# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 2289592'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_publcif_datablock.id            {ff12c422-d02b-43ea-b386-bfa0371c3d3c}

# publcif _publ_body_element loop end
_audit_creation_date             2023-02-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 N3 O2'
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0783(7)
_cell_length_b                   7.7116(7)
_cell_length_c                   10.2340(10)
_cell_angle_alpha                84.195(4)
_cell_angle_beta                 86.746(4)
_cell_angle_gamma                82.030(3)
_cell_volume                     549.87(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5978
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0750 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8723.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13478
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.909
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1992
_reflns_number_total             2234
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.2809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.27640(14) 0.50423(13) 0.47204(9) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.00181(13) 0.52387(13) 0.17656(9) 0.0228(2) Uani 1 1 d . . . . .
N1 N 0.1326(2) -0.03469(18) 0.34470(13) 0.0341(3) Uani 1 1 d . . . . .
N2 N 0.15673(19) 0.29006(18) 0.60720(12) 0.0248(3) Uani 1 1 d . . . . .
N3 N 0.22865(16) 0.37917(16) 0.04269(11) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.1801(2) 0.0990(2) 0.35918(13) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.23648(19) 0.26311(19) 0.37316(13) 0.0204(3) Uani 1 1 d . . . . .
C3 C 0.31210(19) 0.38258(18) 0.26138(13) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.4775(2) 0.29882(18) 0.17883(14) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.6603(2) 0.2263(2) 0.21075(16) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.702198 0.226273 0.297315 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7822(2) 0.1531(2) 0.11283(17) 0.0320(4) Uani 1 1 d . . . . .
H6 H 0.909114 0.103987 0.132599 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7198(2) 0.1514(2) -0.01313(16) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.804946 0.100222 -0.078082 0.034 Uiso 1 1 calc R U . . .
C8 C 0.21824(19) 0.34460(18) 0.48630(13) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.3495(2) 0.53744(19) 0.33745(13) 0.0215(3) Uani 1 1 d . . . . .
H9A H 0.488026 0.545246 0.335942 0.026 Uiso 1 1 calc R U . . .
H9B H 0.283705 0.649770 0.296441 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5354(2) 0.22270(19) -0.04652(14) 0.0231(3) Uani 1 1 d . . . . .
H10 H 0.491993 0.220364 -0.132401 0.028 Uiso 1 1 calc R U . . .
C11 C 0.41855(19) 0.29712(18) 0.05144(13) 0.0195(3) Uani 1 1 d . . . . .
C12 C 0.16017(19) 0.43942(18) 0.15711(13) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.160(3) 0.399(2) -0.0330(19) 0.036(5) Uiso 1 1 d . . . . .
H2A H 0.124(3) 0.369(2) 0.6648(18) 0.030(5) Uiso 1 1 d . . . . .
H2B H 0.087(3) 0.200(2) 0.6162(17) 0.032(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 C8 1.3430(17) . ?
O1 C9 1.4542(16) . ?
O2 C12 1.2324(17) . ?
N1 C1 1.153(2) . ?
N2 C8 1.3348(18) . ?
N2 H2A 0.886(19) . ?
N2 H2B 0.900(19) . ?
N3 C11 1.4077(18) . ?
N3 C12 1.3436(17) . ?
N3 H3 0.928(19) . ?
C1 C2 1.402(2) . ?
C2 C3 1.5160(19) . ?
C2 C8 1.3638(19) . ?
C3 C4 1.5135(19) . ?
C3 C9 1.5496(19) . ?
C3 C12 1.5467(18) . ?
C4 C5 1.379(2) . ?
C4 C11 1.393(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C7 H7 0.9500 . ?
C7 C10 1.391(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C11 1.3816(19) . ?

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
C8 O1 C9 108.52(10) . . ?
C8 N2 H2A 118.8(12) . . ?
C8 N2 H2B 118.0(11) . . ?
H2A N2 H2B 114.3(17) . . ?
C11 N3 H3 125.8(11) . . ?
C12 N3 C11 111.57(11) . . ?
C12 N3 H3 122.5(11) . . ?
N1 C1 C2 178.40(16) . . ?
C1 C2 C3 124.59(12) . . ?
C8 C2 C1 125.28(13) . . ?
C8 C2 C3 109.96(12) . . ?
C2 C3 C9 100.16(11) . . ?
C2 C3 C12 110.77(11) . . ?
C4 C3 C2 115.68(12) . . ?
C4 C3 C9 116.95(11) . . ?
C4 C3 C12 101.35(11) . . ?
C12 C3 C9 112.36(11) . . ?
C5 C4 C3 131.35(13) . . ?
C5 C4 C11 119.94(13) . . ?
C11 C4 C3 108.69(12) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.42(14) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.66(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C10 121.57(14) . . ?
C10 C7 H7 119.2 . . ?
O1 C8 C2 113.43(12) . . ?
N2 C8 O1 115.91(12) . . ?
N2 C8 C2 130.65(14) . . ?
O1 C9 C3 107.53(11) . . ?
O1 C9 H9A 110.2 . . ?
O1 C9 H9B 110.2 . . ?
C3 C9 H9A 110.2 . . ?
C3 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C7 C10 H10 121.7 . . ?
C11 C10 C7 116.68(14) . . ?
C11 C10 H10 121.7 . . ?
C4 C11 N3 109.48(12) . . ?
C10 C11 N3 127.80(13) . . ?
C10 C11 C4 122.72(13) . . ?
O2 C12 N3 125.84(13) . . ?
O2 C12 C3 125.52(12) . . ?
N3 C12 C3 108.63(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -52.87(18) . . . . ?
C1 C2 C3 C9 -179.53(13) . . . . ?
C1 C2 C3 C12 61.70(17) . . . . ?
C1 C2 C8 O1 -177.48(13) . . . . ?
C1 C2 C8 N2 4.1(3) . . . . ?
C2 C3 C4 C5 -62.6(2) . . . . ?
C2 C3 C4 C11 115.49(13) . . . . ?
C2 C3 C9 O1 -6.15(13) . . . . ?
C2 C3 C12 O2 61.18(18) . . . . ?
C2 C3 C12 N3 -117.93(12) . . . . ?
C3 C2 C8 O1 -2.06(16) . . . . ?
C3 C2 C8 N2 179.55(14) . . . . ?
C3 C4 C5 C6 178.17(15) . . . . ?
C3 C4 C11 N3 2.08(15) . . . . ?
C3 C4 C11 C10 -177.44(13) . . . . ?
C4 C3 C9 O1 -131.95(12) . . . . ?
C4 C3 C12 O2 -175.54(13) . . . . ?
C4 C3 C12 N3 5.35(14) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C4 C11 N3 -179.54(13) . . . . ?
C5 C4 C11 C10 0.9(2) . . . . ?
C5 C6 C7 C10 0.4(2) . . . . ?
C6 C7 C10 C11 0.7(2) . . . . ?
C7 C10 C11 N3 179.18(13) . . . . ?
C7 C10 C11 C4 -1.4(2) . . . . ?
C8 O1 C9 C3 5.48(14) . . . . ?
C8 C2 C3 C4 131.67(13) . . . . ?
C8 C2 C3 C9 5.02(14) . . . . ?
C8 C2 C3 C12 -113.75(13) . . . . ?
C9 O1 C8 N2 176.39(12) . . . . ?
C9 O1 C8 C2 -2.25(15) . . . . ?
C9 C3 C4 C5 55.0(2) . . . . ?
C9 C3 C4 C11 -126.87(13) . . . . ?
C9 C3 C12 O2 -49.92(18) . . . . ?
C9 C3 C12 N3 130.97(12) . . . . ?
C11 N3 C12 O2 176.37(13) . . . . ?
C11 N3 C12 C3 -4.52(15) . . . . ?
C11 C4 C5 C6 0.2(2) . . . . ?
C12 N3 C11 C4 1.62(16) . . . . ?
C12 N3 C11 C10 -178.90(14) . . . . ?
C12 C3 C4 C5 177.50(15) . . . . ?
C12 C3 C4 C11 -4.37(14) . . . . ?
C12 C3 C9 O1 111.45(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_2aa
_database_code_depnum_ccdc_archive 'CCDC 2289593'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_publcif_datablock.id            {c6d37097-513b-48a7-aeee-217e3c7154af}

# publcif _publ_body_element loop end
_audit_creation_date             2023-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N2 O4'
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   7.8790(3)
_cell_length_b                   12.9879(4)
_cell_length_c                   25.3279(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2591.85(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6015
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.8065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30373
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.729
_diffrn_reflns_theta_min         3.045
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2904
_reflns_number_total             3358
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+1.0674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1029
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C7(H7), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O4 O 0.78775(10) 0.80326(6) 0.62373(3) 0.01719(19) Uani 1 1 d . . . . .
N2 N 0.63113(15) 0.52590(8) 0.70920(4) 0.0197(2) Uani 1 1 d . . . . .
H2A H 0.745(2) 0.5244(13) 0.7056(6) 0.030(4) Uiso 1 1 d . . . . .
H2B H 0.577(2) 0.4839(13) 0.7308(7) 0.029(4) Uiso 1 1 d . . . . .
O1 O 0.55561(12) 0.89638(7) 0.72175(3) 0.0218(2) Uani 1 1 d . . . . .
O3 O 0.89660(11) 0.65203(6) 0.65346(3) 0.01926(19) Uani 1 1 d . . . . .
O2 O 0.38456(11) 0.61394(6) 0.70641(3) 0.01935(19) Uani 1 1 d . . . . .
N1 N 0.47011(13) 0.94452(7) 0.63848(4) 0.0200(2) Uani 1 1 d . . . . .
H1 H 0.482727 1.011568 0.641610 0.024 Uiso 1 1 calc R U . . .
C12 C 0.77433(15) 0.71034(8) 0.64784(4) 0.0143(2) Uani 1 1 d . . . . .
C11 C 0.60480(15) 0.69332(8) 0.66494(4) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.50149(15) 0.87600(8) 0.67756(5) 0.0169(2) Uani 1 1 d . . . . .
C10 C 0.55006(15) 0.60981(8) 0.69355(4) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.45818(14) 0.76710(8) 0.65752(4) 0.0145(2) Uani 1 1 d . . . . .
C3 C 0.40412(15) 0.78899(9) 0.60136(5) 0.0160(2) Uani 1 1 d . . . . .
C8 C 0.41478(15) 0.89486(9) 0.59224(5) 0.0187(2) Uani 1 1 d . . . . .
C9 C 0.32084(16) 0.71551(9) 0.69282(5) 0.0187(2) Uani 1 1 d . . . . .
H9A H 0.301613 0.756777 0.725131 0.022 Uiso 1 1 calc R U . . .
H9B H 0.212196 0.709794 0.673397 0.022 Uiso 1 1 calc R U . . .
C4 C 0.34742(16) 0.72419(9) 0.56192(5) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.339698 0.652086 0.567750 0.025 Uiso 1 1 calc R U . . .
C13 C 0.95539(15) 0.83912(9) 0.60989(5) 0.0205(2) Uani 1 1 d . . . . .
H13A H 1.013517 0.788250 0.587078 0.025 Uiso 1 1 calc R U . . .
H13B H 1.024572 0.849906 0.642046 0.025 Uiso 1 1 calc R U . . .
C7 C 0.37342(18) 0.93789(10) 0.54401(5) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.383749 1.009804 0.537954 0.032 Uiso 1 1 calc R U . . .
C14 C 0.93106(17) 0.93959(9) 0.58073(6) 0.0247(3) Uani 1 1 d . . . . .
H14A H 1.042045 0.970429 0.573308 0.037 Uiso 1 1 calc R U . . .
H14B H 0.864003 0.986820 0.602534 0.037 Uiso 1 1 calc R U . . .
H14C H 0.871355 0.926664 0.547439 0.037 Uiso 1 1 calc R U . . .
C5 C 0.30151(18) 0.76672(11) 0.51319(5) 0.0275(3) Uani 1 1 d . . . . .
H5 H 0.260184 0.723354 0.485863 0.033 Uiso 1 1 calc R U . . .
C6 C 0.31596(19) 0.87155(12) 0.50460(5) 0.0304(3) Uani 1 1 d . . . . .
H6 H 0.286061 0.898948 0.471087 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C12 1.3566(13) . ?
O4 C13 1.4438(14) . ?
N2 H2A 0.899(19) . ?
N2 H2B 0.883(18) . ?
N2 C10 1.3240(15) . ?
O1 C1 1.2267(15) . ?
O3 C12 1.2336(14) . ?
O2 C10 1.3451(14) . ?
O2 C9 1.4530(14) . ?
N1 H1 0.8800 . ?
N1 C1 1.3538(16) . ?
N1 C8 1.4062(16) . ?
C12 C11 1.4214(16) . ?
C11 C10 1.3739(15) . ?
C11 C2 1.5127(15) . ?
C1 C2 1.5409(15) . ?
C2 C3 1.5120(16) . ?
C2 C9 1.5553(16) . ?
C3 C8 1.3968(16) . ?
C3 C4 1.3803(17) . ?
C8 C7 1.3824(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3998(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5116(17) . ?
C7 H7 0.9500 . ?
C7 C6 1.394(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C6 H6 0.9500 . ?

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
C12 O4 C13 117.88(9) . . ?
H2A N2 H2B 122.0(15) . . ?
C10 N2 H2A 117.9(11) . . ?
C10 N2 H2B 117.5(11) . . ?
C10 O2 C9 108.28(9) . . ?
C1 N1 H1 124.3 . . ?
C1 N1 C8 111.34(9) . . ?
C8 N1 H1 124.3 . . ?
O4 C12 C11 110.41(9) . . ?
O3 C12 O4 122.49(10) . . ?
O3 C12 C11 127.10(10) . . ?
C12 C11 C2 125.54(10) . . ?
C10 C11 C12 125.34(10) . . ?
C10 C11 C2 109.01(10) . . ?
O1 C1 N1 126.07(11) . . ?
O1 C1 C2 125.14(10) . . ?
N1 C1 C2 108.80(10) . . ?
N2 C10 O2 115.34(10) . . ?
N2 C10 C11 131.02(11) . . ?
O2 C10 C11 113.62(10) . . ?
C11 C2 C1 111.81(9) . . ?
C11 C2 C9 100.78(9) . . ?
C1 C2 C9 111.11(9) . . ?
C3 C2 C11 116.81(9) . . ?
C3 C2 C1 101.52(9) . . ?
C3 C2 C9 115.20(10) . . ?
C8 C3 C2 108.88(10) . . ?
C4 C3 C2 131.10(10) . . ?
C4 C3 C8 120.01(11) . . ?
C3 C8 N1 109.43(10) . . ?
C7 C8 N1 128.58(11) . . ?
C7 C8 C3 121.99(12) . . ?
O2 C9 C2 106.68(9) . . ?
O2 C9 H9A 110.4 . . ?
O2 C9 H9B 110.4 . . ?
C2 C9 H9A 110.4 . . ?
C2 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.75(12) . . ?
C5 C4 H4 120.6 . . ?
O4 C13 H13A 110.5 . . ?
O4 C13 H13B 110.5 . . ?
O4 C13 C14 106.33(10) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C8 C7 H7 121.3 . . ?
C8 C7 C6 117.35(12) . . ?
C6 C7 H7 121.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.39(13) . . ?
C6 C5 H5 119.8 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.48(12) . . ?
C5 C6 H6 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C12 C11 C10 -175.78(11) . . . . ?
O4 C12 C11 C2 0.21(15) . . . . ?
O1 C1 C2 C11 -53.10(15) . . . . ?
O1 C1 C2 C3 -178.37(11) . . . . ?
O1 C1 C2 C9 58.65(15) . . . . ?
O3 C12 C11 C10 3.69(19) . . . . ?
O3 C12 C11 C2 179.69(11) . . . . ?
N1 C1 C2 C11 126.84(10) . . . . ?
N1 C1 C2 C3 1.58(12) . . . . ?
N1 C1 C2 C9 -121.41(11) . . . . ?
N1 C8 C7 C6 -177.87(12) . . . . ?
C12 O4 C13 C14 176.27(10) . . . . ?
C12 C11 C10 N2 -4.2(2) . . . . ?
C12 C11 C10 O2 177.68(10) . . . . ?
C12 C11 C2 C1 -51.87(14) . . . . ?
C12 C11 C2 C3 64.44(15) . . . . ?
C12 C11 C2 C9 -169.98(11) . . . . ?
C11 C2 C3 C8 -122.38(11) . . . . ?
C11 C2 C3 C4 59.07(17) . . . . ?
C11 C2 C9 O2 -11.47(11) . . . . ?
C1 N1 C8 C3 1.77(14) . . . . ?
C1 N1 C8 C7 -178.75(12) . . . . ?
C1 C2 C3 C8 -0.53(12) . . . . ?
C1 C2 C3 C4 -179.08(12) . . . . ?
C1 C2 C9 O2 -130.09(10) . . . . ?
C10 O2 C9 C2 12.91(12) . . . . ?
C10 C11 C2 C1 124.68(10) . . . . ?
C10 C11 C2 C3 -119.02(11) . . . . ?
C10 C11 C2 C9 6.56(12) . . . . ?
C2 C11 C10 N2 179.22(12) . . . . ?
C2 C11 C10 O2 1.13(14) . . . . ?
C2 C3 C8 N1 -0.65(13) . . . . ?
C2 C3 C8 C7 179.83(11) . . . . ?
C2 C3 C4 C5 178.44(12) . . . . ?
C3 C2 C9 O2 115.19(10) . . . . ?
C3 C8 C7 C6 1.55(19) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C8 N1 C1 O1 177.84(11) . . . . ?
C8 N1 C1 C2 -2.10(13) . . . . ?
C8 C3 C4 C5 0.02(18) . . . . ?
C8 C7 C6 C5 -0.3(2) . . . . ?
C9 O2 C10 N2 172.50(10) . . . . ?
C9 O2 C10 C11 -9.09(13) . . . . ?
C9 C2 C3 C8 119.62(11) . . . . ?
C9 C2 C3 C4 -58.93(17) . . . . ?
C4 C3 C8 N1 178.09(11) . . . . ?
C4 C3 C8 C7 -1.44(18) . . . . ?
C4 C5 C6 C7 -1.1(2) . . . . ?
C13 O4 C12 O3 -7.32(16) . . . . ?
C13 O4 C12 C11 172.18(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



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

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2289594'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_publcif_datablock.id            {42307eda-955d-4373-9637-5b25b925a92e}

# publcif _publ_body_element loop end
_audit_creation_date             2023-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 N6 O2, 2(H2 O)'
_chemical_formula_sum            'C22 H16 N6 O4'
_chemical_formula_weight         428.41
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.0247(18)
_cell_length_b                   8.9614(11)
_cell_length_c                   13.2287(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2018.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5583
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.7490.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17679
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.568
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3975
_reflns_number_total             4061
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4061
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+0.3804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3C,H3D), O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C9(H9), C10(H10), C11(H11), C12(H12),
 C21(H21), C22(H22)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O3 O 0.43809(9) 0.74764(18) 0.22285(11) 0.0247(3) Uani 1 1 d G . . . .
H3C H 0.433831 0.660232 0.250923 0.037 Uiso 1 1 d G U . . .
H3D H 0.445842 0.808451 0.273105 0.037 Uiso 1 1 d G U . . .
O4 O 0.52135(11) 0.8700(2) 0.44113(14) 0.0350(4) Uani 1 1 d G . . . .
H4A H 0.522699 0.783817 0.471391 0.052 Uiso 1 1 d G U . . .
H4B H 0.563405 0.871063 0.403751 0.052 Uiso 1 1 d G U . . .
O1 O 0.41077(9) 0.50576(17) 0.34563(12) 0.0243(3) Uani 1 1 d . . . . .
N3 N 0.47450(10) 0.1465(2) 0.55353(14) 0.0218(4) Uani 1 1 d . . . . .
H3A H 0.489296 0.068258 0.518115 0.026 Uiso 1 1 calc R U . . .
H3B H 0.498753 0.168654 0.610321 0.026 Uiso 1 1 calc R U . . .
O2 O 0.24765(8) 0.19376(15) 0.61691(11) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.28299(11) 0.50254(19) 0.28684(14) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.285323 0.576598 0.243262 0.026 Uiso 1 1 calc R U . . .
N4 N 0.40008(14) 0.0292(3) 0.29805(17) 0.0366(5) Uani 1 1 d . . . . .
N5 N 0.49683(11) 0.5808(2) 0.56409(17) 0.0292(4) Uani 1 1 d . . . . .
N6 N 0.37797(12) 0.3145(2) 0.77681(15) 0.0300(5) Uani 1 1 d . . . . .
N2 N 0.18901(10) 0.42518(19) 0.62058(13) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.145484 0.401358 0.652634 0.023 Uiso 1 1 calc R U . . .
C1 C 0.09078(14) 0.3067(3) 0.27205(18) 0.0285(5) Uani 1 1 d . . . . .
H1A H 0.042240 0.305523 0.236642 0.034 Uiso 1 1 calc R U . . .
C2 C 0.14678(13) 0.4140(3) 0.24755(17) 0.0258(5) Uani 1 1 d . . . . .
H2A H 0.137778 0.485292 0.195664 0.031 Uiso 1 1 calc R U . . .
C3 C 0.21613(13) 0.4123(2) 0.30213(16) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.23052(12) 0.3099(2) 0.37986(15) 0.0182(4) Uani 1 1 d . . . . .
C5 C 0.31116(11) 0.3427(2) 0.42336(15) 0.0167(4) Uani 1 1 d . . . . .
C6 C 0.30874(11) 0.4120(2) 0.53402(15) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.28048(11) 0.5713(2) 0.54045(14) 0.0168(4) Uani 1 1 d . . . . .
C8 C 0.20805(12) 0.5715(2) 0.58982(15) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.16398(12) 0.7003(2) 0.60179(16) 0.0220(4) Uani 1 1 d . . . . .
H9 H 0.114467 0.698684 0.634894 0.026 Uiso 1 1 calc R U . . .
C10 C 0.19518(13) 0.8318(2) 0.56338(18) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.166214 0.921869 0.570128 0.029 Uiso 1 1 calc R U . . .
C11 C 0.10430(13) 0.2009(3) 0.34731(19) 0.0270(5) Uani 1 1 d . . . . .
H11 H 0.065500 0.127728 0.361753 0.032 Uiso 1 1 calc R U . . .
C12 C 0.17477(13) 0.2020(2) 0.40164(16) 0.0220(4) Uani 1 1 d . . . . .
H12 H 0.184268 0.129804 0.452771 0.026 Uiso 1 1 calc R U . . .
C13 C 0.34274(12) 0.4612(2) 0.34723(15) 0.0189(4) Uani 1 1 d . . . . .
C14 C 0.36992(12) 0.2189(2) 0.43692(15) 0.0172(4) Uani 1 1 d . . . . .
C15 C 0.38526(12) 0.1132(2) 0.36074(16) 0.0222(4) Uani 1 1 d . . . . .
C16 C 0.41542(12) 0.2313(2) 0.52118(15) 0.0170(4) Uani 1 1 d . . . . .
C17 C 0.39062(11) 0.3699(2) 0.58184(15) 0.0170(4) Uani 1 1 d . . . . .
C18 C 0.45058(11) 0.4893(2) 0.57052(16) 0.0205(4) Uani 1 1 d . . . . .
C19 C 0.38387(12) 0.3385(2) 0.69257(16) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.24486(11) 0.3267(2) 0.59533(14) 0.0164(4) Uani 1 1 d . . . . .
C21 C 0.31108(13) 0.7047(2) 0.50261(17) 0.0208(4) Uani 1 1 d . . . . .
H21 H 0.360367 0.706528 0.468952 0.025 Uiso 1 1 calc R U . . .
C22 C 0.26756(13) 0.8348(2) 0.51543(17) 0.0242(5) Uani 1 1 d . . . . .
H22 H 0.287722 0.926848 0.491012 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3C 0.8699 . ?
O3 H3D 0.8696 . ?
O4 H4A 0.8705 . ?
O4 H4B 0.8703 . ?
O1 C13 1.225(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C16 1.331(3) . ?
O2 C20 1.226(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.411(3) . ?
N1 C13 1.345(3) . ?
N4 C15 1.148(3) . ?
N5 C18 1.140(3) . ?
N6 C19 1.139(3) . ?
N2 H2 0.8800 . ?
N2 C8 1.411(3) . ?
N2 C20 1.339(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.393(3) . ?
C1 C11 1.394(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.517(3) . ?
C4 C12 1.385(3) . ?
C5 C6 1.590(3) . ?
C5 C13 1.559(3) . ?
C5 C14 1.505(3) . ?
C6 C7 1.509(3) . ?
C6 C17 1.576(3) . ?
C6 C20 1.557(3) . ?
C7 C8 1.395(3) . ?
C7 C21 1.397(3) . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C22 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.407(3) . ?
C14 C16 1.362(3) . ?
C16 C17 1.538(3) . ?
C17 C18 1.486(3) . ?
C17 C19 1.496(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.392(3) . ?
C22 H22 0.9500 . ?

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
H3C O3 H3D 104.5 . . ?
H4A O4 H4B 104.4 . . ?
H3A N3 H3B 120.0 . . ?
C16 N3 H3A 120.0 . . ?
C16 N3 H3B 120.0 . . ?
C3 N1 H1 124.2 . . ?
C13 N1 H1 124.2 . . ?
C13 N1 C3 111.53(17) . . ?
C8 N2 H2 123.9 . . ?
C20 N2 H2 123.9 . . ?
C20 N2 C8 112.16(16) . . ?
C2 C1 H1A 119.2 . . ?
C2 C1 C11 121.5(2) . . ?
C11 C1 H1A 119.2 . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2A 121.5 . . ?
C2 C3 N1 127.4(2) . . ?
C2 C3 C4 122.7(2) . . ?
C4 C3 N1 109.87(18) . . ?
C3 C4 C5 108.03(18) . . ?
C12 C4 C3 119.37(19) . . ?
C12 C4 C5 132.58(19) . . ?
C4 C5 C6 113.66(16) . . ?
C4 C5 C13 101.49(16) . . ?
C13 C5 C6 109.76(16) . . ?
C14 C5 C4 120.24(17) . . ?
C14 C5 C6 101.25(15) . . ?
C14 C5 C13 110.48(16) . . ?
C7 C6 C5 115.42(16) . . ?
C7 C6 C17 119.03(17) . . ?
C7 C6 C20 102.24(16) . . ?
C17 C6 C5 104.67(15) . . ?
C20 C6 C5 107.83(15) . . ?
C20 C6 C17 106.94(15) . . ?
C8 C7 C6 108.04(18) . . ?
C8 C7 C21 119.74(18) . . ?
C21 C7 C6 132.11(18) . . ?
C7 C8 N2 109.67(17) . . ?
C9 C8 N2 128.08(19) . . ?
C9 C8 C7 122.23(19) . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.25(19) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 119.2 . . ?
C22 C10 C9 121.6(2) . . ?
C22 C10 H10 119.2 . . ?
C1 C11 H11 119.9 . . ?
C1 C11 C12 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C4 C12 C11 119.1(2) . . ?
C4 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O1 C13 N1 127.92(19) . . ?
O1 C13 C5 124.00(18) . . ?
N1 C13 C5 108.08(17) . . ?
C15 C14 C5 122.29(18) . . ?
C16 C14 C5 114.56(18) . . ?
C16 C14 C15 122.37(19) . . ?
N4 C15 C14 177.8(2) . . ?
N3 C16 C14 130.3(2) . . ?
N3 C16 C17 120.06(18) . . ?
C14 C16 C17 109.67(17) . . ?
C16 C17 C6 103.08(15) . . ?
C18 C17 C6 113.26(16) . . ?
C18 C17 C16 109.89(16) . . ?
C18 C17 C19 106.67(16) . . ?
C19 C17 C6 111.71(16) . . ?
C19 C17 C16 112.33(17) . . ?
N5 C18 C17 178.5(2) . . ?
N6 C19 C17 179.4(2) . . ?
O2 C20 N2 127.56(18) . . ?
O2 C20 C6 124.81(18) . . ?
N2 C20 C6 107.61(16) . . ?
C7 C21 H21 120.8 . . ?
C22 C21 C7 118.34(19) . . ?
C22 C21 H21 120.8 . . ?
C10 C22 C21 120.8(2) . . ?
C10 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C16 C17 C6 -166.57(18) . . . . ?
N3 C16 C17 C18 72.4(2) . . . . ?
N3 C16 C17 C19 -46.2(3) . . . . ?
N1 C3 C4 C5 4.0(2) . . . . ?
N1 C3 C4 C12 -174.67(18) . . . . ?
N2 C8 C9 C10 -179.1(2) . . . . ?
C1 C2 C3 N1 175.5(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C11 C12 C4 0.3(3) . . . . ?
C2 C1 C11 C12 1.1(3) . . . . ?
C2 C3 C4 C5 -179.06(19) . . . . ?
C2 C3 C4 C12 2.2(3) . . . . ?
C3 N1 C13 O1 171.8(2) . . . . ?
C3 N1 C13 C5 -8.3(2) . . . . ?
C3 C4 C5 C6 109.56(19) . . . . ?
C3 C4 C5 C13 -8.2(2) . . . . ?
C3 C4 C5 C14 -130.32(19) . . . . ?
C3 C4 C12 C11 -1.9(3) . . . . ?
C4 C5 C6 C7 -72.0(2) . . . . ?
C4 C5 C6 C17 155.17(16) . . . . ?
C4 C5 C6 C20 41.5(2) . . . . ?
C4 C5 C13 O1 -170.2(2) . . . . ?
C4 C5 C13 N1 10.0(2) . . . . ?
C4 C5 C14 C15 46.4(3) . . . . ?
C4 C5 C14 C16 -143.48(19) . . . . ?
C5 C4 C12 C11 179.8(2) . . . . ?
C5 C6 C7 C8 111.98(19) . . . . ?
C5 C6 C7 C21 -64.0(3) . . . . ?
C5 C6 C17 C16 -24.17(19) . . . . ?
C5 C6 C17 C18 94.53(18) . . . . ?
C5 C6 C17 C19 -144.99(17) . . . . ?
C5 C6 C20 O2 64.2(2) . . . . ?
C5 C6 C20 N2 -117.02(17) . . . . ?
C5 C14 C16 N3 -176.8(2) . . . . ?
C5 C14 C16 C17 2.1(2) . . . . ?
C6 C5 C13 O1 69.3(3) . . . . ?
C6 C5 C13 N1 -110.59(18) . . . . ?
C6 C5 C14 C15 172.56(19) . . . . ?
C6 C5 C14 C16 -17.4(2) . . . . ?
C6 C7 C8 N2 3.0(2) . . . . ?
C6 C7 C8 C9 -175.61(19) . . . . ?
C6 C7 C21 C22 175.4(2) . . . . ?
C7 C6 C17 C16 -154.92(17) . . . . ?
C7 C6 C17 C18 -36.2(3) . . . . ?
C7 C6 C17 C19 84.3(2) . . . . ?
C7 C6 C20 O2 -173.75(18) . . . . ?
C7 C6 C20 N2 5.1(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C21 C22 C10 -0.8(3) . . . . ?
C8 N2 C20 O2 175.16(19) . . . . ?
C8 N2 C20 C6 -3.6(2) . . . . ?
C8 C7 C21 C22 -0.2(3) . . . . ?
C8 C9 C10 C22 -0.3(3) . . . . ?
C9 C10 C22 C21 1.1(3) . . . . ?
C11 C1 C2 C3 -0.8(3) . . . . ?
C12 C4 C5 C6 -72.0(3) . . . . ?
C12 C4 C5 C13 170.3(2) . . . . ?
C12 C4 C5 C14 48.1(3) . . . . ?
C13 N1 C3 C2 -173.9(2) . . . . ?
C13 N1 C3 C4 2.9(2) . . . . ?
C13 C5 C6 C7 40.9(2) . . . . ?
C13 C5 C6 C17 -91.97(18) . . . . ?
C13 C5 C6 C20 154.41(16) . . . . ?
C13 C5 C14 C15 -71.2(2) . . . . ?
C13 C5 C14 C16 98.9(2) . . . . ?
C14 C5 C6 C7 157.63(17) . . . . ?
C14 C5 C6 C17 24.80(18) . . . . ?
C14 C5 C6 C20 -88.82(18) . . . . ?
C14 C5 C13 O1 -41.5(3) . . . . ?
C14 C5 C13 N1 138.60(17) . . . . ?
C14 C16 C17 C6 14.5(2) . . . . ?
C14 C16 C17 C18 -106.55(19) . . . . ?
C14 C16 C17 C19 134.86(18) . . . . ?
C15 C14 C16 N3 -6.7(4) . . . . ?
C15 C14 C16 C17 172.13(19) . . . . ?
C17 C6 C7 C8 -122.25(19) . . . . ?
C17 C6 C7 C21 61.8(3) . . . . ?
C17 C6 C20 O2 -47.9(2) . . . . ?
C17 C6 C20 N2 130.89(16) . . . . ?
C20 N2 C8 C7 0.5(2) . . . . ?
C20 N2 C8 C9 179.0(2) . . . . ?
C20 C6 C7 C8 -4.8(2) . . . . ?
C20 C6 C7 C21 179.2(2) . . . . ?
C20 C6 C17 C16 90.08(17) . . . . ?
C20 C6 C17 C18 -151.22(17) . . . . ?
C20 C6 C17 C19 -30.7(2) . . . . ?
C21 C7 C8 N2 179.58(18) . . . . ?
C21 C7 C8 C9 1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_3h
_database_code_depnum_ccdc_archive 'CCDC 2289595'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_publcif_datablock.id            {ad868439-4a6b-4757-9451-8e7769778005}

# publcif _publ_body_element loop end
_audit_creation_date             2023-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 N6 O4, H2 O'
_chemical_formula_sum            'C28 H26 N6 O5'
_chemical_formula_weight         526.55
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4292(12)
_cell_length_b                   9.9284(8)
_cell_length_c                   17.7983(16)
_cell_angle_alpha                90
_cell_angle_beta                 113.305(3)
_cell_angle_gamma                90
_cell_volume                     2504.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6143
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1473 before and 0.0841 after correction.
The Ratio of minimum to maximum transmission is 0.8236.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            123205
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.333
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4604
_reflns_number_total             5466
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5466
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      16.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+1.2558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-H25
 0.82 with sigma of 0.01
 O4-H26
 0.82 with sigma of 0.01
 H25-H26
 1.296731 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.50357(12) 1.05817(18) 0.37648(11) 0.0300(4) Uani 1 1 d . . . . .
H1A H 0.457745 1.107282 0.331991 0.045 Uiso 1 1 calc R U . . .
H1B H 0.506363 1.094187 0.427446 0.045 Uiso 1 1 calc R U . . .
H1C H 0.485791 0.964944 0.372515 0.045 Uiso 1 1 calc R U . . .
C2 C 0.59391(11) 1.03713(15) 0.29486(9) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.653121 1.066428 0.293237 0.026 Uiso 1 1 calc R U . . .
H2B H 0.543579 1.086687 0.253099 0.026 Uiso 1 1 calc R U . . .
C3 C 0.58095(10) 0.88778(15) 0.27436(9) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.521014 0.858993 0.274675 0.022 Uiso 1 1 calc R U . . .
H3B H 0.578068 0.874746 0.219413 0.022 Uiso 1 1 calc R U . . .
C4 C 0.64232(9) 0.71257(13) 0.38205(8) 0.0132(3) Uani 1 1 d . . . . .
C5 C 0.73363(9) 0.62744(13) 0.42315(8) 0.0125(3) Uani 1 1 d . . . . .
C6 C 0.77178(9) 0.63618(13) 0.51893(8) 0.0125(3) Uani 1 1 d . . . . .
C7 C 0.87867(9) 0.59941(14) 0.55637(8) 0.0139(3) Uani 1 1 d . . . . .
C8 C 1.02785(10) 0.69813(16) 0.65310(10) 0.0239(3) Uani 1 1 d . . . . .
H8A H 1.045206 0.606122 0.671092 0.029 Uiso 1 1 calc R U . . .
H8B H 1.042046 0.753559 0.701407 0.029 Uiso 1 1 calc R U . . .
C9 C 1.08628(11) 0.74555(18) 0.60759(12) 0.0311(4) Uani 1 1 d . . . . .
H9A H 1.152856 0.734312 0.641439 0.037 Uiso 1 1 calc R U . . .
H9B H 1.071321 0.692958 0.558100 0.037 Uiso 1 1 calc R U . . .
C10 C 1.11342(14) 0.9315(2) 0.53911(13) 0.0418(5) Uani 1 1 d . . . . .
H10A H 1.180363 0.922934 0.568818 0.063 Uiso 1 1 calc R U . . .
H10B H 1.097580 1.024570 0.526293 0.063 Uiso 1 1 calc R U . . .
H10C H 1.094219 0.880357 0.489373 0.063 Uiso 1 1 calc R U . . .
C11 C 0.74720(10) 0.78838(14) 0.33047(8) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.79656(10) 0.68607(14) 0.38403(8) 0.0138(3) Uani 1 1 d . . . . .
C13 C 0.70733(9) 0.48016(13) 0.40805(8) 0.0128(3) Uani 1 1 d . . . . .
C14 C 0.68721(9) 0.41636(14) 0.33200(9) 0.0150(3) Uani 1 1 d . . . . .
C15 C 0.69359(9) 0.42017(13) 0.47103(8) 0.0131(3) Uani 1 1 d . . . . .
C16 C 0.71894(9) 0.51769(13) 0.54306(8) 0.0123(3) Uani 1 1 d . . . . .
C17 C 0.86493(10) 0.80866(14) 0.60387(9) 0.0171(3) Uani 1 1 d . . . . .
C18 C 0.77157(10) 0.77307(13) 0.55597(8) 0.0146(3) Uani 1 1 d . . . . .
C19 C 0.69913(11) 0.86066(14) 0.54934(9) 0.0188(3) Uani 1 1 d . . . . .
H19 H 0.636693 0.838690 0.517487 0.023 Uiso 1 1 calc R U . . .
C20 C 0.72194(12) 0.98285(15) 0.59159(10) 0.0233(3) Uani 1 1 d . . . . .
H20 H 0.674034 1.042461 0.588200 0.028 Uiso 1 1 calc R U . . .
C21 C 0.81484(12) 1.01637(16) 0.63842(10) 0.0259(3) Uani 1 1 d . . . . .
H21 H 0.828312 1.098224 0.666072 0.031 Uiso 1 1 calc R U . . .
C22 C 0.88837(11) 0.93012(15) 0.64494(10) 0.0237(3) Uani 1 1 d . . . . .
H22 H 0.950893 0.953193 0.675710 0.028 Uiso 1 1 calc R U . . .
C23 C 0.63496(10) 0.56462(14) 0.55651(8) 0.0162(3) Uani 1 1 d . . . . .
C24 C 0.78175(10) 0.44784(14) 0.61965(9) 0.0164(3) Uani 1 1 d . . . . .
C25 C 0.88623(10) 0.65243(14) 0.39037(9) 0.0166(3) Uani 1 1 d . . . . .
H25 H 0.919493 0.582863 0.424645 0.020 Uiso 1 1 calc DR U . . .
C26 C 0.92570(10) 0.72379(15) 0.34497(9) 0.0194(3) Uani 1 1 d . . . . .
H26 H 0.986167 0.702408 0.349251 0.023 Uiso 1 1 calc DR U . . .
C27 C 0.87619(11) 0.82676(15) 0.29319(9) 0.0204(3) Uani 1 1 d . . . . .
H27 H 0.904291 0.874378 0.263789 0.024 Uiso 1 1 calc R U . . .
C28 C 0.78518(10) 0.86000(15) 0.28450(9) 0.0195(3) Uani 1 1 d . . . . .
H28 H 0.751277 0.927896 0.249052 0.023 Uiso 1 1 calc R U . . .
N1 N 0.65571(8) 0.80233(12) 0.33054(7) 0.0145(2) Uani 1 1 d . . . . .
N2 N 0.92642(8) 0.70389(12) 0.60344(7) 0.0169(3) Uani 1 1 d . . . . .
O3 O 1.06612(9) 0.88201(12) 0.58778(8) 0.0329(3) Uani 1 1 d . . . . .
N4 N 0.67101(9) 0.36267(13) 0.27061(8) 0.0223(3) Uani 1 1 d . . . . .
N5 N 0.66631(9) 0.29610(12) 0.47920(8) 0.0183(3) Uani 1 1 d . . . . .
N6 N 0.57322(9) 0.60345(13) 0.57037(8) 0.0232(3) Uani 1 1 d . . . . .
N7 N 0.83088(9) 0.39305(13) 0.67736(8) 0.0233(3) Uani 1 1 d . . . . .
O1 O 0.59404(8) 1.07022(11) 0.37274(7) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.91236(7) 0.49288(10) 0.54720(6) 0.0180(2) Uani 1 1 d . . . . .
O5 O 0.56948(7) 0.69504(10) 0.39253(6) 0.0176(2) Uani 1 1 d . . . . .
O4 O 0.38529(9) 0.72270(12) 0.38589(8) 0.0258(3) Uani 1 1 d D . . . .
H4A H 0.4420(19) 0.706(3) 0.3931(16) 0.059(7) Uiso 1 1 d . . . . .
H4B H 0.3618(17) 0.760(3) 0.3379(16) 0.053(7) Uiso 1 1 d . . . . .
H5A H 0.6530(14) 0.279(2) 0.5214(13) 0.035(5) Uiso 1 1 d . . . . .
H5B H 0.6476(14) 0.236(2) 0.4363(13) 0.037(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.4285(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(2) . ?
C2 O1 1.4238(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 N1 1.4621(18) . ?
C4 C5 1.5552(18) . ?
C4 N1 1.3517(18) . ?
C4 O5 1.2224(17) . ?
C5 C6 1.5703(18) . ?
C5 C12 1.5170(18) . ?
C5 C13 1.5128(18) . ?
C6 C7 1.5581(18) . ?
C6 C16 1.5844(18) . ?
C6 C18 1.5111(18) . ?
C7 N2 1.3536(18) . ?
C7 O2 1.2177(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.506(2) . ?
C8 N2 1.4626(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 O3 1.404(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 O3 1.423(2) . ?
C11 C12 1.3951(19) . ?
C11 C28 1.378(2) . ?
C11 N1 1.4189(17) . ?
C12 C25 1.3839(19) . ?
C13 C14 1.4132(19) . ?
C13 C15 1.3581(19) . ?
C14 N4 1.1508(19) . ?
C15 C16 1.5288(18) . ?
C15 N5 1.3282(18) . ?
C16 C23 1.4828(19) . ?
C16 C24 1.4943(19) . ?
C17 C18 1.398(2) . ?
C17 C22 1.382(2) . ?
C17 N2 1.4100(18) . ?
C18 C19 1.384(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.389(2) . ?
C22 H22 0.9300 . ?
C23 N6 1.1415(19) . ?
C24 N7 1.1444(19) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.386(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.390(2) . ?
C28 H28 0.9300 . ?
N5 H5A 0.87(2) . ?
N5 H5B 0.92(2) . ?
O4 H4A 0.85(3) . ?
O4 H4B 0.87(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
O1 C2 H2A 108.7 . . ?
O1 C2 H2B 108.7 . . ?
O1 C2 C3 114.07(12) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C3 C2 114.10(12) . . ?
N1 C3 H3A 108.7 . . ?
N1 C3 H3B 108.7 . . ?
N1 C4 C5 108.92(11) . . ?
O5 C4 C5 124.56(12) . . ?
O5 C4 N1 126.43(13) . . ?
C4 C5 C6 111.19(10) . . ?
C12 C5 C4 101.58(11) . . ?
C12 C5 C6 116.35(11) . . ?
C13 C5 C4 108.20(11) . . ?
C13 C5 C6 101.85(10) . . ?
C13 C5 C12 117.69(11) . . ?
C5 C6 C16 103.95(10) . . ?
C7 C6 C5 109.28(10) . . ?
C7 C6 C16 106.33(10) . . ?
C18 C6 C5 117.30(11) . . ?
C18 C6 C7 102.05(11) . . ?
C18 C6 C16 117.35(11) . . ?
N2 C7 C6 108.06(11) . . ?
O2 C7 C6 125.59(12) . . ?
O2 C7 N2 126.29(13) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
N2 C8 C9 112.81(13) . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O3 C9 C8 108.45(14) . . ?
O3 C9 H9A 110.0 . . ?
O3 C9 H9B 110.0 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
C12 C11 N1 110.17(12) . . ?
C28 C11 C12 122.43(13) . . ?
C28 C11 N1 127.39(13) . . ?
C11 C12 C5 108.52(11) . . ?
C25 C12 C5 132.13(13) . . ?
C25 C12 C11 119.29(13) . . ?
C14 C13 C5 123.04(12) . . ?
C15 C13 C5 113.31(12) . . ?
C15 C13 C14 123.17(13) . . ?
N4 C14 C13 179.03(15) . . ?
C13 C15 C16 110.04(12) . . ?
N5 C15 C13 131.06(13) . . ?
N5 C15 C16 118.86(12) . . ?
C15 C16 C6 103.37(10) . . ?
C23 C16 C6 112.75(11) . . ?
C23 C16 C15 112.60(11) . . ?
C23 C16 C24 106.94(11) . . ?
C24 C16 C6 111.98(11) . . ?
C24 C16 C15 109.24(11) . . ?
C18 C17 N2 110.08(12) . . ?
C22 C17 C18 122.27(14) . . ?
C22 C17 N2 127.64(14) . . ?
C17 C18 C6 108.29(12) . . ?
C19 C18 C6 132.00(13) . . ?
C19 C18 C17 119.71(13) . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.48(14) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.89(14) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.28(14) . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 117.35(14) . . ?
C17 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
N6 C23 C16 176.66(15) . . ?
N7 C24 C16 178.49(15) . . ?
C12 C25 H25 120.5 . . ?
C12 C25 C26 119.05(13) . . ?
C26 C25 H25 120.5 . . ?
C25 C26 H26 119.6 . . ?
C25 C26 C27 120.77(13) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.5 . . ?
C26 C27 C28 121.06(13) . . ?
C28 C27 H27 119.5 . . ?
C11 C28 C27 117.36(13) . . ?
C11 C28 H28 121.3 . . ?
C27 C28 H28 121.3 . . ?
C4 N1 C3 123.74(12) . . ?
C4 N1 C11 110.81(11) . . ?
C11 N1 C3 124.90(12) . . ?
C7 N2 C8 122.30(12) . . ?
C7 N2 C17 111.47(12) . . ?
C17 N2 C8 125.94(12) . . ?
C9 O3 C10 111.72(15) . . ?
C15 N5 H5A 117.7(14) . . ?
C15 N5 H5B 121.3(13) . . ?
H5A N5 H5B 119.3(19) . . ?
C2 O1 C1 113.64(12) . . ?
H4A O4 H4B 104(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3B N6 0.97 2.63 3.586(2) 167.6 4_575 yes
C8 H8B N7 0.97 2.66 3.521(2) 148.2 2_756 yes
C10 H10B O3 0.96 2.70 3.354(3) 125.7 3_776 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 N1 C4 112.80(15) . . . . ?
C2 C3 N1 C11 -76.51(17) . . . . ?
C3 C2 O1 C1 -71.01(16) . . . . ?
C4 C5 C6 C7 -158.30(11) . . . . ?
C4 C5 C6 C16 88.50(12) . . . . ?
C4 C5 C6 C18 -42.87(15) . . . . ?
C4 C5 C12 C11 0.51(14) . . . . ?
C4 C5 C12 C25 -176.56(15) . . . . ?
C4 C5 C13 C14 76.03(15) . . . . ?
C4 C5 C13 C15 -96.24(13) . . . . ?
C5 C4 N1 C3 172.41(12) . . . . ?
C5 C4 N1 C11 0.57(15) . . . . ?
C5 C6 C7 N2 123.12(12) . . . . ?
C5 C6 C7 O2 -59.55(17) . . . . ?
C5 C6 C16 C15 23.97(12) . . . . ?
C5 C6 C16 C23 -97.90(12) . . . . ?
C5 C6 C16 C24 141.44(11) . . . . ?
C5 C6 C18 C17 -117.17(13) . . . . ?
C5 C6 C18 C19 62.2(2) . . . . ?
C5 C12 C25 C26 178.57(14) . . . . ?
C5 C13 C15 C16 -5.76(16) . . . . ?
C5 C13 C15 N5 176.74(14) . . . . ?
C6 C5 C12 C11 -120.37(13) . . . . ?
C6 C5 C12 C25 62.6(2) . . . . ?
C6 C5 C13 C14 -166.72(12) . . . . ?
C6 C5 C13 C15 21.00(14) . . . . ?
C6 C7 N2 C8 174.89(12) . . . . ?
C6 C7 N2 C17 0.69(15) . . . . ?
C6 C18 C19 C20 -179.66(14) . . . . ?
C7 C6 C16 C15 -91.32(12) . . . . ?
C7 C6 C16 C23 146.80(11) . . . . ?
C7 C6 C16 C24 26.14(14) . . . . ?
C7 C6 C18 C17 2.18(14) . . . . ?
C7 C6 C18 C19 -178.45(15) . . . . ?
C8 C9 O3 C10 -175.52(14) . . . . ?
C9 C8 N2 C7 89.60(17) . . . . ?
C9 C8 N2 C17 -97.08(17) . . . . ?
C11 C12 C25 C26 1.8(2) . . . . ?
C12 C5 C6 C7 -42.69(15) . . . . ?
C12 C5 C6 C16 -155.89(11) . . . . ?
C12 C5 C6 C18 72.74(15) . . . . ?
C12 C5 C13 C14 -38.24(18) . . . . ?
C12 C5 C13 C15 149.48(12) . . . . ?
C12 C11 C28 C27 0.0(2) . . . . ?
C12 C11 N1 C3 -171.96(12) . . . . ?
C12 C11 N1 C4 -0.23(16) . . . . ?
C12 C25 C26 C27 -0.6(2) . . . . ?
C13 C5 C6 C7 86.64(12) . . . . ?
C13 C5 C6 C16 -26.56(12) . . . . ?
C13 C5 C6 C18 -157.93(11) . . . . ?
C13 C5 C12 C11 118.39(13) . . . . ?
C13 C5 C12 C25 -58.7(2) . . . . ?
C13 C15 C16 C6 -12.06(14) . . . . ?
C13 C15 C16 C23 109.91(13) . . . . ?
C13 C15 C16 C24 -131.43(12) . . . . ?
C14 C13 C15 C16 -178.02(12) . . . . ?
C14 C13 C15 N5 4.5(2) . . . . ?
C16 C6 C7 N2 -125.24(12) . . . . ?
C16 C6 C7 O2 52.09(17) . . . . ?
C16 C6 C18 C17 117.91(13) . . . . ?
C16 C6 C18 C19 -62.7(2) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C6 C7 N2 -1.74(14) . . . . ?
C18 C6 C7 O2 175.59(13) . . . . ?
C18 C6 C16 C15 155.32(11) . . . . ?
C18 C6 C16 C23 33.44(16) . . . . ?
C18 C6 C16 C24 -87.22(14) . . . . ?
C18 C17 C22 C21 1.3(2) . . . . ?
C18 C17 N2 C7 0.77(16) . . . . ?
C18 C17 N2 C8 -173.16(13) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C17 -1.0(2) . . . . ?
C22 C17 C18 C6 178.85(13) . . . . ?
C22 C17 C18 C19 -0.6(2) . . . . ?
C22 C17 N2 C7 179.95(14) . . . . ?
C22 C17 N2 C8 6.0(2) . . . . ?
C25 C26 C27 C28 -0.9(2) . . . . ?
C26 C27 C28 C11 1.2(2) . . . . ?
C28 C11 C12 C5 -178.98(13) . . . . ?
C28 C11 C12 C25 -1.5(2) . . . . ?
C28 C11 N1 C3 6.7(2) . . . . ?
C28 C11 N1 C4 178.45(14) . . . . ?
N1 C4 C5 C6 123.77(12) . . . . ?
N1 C4 C5 C12 -0.66(14) . . . . ?
N1 C4 C5 C13 -125.17(12) . . . . ?
N1 C11 C12 C5 -0.22(15) . . . . ?
N1 C11 C12 C25 177.29(12) . . . . ?
N1 C11 C28 C27 -178.56(14) . . . . ?
N2 C8 C9 O3 63.51(17) . . . . ?
N2 C17 C18 C6 -1.93(16) . . . . ?
N2 C17 C18 C19 178.61(12) . . . . ?
N2 C17 C22 C21 -177.79(14) . . . . ?
N5 C15 C16 C6 165.80(12) . . . . ?
N5 C15 C16 C23 -72.23(16) . . . . ?
N5 C15 C16 C24 46.43(16) . . . . ?
O1 C2 C3 N1 -61.70(17) . . . . ?
O2 C7 N2 C8 -2.4(2) . . . . ?
O2 C7 N2 C17 -176.62(13) . . . . ?
O5 C4 C5 C6 -59.44(17) . . . . ?
O5 C4 C5 C12 176.13(13) . . . . ?
O5 C4 C5 C13 51.62(17) . . . . ?
O5 C4 N1 C3 -4.3(2) . . . . ?
O5 C4 N1 C11 -176.15(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
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