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

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

data_NKS_MKG_TR-PEP
_database_code_depnum_ccdc_archive 'CCDC 2174977'
loop_
_audit_author_name
_audit_author_address
'Nagendra K Sharma'
;SCS, National Institute of Science Education and Research (NISER) Bhubaneswar
India
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_chemical_formula_moiety         'C10 H13 N2 O3, C2 F3 O2'
_chemical_formula_sum            'C12 H13 F3 N2 O5'
_chemical_formula_weight         322.243
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C13 H15 N1 O8 '
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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'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 0.250800013542
'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 -11.5290002823
'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           1
_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

_symmetry_Int_Tables_number      1
_cell_length_a                   4.9797(3)
_cell_length_b                   6.2209(3)
_cell_length_c                   11.7288(6)
_cell_angle_alpha                76.575(4)
_cell_angle_beta                 80.995(5)
_cell_angle_gamma                77.331(4)
_cell_volume                     342.66(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2340
_cell_measurement_theta_min      3.5280
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       plate
_exptl_crystal_F_000             166.140
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.8749
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13896
_diffrn_reflns_point_group_measured_fraction_full 0.9850
_diffrn_reflns_point_group_measured_fraction_max 0.8186
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.36
_diffrn_reflns_theta_min         3.43
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8749
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  38.00   0.50   24.00    --    6.83 -91.00-112.00  134
  2  ω    -29.00  24.00   0.50   24.00    --   -7.14 -91.00-112.00  106
  3  ω    -38.00   8.00   0.50   24.00    --   -7.14  91.00   1.00   92
  4  ω      1.00  76.00   0.50   24.00    --    6.83  19.00  60.00  150
  5  ω    -61.00  13.00   0.50   24.00    --    6.83 -19.00  90.00  148
  6  ω      4.00  73.00   0.50   24.00    --    6.83  38.00 120.00  138
  7  ω     -9.00  50.00   0.50   24.00    --    6.83-111.00 176.63  118
  8  ω      1.00  76.00   0.50   24.00    --    6.83  19.00 -60.00  150
  9  ω      4.00  73.00   0.50   24.00    --    6.83  38.00-180.00  138
 10  ω    -59.00  10.00   0.50   24.00    --    6.83 -38.00 -30.00  138
 11  ω     -5.00  70.00   0.50   24.00    --    6.83  57.00  60.00  150
 12  ω    -70.00   4.00   0.50   24.00    --   -7.14 -57.00-180.00  148
 13  ω    -68.00 -33.00   0.50   24.00    --   -7.14 141.00  97.62   70
 14  ω    -59.00 -24.00   0.50   24.00    --   -7.14 126.00-135.18   70
 15  ω    -75.00 -36.00   0.50   24.00    --   -7.14 150.00-129.34   78
 16  ω    -20.00  29.00   0.50   24.00    --   -7.14 -99.00-120.00   98
 17  ω    -61.00 -27.00   0.50   24.00    --   -7.14 129.00  -8.08   68
 18  ω    -60.00 -26.00   0.50   24.00    --   -7.14 128.00 -45.63   68
 19  ω    -71.00  16.00   0.50   24.00    --   -7.14 -77.00  60.00  174
 20  ω    -63.00 -29.00   0.50   24.00    --   -7.14 133.00 175.22   68
 21  ω    -62.00 -27.00   0.50   24.00    --   -7.14 131.00  33.77   70
 22  ω      4.00  73.00   0.50   24.00    --    6.83  38.00-150.00  138
 23  ω    -58.00 -28.00   0.50   24.00    --   -7.14 125.00 148.68   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1108291000
_diffrn_orient_matrix_UB_12      0.0055929000
_diffrn_orient_matrix_UB_13      -0.0325687000
_diffrn_orient_matrix_UB_21      -0.0568159000
_diffrn_orient_matrix_UB_22      -0.0770087000
_diffrn_orient_matrix_UB_23      0.0471795000
_diffrn_orient_matrix_UB_31      -0.0779123000
_diffrn_orient_matrix_UB_32      0.0910846000
_diffrn_orient_matrix_UB_33      0.0250498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.762
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                2919
_reflns_number_total             3692
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1990
_refine_diff_density_min         -0.2040
_refine_diff_density_rms         0.0473
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_d_res_high            0.6829
_refine_ls_d_res_low             5.9401
_refine_ls_goodness_of_fit_ref   1.0394
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.0394
_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)+(0.0616P)²+0.0052P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1094
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C4(H4), C5(H5), C6(H6), N1(H1)
2.d Idealised Me refined as rotating group:
 N2(H2a,H2b,H2c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     dual
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
O2 O -1.0935(3) -0.6033(2) -0.39951(12) 0.0470(3) Uani 1.000000 .
O3 O -1.0890(3) -0.6103(2) -0.58910(12) 0.0469(3) Uani 1.000000 .
O1 O -0.4272(3) 0.1345(2) -0.38094(12) 0.0430(3) Uani 1.000000 .
O4 O -0.5042(3) -0.8324(2) -0.68238(12) 0.0481(3) Uani 1.000000 .
F1 F -0.2421(4) -0.5670(2) -0.85043(15) 0.0876(6) Uani 1.000000 .
O5 O -0.2344(3) -1.1364(2) -0.73509(16) 0.0575(4) Uani 1.000000 .
N1 N -0.7018(3) -0.1042(2) -0.44520(13) 0.0358(3) Uani 1.000000 .
F3 F -0.2423(4) -0.8080(3) -0.95249(12) 0.0836(5) Uani 1.000000 .
C10 C -1.0068(4) -0.5530(3) -0.51201(16) 0.0343(4) Uani 1.000000 .
N2 N -0.6765(3) -0.3852(2) -0.66160(14) 0.0387(3) Uani 1.000000 .
F2 F 0.0943(3) -0.8408(4) -0.85567(17) 0.0939(6) Uani 1.000000 .
C11 C -0.3197(4) -0.9313(3) -0.74492(16) 0.0373(4) Uani 1.000000 .
C2 C -0.6877(4) -0.1447(3) -0.32898(15) 0.0353(4) Uani 1.000000 .
C1 C -0.5315(3) 0.0016(3) -0.29519(16) 0.0351(3) Uani 1.000000 .
C9 C -0.7836(3) -0.4105(3) -0.53510(15) 0.0325(3) Uani 1.000000 .
C8 C -0.8929(4) -0.1805(3) -0.50085(16) 0.0360(4) Uani 1.000000 .
C3 C -0.8124(4) -0.3115(3) -0.25178(18) 0.0477(5) Uani 1.000000 .
C12 C -0.1774(5) -0.7845(3) -0.85118(18) 0.0477(5) Uani 1.000000 .
C7 C -0.4937(5) 0.0000(4) -0.1779(2) 0.0516(5) Uani 1.000000 .
C4 C -0.8324(6) -0.3766(4) -0.1304(2) 0.0623(6) Uani 1.000000 .
C5 C -0.7347(7) -0.2968(5) -0.0486(2) 0.0709(7) Uani 1.000000 .
C6 C -0.5832(6) -0.1272(5) -0.0716(2) 0.0675(7) Uani 1.000000 .
H9 H -0.6321(3) -0.4917(3) -0.48822(15) 0.0390(4) Uiso 1.000000 R
H8a H -1.0619(4) -0.1887(3) -0.44758(16) 0.0432(4) Uiso 1.000000 R
H8b H -0.9399(4) -0.0693(3) -0.57134(16) 0.0432(4) Uiso 1.000000 R
H3 H -0.8964(4) -0.3926(3) -0.28849(18) 0.0572(5) Uiso 1.000000 R
H7 H -0.3899(5) 0.1031(4) -0.1713(2) 0.0619(6) Uiso 1.000000 R
H4 H -0.9278(6) -0.4937(4) -0.0990(2) 0.0748(7) Uiso 1.000000 R
H5 H -0.7742(7) -0.3633(5) 0.0302(2) 0.0851(9) Uiso 1.000000 R
H6 H -0.5342(6) -0.0936(5) -0.0053(2) 0.0810(8) Uiso 1.000000 R
H1 H -0.5884(3) -0.0266(2) -0.49040(13) 0.0429(4) Uiso 1.000000 R
H2a H -0.8118(8) -0.310(2) -0.70523(14) 0.0464(4) Uiso 1.000000 GR
H2b H -0.5385(19) -0.309(2) -0.6767(3) 0.0464(4) Uiso 1.000000 GR
H2c H -0.615(3) -0.5206(2) -0.6789(3) 0.0464(4) Uiso 1.000000 GR
H2 H -1.189(5) -0.700(4) -0.3882(4) 0.0705(5) 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
O2 C10 1.309(2) . ?
O3 C10 1.200(2) . ?
O1 C1 1.266(2) . ?
O4 C11 1.229(2) . ?
F1 C12 1.322(3) . ?
O5 C11 1.238(2) . ?
N1 C2 1.338(2) . ?
N1 C8 1.447(2) . ?
F3 C12 1.326(3) . ?
C10 C9 1.524(2) . ?
N2 C9 1.480(2) . ?
F2 C12 1.317(3) . ?
C11 C12 1.539(3) . ?
C2 C1 1.471(2) . ?
C2 C3 1.397(2) . ?
C1 C7 1.415(3) . ?
C9 C8 1.537(2) . ?
C3 C4 1.381(3) . ?
C7 C6 1.379(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.381(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C2 125.15(14) . . ?
O3 C10 O2 125.38(15) . . ?
C9 C10 O2 111.64(14) . . ?
C9 C10 O3 122.98(16) . . ?
O5 C11 O4 128.39(18) . . ?
C12 C11 O4 116.84(16) . . ?
C12 C11 O5 114.76(17) . . ?
C1 C2 N1 113.09(14) . . ?
C3 C2 N1 121.13(16) . . ?
C3 C2 C1 125.78(17) . . ?
C2 C1 O1 114.60(16) . . ?
C7 C1 O1 120.63(16) . . ?
C7 C1 C2 124.77(17) . . ?
N2 C9 C10 107.57(14) . . ?
C8 C9 C10 112.16(13) . . ?
C8 C9 N2 111.40(13) . . ?
C9 C8 N1 114.77(14) . . ?
C4 C3 C2 131.10(19) . . ?
F3 C12 F1 106.7(2) . . ?
F2 C12 F1 106.62(19) . . ?
F2 C12 F3 106.4(2) . . ?
C11 C12 F1 113.64(17) . . ?
C11 C12 F3 111.62(17) . . ?
C11 C12 F2 111.46(18) . . ?
C6 C7 C1 131.5(2) . . ?
C5 C4 C3 130.5(2) . . ?
C6 C5 C4 126.4(2) . . ?
C5 C6 C7 129.8(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_mkg-660
_database_code_depnum_ccdc_archive 'CCDC 2212187'
loop_
_audit_author_name
_audit_author_address
'Nagendra Sharma'
;SCS, National Institute of science Education and Research (NISER), Bhubaneswar, India
India
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N3 O5'
_chemical_formula_sum            'C18 H23 N3 O5'
_chemical_formula_weight         361.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H92 N12 O20 '
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                   12.8343(4)
_cell_length_b                   8.2701(3)
_cell_length_c                   17.3938(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.530(4)
_cell_angle_gamma                90
_cell_volume                     1750.48(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10607
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5750
_cell_measurement_theta_min      3.4110
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16538
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.288
_diffrn_reflns_theta_min         3.422
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.812
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  -1.00   0.50    6.46    --   -4.14 -28.00  93.00  142
  2  ω     -6.00  59.00   0.50    6.46    --   -4.14  28.00-104.00  130
  3  ω    -67.00  -2.00   0.50    6.46    --   -4.14 -57.00-120.00  130
  4  ω    -11.00  32.00   0.50    6.46    --   -4.14 -99.00 150.00   86
  5  ω    -70.00 -45.00   0.50    6.46    --   -4.14 -37.00 150.00   50
  6  ω    -14.00  27.00   0.50    6.46    --   -4.14 -99.00  30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0491755000
_diffrn_orient_matrix_UB_12      0.0309840000
_diffrn_orient_matrix_UB_13      0.0046728000
_diffrn_orient_matrix_UB_21      0.0239957000
_diffrn_orient_matrix_UB_22      -0.0033525000
_diffrn_orient_matrix_UB_23      0.0427367000
_diffrn_orient_matrix_UB_31      0.0200704000
_diffrn_orient_matrix_UB_32      0.0799327000
_diffrn_orient_matrix_UB_33      -0.0000362000
_diffrn_oxdiff_digest_frames     
;
01d2cd25d004e4f183a468d8bc5afe211600620ca2b
;
_diffrn_oxdiff_digest_hkl        
;
01527e4dd9f46785259c937f0cb8d16234c4f5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3825
_reflns_number_total             4265
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.063
_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)+(0.0483P)²+0.5819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C5(H5), C7(H7), C6(H6), C4(H4)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C)
;
_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
O5 O 0.92897(6) 0.20516(9) 0.43142(4) 0.01694(17) Uani 1 1 d . . . . .
O3 O 0.89990(6) 0.36353(10) 0.56046(5) 0.02103(18) Uani 1 1 d . . . . .
O4 O 0.77023(6) 0.16041(10) 0.32795(5) 0.01992(17) Uani 1 1 d . . . . .
O2 O 0.53473(6) 0.27336(10) 0.51558(5) 0.02094(18) Uani 1 1 d . . . . .
O1 O 0.29218(6) -0.00571(10) 0.35954(5) 0.02249(18) Uani 1 1 d . . . . .
N3 N 0.76648(7) 0.23668(11) 0.45231(5) 0.01508(18) Uani 1 1 d . . . . .
N2 N 0.71848(7) 0.33818(11) 0.55535(5) 0.01567(18) Uani 1 1 d . . . . .
N1 N 0.49633(7) 0.01656(11) 0.38266(5) 0.01783(19) Uani 1 1 d . . . . .
H1 H 0.462725 -0.017403 0.415162 0.021 Uiso 1 1 calc R . . . .
C14 C 0.82156(8) 0.19812(12) 0.39681(6) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.31483(8) 0.03412(13) 0.29731(7) 0.0170(2) Uani 1 1 d . . . . .
C13 C 0.80807(8) 0.31759(12) 0.52676(6) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.43389(8) 0.04878(12) 0.30595(6) 0.0158(2) Uani 1 1 d . . . . .
C3 C 0.48024(9) 0.08972(13) 0.24641(6) 0.0180(2) Uani 1 1 d . . . . .
H3 H 0.556546 0.095874 0.264114 0.022 Uiso 1 1 calc R . . . .
C9 C 0.64765(8) 0.21248(13) 0.42969(6) 0.0148(2) Uani 1 1 d . . . . .
H9 H 0.609736 0.276734 0.381584 0.018 Uiso 1 1 calc R . . . .
C10 C 0.62278(8) 0.27804(13) 0.50356(6) 0.0156(2) Uani 1 1 d . . . . .
C8 C 0.61405(8) 0.03344(13) 0.41563(6) 0.0170(2) Uani 1 1 d . . . . .
H8A H 0.648048 -0.014010 0.378494 0.020 Uiso 1 1 calc R . . . .
H8B H 0.640364 -0.024604 0.466631 0.020 Uiso 1 1 calc R . . . .
C5 C 0.32085(10) 0.12918(14) 0.11884(7) 0.0222(2) Uani 1 1 d . . . . .
H5 H 0.304708 0.152092 0.063942 0.027 Uiso 1 1 calc R . . . .
C11 C 0.73059(9) 0.39794(13) 0.63696(6) 0.0187(2) Uani 1 1 d . . . . .
H11A H 0.807688 0.394911 0.669129 0.022 Uiso 1 1 calc R . . . .
H11B H 0.691219 0.326482 0.662320 0.022 Uiso 1 1 calc R . . . .
C7 C 0.22865(9) 0.06509(14) 0.22309(7) 0.0205(2) Uani 1 1 d . . . . .
H7 H 0.158375 0.057153 0.227284 0.025 Uiso 1 1 calc R . . . .
C6 C 0.23049(9) 0.10424(14) 0.14702(7) 0.0229(2) Uani 1 1 d . . . . .
H6 H 0.161847 0.116181 0.108116 0.027 Uiso 1 1 calc R . . . .
C17 C 0.99458(9) 0.27371(14) 0.31721(7) 0.0195(2) Uani 1 1 d . . . . .
H17A H 0.921804 0.268033 0.279006 0.029 Uiso 1 1 calc GR . . . .
H17B H 1.047215 0.246441 0.290540 0.029 Uiso 1 1 calc GR . . . .
H17C H 1.008428 0.381416 0.338614 0.029 Uiso 1 1 calc GR . . . .
C4 C 0.42996(9) 0.12320(13) 0.16382(7) 0.0202(2) Uani 1 1 d . . . . .
H4 H 0.478288 0.144755 0.135028 0.024 Uiso 1 1 calc R . . . .
C15 C 1.00451(8) 0.15553(13) 0.38591(6) 0.0167(2) Uani 1 1 d . . . . .
C12 C 0.68798(10) 0.56869(14) 0.63731(7) 0.0245(2) Uani 1 1 d . . . . .
H12A H 0.612293 0.573438 0.604150 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.730427 0.641475 0.616172 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.694206 0.599358 0.691820 0.037 Uiso 1 1 calc GR . . . .
C16 C 1.11578(9) 0.17141(16) 0.45048(7) 0.0228(2) Uani 1 1 d . . . . .
H16A H 1.127419 0.281862 0.468108 0.034 Uiso 1 1 calc GR . . . .
H16B H 1.172288 0.138906 0.428453 0.034 Uiso 1 1 calc GR . . . .
H16C H 1.118093 0.103520 0.495760 0.034 Uiso 1 1 calc GR . . . .
C18 C 0.98192(10) -0.01807(14) 0.35729(7) 0.0235(2) Uani 1 1 d . . . . .
H18A H 0.980380 -0.085264 0.401919 0.035 Uiso 1 1 calc GR . . . .
H18B H 1.038834 -0.054777 0.336629 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.912262 -0.024033 0.315204 0.035 Uiso 1 1 calc GR . . . .


_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
O5 C14 1.3186(12) . ?
O5 C15 1.4909(12) . ?
O3 C13 1.1991(13) . ?
O4 C14 1.2101(13) . ?
O2 C10 1.2134(13) . ?
O1 C1 1.2508(13) . ?
N3 C14 1.4025(13) . ?
N3 C13 1.4036(13) . ?
N3 C9 1.4627(12) . ?
N2 C13 1.4007(13) . ?
N2 C10 1.3653(13) . ?
N2 C11 1.4640(13) . ?
N1 C2 1.3468(14) . ?
N1 C8 1.4422(13) . ?
C1 C2 1.4921(14) . ?
C1 C7 1.4311(15) . ?
C2 C3 1.3901(14) . ?
C3 C4 1.4027(15) . ?
C9 C10 1.5192(14) . ?
C9 C8 1.5399(14) . ?
C5 C6 1.4104(17) . ?
C5 C4 1.3708(16) . ?
C11 C12 1.5150(16) . ?
C7 C6 1.3696(17) . ?
C17 C15 1.5174(15) . ?
C15 C16 1.5162(15) . ?
C15 C18 1.5170(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O5 C15 120.48(8) . . ?
C14 N3 C13 128.04(9) . . ?
C14 N3 C9 119.62(8) . . ?
C13 N3 C9 111.82(8) . . ?
C13 N2 C11 122.62(9) . . ?
C10 N2 C13 112.92(8) . . ?
C10 N2 C11 123.97(9) . . ?
C2 N1 C8 126.38(9) . . ?
O5 C14 N3 110.99(9) . . ?
O4 C14 O5 128.66(10) . . ?
O4 C14 N3 120.32(9) . . ?
O1 C1 C2 116.52(10) . . ?
O1 C1 C7 120.14(9) . . ?
C7 C1 C2 123.33(9) . . ?
O3 C13 N3 128.95(9) . . ?
O3 C13 N2 125.31(9) . . ?
N2 C13 N3 105.73(8) . . ?
N1 C2 C1 110.59(9) . . ?
N1 C2 C3 121.70(9) . . ?
C3 C2 C1 127.72(10) . . ?
C2 C3 C4 130.13(10) . . ?
N3 C9 C10 101.83(8) . . ?
N3 C9 C8 112.94(8) . . ?
C10 C9 C8 110.73(8) . . ?
O2 C10 N2 126.14(10) . . ?
O2 C10 C9 126.29(10) . . ?
N2 C10 C9 107.53(8) . . ?
N1 C8 C9 111.18(8) . . ?
C4 C5 C6 126.87(10) . . ?
N2 C11 C12 113.04(9) . . ?
C6 C7 C1 131.92(10) . . ?
C7 C6 C5 129.71(11) . . ?
C5 C4 C3 130.22(10) . . ?
O5 C15 C17 109.56(8) . . ?
O5 C15 C16 101.61(8) . . ?
O5 C15 C18 110.25(8) . . ?
C16 C15 C17 110.56(9) . . ?
C16 C15 C18 111.21(9) . . ?
C18 C15 C17 113.06(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.307
_oxdiff_exptl_absorpt_empirical_full_min 0.647
