# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_d8v18303_0m
_database_code_depnum_ccdc_archive 'CCDC 2024020'
loop_
_audit_author_name
_audit_author_address
'Gao xinhua'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        PR-9
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O5'
_chemical_formula_weight         289.28

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.14340(10)
_cell_length_b                   10.1986(2)
_cell_length_c                   11.1002(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.6270(10)
_cell_angle_gamma                90
_cell_volume                     693.21(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7436
_cell_measurement_theta_min      8.670
_cell_measurement_theta_max      140.316

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8372
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         7.983
_diffrn_reflns_theta_max         70.152
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2531
_reflns_number_gt                2493
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.958

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+0.0691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.074(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.09(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.2364(3) 0.2606(2) 0.22675(17) 0.0519(4) Uani 1 1 d . . . . .
O1 O 0.1366(2) 0.76142(14) 0.52451(15) 0.0509(4) Uani 1 1 d . . . . .
O2 O 0.3506(2) 0.64544(14) 0.41122(12) 0.0433(4) Uani 1 1 d . . . . .
O3 O -0.0111(2) 0.53021(16) 0.70004(15) 0.0526(4) Uani 1 1 d . . . . .
H3 H -0.0816 0.5923 0.7232 0.079 Uiso 1 1 calc R U . . .
O4 O 0.8220(4) 0.4473(2) 0.02579(17) 0.0752(6) Uani 1 1 d . . . . .
O5 O 0.6802(3) 0.25093(19) -0.02322(15) 0.0620(5) Uani 1 1 d . . . . .
C1 C 0.2686(3) 0.3431(2) 0.32105(19) 0.0461(5) Uani 1 1 d . . . . .
H1 H 0.1751 0.3389 0.3827 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3713(4) 0.2705(2) 0.1389(2) 0.0469(5) Uani 1 1 d . . . . .
H3A H 0.3484 0.2147 0.0728 0.056 Uiso 1 1 calc R U . . .
C4 C 0.5444(3) 0.3590(2) 0.13960(17) 0.0408(4) Uani 1 1 d . . . . .
C5 C 0.5768(3) 0.44281(18) 0.23813(17) 0.0378(4) Uani 1 1 d . . . . .
C6 C 0.7485(3) 0.5451(2) 0.26886(19) 0.0459(5) Uani 1 1 d . . . . .
H6A H 0.7196 0.6242 0.2216 0.055 Uiso 1 1 calc R U . . .
H6B H 0.8927 0.5127 0.2548 0.055 Uiso 1 1 calc R U . . .
C7 C 0.7290(3) 0.5710(2) 0.4044(2) 0.0460(5) Uani 1 1 d . . . . .
H7A H 0.8350 0.5192 0.4532 0.055 Uiso 1 1 calc R U . . .
H7B H 0.7539 0.6630 0.4230 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4953(3) 0.5311(2) 0.42893(18) 0.0396(4) Uani 1 1 d . . . . .
C9 C 0.4353(3) 0.43341(18) 0.32922(16) 0.0378(4) Uani 1 1 d . . . . .
C10 C 0.4594(3) 0.48726(19) 0.55424(18) 0.0414(4) Uani 1 1 d . . . . .
H10 H 0.5299 0.4166 0.5933 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3139(3) 0.56254(18) 0.60189(18) 0.0395(4) Uani 1 1 d . . . . .
C12 C 0.2506(3) 0.66668(18) 0.51445(18) 0.0392(4) Uani 1 1 d . . . . .
C13 C 0.2153(3) 0.5569(2) 0.72190(17) 0.0444(5) Uani 1 1 d . . . . .
H13 H 0.2325 0.6430 0.7606 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3230(5) 0.4560(3) 0.8057(2) 0.0699(7) Uani 1 1 d . . . . .
H14A H 0.2591 0.4588 0.8817 0.105 Uiso 1 1 calc R U . . .
H14B H 0.4764 0.4744 0.8182 0.105 Uiso 1 1 calc R U . . .
H14C H 0.3022 0.3705 0.7705 0.105 Uiso 1 1 calc R U . . .
C15 C 0.6973(3) 0.3591(2) 0.04203(18) 0.0482(5) Uani 1 1 d . . . . .
C16 C 0.8310(5) 0.2366(4) -0.1164(3) 0.0814(9) Uani 1 1 d . . . . .
H16A H 0.8434 0.3186 -0.1578 0.122 Uiso 1 1 calc R U . . .
H16B H 0.7776 0.1707 -0.1730 0.122 Uiso 1 1 calc R U . . .
H16C H 0.9718 0.2111 -0.0801 0.122 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.334(3) . ?
N1 C1 1.345(3) . ?
O1 C12 1.204(2) . ?
O2 C12 1.361(2) . ?
O2 C8 1.469(2) . ?
O3 C13 1.419(3) . ?
O3 H3 0.8200 . ?
O4 C15 1.204(3) . ?
O5 C15 1.319(3) . ?
O5 C16 1.451(3) . ?
C1 C9 1.375(3) . ?
C1 H1 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.390(3) . ?
C4 C15 1.490(3) . ?
C5 C9 1.389(2) . ?
C5 C6 1.503(3) . ?
C6 C7 1.541(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.538(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.494(3) . ?
C8 C9 1.513(3) . ?
C10 C11 1.321(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.470(3) . ?
C11 C13 1.508(3) . ?
C13 C14 1.503(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C3 N1 C1 117.44(18) . . ?
C12 O2 C8 108.84(14) . . ?
C13 O3 H3 109.5 . . ?
C15 O5 C16 116.6(2) . . ?
N1 C1 C9 122.18(18) . . ?
N1 C1 H1 118.9 . . ?
C9 C1 H1 118.9 . . ?
N1 C3 C4 124.3(2) . . ?
N1 C3 H3A 117.9 . . ?
C4 C3 H3A 117.9 . . ?
C5 C4 C3 117.63(17) . . ?
C5 C4 C15 120.83(17) . . ?
C3 C4 C15 121.45(19) . . ?
C9 C5 C4 118.16(17) . . ?
C9 C5 C6 110.58(17) . . ?
C4 C5 C6 131.24(16) . . ?
C5 C6 C7 103.43(16) . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C6 105.95(16) . . ?
C8 C7 H7A 110.5 . . ?
C6 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
O2 C8 C10 103.25(14) . . ?
O2 C8 C9 108.41(15) . . ?
C10 C8 C9 115.99(17) . . ?
O2 C8 C7 109.25(16) . . ?
C10 C8 C7 117.01(17) . . ?
C9 C8 C7 102.73(15) . . ?
C1 C9 C5 120.32(18) . . ?
C1 C9 C8 128.75(17) . . ?
C5 C9 C8 110.94(16) . . ?
C11 C10 C8 110.74(17) . . ?
C11 C10 H10 124.6 . . ?
C8 C10 H10 124.6 . . ?
C10 C11 C12 107.88(18) . . ?
C10 C11 C13 131.63(18) . . ?
C12 C11 C13 120.49(16) . . ?
O1 C12 O2 120.76(18) . . ?
O1 C12 C11 130.06(19) . . ?
O2 C12 C11 109.14(15) . . ?
O3 C13 C14 110.54(19) . . ?
O3 C13 C11 108.31(15) . . ?
C14 C13 C11 112.62(18) . . ?
O3 C13 H13 108.4 . . ?
C14 C13 H13 108.4 . . ?
C11 C13 H13 108.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O5 124.46(19) . . ?
O4 C15 C4 123.8(2) . . ?
O5 C15 C4 111.78(19) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C9 -1.0(3) . . . . ?
C1 N1 C3 C4 1.0(3) . . . . ?
N1 C3 C4 C5 -0.5(3) . . . . ?
N1 C3 C4 C15 176.1(2) . . . . ?
C3 C4 C5 C9 -0.1(3) . . . . ?
C15 C4 C5 C9 -176.73(18) . . . . ?
C3 C4 C5 C6 177.9(2) . . . . ?
C15 C4 C5 C6 1.3(3) . . . . ?
C9 C5 C6 C7 14.2(2) . . . . ?
C4 C5 C6 C7 -163.9(2) . . . . ?
C5 C6 C7 C8 -23.9(2) . . . . ?
C12 O2 C8 C10 1.76(19) . . . . ?
C12 O2 C8 C9 125.33(16) . . . . ?
C12 O2 C8 C7 -123.44(17) . . . . ?
C6 C7 C8 O2 -90.54(19) . . . . ?
C6 C7 C8 C10 152.69(17) . . . . ?
C6 C7 C8 C9 24.4(2) . . . . ?
N1 C1 C9 C5 0.5(3) . . . . ?
N1 C1 C9 C8 -179.1(2) . . . . ?
C4 C5 C9 C1 0.1(3) . . . . ?
C6 C5 C9 C1 -178.32(18) . . . . ?
C4 C5 C9 C8 179.75(17) . . . . ?
C6 C5 C9 C8 1.4(2) . . . . ?
O2 C8 C9 C1 -81.1(2) . . . . ?
C10 C8 C9 C1 34.4(3) . . . . ?
C7 C8 C9 C1 163.3(2) . . . . ?
O2 C8 C9 C5 99.24(17) . . . . ?
C10 C8 C9 C5 -145.23(16) . . . . ?
C7 C8 C9 C5 -16.3(2) . . . . ?
O2 C8 C10 C11 0.9(2) . . . . ?
C9 C8 C10 C11 -117.48(19) . . . . ?
C7 C8 C10 C11 120.9(2) . . . . ?
C8 C10 C11 C12 -3.0(2) . . . . ?
C8 C10 C11 C13 177.35(19) . . . . ?
C8 O2 C12 O1 174.34(18) . . . . ?
C8 O2 C12 C11 -3.6(2) . . . . ?
C10 C11 C12 O1 -173.5(2) . . . . ?
C13 C11 C12 O1 6.2(3) . . . . ?
C10 C11 C12 O2 4.2(2) . . . . ?
C13 C11 C12 O2 -176.11(16) . . . . ?
C10 C11 C13 O3 -114.8(2) . . . . ?
C12 C11 C13 O3 65.7(2) . . . . ?
C10 C11 C13 C14 7.8(3) . . . . ?
C12 C11 C13 C14 -171.8(2) . . . . ?
C16 O5 C15 O4 3.2(4) . . . . ?
C16 O5 C15 C4 -176.3(2) . . . . ?
C5 C4 C15 O4 -18.0(3) . . . . ?
C3 C4 C15 O4 165.5(2) . . . . ?
C5 C4 C15 O5 161.52(19) . . . . ?
C3 C4 C15 O5 -15.0(3) . . . . ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mjl18230_0m
_database_code_depnum_ccdc_archive 'CCDC 2024022'
loop_
_audit_author_name
_audit_author_address
'Gao xinhua'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 N O5'
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9407(4)
_cell_length_b                   23.6776(12)
_cell_length_c                   8.0529(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.765(2)
_cell_angle_gamma                90
_cell_volume                     1322.78(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.925
_cell_measurement_theta_min      4.877
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1046 before and 0.0509 after correction. The Ratio of minimum to maximum transmission is 0.8351. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15931
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.900
_diffrn_reflns_theta_min         5.783
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                4845
_reflns_number_total             4889
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 2312 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4889
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0744
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C13A(H13A)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C10(H10), C1A(H1A), C3A(H3A), C6A(H6A),
 C7A(H7A), C10A(H10A)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C14A(H14D,H14E,H14F), C16A(H16D,
 H16E,H16F)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4140(3) 0.83237(6) 1.2752(2) 0.0387(4) Uani 1 1 d . . . . .
O2 O 0.5024(3) 0.80425(7) 1.5324(2) 0.0393(4) Uani 1 1 d . . . . .
O3 O 0.18604(19) 0.61328(5) 0.94298(17) 0.0228(3) Uani 1 1 d . . . . .
O4 O 0.1102(2) 0.52829(6) 0.83823(18) 0.0285(3) Uani 1 1 d . . . . .
O5 O 0.6612(2) 0.54562(6) 0.59594(17) 0.0281(3) Uani 1 1 d . . . . .
H5 H 0.619739 0.573548 0.541365 0.042 Uiso 1 1 calc GR . . . .
N2 N 0.5096(3) 0.63736(7) 1.4122(2) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.4588(3) 0.62031(8) 1.2553(2) 0.0243(4) Uani 1 1 d . . . . .
H1 H 0.453561 0.581104 1.230491 0.029 Uiso 1 1 calc R . . . .
C3 C 0.5114(3) 0.69248(9) 1.4435(2) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.547088 0.704192 1.552965 0.031 Uiso 1 1 calc R . . . .
C4 C 0.4645(3) 0.73466(8) 1.3266(2) 0.0232(4) Uani 1 1 d . . . . .
C5 C 0.4172(3) 0.71666(8) 1.1659(2) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.3582(3) 0.74652(8) 1.0120(2) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.350876 0.786370 0.999538 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3167(3) 0.70885(8) 0.8927(2) 0.0231(4) Uani 1 1 d . . . . .
H7 H 0.268947 0.718237 0.784355 0.028 Uiso 1 1 calc R . . . .
C8 C 0.3561(3) 0.64887(7) 0.9531(2) 0.0203(4) Uani 1 1 d . . . . .
C9 C 0.4150(3) 0.65882(8) 1.1328(2) 0.0208(4) Uani 1 1 d . . . . .
C10 C 0.5025(3) 0.61727(8) 0.8543(2) 0.0214(4) Uani 1 1 d . . . . .
H10 H 0.629403 0.630047 0.834231 0.026 Uiso 1 1 calc R . . . .
C11 C 0.4271(3) 0.56882(8) 0.7995(2) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.2277(3) 0.56490(8) 0.8578(2) 0.0208(4) Uani 1 1 d . . . . .
C13 C 0.5114(3) 0.52347(8) 0.6928(2) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.407834 0.507678 0.617273 0.028 Uiso 1 1 calc R . . . .
C14 C 0.5980(3) 0.47606(9) 0.7987(3) 0.0326(5) Uani 1 1 d . . . . .
H14A H 0.640696 0.445497 0.726471 0.049 Uiso 1 1 calc GR . . . .
H14B H 0.500599 0.461610 0.873357 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.708414 0.490537 0.864474 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.4583(3) 0.79541(9) 1.3718(3) 0.0279(4) Uani 1 1 d . . . . .
C16 C 0.4875(5) 0.86246(11) 1.5864(4) 0.0507(7) Uani 1 1 d . . . . .
H16A H 0.586406 0.885150 1.533290 0.076 Uiso 1 1 calc GR . . . .
H16B H 0.506514 0.864381 1.707312 0.076 Uiso 1 1 calc GR . . . .
H16C H 0.359585 0.877200 1.554918 0.076 Uiso 1 1 calc GR . . . .
O1A O 0.9556(3) 0.24745(7) -0.51874(18) 0.0382(4) Uani 1 1 d . . . . .
O2A O 1.0277(2) 0.16244(6) -0.41273(19) 0.0318(3) Uani 1 1 d . . . . .
O3A O 1.26780(18) 0.40609(5) 0.04369(17) 0.0234(3) Uani 1 1 d . . . . .
O4A O 1.3227(2) 0.47582(7) 0.22701(19) 0.0323(3) Uani 1 1 d . . . . .
O5A O 0.9253(3) 0.46861(7) 0.44061(19) 0.0416(4) Uani 1 1 d . . . . .
H5A H 0.861876 0.490055 0.501528 0.062 Uiso 1 1 calc GR . . . .
N2A N 1.1509(2) 0.22057(7) 0.0542(2) 0.0234(3) Uani 1 1 d . . . . .
C1A C 1.1502(3) 0.27681(8) 0.0839(2) 0.0228(4) Uani 1 1 d . . . . .
H1A H 1.175867 0.289916 0.193888 0.027 Uiso 1 1 calc R . . . .
C3A C 1.1060(3) 0.20378(8) -0.1004(2) 0.0216(4) Uani 1 1 d . . . . .
H3A H 1.102133 0.164284 -0.120968 0.026 Uiso 1 1 calc R . . . .
C4A C 1.0638(3) 0.23992(8) -0.2354(2) 0.0204(4) Uani 1 1 d . . . . .
C5A C 1.0727(3) 0.29780(8) -0.2042(2) 0.0210(4) Uani 1 1 d . . . . .
C6A C 1.0539(3) 0.34767(8) -0.3114(2) 0.0249(4) Uani 1 1 d . . . . .
H6A H 1.027476 0.346994 -0.427879 0.030 Uiso 1 1 calc R . . . .
C7A C 1.0797(3) 0.39415(8) -0.2197(2) 0.0250(4) Uani 1 1 d . . . . .
H7A H 1.083656 0.431413 -0.263250 0.030 Uiso 1 1 calc R . . . .
C8A C 1.1018(3) 0.37952(7) -0.0363(2) 0.0216(4) Uani 1 1 d . . . . .
C9A C 1.1135(3) 0.31558(7) -0.0402(2) 0.0209(4) Uani 1 1 d . . . . .
C10A C 0.9347(3) 0.40272(8) 0.0571(2) 0.0235(4) Uani 1 1 d . . . . .
H10A H 0.804381 0.391193 0.040518 0.028 Uiso 1 1 calc R . . . .
C11A C 0.9946(3) 0.44150(8) 0.1659(2) 0.0231(4) Uani 1 1 d . . . . .
C12A C 1.2077(3) 0.44552(8) 0.1560(2) 0.0234(4) Uani 1 1 d . . . . .
C13A C 0.8754(3) 0.47961(8) 0.2710(2) 0.0264(4) Uani 1 1 d . . . . .
H13A H 0.736200 0.470130 0.250890 0.032 Uiso 1 1 calc R . . . .
C14A C 0.9065(3) 0.54119(8) 0.2252(3) 0.0307(4) Uani 1 1 d . . . . .
H14D H 0.821958 0.565154 0.290326 0.046 Uiso 1 1 calc GR . . . .
H14E H 0.876513 0.546573 0.106575 0.046 Uiso 1 1 calc GR . . . .
H14F H 1.041254 0.551522 0.249293 0.046 Uiso 1 1 calc GR . . . .
C15A C 1.0109(3) 0.21845(8) -0.4037(2) 0.0234(4) Uani 1 1 d . . . . .
C16A C 0.9769(3) 0.13738(9) -0.5722(3) 0.0338(5) Uani 1 1 d . . . . .
H16D H 1.039203 0.158464 -0.660462 0.051 Uiso 1 1 calc GR . . . .
H16E H 0.836689 0.138702 -0.590475 0.051 Uiso 1 1 calc GR . . . .
H16F H 1.020339 0.098005 -0.573623 0.051 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
O1 C15 1.205(3) . ?
O2 C15 1.336(3) . ?
O2 C16 1.450(3) . ?
O3 C8 1.450(2) . ?
O3 C12 1.370(2) . ?
O4 C12 1.198(2) . ?
O5 H5 0.8400 . ?
O5 C13 1.419(2) . ?
N2 C1 1.363(3) . ?
N2 C3 1.329(3) . ?
C1 H1 0.9500 . ?
C1 C9 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 C5 1.393(3) . ?
C4 C15 1.485(3) . ?
C5 C6 1.474(3) . ?
C5 C9 1.395(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.336(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.523(3) . ?
C8 C9 1.510(3) . ?
C8 C10 1.508(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.330(3) . ?
C11 C12 1.478(3) . ?
C11 C13 1.505(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.522(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1A C15A 1.206(3) . ?
O2A C15A 1.333(2) . ?
O2A C16A 1.449(2) . ?
O3A C8A 1.447(2) . ?
O3A C12A 1.374(2) . ?
O4A C12A 1.204(2) . ?
O5A H5A 0.8400 . ?
O5A C13A 1.423(3) . ?
N2A C1A 1.353(2) . ?
N2A C3A 1.335(3) . ?
C1A H1A 0.9500 . ?
C1A C9A 1.375(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.407(3) . ?
C4A C5A 1.394(3) . ?
C4A C15A 1.483(3) . ?
C5A C6A 1.466(3) . ?
C5A C9A 1.407(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.334(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.521(3) . ?
C8A C9A 1.516(2) . ?
C8A C10A 1.506(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.327(3) . ?
C11A C12A 1.487(3) . ?
C11A C13A 1.503(3) . ?
C13A H13A 1.0000 . ?
C13A C14A 1.521(3) . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C16 115.01(19) . . ?
C12 O3 C8 109.25(14) . . ?
C13 O5 H5 109.5 . . ?
C3 N2 C1 117.84(17) . . ?
N2 C1 H1 119.5 . . ?
N2 C1 C9 121.05(18) . . ?
C9 C1 H1 119.5 . . ?
N2 C3 H3 117.6 . . ?
N2 C3 C4 124.85(19) . . ?
C4 C3 H3 117.6 . . ?
C3 C4 C15 122.20(19) . . ?
C5 C4 C3 116.64(18) . . ?
C5 C4 C15 121.12(19) . . ?
C4 C5 C6 133.33(18) . . ?
C4 C5 C9 118.61(17) . . ?
C9 C5 C6 108.02(16) . . ?
C5 C6 H6 125.3 . . ?
C7 C6 C5 109.42(16) . . ?
C7 C6 H6 125.3 . . ?
C6 C7 H7 124.4 . . ?
C6 C7 C8 111.12(16) . . ?
C8 C7 H7 124.4 . . ?
O3 C8 C7 112.71(15) . . ?
O3 C8 C9 109.91(14) . . ?
O3 C8 C10 104.03(14) . . ?
C9 C8 C7 101.61(14) . . ?
C10 C8 C7 114.27(15) . . ?
C10 C8 C9 114.57(15) . . ?
C1 C9 C5 120.97(18) . . ?
C1 C9 C8 129.31(17) . . ?
C5 C9 C8 109.71(16) . . ?
C8 C10 H10 125.1 . . ?
C11 C10 C8 109.77(16) . . ?
C11 C10 H10 125.1 . . ?
C10 C11 C12 108.12(16) . . ?
C10 C11 C13 130.46(18) . . ?
C12 C11 C13 121.40(16) . . ?
O3 C12 C11 108.71(15) . . ?
O4 C12 O3 121.16(17) . . ?
O4 C12 C11 130.12(17) . . ?
O5 C13 C11 110.75(15) . . ?
O5 C13 H13 109.2 . . ?
O5 C13 C14 107.30(16) . . ?
C11 C13 H13 109.2 . . ?
C11 C13 C14 111.10(15) . . ?
C14 C13 H13 109.2 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 O2 123.89(19) . . ?
O1 C15 C4 123.65(19) . . ?
O2 C15 C4 112.44(18) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15A O2A C16A 115.87(16) . . ?
C12A O3A C8A 109.56(14) . . ?
C13A O5A H5A 109.5 . . ?
C3A N2A C1A 117.15(17) . . ?
N2A C1A H1A 119.0 . . ?
N2A C1A C9A 121.99(18) . . ?
C9A C1A H1A 119.0 . . ?
N2A C3A H3A 117.4 . . ?
N2A C3A C4A 125.21(17) . . ?
C4A C3A H3A 117.4 . . ?
C3A C4A C15A 122.50(17) . . ?
C5A C4A C3A 116.84(17) . . ?
C5A C4A C15A 120.66(17) . . ?
C4A C5A C6A 133.07(18) . . ?
C4A C5A C9A 118.03(17) . . ?
C9A C5A C6A 108.87(16) . . ?
C5A C6A H6A 125.4 . . ?
C7A C6A C5A 109.29(17) . . ?
C7A C6A H6A 125.4 . . ?
C6A C7A H7A 124.5 . . ?
C6A C7A C8A 110.95(17) . . ?
C8A C7A H7A 124.5 . . ?
O3A C8A C7A 112.87(15) . . ?
O3A C8A C9A 113.65(15) . . ?
O3A C8A C10A 103.55(14) . . ?
C9A C8A C7A 102.18(15) . . ?
C10A C8A C7A 110.24(15) . . ?
C10A C8A C9A 114.66(15) . . ?
C1A C9A C5A 120.67(17) . . ?
C1A C9A C8A 131.29(17) . . ?
C5A C9A C8A 108.02(16) . . ?
C8A C10A H10A 124.7 . . ?
C11A C10A C8A 110.58(17) . . ?
C11A C10A H10A 124.7 . . ?
C10A C11A C12A 107.52(16) . . ?
C10A C11A C13A 128.33(19) . . ?
C12A C11A C13A 123.90(17) . . ?
O3A C12A C11A 108.34(15) . . ?
O4A C12A O3A 120.48(17) . . ?
O4A C12A C11A 131.18(18) . . ?
O5A C13A C11A 107.97(16) . . ?
O5A C13A H13A 108.7 . . ?
O5A C13A C14A 112.07(18) . . ?
C11A C13A H13A 108.7 . . ?
C11A C13A C14A 110.75(16) . . ?
C14A C13A H13A 108.7 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
O1A C15A O2A 123.42(19) . . ?
O1A C15A C4A 124.78(18) . . ?
O2A C15A C4A 111.78(17) . . ?
O2A C16A H16D 109.5 . . ?
O2A C16A H16E 109.5 . . ?
O2A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 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
O5 H5 N2 0.84 1.97 2.814(2) 177.2 1_554
O5A H5A O5 0.84 2.08 2.897(2) 165.0 .

_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_22020101_0m
_database_code_depnum_ccdc_archive 'CCDC 2024021'
loop_
_audit_author_name
_audit_author_address
'Gao xinhua'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_audit_creation_date             2020-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C15 H13 N O5), 0.5(C15 H15 N O5)'
_chemical_formula_sum            'C15 H14 N O5'
_chemical_formula_weight         288.27
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3810(4)
_cell_length_b                   16.4425(7)
_cell_length_c                   20.4203(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2814.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    240
_cell_measurement_theta_max      74.469
_cell_measurement_theta_min      3.451
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1609 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19899
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.757
_diffrn_reflns_theta_min         3.451
_diffrn_ambient_temperature      240
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5172
_reflns_number_total             5732
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0948P)²+0.0325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C26(H26), C10(H10), C19(H19), C16(H16), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C00Y(H00A,H00B,H00C), C15(H15A,H15B,H15C), C31(H31A,H31B,
 H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O8(H8)
;
_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
O10 O 1.1623(3) 0.66566(11) 0.50584(10) 0.0511(4) Uani 1 1 d . . . . .
O3 O 1.1105(3) 0.44832(14) 0.75048(9) 0.0544(5) Uani 1 1 d . . . . .
O1 O 0.7625(3) 0.54311(14) 0.91339(11) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.702078 0.504194 0.906029 0.086 Uiso 1 1 calc GR . . . .
O7 O 0.8029(3) 0.42074(17) 0.66046(10) 0.0650(6) Uani 1 1 d . . . . .
O8 O 0.4588(3) 0.25613(12) 0.53703(12) 0.0581(5) Uani 1 1 d . . . . .
H8 H 0.401317 0.296554 0.530950 0.087 Uiso 1 1 calc GR . . . .
O9 O 1.4101(3) 0.61577(13) 0.50891(13) 0.0610(5) Uani 1 1 d . . . . .
O2 O 0.9970(3) 0.56585(16) 0.72007(11) 0.0655(6) Uani 1 1 d . . . . .
O4 O 1.4962(3) 0.15886(14) 0.80144(12) 0.0623(5) Uani 1 1 d . . . . .
N2 N 1.5248(3) 0.43194(15) 0.87732(11) 0.0500(5) Uani 1 1 d . . . . .
O5 O 1.7140(4) 0.20394(17) 0.85333(13) 0.0694(6) Uani 1 1 d . . . . .
N18 N 1.2387(3) 0.38461(15) 0.54733(18) 0.0621(7) Uani 1 1 d . . . . .
C1 C 1.3722(4) 0.44625(16) 0.86090(13) 0.0478(6) Uani 1 1 d . . . . .
H1A H 1.328381 0.497922 0.868972 0.057 Uiso 1 1 calc R . . . .
O6 O 0.6815(5) 0.3283(3) 0.72278(12) 0.1080(14) Uani 1 1 d . . . . .
C21 C 1.0346(3) 0.51827(13) 0.55369(11) 0.0377(5) Uani 1 1 d . . . . .
C9 C 1.2779(3) 0.38713(15) 0.83250(12) 0.0437(5) Uani 1 1 d . . . . .
C4 C 1.4946(3) 0.29364(16) 0.83959(11) 0.0438(5) Uani 1 1 d . . . . .
C27 C 0.6430(3) 0.32895(16) 0.60580(12) 0.0449(5) Uani 1 1 d . . . . .
C12 C 1.0137(4) 0.51360(17) 0.76024(13) 0.0486(6) Uani 1 1 d . . . . .
C20 C 1.1928(3) 0.52822(14) 0.53473(12) 0.0416(5) Uani 1 1 d . . . . .
C11 C 0.9428(3) 0.50680(15) 0.82641(12) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.8312(4) 0.56978(16) 0.85411(13) 0.0488(6) Uani 1 1 d . . . . .
H13 H 0.745129 0.580419 0.822030 0.059 Uiso 1 1 calc R . . . .
C24 C 0.8104(4) 0.43951(16) 0.59058(13) 0.0472(6) Uani 1 1 d . . . . .
C5 C 1.3384(3) 0.30948(14) 0.82073(11) 0.0421(5) Uani 1 1 d . . . . .
C25 C 0.9824(3) 0.44054(15) 0.56963(12) 0.0437(5) Uani 1 1 d . . . . .
C8 C 1.1089(4) 0.39606(16) 0.80851(14) 0.0488(6) Uani 1 1 d . . . . .
C3 C 1.5810(4) 0.35792(18) 0.86689(12) 0.0489(6) Uani 1 1 d . . . . .
H3 H 1.687533 0.347742 0.878773 0.059 Uiso 1 1 calc R . . . .
C26 C 0.7060(3) 0.37666(16) 0.56048(12) 0.0432(5) Uani 1 1 d . . . . .
H26 H 0.687278 0.371516 0.515287 0.052 Uiso 1 1 calc R . . . .
C00S C 1.5812(4) 0.21478(18) 0.83257(13) 0.0508(6) Uani 1 1 d . . . . .
C14 C 0.9191(5) 0.64911(18) 0.86820(18) 0.0630(8) Uani 1 1 d . . . . .
H14A H 0.843549 0.689708 0.883261 0.094 Uiso 1 1 calc GR . . . .
H14B H 0.970612 0.668139 0.828526 0.094 Uiso 1 1 calc GR . . . .
H14C H 0.998931 0.639917 0.901777 0.094 Uiso 1 1 calc GR . . . .
C10 C 0.9975(3) 0.43902(15) 0.85354(13) 0.0453(5) Uani 1 1 d . . . . .
H10 H 0.969664 0.420571 0.895590 0.054 Uiso 1 1 calc R . . . .
C28 C 0.7054(5) 0.3560(3) 0.66949(14) 0.0639(8) Uani 1 1 d . . . . .
C30 C 0.5263(4) 0.26006(16) 0.60001(16) 0.0527(6) Uani 1 1 d . . . . .
H30 H 0.439567 0.268776 0.632153 0.063 Uiso 1 1 calc R . . . .
C19 C 1.2890(4) 0.45963(17) 0.53247(16) 0.0525(6) Uani 1 1 d . . . . .
H19 H 1.396029 0.466237 0.519740 0.063 Uiso 1 1 calc R . . . .
C00Y C 1.2273(5) 0.74418(18) 0.48927(16) 0.0577(7) Uani 1 1 d . . . . .
H00A H 1.296371 0.738938 0.451388 0.087 Uiso 1 1 calc GR . . . .
H00B H 1.288340 0.764955 0.526003 0.087 Uiso 1 1 calc GR . . . .
H00C H 1.140992 0.781462 0.479278 0.087 Uiso 1 1 calc GR . . . .
C6 C 1.2146(4) 0.25784(17) 0.78704(15) 0.0526(6) Uani 1 1 d . . . . .
H6A H 1.202562 0.205373 0.809259 0.063 Uiso 1 1 calc R . . . .
H6B H 1.243896 0.248091 0.741239 0.063 Uiso 1 1 calc R . . . .
C16 C 1.0861(4) 0.37560(16) 0.56542(17) 0.0562(7) Uani 1 1 d . . . . .
H16 H 1.048416 0.323255 0.575591 0.067 Uiso 1 1 calc R . . . .
C22 C 0.9019(4) 0.57848(15) 0.56156(13) 0.0470(6) Uani 1 1 d . . . . .
H22 H 0.907589 0.635301 0.557079 0.056 Uiso 1 1 calc R . . . .
C012 C 1.2686(4) 0.60669(15) 0.51572(12) 0.0445(6) Uani 1 1 d . . . . .
C7 C 1.0612(4) 0.30743(19) 0.7915(2) 0.0709(10) Uani 1 1 d . . . . .
H7A H 0.991420 0.285164 0.825607 0.085 Uiso 1 1 calc R . . . .
H7B H 1.003989 0.305860 0.749681 0.085 Uiso 1 1 calc R . . . .
C15 C 1.5746(6) 0.0809(2) 0.7932(2) 0.0760(10) Uani 1 1 d . . . . .
H15A H 1.505664 0.044687 0.768650 0.114 Uiso 1 1 calc GR . . . .
H15B H 1.596556 0.057499 0.835874 0.114 Uiso 1 1 calc GR . . . .
H15C H 1.673973 0.088495 0.769658 0.114 Uiso 1 1 calc GR . . . .
C31 C 0.6048(5) 0.1787(2) 0.6144(3) 0.0802(12) Uani 1 1 d . . . . .
H31A H 0.524950 0.136028 0.613246 0.120 Uiso 1 1 calc GR . . . .
H31B H 0.653614 0.180345 0.657463 0.120 Uiso 1 1 calc GR . . . .
H31C H 0.685997 0.167784 0.581712 0.120 Uiso 1 1 calc GR . . . .
C23 C 0.7562(5) 0.52789(19) 0.5783(3) 0.0805(13) Uani 1 1 d . . . . .
H23 H 0.650781 0.547110 0.580826 0.097 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
O10 C00Y 1.442(3) . ?
O10 C012 1.332(4) . ?
O3 C12 1.360(4) . ?
O3 C8 1.464(4) . ?
O1 C13 1.410(4) . ?
O7 C24 1.461(4) . ?
O7 C28 1.354(5) . ?
O8 C30 1.407(4) . ?
O9 C012 1.204(4) . ?
O2 C12 1.196(4) . ?
O4 C00S 1.325(4) . ?
O4 C15 1.449(4) . ?
N2 C1 1.343(4) . ?
N2 C3 1.322(4) . ?
O5 C00S 1.204(5) . ?
N18 C19 1.338(4) . ?
N18 C16 1.339(5) . ?
C1 C9 1.380(4) . ?
O6 C28 1.197(4) . ?
C21 C20 1.391(4) . ?
C21 C25 1.390(3) . ?
C21 C22 1.498(3) . ?
C9 C5 1.395(4) . ?
C9 C8 1.506(4) . ?
C4 C5 1.389(4) . ?
C4 C3 1.398(4) . ?
C4 C00S 1.493(4) . ?
C27 C26 1.323(4) . ?
C27 C28 1.471(4) . ?
C27 C30 1.501(4) . ?
C12 C11 1.480(4) . ?
C20 C19 1.387(4) . ?
C20 C012 1.489(3) . ?
C11 C13 1.506(4) . ?
C11 C10 1.326(4) . ?
C13 C14 1.525(4) . ?
C24 C25 1.504(4) . ?
C24 C26 1.487(4) . ?
C24 C23 1.543(4) . ?
C5 C6 1.506(4) . ?
C25 C16 1.379(4) . ?
C8 C10 1.488(4) . ?
C8 C7 1.551(4) . ?
C30 C31 1.520(4) . ?
C6 C7 1.525(5) . ?
C22 C23 1.516(5) . ?

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
C012 O10 C00Y 115.8(2) . . ?
C12 O3 C8 109.8(2) . . ?
C28 O7 C24 109.0(2) . . ?
C00S O4 C15 115.2(3) . . ?
C3 N2 C1 117.4(2) . . ?
C16 N18 C19 117.7(2) . . ?
N2 C1 C9 121.8(3) . . ?
C20 C21 C22 131.3(2) . . ?
C25 C21 C20 118.2(2) . . ?
C25 C21 C22 110.4(2) . . ?
C1 C9 C5 120.6(3) . . ?
C1 C9 C8 127.3(2) . . ?
C5 C9 C8 112.0(2) . . ?
C5 C4 C3 117.2(3) . . ?
C5 C4 C00S 126.5(3) . . ?
C3 C4 C00S 116.3(3) . . ?
C26 C27 C28 107.3(3) . . ?
C26 C27 C30 130.7(3) . . ?
C28 C27 C30 122.0(3) . . ?
O3 C12 C11 108.3(2) . . ?
O2 C12 O3 122.4(3) . . ?
O2 C12 C11 129.3(3) . . ?
C21 C20 C012 125.5(2) . . ?
C19 C20 C21 117.9(2) . . ?
C19 C20 C012 116.6(3) . . ?
C12 C11 C13 122.7(2) . . ?
C10 C11 C12 107.8(2) . . ?
C10 C11 C13 129.5(3) . . ?
O1 C13 C11 111.2(2) . . ?
O1 C13 C14 107.5(2) . . ?
C11 C13 C14 111.0(3) . . ?
O7 C24 C25 108.8(2) . . ?
O7 C24 C26 103.4(2) . . ?
O7 C24 C23 110.2(3) . . ?
C25 C24 C23 103.0(2) . . ?
C26 C24 C25 117.0(2) . . ?
C26 C24 C23 114.5(3) . . ?
C9 C5 C6 110.2(3) . . ?
C4 C5 C9 117.8(2) . . ?
C4 C5 C6 132.0(2) . . ?
C21 C25 C24 112.2(2) . . ?
C16 C25 C21 119.9(3) . . ?
C16 C25 C24 127.8(2) . . ?
O3 C8 C9 108.2(2) . . ?
O3 C8 C10 103.1(2) . . ?
O3 C8 C7 111.9(3) . . ?
C9 C8 C7 102.9(2) . . ?
C10 C8 C9 115.8(2) . . ?
C10 C8 C7 115.0(3) . . ?
N2 C3 C4 125.1(3) . . ?
C27 C26 C24 111.0(2) . . ?
O4 C00S C4 112.8(3) . . ?
O5 C00S O4 124.3(3) . . ?
O5 C00S C4 123.0(3) . . ?
C11 C10 C8 110.9(2) . . ?
O7 C28 C27 109.4(2) . . ?
O6 C28 O7 121.6(3) . . ?
O6 C28 C27 129.0(4) . . ?
O8 C30 C27 111.7(2) . . ?
O8 C30 C31 108.1(3) . . ?
C27 C30 C31 111.5(3) . . ?
N18 C19 C20 124.0(3) . . ?
C5 C6 C7 104.6(2) . . ?
N18 C16 C25 122.2(3) . . ?
C21 C22 C23 105.0(2) . . ?
O10 C012 C20 112.6(2) . . ?
O9 C012 O10 123.5(2) . . ?
O9 C012 C20 123.9(3) . . ?
C6 C7 C8 107.4(3) . . ?
C22 C23 C24 108.4(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_22020060_0m
_database_code_depnum_ccdc_archive 'CCDC 2024023'
loop_
_audit_author_name
_audit_author_address
'Gao xinhua'
;Shanghai Institute of Materia Medica, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_audit_creation_date             2020-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_absolute_configuration rmad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4661(2)
_cell_length_b                   8.8867(2)
_cell_length_c                   15.5541(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1170.22(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4631
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.64
_cell_measurement_theta_min      5.69
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1804 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.8375. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13255
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.907
_diffrn_reflns_theta_min         5.689
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2333
_reflns_number_total             2397
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.095
_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)+(0.0415P)²+0.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C3(H3A), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.72844(14) 0.46782(14) 0.48603(8) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.86715(16) 0.64413(16) 0.55607(9) 0.0454(3) Uani 1 1 d . . . . .
O3 O 1.07551(15) 0.71881(16) 0.29903(9) 0.0435(3) Uani 1 1 d . . . . .
H3 H 1.149163 0.655481 0.298409 0.065 Uiso 1 1 calc GR . . . .
N2 N 0.30393(18) 0.4924(2) 0.32044(12) 0.0465(4) Uani 1 1 d . . . . .
C12 C 0.83514(19) 0.5827(2) 0.48919(11) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.4546(2) 0.5172(2) 0.34309(12) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.495213 0.616770 0.340805 0.049 Uiso 1 1 calc R . . . .
C10 C 0.83288(18) 0.5078(2) 0.35013(11) 0.0344(4) Uani 1 1 d . . . . .
H10 H 0.853633 0.499838 0.290273 0.041 Uiso 1 1 calc R . . . .
C8 C 0.72302(19) 0.4074(2) 0.39880(11) 0.0335(4) Uani 1 1 d . . . . .
C7 C 0.7713(2) 0.2399(2) 0.40017(12) 0.0384(4) Uani 1 1 d . . . . .
H7A H 0.826420 0.212459 0.346253 0.046 Uiso 1 1 calc R . . . .
H7B H 0.842609 0.219260 0.449229 0.046 Uiso 1 1 calc R . . . .
C11 C 0.89754(18) 0.6094(2) 0.40178(11) 0.0335(4) Uani 1 1 d . . . . .
C9 C 0.55196(19) 0.4016(2) 0.36963(11) 0.0341(3) Uani 1 1 d . . . . .
C5 C 0.4945(2) 0.2561(2) 0.37492(11) 0.0370(4) Uani 1 1 d . . . . .
C3 C 0.2501(2) 0.3500(2) 0.32451(13) 0.0456(4) Uani 1 1 d . . . . .
H3A H 0.143781 0.331936 0.308010 0.055 Uiso 1 1 calc R . . . .
C4 C 0.3391(2) 0.2288(2) 0.35099(12) 0.0430(4) Uani 1 1 d . . . . .
H4 H 0.295737 0.130204 0.352810 0.052 Uiso 1 1 calc R . . . .
C6 C 0.6173(2) 0.1499(2) 0.40928(14) 0.0438(4) Uani 1 1 d . . . . .
H6A H 0.621155 0.056060 0.375029 0.053 Uiso 1 1 calc R . . . .
H6B H 0.596269 0.124254 0.470158 0.053 Uiso 1 1 calc R . . . .
C14 C 0.9402(3) 0.8859(2) 0.39349(14) 0.0475(5) Uani 1 1 d . . . . .
H14A H 1.019609 0.963569 0.382010 0.071 Uiso 1 1 calc GR . . . .
H14B H 0.900052 0.897528 0.452206 0.071 Uiso 1 1 calc GR . . . .
H14C H 0.852865 0.896177 0.352578 0.071 Uiso 1 1 calc GR . . . .
C13 C 1.0148(2) 0.7315(2) 0.38372(12) 0.0375(4) Uani 1 1 d . . . . .
H13 H 1.104144 0.722560 0.425437 0.045 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
O1 C12 1.364(2) . ?
O1 C8 1.460(2) . ?
O2 C12 1.206(2) . ?
O3 H3 0.8400 . ?
O3 C13 1.418(2) . ?
N2 C1 1.341(2) . ?
N2 C3 1.346(3) . ?
C12 C11 1.478(2) . ?
C1 H1 0.9500 . ?
C1 C9 1.380(2) . ?
C10 H10 0.9500 . ?
C10 C8 1.494(2) . ?
C10 C11 1.327(3) . ?
C8 C7 1.545(2) . ?
C8 C9 1.519(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.536(3) . ?
C11 C13 1.497(3) . ?
C9 C5 1.384(3) . ?
C5 C4 1.389(3) . ?
C5 C6 1.502(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C13 1.517(3) . ?
C13 H13 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C8 109.23(13) . . ?
C13 O3 H3 109.5 . . ?
C1 N2 C3 117.64(17) . . ?
O1 C12 C11 108.89(14) . . ?
O2 C12 O1 121.24(16) . . ?
O2 C12 C11 129.86(16) . . ?
N2 C1 H1 119.2 . . ?
N2 C1 C9 121.60(18) . . ?
C9 C1 H1 119.2 . . ?
C8 C10 H10 124.6 . . ?
C11 C10 H10 124.6 . . ?
C11 C10 C8 110.86(15) . . ?
O1 C8 C10 103.42(14) . . ?
O1 C8 C7 109.47(13) . . ?
O1 C8 C9 108.68(13) . . ?
C10 C8 C7 114.67(14) . . ?
C10 C8 C9 117.55(14) . . ?
C9 C8 C7 102.93(14) . . ?
C8 C7 H7A 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C6 C7 C8 106.16(14) . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
C12 C11 C13 121.74(15) . . ?
C10 C11 C12 107.47(15) . . ?
C10 C11 C13 130.78(17) . . ?
C1 C9 C8 129.32(16) . . ?
C1 C9 C5 120.21(16) . . ?
C5 C9 C8 110.43(15) . . ?
C9 C5 C4 118.69(17) . . ?
C9 C5 C6 111.41(15) . . ?
C4 C5 C6 129.89(18) . . ?
N2 C3 H3A 117.8 . . ?
N2 C3 C4 124.36(17) . . ?
C4 C3 H3A 117.8 . . ?
C5 C4 H4 121.3 . . ?
C3 C4 C5 117.48(18) . . ?
C3 C4 H4 121.3 . . ?
C7 C6 H6A 111.1 . . ?
C7 C6 H6B 111.1 . . ?
C5 C6 C7 103.16(15) . . ?
C5 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
O3 C13 C11 110.90(15) . . ?
O3 C13 C14 108.42(15) . . ?
O3 C13 H13 108.8 . . ?
C11 C13 C14 111.14(15) . . ?
C11 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
