# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_complex-1
_database_code_depnum_ccdc_archive 'CCDC 2239945'
loop_
_audit_author_name
_audit_author_address
Panja
;Gokhale Memorial Girls College
India
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N3 O3'
_chemical_formula_weight         223.23

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.1754(6)
_cell_length_b                   13.8861(11)
_cell_length_c                   10.7991(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.604(3)
_cell_angle_gamma                90
_cell_volume                     1041.24(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    498
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.12

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_T_max  0.7496
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27327
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.086
_diffrn_reflns_theta_max         30.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3167
_reflns_number_gt                2678
_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 Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al 2008)'
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0622P)²+0.2925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33471(11) 0.36451(5) 0.47916(7) 0.02178(16) Uani 1 1 d . . . . .
O2 O 0.19927(12) 0.37669(5) 0.23218(7) 0.02621(18) Uani 1 1 d . . . . .
O3 O 0.61867(13) 0.38884(6) 1.02544(7) 0.02980(19) Uani 1 1 d . . . . .
N1 N 0.40325(11) 0.44975(6) 0.70586(7) 0.01907(17) Uani 1 1 d . . . . .
N2 N 0.46581(13) 0.45507(6) 0.83685(8) 0.02221(18) Uani 1 1 d . . . . .
N3 N 0.59551(14) 0.30156(6) 0.84524(9) 0.0276(2) Uani 1 1 d . . . . .
C1 C 0.25114(13) 0.44975(6) 0.43255(8) 0.01733(17) Uani 1 1 d . . . . .
C6 C 0.23893(12) 0.52840(6) 0.51075(8) 0.01735(17) Uani 1 1 d . . . . .
C7 C 0.31615(13) 0.52496(7) 0.64911(9) 0.01892(18) Uani 1 1 d . . . . .
H7 H 0.301939 0.579609 0.698861 0.023 Uiso 1 1 calc R U . . .
C3 C 0.08160(13) 0.54031(7) 0.24718(9) 0.02065(19) Uani 1 1 d . . . . .
H3 H 0.028677 0.544168 0.157342 0.025 Uiso 1 1 calc R U . . .
C2 C 0.17373(13) 0.45674(6) 0.29953(8) 0.01881(18) Uani 1 1 d . . . . .
C4 C 0.06496(13) 0.61958(7) 0.32458(9) 0.02002(19) Uani 1 1 d . . . . .
C5 C 0.14537(13) 0.61288(6) 0.45510(9) 0.01949(18) Uani 1 1 d . . . . .
H5 H 0.137248 0.666412 0.508255 0.023 Uiso 1 1 calc R U . . .
C10 C -0.04120(15) 0.70863(7) 0.26472(10) 0.0256(2) Uani 1 1 d . . . . .
H10A H -0.058938 0.752198 0.332227 0.038 Uiso 1 1 calc R U . . .
H10B H -0.167251 0.690262 0.210313 0.038 Uiso 1 1 calc R U . . .
H10C H 0.033674 0.741241 0.212775 0.038 Uiso 1 1 calc R U . . .
C8 C 0.56404(14) 0.38093(7) 0.90716(9) 0.02072(19) Uani 1 1 d . . . . .
C9 C 0.12386(17) 0.37869(8) 0.09675(10) 0.0288(2) Uani 1 1 d . . . . .
H9A H -0.016073 0.387553 0.076545 0.043 Uiso 1 1 calc R U . . .
H9B H 0.153540 0.317788 0.060018 0.043 Uiso 1 1 calc R U . . .
H9C H 0.182273 0.432089 0.060613 0.043 Uiso 1 1 calc R U . . .
H3A H 0.571(2) 0.3028(12) 0.7582(18) 0.046(5) Uiso 1 1 d . . . . .
H3B H 0.672(2) 0.2562(12) 0.8909(15) 0.036(4) Uiso 1 1 d . . . . .
H1 H 0.373(2) 0.3700(12) 0.5623(18) 0.045(5) Uiso 1 1 d . . . . .
H2 H 0.436(2) 0.5086(13) 0.8784(16) 0.040(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3645(11) . ?
O1 H1 0.874(19) . ?
O2 C2 1.3658(11) . ?
O2 C9 1.4260(12) . ?
O3 C8 1.2428(12) . ?
N1 C7 1.2898(12) . ?
N1 N2 1.3739(11) . ?
N2 C8 1.3651(12) . ?
N2 H2 0.922(17) . ?
N3 C8 1.3376(13) . ?
N3 H3A 0.912(18) . ?
N3 H3B 0.898(16) . ?
C1 C6 1.3967(12) . ?
C1 C2 1.4069(12) . ?
C6 C5 1.4087(12) . ?
C6 C7 1.4576(12) . ?
C7 H7 0.9500 . ?
C3 C2 1.3838(13) . ?
C3 C4 1.4053(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3850(13) . ?
C4 C10 1.5096(13) . ?
C5 H5 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 107.4(11) . . ?
C2 O2 C9 117.59(8) . . ?
C7 N1 N2 116.04(8) . . ?
C8 N2 N1 121.40(8) . . ?
C8 N2 H2 119.3(10) . . ?
N1 N2 H2 119.3(10) . . ?
C8 N3 H3A 119.1(11) . . ?
C8 N3 H3B 117.4(10) . . ?
H3A N3 H3B 120.7(15) . . ?
O1 C1 C6 122.96(8) . . ?
O1 C1 C2 117.40(8) . . ?
C6 C1 C2 119.64(8) . . ?
C1 C6 C5 119.28(8) . . ?
C1 C6 C7 121.91(8) . . ?
C5 C6 C7 118.80(8) . . ?
N1 C7 C6 121.81(8) . . ?
N1 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C2 C3 C4 121.16(8) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
O2 C2 C3 125.41(8) . . ?
O2 C2 C1 114.59(8) . . ?
C3 C2 C1 120.00(8) . . ?
C5 C4 C3 118.46(8) . . ?
C5 C4 C10 121.78(9) . . ?
C3 C4 C10 119.76(8) . . ?
C4 C5 C6 121.44(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C8 N3 122.51(9) . . ?
O3 C8 N2 119.33(9) . . ?
N3 C8 N2 118.16(9) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 -178.35(9) . . . . ?
O1 C1 C6 C5 -178.22(8) . . . . ?
C2 C1 C6 C5 1.35(13) . . . . ?
O1 C1 C6 C7 0.23(14) . . . . ?
C2 C1 C6 C7 179.80(8) . . . . ?
N2 N1 C7 C6 -178.74(8) . . . . ?
C1 C6 C7 N1 1.51(14) . . . . ?
C5 C6 C7 N1 179.97(9) . . . . ?
C9 O2 C2 C3 -0.48(15) . . . . ?
C9 O2 C2 C1 179.83(9) . . . . ?
C4 C3 C2 O2 -179.07(9) . . . . ?
C4 C3 C2 C1 0.60(14) . . . . ?
O1 C1 C2 O2 -2.40(12) . . . . ?
C6 C1 C2 O2 178.00(8) . . . . ?
O1 C1 C2 C3 177.89(8) . . . . ?
C6 C1 C2 C3 -1.70(13) . . . . ?
C2 C3 C4 C5 0.84(14) . . . . ?
C2 C3 C4 C10 -178.33(9) . . . . ?
C3 C4 C5 C6 -1.19(14) . . . . ?
C10 C4 C5 C6 177.96(9) . . . . ?
C1 C6 C5 C4 0.10(14) . . . . ?
C7 C6 C5 C4 -178.40(8) . . . . ?
N1 N2 C8 O3 179.74(9) . . . . ?
N1 N2 C8 N3 -1.11(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
_geom_hbond_publ_flag
C9 H9A O3 0.98 2.54 3.5136(15) 173.2 1_454 yes
N3 H3B O1 0.898(16) 2.125(16) 3.0172(11) 172.2(14) 4_666 yes
O1 H1 N1 0.874(19) 1.872(18) 2.6513(10) 147.5(16) . yes
N2 H2 O3 0.922(17) 1.861(18) 2.7805(11) 175.4(15) 3_667 yes
C9 H9A O3 0.98 2.54 3.5136(15) 173.2 1_454 yes
N3 H3B O1 0.898(16) 2.125(16) 3.0172(11) 172.2(14) 4_666 yes
O1 H1 N1 0.874(19) 1.872(18) 2.6513(10) 147.5(16) . yes
N2 H2 O3 0.922(17) 1.861(18) 2.7805(11) 175.4(15) 3_667 yes

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.186
_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_complex-2
_database_code_depnum_ccdc_archive 'CCDC 2239946'
loop_
_audit_author_name
_audit_author_address
Panja
;Gokhale Memorial Girls College
India
;
_audit_update_record             
;
2023-02-05 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N3 O2 S'
_chemical_formula_weight         239.29

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                   7.919(8)
_cell_length_b                   10.604(9)
_cell_length_c                   13.971(14)
_cell_angle_alpha                89.16(3)
_cell_angle_beta                 78.00(4)
_cell_angle_gamma                78.24(3)
_cell_volume                     1123.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    491
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_T_max  0.7855
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57084
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         30.710
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6879
_reflns_number_gt                5728
_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 Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al 2008)'
_computing_publication_material  'SHELXL-2016/4 (Sheldrick, 2016)'
_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)+(0.0637P)²+0.4204P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6879
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28924(5) 1.05030(3) 0.13473(2) 0.02848(9) Uani 1 1 d . . . . .
S1A S 0.17095(5) 0.55514(3) 0.36509(2) 0.02983(9) Uani 1 1 d . . . . .
O1A O 0.00375(13) -0.00290(8) 0.67010(6) 0.02455(19) Uani 1 1 d . . . . .
O1 O 0.54518(12) 0.46706(8) 0.14888(6) 0.02428(19) Uani 1 1 d . . . . .
O2 O 0.67633(13) 0.22233(8) 0.13792(7) 0.0284(2) Uani 1 1 d . . . . .
O2A O 0.11753(14) -0.24936(9) 0.68912(7) 0.0283(2) Uani 1 1 d . . . . .
N1 N 0.54555(14) 0.69542(9) 0.07309(7) 0.01962(19) Uani 1 1 d . . . . .
N2 N 0.48794(14) 0.82608(9) 0.06913(7) 0.0217(2) Uani 1 1 d . . . . .
N2A N 0.15288(15) 0.32614(9) 0.43751(8) 0.0231(2) Uani 1 1 d . . . . .
N1A N 0.21368(14) 0.19520(9) 0.43746(7) 0.0218(2) Uani 1 1 d . . . . .
N3 N 0.29653(16) 0.82322(10) 0.21676(8) 0.0257(2) Uani 1 1 d . . . . .
N3A N 0.33819(18) 0.32438(11) 0.28888(9) 0.0323(3) Uani 1 1 d . . . . .
C8 C 0.36052(16) 0.89012(11) 0.14199(8) 0.0200(2) Uani 1 1 d . . . . .
C7 C 0.66747(16) 0.64126(11) 0.00100(9) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.711103 0.692387 -0.051050 0.025 Uiso 1 1 calc R U . . .
C6 C 0.73919(15) 0.50397(10) -0.00216(8) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.88744(17) 0.24152(11) -0.01337(9) 0.0226(2) Uani 1 1 d . . . . .
H3 H 0.939708 0.152316 -0.016096 0.027 Uiso 1 1 calc R U . . .
C6A C 0.21331(16) -0.00102(11) 0.52009(8) 0.0189(2) Uani 1 1 d . . . . .
C1 C 0.67839(15) 0.42360(10) 0.07087(8) 0.0185(2) Uani 1 1 d . . . . .
C8A C 0.22545(17) 0.39263(11) 0.36257(8) 0.0218(2) Uani 1 1 d . . . . .
C1A C 0.14008(16) -0.06645(11) 0.59935(8) 0.0191(2) Uani 1 1 d . . . . .
C7A C 0.14769(16) 0.13644(11) 0.51203(8) 0.0209(2) Uani 1 1 d . . . . .
H7A H 0.056309 0.182253 0.561925 0.025 Uiso 1 1 calc R U . . .
C2A C 0.20365(16) -0.19843(11) 0.60795(8) 0.0209(2) Uani 1 1 d . . . . .
C5 C 0.87317(17) 0.45037(12) -0.08203(9) 0.0233(2) Uani 1 1 d . . . . .
H5 H 0.912814 0.504631 -0.132839 0.028 Uiso 1 1 calc R U . . .
C2 C 0.75204(16) 0.29158(11) 0.06458(8) 0.0202(2) Uani 1 1 d . . . . .
C4 C 0.94832(17) 0.32068(12) -0.08821(9) 0.0230(2) Uani 1 1 d . . . . .
C4A C 0.41684(17) -0.20008(12) 0.45705(9) 0.0237(2) Uani 1 1 d . . . . .
C3A C 0.34032(17) -0.26474(11) 0.53756(9) 0.0238(2) Uani 1 1 d . . . . .
H3AC H 0.382714 -0.354366 0.543603 0.029 Uiso 1 1 calc R U . . .
C5A C 0.35335(17) -0.07021(12) 0.44899(9) 0.0223(2) Uani 1 1 d . . . . .
H5A H 0.405024 -0.026407 0.394388 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7542(2) 0.08897(12) 0.13988(11) 0.0314(3) Uani 1 1 d . . . . .
H9A H 0.742426 0.044539 0.081351 0.047 Uiso 1 1 calc R U . . .
H9B H 0.694264 0.051360 0.198471 0.047 Uiso 1 1 calc R U . . .
H9C H 0.879427 0.079320 0.141180 0.047 Uiso 1 1 calc R U . . .
C10A C 0.56595(19) -0.27393(14) 0.38103(11) 0.0332(3) Uani 1 1 d . . . . .
H10D H 0.609963 -0.214509 0.332294 0.050 Uiso 1 1 calc R U . . .
H10E H 0.523641 -0.339143 0.348752 0.050 Uiso 1 1 calc R U . . .
H10F H 0.661412 -0.316253 0.412508 0.050 Uiso 1 1 calc R U . . .
C9A C 0.1763(2) -0.38318(13) 0.70246(12) 0.0349(3) Uani 1 1 d . . . . .
H9AA H 0.155510 -0.432853 0.649017 0.052 Uiso 1 1 calc R U . . .
H9AB H 0.111263 -0.407881 0.765081 0.052 Uiso 1 1 calc R U . . .
H9AC H 0.302715 -0.400984 0.702477 0.052 Uiso 1 1 calc R U . . .
C10 C 1.09170(19) 0.26453(14) -0.17431(10) 0.0319(3) Uani 1 1 d . . . . .
H10A H 1.110982 0.331778 -0.221805 0.048 Uiso 1 1 calc R U . . .
H10B H 1.056369 0.194610 -0.205333 0.048 Uiso 1 1 calc R U . . .
H10C H 1.201046 0.230688 -0.151827 0.048 Uiso 1 1 calc R U . . .
H1 H 0.511(3) 0.544(2) 0.1438(15) 0.048 Uiso 1 1 d . U . . .
H1A H -0.024(3) -0.059(2) 0.7032(16) 0.048 Uiso 1 1 d . U . . .
H2A H 0.070(3) 0.3653(19) 0.4889(15) 0.038 Uiso 1 1 d . U . . .
H3A H 0.326(3) 0.739(2) 0.2173(14) 0.038 Uiso 1 1 d . U . . .
H2 H 0.537(3) 0.8645(19) 0.0170(15) 0.038 Uiso 1 1 d . U . . .
H3B H 0.209(3) 0.8634(19) 0.2666(14) 0.038 Uiso 1 1 d . U . . .
H3AA H 0.362(3) 0.242(2) 0.2932(15) 0.043(5) Uiso 1 1 d . . . . .
H3AB H 0.396(3) 0.3594(19) 0.2441(14) 0.037(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.6858(18) . ?
S1A C8A 1.6880(19) . ?
O1A C1A 1.3697(17) . ?
O1A H1A 0.78(2) . ?
O1 C1 1.3608(17) . ?
O1 H1 0.82(2) . ?
O2 C2 1.3604(17) . ?
O2 C9 1.4252(18) . ?
O2A C2A 1.3614(17) . ?
O2A C9A 1.4228(19) . ?
N1 C7 1.2897(18) . ?
N1 N2 1.3717(17) . ?
N2 C8 1.3526(18) . ?
N2 H2 0.88(2) . ?
N2A C8A 1.3481(17) . ?
N2A N1A 1.3737(17) . ?
N2A H2A 0.91(2) . ?
N1A C7A 1.2784(17) . ?
N3 C8 1.3252(17) . ?
N3 H3A 0.88(2) . ?
N3 H3B 0.91(2) . ?
N3A C8A 1.3256(19) . ?
N3A H3AA 0.86(2) . ?
N3A H3AB 0.83(2) . ?
C7 C6 1.4486(19) . ?
C7 H7 0.9500 . ?
C6 C1 1.3916(18) . ?
C6 C5 1.4052(19) . ?
C3 C2 1.3845(19) . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C6A C1A 1.3851(18) . ?
C6A C5A 1.4095(19) . ?
C6A C7A 1.4554(19) . ?
C1 C2 1.3991(19) . ?
C1A C2A 1.3999(19) . ?
C7A H7A 0.9500 . ?
C2A C3A 1.379(2) . ?
C5 C4 1.379(2) . ?
C5 H5 0.9500 . ?
C4 C10 1.506(2) . ?
C4A C5A 1.378(2) . ?
C4A C3A 1.402(2) . ?
C4A C10A 1.504(2) . ?
C3A H3AC 0.9500 . ?
C5A H5A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 103.2(16) . . ?
C1 O1 H1 108.4(15) . . ?
C2 O2 C9 117.12(11) . . ?
C2A O2A C9A 116.50(11) . . ?
C7 N1 N2 116.53(10) . . ?
C8 N2 N1 120.16(10) . . ?
C8 N2 H2 122.9(13) . . ?
N1 N2 H2 116.9(13) . . ?
C8A N2A N1A 118.32(11) . . ?
C8A N2A H2A 122.3(13) . . ?
N1A N2A H2A 119.3(13) . . ?
C7A N1A N2A 116.47(11) . . ?
C8 N3 H3A 122.2(13) . . ?
C8 N3 H3B 120.1(12) . . ?
H3A N3 H3B 117.3(18) . . ?
C8A N3A H3AA 118.1(14) . . ?
C8A N3A H3AB 121.4(13) . . ?
H3AA N3A H3AB 119.8(19) . . ?
N3 C8 N2 118.02(12) . . ?
N3 C8 S1 122.60(10) . . ?
N2 C8 S1 119.38(9) . . ?
N1 C7 C6 121.28(11) . . ?
N1 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C1 C6 C5 119.11(12) . . ?
C1 C6 C7 122.06(11) . . ?
C5 C6 C7 118.82(11) . . ?
C2 C3 C4 120.85(12) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C1A C6A C5A 118.48(12) . . ?
C1A C6A C7A 120.22(11) . . ?
C5A C6A C7A 121.29(11) . . ?
O1 C1 C6 122.79(11) . . ?
O1 C1 C2 117.26(10) . . ?
C6 C1 C2 119.93(11) . . ?
N3A C8A N2A 116.86(12) . . ?
N3A C8A S1A 123.01(10) . . ?
N2A C8A S1A 120.13(10) . . ?
O1A C1A C6A 120.38(11) . . ?
O1A C1A C2A 119.13(11) . . ?
C6A C1A C2A 120.49(11) . . ?
N1A C7A C6A 119.64(11) . . ?
N1A C7A H7A 120.2 . . ?
C6A C7A H7A 120.2 . . ?
O2A C2A C3A 126.05(12) . . ?
O2A C2A C1A 113.67(11) . . ?
C3A C2A C1A 120.27(11) . . ?
C4 C5 C6 121.38(11) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O2 C2 C3 125.61(12) . . ?
O2 C2 C1 114.43(11) . . ?
C3 C2 C1 119.93(11) . . ?
C5 C4 C3 118.75(12) . . ?
C5 C4 C10 120.81(12) . . ?
C3 C4 C10 120.44(12) . . ?
C5A C4A C3A 119.30(12) . . ?
C5A C4A C10A 121.33(12) . . ?
C3A C4A C10A 119.36(13) . . ?
C2A C3A C4A 120.09(12) . . ?
C2A C3A H3AC 120.0 . . ?
C4A C3A H3AC 120.0 . . ?
C4A C5A C6A 121.36(11) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4A C10A H10D 109.5 . . ?
C4A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C4A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
O2A C9A H9AA 109.5 . . ?
O2A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
O2A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 -179.90(11) . . . . ?
C8A N2A N1A C7A 176.73(12) . . . . ?
N1 N2 C8 N3 0.99(18) . . . . ?
N1 N2 C8 S1 -178.97(9) . . . . ?
N2 N1 C7 C6 179.54(11) . . . . ?
N1 C7 C6 C1 1.27(19) . . . . ?
N1 C7 C6 C5 -179.34(12) . . . . ?
C5 C6 C1 O1 -177.76(11) . . . . ?
C7 C6 C1 O1 1.62(18) . . . . ?
C5 C6 C1 C2 0.69(18) . . . . ?
C7 C6 C1 C2 -179.93(11) . . . . ?
N1A N2A C8A N3A 6.76(18) . . . . ?
N1A N2A C8A S1A -173.53(9) . . . . ?
C5A C6A C1A O1A -179.98(11) . . . . ?
C7A C6A C1A O1A 0.92(18) . . . . ?
C5A C6A C1A C2A -0.35(18) . . . . ?
C7A C6A C1A C2A -179.44(11) . . . . ?
N2A N1A C7A C6A -176.22(10) . . . . ?
C1A C6A C7A N1A -178.46(11) . . . . ?
C5A C6A C7A N1A 2.47(18) . . . . ?
C9A O2A C2A C3A 0.76(19) . . . . ?
C9A O2A C2A C1A -179.73(11) . . . . ?
O1A C1A C2A O2A 0.22(16) . . . . ?
C6A C1A C2A O2A -179.42(11) . . . . ?
O1A C1A C2A C3A 179.77(11) . . . . ?
C6A C1A C2A C3A 0.13(18) . . . . ?
C1 C6 C5 C4 -1.62(19) . . . . ?
C7 C6 C5 C4 178.98(12) . . . . ?
C9 O2 C2 C3 6.46(19) . . . . ?
C9 O2 C2 C1 -175.29(11) . . . . ?
C4 C3 C2 O2 176.00(12) . . . . ?
C4 C3 C2 C1 -2.16(19) . . . . ?
O1 C1 C2 O2 1.34(16) . . . . ?
C6 C1 C2 O2 -177.19(11) . . . . ?
O1 C1 C2 C3 179.70(11) . . . . ?
C6 C1 C2 C3 1.17(18) . . . . ?
C6 C5 C4 C3 0.66(19) . . . . ?
C6 C5 C4 C10 179.94(12) . . . . ?
C2 C3 C4 C5 1.24(19) . . . . ?
C2 C3 C4 C10 -178.04(12) . . . . ?
O2A C2A C3A C4A 179.71(12) . . . . ?
C1A C2A C3A C4A 0.22(19) . . . . ?
C5A C4A C3A C2A -0.34(19) . . . . ?
C10A C4A C3A C2A 179.93(12) . . . . ?
C3A C4A C5A C6A 0.12(19) . . . . ?
C10A C4A C5A C6A 179.84(12) . . . . ?
C1A C6A C5A C4A 0.22(18) . . . . ?
C7A C6A C5A C4A 179.31(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7 S1 0.95 2.95 3.797(3) 148.8 2_675 yes
C9A H9AC O1 0.98 2.63 3.319(3) 127.7 2_656 yes
O1 H1 N1 0.82(2) 1.91(2) 2.629(2) 147(2) . yes
O1A H1A S1 0.78(2) 2.74(2) 3.298(3) 130.2(19) 2_566 yes
O1A H1A O2A 0.78(2) 2.09(2) 2.614(2) 124(2) . yes
N2A H2A S1A 0.91(2) 2.51(2) 3.408(3) 172.2(17) 2_566 yes
N2 H2 S1 0.88(2) 2.54(2) 3.419(3) 172.4(17) 2_675 yes
N3 H3B O1A 0.91(2) 2.05(2) 2.909(3) 155.5(17) 2_566 yes
N3A H3AB O1 0.83(2) 2.08(2) 2.897(2) 170.8(18) . yes
N3A H3AB O2 0.83(2) 2.574(19) 3.054(3) 118.4(16) . yes
C7 H7 S1 0.95 2.95 3.797(3) 148.8 2_675 yes
C9A H9AC O1 0.98 2.63 3.319(3) 127.7 2_656 yes
O1 H1 N1 0.82(2) 1.91(2) 2.629(2) 147(2) . yes
O1A H1A S1 0.78(2) 2.74(2) 3.298(3) 130.2(19) 2_566 yes
O1A H1A O2A 0.78(2) 2.09(2) 2.614(2) 124(2) . yes
N2A H2A S1A 0.91(2) 2.51(2) 3.408(3) 172.2(17) 2_566 yes
N2 H2 S1 0.88(2) 2.54(2) 3.419(3) 172.4(17) 2_675 yes
N3 H3B O1A 0.91(2) 2.05(2) 2.909(3) 155.5(17) 2_566 yes
N3A H3AB O1 0.83(2) 2.08(2) 2.897(2) 170.8(18) . yes
N3A H3AB O2 0.83(2) 2.574(19) 3.054(3) 118.4(16) . yes

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.057

