# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 
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data_mo_190327e_0m
_audit_block_doi                 10.5517/ccdc.csd.cc22ygwd
_database_code_depnum_ccdc_archive 'CCDC 1934954'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.bioorg.2019.103464 2019
loop_
_audit_author_name
_audit_author_address
'piperine hydrazone derivative'
;Huazhong agriculture university
China
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N3 O4, C H4 O'
_chemical_formula_sum            'C24 H29 N3 O5'
_chemical_formula_weight         439.50
_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                   11.298(3)
_cell_length_b                   13.398(3)
_cell_length_c                   15.678(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.247(4)
_cell_angle_gamma                90
_cell_volume                     2266.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2466
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17545
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.887
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2716
_reflns_number_total             4630
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+0.0523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1535
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C2(H2A,H2B), C4(H4A,H4B), C23(H23A,H23B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C6(H6), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), 
 C18(H18), C21(H21), C22(H22), N3(H3) 
2.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C24(H24A,H24B,H24C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O1(H1), O5(H5) 
;
_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
C1 C 0.0953(2) 0.39825(18) -0.31984(16) 0.0642(6) Uani 1 1 d . . . . .
H1A H 0.1225 0.3673 -0.3660 0.096 Uiso 1 1 calc GR . . . .
H1B H 0.1660 0.4159 -0.2708 0.096 Uiso 1 1 calc GR . . . .
H1C H 0.0486 0.4573 -0.3430 0.096 Uiso 1 1 calc GR . . . .
C2 C 0.01545(18) 0.32701(15) -0.28826(14) 0.0505(5) Uani 1 1 d . . . . .
H2A H -0.0128 0.3593 -0.2425 0.061 Uiso 1 1 calc R . . . .
H2B H -0.0571 0.3113 -0.3378 0.061 Uiso 1 1 calc R . . . .
C3 C -0.0332(3) 0.09182(19) -0.33995(18) 0.0786(8) Uani 1 1 d . . . . .
H3A H -0.0262 0.0419 -0.3821 0.118 Uiso 1 1 calc GR . . . .
H3B H -0.1061 0.1312 -0.3654 0.118 Uiso 1 1 calc GR . . . .
H3C H -0.0391 0.0600 -0.2865 0.118 Uiso 1 1 calc GR . . . .
C4 C 0.0784(2) 0.15757(16) -0.31795(14) 0.0568(6) Uani 1 1 d . . . . .
H4A H 0.1518 0.1166 -0.2953 0.068 Uiso 1 1 calc R . . . .
H4B H 0.0834 0.1894 -0.3723 0.068 Uiso 1 1 calc R . . . .
C5 C 0.14260(18) 0.22484(15) -0.16421(14) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.16632(19) 0.30732(15) -0.10652(14) 0.0503(5) Uani 1 1 d . . . . .
H6 H 0.1367 0.3697 -0.1291 0.060 Uiso 1 1 calc R . . . .
C7 C 0.23146(18) 0.29891(15) -0.01830(14) 0.0456(5) Uani 1 1 d . . . . .
C8 C 0.27656(17) 0.20627(15) 0.01969(13) 0.0443(5) Uani 1 1 d . . . . .
C9 C 0.25139(19) 0.12485(15) -0.03816(14) 0.0501(5) Uani 1 1 d . . . . .
H9 H 0.2794 0.0623 -0.0152 0.060 Uiso 1 1 calc R . . . .
C10 C 0.18797(19) 0.13193(15) -0.12643(15) 0.0524(6) Uani 1 1 d . . . . .
H10 H 0.1745 0.0751 -0.1621 0.063 Uiso 1 1 calc R . . . .
C11 C 0.34419(18) 0.19449(16) 0.11158(14) 0.0483(5) Uani 1 1 d . . . . .
H11 H 0.3689 0.1308 0.1333 0.058 Uiso 1 1 calc R . . . .
C12 C 0.47254(17) 0.32111(16) 0.31255(14) 0.0459(5) Uani 1 1 d . . . . .
C13 C 0.53305(18) 0.28560(16) 0.40295(14) 0.0494(5) Uani 1 1 d . . . . .
H13 H 0.5489 0.2176 0.4115 0.059 Uiso 1 1 calc R . . . .
C14 C 0.56667(17) 0.34510(16) 0.47365(14) 0.0483(5) Uani 1 1 d . . . . .
H14 H 0.5510 0.4130 0.4643 0.058 Uiso 1 1 calc R . . . .
C15 C 0.62494(18) 0.31298(16) 0.56291(14) 0.0508(5) Uani 1 1 d . . . . .
H15 H 0.6466 0.2459 0.5711 0.061 Uiso 1 1 calc R . . . .
C16 C 0.65111(17) 0.36977(15) 0.63546(14) 0.0480(5) Uani 1 1 d . . . . .
H16 H 0.6297 0.4368 0.6266 0.058 Uiso 1 1 calc R . . . .
C17 C 0.70934(17) 0.33906(15) 0.72709(14) 0.0450(5) Uani 1 1 d . . . . .
C18 C 0.73949(18) 0.23894(16) 0.74914(14) 0.0501(5) Uani 1 1 d . . . . .
H18 H 0.7197 0.1891 0.7059 0.060 Uiso 1 1 calc R . . . .
C19 C 0.79834(19) 0.21749(15) 0.83550(15) 0.0504(5) Uani 1 1 d . . . . .
C20 C 0.82769(19) 0.28881(17) 0.90149(14) 0.0522(5) Uani 1 1 d . . . . .
C21 C 0.7972(2) 0.38588(16) 0.88303(16) 0.0579(6) Uani 1 1 d . . . . .
H21 H 0.8154 0.4343 0.9275 0.069 Uiso 1 1 calc R . . . .
C22 C 0.73764(18) 0.40949(16) 0.79479(14) 0.0510(5) Uani 1 1 d . . . . .
H22 H 0.7156 0.4756 0.7803 0.061 Uiso 1 1 calc R . . . .
C23 C 0.9009(2) 0.1436(2) 0.96228(16) 0.0734(7) Uani 1 1 d . . . . .
H23A H 0.9883 0.1305 0.9717 0.088 Uiso 1 1 calc R . . . .
H23B H 0.8718 0.1000 1.0012 0.088 Uiso 1 1 calc R . . . .
C24 C 0.4339(3) 0.0046(2) 0.3784(2) 0.1005(10) Uani 1 1 d . . . . .
H24A H 0.3902 -0.0578 0.3687 0.151 Uiso 1 1 calc GR . . . .
H24B H 0.3909 0.0513 0.4050 0.151 Uiso 1 1 calc GR . . . .
H24C H 0.5162 -0.0055 0.4176 0.151 Uiso 1 1 calc GR . . . .
N2 N 0.37199(15) 0.26897(13) 0.16520(11) 0.0493(5) Uani 1 1 d . . . . .
N1 N 0.07828(16) 0.23447(13) -0.25234(11) 0.0529(5) Uani 1 1 d . . . . .
N3 N 0.43235(15) 0.24802(13) 0.25284(11) 0.0489(4) Uani 1 1 d . . . . .
H3 H 0.4446 0.1868 0.2698 0.059 Uiso 1 1 calc R . . . .
O1 O 0.25325(16) 0.38367(10) 0.03115(10) 0.0637(5) Uani 1 1 d . . . . .
H1 H 0.2927 0.3702 0.0828 0.096 Uiso 1 1 calc GR . . . .
O2 O 0.45973(14) 0.40982(11) 0.29319(10) 0.0624(4) Uani 1 1 d . . . . .
O3 O 0.83383(17) 0.12534(12) 0.87230(11) 0.0780(5) Uani 1 1 d . . . . .
O4 O 0.88325(16) 0.24463(13) 0.98205(10) 0.0721(5) Uani 1 1 d . . . . .
O5 O 0.4402(2) 0.04112(13) 0.29928(14) 0.0879(6) Uani 1 1 d . . . . .
H5 H 0.4728 -0.0004 0.2750 0.132 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.495(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 N1 1.456(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C3 C4 1.492(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 N1 1.456(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.408(3) . ?
C5 N1 1.363(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.365(3) . ?
C7 C8 1.405(3) . ?
C7 O1 1.356(2) . ?
C8 C9 1.393(3) . ?
C8 C11 1.425(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.360(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 N2 1.282(3) . ?
C12 C13 1.459(3) . ?
C12 N3 1.338(3) . ?
C12 O2 1.225(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.326(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.425(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.327(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.451(3) . ?
C17 C18 1.402(3) . ?
C17 C22 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.351(3) . ?
C19 C20 1.375(3) . ?
C19 O3 1.371(2) . ?
C20 C21 1.355(3) . ?
C20 O4 1.367(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 O3 1.411(3) . ?
C23 O4 1.416(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 O5 1.355(3) . ?
N2 N3 1.370(2) . ?
N3 H3 0.8600 . ?
O1 H1 0.8200 . ?
O5 H5 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C2 C1 113.51(18) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N1 C4 C3 113.8(2) . . ?
N1 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C6 C5 C10 116.68(19) . . ?
N1 C5 C6 121.43(18) . . ?
N1 C5 C10 121.88(18) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.06(19) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 121.40(19) . . ?
O1 C7 C6 117.52(18) . . ?
O1 C7 C8 121.06(19) . . ?
C7 C8 C11 122.99(19) . . ?
C9 C8 C7 115.94(19) . . ?
C9 C8 C11 121.07(19) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 C8 123.51(19) . . ?
C10 C9 H9 118.2 . . ?
C5 C10 H10 119.8 . . ?
C9 C10 C5 120.39(19) . . ?
C9 C10 H10 119.8 . . ?
C8 C11 H11 119.0 . . ?
N2 C11 C8 122.01(19) . . ?
N2 C11 H11 119.0 . . ?
N3 C12 C13 113.91(19) . . ?
O2 C12 C13 123.0(2) . . ?
O2 C12 N3 123.1(2) . . ?
C12 C13 H13 118.3 . . ?
C14 C13 C12 123.5(2) . . ?
C14 C13 H13 118.3 . . ?
C13 C14 H14 117.5 . . ?
C13 C14 C15 125.0(2) . . ?
C15 C14 H14 117.5 . . ?
C14 C15 H15 116.9 . . ?
C16 C15 C14 126.1(2) . . ?
C16 C15 H15 116.9 . . ?
C15 C16 H16 116.3 . . ?
C15 C16 C17 127.3(2) . . ?
C17 C16 H16 116.3 . . ?
C18 C17 C16 121.41(19) . . ?
C22 C17 C16 119.97(19) . . ?
C22 C17 C18 118.61(19) . . ?
C17 C18 H18 121.2 . . ?
C19 C18 C17 117.53(19) . . ?
C19 C18 H18 121.2 . . ?
C18 C19 C20 122.9(2) . . ?
C18 C19 O3 127.51(19) . . ?
O3 C19 C20 109.50(19) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 O4 129.1(2) . . ?
O4 C20 C19 109.67(19) . . ?
C20 C21 H21 121.6 . . ?
C20 C21 C22 116.8(2) . . ?
C22 C21 H21 121.6 . . ?
C17 C22 H22 118.5 . . ?
C21 C22 C17 122.9(2) . . ?
C21 C22 H22 118.5 . . ?
H23A C23 H23B 108.4 . . ?
O3 C23 H23A 110.0 . . ?
O3 C23 H23B 110.0 . . ?
O3 C23 O4 108.40(18) . . ?
O4 C23 H23A 110.0 . . ?
O4 C23 H23B 110.0 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
C11 N2 N3 116.77(18) . . ?
C4 N1 C2 115.57(17) . . ?
C5 N1 C2 121.65(16) . . ?
C5 N1 C4 122.49(17) . . ?
C12 N3 N2 121.11(18) . . ?
C12 N3 H3 119.4 . . ?
N2 N3 H3 119.4 . . ?
C7 O1 H1 109.5 . . ?
C19 O3 C23 105.55(17) . . ?
C20 O4 C23 105.52(17) . . ?
C24 O5 H5 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
N3 H3 O5 0.86 2.01 2.861(3) 169.7 .
O1 H1 N2 0.82 1.90 2.628(2) 146.7 .
O5 H5 O2 0.82 1.91 2.729(2) 174.0 2_645

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N1 C4 -84.4(2) . . . . ?
C1 C2 N1 C5 89.6(2) . . . . ?
C3 C4 N1 C2 -87.0(2) . . . . ?
C3 C4 N1 C5 99.1(2) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C5 C6 C7 O1 177.69(18) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C5 N1 C2 -9.2(3) . . . . ?
C6 C5 N1 C4 164.3(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C11 -179.58(18) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C11 N2 -2.4(3) . . . . ?
C8 C9 C10 C5 -0.6(3) . . . . ?
C8 C11 N2 N3 177.17(16) . . . . ?
C9 C8 C11 N2 177.55(18) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C10 C5 N1 C2 170.48(19) . . . . ?
C10 C5 N1 C4 -16.0(3) . . . . ?
C11 C8 C9 C10 -179.60(18) . . . . ?
C11 N2 N3 C12 175.46(17) . . . . ?
C12 C13 C14 C15 179.44(18) . . . . ?
C13 C12 N3 N2 179.10(15) . . . . ?
C13 C14 C15 C16 -174.7(2) . . . . ?
C14 C15 C16 C17 179.45(18) . . . . ?
C15 C16 C17 C18 -3.5(3) . . . . ?
C15 C16 C17 C22 175.7(2) . . . . ?
C16 C17 C18 C19 177.20(18) . . . . ?
C16 C17 C22 C21 -177.58(18) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C17 C18 C19 O3 178.3(2) . . . . ?
C18 C17 C22 C21 1.7(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C18 C19 C20 O4 178.21(18) . . . . ?
C18 C19 O3 C23 174.9(2) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C19 C20 O4 C23 6.7(2) . . . . ?
C20 C19 O3 C23 -7.3(2) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C21 C20 O4 C23 -176.1(2) . . . . ?
C22 C17 C18 C19 -2.0(3) . . . . ?
N1 C5 C6 C7 -179.45(18) . . . . ?
N1 C5 C10 C9 -179.74(18) . . . . ?
N3 C12 C13 C14 -171.99(18) . . . . ?
O1 C7 C8 C9 -178.26(18) . . . . ?
O1 C7 C8 C11 1.7(3) . . . . ?
O2 C12 C13 C14 8.0(3) . . . . ?
O2 C12 N3 N2 -0.9(3) . . . . ?
O3 C19 C20 C21 -177.1(2) . . . . ?
O3 C19 C20 O4 0.4(2) . . . . ?
O3 C23 O4 C20 -11.3(3) . . . . ?
O4 C20 C21 C22 -178.1(2) . . . . ?
O4 C23 O3 C19 11.5(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_mo_190508e_0m
_database_code_depnum_ccdc_archive 'CCDC 1984255'
loop_
_audit_author_name
_audit_author_address
'Ahmed Tantawy'
;Huazhong agriculture university
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H18 F2 N2 O3'
_chemical_formula_sum            'C25 H18 F2 N2 O3'
_chemical_formula_weight         432.41
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.329(3)
_cell_length_b                   10.708(5)
_cell_length_c                   15.496(7)
_cell_angle_alpha                83.878(9)
_cell_angle_beta                 87.608(9)
_cell_angle_gamma                82.240(9)
_cell_volume                     870.8(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.64
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5798
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1408 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.7772.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             448
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0793
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6085
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.23
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1879
_reflns_number_total             3045
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.243(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1019P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1941
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), N2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 1.4016(6) 1.1771(3) 0.10693(19) 0.0407(7) Uani 1 d . . .
C2 C 1.2191(7) 1.2696(4) 0.1081(3) 0.0732(11) Uani 1 d . . .
H2 H 1.0963 1.2685 0.1525 0.088 Uiso 1 calc . . R
C3 C 1.2059(9) 1.3641(4) 0.0477(3) 0.0858(14) Uani 1 d . . .
H3 H 1.0736 1.4303 0.0483 0.103 Uiso 1 calc . . R
C4 C 1.3740(8) 1.3650(3) -0.0118(2) 0.0552(9) Uani 1 d . . .
C5 C 1.5558(7) 1.2776(3) -0.0149(2) 0.0554(9) Uani 1 d . . .
H5 H 1.6780 1.2805 -0.0594 0.066 Uiso 1 calc . . R
C6 C 1.5694(6) 1.1834(3) 0.0452(2) 0.0516(9) Uani 1 d . . .
H6 H 1.7041 1.1186 0.0436 0.062 Uiso 1 calc . . R
C7 C 1.4151(6) 1.0794(3) 0.17370(19) 0.0415(7) Uani 1 d . . .
C8 C 1.5704(6) 1.0839(3) 0.24312(18) 0.0416(7) Uani 1 d . . .
C9 C 1.7148(7) 1.1717(3) 0.2423(2) 0.0541(9) Uani 1 d . . .
H9 H 1.7105 1.2339 0.1954 0.065 Uiso 1 calc . . R
C10 C 1.8653(7) 1.1751(3) 0.3052(2) 0.0617(10) Uani 1 d . . .
H10 H 1.9717 1.2375 0.3032 0.074 Uiso 1 calc . . R
C11 C 1.8644(7) 1.0920(3) 0.3693(2) 0.0551(9) Uani 1 d . . .
C12 C 1.7235(8) 1.0047(3) 0.3753(2) 0.0644(10) Uani 1 d . . .
H12 H 1.7252 0.9457 0.4239 0.077 Uiso 1 calc . . R
C13 C 1.5766(7) 1.0008(3) 0.3109(2) 0.0619(10) Uani 1 d . . .
H13 H 1.4734 0.9369 0.3134 0.074 Uiso 1 calc . . R
C14 C 1.0006(6) 0.9002(3) 0.1170(2) 0.0439(8) Uani 1 d . . .
C15 C 0.9935(6) 0.8180(3) 0.1904(2) 0.0496(8) Uani 1 d . . .
H15 H 1.1064 0.8202 0.2343 0.060 Uiso 1 calc . . R
C16 C 0.8390(6) 0.7406(3) 0.19962(19) 0.0489(8) Uani 1 d . . .
H16 H 0.7292 0.7416 0.1544 0.059 Uiso 1 calc . . R
C17 C 0.8146(7) 0.6551(3) 0.2688(2) 0.0533(9) Uani 1 d . . .
H17 H 0.9252 0.6512 0.3141 0.064 Uiso 1 calc . . R
C18 C 0.6510(7) 0.5804(3) 0.2754(2) 0.0532(9) Uani 1 d . . .
H18 H 0.5423 0.5871 0.2293 0.064 Uiso 1 calc . . R
C19 C 0.6132(6) 0.4899(3) 0.3428(2) 0.0475(8) Uani 1 d . . .
C20 C 0.4224(7) 0.4250(3) 0.3409(2) 0.0580(9) Uani 1 d . . .
H20 H 0.3173 0.4408 0.2935 0.070 Uiso 1 calc . . R
C21 C 0.3747(7) 0.3391(3) 0.4031(2) 0.0611(10) Uani 1 d . . .
H21 H 0.2365 0.2949 0.4016 0.073 Uiso 1 calc . . R
C22 C 0.5250(7) 0.3185(3) 0.4656(2) 0.0515(8) Uani 1 d . . .
C23 C 0.7143(6) 0.3808(3) 0.4692(2) 0.0458(8) Uani 1 d . . .
C24 C 0.7640(6) 0.4666(3) 0.4098(2) 0.0486(8) Uani 1 d . . .
H24 H 0.9009 0.5111 0.4135 0.058 Uiso 1 calc . . R
C25 C 0.7211(8) 0.2478(4) 0.5787(2) 0.0635(10) Uani 1 d . . .
H25A H 0.6692 0.2658 0.6374 0.076 Uiso 1 calc . . R
H25B H 0.8356 0.1690 0.5820 0.076 Uiso 1 calc . . R
F1 F 1.3590(5) 1.45741(18) -0.07088(13) 0.0810(8) Uani 1 d . . .
F2 F 2.0110(5) 1.0967(2) 0.43265(14) 0.0845(8) Uani 1 d . . .
N1 N 1.2936(5) 0.9909(2) 0.17772(15) 0.0431(7) Uani 1 d . . .
N2 N 1.1498(5) 0.9847(2) 0.11339(16) 0.0455(7) Uani 1 d . . .
H2A H 1.1547 1.0380 0.0679 0.055 Uiso 1 calc . . R
O1 O 0.8772(4) 0.89714(19) 0.05775(14) 0.0528(7) Uani 1 d . . .
O2 O 0.5183(5) 0.2373(2) 0.53343(16) 0.0689(8) Uani 1 d . . .
O3 O 0.8369(5) 0.3411(2) 0.53941(15) 0.0658(8) Uani 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.292(5) . ?
C1 C6 1.285(4) . ?
C1 C7 1.388(4) . ?
C2 C3 1.301(5) . ?
C3 C4 1.258(5) . ?
C4 C5 1.256(5) . ?
C4 F1 1.271(3) . ?
C5 C6 1.294(4) . ?
C7 C8 1.393(4) . ?
C7 N1 1.212(4) . ?
C8 C9 1.292(4) . ?
C8 C13 1.301(4) . ?
C9 C10 1.295(4) . ?
C10 C11 1.262(5) . ?
C11 C12 1.269(5) . ?
C11 F2 1.289(3) . ?
C12 C13 1.301(4) . ?
C14 C15 1.365(4) . ?
C14 N2 1.279(4) . ?
C14 O1 1.157(3) . ?
C15 C16 1.239(4) . ?
C16 C17 1.347(4) . ?
C17 C18 1.254(4) . ?
C18 C19 1.374(4) . ?
C19 C20 1.310(4) . ?
C19 C24 1.322(4) . ?
C20 C21 1.300(4) . ?
C21 C22 1.265(4) . ?
C22 C23 1.288(5) . ?
C22 O2 1.293(4) . ?
C23 C24 1.276(4) . ?
C23 O3 1.295(3) . ?
C25 O2 1.337(4) . ?
C25 O3 1.325(4) . ?
N1 N2 1.295(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 119.2(3) . . ?
C6 C1 C2 117.7(3) . . ?
C6 C1 C7 123.0(3) . . ?
C1 C2 C3 120.5(4) . . ?
C4 C3 C2 119.2(4) . . ?
C3 C4 F1 118.8(4) . . ?
C5 C4 C3 122.2(3) . . ?
C5 C4 F1 118.9(4) . . ?
C4 C5 C6 118.7(3) . . ?
C1 C6 C5 121.7(3) . . ?
C1 C7 C8 118.7(3) . . ?
N1 C7 C1 124.5(3) . . ?
N1 C7 C8 116.7(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 C13 117.4(3) . . ?
C13 C8 C7 121.8(3) . . ?
C8 C9 C10 121.5(3) . . ?
C11 C10 C9 118.5(3) . . ?
C10 C11 C12 123.3(3) . . ?
C10 C11 F2 118.5(3) . . ?
C12 C11 F2 118.2(3) . . ?
C11 C12 C13 117.6(3) . . ?
C8 C13 C12 121.6(3) . . ?
N2 C14 C15 118.6(3) . . ?
O1 C14 C15 123.0(3) . . ?
O1 C14 N2 118.4(3) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 126.3(3) . . ?
C18 C17 C16 123.7(3) . . ?
C17 C18 C19 127.8(3) . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 C24 118.9(3) . . ?
C24 C19 C18 121.7(3) . . ?
C21 C20 C19 122.3(3) . . ?
C22 C21 C20 116.9(3) . . ?
C21 C22 C23 122.1(3) . . ?
C21 C22 O2 128.0(3) . . ?
C23 C22 O2 109.8(3) . . ?
C22 C23 O3 109.6(3) . . ?
C24 C23 C22 122.4(3) . . ?
C24 C23 O3 128.0(3) . . ?
C23 C24 C19 117.3(3) . . ?
O3 C25 O2 108.6(3) . . ?
C7 N1 N2 117.5(3) . . ?
C14 N2 N1 120.6(3) . . ?
C22 O2 C25 105.7(3) . . ?
C23 O3 C25 106.1(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_cu_190429a_0m
_database_code_depnum_ccdc_archive 'CCDC 1984254'
loop_
_audit_author_name
_audit_author_address
'Ahmed Tantawy'
;Huazhong agriculture university
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N3 O3, H2 O, H1.86 O0.41'
_chemical_formula_sum            'C21 H24.75 N3 O4.42'
_chemical_formula_weight         389.87
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.6957(16)
_cell_length_b                   6.3687(7)
_cell_length_c                   24.058(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.090(6)
_cell_angle_gamma                90
_cell_volume                     2035.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1618
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      50.80
_cell_measurement_theta_min      3.40
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.4535
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9153
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        57.702
_diffrn_reflns_theta_max         57.702
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1746
_reflns_number_total             2692
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.029
_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)+(0.0983P)²+0.5300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2150
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), N1(H1)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.042
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2311(3) 1.5694(8) -0.0130(3) 0.112(2) Uani 1 1 d . . . . .
H1A H 0.2180 1.7024 0.0035 0.135 Uiso 1 1 calc R . . . .
H1B H 0.2003 1.5727 -0.0538 0.135 Uiso 1 1 calc R . . . .
C2 C 0.2699(3) 1.2691(7) 0.03573(18) 0.0697(12) Uani 1 1 d . . . . .
C3 C 0.3576(3) 1.3487(6) 0.02624(17) 0.0658(12) Uani 1 1 d . . . . .
C4 C 0.4478(3) 1.2494(6) 0.04342(17) 0.0656(11) Uani 1 1 d . . . . .
H4 H 0.5063 1.3069 0.0367 0.079 Uiso 1 1 calc R . . . .
C5 C 0.4488(3) 1.0564(6) 0.07167(15) 0.0577(10) Uani 1 1 d . . . . .
C6 C 0.3596(3) 0.9786(7) 0.08074(16) 0.0690(12) Uani 1 1 d . . . . .
H6 H 0.3607 0.8502 0.0993 0.083 Uiso 1 1 calc R . . . .
C7 C 0.2679(3) 1.0844(8) 0.06321(19) 0.0783(13) Uani 1 1 d . . . . .
H7 H 0.2087 1.0308 0.0701 0.094 Uiso 1 1 calc R . . . .
C8 C 0.5405(3) 0.9360(6) 0.09152(16) 0.0639(11) Uani 1 1 d . . . . .
H8 H 0.5323 0.8017 0.1049 0.077 Uiso 1 1 calc R . . . .
C9 C 0.6350(3) 0.9920(7) 0.09324(16) 0.0662(11) Uani 1 1 d . . . . .
H9 H 0.6456 1.1267 0.0810 0.079 Uiso 1 1 calc R . . . .
C10 C 0.7218(3) 0.8599(6) 0.11256(16) 0.0620(11) Uani 1 1 d . . . . .
H10 H 0.7102 0.7230 0.1227 0.074 Uiso 1 1 calc R . . . .
C11 C 0.8165(3) 0.9144(6) 0.11721(17) 0.0671(11) Uani 1 1 d . . . . .
H11 H 0.8299 1.0514 0.1079 0.081 Uiso 1 1 calc R . . . .
C12 C 0.9007(3) 0.7719(7) 0.13611(17) 0.0635(11) Uani 1 1 d . . . . .
C13 C 1.1589(3) 0.8569(6) 0.17762(15) 0.0559(10) Uani 1 1 d . . . . .
H13 H 1.1514 0.9991 0.1843 0.067 Uiso 1 1 calc R . . . .
C14 C 1.2594(2) 0.7694(5) 0.19062(15) 0.0479(9) Uani 1 1 d . . . . .
C15 C 1.2826(3) 0.5690(5) 0.17311(15) 0.0532(10) Uani 1 1 d . . . . .
H15 H 1.2308 0.4829 0.1533 0.064 Uiso 1 1 calc R . . . .
C16 C 1.3796(3) 0.4979(5) 0.18450(15) 0.0532(10) Uani 1 1 d . . . . .
H16 H 1.3923 0.3644 0.1723 0.064 Uiso 1 1 calc R . . . .
C17 C 1.4607(3) 0.6218(6) 0.21429(15) 0.0522(10) Uani 1 1 d . . . . .
C18 C 1.4367(3) 0.8198(6) 0.23312(16) 0.0566(10) Uani 1 1 d . . . . .
H18 H 1.4877 0.9044 0.2542 0.068 Uiso 1 1 calc R . . . .
C19 C 1.3398(3) 0.8895(6) 0.22090(15) 0.0554(10) Uani 1 1 d . . . . .
H19 H 1.3269 1.0227 0.2333 0.066 Uiso 1 1 calc R . . . .
C20 C 1.5830(3) 0.3510(7) 0.2050(2) 0.0944(16) Uani 1 1 d . . . . .
H20A H 1.5408 0.2463 0.2159 0.142 Uiso 1 1 calc GR . . . .
H20B H 1.6523 0.3189 0.2221 0.142 Uiso 1 1 calc GR . . . .
H20C H 1.5721 0.3525 0.1641 0.142 Uiso 1 1 calc GR . . . .
C21 C 1.6407(3) 0.6943(7) 0.24970(19) 0.0777(13) Uani 1 1 d . . . . .
H21A H 1.6408 0.8113 0.2245 0.116 Uiso 1 1 calc GR . . . .
H21B H 1.7035 0.6203 0.2554 0.116 Uiso 1 1 calc GR . . . .
H21C H 1.6324 0.7444 0.2859 0.116 Uiso 1 1 calc GR . . . .
N1 N 0.9914(2) 0.8639(5) 0.14331(13) 0.0639(9) Uani 1 1 d . . . . .
H1 H 0.9948 0.9976 0.1392 0.077 Uiso 1 1 calc R . . . .
N2 N 1.0796(2) 0.7473(5) 0.15725(13) 0.0593(9) Uani 1 1 d . . . . .
N3 N 1.5588(2) 0.5543(5) 0.22449(15) 0.0705(10) Uani 1 1 d . . . . .
O1 O 0.3376(2) 1.5365(5) -0.00324(16) 0.1055(12) Uani 1 1 d . . . . .
O2 O 0.1899(2) 1.4004(5) 0.01342(15) 0.0978(11) Uani 1 1 d . . . . .
O3 O 0.89134(19) 0.5832(5) 0.14560(13) 0.0836(10) Uani 1 1 d . . . . .
O4 O 1.0189(3) 0.2865(5) 0.10864(19) 0.1213(13) Uani 1 1 d . . . . .
H4A H 1.0172 0.3167 0.0740 0.182 Uiso 1 1 d G . . . .
H4B H 0.9958 0.3951 0.1216 0.182 Uiso 1 1 d G . . . .
O5 O 0.9798(9) 0.228(4) -0.0069(7) 0.176(11) Uani 0.41(2) 1 d . . . . .
H5A H 0.9880 0.1131 0.0114 0.263 Uiso 1.0(2) 1 d G . . . .
H5B H 1.0369 0.2788 -0.0078 0.263 Uiso 0.88(14) 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.434(5) . ?
C1 O2 1.434(6) . ?
C2 C3 1.373(5) . ?
C2 C7 1.353(6) . ?
C2 O2 1.379(4) . ?
C3 C4 1.360(5) . ?
C3 O1 1.384(5) . ?
C4 C5 1.403(5) . ?
C5 C6 1.384(5) . ?
C5 C8 1.449(5) . ?
C6 C7 1.397(5) . ?
C8 C9 1.334(5) . ?
C9 C10 1.438(5) . ?
C10 C11 1.320(5) . ?
C11 C12 1.451(5) . ?
C12 N1 1.346(5) . ?
C12 O3 1.236(4) . ?
C13 C14 1.447(5) . ?
C13 N2 1.283(4) . ?
C14 C15 1.404(5) . ?
C14 C19 1.392(5) . ?
C15 C16 1.366(4) . ?
C16 C17 1.408(4) . ?
C17 C18 1.405(5) . ?
C17 N3 1.375(4) . ?
C18 C19 1.361(4) . ?
C20 N3 1.443(5) . ?
C21 N3 1.446(4) . ?
N1 N2 1.388(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
O2 C1 O1 108.2(4) . . ?
C3 C2 O2 110.9(4) . . ?
C7 C2 C3 121.6(4) . . ?
C7 C2 O2 127.5(4) . . ?
C2 C3 O1 109.4(4) . . ?
C4 C3 C2 123.0(4) . . ?
C4 C3 O1 127.6(4) . . ?
C3 C4 C5 117.1(4) . . ?
C4 C5 C8 121.9(4) . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 C8 119.1(4) . . ?
C5 C6 C7 122.9(4) . . ?
C2 C7 C6 116.3(4) . . ?
C9 C8 C5 128.7(4) . . ?
C8 C9 C10 125.0(4) . . ?
C11 C10 C9 126.2(4) . . ?
C10 C11 C12 123.5(4) . . ?
N1 C12 C11 114.0(4) . . ?
O3 C12 C11 123.8(4) . . ?
O3 C12 N1 122.2(3) . . ?
N2 C13 C14 123.0(3) . . ?
C15 C14 C13 123.9(3) . . ?
C19 C14 C13 119.4(3) . . ?
C19 C14 C15 116.7(3) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C17 121.6(3) . . ?
C18 C17 C16 116.7(3) . . ?
N3 C17 C16 122.1(3) . . ?
N3 C17 C18 121.2(3) . . ?
C19 C18 C17 121.0(3) . . ?
C18 C19 C14 122.6(3) . . ?
C12 N1 N2 121.4(3) . . ?
C13 N2 N1 114.0(3) . . ?
C17 N3 C20 121.0(3) . . ?
C17 N3 C21 120.5(3) . . ?
C20 N3 C21 118.2(3) . . ?
C3 O1 C1 106.1(3) . . ?
C2 O2 C1 105.4(4) . . ?

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
N1 H1 O4 0.86 2.04 2.870(5) 162.5 1_565
O4 H4A O5 0.85 1.97 2.726(16) 147.4 .
O4 H4B O3 0.85 2.05 2.858(5) 157.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 0.4(6) . . . . ?
C2 C3 O1 C1 -1.1(5) . . . . ?
C3 C2 C7 C6 -0.7(6) . . . . ?
C3 C2 O2 C1 1.7(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C8 179.6(3) . . . . ?
C4 C3 O1 C1 177.9(4) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
C4 C5 C8 C9 8.7(6) . . . . ?
C5 C6 C7 C2 0.8(6) . . . . ?
C5 C8 C9 C10 -178.5(4) . . . . ?
C6 C5 C8 C9 -171.4(4) . . . . ?
C7 C2 C3 C4 0.1(7) . . . . ?
C7 C2 C3 O1 179.1(4) . . . . ?
C7 C2 O2 C1 -177.8(5) . . . . ?
C8 C5 C6 C7 179.8(4) . . . . ?
C8 C9 C10 C11 -176.6(4) . . . . ?
C9 C10 C11 C12 -178.9(4) . . . . ?
C10 C11 C12 N1 -173.8(4) . . . . ?
C10 C11 C12 O3 5.4(7) . . . . ?
C11 C12 N1 N2 -175.3(3) . . . . ?
C12 N1 N2 C13 -162.2(4) . . . . ?
C13 C14 C15 C16 177.1(3) . . . . ?
C13 C14 C19 C18 -178.0(3) . . . . ?
C14 C13 N2 N1 -174.9(3) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C14 C19 C18 0.4(5) . . . . ?
C15 C16 C17 C18 1.7(5) . . . . ?
C15 C16 C17 N3 -178.0(3) . . . . ?
C16 C17 C18 C19 -2.4(5) . . . . ?
C16 C17 N3 C20 -0.2(6) . . . . ?
C16 C17 N3 C21 173.3(4) . . . . ?
C17 C18 C19 C14 1.5(6) . . . . ?
C18 C17 N3 C20 -179.9(4) . . . . ?
C18 C17 N3 C21 -6.4(6) . . . . ?
C19 C14 C15 C16 -1.1(5) . . . . ?
N2 C13 C14 C15 11.9(6) . . . . ?
N2 C13 C14 C19 -169.8(3) . . . . ?
N3 C17 C18 C19 177.3(4) . . . . ?
O1 C1 O2 C2 -2.3(5) . . . . ?
O1 C3 C4 C5 -178.4(4) . . . . ?
O2 C1 O1 C3 2.2(5) . . . . ?
O2 C2 C3 C4 -179.4(4) . . . . ?
O2 C2 C3 O1 -0.3(5) . . . . ?
O2 C2 C7 C6 178.7(4) . . . . ?
O3 C12 N1 N2 5.5(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_cu_190418a_0m
_audit_block_doi                 10.5517/ccdc.csd.cc24ls3n
_database_code_depnum_ccdc_archive 'CCDC 1984251'
loop_
_audit_author_name
_audit_author_address
'Ahmed Tantawy'
;Huazhong agriculture university
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-04-19
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O4, C H4 O'
_chemical_formula_sum            'C20 H20 N2 O5'
_chemical_formula_weight         368.38
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9249(5)
_cell_length_b                   6.5740(3)
_cell_length_c                   25.7341(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.790(3)
_cell_angle_gamma                90
_cell_volume                     1841.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.2901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10352
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        64.989
_diffrn_reflns_theta_max         64.989
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2415
_reflns_number_total             3035
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0068(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0925
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2530
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C13(H13), C16(H16), C8(H8), C9(H9), C19(H19), N1(H1), C15(H15), C4(H4A), 
 C6(H6), C18(H18), C7(H7), C10(H10), C11(H11) 
2.c Idealised Me refined as rotating group: 
 C20(H20A,H20B,H20C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O4(H4), O5(H5) 
;
_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
C14 C 0.4694(2) 0.1472(3) 0.06965(9) 0.0390(6) Uani 1 1 d . . . . .
O4 O 0.77887(18) 0.4303(3) 0.14088(8) 0.0615(6) Uani 1 1 d . . . . .
H4 H 0.7939 0.5346 0.1251 0.092 Uiso 1 1 calc GR . . . .
N2 N 0.30150(18) 0.1279(3) 0.00497(8) 0.0435(5) Uani 1 1 d . . . . .
C17 C 0.6750(2) 0.3421(4) 0.11774(10) 0.0442(6) Uani 1 1 d . . . . .
C13 C 0.3682(2) 0.0404(3) 0.04116(10) 0.0423(6) Uani 1 1 d . . . . .
H13 H 0.3521 -0.0940 0.0496 0.051 Uiso 1 1 calc R . . . .
C5 C -0.3273(2) -0.1412(3) -0.20565(9) 0.0389(6) Uani 1 1 d . . . . .
C16 C 0.5970(2) 0.4449(4) 0.08145(10) 0.0462(6) Uani 1 1 d . . . . .
H16 H 0.6132 0.5794 0.0732 0.055 Uiso 1 1 calc R . . . .
C8 C -0.2199(2) -0.0335(4) -0.18131(9) 0.0432(6) Uani 1 1 d . . . . .
H8 H -0.2115 0.1015 -0.1911 0.052 Uiso 1 1 calc R . . . .
C9 C -0.1333(2) -0.1050(4) -0.14702(10) 0.0456(6) Uani 1 1 d . . . . .
H9 H -0.1357 -0.2422 -0.1384 0.055 Uiso 1 1 calc R . . . .
C3 C -0.4631(2) -0.4225(4) -0.21379(10) 0.0435(6) Uani 1 1 d . . . . .
C2 C -0.5354(2) -0.3198(4) -0.25176(11) 0.0487(7) Uani 1 1 d . . . . .
C19 C 0.5449(2) 0.0486(3) 0.10781(9) 0.0436(6) Uani 1 1 d . . . . .
H19 H 0.5267 -0.0839 0.1172 0.052 Uiso 1 1 calc R . . . .
N1 N 0.21128(19) 0.0127(3) -0.02131(8) 0.0447(6) Uani 1 1 d . . . . .
H1 H 0.2010 -0.1121 -0.0127 0.054 Uiso 1 1 calc R . . . .
C15 C 0.4957(2) 0.3483(4) 0.05763(10) 0.0448(6) Uani 1 1 d . . . . .
H15 H 0.4440 0.4180 0.0332 0.054 Uiso 1 1 calc R . . . .
C4 C -0.3584(2) -0.3394(3) -0.18991(9) 0.0426(6) Uani 1 1 d . . . . .
H4A H -0.3099 -0.4099 -0.1645 0.051 Uiso 1 1 calc R . . . .
O1 O -0.63499(16) -0.4378(3) -0.26794(9) 0.0688(7) Uani 1 1 d . . . . .
C6 C -0.4013(2) -0.0423(4) -0.24407(10) 0.0470(6) Uani 1 1 d . . . . .
H6 H -0.3794 0.0876 -0.2542 0.056 Uiso 1 1 calc R . . . .
C12 C 0.1398(2) 0.0957(3) -0.06023(10) 0.0419(6) Uani 1 1 d . . . . .
C18 C 0.6475(2) 0.1457(4) 0.13218(10) 0.0483(6) Uani 1 1 d . . . . .
H18 H 0.6971 0.0791 0.1579 0.058 Uiso 1 1 calc R . . . .
C7 C -0.5075(2) -0.1309(4) -0.26820(11) 0.0539(7) Uani 1 1 d . . . . .
H7 H -0.5563 -0.0639 -0.2941 0.065 Uiso 1 1 calc R . . . .
O3 O 0.14896(16) 0.2760(2) -0.07355(7) 0.0541(6) Uani 1 1 d . . . . .
C10 C -0.0355(2) 0.0178(4) -0.12233(10) 0.0436(6) Uani 1 1 d . . . . .
H10 H -0.0310 0.1522 -0.1333 0.052 Uiso 1 1 calc R . . . .
O2 O -0.51221(17) -0.6089(3) -0.20492(9) 0.0625(6) Uani 1 1 d . . . . .
O5 O 0.1914(2) 0.5938(3) 0.00281(8) 0.0728(7) Uani 1 1 d . . . . .
H5 H 0.1948 0.4948 -0.0164 0.109 Uiso 1 1 calc GR . . . .
C11 C 0.0480(2) -0.0429(4) -0.08574(10) 0.0477(7) Uani 1 1 d . . . . .
H11 H 0.0488 -0.1788 -0.0756 0.057 Uiso 1 1 calc R . . . .
C20 C 0.1548(4) 0.5328(6) 0.05015(16) 0.0883(12) Uani 1 1 d . . . . .
H20A H 0.0673 0.5148 0.0474 0.132 Uiso 1 1 calc GR . . . .
H20B H 0.1774 0.6345 0.0760 0.132 Uiso 1 1 calc GR . . . .
H20C H 0.1941 0.4065 0.0601 0.132 Uiso 1 1 calc GR . . . .
C1 C -0.6201(3) -0.6227(5) -0.24021(15) 0.0748(10) Uani 1 1 d . . . . .
H1A H -0.6122 -0.7344 -0.2643 0.090 Uiso 1 1 calc R . . . .
H1B H -0.6913 -0.6480 -0.2210 0.090 Uiso 1 1 calc R . . . .


_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
C14 C13 1.455(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.392(3) . ?
O4 H4 0.8200 . ?
O4 C17 1.366(3) . ?
N2 C13 1.271(3) . ?
N2 N1 1.375(3) . ?
C17 C16 1.386(3) . ?
C17 C18 1.383(4) . ?
C13 H13 0.9300 . ?
C5 C8 1.466(3) . ?
C5 C4 1.414(3) . ?
C5 C6 1.386(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.375(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.325(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.444(3) . ?
C3 C2 1.381(4) . ?
C3 C4 1.367(3) . ?
C3 O2 1.364(3) . ?
C2 O1 1.372(3) . ?
C2 C7 1.355(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.393(3) . ?
N1 H1 0.8600 . ?
N1 C12 1.334(3) . ?
C15 H15 0.9300 . ?
C4 H4A 0.9300 . ?
O1 C1 1.412(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(4) . ?
C12 O3 1.240(3) . ?
C12 C11 1.469(3) . ?
C18 H18 0.9300 . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.317(4) . ?
O2 C1 1.430(3) . ?
O5 H5 0.8200 . ?
O5 C20 1.374(4) . ?
C11 H11 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C1 H1A 0.9700 . ?
C1 H1B 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
C19 C14 C13 120.8(2) . . ?
C19 C14 C15 118.6(2) . . ?
C15 C14 C13 120.5(2) . . ?
C17 O4 H4 109.5 . . ?
C13 N2 N1 117.07(19) . . ?
O4 C17 C16 121.9(2) . . ?
O4 C17 C18 118.0(2) . . ?
C18 C17 C16 120.1(2) . . ?
C14 C13 H13 119.5 . . ?
N2 C13 C14 121.1(2) . . ?
N2 C13 H13 119.5 . . ?
C4 C5 C8 121.7(2) . . ?
C6 C5 C8 118.5(2) . . ?
C6 C5 C4 119.8(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.1(2) . . ?
C15 C16 H16 119.9 . . ?
C5 C8 H8 116.0 . . ?
C9 C8 C5 128.0(2) . . ?
C9 C8 H8 116.0 . . ?
C8 C9 H9 118.1 . . ?
C8 C9 C10 123.8(2) . . ?
C10 C9 H9 118.1 . . ?
C4 C3 C2 122.1(2) . . ?
O2 C3 C2 110.4(2) . . ?
O2 C3 C4 127.6(2) . . ?
O1 C2 C3 109.3(2) . . ?
C7 C2 C3 122.6(2) . . ?
C7 C2 O1 128.1(2) . . ?
C14 C19 H19 119.6 . . ?
C14 C19 C18 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
N2 N1 H1 120.2 . . ?
C12 N1 N2 119.64(18) . . ?
C12 N1 H1 120.2 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C5 C4 H4A 121.6 . . ?
C3 C4 C5 116.9(2) . . ?
C3 C4 H4A 121.6 . . ?
C2 O1 C1 106.2(2) . . ?
C5 C6 H6 118.8 . . ?
C5 C6 C7 122.3(2) . . ?
C7 C6 H6 118.8 . . ?
N1 C12 C11 114.62(19) . . ?
O3 C12 N1 122.9(2) . . ?
O3 C12 C11 122.5(2) . . ?
C17 C18 C19 119.4(2) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C2 C7 C6 116.4(2) . . ?
C2 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C9 C10 H10 117.0 . . ?
C11 C10 C9 126.0(2) . . ?
C11 C10 H10 117.0 . . ?
C3 O2 C1 105.4(2) . . ?
C20 O5 H5 109.5 . . ?
C12 C11 H11 118.7 . . ?
C10 C11 C12 122.5(2) . . ?
C10 C11 H11 118.7 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C1 O2 108.7(2) . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
O2 C1 H1A 110.0 . . ?
O2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?

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
O4 H4 O3 0.82 1.96 2.754(3) 162.6 3_665
N1 H1 O5 0.86 1.98 2.835(3) 174.2 1_545
O5 H5 O3 0.82 2.09 2.879(3) 162.0 .

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
C14 C19 C18 C17 -0.7(4) . . . . ?
O4 C17 C16 C15 177.6(2) . . . . ?
O4 C17 C18 C19 -177.5(2) . . . . ?
N2 N1 C12 O3 -1.5(4) . . . . ?
N2 N1 C12 C11 179.2(2) . . . . ?
C17 C16 C15 C14 0.3(4) . . . . ?
C13 C14 C19 C18 174.9(2) . . . . ?
C13 C14 C15 C16 -174.7(2) . . . . ?
C13 N2 N1 C12 -178.9(2) . . . . ?
C5 C8 C9 C10 -175.3(2) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C16 C17 C18 C19 3.6(4) . . . . ?
C8 C5 C4 C3 177.5(2) . . . . ?
C8 C5 C6 C7 -178.0(2) . . . . ?
C8 C9 C10 C11 175.5(3) . . . . ?
C9 C10 C11 C12 -175.9(2) . . . . ?
C3 C2 O1 C1 -2.3(3) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C3 O2 C1 O1 -2.4(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 O2 C1 1.0(3) . . . . ?
C2 O1 C1 O2 3.0(3) . . . . ?
C19 C14 C13 N2 -177.6(2) . . . . ?
C19 C14 C15 C16 2.6(4) . . . . ?
N1 N2 C13 C14 177.33(19) . . . . ?
N1 C12 C11 C10 175.1(2) . . . . ?
C15 C14 C13 N2 -0.3(4) . . . . ?
C15 C14 C19 C18 -2.4(4) . . . . ?
C4 C5 C8 C9 7.1(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C4 C3 C2 O1 -178.9(2) . . . . ?
C4 C3 C2 C7 0.5(4) . . . . ?
C4 C3 O2 C1 -179.3(3) . . . . ?
O1 C2 C7 C6 178.4(3) . . . . ?
C6 C5 C8 C9 -174.6(2) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C18 C17 C16 C15 -3.5(4) . . . . ?
C7 C2 O1 C1 178.4(3) . . . . ?
O3 C12 C11 C10 -4.2(4) . . . . ?
O2 C3 C2 O1 0.8(3) . . . . ?
O2 C3 C2 C7 -179.8(2) . . . . ?
O2 C3 C4 C5 -179.3(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_cu_190523c_0m
_database_code_depnum_ccdc_archive 'CCDC 1984253'
loop_
_audit_author_name
_audit_author_address
'Ahmed Tantawy'
;Huazhong agriculture university
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 O5, C H4 O'
_chemical_formula_sum            'C20 H20 N2 O6'
_chemical_formula_weight         384.38
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.6192(6)
_cell_length_b                   19.7039(17)
_cell_length_c                   14.2723(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.079(5)
_cell_angle_gamma                90
_cell_volume                     1838.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.41
_cell_measurement_theta_min      3.86
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.4681
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10609
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        64.992
_diffrn_reflns_theta_max         64.992
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2642
_reflns_number_total             2973
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0675P)²+0.6832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1332
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C19(H19A,H19B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), 
 C14(H14), C15(H15), C18(H18), N2(H2) 
2.c Idealised Me refined as rotating group: 
 C20(H20A,H20B,H20C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O1(H1), O2(H2A), O022(H022) 
;
_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
C1 C 0.6401(3) 0.52542(8) 0.15648(12) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.8446(3) 0.53847(8) 0.19490(12) 0.0249(4) Uani 1 1 d . . . . .
C3 C 0.9125(3) 0.60464(8) 0.21247(13) 0.0266(4) Uani 1 1 d . . . . .
H3 H 1.0481 0.6128 0.2386 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7778(3) 0.65864(8) 0.19094(13) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.5760(3) 0.64704(9) 0.14951(13) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.4873 0.6832 0.1326 0.033 Uiso 1 1 calc R . . . .
C6 C 0.5098(3) 0.58110(9) 0.13395(13) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.3742 0.5733 0.1076 0.032 Uiso 1 1 calc R . . . .
C7 C 0.5569(3) 0.45760(8) 0.14254(13) 0.0254(4) Uani 1 1 d . . . . .
H7 H 0.4169 0.4524 0.1229 0.030 Uiso 1 1 calc R . . . .
C8 C 0.6597(3) 0.28366(8) 0.15149(12) 0.0225(4) Uani 1 1 d . . . . .
C9 C 0.5223(3) 0.22530(8) 0.13525(13) 0.0268(4) Uani 1 1 d . . . . .
H9 H 0.3817 0.2323 0.1274 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5942(3) 0.16222(8) 0.13146(12) 0.0249(4) Uani 1 1 d . . . . .
H10 H 0.7355 0.1576 0.1378 0.030 Uiso 1 1 calc R . . . .
C11 C 0.4765(3) 0.10080(8) 0.11864(13) 0.0263(4) Uani 1 1 d . . . . .
H11 H 0.3348 0.1035 0.1041 0.032 Uiso 1 1 calc R . . . .
C12 C 0.5667(3) 0.03958(9) 0.12714(12) 0.0256(4) Uani 1 1 d . . . . .
H12 H 0.7087 0.0394 0.1413 0.031 Uiso 1 1 calc R . . . .
C13 C 0.4675(3) -0.02668(9) 0.11675(12) 0.0248(4) Uani 1 1 d . . . . .
C14 C 0.5879(3) -0.08410(9) 0.14317(13) 0.0275(4) Uani 1 1 d . . . . .
H14 H 0.7256 -0.0784 0.1676 0.033 Uiso 1 1 calc R . . . .
C15 C 0.5071(3) -0.14982(9) 0.13386(14) 0.0294(4) Uani 1 1 d . . . . .
H15 H 0.5872 -0.1878 0.1522 0.035 Uiso 1 1 calc R . . . .
C16 C 0.3058(3) -0.15535(8) 0.09668(13) 0.0269(4) Uani 1 1 d . . . . .
C17 C 0.1843(3) -0.09908(9) 0.06971(13) 0.0280(4) Uani 1 1 d . . . . .
C18 C 0.2593(3) -0.03437(8) 0.07949(13) 0.0276(4) Uani 1 1 d . . . . .
H18 H 0.1759 0.0030 0.0622 0.033 Uiso 1 1 calc R . . . .
C19 C -0.0018(3) -0.19209(9) 0.02916(16) 0.0368(5) Uani 1 1 d . . . . .
H19A H -0.1121 -0.2117 0.0576 0.044 Uiso 1 1 calc R . . . .
H19B H -0.0166 -0.2069 -0.0364 0.044 Uiso 1 1 calc R . . . .
N1 N 0.6695(2) 0.40416(7) 0.15631(11) 0.0245(4) Uani 1 1 d . . . . .
N2 N 0.5634(2) 0.34380(7) 0.14187(11) 0.0243(4) Uani 1 1 d . . . . .
H2 H 0.4324 0.3447 0.1264 0.029 Uiso 1 1 calc R . . . .
O1 O 0.9841(2) 0.48810(6) 0.21611(10) 0.0329(3) Uani 1 1 d . . . . .
H1 H 0.9275 0.4512 0.2060 0.049 Uiso 1 1 calc GR . . . .
O2 O 0.8355(2) 0.72432(5) 0.20715(10) 0.0308(3) Uani 1 1 d . . . . .
H2A H 0.9512 0.7256 0.2377 0.046 Uiso 1 1 calc GR . . . .
O3 O 0.84945(19) 0.27811(6) 0.17154(9) 0.0279(3) Uani 1 1 d . . . . .
O4 O 0.1899(2) -0.21354(6) 0.07931(11) 0.0365(4) Uani 1 1 d . . . . .
O5 O -0.0101(2) -0.11954(6) 0.03346(12) 0.0429(4) Uani 1 1 d . . . . .
C20 C 1.0456(3) 0.38319(10) 0.02270(15) 0.0382(5) Uani 1 1 d . . . . .
H20A H 1.1510 0.3981 -0.0116 0.057 Uiso 1 1 calc GR . . . .
H20B H 0.9594 0.4209 0.0325 0.057 Uiso 1 1 calc GR . . . .
H20C H 0.9650 0.3487 -0.0131 0.057 Uiso 1 1 calc GR . . . .
O022 O 1.13589(19) 0.35648(7) 0.11156(10) 0.0350(4) Uani 1 1 d . . . . .
H022 H 1.0504 0.3346 0.1345 0.052 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
C1 C2 1.401(3) . ?
C1 C6 1.401(2) . ?
C1 C7 1.447(2) . ?
C2 C3 1.389(2) . ?
C2 O1 1.357(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C4 C5 1.392(3) . ?
C4 O2 1.3586(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 N1 1.287(2) . ?
C8 C9 1.462(2) . ?
C8 N2 1.342(2) . ?
C8 O3 1.248(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.335(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.435(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.343(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.458(2) . ?
C13 C14 1.401(2) . ?
C13 C18 1.405(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.359(3) . ?
C16 C17 1.388(3) . ?
C16 O4 1.380(2) . ?
C17 C18 1.367(2) . ?
C17 O5 1.370(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 O4 1.419(3) . ?
C19 O5 1.432(2) . ?
N1 N2 1.3803(19) . ?
N2 H2 0.8600 . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 O022 1.415(2) . ?
O022 H022 0.8200 . ?

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
C2 C1 C7 123.13(15) . . ?
C6 C1 C2 117.87(15) . . ?
C6 C1 C7 118.96(16) . . ?
C3 C2 C1 120.54(16) . . ?
O1 C2 C1 122.30(15) . . ?
O1 C2 C3 117.16(16) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.00(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.46(15) . . ?
O2 C4 C3 122.55(16) . . ?
O2 C4 C5 116.98(15) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.86(16) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.20(17) . . ?
C5 C6 H6 118.9 . . ?
C1 C7 H7 118.8 . . ?
N1 C7 C1 122.37(17) . . ?
N1 C7 H7 118.8 . . ?
N2 C8 C9 113.86(16) . . ?
O3 C8 C9 123.09(15) . . ?
O3 C8 N2 123.05(15) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.45(17) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 116.6 . . ?
C9 C10 C11 126.89(17) . . ?
C11 C10 H10 116.6 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.44(18) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 116.2 . . ?
C11 C12 C13 127.51(18) . . ?
C13 C12 H12 116.2 . . ?
C14 C13 C12 117.91(17) . . ?
C14 C13 C18 119.82(16) . . ?
C18 C13 C12 122.26(15) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.95(18) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 121.7 . . ?
C16 C15 C14 116.61(16) . . ?
C16 C15 H15 121.7 . . ?
C15 C16 C17 122.26(16) . . ?
C15 C16 O4 128.31(15) . . ?
O4 C16 C17 109.43(16) . . ?
C18 C17 C16 122.11(18) . . ?
C18 C17 O5 128.12(17) . . ?
O5 C17 C16 109.77(15) . . ?
C13 C18 H18 121.4 . . ?
C17 C18 C13 117.24(16) . . ?
C17 C18 H18 121.4 . . ?
H19A C19 H19B 108.4 . . ?
O4 C19 H19A 110.1 . . ?
O4 C19 H19B 110.1 . . ?
O4 C19 O5 108.23(15) . . ?
O5 C19 H19A 110.1 . . ?
O5 C19 H19B 110.1 . . ?
C7 N1 N2 114.40(15) . . ?
C8 N2 N1 121.53(15) . . ?
C8 N2 H2 119.2 . . ?
N1 N2 H2 119.2 . . ?
C2 O1 H1 109.5 . . ?
C4 O2 H2A 109.5 . . ?
C16 O4 C19 105.70(13) . . ?
C17 O5 C19 105.65(14) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O022 C20 H20A 109.5 . . ?
O022 C20 H20B 109.5 . . ?
O022 C20 H20C 109.5 . . ?
C20 O022 H022 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
N2 H2 O022 0.86 1.95 2.805(2) 169.8 1_455
O1 H1 N1 0.82 1.97 2.6905(19) 145.5 .
O2 H2A O3 0.82 1.99 2.7075(18) 146.2 2_755
O022 H022 O3 0.82 1.87 2.6878(17) 172.2 .

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
C1 C2 C3 C4 -0.7(3) . . . . ?
C1 C7 N1 N2 178.44(14) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C7 N1 -6.6(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 O2 179.57(16) . . . . ?
C3 C4 C5 C6 2.7(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C6 C1 C2 C3 1.9(3) . . . . ?
C6 C1 C2 O1 -177.78(16) . . . . ?
C6 C1 C7 N1 175.78(16) . . . . ?
C7 C1 C2 C3 -175.70(16) . . . . ?
C7 C1 C2 O1 4.6(3) . . . . ?
C7 C1 C6 C5 176.88(16) . . . . ?
C7 N1 N2 C8 178.60(15) . . . . ?
C8 C9 C10 C11 178.17(16) . . . . ?
C9 C8 N2 N1 178.87(14) . . . . ?
C9 C10 C11 C12 -172.02(17) . . . . ?
C10 C11 C12 C13 179.59(16) . . . . ?
C11 C12 C13 C14 -170.15(17) . . . . ?
C11 C12 C13 C18 11.4(3) . . . . ?
C12 C13 C14 C15 -178.66(16) . . . . ?
C12 C13 C18 C17 177.63(16) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C13 C18 C17 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C14 C15 C16 O4 179.38(17) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C15 C16 C17 O5 179.08(17) . . . . ?
C15 C16 O4 C19 -172.56(19) . . . . ?
C16 C17 C18 C13 1.1(3) . . . . ?
C16 C17 O5 C19 -6.0(2) . . . . ?
C17 C16 O4 C19 7.3(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
C18 C17 O5 C19 173.53(19) . . . . ?
N2 C8 C9 C10 172.35(16) . . . . ?
O1 C2 C3 C4 179.02(16) . . . . ?
O2 C4 C5 C6 -178.45(16) . . . . ?
O3 C8 C9 C10 -7.0(3) . . . . ?
O3 C8 N2 N1 -1.8(3) . . . . ?
O4 C16 C17 C18 179.62(16) . . . . ?
O4 C16 C17 O5 -0.8(2) . . . . ?
O4 C19 O5 C17 10.5(2) . . . . ?
O5 C17 C18 C13 -178.35(17) . . . . ?
O5 C19 O4 C16 -11.0(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_cu_190528e_0m
_database_code_depnum_ccdc_archive 'CCDC 2009516'
loop_
_audit_author_name
_audit_author_address
'Ahmed H. Tantawy'
;Huazhong Agriculture University
China
;
_audit_update_record             
;
2020-06-12 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-30
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   18.1988(7)
_cell_length_b                   4.8105(2)
_cell_length_c                   22.1672(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.874(3)
_cell_angle_gamma                90
_cell_volume                     1788.03(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      64.10
_cell_measurement_theta_min      4.10
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1274 before and 0.0607 after correction. The Ra '
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14927
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        65.921
_diffrn_reflns_theta_max         65.921
_diffrn_reflns_theta_min         2.635
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             3069
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1575
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C20(H20A,H20B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), 
 C15(H15), C16(H16), C19(H19), N2(H2A) 
2.c Idealised Me refined as rotating group: 
 C7(H7A,H7B,H7C) 
2.d Idealised tetrahedral OH refined as rotating group: 
 O2(H2B) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.35046(13) -0.0588(4) 0.02034(10) 0.0447(5) Uani 1 1 d . . . . .
C2 C 0.40926(13) 0.1462(4) 0.04431(10) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.4244 0.2484 0.0154 0.056 Uiso 1 1 calc R . . . .
C3 C 0.44484(13) 0.1971(5) 0.11054(10) 0.0489(6) Uani 1 1 d . . . . .
C4 C 0.42036(14) 0.0507(5) 0.15411(11) 0.0525(6) Uani 1 1 d . . . . .
C5 C 0.36294(15) -0.1505(5) 0.13104(12) 0.0609(7) Uani 1 1 d . . . . .
H5 H 0.3467 -0.2482 0.1599 0.073 Uiso 1 1 calc R . . . .
C6 C 0.32912(14) -0.2085(5) 0.06451(11) 0.0548(6) Uani 1 1 d . . . . .
H6 H 0.2915 -0.3499 0.0493 0.066 Uiso 1 1 calc R . . . .
C7 C 0.54046(15) 0.5202(6) 0.10291(14) 0.0691(7) Uani 1 1 d . . . . .
H7A H 0.5011 0.6334 0.0707 0.104 Uiso 1 1 calc GR . . . .
H7B H 0.5611 0.3864 0.0814 0.104 Uiso 1 1 calc GR . . . .
H7C H 0.5831 0.6357 0.1308 0.104 Uiso 1 1 calc GR . . . .
C8 C 0.31287(13) -0.1229(5) -0.04891(10) 0.0457(5) Uani 1 1 d . . . . .
H8 H 0.2920 -0.2998 -0.0617 0.055 Uiso 1 1 calc R . . . .
C9 C 0.24917(13) 0.1389(4) -0.20754(10) 0.0436(5) Uani 1 1 d . . . . .
C10 C 0.21373(14) 0.0028(5) -0.27161(11) 0.0484(6) Uani 1 1 d . . . . .
H10 H 0.2004 -0.1844 -0.2731 0.058 Uiso 1 1 calc R . . . .
C11 C 0.19976(13) 0.1351(5) -0.32771(10) 0.0477(6) Uani 1 1 d . . . . .
H11 H 0.2151 0.3205 -0.3255 0.057 Uiso 1 1 calc R . . . .
C12 C 0.16284(13) 0.0127(5) -0.39112(10) 0.0489(6) Uani 1 1 d . . . . .
H12 H 0.1408 -0.1637 -0.3938 0.059 Uiso 1 1 calc R . . . .
C13 C 0.15768(13) 0.1340(5) -0.44697(11) 0.0492(6) Uani 1 1 d . . . . .
H13 H 0.1789 0.3119 -0.4437 0.059 Uiso 1 1 calc R . . . .
C14 C 0.12194(13) 0.0142(5) -0.51255(10) 0.0458(5) Uani 1 1 d . . . . .
C15 C 0.14739(14) 0.1054(5) -0.56074(11) 0.0543(6) Uani 1 1 d . . . . .
H15 H 0.1843 0.2492 -0.5509 0.065 Uiso 1 1 calc R . . . .
C16 C 0.11978(15) -0.0101(5) -0.62272(12) 0.0591(6) Uani 1 1 d . . . . .
H16 H 0.1387 0.0480 -0.6540 0.071 Uiso 1 1 calc R . . . .
C17 C 0.06331(14) -0.2136(5) -0.63579(11) 0.0517(6) Uani 1 1 d . . . . .
C18 C 0.03554(13) -0.3008(5) -0.58953(10) 0.0469(5) Uani 1 1 d . . . . .
C19 C 0.06363(13) -0.1959(5) -0.52779(10) 0.0461(5) Uani 1 1 d . . . . .
H19 H 0.0450 -0.2603 -0.4968 0.055 Uiso 1 1 calc R . . . .
C20 C -0.03308(16) -0.5247(6) -0.68314(12) 0.0612(7) Uani 1 1 d . . . . .
H20A H -0.0856 -0.4555 -0.7105 0.073 Uiso 1 1 calc R . . . .
H20B H -0.0292 -0.7169 -0.6948 0.073 Uiso 1 1 calc R . . . .
N1 N 0.30761(11) 0.0563(4) -0.09272(8) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.27210(11) -0.0397(4) -0.15635(8) 0.0475(5) Uani 1 1 d . . . . .
H2A H 0.2645 -0.2152 -0.1635 0.057 Uiso 1 1 calc R . . . .
O1 O 0.50512(11) 0.3803(4) 0.14094(8) 0.0695(6) Uani 1 1 d . . . . .
O2 O 0.45540(13) 0.0990(4) 0.21964(8) 0.0734(6) Uani 1 1 d . . . . .
H2B H 0.4798 0.2466 0.2262 0.110 Uiso 1 1 calc GR . . . .
O3 O 0.25559(11) 0.3921(3) -0.20059(7) 0.0596(5) Uani 1 1 d . . . . .
O4 O 0.02702(11) -0.3619(4) -0.69268(8) 0.0714(5) Uani 1 1 d . . . . .
O5 O -0.02112(10) -0.5052(4) -0.61582(8) 0.0621(5) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.399(3) . ?
C1 C6 1.387(3) . ?
C1 C8 1.450(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C3 C4 1.401(3) . ?
C3 O1 1.363(3) . ?
C4 C5 1.369(3) . ?
C4 O2 1.360(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 O1 1.414(3) . ?
C8 H8 0.9300 . ?
C8 N1 1.274(3) . ?
C9 C10 1.466(3) . ?
C9 N2 1.353(3) . ?
C9 O3 1.228(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.331(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.428(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.339(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.461(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.408(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.366(3) . ?
C17 C18 1.373(3) . ?
C17 O4 1.374(3) . ?
C18 C19 1.358(3) . ?
C18 O5 1.379(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 O4 1.426(3) . ?
C20 O5 1.425(3) . ?
N1 N2 1.383(2) . ?
N2 H2A 0.8600 . ?
O2 H2B 0.8200 . ?

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
C2 C1 C8 121.87(19) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 C8 119.4(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.1(2) . . ?
O1 C3 C2 126.6(2) . . ?
O1 C3 C4 113.23(19) . . ?
C5 C4 C3 119.9(2) . . ?
O2 C4 C3 120.5(2) . . ?
O2 C4 C5 119.5(2) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 121.0(2) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
C1 C8 H8 119.1 . . ?
N1 C8 C1 121.9(2) . . ?
N1 C8 H8 119.1 . . ?
N2 C9 C10 113.89(19) . . ?
O3 C9 C10 123.3(2) . . ?
O3 C9 N2 122.77(19) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.0(2) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 117.7 . . ?
C10 C11 C12 124.6(2) . . ?
C12 C11 H11 117.7 . . ?
C11 C12 H12 117.7 . . ?
C13 C12 C11 124.6(2) . . ?
C13 C12 H12 117.7 . . ?
C12 C13 H13 116.8 . . ?
C12 C13 C14 126.3(2) . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 C19 119.1(2) . . ?
C19 C14 C13 121.63(19) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 121.6 . . ?
C17 C16 C15 116.8(2) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 O4 128.3(2) . . ?
C18 C17 O4 110.0(2) . . ?
C17 C18 O5 109.51(19) . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 O5 128.1(2) . . ?
C14 C19 H19 121.2 . . ?
C18 C19 C14 117.5(2) . . ?
C18 C19 H19 121.2 . . ?
H20A C20 H20B 108.5 . . ?
O4 C20 H20A 110.2 . . ?
O4 C20 H20B 110.2 . . ?
O5 C20 H20A 110.2 . . ?
O5 C20 H20B 110.2 . . ?
O5 C20 O4 107.78(19) . . ?
C8 N1 N2 114.73(18) . . ?
C9 N2 N1 120.85(18) . . ?
C9 N2 H2A 119.6 . . ?
N1 N2 H2A 119.6 . . ?
C3 O1 C7 118.55(18) . . ?
C4 O2 H2B 109.5 . . ?
C17 O4 C20 105.78(18) . . ?
C18 O5 C20 105.92(17) . . ?

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
N2 H2A O3 0.86 2.04 2.880(2) 164.6 1_545

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -2.3(3) . . . . ?
C1 C2 C3 O1 176.8(2) . . . . ?
C1 C8 N1 N2 178.29(18) . . . . ?
C2 C1 C6 C5 2.4(3) . . . . ?
C2 C1 C8 N1 -26.3(3) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
C2 C3 C4 O2 179.7(2) . . . . ?
C2 C3 O1 C7 -5.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C3 O1 C7 173.7(2) . . . . ?
C4 C5 C6 C1 -2.3(4) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C8 N1 155.2(2) . . . . ?
C8 C1 C2 C3 -178.6(2) . . . . ?
C8 C1 C6 C5 -179.1(2) . . . . ?
C8 N1 N2 C9 167.5(2) . . . . ?
C9 C10 C11 C12 -177.7(2) . . . . ?
C10 C9 N2 N1 179.08(18) . . . . ?
C10 C11 C12 C13 -171.3(2) . . . . ?
C11 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 -154.5(2) . . . . ?
C12 C13 C14 C19 24.0(4) . . . . ?
C13 C14 C15 C16 176.0(2) . . . . ?
C13 C14 C19 C18 -178.0(2) . . . . ?
C14 C15 C16 C17 2.4(4) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 O4 -179.3(2) . . . . ?
C16 C17 C18 C19 -1.6(4) . . . . ?
C16 C17 C18 O5 179.6(2) . . . . ?
C16 C17 O4 C20 -173.7(3) . . . . ?
C17 C18 C19 C14 1.5(3) . . . . ?
C17 C18 O5 C20 -5.2(2) . . . . ?
C18 C17 O4 C20 7.2(3) . . . . ?
C19 C14 C15 C16 -2.5(3) . . . . ?
C19 C18 O5 C20 176.0(2) . . . . ?
N2 C9 C10 C11 -168.4(2) . . . . ?
O1 C3 C4 C5 -176.8(2) . . . . ?
O1 C3 C4 O2 0.6(3) . . . . ?
O2 C4 C5 C6 -177.5(2) . . . . ?
O3 C9 C10 C11 13.5(4) . . . . ?
O3 C9 N2 N1 -2.8(3) . . . . ?
O4 C17 C18 C19 177.5(2) . . . . ?
O4 C17 C18 O5 -1.3(3) . . . . ?
O4 C20 O5 C18 9.6(2) . . . . ?
O5 C18 C19 C14 -179.9(2) . . . . ?
O5 C20 O4 C17 -10.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
