# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2023

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

data_L13_044
_database_code_depnum_ccdc_archive 'CCDC 2205752'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;MLSU
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_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 0.00347 0.00161 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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                   15.625(3)
_cell_length_b                   6.8164(14)
_cell_length_c                   12.177(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.91(3)
_cell_angle_gamma                90
_cell_volume                     1296.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9099
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.26
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             564.449
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.9991
_diffrn_reflns_Laue_measured_fraction_max 0.9980
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12280
_diffrn_reflns_point_group_measured_fraction_full 0.9991
_diffrn_reflns_point_group_measured_fraction_max 0.9980
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9980
_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              8
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2241
_reflns_number_total             2958
_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         0.3071
_refine_diff_density_min         -0.2334
_refine_diff_density_rms         0.0590
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             6.2472
_refine_ls_goodness_of_fit_ref   1.0782
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.0782
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.3742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1149
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3a), C1D(H1D)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C2D(H2Da,H2Db,H2Dc), C3D(H3Da,H3Db,H3Dc)
2.c 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 0.96265(7) 0.43233(17) 0.68402(10) 0.0411(3) Uani 1.000000 .
O2 O 0.80600(7) -0.13637(15) 0.65904(9) 0.0347(3) Uani 1.000000 .
O3 O 0.69952(7) 0.22371(18) 0.62399(9) 0.0370(3) Uani 1.000000 .
H3 H 0.6474(2) 0.210(3) 0.6067(4) 0.0555(4) Uiso 1.000000 GR
O4 O 0.65780(7) 0.12480(19) 0.78902(9) 0.0421(3) Uani 1.000000 .
N1 N 0.86554(7) 0.17045(17) 0.68899(10) 0.0261(3) Uani 1.000000 .
C1 C 0.93737(9) 0.2732(2) 0.65375(12) 0.0282(3) Uani 1.000000 .
C2 C 0.97708(8) 0.1447(2) 0.56989(11) 0.0252(3) Uani 1.000000 .
C3 C 1.04662(9) 0.1823(2) 0.50544(12) 0.0272(3) Uani 1.000000 .
H3a H 1.07731(9) 0.3026(2) 0.50873(12) 0.0327(4) Uiso 1.000000 R
C4 C 0.93215(8) -0.0305(2) 0.56420(11) 0.0255(3) Uani 1.000000 .
C5 C 0.86042(9) -0.0163(2) 0.64093(12) 0.0266(3) Uani 1.000000 .
C6 C 0.80321(9) 0.2277(2) 0.77265(12) 0.0290(3) Uani 1.000000 .
C7 C 0.80359(10) 0.4484(2) 0.79409(14) 0.0389(4) Uani 1.000000 .
H7a H 0.8587(3) 0.4867(4) 0.8283(9) 0.0584(6) Uiso 1.000000 GR
H7b H 0.7949(8) 0.5186(2) 0.72437(18) 0.0584(6) Uiso 1.000000 GR
H7c H 0.7574(5) 0.4816(3) 0.8433(8) 0.0584(6) Uiso 1.000000 GR
C8 C 0.82282(11) 0.1126(3) 0.87817(13) 0.0388(4) Uani 1.000000 .
H8a H 0.8132(7) -0.0275(3) 0.8646(3) 0.0581(6) Uiso 1.000000 GR
H8b H 0.8827(2) 0.1339(14) 0.9018(6) 0.0581(6) Uiso 1.000000 GR
H8c H 0.7852(5) 0.1577(13) 0.9358(3) 0.0581(6) Uiso 1.000000 GR
C9 C 0.71233(9) 0.1811(2) 0.72818(12) 0.0294(3) Uani 1.000000 .
O1D O 0.54084(7) 0.21223(18) 0.57014(10) 0.0416(3) Uani 1.000000 .
N1D N 0.44476(8) 0.27857(19) 0.43220(10) 0.0317(3) Uani 1.000000 .
C1D C 0.52279(10) 0.2480(2) 0.47226(14) 0.0338(3) Uani 1.000000 .
H1D H 0.56849(10) 0.2537(2) 0.42281(14) 0.0406(4) Uiso 1.000000 R
C2D C 0.42882(13) 0.3139(3) 0.31533(14) 0.0457(4) Uani 1.000000 .
H2Da H 0.48344(14) 0.318(2) 0.2781(2) 0.0685(6) Uiso 1.000000 GR
H2Db H 0.3932(7) 0.2080(11) 0.2841(3) 0.0685(6) Uiso 1.000000 GR
H2Dc H 0.3990(8) 0.4394(10) 0.30512(15) 0.0685(6) Uiso 1.000000 GR
C3D C 0.37154(11) 0.2695(3) 0.50207(15) 0.0486(5) Uani 1.000000 .
H3Da H 0.39134(11) 0.252(2) 0.5786(2) 0.0729(7) Uiso 1.000000 GR
H3Db H 0.3388(5) 0.3918(9) 0.4952(9) 0.0729(7) Uiso 1.000000 GR
H3Dc H 0.3350(5) 0.1588(13) 0.4796(8) 0.0729(7) 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 1.2077(19) . ?
O2 C5 1.2059(17) . ?
O3 H3 0.8400 . ?
O3 C9 1.3104(18) . ?
O4 C9 1.2098(18) . ?
N1 C1 1.4023(18) . ?
N1 C5 1.4021(18) . ?
N1 C6 1.4846(18) . ?
C1 C2 1.496(2) . ?
C2 C3 1.385(2) . ?
C2 C4 1.3857(19) . ?
C3 H3a 0.9500 . ?
C3 C4 1.385(2) 3_756 ?
C4 C5 1.4860(19) . ?
C6 C7 1.527(2) . ?
C6 C8 1.528(2) . ?
C6 C9 1.536(2) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
O1D C1D 1.240(2) . ?
N1D C1D 1.315(2) . ?
N1D C2D 1.457(2) . ?
N1D C3D 1.450(2) . ?
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 111.15(11) . . ?
C6 N1 C1 128.95(12) . . ?
C6 N1 C5 119.69(11) . . ?
N1 C1 O1 127.75(14) . . ?
C2 C1 O1 126.54(13) . . ?
C2 C1 N1 105.71(12) . . ?
C3 C2 C1 129.01(13) . . ?
C4 C2 C1 108.53(12) . . ?
C4 C2 C3 122.45(13) . . ?
H3a C3 C2 122.68(8) . . ?
C4 C3 C2 114.64(13) 3_756 . ?
C4 C3 H3a 122.68(8) 3_756 . ?
C3 C4 C2 122.90(13) 3_756 . ?
C5 C4 C2 107.69(12) . . ?
C5 C4 C3 129.38(13) . 3_756 ?
N1 C5 O2 124.79(13) . . ?
C4 C5 O2 128.46(13) . . ?
C4 C5 N1 106.73(11) . . ?
C7 C6 N1 112.17(12) . . ?
C8 C6 N1 108.93(12) . . ?
C8 C6 C7 111.25(13) . . ?
C9 C6 N1 108.88(11) . . ?
C9 C6 C7 105.21(12) . . ?
C9 C6 C8 110.34(12) . . ?
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 109.5 . . ?
H8b C8 C6 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C6 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
O4 C9 O3 125.11(14) . . ?
C6 C9 O3 113.89(12) . . ?
C6 C9 O4 120.75(13) . . ?
C2D N1D C1D 121.01(14) . . ?
C3D N1D C1D 121.05(14) . . ?
C3D N1D C2D 117.89(14) . . ?
N1D C1D O1D 124.50(15) . . ?
H1D C1D O1D 117.75(9) . . ?
H1D C1D N1D 117.75(9) . . ?
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 1.709(3) 2.5446(16) 173(2) .

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 -175.61(16) . . . . ?
O1 C1 N1 C6 -1.0(2) . . . . ?
O1 C1 C2 C3 -4.0(2) . . . . ?
O1 C1 C2 C4 175.99(17) . . . . ?
O2 C5 N1 C1 178.26(15) . . . . ?
O2 C5 N1 C6 3.04(17) . . . . ?
O2 C5 C4 C2 178.99(16) . . . . ?
O2 C5 C4 C3 0.8(2) . . . 3_756 ?
O3 C9 C6 N1 -40.84(13) . . . . ?
O3 C9 C6 C7 79.58(14) . . . . ?
O3 C9 C6 C8 -160.34(14) . . . . ?
O4 C9 C6 N1 144.59(15) . . . . ?
O4 C9 C6 C7 -95.00(16) . . . . ?
O4 C9 C6 C8 25.09(17) . . . . ?
N1 C1 C2 C3 175.99(11) . . . . ?
N1 C1 C2 C4 -4.02(12) . . . . ?
N1 C5 C4 C2 0.48(12) . . . . ?
N1 C5 C4 C3 -177.74(10) . . . 3_756 ?
C1 C2 C3 C4 179.51(15) . . . 3_756 ?
C1 C2 C4 C3 -179.47(11) . . . 3_756 ?
C1 C2 C4 C5 2.16(12) . . . . ?
C2 C3 C4 C2 0.48(13) . . 3_756 3_756 ?
C2 C3 C4 C5 -177.50(11) . . 3_756 3_756 ?
C2 C4 C3 C2 -0.48(12) . . 3_756 3_756 ?
O1D C1D N1D C2D -178.12(16) . . . . ?
O1D C1D N1D C3D -0.9(2) . . . . ?


_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_039
_database_code_depnum_ccdc_archive 'CCDC 2205757'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University 
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C4 H8 O2)'
_chemical_formula_sum            'C26 H32 N2 O12'
_chemical_formula_weight         564.53
_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                   12.514(3)
_cell_length_b                   9.5933(19)
_cell_length_c                   11.344(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.58(3)
_cell_angle_gamma                90
_cell_volume                     1361.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6480
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.20
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.198
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                1549
_reflns_number_total             3117
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.083
_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)+(0.1002P)²+0.4475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.2197
_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
 Fixed Sof: C61(0.52) H61(0.52) C71(0.6) H71A(0.6) H71B(0.6) C81(0.5)
 H81A(0.5) H81B(0.5) H81C(0.5) C62(0.48) H62(0.48) C72(0.4) H72A(0.4) H72B(0.4)
 C82(0.5) H82A(0.5) H82B(0.5) H82C(0.5)
3.a Ternary CH refined with riding coordinates:
 C61(H61), C62(H62)
3.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C72(H72A,H72B), C1D(H1DA,H1DB), C2D(H2DA,H2DB), C3D(H3DA,
 H3DB), C4D(H4DA,H4DB)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3A)
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     dual
_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 0.26105(17) 0.5415(2) 0.3454(2) 0.0562(7) Uani 1 1 d . . . . .
O2 O -0.02546(19) 0.2746(2) 0.2283(2) 0.0604(7) Uani 1 1 d . . . . .
O3 O 0.28020(17) 0.1521(2) 0.09357(18) 0.0459(6) Uani 1 1 d . . . . .
H3 H 0.302495 0.072086 0.111641 0.069 Uiso 1 1 calc R U . . .
O4 O 0.2180(2) 0.1480(3) 0.2761(2) 0.0818(9) Uani 1 1 d . . . . .
N1 N 0.1299(2) 0.4022(3) 0.2578(2) 0.0491(7) Uani 1 1 d . . . . .
C1 C 0.1726(2) 0.4903(3) 0.3456(3) 0.0432(7) Uani 1 1 d . . . . .
C2 C 0.0890(2) 0.5054(3) 0.4343(2) 0.0352(7) Uani 1 1 d . . . . .
C3 C 0.0901(2) 0.5826(3) 0.5370(3) 0.0390(7) Uani 1 1 d . . . . .
H3A H 0.149842 0.637632 0.561501 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0013(2) 0.4257(3) 0.3985(2) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.0278(3) 0.3559(3) 0.2861(3) 0.0458(8) Uani 1 1 d . . . . .
C61 C 0.2067(7) 0.3509(16) 0.1693(9) 0.034(2) Uani 0.52 1 d . . P A 1
H61 H 0.274752 0.404795 0.179503 0.040 Uiso 0.52 1 calc R U P A 1
C71 C 0.1544(5) 0.3894(6) 0.0463(4) 0.0448(12) Uani 0.6 1 d . . P A 1
H71A H 0.080111 0.354197 0.041012 0.054 Uiso 0.6 1 calc R U P A 1
H71B H 0.195255 0.346060 -0.017609 0.054 Uiso 0.6 1 calc R U P A 1
C81 C 0.155(2) 0.553(2) 0.033(2) 0.076(6) Uani 0.5 1 d . . P A 1
H81A H 0.123120 0.595887 0.101736 0.115 Uiso 0.5 1 calc R U P A 1
H81B H 0.113860 0.579574 -0.038565 0.115 Uiso 0.5 1 calc R U P A 1
H81C H 0.228990 0.585877 0.026220 0.115 Uiso 0.5 1 calc R U P A 1
C62 C 0.1679(8) 0.3462(17) 0.1453(11) 0.045(3) Uani 0.48 1 d . . P A 2
H62 H 0.103351 0.316799 0.097714 0.054 Uiso 0.48 1 calc R U P A 2
C72 C 0.2285(8) 0.4452(8) 0.0717(7) 0.051(2) Uani 0.4 1 d . . P A 2
H72A H 0.262727 0.395748 0.006127 0.061 Uiso 0.4 1 calc R U P A 2
H72B H 0.284407 0.493504 0.119667 0.061 Uiso 0.4 1 calc R U P A 2
C82 C 0.141(2) 0.5534(18) 0.022(2) 0.066(6) Uani 0.5 1 d . . P A 2
H82A H 0.097518 0.508982 -0.039894 0.099 Uiso 0.5 1 calc R U P A 2
H82B H 0.177493 0.635037 -0.009883 0.099 Uiso 0.5 1 calc R U P A 2
H82C H 0.095617 0.582709 0.086573 0.099 Uiso 0.5 1 calc R U P A 2
C9 C 0.2304(2) 0.2070(3) 0.1843(3) 0.0431(7) Uani 1 1 d . . . . .
O1D O 0.65461(19) 0.1080(3) 0.8492(2) 0.0642(7) Uani 1 1 d . . . . .
O2D O 0.4547(2) 0.1955(4) 0.7575(3) 0.1010(12) Uani 1 1 d . . . . .
C1D C 0.6368(4) 0.1322(5) 0.7238(4) 0.0900(15) Uani 1 1 d . . . . .
H1DA H 0.681886 0.068400 0.677890 0.108 Uiso 1 1 calc R U . . .
H1DB H 0.656179 0.229306 0.703855 0.108 Uiso 1 1 calc R U . . .
C2D C 0.5192(5) 0.1065(6) 0.6936(4) 0.0997(18) Uani 1 1 d . . . . .
H2DA H 0.505718 0.121665 0.608140 0.120 Uiso 1 1 calc R U . . .
H2DB H 0.500977 0.008502 0.711776 0.120 Uiso 1 1 calc R U . . .
C3D C 0.4720(3) 0.1653(6) 0.8772(4) 0.0930(15) Uani 1 1 d . . . . .
H3DA H 0.453256 0.066695 0.892065 0.112 Uiso 1 1 calc R U . . .
H3DB H 0.424993 0.224630 0.924845 0.112 Uiso 1 1 calc R U . . .
C4D C 0.5830(3) 0.1893(4) 0.9134(4) 0.0639(10) Uani 1 1 d . . . . .
H4DA H 0.600282 0.289099 0.902400 0.077 Uiso 1 1 calc R U . . .
H4DB H 0.592411 0.167484 0.998313 0.077 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 1.212(4) . ?
O2 C5 1.208(4) . ?
O3 H3 0.8400 . ?
O3 C9 1.327(4) . ?
O4 C9 1.199(4) . ?
N1 C1 1.401(4) . ?
N1 C5 1.399(4) . ?
N1 C61 1.492(12) . ?
N1 C62 1.475(13) . ?
C1 C2 1.478(4) . ?
C2 C3 1.381(4) . ?
C2 C4 1.389(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.377(4) 3_566 ?
C4 C5 1.486(4) . ?
C61 H61 1.0000 . ?
C61 C71 1.569(10) . ?
C61 C9 1.421(15) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C71 C81 1.58(2) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C62 H62 1.0000 . ?
C62 C72 1.485(17) . ?
C62 C9 1.604(14) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C72 C82 1.60(2) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
O1D C1D 1.452(5) . ?
O1D C4D 1.406(4) . ?
O2D C2D 1.393(7) . ?
O2D C3D 1.400(5) . ?
C1D H1DA 0.9900 . ?
C1D H1DB 0.9900 . ?
C1D C2D 1.523(7) . ?
C2D H2DA 0.9900 . ?
C2D H2DB 0.9900 . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.456(5) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?

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 116.0(5) . . ?
C1 N1 C62 135.2(6) . . ?
C5 N1 C1 111.1(2) . . ?
C5 N1 C61 131.3(5) . . ?
C5 N1 C62 113.7(6) . . ?
O1 C1 N1 124.9(3) . . ?
O1 C1 C2 128.8(3) . . ?
N1 C1 C2 106.3(2) . . ?
C3 C2 C1 129.5(3) . . ?
C3 C2 C4 122.1(2) . . ?
C4 C2 C1 108.4(3) . . ?
C2 C3 H3A 122.3 . . ?
C4 C3 C2 115.3(3) 3_566 . ?
C4 C3 H3A 122.3 3_566 . ?
C2 C4 C5 107.8(2) . . ?
C3 C4 C2 122.6(3) 3_566 . ?
C3 C4 C5 129.6(3) 3_566 . ?
O2 C5 N1 125.0(3) . . ?
O2 C5 C4 128.6(3) . . ?
N1 C5 C4 106.3(3) . . ?
N1 C61 H61 108.3 . . ?
N1 C61 C71 105.1(6) . . ?
C71 C61 H61 108.3 . . ?
C9 C61 N1 112.1(8) . . ?
C9 C61 H61 108.3 . . ?
C9 C61 C71 114.6(8) . . ?
C61 C71 H71A 110.0 . . ?
C61 C71 H71B 110.0 . . ?
C61 C71 C81 108.6(11) . . ?
H71A C71 H71B 108.4 . . ?
C81 C71 H71A 110.0 . . ?
C81 C71 H71B 110.0 . . ?
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 H62 107.1 . . ?
N1 C62 C72 115.8(11) . . ?
N1 C62 C9 103.3(8) . . ?
C72 C62 H62 107.1 . . ?
C72 C62 C9 115.8(8) . . ?
C9 C62 H62 107.1 . . ?
C62 C72 H72A 110.7 . . ?
C62 C72 H72B 110.7 . . ?
C62 C72 C82 105.0(10) . . ?
H72A C72 H72B 108.8 . . ?
C82 C72 H72A 110.7 . . ?
C82 C72 H72B 110.7 . . ?
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 C61 113.2(5) . . ?
O3 C9 C62 110.6(5) . . ?
O4 C9 O3 124.1(3) . . ?
O4 C9 C61 122.1(5) . . ?
O4 C9 C62 124.0(5) . . ?
C4D O1D C1D 109.7(3) . . ?
C2D O2D C3D 107.5(4) . . ?
O1D C1D H1DA 110.0 . . ?
O1D C1D H1DB 110.0 . . ?
O1D C1D C2D 108.4(4) . . ?
H1DA C1D H1DB 108.4 . . ?
C2D C1D H1DA 110.0 . . ?
C2D C1D H1DB 110.0 . . ?
O2D C2D C1D 110.7(4) . . ?
O2D C2D H2DA 109.5 . . ?
O2D C2D H2DB 109.5 . . ?
C1D C2D H2DA 109.5 . . ?
C1D C2D H2DB 109.5 . . ?
H2DA C2D H2DB 108.1 . . ?
O2D C3D H3DA 109.4 . . ?
O2D C3D H3DB 109.4 . . ?
O2D C3D C4D 111.2(4) . . ?
H3DA C3D H3DB 108.0 . . ?
C4D C3D H3DA 109.4 . . ?
C4D C3D H3DB 109.4 . . ?
O1D C4D C3D 112.5(4) . . ?
O1D C4D H4DA 109.1 . . ?
O1D C4D H4DB 109.1 . . ?
C3D C4D H4DA 109.1 . . ?
C3D C4D H4DB 109.1 . . ?
H4DA C4D H4DB 107.8 . . ?

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 O1D 0.84 1.86 2.699(3) 177.3 3_656 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 1.0(5) . . . . ?
O1 C1 C2 C4 -179.0(3) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
N1 C1 C2 C4 1.0(3) . . . . ?
N1 C61 C71 C81 68.3(12) . . . . ?
N1 C61 C9 O3 166.9(4) . . . . ?
N1 C61 C9 O4 -21.8(8) . . . . ?
N1 C62 C72 C82 -71.3(12) . . . . ?
N1 C62 C9 O3 -173.0(5) . . . . ?
N1 C62 C9 O4 19.4(10) . . . . ?
C1 N1 C5 O2 -176.9(3) . . . . ?
C1 N1 C5 C4 2.9(3) . . . . ?
C1 N1 C61 C71 -126.6(6) . . . . ?
C1 N1 C61 C9 108.3(6) . . . . ?
C1 N1 C62 C72 -40.2(12) . . . . ?
C1 N1 C62 C9 87.4(11) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . 3_566 ?
C1 C2 C4 C3 179.7(3) . . . 3_566 ?
C1 C2 C4 C5 0.7(3) . . . . ?
C2 C4 C5 O2 177.6(3) . . . . ?
C2 C4 C5 N1 -2.1(3) . . . . ?
C3 C2 C4 C3 -0.3(5) . . . 3_566 ?
C3 C2 C4 C5 -179.3(2) . . . . ?
C3 C4 C5 O2 -1.3(5) 3_566 . . . ?
C3 C4 C5 N1 179.0(3) 3_566 . . . ?
C4 C2 C3 C4 0.3(4) . . . 3_566 ?
C5 N1 C1 O1 177.5(3) . . . . ?
C5 N1 C1 C2 -2.4(3) . . . . ?
C5 N1 C61 C71 69.5(10) . . . . ?
C5 N1 C61 C9 -55.5(7) . . . . ?
C5 N1 C62 C72 141.0(7) . . . . ?
C5 N1 C62 C9 -91.4(6) . . . . ?
C61 N1 C1 O1 10.5(7) . . . . ?
C61 N1 C1 C2 -169.5(6) . . . . ?
C61 N1 C5 O2 -12.5(8) . . . . ?
C61 N1 C5 C4 167.3(6) . . . . ?
C71 C61 C9 O3 47.3(8) . . . . ?
C71 C61 C9 O4 -141.4(6) . . . . ?
C62 N1 C1 O1 -1.3(9) . . . . ?
C62 N1 C1 C2 178.7(8) . . . . ?
C62 N1 C5 O2 2.2(7) . . . . ?
C62 N1 C5 C4 -178.1(6) . . . . ?
C72 C62 C9 O3 -45.3(10) . . . . ?
C72 C62 C9 O4 147.1(7) . . . . ?
C9 C61 C71 C81 -168.3(11) . . . . ?
C9 C62 C72 C82 167.6(11) . . . . ?
O1D C1D C2D O2D 59.7(5) . . . . ?
O2D C3D C4D O1D -59.1(5) . . . . ?
C1D O1D C4D C3D 55.0(5) . . . . ?
C2D O2D C3D C4D 61.2(5) . . . . ?
C3D O2D C2D C1D -62.3(5) . . . . ?
C4D O1D C1D C2D -54.0(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_p13_053mono
_database_code_depnum_ccdc_archive 'CCDC 2205755'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University 
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_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         534.52
_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 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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                   12.632(3)
_cell_length_b                   9.2860(19)
_cell_length_c                   11.744(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.95(3)
_cell_angle_gamma                90
_cell_volume                     1310.5(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24242
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      3.39
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9993
_exptl_absorpt_correction_T_min  0.9959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13278
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.544
_diffrn_reflns_theta_min         3.339
_diffrn_ambient_temperature      99.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.700
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3396
_reflns_number_total             3782
_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       HKL3000
_computing_data_collection       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL-XS'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.065
_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)+(0.0697P)²+0.6124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1469
_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. Restrained distances
 O4-C9 \\sim O4A-C9
 with sigma of 0.02
3. Others
 Sof(C62)=Sof(H62)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(C82)=Sof(H82A)=Sof(H82B)=
 Sof(H82C)=1-FVAR(1)
 Sof(C61)=Sof(H61)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(C81)=Sof(H81A)=Sof(H81B)=
 Sof(H81C)=FVAR(1)
 Sof(O4A)=1-FVAR(2)
 Sof(O4)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C61(H61), C62(H62)
4.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C72(H72A,H72B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C1D(H1D)
4.d Idealised Me refined as rotating group:
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C), C2D(H2DC,H2DB,H2DA), C3D(H3DB,H3DA,
 H3DC)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.76603(8) 1.02520(13) 0.41871(11) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.44954(11) 0.78053(12) 0.21680(10) 0.0405(3) Uani 1 1 d . . . . .
O3 O 0.78771(7) 0.64132(10) 0.20303(8) 0.0233(2) Uani 1 1 d . . . . .
H3 H 0.820860 0.567938 0.238491 0.035 Uiso 1 1 calc R U . . .
O4 O 0.733(2) 0.665(2) 0.3662(10) 0.0340(19) Uani 0.53(8) 1 d D . P A 1
N1 N 0.61702(11) 0.90231(12) 0.28982(12) 0.0325(3) Uani 1 1 d . . . . .
C1 C 0.67103(11) 0.98292(14) 0.39140(13) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.58900(9) 1.00268(12) 0.45857(11) 0.0206(2) Uani 1 1 d . . . . .
C3 C 0.60040(10) 1.07630(13) 0.56429(11) 0.0216(2) Uani 1 1 d . . . . .
H3A H 0.666459 1.126267 0.606527 0.026 Uiso 1 1 calc R U . . .
C4 C 0.49258(10) 0.92892(12) 0.39659(10) 0.0206(2) Uani 1 1 d . . . . .
C5 C 0.51086(13) 0.85966(13) 0.28927(12) 0.0287(3) Uani 1 1 d . . . . .
C61 C 0.6600(2) 0.8304(2) 0.1993(2) 0.0169(4) Uani 0.603(5) 1 d . . P A 1
H61 H 0.595308 0.791895 0.133731 0.020 Uiso 0.603(5) 1 calc R U P A 1
C71 C 0.72494(17) 0.9340(2) 0.14467(17) 0.0217(5) Uani 0.603(5) 1 d . . P A 1
H71A H 0.786315 0.977672 0.209390 0.026 Uiso 0.603(5) 1 calc R U P A 1
H71B H 0.758181 0.879708 0.091601 0.026 Uiso 0.603(5) 1 calc R U P A 1
C81 C 0.6509(7) 1.0524(10) 0.0734(8) 0.042(2) Uani 0.603(5) 1 d . . P A 1
H81A H 0.591345 1.009562 0.007833 0.063 Uiso 0.603(5) 1 calc R U P A 1
H81B H 0.695309 1.117236 0.040443 0.063 Uiso 0.603(5) 1 calc R U P A 1
H81C H 0.618382 1.106762 0.125867 0.063 Uiso 0.603(5) 1 calc R U P A 1
C62 C 0.7017(4) 0.8516(4) 0.2365(4) 0.0205(7) Uani 0.397(5) 1 d . . P A 2
H62 H 0.770149 0.911997 0.267200 0.025 Uiso 0.397(5) 1 calc R U P A 2
C72 C 0.6505(3) 0.8775(3) 0.1023(3) 0.0246(8) Uani 0.397(5) 1 d . . P A 2
H72A H 0.697339 0.831206 0.058990 0.030 Uiso 0.397(5) 1 calc R U P A 2
H72B H 0.575758 0.832732 0.074565 0.030 Uiso 0.397(5) 1 calc R U P A 2
C82 C 0.6404(13) 1.0378(15) 0.0733(10) 0.040(3) Uani 0.397(5) 1 d . . P A 2
H82A H 0.583160 1.080380 0.103352 0.060 Uiso 0.397(5) 1 calc R U P A 2
H82B H 0.619642 1.051194 -0.013562 0.060 Uiso 0.397(5) 1 calc R U P A 2
H82C H 0.711940 1.085082 0.111537 0.060 Uiso 0.397(5) 1 calc R U P A 2
C9 C 0.73042(10) 0.70048(13) 0.26715(10) 0.0205(2) Uani 1 1 d D . . . .
O1D O 0.88854(11) 0.41565(13) 0.29788(9) 0.0408(3) Uani 1 1 d . . . . .
N1D N 0.94938(9) 0.28589(13) 0.46845(9) 0.0254(2) Uani 1 1 d . . . . .
C1D C 0.88962(12) 0.38823(17) 0.40211(12) 0.0322(3) Uani 1 1 d . . . . .
H1D H 0.844203 0.445160 0.435615 0.039 Uiso 1 1 calc R U . . .
C2D C 0.94298(13) 0.2534(2) 0.58731(12) 0.0359(3) Uani 1 1 d . . . . .
H2DC H 0.899129 0.327887 0.611304 0.054 Uiso 1 1 calc R U . . .
H2DB H 1.018171 0.251046 0.644473 0.054 Uiso 1 1 calc R U . . .
H2DA H 0.907315 0.159504 0.586225 0.054 Uiso 1 1 calc R U . . .
C3D C 1.01703(14) 0.1911(2) 0.42154(14) 0.0410(4) Uani 1 1 d . . . . .
H3DB H 0.976321 0.101544 0.393512 0.062 Uiso 1 1 calc R U . . .
H3DA H 1.086502 0.169272 0.484714 0.062 Uiso 1 1 calc R U . . .
H3DC H 1.034047 0.238433 0.354644 0.062 Uiso 1 1 calc R U . . .
O4A O 0.709(2) 0.638(3) 0.350(2) 0.035(3) Uani 0.47(8) 1 d D . P A 2


_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 1.2082(18) . ?
O2 C5 1.2075(19) . ?
O3 H3 0.8400 . ?
O3 C9 1.3147(13) . ?
O4 C9 1.201(8) . ?
N1 C1 1.395(2) . ?
N1 C5 1.3962(19) . ?
N1 C61 1.492(2) . ?
N1 C62 1.474(3) . ?
C1 C2 1.4945(15) . ?
C2 C3 1.3853(17) . ?
C2 C4 1.3915(18) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3876(15) 3_676 ?
C4 C5 1.4950(16) . ?
C61 H61 1.0000 . ?
C61 C71 1.528(3) . ?
C61 C9 1.563(3) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C71 C81 1.517(7) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C62 H62 1.0000 . ?
C62 C72 1.527(5) . ?
C62 C9 1.466(4) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C72 C82 1.524(14) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
C9 O4A 1.227(9) . ?
O1D C1D 1.2462(16) . ?
N1D C1D 1.3106(17) . ?
N1D C2D 1.4544(16) . ?
N1D C3D 1.4487(17) . ?
C1D H1D 0.9500 . ?
C2D H2DC 0.9800 . ?
C2D H2DB 0.9800 . ?
C2D H2DA 0.9800 . ?
C3D H3DB 0.9800 . ?
C3D H3DA 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 . . ?
C1 N1 C5 111.84(10) . . ?
C1 N1 C61 131.29(16) . . ?
C1 N1 C62 107.9(2) . . ?
C5 N1 C61 115.42(16) . . ?
C5 N1 C62 136.8(2) . . ?
O1 C1 N1 125.82(12) . . ?
O1 C1 C2 127.84(14) . . ?
N1 C1 C2 106.34(11) . . ?
C3 C2 C1 129.51(12) . . ?
C3 C2 C4 122.97(10) . . ?
C4 C2 C1 107.51(11) . . ?
C2 C3 H3A 122.8 . . ?
C2 C3 C4 114.50(11) . 3_676 ?
C4 C3 H3A 122.7 3_676 . ?
C2 C4 C5 108.37(10) . . ?
C3 C4 C2 122.53(11) 3_676 . ?
C3 C4 C5 129.09(12) 3_676 . ?
O2 C5 N1 125.63(12) . . ?
O2 C5 C4 128.59(13) . . ?
N1 C5 C4 105.77(12) . . ?
N1 C61 H61 108.6 . . ?
N1 C61 C71 112.17(18) . . ?
N1 C61 C9 104.90(15) . . ?
C71 C61 H61 108.6 . . ?
C71 C61 C9 113.87(19) . . ?
C9 C61 H61 108.6 . . ?
C61 C71 H71A 109.3 . . ?
C61 C71 H71B 109.3 . . ?
H71A C71 H71B 108.0 . . ?
C81 C71 C61 111.6(4) . . ?
C81 C71 H71A 109.3 . . ?
C81 C71 H71B 109.3 . . ?
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 H62 109.1 . . ?
N1 C62 C72 104.8(3) . . ?
C72 C62 H62 109.1 . . ?
C9 C62 N1 111.0(2) . . ?
C9 C62 H62 109.1 . . ?
C9 C62 C72 113.5(3) . . ?
C62 C72 H72A 109.4 . . ?
C62 C72 H72B 109.4 . . ?
H72A C72 H72B 108.0 . . ?
C82 C72 C62 111.4(5) . . ?
C82 C72 H72A 109.4 . . ?
C82 C72 H72B 109.4 . . ?
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 C61 110.96(11) . . ?
O3 C9 C62 113.43(15) . . ?
O4 C9 O3 126.1(6) . . ?
O4 C9 C61 122.9(6) . . ?
O4A C9 O3 123.2(9) . . ?
O4A C9 C62 123.3(10) . . ?
C1D N1D C2D 121.91(11) . . ?
C1D N1D C3D 120.91(11) . . ?
C3D N1D C2D 116.93(12) . . ?
O1D C1D N1D 124.19(12) . . ?
O1D C1D H1D 117.9 . . ?
N1D C1D H1D 117.9 . . ?
N1D C2D H2DC 109.5 . . ?
N1D C2D H2DB 109.5 . . ?
N1D C2D H2DA 109.5 . . ?
H2DC C2D H2DB 109.5 . . ?
H2DC C2D H2DA 109.5 . . ?
H2DB C2D H2DA 109.5 . . ?
N1D C3D H3DB 109.5 . . ?
N1D C3D H3DA 109.5 . . ?
N1D C3D H3DC 109.5 . . ?
H3DB C3D H3DA 109.5 . . ?
H3DB C3D H3DC 109.5 . . ?
H3DA C3D H3DC 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
_geom_hbond_publ_flag
O3 H3 O1D 0.84 1.69 2.5259(14) 174.9 . 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 2.1(2) . . . . ?
O1 C1 C2 C4 -176.71(13) . . . . ?
N1 C1 C2 C3 -178.95(11) . . . . ?
N1 C1 C2 C4 2.20(13) . . . . ?
N1 C61 C71 C81 -64.7(4) . . . . ?
N1 C61 C9 O3 -169.89(14) . . . . ?
N1 C61 C9 O4 8.1(17) . . . . ?
N1 C62 C72 C82 68.4(7) . . . . ?
N1 C62 C9 O3 166.9(2) . . . . ?
N1 C62 C9 O4A -17.6(19) . . . . ?
C1 N1 C5 O2 -174.29(13) . . . . ?
C1 N1 C5 C4 4.39(14) . . . . ?
C1 N1 C61 C71 -53.7(3) . . . . ?
C1 N1 C61 C9 70.4(2) . . . . ?
C1 N1 C62 C72 -135.8(3) . . . . ?
C1 N1 C62 C9 101.3(3) . . . . ?
C1 C2 C3 C4 -178.93(11) . . . 3_676 ?
C1 C2 C4 C3 179.20(10) . . . 3_676 ?
C1 C2 C4 C5 0.40(12) . . . . ?
C2 C4 C5 O2 175.78(14) . . . . ?
C2 C4 C5 N1 -2.85(13) . . . . ?
C3 C2 C4 C3 0.25(19) . . . 3_676 ?
C3 C2 C4 C5 -178.54(10) . . . . ?
C3 C4 C5 O2 -2.9(2) 3_676 . . . ?
C3 C4 C5 N1 178.46(12) 3_676 . . . ?
C4 C2 C3 C4 -0.23(18) . . . 3_676 ?
C5 N1 C1 O1 174.76(13) . . . . ?
C5 N1 C1 C2 -4.18(14) . . . . ?
C5 N1 C61 C71 141.42(19) . . . . ?
C5 N1 C61 C9 -94.5(2) . . . . ?
C5 N1 C62 C72 68.0(3) . . . . ?
C5 N1 C62 C9 -54.9(5) . . . . ?
C61 N1 C1 O1 9.4(2) . . . . ?
C61 N1 C1 C2 -169.51(15) . . . . ?
C61 N1 C5 O2 -6.4(2) . . . . ?
C61 N1 C5 C4 172.23(13) . . . . ?
C71 C61 C9 O3 -46.9(2) . . . . ?
C71 C61 C9 O4 131.1(16) . . . . ?
C62 N1 C1 O1 12.1(2) . . . . ?
C62 N1 C1 C2 -166.88(16) . . . . ?
C62 N1 C5 O2 -18.7(3) . . . . ?
C62 N1 C5 C4 160.0(3) . . . . ?
C72 C62 C9 O3 49.2(4) . . . . ?
C72 C62 C9 O4A -135.3(19) . . . . ?
C9 C61 C71 C81 176.4(4) . . . . ?
C9 C62 C72 C82 -170.3(7) . . . . ?
C2D N1D C1D O1D -176.63(16) . . . . ?
C3D N1D C1D O1D -2.5(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_p13_052mono
_database_code_depnum_ccdc_archive 'CCDC 2205756'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;Mohanlal Sukhadia University 
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H28 N2 O10 S2'
_chemical_formula_weight         544.58
_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 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1220 0.1202 '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                   12.768(3)
_cell_length_b                   9.2840(19)
_cell_length_c                   11.394(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.03(3)
_cell_angle_gamma                90
_cell_volume                     1260.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26463
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL3000 Scalepack'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12939
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.557
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.700
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3201
_reflns_number_total             3664
_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       HKL3000
_computing_data_collection       'PAL ADSC Quantum-210 ADX Program'
_computing_data_reduction        HKL3000
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL-XS'
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.084(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.076
_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)+(0.0843P)²+0.3199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1506
_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. Restrained distances
 O4-C9 \\sim O4A-C9
 with sigma of 0.02
3. Others
 Fixed Sof: O4(0.5) C61(0.5) H61(0.5) C71(0.5) H71A(0.5) H71B(0.5) C81(0.5)
 H81A(0.5) H81B(0.5) H81C(0.5) C62(0.5) H62(0.5) C72(0.5) H72A(0.5) H72B(0.5)
 C82(0.5) H82A(0.5) H82B(0.5) H82C(0.5) O4A(0.5)
4.a Ternary CH refined with riding coordinates:
 C61(H61), C62(H62)
4.b Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C72(H72A,H72B)
4.c Me refined with riding coordinates:
 C81(H81A,H81B,H81C), C82(H82A,H82B,H82C)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3A)
4.e Idealised Me refined as rotating group:
 C1D(H1DA,H1DB,H1DC), C2D(H2DA,H2DB,H2DC)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.22385(11) 0.52106(15) 0.05070(13) 0.0428(3) Uani 1 1 d . . . . .
O2 O 0.53571(15) 0.26284(13) 0.28123(12) 0.0484(4) Uani 1 1 d . . . . .
O3 O 0.19783(10) 0.13783(10) 0.28929(9) 0.0270(2) Uani 1 1 d . . . . .
H3 H 0.165428 0.060603 0.258199 0.041 Uiso 1 1 calc R U . . .
O4 O 0.2729(4) 0.1159(5) 0.1390(4) 0.0409(10) Uani 0.5 1 d D . P A 1
N1 N 0.36697(15) 0.38441(13) 0.18920(15) 0.0375(4) Uani 1 1 d . . . . .
C1 C 0.31833(14) 0.47384(16) 0.08571(15) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.40624(12) 0.49804(13) 0.03003(12) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.40149(12) 0.58066(14) -0.07305(12) 0.0234(3) Uani 1 1 d . . . . .
H3A H 0.336649 0.633675 -0.121169 0.028 Uiso 1 1 calc R U . . .
C4 C 0.50115(13) 0.42025(13) 0.10029(12) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.47602(17) 0.34372(15) 0.20268(14) 0.0336(4) Uani 1 1 d . . . . .
C61 C 0.3283(3) 0.3158(4) 0.2873(3) 0.0212(6) Uani 0.5 1 d . . P A 1
H61 H 0.394914 0.275954 0.356446 0.025 Uiso 0.5 1 calc R U P A 1
C71 C 0.2701(3) 0.4274(3) 0.3428(3) 0.0263(6) Uani 0.5 1 d . . P A 1
H71A H 0.207036 0.472657 0.274584 0.032 Uiso 0.5 1 calc R U P A 1
H71B H 0.239715 0.379676 0.401465 0.032 Uiso 0.5 1 calc R U P A 1
C81 C 0.3519(11) 0.5370(14) 0.4095(12) 0.044(3) Uani 0.5 1 d . . P A 1
H81A H 0.315646 0.608801 0.445244 0.066 Uiso 0.5 1 calc R U P A 1
H81B H 0.413823 0.491562 0.477208 0.066 Uiso 0.5 1 calc R U P A 1
H81C H 0.381242 0.584266 0.350705 0.066 Uiso 0.5 1 calc R U P A 1
C62 C 0.2866(4) 0.3423(4) 0.2466(3) 0.0249(6) Uani 0.5 1 d . . P A 2
H62 H 0.218550 0.404138 0.209635 0.030 Uiso 0.5 1 calc R U P A 2
C72 C 0.3382(3) 0.3775(3) 0.3857(3) 0.0305(6) Uani 0.5 1 d . . P A 2
H72A H 0.413145 0.331903 0.419722 0.037 Uiso 0.5 1 calc R U P A 2
H72B H 0.291258 0.332977 0.428632 0.037 Uiso 0.5 1 calc R U P A 2
C82 C 0.3516(10) 0.5404(13) 0.4201(13) 0.043(3) Uani 0.5 1 d . . P A 2
H82A H 0.385515 0.551130 0.511580 0.065 Uiso 0.5 1 calc R U P A 2
H82B H 0.400057 0.585821 0.380690 0.065 Uiso 0.5 1 calc R U P A 2
H82C H 0.277803 0.586898 0.389627 0.065 Uiso 0.5 1 calc R U P A 2
C9 C 0.25059(13) 0.18915(15) 0.21823(12) 0.0250(3) Uani 1 1 d D . . . .
S1D S 0.12174(3) 0.78615(4) 0.15126(3) 0.02709(15) Uani 1 1 d . . . . .
O1D O 0.08064(12) 0.91125(12) 0.20922(11) 0.0369(3) Uani 1 1 d . . . . .
C1D C 0.0883(2) 0.8308(2) -0.00971(17) 0.0465(5) Uani 1 1 d . . . . .
H1DA H 0.008697 0.856695 -0.047039 0.070 Uiso 1 1 calc R U . . .
H1DB H 0.103295 0.747771 -0.054389 0.070 Uiso 1 1 calc R U . . .
H1DC H 0.134286 0.912566 -0.016508 0.070 Uiso 1 1 calc R U . . .
C2D C 0.02070(16) 0.64876(17) 0.13288(17) 0.0356(4) Uani 1 1 d . . . . .
H2DA H 0.022310 0.617981 0.215784 0.053 Uiso 1 1 calc R U . . .
H2DB H 0.038001 0.566517 0.089053 0.053 Uiso 1 1 calc R U . . .
H2DC H -0.054084 0.685825 0.083645 0.053 Uiso 1 1 calc R U . . .
O4A O 0.2343(4) 0.1516(5) 0.1130(4) 0.0385(9) Uani 0.5 1 d D . P A 2


_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 1.209(2) . ?
O2 C5 1.207(2) . ?
O3 H3 0.8400 . ?
O3 C9 1.3144(16) . ?
O4 C9 1.242(5) . ?
N1 C1 1.393(2) . ?
N1 C5 1.397(2) . ?
N1 C61 1.515(3) . ?
N1 C62 1.455(4) . ?
C1 C2 1.491(2) . ?
C2 C3 1.3858(18) . ?
C2 C4 1.391(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.385(2) 3_665 ?
C4 C5 1.4958(18) . ?
C61 H61 1.0000 . ?
C61 C71 1.536(4) . ?
C61 C9 1.558(4) . ?
C71 H71A 0.9900 . ?
C71 H71B 0.9900 . ?
C71 C81 1.461(14) . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C62 H62 1.0000 . ?
C62 C72 1.517(5) . ?
C62 C9 1.493(3) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C72 C82 1.556(13) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
C9 O4A 1.193(4) . ?
S1D O1D 1.5196(12) . ?
S1D C1D 1.7765(17) . ?
S1D C2D 1.7723(16) . ?
C1D H1DA 0.9800 . ?
C1D H1DB 0.9800 . ?
C1D H1DC 0.9800 . ?
C2D H2DA 0.9800 . ?
C2D H2DB 0.9800 . ?
C2D H2DC 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 . . ?
C1 N1 C5 112.23(12) . . ?
C1 N1 C61 135.3(2) . . ?
C1 N1 C62 111.7(2) . . ?
C5 N1 C61 112.41(19) . . ?
C5 N1 C62 135.6(2) . . ?
O1 C1 N1 125.78(15) . . ?
O1 C1 C2 128.27(16) . . ?
N1 C1 C2 105.95(14) . . ?
C3 C2 C1 129.28(14) . . ?
C3 C2 C4 122.64(13) . . ?
C4 C2 C1 108.08(12) . . ?
C2 C3 H3A 122.7 . . ?
C4 C3 C2 114.62(13) 3_665 . ?
C4 C3 H3A 122.7 3_665 . ?
C2 C4 C5 108.00(13) . . ?
C3 C4 C2 122.74(12) 3_665 . ?
C3 C4 C5 129.26(14) 3_665 . ?
O2 C5 N1 126.09(14) . . ?
O2 C5 C4 128.24(17) . . ?
N1 C5 C4 105.67(14) . . ?
N1 C61 H61 109.0 . . ?
N1 C61 C71 110.7(2) . . ?
N1 C61 C9 105.1(2) . . ?
C71 C61 H61 109.0 . . ?
C71 C61 C9 113.7(3) . . ?
C9 C61 H61 109.0 . . ?
C61 C71 H71A 109.9 . . ?
C61 C71 H71B 109.9 . . ?
H71A C71 H71B 108.3 . . ?
C81 C71 C61 108.8(6) . . ?
C81 C71 H71A 109.9 . . ?
C81 C71 H71B 109.9 . . ?
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 H62 107.6 . . ?
N1 C62 C72 107.4(3) . . ?
N1 C62 C9 111.7(2) . . ?
C72 C62 H62 107.6 . . ?
C9 C62 H62 107.6 . . ?
C9 C62 C72 114.6(3) . . ?
C62 C72 H72A 108.3 . . ?
C62 C72 H72B 108.3 . . ?
C62 C72 C82 116.1(6) . . ?
H72A C72 H72B 107.4 . . ?
C82 C72 H72A 108.3 . . ?
C82 C72 H72B 108.3 . . ?
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 C61 109.65(15) . . ?
O3 C9 C62 113.42(16) . . ?
O4 C9 O3 123.4(3) . . ?
O4 C9 C61 120.7(3) . . ?
O4A C9 O3 124.8(3) . . ?
O4A C9 C62 115.2(3) . . ?
O1D S1D C1D 106.12(8) . . ?
O1D S1D C2D 104.55(7) . . ?
C2D S1D C1D 98.66(10) . . ?
S1D C1D H1DA 109.5 . . ?
S1D C1D H1DB 109.5 . . ?
S1D C1D H1DC 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
S1D C2D H2DA 109.5 . . ?
S1D C2D H2DB 109.5 . . ?
S1D C2D H2DC 109.5 . . ?
H2DA C2D H2DB 109.5 . . ?
H2DA C2D H2DC 109.5 . . ?
H2DB C2D H2DC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 0.8(2) . . . . ?
O1 C1 C2 C4 -178.95(14) . . . . ?
N1 C1 C2 C3 -178.92(13) . . . . ?
N1 C1 C2 C4 1.32(14) . . . . ?
N1 C61 C71 C81 -64.2(6) . . . . ?
N1 C61 C9 O3 -169.50(18) . . . . ?
N1 C61 C9 O4 37.4(4) . . . . ?
N1 C62 C72 C82 68.6(6) . . . . ?
N1 C62 C9 O3 166.1(2) . . . . ?
N1 C62 C9 O4A -41.0(4) . . . . ?
C1 N1 C5 O2 -177.13(15) . . . . ?
C1 N1 C5 C4 2.59(16) . . . . ?
C1 N1 C61 C71 -48.0(4) . . . . ?
C1 N1 C61 C9 75.2(3) . . . . ?
C1 N1 C62 C72 -127.5(2) . . . . ?
C1 N1 C62 C9 106.0(3) . . . . ?
C1 C2 C3 C4 -179.84(12) . . . 3_665 ?
C1 C2 C4 C3 179.90(12) . . . 3_665 ?
C1 C2 C4 C5 0.20(14) . . . . ?
C2 C4 C5 O2 178.07(15) . . . . ?
C2 C4 C5 N1 -1.65(15) . . . . ?
C3 C2 C4 C3 0.1(2) . . . 3_665 ?
C3 C2 C4 C5 -179.57(12) . . . . ?
C3 C4 C5 O2 -1.6(3) 3_665 . . . ?
C3 C4 C5 N1 178.68(13) 3_665 . . . ?
C4 C2 C3 C4 -0.1(2) . . . 3_665 ?
C5 N1 C1 O1 177.78(14) . . . . ?
C5 N1 C1 C2 -2.48(16) . . . . ?
C5 N1 C61 C71 135.1(2) . . . . ?
C5 N1 C61 C9 -101.7(2) . . . . ?
C5 N1 C62 C72 62.1(3) . . . . ?
C5 N1 C62 C9 -64.4(4) . . . . ?
C61 N1 C1 O1 0.9(3) . . . . ?
C61 N1 C1 C2 -179.4(2) . . . . ?
C61 N1 C5 O2 0.5(3) . . . . ?
C61 N1 C5 C4 -179.76(16) . . . . ?
C71 C61 C9 O3 -48.2(3) . . . . ?
C71 C61 C9 O4 158.7(3) . . . . ?
C62 N1 C1 O1 5.0(2) . . . . ?
C62 N1 C1 C2 -175.25(16) . . . . ?
C62 N1 C5 O2 -6.7(3) . . . . ?
C62 N1 C5 C4 173.0(2) . . . . ?
C72 C62 C9 O3 43.6(4) . . . . ?
C72 C62 C9 O4A -163.5(3) . . . . ?
C9 C61 C71 C81 177.6(5) . . . . ?
C9 C62 C72 C82 -166.5(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_036
_database_code_depnum_ccdc_archive 'CCDC 2205754'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;MLSU
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 3(C4 H8 O2)'
_chemical_formula_sum            'C30 H40 N2 O14'
_chemical_formula_weight         652.657
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 0.00347 0.00161 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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                   6.4872(13)
_cell_length_b                   9.976(2)
_cell_length_c                   12.810(3)
_cell_angle_alpha                71.54(3)
_cell_angle_beta                 86.66(3)
_cell_angle_gamma                85.26(3)
_cell_volume                     783.2(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.12
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             346.278
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9919
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7778
_diffrn_reflns_point_group_measured_fraction_full 0.9986
_diffrn_reflns_point_group_measured_fraction_max 0.9919
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.12
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9919
_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              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2052
_reflns_number_total             3560
_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         0.6430
_refine_diff_density_min         -0.4874
_refine_diff_density_rms         0.1036
_refine_ls_d_res_high            0.7704
_refine_ls_d_res_low             6.5276
_refine_ls_goodness_of_fit_ref   1.1022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.1022
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²+0.1396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1691
_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 Secondary CH2 refined with riding coordinates:
 C1D(H1Da,H1Db), C2D(H2Da,H2Db), C3D(H3Da,H3Db), C4D(H4Da,H4Db), C5D(H5Da,
 H5Db), C6D(H6Da,H6Db)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3a)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c)
2.d 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 0.4677(3) 0.47906(18) 0.66811(14) 0.0358(4) Uani 1.000000 .
O2 O 0.0423(3) 0.12594(16) 0.69530(14) 0.0314(4) Uani 1.000000 .
O3 O 0.0221(2) 0.17694(16) 0.90422(14) 0.0308(4) Uani 1.000000 .
H3 H -0.0589(18) 0.1241(7) 0.9493(18) 0.0461(6) Uiso 1.000000 GR
O4 O 0.2287(3) -0.02203(16) 0.94393(14) 0.0315(4) Uani 1.000000 .
N1 N 0.2601(3) 0.28675(19) 0.71802(16) 0.0246(4) Uani 1.000000 .
C1 C 0.3173(4) 0.4231(2) 0.65577(19) 0.0263(5) Uani 1.000000 .
C2 C 0.1602(3) 0.4784(2) 0.56882(18) 0.0244(5) Uani 1.000000 .
C3 C 0.1341(3) 0.6124(2) 0.49293(19) 0.0260(5) Uani 1.000000 .
H3a H 0.2214(3) 0.6862(2) 0.48818(19) 0.0312(6) Uiso 1.000000 R
C4 C 0.0314(3) 0.3704(2) 0.57586(18) 0.0238(5) Uani 1.000000 .
C5 C 0.1030(3) 0.2446(2) 0.66692(18) 0.0251(5) Uani 1.000000 .
C6 C 0.3594(4) 0.1892(2) 0.81709(19) 0.0257(5) Uani 1.000000 .
C7 C 0.4441(4) 0.2727(3) 0.8858(2) 0.0311(6) Uani 1.000000 .
H7a H 0.5694(15) 0.3170(15) 0.8492(7) 0.0466(8) Uiso 1.000000 GR
H7b H 0.3394(11) 0.3462(12) 0.8930(12) 0.0466(8) Uiso 1.000000 GR
H7c H 0.477(2) 0.2081(4) 0.9591(5) 0.0466(8) Uiso 1.000000 GR
C8 C 0.5277(4) 0.0921(3) 0.7855(2) 0.0344(6) Uani 1.000000 .
H8a H 0.4662(6) 0.0347(14) 0.7476(13) 0.0516(9) Uiso 1.000000 GR
H8b H 0.6315(15) 0.1494(3) 0.7366(12) 0.0516(9) Uiso 1.000000 GR
H8c H 0.5937(19) 0.0298(13) 0.8521(2) 0.0516(9) Uiso 1.000000 GR
C9 C 0.1924(3) 0.1033(2) 0.89234(18) 0.0243(5) Uani 1.000000 .
O1D O 0.2590(4) 0.2537(2) 0.17269(19) 0.0561(6) Uani 1.000000 .
O2D O -0.0784(3) 0.4390(2) 0.1953(2) 0.0654(7) Uani 1.000000 .
C1D C 0.2743(5) 0.4014(3) 0.1429(3) 0.0580(9) Uani 1.000000 .
H1Da H 0.4170(5) 0.4208(3) 0.1543(3) 0.0696(11) Uiso 1.000000 R
H1Db H 0.2461(5) 0.4447(3) 0.0637(3) 0.0696(11) Uiso 1.000000 R
C2D C 0.1275(5) 0.4667(3) 0.2079(3) 0.0559(9) Uani 1.000000 .
H2Da H 0.1406(5) 0.5703(3) 0.1836(3) 0.0671(10) Uiso 1.000000 R
H2Db H 0.1616(5) 0.4286(3) 0.2867(3) 0.0671(10) Uiso 1.000000 R
C3D C -0.0937(6) 0.2885(4) 0.2263(4) 0.0713(11) Uani 1.000000 .
H3Da H -0.0660(6) 0.2454(4) 0.3056(4) 0.0856(13) Uiso 1.000000 R
H3Db H -0.2358(6) 0.2684(4) 0.2144(4) 0.0856(13) Uiso 1.000000 R
C4D C 0.0564(6) 0.2251(4) 0.1607(3) 0.0692(11) Uani 1.000000 .
H4Da H 0.0219(6) 0.2633(4) 0.0820(3) 0.0830(13) Uiso 1.000000 R
H4Db H 0.0454(6) 0.1213(4) 0.1846(3) 0.0830(13) Uiso 1.000000 R
O3D O 0.4163(3) 0.8811(2) 0.48574(16) 0.0465(5) Uani 1.000000 .
C5D C 0.5578(5) 0.8677(3) 0.5695(3) 0.0526(8) Uani 1.000000 .
H5Da H 0.4798(5) 0.8672(3) 0.6384(3) 0.0631(10) Uiso 1.000000 R
H5Db H 0.6411(5) 0.7764(3) 0.5838(3) 0.0631(10) Uiso 1.000000 R
C6D C 0.3019(5) 1.0145(3) 0.4622(3) 0.0500(8) Uani 1.000000 .
H6Da H 0.2078(5) 1.0257(3) 0.4014(3) 0.0600(9) Uiso 1.000000 R
H6Db H 0.2162(5) 1.0182(3) 0.5279(3) 0.0600(9) 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 1.205(3) . ?
O2 C5 1.215(3) . ?
O3 H3 0.8400 . ?
O3 C9 1.304(3) . ?
O4 C9 1.225(3) . ?
N1 C1 1.409(3) . ?
N1 C5 1.402(3) . ?
N1 C6 1.477(3) . ?
C1 C2 1.494(3) . ?
C2 C3 1.385(3) . ?
C2 C4 1.395(3) . ?
C3 H3a 0.9500 . ?
C3 C4 1.394(3) 2_566 ?
C4 C5 1.481(3) . ?
C6 C7 1.539(3) . ?
C6 C8 1.521(3) . ?
C6 C9 1.532(3) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
O1D C1D 1.411(4) . ?
O1D C4D 1.395(4) . ?
O2D C2D 1.414(4) . ?
O2D C3D 1.436(4) . ?
C1D H1Da 0.9900 . ?
C1D H1Db 0.9900 . ?
C1D C2D 1.475(4) . ?
C2D H2Da 0.9900 . ?
C2D H2Db 0.9900 . ?
C3D H3Da 0.9900 . ?
C3D H3Db 0.9900 . ?
C3D C4D 1.482(5) . ?
C4D H4Da 0.9900 . ?
C4D H4Db 0.9900 . ?
O3D C5D 1.420(3) . ?
O3D C6D 1.422(4) . ?
C5D H5Da 0.9900 . ?
C5D H5Db 0.9900 . ?
C5D C6D 1.485(4) 2_676 ?
C6D H6Da 0.9900 . ?
C6D H6Db 0.9900 . ?

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 110.69(18) . . ?
C6 N1 C1 127.39(17) . . ?
C6 N1 C5 121.61(17) . . ?
N1 C1 O1 126.4(2) . . ?
C2 C1 O1 127.9(2) . . ?
C2 C1 N1 105.64(17) . . ?
C3 C2 C1 128.93(19) . . ?
C4 C2 C1 108.28(19) . . ?
C4 C2 C3 122.8(2) . . ?
H3a C3 C2 122.91(13) . . ?
C4 C3 C2 114.2(2) 2_566 . ?
C4 C3 H3a 122.91(13) 2_566 . ?
C3 C4 C2 123.0(2) 2_566 . ?
C5 C4 C2 107.65(18) . . ?
C5 C4 C3 129.3(2) . 2_566 ?
N1 C5 O2 124.5(2) . . ?
C4 C5 O2 128.7(2) . . ?
C4 C5 N1 106.85(17) . . ?
C7 C6 N1 110.54(18) . . ?
C8 C6 N1 110.71(19) . . ?
C8 C6 C7 111.7(2) . . ?
C9 C6 N1 108.41(17) . . ?
C9 C6 C7 104.31(18) . . ?
C9 C6 C8 110.93(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 109.5 . . ?
H8b C8 C6 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C6 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
O4 C9 O3 124.1(2) . . ?
C6 C9 O3 114.79(19) . . ?
C6 C9 O4 120.7(2) . . ?
C4D O1D C1D 109.7(2) . . ?
C3D O2D C2D 109.1(2) . . ?
H1Da C1D O1D 109.25(17) . . ?
H1Db C1D O1D 109.25(19) . . ?
H1Db C1D H1Da 107.9 . . ?
C2D C1D O1D 111.8(3) . . ?
C2D C1D H1Da 109.25(19) . . ?
C2D C1D H1Db 109.3(2) . . ?
C1D C2D O2D 110.9(3) . . ?
H2Da C2D O2D 109.46(16) . . ?
H2Da C2D C1D 109.46(18) . . ?
H2Db C2D O2D 109.46(19) . . ?
H2Db C2D C1D 109.5(2) . . ?
H2Db C2D H2Da 108.0 . . ?
H3Da C3D O2D 109.5(2) . . ?
H3Db C3D O2D 109.52(18) . . ?
H3Db C3D H3Da 108.1 . . ?
C4D C3D O2D 110.7(3) . . ?
C4D C3D H3Da 109.5(2) . . ?
C4D C3D H3Db 109.5(2) . . ?
C3D C4D O1D 111.7(3) . . ?
H4Da C4D O1D 109.29(19) . . ?
H4Da C4D C3D 109.3(2) . . ?
H4Db C4D O1D 109.29(16) . . ?
H4Db C4D C3D 109.29(19) . . ?
H4Db C4D H4Da 108.0 . . ?
C6D O3D C5D 109.5(2) . . ?
H5Da C5D O3D 109.32(17) . . ?
H5Db C5D O3D 109.32(15) . . ?
H5Db C5D H5Da 108.0 . . ?
C6D C5D O3D 111.5(2) 2_676 . ?
C6D C5D H5Da 109.32(18) 2_676 . ?
C6D C5D H5Db 109.32(18) 2_676 . ?
C5D C6D O3D 111.0(2) 2_676 . ?
H6Da C6D O3D 109.44(14) . . ?
H6Da C6D C5D 109.44(17) . 2_676 ?
H6Db C6D O3D 109.44(16) . . ?
H6Db C6D C5D 109.44(18) . 2_676 ?
H6Db C6D H6Da 108.0 . . ?

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 O4 0.8400 1.802(4) 2.639(2) 174(3) 2_557

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 -167.5(3) . . . . ?
O1 C1 N1 C6 6.1(3) . . . . ?
O1 C1 C2 C3 -10.0(3) . . . . ?
O1 C1 C2 C4 171.2(3) . . . . ?
O2 C5 N1 C1 170.6(2) . . . . ?
O2 C5 N1 C6 -3.4(3) . . . . ?
O2 C5 C4 C2 -174.5(3) . . . . ?
O2 C5 C4 C3 6.4(3) . . . 2_566 ?
O3 C9 C6 N1 -44.2(2) . . . . ?
O3 C9 C6 C7 73.6(2) . . . . ?
O3 C9 C6 C8 -166.0(2) . . . . ?
O4 C9 C6 N1 142.2(2) . . . . ?
O4 C9 C6 C7 -100.0(2) . . . . ?
O4 C9 C6 C8 20.4(2) . . . . ?
N1 C1 C2 C3 173.20(17) . . . . ?
N1 C1 C2 C4 -5.6(2) . . . . ?
N1 C5 C4 C2 5.7(2) . . . . ?
N1 C5 C4 C3 -173.41(17) . . . 2_566 ?
C1 C2 C3 C4 -178.9(2) . . . 2_566 ?
C1 C2 C4 C3 179.16(18) . . . 2_566 ?
C1 C2 C4 C5 -0.0(2) . . . . ?
C2 C3 C4 C2 0.2(2) . . 2_566 2_566 ?
C2 C3 C4 C5 -178.74(18) . . 2_566 2_566 ?
C2 C4 C3 C2 -0.2(2) . . 2_566 2_566 ?
O1D C1D C2D O2D -57.9(3) . . . . ?
O1D C4D C3D O2D 57.7(3) . . . . ?
O3D C5D C6D O3D 57.7(3) . . 2_676 2_676 ?
O3D C6D C5D O3D -57.7(2) . . 2_676 2_676 ?


_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_042
_database_code_depnum_ccdc_archive 'CCDC 2205753'
loop_
_audit_author_name
_audit_author_address
'Devendra Singh'
;MLSU
India
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H16 N2 O8, 2(C2 H6 O S)'
_chemical_formula_sum            'C22 H28 N2 O10 S2'
_chemical_formula_weight         544.607
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 0.00347 0.00161 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 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)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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                   16.231(3)
_cell_length_b                   7.0373(14)
_cell_length_c                   11.685(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.43(3)
_cell_angle_gamma                90
_cell_volume                     1292.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9709
_cell_measurement_temperature    206(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.17
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.9067
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             572.908
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.9923
_diffrn_reflns_Laue_measured_fraction_max 0.9875
_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       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11958
_diffrn_reflns_point_group_measured_fraction_full 0.9923
_diffrn_reflns_point_group_measured_fraction_max 0.9875
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      206.15
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.9875
_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              -21
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2487
_reflns_number_total             2919
_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         0.3616
_refine_diff_density_min         -0.2375
_refine_diff_density_rms         0.0655
_refine_ls_d_res_high            0.7705
_refine_ls_d_res_low             6.4230
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.0660
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+0.2546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0936
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3a)
2.b Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C1D(H1Da,H1Db,H1Dc), C2D(H2Da,H2Db,H2Dc)
2.c 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 0.31172(6) 0.34680(14) 0.75744(10) 0.0409(3) Uani 1.000000 .
O2 O 0.45355(7) 0.91694(14) 0.79292(10) 0.0418(3) Uani 1.000000 .
O3 O 0.19859(6) 0.68517(16) 0.75615(9) 0.0369(2) Uani 1.000000 .
H3 H 0.1476(2) 0.670(3) 0.7544(5) 0.0554(4) Uiso 1.000000 GR
O4 O 0.15757(7) 0.58106(17) 0.57017(10) 0.0446(3) Uani 1.000000 .
N1 N 0.36346(7) 0.65226(16) 0.74973(10) 0.0283(2) Uani 1.000000 .
C1 C 0.36255(8) 0.46963(19) 0.79803(12) 0.0297(3) Uani 1.000000 .
C2 C 0.43371(8) 0.46320(19) 0.90651(11) 0.0272(3) Uani 1.000000 .
C3 C 0.45781(8) 0.31768(18) 0.98781(12) 0.0291(3) Uani 1.000000 .
H3a H 0.43044(8) 0.19894(18) 0.97960(12) 0.0349(3) Uiso 1.000000 R
C4 C 0.47432(8) 0.63825(18) 0.91766(11) 0.0267(3) Uani 1.000000 .
C5 C 0.43200(8) 0.75936(19) 0.81475(11) 0.0287(3) Uani 1.000000 .
C6 C 0.29982(8) 0.7029(2) 0.63932(12) 0.0300(3) Uani 1.000000 .
C7 C 0.29468(10) 0.9180(2) 0.61807(15) 0.0414(4) Uani 1.000000 .
H7a H 0.2859(7) 0.9816(2) 0.6877(4) 0.0621(5) Uiso 1.000000 GR
H7b H 0.3473(3) 0.9623(3) 0.6022(10) 0.0621(5) Uiso 1.000000 GR
H7c H 0.2476(5) 0.9462(2) 0.5509(6) 0.0621(5) Uiso 1.000000 GR
C8 C 0.32101(10) 0.5987(2) 0.53552(13) 0.0395(3) Uani 1.000000 .
H8a H 0.3792(3) 0.6264(14) 0.5338(6) 0.0592(5) Uiso 1.000000 GR
H8b H 0.3145(7) 0.4630(3) 0.5446(6) 0.0592(5) Uiso 1.000000 GR
H8c H 0.2828(5) 0.6408(12) 0.46225(15) 0.0592(5) Uiso 1.000000 GR
C9 C 0.21112(8) 0.6444(2) 0.65200(12) 0.0309(3) Uani 1.000000 .
S1D S 0.02612(2) 0.40223(5) 0.35180(3) 0.03126(12) Uani 1.000000 .
O1D O -0.04221(6) 0.33493(17) 0.24516(9) 0.0412(3) Uani 1.000000 .
C1D C 0.03946(12) 0.2148(2) 0.45678(14) 0.0451(4) Uani 1.000000 .
H1Da H -0.0102(4) 0.2078(12) 0.4887(8) 0.0677(6) Uiso 1.000000 GR
H1Db H 0.0462(8) 0.0955(3) 0.4186(3) 0.0677(6) Uiso 1.000000 GR
H1Dc H 0.0896(5) 0.2388(9) 0.5203(6) 0.0677(6) Uiso 1.000000 GR
C2D C 0.12172(9) 0.3674(2) 0.30598(15) 0.0440(4) Uani 1.000000 .
H2Da H 0.1241(4) 0.2374(5) 0.2795(10) 0.0660(6) Uiso 1.000000 GR
H2Db H 0.1229(4) 0.4537(13) 0.2417(7) 0.0660(6) Uiso 1.000000 GR
H2Dc H 0.17025(9) 0.3921(17) 0.3718(3) 0.0660(6) 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 1.2074(16) . ?
O2 C5 1.2090(16) . ?
O3 H3 0.8300 . ?
O3 C9 1.3147(17) . ?
O4 C9 1.2058(17) . ?
N1 C1 1.4052(18) . ?
N1 C5 1.4007(16) . ?
N1 C6 1.4813(17) . ?
C1 C2 1.4878(19) . ?
C2 C3 1.3853(19) . ?
C2 C4 1.3879(18) . ?
C3 H3a 0.9400 . ?
C3 C4 1.3869(18) 3_667 ?
C4 C5 1.4942(19) . ?
C6 C7 1.533(2) . ?
C6 C8 1.528(2) . ?
C6 C9 1.5396(18) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 H7c 0.9700 . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C8 H8c 0.9700 . ?
S1D O1D 1.5227(12) . ?
S1D C1D 1.7774(16) . ?
S1D C2D 1.7800(16) . ?
C1D H1Da 0.9700 . ?
C1D H1Db 0.9700 . ?
C1D H1Dc 0.9700 . ?
C2D H2Da 0.9700 . ?
C2D H2Db 0.9700 . ?
C2D H2Dc 0.9700 . ?

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 111.14(11) . . ?
C6 N1 C1 119.65(10) . . ?
C6 N1 C5 129.08(11) . . ?
N1 C1 O1 124.86(13) . . ?
C2 C1 O1 128.49(13) . . ?
C2 C1 N1 106.64(11) . . ?
C3 C2 C1 129.30(12) . . ?
C4 C2 C1 107.62(11) . . ?
C4 C2 C3 123.05(12) . . ?
H3a C3 C2 122.79(7) . . ?
C4 C3 C2 114.42(12) 3_667 . ?
C4 C3 H3a 122.79(8) 3_667 . ?
C3 C4 C2 122.52(12) 3_667 . ?
C5 C4 C2 108.57(11) . . ?
C5 C4 C3 128.91(12) . 3_667 ?
N1 C5 O2 127.71(12) . . ?
C4 C5 O2 126.43(12) . . ?
C4 C5 N1 105.86(11) . . ?
C7 C6 N1 112.11(11) . . ?
C8 C6 N1 109.28(11) . . ?
C8 C6 C7 111.04(12) . . ?
C9 C6 N1 108.53(10) . . ?
C9 C6 C7 105.38(11) . . ?
C9 C6 C8 110.43(11) . . ?
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 109.5 . . ?
H8b C8 C6 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C6 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
O4 C9 O3 124.57(12) . . ?
C6 C9 O3 113.25(11) . . ?
C6 C9 O4 121.94(12) . . ?
C1D S1D O1D 105.82(7) . . ?
C2D S1D O1D 102.88(7) . . ?
C2D S1D C1D 98.05(8) . . ?
H1Da C1D S1D 109.5 . . ?
H1Db C1D S1D 109.5 . . ?
H1Db C1D H1Da 109.5 . . ?
H1Dc C1D S1D 109.5 . . ?
H1Dc C1D H1Da 109.5 . . ?
H1Dc C1D H1Db 109.5 . . ?
H2Da C2D S1D 109.5 . . ?
H2Db C2D S1D 109.5 . . ?
H2Db C2D H2Da 109.5 . . ?
H2Dc C2D S1D 109.5 . . ?
H2Dc C2D H2Da 109.5 . . ?
H2Dc C2D H2Db 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 0.8300 1.712(2) 2.5383(15) 173.7(18) 3_566

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 -177.90(14) . . . . ?
O1 C1 N1 C6 -1.54(17) . . . . ?
O1 C1 C2 C3 -1.36(19) . . . . ?
O1 C1 C2 C4 -179.64(15) . . . . ?
O2 C5 N1 C1 175.46(15) . . . . ?
O2 C5 N1 C6 -0.46(19) . . . . ?
O2 C5 C4 C2 -176.04(14) . . . . ?
O2 C5 C4 C3 4.46(18) . . . 3_667 ?
O3 C9 C6 N1 42.32(12) . . . . ?
O3 C9 C6 C7 -77.93(13) . . . . ?
O3 C9 C6 C8 162.09(12) . . . . ?
O4 C9 C6 N1 -142.95(14) . . . . ?
O4 C9 C6 C7 96.79(15) . . . . ?
O4 C9 C6 C8 -23.19(16) . . . . ?
N1 C1 C2 C3 177.50(10) . . . . ?
N1 C1 C2 C4 -0.79(11) . . . . ?
N1 C5 C4 C2 3.60(11) . . . . ?
N1 C5 C4 C3 -175.90(10) . . . 3_667 ?
C1 C2 C3 C4 -177.50(14) . . . 3_667 ?
C1 C2 C4 C3 177.82(10) . . . 3_667 ?
C1 C2 C4 C5 -1.72(11) . . . . ?
C2 C3 C4 C2 -0.55(12) . . 3_667 3_667 ?
C2 C3 C4 C5 -179.98(10) . . 3_667 3_667 ?
C2 C4 C3 C2 0.55(11) . . 3_667 3_667 ?


_olex2_submission_special_instructions 'No special instructions were received'
