# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_at77m
_database_code_depnum_ccdc_archive 'CCDC 2159446'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'TORASEMIDE FUMARATE (1:1) SALT'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N4 O3 S, C4 H3 O4'
_chemical_formula_sum            'C20 H24 N4 O7 S'
_chemical_formula_weight         464.49

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/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                   12.3437(15)
_cell_length_b                   8.2271(10)
_cell_length_c                   22.439(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.322(2)
_cell_angle_gamma                90
_cell_volume                     2226.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7545
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.82

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22350
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4369
_reflns_number_gt                3916
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.8943P] 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         4369
_refine_ls_number_parameters     312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.4746(2) 0.8816(3) 0.41100(11) 0.0538(6) Uani 1 1 d . . . . .
H1 H 0.464380 0.993586 0.410563 0.065 Uiso 1 1 calc R U . . .
N1 N 0.38672(17) 0.7859(2) 0.39038(9) 0.0498(5) Uani 1 1 d . . . . .
O1 O 0.57589(14) 0.28595(18) 0.46470(7) 0.0501(4) Uani 1 1 d . . . . .
S1 S 0.50254(4) 0.34101(6) 0.41093(2) 0.03819(16) Uani 1 1 d . . . . .
C2 C 0.57680(19) 0.8221(2) 0.43225(11) 0.0488(5) Uani 1 1 d . . . . .
H2 H 0.635220 0.892635 0.447018 0.059 Uiso 1 1 calc R U . . .
N2 N 0.69650(15) 0.5862(2) 0.44925(9) 0.0490(5) Uani 1 1 d . . . . .
O2 O 0.38992(13) 0.28978(19) 0.39783(8) 0.0551(4) Uani 1 1 d . . . . .
C3 C 0.59613(16) 0.6522(2) 0.43229(9) 0.0396(4) Uani 1 1 d . . . . .
N3 N 0.55200(14) 0.2865(2) 0.35286(8) 0.0433(4) Uani 1 1 d . . . . .
O3 O 0.73996(12) 0.2959(2) 0.39356(7) 0.0557(4) Uani 1 1 d . . . . .
O4 O 0.16220(14) 1.52636(18) 0.29535(8) 0.0549(4) Uani 1 1 d . . . . .
C4 C 0.50004(16) 0.5551(2) 0.41134(9) 0.0363(4) Uani 1 1 d . . . . .
N4 N 0.67440(16) 0.1441(2) 0.31027(9) 0.0470(4) Uani 1 1 d . . . . .
O5 O 0.01215(15) 1.42921(19) 0.23341(9) 0.0741(6) Uani 1 1 d . . . . .
C5 C 0.39858(17) 0.6256(2) 0.39107(9) 0.0424(5) Uani 1 1 d . . . . .
H5 H 0.336828 0.560102 0.377542 0.051 Uiso 1 1 calc R U . . .
O6 O 0.20515(14) 0.93775(18) 0.33815(8) 0.0599(5) Uani 1 1 d . . . . .
C6 C 0.79918(17) 0.6683(2) 0.47238(10) 0.0431(5) Uani 1 1 d . . . . .
O7 O 0.09233(13) 0.82264(16) 0.25946(7) 0.0503(4) Uani 1 1 d . . . . .
C7 C 0.81235(19) 0.7673(3) 0.52326(11) 0.0518(5) Uani 1 1 d . . . . .
H7 H 0.753010 0.789030 0.541537 0.062 Uiso 1 1 calc R U . . .
C8 C 0.9158(2) 0.8331(3) 0.54625(12) 0.0616(7) Uani 1 1 d . . . . .
H8 H 0.926479 0.900053 0.580405 0.074 Uiso 1 1 calc R U . . .
C9 C 1.0031(2) 0.8000(3) 0.51882(12) 0.0611(7) Uani 1 1 d . . . . .
H9 H 1.072333 0.844714 0.535051 0.073 Uiso 1 1 calc R U . . .
C10 C 0.99049(18) 0.7019(3) 0.46777(11) 0.0514(6) Uani 1 1 d . . . . .
C11 C 0.88686(18) 0.6356(3) 0.44525(10) 0.0459(5) Uani 1 1 d . . . . .
H11 H 0.876248 0.568057 0.411276 0.055 Uiso 1 1 calc R U . . .
C12 C 1.0854(2) 0.6705(4) 0.43691(15) 0.0757(8) Uani 1 1 d . . . . .
H12A H 1.154131 0.695871 0.464484 0.114 Uiso 1 1 calc R U . . .
H12B H 1.077361 0.737393 0.401185 0.114 Uiso 1 1 calc R U . . .
H12C H 1.085373 0.558086 0.425372 0.114 Uiso 1 1 calc R U . . .
C13 C 0.66349(16) 0.2431(2) 0.35523(9) 0.0393(4) Uani 1 1 d . . . . .
C14 C 0.78240(19) 0.0862(3) 0.30277(11) 0.0523(6) Uani 1 1 d . . . . .
H14 H 0.835359 0.176257 0.311553 0.063 Uiso 1 1 calc R U . . .
C15 C 0.7722(3) 0.0359(4) 0.23715(14) 0.0791(9) Uani 1 1 d . . . . .
H15A H 0.841573 -0.008124 0.231856 0.119 Uiso 1 1 calc R U . . .
H15B H 0.753277 0.128855 0.211151 0.119 Uiso 1 1 calc R U . . .
H15C H 0.715308 -0.045048 0.226673 0.119 Uiso 1 1 calc R U . . .
C16 C 0.8239(3) -0.0507(4) 0.34583(15) 0.0823(9) Uani 1 1 d . . . . .
H16A H 0.826686 -0.015910 0.386978 0.123 Uiso 1 1 calc R U . . .
H16B H 0.896762 -0.081726 0.341535 0.123 Uiso 1 1 calc R U . . .
H16C H 0.774635 -0.141857 0.336526 0.123 Uiso 1 1 calc R U . . .
C17 C 0.09741(17) 1.4087(2) 0.26997(9) 0.0416(5) Uani 1 1 d . . . . .
C18 C 0.14007(17) 1.2444(2) 0.29087(9) 0.0411(5) Uani 1 1 d . . . . .
H18 H 0.203724 1.237466 0.321601 0.049 Uiso 1 1 calc R U . . .
C19 C 0.09238(16) 1.1093(2) 0.26811(9) 0.0381(4) Uani 1 1 d . . . . .
H19 H 0.029648 1.116164 0.236771 0.046 Uiso 1 1 calc R U . . .
C20 C 0.13415(16) 0.9438(2) 0.29022(9) 0.0369(4) Uani 1 1 d . . . . .
H1N H 0.320(2) 0.827(3) 0.3736(12) 0.068(8) Uiso 1 1 d . . . . .
H2N H 0.704(2) 0.483(4) 0.4399(11) 0.062(7) Uiso 1 1 d . . . . .
H3N H 0.504(2) 0.299(3) 0.3187(12) 0.059(7) Uiso 1 1 d . . . . .
H4N H 0.6198(19) 0.101(3) 0.2932(10) 0.042(6) Uiso 1 1 d . . . . .
H4O H 0.137(2) 1.618(4) 0.2830(12) 0.060(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(3) . ?
C1 C2 1.342(3) . ?
N1 C5 1.327(3) . ?
O1 S1 1.4194(16) . ?
S1 O2 1.4221(16) . ?
S1 N3 1.6158(19) . ?
S1 C4 1.7620(19) . ?
C2 C3 1.418(3) . ?
N2 C3 1.332(3) . ?
N2 C6 1.432(3) . ?
C3 C4 1.424(3) . ?
N3 C13 1.412(3) . ?
O3 C13 1.214(2) . ?
O4 C17 1.306(2) . ?
C4 C5 1.367(3) . ?
N4 C13 1.326(3) . ?
N4 C14 1.459(3) . ?
O5 C17 1.200(2) . ?
O6 C20 1.235(2) . ?
C6 C11 1.377(3) . ?
C6 C7 1.384(3) . ?
O7 C20 1.259(2) . ?
C7 C8 1.381(3) . ?
C8 C9 1.379(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.383(3) . ?
C10 C12 1.506(3) . ?
C14 C16 1.501(4) . ?
C14 C15 1.509(4) . ?
C17 C18 1.490(3) . ?
C18 C19 1.309(3) . ?
C19 C20 1.503(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.6(2) . . ?
C5 N1 C1 120.0(2) . . ?
O1 S1 O2 119.95(10) . . ?
O1 S1 N3 108.34(10) . . ?
O2 S1 N3 105.78(10) . . ?
O1 S1 C4 108.86(9) . . ?
O2 S1 C4 106.26(9) . . ?
N3 S1 C4 106.96(10) . . ?
C1 C2 C3 120.3(2) . . ?
C3 N2 C6 127.51(18) . . ?
N2 C3 C2 123.24(19) . . ?
N2 C3 C4 121.64(18) . . ?
C2 C3 C4 115.10(18) . . ?
C13 N3 S1 124.95(15) . . ?
C5 C4 C3 120.77(18) . . ?
C5 C4 S1 115.99(15) . . ?
C3 C4 S1 123.23(14) . . ?
C13 N4 C14 122.15(19) . . ?
N1 C5 C4 121.1(2) . . ?
C11 C6 C7 121.0(2) . . ?
C11 C6 N2 117.79(19) . . ?
C7 C6 N2 121.0(2) . . ?
C8 C7 C6 118.4(2) . . ?
C9 C8 C7 120.3(2) . . ?
C8 C9 C10 121.6(2) . . ?
C9 C10 C11 117.7(2) . . ?
C9 C10 C12 121.3(2) . . ?
C11 C10 C12 121.0(2) . . ?
C6 C11 C10 121.0(2) . . ?
O3 C13 N4 124.7(2) . . ?
O3 C13 N3 122.72(18) . . ?
N4 C13 N3 112.54(18) . . ?
N4 C14 C16 111.4(2) . . ?
N4 C14 C15 108.3(2) . . ?
C16 C14 C15 111.6(2) . . ?
O5 C17 O4 124.07(19) . . ?
O5 C17 C18 122.82(19) . . ?
O4 C17 C18 113.12(17) . . ?
C19 C18 C17 123.25(18) . . ?
C18 C19 C20 123.14(17) . . ?
O6 C20 O7 125.28(17) . . ?
O6 C20 C19 116.98(17) . . ?
O7 C20 C19 117.71(17) . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.053



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile and water'
####################################################################### 
# 
# 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_BA54M
_database_code_depnum_ccdc_archive 'CCDC 2159447'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'TORASEMIDE OXALATE SALT'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N4 O3 S, 0.5(C2 O4)'
_chemical_formula_sum            'C17 H21 N4 O5 S'
_chemical_formula_weight         393.44

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      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                   8.9904(10)
_cell_length_b                   11.8567(13)
_cell_length_c                   18.285(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.807(2)
_cell_angle_gamma                90
_cell_volume                     1900.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6413
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.02

_exptl_crystal_description       'FLOWER LIKE NEEDLES'
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19334
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.063
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3723
_reflns_number_gt                3426
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+1.2763P] 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         3723
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35952(8) 0.96523(5) 0.20243(3) 0.0429(2) Uani 1 1 d . . . . .
O1 O 0.4126(3) 0.96457(19) 0.13503(10) 0.0626(6) Uani 1 1 d . . . . .
O2 O 0.3226(2) 1.06947(15) 0.23286(10) 0.0509(5) Uani 1 1 d . . . . .
O3 O 0.5004(3) 0.73922(19) 0.20810(11) 0.0675(6) Uani 1 1 d . . . . .
C17 C -0.0042(3) 0.53984(19) -0.03433(12) 0.0343(5) Uani 1 1 d . . . . .
C2 C -0.0191(3) 0.7948(2) 0.22315(14) 0.0435(6) Uani 1 1 d . . . . .
H2 H -0.085493 0.787331 0.255275 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1062(3) 0.86841(19) 0.24204(12) 0.0370(5) Uani 1 1 d . . . . .
C4 C 0.1969(3) 0.87852(19) 0.18792(12) 0.0367(5) Uani 1 1 d . . . . .
C5 C 0.1650(3) 0.8143(2) 0.12464(13) 0.0420(6) Uani 1 1 d . . . . .
H5 H 0.227791 0.819663 0.090665 0.050 Uiso 1 1 calc R U . . .
C6 C 0.0621(3) 0.8983(2) 0.36675(13) 0.0450(6) Uani 1 1 d . . . . .
C7 C -0.0561(4) 0.9642(3) 0.37743(18) 0.0644(8) Uani 1 1 d . . . . .
H7 H -0.087039 1.026860 0.347305 0.077 Uiso 1 1 calc R U . . .
C8 C -0.1278(4) 0.9356(4) 0.4337(2) 0.0840(12) Uani 1 1 d . . . . .
H8 H -0.208816 0.979193 0.441707 0.101 Uiso 1 1 calc R U . . .
C9 C -0.0816(5) 0.8442(4) 0.4780(2) 0.0810(12) Uani 1 1 d . . . . .
H9 H -0.132812 0.826032 0.515388 0.097 Uiso 1 1 calc R U . . .
C10 C 0.0398(4) 0.7772(3) 0.46889(16) 0.0666(9) Uani 1 1 d . . . . .
C11 C 0.1108(3) 0.8063(3) 0.41128(15) 0.0541(7) Uani 1 1 d . . . . .
H11 H 0.191822 0.763135 0.402867 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0930(6) 0.6763(4) 0.5172(2) 0.1089(16) Uani 1 1 d . . . . .
H12A H 0.032459 0.611884 0.497540 0.163 Uiso 1 1 calc R U . . .
H12B H 0.082540 0.690832 0.567446 0.163 Uiso 1 1 calc R U . . .
H12C H 0.198150 0.661529 0.517459 0.163 Uiso 1 1 calc R U . . .
C13 C 0.5136(3) 0.7884(2) 0.26741(14) 0.0455(6) Uani 1 1 d . . . . .
C14 C 0.5912(3) 0.6209(2) 0.34315(16) 0.0504(7) Uani 1 1 d . . . . .
H14 H 0.513359 0.580687 0.306374 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7454(4) 0.5921(3) 0.3278(2) 0.0788(10) Uani 1 1 d . . . . .
H15A H 0.759589 0.511810 0.330317 0.118 Uiso 1 1 calc R U . . .
H15B H 0.824017 0.627697 0.364716 0.118 Uiso 1 1 calc R U . . .
H15C H 0.750302 0.618432 0.278801 0.118 Uiso 1 1 calc R U . . .
C16 C 0.5770(5) 0.5846(3) 0.4202(2) 0.0843(12) Uani 1 1 d . . . . .
H16A H 0.477275 0.603623 0.427166 0.126 Uiso 1 1 calc R U . . .
H16B H 0.652775 0.622526 0.457258 0.126 Uiso 1 1 calc R U . . .
H16C H 0.591823 0.504577 0.425179 0.126 Uiso 1 1 calc R U . . .
O4 O -0.0305(3) 0.49395(15) -0.09697(9) 0.0554(5) Uani 1 1 d . . . . .
O5 O 0.0166(2) 0.64229(14) -0.02239(9) 0.0462(4) Uani 1 1 d . . . . .
N1 N 0.0472(3) 0.74431(18) 0.10996(12) 0.0473(6) Uani 1 1 d . . . . .
H1N H 0.036(4) 0.698(3) 0.0673(19) 0.071(10) Uiso 1 1 d . . . . .
N2 N 0.1369(3) 0.9243(2) 0.30704(11) 0.0475(6) Uani 1 1 d . . . . .
N3 N 0.4797(3) 0.9043(2) 0.27032(13) 0.0469(6) Uani 1 1 d . . . . .
H3N H 0.478(3) 0.932(2) 0.3092(17) 0.049(8) Uiso 1 1 d . . . . .
N4 N 0.5587(3) 0.7412(2) 0.33465(13) 0.0502(6) Uani 1 1 d . . . . .
H4N H 0.555(3) 0.781(3) 0.3710(17) 0.053(8) Uiso 1 1 d . . . . .
C1 C -0.0439(3) 0.7349(2) 0.15867(15) 0.0491(6) Uani 1 1 d . . . . .
H1 H -0.126433 0.685702 0.147784 0.059 Uiso 1 1 calc R U . . .
H2N H 0.201(3) 0.975(3) 0.3129(15) 0.047(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4170(19) . ?
S1 O2 1.425(2) . ?
S1 N3 1.624(2) . ?
S1 C4 1.759(2) . ?
O3 C13 1.214(3) . ?
C17 O5 1.241(3) . ?
C17 O4 1.243(3) . ?
C17 C17 1.560(4) 3_565 ?
C2 C1 1.352(4) . ?
C2 C3 1.406(4) . ?
C3 N2 1.335(3) . ?
C3 C4 1.420(3) . ?
C4 C5 1.362(3) . ?
C5 N1 1.325(3) . ?
C6 C7 1.367(4) . ?
C6 C11 1.374(4) . ?
C6 N2 1.437(3) . ?
C7 C8 1.373(5) . ?
C8 C9 1.362(6) . ?
C9 C10 1.389(6) . ?
C10 C11 1.391(4) . ?
C10 C12 1.502(5) . ?
C13 N4 1.330(3) . ?
C13 N3 1.411(3) . ?
C14 N4 1.457(4) . ?
C14 C16 1.505(4) . ?
C14 C15 1.513(4) . ?
N1 C1 1.342(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.82(12) . . ?
O1 S1 N3 111.53(14) . . ?
O2 S1 N3 105.13(12) . . ?
O1 S1 C4 107.14(12) . . ?
O2 S1 C4 107.94(12) . . ?
N3 S1 C4 104.19(12) . . ?
O5 C17 O4 125.5(2) . . ?
O5 C17 C17 118.2(2) . 3_565 ?
O4 C17 C17 116.2(2) . 3_565 ?
C1 C2 C3 120.6(2) . . ?
N2 C3 C2 121.5(2) . . ?
N2 C3 C4 122.8(2) . . ?
C2 C3 C4 115.7(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 S1 117.84(19) . . ?
C3 C4 S1 122.05(17) . . ?
N1 C5 C4 122.1(2) . . ?
C7 C6 C11 121.7(3) . . ?
C7 C6 N2 119.7(3) . . ?
C11 C6 N2 118.7(3) . . ?
C6 C7 C8 118.4(3) . . ?
C9 C8 C7 120.7(4) . . ?
C8 C9 C10 121.9(3) . . ?
C9 C10 C11 117.0(3) . . ?
C9 C10 C12 122.8(3) . . ?
C11 C10 C12 120.2(4) . . ?
C6 C11 C10 120.4(3) . . ?
O3 C13 N4 125.0(3) . . ?
O3 C13 N3 121.5(3) . . ?
N4 C13 N3 113.5(2) . . ?
N4 C14 C16 108.8(2) . . ?
N4 C14 C15 111.8(3) . . ?
C16 C14 C15 112.3(3) . . ?
C5 N1 C1 119.7(2) . . ?
C3 N2 C6 122.1(2) . . ?
C13 N3 S1 121.17(19) . . ?
C13 N4 C14 121.6(2) . . ?
N1 C1 C2 121.9(3) . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_AZ65
_database_code_depnum_ccdc_archive 'CCDC 2159448'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2022-03-16 deposited with the CCDC.	2022-05-03 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         '2(C16 H21 N4 O3 S), C2 O4, 0.56(C H4 O)'
_chemical_formula_sum            'C34.56 H44.24 N8 O10.56 S2'
_chemical_formula_weight         804.83

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                   20.8221(17)
_cell_length_b                   12.0329(10)
_cell_length_c                   17.7085(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.4650(10)
_cell_angle_gamma                90
_cell_volume                     4070.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9206
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.50

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.195
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38096
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.066
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7171
_reflns_number_gt                5478
_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    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+1.8898P] 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         7171
_refine_ls_number_parameters     590
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
C1A C 0.41074(18) 0.2597(2) 0.09536(18) 0.0570(8) Uani 1 1 d . . . . .
H1A H 0.376310 0.306471 0.060078 0.068 Uiso 1 1 calc R U . . .
N1A N 0.47299(15) 0.2559(2) 0.09069(15) 0.0573(7) Uani 1 1 d . . . . .
O1A O 0.55608(12) -0.06637(15) 0.26827(13) 0.0658(6) Uani 1 1 d . . . . .
S1A S 0.58258(4) 0.04037(6) 0.25991(5) 0.0565(2) Uani 1 1 d . . . . .
C2A C 0.39623(16) 0.1965(2) 0.15060(17) 0.0530(7) Uani 1 1 d . . . . .
H2A H 0.352318 0.200536 0.152566 0.064 Uiso 1 1 calc R U . . .
N2A N 0.43683(15) 0.0655(2) 0.26241(16) 0.0568(7) Uani 1 1 d . . . . .
O2A O 0.63661(13) 0.0477(2) 0.23049(15) 0.0801(7) Uani 1 1 d . . . . .
C3A C 0.44731(15) 0.1259(2) 0.20424(16) 0.0468(6) Uani 1 1 d . . . . .
N3A N 0.60543(14) 0.0981(2) 0.34956(15) 0.0555(6) Uani 1 1 d . . . . .
O3A O 0.63856(14) 0.2632(2) 0.31062(17) 0.0846(8) Uani 1 1 d . . . . .
C4A C 0.51155(16) 0.1211(2) 0.19466(16) 0.0487(7) Uani 1 1 d . . . . .
O4A O 0.54638(11) 0.51219(15) -0.06224(12) 0.0584(5) Uani 1 1 d . . . . .
C5A C 0.52245(17) 0.1891(2) 0.13909(17) 0.0533(7) Uani 1 1 d . . . . .
H5A H 0.565733 0.188220 0.135307 0.064 Uiso 1 1 calc R U . . .
O5A O 0.52850(11) 0.36283(15) -0.00018(12) 0.0588(5) Uani 1 1 d . . . . .
C6A C 0.38455(15) 0.0847(2) 0.29401(18) 0.0538(7) Uani 1 1 d . . . . .
C7A C 0.35198(18) -0.0055(3) 0.3107(2) 0.0696(9) Uani 1 1 d . . . . .
H7A H 0.360931 -0.076775 0.297069 0.084 Uiso 1 1 calc R U . . .
C8A C 0.3057(2) 0.0112(3) 0.3479(3) 0.0834(11) Uani 1 1 d . . . . .
H8A H 0.284054 -0.049346 0.360624 0.100 Uiso 1 1 calc R U . . .
C9A C 0.29160(19) 0.1161(4) 0.3660(2) 0.0796(10) Uani 1 1 d . . . . .
H9A H 0.259499 0.126021 0.389887 0.095 Uiso 1 1 calc R U . . .
C10A C 0.32376(18) 0.2081(3) 0.3498(2) 0.0676(9) Uani 1 1 d . . . . .
C11A C 0.37146(16) 0.1901(3) 0.31402(19) 0.0628(8) Uani 1 1 d . . . . .
H11A H 0.394750 0.250247 0.303511 0.075 Uiso 1 1 calc R U . . .
C12A C 0.3097(3) 0.3206(4) 0.3714(3) 0.1135(15) Uani 1 1 d . . . . .
H12A H 0.281624 0.360147 0.322136 0.170 Uiso 1 1 calc R U . . .
H12B H 0.353170 0.359205 0.399011 0.170 Uiso 1 1 calc R U . . .
H12C H 0.285088 0.316178 0.407006 0.170 Uiso 1 1 calc R U . . .
C17A C 0.52184(15) 0.4638(2) -0.01753(15) 0.0456(6) Uani 1 1 d . . . . .
C1B C 0.9160(2) 0.2545(3) 0.8225(2) 0.0658(9) Uani 1 1 d . . . . .
H1B H 0.880318 0.298332 0.825348 0.079 Uiso 1 1 calc R U . . .
N1B N 0.97923(16) 0.2581(2) 0.88383(17) 0.0593(7) Uani 1 1 d . . . . .
O1B O 1.07239(13) -0.05839(16) 0.79051(13) 0.0694(6) Uani 1 1 d . . . . .
S1B S 1.09450(4) 0.05180(7) 0.81873(4) 0.0591(2) Uani 1 1 d . . . . .
C2B C 0.90248(17) 0.1877(2) 0.7551(2) 0.0607(8) Uani 1 1 d . . . . .
H2B H 0.857787 0.185652 0.713418 0.073 Uiso 1 1 calc R U . . .
N2B N 0.94544(15) 0.0599(2) 0.68229(14) 0.0564(6) Uani 1 1 d . . . . .
O2B O 1.14954(13) 0.0679(2) 0.89687(13) 0.0853(8) Uani 1 1 d . . . . .
C3B C 0.95603(16) 0.1225(2) 0.74927(17) 0.0494(7) Uani 1 1 d . . . . .
N3B N 1.11170(14) 0.1091(2) 0.74605(15) 0.0580(7) Uani 1 1 d . . . . .
O3B O 1.13225(13) 0.28122(19) 0.80571(13) 0.0753(7) Uani 1 1 d . . . . .
C4B C 1.02121(16) 0.1254(2) 0.81736(16) 0.0487(7) Uani 1 1 d . . . . .
N4B N 1.11811(17) 0.2626(2) 0.67275(17) 0.0688(8) Uani 1 1 d . . . . .
O4B O 1.03541(11) 0.36620(15) 1.02456(11) 0.0568(5) Uani 1 1 d . . . . .
C5B C 1.03077(17) 0.1959(2) 0.88182(16) 0.0515(7) Uani 1 1 d . . . . .
H5B H 1.074565 0.200014 0.925102 0.062 Uiso 1 1 calc R U . . .
O5B O 1.05012(11) 0.51291(15) 1.10492(11) 0.0561(5) Uani 1 1 d . . . . .
C6B C 0.89209(15) 0.0773(2) 0.60280(17) 0.0522(7) Uani 1 1 d . . . . .
C7B C 0.88037(19) 0.1825(3) 0.5680(2) 0.0721(9) Uani 1 1 d . . . . .
H7B H 0.904556 0.243655 0.598033 0.087 Uiso 1 1 calc R U . . .
C8B C 0.8321(2) 0.1947(4) 0.4880(3) 0.0887(12) Uani 1 1 d . . . . .
H8B H 0.823653 0.264704 0.463742 0.106 Uiso 1 1 calc R U . . .
C9B C 0.7965(2) 0.1044(4) 0.4440(2) 0.0832(11) Uani 1 1 d . . . . .
H9B H 0.764080 0.114280 0.390211 0.100 Uiso 1 1 calc R U . . .
C10B C 0.80779(17) -0.0007(3) 0.4777(2) 0.0689(9) Uani 1 1 d . . . . .
C11B C 0.85601(16) -0.0129(3) 0.55783(18) 0.0567(7) Uani 1 1 d . . . . .
H11B H 0.864272 -0.083032 0.581821 0.068 Uiso 1 1 calc R U . . .
C12B C 0.7706(2) -0.0994(4) 0.4289(3) 0.1189(17) Uani 1 1 d . . . . .
H12D H 0.722138 -0.081635 0.398671 0.178 Uiso 1 1 calc R U . . .
H12E H 0.774538 -0.160464 0.465317 0.178 Uiso 1 1 calc R U . . .
H12F H 0.791343 -0.119643 0.391094 0.178 Uiso 1 1 calc R U . . .
C13B C 1.12124(16) 0.2250(3) 0.74481(18) 0.0571(8) Uani 1 1 d . . . . .
C14B C 1.1243(2) 0.3800(3) 0.6575(2) 0.0778(10) Uani 1 1 d . . . . .
H14C H 1.136093 0.420304 0.709424 0.093 Uiso 1 1 calc R U . . .
C15B C 1.0550(3) 0.4229(3) 0.5963(3) 0.1058(14) Uani 1 1 d . . . . .
H15G H 1.058951 0.500813 0.587420 0.159 Uiso 1 1 calc R U . . .
H15H H 1.019633 0.411396 0.617456 0.159 Uiso 1 1 calc R U . . .
H15I H 1.042460 0.383710 0.545217 0.159 Uiso 1 1 calc R U . . .
C16B C 1.1819(2) 0.3984(4) 0.6279(3) 0.1079(14) Uani 1 1 d . . . . .
H16G H 1.169024 0.365430 0.574538 0.162 Uiso 1 1 calc R U . . .
H16H H 1.224312 0.364861 0.665851 0.162 Uiso 1 1 calc R U . . .
H16I H 1.189121 0.476736 0.624528 0.162 Uiso 1 1 calc R U . . .
C17B C 1.02472(15) 0.4656(2) 1.03708(15) 0.0444(6) Uani 1 1 d . . . . .
H1AN H 0.4802(17) 0.301(3) 0.059(2) 0.077(11) Uiso 1 1 d . . . . .
H2AN H 0.4673(15) 0.014(3) 0.2852(18) 0.055(9) Uiso 1 1 d . . . . .
H3AN H 0.5857(16) 0.064(3) 0.3795(19) 0.063(9) Uiso 1 1 d . . . . .
H1BN H 0.991(2) 0.302(3) 0.932(3) 0.105(13) Uiso 1 1 d . . . . .
H2BN H 0.9773(18) 0.012(3) 0.684(2) 0.077(11) Uiso 1 1 d . . . . .
H3BN H 1.0947(17) 0.069(3) 0.701(2) 0.076(11) Uiso 1 1 d . . . . .
H4BN H 1.1034(17) 0.221(3) 0.631(2) 0.070(10) Uiso 1 1 d . . . . .
N4A N 0.6041(5) 0.2634(10) 0.4152(6) 0.060(2) Uani 0.598(11) 1 d . U P A 1
H4AN H 0.587048 0.227722 0.445102 0.072 Uiso 0.598(11) 1 calc R U P A 1
C13A C 0.6201(12) 0.2047(17) 0.3595(10) 0.055(3) Uani 0.598(11) 1 d . U P A 1
C14A C 0.6141(6) 0.3842(7) 0.4279(6) 0.068(2) Uani 0.598(11) 1 d . . P A 1
H14A H 0.592211 0.419611 0.373720 0.082 Uiso 0.598(11) 1 calc R U P A 1
C15A C 0.6901(5) 0.4177(8) 0.4637(7) 0.126(4) Uani 0.598(11) 1 d . . P A 1
H15A H 0.713810 0.380818 0.515491 0.189 Uiso 0.598(11) 1 calc R U P A 1
H15B H 0.693649 0.496674 0.471895 0.189 Uiso 0.598(11) 1 calc R U P A 1
H15C H 0.711257 0.396884 0.426488 0.189 Uiso 0.598(11) 1 calc R U P A 1
C16A C 0.5715(12) 0.4153(12) 0.4762(13) 0.108(6) Uani 0.598(11) 1 d . . P A 1
H16A H 0.524447 0.388735 0.448132 0.162 Uiso 0.598(11) 1 calc R U P A 1
H16B H 0.571003 0.494680 0.481461 0.162 Uiso 0.598(11) 1 calc R U P A 1
H16C H 0.591879 0.382326 0.529985 0.162 Uiso 0.598(11) 1 calc R U P A 1
N4D N 0.6282(9) 0.2447(16) 0.4374(10) 0.072(3) Uani 0.402(11) 1 d D U P A 2
H4D H 0.620637 0.192246 0.465819 0.086 Uiso 0.402(11) 1 calc R U P A 2
C13D C 0.623(2) 0.227(3) 0.3558(15) 0.068(6) Uani 0.402(11) 1 d D U P A 2
C14D C 0.6475(12) 0.3574(14) 0.4712(14) 0.108(6) Uani 0.402(11) 1 d . . P A 2
H14D H 0.668732 0.394984 0.437753 0.130 Uiso 0.402(11) 1 calc R U P A 2
C15D C 0.6984(7) 0.3581(15) 0.5548(12) 0.153(9) Uani 0.402(11) 1 d . . P A 2
H15D H 0.685839 0.303683 0.586173 0.230 Uiso 0.402(11) 1 calc R U P A 2
H15E H 0.699545 0.430401 0.578295 0.230 Uiso 0.402(11) 1 calc R U P A 2
H15F H 0.743680 0.340842 0.555744 0.230 Uiso 0.402(11) 1 calc R U P A 2
C16D C 0.5817(16) 0.427(2) 0.4637(17) 0.119(11) Uani 0.402(11) 1 d . . P A 2
H16D H 0.546856 0.421393 0.408468 0.178 Uiso 0.402(11) 1 calc R U P A 2
H16E H 0.594773 0.502885 0.476725 0.178 Uiso 0.402(11) 1 calc R U P A 2
H16F H 0.562970 0.397773 0.501320 0.178 Uiso 0.402(11) 1 calc R U P A 2
C1S C 0.7521(8) 0.1436(16) 0.1943(11) 0.276(12) Uani 0.560(8) 1 d D . P B 1
H1S1 H 0.797145 0.109557 0.221865 0.414 Uiso 0.560(8) 1 calc R U P B 1
H1S2 H 0.747413 0.169453 0.141106 0.414 Uiso 0.560(8) 1 calc R U P B 1
H1S3 H 0.716080 0.090044 0.187946 0.414 Uiso 0.560(8) 1 calc R U P B 1
O1S O 0.7456(3) 0.2336(6) 0.2411(5) 0.121(3) Uani 0.560(8) 1 d D . P B 1
H1S H 0.710563 0.225274 0.250854 0.181 Uiso 0.560(8) 1 calc R U P B 1


_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
C1A N1A 1.332(4) . ?
C1A C2A 1.364(4) . ?
N1A C5A 1.319(4) . ?
O1A S1A 1.429(2) . ?
S1A O2A 1.419(2) . ?
S1A N3A 1.621(3) . ?
S1A C4A 1.762(3) . ?
C2A C3A 1.397(4) . ?
N2A C3A 1.348(3) . ?
N2A C6A 1.427(4) . ?
C3A C4A 1.415(4) . ?
N3A C13A 1.31(2) . ?
N3A C13D 1.58(3) . ?
O3A C13D 1.08(3) . ?
O3A C13A 1.288(16) . ?
C4A C5A 1.366(4) . ?
O4A C17A 1.245(3) . ?
O5A C17A 1.248(3) . ?
C6A C7A 1.372(4) . ?
C6A C11A 1.373(4) . ?
C7A C8A 1.383(5) . ?
C8A C9A 1.362(5) . ?
C9A C10A 1.382(5) . ?
C10A C11A 1.392(4) . ?
C10A C12A 1.467(5) . ?
C17A C17A 1.555(5) 3_665 ?
C1B N1B 1.332(4) . ?
C1B C2B 1.371(4) . ?
N1B C5B 1.320(4) . ?
O1B S1B 1.427(2) . ?
S1B O2B 1.415(2) . ?
S1B N3B 1.621(3) . ?
S1B C4B 1.756(3) . ?
C2B C3B 1.400(4) . ?
N2B C3B 1.347(3) . ?
N2B C6B 1.419(4) . ?
C3B C4B 1.412(4) . ?
N3B C13B 1.410(4) . ?
O3B C13B 1.215(3) . ?
C4B C5B 1.371(4) . ?
N4B C13B 1.331(4) . ?
N4B C14B 1.453(4) . ?
O4B C17B 1.252(3) . ?
O5B C17B 1.241(3) . ?
C6B C11B 1.378(4) . ?
C6B C7B 1.386(4) . ?
C7B C8B 1.381(5) . ?
C8B C9B 1.369(6) . ?
C9B C10B 1.379(5) . ?
C10B C11B 1.381(4) . ?
C10B C12B 1.491(5) . ?
C14B C16B 1.505(6) . ?
C14B C15B 1.508(6) . ?
C17B C17B 1.547(5) 3_767 ?
N4A C13A 1.358(17) . ?
N4A C14A 1.473(15) . ?
C14A C15A 1.506(14) . ?
C14A C16A 1.51(2) . ?
N4D C13D 1.419(19) . ?
N4D C14D 1.47(2) . ?
C14D C15D 1.44(2) . ?
C14D C16D 1.56(3) . ?
C1S O1S 1.402(13) . ?

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
N1A C1A C2A 121.6(3) . . ?
C5A N1A C1A 120.5(3) . . ?
O2A S1A O1A 119.33(14) . . ?
O2A S1A N3A 111.50(15) . . ?
O1A S1A N3A 104.99(13) . . ?
O2A S1A C4A 107.81(13) . . ?
O1A S1A C4A 107.80(14) . . ?
N3A S1A C4A 104.38(13) . . ?
C1A C2A C3A 120.0(3) . . ?
C3A N2A C6A 126.4(3) . . ?
N2A C3A C2A 122.5(3) . . ?
N2A C3A C4A 121.2(3) . . ?
C2A C3A C4A 116.3(2) . . ?
C13A N3A S1A 120.8(6) . . ?
C13D N3A S1A 117.2(8) . . ?
C5A C4A C3A 119.9(3) . . ?
C5A C4A S1A 117.7(2) . . ?
C3A C4A S1A 122.02(19) . . ?
N1A C5A C4A 121.5(3) . . ?
C7A C6A C11A 120.6(3) . . ?
C7A C6A N2A 118.4(3) . . ?
C11A C6A N2A 120.8(3) . . ?
C6A C7A C8A 119.1(3) . . ?
C9A C8A C7A 120.2(3) . . ?
C8A C9A C10A 121.7(3) . . ?
C9A C10A C11A 117.6(3) . . ?
C9A C10A C12A 121.5(3) . . ?
C11A C10A C12A 121.0(4) . . ?
C6A C11A C10A 120.8(3) . . ?
O4A C17A O5A 125.3(2) . . ?
O4A C17A C17A 116.5(3) . 3_665 ?
O5A C17A C17A 118.2(3) . 3_665 ?
N1B C1B C2B 121.5(3) . . ?
C5B N1B C1B 120.6(3) . . ?
O2B S1B O1B 119.52(15) . . ?
O2B S1B N3B 111.66(16) . . ?
O1B S1B N3B 105.05(13) . . ?
O2B S1B C4B 107.76(14) . . ?
O1B S1B C4B 107.84(14) . . ?
N3B S1B C4B 103.89(13) . . ?
C1B C2B C3B 119.9(3) . . ?
C3B N2B C6B 125.4(3) . . ?
N2B C3B C2B 121.5(3) . . ?
N2B C3B C4B 122.0(3) . . ?
C2B C3B C4B 116.5(2) . . ?
C13B N3B S1B 120.7(2) . . ?
C5B C4B C3B 119.8(3) . . ?
C5B C4B S1B 117.6(2) . . ?
C3B C4B S1B 122.25(19) . . ?
C13B N4B C14B 122.3(3) . . ?
N1B C5B C4B 121.5(3) . . ?
C11B C6B C7B 120.2(3) . . ?
C11B C6B N2B 119.2(3) . . ?
C7B C6B N2B 120.3(3) . . ?
C8B C7B C6B 118.7(3) . . ?
C9B C8B C7B 120.5(4) . . ?
C8B C9B C10B 121.4(3) . . ?
C9B C10B C11B 118.1(3) . . ?
C9B C10B C12B 121.3(4) . . ?
C11B C10B C12B 120.6(4) . . ?
C6B C11B C10B 121.1(3) . . ?
O3B C13B N4B 125.6(3) . . ?
O3B C13B N3B 121.0(3) . . ?
N4B C13B N3B 113.4(3) . . ?
N4B C14B C16B 110.4(3) . . ?
N4B C14B C15B 109.7(3) . . ?
C16B C14B C15B 111.4(3) . . ?
O5B C17B O4B 124.9(2) . . ?
O5B C17B C17B 117.3(3) . 3_767 ?
O4B C17B C17B 117.8(3) . 3_767 ?
C13A N4A C14A 124.2(12) . . ?
O3A C13A N3A 124.0(10) . . ?
O3A C13A N4A 115.4(17) . . ?
N3A C13A N4A 119.6(12) . . ?
N4A C14A C15A 112.9(8) . . ?
N4A C14A C16A 104.6(10) . . ?
C15A C14A C16A 116.9(11) . . ?
C13D N4D C14D 117(2) . . ?
O3A C13D N4D 140(3) . . ?
O3A C13D N3A 118(2) . . ?
N4D C13D N3A 98(2) . . ?
C15D C14D N4D 113.2(15) . . ?
C15D C14D C16D 110.3(16) . . ?
N4D C14D C16D 111.6(17) . . ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
