# Supplementary Information (SI) for Materials Advances.
# 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_L14_001P21n
_database_code_depnum_ccdc_archive 'CCDC 2324804'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C24 H30 N4 O10'
_chemical_formula_weight         534.527
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.884(2)
_cell_length_b                   9.934(2)
_cell_length_c                   12.344(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.79(3)
_cell_angle_gamma                90
_cell_volume                     1312.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7901
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.17
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12360
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9963
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -15
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                1970
_reflns_number_total             2976
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.6587
_refine_diff_density_min         -0.3374
_refine_diff_density_rms         0.0639
_refine_ls_d_res_high            0.7717
_refine_ls_d_res_low             6.4357
_refine_ls_goodness_of_fit_ref   1.0425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.0425
_refine_ls_shift/su_max          0.0023
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+1.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1785
_refine_ls_wR_factor_ref         0.1925
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3a), C1D(H1D)
2.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C2D(H2Da,H2Db,H2Dc), C3D(H3Da,H3Db,H3Dc)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
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_refinement_flags_posn
O1 O 0.4439(2) 0.6118(2) 0.18888(17) 0.0636(6) Uani 1.000000 .
O2 O 0.2927(2) 0.2303(3) 0.29004(19) 0.0728(7) Uani 1.000000 .
O3 O 0.0245(3) 0.5179(3) -0.1708(2) 0.0819(7) Uani 1.000000 .
H3 H -0.016(3) 0.4967(16) -0.2435(9) 0.1229(11) Uiso 1.000000 GR
O4 O 0.0888(2) 0.3049(3) -0.1570(2) 0.0738(7) Uani 1.000000 .
N1 N 0.3508(2) 0.4123(3) 0.20705(19) 0.0564(6) Uani 1.000000 .
C1 C 0.4216(3) 0.5290(3) 0.2488(2) 0.0541(7) Uani 1.000000 .
C2 C 0.4681(2) 0.5284(3) 0.3829(2) 0.0490(6) Uani 1.000000 .
C3 C 0.5421(3) 0.6231(3) 0.4670(2) 0.0525(7) Uani 1.000000 .
H3a H 0.5692(3) 0.7041(3) 0.4448(2) 0.0629(8) Uiso 1.000000 R
C4 C 0.4270(2) 0.4103(3) 0.4141(2) 0.0511(7) Uani 1.000000 .
C5 C 0.3488(3) 0.3349(3) 0.3012(2) 0.0554(7) Uani 1.000000 .
C6 C 0.2866(3) 0.3683(4) 0.0791(2) 0.0639(9) Uani 1.000000 .
H6 H 0.2557(3) 0.2749(4) 0.0801(2) 0.0767(10) Uiso 1.000000 R
C7 C 0.3773(3) 0.3580(4) 0.0245(3) 0.0658(8) Uani 1.000000 .
H7a H 0.4145(17) 0.4465(6) 0.0264(19) 0.0987(13) Uiso 1.000000 GR
H7b H 0.4432(13) 0.2935(18) 0.0705(13) 0.0987(13) Uiso 1.000000 GR
H7c H 0.3331(5) 0.327(2) -0.0590(7) 0.0987(13) Uiso 1.000000 GR
C8 C 0.1747(3) 0.4528(4) 0.0166(3) 0.0753(10) Uani 1.000000 .
H8a H 0.1238(3) 0.4488(4) 0.0623(3) 0.0903(12) Uiso 1.000000 R
H8b H 0.2021(3) 0.5473(4) 0.0187(3) 0.0903(12) Uiso 1.000000 R
C9 C 0.0925(3) 0.4159(4) -0.1118(3) 0.0596(8) Uani 1.000000 .
O1D O 0.6109(3) -0.0180(3) -0.0996(2) 0.0939(9) Uani 1.000000 .
N1D N 0.6906(2) 0.1016(2) 0.0724(2) 0.0576(6) Uani 1.000000 .
C1D C 0.6343(3) 0.0905(4) -0.0452(3) 0.0683(9) Uani 1.000000 .
H1D H 0.6101(3) 0.1708(4) -0.0914(3) 0.0819(10) Uiso 1.000000 R
C2D C 0.7141(4) 0.2310(4) 0.1324(3) 0.0755(10) Uani 1.000000 .
H2Da H 0.680(2) 0.3027(4) 0.0723(4) 0.1132(15) Uiso 1.000000 GR
H2Db H 0.674(2) 0.2339(10) 0.1867(18) 0.1132(15) Uiso 1.000000 GR
H2Dc H 0.8044(4) 0.2439(12) 0.1789(19) 0.1132(15) Uiso 1.000000 GR
C3D C 0.7295(4) -0.0173(4) 0.1486(3) 0.0771(10) Uani 1.000000 .
H3Da H 0.6665(12) -0.0391(16) 0.177(2) 0.1156(15) Uiso 1.000000 GR
H3Db H 0.739(2) -0.0933(8) 0.1024(8) 0.1156(15) Uiso 1.000000 GR
H3Dc H 0.8098(13) 0.0003(10) 0.2178(13) 0.1156(15) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.211(3) . ?
O2 C5 1.209(4) . ?
O3 H3 0.8400 . ?
O3 C9 1.303(4) . ?
O4 C9 1.228(4) . ?
N1 C1 1.393(4) . ?
N1 C5 1.403(4) . ?
N1 C6 1.490(3) . ?
C1 C2 1.499(4) . ?
C2 C3 1.394(4) . ?
C2 C4 1.387(4) . ?
C3 H3a 0.9500 . ?
C3 C4 1.390(4) 3_666 ?
C4 C5 1.497(4) . ?
C6 H6 1.0000 . ?
C6 C7 1.502(4) . ?
C6 C8 1.475(4) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.501(4) . ?
O1D C1D 1.236(4) . ?
N1D C1D 1.312(4) . ?
N1D C2D 1.449(4) . ?
N1D C3D 1.455(4) . ?
C1D H1D 0.9500 . ?
C2D H2Da 0.9800 . ?
C2D H2Db 0.9800 . ?
C2D H2Dc 0.9800 . ?
C3D H3Da 0.9800 . ?
C3D H3Db 0.9800 . ?
C3D H3Dc 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 H3 109.5 . . ?
C5 N1 C1 112.0(2) . . ?
C6 N1 C1 125.8(2) . . ?
C6 N1 C5 122.1(3) . . ?
N1 C1 O1 126.6(3) . . ?
C2 C1 O1 127.2(3) . . ?
C2 C1 N1 106.2(2) . . ?
C3 C2 C1 129.0(3) . . ?
C4 C2 C1 107.7(2) . . ?
C4 C2 C3 123.2(2) . . ?
H3a C3 C2 122.69(16) . . ?
C4 C3 C2 114.6(3) 3_666 . ?
C4 C3 H3a 122.69(17) 3_666 . ?
C3 C4 C2 122.2(3) 3_666 . ?
C5 C4 C2 108.4(2) . . ?
C5 C4 C3 129.4(3) . 3_666 ?
N1 C5 O2 125.8(3) . . ?
C4 C5 O2 128.6(3) . . ?
C4 C5 N1 105.6(2) . . ?
H6 C6 N1 106.34(17) . . ?
C7 C6 N1 111.0(2) . . ?
C7 C6 H6 106.3(2) . . ?
C8 C6 N1 108.5(3) . . ?
C8 C6 H6 106.3(2) . . ?
C8 C6 C7 117.6(3) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C6 108.30(19) . . ?
H8b C8 C6 108.3(2) . . ?
H8b C8 H8a 107.4 . . ?
C9 C8 C6 115.9(3) . . ?
C9 C8 H8a 108.30(18) . . ?
C9 C8 H8b 108.3(2) . . ?
O4 C9 O3 123.6(3) . . ?
C8 C9 O3 111.2(3) . . ?
C8 C9 O4 125.3(3) . . ?
C2D N1D C1D 122.2(3) . . ?
C3D N1D C1D 120.8(3) . . ?
C3D N1D C2D 117.0(3) . . ?
N1D C1D O1D 124.1(3) . . ?
H1D C1D O1D 117.97(19) . . ?
H1D C1D N1D 117.97(19) . . ?
H2Da C2D N1D 109.5 . . ?
H2Db C2D N1D 109.5 . . ?
H2Db C2D H2Da 109.5 . . ?
H2Dc C2D N1D 109.5 . . ?
H2Dc C2D H2Da 109.5 . . ?
H2Dc C2D H2Db 109.5 . . ?
H3Da C3D N1D 109.5 . . ?
H3Db C3D N1D 109.5 . . ?
H3Db C3D H3Da 109.5 . . ?
H3Dc C3D N1D 109.5 . . ?
H3Dc C3D H3Da 109.5 . . ?
H3Dc C3D H3Db 109.5 . . ?

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
O3 H3 O1D 0.8400 1.772(3) 2.604(3) 170.0(6) 2_554

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
O1 C1 N1 C5 176.9(3) . . . . ?
O1 C1 N1 C6 -1.2(4) . . . . ?
O1 C1 C2 C3 2.6(4) . . . . ?
O1 C1 C2 C4 -175.8(3) . . . . ?
O2 C5 N1 C1 178.6(3) . . . . ?
O2 C5 N1 C6 -3.2(4) . . . . ?
O2 C5 C4 C2 -177.1(3) . . . . ?
O2 C5 C4 C3 2.6(4) . . . 3_666 ?
O3 C9 C8 C6 -157.7(3) . . . . ?
O4 C9 C8 C6 22.2(4) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
N1 C1 C2 C4 2.2(3) . . . . ?
N1 C5 C4 C2 1.7(3) . . . . ?
N1 C5 C4 C3 -178.6(2) . . . 3_666 ?
N1 C6 C8 C9 -175.6(3) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . 3_666 ?
C1 C2 C4 C3 177.9(2) . . . 3_666 ?
C1 C2 C4 C5 -2.4(2) . . . . ?
C2 C3 C4 C2 -0.6(3) . . 3_666 3_666 ?
C2 C3 C4 C5 179.1(2) . . 3_666 3_666 ?
C2 C4 C3 C2 0.6(3) . . 3_666 3_666 ?
O1D C1D N1D C2D -178.8(4) . . . . ?
O1D C1D N1D C3D -0.4(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_l13_041p-1
_database_code_depnum_ccdc_archive 'CCDC 2324808'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C9 H7 N)'
_chemical_formula_sum            'C36 H30 N4 O8'
_chemical_formula_weight         646.64
_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                   10.925(2)
_cell_length_b                   12.294(3)
_cell_length_c                   13.214(3)
_cell_angle_alpha                71.23(3)
_cell_angle_beta                 89.97(3)
_cell_angle_gamma                68.84(3)
_cell_volume                     1553.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6472
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.18
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12357
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.176
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2229
_reflns_number_total             5459
_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       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2359
_refine_ls_R_factor_gt           0.1153
_refine_ls_restrained_S_all      1.072
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2974
_refine_ls_wR_factor_ref         0.3779
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C1Q(H1Q), C2Q(H2Q), C3Q(H3Q), C5Q(H5Q), C6Q(H6Q), C7Q(H7Q),
 C8Q(H8Q), C10Q(H10Q), C11Q(H11Q), C12Q(H12Q), C14Q(H14Q), C15Q(H15Q),
 C16Q(H16Q), C17Q(H17Q)
2.d Tetrahedral OH refined with riding coordinates:
 O5(H5), O7(H7)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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 0.9011(5) 0.0153(4) 0.0988(4) 0.0572(13) Uani 1 1 d . . . . .
O2 O 0.7696(6) 0.5097(4) 0.1588(4) 0.0645(15) Uani 1 1 d . . . . .
O3 O 1.0299(5) 0.3138(4) 0.4858(4) 0.0579(13) Uani 1 1 d . . . . .
O4 O 1.1630(5) -0.1782(4) 0.4258(4) 0.0542(13) Uani 1 1 d . . . . .
O5 O 1.1505(6) -0.4614(5) 0.2338(5) 0.0829(19) Uani 1 1 d . . . . .
H5 H 1.155627 -0.521233 0.214086 0.124 Uiso 1 1 calc R U . . .
O6 O 1.2302(8) -0.4058(6) 0.0811(6) 0.112(2) Uani 1 1 d . . . . .
O7 O 0.7109(7) 0.8134(5) 0.2535(5) 0.101(2) Uani 1 1 d . . . . .
H7 H 0.686751 0.888655 0.246976 0.151 Uiso 1 1 calc R U . . .
O8 O 0.6255(6) 0.8030(5) 0.4063(5) 0.0805(17) Uani 1 1 d . . . . .
N1 N 1.0407(6) -0.1096(5) 0.2584(5) 0.0498(15) Uani 1 1 d . . . . .
N2 N 0.8880(6) 0.4417(5) 0.3258(5) 0.0496(15) Uani 1 1 d . . . . .
C1 C 0.9559(7) 0.0025(6) 0.1822(6) 0.0472(17) Uani 1 1 d . . . . .
C2 C 0.9526(6) 0.1010(6) 0.2293(5) 0.0438(16) Uani 1 1 d . . . . .
C3 C 0.8848(7) 0.2287(5) 0.1880(5) 0.0471(17) Uani 1 1 d . . . . .
H3 H 0.832382 0.270023 0.119397 0.057 Uiso 1 1 calc R U . . .
C4 C 0.8993(7) 0.2908(6) 0.2535(5) 0.0454(16) Uani 1 1 d . . . . .
C5 C 0.8416(8) 0.4271(6) 0.2342(6) 0.0516(18) Uani 1 1 d . . . . .
C6 C 0.9726(7) 0.3275(6) 0.4014(6) 0.0508(18) Uani 1 1 d . . . . .
C7 C 0.9765(6) 0.2317(5) 0.3535(5) 0.0433(16) Uani 1 1 d . . . . .
C8 C 1.0433(6) 0.1049(6) 0.3956(5) 0.0431(16) Uani 1 1 d . . . . .
H8 H 1.095527 0.064331 0.464324 0.052 Uiso 1 1 calc R U . . .
C9 C 1.0287(7) 0.0403(5) 0.3299(5) 0.0438(16) Uani 1 1 d . . . . .
C10 C 1.0886(7) -0.0968(7) 0.3500(6) 0.0523(18) Uani 1 1 d . . . . .
C11 C 1.0627(7) -0.2306(6) 0.2487(6) 0.0554(19) Uani 1 1 d . . . . .
H11A H 0.982070 -0.225713 0.210304 0.066 Uiso 1 1 calc R U . . .
H11B H 1.079718 -0.293802 0.321601 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1840(8) -0.2713(8) 0.1856(10) 0.096(3) Uani 1 1 d . . . . .
H12 H 1.165029 -0.203747 0.113881 0.115 Uiso 1 1 calc R U . . .
C13 C 1.3095(12) -0.2921(9) 0.2329(9) 0.111(4) Uani 1 1 d . . . . .
H13A H 1.338391 -0.367257 0.297256 0.166 Uiso 1 1 calc R U . . .
H13B H 1.304260 -0.220795 0.253256 0.166 Uiso 1 1 calc R U . . .
H13C H 1.373147 -0.302804 0.181127 0.166 Uiso 1 1 calc R U . . .
C14 C 1.1872(10) -0.3879(10) 0.1642(10) 0.096(3) Uani 1 1 d . . . . .
C15 C 0.8587(8) 0.5624(6) 0.3356(6) 0.060(2) Uani 1 1 d . . . . .
H15A H 0.864692 0.620860 0.265755 0.071 Uiso 1 1 calc R U . . .
H15B H 0.926122 0.554978 0.390127 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7233(10) 0.6147(6) 0.3677(7) 0.086(3) Uani 1 1 d . . . . .
H16 H 0.663782 0.612916 0.311311 0.104 Uiso 1 1 calc R U . . .
C17 C 0.6898(12) 0.5476(8) 0.4650(10) 0.121(4) Uani 1 1 d . . . . .
H17A H 0.725292 0.561820 0.525527 0.181 Uiso 1 1 calc R U . . .
H17B H 0.727523 0.458670 0.475560 0.181 Uiso 1 1 calc R U . . .
H17C H 0.593200 0.575714 0.461340 0.181 Uiso 1 1 calc R U . . .
C18 C 0.6832(9) 0.7518(7) 0.3465(7) 0.068(2) Uani 1 1 d . . . . .
N1Q N 0.6109(8) 0.0614(7) 0.1703(8) 0.097(3) Uani 1 1 d . . . . .
C1Q C 0.5534(9) 0.1088(10) 0.0717(7) 0.084(3) Uani 1 1 d . . . . .
H1Q H 0.559310 0.050792 0.036832 0.101 Uiso 1 1 calc R U . . .
C2Q C 0.4833(8) 0.2345(9) 0.0093(7) 0.077(2) Uani 1 1 d . . . . .
H2Q H 0.445625 0.256855 -0.062766 0.092 Uiso 1 1 calc R U . . .
C3Q C 0.4705(9) 0.3211(10) 0.0518(8) 0.088(3) Uani 1 1 d . . . . .
H3Q H 0.423464 0.406991 0.012910 0.105 Uiso 1 1 calc R U . . .
C4Q C 0.5372(8) 0.2731(7) 0.1691(7) 0.069(2) Uani 1 1 d . . . . .
C5Q C 0.5288(11) 0.3558(11) 0.2185(12) 0.110(4) Uani 1 1 d . . . . .
H5Q H 0.484138 0.442868 0.183668 0.132 Uiso 1 1 calc R U . . .
C6Q C 0.5888(11) 0.3048(12) 0.3214(10) 0.108(4) Uani 1 1 d . . . . .
H6Q H 0.586383 0.359664 0.358900 0.130 Uiso 1 1 calc R U . . .
C7Q C 0.6553(9) 0.1751(10) 0.3778(8) 0.080(3) Uani 1 1 d . . . . .
H7Q H 0.694254 0.147093 0.450450 0.096 Uiso 1 1 calc R U . . .
C8Q C 0.6637(9) 0.0931(10) 0.3311(8) 0.087(3) Uani 1 1 d . . . . .
H8Q H 0.706191 0.006265 0.368428 0.105 Uiso 1 1 calc R U . . .
C9Q C 0.6000(7) 0.1468(7) 0.2107(7) 0.066(2) Uani 1 1 d . . . . .
N2Q N 0.2297(6) 0.3040(6) 0.2529(6) 0.0659(18) Uani 1 1 d . . . . .
C10Q C 0.2967(8) 0.2300(8) 0.3457(7) 0.068(2) Uani 1 1 d . . . . .
H10Q H 0.307312 0.267277 0.396079 0.081 Uiso 1 1 calc R U . . .
C11Q C 0.3533(8) 0.1045(9) 0.3781(7) 0.073(2) Uani 1 1 d . . . . .
H11Q H 0.397883 0.057555 0.449274 0.088 Uiso 1 1 calc R U . . .
C12Q C 0.3455(8) 0.0447(8) 0.3060(8) 0.079(3) Uani 1 1 d . . . . .
H12Q H 0.387455 -0.042972 0.325568 0.095 Uiso 1 1 calc R U . . .
C13Q C 0.2708(7) 0.1213(6) 0.2003(6) 0.0509(18) Uani 1 1 d . . . . .
C14Q C 0.2510(10) 0.0751(9) 0.1206(9) 0.080(3) Uani 1 1 d . . . . .
H14Q H 0.287173 -0.011802 0.134126 0.096 Uiso 1 1 calc R U . . .
C15Q C 0.1818(10) 0.1527(11) 0.0265(9) 0.084(3) Uani 1 1 d . . . . .
H15Q H 0.168269 0.119244 -0.026155 0.100 Uiso 1 1 calc R U . . .
C16Q C 0.1291(9) 0.2779(9) 0.0014(7) 0.075(2) Uani 1 1 d . . . . .
H16Q H 0.081332 0.328775 -0.068124 0.090 Uiso 1 1 calc R U . . .
C17Q C 0.1430(8) 0.3341(7) 0.0747(6) 0.065(2) Uani 1 1 d . . . . .
H17Q H 0.106090 0.421713 0.057302 0.078 Uiso 1 1 calc R U . . .
C18Q C 0.2184(7) 0.2494(6) 0.1805(6) 0.0525(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.192(8) . ?
O2 C5 1.189(8) . ?
O3 C6 1.212(8) . ?
O4 C10 1.198(8) . ?
O5 H5 0.8400 . ?
O5 C14 1.245(13) . ?
O6 C14 1.246(11) . ?
O7 H7 0.8400 . ?
O7 C18 1.320(9) . ?
O8 C18 1.205(9) . ?
N1 C1 1.398(8) . ?
N1 C10 1.395(9) . ?
N1 C11 1.467(8) . ?
N2 C5 1.399(9) . ?
N2 C6 1.408(9) . ?
N2 C15 1.450(8) . ?
C1 C2 1.519(9) . ?
C2 C3 1.386(9) . ?
C2 C9 1.390(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(9) . ?
C4 C5 1.494(9) . ?
C4 C7 1.387(9) . ?
C6 C7 1.494(9) . ?
C7 C8 1.376(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(8) . ?
C9 C10 1.502(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.579(11) . ?
C12 H12 1.0000 . ?
C12 C13 1.408(13) . ?
C12 C14 1.536(12) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.506(11) . ?
C16 H16 1.0000 . ?
C16 C17 1.416(12) . ?
C16 C18 1.508(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1Q C1Q 1.296(11) . ?
N1Q C9Q 1.293(11) . ?
C1Q H1Q 0.9500 . ?
C1Q C2Q 1.407(12) . ?
C2Q H2Q 0.9500 . ?
C2Q C3Q 1.322(12) . ?
C3Q H3Q 0.9500 . ?
C3Q C4Q 1.543(13) . ?
C4Q C5Q 1.352(13) . ?
C4Q C9Q 1.366(11) . ?
C5Q H5Q 0.9500 . ?
C5Q C6Q 1.352(15) . ?
C6Q H6Q 0.9500 . ?
C6Q C7Q 1.423(14) . ?
C7Q H7Q 0.9500 . ?
C7Q C8Q 1.319(12) . ?
C8Q H8Q 0.9500 . ?
C8Q C9Q 1.563(12) . ?
N2Q C10Q 1.291(10) . ?
N2Q C18Q 1.363(9) . ?
C10Q H10Q 0.9500 . ?
C10Q C11Q 1.353(11) . ?
C11Q H11Q 0.9500 . ?
C11Q C12Q 1.397(12) . ?
C12Q H12Q 0.9500 . ?
C12Q C13Q 1.451(11) . ?
C13Q C14Q 1.396(11) . ?
C13Q C18Q 1.401(9) . ?
C14Q H14Q 0.9500 . ?
C14Q C15Q 1.322(12) . ?
C15Q H15Q 0.9500 . ?
C15Q C16Q 1.358(12) . ?
C16Q H16Q 0.9500 . ?
C16Q C17Q 1.394(11) . ?
C17Q H17Q 0.9500 . ?
C17Q C18Q 1.471(10) . ?

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 O5 H5 109.5 . . ?
C18 O7 H7 109.5 . . ?
C1 N1 C11 122.5(6) . . ?
C10 N1 C1 114.0(5) . . ?
C10 N1 C11 123.0(6) . . ?
C5 N2 C6 112.1(5) . . ?
C5 N2 C15 122.7(6) . . ?
C6 N2 C15 125.1(6) . . ?
O1 C1 N1 126.5(6) . . ?
O1 C1 C2 128.8(6) . . ?
N1 C1 C2 104.7(6) . . ?
C3 C2 C1 129.8(6) . . ?
C3 C2 C9 122.7(6) . . ?
C9 C2 C1 107.5(6) . . ?
C2 C3 H3 122.5 . . ?
C4 C3 C2 114.9(6) . . ?
C4 C3 H3 122.5 . . ?
C3 C4 C5 128.9(7) . . ?
C3 C4 C7 123.1(6) . . ?
C7 C4 C5 108.0(6) . . ?
O2 C5 N2 124.8(6) . . ?
O2 C5 C4 129.2(7) . . ?
N2 C5 C4 105.9(6) . . ?
O3 C6 N2 125.8(6) . . ?
O3 C6 C7 129.0(7) . . ?
N2 C6 C7 105.2(6) . . ?
C4 C7 C6 108.8(6) . . ?
C8 C7 C4 122.5(6) . . ?
C8 C7 C6 128.7(6) . . ?
C7 C8 H8 122.5 . . ?
C7 C8 C9 115.0(6) . . ?
C9 C8 H8 122.5 . . ?
C2 C9 C8 121.8(6) . . ?
C2 C9 C10 109.3(6) . . ?
C8 C9 C10 128.9(6) . . ?
O4 C10 N1 126.8(6) . . ?
O4 C10 C9 128.7(6) . . ?
N1 C10 C9 104.5(6) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
N1 C11 C12 111.2(6) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12 107.1 . . ?
C13 C12 C11 117.3(9) . . ?
C13 C12 H12 107.1 . . ?
C13 C12 C14 110.0(7) . . ?
C14 C12 C11 107.8(7) . . ?
C14 C12 H12 107.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 O6 123.9(9) . . ?
O5 C14 C12 117.2(9) . . ?
O6 C14 C12 118.8(11) . . ?
N2 C15 H15A 109.0 . . ?
N2 C15 H15B 109.0 . . ?
N2 C15 C16 112.8(6) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16 102.9 . . ?
C15 C16 C18 110.2(7) . . ?
C17 C16 C15 119.9(8) . . ?
C17 C16 H16 102.9 . . ?
C17 C16 C18 115.3(7) . . ?
C18 C16 H16 102.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 C18 C16 114.3(7) . . ?
O8 C18 O7 122.1(7) . . ?
O8 C18 C16 123.6(8) . . ?
C9Q N1Q C1Q 111.4(9) . . ?
N1Q C1Q H1Q 115.6 . . ?
N1Q C1Q C2Q 128.7(10) . . ?
C2Q C1Q H1Q 115.6 . . ?
C1Q C2Q H2Q 120.3 . . ?
C3Q C2Q C1Q 119.4(9) . . ?
C3Q C2Q H2Q 120.3 . . ?
C2Q C3Q H3Q 122.3 . . ?
C2Q C3Q C4Q 115.4(9) . . ?
C4Q C3Q H3Q 122.3 . . ?
C5Q C4Q C3Q 119.1(10) . . ?
C5Q C4Q C9Q 127.5(10) . . ?
C9Q C4Q C3Q 113.4(8) . . ?
C4Q C5Q H5Q 122.6 . . ?
C4Q C5Q C6Q 114.8(12) . . ?
C6Q C5Q H5Q 122.6 . . ?
C5Q C6Q H6Q 117.6 . . ?
C5Q C6Q C7Q 124.9(12) . . ?
C7Q C6Q H6Q 117.6 . . ?
C6Q C7Q H7Q 119.4 . . ?
C8Q C7Q C6Q 121.2(10) . . ?
C8Q C7Q H7Q 119.4 . . ?
C7Q C8Q H8Q 121.9 . . ?
C7Q C8Q C9Q 116.3(9) . . ?
C9Q C8Q H8Q 121.9 . . ?
N1Q C9Q C4Q 131.6(9) . . ?
N1Q C9Q C8Q 113.0(8) . . ?
C4Q C9Q C8Q 115.3(8) . . ?
C10Q N2Q C18Q 116.1(7) . . ?
N2Q C10Q H10Q 116.8 . . ?
N2Q C10Q C11Q 126.5(8) . . ?
C11Q C10Q H10Q 116.8 . . ?
C10Q C11Q H11Q 120.3 . . ?
C10Q C11Q C12Q 119.4(8) . . ?
C12Q C11Q H11Q 120.3 . . ?
C11Q C12Q H12Q 121.2 . . ?
C11Q C12Q C13Q 117.6(8) . . ?
C13Q C12Q H12Q 121.2 . . ?
C14Q C13Q C12Q 124.4(8) . . ?
C14Q C13Q C18Q 120.3(8) . . ?
C18Q C13Q C12Q 115.4(7) . . ?
C13Q C14Q H14Q 120.1 . . ?
C15Q C14Q C13Q 119.8(8) . . ?
C15Q C14Q H14Q 120.1 . . ?
C14Q C15Q H15Q 118.5 . . ?
C14Q C15Q C16Q 123.1(9) . . ?
C16Q C15Q H15Q 118.5 . . ?
C15Q C16Q H16Q 119.0 . . ?
C15Q C16Q C17Q 121.9(8) . . ?
C17Q C16Q H16Q 119.0 . . ?
C16Q C17Q H17Q 122.1 . . ?
C16Q C17Q C18Q 115.9(7) . . ?
C18Q C17Q H17Q 122.1 . . ?
N2Q C18Q C13Q 125.1(7) . . ?
N2Q C18Q C17Q 115.9(6) . . ?
C13Q C18Q C17Q 119.0(6) . . ?

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
O5 H5 N2Q 0.84 1.89 2.619(8) 144.5 1_645 yes
O7 H7 N1Q 0.84 1.89 2.672(9) 154.4 1_565 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
O1 C1 C2 C3 0.7(12) . . . . ?
O1 C1 C2 C9 178.1(7) . . . . ?
O3 C6 C7 C4 -177.5(7) . . . . ?
O3 C6 C7 C8 2.2(12) . . . . ?
N1 C1 C2 C3 179.8(6) . . . . ?
N1 C1 C2 C9 -2.9(7) . . . . ?
N1 C11 C12 C13 63.7(11) . . . . ?
N1 C11 C12 C14 -171.6(7) . . . . ?
N2 C6 C7 C4 1.3(7) . . . . ?
N2 C6 C7 C8 -179.0(6) . . . . ?
N2 C15 C16 C17 58.4(12) . . . . ?
N2 C15 C16 C18 -164.1(7) . . . . ?
C1 N1 C10 O4 -179.3(7) . . . . ?
C1 N1 C10 C9 -0.7(7) . . . . ?
C1 N1 C11 C12 91.0(8) . . . . ?
C1 C2 C3 C4 177.5(6) . . . . ?
C1 C2 C9 C8 -178.5(6) . . . . ?
C1 C2 C9 C10 2.5(7) . . . . ?
C2 C3 C4 C5 179.5(6) . . . . ?
C2 C3 C4 C7 0.6(10) . . . . ?
C2 C9 C10 O4 177.4(7) . . . . ?
C2 C9 C10 N1 -1.2(7) . . . . ?
C3 C2 C9 C8 -0.9(10) . . . . ?
C3 C2 C9 C10 -179.9(6) . . . . ?
C3 C4 C5 O2 1.3(12) . . . . ?
C3 C4 C5 N2 -179.5(6) . . . . ?
C3 C4 C7 C6 178.6(6) . . . . ?
C3 C4 C7 C8 -1.2(10) . . . . ?
C4 C7 C8 C9 0.6(9) . . . . ?
C5 N2 C6 O3 177.3(7) . . . . ?
C5 N2 C6 C7 -1.6(7) . . . . ?
C5 N2 C15 C16 80.7(9) . . . . ?
C5 C4 C7 C6 -0.6(7) . . . . ?
C5 C4 C7 C8 179.7(6) . . . . ?
C6 N2 C5 O2 -179.5(7) . . . . ?
C6 N2 C5 C4 1.3(7) . . . . ?
C6 N2 C15 C16 -104.3(8) . . . . ?
C6 C7 C8 C9 -179.1(6) . . . . ?
C7 C4 C5 O2 -179.6(7) . . . . ?
C7 C4 C5 N2 -0.4(7) . . . . ?
C7 C8 C9 C2 0.4(9) . . . . ?
C7 C8 C9 C10 179.1(6) . . . . ?
C8 C9 C10 O4 -1.5(12) . . . . ?
C8 C9 C10 N1 179.9(6) . . . . ?
C9 C2 C3 C4 0.4(10) . . . . ?
C10 N1 C1 O1 -178.7(7) . . . . ?
C10 N1 C1 C2 2.2(7) . . . . ?
C10 N1 C11 C12 -97.3(8) . . . . ?
C11 N1 C1 O1 -6.3(11) . . . . ?
C11 N1 C1 C2 174.6(6) . . . . ?
C11 N1 C10 O4 8.3(11) . . . . ?
C11 N1 C10 C9 -173.0(6) . . . . ?
C11 C12 C14 O5 -33.7(12) . . . . ?
C11 C12 C14 O6 148.8(9) . . . . ?
C13 C12 C14 O5 95.3(12) . . . . ?
C13 C12 C14 O6 -82.2(13) . . . . ?
C15 N2 C5 O2 -3.9(11) . . . . ?
C15 N2 C5 C4 176.9(6) . . . . ?
C15 N2 C6 O3 1.8(11) . . . . ?
C15 N2 C6 C7 -177.1(6) . . . . ?
C15 C16 C18 O7 42.8(11) . . . . ?
C15 C16 C18 O8 -140.3(9) . . . . ?
C17 C16 C18 O7 -177.6(10) . . . . ?
C17 C16 C18 O8 -0.6(15) . . . . ?
N1Q C1Q C2Q C3Q 0.0(15) . . . . ?
C1Q N1Q C9Q C4Q 2.1(13) . . . . ?
C1Q N1Q C9Q C8Q 177.9(7) . . . . ?
C1Q C2Q C3Q C4Q 0.5(12) . . . . ?
C2Q C3Q C4Q C5Q 180.0(9) . . . . ?
C2Q C3Q C4Q C9Q 0.1(11) . . . . ?
C3Q C4Q C5Q C6Q 179.2(8) . . . . ?
C3Q C4Q C9Q N1Q -1.7(13) . . . . ?
C3Q C4Q C9Q C8Q -177.4(7) . . . . ?
C4Q C5Q C6Q C7Q -0.9(16) . . . . ?
C5Q C4Q C9Q N1Q 178.5(10) . . . . ?
C5Q C4Q C9Q C8Q 2.8(13) . . . . ?
C5Q C6Q C7Q C8Q 0.5(16) . . . . ?
C6Q C7Q C8Q C9Q 1.4(13) . . . . ?
C7Q C8Q C9Q N1Q -179.4(8) . . . . ?
C7Q C8Q C9Q C4Q -2.9(11) . . . . ?
C9Q N1Q C1Q C2Q -1.2(14) . . . . ?
C9Q C4Q C5Q C6Q -1.0(15) . . . . ?
N2Q C10Q C11Q C12Q 2.5(13) . . . . ?
C10Q N2Q C18Q C13Q 1.4(11) . . . . ?
C10Q N2Q C18Q C17Q -179.5(7) . . . . ?
C10Q C11Q C12Q C13Q -2.7(12) . . . . ?
C11Q C12Q C13Q C14Q -178.2(7) . . . . ?
C11Q C12Q C13Q C18Q 2.4(10) . . . . ?
C12Q C13Q C14Q C15Q -179.8(8) . . . . ?
C12Q C13Q C18Q N2Q -1.9(10) . . . . ?
C12Q C13Q C18Q C17Q 179.1(6) . . . . ?
C13Q C14Q C15Q C16Q 1.0(14) . . . . ?
C14Q C13Q C18Q N2Q 178.7(7) . . . . ?
C14Q C13Q C18Q C17Q -0.3(10) . . . . ?
C14Q C15Q C16Q C17Q -0.9(14) . . . . ?
C15Q C16Q C17Q C18Q 0.1(12) . . . . ?
C16Q C17Q C18Q N2Q -178.7(7) . . . . ?
C16Q C17Q C18Q C13Q 0.4(10) . . . . ?
C18Q N2Q C10Q C11Q -1.7(12) . . . . ?
C18Q C13Q C14Q C15Q -0.4(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_l13_034
_database_code_depnum_ccdc_archive 'CCDC 2324807'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C5 H5 N)'
_chemical_formula_sum            'C28 H26 N4 O8'
_chemical_formula_weight         546.53
_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                   16.796(3)
_cell_length_b                   7.5311(15)
_cell_length_c                   10.637(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.17(3)
_cell_angle_gamma                90
_cell_volume                     1340.0(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8407
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12531
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2456
_reflns_number_total             3061
_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       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0796
_refine_ls_restrained_S_all      1.109
_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)+(0.0531P)²+2.1566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.1959
_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, All O(H) groups
2. Others
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(C72)=Sof(H72)=Sof(C82)=Sof(H82A)=Sof(H82B)=
 Sof(H82C)=1-FVAR(1)
 Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(C71)=Sof(H71)=Sof(C81)=Sof(H81A)=Sof(H81B)=
 Sof(H81C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C71(H71), C72(H72)
3.b Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C62(H62A,H62B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C1P(H1P), C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P)
3.d Idealised Me refined as rotating group:
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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 0.34528(12) 0.4129(3) 0.72606(19) 0.0453(5) Uani 1 1 d . . . . .
O2 O 0.46484(12) 0.9429(3) 0.83610(19) 0.0428(5) Uani 1 1 d . . . . .
O3 O 0.24982(17) 0.9705(5) 0.4764(3) 0.0850(10) Uani 1 1 d . . . . .
H3 H 0.215994 0.996817 0.416277 0.128 Uiso 1 1 calc R U . . .
O4 O 0.14111(17) 0.8907(5) 0.5616(3) 0.0861(10) Uani 1 1 d . . . . .
N1 N 0.39049(13) 0.7008(3) 0.7603(2) 0.0363(5) Uani 1 1 d . . . . .
C1 C 0.38646(15) 0.5193(4) 0.7870(3) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.44414(14) 0.4888(4) 0.9000(2) 0.0319(5) Uani 1 1 d . . . . .
C3 C 0.46044(15) 0.3328(4) 0.9674(2) 0.0331(6) Uani 1 1 d . . . . .
H3A H 0.434394 0.223439 0.946255 0.040 Uiso 1 1 calc R U . . .
C4 C 0.48174(15) 0.6486(4) 0.9315(2) 0.0321(6) Uani 1 1 d . . . . .
C5 C 0.44771(15) 0.7868(4) 0.8412(2) 0.0352(6) Uani 1 1 d . . . . .
C61 C 0.3470(9) 0.7898(18) 0.6527(16) 0.035(2) Uani 0.760(15) 1 d . . P A 1
H61A H 0.345197 0.711990 0.577509 0.042 Uiso 0.760(15) 1 calc R U P A 1
H61B H 0.374915 0.900868 0.633351 0.042 Uiso 0.760(15) 1 calc R U P A 1
C71 C 0.2613(3) 0.8327(9) 0.6837(4) 0.0369(12) Uani 0.760(15) 1 d . . P A 1
H71 H 0.235251 0.722021 0.711771 0.044 Uiso 0.760(15) 1 calc R U P A 1
C81 C 0.2589(5) 0.9766(11) 0.7870(7) 0.0493(16) Uani 0.760(15) 1 d . . P A 1
H81A H 0.284523 1.085151 0.759668 0.074 Uiso 0.760(15) 1 calc R U P A 1
H81B H 0.287327 0.933816 0.865593 0.074 Uiso 0.760(15) 1 calc R U P A 1
H81C H 0.203136 1.002180 0.801041 0.074 Uiso 0.760(15) 1 calc R U P A 1
C62 C 0.333(3) 0.765(6) 0.656(6) 0.044(9) Uani 0.240(15) 1 d . . P A 2
H62A H 0.362722 0.792747 0.582794 0.053 Uiso 0.240(15) 1 calc R U P A 2
H62B H 0.295516 0.666692 0.631125 0.053 Uiso 0.240(15) 1 calc R U P A 2
C72 C 0.2846(11) 0.923(3) 0.6838(12) 0.040(4) Uani 0.240(15) 1 d . . P A 2
H72 H 0.315189 1.036750 0.681335 0.048 Uiso 0.240(15) 1 calc R U P A 2
C82 C 0.2454(17) 0.900(4) 0.803(3) 0.059(7) Uani 0.240(15) 1 d . . P A 2
H82A H 0.216046 0.787276 0.799730 0.089 Uiso 0.240(15) 1 calc R U P A 2
H82B H 0.208189 0.998177 0.812254 0.089 Uiso 0.240(15) 1 calc R U P A 2
H82C H 0.286210 0.898841 0.874690 0.089 Uiso 0.240(15) 1 calc R U P A 2
C9 C 0.2139(3) 0.9048(6) 0.5674(3) 0.0693(12) Uani 1 1 d . . . . .
N1P N 0.1375(2) 0.4331(5) 0.7843(4) 0.0699(10) Uani 1 1 d . . . . .
C1P C 0.0650(3) 0.4360(5) 0.8126(3) 0.0737(13) Uani 1 1 d . . . . .
H1P H 0.053581 0.471500 0.894817 0.088 Uiso 1 1 calc R U . . .
C2P C -0.0012(3) 0.3844(6) 0.7182(6) 0.0860(16) Uani 1 1 d . . . . .
H2P H -0.055662 0.383876 0.735947 0.103 Uiso 1 1 calc R U . . .
C3P C 0.0234(2) 0.3361(5) 0.5997(4) 0.0673(11) Uani 1 1 d . . . . .
H3P H -0.014339 0.301258 0.532309 0.081 Uiso 1 1 calc R U . . .
C4P C 0.1011(3) 0.3408(5) 0.5852(4) 0.0695(11) Uani 1 1 d . . . . .
H4P H 0.118713 0.307927 0.506045 0.083 Uiso 1 1 calc R U . . .
C5P C 0.1535(3) 0.3886(6) 0.6752(5) 0.0733(12) Uani 1 1 d . . . . .
H5P H 0.208019 0.390305 0.657916 0.088 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
O1 C1 1.208(3) . ?
O2 C5 1.212(3) . ?
O3 H3 0.8400 . ?
O3 C9 1.284(5) . ?
O4 C9 1.224(5) . ?
N1 C1 1.399(4) . ?
N1 C5 1.392(4) . ?
N1 C61 1.464(15) . ?
N1 C62 1.49(6) . ?
C1 C2 1.492(4) . ?
C2 C3 1.390(4) . ?
C2 C4 1.387(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.390(4) 3_667 ?
C4 C5 1.494(4) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C71 1.538(16) . ?
C71 H71 1.0000 . ?
C71 C81 1.546(11) . ?
C71 C9 1.511(5) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 C72 1.48(6) . ?
C72 H72 1.0000 . ?
C72 C82 1.49(4) . ?
C72 C9 1.642(16) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
N1P C1P 1.281(6) . ?
N1P C5P 1.260(6) . ?
C1P H1P 0.9500 . ?
C1P C2P 1.482(7) . ?
C2P H2P 0.9500 . ?
C2P C3P 1.409(7) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.328(6) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.292(6) . ?
C5P H5P 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
C9 O3 H3 109.5 . . ?
C1 N1 C61 125.2(6) . . ?
C1 N1 C62 115.4(18) . . ?
C5 N1 C1 111.9(2) . . ?
C5 N1 C61 122.6(6) . . ?
C5 N1 C62 132.7(19) . . ?
O1 C1 N1 125.1(3) . . ?
O1 C1 C2 128.9(3) . . ?
N1 C1 C2 105.9(2) . . ?
C3 C2 C1 129.0(2) . . ?
C4 C2 C1 108.0(2) . . ?
C4 C2 C3 123.0(2) . . ?
C2 C3 H3A 123.0 . . ?
C4 C3 C2 113.9(2) 3_667 . ?
C4 C3 H3A 123.0 3_667 . ?
C2 C4 C3 123.1(2) . 3_667 ?
C2 C4 C5 108.1(2) . . ?
C3 C4 C5 128.9(3) 3_667 . ?
O2 C5 N1 125.2(3) . . ?
O2 C5 C4 128.7(3) . . ?
N1 C5 C4 106.0(2) . . ?
N1 C61 H61A 109.7 . . ?
N1 C61 H61B 109.7 . . ?
N1 C61 C71 109.9(10) . . ?
H61A C61 H61B 108.2 . . ?
C71 C61 H61A 109.7 . . ?
C71 C61 H61B 109.7 . . ?
C61 C71 H71 109.4 . . ?
C61 C71 C81 112.6(8) . . ?
C81 C71 H71 109.4 . . ?
C9 C71 C61 109.5(7) . . ?
C9 C71 H71 109.4 . . ?
C9 C71 C81 106.5(5) . . ?
C71 C81 H81A 109.5 . . ?
C71 C81 H81B 109.5 . . ?
C71 C81 H81C 109.5 . . ?
H81A C81 H81B 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
N1 C62 H62A 108.2 . . ?
N1 C62 H62B 108.2 . . ?
H62A C62 H62B 107.3 . . ?
C72 C62 N1 116(4) . . ?
C72 C62 H62A 108.2 . . ?
C72 C62 H62B 108.2 . . ?
C62 C72 H72 113.0 . . ?
C62 C72 C82 111(3) . . ?
C62 C72 C9 99(3) . . ?
C82 C72 H72 113.0 . . ?
C82 C72 C9 106.7(19) . . ?
C9 C72 H72 113.0 . . ?
C72 C82 H82A 109.5 . . ?
C72 C82 H82B 109.5 . . ?
C72 C82 H82C 109.5 . . ?
H82A C82 H82B 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
O3 C9 C71 120.5(4) . . ?
O3 C9 C72 100.4(8) . . ?
O4 C9 O3 122.0(3) . . ?
O4 C9 C71 117.4(4) . . ?
O4 C9 C72 134.1(7) . . ?
C5P N1P C1P 120.5(4) . . ?
N1P C1P H1P 119.8 . . ?
N1P C1P C2P 120.5(4) . . ?
C2P C1P H1P 119.8 . . ?
C1P C2P H2P 122.9 . . ?
C3P C2P C1P 114.3(3) . . ?
C3P C2P H2P 122.9 . . ?
C2P C3P H3P 121.1 . . ?
C4P C3P C2P 117.9(4) . . ?
C4P C3P H3P 121.1 . . ?
C3P C4P H4P 118.9 . . ?
C5P C4P C3P 122.2(4) . . ?
C5P C4P H4P 118.9 . . ?
N1P C5P C4P 124.7(4) . . ?
N1P C5P H5P 117.7 . . ?
C4P C5P H5P 117.7 . . ?

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
O3 H3 N1P 0.84 1.91 2.751(4) 177.1 4_575 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
O1 C1 C2 C3 -4.8(5) . . . . ?
O1 C1 C2 C4 175.6(3) . . . . ?
N1 C1 C2 C3 177.1(3) . . . . ?
N1 C1 C2 C4 -2.5(3) . . . . ?
N1 C61 C71 C81 68.3(12) . . . . ?
N1 C61 C71 C9 -173.4(7) . . . . ?
N1 C62 C72 C82 -51(4) . . . . ?
N1 C62 C72 C9 -163(3) . . . . ?
C1 N1 C5 O2 177.7(3) . . . . ?
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 N1 C61 C71 82.7(11) . . . . ?
C1 N1 C62 C72 130(3) . . . . ?
C1 C2 C3 C4 179.9(2) . . . 3_667 ?
C1 C2 C4 C3 -179.8(2) . . . 3_667 ?
C1 C2 C4 C5 1.3(3) . . . . ?
C2 C4 C5 O2 -179.4(3) . . . . ?
C2 C4 C5 N1 0.4(3) . . . . ?
C3 C2 C4 C3 0.6(4) . . . 3_667 ?
C3 C2 C4 C5 -178.4(2) . . . . ?
C3 C4 C5 O2 1.7(5) 3_667 . . . ?
C3 C4 C5 N1 -178.4(3) 3_667 . . . ?
C4 C2 C3 C4 -0.5(4) . . . 3_667 ?
C5 N1 C1 O1 -175.3(3) . . . . ?
C5 N1 C1 C2 2.9(3) . . . . ?
C5 N1 C61 C71 -104.1(9) . . . . ?
C5 N1 C62 C72 -48(5) . . . . ?
C61 N1 C1 O1 -1.5(9) . . . . ?
C61 N1 C1 C2 176.7(8) . . . . ?
C61 N1 C5 O2 3.7(8) . . . . ?
C61 N1 C5 C4 -176.1(8) . . . . ?
C61 C71 C9 O3 -20.5(9) . . . . ?
C61 C71 C9 O4 156.4(7) . . . . ?
C81 C71 C9 O3 101.6(6) . . . . ?
C81 C71 C9 O4 -81.5(7) . . . . ?
C62 N1 C1 O1 7(3) . . . . ?
C62 N1 C1 C2 -175(3) . . . . ?
C62 N1 C5 O2 -5(3) . . . . ?
C62 N1 C5 C4 176(3) . . . . ?
C62 C72 C9 O3 -80(2) . . . . ?
C62 C72 C9 O4 122(2) . . . . ?
C82 C72 C9 O3 164.4(18) . . . . ?
C82 C72 C9 O4 6(3) . . . . ?
N1P C1P C2P C3P -0.6(6) . . . . ?
C1P N1P C5P C4P -1.1(7) . . . . ?
C1P C2P C3P C4P 0.3(6) . . . . ?
C2P C3P C4P C5P -0.4(7) . . . . ?
C3P C4P C5P N1P 0.8(7) . . . . ?
C5P N1P C1P C2P 1.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_l13_025
_database_code_depnum_ccdc_archive 'CCDC 2324810'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, C9 H7 N, 2(C5 H11 N)'
_chemical_formula_sum            'C37 H45 N5 O8'
_chemical_formula_weight         687.78
_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                   6.8672(14)
_cell_length_b                   7.5914(15)
_cell_length_c                   16.850(3)
_cell_angle_alpha                98.98(3)
_cell_angle_beta                 97.71(3)
_cell_angle_gamma                93.21(3)
_cell_volume                     857.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3797
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             366
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6653
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.003
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1508
_reflns_number_total             3001
_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       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.09(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3001
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1748
_refine_ls_R_factor_gt           0.1057
_refine_ls_restrained_S_all      1.062
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2896
_refine_ls_wR_factor_ref         0.3475
_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, All O(H) groups
2. Shared sites
{C61, C62}
{N1Q, C2Q}
3. Restrained distances
 O32-C9
 1.28 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C82) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C61) = Uanis(C62)
Uanis(N1Q) = Uanis(C2Q)
5. Others
 Fixed Sof: O31(0.5) H31(0.5) O41(0.5) O32(0.5) H32(0.5) O42(0.5) C61(0.5)
 H61A(0.5) H61B(0.5) C71(0.5) H71(0.5) C81(0.5) H81A(0.5) H81B(0.5) H81C(0.5)
 C62(0.5) H62A(0.5) H62B(0.5) C72(0.5) H72(0.5) C82(0.5) H82A(0.5) H82B(0.5)
 H82C(0.5) N1Q(0.5) C2Q(0.5) H2Q(0.5)
6.a Ternary CH refined with riding coordinates:
 C71(H71), C72(H72)
6.b Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C62(H62A,H62B), C1P(H1PA,H1PB), C2P(H2PA,H2PB), C3P(H3PA,
 H3PB), C4P(H4PA,H4PB), C5P(H5PA,H5PB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), N1P(H1P), C1Q(H1Q), C2Q(H2Q), C4Q(H4Q), C5Q(H5Q)
6.d Idealised Me refined as rotating group:
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C)
6.e Idealised tetrahedral OH refined as rotating group:
 O31(H31), O32(H32)
;
_atom_sites_solution_hydrogens   geom
_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 0.9345(6) 0.3787(5) 0.2713(2) 0.0737(11) Uani 1 1 d . . . . .
O2 O 1.1170(6) 0.9285(5) 0.4224(2) 0.0778(12) Uani 1 1 d . . . . .
O31 O 0.7087(18) 0.8764(13) 0.0895(6) 0.072(3) Uani 0.5 1 d . . P A 1
H31 H 0.644108 0.776230 0.077985 0.108 Uiso 0.5 1 calc R U P A 1
O41 O 1.032(3) 0.8726(18) 0.1156(11) 0.083(4) Uani 0.5 1 d . . P A 1
O32 O 1.023(4) 0.807(3) 0.1005(13) 0.166(12) Uani 0.5 1 d D . P A 2
H32 H 1.061614 0.715991 0.118281 0.249 Uiso 0.5 1 calc R U P A 2
O42 O 0.805(3) 0.978(2) 0.1070(11) 0.181(9) Uani 0.5 1 d . . P A 2
N1 N 1.0165(7) 0.6746(5) 0.3294(2) 0.0654(12) Uani 1 1 d . . . . .
C1 C 0.9715(8) 0.4947(7) 0.3313(3) 0.0620(13) Uani 1 1 d . . . . .
C2 C 0.9783(7) 0.4760(6) 0.4172(3) 0.0538(12) Uani 1 1 d . . . . .
C3 C 0.9456(7) 0.3241(6) 0.4519(3) 0.0535(12) Uani 1 1 d . . . . .
H3 H 0.912214 0.208559 0.420448 0.064 Uiso 1 1 calc R U . . .
C4 C 1.0343(7) 0.6450(6) 0.4643(3) 0.0543(12) Uani 1 1 d . . . . .
C5 C 1.0603(8) 0.7716(7) 0.4071(3) 0.0600(13) Uani 1 1 d . . . . .
C61 C 1.0365(9) 0.7469(8) 0.2550(3) 0.0745(16) Uani 0.5 1 d . . P A 1
H61A H 1.101452 0.662305 0.218065 0.089 Uiso 0.5 1 calc R U P A 1
H61B H 1.118617 0.861878 0.268250 0.089 Uiso 0.5 1 calc R U P A 1
C71 C 0.832(2) 0.7752(19) 0.2141(8) 0.055(4) Uani 0.5 1 d . . P A 1
H71 H 0.756652 0.656326 0.194904 0.066 Uiso 0.5 1 calc R U P A 1
C81 C 0.714(3) 0.893(2) 0.2618(13) 0.068(6) Uani 0.5 1 d . . P A 1
H81A H 0.686689 0.840569 0.309237 0.102 Uiso 0.5 1 calc R U P A 1
H81B H 0.588874 0.905850 0.228264 0.102 Uiso 0.5 1 calc R U P A 1
H81C H 0.785809 1.010259 0.279786 0.102 Uiso 0.5 1 calc R U P A 1
C62 C 1.0365(9) 0.7469(8) 0.2550(3) 0.0745(16) Uani 0.5 1 d . . P A 2
H62A H 1.163874 0.820287 0.265138 0.089 Uiso 0.5 1 calc R U P A 2
H62B H 1.049231 0.643892 0.212562 0.089 Uiso 0.5 1 calc R U P A 2
C72 C 0.896(3) 0.849(3) 0.2211(15) 0.119(9) Uani 0.5 1 d . . P A 2
H72 H 0.960793 0.971117 0.244248 0.143 Uiso 0.5 1 calc R U P A 2
C82 C 0.695(5) 0.873(5) 0.2499(16) 0.172(17) Uani 0.5 1 d . U P A 2
H82A H 0.622973 0.755385 0.244574 0.258 Uiso 0.5 1 calc R U P A 2
H82B H 0.618859 0.947407 0.216705 0.258 Uiso 0.5 1 calc R U P A 2
H82C H 0.714462 0.930604 0.306934 0.258 Uiso 0.5 1 calc R U P A 2
C9 C 0.8828(14) 0.8613(9) 0.1353(4) 0.094(2) Uani 1 1 d D . . . .
N1P N 0.2889(14) 0.4751(8) 0.0766(5) 0.137(3) Uani 1 1 d . . . . .
H1P H 0.271157 0.558757 0.046169 0.165 Uiso 1 1 calc R U . . .
C1P C 0.1296(10) 0.3191(12) 0.0828(4) 0.106(2) Uani 1 1 d . . . . .
H1PA H 0.091730 0.335548 0.137970 0.127 Uiso 1 1 calc R U . . .
H1PB H 0.009904 0.322897 0.043335 0.127 Uiso 1 1 calc R U . . .
C2P C 0.2121(10) 0.1469(7) 0.0656(3) 0.0738(17) Uani 1 1 d . . . . .
H2PA H 0.117287 0.050963 0.074152 0.089 Uiso 1 1 calc R U . . .
H2PB H 0.233069 0.124228 0.008022 0.089 Uiso 1 1 calc R U . . .
C3P C 0.3902(15) 0.1420(11) 0.1152(5) 0.118(3) Uani 1 1 d . . . . .
H3PA H 0.448413 0.027686 0.099274 0.142 Uiso 1 1 calc R U . . .
H3PB H 0.368082 0.150600 0.172444 0.142 Uiso 1 1 calc R U . . .
C4P C 0.5314(13) 0.2997(15) 0.1061(6) 0.141(3) Uani 1 1 d . . . . .
H4PA H 0.658041 0.297724 0.141639 0.169 Uiso 1 1 calc R U . . .
H4PB H 0.558302 0.286557 0.049272 0.169 Uiso 1 1 calc R U . . .
C5P C 0.4552(10) 0.4574(7) 0.1258(4) 0.0776(17) Uani 1 1 d . . . . .
H5PA H 0.426830 0.469159 0.182386 0.093 Uiso 1 1 calc R U . . .
H5PB H 0.554261 0.555534 0.123332 0.093 Uiso 1 1 calc R U . . .
C1Q C 0.4320(10) 0.2903(12) 0.3697(5) 0.100(2) Uani 1 1 d . . . . .
H1Q H 0.404783 0.190584 0.327084 0.120 Uiso 1 1 calc R U . B 1
N1Q N 0.4390(9) 0.2667(9) 0.4478(5) 0.1002(19) Uani 0.5 1 d . . P C 1
C2Q C 0.4390(9) 0.2667(9) 0.4478(5) 0.1002(19) Uani 0.5 1 d . . P C 2
H2Q H 0.414503 0.150656 0.460599 0.120 Uiso 0.5 1 calc R U P C 2
C3Q C 0.4830(7) 0.4159(7) 0.5101(3) 0.0668(14) Uani 1 1 d . . . . .
C4Q C 0.4924(8) 0.3953(8) 0.5920(4) 0.0705(15) Uani 1 1 d . . . . .
H4Q H 0.468308 0.280587 0.606159 0.085 Uiso 1 1 calc R U . . .
C5Q C 0.5346(9) 0.5360(13) 0.6481(4) 0.097(2) Uani 1 1 d . . . . .
H5Q H 0.543281 0.521106 0.703347 0.116 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
O1 C1 1.222(6) . ?
O2 C5 1.210(6) . ?
O31 H31 0.8400 . ?
O31 C9 1.354(15) . ?
O41 C9 1.119(17) . ?
O32 H32 0.8400 . ?
O32 C9 1.246(16) . ?
O42 C9 1.192(15) . ?
N1 C1 1.390(7) . ?
N1 C5 1.384(6) . ?
N1 C61 1.464(6) . ?
N1 C62 1.464(6) . ?
C1 C2 1.471(6) . ?
C2 C3 1.392(6) . ?
C2 C4 1.403(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(6) 2_766 ?
C4 C5 1.483(6) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C71 1.520(18) . ?
C71 H71 1.0000 . ?
C71 C81 1.46(2) . ?
C71 C9 1.637(13) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 C72 1.39(2) . ?
C72 H72 1.0000 . ?
C72 C82 1.53(3) . ?
C72 C9 1.45(2) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
N1P H1P 0.8800 . ?
N1P C1P 1.592(10) . ?
N1P C5P 1.344(9) . ?
C1P H1PA 0.9900 . ?
C1P H1PB 0.9900 . ?
C1P C2P 1.457(9) . ?
C2P H2PA 0.9900 . ?
C2P H2PB 0.9900 . ?
C2P C3P 1.391(10) . ?
C3P H3PA 0.9900 . ?
C3P H3PB 0.9900 . ?
C3P C4P 1.537(12) . ?
C4P H4PA 0.9900 . ?
C4P H4PB 0.9900 . ?
C4P C5P 1.346(11) . ?
C5P H5PA 0.9900 . ?
C5P H5PB 0.9900 . ?
C1Q H1Q 0.9500 . ?
C1Q N1Q 1.351(10) . ?
C1Q C2Q 1.351(10) . ?
C1Q C5Q 1.410(11) 2_666 ?
N1Q C3Q 1.408(8) . ?
C2Q H2Q 0.9500 . ?
C2Q C3Q 1.408(8) . ?
C3Q C3Q 1.388(10) 2_666 ?
C3Q C4Q 1.406(8) . ?
C4Q H4Q 0.9500 . ?
C4Q C5Q 1.302(9) . ?
C5Q H5Q 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
C9 O31 H31 109.5 . . ?
C9 O32 H32 109.5 . . ?
C1 N1 C61 123.9(4) . . ?
C1 N1 C62 123.9(4) . . ?
C5 N1 C1 111.1(4) . . ?
C5 N1 C61 124.7(4) . . ?
C5 N1 C62 124.7(4) . . ?
O1 C1 N1 124.5(4) . . ?
O1 C1 C2 128.5(5) . . ?
N1 C1 C2 107.0(4) . . ?
C3 C2 C1 129.9(4) . . ?
C3 C2 C4 122.3(4) . . ?
C4 C2 C1 107.8(4) . . ?
C2 C3 H3 122.7 . . ?
C4 C3 C2 114.6(4) 2_766 . ?
C4 C3 H3 122.7 2_766 . ?
C2 C4 C5 107.0(4) . . ?
C3 C4 C2 123.1(4) 2_766 . ?
C3 C4 C5 129.9(5) 2_766 . ?
O2 C5 N1 124.3(4) . . ?
O2 C5 C4 128.5(5) . . ?
N1 C5 C4 107.1(4) . . ?
N1 C61 H61A 110.0 . . ?
N1 C61 H61B 110.0 . . ?
N1 C61 C71 108.6(6) . . ?
H61A C61 H61B 108.4 . . ?
C71 C61 H61A 110.0 . . ?
C71 C61 H61B 110.0 . . ?
C61 C71 H71 109.1 . . ?
C61 C71 C9 101.9(9) . . ?
C81 C71 C61 116.9(12) . . ?
C81 C71 H71 109.1 . . ?
C81 C71 C9 110.4(13) . . ?
C9 C71 H71 109.1 . . ?
C71 C81 H81A 109.5 . . ?
C71 C81 H81B 109.5 . . ?
C71 C81 H81C 109.5 . . ?
H81A C81 H81B 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
N1 C62 H62A 106.8 . . ?
N1 C62 H62B 106.8 . . ?
H62A C62 H62B 106.7 . . ?
C72 C62 N1 122.0(9) . . ?
C72 C62 H62A 106.8 . . ?
C72 C62 H62B 106.8 . . ?
C62 C72 H72 98.8 . . ?
C62 C72 C82 123.5(16) . . ?
C62 C72 C9 118.9(16) . . ?
C82 C72 H72 98.8 . . ?
C9 C72 H72 98.8 . . ?
C9 C72 C82 110.6(19) . . ?
C72 C82 H82A 109.5 . . ?
C72 C82 H82B 109.5 . . ?
C72 C82 H82C 109.5 . . ?
H82A C82 H82B 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
O31 C9 C71 107.1(9) . . ?
O41 C9 O31 125.9(12) . . ?
O41 C9 C71 125.4(13) . . ?
O32 C9 C72 116.7(15) . . ?
O42 C9 O32 113.5(14) . . ?
O42 C9 C72 122.1(13) . . ?
C1P N1P H1P 125.8 . . ?
C5P N1P H1P 125.8 . . ?
C5P N1P C1P 108.4(5) . . ?
N1P C1P H1PA 109.8 . . ?
N1P C1P H1PB 109.8 . . ?
H1PA C1P H1PB 108.2 . . ?
C2P C1P N1P 109.5(6) . . ?
C2P C1P H1PA 109.8 . . ?
C2P C1P H1PB 109.8 . . ?
C1P C2P H2PA 109.3 . . ?
C1P C2P H2PB 109.3 . . ?
H2PA C2P H2PB 108.0 . . ?
C3P C2P C1P 111.5(6) . . ?
C3P C2P H2PA 109.3 . . ?
C3P C2P H2PB 109.3 . . ?
C2P C3P H3PA 109.9 . . ?
C2P C3P H3PB 109.9 . . ?
C2P C3P C4P 108.9(6) . . ?
H3PA C3P H3PB 108.3 . . ?
C4P C3P H3PA 109.9 . . ?
C4P C3P H3PB 109.9 . . ?
C3P C4P H4PA 109.3 . . ?
C3P C4P H4PB 109.3 . . ?
H4PA C4P H4PB 108.0 . . ?
C5P C4P C3P 111.5(7) . . ?
C5P C4P H4PA 109.3 . . ?
C5P C4P H4PB 109.3 . . ?
N1P C5P C4P 112.9(6) . . ?
N1P C5P H5PA 109.0 . . ?
N1P C5P H5PB 109.0 . . ?
C4P C5P H5PA 109.0 . . ?
C4P C5P H5PB 109.0 . . ?
H5PA C5P H5PB 107.8 . . ?
N1Q C1Q H1Q 120.2 . . ?
N1Q C1Q C5Q 119.5(6) . 2_666 ?
C2Q C1Q C5Q 119.5(6) . 2_666 ?
C5Q C1Q H1Q 120.2 2_666 . ?
C1Q N1Q C3Q 119.3(7) . . ?
C1Q C2Q H2Q 120.4 . . ?
C1Q C2Q C3Q 119.3(7) . . ?
C3Q C2Q H2Q 120.4 . . ?
C3Q C3Q N1Q 119.3(7) 2_666 . ?
C3Q C3Q C2Q 119.3(7) 2_666 . ?
C3Q C3Q C4Q 120.2(6) 2_666 . ?
C4Q C3Q N1Q 120.6(5) . . ?
C4Q C3Q C2Q 120.6(5) . . ?
C3Q C4Q H4Q 120.5 . . ?
C5Q C4Q C3Q 118.9(6) . . ?
C5Q C4Q H4Q 120.5 . . ?
C1Q C5Q H5Q 118.6 2_666 . ?
C4Q C5Q C1Q 122.8(6) . 2_666 ?
C4Q C5Q H5Q 118.6 . . ?

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
O1 C1 C2 C3 0.2(9) . . . . ?
O1 C1 C2 C4 177.8(5) . . . . ?
N1 C1 C2 C3 -179.7(5) . . . . ?
N1 C1 C2 C4 -2.1(5) . . . . ?
N1 C61 C71 C81 57.7(14) . . . . ?
N1 C61 C71 C9 178.1(6) . . . . ?
N1 C62 C72 C82 -10(3) . . . . ?
N1 C62 C72 C9 -157.5(12) . . . . ?
C1 N1 C5 O2 174.9(5) . . . . ?
C1 N1 C5 C4 -2.3(5) . . . . ?
C1 N1 C61 C71 82.5(8) . . . . ?
C1 N1 C62 C72 107.8(15) . . . . ?
C1 C2 C3 C4 179.6(5) . . . 2_766 ?
C1 C2 C4 C3 179.7(4) . . . 2_766 ?
C1 C2 C4 C5 0.7(5) . . . . ?
C2 C4 C5 O2 -176.1(5) . . . . ?
C2 C4 C5 N1 0.9(5) . . . . ?
C3 C2 C4 C3 -2.5(8) . . . 2_766 ?
C3 C2 C4 C5 178.6(4) . . . . ?
C3 C4 C5 O2 5.0(9) 2_766 . . . ?
C3 C4 C5 N1 -178.0(5) 2_766 . . . ?
C4 C2 C3 C4 2.3(7) . . . 2_766 ?
C5 N1 C1 O1 -177.2(5) . . . . ?
C5 N1 C1 C2 2.7(5) . . . . ?
C5 N1 C61 C71 -104.9(8) . . . . ?
C5 N1 C62 C72 -79.6(15) . . . . ?
C61 N1 C1 O1 -3.7(8) . . . . ?
C61 N1 C1 C2 176.2(4) . . . . ?
C61 N1 C5 O2 1.4(8) . . . . ?
C61 N1 C5 C4 -175.7(4) . . . . ?
C61 C71 C9 O31 174.2(8) . . . . ?
C61 C71 C9 O41 8.0(16) . . . . ?
C81 C71 C9 O31 -60.9(14) . . . . ?
C81 C71 C9 O41 132.9(16) . . . . ?
C62 N1 C1 O1 -3.7(8) . . . . ?
C62 N1 C1 C2 176.2(4) . . . . ?
C62 N1 C5 O2 1.4(8) . . . . ?
C62 N1 C5 C4 -175.7(4) . . . . ?
C62 C72 C9 O32 -13(3) . . . . ?
C62 C72 C9 O42 -160.5(19) . . . . ?
C82 C72 C9 O32 -165(2) . . . . ?
C82 C72 C9 O42 48(3) . . . . ?
N1P C1P C2P C3P 54.1(7) . . . . ?
C1P N1P C5P C4P 60.0(9) . . . . ?
C1P C2P C3P C4P -54.9(8) . . . . ?
C2P C3P C4P C5P 58.4(10) . . . . ?
C3P C4P C5P N1P -63.1(10) . . . . ?
C5P N1P C1P C2P -54.4(7) . . . . ?
C1Q N1Q C3Q C3Q 0.4(9) . . . 2_666 ?
C1Q N1Q C3Q C4Q -179.6(5) . . . . ?
C1Q C2Q C3Q C3Q 0.4(9) . . . 2_666 ?
C1Q C2Q C3Q C4Q -179.6(5) . . . . ?
N1Q C3Q C4Q C5Q 179.6(5) . . . . ?
C2Q C3Q C4Q C5Q 179.6(5) . . . . ?
C3Q C3Q C4Q C5Q -0.4(9) 2_666 . . . ?
C3Q C4Q C5Q C1Q 1.2(9) . . . 2_666 ?
C5Q C1Q N1Q C3Q -1.1(9) 2_666 . . . ?
C5Q C1Q C2Q C3Q -1.1(9) 2_666 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L13_032
_database_code_depnum_ccdc_archive 'CCDC 2324805'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C5 H5 N)'
_chemical_formula_sum            'C28 H26 N4 O8'
_chemical_formula_weight         546.541
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.6234(13)
_cell_length_b                   7.8504(16)
_cell_length_c                   12.820(3)
_cell_angle_alpha                77.85(3)
_cell_angle_beta                 85.83(3)
_cell_angle_gamma                83.68(3)
_cell_volume                     646.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4423
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.10
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9342
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             286.215
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9906
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6383
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9906
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9906
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1837
_reflns_number_total             2938
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.4725
_refine_diff_density_min         -0.3819
_refine_diff_density_rms         0.0852
_refine_ls_d_res_high            0.7706
_refine_ls_d_res_low             6.5746
_refine_ls_goodness_of_fit_ref   0.9930
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      0.9930
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.5375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1245
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3a), C1P(H1P), C2P(H2P), C3P(H3P), C4P(H4P), C5P(H5P)
2.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
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_refinement_flags_posn
O1 O 0.9886(2) 0.9744(2) 0.13991(13) 0.0418(4) Uani 1.000000 .
O2 O 0.6283(2) 0.51926(19) 0.11605(13) 0.0416(4) Uani 1.000000 .
O3 O 1.0407(3) 0.2714(2) 0.44428(14) 0.0539(5) Uani 1.000000 .
H3 H 1.1389(17) 0.224(2) 0.4813(18) 0.0808(7) Uiso 1.000000 GR
O4 O 1.2556(3) 0.4695(2) 0.38138(18) 0.0701(6) Uani 1.000000 .
N1 N 0.8465(3) 0.7160(2) 0.14327(14) 0.0343(4) Uani 1.000000 .
C1 C 0.8565(3) 0.8970(3) 0.11707(16) 0.0318(5) Uani 1.000000 .
C2 C 0.6728(3) 0.9702(3) 0.05448(15) 0.0288(4) Uani 1.000000 .
C3 C 0.6109(3) 1.1434(3) 0.01014(16) 0.0317(5) Uani 1.000000 .
H3a H 0.6835(3) 1.2379(3) 0.01711(16) 0.0381(6) Uiso 1.000000 R
C4 C 0.5658(3) 0.8327(3) 0.04522(15) 0.0295(4) Uani 1.000000 .
C5 C 0.6752(3) 0.6669(3) 0.10404(16) 0.0318(5) Uani 1.000000 .
C6 C 1.0055(3) 0.5946(3) 0.20291(18) 0.0389(5) Uani 1.000000 .
H6 H 1.1147(3) 0.6670(3) 0.21337(18) 0.0467(6) Uiso 1.000000 R
C7 C 1.1028(4) 0.4629(3) 0.13921(19) 0.0455(6) Uani 1.000000 .
H7a H 1.0082(10) 0.3757(13) 0.1382(11) 0.0683(9) Uiso 1.000000 GR
H7b H 1.136(2) 0.5232(4) 0.0659(4) 0.0683(9) Uiso 1.000000 GR
H7c H 1.2278(14) 0.4044(16) 0.1722(8) 0.0683(9) Uiso 1.000000 GR
C8 C 0.9225(4) 0.5131(3) 0.31311(18) 0.0443(6) Uani 1.000000 .
H8a H 0.8496(4) 0.6059(3) 0.34709(18) 0.0531(7) Uiso 1.000000 R
H8b H 0.8237(4) 0.4305(3) 0.30649(18) 0.0531(7) Uiso 1.000000 R
C9 C 1.0907(4) 0.4161(3) 0.38361(18) 0.0410(5) Uani 1.000000 .
N1P N 0.3305(3) 0.1216(2) 0.57188(15) 0.0398(5) Uani 1.000000 .
C1P C 0.3109(3) -0.0343(3) 0.63620(18) 0.0405(5) Uani 1.000000 .
H1P H 0.1928(3) -0.0912(3) 0.63290(18) 0.0486(6) Uiso 1.000000 R
C2P C 0.4561(4) -0.1156(3) 0.70730(18) 0.0413(5) Uani 1.000000 .
H2P H 0.4389(4) -0.2268(3) 0.75173(18) 0.0496(7) Uiso 1.000000 R
C3P C 0.6262(4) -0.0322(3) 0.71237(19) 0.0420(6) Uani 1.000000 .
H3P H 0.7273(4) -0.0844(3) 0.76131(19) 0.0504(7) Uiso 1.000000 R
C4P C 0.6482(4) 0.1269(3) 0.64611(19) 0.0438(6) Uani 1.000000 .
H4P H 0.7652(4) 0.1860(3) 0.64785(19) 0.0526(7) Uiso 1.000000 R
C5P C 0.4971(4) 0.1995(3) 0.57677(19) 0.0424(6) Uani 1.000000 .
H5P H 0.5128(4) 0.3096(3) 0.53069(19) 0.0509(7) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.204(3) . ?
O2 C5 1.208(2) . ?
O3 H3 0.8400 . ?
O3 C9 1.296(3) . ?
O4 C9 1.209(3) . ?
N1 C1 1.397(3) . ?
N1 C5 1.396(3) . ?
N1 C6 1.481(2) . ?
C1 C2 1.499(3) . ?
C2 C3 1.388(3) . ?
C2 C4 1.384(3) . ?
C3 H3a 0.9500 . ?
C3 C4 1.387(3) 2_675 ?
C4 C5 1.499(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.511(3) . ?
C6 C8 1.514(3) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.519(3) . ?
N1P C1P 1.338(3) . ?
N1P C5P 1.331(3) . ?
C1P H1P 0.9500 . ?
C1P C2P 1.383(3) . ?
C2P H2P 0.9500 . ?
C2P C3P 1.376(3) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.371(3) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.381(3) . ?
C5P H5P 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
C9 O3 H3 109.5 . . ?
C5 N1 C1 112.07(15) . . ?
C6 N1 C1 122.42(17) . . ?
C6 N1 C5 125.49(17) . . ?
N1 C1 O1 125.99(18) . . ?
C2 C1 O1 128.36(19) . . ?
C2 C1 N1 105.64(17) . . ?
C3 C2 C1 128.84(19) . . ?
C4 C2 C1 108.43(17) . . ?
C4 C2 C3 122.74(18) . . ?
H3a C3 C2 122.75(12) . . ?
C4 C3 C2 114.51(19) 2_675 . ?
C4 C3 H3a 122.75(12) 2_675 . ?
C3 C4 C2 122.75(17) 2_675 . ?
C5 C4 C2 107.80(17) . . ?
C5 C4 C3 129.44(19) . 2_675 ?
N1 C5 O2 125.89(18) . . ?
C4 C5 O2 128.06(19) . . ?
C4 C5 N1 106.05(17) . . ?
H6 C6 N1 106.79(12) . . ?
C7 C6 N1 111.58(17) . . ?
C7 C6 H6 106.79(13) . . ?
C8 C6 N1 110.52(18) . . ?
C8 C6 H6 106.79(13) . . ?
C8 C6 C7 113.92(19) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C6 109.29(12) . . ?
H8b C8 C6 109.29(13) . . ?
H8b C8 H8a 107.9 . . ?
C9 C8 C6 111.68(19) . . ?
C9 C8 H8a 109.29(13) . . ?
C9 C8 H8b 109.29(14) . . ?
O4 C9 O3 123.9(2) . . ?
C8 C9 O3 113.6(2) . . ?
C8 C9 O4 122.5(2) . . ?
C5P N1P C1P 118.25(19) . . ?
H1P C1P N1P 118.81(13) . . ?
C2P C1P N1P 122.4(2) . . ?
C2P C1P H1P 118.81(14) . . ?
H2P C2P C1P 120.69(14) . . ?
C3P C2P C1P 118.6(2) . . ?
C3P C2P H2P 120.69(13) . . ?
H3P C3P C2P 120.34(13) . . ?
C4P C3P C2P 119.3(2) . . ?
C4P C3P H3P 120.34(14) . . ?
H4P C4P C3P 120.63(14) . . ?
C5P C4P C3P 118.7(2) . . ?
C5P C4P H4P 120.63(14) . . ?
C4P C5P N1P 122.7(2) . . ?
H5P C5P N1P 118.67(12) . . ?
H5P C5P C4P 118.67(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 N1P 0.8400 1.789(4) 2.626(2) 174(3) 1_655

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
O1 C1 N1 C5 -179.3(2) . . . . ?
O1 C1 N1 C6 -1.1(3) . . . . ?
O1 C1 C2 C3 -1.2(3) . . . . ?
O1 C1 C2 C4 178.3(2) . . . . ?
O2 C5 N1 C1 -179.2(2) . . . . ?
O2 C5 N1 C6 2.7(3) . . . . ?
O2 C5 C4 C2 178.7(2) . . . . ?
O2 C5 C4 C3 -1.1(3) . . . 2_675 ?
O3 C9 C8 C6 -141.3(2) . . . . ?
O4 C9 C8 C6 37.8(3) . . . . ?
N1 C1 C2 C3 179.69(16) . . . . ?
N1 C1 C2 C4 -0.79(18) . . . . ?
N1 C5 C4 C2 -1.43(19) . . . . ?
N1 C5 C4 C3 178.77(16) . . . 2_675 ?
N1 C6 C8 C9 -168.95(19) . . . . ?
C1 C2 C3 C4 178.8(2) . . . 2_675 ?
C1 C2 C4 C3 -178.83(16) . . . 2_675 ?
C1 C2 C4 C5 1.35(18) . . . . ?
C2 C3 C4 C2 0.67(19) . . 2_675 2_675 ?
C2 C3 C4 C5 -179.11(17) . . 2_675 2_675 ?
C2 C4 C3 C2 -0.67(19) . . 2_675 2_675 ?
N1P C1P C2P C3P 0.5(3) . . . . ?
N1P C5P C4P C3P 0.2(3) . . . . ?
C1P C2P C3P C4P -1.0(3) . . . . ?
C2P C3P C4P C5P 0.7(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L13_037
_database_code_depnum_ccdc_archive 'CCDC 2324809'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C9 H7 N)'
_chemical_formula_sum            'C36 H30 N4 O8'
_chemical_formula_weight         646.662
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.8709(14)
_cell_length_b                   10.625(2)
_cell_length_c                   11.972(2)
_cell_angle_alpha                64.27(3)
_cell_angle_beta                 80.50(3)
_cell_angle_gamma                81.26(3)
_cell_volume                     773.4(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3114
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.02
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9852
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             338.243
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_unetI/netI     0.1731
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7623
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9982
_diffrn_reflns_theta_full        24.9979
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1089
_reflns_number_total             2716
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.6115
_refine_diff_density_min         -0.5971
_refine_diff_density_rms         0.1498
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.7489
_refine_ls_goodness_of_fit_ref   1.0385
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2190
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.0385
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1032P)²+0.2610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2614
_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.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3a), C1Q(H1Q), C2Q(H2Q), C3Q(H3Q), C5Q(H5Q), C6Q(H6Q), C7Q(H7Q), C8Q(H8Q)
2.d Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
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_refinement_flags_posn
O1 O 0.9731(6) 0.9220(5) 0.1490(4) 0.0728(14) Uani 1.000000 .
O2 O 0.6499(7) 0.6194(5) 0.0823(4) 0.0788(14) Uani 1.000000 .
O3 O 1.0897(7) 0.3204(5) 0.4418(4) 0.0767(15) Uani 1.000000 .
O4 O 1.2614(8) 0.5027(5) 0.3853(5) 0.0944(17) Uani 1.000000 .
N1 N 0.8525(7) 0.7445(6) 0.1252(4) 0.0649(16) Uani 1.000000 .
C1 C 0.8527(10) 0.8795(6) 0.1155(5) 0.0562(16) Uani 1.000000 .
C2 C 0.6689(8) 0.9573(7) 0.0542(5) 0.0555(16) Uani 1.000000 .
C3 C 0.6042(9) 1.0950(6) 0.0198(5) 0.0571(17) Uani 1.000000 .
H3a H 0.6729(9) 1.1583(6) 0.0320(5) 0.069(2) Uiso 1.000000 R
C4 C 0.5718(10) 0.8652(7) 0.0350(5) 0.0612(17) Uani 1.000000 .
C5 C 0.6893(11) 0.7261(7) 0.0827(6) 0.070(2) Uani 1.000000 .
C6 C 1.0156(11) 0.6351(7) 0.1795(6) 0.086(2) Uani 1.000000 .
H6 H 1.1157(11) 0.6877(7) 0.1893(6) 0.103(3) Uiso 1.000000 R
C7 C 1.1196(11) 0.5775(7) 0.0944(7) 0.094(3) Uani 1.000000 .
H7a H 1.039(3) 0.512(4) 0.090(4) 0.142(4) Uiso 1.000000 GR
H7b H 1.144(6) 0.6537(9) 0.0113(13) 0.142(4) Uiso 1.000000 GR
H7c H 1.246(4) 0.528(5) 0.124(3) 0.142(4) Uiso 1.000000 GR
C8 C 0.9456(9) 0.5401(6) 0.3098(6) 0.072(2) Uani 1.000000 .
H8a H 0.8707(9) 0.5969(6) 0.3526(6) 0.086(2) Uiso 1.000000 R
H8b H 0.8543(9) 0.4775(6) 0.3079(6) 0.086(2) Uiso 1.000000 R
C9 C 1.1154(10) 0.4516(7) 0.3830(6) 0.0634(18) Uani 1.000000 .
N1Q N 0.3824(7) 1.1771(5) 0.5784(4) 0.0559(13) Uani 1.000000 .
C1Q C 0.5256(9) 1.2366(7) 0.5921(5) 0.0609(17) Uani 1.000000 .
H1Q H 0.5163(9) 1.3362(7) 0.5570(5) 0.073(2) Uiso 1.000000 R
C2Q C 0.6922(9) 1.1633(7) 0.6550(6) 0.0623(17) Uani 1.000000 .
H2Q H 0.7925(9) 1.2117(7) 0.6612(6) 0.075(2) Uiso 1.000000 R
C3Q C 0.7040(9) 1.0217(7) 0.7061(5) 0.0599(17) Uani 1.000000 .
H3Q H 0.8130(9) 0.9694(7) 0.7506(5) 0.072(2) Uiso 1.000000 R
C4Q C 0.5568(9) 0.9507(6) 0.6942(5) 0.0528(16) Uani 1.000000 .
C5Q C 0.5578(10) 0.8049(6) 0.7435(5) 0.0636(18) Uani 1.000000 .
H5Q H 0.6654(10) 0.7473(6) 0.7867(5) 0.076(2) Uiso 1.000000 R
C6Q C 0.4091(11) 0.7450(7) 0.7309(6) 0.0730(19) Uani 1.000000 .
H6Q H 0.4122(11) 0.6457(7) 0.7661(6) 0.088(2) Uiso 1.000000 R
C7Q C 0.2490(10) 0.8276(7) 0.6663(6) 0.0667(18) Uani 1.000000 .
H7Q H 0.1447(10) 0.7839(7) 0.6581(6) 0.080(2) Uiso 1.000000 R
C8Q C 0.2433(9) 0.9715(6) 0.6150(5) 0.0599(17) Uani 1.000000 .
H8Q H 0.1369(9) 1.0276(6) 0.5696(5) 0.072(2) Uiso 1.000000 R
C9Q C 0.3968(8) 1.0353(6) 0.6302(5) 0.0470(14) Uani 1.000000 .
H3 H 1.214(12) 0.278(8) 0.493(7) 0.14(3) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.195(7) . ?
O2 C5 1.207(7) . ?
O3 C9 1.286(7) . ?
O3 H3 1.06(8) . ?
O4 C9 1.221(7) . ?
N1 C1 1.388(8) . ?
N1 C5 1.378(8) . ?
N1 C6 1.489(7) . ?
C1 C2 1.509(8) . ?
C2 C3 1.359(8) . ?
C2 C4 1.378(8) . ?
C3 H3a 0.9500 . ?
C3 C4 1.392(8) 2_675 ?
C4 C5 1.489(8) . ?
C6 H6 1.0000 . ?
C6 C7 1.446(9) . ?
C6 C8 1.488(9) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.517(8) . ?
N1Q C1Q 1.314(7) . ?
N1Q C9Q 1.352(7) . ?
C1Q H1Q 0.9500 . ?
C1Q C2Q 1.410(8) . ?
C2Q H2Q 0.9500 . ?
C2Q C3Q 1.350(8) . ?
C3Q H3Q 0.9500 . ?
C3Q C4Q 1.410(8) . ?
C4Q C5Q 1.397(8) . ?
C4Q C9Q 1.408(7) . ?
C5Q H5Q 0.9500 . ?
C5Q C6Q 1.343(8) . ?
C6Q H6Q 0.9500 . ?
C6Q C7Q 1.406(8) . ?
C7Q H7Q 0.9500 . ?
C7Q C8Q 1.376(8) . ?
C8Q H8Q 0.9500 . ?
C8Q C9Q 1.411(8) . ?

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
H3 O3 C9 103(4) . . ?
C5 N1 C1 113.2(5) . . ?
C6 N1 C1 120.8(5) . . ?
C6 N1 C5 126.1(6) . . ?
N1 C1 O1 126.7(6) . . ?
C2 C1 O1 128.9(6) . . ?
C2 C1 N1 104.4(5) . . ?
C3 C2 C1 128.0(6) . . ?
C4 C2 C1 108.6(5) . . ?
C4 C2 C3 123.4(5) . . ?
H3a C3 C2 123.0(4) . . ?
C4 C3 C2 114.0(6) 2_675 . ?
C4 C3 H3a 123.0(4) 2_675 . ?
C3 C4 C2 122.7(5) 2_675 . ?
C5 C4 C2 107.5(6) . . ?
C5 C4 C3 129.9(7) . 2_675 ?
N1 C5 O2 127.2(6) . . ?
C4 C5 O2 126.6(7) . . ?
C4 C5 N1 106.3(6) . . ?
H6 C6 N1 104.2(4) . . ?
C7 C6 N1 113.2(5) . . ?
C7 C6 H6 104.2(5) . . ?
C8 C6 N1 109.1(5) . . ?
C8 C6 H6 104.2(4) . . ?
C8 C6 C7 120.2(6) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C6 109.2(4) . . ?
H8b C8 C6 109.2(4) . . ?
H8b C8 H8a 107.873751109(16) . . ?
C9 C8 C6 112.2(5) . . ?
C9 C8 H8a 109.2(4) . . ?
C9 C8 H8b 109.2(4) . . ?
O4 C9 O3 124.0(6) . . ?
C8 C9 O3 114.0(6) . . ?
C8 C9 O4 122.1(6) . . ?
C9Q N1Q C1Q 116.9(5) . . ?
H1Q C1Q N1Q 117.6(3) . . ?
C2Q C1Q N1Q 124.7(6) . . ?
C2Q C1Q H1Q 117.6(4) . . ?
H2Q C2Q C1Q 121.2(4) . . ?
C3Q C2Q C1Q 117.6(6) . . ?
C3Q C2Q H2Q 121.2(4) . . ?
H3Q C3Q C2Q 119.6(4) . . ?
C4Q C3Q C2Q 120.9(6) . . ?
C4Q C3Q H3Q 119.6(3) . . ?
C5Q C4Q C3Q 124.6(6) . . ?
C9Q C4Q C3Q 116.3(6) . . ?
C9Q C4Q C5Q 119.0(6) . . ?
H5Q C5Q C4Q 119.5(4) . . ?
C6Q C5Q C4Q 121.0(6) . . ?
C6Q C5Q H5Q 119.5(4) . . ?
H6Q C6Q C5Q 119.6(4) . . ?
C7Q C6Q C5Q 120.8(6) . . ?
C7Q C6Q H6Q 119.6(4) . . ?
H7Q C7Q C6Q 120.0(4) . . ?
C8Q C7Q C6Q 120.0(6) . . ?
C8Q C7Q H7Q 120.0(4) . . ?
H8Q C8Q C7Q 120.3(4) . . ?
C9Q C8Q C7Q 119.5(6) . . ?
C9Q C8Q H8Q 120.3(3) . . ?
C4Q C9Q N1Q 123.6(5) . . ?
C8Q C9Q N1Q 116.8(5) . . ?
C8Q C9Q C4Q 119.6(6) . . ?

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
O3 H3 N1Q 1.06(8) 1.62(8) 2.652(6) 166(7) 1_645

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
O1 C1 N1 C5 177.6(6) . . . . ?
O1 C1 N1 C6 -1.3(8) . . . . ?
O1 C1 C2 C3 2.4(8) . . . . ?
O1 C1 C2 C4 -178.5(7) . . . . ?
O2 C5 N1 C1 -178.6(7) . . . . ?
O2 C5 N1 C6 0.3(9) . . . . ?
O2 C5 C4 C2 179.7(7) . . . . ?
O2 C5 C4 C3 -0.3(9) . . . 2_675 ?
O3 C9 C8 C6 -131.5(6) . . . . ?
O4 C9 C8 C6 49.0(8) . . . . ?
N1 C1 C2 C3 -177.6(4) . . . . ?
N1 C1 C2 C4 1.5(5) . . . . ?
N1 C5 C4 C2 -1.2(6) . . . . ?
N1 C5 C4 C3 178.8(4) . . . 2_675 ?
N1 C6 C8 C9 -164.4(6) . . . . ?
C1 C2 C3 C4 180.0(6) . . . 2_675 ?
C1 C2 C4 C3 179.7(4) . . . 2_675 ?
C1 C2 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C2 -1.0(5) . . 2_675 2_675 ?
C2 C3 C4 C5 179.1(5) . . 2_675 2_675 ?
C2 C4 C3 C2 1.0(5) . . 2_675 2_675 ?
N1Q C1Q C2Q C3Q -0.8(7) . . . . ?
N1Q C9Q C4Q C3Q 1.9(6) . . . . ?
N1Q C9Q C4Q C5Q -179.6(5) . . . . ?
N1Q C9Q C8Q C7Q -179.5(5) . . . . ?
C1Q C2Q C3Q C4Q 1.4(7) . . . . ?
C2Q C3Q C4Q C5Q 179.7(6) . . . . ?
C2Q C3Q C4Q C9Q -1.9(6) . . . . ?
C3Q C4Q C5Q C6Q 178.3(6) . . . . ?
C3Q C4Q C9Q C8Q -179.8(5) . . . . ?
C4Q C5Q C6Q C7Q 0.8(7) . . . . ?
C4Q C9Q C8Q C7Q 2.1(6) . . . . ?
C5Q C6Q C7Q C8Q 0.0(8) . . . . ?
C6Q C7Q C8Q C9Q -1.5(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L14_002
_database_code_depnum_ccdc_archive 'CCDC 2324806'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University Udaipur
India
;
_audit_update_record             
;
2024-01-11 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C24 H30 N4 O10'
_chemical_formula_weight         534.527
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   16.173(3)
_cell_length_b                   7.3318(15)
_cell_length_c                   11.298(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.52(3)
_cell_angle_gamma                90
_cell_volume                     1339.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6781
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.05
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.9974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12717
_diffrn_reflns_point_group_measured_fraction_full 0.9992
_diffrn_reflns_point_group_measured_fraction_max 0.9974
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9974
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1559
_reflns_number_total             3069
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.7476
_refine_diff_density_min         -0.4076
_refine_diff_density_rms         0.0900
_refine_ls_d_res_high            0.7700
_refine_ls_d_res_low             6.6776
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9856
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0628
_refine_ls_restrained_S_all      0.9856
_refine_ls_shift/su_max          -0.0023
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0834P)²+0.8097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1999
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3a), C1D(H1D)
2.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C2D(H2Da,H2Db,H2Dc), C3D(H3Da,H3Db,H3Dc)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
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_refinement_flags_posn
O1 O 1.02856(13) 1.4447(3) 0.66421(19) 0.0605(6) Uani 1.000000 .
O2 O 0.83756(13) 1.0931(3) 0.2644(2) 0.0635(6) Uani 1.000000 .
O3 O 0.63932(14) 0.6099(4) 0.0963(2) 0.0891(9) Uani 1.000000 .
H3 H 0.61940(16) 0.574(7) 0.0316(15) 0.1337(13) Uiso 1.000000 GR
O4 O 0.75569(16) 0.5674(5) 0.0033(3) 0.1117(12) Uani 1.000000 .
N1 N 0.89128(14) 0.8025(3) 0.2800(2) 0.0496(6) Uani 1.000000 .
C1 C 1.04887(17) 1.2864(4) 0.6529(2) 0.0481(7) Uani 1.000000 .
C2 C 1.01681(16) 1.1494(3) 0.5672(2) 0.0441(7) Uani 1.000000 .
C3 C 0.95673(17) 1.1695(4) 0.4795(2) 0.0473(7) Uani 1.000000 .
H3a H 0.92823(17) 1.2809(4) 0.4660(2) 0.0568(8) Uiso 1.000000 R
C4 C 0.94181(16) 1.0136(4) 0.4134(2) 0.0452(7) Uani 1.000000 .
C5 C 0.88359(17) 0.9848(4) 0.3123(3) 0.0499(7) Uani 1.000000 .
C7 C 0.84873(18) 0.7229(4) 0.1783(2) 0.0560(8) Uani 1.000000 .
H7a H 0.84951(18) 0.8112(4) 0.1120(2) 0.0671(10) Uiso 1.000000 R
H7b H 0.87893(18) 0.6124(4) 0.1529(2) 0.0671(10) Uiso 1.000000 R
C8 C 0.76117(19) 0.6728(5) 0.2040(3) 0.0640(9) Uani 1.000000 .
H8 H 0.73265(19) 0.7872(5) 0.2292(3) 0.0768(11) Uiso 1.000000 R
C9 C 0.7497(2) 0.5363(6) 0.3015(3) 0.0824(12) Uani 1.000000 .
H9a H 0.7792(14) 0.4236(14) 0.2821(12) 0.1235(18) Uiso 1.000000 GR
H9b H 0.7717(15) 0.5862(15) 0.3759(6) 0.1235(18) Uiso 1.000000 GR
H9c H 0.6906(3) 0.510(3) 0.3103(16) 0.1235(18) Uiso 1.000000 GR
O1D O 0.57215(16) -0.0132(5) 0.3977(2) 0.1012(10) Uani 1.000000 .
N1D N 0.58713(17) 0.0597(4) 0.2056(2) 0.0676(8) Uani 1.000000 .
C10 C 0.7191(2) 0.6104(5) 0.0907(3) 0.0662(9) Uani 1.000000 .
C1D C 0.6143(2) 0.0399(5) 0.3153(3) 0.0689(10) Uani 1.000000 .
H1D H 0.6705(2) 0.0690(5) 0.3314(3) 0.0827(12) Uiso 1.000000 R
C2D C 0.6410(3) 0.1147(6) 0.1108(4) 0.0906(13) Uani 1.000000 .
H2Da H 0.6965(5) 0.139(4) 0.1428(5) 0.1359(19) Uiso 1.000000 GR
H2Db H 0.6438(14) 0.0172(17) 0.0517(13) 0.1359(19) Uiso 1.000000 GR
H2Dc H 0.6193(10) 0.226(2) 0.0737(17) 0.1359(19) Uiso 1.000000 GR
C3D C 0.5025(2) 0.0144(7) 0.1746(4) 0.1020(15) Uani 1.000000 .
H3Da H 0.5015(3) -0.098(2) 0.128(3) 0.153(2) Uiso 1.000000 GR
H3Db H 0.4704(5) -0.003(5) 0.2470(4) 0.153(2) Uiso 1.000000 GR
H3Dc H 0.4782(7) 0.114(2) 0.128(2) 0.153(2) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(3) . ?
O2 C5 1.213(3) . ?
O3 H3 0.8400 . ?
O3 C10 1.293(4) . ?
O4 C10 1.198(4) . ?
N1 C1 1.386(3) 3_776 ?
N1 C5 1.391(4) . ?
N1 C7 1.456(3) . ?
C1 C2 1.486(4) . ?
C2 C3 1.390(4) . ?
C2 C4 1.386(4) 3_776 ?
C3 H3a 0.9500 . ?
C3 C4 1.385(4) . ?
C4 C5 1.488(4) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 C8 1.494(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.502(5) . ?
C8 C10 1.515(4) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
O1D C1D 1.222(4) . ?
N1D C1D 1.319(4) . ?
N1D C2D 1.444(5) . ?
N1D C3D 1.449(4) . ?
C1D H1D 0.9500 . ?
C2D H2Da 0.9800 . ?
C2D H2Db 0.9800 . ?
C2D H2Dc 0.9800 . ?
C3D H3Da 0.9800 . ?
C3D H3Db 0.9800 . ?
C3D H3Dc 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 H3 109.5 . . ?
C5 N1 C1 111.8(2) . 3_776 ?
C7 N1 C1 124.4(2) . 3_776 ?
C7 N1 C5 123.3(2) . . ?
N1 C1 O1 125.5(3) 3_776 . ?
C2 C1 O1 128.5(3) . . ?
C2 C1 N1 106.0(2) . 3_776 ?
C3 C2 C1 129.1(2) . . ?
C4 C2 C1 108.4(2) 3_776 . ?
C4 C2 C3 122.5(2) 3_776 . ?
H3a C3 C2 122.76(16) . . ?
C4 C3 C2 114.5(2) . . ?
C4 C3 H3a 122.76(16) . . ?
C3 C4 C2 123.0(2) . 3_776 ?
C5 C4 C2 107.5(2) . 3_776 ?
C5 C4 C3 129.6(2) . . ?
N1 C5 O2 124.6(3) . . ?
C4 C5 O2 129.1(3) . . ?
C4 C5 N1 106.3(2) . . ?
H7a C7 N1 109.03(16) . . ?
H7b C7 N1 109.03(16) . . ?
H7b C7 H7a 107.8 . . ?
C8 C7 N1 112.8(2) . . ?
C8 C7 H7a 109.03(18) . . ?
C8 C7 H7b 109.03(19) . . ?
H8 C8 C7 106.83(19) . . ?
C9 C8 C7 115.5(3) . . ?
C9 C8 H8 106.8(2) . . ?
C10 C8 C7 109.2(3) . . ?
C10 C8 H8 106.8(2) . . ?
C10 C8 C9 111.2(3) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
C2D N1D C1D 121.9(3) . . ?
C3D N1D C1D 120.5(3) . . ?
C3D N1D C2D 117.5(3) . . ?
O4 C10 O3 122.7(3) . . ?
C8 C10 O3 113.6(3) . . ?
C8 C10 O4 123.7(3) . . ?
N1D C1D O1D 124.5(3) . . ?
H1D C1D O1D 117.73(19) . . ?
H1D C1D N1D 117.7(2) . . ?
H2Da C2D N1D 109.5 . . ?
H2Db C2D N1D 109.5 . . ?
H2Db C2D H2Da 109.5 . . ?
H2Dc C2D N1D 109.5 . . ?
H2Dc C2D H2Da 109.5 . . ?
H2Dc C2D H2Db 109.5 . . ?
H3Da C3D N1D 109.5 . . ?
H3Db C3D N1D 109.5 . . ?
H3Db C3D H3Da 109.5 . . ?
H3Dc C3D N1D 109.5 . . ?
H3Dc C3D H3Da 109.5 . . ?
H3Dc C3D H3Db 109.5 . . ?

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
O3 H3 O1D 0.8400 1.746(5) 2.584(3) 175(4) 4_565

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
O1 C1 N1 C5 178.5(3) . . 3_776 3_776 ?
O1 C1 N1 C7 5.8(4) . . 3_776 3_776 ?
O1 C1 C2 C3 0.5(4) . . . . ?
O1 C1 C2 C4 179.9(3) . . . 3_776 ?
O2 C5 N1 C1 177.4(3) . . . 3_776 ?
O2 C5 N1 C7 4.6(4) . . . . ?
O2 C5 C4 C2 -177.6(3) . . . 3_776 ?
O2 C5 C4 C3 1.6(4) . . . . ?
O3 C10 C8 C7 -162.9(3) . . . . ?
O3 C10 C8 C9 68.5(4) . . . . ?
O4 C10 C8 C7 16.2(5) . . . . ?
O4 C10 C8 C9 -112.3(4) . . . . ?
N1 C1 C2 C3 -179.3(2) 3_776 . . . ?
N1 C1 C2 C4 -0.1(2) . 3_776 3_776 . ?
N1 C5 C4 C2 2.4(3) . . . 3_776 ?
N1 C5 C4 C3 -178.5(2) . . . . ?
N1 C7 C8 C9 -59.8(3) . . . . ?
N1 C7 C8 C10 174.0(3) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C1 C2 C4 C3 -179.4(2) . . 3_776 3_776 ?
C1 C2 C4 C5 1.4(2) . . 3_776 3_776 ?
C2 C3 C4 C2 0.0(2) . . . 3_776 ?
C2 C3 C4 C5 -179.0(2) . . . . ?
C2 C4 C3 C2 0.0(3) 3_776 . . . ?
O1D C1D N1D C2D -177.0(4) . . . . ?
O1D C1D N1D C3D -1.2(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
