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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_211215o_0m
_database_code_depnum_ccdc_archive 'CCDC 2213948'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-12-16
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.0253(4)
_cell_length_b                   10.2408(5)
_cell_length_c                   20.0504(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1647.85(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9093
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.32
_cell_measurement_theta_min      4.22
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_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  0.0387
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            79808
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.311
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                4732
_reflns_number_total             4751
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2042 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       0.082(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.052
_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)+(0.0513P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0886
_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 
2.a Ternary CH refined with riding coordinates: 
 C4(H4) 
2.b Secondary CH2 refined with riding coordinates: 
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), 
 C18(H18A,H18B), C19(H19A,H19B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C1(H1), C14(H14), C17(H17) 
2.d Idealised Me refined as rotating group: 
 C20(H20A,H20B,H20C) 
;
_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 0.70087(16) 0.46717(14) 0.77751(6) 0.0317(3) Uani 1 1 d . . . . .
H1 H 0.595820 0.469691 0.799309 0.038 Uiso 1 1 calc R U . . .
C2 C 0.84645(16) 0.49126(14) 0.80795(5) 0.0307(2) Uani 1 1 d . . . . .
C3 C 0.98758(15) 0.48093(13) 0.76052(5) 0.0280(2) Uani 1 1 d . . . . .
C4 C 0.91661(14) 0.42367(11) 0.69625(5) 0.0248(2) Uani 1 1 d . . . . .
H4 H 0.942624 0.328200 0.697321 0.030 Uiso 1 1 calc R U . . .
C5 C 0.72379(15) 0.43528(12) 0.70380(5) 0.0260(2) Uani 1 1 d . . . . .
C6 C 0.6322(2) 0.31061(14) 0.68207(7) 0.0376(3) Uani 1 1 d . . . . .
H6A H 0.691204 0.268065 0.644543 0.045 Uiso 1 1 calc R U . . .
H6B H 0.624566 0.248000 0.719565 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4584(2) 0.35548(19) 0.66047(10) 0.0494(4) Uani 1 1 d . . . . .
H7A H 0.427987 0.316843 0.616874 0.059 Uiso 1 1 calc R U . . .
H7B H 0.373712 0.329908 0.693907 0.059 Uiso 1 1 calc R U . . .
C8 C 0.47096(17) 0.50352(17) 0.65533(7) 0.0398(3) Uani 1 1 d . . . . .
H8A H 0.421932 0.535041 0.612983 0.048 Uiso 1 1 calc R U . . .
H8B H 0.412844 0.546155 0.693051 0.048 Uiso 1 1 calc R U . . .
C10 C 0.68957(19) 0.66786(13) 0.66522(7) 0.0355(3) Uani 1 1 d . . . . .
H10A H 0.645061 0.698762 0.708484 0.043 Uiso 1 1 calc R U . . .
H10B H 0.632946 0.717590 0.629455 0.043 Uiso 1 1 calc R U . . .
C11 C 0.87681(19) 0.69676(11) 0.66242(6) 0.0317(3) Uani 1 1 d . . . . .
H11A H 0.893084 0.788241 0.647848 0.038 Uiso 1 1 calc R U . . .
H11B H 0.923800 0.688321 0.707868 0.038 Uiso 1 1 calc R U . . .
C12 C 0.97172(16) 0.60772(11) 0.61597(5) 0.0267(2) Uani 1 1 d . . . . .
C13 C 0.98860(14) 0.47493(11) 0.63220(5) 0.0238(2) Uani 1 1 d . . . . .
C14 C 1.06831(16) 0.38788(12) 0.58851(6) 0.0272(2) Uani 1 1 d . . . . .
H14 H 1.078815 0.297793 0.598997 0.033 Uiso 1 1 calc R U . . .
C15 C 1.13068(16) 0.43806(13) 0.52988(6) 0.0300(3) Uani 1 1 d . . . . .
C16 C 1.11654(18) 0.56902(13) 0.51464(6) 0.0332(3) Uani 1 1 d . . . . .
C17 C 1.0377(2) 0.65630(12) 0.55617(6) 0.0337(3) Uani 1 1 d . . . . .
H17 H 1.028409 0.746047 0.544774 0.040 Uiso 1 1 calc R U . . .
C18 C 1.2250(2) 0.46713(18) 0.42699(7) 0.0429(3) Uani 1 1 d . . . . .
H18A H 1.335506 0.464346 0.405091 0.052 Uiso 1 1 calc R U . . .
H18B H 1.138777 0.446719 0.393248 0.052 Uiso 1 1 calc R U . . .
C19 C 0.75292(18) 0.51600(17) 0.91978(6) 0.0372(3) Uani 1 1 d . . . . .
H19A H 0.695428 0.430623 0.917200 0.045 Uiso 1 1 calc R U . . .
H19B H 0.670501 0.585888 0.911077 0.045 Uiso 1 1 calc R U . . .
C20 C 0.8302(2) 0.53387(16) 0.98757(6) 0.0397(3) Uani 1 1 d . . . . .
H20A H 0.884679 0.619409 0.989780 0.060 Uiso 1 1 calc R U . . .
H20B H 0.912903 0.465081 0.995236 0.060 Uiso 1 1 calc R U . . .
H20C H 0.743347 0.528759 1.021824 0.060 Uiso 1 1 calc R U . . .
N9 N 0.65049(13) 0.53026(10) 0.65763(5) 0.0282(2) Uani 1 1 d . . . . .
O1 O 0.88576(13) 0.52182(12) 0.87157(4) 0.0377(2) Uani 1 1 d . . . . .
O2 O 1.13096(12) 0.50926(12) 0.77226(5) 0.0392(2) Uani 1 1 d . . . . .
O3 O 1.21846(17) 0.37429(11) 0.48043(5) 0.0441(3) Uani 1 1 d . . . . .
O4 O 1.19613(19) 0.59328(12) 0.45481(6) 0.0503(3) 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 H1 0.9500 . ?
C1 C2 1.3410(17) . ?
C1 C5 1.5247(16) . ?
C2 C3 1.4826(16) . ?
C2 O1 1.3509(13) . ?
C3 C4 1.5261(16) . ?
C3 O2 1.2098(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.5593(16) . ?
C4 C13 1.5027(14) . ?
C5 C6 1.5361(18) . ?
C5 N9 1.4660(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.531(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.523(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N9 1.4673(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(2) . ?
C10 N9 1.4517(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5096(17) . ?
C12 C13 1.4049(16) . ?
C12 C17 1.4021(16) . ?
C13 C14 1.4040(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3771(15) . ?
C15 C16 1.3802(19) . ?
C15 O3 1.3806(15) . ?
C16 C17 1.3756(19) . ?
C16 O4 1.3815(15) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 O3 1.4335(19) . ?
C18 O4 1.426(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5052(19) . ?
C19 O1 1.4401(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C2 C1 H1 124.0 . . ?
C2 C1 C5 112.05(11) . . ?
C5 C1 H1 124.0 . . ?
C1 C2 C3 111.14(10) . . ?
C1 C2 O1 132.52(11) . . ?
O1 C2 C3 116.35(11) . . ?
C2 C3 C4 106.49(10) . . ?
O2 C3 C2 125.78(11) . . ?
O2 C3 C4 127.69(11) . . ?
C3 C4 H4 106.2 . . ?
C3 C4 C5 105.02(9) . . ?
C5 C4 H4 106.2 . . ?
C13 C4 C3 116.35(10) . . ?
C13 C4 H4 106.2 . . ?
C13 C4 C5 115.97(9) . . ?
C1 C5 C4 103.31(9) . . ?
C1 C5 C6 113.28(11) . . ?
C6 C5 C4 112.57(11) . . ?
N9 C5 C1 114.93(10) . . ?
N9 C5 C4 112.80(9) . . ?
N9 C5 C6 100.39(10) . . ?
C5 C6 H6A 110.6 . . ?
C5 C6 H6B 110.6 . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 C5 105.47(13) . . ?
C7 C6 H6A 110.6 . . ?
C7 C6 H6B 110.6 . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 C6 104.92(12) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
N9 C8 C7 104.40(13) . . ?
N9 C8 H8A 110.9 . . ?
N9 C8 H8B 110.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
N9 C10 H10A 108.9 . . ?
N9 C10 H10B 108.9 . . ?
N9 C10 C11 113.29(11) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.62(11) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C13 C12 C11 119.37(10) . . ?
C17 C12 C11 120.26(11) . . ?
C17 C12 C13 120.34(11) . . ?
C12 C13 C4 119.93(10) . . ?
C14 C13 C4 119.12(10) . . ?
C14 C13 C12 120.93(10) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.47(11) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 121.45(11) . . ?
C14 C15 O3 128.47(12) . . ?
C16 C15 O3 110.03(11) . . ?
C15 C16 O4 109.21(12) . . ?
C17 C16 C15 122.35(11) . . ?
C17 C16 O4 128.42(13) . . ?
C12 C17 H17 121.3 . . ?
C16 C17 C12 117.44(11) . . ?
C16 C17 H17 121.3 . . ?
H18A C18 H18B 108.5 . . ?
O3 C18 H18A 110.2 . . ?
O3 C18 H18B 110.2 . . ?
O4 C18 H18A 110.2 . . ?
O4 C18 H18B 110.2 . . ?
O4 C18 O3 107.60(11) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
O1 C19 H19A 110.3 . . ?
O1 C19 H19B 110.3 . . ?
O1 C19 C20 107.22(12) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 N9 C8 106.86(10) . . ?
C10 N9 C5 119.42(10) . . ?
C10 N9 C8 113.37(11) . . ?
C2 O1 C19 116.83(11) . . ?
C15 O3 C18 103.99(11) . . ?
C16 O4 C18 104.59(11) . . ?

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 -9.35(15) . . . . ?
C1 C2 C3 O2 172.66(15) . . . . ?
C1 C2 O1 C19 7.5(2) . . . . ?
C1 C5 C6 C7 89.65(14) . . . . ?
C1 C5 N9 C8 -78.68(13) . . . . ?
C1 C5 N9 C10 51.61(15) . . . . ?
C2 C1 C5 C4 8.18(15) . . . . ?
C2 C1 C5 C6 130.27(14) . . . . ?
C2 C1 C5 N9 -115.11(13) . . . . ?
C2 C3 C4 C5 13.81(13) . . . . ?
C2 C3 C4 C13 143.52(11) . . . . ?
C3 C2 O1 C19 -172.40(13) . . . . ?
C3 C4 C5 C1 -13.10(12) . . . . ?
C3 C4 C5 C6 -135.66(10) . . . . ?
C3 C4 C5 N9 111.59(11) . . . . ?
C3 C4 C13 C12 -62.23(15) . . . . ?
C3 C4 C13 C14 119.44(12) . . . . ?
C4 C5 C6 C7 -153.59(12) . . . . ?
C4 C5 N9 C8 163.24(10) . . . . ?
C4 C5 N9 C10 -66.47(14) . . . . ?
C4 C13 C14 C15 179.11(11) . . . . ?
C5 C1 C2 C3 0.54(17) . . . . ?
C5 C1 C2 O1 -179.35(15) . . . . ?
C5 C4 C13 C12 62.03(14) . . . . ?
C5 C4 C13 C14 -116.30(12) . . . . ?
C5 C6 C7 C8 12.69(17) . . . . ?
C6 C5 N9 C8 43.21(13) . . . . ?
C6 C5 N9 C10 173.50(12) . . . . ?
C6 C7 C8 N9 13.13(17) . . . . ?
C7 C8 N9 C5 -36.12(15) . . . . ?
C7 C8 N9 C10 -169.75(13) . . . . ?
C10 C11 C12 C13 -68.14(15) . . . . ?
C10 C11 C12 C17 109.83(14) . . . . ?
C11 C10 N9 C5 56.94(15) . . . . ?
C11 C10 N9 C8 -175.73(11) . . . . ?
C11 C12 C13 C4 -1.71(17) . . . . ?
C11 C12 C13 C14 176.58(11) . . . . ?
C11 C12 C17 C16 -177.21(13) . . . . ?
C12 C13 C14 C15 0.80(18) . . . . ?
C13 C4 C5 C1 -143.04(10) . . . . ?
C13 C4 C5 C6 94.40(12) . . . . ?
C13 C4 C5 N9 -18.34(14) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C13 C14 C15 C16 0.39(19) . . . . ?
C13 C14 C15 O3 177.46(13) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C14 C15 C16 O4 177.22(13) . . . . ?
C14 C15 O3 C18 170.11(14) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C15 C16 O4 C18 13.18(17) . . . . ?
C16 C15 O3 C18 -12.55(16) . . . . ?
C17 C12 C13 C4 -179.68(12) . . . . ?
C17 C12 C13 C14 -1.38(18) . . . . ?
C17 C16 O4 C18 -168.70(16) . . . . ?
C20 C19 O1 C2 171.75(13) . . . . ?
N9 C5 C6 C7 -33.40(14) . . . . ?
N9 C10 C11 C12 33.66(15) . . . . ?
O1 C2 C3 C4 170.56(12) . . . . ?
O1 C2 C3 O2 -7.4(2) . . . . ?
O2 C3 C4 C5 -168.25(14) . . . . ?
O2 C3 C4 C13 -38.55(19) . . . . ?
O3 C15 C16 C17 -178.60(14) . . . . ?
O3 C15 C16 O4 -0.34(17) . . . . ?
O3 C18 O4 C16 -20.96(17) . . . . ?
O4 C16 C17 C12 -177.45(14) . . . . ?
O4 C18 O3 C15 20.65(17) . . . . ?

_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_210915k_0m
_database_code_depnum_ccdc_archive 'CCDC 2213952'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-15
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N O4'
_chemical_formula_sum            'C19 H23 N O4'
_chemical_formula_weight         329.38
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5187(5)
_cell_length_b                   9.2274(6)
_cell_length_c                   23.3001(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1616.52(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      4.48
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.490
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            40611
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.369
_diffrn_reflns_theta_min         4.484
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4790
_reflns_number_total             4813
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2043 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.092
_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)+(0.0517P)²+0.1415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0839
_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: 
 C3(H3A) 
2.b Secondary CH2 refined with riding coordinates: 
 C4(H4A,H4B), C8(H8A,H8B), C7(H7A,H7B), C12(H12A,H12B), C10(H10A,H10B), 
 C19(H19A,H19B), C11(H11A,H11B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C15(H15), C1(H1), C18(H18), C2(H2) 
2.d Idealised Me refined as rotating group: 
 C9(H9A,H9B,H9C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_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
O3 O -0.23729(12) 0.41599(10) 0.39146(4) 0.02820(18) Uani 1 1 d . . . . .
H3 H -0.262623 0.339596 0.409277 0.042 Uiso 1 1 calc R U . . .
C14 C 0.12918(14) 0.38136(12) 0.36920(4) 0.02250(19) Uani 1 1 d . . . . .
N1 N 0.15977(13) 0.60762(11) 0.43058(4) 0.02452(19) Uani 1 1 d . . . . .
C5 C 0.07717(14) 0.46529(11) 0.42414(5) 0.02177(19) Uani 1 1 d . . . . .
C6 C -0.12746(14) 0.50470(12) 0.42631(5) 0.02313(19) Uani 1 1 d . . . . .
O4 O 0.14031(18) 0.35617(11) 0.57880(4) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.28797(19) 0.10525(12) 0.23867(5) 0.0477(3) Uani 1 1 d . . . . .
C4 C 0.13221(17) 0.37294(13) 0.47691(5) 0.0272(2) Uani 1 1 d . . . . .
H4A H 0.067572 0.279490 0.476094 0.033 Uiso 1 1 calc R U . . .
H4B H 0.261186 0.351898 0.474938 0.033 Uiso 1 1 calc R U . . .
C8 C 0.03830(16) 0.72875(12) 0.42214(5) 0.0270(2) Uani 1 1 d . . . . .
H8A H 0.085427 0.797206 0.393168 0.032 Uiso 1 1 calc R U . . .
H8B H 0.018268 0.781561 0.458553 0.032 Uiso 1 1 calc R U . . .
O1 O 0.12939(19) 0.00266(11) 0.31376(4) 0.0453(3) Uani 1 1 d . . . . .
C15 C 0.09148(17) 0.23091(13) 0.36832(5) 0.0271(2) Uani 1 1 d . . . . .
H15 H 0.028782 0.186843 0.399119 0.033 Uiso 1 1 calc R U . . .
C1 C -0.19794(16) 0.50739(14) 0.48697(5) 0.0290(2) Uani 1 1 d . . . . .
H1 H -0.321638 0.524772 0.491632 0.035 Uiso 1 1 calc R U . . .
C18 C 0.27482(18) 0.35590(15) 0.27572(5) 0.0302(2) Uani 1 1 d . . . . .
H18 H 0.337424 0.396866 0.244238 0.036 Uiso 1 1 calc R U . . .
C13 C 0.21703(16) 0.44412(12) 0.32182(5) 0.0250(2) Uani 1 1 d . . . . .
C7 C -0.13273(16) 0.65805(12) 0.40119(6) 0.0283(2) Uani 1 1 d . . . . .
H7A H -0.136310 0.654951 0.358735 0.034 Uiso 1 1 calc R U . . .
H7B H -0.238111 0.711664 0.415268 0.034 Uiso 1 1 calc R U . . .
C12 C 0.25107(19) 0.60553(13) 0.31483(5) 0.0303(2) Uani 1 1 d . . . . .
H12A H 0.136993 0.657589 0.319844 0.036 Uiso 1 1 calc R U . . .
H12B H 0.292320 0.623476 0.275106 0.036 Uiso 1 1 calc R U . . .
C10 C 0.34731(16) 0.62401(15) 0.41823(5) 0.0299(2) Uani 1 1 d . . . . .
H10A H 0.407960 0.530813 0.425984 0.036 Uiso 1 1 calc R U . . .
H10B H 0.397840 0.697312 0.444623 0.036 Uiso 1 1 calc R U . . .
C19 C 0.2025(2) -0.02369(14) 0.25807(6) 0.0340(3) Uani 1 1 d . . . . .
H19A H 0.289435 -0.104110 0.259928 0.041 Uiso 1 1 calc R U . . .
H19B H 0.106705 -0.051365 0.231046 0.041 Uiso 1 1 calc R U . . .
C3 C 0.09121(18) 0.45140(13) 0.53264(5) 0.0275(2) Uani 1 1 d . . . . .
H3A H 0.162935 0.542490 0.534888 0.033 Uiso 1 1 calc R U . . .
C16 C 0.14679(18) 0.15004(13) 0.32241(5) 0.0285(2) Uani 1 1 d . . . . .
C17 C 0.23896(19) 0.21098(14) 0.27732(5) 0.0301(2) Uani 1 1 d . . . . .
C2 C -0.10303(18) 0.48770(14) 0.53445(5) 0.0299(2) Uani 1 1 d . . . . .
H2 H -0.160037 0.496908 0.570654 0.036 Uiso 1 1 calc R U . . .
C11 C 0.38700(18) 0.66982(17) 0.35628(6) 0.0359(3) Uani 1 1 d . . . . .
H11A H 0.384345 0.776861 0.353497 0.043 Uiso 1 1 calc R U . . .
H11B H 0.507686 0.636723 0.345469 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1485(3) 0.42532(19) 0.63325(6) 0.0474(4) Uani 1 1 d . . . . .
H9A H 0.231735 0.506909 0.631404 0.071 Uiso 1 1 calc R U . . .
H9B H 0.189289 0.355763 0.662175 0.071 Uiso 1 1 calc R U . . .
H9C H 0.030060 0.460978 0.643705 0.071 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
O3 H3 0.8400 . ?
O3 C6 1.4182(13) . ?
C14 C5 1.5463(15) . ?
C14 C15 1.4171(15) . ?
C14 C13 1.4107(15) . ?
N1 C5 1.4605(14) . ?
N1 C8 1.4568(15) . ?
N1 C10 1.4471(15) . ?
C5 C6 1.5818(15) . ?
C5 C4 1.5522(15) . ?
C6 C1 1.5097(16) . ?
C6 C7 1.5318(16) . ?
O4 C3 1.4372(14) . ?
O4 C9 1.4213(16) . ?
O2 C19 1.4259(18) . ?
O2 C17 1.3780(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5183(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5223(16) . ?
O1 C19 1.4299(16) . ?
O1 C16 1.3810(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.3690(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3291(18) . ?
C18 H18 0.9500 . ?
C18 C13 1.4161(16) . ?
C18 C17 1.3646(18) . ?
C13 C12 1.5201(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.5262(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5333(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C3 H3A 1.0000 . ?
C3 C2 1.4989(18) . ?
C16 C17 1.3785(16) . ?
C2 H2 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C6 O3 H3 109.5 . . ?
C15 C14 C5 116.87(9) . . ?
C13 C14 C5 124.10(10) . . ?
C13 C14 C15 118.98(10) . . ?
C8 N1 C5 114.17(9) . . ?
C10 N1 C5 119.20(10) . . ?
C10 N1 C8 120.26(10) . . ?
C14 C5 C6 112.80(9) . . ?
C14 C5 C4 108.26(8) . . ?
N1 C5 C14 115.33(9) . . ?
N1 C5 C6 101.75(8) . . ?
N1 C5 C4 107.39(9) . . ?
C4 C5 C6 111.12(9) . . ?
O3 C6 C5 114.54(9) . . ?
O3 C6 C1 109.95(9) . . ?
O3 C6 C7 107.42(9) . . ?
C1 C6 C5 112.03(9) . . ?
C1 C6 C7 109.48(10) . . ?
C7 C6 C5 103.02(9) . . ?
C9 O4 C3 113.87(10) . . ?
C17 O2 C19 105.25(10) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 C5 111.19(9) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
N1 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
N1 C8 C7 104.13(9) . . ?
H8A C8 H8B 108.9 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C16 O1 C19 105.28(10) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 118.98(10) . . ?
C16 C15 H15 120.5 . . ?
C6 C1 H1 117.0 . . ?
C2 C1 C6 126.06(11) . . ?
C2 C1 H1 117.0 . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C13 118.81(11) . . ?
C14 C13 C18 120.08(11) . . ?
C14 C13 C12 124.40(10) . . ?
C18 C13 C12 115.48(10) . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C8 C7 C6 104.57(9) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C13 C12 C11 115.20(11) . . ?
H12A C12 H12B 107.5 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
N1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
N1 C10 C11 113.94(10) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O2 C19 O1 108.60(10) . . ?
O2 C19 H19A 110.0 . . ?
O2 C19 H19B 110.0 . . ?
O1 C19 H19A 110.0 . . ?
O1 C19 H19B 110.0 . . ?
H19A C19 H19B 108.3 . . ?
O4 C3 C4 107.24(9) . . ?
O4 C3 H3A 109.6 . . ?
O4 C3 C2 111.46(11) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 C4 109.18(10) . . ?
C2 C3 H3A 109.6 . . ?
C15 C16 O1 128.47(11) . . ?
C15 C16 C17 121.73(11) . . ?
C17 C16 O1 109.76(10) . . ?
O2 C17 C16 110.10(11) . . ?
C18 C17 O2 128.54(12) . . ?
C18 C17 C16 121.33(11) . . ?
C1 C2 C3 122.02(10) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C12 C11 C10 110.99(10) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O4 0.84 1.97 2.7629(13) 157.5 3_456 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C6 C1 C2 132.11(13) . . . . ?
O3 C6 C7 C8 -156.59(9) . . . . ?
C14 C5 C6 O3 22.13(13) . . . . ?
C14 C5 C6 C1 148.25(9) . . . . ?
C14 C5 C6 C7 -94.19(10) . . . . ?
C14 C5 C4 C3 177.90(10) . . . . ?
C14 C15 C16 O1 177.73(14) . . . . ?
C14 C15 C16 C17 0.42(19) . . . . ?
C14 C13 C12 C11 69.40(16) . . . . ?
N1 C5 C6 O3 146.30(9) . . . . ?
N1 C5 C6 C1 -87.59(11) . . . . ?
N1 C5 C6 C7 29.97(10) . . . . ?
N1 C5 C4 C3 52.76(13) . . . . ?
N1 C8 C7 C6 26.76(12) . . . . ?
N1 C10 C11 C12 -33.38(16) . . . . ?
C5 C14 C15 C16 -175.26(11) . . . . ?
C5 C14 C13 C18 173.84(11) . . . . ?
C5 C14 C13 C12 -8.33(18) . . . . ?
C5 N1 C8 C7 -7.34(13) . . . . ?
C5 N1 C10 C11 92.58(13) . . . . ?
C5 C6 C1 C2 3.53(17) . . . . ?
C5 C6 C7 C8 -35.30(12) . . . . ?
C5 C4 C3 O4 177.95(11) . . . . ?
C5 C4 C3 C2 57.06(13) . . . . ?
C6 C5 C4 C3 -57.71(13) . . . . ?
C6 C1 C2 C3 -3.4(2) . . . . ?
O4 C3 C2 C1 -145.54(12) . . . . ?
C4 C5 C6 O3 -99.65(11) . . . . ?
C4 C5 C6 C1 26.46(12) . . . . ?
C4 C5 C6 C7 144.02(9) . . . . ?
C4 C3 C2 C1 -27.26(17) . . . . ?
C8 N1 C5 C14 108.07(11) . . . . ?
C8 N1 C5 C6 -14.37(12) . . . . ?
C8 N1 C5 C4 -131.16(10) . . . . ?
C8 N1 C10 C11 -57.76(16) . . . . ?
O1 C16 C17 O2 -1.38(17) . . . . ?
O1 C16 C17 C18 -179.65(14) . . . . ?
C15 C14 C5 N1 163.77(10) . . . . ?
C15 C14 C5 C6 -79.91(12) . . . . ?
C15 C14 C5 C4 43.48(13) . . . . ?
C15 C14 C13 C18 -3.42(17) . . . . ?
C15 C14 C13 C12 174.41(12) . . . . ?
C15 C16 C17 O2 176.38(13) . . . . ?
C15 C16 C17 C18 -1.9(2) . . . . ?
C1 C6 C7 C8 84.05(11) . . . . ?
C18 C13 C12 C11 -112.68(12) . . . . ?
C13 C14 C5 N1 -13.55(15) . . . . ?
C13 C14 C5 C6 102.78(12) . . . . ?
C13 C14 C5 C4 -133.84(11) . . . . ?
C13 C14 C15 C16 2.20(17) . . . . ?
C13 C18 C17 O2 -177.29(14) . . . . ?
C13 C18 C17 C16 0.6(2) . . . . ?
C13 C12 C11 C10 -48.80(16) . . . . ?
C7 C6 C1 C2 -110.10(14) . . . . ?
C10 N1 C5 C14 -44.00(13) . . . . ?
C10 N1 C5 C6 -166.44(10) . . . . ?
C10 N1 C5 C4 76.77(12) . . . . ?
C10 N1 C8 C7 144.40(11) . . . . ?
C19 O2 C17 C18 -174.80(14) . . . . ?
C19 O2 C17 C16 7.10(17) . . . . ?
C19 O1 C16 C15 177.49(14) . . . . ?
C19 O1 C16 C17 -4.94(16) . . . . ?
C16 O1 C19 O2 9.33(16) . . . . ?
C17 O2 C19 O1 -10.12(17) . . . . ?
C17 C18 C13 C14 2.02(19) . . . . ?
C17 C18 C13 C12 -176.00(12) . . . . ?
C9 O4 C3 C4 166.33(14) . . . . ?
C9 O4 C3 C2 -74.23(16) . . . . ?

_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_210722e_0m
_database_code_depnum_ccdc_archive 'CCDC 2213951'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-07-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.4578(8)
_cell_length_b                   9.5190(9)
_cell_length_c                   19.2209(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1547.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      72.42
_cell_measurement_theta_min      4.04
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25285
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.992
_diffrn_reflns_theta_min         6.412
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2900
_reflns_number_total             2915
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.074
_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)+(0.0461P)²+0.4317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0818
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C15(H15), C18(H18)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_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 0.4027(2) 0.8033(2) 0.42662(10) 0.0176(4) Uani 1 1 d . . . . .
H1 H 0.316706 0.781045 0.456453 0.021 Uiso 1 1 calc R U . . .
C2 C 0.5164(2) 0.8881(2) 0.44938(9) 0.0180(4) Uani 1 1 d . . . . .
H2 H 0.510890 0.921974 0.495807 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6534(2) 0.9327(2) 0.40455(9) 0.0156(4) Uani 1 1 d . . . . .
H3 H 0.660780 1.037428 0.406485 0.019 Uiso 1 1 calc R U . . .
C4 C 0.6323(2) 0.88970(19) 0.32785(9) 0.0130(4) Uani 1 1 d . . . . .
H4A H 0.735935 0.896356 0.304140 0.016 Uiso 1 1 calc R U . . .
H4B H 0.559935 0.957388 0.305146 0.016 Uiso 1 1 calc R U . . .
C5 C 0.5659(2) 0.73924(19) 0.31752(8) 0.0124(4) Uani 1 1 d . . . . .
C6 C 0.4075(2) 0.74307(19) 0.35574(9) 0.0149(4) Uani 1 1 d . . . . .
C7 C 0.2810(2) 0.7545(2) 0.30404(10) 0.0179(4) Uani 1 1 d . . . . .
H7 H 0.185620 0.813039 0.314326 0.021 Uiso 1 1 calc R U . . .
C8 C 0.3557(2) 0.7611(2) 0.23360(9) 0.0174(4) Uani 1 1 d . . . . .
H8A H 0.297019 0.702286 0.199859 0.021 Uiso 1 1 calc R U . . .
H8B H 0.359116 0.858894 0.216200 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6236(2) 0.7477(2) 0.18844(9) 0.0158(4) Uani 1 1 d . . . . .
H10A H 0.653827 0.847289 0.195068 0.019 Uiso 1 1 calc R U . . .
H10B H 0.566617 0.740449 0.143586 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7728(2) 0.6588(2) 0.18476(9) 0.0161(4) Uani 1 1 d . . . . .
H11A H 0.832586 0.685587 0.142509 0.019 Uiso 1 1 calc R U . . .
H11B H 0.741779 0.559025 0.179655 0.019 Uiso 1 1 calc R U . . .
C12 C 0.8828(2) 0.6721(2) 0.24796(9) 0.0148(4) Uani 1 1 d . . . . .
H12A H 0.987551 0.633294 0.235328 0.018 Uiso 1 1 calc R U . . .
H12B H 0.897391 0.773079 0.258483 0.018 Uiso 1 1 calc R U . . .
C13 C 0.8253(2) 0.59853(19) 0.31352(9) 0.0124(4) Uani 1 1 d . . . . .
C14 C 0.6768(2) 0.62436(18) 0.34432(9) 0.0118(4) Uani 1 1 d . . . . .
C15 C 0.6262(2) 0.5414(2) 0.40098(9) 0.0144(4) Uani 1 1 d . . . . .
H15 H 0.525169 0.555605 0.421441 0.017 Uiso 1 1 calc R U . . .
C16 C 0.7259(2) 0.44000(19) 0.42570(9) 0.0147(4) Uani 1 1 d . . . . .
C17 C 0.8733(2) 0.4179(2) 0.39742(9) 0.0145(4) Uani 1 1 d . . . . .
C18 C 0.9261(2) 0.49480(19) 0.34143(9) 0.0147(4) Uani 1 1 d . . . . .
H18 H 1.027729 0.478422 0.322056 0.018 Uiso 1 1 calc R U . . .
C19 C 0.8497(3) 0.2832(2) 0.49131(10) 0.0217(4) Uani 1 1 d . . . . .
H19A H 0.840572 0.181262 0.500749 0.026 Uiso 1 1 calc R U . . .
H19B H 0.897375 0.329000 0.532520 0.026 Uiso 1 1 calc R U . . .
C20 C 0.9360(2) 0.9274(2) 0.41040(10) 0.0238(4) Uani 1 1 d . . . . .
H20A H 0.953456 0.887946 0.363929 0.036 Uiso 1 1 calc R U . . .
H20B H 1.022839 0.899451 0.441180 0.036 Uiso 1 1 calc R U . . .
H20C H 0.931794 1.030067 0.407373 0.036 Uiso 1 1 calc R U . . .
N1 N 0.51673(18) 0.70590(16) 0.24477(7) 0.0132(3) Uani 1 1 d . . . . .
O1 O 0.79115(16) 0.87622(15) 0.43745(7) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.30536(16) 0.62390(14) 0.34106(7) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.69695(17) 0.34172(15) 0.47743(7) 0.0205(3) Uani 1 1 d . . . . .
O4 O 0.94669(17) 0.30674(15) 0.43087(7) 0.0208(3) 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 H1 0.9500 . ?
C1 C2 1.329(3) . ?
C1 C6 1.479(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.505(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.540(2) . ?
C3 O1 1.430(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.551(2) . ?
C5 C6 1.528(2) . ?
C5 C14 1.530(2) . ?
C5 N1 1.493(2) . ?
C6 C7 1.465(3) . ?
C6 O2 1.454(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.496(3) . ?
C7 O2 1.447(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N1 1.475(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.522(3) . ?
C10 N1 1.465(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.535(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(2) . ?
C13 C14 1.410(2) . ?
C13 C18 1.410(3) . ?
C14 C15 1.412(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.367(3) . ?
C16 C17 1.376(3) . ?
C16 O3 1.387(2) . ?
C17 C18 1.376(3) . ?
C17 O4 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 O3 1.432(2) . ?
C19 O4 1.440(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O1 1.417(2) . ?

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 H1 119.4 . . ?
C2 C1 C6 121.23(17) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.66(16) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 107.9 . . ?
C2 C3 C4 112.56(16) . . ?
C4 C3 H3 107.9 . . ?
O1 C3 C2 105.57(14) . . ?
O1 C3 H3 107.9 . . ?
O1 C3 C4 114.71(15) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.18(14) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C6 C5 C4 103.52(14) . . ?
C6 C5 C14 113.12(14) . . ?
C14 C5 C4 113.26(14) . . ?
N1 C5 C4 114.64(14) . . ?
N1 C5 C6 102.19(13) . . ?
N1 C5 C14 109.52(14) . . ?
C1 C6 C5 118.46(15) . . ?
C7 C6 C1 125.17(16) . . ?
C7 C6 C5 108.43(14) . . ?
O2 C6 C1 117.72(15) . . ?
O2 C6 C5 114.14(15) . . ?
O2 C6 C7 59.45(12) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 107.96(15) . . ?
C8 C7 H7 119.8 . . ?
O2 C7 C6 59.90(11) . . ?
O2 C7 H7 119.8 . . ?
O2 C7 C8 114.87(16) . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 109.0 . . ?
N1 C8 C7 104.11(14) . . ?
N1 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
N1 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
N1 C10 C11 113.26(15) . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
C10 C11 C12 114.83(15) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 115.06(15) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C14 C13 C12 123.51(16) . . ?
C14 C13 C18 120.04(16) . . ?
C18 C13 C12 116.36(15) . . ?
C13 C14 C5 121.97(16) . . ?
C13 C14 C15 119.76(17) . . ?
C15 C14 C5 118.27(15) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.40(17) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 121.99(17) . . ?
C15 C16 O3 128.02(17) . . ?
C17 C16 O3 109.90(16) . . ?
C16 C17 O4 109.82(16) . . ?
C18 C17 C16 121.43(17) . . ?
C18 C17 O4 128.64(17) . . ?
C13 C18 H18 120.8 . . ?
C17 C18 C13 118.30(17) . . ?
C17 C18 H18 120.8 . . ?
H19A C19 H19B 108.5 . . ?
O3 C19 H19A 110.2 . . ?
O3 C19 H19B 110.2 . . ?
O3 C19 O4 107.64(14) . . ?
O4 C19 H19A 110.2 . . ?
O4 C19 H19B 110.2 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
C8 N1 C5 108.53(14) . . ?
C10 N1 C5 117.55(14) . . ?
C10 N1 C8 111.42(14) . . ?
C20 O1 C3 114.38(15) . . ?
C7 O2 C6 60.65(11) . . ?
C16 O3 C19 103.68(14) . . ?
C17 O4 C19 103.80(14) . . ?

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 9.4(3) . . . . ?
C1 C2 C3 O1 -116.5(2) . . . . ?
C1 C6 C7 C8 146.97(18) . . . . ?
C1 C6 C7 O2 -104.17(19) . . . . ?
C1 C6 O2 C7 116.45(18) . . . . ?
C2 C1 C6 C5 19.5(3) . . . . ?
C2 C1 C6 C7 -125.7(2) . . . . ?
C2 C1 C6 O2 163.67(17) . . . . ?
C2 C3 C4 C5 -42.3(2) . . . . ?
C2 C3 O1 C20 -169.16(16) . . . . ?
C3 C4 C5 C6 58.72(18) . . . . ?
C3 C4 C5 C14 -64.16(19) . . . . ?
C3 C4 C5 N1 169.17(15) . . . . ?
C4 C3 O1 C20 66.3(2) . . . . ?
C4 C5 C6 C1 -47.51(19) . . . . ?
C4 C5 C6 C7 103.10(16) . . . . ?
C4 C5 C6 O2 167.14(14) . . . . ?
C4 C5 C14 C13 -66.0(2) . . . . ?
C4 C5 C14 C15 114.90(18) . . . . ?
C4 C5 N1 C8 -82.78(17) . . . . ?
C4 C5 N1 C10 44.7(2) . . . . ?
C5 C6 C7 C8 -1.2(2) . . . . ?
C5 C6 C7 O2 107.69(16) . . . . ?
C5 C6 O2 C7 -97.92(16) . . . . ?
C5 C14 C15 C16 -179.05(16) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C6 C5 C14 C13 176.59(15) . . . . ?
C6 C5 C14 C15 -2.5(2) . . . . ?
C6 C5 N1 C8 28.45(18) . . . . ?
C6 C5 N1 C10 155.98(15) . . . . ?
C6 C7 C8 N1 18.5(2) . . . . ?
C7 C8 N1 C5 -29.71(19) . . . . ?
C7 C8 N1 C10 -160.66(15) . . . . ?
C8 C7 O2 C6 97.12(17) . . . . ?
C10 C11 C12 C13 74.1(2) . . . . ?
C11 C10 N1 C5 72.0(2) . . . . ?
C11 C10 N1 C8 -161.88(15) . . . . ?
C11 C12 C13 C14 -55.6(2) . . . . ?
C11 C12 C13 C18 121.25(18) . . . . ?
C12 C13 C14 C5 -5.5(3) . . . . ?
C12 C13 C14 C15 173.58(16) . . . . ?
C12 C13 C18 C17 -174.95(15) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C14 C5 C6 C1 75.5(2) . . . . ?
C14 C5 C6 C7 -133.93(16) . . . . ?
C14 C5 C6 O2 -69.89(18) . . . . ?
C14 C5 N1 C8 148.64(15) . . . . ?
C14 C5 N1 C10 -83.83(19) . . . . ?
C14 C13 C18 C17 2.0(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 O3 -175.61(17) . . . . ?
C15 C16 C17 C18 -1.7(3) . . . . ?
C15 C16 C17 O4 -178.19(17) . . . . ?
C15 C16 O3 C19 -168.72(19) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C16 C17 O4 C19 -12.52(19) . . . . ?
C17 C16 O3 C19 14.7(2) . . . . ?
C18 C13 C14 C5 177.80(16) . . . . ?
C18 C13 C14 C15 -3.1(3) . . . . ?
C18 C17 O4 C19 171.35(19) . . . . ?
N1 C5 C6 C1 -166.89(15) . . . . ?
N1 C5 C6 C7 -16.29(18) . . . . ?
N1 C5 C6 O2 47.75(18) . . . . ?
N1 C5 C14 C13 63.3(2) . . . . ?
N1 C5 C14 C15 -115.76(17) . . . . ?
N1 C10 C11 C12 -64.9(2) . . . . ?
O1 C3 C4 C5 78.4(2) . . . . ?
O2 C6 C7 C8 -108.86(17) . . . . ?
O2 C7 C8 N1 -46.0(2) . . . . ?
O3 C16 C17 C18 175.06(17) . . . . ?
O3 C16 C17 O4 -1.4(2) . . . . ?
O3 C19 O4 C17 21.66(19) . . . . ?
O4 C17 C18 C13 176.15(17) . . . . ?
O4 C19 O3 C16 -22.4(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_211123j_0m
_database_code_depnum_ccdc_archive 'CCDC 2213949'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.3100(17)
_cell_length_b                   10.917(2)
_cell_length_c                   17.120(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1553.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8473
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.36
_cell_measurement_theta_min      3.52
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32663
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         4.494
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4606
_reflns_number_total             4627
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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         -0.270
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1979 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_coef       0.041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.079
_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)+(0.0580P)²+0.1568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0948
_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: 
 C3(H3), C4(H4), C11(H11) 
2.b Secondary CH2 refined with riding coordinates: 
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C1(H1), C14(H14), C17(H17) 
2.d Idealised Me refined as rotating group: 
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3A) 
;
_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 0.25052(16) 0.50245(12) 0.71290(7) 0.0202(2) Uani 1 1 d . . . . .
H1 H 0.191676 0.453801 0.748970 0.024 Uiso 1 1 calc R U . . .
C2 C 0.36614(16) 0.58236(12) 0.73201(7) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.43784(16) 0.64327(11) 0.66150(7) 0.0185(2) Uani 1 1 d . . . . .
H3 H 0.455965 0.732437 0.671556 0.022 Uiso 1 1 calc R U . . .
C4 C 0.30594(15) 0.62497(11) 0.59946(7) 0.0173(2) Uani 1 1 d . . . . .
H4 H 0.224557 0.691966 0.604584 0.021 Uiso 1 1 calc R U . . .
C5 C 0.22739(15) 0.50120(12) 0.62452(7) 0.0183(2) Uani 1 1 d . . . . .
C6 C 0.05266(16) 0.48128(14) 0.59969(8) 0.0238(3) Uani 1 1 d . . . . .
H6A H 0.033358 0.513758 0.546518 0.029 Uiso 1 1 calc R U . . .
H6B H -0.022462 0.521404 0.636563 0.029 Uiso 1 1 calc R U . . .
C7 C 0.03283(19) 0.34052(15) 0.60165(9) 0.0292(3) Uani 1 1 d . . . . .
H7A H -0.023716 0.314398 0.649747 0.035 Uiso 1 1 calc R U . . .
H7B H -0.028766 0.311585 0.555722 0.035 Uiso 1 1 calc R U . . .
C8 C 0.20608(19) 0.29012(13) 0.60007(9) 0.0271(3) Uani 1 1 d . . . . .
H8A H 0.234703 0.252576 0.650844 0.033 Uiso 1 1 calc R U . . .
H8B H 0.218825 0.228078 0.558355 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3637(2) 0.55236(16) 0.86749(8) 0.0334(3) Uani 1 1 d . . . . .
H9A H 0.379491 0.463864 0.861723 0.050 Uiso 1 1 calc R U . . .
H9B H 0.248310 0.570288 0.870557 0.050 Uiso 1 1 calc R U . . .
H9C H 0.416821 0.580541 0.915332 0.050 Uiso 1 1 calc R U . . .
C10 C 0.47649(16) 0.38092(11) 0.60008(7) 0.0204(2) Uani 1 1 d . . . . .
H10A H 0.515826 0.309045 0.570431 0.024 Uiso 1 1 calc R U . . .
H10B H 0.491678 0.363683 0.656370 0.024 Uiso 1 1 calc R U . . .
C11 C 0.57675(15) 0.49351(11) 0.57761(7) 0.0179(2) Uani 1 1 d . . . . .
H11 H 0.688318 0.464896 0.565521 0.022 Uiso 1 1 calc R U . . .
C12 C 0.51296(15) 0.55781(11) 0.50643(7) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.37533(15) 0.62771(11) 0.51855(7) 0.0171(2) Uani 1 1 d . . . . .
C14 C 0.31437(15) 0.69936(11) 0.45773(7) 0.0178(2) Uani 1 1 d . . . . .
H14 H 0.221722 0.748632 0.466075 0.021 Uiso 1 1 calc R U . . .
C15 C 0.38904(15) 0.69874(11) 0.38492(7) 0.0172(2) Uani 1 1 d . . . . .
C16 C 0.52561(15) 0.62540(11) 0.37240(7) 0.0170(2) Uani 1 1 d . . . . .
C17 C 0.58816(15) 0.55570(11) 0.43355(7) 0.0179(2) Uani 1 1 d . . . . .
H17 H 0.681511 0.507023 0.425638 0.021 Uiso 1 1 calc R U . . .
C18 C 0.71994(18) 0.55118(14) 0.28205(8) 0.0267(3) Uani 1 1 d . . . . .
H18A H 0.756189 0.564428 0.228242 0.040 Uiso 1 1 calc R U . . .
H18B H 0.683586 0.466310 0.288085 0.040 Uiso 1 1 calc R U . . .
H18C H 0.809178 0.566981 0.318095 0.040 Uiso 1 1 calc R U . . .
N9 N 0.30587(13) 0.39766(10) 0.58445(6) 0.0195(2) Uani 1 1 d . . . . .
O1 O 0.43133(14) 0.61408(10) 0.80177(5) 0.0257(2) Uani 1 1 d . . . . .
O2 O 0.58763(11) 0.58330(9) 0.64063(5) 0.01937(19) Uani 1 1 d . . . . .
O3 O 0.33511(12) 0.76610(9) 0.32316(5) 0.0214(2) Uani 1 1 d . . . . .
H3A H 0.260579 0.812568 0.338013 0.032 Uiso 1 1 calc R U . . .
O4 O 0.59058(12) 0.63220(9) 0.29909(5) 0.0215(2) 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 H1 0.9500 . ?
C1 C2 1.3384(18) . ?
C1 C5 1.5252(17) . ?
C2 C3 1.5014(17) . ?
C2 O1 1.3565(14) . ?
C3 H3 1.0000 . ?
C3 C4 1.5392(17) . ?
C3 O2 1.4510(16) . ?
C4 H4 1.0000 . ?
C4 C5 1.5608(18) . ?
C4 C13 1.5007(16) . ?
C5 C6 1.5285(18) . ?
C5 N9 1.4743(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.546(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.542(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N9 1.4620(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 O1 1.4268(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5340(18) . ?
C10 N9 1.4544(17) . ?
C11 H11 1.0000 . ?
C11 C12 1.5030(16) . ?
C11 O2 1.4605(15) . ?
C12 C13 1.3905(16) . ?
C12 C17 1.3956(16) . ?
C13 C14 1.3974(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3923(16) . ?
C15 C16 1.4053(17) . ?
C15 O3 1.3636(14) . ?
C16 C17 1.3948(16) . ?
C16 O4 1.3683(14) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O4 1.4223(16) . ?
O3 H3A 0.8400 . ?

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 H1 125.1 . . ?
C2 C1 C5 109.80(11) . . ?
C5 C1 H1 125.1 . . ?
C1 C2 C3 112.15(11) . . ?
C1 C2 O1 131.94(11) . . ?
O1 C2 C3 115.87(11) . . ?
C2 C3 H3 110.6 . . ?
C2 C3 C4 102.40(10) . . ?
C4 C3 H3 110.6 . . ?
O2 C3 C2 109.79(10) . . ?
O2 C3 H3 110.6 . . ?
O2 C3 C4 112.49(9) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C5 102.74(9) . . ?
C5 C4 H4 109.0 . . ?
C13 C4 C3 111.14(10) . . ?
C13 C4 H4 109.0 . . ?
C13 C4 C5 115.57(10) . . ?
C1 C5 C4 102.25(10) . . ?
C1 C5 C6 113.38(10) . . ?
C6 C5 C4 116.36(11) . . ?
N9 C5 C1 114.37(10) . . ?
N9 C5 C4 110.54(10) . . ?
N9 C5 C6 100.47(10) . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C5 C6 C7 103.69(12) . . ?
H6A C6 H6B 109.0 . . ?
C7 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C6 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C6 104.76(11) . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
N9 C8 C7 104.26(12) . . ?
N9 C8 H8A 110.9 . . ?
N9 C8 H8B 110.9 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
N9 C10 H10A 109.1 . . ?
N9 C10 H10B 109.1 . . ?
N9 C10 C11 112.50(10) . . ?
C10 C11 H11 107.8 . . ?
C12 C11 C10 112.71(10) . . ?
C12 C11 H11 107.8 . . ?
O2 C11 C10 112.72(10) . . ?
O2 C11 H11 107.8 . . ?
O2 C11 C12 107.90(9) . . ?
C13 C12 C11 115.18(10) . . ?
C13 C12 C17 120.72(11) . . ?
C17 C12 C11 124.00(11) . . ?
C12 C13 C4 116.29(10) . . ?
C12 C13 C14 119.61(11) . . ?
C14 C13 C4 124.03(11) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.18(11) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 119.95(10) . . ?
O3 C15 C14 123.03(11) . . ?
O3 C15 C16 117.02(10) . . ?
C17 C16 C15 119.82(11) . . ?
O4 C16 C15 115.32(10) . . ?
O4 C16 C17 124.82(11) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 C12 119.68(11) . . ?
C16 C17 H17 120.2 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
C8 N9 C5 106.24(10) . . ?
C10 N9 C5 116.24(10) . . ?
C10 N9 C8 114.74(11) . . ?
C2 O1 C9 114.61(11) . . ?
C3 O2 C11 115.57(9) . . ?
C15 O3 H3A 109.5 . . ?
C16 O4 C18 116.91(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.84 1.87 2.7050(14) 173.6 2_466 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 20.85(15) . . . . ?
C1 C2 C3 O2 -98.84(13) . . . . ?
C1 C2 O1 C9 -0.8(2) . . . . ?
C1 C5 C6 C7 -84.00(13) . . . . ?
C1 C5 N9 C8 75.56(13) . . . . ?
C1 C5 N9 C10 -53.45(14) . . . . ?
C2 C1 C5 C4 -19.01(14) . . . . ?
C2 C1 C5 C6 -145.09(12) . . . . ?
C2 C1 C5 N9 100.49(13) . . . . ?
C2 C3 C4 C5 -30.87(11) . . . . ?
C2 C3 C4 C13 -155.06(10) . . . . ?
C2 C3 O2 C11 98.54(11) . . . . ?
C3 C2 O1 C9 -178.42(13) . . . . ?
C3 C4 C5 C1 30.40(12) . . . . ?
C3 C4 C5 C6 154.51(10) . . . . ?
C3 C4 C5 N9 -91.76(11) . . . . ?
C3 C4 C13 C12 46.91(14) . . . . ?
C3 C4 C13 C14 -130.09(12) . . . . ?
C4 C3 O2 C11 -14.78(13) . . . . ?
C4 C5 C6 C7 157.81(11) . . . . ?
C4 C5 N9 C8 -169.70(10) . . . . ?
C4 C5 N9 C10 61.29(13) . . . . ?
C4 C13 C14 C15 178.27(11) . . . . ?
C5 C1 C2 C3 -0.98(16) . . . . ?
C5 C1 C2 O1 -178.63(14) . . . . ?
C5 C4 C13 C12 -69.65(14) . . . . ?
C5 C4 C13 C14 113.34(14) . . . . ?
C5 C6 C7 C8 -18.32(13) . . . . ?
C6 C5 N9 C8 -46.24(12) . . . . ?
C6 C5 N9 C10 -175.24(10) . . . . ?
C6 C7 C8 N9 -9.07(14) . . . . ?
C7 C8 N9 C5 34.82(13) . . . . ?
C7 C8 N9 C10 164.70(11) . . . . ?
C10 C11 C12 C13 75.53(13) . . . . ?
C10 C11 C12 C17 -108.16(13) . . . . ?
C10 C11 O2 C3 -66.42(12) . . . . ?
C11 C10 N9 C5 -59.02(14) . . . . ?
C11 C10 N9 C8 176.21(10) . . . . ?
C11 C12 C13 C4 -2.56(16) . . . . ?
C11 C12 C13 C14 174.59(11) . . . . ?
C11 C12 C17 C16 -175.47(11) . . . . ?
C12 C11 O2 C3 58.68(12) . . . . ?
C12 C13 C14 C15 1.36(18) . . . . ?
C13 C4 C5 C1 151.60(11) . . . . ?
C13 C4 C5 C6 -84.28(13) . . . . ?
C13 C4 C5 N9 29.44(14) . . . . ?
C13 C12 C17 C16 0.65(18) . . . . ?
C13 C14 C15 C16 0.33(18) . . . . ?
C13 C14 C15 O3 179.69(11) . . . . ?
C14 C15 C16 C17 -1.53(18) . . . . ?
C14 C15 C16 O4 -179.48(11) . . . . ?
C15 C16 C17 C12 1.05(18) . . . . ?
C15 C16 O4 C18 -174.51(11) . . . . ?
C17 C12 C13 C4 -179.00(11) . . . . ?
C17 C12 C13 C14 -1.85(18) . . . . ?
C17 C16 O4 C18 7.66(18) . . . . ?
N9 C5 C6 C7 38.48(12) . . . . ?
N9 C10 C11 C12 -34.85(14) . . . . ?
N9 C10 C11 O2 87.58(12) . . . . ?
O1 C2 C3 C4 -161.09(11) . . . . ?
O1 C2 C3 O2 79.22(13) . . . . ?
O2 C3 C4 C5 86.92(11) . . . . ?
O2 C3 C4 C13 -37.27(13) . . . . ?
O2 C11 C12 C13 -49.57(14) . . . . ?
O2 C11 C12 C17 126.74(12) . . . . ?
O3 C15 C16 C17 179.06(11) . . . . ?
O3 C15 C16 O4 1.12(16) . . . . ?
O4 C16 C17 C12 178.78(11) . . . . ?

_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_211211c_0m
_database_code_depnum_ccdc_archive 'CCDC 2213950'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   6.6976(4)
_cell_length_b                   10.7016(6)
_cell_length_c                   11.0783(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.0760(10)
_cell_angle_gamma                90
_cell_volume                     792.03(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9424
_cell_measurement_theta_min      5.76
_cell_measurement_theta_max      72.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.535
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker PhotonIII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30485
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.762
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4610
_reflns_number_gt                4586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.947
_reflns_Friedel_fraction_full    0.969

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0690P)²+0.0482P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2112 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4610
_refine_ls_number_parameters     219
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.7447(2) 0.76871(13) 0.56813(13) 0.0288(3) Uani 1 1 d . . . . .
H1A H 0.650847 0.825292 0.521720 0.035 Uiso 1 1 calc R U . . .
H1B H 0.855178 0.819320 0.606886 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8271(2) 0.67099(13) 0.48436(11) 0.0257(2) Uani 1 1 d . . . . .
H2 H 0.729318 0.659183 0.412778 0.031 Uiso 1 1 calc R U . . .
C3 C 0.83630(18) 0.55003(12) 0.55999(11) 0.0219(2) Uani 1 1 d . . . . .
C4 C 0.64152(17) 0.55840(12) 0.62584(10) 0.0200(2) Uani 1 1 d . . . . .
H4 H 0.525286 0.541346 0.566413 0.024 Uiso 1 1 calc R U . . .
C5 C 0.63417(17) 0.69701(11) 0.66566(11) 0.0207(2) Uani 1 1 d . . . . .
C6 C 0.42417(19) 0.74605(13) 0.68187(13) 0.0281(3) Uani 1 1 d . . . . .
H6A H 0.344351 0.684210 0.724268 0.034 Uiso 1 1 calc R U . . .
H6B H 0.353395 0.766466 0.602831 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4621(2) 0.86422(14) 0.75897(14) 0.0308(3) Uani 1 1 d . . . . .
H7A H 0.358587 0.874056 0.817785 0.037 Uiso 1 1 calc R U . . .
H7B H 0.462615 0.939709 0.707345 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6708(2) 0.84186(13) 0.82476(13) 0.0260(2) Uani 1 1 d . . . . .
H8A H 0.769692 0.902780 0.797873 0.031 Uiso 1 1 calc R U . . .
H8B H 0.664914 0.848732 0.913546 0.031 Uiso 1 1 calc R U . . .
C10 C 0.93194(18) 0.68185(13) 0.81501(12) 0.0246(2) Uani 1 1 d . . . . .
H10A H 0.966194 0.686905 0.903287 0.029 Uiso 1 1 calc R U . . .
H10B H 1.016174 0.743076 0.774950 0.029 Uiso 1 1 calc R U . . .
C11 C 0.97878(17) 0.55017(13) 0.77065(11) 0.0218(2) Uani 1 1 d . . . . .
H11 H 1.107016 0.522843 0.814512 0.026 Uiso 1 1 calc R U . . .
C12 C 0.81920(16) 0.45757(11) 0.79965(11) 0.0209(2) Uani 1 1 d . . . . .
C13 C 0.64105(17) 0.46455(11) 0.72605(10) 0.0199(2) Uani 1 1 d . . . . .
C14 C 0.47874(17) 0.38501(12) 0.74472(11) 0.0223(2) Uani 1 1 d . . . . .
H14 H 0.356873 0.389280 0.695485 0.027 Uiso 1 1 calc R U . . .
C15 C 0.50633(19) 0.30055(12) 0.83840(11) 0.0236(2) Uani 1 1 d . . . . .
C16 C 0.6840(2) 0.29311(13) 0.91045(12) 0.0254(2) Uani 1 1 d . . . . .
C17 C 0.84412(19) 0.37075(13) 0.89404(12) 0.0251(2) Uani 1 1 d . . . . .
H17 H 0.964977 0.365604 0.944150 0.030 Uiso 1 1 calc R U . . .
C18 C 0.4877(2) 0.13588(15) 0.96062(14) 0.0320(3) Uani 1 1 d . . . . .
H18A H 0.411921 0.118174 1.032235 0.038 Uiso 1 1 calc R U . . .
H18B H 0.518433 0.055558 0.921676 0.038 Uiso 1 1 calc R U . . .
C19 C 1.0915(4) 0.6385(2) 0.3531(2) 0.0503(5) Uani 1 1 d . . . . .
H19A H 0.988595 0.624310 0.287125 0.075 Uiso 1 1 calc R U . . .
H19B H 1.134753 0.558055 0.388290 0.075 Uiso 1 1 calc R U . . .
H19C H 1.206329 0.681049 0.321449 0.075 Uiso 1 1 calc R U . . .
N9 N 0.72276(14) 0.71439(10) 0.78995(9) 0.02073(19) Uani 1 1 d . . . . .
O1 O 1.01150(18) 0.71381(11) 0.44356(10) 0.0332(2) Uani 1 1 d . . . . .
O2 O 0.84469(17) 0.44685(9) 0.48361(9) 0.0291(2) Uani 1 1 d . . . . .
H2A H 0.882666 0.383887 0.524295 0.044 Uiso 1 1 calc R U . . .
O3 O 1.00901(13) 0.55035(10) 0.64277(9) 0.02461(19) Uani 1 1 d . . . . .
O4 O 0.37202(16) 0.21437(12) 0.87690(10) 0.0339(2) Uani 1 1 d . . . . .
O5 O 0.66945(18) 0.20144(12) 0.99631(11) 0.0362(3) 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 1.5273(19) . ?
C1 C5 1.5549(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.4208(17) . ?
C2 C3 1.5408(18) . ?
C2 H2 1.0000 . ?
C3 O2 1.3946(15) . ?
C3 O3 1.4242(14) . ?
C3 C4 1.5419(17) . ?
C4 C13 1.4972(16) . ?
C4 C5 1.5494(17) . ?
C4 H4 1.0000 . ?
C5 N9 1.4719(15) . ?
C5 C6 1.5237(17) . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.549(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N9 1.4661(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 N9 1.4511(15) . ?
C10 C11 1.5323(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.4452(15) . ?
C11 C12 1.5088(17) . ?
C11 H11 1.0000 . ?
C12 C13 1.3985(15) . ?
C12 C17 1.3999(17) . ?
C13 C14 1.4075(16) . ?
C14 C15 1.3787(17) . ?
C14 H14 0.9500 . ?
C15 O4 1.3771(16) . ?
C15 C16 1.3875(17) . ?
C16 O5 1.3747(16) . ?
C16 C17 1.3787(18) . ?
C17 H17 0.9500 . ?
C18 O5 1.4360(19) . ?
C18 O4 1.4365(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O1 1.421(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 H2A 0.8400 . ?

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 C5 107.15(10) . . ?
C2 C1 H1A 110.3 . . ?
C5 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C5 C1 H1B 110.3 . . ?
H1A C1 H1B 108.5 . . ?
O1 C2 C1 109.41(11) . . ?
O1 C2 C3 116.23(12) . . ?
C1 C2 C3 104.30(10) . . ?
O1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
O2 C3 O3 109.07(10) . . ?
O2 C3 C2 109.69(10) . . ?
O3 C3 C2 110.32(10) . . ?
O2 C3 C4 113.89(10) . . ?
O3 C3 C4 111.78(9) . . ?
C2 C3 C4 101.89(10) . . ?
C13 C4 C3 111.00(10) . . ?
C13 C4 C5 115.42(9) . . ?
C3 C4 C5 103.62(9) . . ?
C13 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
N9 C5 C6 99.23(9) . . ?
N9 C5 C4 111.62(9) . . ?
C6 C5 C4 114.31(10) . . ?
N9 C5 C1 114.05(10) . . ?
C6 C5 C1 113.63(10) . . ?
C4 C5 C1 104.37(10) . . ?
C5 C6 C7 103.39(10) . . ?
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 . . ?
C6 C7 C8 104.02(10) . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
N9 C8 C7 104.07(10) . . ?
N9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
N9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 109.0 . . ?
N9 C10 C11 112.10(10) . . ?
N9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C12 111.12(10) . . ?
O3 C11 C10 111.05(11) . . ?
C12 C11 C10 111.81(10) . . ?
O3 C11 H11 107.5 . . ?
C12 C11 H11 107.5 . . ?
C10 C11 H11 107.5 . . ?
C13 C12 C17 121.50(11) . . ?
C13 C12 C11 115.39(10) . . ?
C17 C12 C11 123.11(10) . . ?
C12 C13 C14 121.19(11) . . ?
C12 C13 C4 114.93(10) . . ?
C14 C13 C4 123.85(10) . . ?
C15 C14 C13 116.33(11) . . ?
C15 C14 H14 121.8 . . ?
C13 C14 H14 121.8 . . ?
O4 C15 C14 128.07(11) . . ?
O4 C15 C16 109.63(11) . . ?
C14 C15 C16 122.30(11) . . ?
O5 C16 C17 127.99(12) . . ?
O5 C16 C15 109.80(12) . . ?
C17 C16 C15 122.20(12) . . ?
C16 C17 C12 116.48(11) . . ?
C16 C17 H17 121.8 . . ?
C12 C17 H17 121.8 . . ?
O5 C18 O4 107.45(12) . . ?
O5 C18 H18A 110.2 . . ?
O4 C18 H18A 110.2 . . ?
O5 C18 H18B 110.2 . . ?
O4 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 N9 C8 114.63(10) . . ?
C10 N9 C5 117.91(10) . . ?
C8 N9 C5 106.03(10) . . ?
C19 O1 C2 114.91(13) . . ?
C3 O2 H2A 109.5 . . ?
C3 O3 C11 117.85(9) . . ?
C15 O4 C18 104.91(11) . . ?
C16 O5 C18 104.99(11) . . ?

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
C5 C1 C2 O1 -146.29(11) . . . . ?
C5 C1 C2 C3 -21.30(14) . . . . ?
O1 C2 C3 O2 -79.08(14) . . . . ?
C1 C2 C3 O2 160.39(11) . . . . ?
O1 C2 C3 O3 41.09(15) . . . . ?
C1 C2 C3 O3 -79.44(13) . . . . ?
O1 C2 C3 C4 159.92(11) . . . . ?
C1 C2 C3 C4 39.40(12) . . . . ?
O2 C3 C4 C13 74.78(12) . . . . ?
O3 C3 C4 C13 -49.39(13) . . . . ?
C2 C3 C4 C13 -167.19(9) . . . . ?
O2 C3 C4 C5 -160.73(10) . . . . ?
O3 C3 C4 C5 75.09(12) . . . . ?
C2 C3 C4 C5 -42.71(11) . . . . ?
C13 C4 C5 N9 27.44(13) . . . . ?
C3 C4 C5 N9 -94.12(11) . . . . ?
C13 C4 C5 C6 -84.17(13) . . . . ?
C3 C4 C5 C6 154.27(10) . . . . ?
C13 C4 C5 C1 151.09(10) . . . . ?
C3 C4 C5 C1 29.53(12) . . . . ?
C2 C1 C5 N9 116.97(12) . . . . ?
C2 C1 C5 C6 -130.27(12) . . . . ?
C2 C1 C5 C4 -5.10(14) . . . . ?
N9 C5 C6 C7 43.14(13) . . . . ?
C4 C5 C6 C7 162.02(11) . . . . ?
C1 C5 C6 C7 -78.31(13) . . . . ?
C5 C6 C7 C8 -23.75(14) . . . . ?
C6 C7 C8 N9 -4.88(14) . . . . ?
N9 C10 C11 O3 81.86(12) . . . . ?
N9 C10 C11 C12 -42.88(14) . . . . ?
O3 C11 C12 C13 -49.00(14) . . . . ?
C10 C11 C12 C13 75.71(14) . . . . ?
O3 C11 C12 C17 131.60(12) . . . . ?
C10 C11 C12 C17 -103.70(14) . . . . ?
C17 C12 C13 C14 0.54(19) . . . . ?
C11 C12 C13 C14 -178.88(11) . . . . ?
C17 C12 C13 C4 -177.41(11) . . . . ?
C11 C12 C13 C4 3.17(16) . . . . ?
C3 C4 C13 C12 45.46(14) . . . . ?
C5 C4 C13 C12 -72.03(14) . . . . ?
C3 C4 C13 C14 -132.42(12) . . . . ?
C5 C4 C13 C14 110.08(13) . . . . ?
C12 C13 C14 C15 -0.31(18) . . . . ?
C4 C13 C14 C15 177.45(11) . . . . ?
C13 C14 C15 O4 178.87(13) . . . . ?
C13 C14 C15 C16 -0.33(19) . . . . ?
O4 C15 C16 O5 0.54(17) . . . . ?
C14 C15 C16 O5 179.87(12) . . . . ?
O4 C15 C16 C17 -178.56(13) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
O5 C16 C17 C12 -179.45(14) . . . . ?
C15 C16 C17 C12 -0.5(2) . . . . ?
C13 C12 C17 C16 -0.11(19) . . . . ?
C11 C12 C17 C16 179.26(12) . . . . ?
C11 C10 N9 C8 -177.01(10) . . . . ?
C11 C10 N9 C5 -51.09(15) . . . . ?
C7 C8 N9 C10 165.29(11) . . . . ?
C7 C8 N9 C5 33.41(13) . . . . ?
C6 C5 N9 C10 -178.08(11) . . . . ?
C4 C5 N9 C10 61.06(14) . . . . ?
C1 C5 N9 C10 -56.93(14) . . . . ?
C6 C5 N9 C8 -48.07(12) . . . . ?
C4 C5 N9 C8 -168.93(10) . . . . ?
C1 C5 N9 C8 73.08(12) . . . . ?
C1 C2 O1 C19 -172.53(16) . . . . ?
C3 C2 O1 C19 69.73(18) . . . . ?
O2 C3 O3 C11 -123.03(11) . . . . ?
C2 C3 O3 C11 116.43(12) . . . . ?
C4 C3 O3 C11 3.80(15) . . . . ?
C12 C11 O3 C3 44.52(15) . . . . ?
C10 C11 O3 C3 -80.62(13) . . . . ?
C14 C15 O4 C18 169.45(13) . . . . ?
C16 C15 O4 C18 -11.27(16) . . . . ?
O5 C18 O4 C15 17.59(15) . . . . ?
C17 C16 O5 C18 -170.53(15) . . . . ?
C15 C16 O5 C18 10.44(16) . . . . ?
O4 C18 O5 C16 -17.28(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2A O1 0.84 1.98 2.7727(15) 157.9 2_746 yes

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_210917n_0m
_database_code_depnum_ccdc_archive 'CCDC 2213954'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-11-24
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O4'
_chemical_formula_sum            'C19 H21 N O4'
_chemical_formula_weight         327.37
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   6.6669(6)
_cell_length_b                   21.971(2)
_cell_length_c                   11.9519(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.559(4)
_cell_angle_gamma                90
_cell_volume                     1701.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.98
_cell_measurement_theta_min      3.50
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_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  0.0455
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            65775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.359
_diffrn_reflns_theta_min         3.500
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4131
_reflns_number_total             5114
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0054(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         5114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.040
_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)+(0.0579P)²+0.3971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1217
_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 
2.a Ternary CH refined with riding coordinates: 
 C4(H4) 
2.b Secondary CH2 refined with riding coordinates: 
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), 
 C18(H18A,H18B), C19(H19A,H19B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C1(H1), C14(H14), C17(H17) 
2.d Idealised Me refined as rotating group: 
 C20(H20A,H20B,H20C) 
;
_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 0.62587(16) 0.73927(5) 0.72880(9) 0.0315(2) Uani 1 1 d . . . . .
H1 H 0.661095 0.761337 0.799039 0.038 Uiso 1 1 calc R U . . .
C2 C 0.51615(15) 0.76269(5) 0.62978(9) 0.0292(2) Uani 1 1 d . . . . .
C3 C 0.48824(14) 0.71743(5) 0.53635(9) 0.0271(2) Uani 1 1 d . . . . .
C4 C 0.57842(15) 0.65750(5) 0.58945(9) 0.02677(19) Uani 1 1 d . . . . .
H4 H 0.459196 0.630487 0.592710 0.032 Uiso 1 1 calc R U . . .
C5 C 0.68789(15) 0.67337(5) 0.71635(9) 0.0286(2) Uani 1 1 d . . . . .
C6 C 0.6241(2) 0.63135(6) 0.80608(11) 0.0428(3) Uani 1 1 d . . . . .
H6A H 0.510798 0.650013 0.834987 0.051 Uiso 1 1 calc R U . . .
H6B H 0.577010 0.591384 0.771425 0.051 Uiso 1 1 calc R U . . .
C7 C 0.8146(3) 0.62390(9) 0.90279(13) 0.0625(4) Uani 1 1 d . . . . .
H7A H 0.791714 0.641784 0.974810 0.075 Uiso 1 1 calc R U . . .
H7B H 0.848637 0.580249 0.916262 0.075 Uiso 1 1 calc R U . . .
C8 C 0.9859(2) 0.65648(7) 0.86600(10) 0.0443(3) Uani 1 1 d . . . . .
H8A H 1.011103 0.696875 0.903353 0.053 Uiso 1 1 calc R U . . .
H8B H 1.115091 0.632479 0.885699 0.053 Uiso 1 1 calc R U . . .
C10 C 1.03599(16) 0.70510(6) 0.69151(11) 0.0364(2) Uani 1 1 d . . . . .
H10A H 1.181782 0.691659 0.711619 0.044 Uiso 1 1 calc R U . . .
H10B H 1.029415 0.745882 0.725690 0.044 Uiso 1 1 calc R U . . .
C11 C 0.96333(16) 0.70988(5) 0.56048(10) 0.0321(2) Uani 1 1 d . . . . .
H11A H 0.849696 0.739901 0.541340 0.039 Uiso 1 1 calc R U . . .
H11B H 1.078527 0.725275 0.529090 0.039 Uiso 1 1 calc R U . . .
C12 C 0.88955(15) 0.65022(5) 0.50302(9) 0.0283(2) Uani 1 1 d . . . . .
C13 C 0.70547(15) 0.62434(5) 0.51929(9) 0.0267(2) Uani 1 1 d . . . . .
C14 C 0.63444(16) 0.56841(5) 0.46879(9) 0.0304(2) Uani 1 1 d . . . . .
H14 H 0.508658 0.551108 0.477931 0.036 Uiso 1 1 calc R U . . .
C15 C 0.75371(18) 0.53958(5) 0.40558(10) 0.0333(2) Uani 1 1 d . . . . .
C16 C 0.93394(18) 0.56486(5) 0.38928(10) 0.0349(2) Uani 1 1 d . . . . .
C17 C 1.00536(16) 0.62010(5) 0.43575(10) 0.0330(2) Uani 1 1 d . . . . .
H17 H 1.128689 0.637333 0.422851 0.040 Uiso 1 1 calc R U . . .
C18 C 0.8807(2) 0.47768(6) 0.29109(13) 0.0500(3) Uani 1 1 d . . . . .
H18A H 0.953269 0.438540 0.312275 0.060 Uiso 1 1 calc R U . . .
H18B H 0.822609 0.477818 0.206889 0.060 Uiso 1 1 calc R U . . .
C19 C 0.4639(2) 0.86200(6) 0.69337(12) 0.0471(3) Uani 1 1 d . . . . .
H19A H 0.613383 0.868647 0.724751 0.057 Uiso 1 1 calc R U . . .
H19B H 0.402638 0.847384 0.756325 0.057 Uiso 1 1 calc R U . . .
C20 C 0.3618(3) 0.92018(7) 0.64377(16) 0.0708(5) Uani 1 1 d . . . . .
H20A H 0.420100 0.933336 0.579695 0.106 Uiso 1 1 calc R U . . .
H20B H 0.385669 0.951725 0.703400 0.106 Uiso 1 1 calc R U . . .
H20C H 0.213189 0.913415 0.615872 0.106 Uiso 1 1 calc R U . . .
N9 N 0.91272(13) 0.66274(4) 0.74122(8) 0.03085(19) Uani 1 1 d . . . . .
O1 O 0.43119(13) 0.81801(4) 0.60137(7) 0.03712(19) Uani 1 1 d . . . . .
O2 O 0.40328(12) 0.72602(4) 0.43575(7) 0.03430(18) Uani 1 1 d . . . . .
O3 O 1.02161(16) 0.52690(5) 0.32221(9) 0.0526(3) Uani 1 1 d . . . . .
O4 O 0.71819(16) 0.48408(4) 0.35018(9) 0.0484(2) 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 H1 0.9500 . ?
C1 C2 1.3396(15) . ?
C1 C5 1.5224(15) . ?
C2 C3 1.4741(14) . ?
C2 O1 1.3502(13) . ?
C3 C4 1.5228(14) . ?
C3 O2 1.2177(13) . ?
C4 H4 1.0000 . ?
C4 C5 1.5607(14) . ?
C4 C13 1.5113(14) . ?
C5 C6 1.5484(15) . ?
C5 N9 1.4767(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.512(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.499(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N9 1.4628(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5306(17) . ?
C10 N9 1.4572(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5076(15) . ?
C12 C13 1.4069(14) . ?
C12 C17 1.4043(14) . ?
C13 C14 1.4017(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.3732(15) . ?
C15 C16 1.3784(17) . ?
C15 O4 1.3813(13) . ?
C16 C17 1.3727(16) . ?
C16 O3 1.3781(13) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 O3 1.4237(19) . ?
C18 O4 1.4322(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.503(2) . ?
C19 O1 1.4417(14) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C2 C1 H1 123.7 . . ?
C2 C1 C5 112.55(9) . . ?
C5 C1 H1 123.7 . . ?
C1 C2 C3 110.85(9) . . ?
C1 C2 O1 132.68(10) . . ?
O1 C2 C3 116.47(9) . . ?
C2 C3 C4 107.47(8) . . ?
O2 C3 C2 126.17(10) . . ?
O2 C3 C4 126.33(9) . . ?
C3 C4 H4 106.8 . . ?
C3 C4 C5 105.11(8) . . ?
C5 C4 H4 106.8 . . ?
C13 C4 C3 113.79(8) . . ?
C13 C4 H4 106.8 . . ?
C13 C4 C5 116.85(8) . . ?
C1 C5 C4 103.40(8) . . ?
C1 C5 C6 111.98(9) . . ?
C6 C5 C4 113.45(9) . . ?
N9 C5 C1 114.64(9) . . ?
N9 C5 C4 112.43(8) . . ?
N9 C5 C6 101.36(9) . . ?
C5 C6 H6A 110.5 . . ?
C5 C6 H6B 110.5 . . ?
H6A C6 H6B 108.7 . . ?
C7 C6 C5 106.02(11) . . ?
C7 C6 H6A 110.5 . . ?
C7 C6 H6B 110.5 . . ?
C6 C7 H7A 110.4 . . ?
C6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 C6 106.58(11) . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
N9 C8 C7 104.42(10) . . ?
N9 C8 H8A 110.9 . . ?
N9 C8 H8B 110.9 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
N9 C10 H10A 109.0 . . ?
N9 C10 H10B 109.0 . . ?
N9 C10 C11 112.80(8) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.43(9) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 119.37(9) . . ?
C17 C12 C11 120.40(9) . . ?
C17 C12 C13 120.21(10) . . ?
C12 C13 C4 120.15(9) . . ?
C14 C13 C4 119.00(9) . . ?
C14 C13 C12 120.83(9) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.42(10) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 121.90(10) . . ?
C14 C15 O4 127.92(11) . . ?
C16 C15 O4 110.18(10) . . ?
C17 C16 C15 122.02(10) . . ?
C17 C16 O3 128.03(11) . . ?
O3 C16 C15 109.95(10) . . ?
C12 C17 H17 121.2 . . ?
C16 C17 C12 117.60(10) . . ?
C16 C17 H17 121.2 . . ?
H18A C18 H18B 108.3 . . ?
O3 C18 H18A 109.9 . . ?
O3 C18 H18B 109.9 . . ?
O3 C18 O4 109.01(10) . . ?
O4 C18 H18A 109.9 . . ?
O4 C18 H18B 109.9 . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.3 . . ?
C20 C19 H19B 110.3 . . ?
O1 C19 H19A 110.3 . . ?
O1 C19 H19B 110.3 . . ?
O1 C19 C20 107.21(11) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N9 C5 107.48(9) . . ?
C10 N9 C5 117.37(9) . . ?
C10 N9 C8 112.98(9) . . ?
C2 O1 C19 115.61(9) . . ?
C16 O3 C18 105.53(10) . . ?
C15 O4 C18 104.99(10) . . ?

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 5.31(11) . . . . ?
C1 C2 C3 O2 -176.61(10) . . . . ?
C1 C2 O1 C19 0.85(18) . . . . ?
C1 C5 C6 C7 -97.97(13) . . . . ?
C1 C5 N9 C8 83.24(11) . . . . ?
C1 C5 N9 C10 -45.37(12) . . . . ?
C2 C1 C5 C4 -4.51(11) . . . . ?
C2 C1 C5 C6 -127.01(10) . . . . ?
C2 C1 C5 N9 118.22(10) . . . . ?
C2 C3 C4 C5 -7.76(10) . . . . ?
C2 C3 C4 C13 -136.84(8) . . . . ?
C3 C2 O1 C19 -178.75(10) . . . . ?
C3 C4 C5 C1 7.26(10) . . . . ?
C3 C4 C5 C6 128.78(9) . . . . ?
C3 C4 C5 N9 -116.93(9) . . . . ?
C3 C4 C13 C12 64.73(12) . . . . ?
C3 C4 C13 C14 -113.76(10) . . . . ?
C4 C5 C6 C7 145.45(12) . . . . ?
C4 C5 N9 C8 -159.05(9) . . . . ?
C4 C5 N9 C10 72.34(11) . . . . ?
C4 C13 C14 C15 179.95(9) . . . . ?
C5 C1 C2 C3 -0.37(12) . . . . ?
C5 C1 C2 O1 -179.99(11) . . . . ?
C5 C4 C13 C12 -58.14(13) . . . . ?
C5 C4 C13 C14 123.37(10) . . . . ?
C5 C6 C7 C8 -4.10(17) . . . . ?
C6 C5 N9 C8 -37.57(11) . . . . ?
C6 C5 N9 C10 -166.18(9) . . . . ?
C6 C7 C8 N9 -18.56(17) . . . . ?
C7 C8 N9 C5 35.97(14) . . . . ?
C7 C8 N9 C10 167.05(12) . . . . ?
C10 C11 C12 C13 68.96(12) . . . . ?
C10 C11 C12 C17 -109.77(11) . . . . ?
C11 C10 N9 C5 -56.00(13) . . . . ?
C11 C10 N9 C8 178.06(10) . . . . ?
C11 C12 C13 C4 2.68(15) . . . . ?
C11 C12 C13 C14 -178.86(10) . . . . ?
C11 C12 C17 C16 177.60(10) . . . . ?
C12 C13 C14 C15 1.47(15) . . . . ?
C13 C4 C5 C1 134.50(9) . . . . ?
C13 C4 C5 C6 -103.98(11) . . . . ?
C13 C4 C5 N9 10.31(12) . . . . ?
C13 C12 C17 C16 -1.12(16) . . . . ?
C13 C14 C15 C16 -1.61(16) . . . . ?
C13 C14 C15 O4 178.61(11) . . . . ?
C14 C15 C16 C17 0.37(18) . . . . ?
C14 C15 C16 O3 -179.49(10) . . . . ?
C14 C15 O4 C18 176.02(12) . . . . ?
C15 C16 C17 C12 1.02(17) . . . . ?
C15 C16 O3 C18 3.31(14) . . . . ?
C16 C15 O4 C18 -3.78(13) . . . . ?
C17 C12 C13 C4 -178.59(9) . . . . ?
C17 C12 C13 C14 -0.12(16) . . . . ?
C17 C16 O3 C18 -176.55(12) . . . . ?
C20 C19 O1 C2 178.88(13) . . . . ?
N9 C5 C6 C7 24.69(14) . . . . ?
N9 C10 C11 C12 -36.66(12) . . . . ?
O1 C2 C3 C4 -175.01(8) . . . . ?
O1 C2 C3 O2 3.07(15) . . . . ?
O2 C3 C4 C5 174.16(9) . . . . ?
O2 C3 C4 C13 45.08(13) . . . . ?
O3 C16 C17 C12 -179.14(11) . . . . ?
O3 C18 O4 C15 5.82(14) . . . . ?
O4 C15 C16 C17 -179.81(10) . . . . ?
O4 C15 C16 O3 0.32(14) . . . . ?
O4 C18 O3 C16 -5.66(14) . . . . ?

_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_211211b_0m
_database_code_depnum_ccdc_archive 'CCDC 2213953'
loop_
_audit_author_name
_audit_author_address
'Guanqun Zhan'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2022-10-19 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H39 N O11'
_chemical_formula_weight         553.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   9.4013(5)
_cell_length_b                   26.2244(16)
_cell_length_c                   12.2587(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.836(2)
_cell_angle_gamma                90
_cell_volume                     3022.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9836
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      62.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.503
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Ventrue'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            81736
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         63.132
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             14799
_reflns_number_gt                13014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT V8.40B'
_computing_data_reduction        'Bruker SAINT V8.40B'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1077P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 5651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         14799
_refine_ls_number_parameters     739
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_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
C1 C 0.0170(3) 0.38567(10) 0.4716(2) 0.0351(5) Uani 1 1 d . . . . .
H1 H 0.034398 0.418812 0.443489 0.042 Uiso 1 1 calc R U . . .
C1' C -0.2106(3) 0.23191(10) 0.48389(19) 0.0306(5) Uani 1 1 d . . . . .
C2 C -0.1128(3) 0.36513(10) 0.4832(2) 0.0340(5) Uani 1 1 d . . . . .
C2' C -0.2775(3) 0.19794(10) 0.39373(18) 0.0307(5) Uani 1 1 d . . . . .
C3 C -0.1091(3) 0.31171(10) 0.52673(19) 0.0310(5) Uani 1 1 d . . . . .
H3 H -0.157124 0.310281 0.598906 0.037 Uiso 1 1 calc R U . . .
C3' C -0.4412(3) 0.19974(11) 0.4077(2) 0.0351(5) Uani 1 1 d . . . . .
H3' H -0.485914 0.180378 0.345835 0.042 Uiso 1 1 calc R U . . .
C4 C 0.0511(3) 0.29938(10) 0.54128(18) 0.0319(5) Uani 1 1 d . . . . .
H4 H 0.068121 0.294764 0.621382 0.038 Uiso 1 1 calc R U . . .
C4' C -0.4991(3) 0.25468(11) 0.4039(2) 0.0377(5) Uani 1 1 d . . . . .
C5 C 0.1308(3) 0.34926(10) 0.5090(2) 0.0361(5) Uani 1 1 d . . . . .
C5' C -0.2162(3) 0.14451(10) 0.4031(2) 0.0354(5) Uani 1 1 d . . . . .
H5'A H -0.113708 0.145792 0.385904 0.042 Uiso 1 1 calc R U . . .
H5'B H -0.224690 0.132782 0.479465 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2260(4) 0.37043(14) 0.6014(3) 0.0542(8) Uani 1 1 d . . . . .
H6B H 0.172371 0.395454 0.645075 0.065 Uiso 1 1 calc R U . . .
H6C H 0.257500 0.342403 0.650134 0.065 Uiso 1 1 calc R U . . .
C6' C -0.2882(4) 0.10606(12) 0.3286(2) 0.0459(6) Uani 1 1 d . . . . .
H6'A H -0.296869 0.120892 0.254495 0.055 Uiso 1 1 calc R U . . .
H6'B H -0.385571 0.099686 0.355073 0.055 Uiso 1 1 calc R U . . .
C7 C 0.3526(5) 0.3957(2) 0.5513(5) 0.0860(16) Uani 1 1 d . . . . .
H7D H 0.441819 0.381453 0.582606 0.103 Uiso 1 1 calc R U . . .
H7E H 0.350909 0.432827 0.565362 0.103 Uiso 1 1 calc R U . . .
C7' C -0.2096(5) 0.05515(13) 0.3212(3) 0.0573(8) Uani 1 1 d . . . . .
H7' H -0.116577 0.061781 0.285290 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3437(4) 0.38532(13) 0.4306(4) 0.0623(10) Uani 1 1 d . . . . .
H8A H 0.438302 0.376383 0.401672 0.075 Uiso 1 1 calc R U . . .
H8B H 0.306445 0.415391 0.390597 0.075 Uiso 1 1 calc R U . . .
C8' C -0.2944(7) 0.01833(17) 0.2475(4) 0.0822(14) Uani 1 1 d . . . . .
H8'A H -0.391143 0.014688 0.275282 0.123 Uiso 1 1 calc R U . . .
H8'B H -0.247569 -0.015046 0.247305 0.123 Uiso 1 1 calc R U . . .
H8'C H -0.298703 0.031872 0.173039 0.123 Uiso 1 1 calc R U . . .
C9' C -0.1779(8) 0.03211(19) 0.4314(4) 0.0932(17) Uani 1 1 d . . . . .
H9'A H -0.121861 0.056225 0.475437 0.140 Uiso 1 1 calc R U . . .
H9'B H -0.123724 0.000495 0.422244 0.140 Uiso 1 1 calc R U . . .
H9'C H -0.267290 0.024608 0.468197 0.140 Uiso 1 1 calc R U . . .
C10 C 0.1895(4) 0.33173(13) 0.3073(3) 0.0482(7) Uani 1 1 d . . . . .
H10C H 0.270736 0.322059 0.261147 0.058 Uiso 1 1 calc R U . . .
H10D H 0.149097 0.363856 0.277901 0.058 Uiso 1 1 calc R U . . .
C11 C 0.0766(3) 0.29009(12) 0.29994(19) 0.0408(6) Uani 1 1 d . . . . .
H11C H -0.016635 0.304582 0.320065 0.049 Uiso 1 1 calc R U . . .
H11D H 0.068952 0.277879 0.223662 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1106(3) 0.24559(11) 0.3738(2) 0.0365(5) Uani 1 1 d . . . . .
C13 C 0.1022(3) 0.25077(10) 0.4872(2) 0.0321(5) Uani 1 1 d . . . . .
C14 C 0.1400(3) 0.20979(10) 0.5561(2) 0.0338(5) Uani 1 1 d . . . . .
H14 H 0.134260 0.212686 0.633190 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1855(3) 0.16525(11) 0.5076(2) 0.0407(6) Uani 1 1 d . . . . .
C16 C 0.1946(3) 0.16065(12) 0.3962(3) 0.0438(6) Uani 1 1 d . . . . .
C17 C 0.1566(3) 0.19944(12) 0.3272(2) 0.0437(6) Uani 1 1 d . . . . .
H17 H 0.161096 0.195394 0.250339 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2651(5) 0.08722(14) 0.4703(4) 0.0666(10) Uani 1 1 d . . . . .
H18C H 0.365877 0.076687 0.478301 0.080 Uiso 1 1 calc R U . . .
H18D H 0.205108 0.056223 0.472247 0.080 Uiso 1 1 calc R U . . .
C19 C -0.2420(4) 0.43648(12) 0.4242(3) 0.0518(7) Uani 1 1 d . . . . .
H19D H -0.193945 0.459089 0.476629 0.078 Uiso 1 1 calc R U . . .
H19E H -0.340273 0.447967 0.412657 0.078 Uiso 1 1 calc R U . . .
H19F H -0.191757 0.437287 0.354734 0.078 Uiso 1 1 calc R U . . .
N9 N 0.2423(3) 0.34081(9) 0.4206(2) 0.0415(5) Uani 1 1 d D . . . .
H9 H 0.294(4) 0.3147(11) 0.435(3) 0.050 Uiso 1 1 d D U . . .
O1 O -0.2421(2) 0.38548(8) 0.46593(18) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.2280(3) 0.12071(9) 0.5582(2) 0.0568(6) Uani 1 1 d . . . . .
O3 O 0.2442(3) 0.11287(9) 0.3699(2) 0.0642(7) Uani 1 1 d . . . . .
O4 O -0.18276(19) 0.27880(7) 0.44885(13) 0.0309(3) Uani 1 1 d . . . . .
O5 O -0.1892(2) 0.21756(8) 0.57668(14) 0.0368(4) Uani 1 1 d . . . . .
O6 O -0.2450(2) 0.21662(8) 0.28867(13) 0.0372(4) Uani 1 1 d . . . . .
H6 H -0.287273 0.244425 0.278035 0.056 Uiso 1 1 calc R U . . .
O7 O -0.4818(2) 0.17589(8) 0.50641(17) 0.0420(4) Uani 1 1 d . . . . .
H7 H -0.532323 0.196010 0.542499 0.063 Uiso 1 1 calc R U . . .
O8 O -0.4749(2) 0.28033(9) 0.31980(17) 0.0478(5) Uani 1 1 d . . . . .
O9 O -0.5667(2) 0.26862(9) 0.48626(18) 0.0450(5) Uani 1 1 d . . . . .
C1A C 0.5738(3) 0.11311(11) 0.9791(2) 0.0397(6) Uani 1 1 d . . . . .
H1A H 0.556122 0.079590 0.952859 0.048 Uiso 1 1 calc R U . . .
C1B C 0.8006(3) 0.26716(10) 0.9836(2) 0.0323(5) Uani 1 1 d . . . . .
C2A C 0.7028(3) 0.13379(10) 0.9896(2) 0.0364(5) Uani 1 1 d . . . . .
C2B C 0.8633(3) 0.30017(10) 0.89291(19) 0.0344(5) Uani 1 1 d . . . . .
C3A C 0.7013(3) 0.18772(10) 1.02968(19) 0.0323(5) Uani 1 1 d . . . . .
H3A H 0.752356 0.190108 1.101612 0.039 Uiso 1 1 calc R U . . .
C3B C 1.0274(3) 0.29923(12) 0.9074(2) 0.0381(5) Uani 1 1 d . . . . .
H3B H 1.069506 0.318536 0.845340 0.046 Uiso 1 1 calc R U . . .
C4A C 0.5408(3) 0.19972(10) 1.04412(18) 0.0307(5) Uani 1 1 d . . . . .
H4A H 0.527393 0.204759 1.124171 0.037 Uiso 1 1 calc R U . . .
C4B C 1.0856(3) 0.24414(12) 0.9041(2) 0.0402(6) Uani 1 1 d . . . . .
C5A C 0.4604(3) 0.14941(10) 1.0141(2) 0.0353(5) Uani 1 1 d . . . . .
C5B C 0.8024(3) 0.35388(11) 0.9015(2) 0.0408(6) Uani 1 1 d . . . . .
H5BA H 0.816104 0.366061 0.977320 0.049 Uiso 1 1 calc R U . . .
H5BB H 0.698707 0.352327 0.886493 0.049 Uiso 1 1 calc R U . . .
C6A C 0.3683(4) 0.12981(13) 1.1073(3) 0.0473(7) Uani 1 1 d . . . . .
H6AA H 0.426461 0.110169 1.160586 0.057 Uiso 1 1 calc R U . . .
H6AB H 0.322371 0.158508 1.145642 0.057 Uiso 1 1 calc R U . . .
C6B C 0.8681(5) 0.39269(14) 0.8242(3) 0.0606(9) Uani 1 1 d D . . . .
H6BA H 0.966966 0.399322 0.849338 0.073 Uiso 0.715(7) 1 calc R U P A 1
H6BB H 0.873194 0.377008 0.750940 0.073 Uiso 0.715(7) 1 calc R U P A 1
H6BC H 0.970653 0.396792 0.841618 0.073 Uiso 0.285(7) 1 calc R U P A 2
H6BD H 0.858360 0.380672 0.747943 0.073 Uiso 0.285(7) 1 calc R U P A 2
C7A C 0.2567(6) 0.0956(2) 1.0522(4) 0.0831(15) Uani 1 1 d . . . . .
H7AA H 0.285941 0.059361 1.056998 0.100 Uiso 1 1 calc R U . . .
H7AB H 0.163632 0.099471 1.088003 0.100 Uiso 1 1 calc R U . . .
C7B C 0.7928(12) 0.4432(4) 0.8131(7) 0.0595(18) Uani 0.715(7) 1 d D . P A 1
H7B H 0.768955 0.454911 0.888244 0.071 Uiso 0.715(7) 1 calc R U P A 1
C7C C 0.792(3) 0.4434(10) 0.837(2) 0.0595(18) Uani 0.285(7) 1 d D . P A 2
H7C H 0.856318 0.464401 0.885010 0.071 Uiso 0.285(7) 1 calc R U P A 2
C8A C 0.2464(4) 0.11207(15) 0.9357(3) 0.0591(8) Uani 1 1 d . . . . .
H8AA H 0.147703 0.122150 0.916581 0.071 Uiso 1 1 calc R U . . .
H8AB H 0.275531 0.084068 0.886668 0.071 Uiso 1 1 calc R U . . .
C8B C 0.6596(9) 0.4376(4) 0.7527(8) 0.104(3) Uani 0.715(7) 1 d D . P A 1
H8BA H 0.679374 0.427681 0.677339 0.156 Uiso 0.715(7) 1 calc R U P A 1
H8BB H 0.608123 0.470098 0.752855 0.156 Uiso 0.715(7) 1 calc R U P A 1
H8BC H 0.601534 0.411271 0.787135 0.156 Uiso 0.715(7) 1 calc R U P A 1
C8C C 0.650(2) 0.4514(9) 0.880(2) 0.104(3) Uani 0.285(7) 1 d D . P A 2
H8CA H 0.587910 0.424254 0.852225 0.156 Uiso 0.285(7) 1 d R U P A 2
H8CB H 0.613430 0.484574 0.856315 0.156 Uiso 0.285(7) 1 d R U P A 2
H8CC H 0.652540 0.450144 0.960285 0.156 Uiso 0.285(7) 1 d R U P A 2
C9B C 0.8890(10) 0.4835(3) 0.7635(7) 0.088(2) Uani 0.715(7) 1 d D . P A 1
H9BA H 0.979284 0.467775 0.742871 0.131 Uiso 0.715(7) 1 calc R U P A 1
H9BB H 0.907219 0.510507 0.817112 0.131 Uiso 0.715(7) 1 calc R U P A 1
H9BC H 0.842373 0.498063 0.698653 0.131 Uiso 0.715(7) 1 calc R U P A 1
C9C C 0.777(3) 0.4733(6) 0.7320(15) 0.088(2) Uani 0.285(7) 1 d D . P A 2
H9CA H 0.768495 0.509743 0.748709 0.131 Uiso 0.285(7) 1 calc R U P A 2
H9CB H 0.692348 0.461870 0.691780 0.131 Uiso 0.285(7) 1 calc R U P A 2
H9CC H 0.861609 0.467747 0.687518 0.131 Uiso 0.285(7) 1 calc R U P A 2
C10A C 0.3930(4) 0.16523(13) 0.8106(2) 0.0455(7) Uani 1 1 d . . . . .
H10A H 0.309544 0.174293 0.764382 0.055 Uiso 1 1 calc R U . . .
H10B H 0.433454 0.133140 0.782013 0.055 Uiso 1 1 calc R U . . .
C11A C 0.5035(4) 0.20721(12) 0.8029(2) 0.0439(6) Uani 1 1 d . . . . .
H11A H 0.597865 0.193165 0.823465 0.053 Uiso 1 1 calc R U . . .
H11B H 0.508110 0.219053 0.726390 0.053 Uiso 1 1 calc R U . . .
C12A C 0.4715(3) 0.25196(11) 0.8753(2) 0.0361(5) Uani 1 1 d . . . . .
C13A C 0.4861(3) 0.24831(10) 0.98927(19) 0.0319(5) Uani 1 1 d . . . . .
C14A C 0.4508(3) 0.28950(11) 1.0564(2) 0.0354(5) Uani 1 1 d . . . . .
H14A H 0.459801 0.287152 1.133477 0.043 Uiso 1 1 calc R U . . .
C15A C 0.4028(3) 0.33335(11) 1.0072(2) 0.0406(6) Uani 1 1 d . . . . .
C16A C 0.3868(3) 0.33670(12) 0.8949(3) 0.0435(6) Uani 1 1 d . . . . .
C17A C 0.4201(3) 0.29773(12) 0.8275(2) 0.0446(6) Uani 1 1 d . . . . .
H17A H 0.409373 0.300959 0.750663 0.054 Uiso 1 1 calc R U . . .
C18A C 0.3184(5) 0.41089(14) 0.9693(4) 0.0680(11) Uani 1 1 d . . . . .
H18A H 0.379197 0.441708 0.969706 0.082 Uiso 1 1 calc R U . . .
H18B H 0.218374 0.421708 0.978403 0.082 Uiso 1 1 calc R U . . .
C19A C 0.8325(5) 0.06204(14) 0.9339(3) 0.0605(9) Uani 1 1 d . . . . .
H19A H 0.790743 0.060967 0.860220 0.091 Uiso 1 1 calc R U . . .
H19B H 0.776701 0.040452 0.982540 0.091 Uiso 1 1 calc R U . . .
H19C H 0.930652 0.049516 0.932015 0.091 Uiso 1 1 calc R U . . .
N9A N 0.3452(3) 0.15668(10) 0.92547(19) 0.0405(5) Uani 1 1 d D . . . .
H9A H 0.292(4) 0.1819(11) 0.944(3) 0.049 Uiso 1 1 d D U . . .
O1A O 0.8317(2) 0.11373(9) 0.97345(19) 0.0479(5) Uani 1 1 d . . . . .
O2A O 0.3330(3) 0.38424(9) 0.8686(2) 0.0596(6) Uani 1 1 d . . . . .
O3A O 0.3599(3) 0.37788(9) 1.0559(2) 0.0560(6) Uani 1 1 d . . . . .
O4A O 0.77078(19) 0.21984(7) 0.95000(14) 0.0334(4) Uani 1 1 d . . . . .
O5A O 0.7833(2) 0.28128(8) 1.07627(14) 0.0398(4) Uani 1 1 d . . . . .
O6A O 0.8260(2) 0.28162(8) 0.78797(14) 0.0400(4) Uani 1 1 d . . . . .
H6A H 0.883055 0.258531 0.770175 0.060 Uiso 1 1 calc R U . . .
O7A O 1.0706(2) 0.32326(9) 1.00528(17) 0.0452(5) Uani 1 1 d . . . . .
H7A H 1.112037 0.301984 1.045924 0.068 Uiso 1 1 calc R U . . .
O8A O 1.0604(2) 0.21875(9) 0.82005(17) 0.0486(5) Uani 1 1 d . . . . .
O9A O 1.1546(2) 0.23019(9) 0.98716(17) 0.0460(5) Uani 1 1 d . . . . .
O1W O -0.0979(4) 0.13719(11) 0.7178(2) 0.0725(8) Uani 1 1 d G . . . .
H1WA H -0.104868 0.165396 0.680815 0.109 Uiso 1 1 d G U . . .
H1WB H -0.054081 0.145883 0.777973 0.109 Uiso 1 1 d G U . . .
O2W O 0.6223(4) 0.10210(12) 0.6563(3) 0.0785(9) Uani 1 1 d . . . . .
H2WA H 0.583136 0.128696 0.625993 0.118 Uiso 1 1 d R U . . .
H2WB H 0.700346 0.116136 0.680703 0.118 Uiso 1 1 d R U . . .
O3W O 0.6968(4) 0.36195(11) 1.2157(2) 0.0750(9) Uani 1 1 d G . . . .
H3WA H 0.703370 0.344339 1.155799 0.112 Uiso 1 1 d G U . . .
H3WB H 0.673290 0.339687 1.264859 0.112 Uiso 1 1 d G U . . .
O4W O 0.9718(5) 0.39956(14) 1.1451(3) 0.0874(10) Uani 1 1 d G . . . .
H4WA H 0.977054 0.369057 1.090002 0.131 Uiso 1 1 d G U . . .
H4WB H 1.010197 0.427018 1.118604 0.131 Uiso 1 1 d G 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
C1 C2 1.343(4) . ?
C1 C5 1.501(4) . ?
C1 H1 0.9500 . ?
C1' O5 1.212(3) . ?
C1' O4 1.330(3) . ?
C1' C2' 1.546(3) . ?
C2 O1 1.341(3) . ?
C2 C3 1.499(4) . ?
C2' O6 1.416(3) . ?
C2' C5' 1.519(4) . ?
C2' C3' 1.551(4) . ?
C3 O4 1.455(3) . ?
C3 C4 1.548(4) . ?
C3 H3 1.0000 . ?
C3' O7 1.419(3) . ?
C3' C4' 1.541(4) . ?
C3' H3' 1.0000 . ?
C4 C13 1.518(4) . ?
C4 C5 1.561(4) . ?
C4 H4 1.0000 . ?
C4' O8 1.254(4) . ?
C4' O9 1.256(4) . ?
C5 N9 1.534(4) . ?
C5 C6 1.537(4) . ?
C5' C6' 1.514(4) . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C6 C7 1.501(6) . ?
C6 H6B 0.9900 . ?
C6 H6C 0.9900 . ?
C6' C7' 1.529(5) . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C7 C8 1.506(7) . ?
C7 H7D 0.9900 . ?
C7 H7E 0.9900 . ?
C7' C9' 1.506(7) . ?
C7' C8' 1.537(6) . ?
C7' H7' 1.0000 . ?
C8 N9 1.511(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8' H8'A 0.9800 . ?
C8' H8'B 0.9800 . ?
C8' H8'C 0.9800 . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10 N9 1.488(4) . ?
C10 C11 1.525(5) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C11 C12 1.508(4) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C12 C13 1.400(3) . ?
C12 C17 1.409(4) . ?
C13 C14 1.409(4) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(4) . ?
C15 O2 1.378(4) . ?
C16 C17 1.367(5) . ?
C16 O3 1.377(4) . ?
C17 H17 0.9500 . ?
C18 O3 1.414(6) . ?
C18 O2 1.436(5) . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C19 O1 1.432(4) . ?
C19 H19D 0.9800 . ?
C19 H19E 0.9800 . ?
C19 H19F 0.9800 . ?
N9 H9 0.857(14) . ?
O6 H6 0.8400 . ?
O7 H7 0.8400 . ?
C1A C2A 1.333(4) . ?
C1A C5A 1.497(4) . ?
C1A H1A 0.9500 . ?
C1B O5A 1.208(3) . ?
C1B O4A 1.336(3) . ?
C1B C2B 1.533(3) . ?
C2A O1A 1.338(3) . ?
C2A C3A 1.497(4) . ?
C2B O6A 1.415(3) . ?
C2B C5B 1.524(4) . ?
C2B C3B 1.551(4) . ?
C3A O4A 1.452(3) . ?
C3A C4A 1.553(4) . ?
C3A H3A 1.0000 . ?
C3B O7A 1.410(3) . ?
C3B C4B 1.546(4) . ?
C3B H3B 1.0000 . ?
C4A C13A 1.527(4) . ?
C4A C5A 1.562(4) . ?
C4A H4A 1.0000 . ?
C4B O8A 1.246(4) . ?
C4B O9A 1.254(4) . ?
C5A C6A 1.532(4) . ?
C5A N9A 1.535(4) . ?
C5B C6B 1.527(4) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6A C7A 1.531(6) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6B C7B 1.507(8) . ?
C6B C7C 1.52(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C6B H6BC 0.9900 . ?
C6B H6BD 0.9900 . ?
C7A C8A 1.494(6) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7B C8B 1.453(14) . ?
C7B C9B 1.522(12) . ?
C7B H7B 1.0000 . ?
C7C C8C 1.46(2) . ?
C7C C9C 1.51(2) . ?
C7C H7C 1.0000 . ?
C8A N9A 1.500(4) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C8C H8CA 0.9801 . ?
C8C H8CB 0.9802 . ?
C8C H8CC 0.9801 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C9C H9CA 0.9800 . ?
C9C H9CB 0.9800 . ?
C9C H9CC 0.9800 . ?
C10A N9A 1.501(4) . ?
C10A C11A 1.518(5) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.504(4) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.405(3) . ?
C12A C17A 1.418(4) . ?
C13A C14A 1.400(4) . ?
C14A C15A 1.372(4) . ?
C14A H14A 0.9500 . ?
C15A O3A 1.375(4) . ?
C15A C16A 1.385(4) . ?
C16A C17A 1.354(5) . ?
C16A O2A 1.382(4) . ?
C17A H17A 0.9500 . ?
C18A O3A 1.420(5) . ?
C18A O2A 1.427(5) . ?
C18A H18A 0.9900 . ?
C18A H18B 0.9900 . ?
C19A O1A 1.440(4) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
N9A H9A 0.859(14) . ?
O6A H6A 0.8400 . ?
O7A H7A 0.8400 . ?
O1W H1WA 0.8694 . ?
O1W H1WB 0.8701 . ?
O2W H2WA 0.8695 . ?
O2W H2WB 0.8700 . ?
O3W H3WA 0.8702 . ?
O3W H3WB 0.8700 . ?
O4W H4WA 1.0486 . ?
O4W H4WB 0.8703 . ?

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 C5 110.9(2) . . ?
C2 C1 H1 124.5 . . ?
C5 C1 H1 124.5 . . ?
O5 C1' O4 124.0(2) . . ?
O5 C1' C2' 123.5(2) . . ?
O4 C1' C2' 112.4(2) . . ?
O1 C2 C1 130.3(3) . . ?
O1 C2 C3 116.4(2) . . ?
C1 C2 C3 113.3(2) . . ?
O6 C2' C5' 107.5(2) . . ?
O6 C2' C1' 111.1(2) . . ?
C5' C2' C1' 109.1(2) . . ?
O6 C2' C3' 108.5(2) . . ?
C5' C2' C3' 113.3(2) . . ?
C1' C2' C3' 107.3(2) . . ?
O4 C3 C2 108.20(19) . . ?
O4 C3 C4 113.88(19) . . ?
C2 C3 C4 104.7(2) . . ?
O4 C3 H3 110.0 . . ?
C2 C3 H3 110.0 . . ?
C4 C3 H3 110.0 . . ?
O7 C3' C4' 109.8(2) . . ?
O7 C3' C2' 111.1(2) . . ?
C4' C3' C2' 112.1(2) . . ?
O7 C3' H3' 107.9 . . ?
C4' C3' H3' 107.9 . . ?
C2' C3' H3' 107.9 . . ?
C13 C4 C3 116.0(2) . . ?
C13 C4 C5 115.9(2) . . ?
C3 C4 C5 105.4(2) . . ?
C13 C4 H4 106.3 . . ?
C3 C4 H4 106.3 . . ?
C5 C4 H4 106.3 . . ?
O8 C4' O9 127.2(3) . . ?
O8 C4' C3' 117.3(2) . . ?
O9 C4' C3' 115.5(2) . . ?
C1 C5 N9 111.6(2) . . ?
C1 C5 C6 113.6(2) . . ?
N9 C5 C6 100.1(2) . . ?
C1 C5 C4 105.5(2) . . ?
N9 C5 C4 113.2(2) . . ?
C6 C5 C4 113.1(2) . . ?
C6' C5' C2' 113.8(2) . . ?
C6' C5' H5'A 108.8 . . ?
C2' C5' H5'A 108.8 . . ?
C6' C5' H5'B 108.8 . . ?
C2' C5' H5'B 108.8 . . ?
H5'A C5' H5'B 107.7 . . ?
C7 C6 C5 108.3(3) . . ?
C7 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
C7 C6 H6C 110.0 . . ?
C5 C6 H6C 110.0 . . ?
H6B C6 H6C 108.4 . . ?
C5' C6' C7' 113.9(3) . . ?
C5' C6' H6'A 108.8 . . ?
C7' C6' H6'A 108.8 . . ?
C5' C6' H6'B 108.8 . . ?
C7' C6' H6'B 108.8 . . ?
H6'A C6' H6'B 107.7 . . ?
C6 C7 C8 106.8(3) . . ?
C6 C7 H7D 110.4 . . ?
C8 C7 H7D 110.4 . . ?
C6 C7 H7E 110.4 . . ?
C8 C7 H7E 110.4 . . ?
H7D C7 H7E 108.6 . . ?
C9' C7' C6' 112.7(3) . . ?
C9' C7' C8' 111.7(4) . . ?
C6' C7' C8' 109.7(4) . . ?
C9' C7' H7' 107.5 . . ?
C6' C7' H7' 107.5 . . ?
C8' C7' H7' 107.5 . . ?
C7 C8 N9 104.1(3) . . ?
C7 C8 H8A 110.9 . . ?
N9 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
N9 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C7' C8' H8'A 109.5 . . ?
C7' C8' H8'B 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
C7' C8' H8'C 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
C7' C9' H9'A 109.5 . . ?
C7' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
C7' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
N9 C10 C11 113.1(2) . . ?
N9 C10 H10C 109.0 . . ?
C11 C10 H10C 109.0 . . ?
N9 C10 H10D 109.0 . . ?
C11 C10 H10D 109.0 . . ?
H10C C10 H10D 107.8 . . ?
C12 C11 C10 112.2(2) . . ?
C12 C11 H11C 109.2 . . ?
C10 C11 H11C 109.2 . . ?
C12 C11 H11D 109.2 . . ?
C10 C11 H11D 109.2 . . ?
H11C C11 H11D 107.9 . . ?
C13 C12 C17 120.5(3) . . ?
C13 C12 C11 120.4(2) . . ?
C17 C12 C11 119.0(2) . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 C4 122.5(2) . . ?
C14 C13 C4 117.2(2) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C16 C15 O2 110.5(3) . . ?
C16 C15 C14 121.7(3) . . ?
O2 C15 C14 127.8(3) . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 O3 128.2(3) . . ?
C15 C16 O3 109.8(3) . . ?
C16 C17 C12 117.9(3) . . ?
C16 C17 H17 121.1 . . ?
C12 C17 H17 121.1 . . ?
O3 C18 O2 109.2(3) . . ?
O3 C18 H18C 109.8 . . ?
O2 C18 H18C 109.8 . . ?
O3 C18 H18D 109.8 . . ?
O2 C18 H18D 109.8 . . ?
H18C C18 H18D 108.3 . . ?
O1 C19 H19D 109.5 . . ?
O1 C19 H19E 109.5 . . ?
H19D C19 H19E 109.5 . . ?
O1 C19 H19F 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
C10 N9 C8 113.6(3) . . ?
C10 N9 C5 117.4(2) . . ?
C8 N9 C5 105.6(2) . . ?
C10 N9 H9 104(3) . . ?
C8 N9 H9 104(3) . . ?
C5 N9 H9 112(3) . . ?
C2 O1 C19 115.0(3) . . ?
C15 O2 C18 104.7(3) . . ?
C16 O3 C18 105.8(3) . . ?
C1' O4 C3 115.50(18) . . ?
C2' O6 H6 109.5 . . ?
C3' O7 H7 109.5 . . ?
C2A C1A C5A 111.4(3) . . ?
C2A C1A H1A 124.3 . . ?
C5A C1A H1A 124.3 . . ?
O5A C1B O4A 123.0(2) . . ?
O5A C1B C2B 124.5(2) . . ?
O4A C1B C2B 112.5(2) . . ?
C1A C2A O1A 130.6(3) . . ?
C1A C2A C3A 113.7(2) . . ?
O1A C2A C3A 115.7(3) . . ?
O6A C2B C5B 107.0(2) . . ?
O6A C2B C1B 111.9(2) . . ?
C5B C2B C1B 108.9(2) . . ?
O6A C2B C3B 109.4(2) . . ?
C5B C2B C3B 112.4(2) . . ?
C1B C2B C3B 107.5(2) . . ?
O4A C3A C2A 108.68(19) . . ?
O4A C3A C4A 114.0(2) . . ?
C2A C3A C4A 104.1(2) . . ?
O4A C3A H3A 110.0 . . ?
C2A C3A H3A 110.0 . . ?
C4A C3A H3A 110.0 . . ?
O7A C3B C4B 110.0(2) . . ?
O7A C3B C2B 111.3(2) . . ?
C4B C3B C2B 111.3(2) . . ?
O7A C3B H3B 108.0 . . ?
C4B C3B H3B 108.0 . . ?
C2B C3B H3B 108.0 . . ?
C13A C4A C3A 116.1(2) . . ?
C13A C4A C5A 116.3(2) . . ?
C3A C4A C5A 105.6(2) . . ?
C13A C4A H4A 106.0 . . ?
C3A C4A H4A 106.0 . . ?
C5A C4A H4A 106.0 . . ?
O8A C4B O9A 127.3(3) . . ?
O8A C4B C3B 117.2(3) . . ?
O9A C4B C3B 115.5(2) . . ?
C1A C5A C6A 114.4(2) . . ?
C1A C5A N9A 112.0(2) . . ?
C6A C5A N9A 99.7(2) . . ?
C1A C5A C4A 105.1(2) . . ?
C6A C5A C4A 112.6(2) . . ?
N9A C5A C4A 113.3(2) . . ?
C2B C5B C6B 114.7(3) . . ?
C2B C5B H5BA 108.6 . . ?
C6B C5B H5BA 108.6 . . ?
C2B C5B H5BB 108.6 . . ?
C6B C5B H5BB 108.6 . . ?
H5BA C5B H5BB 107.6 . . ?
C7A C6A C5A 105.0(3) . . ?
C7A C6A H6AA 110.7 . . ?
C5A C6A H6AA 110.7 . . ?
C7A C6A H6AB 110.7 . . ?
C5A C6A H6AB 110.7 . . ?
H6AA C6A H6AB 108.8 . . ?
C7B C6B C5B 116.6(4) . . ?
C7C C6B C5B 108.8(9) . . ?
C7B C6B H6BA 108.1 . . ?
C5B C6B H6BA 108.1 . . ?
C7B C6B H6BB 108.1 . . ?
C5B C6B H6BB 108.1 . . ?
H6BA C6B H6BB 107.3 . . ?
C7C C6B H6BC 109.9 . . ?
C5B C6B H6BC 109.9 . . ?
C7C C6B H6BD 109.9 . . ?
C5B C6B H6BD 109.9 . . ?
H6BC C6B H6BD 108.3 . . ?
C8A C7A C6A 106.6(3) . . ?
C8A C7A H7AA 110.4 . . ?
C6A C7A H7AA 110.4 . . ?
C8A C7A H7AB 110.4 . . ?
C6A C7A H7AB 110.4 . . ?
H7AA C7A H7AB 108.6 . . ?
C8B C7B C6B 111.0(8) . . ?
C8B C7B C9B 112.3(7) . . ?
C6B C7B C9B 111.4(7) . . ?
C8B C7B H7B 107.3 . . ?
C6B C7B H7B 107.3 . . ?
C9B C7B H7B 107.3 . . ?
C8C C7C C9C 99.4(18) . . ?
C8C C7C C6B 127(2) . . ?
C9C C7C C6B 113.6(18) . . ?
C8C C7C H7C 105.1 . . ?
C9C C7C H7C 105.1 . . ?
C6B C7C H7C 105.1 . . ?
C7A C8A N9A 105.9(3) . . ?
C7A C8A H8AA 110.5 . . ?
N9A C8A H8AA 110.6 . . ?
C7A C8A H8AB 110.6 . . ?
N9A C8A H8AB 110.6 . . ?
H8AA C8A H8AB 108.7 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
C7B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C7C C8C H8CA 108.3 . . ?
C7C C8C H8CB 109.7 . . ?
H8CA C8C H8CB 109.5 . . ?
C7C C8C H8CC 110.4 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
C7B C9B H9BA 109.5 . . ?
C7B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C7B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C7C C9C H9CA 109.5 . . ?
C7C C9C H9CB 109.5 . . ?
H9CA C9C H9CB 109.5 . . ?
C7C C9C H9CC 109.5 . . ?
H9CA C9C H9CC 109.5 . . ?
H9CB C9C H9CC 109.5 . . ?
N9A C10A C11A 112.4(2) . . ?
N9A C10A H10A 109.1 . . ?
C11A C10A H10A 109.1 . . ?
N9A C10A H10B 109.1 . . ?
C11A C10A H10B 109.1 . . ?
H10A C10A H10B 107.9 . . ?
C12A C11A C10A 112.7(2) . . ?
C12A C11A H11A 109.0 . . ?
C10A C11A H11A 109.0 . . ?
C12A C11A H11B 109.0 . . ?
C10A C11A H11B 109.0 . . ?
H11A C11A H11B 107.8 . . ?
C13A C12A C17A 119.7(2) . . ?
C13A C12A C11A 121.1(2) . . ?
C17A C12A C11A 119.1(2) . . ?
C14A C13A C12A 120.7(2) . . ?
C14A C13A C4A 117.8(2) . . ?
C12A C13A C4A 121.5(2) . . ?
C15A C14A C13A 117.9(2) . . ?
C15A C14A H14A 121.1 . . ?
C13A C14A H14A 121.1 . . ?
C14A C15A O3A 128.1(3) . . ?
C14A C15A C16A 121.4(3) . . ?
O3A C15A C16A 110.5(3) . . ?
C17A C16A O2A 128.7(3) . . ?
C17A C16A C15A 122.4(3) . . ?
O2A C16A C15A 108.9(3) . . ?
C16A C17A C12A 117.9(3) . . ?
C16A C17A H17A 121.1 . . ?
C12A C17A H17A 121.1 . . ?
O3A C18A O2A 108.6(3) . . ?
O3A C18A H18A 110.0 . . ?
O2A C18A H18A 110.0 . . ?
O3A C18A H18B 110.0 . . ?
O2A C18A H18B 110.0 . . ?
H18A C18A H18B 108.3 . . ?
O1A C19A H19A 109.5 . . ?
O1A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
O1A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C8A N9A C10A 112.9(3) . . ?
C8A N9A C5A 106.0(2) . . ?
C10A N9A C5A 117.7(2) . . ?
C8A N9A H9A 102(3) . . ?
C10A N9A H9A 108(3) . . ?
C5A N9A H9A 108(3) . . ?
C2A O1A C19A 115.4(3) . . ?
C16A O2A C18A 106.2(3) . . ?
C15A O3A C18A 105.8(3) . . ?
C1B O4A C3A 115.21(19) . . ?
C2B O6A H6A 109.5 . . ?
C3B O7A H7A 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 99.0 . . ?
H3WA O3W H3WB 104.5 . . ?
H4WA O4W H4WB 111.5 . . ?

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
C5 C1 C2 O1 175.7(2) . . . . ?
C5 C1 C2 C3 -1.6(3) . . . . ?
O5 C1' C2' O6 -159.2(2) . . . . ?
O4 C1' C2' O6 22.4(3) . . . . ?
O5 C1' C2' C5' -40.9(3) . . . . ?
O4 C1' C2' C5' 140.7(2) . . . . ?
O5 C1' C2' C3' 82.3(3) . . . . ?
O4 C1' C2' C3' -96.1(2) . . . . ?
O1 C2 C3 O4 59.8(3) . . . . ?
C1 C2 C3 O4 -122.5(2) . . . . ?
O1 C2 C3 C4 -178.4(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
O6 C2' C3' O7 173.1(2) . . . . ?
C5' C2' C3' O7 53.7(3) . . . . ?
C1' C2' C3' O7 -66.8(3) . . . . ?
O6 C2' C3' C4' -63.7(3) . . . . ?
C5' C2' C3' C4' 177.0(2) . . . . ?
C1' C2' C3' C4' 56.5(3) . . . . ?
O4 C3 C4 C13 -9.1(3) . . . . ?
C2 C3 C4 C13 -127.0(2) . . . . ?
O4 C3 C4 C5 120.6(2) . . . . ?
C2 C3 C4 C5 2.6(2) . . . . ?
O7 C3' C4' O8 -178.2(2) . . . . ?
C2' C3' C4' O8 57.8(3) . . . . ?
O7 C3' C4' O9 1.4(3) . . . . ?
C2' C3' C4' O9 -122.6(3) . . . . ?
C2 C1 C5 N9 126.5(2) . . . . ?
C2 C1 C5 C6 -121.2(3) . . . . ?
C2 C1 C5 C4 3.2(3) . . . . ?
C13 C4 C5 C1 126.3(2) . . . . ?
C3 C4 C5 C1 -3.5(3) . . . . ?
C13 C4 C5 N9 4.0(3) . . . . ?
C3 C4 C5 N9 -125.8(2) . . . . ?
C13 C4 C5 C6 -109.0(3) . . . . ?
C3 C4 C5 C6 121.3(3) . . . . ?
O6 C2' C5' C6' -67.1(3) . . . . ?
C1' C2' C5' C6' 172.3(2) . . . . ?
C3' C2' C5' C6' 52.8(3) . . . . ?
C1 C5 C6 C7 -92.3(4) . . . . ?
N9 C5 C6 C7 26.8(4) . . . . ?
C4 C5 C6 C7 147.5(3) . . . . ?
C2' C5' C6' C7' 168.8(3) . . . . ?
C5 C6 C7 C8 -5.9(5) . . . . ?
C5' C6' C7' C9' 52.6(5) . . . . ?
C5' C6' C7' C8' 177.7(3) . . . . ?
C6 C7 C8 N9 -18.2(5) . . . . ?
N9 C10 C11 C12 -40.3(3) . . . . ?
C10 C11 C12 C13 70.3(3) . . . . ?
C10 C11 C12 C17 -107.2(3) . . . . ?
C17 C12 C13 C14 0.1(4) . . . . ?
C11 C12 C13 C14 -177.3(3) . . . . ?
C17 C12 C13 C4 -179.0(3) . . . . ?
C11 C12 C13 C4 3.6(4) . . . . ?
C3 C4 C13 C12 69.8(3) . . . . ?
C5 C4 C13 C12 -54.6(3) . . . . ?
C3 C4 C13 C14 -109.3(3) . . . . ?
C5 C4 C13 C14 126.3(2) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C4 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C13 C14 C15 O2 179.7(3) . . . . ?
O2 C15 C16 C17 179.1(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
O2 C15 C16 O3 -0.4(4) . . . . ?
C14 C15 C16 O3 179.3(3) . . . . ?
C15 C16 C17 C12 1.6(5) . . . . ?
O3 C16 C17 C12 -179.0(3) . . . . ?
C13 C12 C17 C16 -1.1(4) . . . . ?
C11 C12 C17 C16 176.3(3) . . . . ?
C11 C10 N9 C8 -174.5(3) . . . . ?
C11 C10 N9 C5 -50.7(3) . . . . ?
C7 C8 N9 C10 165.9(3) . . . . ?
C7 C8 N9 C5 35.9(4) . . . . ?
C1 C5 N9 C10 -45.4(3) . . . . ?
C6 C5 N9 C10 -165.9(3) . . . . ?
C4 C5 N9 C10 73.4(3) . . . . ?
C1 C5 N9 C8 82.3(3) . . . . ?
C6 C5 N9 C8 -38.2(3) . . . . ?
C4 C5 N9 C8 -158.8(2) . . . . ?
C1 C2 O1 C19 2.9(4) . . . . ?
C3 C2 O1 C19 -179.9(2) . . . . ?
C16 C15 O2 C18 0.1(4) . . . . ?
C14 C15 O2 C18 -179.5(3) . . . . ?
O3 C18 O2 C15 0.2(4) . . . . ?
C17 C16 O3 C18 -179.0(4) . . . . ?
C15 C16 O3 C18 0.5(4) . . . . ?
O2 C18 O3 C16 -0.4(4) . . . . ?
O5 C1' O4 C3 6.4(3) . . . . ?
C2' C1' O4 C3 -175.24(19) . . . . ?
C2 C3 O4 C1' -168.7(2) . . . . ?
C4 C3 O4 C1' 75.3(2) . . . . ?
C5A C1A C2A O1A 175.8(3) . . . . ?
C5A C1A C2A C3A -1.7(3) . . . . ?
O5A C1B C2B O6A -159.1(3) . . . . ?
O4A C1B C2B O6A 22.9(3) . . . . ?
O5A C1B C2B C5B -41.1(4) . . . . ?
O4A C1B C2B C5B 140.9(2) . . . . ?
O5A C1B C2B C3B 80.8(3) . . . . ?
O4A C1B C2B C3B -97.2(3) . . . . ?
C1A C2A C3A O4A -122.1(2) . . . . ?
O1A C2A C3A O4A 60.0(3) . . . . ?
C1A C2A C3A C4A -0.3(3) . . . . ?
O1A C2A C3A C4A -178.2(2) . . . . ?
O6A C2B C3B O7A 172.6(2) . . . . ?
C5B C2B C3B O7A 54.0(3) . . . . ?
C1B C2B C3B O7A -65.7(3) . . . . ?
O6A C2B C3B C4B -64.2(3) . . . . ?
C5B C2B C3B C4B 177.2(2) . . . . ?
C1B C2B C3B C4B 57.4(3) . . . . ?
O4A C3A C4A C13A -10.2(3) . . . . ?
C2A C3A C4A C13A -128.5(2) . . . . ?
O4A C3A C4A C5A 120.2(2) . . . . ?
C2A C3A C4A C5A 2.0(2) . . . . ?
O7A C3B C4B O8A -177.4(2) . . . . ?
C2B C3B C4B O8A 58.7(3) . . . . ?
O7A C3B C4B O9A 2.1(3) . . . . ?
C2B C3B C4B O9A -121.8(3) . . . . ?
C2A C1A C5A C6A -121.1(3) . . . . ?
C2A C1A C5A N9A 126.4(2) . . . . ?
C2A C1A C5A C4A 2.9(3) . . . . ?
C13A C4A C5A C1A 127.5(2) . . . . ?
C3A C4A C5A C1A -2.9(2) . . . . ?
C13A C4A C5A C6A -107.4(3) . . . . ?
C3A C4A C5A C6A 122.2(2) . . . . ?
C13A C4A C5A N9A 4.8(3) . . . . ?
C3A C4A C5A N9A -125.6(2) . . . . ?
O6A C2B C5B C6B -65.6(3) . . . . ?
C1B C2B C5B C6B 173.4(3) . . . . ?
C3B C2B C5B C6B 54.4(3) . . . . ?
C1A C5A C6A C7A -82.2(4) . . . . ?
N9A C5A C6A C7A 37.5(4) . . . . ?
C4A C5A C6A C7A 157.9(3) . . . . ?
C2B C5B C6B C7B 168.1(6) . . . . ?
C2B C5B C6B C7C 176.9(16) . . . . ?
C5A C6A C7A C8A -22.6(5) . . . . ?
C5B C6B C7B C8B -71.4(7) . . . . ?
C5B C6B C7B C9B 162.6(6) . . . . ?
C5B C6B C7C C8C -22(4) . . . . ?
C5B C6B C7C C9C -145(2) . . . . ?
C6A C7A C8A N9A -2.7(5) . . . . ?
N9A C10A C11A C12A -40.4(3) . . . . ?
C10A C11A C12A C13A 71.3(3) . . . . ?
C10A C11A C12A C17A -106.0(3) . . . . ?
C17A C12A C13A C14A -0.2(4) . . . . ?
C11A C12A C13A C14A -177.5(3) . . . . ?
C17A C12A C13A C4A 179.9(3) . . . . ?
C11A C12A C13A C4A 2.7(4) . . . . ?
C3A C4A C13A C14A -108.8(3) . . . . ?
C5A C4A C13A C14A 125.9(2) . . . . ?
C3A C4A C13A C12A 71.0(3) . . . . ?
C5A C4A C13A C12A -54.2(3) . . . . ?
C12A C13A C14A C15A -0.4(4) . . . . ?
C4A C13A C14A C15A 179.4(2) . . . . ?
C13A C14A C15A O3A 178.7(3) . . . . ?
C13A C14A C15A C16A 1.3(4) . . . . ?
C14A C15A C16A C17A -1.5(5) . . . . ?
O3A C15A C16A C17A -179.3(3) . . . . ?
C14A C15A C16A O2A 178.1(3) . . . . ?
O3A C15A C16A O2A 0.2(4) . . . . ?
O2A C16A C17A C12A -178.7(3) . . . . ?
C15A C16A C17A C12A 0.7(5) . . . . ?
C13A C12A C17A C16A 0.1(4) . . . . ?
C11A C12A C17A C16A 177.4(3) . . . . ?
C7A C8A N9A C10A 157.3(4) . . . . ?
C7A C8A N9A C5A 27.1(4) . . . . ?
C11A C10A N9A C8A -174.6(3) . . . . ?
C11A C10A N9A C5A -50.6(3) . . . . ?
C1A C5A N9A C8A 81.5(3) . . . . ?
C6A C5A N9A C8A -39.8(3) . . . . ?
C4A C5A N9A C8A -159.8(2) . . . . ?
C1A C5A N9A C10A -45.8(3) . . . . ?
C6A C5A N9A C10A -167.2(3) . . . . ?
C4A C5A N9A C10A 72.9(3) . . . . ?
C1A C2A O1A C19A 3.0(4) . . . . ?
C3A C2A O1A C19A -179.4(3) . . . . ?
C17A C16A O2A C18A -179.4(4) . . . . ?
C15A C16A O2A C18A 1.0(4) . . . . ?
O3A C18A O2A C16A -1.9(4) . . . . ?
C14A C15A O3A C18A -179.1(3) . . . . ?
C16A C15A O3A C18A -1.4(4) . . . . ?
O2A C18A O3A C15A 2.0(5) . . . . ?
O5A C1B O4A C3A 6.4(4) . . . . ?
C2B C1B O4A C3A -175.6(2) . . . . ?
C2A C3A O4A C1B -168.2(2) . . . . ?
C4A C3A O4A C1B 76.2(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
_geom_hbond_publ_flag
C11 H11C O4 0.99 2.34 3.081(3) 131.3 . yes
C11A H11A O4A 0.99 2.34 3.089(4) 132.0 . yes
N9 H9 O9 0.857(14) 1.882(17) 2.722(3) 166(4) 1_655 yes
N9A H9A O9A 0.859(14) 1.892(16) 2.745(3) 172(4) 1_455 yes
O1W H1WA O5 0.87 2.02 2.851(3) 158.3 . yes
O1W H1WB O8A 0.87 2.25 2.882(4) 129.5 1_455 yes
O2W H2WA O7 0.87 2.01 2.833(4) 158.3 1_655 yes
O3W H3WA O5A 0.87 2.07 2.846(3) 148.6 . yes
O3W H3WB O8 0.87 2.20 2.979(4) 148.7 1_656 yes
O4W H4WA O7A 1.05 1.82 2.802(4) 153.8 . yes
O6 H6 O8 0.84 2.07 2.763(3) 139.4 . yes
O6A H6A O8A 0.84 2.05 2.776(3) 143.9 . yes
O2W H2WB O1W 0.87 2.02 2.877(5) 167.7 1_655 yes

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.053



