1.2365 0.569 Uiso 1 1 calc R U . . .
H19C H 0.9408 0.3370 1.1772 0.569 Uiso 1 1 calc R U . . .
S1 S 0.80899(11) 0.55657(3) 0.93088(11) 0.0514(3) 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
C1 C2 1.364(6) . ?
C1 C7 1.372(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(6) . ?
C2 H2 0.9300 . ?
C3 O1 1.367(5) . ?
C3 C5 1.371(6) . ?
C4 O1 1.406(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.377(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.507(5) . ?
C8 C13 1.504(5) . ?
C8 C9 1.537(4) . ?
C8 S1 1.829(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.511(4) . ?
C9 H9 0.9800 . ?
C10 C12 1.356(5) . ?
C10 C11 1.401(5) . ?
C11 N1 1.139(4) . ?
C12 N2 1.336(4) . ?
C12 S1 1.756(3) . ?
C13 O2 1.215(4) . ?
C13 N3 1.366(4) . ?
C14 O3 1.219(4) . ?
C14 N4 1.328(5) . ?
C14 N3 1.386(5) . ?
C15 C16 1.484(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 N4 1.447(5) . ?
C16 C17 1.560(9) . ?
C16 H16 0.9800 . ?
C17 O4 1.173(7) . ?
C17 O5 1.265(7) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
O5 C18 1.579(12) . ?
C18 C19 1.279(15) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 C1 C7 121.5(4) . . ?
C2 C1 H1 119.3 . . ?
C7 C1 H1 119.3 . . ?
C3 C2 C1 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 O1 117.9(4) . . ?
C2 C3 C5 118.5(4) . . ?
O1 C3 C5 123.5(4) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 119.6(4) . . ?
C3 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 122.3(4) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C1 C7 C6 116.6(3) . . ?
C1 C7 C9 120.2(3) . . ?
C6 C7 C9 123.1(3) . . ?
C13 C8 C9 113.5(3) . . ?
C13 C8 S1 106.5(2) . . ?
C9 C8 S1 106.9(2) . . ?
C13 C8 H8 109.9 . . ?
C9 C8 H8 109.9 . . ?
S1 C8 H8 109.9 . . ?
C7 C9 C10 113.8(3) . . ?
C7 C9 C8 111.8(3) . . ?
C10 C9 C8 105.0(3) . . ?
C7 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C12 C10 C11 123.2(3) . . ?
C12 C10 C9 115.4(3) . . ?
C11 C10 C9 121.4(3) . . ?
N1 C11 C10 177.9(4) . . ?
N2 C12 C10 129.1(3) . . ?
N2 C12 S1 117.6(3) . . ?
C10 C12 S1 113.3(3) . . ?
O2 C13 N3 123.0(3) . . ?
O2 C13 C8 123.2(3) . . ?
N3 C13 C8 113.7(3) . . ?
O3 C14 N4 124.2(4) . . ?
O3 C14 N3 119.5(4) . . ?
N4 C14 N3 116.2(3) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C15 111.1(4) . . ?
N4 C16 C17 106.1(4) . . ?
C15 C16 C17 114.2(5) . . ?
N4 C16 H16 108.4 . . ?
C15 C16 H16 108.4 . . ?
C17 C16 H16 108.4 . . ?
O4 C17 O5 126.1(7) . . ?
O4 C17 C16 123.2(5) . . ?
O5 C17 C16 110.2(6) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 129.3(3) . . ?
C13 N3 H3 115.3 . . ?
C14 N3 H3 115.3 . . ?
C14 N4 C16 122.7(4) . . ?
C14 N4 H4 118.7 . . ?
C16 N4 H4 118.7 . . ?
C3 O1 C4 117.7(4) . . ?
C17 O5 C18 114.7(10) . . ?
C19 C18 O5 97.1(14) . . ?
C19 C18 H18A 112.3 . . ?
O5 C18 H18A 112.3 . . ?
C19 C18 H18B 112.3 . . ?
O5 C18 H18B 112.3 . . ?
H18A C18 H18B 109.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 S1 C8 90.79(15) . . ?

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
N3 H3 N1 0.86 2.15 2.942(5) 152.0 1_655
N2 H2A O2 0.86 2.50 3.071(4) 124.4 3_667
N2 H2B O3 0.86 2.06 2.899(5) 164.6 3_767
N4 H4 O2 0.86 2.04 2.688(4) 132.1 .

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 1823987'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O4 S'
_chemical_formula_sum            'C18 H18 N4 O4 S'
_chemical_formula_weight         386.42

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3930(4)
_cell_length_b                   12.5630(6)
_cell_length_c                   13.1829(7)
_cell_angle_alpha                69.1600(15)
_cell_angle_beta                 76.3073(18)
_cell_angle_gamma                84.3478(17)
_cell_volume                     961.28(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4656
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      23.96

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15143
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4392
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0960P)²+0.5324P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4392
_refine_ls_number_parameters     245
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1996
_refine_ls_wR_factor_gt          0.1723
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7955(6) 0.9996(3) 0.7771(3) 0.0622(9) Uani 1 1 d . U . . .
H1 H 0.6875 0.9779 0.8413 0.075 Uiso 1 1 calc R U . . .
C2 C 0.7548(6) 1.0847(3) 0.6821(3) 0.0675(9) Uani 1 1 d . U . . .
H2 H 0.6196 1.1198 0.6840 0.081 Uiso 1 1 calc R U . . .
C3 C 0.9096(6) 1.1183(3) 0.5858(3) 0.0533(8) Uani 1 1 d . U . . .
C4 C 0.8590(7) 1.2108(3) 0.4834(3) 0.0794(11) Uani 1 1 d . U . . .
H4A H 0.7123 1.2361 0.4998 0.119 Uiso 0.5 1 calc R U P . .
H4B H 0.9534 1.2736 0.4617 0.119 Uiso 0.5 1 calc R U P . .
H4C H 0.8792 1.1811 0.4239 0.119 Uiso 0.5 1 calc R U P . .
H4D H 0.9843 1.2245 0.4238 0.119 Uiso 0.5 1 calc R U P . .
H4E H 0.7432 1.1870 0.4619 0.119 Uiso 0.5 1 calc R U P . .
H4F H 0.8175 1.2795 0.4997 0.119 Uiso 0.5 1 calc R U P . .
C5 C 1.1072(6) 1.0662(3) 0.5868(3) 0.0607(9) Uani 1 1 d . U . . .
H5 H 1.2152 1.0887 0.5226 0.073 Uiso 1 1 calc R U . . .
C6 C 1.1521(5) 0.9809(3) 0.6803(2) 0.0523(7) Uani 1 1 d . U . . .
H6 H 1.2880 0.9466 0.6781 0.063 Uiso 1 1 calc R U . . .
C7 C 0.9952(5) 0.9470(2) 0.7766(2) 0.0412(6) Uani 1 1 d . U . . .
C8 C 1.2071(5) 0.7806(2) 1.0315(2) 0.0471(7) Uani 1 1 d . U . . .
C9 C 1.1793(4) 0.8752(2) 0.9395(2) 0.0423(6) Uani 1 1 d . U . . .
C10 C 1.2601(4) 0.9834(3) 0.9201(2) 0.0434(7) Uani 1 1 d . U . . .
C11 C 1.0388(5) 0.8561(2) 0.8786(2) 0.0414(6) Uani 1 1 d . U . . .
C12 C 0.9550(5) 0.7487(2) 0.9271(2) 0.0445(7) Uani 1 1 d . U . . .
C13 C 0.7988(5) 0.6899(2) 0.9014(2) 0.0467(7) Uani 1 1 d . U . . .
C14 C 0.5868(5) 0.7101(3) 0.7574(2) 0.0497(7) Uani 1 1 d . U . . .
C15 C 0.3168(6) 0.5798(3) 0.7809(3) 0.0563(8) Uani 1 1 d . U . . .
H15A H 0.2644 0.6441 0.7255 0.068 Uiso 1 1 calc R U . . .
H15B H 0.1959 0.5494 0.8423 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4032(7) 0.4901(3) 0.7308(3) 0.0653(9) Uani 1 1 d . U . . .
C17 C 0.3262(11) 0.3719(5) 0.6443(6) 0.1337(18) Uani 1 1 d D U . . .
H17A H 0.3184 0.3015 0.7073 0.160 Uiso 1 1 calc R U . . .
H17B H 0.4725 0.3808 0.6004 0.160 Uiso 1 1 calc R U . . .
C18 C 0.1729(14) 0.3708(8) 0.5757(8) 0.202(3) Uani 1 1 d D U . . .
H18A H 0.0309 0.3552 0.6219 0.304 Uiso 1 1 calc R U . . .
H18B H 0.2164 0.3129 0.5429 0.304 Uiso 1 1 calc R U . . .
H18C H 0.1725 0.4437 0.5181 0.304 Uiso 1 1 calc R U . . .
N1 N 1.3287(5) 0.7711(2) 1.1031(2) 0.0684(8) Uani 1 1 d . . . . .
H1A H 1.4029 0.8280 1.0956 0.082 Uiso 1 1 calc R U . . .
H1B H 1.3334 0.7081 1.1571 0.082 Uiso 1 1 calc R U . . .
N2 N 1.3241(4) 1.0696(2) 0.9085(2) 0.0581(7) Uani 1 1 d . . . . .
N3 N 0.7426(4) 0.7412(2) 0.8016(2) 0.0542(7) Uani 1 1 d . . . . .
H3 H 0.8125 0.8018 0.7589 0.065 Uiso 1 1 calc R U . . .
N4 N 0.4753(4) 0.6184(2) 0.8203(2) 0.0561(7) Uani 1 1 d . . . . .
H4 H 0.4974 0.5813 0.8857 0.067 Uiso 1 1 calc R U . . .
O1 O 0.7252(4) 0.59864(18) 0.96703(19) 0.0653(7) Uani 1 1 d . . . . .
O2 O 0.5629(4) 0.7701(2) 0.66591(19) 0.0771(8) Uani 1 1 d . . . . .
O3 O 0.5732(5) 0.4422(2) 0.7357(2) 0.0901(9) Uani 1 1 d . . . . .
O4 O 0.2599(5) 0.4704(3) 0.6825(3) 0.0945(10) Uani 1 1 d . . . . .
S1 S 1.05294(14) 0.66964(6) 1.04492(7) 0.0546(3) 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
C1 C7 1.378(4) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.365(5) . ?
C3 C4 1.514(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
C4 H4F 0.9600 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C11 1.487(4) . ?
C8 N1 1.327(4) . ?
C8 C9 1.396(4) . ?
C8 S1 1.720(3) . ?
C9 C10 1.417(4) . ?
C9 C11 1.425(4) . ?
C10 N2 1.142(4) . ?
C11 C12 1.372(4) . ?
C12 C13 1.463(4) . ?
C12 S1 1.741(3) . ?
C13 O1 1.222(3) . ?
C13 N3 1.359(4) . ?
C14 O2 1.210(4) . ?
C14 N4 1.314(4) . ?
C14 N3 1.413(4) . ?
C15 N4 1.435(4) . ?
C15 C16 1.498(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.194(5) . ?
C16 O4 1.319(5) . ?
C17 O4 1.484(6) . ?
C17 C18 1.485(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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
C7 C1 C2 120.3(3) . . ?
C7 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C5 C3 C2 117.6(3) . . ?
C5 C3 C4 122.4(3) . . ?
C2 C3 C4 120.0(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4A C4 H4D 141.1 . . ?
H4B C4 H4D 56.3 . . ?
H4C C4 H4D 56.3 . . ?
C3 C4 H4E 109.5 . . ?
H4A C4 H4E 56.3 . . ?
H4B C4 H4E 141.1 . . ?
H4C C4 H4E 56.3 . . ?
H4D C4 H4E 109.5 . . ?
C3 C4 H4F 109.5 . . ?
H4A C4 H4F 56.3 . . ?
H4B C4 H4F 56.3 . . ?
H4C C4 H4F 141.1 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
C3 C5 C6 122.2(3) . . ?
C3 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C1 118.6(3) . . ?
C6 C7 C11 121.2(3) . . ?
C1 C7 C11 120.3(2) . . ?
N1 C8 C9 128.1(3) . . ?
N1 C8 S1 121.5(2) . . ?
C9 C8 S1 110.4(2) . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 C11 113.8(2) . . ?
C10 C9 C11 123.9(2) . . ?
N2 C10 C9 177.5(3) . . ?
C12 C11 C9 111.6(2) . . ?
C12 C11 C7 127.4(3) . . ?
C9 C11 C7 120.9(2) . . ?
C11 C12 C13 133.1(3) . . ?
C11 C12 S1 111.9(2) . . ?
C13 C12 S1 114.9(2) . . ?
O1 C13 N3 122.4(3) . . ?
O1 C13 C12 120.7(3) . . ?
N3 C13 C12 116.9(3) . . ?
O2 C14 N4 124.7(3) . . ?
O2 C14 N3 118.3(3) . . ?
N4 C14 N3 117.0(3) . . ?
N4 C15 C16 112.7(3) . . ?
N4 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N4 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O3 C16 O4 125.2(4) . . ?
O3 C16 C15 125.4(4) . . ?
O4 C16 C15 109.3(3) . . ?
O4 C17 C18 105.8(5) . . ?
O4 C17 H17A 110.6 . . ?
C18 C17 H17A 110.6 . . ?
O4 C17 H17B 110.6 . . ?
C18 C17 H17B 110.6 . . ?
H17A C17 H17B 108.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C13 N3 C14 129.9(3) . . ?
C13 N3 H3 115.1 . . ?
C14 N3 H3 115.1 . . ?
C14 N4 C15 120.5(3) . . ?
C14 N4 H4 119.7 . . ?
C15 N4 H4 119.7 . . ?
C16 O4 C17 111.2(4) . . ?
C8 S1 C12 92.23(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.86 2.25 3.073(4) 161.1 2_877
N1 H1B O3 0.86 2.05 2.887(4) 165.0 2_767
N4 H4 O1 0.86 2.07 2.720(3) 131.8 .

_refine_diff_density_max         0.657
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1823982'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 N4 O5 S'
_chemical_formula_sum            'C25 H26 N4 O5 S'
_chemical_formula_weight         494.56

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

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

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

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

_cell_length_a                   8.4873(16)
_cell_length_b                   34.193(5)
_cell_length_c                   8.7571(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.759(6)
_cell_angle_gamma                90
_cell_volume                     2518.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7229
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28831
_diffrn_reflns_av_unetI/netI     0.1004
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         27.780
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11133
_reflns_number_gt                6336
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.967
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.4230P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11133
_refine_ls_number_parameters     636
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.014
_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
C1 C 0.5653(6) 0.37188(13) 0.5162(6) 0.0466(13) Uani 1 1 d . . . . .
H1 H 0.5582 0.3680 0.4104 0.056 Uiso 1 1 calc R U . . .
C2 C 0.5645(7) 0.40964(16) 0.5762(8) 0.0627(16) Uani 1 1 d . . . . .
C3 C 0.5229(12) 0.4383(2) 0.3272(11) 0.127(3) Uani 1 1 d . . . . .
H3A H 0.6069 0.4240 0.2895 0.190 Uiso 1 1 calc R U . . .
H3B H 0.5138 0.4637 0.2797 0.190 Uiso 1 1 calc R U . . .
H3C H 0.4245 0.4244 0.3026 0.190 Uiso 1 1 calc R U . . .
C4 C 0.5721(7) 0.4150(2) 0.7329(10) 0.081(2) Uani 1 1 d . . . . .
H4 H 0.5698 0.4402 0.7723 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5827(7) 0.3842(2) 0.8306(8) 0.079(2) Uani 1 1 d . . . . .
H5 H 0.5879 0.3883 0.9361 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5858(6) 0.34611(17) 0.7735(6) 0.0544(14) Uani 1 1 d . . . . .
H6 H 0.5940 0.3250 0.8409 0.065 Uiso 1 1 calc R U . . .
C7 C 0.5768(5) 0.33995(13) 0.6168(6) 0.0388(12) Uani 1 1 d . . . . .
C8 C 0.3938(5) 0.28544(12) 0.5021(6) 0.0384(12) Uani 1 1 d . . . . .
H8 H 0.3226 0.3023 0.5523 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5680(5) 0.29860(12) 0.5518(5) 0.0380(11) Uani 1 1 d . . . . .
H9 H 0.6163 0.2808 0.6326 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6511(5) 0.29300(13) 0.4118(6) 0.0367(11) Uani 1 1 d . . . . .
C11 C 0.8199(7) 0.29378(13) 0.4225(6) 0.0416(12) Uani 1 1 d . . . . .
C12 C 0.5559(5) 0.29061(13) 0.2745(6) 0.0377(11) Uani 1 1 d . . . . .
C13 C 0.3610(6) 0.24286(13) 0.5384(5) 0.0375(12) Uani 1 1 d . . . . .
C14 C 0.1279(6) 0.19992(14) 0.5698(5) 0.0387(11) Uani 1 1 d . . . . .
C15 C 0.3121(8) 0.05488(14) 0.4293(7) 0.0642(16) Uani 1 1 d . . . . .
H15 H 0.2660 0.0387 0.4963 0.077 Uiso 1 1 calc R U . . .
C16 C 0.4407(8) 0.04147(16) 0.3620(7) 0.0724(18) Uani 1 1 d . . . . .
H16 H 0.4792 0.0163 0.3838 0.087 Uiso 1 1 calc R U . . .
C17 C 0.5120(8) 0.06475(18) 0.2637(7) 0.0718(17) Uani 1 1 d . . . . .
H17 H 0.5991 0.0559 0.2196 0.086 Uiso 1 1 calc R U . . .
C18 C 0.4508(8) 0.10181(16) 0.2319(7) 0.0694(17) Uani 1 1 d . . . . .
H18 H 0.4965 0.1178 0.1641 0.083 Uiso 1 1 calc R U . . .
C19 C 0.3241(7) 0.11541(15) 0.2983(7) 0.0618(15) Uani 1 1 d . . . . .
H19 H 0.2865 0.1406 0.2761 0.074 Uiso 1 1 calc R U . . .
C20 C 0.2513(7) 0.09231(14) 0.3976(6) 0.0524(14) Uani 1 1 d . . . . .
C21 C 0.1071(7) 0.10640(14) 0.4659(7) 0.0598(16) Uani 1 1 d . . . . .
H21A H 0.0438 0.0838 0.4863 0.072 Uiso 1 1 calc R U . . .
H21B H 0.0429 0.1224 0.3899 0.072 Uiso 1 1 calc R U . . .
C22 C 0.1440(6) 0.13031(14) 0.6164(6) 0.0518(14) Uani 1 1 d . . . . .
H22 H 0.0427 0.1357 0.6543 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2479(8) 0.10849(16) 0.7409(7) 0.0603(16) Uani 1 1 d . . . . .
C24 C 0.2706(12) 0.0495(2) 0.8897(10) 0.140(4) Uani 1 1 d . . . . .
H24A H 0.3798 0.0468 0.8697 0.168 Uiso 1 1 calc R U . . .
H24B H 0.2716 0.0616 0.9900 0.168 Uiso 1 1 calc R U . . .
C25 C 0.2018(13) 0.0134(3) 0.8900(13) 0.169(5) Uani 1 1 d . . . . .
H25A H 0.0972 0.0159 0.9192 0.254 Uiso 1 1 calc R U . . .
H25B H 0.2653 -0.0032 0.9624 0.254 Uiso 1 1 calc R U . . .
H25C H 0.1945 0.0022 0.7889 0.254 Uiso 1 1 calc R U . . .
C26 C 0.7754(6) 0.11155(14) 0.9465(6) 0.0482(13) Uani 1 1 d . . . . .
H26 H 0.7996 0.1158 1.0520 0.058 Uiso 1 1 calc R U . . .
C27 C 0.7640(7) 0.07338(15) 0.8905(7) 0.0562(14) Uani 1 1 d . . . . .
C28 C 0.7421(9) 0.00521(17) 0.9518(9) 0.107(3) Uani 1 1 d . . . . .
H28A H 0.6296 0.0046 0.9186 0.161 Uiso 1 1 calc R U . . .
H28B H 0.7675 -0.0123 1.0372 0.161 Uiso 1 1 calc R U . . .
H28C H 0.7976 -0.0027 0.8685 0.161 Uiso 1 1 calc R U . . .
C29 C 0.7319(7) 0.06721(18) 0.7334(8) 0.0702(18) Uani 1 1 d . . . . .
H29 H 0.7251 0.0419 0.6944 0.084 Uiso 1 1 calc R U . . .
C30 C 0.7103(8) 0.09857(19) 0.6352(7) 0.0733(18) Uani 1 1 d . . . . .
H30 H 0.6892 0.0944 0.5295 0.088 Uiso 1 1 calc R U . . .
C31 C 0.7195(6) 0.13647(16) 0.6920(6) 0.0572(15) Uani 1 1 d . . . . .
H31 H 0.7039 0.1575 0.6243 0.069 Uiso 1 1 calc R U . . .
C32 C 0.7515(5) 0.14313(14) 0.8486(6) 0.0388(12) Uani 1 1 d . . . . .
C33 C 0.9318(5) 0.19874(12) 0.9607(5) 0.0366(11) Uani 1 1 d . . . . .
H33 H 1.0062 0.1821 0.9138 0.044 Uiso 1 1 calc R U . . .
C34 C 0.7585(5) 0.18506(12) 0.9083(5) 0.0368(11) Uani 1 1 d . . . . .
H34 H 0.7110 0.2023 0.8252 0.044 Uiso 1 1 calc R U . . .
C35 C 0.6711(5) 0.19090(12) 1.0466(6) 0.0362(11) Uani 1 1 d . . . . .
C36 C 0.5032(7) 0.19287(13) 1.0341(6) 0.0417(12) Uani 1 1 d . . . . .
C37 C 0.7631(5) 0.19434(13) 1.1848(6) 0.0372(11) Uani 1 1 d . . . . .
C38 C 0.9576(6) 0.24145(13) 0.9212(5) 0.0402(12) Uani 1 1 d . . . . .
C39 C 1.1781(6) 0.28736(13) 0.8848(5) 0.0383(11) Uani 1 1 d . . . . .
C40 C 0.9671(7) 0.44951(16) 0.7392(7) 0.0680(16) Uani 1 1 d . . . . .
H40 H 0.8918 0.4436 0.8036 0.082 Uiso 1 1 calc R U . . .
C41 C 0.9955(8) 0.48846(17) 0.7057(9) 0.084(2) Uani 1 1 d . . . . .
H41 H 0.9394 0.5083 0.7471 0.101 Uiso 1 1 calc R U . . .
C42 C 1.1048(9) 0.49716(18) 0.6130(9) 0.089(2) Uani 1 1 d . . . . .
H42 H 1.1230 0.5231 0.5890 0.107 Uiso 1 1 calc R U . . .
C43 C 1.1895(8) 0.46810(19) 0.5536(9) 0.087(2) Uani 1 1 d . . . . .
H43 H 1.2662 0.4743 0.4910 0.104 Uiso 1 1 calc R U . . .
C44 C 1.1598(7) 0.42942(16) 0.5875(7) 0.0623(16) Uani 1 1 d . . . . .
H44 H 1.2174 0.4097 0.5470 0.075 Uiso 1 1 calc R U . . .
C45 C 1.0478(6) 0.41951(14) 0.6793(6) 0.0477(13) Uani 1 1 d . . . . .
C46 C 1.0123(6) 0.37736(13) 0.7090(6) 0.0508(13) Uani 1 1 d . . . . .
H46A H 1.0068 0.3632 0.6124 0.061 Uiso 1 1 calc R U . . .
H46B H 0.9081 0.3759 0.7425 0.061 Uiso 1 1 calc R U . . .
C47 C 1.1308(6) 0.35660(13) 0.8280(6) 0.0438(12) Uani 1 1 d . . . . .
H47 H 1.2337 0.3556 0.7891 0.053 Uiso 1 1 calc R U . . .
C48 C 1.1527(7) 0.37801(16) 0.9804(7) 0.0568(15) Uani 1 1 d . . . . .
C49 C 1.0453(12) 0.3902(3) 1.2084(9) 0.141(4) Uani 1 1 d D . . . .
H49A H 1.0968 0.3727 1.2868 0.170 Uiso 1 1 calc R U . . .
H49B H 1.1068 0.4141 1.2104 0.170 Uiso 1 1 calc R U . . .
C50 C 0.8887(13) 0.3983(4) 1.2353(13) 0.219(7) Uani 1 1 d D . . . .
H50A H 0.8480 0.4201 1.1732 0.328 Uiso 1 1 calc R U . . .
H50B H 0.8884 0.4044 1.3422 0.328 Uiso 1 1 calc R U . . .
H50C H 0.8229 0.3758 1.2088 0.328 Uiso 1 1 calc R U . . .
N1 N 0.9554(6) 0.29459(14) 0.4330(6) 0.0603(12) Uani 1 1 d . . . . .
N2 N 0.5966(5) 0.28850(11) 0.1307(5) 0.0534(11) Uani 1 1 d . . . . .
H2A H 0.6952 0.2886 0.1176 0.064 Uiso 1 1 calc R U . . .
H2B H 0.5239 0.2871 0.0523 0.064 Uiso 1 1 calc R U . . .
N3 N 0.2042(5) 0.23548(10) 0.5445(5) 0.0395(10) Uani 1 1 d . . . . .
H3 H 0.1426 0.2555 0.5308 0.047 Uiso 1 1 calc R U . . .
N4 N 0.2189(5) 0.16816(11) 0.5912(5) 0.0510(12) Uani 1 1 d . . . . .
H4A H 0.3199 0.1697 0.5904 0.061 Uiso 1 1 calc R U . . .
N5 N 0.3671(6) 0.19535(14) 1.0269(6) 0.0633(13) Uani 1 1 d . . . . .
N6 N 0.7189(5) 0.19689(12) 1.3261(4) 0.0507(10) Uani 1 1 d . . . . .
H6A H 0.6197 0.1964 1.3370 0.061 Uiso 1 1 calc R U . . .
H6B H 0.7898 0.1990 1.4057 0.061 Uiso 1 1 calc R U . . .
N7 N 1.1126(4) 0.25112(10) 0.9156(4) 0.0361(9) Uani 1 1 d . . . . .
H7 H 1.1797 0.2323 0.9336 0.043 Uiso 1 1 calc R U . . .
N8 N 1.0768(5) 0.31659(11) 0.8464(5) 0.0479(11) Uani 1 1 d . . . . .
H8A H 0.9765 0.3117 0.8321 0.058 Uiso 1 1 calc R U . . .
O1 O 0.5573(6) 0.44262(11) 0.4873(7) 0.1027(17) Uani 1 1 d . . . . .
O2 O 0.4649(4) 0.21818(9) 0.5564(5) 0.0634(11) Uani 1 1 d . . . . .
O3 O -0.0161(4) 0.20053(10) 0.5720(4) 0.0537(9) Uani 1 1 d . . . . .
O4 O 0.3751(6) 0.11886(13) 0.8034(5) 0.0895(14) Uani 1 1 d . . . . .
O5 O 0.1817(5) 0.07455(11) 0.7701(5) 0.0822(13) Uani 1 1 d . . . . .
O6 O 0.7895(6) 0.04432(10) 0.9989(5) 0.0805(13) Uani 1 1 d . . . . .
O7 O 0.8482(4) 0.26489(10) 0.8978(5) 0.0596(10) Uani 1 1 d . . . . .
O8 O 1.3228(4) 0.29020(10) 0.8914(4) 0.0603(10) Uani 1 1 d . . . . .
O9 O 1.2601(6) 0.39934(14) 1.0244(5) 0.0952(15) Uani 1 1 d . . . . .
O10 O 1.0338(6) 0.37170(16) 1.0551(5) 0.1130(19) Uani 1 1 d . . . . .
S1 S 0.35151(14) 0.29218(4) 0.29164(15) 0.0481(3) Uani 1 1 d . . . . .
S2 S 0.96874(15) 0.19422(3) 1.17206(14) 0.0435(3) 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
C1 C2 1.394(7) . ?
C1 C7 1.398(7) . ?
C1 H1 0.9300 . ?
C2 O1 1.367(7) . ?
C2 C4 1.378(9) . ?
C3 O1 1.401(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.353(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(7) . ?
C6 H6 0.9300 . ?
C7 C9 1.522(6) . ?
C8 C13 1.524(6) . ?
C8 C9 1.551(6) . ?
C8 S1 1.844(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.507(6) . ?
C9 H9 0.9800 . ?
C10 C12 1.357(6) . ?
C10 C11 1.423(7) . ?
C11 N1 1.142(6) . ?
C12 N2 1.352(6) . ?
C12 S1 1.762(5) . ?
C13 O2 1.215(5) . ?
C13 N3 1.362(6) . ?
C14 O3 1.226(5) . ?
C14 N4 1.331(6) . ?
C14 N3 1.409(6) . ?
C15 C16 1.387(8) . ?
C15 C20 1.394(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.512(7) . ?
C21 C22 1.546(7) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.471(6) . ?
C22 C23 1.505(8) . ?
C22 H22 0.9800 . ?
C23 O4 1.196(7) . ?
C23 O5 1.329(6) . ?
C24 C25 1.365(11) . ?
C24 O5 1.479(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C32 1.377(7) . ?
C26 C27 1.393(7) . ?
C26 H26 0.9300 . ?
C27 O6 1.371(7) . ?
C27 C29 1.383(8) . ?
C28 O6 1.440(7) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.371(9) . ?
C29 H29 0.9300 . ?
C30 C31 1.386(8) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(7) . ?
C31 H31 0.9300 . ?
C32 C34 1.524(6) . ?
C33 C38 1.523(6) . ?
C33 C34 1.552(6) . ?
C33 S2 1.842(4) . ?
C33 H33 0.9800 . ?
C34 C35 1.517(6) . ?
C34 H34 0.9800 . ?
C35 C37 1.353(6) . ?
C35 C36 1.416(7) . ?
C36 N5 1.151(6) . ?
C37 N6 1.344(6) . ?
C37 S2 1.764(5) . ?
C38 O7 1.223(5) . ?
C38 N7 1.364(6) . ?
C39 O8 1.225(5) . ?
C39 N8 1.332(6) . ?
C39 N7 1.399(6) . ?
C40 C45 1.376(7) . ?
C40 C41 1.392(8) . ?
C40 H40 0.9300 . ?
C41 C42 1.346(9) . ?
C41 H41 0.9300 . ?
C42 C43 1.369(9) . ?
C42 H42 0.9300 . ?
C43 C44 1.386(8) . ?
C43 H43 0.9300 . ?
C44 C45 1.367(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.502(6) . ?
C46 C47 1.523(7) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 N8 1.459(6) . ?
C47 C48 1.511(7) . ?
C47 H47 0.9800 . ?
C48 O9 1.191(6) . ?
C48 O10 1.292(7) . ?
C49 C50 1.409(10) . ?
C49 O10 1.475(8) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4A 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 H7 0.8600 . ?
N8 H8A 0.8600 . ?

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 C1 C7 119.3(5) . . ?
C2 C1 H1 120.3 . . ?
C7 C1 H1 120.3 . . ?
O1 C2 C4 116.7(6) . . ?
O1 C2 C1 123.5(6) . . ?
C4 C2 C1 119.8(6) . . ?
O1 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C2 C4 H4 119.5 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C1 119.8(4) . . ?
C6 C7 C9 120.4(4) . . ?
C1 C7 C9 119.7(4) . . ?
C13 C8 C9 114.4(4) . . ?
C13 C8 S1 108.2(3) . . ?
C9 C8 S1 107.1(3) . . ?
C13 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
S1 C8 H8 109.0 . . ?
C10 C9 C7 114.7(4) . . ?
C10 C9 C8 105.5(4) . . ?
C7 C9 C8 111.8(4) . . ?
C10 C9 H9 108.2 . . ?
C7 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C12 C10 C11 122.2(4) . . ?
C12 C10 C9 116.1(4) . . ?
C11 C10 C9 121.4(4) . . ?
N1 C11 C10 179.1(6) . . ?
N2 C12 C10 129.2(4) . . ?
N2 C12 S1 117.3(4) . . ?
C10 C12 S1 113.4(4) . . ?
O2 C13 N3 124.2(4) . . ?
O2 C13 C8 122.7(4) . . ?
N3 C13 C8 113.1(4) . . ?
O3 C14 N4 124.9(4) . . ?
O3 C14 N3 117.9(4) . . ?
N4 C14 N3 117.1(4) . . ?
C16 C15 C20 120.7(5) . . ?
C16 C15 H15 119.6 . . ?
C20 C15 H15 119.6 . . ?
C17 C16 C15 120.9(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.2(6) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 121.3(6) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.1(5) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 117.7(5) . . ?
C19 C20 C21 121.5(5) . . ?
C15 C20 C21 120.8(5) . . ?
C20 C21 C22 115.1(4) . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
N4 C22 C23 108.8(4) . . ?
N4 C22 C21 112.3(4) . . ?
C23 C22 C21 112.8(4) . . ?
N4 C22 H22 107.6 . . ?
C23 C22 H22 107.6 . . ?
C21 C22 H22 107.6 . . ?
O4 C23 O5 123.3(6) . . ?
O4 C23 C22 126.1(5) . . ?
O5 C23 C22 110.5(5) . . ?
C25 C24 O5 110.4(7) . . ?
C25 C24 H24A 109.6 . . ?
O5 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
O5 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C26 C27 121.2(5) . . ?
C32 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
O6 C27 C29 124.7(5) . . ?
O6 C27 C26 116.0(5) . . ?
C29 C27 C26 119.2(5) . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C27 119.8(5) . . ?
C30 C29 H29 120.1 . . ?
C27 C29 H29 120.1 . . ?
C29 C30 C31 120.7(6) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 120.3(5) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C26 C32 C31 118.8(5) . . ?
C26 C32 C34 121.9(4) . . ?
C31 C32 C34 119.3(5) . . ?
C38 C33 C34 112.4(4) . . ?
C38 C33 S2 107.3(3) . . ?
C34 C33 S2 107.3(3) . . ?
C38 C33 H33 109.9 . . ?
C34 C33 H33 109.9 . . ?
S2 C33 H33 109.9 . . ?
C35 C34 C32 113.4(4) . . ?
C35 C34 C33 105.7(4) . . ?
C32 C34 C33 112.1(4) . . ?
C35 C34 H34 108.5 . . ?
C32 C34 H34 108.5 . . ?
C33 C34 H34 108.5 . . ?
C37 C35 C36 121.2(4) . . ?
C37 C35 C34 116.1(4) . . ?
C36 C35 C34 122.7(4) . . ?
N5 C36 C35 178.0(5) . . ?
N6 C37 C35 129.1(4) . . ?
N6 C37 S2 117.4(4) . . ?
C35 C37 S2 113.6(3) . . ?
O7 C38 N7 123.3(4) . . ?
O7 C38 C33 122.5(4) . . ?
N7 C38 C33 114.2(4) . . ?
O8 C39 N8 124.1(4) . . ?
O8 C39 N7 118.9(4) . . ?
N8 C39 N7 117.0(4) . . ?
C45 C40 C41 121.6(6) . . ?
C45 C40 H40 119.2 . . ?
C41 C40 H40 119.2 . . ?
C42 C41 C40 119.4(6) . . ?
C42 C41 H41 120.3 . . ?
C40 C41 H41 120.3 . . ?
C41 C42 C43 120.6(6) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 H42 119.7 . . ?
C42 C43 C44 119.4(6) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C45 C44 C43 121.6(6) . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
C44 C45 C40 117.4(5) . . ?
C44 C45 C46 120.7(5) . . ?
C40 C45 C46 121.8(5) . . ?
C45 C46 C47 115.9(4) . . ?
C45 C46 H46A 108.3 . . ?
C47 C46 H46A 108.3 . . ?
C45 C46 H46B 108.3 . . ?
C47 C46 H46B 108.3 . . ?
H46A C46 H46B 107.4 . . ?
N8 C47 C48 111.1(4) . . ?
N8 C47 C46 108.9(4) . . ?
C48 C47 C46 111.7(4) . . ?
N8 C47 H47 108.3 . . ?
C48 C47 H47 108.3 . . ?
C46 C47 H47 108.3 . . ?
O9 C48 O10 123.7(6) . . ?
O9 C48 C47 125.4(6) . . ?
O10 C48 C47 110.8(5) . . ?
C50 C49 O10 106.8(8) . . ?
C50 C49 H49A 110.4 . . ?
O10 C49 H49A 110.4 . . ?
C50 C49 H49B 110.4 . . ?
O10 C49 H49B 110.4 . . ?
H49A C49 H49B 108.6 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 129.6(4) . . ?
C13 N3 H3 115.2 . . ?
C14 N3 H3 115.2 . . ?
C14 N4 C22 119.0(4) . . ?
C14 N4 H4A 120.5 . . ?
C22 N4 H4A 120.5 . . ?
C37 N6 H6A 120.0 . . ?
C37 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C38 N7 C39 129.2(4) . . ?
C38 N7 H7 115.4 . . ?
C39 N7 H7 115.4 . . ?
C39 N8 C47 122.0(4) . . ?
C39 N8 H8A 119.0 . . ?
C47 N8 H8A 119.0 . . ?
C2 O1 C3 118.1(5) . . ?
C23 O5 C24 117.0(5) . . ?
C27 O6 C28 117.6(5) . . ?
C48 O10 C49 115.4(5) . . ?
C12 S1 C8 91.2(2) . . ?
C37 S2 C33 91.6(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
C7 C1 C2 O1 178.5(5) . . . . ?
C7 C1 C2 C4 -1.2(8) . . . . ?
O1 C2 C4 C5 -178.7(6) . . . . ?
C1 C2 C4 C5 1.0(9) . . . . ?
C2 C4 C5 C6 -0.1(10) . . . . ?
C4 C5 C6 C7 -0.5(9) . . . . ?
C5 C6 C7 C1 0.3(8) . . . . ?
C5 C6 C7 C9 -175.6(5) . . . . ?
C2 C1 C7 C6 0.6(7) . . . . ?
C2 C1 C7 C9 176.5(4) . . . . ?
C6 C7 C9 C10 -145.8(5) . . . . ?
C1 C7 C9 C10 38.4(6) . . . . ?
C6 C7 C9 C8 94.2(5) . . . . ?
C1 C7 C9 C8 -81.7(5) . . . . ?
C13 C8 C9 C10 93.7(4) . . . . ?
S1 C8 C9 C10 -26.1(4) . . . . ?
C13 C8 C9 C7 -141.0(4) . . . . ?
S1 C8 C9 C7 99.2(4) . . . . ?
C7 C9 C10 C12 -103.9(5) . . . . ?
C8 C9 C10 C12 19.6(5) . . . . ?
C7 C9 C10 C11 70.6(6) . . . . ?
C8 C9 C10 C11 -165.9(4) . . . . ?
C11 C10 C12 N2 0.2(8) . . . . ?
C9 C10 C12 N2 174.7(4) . . . . ?
C11 C10 C12 S1 -177.5(3) . . . . ?
C9 C10 C12 S1 -3.1(5) . . . . ?
C9 C8 C13 O2 -22.9(7) . . . . ?
S1 C8 C13 O2 96.3(5) . . . . ?
C9 C8 C13 N3 158.6(4) . . . . ?
S1 C8 C13 N3 -82.2(4) . . . . ?
C20 C15 C16 C17 0.5(9) . . . . ?
C15 C16 C17 C18 -0.8(9) . . . . ?
C16 C17 C18 C19 1.1(9) . . . . ?
C17 C18 C19 C20 -1.0(9) . . . . ?
C18 C19 C20 C15 0.7(8) . . . . ?
C18 C19 C20 C21 -177.3(5) . . . . ?
C16 C15 C20 C19 -0.4(8) . . . . ?
C16 C15 C20 C21 177.6(5) . . . . ?
C19 C20 C21 C22 -86.8(6) . . . . ?
C15 C20 C21 C22 95.3(6) . . . . ?
C20 C21 C22 N4 66.9(6) . . . . ?
C20 C21 C22 C23 -56.4(6) . . . . ?
N4 C22 C23 O4 -4.2(8) . . . . ?
C21 C22 C23 O4 121.1(6) . . . . ?
N4 C22 C23 O5 178.2(4) . . . . ?
C21 C22 C23 O5 -56.6(6) . . . . ?
C32 C26 C27 O6 -179.7(5) . . . . ?
C32 C26 C27 C29 1.6(8) . . . . ?
O6 C27 C29 C30 -179.2(6) . . . . ?
C26 C27 C29 C30 -0.7(9) . . . . ?
C27 C29 C30 C31 -0.3(10) . . . . ?
C29 C30 C31 C32 0.4(9) . . . . ?
C27 C26 C32 C31 -1.6(8) . . . . ?
C27 C26 C32 C34 178.1(4) . . . . ?
C30 C31 C32 C26 0.6(8) . . . . ?
C30 C31 C32 C34 -179.1(5) . . . . ?
C26 C32 C34 C35 -44.4(6) . . . . ?
C31 C32 C34 C35 135.3(5) . . . . ?
C26 C32 C34 C33 75.2(6) . . . . ?
C31 C32 C34 C33 -105.1(5) . . . . ?
C38 C33 C34 C35 -93.4(4) . . . . ?
S2 C33 C34 C35 24.4(4) . . . . ?
C38 C33 C34 C32 142.6(4) . . . . ?
S2 C33 C34 C32 -99.6(4) . . . . ?
C32 C34 C35 C37 104.4(5) . . . . ?
C33 C34 C35 C37 -18.8(5) . . . . ?
C32 C34 C35 C36 -75.9(5) . . . . ?
C33 C34 C35 C36 160.9(4) . . . . ?
C36 C35 C37 N6 5.5(8) . . . . ?
C34 C35 C37 N6 -174.7(4) . . . . ?
C36 C35 C37 S2 -176.1(3) . . . . ?
C34 C35 C37 S2 3.7(5) . . . . ?
C34 C33 C38 O7 21.7(6) . . . . ?
S2 C33 C38 O7 -96.1(5) . . . . ?
C34 C33 C38 N7 -158.8(4) . . . . ?
S2 C33 C38 N7 83.4(4) . . . . ?
C45 C40 C41 C42 -0.2(10) . . . . ?
C40 C41 C42 C43 -1.0(11) . . . . ?
C41 C42 C43 C44 1.1(11) . . . . ?
C42 C43 C44 C45 -0.1(10) . . . . ?
C43 C44 C45 C40 -1.1(9) . . . . ?
C43 C44 C45 C46 177.3(6) . . . . ?
C41 C40 C45 C44 1.2(9) . . . . ?
C41 C40 C45 C46 -177.1(5) . . . . ?
C44 C45 C46 C47 78.6(7) . . . . ?
C40 C45 C46 C47 -103.1(6) . . . . ?
C45 C46 C47 N8 178.3(4) . . . . ?
C45 C46 C47 C48 55.3(6) . . . . ?
N8 C47 C48 O9 138.4(6) . . . . ?
C46 C47 C48 O9 -99.7(7) . . . . ?
N8 C47 C48 O10 -44.8(6) . . . . ?
C46 C47 C48 O10 77.0(6) . . . . ?
O2 C13 N3 C14 -0.6(8) . . . . ?
C8 C13 N3 C14 177.8(4) . . . . ?
O3 C14 N3 C13 179.2(5) . . . . ?
N4 C14 N3 C13 -0.1(7) . . . . ?
O3 C14 N4 C22 1.4(7) . . . . ?
N3 C14 N4 C22 -179.3(4) . . . . ?
C23 C22 N4 C14 -138.8(5) . . . . ?
C21 C22 N4 C14 95.7(5) . . . . ?
O7 C38 N7 C39 0.3(8) . . . . ?
C33 C38 N7 C39 -179.2(4) . . . . ?
O8 C39 N7 C38 177.1(4) . . . . ?
N8 C39 N7 C38 -4.3(7) . . . . ?
O8 C39 N8 C47 -8.3(7) . . . . ?
N7 C39 N8 C47 173.2(4) . . . . ?
C48 C47 N8 C39 -86.5(6) . . . . ?
C46 C47 N8 C39 150.1(4) . . . . ?
C4 C2 O1 C3 -169.5(7) . . . . ?
C1 C2 O1 C3 10.8(9) . . . . ?
O4 C23 O5 C24 1.8(9) . . . . ?
C22 C23 O5 C24 179.6(6) . . . . ?
C25 C24 O5 C23 -170.4(8) . . . . ?
C29 C27 O6 C28 -16.0(9) . . . . ?
C26 C27 O6 C28 165.4(5) . . . . ?
O9 C48 O10 C49 -5.2(10) . . . . ?
C47 C48 O10 C49 178.0(7) . . . . ?
C50 C49 O10 C48 149.7(9) . . . . ?
N2 C12 S1 C8 170.2(4) . . . . ?
C10 C12 S1 C8 -11.7(4) . . . . ?
C13 C8 S1 C12 -101.7(3) . . . . ?
C9 C8 S1 C12 22.1(3) . . . . ?
N6 C37 S2 C33 -171.1(4) . . . . ?
C35 C37 S2 C33 10.3(4) . . . . ?
C38 C33 S2 C37 100.7(3) . . . . ?
C34 C33 S2 C37 -20.3(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
N2 H2A O7 0.86 2.59 3.248(5) 133.8 1_554
N2 H2B O8 0.86 2.06 2.912(6) 168.5 1_454
N3 H3 N1 0.86 2.16 2.990(6) 161.3 1_455
N4 H4A O2 0.86 2.11 2.748(5) 130.7 .
N6 H6A O2 0.86 2.58 3.228(5) 133.0 1_556
N6 H6B O3 0.86 2.05 2.899(5) 170.6 1_656
N7 H7 N5 0.86 2.11 2.946(6) 165.0 1_655
N8 H8A O7 0.86 2.06 2.707(5) 131.2 .

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1823980'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N4 O4 S'
_chemical_formula_sum            'C18 H20 N4 O4 S'
_chemical_formula_weight         388.44

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0489(3)
_cell_length_b                   11.7701(6)
_cell_length_c                   14.2912(7)
_cell_angle_alpha                106.8458(17)
_cell_angle_beta                 91.1007(18)
_cell_angle_gamma                94.0053(19)
_cell_volume                     970.61(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5413
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      22.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15407
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         27.650
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4477
_reflns_number_gt                3104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.4437P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4477
_refine_ls_number_parameters     266
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6620(5) 0.3163(3) 0.8658(2) 0.0562(7) Uani 1 1 d . . . . .
H1 H 0.5315 0.3231 0.8330 0.067 Uiso 1 1 calc R U . . .
C2 C 0.6860(6) 0.3665(3) 0.9665(2) 0.0671(8) Uani 1 1 d . . . . .
H2 H 0.5709 0.4065 1.0001 0.080 Uiso 1 1 calc R U . . .
C3 C 0.8755(5) 0.3582(2) 1.01745(18) 0.0547(7) Uani 1 1 d . . . . .
C4 C 0.9067(7) 0.4165(3) 1.1267(2) 0.0827(11) Uani 1 1 d . . . . .
H4A H 0.7688 0.4446 1.1526 0.124 Uiso 1 1 calc R U . . .
H4B H 1.0171 0.4823 1.1390 0.124 Uiso 1 1 calc R U . . .
H4C H 0.9539 0.3595 1.1576 0.124 Uiso 1 1 calc R U . . .
C5 C 1.0400(5) 0.2964(3) 0.96564(19) 0.0574(7) Uani 1 1 d . . . . .
H5 H 1.1691 0.2882 0.9987 0.069 Uiso 1 1 calc R U . . .
C6 C 1.0178(4) 0.2461(2) 0.86553(17) 0.0491(6) Uani 1 1 d . . . . .
H6 H 1.1318 0.2045 0.8324 0.059 Uiso 1 1 calc R U . . .
C7 C 0.8294(4) 0.2566(2) 0.81398(15) 0.0354(5) Uani 1 1 d . . . . .
C8 C 0.8896(3) 0.30096(18) 0.65229(15) 0.0311(5) Uani 1 1 d . . . . .
H8 H 0.8796 0.3812 0.6967 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8054(4) 0.20771(19) 0.70290(15) 0.0333(5) Uani 1 1 d . . . . .
H9 H 0.6479 0.1856 0.6844 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9335(4) 0.10158(18) 0.65834(15) 0.0331(5) Uani 1 1 d . . . . .
C11 C 0.8622(4) -0.0165(2) 0.65617(17) 0.0426(6) Uani 1 1 d . . . . .
C12 C 1.1304(4) 0.12582(18) 0.62119(15) 0.0320(5) Uani 1 1 d . . . . .
C13 C 0.7621(3) 0.28867(18) 0.55629(15) 0.0296(5) Uani 1 1 d . . . . .
C14 C 0.7217(4) 0.3941(2) 0.43021(17) 0.0412(6) Uani 1 1 d . . . . .
C15 C 0.4296(5) 0.3398(2) 0.30416(18) 0.0511(7) Uani 1 1 d . . . . .
H15A H 0.4785 0.4161 0.2952 0.061 Uiso 1 1 calc R U . . .
H15B H 0.2706 0.3388 0.3120 0.061 Uiso 1 1 calc R U . . .
C16 C 0.4740(6) 0.2437(3) 0.2132(2) 0.0684(9) Uani 1 1 d . . . . .
C17 C 0.7160(12) 0.1016(5) 0.1360(4) 0.1046(9) Uani 0.623(5) 1 d D U P A 1
H17A H 0.8745 0.0956 0.1419 0.125 Uiso 0.623(5) 1 calc R U P A 1
H17B H 0.6838 0.1297 0.0801 0.125 Uiso 0.623(5) 1 calc R U P A 1
C18 C 0.5872(12) -0.0166(5) 0.1275(5) 0.1082(13) Uani 0.623(5) 1 d D U P A 1
H18A H 0.6224 -0.0423 0.1836 0.162 Uiso 0.623(5) 1 calc R U P A 1
H18B H 0.6266 -0.0751 0.0692 0.162 Uiso 0.623(5) 1 calc R U P A 1
H18C H 0.4310 -0.0074 0.1243 0.162 Uiso 0.623(5) 1 calc R U P A 1
C17' C 0.6333(18) 0.0562(6) 0.1623(7) 0.1040(10) Uani 0.377(5) 1 d D U P A 2
H17C H 0.4963 0.0338 0.1228 0.125 Uiso 0.377(5) 1 calc R U P A 2
H17D H 0.6457 0.0019 0.2015 0.125 Uiso 0.377(5) 1 calc R U P A 2
C18' C 0.8300(17) 0.0502(10) 0.0971(7) 0.1065(14) Uani 0.377(5) 1 d D U P A 2
H18D H 0.8092 0.0984 0.0542 0.160 Uiso 0.377(5) 1 calc R U P A 2
H18E H 0.8418 -0.0309 0.0589 0.160 Uiso 0.377(5) 1 calc R U P A 2
H18F H 0.9633 0.0792 0.1369 0.160 Uiso 0.377(5) 1 calc R U P A 2
N1 N 0.8065(5) -0.1129(2) 0.6507(2) 0.0702(7) Uani 1 1 d . . . . .
N2 N 1.2906(3) 0.05301(17) 0.58665(15) 0.0440(5) Uani 1 1 d . . . . .
H2A H 1.2750 -0.0203 0.5863 0.053 Uiso 1 1 calc R U . . .
H2B H 1.4088 0.0797 0.5649 0.053 Uiso 1 1 calc R U . . .
N3 N 0.8111(3) 0.37776(16) 0.51637(14) 0.0439(5) Uani 1 1 d . . . . .
H3 H 0.9106 0.4318 0.5480 0.053 Uiso 1 1 calc R U . . .
N4 N 0.5342(3) 0.33163(17) 0.39328(14) 0.0444(5) Uani 1 1 d . . . . .
H4 H 0.4726 0.2847 0.4232 0.053 Uiso 1 1 calc R U . . .
O1 O 0.6266(2) 0.20511(13) 0.51960(11) 0.0371(4) Uani 1 1 d . . . . .
O2 O 0.8186(3) 0.46715(16) 0.39620(13) 0.0615(6) Uani 1 1 d . . . . .
O3 O 0.3745(5) 0.2292(3) 0.13751(17) 0.1157(10) Uani 1 1 d . . . . .
O4 O 0.6334(5) 0.1798(2) 0.22630(17) 0.1020(8) Uani 1 1 d D U . . .
S1 S 1.18067(9) 0.27639(5) 0.62607(4) 0.03609(18) 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
C1 C7 1.376(3) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C5 1.373(4) . ?
C3 C4 1.514(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 C9 1.524(3) . ?
C8 C13 1.525(3) . ?
C8 C9 1.544(3) . ?
C8 S1 1.832(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.503(3) . ?
C9 H9 0.9800 . ?
C10 C12 1.359(3) . ?
C10 C11 1.417(3) . ?
C11 N1 1.141(3) . ?
C12 N2 1.344(3) . ?
C12 S1 1.758(2) . ?
C13 O1 1.219(2) . ?
C13 N3 1.350(3) . ?
C14 O2 1.225(3) . ?
C14 N4 1.320(3) . ?
C14 N3 1.404(3) . ?
C15 N4 1.442(3) . ?
C15 C16 1.498(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O3 1.190(3) . ?
C16 O4 1.306(4) . ?
C17 O4 1.471(4) . ?
C17 C18 1.518(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17' O4 1.477(5) . ?
C17' C18' 1.519(5) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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
C7 C1 C2 120.6(3) . . ?
C7 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C5 117.6(2) . . ?
C2 C3 C4 121.9(3) . . ?
C5 C3 C4 120.5(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.4(3) . . ?
C3 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C7 C6 117.9(2) . . ?
C1 C7 C9 120.0(2) . . ?
C6 C7 C9 122.1(2) . . ?
C13 C8 C9 112.83(16) . . ?
C13 C8 S1 108.56(14) . . ?
C9 C8 S1 106.69(14) . . ?
C13 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
S1 C8 H8 109.6 . . ?
C10 C9 C7 115.25(18) . . ?
C10 C9 C8 104.29(17) . . ?
C7 C9 C8 111.76(17) . . ?
C10 C9 H9 108.4 . . ?
C7 C9 H9 108.4 . . ?
C8 C9 H9 108.4 . . ?
C12 C10 C11 120.7(2) . . ?
C12 C10 C9 115.40(18) . . ?
C11 C10 C9 123.8(2) . . ?
N1 C11 C10 177.4(3) . . ?
N2 C12 C10 129.2(2) . . ?
N2 C12 S1 117.42(16) . . ?
C10 C12 S1 113.31(17) . . ?
O1 C13 N3 123.32(19) . . ?
O1 C13 C8 122.18(18) . . ?
N3 C13 C8 114.50(17) . . ?
O2 C14 N4 124.6(2) . . ?
O2 C14 N3 118.2(2) . . ?
N4 C14 N3 117.10(19) . . ?
N4 C15 C16 115.6(2) . . ?
N4 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
N4 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
O3 C16 O4 124.4(3) . . ?
O3 C16 C15 122.8(3) . . ?
O4 C16 C15 112.8(2) . . ?
O4 C17 C18 102.3(4) . . ?
O4 C17 H17A 111.3 . . ?
C18 C17 H17A 111.3 . . ?
O4 C17 H17B 111.3 . . ?
C18 C17 H17B 111.3 . . ?
H17A C17 H17B 109.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C17' C18' 107.8(6) . . ?
O4 C17' H17C 110.1 . . ?
C18' C17' H17C 110.1 . . ?
O4 C17' H17D 110.1 . . ?
C18' C17' H17D 110.1 . . ?
H17C C17' H17D 108.5 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 128.74(18) . . ?
C13 N3 H3 115.6 . . ?
C14 N3 H3 115.6 . . ?
C14 N4 C15 121.81(19) . . ?
C14 N4 H4 119.1 . . ?
C15 N4 H4 119.1 . . ?
C16 O4 C17 115.0(4) . . ?
C16 O4 C17' 118.4(6) . . ?
C12 S1 C8 90.30(10) . . ?

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
N2 H2A O1 0.86 2.38 3.058(2) 135.7 2_756
N2 H2B O1 0.86 2.16 2.969(2) 157.5 1_655
N3 H3 O2 0.86 1.97 2.812(2) 167.9 2_766
N4 H4 N1 0.86 2.50 3.089(3) 125.9 2_656
N4 H4 O1 0.86 2.11 2.725(2) 127.6 .

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_2l
_database_code_depnum_ccdc_archive 'CCDC 1823984'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H28 N4 O5 S'
_chemical_formula_sum            'C26 H28 N4 O5 S'
_chemical_formula_weight         508.58

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.559
_cell_length_b                   17.5588(13)
_cell_length_c                   8.3081(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2561.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4278
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      22.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20711
_diffrn_reflns_av_unetI/netI     0.1896
_diffrn_reflns_av_R_equivalents  0.1632
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.891
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             4614
_reflns_number_gt                2499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.931
_reflns_Friedel_fraction_full    0.924

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0183P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 761 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4614
_refine_ls_number_parameters     327
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2031(3) 0.4212(3) 0.5439(7) 0.0444(15) Uani 1 1 d . . . . .
H1 H 0.2237 0.4614 0.6025 0.053 Uiso 1 1 calc R U . . .
C2 C 0.1248(3) 0.4115(4) 0.5374(7) 0.0552(17) Uani 1 1 d . . . . .
H2 H 0.0933 0.4463 0.5894 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0933(3) 0.3520(4) 0.4562(7) 0.0440(15) Uani 1 1 d . . . . .
C4 C -0.0196(4) 0.2995(4) 0.3426(8) 0.066(2) Uani 1 1 d . . . . .
H4A H -0.0023 0.3124 0.2365 0.099 Uiso 1 1 calc R U . . .
H4B H -0.0738 0.3057 0.3484 0.099 Uiso 1 1 calc R U . . .
H4C H -0.0065 0.2476 0.3658 0.099 Uiso 1 1 calc R U . . .
C5 C 0.1403(3) 0.2996(3) 0.3789(7) 0.0434(15) Uani 1 1 d . . . . .
H5 H 0.1198 0.2578 0.3256 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2180(3) 0.3113(3) 0.3834(7) 0.0429(15) Uani 1 1 d . . . . .
H6 H 0.2493 0.2769 0.3299 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2513(3) 0.3709(3) 0.4627(6) 0.0325(13) Uani 1 1 d . . . . .
C8 C 0.3385(3) 0.3798(3) 0.4643(6) 0.0301(12) Uani 1 1 d . . . . .
H8 H 0.3607 0.3309 0.4966 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3684(3) 0.4403(3) 0.5773(6) 0.0325(13) Uani 1 1 d . . . . .
C10 C 0.3655(3) 0.4323(3) 0.7491(7) 0.0383(14) Uani 1 1 d . . . . .
C11 C 0.3951(3) 0.5038(3) 0.5108(6) 0.0346(12) Uani 1 1 d . . . . .
C12 C 0.3718(3) 0.4012(3) 0.2981(6) 0.0305(12) Uani 1 1 d . . . . .
H12 H 0.3353 0.3881 0.2132 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4488(3) 0.3618(3) 0.2652(6) 0.0290(12) Uani 1 1 d . . . . .
C14 C 0.5352(3) 0.3304(3) 0.0364(7) 0.0335(13) Uani 1 1 d . . . . .
C15 C 0.8555(3) 0.3172(4) -0.0743(9) 0.0562(18) Uani 1 1 d . . . . .
H15 H 0.8870 0.2932 0.0001 0.067 Uiso 1 1 calc R U . . .
C16 C 0.8824(4) 0.3311(4) -0.2260(9) 0.0649(19) Uani 1 1 d . . . . .
H16 H 0.9318 0.3173 -0.2535 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8356(4) 0.3659(4) -0.3389(9) 0.0654(19) Uani 1 1 d . . . . .
H17 H 0.8532 0.3756 -0.4424 0.078 Uiso 1 1 calc R U . . .
C18 C 0.7630(4) 0.3858(4) -0.2951(11) 0.065(2) Uani 1 1 d . . . . .
H18 H 0.7312 0.4088 -0.3703 0.078 Uiso 1 1 calc R U . . .
C19 C 0.7366(4) 0.3726(4) -0.1447(10) 0.058(2) Uani 1 1 d . . . . .
H19 H 0.6871 0.3870 -0.1186 0.070 Uiso 1 1 calc R U . . .
C20 C 0.7816(3) 0.3383(4) -0.0284(8) 0.0507(17) Uani 1 1 d . . . . .
C21 C 0.7526(4) 0.3251(4) 0.1401(9) 0.064(2) Uani 1 1 d . . . . .
H21A H 0.7167 0.3651 0.1669 0.077 Uiso 1 1 calc R U . . .
H21B H 0.7950 0.3289 0.2145 0.077 Uiso 1 1 calc R U . . .
C22 C 0.7137(3) 0.2480(4) 0.1636(7) 0.0528(17) Uani 1 1 d . . . . .
H22A H 0.7486 0.2079 0.1316 0.063 Uiso 1 1 calc R U . . .
H22B H 0.7024 0.2411 0.2769 0.063 Uiso 1 1 calc R U . . .
C23 C 0.6406(3) 0.2402(3) 0.0676(7) 0.0372(14) Uani 1 1 d . . . . .
H23 H 0.6515 0.2571 -0.0424 0.045 Uiso 1 1 calc R U . . .
C24 C 0.6107(4) 0.1602(4) 0.0571(8) 0.0591(15) Uani 1 1 d . U . . .
C25 C 0.6420(6) 0.0311(4) 0.0147(11) 0.102(2) Uani 1 1 d . U . . .
H25A H 0.6851 0.0004 0.0484 0.122 Uiso 1 1 calc R U . . .
H25B H 0.6007 0.0219 0.0897 0.122 Uiso 1 1 calc R U . . .
C26 C 0.6189(6) 0.0078(5) -0.1428(9) 0.116(3) Uani 1 1 d . U . . .
H26A H 0.5742 0.0356 -0.1739 0.175 Uiso 1 1 calc R U . . .
H26B H 0.6077 -0.0457 -0.1422 0.175 Uiso 1 1 calc R U . . .
H26C H 0.6591 0.0178 -0.2180 0.175 Uiso 1 1 calc R U . . .
N1 N 0.3622(3) 0.4294(3) 0.8847(6) 0.0591(16) Uani 1 1 d . . . . .
N2 N 0.4223(3) 0.5669(3) 0.5800(6) 0.0458(12) Uani 1 1 d . . . . .
H2A H 0.4243 0.5702 0.6832 0.055 Uiso 1 1 calc R U . . .
H2B H 0.4378 0.6041 0.5214 0.055 Uiso 1 1 calc R U . . .
N3 N 0.4703(2) 0.3624(3) 0.1086(5) 0.0332(11) Uani 1 1 d . . . . .
H3 H 0.4399 0.3858 0.0442 0.040 Uiso 1 1 calc R U . . .
N4 N 0.5813(2) 0.2909(3) 0.1326(5) 0.0393(12) Uani 1 1 d . . . . .
H4 H 0.5762 0.2950 0.2352 0.047 Uiso 1 1 calc R U . . .
O1 O 0.0156(2) 0.3478(3) 0.4559(5) 0.0700(14) Uani 1 1 d . . . . .
O2 O 0.4863(2) 0.3339(2) 0.3726(4) 0.0380(9) Uani 1 1 d . . . . .
O3 O 0.5443(2) 0.3409(2) -0.1072(5) 0.0483(10) Uani 1 1 d . . . . .
O4 O 0.5456(3) 0.1433(3) 0.0812(8) 0.0981(17) Uani 1 1 d . U . . .
O5 O 0.6631(3) 0.1111(3) 0.0213(6) 0.0783(14) Uani 1 1 d . U . . .
S1 S 0.38826(8) 0.50348(9) 0.29922(16) 0.0412(4) 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
C1 C2 1.387(8) . ?
C1 C7 1.396(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(8) . ?
C2 H2 0.9300 . ?
C3 O1 1.367(6) . ?
C3 C5 1.392(8) . ?
C4 O1 1.409(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.380(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.540(7) . ?
C8 C9 1.511(7) . ?
C8 C12 1.545(7) . ?
C8 H8 0.9800 . ?
C9 C11 1.330(7) . ?
C9 C10 1.435(8) . ?
C10 N1 1.129(6) . ?
C11 N2 1.336(7) . ?
C11 S1 1.762(5) . ?
C12 C13 1.544(7) . ?
C12 S1 1.819(5) . ?
C12 H12 0.9800 . ?
C13 O2 1.212(6) . ?
C13 N3 1.354(6) . ?
C14 O3 1.218(6) . ?
C14 N4 1.333(7) . ?
C14 N3 1.404(6) . ?
C15 C16 1.368(10) . ?
C15 C20 1.402(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.352(11) . ?
C18 H18 0.9300 . ?
C19 C20 1.386(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.507(10) . ?
C21 C22 1.529(10) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.518(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 N4 1.472(6) . ?
C23 C24 1.502(9) . ?
C23 H23 0.9800 . ?
C24 O4 1.197(7) . ?
C24 O5 1.295(7) . ?
C25 C26 1.430(10) . ?
C25 O5 1.454(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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 C1 C7 120.3(5) . . ?
C2 C1 H1 119.9 . . ?
C7 C1 H1 119.9 . . ?
C3 C2 C1 121.1(6) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 O1 116.6(5) . . ?
C2 C3 C5 119.6(5) . . ?
O1 C3 C5 123.8(5) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 118.4(5) . . ?
C6 C5 H5 120.8 . . ?
C3 C5 H5 120.8 . . ?
C7 C6 C5 123.3(5) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C6 C7 C1 117.3(5) . . ?
C6 C7 C8 120.4(5) . . ?
C1 C7 C8 122.3(5) . . ?
C9 C8 C7 114.9(4) . . ?
C9 C8 C12 104.7(4) . . ?
C7 C8 C12 113.1(4) . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C12 C8 H8 107.9 . . ?
C11 C9 C10 120.4(5) . . ?
C11 C9 C8 117.0(4) . . ?
C10 C9 C8 122.5(5) . . ?
N1 C10 C9 176.9(7) . . ?
C9 C11 N2 130.0(5) . . ?
C9 C11 S1 112.8(4) . . ?
N2 C11 S1 117.2(4) . . ?
C13 C12 C8 112.4(4) . . ?
C13 C12 S1 107.7(3) . . ?
C8 C12 S1 107.2(3) . . ?
C13 C12 H12 109.8 . . ?
C8 C12 H12 109.8 . . ?
S1 C12 H12 109.8 . . ?
O2 C13 N3 124.0(5) . . ?
O2 C13 C12 121.8(4) . . ?
N3 C13 C12 114.3(4) . . ?
O3 C14 N4 125.9(5) . . ?
O3 C14 N3 117.7(5) . . ?
N4 C14 N3 116.4(5) . . ?
C16 C15 C20 121.5(6) . . ?
C16 C15 H15 119.3 . . ?
C20 C15 H15 119.3 . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 118.9(7) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C19 C18 C17 121.3(7) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 121.6(6) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C15 116.9(7) . . ?
C19 C20 C21 121.4(6) . . ?
C15 C20 C21 121.6(6) . . ?
C20 C21 C22 113.9(6) . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 113.0(5) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N4 C23 C24 109.8(4) . . ?
N4 C23 C22 110.6(4) . . ?
C24 C23 C22 114.2(5) . . ?
N4 C23 H23 107.3 . . ?
C24 C23 H23 107.3 . . ?
C22 C23 H23 107.3 . . ?
O4 C24 O5 123.5(7) . . ?
O4 C24 C23 123.7(6) . . ?
O5 C24 C23 112.8(6) . . ?
C26 C25 O5 112.5(7) . . ?
C26 C25 H25A 109.1 . . ?
O5 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
O5 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 129.3(5) . . ?
C13 N3 H3 115.4 . . ?
C14 N3 H3 115.4 . . ?
C14 N4 C23 121.7(4) . . ?
C14 N4 H4 119.2 . . ?
C23 N4 H4 119.2 . . ?
C3 O1 C4 118.1(5) . . ?
C24 O5 C25 118.1(7) . . ?
C11 S1 C12 91.1(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
N2 H2A O3 0.86 2.40 3.117(6) 140.9 2_666
N2 H2B O2 0.86 2.12 2.929(6) 157.0 2_665
N3 H3 N1 0.86 2.05 2.907(7) 173.4 1_554
N4 H4 O2 0.86 2.07 2.707(5) 130.9 .

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1823981'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 N4 O5 S'
_chemical_formula_sum            'C25 H26 N4 O5 S'
_chemical_formula_weight         494.56

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

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

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

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

_cell_length_a                   8.4154(17)
_cell_length_b                   34.970(7)
_cell_length_c                   8.6188(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.377(7)
_cell_angle_gamma                90
_cell_volume                     2494.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.26

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25800
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         27.550
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_point_group_measured_fraction_full 0.875
_reflns_number_total             9462
_reflns_number_gt                7071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_max     0.648
_reflns_Friedel_fraction_full    0.750

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0501P)²+0.1202P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9462
_refine_ls_number_parameters     635
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0518(4) 0.59839(10) 0.7533(4) 0.0398(8) Uani 1 1 d . . . . .
H1 H -0.0579 0.5780 0.6830 0.048 Uiso 1 1 calc R U . . .
C2 C -0.0461(4) 0.63551(11) 0.6958(5) 0.0450(9) Uani 1 1 d . . . . .
H2 H -0.0466 0.6399 0.5893 0.054 Uiso 1 1 calc R U . . .
C3 C -0.0399(4) 0.66557(10) 0.7995(5) 0.0463(10) Uani 1 1 d . . . . .
C4 C 0.0002(7) 0.71104(13) 0.6048(6) 0.0808(15) Uani 1 1 d . . . . .
H4A H 0.0980 0.6981 0.5933 0.121 Uiso 1 1 calc R U . . .
H4B H 0.0139 0.7381 0.5934 0.121 Uiso 1 1 calc R U . . .
H4C H -0.0869 0.7022 0.5252 0.121 Uiso 1 1 calc R U . . .
C5 C -0.0401(5) 0.65865(10) 0.9552(5) 0.0549(11) Uani 1 1 d . . . . .
H5 H -0.0386 0.6791 1.0244 0.066 Uiso 1 1 calc R U . . .
C6 C -0.0427(5) 0.62196(10) 1.0111(5) 0.0456(9) Uani 1 1 d . . . . .
H6 H -0.0402 0.6178 1.1181 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0489(4) 0.59083(9) 0.9091(4) 0.0333(8) Uani 1 1 d . . . . .
C8 C 0.1304(4) 0.53596(9) 1.0247(4) 0.0340(8) Uani 1 1 d . . . . .
H8 H 0.2045 0.5520 0.9776 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0443(4) 0.54996(9) 0.9677(4) 0.0327(7) Uani 1 1 d . . . . .
H9 H -0.0956 0.5335 0.8810 0.039 Uiso 1 1 calc R U . . .
C10 C -0.1306(4) 0.54457(9) 1.1062(4) 0.0315(7) Uani 1 1 d . . . . .
C11 C -0.3002(5) 0.54619(10) 1.0885(4) 0.0405(9) Uani 1 1 d . . . . .
C12 C -0.0335(4) 0.54120(9) 1.2492(4) 0.0362(8) Uani 1 1 d . . . . .
C13 C 0.1586(4) 0.49442(9) 0.9877(4) 0.0344(8) Uani 1 1 d . . . . .
C14 C 0.3908(4) 0.45185(11) 0.9557(4) 0.0362(8) Uani 1 1 d . . . . .
C15 C 0.1999(7) 0.37157(13) 1.2465(6) 0.0723(13) Uani 1 1 d . . . . .
H15 H 0.2403 0.3960 1.2721 0.087 Uiso 1 1 calc R U . . .
C16 C 0.0699(7) 0.35917(14) 1.3056(6) 0.0819(15) Uani 1 1 d . . . . .
H16 H 0.0227 0.3752 1.3704 0.098 Uiso 1 1 calc R U . . .
C17 C 0.0070(7) 0.32334(14) 1.2712(6) 0.0749(13) Uani 1 1 d . . . . .
H17 H -0.0819 0.3149 1.3119 0.090 Uiso 1 1 calc R U . . .
C18 C 0.0786(7) 0.30035(13) 1.1754(6) 0.0755(14) Uani 1 1 d . . . . .
H18 H 0.0378 0.2759 1.1509 0.091 Uiso 1 1 calc R U . . .
C19 C 0.2100(6) 0.31266(11) 1.1146(5) 0.0643(12) Uani 1 1 d . . . . .
H19 H 0.2565 0.2966 1.0494 0.077 Uiso 1 1 calc R U . . .
C20 C 0.2735(5) 0.34876(11) 1.1494(5) 0.0534(11) Uani 1 1 d . . . . .
C21 C 0.4190(5) 0.36252(12) 1.0814(5) 0.0583(11) Uani 1 1 d . . . . .
H21A H 0.4855 0.3406 1.0671 0.070 Uiso 1 1 calc R U . . .
H21B H 0.4832 0.3794 1.1572 0.070 Uiso 1 1 calc R U . . .
C22 C 0.3746(5) 0.38367(10) 0.9234(5) 0.0481(10) Uani 1 1 d . . . . .
H22 H 0.4752 0.3884 0.8844 0.058 Uiso 1 1 calc R U . . .
C23 C 0.2667(5) 0.36061(11) 0.8003(5) 0.0496(10) Uani 1 1 d . . . . .
C24 C 0.2517(9) 0.30111(17) 0.6664(8) 0.120(3) Uani 1 1 d . . . . .
H24A H 0.1368 0.3022 0.6677 0.144 Uiso 1 1 calc R U . . .
H24B H 0.2686 0.3075 0.5611 0.144 Uiso 1 1 calc R U . . .
C25 C 0.3122(11) 0.2639(2) 0.7085(13) 0.206(5) Uani 1 1 d . . . . .
H25A H 0.4209 0.2657 0.7658 0.308 Uiso 1 1 calc R U . . .
H25B H 0.3112 0.2490 0.6147 0.308 Uiso 1 1 calc R U . . .
H25C H 0.2455 0.2517 0.7734 0.308 Uiso 1 1 calc R U . . .
C26 C 0.7878(4) 0.38354(11) 0.8227(4) 0.0447(9) Uani 1 1 d . . . . .
H26 H 0.8076 0.4018 0.9025 0.054 Uiso 1 1 calc R U . . .
C27 C 0.7880(5) 0.34571(12) 0.8616(5) 0.0579(11) Uani 1 1 d . . . . .
H27 H 0.8086 0.3385 0.9672 0.070 Uiso 1 1 calc R U . . .
C28 C 0.7583(5) 0.31836(11) 0.7471(5) 0.0550(11) Uani 1 1 d . . . . .
C29 C 0.7748(9) 0.25167(14) 0.6862(8) 0.121(2) Uani 1 1 d . . . . .
H29A H 0.6769 0.2513 0.6093 0.181 Uiso 1 1 calc R U . . .
H29B H 0.7893 0.2274 0.7387 0.181 Uiso 1 1 calc R U . . .
H29C H 0.8648 0.2566 0.6347 0.181 Uiso 1 1 calc R U . . .
C30 C 0.7272(6) 0.32911(12) 0.5929(5) 0.0638(12) Uani 1 1 d . . . . .
H30 H 0.7068 0.3107 0.5138 0.077 Uiso 1 1 calc R U . . .
C31 C 0.7261(5) 0.36741(10) 0.5546(5) 0.0532(11) Uani 1 1 d . . . . .
H31 H 0.7026 0.3745 0.4489 0.064 Uiso 1 1 calc R U . . .
C32 C 0.7584(4) 0.39539(9) 0.6666(4) 0.0355(8) Uani 1 1 d . . . . .
C33 C 0.5918(4) 0.45376(10) 0.5660(4) 0.0337(7) Uani 1 1 d . . . . .
H33 H 0.5120 0.4383 0.6078 0.040 Uiso 1 1 calc R U . . .
C34 C 0.7637(4) 0.43764(9) 0.6245(4) 0.0329(7) Uani 1 1 d . . . . .
H34 H 0.8147 0.4520 0.7181 0.039 Uiso 1 1 calc R U . . .
C35 C 0.8546(4) 0.44511(9) 0.4927(4) 0.0348(8) Uani 1 1 d . . . . .
C36 C 1.0259(4) 0.44612(9) 0.5149(4) 0.0381(8) Uani 1 1 d . . . . .
C37 C 0.7637(4) 0.44945(9) 0.3480(4) 0.0336(7) Uani 1 1 d . . . . .
C38 C 0.5728(4) 0.49556(9) 0.6066(4) 0.0325(8) Uani 1 1 d . . . . .
C39 C 0.3529(4) 0.54115(10) 0.6382(4) 0.0355(8) Uani 1 1 d . . . . .
C40 C 0.3683(5) 0.68447(14) 0.8905(5) 0.0627(12) Uani 1 1 d . . . . .
H40 H 0.3180 0.6661 0.9428 0.075 Uiso 1 1 calc R U . . .
C41 C 0.3332(7) 0.72260(19) 0.9067(7) 0.0943(19) Uani 1 1 d . . . . .
H41 H 0.2603 0.7297 0.9708 0.113 Uiso 1 1 calc R U . . .
C42 C 0.4034(9) 0.74978(18) 0.8309(10) 0.111(3) Uani 1 1 d . . . . .
H42 H 0.3796 0.7755 0.8431 0.133 Uiso 1 1 calc R U . . .
C43 C 0.5089(8) 0.73945(15) 0.7365(9) 0.102(2) Uani 1 1 d . . . . .
H43 H 0.5557 0.7581 0.6823 0.122 Uiso 1 1 calc R U . . .
C44 C 0.5477(5) 0.70129(12) 0.7201(6) 0.0701(13) Uani 1 1 d . . . . .
H44 H 0.6216 0.6946 0.6566 0.084 Uiso 1 1 calc R U . . .
C45 C 0.4772(4) 0.67337(10) 0.7973(5) 0.0452(9) Uani 1 1 d . . . . .
C46 C 0.5190(5) 0.63186(10) 0.7814(5) 0.0495(10) Uani 1 1 d . . . . .
H46A H 0.5273 0.6197 0.8837 0.059 Uiso 1 1 calc R U . . .
H46B H 0.6241 0.6302 0.7506 0.059 Uiso 1 1 calc R U . . .
C47 C 0.3971(4) 0.60976(10) 0.6619(4) 0.0406(9) Uani 1 1 d . . . . .
H47 H 0.2939 0.6091 0.6995 0.049 Uiso 1 1 calc R U . . .
C48 C 0.3703(5) 0.62872(11) 0.5028(5) 0.0509(10) Uani 1 1 d . . . . .
C49 C 0.4896(8) 0.6413(2) 0.2791(6) 0.105(2) Uani 1 1 d . . . . .
H49A H 0.4358 0.6239 0.1985 0.126 Uiso 1 1 calc R U . . .
H49B H 0.4285 0.6649 0.2720 0.126 Uiso 1 1 calc R U . . .
C50 C 0.6497(9) 0.6487(2) 0.2545(7) 0.120(2) Uani 1 1 d . . . . .
H50A H 0.7020 0.6660 0.3341 0.180 Uiso 1 1 calc R U . . .
H50B H 0.6457 0.6600 0.1523 0.180 Uiso 1 1 calc R U . . .
H50C H 0.7092 0.6252 0.2607 0.180 Uiso 1 1 calc R U . . .
N1 N -0.4390(4) 0.54766(10) 1.0733(4) 0.0602(9) Uani 1 1 d . . . . .
N2 N -0.0737(4) 0.53922(9) 1.3924(3) 0.0489(8) Uani 1 1 d . . . . .
H2A H -0.1737 0.5401 1.4019 0.059 Uiso 1 1 calc R U . . .
H2B H 0.0003 0.5371 1.4749 0.059 Uiso 1 1 calc R U . . .
N3 N 0.3158(3) 0.48676(7) 0.9772(3) 0.0352(7) Uani 1 1 d . . . . .
H3 H 0.3782 0.5064 0.9850 0.042 Uiso 1 1 calc R U . . .
N4 N 0.3004(4) 0.42068(8) 0.9410(4) 0.0451(8) Uani 1 1 d . . . . .
H4 H 0.1986 0.4222 0.9418 0.054 Uiso 1 1 calc R U . . .
N5 N 1.1639(4) 0.44817(10) 0.5282(4) 0.0610(9) Uani 1 1 d . . . . .
N6 N 0.8103(4) 0.45251(9) 0.2075(3) 0.0491(7) Uani 1 1 d . . . . .
H6A H 0.9113 0.4518 0.2020 0.059 Uiso 1 1 calc R U . . .
H6B H 0.7392 0.4552 0.1231 0.059 Uiso 1 1 calc R U . . .
N7 N 0.4183(3) 0.50524(7) 0.6174(3) 0.0330(6) Uani 1 1 d . . . . .
H7 H 0.3514 0.4865 0.6104 0.040 Uiso 1 1 calc R U . . .
N8 N 0.4540(4) 0.57056(8) 0.6532(4) 0.0456(8) Uani 1 1 d . . . . .
H8A H 0.5555 0.5664 0.6580 0.055 Uiso 1 1 calc R U . . .
O1 O -0.0358(4) 0.70322(7) 0.7564(4) 0.0654(8) Uani 1 1 d . . . . .
O2 O 0.0528(3) 0.47045(7) 0.9730(3) 0.0525(7) Uani 1 1 d . . . . .
O3 O 0.5360(3) 0.45235(7) 0.9516(3) 0.0490(6) Uani 1 1 d . . . . .
O4 O 0.1362(4) 0.36964(9) 0.7342(4) 0.0749(9) Uani 1 1 d . . . . .
O5 O 0.3373(4) 0.32767(9) 0.7798(4) 0.0784(10) Uani 1 1 d . . . . .
O6 O 0.7650(5) 0.28089(9) 0.7987(4) 0.0840(10) Uani 1 1 d . . . . .
O7 O 0.6855(3) 0.51800(7) 0.6252(3) 0.0515(7) Uani 1 1 d . . . . .
O8 O 0.2083(3) 0.54348(7) 0.6416(3) 0.0522(7) Uani 1 1 d . . . . .
O9 O 0.2516(4) 0.64603(10) 0.4470(4) 0.0856(10) Uani 1 1 d . . . . .
O10 O 0.4968(4) 0.62427(10) 0.4343(4) 0.0770(9) Uani 1 1 d . . . . .
S1 S 0.17480(10) 0.54165(3) 1.23956(11) 0.0447(2) Uani 1 1 d . . . . .
S2 S 0.55432(10) 0.45111(3) 0.35032(10) 0.0415(2) 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
C1 C7 1.364(5) . ?
C1 C2 1.394(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C5 1.363(5) . ?
C3 O1 1.370(4) . ?
C4 O1 1.420(5) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C9 1.514(4) . ?
C8 C13 1.515(4) . ?
C8 C9 1.544(4) . ?
C8 S1 1.833(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(4) . ?
C9 H9 0.9800 . ?
C10 C12 1.355(5) . ?
C10 C11 1.410(5) . ?
C11 N1 1.152(4) . ?
C12 N2 1.339(4) . ?
C12 S1 1.770(3) . ?
C13 O2 1.213(4) . ?
C13 N3 1.368(4) . ?
C14 O3 1.229(4) . ?
C14 N4 1.322(5) . ?
C14 N3 1.402(4) . ?
C15 C16 1.359(7) . ?
C15 C20 1.381(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.527(6) . ?
C21 C22 1.536(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.457(4) . ?
C22 C23 1.501(6) . ?
C22 H22 0.9800 . ?
C23 O4 1.186(5) . ?
C23 O5 1.322(5) . ?
C24 C25 1.421(10) . ?
C24 O5 1.443(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.365(5) . ?
C26 C32 1.387(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.365(6) . ?
C27 H27 0.9300 . ?
C28 C30 1.360(6) . ?
C28 O6 1.382(5) . ?
C29 O6 1.421(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.379(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.367(5) . ?
C31 H31 0.9300 . ?
C32 C34 1.524(5) . ?
C33 C38 1.518(5) . ?
C33 C34 1.550(4) . ?
C33 S2 1.831(3) . ?
C33 H33 0.9800 . ?
C34 C35 1.502(5) . ?
C34 H34 0.9800 . ?
C35 C37 1.349(5) . ?
C35 C36 1.421(5) . ?
C36 N5 1.148(4) . ?
C37 N6 1.343(4) . ?
C37 S2 1.767(3) . ?
C38 O7 1.219(4) . ?
C38 N7 1.362(4) . ?
C39 O8 1.225(4) . ?
C39 N8 1.326(4) . ?
C39 N7 1.396(4) . ?
C40 C41 1.378(7) . ?
C40 C45 1.379(6) . ?
C40 H40 0.9300 . ?
C41 C42 1.349(9) . ?
C41 H41 0.9300 . ?
C42 C43 1.357(10) . ?
C42 H42 0.9300 . ?
C43 C44 1.387(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.375(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.505(5) . ?
C46 C47 1.527(5) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 N8 1.458(4) . ?
C47 C48 1.503(6) . ?
C47 H47 0.9800 . ?
C48 O9 1.192(4) . ?
C48 O10 1.317(5) . ?
C49 C50 1.424(8) . ?
C49 O10 1.455(6) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 H7 0.8600 . ?
N8 H8A 0.8600 . ?

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
C7 C1 C2 122.3(3) . . ?
C7 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C5 C3 O1 116.2(3) . . ?
C5 C3 C2 119.8(3) . . ?
O1 C3 C2 123.9(3) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.0(3) . . ?
C3 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C1 C7 C6 117.5(3) . . ?
C1 C7 C9 120.4(3) . . ?
C6 C7 C9 122.1(3) . . ?
C13 C8 C9 114.4(3) . . ?
C13 C8 S1 107.8(2) . . ?
C9 C8 S1 107.2(2) . . ?
C13 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
S1 C8 H8 109.1 . . ?
C7 C9 C10 113.1(3) . . ?
C7 C9 C8 111.8(3) . . ?
C10 C9 C8 105.9(3) . . ?
C7 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C12 C10 C11 122.3(3) . . ?
C12 C10 C9 115.5(3) . . ?
C11 C10 C9 121.9(3) . . ?
N1 C11 C10 179.6(5) . . ?
N2 C12 C10 129.1(3) . . ?
N2 C12 S1 117.5(3) . . ?
C10 C12 S1 113.4(2) . . ?
O2 C13 N3 123.9(3) . . ?
O2 C13 C8 123.0(3) . . ?
N3 C13 C8 113.0(3) . . ?
O3 C14 N4 124.5(3) . . ?
O3 C14 N3 117.7(3) . . ?
N4 C14 N3 117.8(3) . . ?
C16 C15 C20 121.5(4) . . ?
C16 C15 H15 119.3 . . ?
C20 C15 H15 119.3 . . ?
C15 C16 C17 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.2(5) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C19 121.2(5) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 120.6(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 117.5(4) . . ?
C15 C20 C21 121.9(4) . . ?
C19 C20 C21 120.6(4) . . ?
C20 C21 C22 114.1(3) . . ?
C20 C21 H21A 108.7 . . ?
C22 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C22 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
N4 C22 C23 109.6(3) . . ?
N4 C22 C21 112.1(3) . . ?
C23 C22 C21 112.8(3) . . ?
N4 C22 H22 107.4 . . ?
C23 C22 H22 107.4 . . ?
C21 C22 H22 107.4 . . ?
O4 C23 O5 124.6(4) . . ?
O4 C23 C22 125.9(4) . . ?
O5 C23 C22 109.5(3) . . ?
C25 C24 O5 107.7(5) . . ?
C25 C24 H24A 110.2 . . ?
O5 C24 H24A 110.2 . . ?
C25 C24 H24B 110.2 . . ?
O5 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C32 121.4(4) . . ?
C27 C26 H26 119.3 . . ?
C32 C26 H26 119.3 . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C30 C28 C27 119.4(4) . . ?
C30 C28 O6 124.5(4) . . ?
C27 C28 O6 116.1(4) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 119.6(4) . . ?
C28 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 122.3(4) . . ?
C32 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
C31 C32 C26 116.7(3) . . ?
C31 C32 C34 122.4(3) . . ?
C26 C32 C34 120.9(3) . . ?
C38 C33 C34 114.0(3) . . ?
C38 C33 S2 106.1(2) . . ?
C34 C33 S2 107.0(2) . . ?
C38 C33 H33 109.9 . . ?
C34 C33 H33 109.9 . . ?
S2 C33 H33 109.9 . . ?
C35 C34 C32 112.9(3) . . ?
C35 C34 C33 105.3(3) . . ?
C32 C34 C33 111.4(3) . . ?
C35 C34 H34 109.1 . . ?
C32 C34 H34 109.1 . . ?
C33 C34 H34 109.1 . . ?
C37 C35 C36 121.0(3) . . ?
C37 C35 C34 116.0(3) . . ?
C36 C35 C34 123.0(3) . . ?
N5 C36 C35 177.1(4) . . ?
N6 C37 C35 129.3(3) . . ?
N6 C37 S2 117.5(2) . . ?
C35 C37 S2 113.2(2) . . ?
O7 C38 N7 124.1(3) . . ?
O7 C38 C33 122.6(3) . . ?
N7 C38 C33 113.4(3) . . ?
O8 C39 N8 124.6(3) . . ?
O8 C39 N7 118.7(3) . . ?
N8 C39 N7 116.7(3) . . ?
C41 C40 C45 120.6(5) . . ?
C41 C40 H40 119.7 . . ?
C45 C40 H40 119.7 . . ?
C42 C41 C40 120.8(6) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C43 119.6(5) . . ?
C41 C42 H42 120.2 . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C44 120.6(6) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C45 C44 C43 120.3(5) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C40 118.1(4) . . ?
C44 C45 C46 120.9(4) . . ?
C40 C45 C46 121.0(4) . . ?
C45 C46 C47 114.2(3) . . ?
C45 C46 H46A 108.7 . . ?
C47 C46 H46A 108.7 . . ?
C45 C46 H46B 108.7 . . ?
C47 C46 H46B 108.7 . . ?
H46A C46 H46B 107.6 . . ?
N8 C47 C48 111.4(3) . . ?
N8 C47 C46 108.9(3) . . ?
C48 C47 C46 111.4(3) . . ?
N8 C47 H47 108.4 . . ?
C48 C47 H47 108.4 . . ?
C46 C47 H47 108.4 . . ?
O9 C48 O10 124.4(4) . . ?
O9 C48 C47 124.7(4) . . ?
O10 C48 C47 110.9(3) . . ?
C50 C49 O10 109.1(5) . . ?
C50 C49 H49A 109.9 . . ?
O10 C49 H49A 109.9 . . ?
C50 C49 H49B 109.9 . . ?
O10 C49 H49B 109.9 . . ?
H49A C49 H49B 108.3 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 130.0(3) . . ?
C13 N3 H3 115.0 . . ?
C14 N3 H3 115.0 . . ?
C14 N4 C22 119.5(3) . . ?
C14 N4 H4 120.2 . . ?
C22 N4 H4 120.2 . . ?
C37 N6 H6A 120.0 . . ?
C37 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C38 N7 C39 129.5(3) . . ?
C38 N7 H7 115.3 . . ?
C39 N7 H7 115.3 . . ?
C39 N8 C47 121.5(3) . . ?
C39 N8 H8A 119.2 . . ?
C47 N8 H8A 119.2 . . ?
C3 O1 C4 117.0(3) . . ?
C23 O5 C24 118.0(4) . . ?
C28 O6 C29 117.8(4) . . ?
C48 O10 C49 117.4(4) . . ?
C12 S1 C8 91.34(15) . . ?
C37 S2 C33 91.34(15) . . ?

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 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C5 -0.3(5) . . . . ?
C1 C2 C3 O1 -179.2(3) . . . . ?
O1 C3 C5 C6 -179.4(4) . . . . ?
C2 C3 C5 C6 1.6(6) . . . . ?
C3 C5 C6 C7 -1.5(6) . . . . ?
C2 C1 C7 C6 1.1(5) . . . . ?
C2 C1 C7 C9 -176.0(3) . . . . ?
C5 C6 C7 C1 0.2(5) . . . . ?
C5 C6 C7 C9 177.2(3) . . . . ?
C1 C7 C9 C10 -148.1(3) . . . . ?
C6 C7 C9 C10 34.9(4) . . . . ?
C1 C7 C9 C8 92.4(4) . . . . ?
C6 C7 C9 C8 -84.5(4) . . . . ?
C13 C8 C9 C7 -143.2(3) . . . . ?
S1 C8 C9 C7 97.3(3) . . . . ?
C13 C8 C9 C10 93.2(3) . . . . ?
S1 C8 C9 C10 -26.3(3) . . . . ?
C7 C9 C10 C12 -103.3(3) . . . . ?
C8 C9 C10 C12 19.5(4) . . . . ?
C7 C9 C10 C11 71.6(4) . . . . ?
C8 C9 C10 C11 -165.6(3) . . . . ?
C11 C10 C12 N2 -0.6(6) . . . . ?
C9 C10 C12 N2 174.2(3) . . . . ?
C11 C10 C12 S1 -177.7(3) . . . . ?
C9 C10 C12 S1 -2.8(4) . . . . ?
C9 C8 C13 O2 -27.3(5) . . . . ?
S1 C8 C13 O2 91.9(4) . . . . ?
C9 C8 C13 N3 154.4(3) . . . . ?
S1 C8 C13 N3 -86.4(3) . . . . ?
C20 C15 C16 C17 0.2(8) . . . . ?
C15 C16 C17 C18 -0.1(8) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C17 C18 C19 C20 0.2(7) . . . . ?
C16 C15 C20 C19 -0.1(7) . . . . ?
C16 C15 C20 C21 179.6(4) . . . . ?
C18 C19 C20 C15 -0.1(6) . . . . ?
C18 C19 C20 C21 -179.8(4) . . . . ?
C15 C20 C21 C22 -88.5(5) . . . . ?
C19 C20 C21 C22 91.2(4) . . . . ?
C20 C21 C22 N4 69.1(4) . . . . ?
C20 C21 C22 C23 -55.1(4) . . . . ?
N4 C22 C23 O4 -4.7(6) . . . . ?
C21 C22 C23 O4 120.9(5) . . . . ?
N4 C22 C23 O5 177.4(3) . . . . ?
C21 C22 C23 O5 -57.0(4) . . . . ?
C32 C26 C27 C28 -0.4(6) . . . . ?
C26 C27 C28 C30 -0.4(7) . . . . ?
C26 C27 C28 O6 178.6(4) . . . . ?
C27 C28 C30 C31 0.0(7) . . . . ?
O6 C28 C30 C31 -178.9(4) . . . . ?
C28 C30 C31 C32 1.3(7) . . . . ?
C30 C31 C32 C26 -2.0(6) . . . . ?
C30 C31 C32 C34 177.6(4) . . . . ?
C27 C26 C32 C31 1.6(5) . . . . ?
C27 C26 C32 C34 -178.1(3) . . . . ?
C31 C32 C34 C35 -44.5(4) . . . . ?
C26 C32 C34 C35 135.1(3) . . . . ?
C31 C32 C34 C33 73.7(4) . . . . ?
C26 C32 C34 C33 -106.7(4) . . . . ?
C38 C33 C34 C35 -89.3(3) . . . . ?
S2 C33 C34 C35 27.6(3) . . . . ?
C38 C33 C34 C32 148.0(3) . . . . ?
S2 C33 C34 C32 -95.1(3) . . . . ?
C32 C34 C35 C37 98.5(3) . . . . ?
C33 C34 C35 C37 -23.2(4) . . . . ?
C32 C34 C35 C36 -78.9(4) . . . . ?
C33 C34 C35 C36 159.3(3) . . . . ?
C36 C35 C37 N6 4.9(5) . . . . ?
C34 C35 C37 N6 -172.6(3) . . . . ?
C36 C35 C37 S2 -175.2(2) . . . . ?
C34 C35 C37 S2 7.3(4) . . . . ?
C34 C33 C38 O7 27.1(4) . . . . ?
S2 C33 C38 O7 -90.3(3) . . . . ?
C34 C33 C38 N7 -153.9(3) . . . . ?
S2 C33 C38 N7 88.7(3) . . . . ?
C45 C40 C41 C42 0.6(8) . . . . ?
C40 C41 C42 C43 0.5(9) . . . . ?
C41 C42 C43 C44 -1.4(10) . . . . ?
C42 C43 C44 C45 1.2(9) . . . . ?
C43 C44 C45 C40 -0.1(7) . . . . ?
C43 C44 C45 C46 -179.6(4) . . . . ?
C41 C40 C45 C44 -0.8(6) . . . . ?
C41 C40 C45 C46 178.7(4) . . . . ?
C44 C45 C46 C47 -98.7(5) . . . . ?
C40 C45 C46 C47 81.8(5) . . . . ?
C45 C46 C47 N8 177.9(3) . . . . ?
C45 C46 C47 C48 54.7(4) . . . . ?
N8 C47 C48 O9 131.6(4) . . . . ?
C46 C47 C48 O9 -106.7(5) . . . . ?
N8 C47 C48 O10 -49.6(4) . . . . ?
C46 C47 C48 O10 72.1(4) . . . . ?
O2 C13 N3 C14 -3.0(5) . . . . ?
C8 C13 N3 C14 175.2(3) . . . . ?
O3 C14 N3 C13 -179.3(3) . . . . ?
N4 C14 N3 C13 0.8(5) . . . . ?
O3 C14 N4 C22 2.0(5) . . . . ?
N3 C14 N4 C22 -178.1(3) . . . . ?
C23 C22 N4 C14 -138.1(3) . . . . ?
C21 C22 N4 C14 95.9(4) . . . . ?
O7 C38 N7 C39 5.4(5) . . . . ?
C33 C38 N7 C39 -173.6(3) . . . . ?
O8 C39 N7 C38 178.6(3) . . . . ?
N8 C39 N7 C38 -1.6(5) . . . . ?
O8 C39 N8 C47 -5.5(5) . . . . ?
N7 C39 N8 C47 174.6(3) . . . . ?
C48 C47 N8 C39 -95.3(4) . . . . ?
C46 C47 N8 C39 141.5(3) . . . . ?
C5 C3 O1 C4 166.5(4) . . . . ?
C2 C3 O1 C4 -14.6(6) . . . . ?
O4 C23 O5 C24 1.5(7) . . . . ?
C22 C23 O5 C24 179.5(5) . . . . ?
C25 C24 O5 C23 -156.3(7) . . . . ?
C30 C28 O6 C29 14.2(7) . . . . ?
C27 C28 O6 C29 -164.8(5) . . . . ?
O9 C48 O10 C49 -0.9(7) . . . . ?
C47 C48 O10 C49 -179.7(4) . . . . ?
C50 C49 O10 C48 154.5(5) . . . . ?
N2 C12 S1 C8 170.7(3) . . . . ?
C10 C12 S1 C8 -11.9(3) . . . . ?
C13 C8 S1 C12 -101.4(2) . . . . ?
C9 C8 S1 C12 22.2(2) . . . . ?
N6 C37 S2 C33 -171.0(3) . . . . ?
C35 C37 S2 C33 9.1(3) . . . . ?
C38 C33 S2 C37 100.5(2) . . . . ?
C34 C33 S2 C37 -21.5(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
N2 H2A O7 0.86 2.55 3.186(4) 131.0 1_456
N2 H2B O8 0.86 2.07 2.904(4) 164.2 1_556
N3 H3 N1 0.86 2.15 2.978(4) 162.4 1_655
N4 H4 O2 0.86 2.13 2.767(4) 130.5 .
N6 H6A O2 0.86 2.57 3.183(4) 129.4 1_654
N6 H6B O3 0.86 2.05 2.891(4) 165.3 1_554
N7 H7 N5 0.86 2.09 2.927(4) 163.0 1_455
N8 H8A O7 0.86 2.06 2.720(4) 132.7 .

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1823986'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H24 N4 O4 S'
_chemical_formula_sum            'C25 H24 N4 O4 S'
_chemical_formula_weight         476.54

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

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

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

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

_cell_length_a                   18.926(3)
_cell_length_b                   9.4145(14)
_cell_length_c                   15.008(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.887(5)
_cell_angle_gamma                90
_cell_volume                     2463.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4353
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12871
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         27.552
_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 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             5518
_reflns_number_gt                3436
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.963

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0552P)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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5518
_refine_ls_number_parameters     309
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.018
_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
C1 C 0.2729(2) 0.5680(4) 0.2513(2) 0.0473(10) Uani 1 1 d . . . . .
H1 H 0.3202 0.6001 0.2538 0.057 Uiso 1 1 calc R U . . .
C2 C 0.2354(3) 0.4606(4) 0.1887(3) 0.0573(11) Uani 1 1 d . . . . .
H2 H 0.2576 0.4216 0.1489 0.069 Uiso 1 1 calc R U . . .
C3 C 0.1659(3) 0.4093(4) 0.1835(3) 0.0611(13) Uani 1 1 d . . . . .
C4 C 0.1226(3) 0.2967(6) 0.1099(4) 0.0937(17) Uani 1 1 d . . . . .
H4A H 0.1570 0.2210 0.1111 0.141 Uiso 1 1 calc R U . . .
H4B H 0.1019 0.3382 0.0465 0.141 Uiso 1 1 calc R U . . .
H4C H 0.0816 0.2597 0.1256 0.141 Uiso 1 1 calc R U . . .
C5 C 0.1353(3) 0.4669(5) 0.2448(3) 0.0691(13) Uani 1 1 d . . . . .
H5 H 0.0894 0.4311 0.2444 0.083 Uiso 1 1 calc R U . . .
C6 C 0.1713(3) 0.5771(4) 0.3069(3) 0.0568(11) Uani 1 1 d . . . . .
H6 H 0.1487 0.6163 0.3462 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2404(2) 0.6288(4) 0.3108(2) 0.0398(9) Uani 1 1 d . . . . .
C8 C 0.3425(2) 0.7691(4) 0.4481(2) 0.0453(10) Uani 1 1 d . . . . .
C9 C 0.2752(2) 0.7582(4) 0.3684(2) 0.0407(9) Uani 1 1 d . . . . .
C10 C 0.1678(2) 0.9179(4) 0.2625(3) 0.0527(11) Uani 1 1 d . . . . .
C11 C 0.2384(2) 0.8921(4) 0.3414(3) 0.0440(10) Uani 1 1 d . . . . .
C12 C 0.2789(2) 1.0039(4) 0.3993(3) 0.0463(10) Uani 1 1 d . . . . .
C13 C 0.3964(3) 0.6655(4) 0.5111(3) 0.0507(11) Uani 1 1 d . . . . .
C14 C 0.4107(2) 0.4070(4) 0.5492(3) 0.0451(10) Uani 1 1 d . . . . .
C15 C 0.5590(3) -0.0248(5) 0.7181(3) 0.0698(14) Uani 1 1 d . . . . .
H15 H 0.5108 -0.0310 0.6683 0.084 Uiso 1 1 calc R U . . .
C16 C 0.5872(3) -0.1397(5) 0.7778(4) 0.0820(15) Uani 1 1 d . . . . .
H16 H 0.5581 -0.2221 0.7682 0.098 Uiso 1 1 calc R U . . .
C17 C 0.6568(3) -0.1333(6) 0.8500(4) 0.0802(15) Uani 1 1 d . . . . .
H17 H 0.6758 -0.2106 0.8910 0.096 Uiso 1 1 calc R U . . .
C18 C 0.6999(3) -0.0114(6) 0.8630(4) 0.0850(17) Uani 1 1 d . . . . .
H18 H 0.7482 -0.0062 0.9128 0.102 Uiso 1 1 calc R U . . .
C19 C 0.6717(3) 0.1024(5) 0.8024(3) 0.0687(13) Uani 1 1 d . . . . .
H19 H 0.7017 0.1834 0.8109 0.082 Uiso 1 1 calc R U . . .
C20 C 0.6000(2) 0.0990(4) 0.7296(3) 0.0512(10) Uani 1 1 d . . . . .
C21 C 0.5672(3) 0.2260(5) 0.6660(3) 0.0602(11) Uani 1 1 d . . . . .
H21A H 0.5417 0.1940 0.5997 0.072 Uiso 1 1 calc R U . . .
H21B H 0.6090 0.2879 0.6688 0.072 Uiso 1 1 calc R U . . .
C22 C 0.5096(2) 0.3125(4) 0.6942(2) 0.0462(10) Uani 1 1 d . . . . .
H22 H 0.4690 0.2492 0.6957 0.055 Uiso 1 1 calc R U . . .
C23 C 0.5498(2) 0.3788(4) 0.7930(3) 0.0469(10) Uani 1 1 d . . . . .
C24 C 0.5957(3) 0.3321(6) 0.9607(3) 0.0917(16) Uani 1 1 d . U . . .
H24A H 0.6421 0.3813 0.9659 0.110 Uiso 1 1 calc R U . . .
H24B H 0.5650 0.3960 0.9816 0.110 Uiso 1 1 calc R U . . .
C25 C 0.6147(4) 0.2057(7) 1.0207(3) 0.122(2) Uani 1 1 d . U . . .
H25A H 0.5689 0.1525 1.0100 0.184 Uiso 1 1 calc R U . . .
H25B H 0.6382 0.2327 1.0875 0.184 Uiso 1 1 calc R U . . .
H25C H 0.6498 0.1481 1.0043 0.184 Uiso 1 1 calc R U . . .
N1 N 0.1115(2) 0.9467(5) 0.2006(3) 0.0800(11) Uani 1 1 d . . . . .
N2 N 0.2575(2) 1.1408(3) 0.3917(3) 0.0635(10) Uani 1 1 d . . . . .
H2A H 0.2147 1.1666 0.3473 0.076 Uiso 1 1 calc R U . . .
H2B H 0.2867 1.2026 0.4311 0.076 Uiso 1 1 calc R U . . .
N3 N 0.37758(19) 0.5252(3) 0.4920(2) 0.0517(9) Uani 1 1 d . . . . .
H3 H 0.3405 0.5076 0.4377 0.062 Uiso 1 1 calc R U . . .
N4 N 0.47545(18) 0.4263(3) 0.6255(2) 0.0539(9) Uani 1 1 d . . . . .
H4 H 0.4977 0.5078 0.6346 0.065 Uiso 1 1 calc R U . . .
O1 O 0.45269(19) 0.7034(3) 0.5801(2) 0.0785(10) Uani 1 1 d . . . . .
O2 O 0.37896(17) 0.2915(3) 0.52671(18) 0.0614(8) Uani 1 1 d . . . . .
O3 O 0.57731(18) 0.4957(3) 0.8061(2) 0.0677(9) Uani 1 1 d . . . . .
O4 O 0.55293(16) 0.2885(3) 0.86131(17) 0.0589(8) Uani 1 1 d . U . . .
S1 S 0.36284(6) 0.94460(10) 0.48759(6) 0.0558(3) 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
C1 C2 1.375(5) . ?
C1 C7 1.389(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C5 1.375(6) . ?
C3 C4 1.521(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.384(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(6) . ?
C6 H6 0.9300 . ?
C7 C9 1.491(5) . ?
C8 C9 1.370(5) . ?
C8 C13 1.463(5) . ?
C8 S1 1.747(3) . ?
C9 C11 1.420(5) . ?
C10 N1 1.142(5) . ?
C10 C11 1.419(6) . ?
C11 C12 1.391(5) . ?
C12 N2 1.342(5) . ?
C12 S1 1.719(4) . ?
C13 O1 1.215(5) . ?
C13 N3 1.369(5) . ?
C14 O2 1.224(4) . ?
C14 N4 1.325(5) . ?
C14 N3 1.397(4) . ?
C15 C20 1.372(6) . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.343(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.505(5) . ?
C21 C22 1.546(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.453(4) . ?
C22 C23 1.512(5) . ?
C22 H22 0.9800 . ?
C23 O3 1.200(4) . ?
C23 O4 1.316(5) . ?
C24 C25 1.450(8) . ?
C24 O4 1.452(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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 C1 C7 120.1(4) . . ?
C2 C1 H1 120.0 . . ?
C7 C1 H1 120.0 . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C5 117.8(4) . . ?
C2 C3 C4 121.3(5) . . ?
C5 C3 C4 120.8(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 C6 121.4(4) . . ?
C3 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.3(4) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C1 118.6(4) . . ?
C6 C7 C9 120.8(4) . . ?
C1 C7 C9 120.2(4) . . ?
C9 C8 C13 133.9(3) . . ?
C9 C8 S1 112.0(3) . . ?
C13 C8 S1 113.9(3) . . ?
C8 C9 C11 111.7(3) . . ?
C8 C9 C7 128.2(3) . . ?
C11 C9 C7 120.2(3) . . ?
N1 C10 C11 176.1(4) . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 C9 113.8(3) . . ?
C10 C11 C9 126.0(3) . . ?
N2 C12 C11 126.8(4) . . ?
N2 C12 S1 122.4(3) . . ?
C11 C12 S1 110.8(3) . . ?
O1 C13 N3 122.2(3) . . ?
O1 C13 C8 121.0(3) . . ?
N3 C13 C8 116.6(4) . . ?
O2 C14 N4 123.4(3) . . ?
O2 C14 N3 118.9(3) . . ?
N4 C14 N3 117.7(3) . . ?
C20 C15 C16 122.0(4) . . ?
C20 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 120.1(5) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.5(4) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.3(5) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 117.1(4) . . ?
C15 C20 C21 121.5(4) . . ?
C19 C20 C21 121.5(4) . . ?
C20 C21 C22 113.9(3) . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
N4 C22 C23 107.9(3) . . ?
N4 C22 C21 111.1(3) . . ?
C23 C22 C21 110.3(3) . . ?
N4 C22 H22 109.2 . . ?
C23 C22 H22 109.2 . . ?
C21 C22 H22 109.2 . . ?
O3 C23 O4 125.4(4) . . ?
O3 C23 C22 124.0(4) . . ?
O4 C23 C22 110.5(3) . . ?
C25 C24 O4 108.1(5) . . ?
C25 C24 H24A 110.1 . . ?
O4 C24 H24A 110.1 . . ?
C25 C24 H24B 110.1 . . ?
O4 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N3 C14 128.5(3) . . ?
C13 N3 H3 115.8 . . ?
C14 N3 H3 115.8 . . ?
C14 N4 C22 121.3(3) . . ?
C14 N4 H4 119.3 . . ?
C22 N4 H4 119.3 . . ?
C23 O4 C24 117.1(3) . . ?
C12 S1 C8 91.71(18) . . ?

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 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C5 -1.3(6) . . . . ?
C1 C2 C3 C4 176.3(4) . . . . ?
C2 C3 C5 C6 2.6(6) . . . . ?
C4 C3 C5 C6 -174.9(4) . . . . ?
C3 C5 C6 C7 -2.0(6) . . . . ?
C5 C6 C7 C1 -0.1(6) . . . . ?
C5 C6 C7 C9 172.7(3) . . . . ?
C2 C1 C7 C6 1.4(5) . . . . ?
C2 C1 C7 C9 -171.4(3) . . . . ?
C13 C8 C9 C11 171.3(4) . . . . ?
S1 C8 C9 C11 -2.2(4) . . . . ?
C13 C8 C9 C7 -9.9(7) . . . . ?
S1 C8 C9 C7 176.6(3) . . . . ?
C6 C7 C9 C8 115.7(5) . . . . ?
C1 C7 C9 C8 -71.6(5) . . . . ?
C6 C7 C9 C11 -65.6(5) . . . . ?
C1 C7 C9 C11 107.1(4) . . . . ?
C8 C9 C11 C12 1.4(5) . . . . ?
C7 C9 C11 C12 -177.5(4) . . . . ?
C8 C9 C11 C10 -179.9(4) . . . . ?
C7 C9 C11 C10 1.2(6) . . . . ?
C10 C11 C12 N2 2.4(6) . . . . ?
C9 C11 C12 N2 -178.9(4) . . . . ?
C10 C11 C12 S1 -178.8(3) . . . . ?
C9 C11 C12 S1 0.0(4) . . . . ?
C9 C8 C13 O1 -178.4(4) . . . . ?
S1 C8 C13 O1 -4.9(5) . . . . ?
C9 C8 C13 N3 -2.5(7) . . . . ?
S1 C8 C13 N3 170.9(3) . . . . ?
C20 C15 C16 C17 -0.1(8) . . . . ?
C15 C16 C17 C18 -0.7(8) . . . . ?
C16 C17 C18 C19 0.0(8) . . . . ?
C17 C18 C19 C20 1.4(8) . . . . ?
C16 C15 C20 C19 1.5(7) . . . . ?
C16 C15 C20 C21 -177.7(4) . . . . ?
C18 C19 C20 C15 -2.2(7) . . . . ?
C18 C19 C20 C21 177.0(4) . . . . ?
C15 C20 C21 C22 78.7(5) . . . . ?
C19 C20 C21 C22 -100.5(5) . . . . ?
C20 C21 C22 N4 -175.2(3) . . . . ?
C20 C21 C22 C23 65.2(4) . . . . ?
N4 C22 C23 O3 -29.7(5) . . . . ?
C21 C22 C23 O3 91.9(5) . . . . ?
N4 C22 C23 O4 153.1(3) . . . . ?
C21 C22 C23 O4 -85.3(4) . . . . ?
O1 C13 N3 C14 8.0(8) . . . . ?
C8 C13 N3 C14 -167.8(4) . . . . ?
O2 C14 N3 C13 169.3(4) . . . . ?
N4 C14 N3 C13 -10.7(6) . . . . ?
O2 C14 N4 C22 -6.3(6) . . . . ?
N3 C14 N4 C22 173.7(3) . . . . ?
C23 C22 N4 C14 -147.7(3) . . . . ?
C21 C22 N4 C14 91.2(4) . . . . ?
O3 C23 O4 C24 -2.3(6) . . . . ?
C22 C23 O4 C24 174.8(4) . . . . ?
C25 C24 O4 C23 -160.5(5) . . . . ?
N2 C12 S1 C8 177.9(4) . . . . ?
C11 C12 S1 C8 -1.1(3) . . . . ?
C9 C8 S1 C12 1.9(3) . . . . ?
C13 C8 S1 C12 -173.0(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
N2 H2B O2 0.86 1.96 2.789(5) 160.2 1_565
N4 H4 O1 0.86 2.06 2.688(4) 129.3 .

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039

