# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_R1
_database_code_depnum_ccdc_archive 'CCDC 2285005'
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-09-27 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N4 O'
_chemical_formula_weight         378.42

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'

_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                   7.602(2)
_cell_length_b                   10.285(3)
_cell_length_c                   12.821(4)
_cell_angle_alpha                88.415(8)
_cell_angle_beta                 87.473(8)
_cell_angle_gamma                73.566(8)
_cell_volume                     960.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16242
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3333
_reflns_number_gt                2818
_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       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.1000P)²+0.0554P] 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         3333
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.05522(13) 0.83095(9) 0.54804(7) 0.0503(3) Uani 1 1 d . . . . .
N3 N 0.24515(16) 0.67361(11) 0.44073(10) 0.0480(3) Uani 1 1 d . . . . .
N1 N 0.14160(16) 0.32303(12) 0.32977(9) 0.0490(3) Uani 1 1 d . . . . .
N4 N 0.12747(18) 0.89755(12) 0.38752(10) 0.0531(3) Uani 1 1 d . . . . .
N2 N 0.27542(17) 0.48452(12) 0.28491(9) 0.0534(3) Uani 1 1 d . . . . .
C14 C 0.13960(18) 0.80070(13) 0.46259(10) 0.0432(3) Uani 1 1 d . . . . .
C8 C 0.23802(17) 0.43993(13) 0.47395(11) 0.0436(3) Uani 1 1 d . . . . .
C7 C 0.21696(17) 0.41924(13) 0.36292(11) 0.0439(3) Uani 1 1 d . . . . .
C20 C 0.37695(19) 0.94492(14) 0.27968(10) 0.0474(4) Uani 1 1 d . . . . .
C13 C 0.25855(17) 0.56196(13) 0.51069(11) 0.0443(3) Uani 1 1 d . . . . .
C15 C 0.2293(2) 0.88540(13) 0.29040(11) 0.0480(4) Uani 1 1 d . . . . .
C9 C 0.2436(2) 0.33434(15) 0.54644(12) 0.0533(4) Uani 1 1 d . . . . .
H9 H 0.229935 0.252844 0.523526 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2982(2) 0.46647(17) 0.68426(12) 0.0605(4) Uani 1 1 d . . . . .
H11 H 0.321106 0.474823 0.754047 0.073 Uiso 1 1 calc R U . . .
C6 C 0.15067(19) 0.32635(14) 0.22266(11) 0.0498(4) Uani 1 1 d . . . . .
C12 C 0.29376(19) 0.57206(16) 0.61492(12) 0.0539(4) Uani 1 1 d . . . . .
H12 H 0.314657 0.651003 0.638306 0.065 Uiso 1 1 calc R U . . .
C19 C 0.4747(2) 0.93590(16) 0.18206(12) 0.0578(4) Uani 1 1 d . . . . .
C21 C 0.4307(2) 1.01204(16) 0.36185(12) 0.0582(4) Uani 1 1 d . . . . .
H21 H 0.367547 1.018809 0.426178 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2361(2) 0.42676(15) 0.19553(12) 0.0542(4) Uani 1 1 d . . . . .
C10 C 0.2687(2) 0.34852(16) 0.65055(12) 0.0604(4) Uani 1 1 d . . . . .
H10 H 0.265747 0.278999 0.697960 0.073 Uiso 1 1 calc R U . . .
C1 C 0.0942(2) 0.25288(18) 0.14828(14) 0.0678(5) Uani 1 1 d . . . . .
H1 H 0.037094 0.186355 0.167229 0.081 Uiso 1 1 calc R U . . .
C18 C 0.4225(3) 0.86972(19) 0.09910(13) 0.0704(5) Uani 1 1 d . . . . .
H18 H 0.486166 0.863393 0.034949 0.084 Uiso 1 1 calc R U . . .
C16 C 0.1821(3) 0.82294(17) 0.20827(13) 0.0652(4) Uani 1 1 d . . . . .
H16 H 0.084559 0.785159 0.215766 0.078 Uiso 1 1 calc R U . . .
C24 C 0.6237(2) 0.9941(2) 0.17247(16) 0.0793(6) Uani 1 1 d . . . . .
H24 H 0.690097 0.988615 0.109259 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2806(3) 0.81537(19) 0.11203(13) 0.0775(5) Uani 1 1 d . . . . .
H17 H 0.247416 0.772251 0.056429 0.093 Uiso 1 1 calc R U . . .
C2 C 0.1263(3) 0.2827(2) 0.04558(15) 0.0790(5) Uani 1 1 d . . . . .
H2 H 0.088979 0.235961 -0.006246 0.095 Uiso 1 1 calc R U . . .
C4 C 0.2702(3) 0.45353(19) 0.09051(13) 0.0766(5) Uani 1 1 d . . . . .
H4 H 0.329637 0.518424 0.070836 0.092 Uiso 1 1 calc R U . . .
C22 C 0.5729(3) 1.0668(2) 0.34859(16) 0.0789(5) Uani 1 1 d . . . . .
H22 H 0.605165 1.111289 0.403704 0.095 Uiso 1 1 calc R U . . .
C3 C 0.2131(3) 0.3812(2) 0.01693(14) 0.0860(6) Uani 1 1 d . . . . .
H3 H 0.233108 0.398399 -0.053537 0.103 Uiso 1 1 calc R U . . .
C23 C 0.6710(3) 1.0575(2) 0.25391(19) 0.0891(6) Uani 1 1 d . . . . .
H23 H 0.769077 1.094638 0.246149 0.107 Uiso 1 1 calc R U . . .
H1N H 0.079(3) 0.2721(19) 0.3747(14) 0.080(5) Uiso 1 1 d . . . . .
H3N H 0.275(2) 0.6540(16) 0.3745(13) 0.060(5) Uiso 1 1 d . . . . .
H4N H 0.068(2) 0.9820(19) 0.4088(13) 0.068(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
O1 C14 1.2459(16) . ?
N3 C14 1.3557(18) . ?
N3 C13 1.4207(17) . ?
N1 C7 1.3613(18) . ?
N1 C6 1.3719(19) . ?
N4 C14 1.3527(17) . ?
N4 C15 1.4262(18) . ?
N2 C7 1.3194(17) . ?
N2 C5 1.387(2) . ?
C8 C9 1.4024(19) . ?
C8 C13 1.404(2) . ?
C8 C7 1.467(2) . ?
C20 C21 1.411(2) . ?
C20 C19 1.419(2) . ?
C20 C15 1.423(2) . ?
C13 C12 1.387(2) . ?
C15 C16 1.361(2) . ?
C9 C10 1.374(2) . ?
C11 C12 1.378(2) . ?
C11 C10 1.378(2) . ?
C6 C1 1.387(2) . ?
C6 C5 1.396(2) . ?
C19 C18 1.408(3) . ?
C19 C24 1.422(2) . ?
C21 C22 1.356(2) . ?
C5 C4 1.395(2) . ?
C1 C2 1.371(3) . ?
C18 C17 1.351(3) . ?
C16 C17 1.407(3) . ?
C24 C23 1.359(3) . ?
C2 C3 1.390(3) . ?
C4 C3 1.375(3) . ?
C22 C23 1.387(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
C14 N3 C13 122.68(12) . . ?
C7 N1 C6 107.32(12) . . ?
C14 N4 C15 127.15(12) . . ?
C7 N2 C5 104.85(12) . . ?
O1 C14 N4 119.48(12) . . ?
O1 C14 N3 122.84(12) . . ?
N4 C14 N3 117.68(12) . . ?
C9 C8 C13 118.06(13) . . ?
C9 C8 C7 119.84(13) . . ?
C13 C8 C7 122.08(12) . . ?
N2 C7 N1 112.61(13) . . ?
N2 C7 C8 125.02(13) . . ?
N1 C7 C8 122.28(12) . . ?
C21 C20 C19 118.62(14) . . ?
C21 C20 C15 122.93(13) . . ?
C19 C20 C15 118.45(14) . . ?
C12 C13 C8 119.67(13) . . ?
C12 C13 N3 120.48(13) . . ?
C8 C13 N3 119.85(13) . . ?
C16 C15 C20 120.51(14) . . ?
C16 C15 N4 120.84(14) . . ?
C20 C15 N4 118.60(13) . . ?
C10 C9 C8 121.51(15) . . ?
C12 C11 C10 120.25(15) . . ?
N1 C6 C1 132.52(14) . . ?
N1 C6 C5 105.26(13) . . ?
C1 C6 C5 122.22(15) . . ?
C11 C12 C13 120.76(15) . . ?
C18 C19 C20 119.38(15) . . ?
C18 C19 C24 122.55(16) . . ?
C20 C19 C24 118.06(16) . . ?
C22 C21 C20 121.10(16) . . ?
N2 C5 C4 130.40(15) . . ?
N2 C5 C6 109.95(13) . . ?
C4 C5 C6 119.65(15) . . ?
C9 C10 C11 119.57(14) . . ?
C2 C1 C6 117.00(17) . . ?
C17 C18 C19 120.46(15) . . ?
C15 C16 C17 120.15(16) . . ?
C23 C24 C19 121.27(17) . . ?
C18 C17 C16 121.05(17) . . ?
C1 C2 C3 121.69(18) . . ?
C3 C4 C5 118.01(17) . . ?
C21 C22 C23 120.88(19) . . ?
C4 C3 C2 121.41(17) . . ?
C24 C23 C22 120.05(18) . . ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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_R2
_database_code_depnum_ccdc_archive 'CCDC 2285016'
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-09-27 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N5 O'
_chemical_formula_weight         353.38

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

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

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

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

_cell_length_a                   16.878(9)
_cell_length_b                   24.478(13)
_cell_length_c                   8.566(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3539(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9699
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      23.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51084
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.465
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6226
_reflns_number_gt                4974
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  ?
_refine_special_details          
'the crystal of receptor R2 diffracted extremely weakly which resulted in high R factor, several attempts were made by using different crystallisation methods to grow better diffracting crystal of receptor R2, although it was unsuccessful'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0872P)²+6.2437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6226
_refine_ls_number_parameters     495
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.2132
_refine_ls_wR_factor_gt          0.2004
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.6479(4) 0.7677(2) 0.6175(5) 0.0532(16) Uani 1 1 d . . . . .
O2 O 0.4567(4) 0.5437(2) 0.1795(6) 0.0457(14) Uani 1 1 d . . . . .
N4 N 0.6485(4) 0.8442(2) 0.4668(6) 0.0386(15) Uani 1 1 d . . . . .
H4N H 0.646992 0.855290 0.371596 0.046 Uiso 1 1 calc R U . . .
N7 N 0.5672(4) 0.5727(2) 0.6947(7) 0.0365(14) Uani 1 1 d . . . . .
N9 N 0.5151(4) 0.4749(2) 0.3149(7) 0.0437(16) Uani 1 1 d . . . . .
H9N H 0.531661 0.465760 0.406183 0.052 Uiso 1 1 calc R U . . .
N3 N 0.6380(4) 0.7591(2) 0.3508(7) 0.0401(15) Uani 1 1 d . . . . .
H3N H 0.623910 0.775820 0.266901 0.048 Uiso 1 1 calc R U . . .
N6 N 0.5969(4) 0.6614(3) 0.7231(7) 0.0365(14) Uani 1 1 d . . . . .
N1 N 0.4868(4) 0.6565(3) 0.0942(7) 0.0424(16) Uani 1 1 d . . . . .
N2 N 0.5392(4) 0.7415(2) 0.0950(7) 0.0405(15) Uani 1 1 d . . . . .
N8 N 0.4713(4) 0.5495(2) 0.4463(6) 0.0411(16) Uani 1 1 d . . . . .
H8N H 0.486059 0.532359 0.529014 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5480(4) 0.6897(3) 0.1400(7) 0.0312(15) Uani 1 1 d . . . . .
C35 C 0.4791(5) 0.5239(3) 0.3042(7) 0.0335(16) Uani 1 1 d . . . . .
C36 C 0.5288(4) 0.4374(3) 0.1961(7) 0.0338(16) Uani 1 1 d . . . . .
C40 C 0.5455(4) 0.4092(3) -0.0687(7) 0.0323(16) Uani 1 1 d . . . . .
C15 C 0.6544(4) 0.8846(3) 0.5800(8) 0.0337(16) Uani 1 1 d . . . . .
C8 C 0.6121(4) 0.6692(3) 0.2373(7) 0.0312(16) Uani 1 1 d . . . . .
C34 C 0.4397(4) 0.6030(3) 0.4621(8) 0.0338(16) Uani 1 1 d . . . . .
N10 N 0.5486(5) 0.4329(3) -0.3634(7) 0.058(2) Uani 1 1 d . . . . .
C14 C 0.6447(5) 0.7885(3) 0.4883(8) 0.0360(17) Uani 1 1 d . . . . .
C27 C 0.6362(4) 0.5772(3) 0.7833(8) 0.0354(17) Uani 1 1 d . . . . .
C28 C 0.5458(4) 0.6239(3) 0.6587(7) 0.0358(17) Uani 1 1 d . . . . .
C13 C 0.6537(4) 0.7023(3) 0.3448(8) 0.0358(16) Uani 1 1 d . . . . .
C26 C 0.6557(5) 0.6334(3) 0.7981(8) 0.0383(17) Uani 1 1 d . . . . .
C29 C 0.4772(4) 0.6400(3) 0.5681(8) 0.0340(16) Uani 1 1 d . . . . .
C41 C 0.5331(4) 0.4511(3) 0.0397(7) 0.0344(16) Uani 1 1 d . . . . .
H41 H 0.527809 0.487228 0.007449 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4339(5) 0.6886(3) 0.0151(8) 0.0380(17) Uani 1 1 d . . . . .
C17 C 0.6609(5) 0.9170(3) 0.8433(8) 0.0411(18) Uani 1 1 d . . . . .
C9 C 0.6314(5) 0.6137(3) 0.2272(9) 0.0431(19) Uani 1 1 d . . . . .
H9 H 0.604751 0.591853 0.155656 0.052 Uiso 1 1 calc R U . . .
C37 C 0.5377(5) 0.3828(3) 0.2396(9) 0.0423(19) Uani 1 1 d . . . . .
H37 H 0.534942 0.373767 0.344880 0.051 Uiso 1 1 calc R U . . .
C39 C 0.5536(5) 0.3544(3) -0.0271(8) 0.0393(18) Uani 1 1 d . . . . .
H39 H 0.560697 0.327265 -0.101818 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6529(5) 0.8739(3) 0.7393(7) 0.0380(17) Uani 1 1 d . . . . .
H16 H 0.646723 0.838394 0.775684 0.046 Uiso 1 1 calc R U . . .
N5 N 0.6609(6) 0.8939(4) 1.1365(8) 0.077(3) Uani 1 1 d . . . . .
C20 C 0.6626(5) 0.9383(3) 0.5285(9) 0.046(2) Uani 1 1 d . . . . .
H20 H 0.663172 0.945490 0.421904 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4656(5) 0.7415(3) 0.0145(8) 0.0415(19) Uani 1 1 d . . . . .
C33 C 0.3741(5) 0.6190(3) 0.3836(9) 0.0434(19) Uani 1 1 d . . . . .
H33 H 0.347501 0.594127 0.320475 0.052 Uiso 1 1 calc R U . . .
C32 C 0.3461(5) 0.6723(3) 0.3966(9) 0.0450(19) Uani 1 1 d . . . . .
H32 H 0.302527 0.683199 0.337790 0.054 Uiso 1 1 calc R U . . .
C30 C 0.4478(5) 0.6927(3) 0.5780(9) 0.0424(18) Uani 1 1 d . . . . .
H30 H 0.473187 0.717829 0.642274 0.051 Uiso 1 1 calc R U . . .
C24 C 0.7718(6) 0.6094(4) 0.9347(10) 0.054(2) Uani 1 1 d . . . . .
H24 H 0.817759 0.618897 0.988076 0.065 Uiso 1 1 calc R U . . .
C38 C 0.5505(5) 0.3420(3) 0.1332(8) 0.047(2) Uani 1 1 d . . . . .
H38 H 0.557037 0.306139 0.166768 0.057 Uiso 1 1 calc R U . . .
C10 C 0.6888(5) 0.5908(4) 0.3207(10) 0.051(2) Uani 1 1 d . . . . .
H10 H 0.700351 0.553706 0.313139 0.061 Uiso 1 1 calc R U . . .
C42 C 0.5463(5) 0.4224(3) -0.2322(8) 0.0385(17) Uani 1 1 d . . . . .
C4 C 0.4269(6) 0.7834(3) -0.0598(9) 0.053(2) Uani 1 1 d . . . . .
H4 H 0.449075 0.818082 -0.066135 0.064 Uiso 1 1 calc R U . . .
C12 C 0.7124(4) 0.6785(3) 0.4354(9) 0.0420(19) Uani 1 1 d . . . . .
H12 H 0.741365 0.699960 0.504368 0.050 Uiso 1 1 calc R U . . .
C31 C 0.3819(5) 0.7088(3) 0.4951(10) 0.049(2) Uani 1 1 d . . . . .
H31 H 0.362039 0.744025 0.505870 0.059 Uiso 1 1 calc R U . . .
C11 C 0.7286(5) 0.6231(4) 0.4246(10) 0.052(2) Uani 1 1 d . . . . .
H11 H 0.766938 0.607665 0.488926 0.063 Uiso 1 1 calc R U . . .
C18 C 0.6685(6) 0.9712(3) 0.7912(10) 0.060(3) Uani 1 1 d . . . . .
H18 H 0.672546 0.999989 0.861558 0.072 Uiso 1 1 calc R U . . .
C21 C 0.6607(6) 0.9051(4) 1.0071(9) 0.057(2) Uani 1 1 d . . . . .
C23 C 0.7522(5) 0.5541(4) 0.9197(11) 0.056(2) Uani 1 1 d . . . . .
H23 H 0.785980 0.527901 0.961468 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6846(5) 0.5378(4) 0.8451(10) 0.051(2) Uani 1 1 d . . . . .
H22 H 0.671811 0.500931 0.836507 0.061 Uiso 1 1 calc R U . . .
C25 C 0.7250(5) 0.6502(4) 0.8726(10) 0.053(2) Uani 1 1 d . . . . .
H25 H 0.738907 0.686861 0.880141 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3539(6) 0.7722(4) -0.1250(9) 0.061(3) Uani 1 1 d . . . . .
H3 H 0.325846 0.800081 -0.173871 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6698(7) 0.9803(4) 0.6304(12) 0.067(3) Uani 1 1 d . . . . .
H19 H 0.675702 1.015740 0.592788 0.080 Uiso 1 1 calc R U . . .
C2 C 0.3212(6) 0.7196(4) -0.1189(9) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.271672 0.713286 -0.162964 0.072 Uiso 1 1 calc R U . . .
C1 C 0.3615(6) 0.6770(4) -0.0484(10) 0.061(2) Uani 1 1 d . . . . .
H1 H 0.340270 0.642013 -0.044355 0.074 Uiso 1 1 calc R U . . .
H1N H 0.458(7) 0.624(5) 0.148(13) 0.10(4) Uiso 1 1 d . . . . .
H6N H 0.600(3) 0.699(2) 0.701(6) 0.003(13) 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 C14 1.219(8) . ?
O2 C35 1.233(8) . ?
N4 C14 1.376(9) . ?
N4 C15 1.388(9) . ?
N4 H4N 0.8600 . ?
N7 C28 1.339(9) . ?
N7 C27 1.396(9) . ?
N9 C35 1.347(9) . ?
N9 C36 1.391(9) . ?
N9 H9N 0.8600 . ?
N3 C14 1.385(9) . ?
N3 C13 1.417(9) . ?
N3 H3N 0.8600 . ?
N6 C26 1.365(10) . ?
N6 C28 1.374(9) . ?
N6 H6N 0.95(6) . ?
N1 C6 1.370(10) . ?
N1 C7 1.371(9) . ?
N1 H1N 1.05(12) . ?
N2 C7 1.335(9) . ?
N2 C5 1.421(10) . ?
N8 C35 1.375(8) . ?
N8 C34 1.422(9) . ?
N8 H8N 0.8600 . ?
C7 C8 1.455(10) . ?
C36 C41 1.384(9) . ?
C36 C37 1.395(10) . ?
C40 C39 1.396(10) . ?
C40 C41 1.399(9) . ?
C40 C42 1.437(10) . ?
C15 C16 1.389(9) . ?
C15 C20 1.395(10) . ?
C8 C9 1.399(10) . ?
C8 C13 1.413(10) . ?
C34 C33 1.353(11) . ?
C34 C29 1.429(10) . ?
N10 C42 1.154(9) . ?
C27 C22 1.371(11) . ?
C27 C26 1.420(10) . ?
C28 C29 1.449(11) . ?
C13 C12 1.388(10) . ?
C26 C25 1.394(11) . ?
C29 C30 1.384(10) . ?
C41 H41 0.9300 . ?
C6 C1 1.367(12) . ?
C6 C5 1.402(11) . ?
C17 C16 1.388(10) . ?
C17 C18 1.405(11) . ?
C17 C21 1.434(10) . ?
C9 C10 1.377(11) . ?
C9 H9 0.9300 . ?
C37 C38 1.369(10) . ?
C37 H37 0.9300 . ?
C39 C38 1.407(10) . ?
C39 H39 0.9300 . ?
C16 H16 0.9300 . ?
N5 C21 1.142(10) . ?
C20 C19 1.354(12) . ?
C20 H20 0.9300 . ?
C5 C4 1.372(11) . ?
C33 C32 1.392(11) . ?
C33 H33 0.9300 . ?
C32 C31 1.371(11) . ?
C32 H32 0.9300 . ?
C30 C31 1.377(12) . ?
C30 H30 0.9300 . ?
C24 C25 1.380(12) . ?
C24 C23 1.397(13) . ?
C24 H24 0.9300 . ?
C38 H38 0.9300 . ?
C10 C11 1.367(12) . ?
C10 H10 0.9300 . ?
C4 C3 1.380(13) . ?
C4 H4 0.9300 . ?
C12 C11 1.387(12) . ?
C12 H12 0.9300 . ?
C31 H31 0.9300 . ?
C11 H11 0.9300 . ?
C18 C19 1.396(13) . ?
C18 H18 0.9300 . ?
C23 C22 1.369(12) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C3 C2 1.400(14) . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?
C2 C1 1.384(13) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?

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
C14 N4 C15 127.9(6) . . ?
C14 N4 H4N 116.0 . . ?
C15 N4 H4N 116.0 . . ?
C28 N7 C27 106.0(6) . . ?
C35 N9 C36 127.8(6) . . ?
C35 N9 H9N 116.1 . . ?
C36 N9 H9N 116.1 . . ?
C14 N3 C13 121.7(6) . . ?
C14 N3 H3N 119.1 . . ?
C13 N3 H3N 119.1 . . ?
C26 N6 C28 108.1(6) . . ?
C26 N6 H6N 123(3) . . ?
C28 N6 H6N 127(3) . . ?
C6 N1 C7 107.0(6) . . ?
C6 N1 H1N 111(6) . . ?
C7 N1 H1N 133(6) . . ?
C7 N2 C5 103.7(6) . . ?
C35 N8 C34 122.7(6) . . ?
C35 N8 H8N 118.6 . . ?
C34 N8 H8N 118.6 . . ?
N2 C7 N1 113.4(6) . . ?
N2 C7 C8 125.1(6) . . ?
N1 C7 C8 121.4(6) . . ?
O2 C35 N9 123.2(6) . . ?
O2 C35 N8 123.9(6) . . ?
N9 C35 N8 112.9(6) . . ?
C41 C36 N9 123.8(6) . . ?
C41 C36 C37 119.1(6) . . ?
N9 C36 C37 117.1(6) . . ?
C39 C40 C41 123.4(6) . . ?
C39 C40 C42 117.7(6) . . ?
C41 C40 C42 118.9(6) . . ?
N4 C15 C16 123.4(7) . . ?
N4 C15 C20 117.3(6) . . ?
C16 C15 C20 119.3(7) . . ?
C9 C8 C13 118.8(7) . . ?
C9 C8 C7 118.1(6) . . ?
C13 C8 C7 123.0(6) . . ?
C33 C34 N8 121.7(6) . . ?
C33 C34 C29 119.7(7) . . ?
N8 C34 C29 118.6(7) . . ?
O1 C14 N4 122.2(6) . . ?
O1 C14 N3 124.0(6) . . ?
N4 C14 N3 113.8(6) . . ?
C22 C27 N7 130.7(7) . . ?
C22 C27 C26 120.7(7) . . ?
N7 C27 C26 108.5(6) . . ?
N7 C28 N6 111.3(7) . . ?
N7 C28 C29 126.3(7) . . ?
N6 C28 C29 122.4(6) . . ?
C12 C13 C8 118.5(7) . . ?
C12 C13 N3 121.8(7) . . ?
C8 C13 N3 119.6(7) . . ?
N6 C26 C25 132.6(7) . . ?
N6 C26 C27 106.0(6) . . ?
C25 C26 C27 121.4(7) . . ?
C30 C29 C34 118.0(7) . . ?
C30 C29 C28 120.5(7) . . ?
C34 C29 C28 121.5(6) . . ?
C36 C41 C40 118.2(6) . . ?
C36 C41 H41 120.9 . . ?
C40 C41 H41 120.9 . . ?
C1 C6 N1 131.3(8) . . ?
C1 C6 C5 122.2(8) . . ?
N1 C6 C5 106.4(7) . . ?
C16 C17 C18 121.5(7) . . ?
C16 C17 C21 118.2(7) . . ?
C18 C17 C21 120.3(7) . . ?
C10 C9 C8 121.6(8) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C38 C37 C36 122.5(7) . . ?
C38 C37 H37 118.7 . . ?
C36 C37 H37 118.7 . . ?
C40 C39 C38 117.0(6) . . ?
C40 C39 H39 121.5 . . ?
C38 C39 H39 121.5 . . ?
C17 C16 C15 119.1(7) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C19 C20 C15 121.4(7) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C4 C5 C6 120.6(8) . . ?
C4 C5 N2 130.0(7) . . ?
C6 C5 N2 109.4(6) . . ?
C34 C33 C32 120.6(7) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C31 C32 C33 120.7(8) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C31 C30 C29 121.6(7) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C25 C24 C23 122.0(8) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C37 C38 C39 119.9(7) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C11 C10 C9 119.2(8) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N10 C42 C40 178.6(9) . . ?
C5 C4 C3 117.7(8) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C11 C12 C13 121.0(8) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C32 C31 C30 119.2(8) . . ?
C32 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
C10 C11 C12 120.8(8) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C19 C18 C17 117.8(7) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
N5 C21 C17 177.9(10) . . ?
C22 C23 C24 121.6(9) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C22 C27 118.1(8) . . ?
C23 C22 H22 121.0 . . ?
C27 C22 H22 121.0 . . ?
C24 C25 C26 116.3(8) . . ?
C24 C25 H25 121.8 . . ?
C26 C25 H25 121.8 . . ?
C4 C3 C2 121.2(8) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C20 C19 C18 120.9(9) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C1 C2 C3 121.0(9) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C6 C1 C2 117.2(9) . . ?
C6 C1 H1 121.4 . . ?
C2 C1 H1 121.4 . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_R1_HSO4
_database_code_depnum_ccdc_archive 'CCDC 2285018'
loop_
_audit_author_name
_audit_author_address
'Oiyao Appun Pegu'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2023-09-27 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H55 N5 O5 S'
_chemical_formula_weight         717.95

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   18.1980(14)
_cell_length_b                   11.6386(9)
_cell_length_c                   18.3823(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3893.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9110
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            99620
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6855
_reflns_number_gt                5128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.1000P)²+0.7509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6855
_refine_ls_number_parameters     472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1875
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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
S001 S 0.68256(8) 0.68004(12) 0.53492(9) 0.0485(4) Uani 1 1 d . . . . .
N1 N 0.7505(3) 0.6842(5) 0.2281(3) 0.0469(13) Uani 1 1 d . . . . .
O4 O 0.6181(2) 0.7067(4) 0.4922(2) 0.0613(12) Uani 1 1 d . . . . .
O1 O 0.5922(3) 1.0803(4) 0.3789(2) 0.0574(11) Uani 1 1 d . . . . .
N4 N 0.5594(3) 0.9287(4) 0.4500(3) 0.0511(13) Uani 1 1 d . . . . .
H4N H 0.574555 0.864712 0.468000 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6029(3) 0.9825(5) 0.4001(3) 0.0450(14) Uani 1 1 d . . . . .
O3 O 0.6935(3) 0.7575(5) 0.5943(3) 0.0792(15) Uani 1 1 d . . . . .
N3 N 0.6610(3) 0.9159(4) 0.3773(3) 0.0483(12) Uani 1 1 d . . . . .
H3N H 0.661681 0.845579 0.391620 0.058 Uiso 1 1 calc R U . . .
O2 O 0.7498(3) 0.7036(5) 0.4846(3) 0.0737(16) Uani 1 1 d . . . . .
N5 N 0.4797(3) 0.3832(4) 0.5312(3) 0.0533(13) Uani 1 1 d . . . . .
N2 N 0.7170(3) 0.6895(4) 0.3438(3) 0.0485(13) Uani 1 1 d . . . . .
C7 C 0.7406(3) 0.7503(5) 0.2872(3) 0.0410(13) Uani 1 1 d . . . . .
C20 C 0.4711(3) 0.9582(5) 0.5483(3) 0.0430(14) Uani 1 1 d . . . . .
O5 O 0.6866(3) 0.5622(4) 0.5546(3) 0.0864(18) Uani 1 1 d . . . . .
C6 C 0.7316(3) 0.5723(5) 0.2461(3) 0.0472(14) Uani 1 1 d . . . . .
C8 C 0.7568(3) 0.8745(5) 0.2883(3) 0.0401(12) Uani 1 1 d . . . . .
C9 C 0.8142(3) 0.9148(6) 0.2453(3) 0.0493(15) Uani 1 1 d . . . . .
H9 H 0.838874 0.863280 0.215249 0.059 Uiso 1 1 calc R U . . .
C21 C 0.5163(3) 0.9052(6) 0.6003(4) 0.0557(17) Uani 1 1 d . . . . .
H21 H 0.562746 0.879763 0.586747 0.067 Uiso 1 1 calc R U . . .
C22 C 0.4931(4) 0.8903(7) 0.6705(4) 0.065(2) Uani 1 1 d . . . . .
H22 H 0.524150 0.855632 0.704174 0.078 Uiso 1 1 calc R U . . .
C13 C 0.7190(3) 0.9523(5) 0.3330(3) 0.0419(13) Uani 1 1 d . . . . .
C15 C 0.4912(3) 0.9716(5) 0.4740(3) 0.0447(14) Uani 1 1 d . . . . .
C5 C 0.7101(4) 0.5779(5) 0.3181(4) 0.0527(16) Uani 1 1 d . . . . .
C25 C 0.4627(3) 0.5099(5) 0.5381(5) 0.0616(16) Uani 1 1 d . . . . .
H25A H 0.485412 0.549950 0.497652 0.074 Uiso 1 1 calc R U . . .
H25B H 0.485211 0.538324 0.582444 0.074 Uiso 1 1 calc R U . . .
C23 C 0.4234(4) 0.9268(7) 0.6920(4) 0.072(2) Uani 1 1 d . . . . .
H23 H 0.407743 0.914677 0.739542 0.087 Uiso 1 1 calc R U . . .
C1 C 0.7314(4) 0.4710(6) 0.2067(4) 0.0609(18) Uani 1 1 d . . . . .
H1 H 0.748179 0.467205 0.158986 0.073 Uiso 1 1 calc R U . . .
C19 C 0.4004(3) 0.9963(5) 0.5705(4) 0.0501(15) Uani 1 1 d . . . . .
C17 C 0.3753(3) 1.0629(5) 0.4508(4) 0.0581(18) Uani 1 1 d . . . . .
H17 H 0.343918 1.098879 0.418060 0.070 Uiso 1 1 calc R U . . .
C11 C 0.7993(4) 1.1027(6) 0.2896(4) 0.0584(17) Uani 1 1 d . . . . .
H11 H 0.813909 1.179217 0.290684 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7414(4) 1.0671(5) 0.3324(4) 0.0552(16) Uani 1 1 d . . . . .
H12 H 0.716966 1.120245 0.361411 0.066 Uiso 1 1 calc R U . . .
C10 C 0.8356(4) 1.0266(6) 0.2455(4) 0.0608(18) Uani 1 1 d . . . . .
H10 H 0.874180 1.051190 0.216160 0.073 Uiso 1 1 calc R U . . .
C18 C 0.3540(3) 1.0510(5) 0.5204(4) 0.0592(18) Uani 1 1 d . . . . .
H18 H 0.308518 1.078915 0.535312 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4438(4) 1.0225(5) 0.4261(4) 0.0540(16) Uani 1 1 d . . . . .
H16 H 0.456808 1.030379 0.377453 0.065 Uiso 1 1 calc R U . . .
C29 C 0.4441(4) 0.3160(6) 0.5922(4) 0.066(2) Uani 1 1 d . . . . .
H29A H 0.391391 0.327362 0.589637 0.080 Uiso 1 1 calc R U . . .
H29B H 0.453556 0.234903 0.584274 0.080 Uiso 1 1 calc R U . . .
C38 C 0.4689(5) 0.3944(8) 0.3909(5) 0.084(2) Uani 1 1 d . . . . .
H38A H 0.451969 0.473352 0.392913 0.101 Uiso 1 1 calc R U . . .
H38B H 0.521897 0.395181 0.385076 0.101 Uiso 1 1 calc R U . . .
C37 C 0.4490(4) 0.3335(6) 0.4605(4) 0.0618(19) Uani 1 1 d . . . . .
H37A H 0.465512 0.254510 0.456569 0.074 Uiso 1 1 calc R U . . .
H37B H 0.395895 0.332059 0.464275 0.074 Uiso 1 1 calc R U . . .
C24 C 0.3791(4) 0.9791(7) 0.6446(4) 0.066(2) Uani 1 1 d . . . . .
H24 H 0.333357 1.004940 0.660061 0.079 Uiso 1 1 calc R U . . .
C33 C 0.5623(3) 0.3723(6) 0.5321(5) 0.0683(18) Uani 1 1 d . . . . .
H33A H 0.580908 0.412642 0.574405 0.082 Uiso 1 1 calc R U . . .
H33B H 0.581727 0.410519 0.489329 0.082 Uiso 1 1 calc R U . . .
C2 C 0.7045(5) 0.3753(6) 0.2434(5) 0.076(2) Uani 1 1 d . . . . .
H2A H 0.701679 0.305573 0.218873 0.092 Uiso 1 1 calc R U . . .
C30 C 0.4695(6) 0.3469(8) 0.6673(5) 0.086(3) Uani 1 1 d . . . . .
H30A H 0.443558 0.415207 0.683112 0.103 Uiso 1 1 calc R U . . .
H30B H 0.521498 0.365308 0.665491 0.103 Uiso 1 1 calc R U . . .
C4 C 0.6843(4) 0.4786(6) 0.3537(5) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.669392 0.480437 0.402073 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6821(5) 0.3806(6) 0.3145(5) 0.081(2) Uani 1 1 d . . . . .
H3 H 0.664634 0.314058 0.336583 0.097 Uiso 1 1 calc R U . . .
C26 C 0.3816(4) 0.5399(7) 0.5396(7) 0.095(3) Uani 1 1 d . . . . .
H26A H 0.360008 0.511793 0.584398 0.114 Uiso 1 1 calc R U . . .
H26B H 0.357011 0.502335 0.499279 0.114 Uiso 1 1 calc R U . . .
C34 C 0.5916(4) 0.2502(8) 0.5336(6) 0.093(3) Uani 1 1 d . . . . .
H34A H 0.567244 0.208141 0.572235 0.111 Uiso 1 1 calc R U . . .
H34B H 0.579612 0.212824 0.487925 0.111 Uiso 1 1 calc R U . . .
C40 C 0.4475(7) 0.3941(10) 0.2568(6) 0.122(4) Uani 1 1 d . . . . .
H40A H 0.427037 0.470089 0.258836 0.183 Uiso 1 1 calc R U . . .
H40B H 0.424547 0.351754 0.218173 0.183 Uiso 1 1 calc R U . . .
H40C H 0.499381 0.398988 0.248010 0.183 Uiso 1 1 calc R U . . .
C31 C 0.4577(7) 0.2533(10) 0.7221(6) 0.111(3) Uani 1 1 d . . . . .
H31A H 0.405295 0.239579 0.726373 0.133 Uiso 1 1 calc R U . . .
H31B H 0.479904 0.183340 0.703715 0.133 Uiso 1 1 calc R U . . .
C27 C 0.3699(5) 0.6697(7) 0.5342(7) 0.101(3) Uani 1 1 d . . . . .
H27A H 0.320921 0.688139 0.551527 0.121 Uiso 1 1 calc R U . . .
H27B H 0.404898 0.708200 0.565624 0.121 Uiso 1 1 calc R U . . .
C32 C 0.4870(6) 0.2754(12) 0.7947(6) 0.125(4) Uani 1 1 d . . . . .
H32A H 0.535149 0.308380 0.790665 0.187 Uiso 1 1 calc R U . . .
H32B H 0.489876 0.204455 0.821237 0.187 Uiso 1 1 calc R U . . .
H32C H 0.455189 0.327733 0.819935 0.187 Uiso 1 1 calc R U . . .
C28 C 0.3783(7) 0.7133(8) 0.4599(6) 0.118(4) Uani 1 1 d . . . . .
H28A H 0.429410 0.712881 0.446844 0.178 Uiso 1 1 calc R U . . .
H28B H 0.359729 0.790346 0.457276 0.178 Uiso 1 1 calc R U . . .
H28C H 0.351411 0.665153 0.426909 0.178 Uiso 1 1 calc R U . . .
C36 C 0.7018(5) 0.1286(9) 0.5503(6) 0.102(3) Uani 1 1 d . . . . .
H36A H 0.742516 0.130135 0.583565 0.153 Uiso 1 1 calc R U . . .
H36B H 0.718599 0.104159 0.503303 0.153 Uiso 1 1 calc R U . . .
H36C H 0.665272 0.075919 0.567849 0.153 Uiso 1 1 calc R U . . .
C35 C 0.6697(5) 0.2444(9) 0.5447(10) 0.142(5) Uani 1 1 d . . . . .
H35A H 0.681423 0.286121 0.588880 0.170 Uiso 1 1 calc R U . . .
H35B H 0.693567 0.284086 0.504719 0.170 Uiso 1 1 calc R U . . .
C39 C 0.4343(6) 0.3346(8) 0.3271(5) 0.098(3) Uani 1 1 d . . . . .
H39A H 0.453604 0.257067 0.323965 0.117 Uiso 1 1 calc R U . . .
H39B H 0.381720 0.329040 0.335173 0.117 Uiso 1 1 calc R U . . .
H2O H 0.741(4) 0.702(6) 0.443(5) 0.06(2) Uiso 1 1 d . . . . .
H1N H 0.762(3) 0.702(5) 0.190(4) 0.031(17) 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
S001 O5 1.420(5) . ?
S001 O3 1.430(5) . ?
S001 O4 1.446(5) . ?
S001 O2 1.558(6) . ?
N1 C7 1.344(8) . ?
N1 C6 1.388(8) . ?
O1 C14 1.219(7) . ?
N4 C14 1.364(8) . ?
N4 C15 1.409(8) . ?
C14 N3 1.376(8) . ?
N3 C13 1.400(7) . ?
N5 C33 1.509(8) . ?
N5 C25 1.512(8) . ?
N5 C29 1.513(9) . ?
N5 C37 1.528(9) . ?
N2 C7 1.329(8) . ?
N2 C5 1.388(8) . ?
C7 C8 1.475(8) . ?
C20 C21 1.402(9) . ?
C20 C19 1.421(8) . ?
C20 C15 1.423(9) . ?
C6 C5 1.381(9) . ?
C6 C1 1.383(9) . ?
C8 C9 1.393(8) . ?
C8 C13 1.403(8) . ?
C9 C10 1.358(9) . ?
C21 C22 1.369(10) . ?
C22 C23 1.395(11) . ?
C13 C12 1.396(8) . ?
C15 C16 1.366(9) . ?
C5 C4 1.410(10) . ?
C25 C26 1.517(10) . ?
C23 C24 1.334(11) . ?
C1 C2 1.391(11) . ?
C19 C18 1.402(9) . ?
C19 C24 1.429(10) . ?
C17 C18 1.344(11) . ?
C17 C16 1.408(9) . ?
C11 C10 1.370(10) . ?
C11 C12 1.379(9) . ?
C29 C30 1.499(11) . ?
C38 C39 1.503(11) . ?
C38 C37 1.507(11) . ?
C33 C34 1.518(11) . ?
C2 C3 1.371(12) . ?
C30 C31 1.500(12) . ?
C4 C3 1.349(11) . ?
C26 C27 1.528(11) . ?
C34 C35 1.438(12) . ?
C40 C39 1.485(13) . ?
C31 C32 1.459(15) . ?
C27 C28 1.465(16) . ?
C36 C35 1.473(14) . ?

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
O5 S001 O3 114.0(3) . . ?
O5 S001 O4 112.8(3) . . ?
O3 S001 O4 113.1(3) . . ?
O5 S001 O2 106.3(4) . . ?
O3 S001 O2 103.4(3) . . ?
O4 S001 O2 106.1(3) . . ?
C7 N1 C6 108.1(5) . . ?
C14 N4 C15 124.0(5) . . ?
O1 C14 N4 123.5(5) . . ?
O1 C14 N3 123.4(5) . . ?
N4 C14 N3 113.1(5) . . ?
C14 N3 C13 125.9(5) . . ?
C33 N5 C25 106.6(5) . . ?
C33 N5 C29 112.0(6) . . ?
C25 N5 C29 110.8(5) . . ?
C33 N5 C37 109.9(6) . . ?
C25 N5 C37 111.5(5) . . ?
C29 N5 C37 106.2(5) . . ?
C7 N2 C5 105.1(5) . . ?
N2 C7 N1 111.9(5) . . ?
N2 C7 C8 125.1(5) . . ?
N1 C7 C8 123.0(5) . . ?
C21 C20 C19 118.2(5) . . ?
C21 C20 C15 123.5(5) . . ?
C19 C20 C15 118.3(5) . . ?
C5 C6 C1 122.8(6) . . ?
C5 C6 N1 104.7(5) . . ?
C1 C6 N1 132.5(6) . . ?
C9 C8 C13 118.9(5) . . ?
C9 C8 C7 118.2(5) . . ?
C13 C8 C7 122.9(5) . . ?
C10 C9 C8 122.4(6) . . ?
C22 C21 C20 121.1(6) . . ?
C21 C22 C23 120.5(7) . . ?
C12 C13 N3 120.9(5) . . ?
C12 C13 C8 118.0(5) . . ?
N3 C13 C8 121.0(5) . . ?
C16 C15 N4 120.6(6) . . ?
C16 C15 C20 120.3(5) . . ?
N4 C15 C20 119.2(5) . . ?
C6 C5 N2 110.2(5) . . ?
C6 C5 C4 120.0(6) . . ?
N2 C5 C4 129.8(6) . . ?
N5 C25 C26 115.1(5) . . ?
C24 C23 C22 120.2(7) . . ?
C6 C1 C2 115.4(6) . . ?
C18 C19 C20 119.9(6) . . ?
C18 C19 C24 121.7(6) . . ?
C20 C19 C24 118.3(6) . . ?
C18 C17 C16 121.9(6) . . ?
C10 C11 C12 120.8(6) . . ?
C11 C12 C13 121.0(6) . . ?
C9 C10 C11 118.9(6) . . ?
C17 C18 C19 119.9(6) . . ?
C15 C16 C17 119.7(6) . . ?
C30 C29 N5 115.2(6) . . ?
C39 C38 C37 110.1(7) . . ?
C38 C37 N5 117.2(6) . . ?
C23 C24 C19 121.5(6) . . ?
N5 C33 C34 115.4(6) . . ?
C3 C2 C1 122.1(7) . . ?
C29 C30 C31 113.6(8) . . ?
C3 C4 C5 117.1(7) . . ?
C4 C3 C2 122.5(7) . . ?
C25 C26 C27 111.3(7) . . ?
C35 C34 C33 113.2(8) . . ?
C32 C31 C30 115.8(9) . . ?
C28 C27 C26 112.8(10) . . ?
C34 C35 C36 116.4(9) . . ?
C40 C39 C38 113.2(7) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043

