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

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

data_20180628-liweidong-fds
_database_code_depnum_ccdc_archive 'CCDC 2115751'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7090(5)
_cell_length_b                   15.8571(6)
_cell_length_c                   10.2126(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.923(5)
_cell_angle_gamma                90
_cell_volume                     1504.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7641
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.309
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3071
_reflns_number_gt                2325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0427P)²+0.7603P] 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_number_reflns         3071
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O2 O 0.86676(16) 0.41579(8) 0.31754(14) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.89359(16) 0.29399(8) 0.49074(15) 0.0445(4) Uani 1 1 d . . . . .
O4 O 0.44558(17) 0.62010(10) 0.94095(15) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.55913(17) 0.59275(10) 0.77747(16) 0.0363(4) Uani 1 1 d . . . . .
O3 O 0.82802(19) 0.82506(10) 0.5966(2) 0.0682(5) Uani 1 1 d . . . . .
C5 C 0.74841(19) 0.52674(11) 0.58619(18) 0.0310(4) Uani 1 1 d . . . . .
C6 C 0.7083(2) 0.61409(11) 0.61525(17) 0.0305(4) Uani 1 1 d . . . . .
C2 C 0.8433(2) 0.36818(11) 0.5279(2) 0.0341(4) Uani 1 1 d . . . . .
C4 C 0.78371(19) 0.51257(11) 0.46416(18) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.7755 0.5567 0.4023 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8304(2) 0.43466(12) 0.43369(19) 0.0328(4) Uani 1 1 d . . . . .
C17 C 0.8079(2) 0.38202(12) 0.6474(2) 0.0365(5) Uani 1 1 d . . . . .
H17 H 0.8157 0.3377 0.7088 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5259(2) 0.72152(12) 0.65707(19) 0.0344(4) Uani 1 1 d . . . . .
H10 H 0.4666 0.7413 0.5675 0.041 Uiso 1 1 calc R U . . .
C13 C 0.56624(19) 0.62818(11) 0.64703(18) 0.0306(4) Uani 1 1 d . . . . .
H13 H 0.4898 0.6020 0.5737 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7604(2) 0.46072(12) 0.67912(19) 0.0340(4) Uani 1 1 d . . . . .
C11 C 0.4360(2) 0.72000(13) 0.7575(2) 0.0402(5) Uani 1 1 d . . . . .
H11A H 0.4566 0.7689 0.8170 0.048 Uiso 1 1 calc R U . . .
H11B H 0.3340 0.7194 0.7089 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7902(2) 0.67909(12) 0.5993(2) 0.0373(5) Uani 1 1 d . . . . .
H7 H 0.8686 0.6678 0.5672 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4794(2) 0.64029(13) 0.8387(2) 0.0380(5) Uani 1 1 d . . . . .
C18 C 0.8602(3) 0.48306(13) 0.2225(2) 0.0457(5) Uani 1 1 d . . . . .
H18A H 0.8956 0.4636 0.1493 0.069 Uiso 1 1 calc R U . . .
H18B H 0.9184 0.5293 0.2685 0.069 Uiso 1 1 calc R U . . .
H18C H 0.7623 0.5014 0.1860 0.069 Uiso 1 1 calc R U . . .
C8 C 0.7635(2) 0.76680(13) 0.6295(2) 0.0417(5) Uani 1 1 d . . . . .
C14 C 0.5836(2) 0.50343(13) 0.8102(2) 0.0458(5) Uani 1 1 d . . . . .
H14A H 0.5141 0.4706 0.7416 0.055 Uiso 1 1 calc R U . . .
H14B H 0.5669 0.4926 0.8978 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6568(2) 0.77856(12) 0.7085(2) 0.0421(5) Uani 1 1 d . . . . .
H9A H 0.6255 0.8369 0.7012 0.050 Uiso 1 1 calc R U . . .
H9B H 0.7033 0.7666 0.8044 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7333(2) 0.47375(14) 0.8165(2) 0.0459(5) Uani 1 1 d . . . . .
H15A H 0.7515 0.4210 0.8666 0.055 Uiso 1 1 calc R U . . .
H15B H 0.8021 0.5147 0.8681 0.055 Uiso 1 1 calc R U . . .
C1 C 0.9056(3) 0.22327(13) 0.5795(2) 0.0507(6) Uani 1 1 d . . . . .
H1A H 0.9520 0.1777 0.5472 0.076 Uiso 1 1 calc R U . . .
H1B H 0.8113 0.2059 0.5809 0.076 Uiso 1 1 calc R U . . .
H1C H 0.9616 0.2386 0.6704 0.076 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
O2 C3 1.366(2) . ?
O2 C18 1.431(2) . ?
O1 C2 1.369(2) . ?
O1 C1 1.426(2) . ?
O4 C12 1.225(2) . ?
N1 C12 1.357(2) . ?
N1 C14 1.459(3) . ?
N1 C13 1.466(2) . ?
O3 C8 1.217(2) . ?
C5 C16 1.395(3) . ?
C5 C4 1.403(2) . ?
C5 C6 1.492(2) . ?
C6 C7 1.340(3) . ?
C6 C13 1.523(2) . ?
C2 C17 1.378(3) . ?
C2 C3 1.408(3) . ?
C4 C3 1.382(3) . ?
C4 H4 0.9300 . ?
C17 C16 1.401(3) . ?
C17 H17 0.9300 . ?
C10 C9 1.524(3) . ?
C10 C11 1.528(3) . ?
C10 C13 1.542(2) . ?
C10 H10 0.9800 . ?
C13 H13 0.9800 . ?
C16 C15 1.515(3) . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 C8 1.464(3) . ?
C7 H7 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C8 C9 1.498(3) . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C18 117.00(14) . . ?
C2 O1 C1 118.00(16) . . ?
C12 N1 C14 120.74(16) . . ?
C12 N1 C13 112.95(16) . . ?
C14 N1 C13 122.17(15) . . ?
C16 C5 C4 119.37(17) . . ?
C16 C5 C6 122.44(16) . . ?
C4 C5 C6 118.07(16) . . ?
C7 C6 C5 119.46(16) . . ?
C7 C6 C13 121.27(17) . . ?
C5 C6 C13 118.92(15) . . ?
O1 C2 C17 125.68(17) . . ?
O1 C2 C3 114.97(16) . . ?
C17 C2 C3 119.35(17) . . ?
C3 C4 C5 121.59(17) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
O2 C3 C4 125.17(17) . . ?
O2 C3 C2 115.81(16) . . ?
C4 C3 C2 119.02(17) . . ?
C2 C17 C16 122.04(17) . . ?
C2 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C9 C10 C11 111.12(16) . . ?
C9 C10 C13 112.95(16) . . ?
C11 C10 C13 103.60(15) . . ?
C9 C10 H10 109.7 . . ?
C11 C10 H10 109.7 . . ?
C13 C10 H10 109.7 . . ?
N1 C13 C6 115.00(15) . . ?
N1 C13 C10 103.14(14) . . ?
C6 C13 C10 114.74(15) . . ?
N1 C13 H13 107.9 . . ?
C6 C13 H13 107.9 . . ?
C10 C13 H13 107.9 . . ?
C5 C16 C17 118.62(17) . . ?
C5 C16 C15 121.68(17) . . ?
C17 C16 C15 119.56(17) . . ?
C12 C11 C10 105.10(15) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C6 C7 C8 123.87(18) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
O4 C12 N1 125.31(19) . . ?
O4 C12 C11 126.05(18) . . ?
N1 C12 C11 108.61(16) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C8 C7 121.73(19) . . ?
O3 C8 C9 123.10(19) . . ?
C7 C8 C9 115.11(17) . . ?
N1 C14 C15 113.77(17) . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C8 C9 C10 112.26(16) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C14 C15 C16 115.25(17) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C5 C6 C7 128.9(2) . . . . ?
C4 C5 C6 C7 -47.1(2) . . . . ?
C16 C5 C6 C13 -57.9(2) . . . . ?
C4 C5 C6 C13 126.16(18) . . . . ?
C1 O1 C2 C17 2.7(3) . . . . ?
C1 O1 C2 C3 -178.29(18) . . . . ?
C16 C5 C4 C3 -0.1(3) . . . . ?
C6 C5 C4 C3 176.01(17) . . . . ?
C18 O2 C3 C4 2.2(3) . . . . ?
C18 O2 C3 C2 -177.55(17) . . . . ?
C5 C4 C3 O2 -179.99(17) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
O1 C2 C3 O2 1.3(2) . . . . ?
C17 C2 C3 O2 -179.64(17) . . . . ?
O1 C2 C3 C4 -178.47(17) . . . . ?
C17 C2 C3 C4 0.6(3) . . . . ?
O1 C2 C17 C16 178.39(18) . . . . ?
C3 C2 C17 C16 -0.6(3) . . . . ?
C12 N1 C13 C6 145.64(17) . . . . ?
C14 N1 C13 C6 -57.1(2) . . . . ?
C12 N1 C13 C10 20.0(2) . . . . ?
C14 N1 C13 C10 177.20(17) . . . . ?
C7 C6 C13 N1 -118.72(19) . . . . ?
C5 C6 C13 N1 68.1(2) . . . . ?
C7 C6 C13 C10 0.7(2) . . . . ?
C5 C6 C13 C10 -172.45(15) . . . . ?
C9 C10 C13 N1 95.19(18) . . . . ?
C11 C10 C13 N1 -25.15(18) . . . . ?
C9 C10 C13 C6 -30.7(2) . . . . ?
C11 C10 C13 C6 -150.99(16) . . . . ?
C4 C5 C16 C17 0.1(3) . . . . ?
C6 C5 C16 C17 -175.79(17) . . . . ?
C4 C5 C16 C15 175.88(17) . . . . ?
C6 C5 C16 C15 0.0(3) . . . . ?
C2 C17 C16 C5 0.2(3) . . . . ?
C2 C17 C16 C15 -175.62(19) . . . . ?
C9 C10 C11 C12 -99.18(19) . . . . ?
C13 C10 C11 C12 22.4(2) . . . . ?
C5 C6 C7 C8 -177.80(18) . . . . ?
C13 C6 C7 C8 9.1(3) . . . . ?
C14 N1 C12 O4 14.8(3) . . . . ?
C13 N1 C12 O4 172.42(19) . . . . ?
C14 N1 C12 C11 -163.38(18) . . . . ?
C13 N1 C12 C11 -5.8(2) . . . . ?
C10 C11 C12 O4 170.62(19) . . . . ?
C10 C11 C12 N1 -11.2(2) . . . . ?
C6 C7 C8 O3 -170.0(2) . . . . ?
C6 C7 C8 C9 12.7(3) . . . . ?
C12 N1 C14 C15 -141.80(19) . . . . ?
C13 N1 C14 C15 62.7(3) . . . . ?
O3 C8 C9 C10 140.0(2) . . . . ?
C7 C8 C9 C10 -42.7(3) . . . . ?
C11 C10 C9 C8 167.33(17) . . . . ?
C13 C10 C9 C8 51.4(2) . . . . ?
N1 C14 C15 C16 -76.7(2) . . . . ?
C5 C16 C15 C14 60.8(3) . . . . ?
C17 C16 C15 C14 -123.5(2) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_20201214-dengjun-fds-20201104-1
_database_code_depnum_ccdc_archive 'CCDC 2115753'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O3'
_chemical_formula_weight         299.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9211(6)
_cell_length_b                   7.5981(3)
_cell_length_c                   17.1600(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.380(6)
_cell_angle_gamma                90
_cell_volume                     1466.24(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6366
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         29.072
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3374
_reflns_number_gt                2421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0577P)²+0.6158P] 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_number_reflns         3374
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O3 O 0.62420(12) 0.6924(2) 0.77712(8) 0.0367(4) Uani 1 1 d . . . . .
O1 O 0.45064(12) 0.8070(2) 0.65017(9) 0.0439(4) Uani 1 1 d . . . . .
O2 O 1.07178(12) 0.8318(2) 0.48390(10) 0.0450(4) Uani 1 1 d . . . . .
N1 N 0.89495(14) 0.7334(2) 0.49210(10) 0.0322(4) Uani 1 1 d . . . . .
C3 C 0.56463(17) 0.7549(3) 0.55781(12) 0.0307(4) Uani 1 1 d . . . . .
H3 H 0.5027 0.7977 0.5130 0.037 Uiso 1 1 calc R U . . .
C15 C 0.75943(16) 0.6278(2) 0.61318(11) 0.0276(4) Uani 1 1 d . . . . .
C17 C 0.64396(17) 0.6896(3) 0.70294(12) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.66878(16) 0.6947(2) 0.54490(11) 0.0271(4) Uani 1 1 d . . . . .
C11 C 0.96610(18) 0.7996(3) 0.45083(13) 0.0337(5) Uani 1 1 d . . . . .
C16 C 0.74576(17) 0.6274(3) 0.69108(12) 0.0300(4) Uani 1 1 d . . . . .
H16 H 0.8070 0.5840 0.7361 0.036 Uiso 1 1 calc R U . . .
C2 C 0.55122(16) 0.7527(3) 0.63471(12) 0.0312(4) Uani 1 1 d . . . . .
C5 C 0.67589(17) 0.6991(2) 0.45991(11) 0.0287(4) Uani 1 1 d . . . . .
C12 C 0.77572(17) 0.7115(3) 0.44050(11) 0.0301(4) Uani 1 1 d . . . . .
C14 C 0.87393(17) 0.5589(3) 0.60586(12) 0.0346(5) Uani 1 1 d . . . . .
H14A H 0.8561 0.4644 0.5656 0.042 Uiso 1 1 calc R U . . .
H14B H 0.9222 0.5104 0.6586 0.042 Uiso 1 1 calc R U . . .
C6 C 0.55754(18) 0.6981(3) 0.38984(12) 0.0367(5) Uani 1 1 d . . . . .
H6A H 0.5198 0.8117 0.3882 0.044 Uiso 1 1 calc R U . . .
H6B H 0.5065 0.6102 0.4018 0.044 Uiso 1 1 calc R U . . .
C9 C 0.78106(19) 0.7140(3) 0.35302(12) 0.0375(5) Uani 1 1 d . . . . .
H9 H 0.7981 0.5937 0.3398 0.045 Uiso 1 1 calc R U . . .
C13 C 0.94411(18) 0.6992(3) 0.58018(12) 0.0375(5) Uani 1 1 d . . . . .
H13A H 0.9430 0.8068 0.6103 0.045 Uiso 1 1 calc R U . . .
H13B H 1.0262 0.6615 0.5940 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7179(2) 0.6305(3) 0.84730(13) 0.0434(6) Uani 1 1 d . . . . .
H18A H 0.7372 0.5115 0.8379 0.065 Uiso 1 1 calc R U . . .
H18B H 0.6931 0.6346 0.8951 0.065 Uiso 1 1 calc R U . . .
H18C H 0.7867 0.7037 0.8563 0.065 Uiso 1 1 calc R U . . .
C10 C 0.89130(19) 0.8243(3) 0.36159(13) 0.0413(5) Uani 1 1 d . . . . .
H10A H 0.9324 0.7820 0.3251 0.050 Uiso 1 1 calc R U . . .
H10B H 0.8707 0.9472 0.3495 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5661(2) 0.6601(3) 0.30458(13) 0.0459(6) Uani 1 1 d . . . . .
H7A H 0.5816 0.5358 0.3002 0.055 Uiso 1 1 calc R U . . .
H7B H 0.4910 0.6882 0.2625 0.055 Uiso 1 1 calc R U . . .
C1 C 0.34279(19) 0.8124(4) 0.58155(15) 0.0500(6) Uani 1 1 d . . . . .
H1A H 0.3442 0.9117 0.5473 0.075 Uiso 1 1 calc R U . . .
H1B H 0.2765 0.8228 0.6012 0.075 Uiso 1 1 calc R U . . .
H1C H 0.3351 0.7061 0.5499 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6644(2) 0.7672(3) 0.28991(13) 0.0440(6) Uani 1 1 d . . . . .
H8A H 0.6663 0.7456 0.2347 0.053 Uiso 1 1 calc R U . . .
H8B H 0.6504 0.8917 0.2951 0.053 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 C17 1.369(2) . ?
O3 C18 1.424(2) . ?
O1 C2 1.374(2) . ?
O1 C1 1.427(3) . ?
O2 C11 1.223(2) . ?
N1 C11 1.369(3) . ?
N1 C12 1.413(2) . ?
N1 C13 1.452(2) . ?
C3 C2 1.381(3) . ?
C3 C4 1.408(3) . ?
C3 H3 0.9300 . ?
C15 C16 1.399(3) . ?
C15 C4 1.400(3) . ?
C15 C14 1.506(3) . ?
C17 C16 1.379(3) . ?
C17 C2 1.401(3) . ?
C4 C5 1.489(3) . ?
C11 C10 1.506(3) . ?
C16 H16 0.9300 . ?
C5 C12 1.341(3) . ?
C5 C6 1.520(3) . ?
C12 C9 1.524(3) . ?
C14 C13 1.508(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 C7 1.528(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C9 C8 1.506(3) . ?
C9 C10 1.524(3) . ?
C9 H9 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O3 C18 116.89(15) . . ?
C2 O1 C1 117.01(17) . . ?
C11 N1 C12 112.72(16) . . ?
C11 N1 C13 119.94(16) . . ?
C12 N1 C13 127.30(16) . . ?
C2 C3 C4 122.29(18) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C16 C15 C4 119.87(17) . . ?
C16 C15 C14 118.37(16) . . ?
C4 C15 C14 121.74(16) . . ?
O3 C17 C16 125.02(17) . . ?
O3 C17 C2 116.10(17) . . ?
C16 C17 C2 118.87(17) . . ?
C15 C4 C3 117.55(17) . . ?
C15 C4 C5 123.29(17) . . ?
C3 C4 C5 119.12(17) . . ?
O2 C11 N1 123.61(19) . . ?
O2 C11 C10 128.18(19) . . ?
N1 C11 C10 108.21(17) . . ?
C17 C16 C15 121.84(17) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
O1 C2 C3 124.46(18) . . ?
O1 C2 C17 115.99(17) . . ?
C3 C2 C17 119.54(18) . . ?
C12 C5 C4 126.03(17) . . ?
C12 C5 C6 118.10(17) . . ?
C4 C5 C6 115.80(17) . . ?
C5 C12 N1 130.06(17) . . ?
C5 C12 C9 125.18(18) . . ?
N1 C12 C9 104.69(16) . . ?
C15 C14 C13 112.63(17) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C5 C6 C7 114.76(18) . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C8 C9 C12 112.41(18) . . ?
C8 C9 C10 118.85(18) . . ?
C12 C9 C10 103.21(16) . . ?
C8 C9 H9 107.3 . . ?
C12 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
N1 C13 C14 111.05(17) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 C10 C9 103.31(17) . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C8 C7 C6 111.06(18) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C8 C7 108.47(18) . . ?
C9 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_fds-20181130-xy
_database_code_depnum_ccdc_archive 'CCDC 2115760'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N O4'
_chemical_formula_weight         313.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.2707(4)
_cell_length_b                   18.5868(5)
_cell_length_c                   16.0997(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.192(4)
_cell_angle_gamma                90
_cell_volume                     3165.39(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15911
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6460
_reflns_number_gt                4528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0610P)²+0.8733P] 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_number_reflns         6460
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.49870(16) 0.22717(8) 0.88081(10) 0.0657(4) Uani 1 1 d . . . . .
O3 O 0.79103(14) 0.42125(9) 0.51293(11) 0.0668(4) Uani 1 1 d . . . . .
N2 N 0.34727(15) 0.85044(8) 0.91019(10) 0.0448(4) Uani 1 1 d . . . . .
O7 O 0.21101(14) 0.83640(9) 0.98645(11) 0.0682(5) Uani 1 1 d . . . . .
O6 O 0.51954(17) 0.85247(9) 0.58676(11) 0.0786(5) Uani 1 1 d . . . . .
N1 N 0.66197(15) 0.40014(9) 0.59334(11) 0.0486(4) Uani 1 1 d . . . . .
O2 O 0.4933(2) 0.36177(9) 0.91498(12) 0.0906(6) Uani 1 1 d . . . . .
O5 O 0.4270(2) 0.98026(9) 0.56551(12) 0.0893(6) Uani 1 1 d . . . . .
O8 O 0.4987(2) 0.59179(9) 0.86072(13) 0.0912(6) Uani 1 1 d . . . . .
O4 O 0.6063(2) 0.65232(9) 0.71883(14) 0.0986(7) Uani 1 1 d . . . . .
C6 C 0.59544(18) 0.37456(10) 0.72083(13) 0.0439(4) Uani 1 1 d . . . . .
C24 C 0.40655(17) 0.85923(10) 0.77696(12) 0.0402(4) Uani 1 1 d . . . . .
C5 C 0.60085(18) 0.30199(10) 0.70278(13) 0.0461(5) Uani 1 1 d . . . . .
C30 C 0.52467(18) 0.77977(11) 0.90429(13) 0.0450(5) Uani 1 1 d . . . . .
H30 H 0.5857 0.8116 0.9384 0.054 Uiso 1 1 calc R U . . .
C29 C 0.39698(17) 0.81008(10) 0.85072(12) 0.0400(4) Uani 1 1 d . . . . .
C23 C 0.36122(18) 0.92910(10) 0.76704(13) 0.0453(5) Uani 1 1 d . . . . .
C4 C 0.57100(19) 0.25165(10) 0.75746(14) 0.0492(5) Uani 1 1 d . . . . .
H4 H 0.5759 0.2029 0.7463 0.059 Uiso 1 1 calc R U . . .
C25 C 0.46213(18) 0.83259(10) 0.71745(13) 0.0462(5) Uani 1 1 d . . . . .
H25 H 0.4961 0.7864 0.7254 0.055 Uiso 1 1 calc R U . . .
C3 C 0.53474(19) 0.27232(11) 0.82701(13) 0.0492(5) Uani 1 1 d . . . . .
C11 C 0.62679(17) 0.43287(10) 0.66487(12) 0.0432(4) Uani 1 1 d . . . . .
C18 C 0.75215(19) 0.43635(11) 0.57339(15) 0.0516(5) Uani 1 1 d . . . . .
C34 C 0.29776(19) 0.74922(11) 0.81903(14) 0.0496(5) Uani 1 1 d . . . . .
H34 H 0.2260 0.7673 0.7693 0.060 Uiso 1 1 calc R U . . .
C36 C 0.26541(19) 0.81269(12) 0.93799(14) 0.0510(5) Uani 1 1 d . . . . .
C26 C 0.4673(2) 0.87362(11) 0.64756(14) 0.0523(5) Uani 1 1 d . . . . .
C12 C 0.51220(19) 0.47990(12) 0.62433(13) 0.0504(5) Uani 1 1 d . . . . .
H12 H 0.4413 0.4594 0.5826 0.060 Uiso 1 1 calc R U . . .
C28 C 0.3682(2) 0.92725(10) 0.92257(14) 0.0521(5) Uani 1 1 d . . . . .
H28A H 0.4581 0.9375 0.9464 0.062 Uiso 1 1 calc R U . . .
H28B H 0.3294 0.9454 0.9636 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6062(2) 0.33252(11) 0.55383(14) 0.0536(5) Uani 1 1 d . . . . .
H10A H 0.6404 0.3182 0.5087 0.064 Uiso 1 1 calc R U . . .
H10B H 0.5154 0.3378 0.5263 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5586(2) 0.39560(11) 0.79161(13) 0.0522(5) Uani 1 1 d . . . . .
H7 H 0.5540 0.4443 0.8033 0.063 Uiso 1 1 calc R U . . .
C22 C 0.3672(2) 0.97023(11) 0.69613(14) 0.0547(5) Uani 1 1 d . . . . .
H22 H 0.3366 1.0171 0.6895 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4171(2) 0.94347(12) 0.63599(14) 0.0572(6) Uani 1 1 d . . . . .
C9 C 0.6359(2) 0.27601(11) 0.62548(14) 0.0559(5) Uani 1 1 d . . . . .
H9A H 0.5895 0.2323 0.6017 0.067 Uiso 1 1 calc R U . . .
H9B H 0.7255 0.2648 0.6455 0.067 Uiso 1 1 calc R U . . .
C8 C 0.5290(2) 0.34543(11) 0.84445(14) 0.0554(5) Uani 1 1 d . . . . .
C31 C 0.5561(2) 0.71048(12) 0.90621(15) 0.0555(6) Uani 1 1 d . . . . .
H31 H 0.6363 0.6965 0.9429 0.067 Uiso 1 1 calc R U . . .
C35 C 0.2549(2) 0.73892(12) 0.89871(15) 0.0561(6) Uani 1 1 d . . . . .
H35A H 0.1684 0.7216 0.8802 0.067 Uiso 1 1 calc R U . . .
H35B H 0.3093 0.7052 0.9407 0.067 Uiso 1 1 calc R U . . .
C20 C 0.5992(2) 0.79280(12) 0.60526(15) 0.0618(6) Uani 1 1 d . . . . .
H20A H 0.6340 0.7867 0.5590 0.093 Uiso 1 1 calc R U . . .
H20B H 0.5521 0.7506 0.6088 0.093 Uiso 1 1 calc R U . . .
H20C H 0.6666 0.7999 0.6607 0.093 Uiso 1 1 calc R U . . .
C27 C 0.3097(2) 0.96268(11) 0.83322(14) 0.0562(6) Uani 1 1 d . . . . .
H27A H 0.3285 1.0138 0.8382 0.067 Uiso 1 1 calc R U . . .
H27B H 0.2186 0.9569 0.8129 0.067 Uiso 1 1 calc R U . . .
C16 C 0.7457(2) 0.47828(11) 0.71256(14) 0.0536(5) Uani 1 1 d . . . . .
H16 H 0.8083 0.4474 0.7549 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7942(2) 0.49744(12) 0.63754(16) 0.0602(6) Uani 1 1 d . . . . .
H17A H 0.7580 0.5425 0.6099 0.072 Uiso 1 1 calc R U . . .
H17B H 0.8856 0.5016 0.6595 0.072 Uiso 1 1 calc R U . . .
C32 C 0.4707(2) 0.65567(12) 0.85364(15) 0.0617(6) Uani 1 1 d . . . . .
C13 C 0.5062(2) 0.54902(13) 0.64455(16) 0.0619(6) Uani 1 1 d . . . . .
H13 H 0.4315 0.5739 0.6166 0.074 Uiso 1 1 calc R U . . .
C33 C 0.3474(2) 0.68143(11) 0.78928(16) 0.0637(6) Uani 1 1 d . . . . .
H33A H 0.2851 0.6435 0.7803 0.076 Uiso 1 1 calc R U . . .
H33B H 0.3577 0.6907 0.7329 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7217(2) 0.54347(12) 0.76200(16) 0.0670(6) Uani 1 1 d . . . . .
H15A H 0.7078 0.5272 0.8151 0.080 Uiso 1 1 calc R U . . .
H15B H 0.7964 0.5737 0.7800 0.080 Uiso 1 1 calc R U . . .
C1 C 0.4978(3) 0.15243(12) 0.86361(17) 0.0745(7) Uani 1 1 d . . . . .
H1A H 0.4469 0.1433 0.8031 0.112 Uiso 1 1 calc R U . . .
H1B H 0.4632 0.1271 0.9019 0.112 Uiso 1 1 calc R U . . .
H1C H 0.5826 0.1362 0.8741 0.112 Uiso 1 1 calc R U . . .
C14 C 0.6106(3) 0.58730(12) 0.70807(17) 0.0657(7) Uani 1 1 d . . . . .
C2 C 0.4572(4) 0.42926(17) 0.9244(2) 0.1118(13) Uani 1 1 d . . . . .
H2A H 0.3946 0.4448 0.8700 0.168 Uiso 1 1 calc R U . . .
H2B H 0.5291 0.4607 0.9390 0.168 Uiso 1 1 calc R U . . .
H2C H 0.4222 0.4305 0.9709 0.168 Uiso 1 1 calc R U . . .
C19 C 0.3794(4) 1.05119(17) 0.5514(3) 0.1244(15) Uani 1 1 d . . . . .
H19A H 0.3913 1.0707 0.4996 0.187 Uiso 1 1 calc R U . . .
H19B H 0.4236 1.0804 0.6017 0.187 Uiso 1 1 calc R U . . .
H19C H 0.2909 1.0508 0.5431 0.187 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.365(2) . ?
O1 C1 1.416(3) . ?
O3 C18 1.230(2) . ?
N2 C36 1.352(2) . ?
N2 C28 1.449(2) . ?
N2 C29 1.471(2) . ?
O7 C36 1.229(2) . ?
O6 C26 1.363(2) . ?
O6 C20 1.393(2) . ?
N1 C18 1.347(2) . ?
N1 C10 1.450(3) . ?
N1 C11 1.473(2) . ?
O2 C2 1.343(3) . ?
O2 C8 1.364(2) . ?
O5 C21 1.362(2) . ?
O5 C19 1.412(3) . ?
O8 C32 1.224(3) . ?
O4 C14 1.224(3) . ?
C6 C5 1.385(3) . ?
C6 C7 1.396(3) . ?
C6 C11 1.527(2) . ?
C24 C23 1.384(2) . ?
C24 C25 1.403(2) . ?
C24 C29 1.531(2) . ?
C5 C4 1.403(3) . ?
C5 C9 1.509(3) . ?
C30 C31 1.333(3) . ?
C30 C29 1.509(3) . ?
C30 H30 0.9300 . ?
C29 C34 1.548(3) . ?
C23 C22 1.395(3) . ?
C23 C27 1.513(3) . ?
C4 C3 1.373(3) . ?
C4 H4 0.9300 . ?
C25 C26 1.377(3) . ?
C25 H25 0.9300 . ?
C3 C8 1.393(3) . ?
C11 C12 1.509(3) . ?
C11 C16 1.545(3) . ?
C18 C17 1.498(3) . ?
C34 C33 1.522(3) . ?
C34 C35 1.531(3) . ?
C34 H34 0.9800 . ?
C36 C35 1.497(3) . ?
C26 C21 1.403(3) . ?
C12 C13 1.333(3) . ?
C12 H12 0.9300 . ?
C28 C27 1.511(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C10 C9 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C22 C21 1.370(3) . ?
C22 H22 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C31 C32 1.455(3) . ?
C31 H31 0.9300 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C16 C15 1.524(3) . ?
C16 C17 1.530(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C32 C33 1.497(3) . ?
C13 C14 1.451(4) . ?
C13 H13 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C15 C14 1.495(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C1 117.57(17) . . ?
C36 N2 C28 124.26(16) . . ?
C36 N2 C29 114.04(16) . . ?
C28 N2 C29 120.74(14) . . ?
C26 O6 C20 118.86(16) . . ?
C18 N1 C10 125.24(17) . . ?
C18 N1 C11 114.14(17) . . ?
C10 N1 C11 120.53(14) . . ?
C2 O2 C8 119.33(18) . . ?
C21 O5 C19 117.87(18) . . ?
C5 C6 C7 119.39(17) . . ?
C5 C6 C11 122.10(17) . . ?
C7 C6 C11 118.50(17) . . ?
C23 C24 C25 119.09(16) . . ?
C23 C24 C29 121.80(15) . . ?
C25 C24 C29 119.11(16) . . ?
C6 C5 C4 118.70(18) . . ?
C6 C5 C9 121.84(17) . . ?
C4 C5 C9 119.46(18) . . ?
C31 C30 C29 124.6(2) . . ?
C31 C30 H30 117.7 . . ?
C29 C30 H30 117.7 . . ?
N2 C29 C30 108.71(15) . . ?
N2 C29 C24 110.19(14) . . ?
C30 C29 C24 110.95(14) . . ?
N2 C29 C34 101.13(13) . . ?
C30 C29 C34 110.70(15) . . ?
C24 C29 C34 114.63(15) . . ?
C24 C23 C22 119.21(17) . . ?
C24 C23 C27 121.46(16) . . ?
C22 C23 C27 119.30(17) . . ?
C3 C4 C5 121.91(18) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C26 C25 C24 121.14(17) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
O1 C3 C4 125.68(19) . . ?
O1 C3 C8 115.29(18) . . ?
C4 C3 C8 118.99(18) . . ?
N1 C11 C12 108.81(15) . . ?
N1 C11 C6 110.36(15) . . ?
C12 C11 C6 109.19(15) . . ?
N1 C11 C16 101.11(14) . . ?
C12 C11 C16 111.38(16) . . ?
C6 C11 C16 115.61(16) . . ?
O3 C18 N1 125.4(2) . . ?
O3 C18 C17 127.19(19) . . ?
N1 C18 C17 107.44(18) . . ?
C33 C34 C35 114.66(17) . . ?
C33 C34 C29 113.99(17) . . ?
C35 C34 C29 102.49(16) . . ?
C33 C34 H34 108.5 . . ?
C35 C34 H34 108.5 . . ?
C29 C34 H34 108.5 . . ?
O7 C36 N2 124.8(2) . . ?
O7 C36 C35 127.77(18) . . ?
N2 C36 C35 107.41(16) . . ?
O6 C26 C25 125.29(18) . . ?
O6 C26 C21 115.23(17) . . ?
C25 C26 C21 119.48(17) . . ?
C13 C12 C11 124.1(2) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N2 C28 C27 107.55(17) . . ?
N2 C28 H28A 110.2 . . ?
C27 C28 H28A 110.2 . . ?
N2 C28 H28B 110.2 . . ?
C27 C28 H28B 110.2 . . ?
H28A C28 H28B 108.5 . . ?
N1 C10 C9 108.63(17) . . ?
N1 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
N1 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C8 C7 C6 121.16(18) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C21 C22 C23 121.83(18) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
O5 C21 C22 125.32(19) . . ?
O5 C21 C26 115.47(18) . . ?
C22 C21 C26 119.17(17) . . ?
C5 C9 C10 110.80(17) . . ?
C5 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C8 C7 124.55(19) . . ?
O2 C8 C3 115.62(18) . . ?
C7 C8 C3 119.83(18) . . ?
C30 C31 C32 123.1(2) . . ?
C30 C31 H31 118.5 . . ?
C32 C31 H31 118.5 . . ?
C36 C35 C34 103.73(16) . . ?
C36 C35 H35A 111.0 . . ?
C34 C35 H35A 111.0 . . ?
C36 C35 H35B 111.0 . . ?
C34 C35 H35B 111.0 . . ?
H35A C35 H35B 109.0 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C28 C27 C23 110.05(16) . . ?
C28 C27 H27A 109.6 . . ?
C23 C27 H27A 109.6 . . ?
C28 C27 H27B 109.6 . . ?
C23 C27 H27B 109.6 . . ?
H27A C27 H27B 108.2 . . ?
C15 C16 C17 113.79(18) . . ?
C15 C16 C11 114.45(17) . . ?
C17 C16 C11 102.71(17) . . ?
C15 C16 H16 108.5 . . ?
C17 C16 H16 108.5 . . ?
C11 C16 H16 108.5 . . ?
C18 C17 C16 104.69(16) . . ?
C18 C17 H17A 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?
O8 C32 C31 121.9(2) . . ?
O8 C32 C33 121.5(2) . . ?
C31 C32 C33 116.62(19) . . ?
C12 C13 C14 123.2(2) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C32 C33 C34 113.67(19) . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C34 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C14 C15 C16 113.2(2) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C14 C13 121.4(3) . . ?
O4 C14 C15 121.5(3) . . ?
C13 C14 C15 117.06(19) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_20220223-fds-1
_database_code_depnum_ccdc_archive 'CCDC 2154740'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N O4'
_chemical_formula_sum            'C18 H23 N O4'
_chemical_formula_weight         317.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H23 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0338(4)
_cell_length_b                   12.5800(6)
_cell_length_c                   13.9834(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1589.15(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1230
_cell_measurement_theta_min      3.6720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.178
_diffrn_reflns_theta_min         3.334
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  55.00   1.00    5.08    --   18.74 -19.00  30.00  105
  2  ω     16.00  56.00   1.00    5.08    --   18.74  57.00 -90.00   40
  3  ω      6.00  56.00   1.00    5.08    --   18.58  38.00-120.00   50
  4  ω    -23.00   3.00   1.00    5.08    --  -18.78 -78.00-104.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0072633000
_diffrn_orient_matrix_UB_12      -0.0351179000
_diffrn_orient_matrix_UB_13      0.0393838000
_diffrn_orient_matrix_UB_21      0.0487270000
_diffrn_orient_matrix_UB_22      0.0324142000
_diffrn_orient_matrix_UB_23      0.0270730000
_diffrn_orient_matrix_UB_31      -0.0611242000
_diffrn_orient_matrix_UB_32      0.0299710000
_diffrn_orient_matrix_UB_33      0.0169425000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                2984
_reflns_number_total             3650
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.9(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.106
_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)+(0.0365P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1149
_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:
 C5(H5), C7(H7), C8(H8), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C4(H4A,H4B), C9(H9A,H9B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O3 O 0.9287(3) 1.00270(18) 0.50020(14) 0.0452(6) Uani 1 1 d . . . . .
O4 O 0.7420(3) 0.89046(19) 0.40513(14) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.7526(3) 0.36586(18) 0.70524(17) 0.0578(7) Uani 1 1 d . . . . .
H2 H 0.790815 0.357725 0.652546 0.087 Uiso 1 1 calc R U . . .
O1 O 0.6240(3) 0.6794(2) 1.02276(16) 0.0560(7) Uani 1 1 d . . . . .
N1 N 0.6378(3) 0.6994(2) 0.86007(17) 0.0363(6) Uani 1 1 d . . . . .
C15 C 0.8627(3) 0.9219(2) 0.5499(2) 0.0318(6) Uani 1 1 d . . . . .
C14 C 0.7614(3) 0.8603(2) 0.49848(19) 0.0328(6) Uani 1 1 d . . . . .
C13 C 0.6894(3) 0.7779(2) 0.5436(2) 0.0335(7) Uani 1 1 d . . . . .
H13 H 0.621798 0.737544 0.509086 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8890(3) 0.8978(2) 0.6445(2) 0.0331(6) Uani 1 1 d . . . . .
H16 H 0.956545 0.938719 0.678664 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8178(3) 0.8139(2) 0.69087(19) 0.0309(6) Uani 1 1 d . . . . .
C12 C 0.7148(3) 0.7528(2) 0.6405(2) 0.0299(6) Uani 1 1 d . . . . .
C1 C 0.5813(3) 0.6578(3) 0.9415(2) 0.0422(8) Uani 1 1 d . . . . .
C6 C 0.7421(3) 0.5577(2) 0.6801(2) 0.0362(7) Uani 1 1 d . . . . .
H6A H 0.788352 0.550709 0.617830 0.043 Uiso 1 1 calc R U . . .
H6B H 0.819760 0.568090 0.727120 0.043 Uiso 1 1 calc R U . . .
C5 C 0.6580(4) 0.4569(2) 0.7032(2) 0.0389(7) Uani 1 1 d . . . . .
H5 H 0.580593 0.446046 0.655078 0.047 Uiso 1 1 calc R U . . .
C7 C 0.6388(3) 0.6547(2) 0.6800(2) 0.0328(6) Uani 1 1 d . . . . .
H7 H 0.562509 0.637504 0.632652 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5536(3) 0.6673(3) 0.7745(2) 0.0352(7) Uani 1 1 d . . . . .
H8 H 0.473974 0.718992 0.764519 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8583(3) 0.7923(3) 0.7939(2) 0.0393(7) Uani 1 1 d . . . . .
H10A H 0.930594 0.844769 0.814016 0.047 Uiso 1 1 calc R U . . .
H10B H 0.905247 0.723088 0.797562 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4833(3) 0.5617(3) 0.8090(2) 0.0415(8) Uani 1 1 d . . . . .
H3 H 0.389834 0.547999 0.775594 0.050 Uiso 1 1 calc R U . . .
C18 C 0.6402(4) 0.8314(3) 0.3494(2) 0.0595(11) Uani 1 1 d . . . . .
H18A H 0.629493 0.864224 0.287844 0.089 Uiso 1 1 calc R U . . .
H18B H 0.545905 0.829909 0.381115 0.089 Uiso 1 1 calc R U . . .
H18C H 0.676034 0.760119 0.341630 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5876(4) 0.4663(3) 0.8003(2) 0.0415(8) Uani 1 1 d . . . . .
H4A H 0.664904 0.472619 0.848148 0.050 Uiso 1 1 calc R U . . .
H4B H 0.532552 0.401806 0.813671 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7297(4) 0.7945(3) 0.8633(2) 0.0415(7) Uani 1 1 d . . . . .
H9A H 0.767980 0.803055 0.927652 0.050 Uiso 1 1 calc R U . . .
H9B H 0.668377 0.855900 0.849248 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4556(4) 0.5851(3) 0.9151(2) 0.0541(10) Uani 1 1 d . . . . .
H2A H 0.360838 0.619823 0.924351 0.065 Uiso 1 1 calc R U . . .
H2B H 0.458148 0.520351 0.952716 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0219(4) 1.0722(3) 0.5515(3) 0.0579(10) Uani 1 1 d . . . . .
H17A H 1.058479 1.126338 0.509287 0.087 Uiso 1 1 calc R U . . .
H17B H 1.103574 1.032927 0.577534 0.087 Uiso 1 1 calc R U . . .
H17C H 0.966979 1.104595 0.602516 0.087 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 C15 1.368(3) . ?
O3 C17 1.409(4) . ?
O4 C14 1.371(3) . ?
O4 C18 1.416(4) . ?
O2 H2 0.8200 . ?
O2 C5 1.429(4) . ?
O1 C1 1.231(4) . ?
N1 C1 1.353(4) . ?
N1 C8 1.474(4) . ?
N1 C9 1.457(4) . ?
C15 C14 1.399(4) . ?
C15 C16 1.379(4) . ?
C14 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.410(4) . ?
C16 H16 0.9300 . ?
C16 C11 1.395(4) . ?
C11 C12 1.397(4) . ?
C11 C10 1.511(4) . ?
C12 C7 1.517(4) . ?
C1 C2 1.504(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.513(4) . ?
C6 C7 1.537(4) . ?
C5 H5 0.9800 . ?
C5 C4 1.505(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.537(4) . ?
C8 H8 0.9800 . ?
C8 C3 1.549(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.515(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.530(5) . ?
C3 C2 1.533(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 C17 117.5(2) . . ?
C14 O4 C18 117.5(3) . . ?
C5 O2 H2 109.5 . . ?
C1 N1 C8 112.4(2) . . ?
C1 N1 C9 120.4(3) . . ?
C9 N1 C8 123.0(2) . . ?
O3 C15 C14 115.8(2) . . ?
O3 C15 C16 125.2(3) . . ?
C16 C15 C14 118.9(3) . . ?
O4 C14 C15 114.8(3) . . ?
O4 C14 C13 125.8(3) . . ?
C13 C14 C15 119.4(2) . . ?
C14 C13 H13 118.9 . . ?
C14 C13 C12 122.2(3) . . ?
C12 C13 H13 118.9 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C11 122.2(3) . . ?
C11 C16 H16 118.9 . . ?
C16 C11 C12 119.3(3) . . ?
C16 C11 C10 117.8(3) . . ?
C12 C11 C10 122.9(3) . . ?
C13 C12 C7 117.3(3) . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 C7 124.4(3) . . ?
O1 C1 N1 125.0(3) . . ?
O1 C1 C2 126.7(3) . . ?
N1 C1 C2 108.3(3) . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.1(2) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
O2 C5 C6 112.0(2) . . ?
O2 C5 H5 109.2 . . ?
O2 C5 C4 107.3(3) . . ?
C6 C5 H5 109.2 . . ?
C4 C5 C6 109.8(3) . . ?
C4 C5 H5 109.2 . . ?
C12 C7 C6 111.8(2) . . ?
C12 C7 H7 104.6 . . ?
C12 C7 C8 117.2(2) . . ?
C6 C7 H7 104.6 . . ?
C8 C7 C6 112.6(2) . . ?
C8 C7 H7 104.6 . . ?
N1 C8 C7 117.9(2) . . ?
N1 C8 H8 108.2 . . ?
N1 C8 C3 101.2(2) . . ?
C7 C8 H8 108.2 . . ?
C7 C8 C3 112.6(3) . . ?
C3 C8 H8 108.2 . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C11 C10 C9 114.9(2) . . ?
H10A C10 H10B 107.5 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C8 C3 H3 110.8 . . ?
C4 C3 C8 113.2(2) . . ?
C4 C3 H3 110.8 . . ?
C4 C3 C2 109.1(3) . . ?
C2 C3 C8 101.7(3) . . ?
C2 C3 H3 110.8 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C5 C4 C3 113.2(3) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
N1 C9 C10 113.7(3) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C1 C2 C3 103.4(3) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C15 C14 O4 -0.4(4) . . . . ?
O3 C15 C14 C13 -179.5(3) . . . . ?
O3 C15 C16 C11 -179.9(3) . . . . ?
O4 C14 C13 C12 -179.3(3) . . . . ?
O2 C5 C4 C3 179.6(3) . . . . ?
O1 C1 C2 C3 -163.2(3) . . . . ?
N1 C1 C2 C3 18.9(4) . . . . ?
N1 C8 C3 C4 -82.7(3) . . . . ?
N1 C8 C3 C2 34.3(3) . . . . ?
C15 C14 C13 C12 -0.4(4) . . . . ?
C15 C16 C11 C12 -0.8(4) . . . . ?
C15 C16 C11 C10 178.2(3) . . . . ?
C14 C15 C16 C11 -0.1(4) . . . . ?
C14 C13 C12 C11 -0.6(4) . . . . ?
C14 C13 C12 C7 -175.0(3) . . . . ?
C13 C12 C7 C6 97.5(3) . . . . ?
C13 C12 C7 C8 -130.4(3) . . . . ?
C16 C15 C14 O4 179.8(3) . . . . ?
C16 C15 C14 C13 0.7(4) . . . . ?
C16 C11 C12 C13 1.1(4) . . . . ?
C16 C11 C12 C7 175.1(3) . . . . ?
C16 C11 C10 C9 123.3(3) . . . . ?
C11 C12 C7 C6 -76.6(3) . . . . ?
C11 C12 C7 C8 55.6(4) . . . . ?
C11 C10 C9 N1 76.8(4) . . . . ?
C12 C11 C10 C9 -57.7(4) . . . . ?
C12 C7 C8 N1 -61.6(4) . . . . ?
C12 C7 C8 C3 -178.8(2) . . . . ?
C1 N1 C8 C7 -148.2(3) . . . . ?
C1 N1 C8 C3 -24.9(3) . . . . ?
C1 N1 C9 C10 141.6(3) . . . . ?
C6 C5 C4 C3 57.6(3) . . . . ?
C6 C7 C8 N1 70.2(3) . . . . ?
C6 C7 C8 C3 -47.1(3) . . . . ?
C5 C6 C7 C12 -170.1(2) . . . . ?
C5 C6 C7 C8 55.5(3) . . . . ?
C7 C6 C5 O2 -179.0(2) . . . . ?
C7 C6 C5 C4 -59.9(3) . . . . ?
C7 C8 C3 C4 44.1(4) . . . . ?
C7 C8 C3 C2 161.1(3) . . . . ?
C8 N1 C1 O1 -173.8(3) . . . . ?
C8 N1 C1 C2 4.1(4) . . . . ?
C8 N1 C9 C10 -63.1(4) . . . . ?
C8 C3 C4 C5 -50.1(4) . . . . ?
C8 C3 C2 C1 -32.7(3) . . . . ?
C10 C11 C12 C13 -177.8(3) . . . . ?
C10 C11 C12 C7 -3.8(4) . . . . ?
C18 O4 C14 C15 -179.7(3) . . . . ?
C18 O4 C14 C13 -0.7(5) . . . . ?
C4 C3 C2 C1 87.2(3) . . . . ?
C9 N1 C1 O1 -16.1(5) . . . . ?
C9 N1 C1 C2 161.9(3) . . . . ?
C9 N1 C8 C7 54.7(4) . . . . ?
C9 N1 C8 C3 178.0(2) . . . . ?
C2 C3 C4 C5 -162.6(3) . . . . ?
C17 O3 C15 C14 174.7(3) . . . . ?
C17 O3 C15 C16 -5.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_20210928-dengjun-fds-20210812
_database_code_depnum_ccdc_archive 'CCDC 2115755'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_audit_creation_date             2021-09-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 N O3'
_chemical_formula_sum            'C18 H23 N O3'
_chemical_formula_weight         301.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H23 N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8274(5)
_cell_length_b                   9.7027(4)
_cell_length_c                   12.2527(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.669(4)
_cell_angle_gamma                90
_cell_volume                     1523.32(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2500
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5530
_cell_measurement_theta_min      4.0890
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6642
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.892
_diffrn_reflns_theta_min         3.622
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  22.00   1.00    3.63    --   18.58 -57.00   0.00   69
  2  ω      1.00  40.00   1.00    3.63    --   18.58  77.00-150.00   39
  3  ω    -50.00  40.00   1.00    3.63    --   18.58 -57.00-120.00   90
  4  ω    -18.00   9.00   1.00    3.63    --  -18.78 -77.00 -90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0549723000
_diffrn_orient_matrix_UB_12      0.0068524000
_diffrn_orient_matrix_UB_13      0.0080884000
_diffrn_orient_matrix_UB_21      -0.0046184000
_diffrn_orient_matrix_UB_22      0.0720855000
_diffrn_orient_matrix_UB_23      -0.0082300000
_diffrn_orient_matrix_UB_31      -0.0059822000
_diffrn_orient_matrix_UB_32      0.0091958000
_diffrn_orient_matrix_UB_33      0.0567165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2333
_reflns_number_total             3436
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.042
_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)+(0.0379P)²+0.6242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1365
_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:
 C7(H7), C8(H8), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.59041(10) 0.71255(15) 0.48285(11) 0.0485(4) Uani 1 1 d . . . . .
O3 O 0.65307(10) 0.54365(16) 0.33493(13) 0.0543(4) Uani 1 1 d . . . . .
N1 N 0.13184(12) 0.40847(18) 0.32012(13) 0.0449(4) Uani 1 1 d . . . . .
O1 O -0.03467(12) 0.3601(2) 0.37127(15) 0.0781(6) Uani 1 1 d . . . . .
C14 C 0.54693(13) 0.5585(2) 0.33937(15) 0.0367(4) Uani 1 1 d . . . . .
C15 C 0.51387(14) 0.64905(19) 0.41896(15) 0.0366(4) Uani 1 1 d . . . . .
C16 C 0.40793(14) 0.6675(2) 0.43008(15) 0.0393(4) Uani 1 1 d . . . . .
H16 H 0.385938 0.727218 0.483714 0.047 Uiso 1 1 calc R U . . .
C13 C 0.47291(13) 0.4923(2) 0.27246(15) 0.0378(4) Uani 1 1 d . . . . .
H13 H 0.495284 0.432935 0.218775 0.045 Uiso 1 1 calc R U . . .
C12 C 0.36539(13) 0.51145(19) 0.28248(14) 0.0353(4) Uani 1 1 d . . . . .
C11 C 0.33304(14) 0.5998(2) 0.36387(15) 0.0384(4) Uani 1 1 d . . . . .
C7 C 0.29066(14) 0.4402(2) 0.20109(15) 0.0412(5) Uani 1 1 d . . . . .
H7 H 0.334887 0.377903 0.160530 0.049 Uiso 1 1 calc R U . . .
C17 C 0.55693(17) 0.8068(2) 0.56231(17) 0.0528(5) Uani 1 1 d . . . . .
H17A H 0.517746 0.879687 0.526816 0.079 Uiso 1 1 calc R U . . .
H17B H 0.616645 0.844818 0.601714 0.079 Uiso 1 1 calc R U . . .
H17C H 0.513707 0.759727 0.612225 0.079 Uiso 1 1 calc R U . . .
C8 C 0.20872(14) 0.3459(2) 0.24943(17) 0.0434(5) Uani 1 1 d . . . . .
H8 H 0.245512 0.273114 0.291168 0.052 Uiso 1 1 calc R U . . .
C18 C 0.69200(16) 0.4313(2) 0.2759(2) 0.0565(6) Uani 1 1 d . . . . .
H18A H 0.679223 0.446713 0.199043 0.085 Uiso 1 1 calc R U . . .
H18B H 0.657537 0.348171 0.296811 0.085 Uiso 1 1 calc R U . . .
H18C H 0.765712 0.422502 0.291700 0.085 Uiso 1 1 calc R U . . .
C9 C 0.16155(16) 0.4923(2) 0.41443(17) 0.0514(5) Uani 1 1 d . . . . .
H9A H 0.205532 0.437986 0.464536 0.062 Uiso 1 1 calc R U . . .
H9B H 0.099201 0.517082 0.451775 0.062 Uiso 1 1 calc R U . . .
C10 C 0.21916(15) 0.6226(2) 0.38625(19) 0.0494(5) Uani 1 1 d . . . . .
H10A H 0.214779 0.687347 0.446207 0.059 Uiso 1 1 calc R U . . .
H10B H 0.184639 0.664125 0.322234 0.059 Uiso 1 1 calc R U . . .
C1 C 0.03955(16) 0.3383(3) 0.3141(2) 0.0574(6) Uani 1 1 d . . . . .
C3 C 0.13683(16) 0.2769(3) 0.16191(19) 0.0573(6) Uani 1 1 d . . . . .
H3 H 0.171702 0.198397 0.128965 0.069 Uiso 1 1 calc R U . . .
C6 C 0.24398(18) 0.5390(3) 0.11443(18) 0.0581(6) Uani 1 1 d . . . . .
H6A H 0.198476 0.604241 0.148712 0.070 Uiso 1 1 calc R U . . .
H6B H 0.299672 0.590445 0.082297 0.070 Uiso 1 1 calc R U . . .
C4 C 0.09640(18) 0.3782(3) 0.07407(19) 0.0667(7) Uani 1 1 d . . . . .
H4A H 0.059278 0.327244 0.016280 0.080 Uiso 1 1 calc R U . . .
H4B H 0.047198 0.440730 0.105826 0.080 Uiso 1 1 calc R U . . .
C5 C 0.18234(19) 0.4613(3) 0.02522(19) 0.0734(8) Uani 1 1 d . . . . .
H5A H 0.152274 0.526166 -0.027629 0.088 Uiso 1 1 calc R U . . .
H5B H 0.228573 0.400265 -0.012433 0.088 Uiso 1 1 calc R U . . .
C2 C 0.04689(19) 0.2289(3) 0.2287(2) 0.0731(8) Uani 1 1 d . . . . .
H2A H -0.017282 0.222836 0.183807 0.088 Uiso 1 1 calc R U . . .
H2B H 0.061678 0.139639 0.261580 0.088 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
O2 C15 1.373(2) . ?
O2 C17 1.417(2) . ?
O3 C14 1.373(2) . ?
O3 C18 1.413(2) . ?
N1 C8 1.473(2) . ?
N1 C9 1.450(3) . ?
N1 C1 1.365(3) . ?
O1 C1 1.226(3) . ?
C14 C15 1.393(3) . ?
C14 C13 1.383(3) . ?
C15 C16 1.384(3) . ?
C16 H16 0.9300 . ?
C16 C11 1.393(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.403(2) . ?
C12 C11 1.393(3) . ?
C12 C7 1.517(3) . ?
C11 C10 1.515(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(3) . ?
C7 C6 1.532(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C3 1.535(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.512(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C1 C2 1.497(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.530(3) . ?
C3 C2 1.518(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.519(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.512(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 C17 116.73(15) . . ?
C14 O3 C18 118.44(16) . . ?
C9 N1 C8 122.78(15) . . ?
C1 N1 C8 111.42(18) . . ?
C1 N1 C9 121.22(17) . . ?
O3 C14 C15 115.39(16) . . ?
O3 C14 C13 125.63(17) . . ?
C13 C14 C15 118.98(16) . . ?
O2 C15 C14 116.68(16) . . ?
O2 C15 C16 124.44(17) . . ?
C16 C15 C14 118.86(17) . . ?
C15 C16 H16 118.8 . . ?
C15 C16 C11 122.40(17) . . ?
C11 C16 H16 118.8 . . ?
C14 C13 H13 118.7 . . ?
C14 C13 C12 122.51(17) . . ?
C12 C13 H13 118.7 . . ?
C13 C12 C7 118.42(16) . . ?
C11 C12 C13 118.10(17) . . ?
C11 C12 C7 123.42(16) . . ?
C16 C11 C12 119.13(16) . . ?
C16 C11 C10 118.06(17) . . ?
C12 C11 C10 122.79(17) . . ?
C12 C7 H7 104.6 . . ?
C12 C7 C8 116.20(15) . . ?
C12 C7 C6 112.66(17) . . ?
C8 C7 H7 104.6 . . ?
C6 C7 H7 104.6 . . ?
C6 C7 C8 112.86(16) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C8 C7 118.09(17) . . ?
N1 C8 H8 108.0 . . ?
N1 C8 C3 101.16(15) . . ?
C7 C8 H8 108.0 . . ?
C7 C8 C3 112.99(17) . . ?
C3 C8 H8 108.0 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
N1 C9 C10 113.60(17) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 C11 113.85(17) . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N1 C1 C2 108.00(18) . . ?
O1 C1 N1 125.3(2) . . ?
O1 C1 C2 126.7(2) . . ?
C8 C3 H3 110.8 . . ?
C4 C3 C8 112.61(19) . . ?
C4 C3 H3 110.8 . . ?
C2 C3 C8 101.80(18) . . ?
C2 C3 H3 110.8 . . ?
C2 C3 C4 109.6(2) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C5 C6 C7 111.2(2) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C3 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 113.05(19) . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
C4 C5 C6 110.16(19) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C1 C2 C3 103.47(19) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C15 C16 C11 -179.42(18) . . . . ?
O3 C14 C15 O2 0.2(2) . . . . ?
O3 C14 C15 C16 -178.70(16) . . . . ?
O3 C14 C13 C12 179.30(18) . . . . ?
N1 C8 C3 C4 81.1(2) . . . . ?
N1 C8 C3 C2 -36.1(2) . . . . ?
N1 C9 C10 C11 -78.4(2) . . . . ?
N1 C1 C2 C3 -18.9(3) . . . . ?
O1 C1 C2 C3 162.8(3) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C14 C13 C12 C11 -0.6(3) . . . . ?
C14 C13 C12 C7 176.70(17) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C15 C16 C11 C12 -0.8(3) . . . . ?
C15 C16 C11 C10 177.39(18) . . . . ?
C16 C11 C10 C9 -119.9(2) . . . . ?
C13 C14 C15 O2 -179.69(16) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C13 C12 C11 C16 1.4(3) . . . . ?
C13 C12 C11 C10 -176.72(18) . . . . ?
C13 C12 C7 C8 123.84(19) . . . . ?
C13 C12 C7 C6 -103.8(2) . . . . ?
C12 C11 C10 C9 58.2(3) . . . . ?
C12 C7 C8 N1 62.8(2) . . . . ?
C12 C7 C8 C3 -179.54(17) . . . . ?
C12 C7 C6 C5 171.72(18) . . . . ?
C11 C12 C7 C8 -59.1(2) . . . . ?
C11 C12 C7 C6 73.3(2) . . . . ?
C7 C12 C11 C16 -175.75(17) . . . . ?
C7 C12 C11 C10 6.2(3) . . . . ?
C7 C8 C3 C4 -46.1(2) . . . . ?
C7 C8 C3 C2 -163.35(19) . . . . ?
C7 C6 C5 C4 58.0(3) . . . . ?
C17 O2 C15 C14 178.74(17) . . . . ?
C17 O2 C15 C16 -2.5(3) . . . . ?
C8 N1 C9 C10 62.7(3) . . . . ?
C8 N1 C1 O1 173.2(2) . . . . ?
C8 N1 C1 C2 -5.1(3) . . . . ?
C8 C7 C6 C5 -54.2(2) . . . . ?
C8 C3 C4 C5 51.2(3) . . . . ?
C8 C3 C2 C1 33.9(2) . . . . ?
C18 O3 C14 C15 165.02(18) . . . . ?
C18 O3 C14 C13 -15.1(3) . . . . ?
C9 N1 C8 C7 -53.5(3) . . . . ?
C9 N1 C8 C3 -177.29(19) . . . . ?
C9 N1 C1 O1 16.5(4) . . . . ?
C9 N1 C1 C2 -161.8(2) . . . . ?
C1 N1 C8 C7 150.31(18) . . . . ?
C1 N1 C8 C3 26.5(2) . . . . ?
C1 N1 C9 C10 -143.4(2) . . . . ?
C3 C4 C5 C6 -57.0(3) . . . . ?
C6 C7 C8 N1 -69.5(2) . . . . ?
C6 C7 C8 C3 48.1(2) . . . . ?
C4 C3 C2 C1 -85.5(2) . . . . ?
C2 C3 C4 C5 163.8(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_20191126-dengjun-fds-20191109
_database_code_depnum_ccdc_archive 'CCDC 2115763'
loop_
_audit_author_name
_audit_author_address
'Da-Shu Fang'
;Chongqing University
China
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_chemical_absolute_configuration UNK
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   19.2614(16)
_cell_length_b                   5.0789(4)
_cell_length_c                   19.9253(17)
_cell_angle_alpha                90
_cell_angle_beta                 115.610(10)
_cell_angle_gamma                90
_cell_volume                     1757.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1760
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0840
_cell_measurement_theta_min      4.0000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7168
_diffrn_reflns_point_group_measured_fraction_full 0.720
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_min         3.689
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.395
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.339
_reflns_number_gt                3847
_reflns_number_total             5660
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5660
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.081
_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)+(0.0597P)²+0.0983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1507
_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 Secondary CH2 refined with riding coordinates:
 C010(H01P,H01Q), C011(H01A,H01B), C015(H01R,H01S), C016(H01C,H01D), C018(H01E,
 H01F), C01B(H01W,H01X)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00L(H00L), C00P(H00P), C00U(H00U), C00Z(H00Z),
 C012(H012), C017(H017)
2.c Idealised Me refined as rotating group:
 C01A(H01T,H01U,H01V), C01C(H01Y,H,HA), C01D(H01G,H01H,H01I), C01E(H01J,H01K,
 H01L), C01F(H01M,H01N,H01O), C01G(H01Z,HB,HC)
;
_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
O001 O 0.6414(2) 1.2796(7) 0.4139(2) 0.0623(10) Uani 1 1 d . . . . .
O002 O 0.45157(19) 0.4873(8) 0.46367(19) 0.0645(11) Uani 1 1 d . . . . .
O003 O 0.46579(18) 0.2961(9) 0.58980(19) 0.0668(11) Uani 1 1 d . . . . .
O004 O -0.0313(2) 0.1266(10) 0.2953(2) 0.0721(12) Uani 1 1 d . . . . .
O005 O 0.6455(2) 0.4270(8) 0.7043(2) 0.0660(11) Uani 1 1 d . . . . .
O006 O 0.9849(2) 0.0619(8) 0.5440(2) 0.0676(11) Uani 1 1 d . . . . .
O007 O 0.2190(2) -0.7211(8) 0.5919(2) 0.0694(11) Uani 1 1 d . . . . .
N008 N 0.7089(2) 0.5225(8) 0.6330(2) 0.0473(10) Uani 1 1 d . . . . .
O009 O 0.8931(2) 0.2848(9) 0.4205(2) 0.0688(11) Uani 1 1 d . . . . .
N00A N 0.0957(2) 0.0348(9) 0.3707(2) 0.0512(10) Uani 1 1 d . . . . .
O00B O 0.1774(3) -0.5333(10) 0.6699(3) 0.0931(15) Uani 1 1 d . . . . .
C00C C 0.8227(3) 0.5059(10) 0.4796(3) 0.0475(11) Uani 1 1 d . . . . .
H00C H 0.7907 0.5865 0.4350 0.057 Uiso 1 1 calc R . . . .
C00D C 0.9292(3) 0.2224(11) 0.5475(3) 0.0513(12) Uani 1 1 d . . . . .
C00E C 0.6995(3) 0.6992(9) 0.5748(2) 0.0433(11) Uani 1 1 d . . . . .
C00F C 0.3922(3) 0.3294(11) 0.4600(3) 0.0492(12) Uani 1 1 d . . . . .
C00G C 0.4010(3) 0.2242(11) 0.5287(3) 0.0490(12) Uani 1 1 d . . . . .
C00H C 0.8806(3) 0.3434(11) 0.4818(3) 0.0490(12) Uani 1 1 d . . . . .
C00I C 0.0176(3) 0.0006(13) 0.3465(3) 0.0600(15) Uani 1 1 d . . . . .
C00J C 0.3267(3) 0.2728(11) 0.3969(3) 0.0493(12) Uani 1 1 d . . . . .
H00J H 0.3209 0.3446 0.3519 0.059 Uiso 1 1 calc R . . . .
C00K C 0.2768(3) 0.0049(10) 0.4657(3) 0.0440(11) Uani 1 1 d . . . . .
C00L C 0.9175(3) 0.2647(10) 0.6105(3) 0.0514(13) Uani 1 1 d . . . . .
H00L H 0.9494 0.1802 0.6545 0.062 Uiso 1 1 calc R . . . .
C00M C 0.6571(3) 1.0761(10) 0.4665(3) 0.0510(12) Uani 1 1 d . . . . .
C00N C 0.8109(3) 0.5533(10) 0.5438(3) 0.0457(11) Uani 1 1 d . . . . .
C00O C 0.0849(3) -0.2965(11) 0.4441(3) 0.0535(13) Uani 1 1 d . . . . .
C00P C 0.7216(3) 0.9260(10) 0.4819(3) 0.0463(11) Uani 1 1 d . . . . .
H00P H 0.7508 0.9584 0.4558 0.056 Uiso 1 1 calc R . . . .
C00Q C 0.2172(3) -0.1657(10) 0.4714(3) 0.0450(11) Uani 1 1 d . . . . .
C00R C 0.6500(3) 0.5527(12) 0.6546(3) 0.0531(13) Uani 1 1 d . . . . .
C00S C 0.7452(2) 0.7250(10) 0.5358(2) 0.0445(11) Uani 1 1 d . . . . .
C00T C 0.1377(3) -0.1421(10) 0.4309(3) 0.0481(12) Uani 1 1 d . . . . .
C00U C 0.3433(3) 0.0621(10) 0.5299(3) 0.0476(12) Uani 1 1 d . . . . .
H00U H 0.3493 -0.0105 0.5749 0.057 Uiso 1 1 calc R . . . .
C00V C 0.8590(3) 0.4310(10) 0.6102(3) 0.0491(12) Uani 1 1 d . . . . .
C00W C 0.2125(4) -0.7073(12) 0.6558(3) 0.0648(15) Uani 1 1 d . . . . .
C00X C 0.2684(3) 0.1110(10) 0.3978(3) 0.0484(12) Uani 1 1 d . . . . .
C00Y C 0.6345(3) 0.8526(10) 0.5584(3) 0.0465(11) Uani 1 1 d . . . . .
C00Z C 0.6127(3) 1.0449(11) 0.5048(3) 0.0525(13) Uani 1 1 d . . . . .
H00Z H 0.5698 1.1499 0.4946 0.063 Uiso 1 1 calc R . . . .
C010 C 0.1965(3) 0.0698(12) 0.3277(3) 0.0569(14) Uani 1 1 d . . . . .
H01P H 0.1869 -0.1175 0.3193 0.068 Uiso 1 1 calc R . . . .
H01Q H 0.2039 0.1411 0.2861 0.068 Uiso 1 1 calc R . . . .
C011 C 0.8484(3) 0.4597(12) 0.6794(3) 0.0549(13) Uani 1 1 d . . . . .
H01A H 0.8503 0.6451 0.6918 0.066 Uiso 1 1 calc R . . . .
H01B H 0.8905 0.3724 0.7199 0.066 Uiso 1 1 calc R . . . .
C012 C 0.2400(3) -0.3641(10) 0.5264(3) 0.0516(12) Uani 1 1 d . . . . .
H012 H 0.2923 -0.3935 0.5550 0.062 Uiso 1 1 calc R . . . .
C013 C 0.5858(4) 1.2535(13) 0.3453(4) 0.0763(18) Uani 1 1 d . . . . .
C014 C 0.1882(3) -0.5143(10) 0.5392(3) 0.0568(14) Uani 1 1 d . . . . .
C015 C 0.1273(3) 0.2003(11) 0.3309(3) 0.0528(13) Uani 1 1 d . . . . .
H01R H 0.1423 0.3692 0.3558 0.063 Uiso 1 1 calc R . . . .
H01S H 0.0881 0.2314 0.2807 0.063 Uiso 1 1 calc R . . . .
C016 C 0.5987(3) 0.7715(12) 0.6091(3) 0.0557(14) Uani 1 1 d . . . . .
H01C H 0.5983 0.9167 0.6406 0.067 Uiso 1 1 calc R . . . .
H01D H 0.5464 0.7097 0.5808 0.067 Uiso 1 1 calc R . . . .
C017 C 0.1097(3) -0.4858(12) 0.4981(3) 0.0593(14) Uani 1 1 d . . . . .
H017 H 0.0751 -0.5915 0.5069 0.071 Uiso 1 1 calc R . . . .
C018 C 0.7724(3) 0.3444(11) 0.6723(3) 0.0528(13) Uani 1 1 d . . . . .
H01E H 0.7629 0.1784 0.6457 0.063 Uiso 1 1 calc R . . . .
H01F H 0.7759 0.3099 0.7215 0.063 Uiso 1 1 calc R . . . .
O019 O 0.5393(3) 1.0736(12) 0.3298(3) 0.116(2) Uani 1 1 d . . . . .
C01A C 0.4418(4) 0.6183(15) 0.3978(3) 0.0774(19) Uani 1 1 d . . . . .
H01T H 0.4381 0.4911 0.3608 0.116 Uiso 1 1 calc GR . . . .
H01U H 0.4851 0.7316 0.4080 0.116 Uiso 1 1 calc GR . . . .
H01V H 0.3955 0.7216 0.3799 0.116 Uiso 1 1 calc GR . . . .
C01B C 0.0046(3) -0.2165(13) 0.3914(3) 0.0679(17) Uani 1 1 d . . . . .
H01W H -0.0238 -0.1528 0.4181 0.082 Uiso 1 1 calc R . . . .
H01X H -0.0232 -0.3623 0.3598 0.082 Uiso 1 1 calc R . . . .
C01C C 0.4707(3) 0.2231(18) 0.6609(3) 0.089(2) Uani 1 1 d . . . . .
H01Y H 0.4648 0.0358 0.6626 0.133 Uiso 1 1 calc GR . . . .
H H 0.4305 0.3097 0.6689 0.133 Uiso 1 1 calc GR . . . .
HA H 0.5198 0.2748 0.6990 0.133 Uiso 1 1 calc GR . . . .
C01D C 0.8401(3) 0.3910(15) 0.3509(3) 0.0724(18) Uani 1 1 d . . . . .
H01G H 0.8574 0.3509 0.3135 0.109 Uiso 1 1 calc GR . . . .
H01H H 0.8372 0.5785 0.3551 0.109 Uiso 1 1 calc GR . . . .
H01I H 0.7902 0.3151 0.3371 0.109 Uiso 1 1 calc GR . . . .
C01E C 0.5840(4) 1.4706(14) 0.2963(3) 0.088(2) Uani 1 1 d . . . . .
H01J H 0.5950 1.6331 0.3236 0.131 Uiso 1 1 calc GR . . . .
H01K H 0.5340 1.4802 0.2551 0.131 Uiso 1 1 calc GR . . . .
H01L H 0.6220 1.4409 0.2780 0.131 Uiso 1 1 calc GR . . . .
C01F C 1.0308(3) -0.0874(14) 0.6095(4) 0.082(2) Uani 1 1 d . . . . .
H01M H 1.0674 -0.1917 0.6003 0.122 Uiso 1 1 calc GR . . . .
H01N H 0.9981 -0.2010 0.6217 0.122 Uiso 1 1 calc GR . . . .
H01O H 1.0577 0.0306 0.6502 0.122 Uiso 1 1 calc GR . . . .
C01G C 0.2526(4) -0.9305(13) 0.7054(4) 0.085(2) Uani 1 1 d . . . . .
H01Z H 0.2338 -1.0935 0.6795 0.128 Uiso 1 1 calc GR . . . .
HB H 0.2432 -0.9254 0.7489 0.128 Uiso 1 1 calc GR . . . .
HC H 0.3070 -0.9172 0.7199 0.128 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00M 1.408(6) . ?
O001 C013 1.330(7) . ?
O002 C00F 1.373(6) . ?
O002 C01A 1.409(6) . ?
O003 C00G 1.364(6) . ?
O003 C01C 1.428(6) . ?
O004 C00I 1.228(6) . ?
O005 C00R 1.214(6) . ?
O006 C00D 1.373(6) . ?
O006 C01F 1.437(7) . ?
O007 C00W 1.333(7) . ?
O007 C014 1.422(6) . ?
N008 C00E 1.415(6) . ?
N008 C00R 1.383(6) . ?
N008 C018 1.449(6) . ?
O009 C00H 1.374(6) . ?
O009 C01D 1.427(6) . ?
N00A C00I 1.378(6) . ?
N00A C00T 1.435(6) . ?
N00A C015 1.457(6) . ?
O00B C00W 1.217(8) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.373(7) . ?
C00C C00N 1.413(7) . ?
C00D C00H 1.382(7) . ?
C00D C00L 1.384(7) . ?
C00E C00S 1.408(6) . ?
C00E C00Y 1.390(6) . ?
C00F C00G 1.409(7) . ?
C00F C00J 1.372(7) . ?
C00G C00U 1.392(7) . ?
C00I C01B 1.507(8) . ?
C00J H00J 0.9300 . ?
C00J C00X 1.398(7) . ?
C00K C00Q 1.482(7) . ?
C00K C00U 1.394(7) . ?
C00K C00X 1.399(7) . ?
C00L H00L 0.9300 . ?
C00L C00V 1.406(7) . ?
C00M C00P 1.375(7) . ?
C00M C00Z 1.379(7) . ?
C00N C00S 1.488(7) . ?
C00N C00V 1.391(6) . ?
C00O C00T 1.398(7) . ?
C00O C017 1.366(8) . ?
C00O C01B 1.502(8) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.408(6) . ?
C00Q C00T 1.393(6) . ?
C00Q C012 1.411(7) . ?
C00R C016 1.503(8) . ?
C00U H00U 0.9300 . ?
C00V C011 1.487(7) . ?
C00W C01G 1.484(8) . ?
C00X C010 1.497(7) . ?
C00Y C00Z 1.373(7) . ?
C00Y C016 1.506(7) . ?
C00Z H00Z 0.9300 . ?
C010 H01P 0.9700 . ?
C010 H01Q 0.9700 . ?
C010 C015 1.515(7) . ?
C011 H01A 0.9700 . ?
C011 H01B 0.9700 . ?
C011 C018 1.525(7) . ?
C012 H012 0.9300 . ?
C012 C014 1.365(7) . ?
C013 O019 1.222(8) . ?
C013 C01E 1.464(9) . ?
C014 C017 1.381(7) . ?
C015 H01R 0.9700 . ?
C015 H01S 0.9700 . ?
C016 H01C 0.9700 . ?
C016 H01D 0.9700 . ?
C017 H017 0.9300 . ?
C018 H01E 0.9700 . ?
C018 H01F 0.9700 . ?
C01A H01T 0.9600 . ?
C01A H01U 0.9600 . ?
C01A H01V 0.9600 . ?
C01B H01W 0.9700 . ?
C01B H01X 0.9700 . ?
C01C H01Y 0.9600 . ?
C01C H 0.9600 . ?
C01C HA 0.9600 . ?
C01D H01G 0.9600 . ?
C01D H01H 0.9600 . ?
C01D H01I 0.9600 . ?
C01E H01J 0.9600 . ?
C01E H01K 0.9600 . ?
C01E H01L 0.9600 . ?
C01F H01M 0.9600 . ?
C01F H01N 0.9600 . ?
C01F H01O 0.9600 . ?
C01G H01Z 0.9600 . ?
C01G HB 0.9600 . ?
C01G HC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C013 O001 C00M 120.6(4) . . ?
C00F O002 C01A 117.0(4) . . ?
C00G O003 C01C 117.3(4) . . ?
C00D O006 C01F 117.1(4) . . ?
C00W O007 C014 119.0(5) . . ?
C00E N008 C018 128.1(4) . . ?
C00R N008 C00E 110.7(4) . . ?
C00R N008 C018 121.0(4) . . ?
C00H O009 C01D 117.2(4) . . ?
C00I N00A C00T 110.4(4) . . ?
C00I N00A C015 122.1(4) . . ?
C00T N00A C015 126.8(4) . . ?
C00H C00C H00C 119.3 . . ?
C00H C00C C00N 121.4(5) . . ?
C00N C00C H00C 119.3 . . ?
O006 C00D C00H 116.0(5) . . ?
O006 C00D C00L 125.1(5) . . ?
C00H C00D C00L 118.8(5) . . ?
C00S C00E N008 128.5(4) . . ?
C00Y C00E N008 109.3(4) . . ?
C00Y C00E C00S 122.2(4) . . ?
O002 C00F C00G 114.9(4) . . ?
C00J C00F O002 125.9(5) . . ?
C00J C00F C00G 119.2(5) . . ?
O003 C00G C00F 116.5(4) . . ?
O003 C00G C00U 124.9(4) . . ?
C00U C00G C00F 118.6(4) . . ?
O009 C00H C00D 116.0(4) . . ?
C00C C00H O009 123.6(4) . . ?
C00C C00H C00D 120.3(5) . . ?
O004 C00I N00A 123.7(6) . . ?
O004 C00I C01B 127.6(5) . . ?
N00A C00I C01B 108.7(5) . . ?
C00F C00J H00J 118.8 . . ?
C00F C00J C00X 122.5(5) . . ?
C00X C00J H00J 118.8 . . ?
C00U C00K C00Q 119.1(4) . . ?
C00U C00K C00X 118.8(4) . . ?
C00X C00K C00Q 122.0(4) . . ?
C00D C00L H00L 118.9 . . ?
C00D C00L C00V 122.2(5) . . ?
C00V C00L H00L 118.9 . . ?
C00P C00M O001 117.1(5) . . ?
C00P C00M C00Z 122.0(5) . . ?
C00Z C00M O001 120.7(5) . . ?
C00C C00N C00S 117.8(4) . . ?
C00V C00N C00C 118.8(4) . . ?
C00V C00N C00S 123.3(4) . . ?
C00T C00O C01B 109.2(5) . . ?
C017 C00O C00T 120.6(5) . . ?
C017 C00O C01B 130.3(5) . . ?
C00M C00P H00P 118.9 . . ?
C00M C00P C00S 122.3(5) . . ?
C00S C00P H00P 118.9 . . ?
C00T C00Q C00K 126.8(4) . . ?
C00T C00Q C012 114.1(4) . . ?
C012 C00Q C00K 119.0(4) . . ?
O005 C00R N008 123.6(5) . . ?
O005 C00R C016 128.3(5) . . ?
N008 C00R C016 108.0(5) . . ?
C00E C00S C00N 126.3(4) . . ?
C00E C00S C00P 114.6(4) . . ?
C00P C00S C00N 119.0(4) . . ?
C00O C00T N00A 108.4(4) . . ?
C00Q C00T N00A 128.3(5) . . ?
C00Q C00T C00O 123.3(5) . . ?
C00G C00U C00K 122.1(4) . . ?
C00G C00U H00U 118.9 . . ?
C00K C00U H00U 118.9 . . ?
C00L C00V C011 119.1(5) . . ?
C00N C00V C00L 118.4(5) . . ?
C00N C00V C011 122.4(4) . . ?
O007 C00W C01G 111.0(6) . . ?
O00B C00W O007 123.4(6) . . ?
O00B C00W C01G 125.6(6) . . ?
C00J C00X C00K 118.8(4) . . ?
C00J C00X C010 119.6(5) . . ?
C00K C00X C010 121.5(4) . . ?
C00E C00Y C016 108.5(4) . . ?
C00Z C00Y C00E 121.4(5) . . ?
C00Z C00Y C016 130.0(5) . . ?
C00M C00Z H00Z 121.3 . . ?
C00Y C00Z C00M 117.4(5) . . ?
C00Y C00Z H00Z 121.3 . . ?
C00X C010 H01P 109.2 . . ?
C00X C010 H01Q 109.2 . . ?
C00X C010 C015 112.1(4) . . ?
H01P C010 H01Q 107.9 . . ?
C015 C010 H01P 109.2 . . ?
C015 C010 H01Q 109.2 . . ?
C00V C011 H01A 109.0 . . ?
C00V C011 H01B 109.0 . . ?
C00V C011 C018 112.8(4) . . ?
H01A C011 H01B 107.8 . . ?
C018 C011 H01A 109.0 . . ?
C018 C011 H01B 109.0 . . ?
C00Q C012 H012 118.8 . . ?
C014 C012 C00Q 122.4(5) . . ?
C014 C012 H012 118.8 . . ?
O001 C013 C01E 112.8(6) . . ?
O019 C013 O001 120.7(6) . . ?
O019 C013 C01E 126.3(6) . . ?
C012 C014 O007 116.4(5) . . ?
C012 C014 C017 122.2(5) . . ?
C017 C014 O007 121.0(5) . . ?
N00A C015 C010 110.6(4) . . ?
N00A C015 H01R 109.5 . . ?
N00A C015 H01S 109.5 . . ?
C010 C015 H01R 109.5 . . ?
C010 C015 H01S 109.5 . . ?
H01R C015 H01S 108.1 . . ?
C00R C016 C00Y 103.5(4) . . ?
C00R C016 H01C 111.1 . . ?
C00R C016 H01D 111.1 . . ?
C00Y C016 H01C 111.1 . . ?
C00Y C016 H01D 111.1 . . ?
H01C C016 H01D 109.0 . . ?
C00O C017 C014 117.5(5) . . ?
C00O C017 H017 121.3 . . ?
C014 C017 H017 121.3 . . ?
N008 C018 C011 111.3(4) . . ?
N008 C018 H01E 109.4 . . ?
N008 C018 H01F 109.4 . . ?
C011 C018 H01E 109.4 . . ?
C011 C018 H01F 109.4 . . ?
H01E C018 H01F 108.0 . . ?
O002 C01A H01T 109.5 . . ?
O002 C01A H01U 109.5 . . ?
O002 C01A H01V 109.5 . . ?
H01T C01A H01U 109.5 . . ?
H01T C01A H01V 109.5 . . ?
H01U C01A H01V 109.5 . . ?
C00I C01B H01W 111.1 . . ?
C00I C01B H01X 111.1 . . ?
C00O C01B C00I 103.2(4) . . ?
C00O C01B H01W 111.1 . . ?
C00O C01B H01X 111.1 . . ?
H01W C01B H01X 109.1 . . ?
O003 C01C H01Y 109.5 . . ?
O003 C01C H 109.5 . . ?
O003 C01C HA 109.5 . . ?
H01Y C01C H 109.5 . . ?
H01Y C01C HA 109.5 . . ?
H C01C HA 109.5 . . ?
O009 C01D H01G 109.5 . . ?
O009 C01D H01H 109.5 . . ?
O009 C01D H01I 109.5 . . ?
H01G C01D H01H 109.5 . . ?
H01G C01D H01I 109.5 . . ?
H01H C01D H01I 109.5 . . ?
C013 C01E H01J 109.5 . . ?
C013 C01E H01K 109.5 . . ?
C013 C01E H01L 109.5 . . ?
H01J C01E H01K 109.5 . . ?
H01J C01E H01L 109.5 . . ?
H01K C01E H01L 109.5 . . ?
O006 C01F H01M 109.5 . . ?
O006 C01F H01N 109.5 . . ?
O006 C01F H01O 109.5 . . ?
H01M C01F H01N 109.5 . . ?
H01M C01F H01O 109.5 . . ?
H01N C01F H01O 109.5 . . ?
C00W C01G H01Z 109.5 . . ?
C00W C01G HB 109.5 . . ?
C00W C01G HC 109.5 . . ?
H01Z C01G HB 109.5 . . ?
H01Z C01G HC 109.5 . . ?
HB C01G HC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00M C00P C00S 177.0(4) . . . . ?
O001 C00M C00Z C00Y -176.0(4) . . . . ?
O002 C00F C00G O003 1.4(7) . . . . ?
O002 C00F C00G C00U 180.0(5) . . . . ?
O002 C00F C00J C00X -179.6(5) . . . . ?
O003 C00G C00U C00K 177.2(5) . . . . ?
O004 C00I C01B C00O 179.1(6) . . . . ?
O005 C00R C016 C00Y 178.5(5) . . . . ?
O006 C00D C00H O009 1.1(7) . . . . ?
O006 C00D C00H C00C 179.5(4) . . . . ?
O006 C00D C00L C00V -179.7(5) . . . . ?
O007 C014 C017 C00O -174.5(5) . . . . ?
N008 C00E C00S C00N 5.4(8) . . . . ?
N008 C00E C00S C00P -178.4(4) . . . . ?
N008 C00E C00Y C00Z 178.7(4) . . . . ?
N008 C00E C00Y C016 0.0(5) . . . . ?
N008 C00R C016 C00Y 1.7(5) . . . . ?
N00A C00I C01B C00O 0.7(6) . . . . ?
C00C C00N C00S C00E 145.9(5) . . . . ?
C00C C00N C00S C00P -30.2(7) . . . . ?
C00C C00N C00V C00L -0.1(7) . . . . ?
C00C C00N C00V C011 -177.1(5) . . . . ?
C00D C00L C00V C00N 0.9(7) . . . . ?
C00D C00L C00V C011 178.0(5) . . . . ?
C00E N008 C00R O005 -178.8(5) . . . . ?
C00E N008 C00R C016 -1.8(5) . . . . ?
C00E N008 C018 C011 33.1(7) . . . . ?
C00E C00Y C00Z C00M 1.4(7) . . . . ?
C00E C00Y C016 C00R -1.0(5) . . . . ?
C00F C00G C00U C00K -1.2(8) . . . . ?
C00F C00J C00X C00K 0.6(7) . . . . ?
C00F C00J C00X C010 176.5(5) . . . . ?
C00G C00F C00J C00X -0.8(8) . . . . ?
C00H C00C C00N C00S -178.0(4) . . . . ?
C00H C00C C00N C00V -0.3(7) . . . . ?
C00H C00D C00L C00V -1.4(8) . . . . ?
C00I N00A C00T C00O 1.2(5) . . . . ?
C00I N00A C00T C00Q -178.6(5) . . . . ?
C00I N00A C015 C010 -138.1(5) . . . . ?
C00J C00F C00G O003 -177.4(5) . . . . ?
C00J C00F C00G C00U 1.1(7) . . . . ?
C00J C00X C010 C015 -110.7(5) . . . . ?
C00K C00Q C00T N00A 5.8(8) . . . . ?
C00K C00Q C00T C00O -174.1(5) . . . . ?
C00K C00Q C012 C014 174.5(5) . . . . ?
C00K C00X C010 C015 65.1(6) . . . . ?
C00L C00D C00H O009 -177.3(5) . . . . ?
C00L C00D C00H C00C 1.1(8) . . . . ?
C00L C00V C011 C018 -113.1(5) . . . . ?
C00M O001 C013 O019 12.0(10) . . . . ?
C00M O001 C013 C01E -173.2(5) . . . . ?
C00M C00P C00S C00E -2.8(7) . . . . ?
C00M C00P C00S C00N 173.7(4) . . . . ?
C00N C00C C00H O009 178.0(5) . . . . ?
C00N C00C C00H C00D -0.3(8) . . . . ?
C00N C00V C011 C018 63.9(7) . . . . ?
C00P C00M C00Z C00Y -1.4(8) . . . . ?
C00Q C00K C00U C00G -178.9(5) . . . . ?
C00Q C00K C00X C00J 179.3(5) . . . . ?
C00Q C00K C00X C010 3.4(7) . . . . ?
C00Q C012 C014 O007 175.0(4) . . . . ?
C00Q C012 C014 C017 1.3(8) . . . . ?
C00R N008 C00E C00S -177.7(5) . . . . ?
C00R N008 C00E C00Y 1.2(5) . . . . ?
C00R N008 C018 C011 -141.3(5) . . . . ?
C00S C00E C00Y C00Z -2.3(7) . . . . ?
C00S C00E C00Y C016 179.0(4) . . . . ?
C00S C00N C00V C00L 177.5(4) . . . . ?
C00S C00N C00V C011 0.5(8) . . . . ?
C00T N00A C00I O004 -179.6(5) . . . . ?
C00T N00A C00I C01B -1.2(5) . . . . ?
C00T N00A C015 C010 31.5(6) . . . . ?
C00T C00O C017 C014 1.0(8) . . . . ?
C00T C00O C01B C00I 0.1(6) . . . . ?
C00T C00Q C012 C014 -1.3(7) . . . . ?
C00U C00K C00Q C00T 144.0(5) . . . . ?
C00U C00K C00Q C012 -31.1(7) . . . . ?
C00U C00K C00X C00J -0.7(7) . . . . ?
C00U C00K C00X C010 -176.5(5) . . . . ?
C00V C00N C00S C00E -31.7(7) . . . . ?
C00V C00N C00S C00P 152.1(5) . . . . ?
C00V C011 C018 N008 -79.4(6) . . . . ?
C00W O007 C014 C012 113.3(6) . . . . ?
C00W O007 C014 C017 -72.8(7) . . . . ?
C00X C00K C00Q C00T -35.9(7) . . . . ?
C00X C00K C00Q C012 148.9(5) . . . . ?
C00X C00K C00U C00G 1.0(7) . . . . ?
C00X C010 C015 N00A -81.7(5) . . . . ?
C00Y C00E C00S C00N -173.4(4) . . . . ?
C00Y C00E C00S C00P 2.9(6) . . . . ?
C00Z C00M C00P C00S 2.2(8) . . . . ?
C00Z C00Y C016 C00R -179.6(5) . . . . ?
C012 C00Q C00T N00A -178.9(4) . . . . ?
C012 C00Q C00T C00O 1.3(7) . . . . ?
C012 C014 C017 C00O -1.0(8) . . . . ?
C013 O001 C00M C00P 104.4(6) . . . . ?
C013 O001 C00M C00Z -80.7(7) . . . . ?
C014 O007 C00W O00B 4.4(9) . . . . ?
C014 O007 C00W C01G -176.1(5) . . . . ?
C015 N00A C00I O004 -8.5(8) . . . . ?
C015 N00A C00I C01B 170.0(5) . . . . ?
C015 N00A C00T C00O -169.4(5) . . . . ?
C015 N00A C00T C00Q 10.7(7) . . . . ?
C016 C00Y C00Z C00M 179.8(5) . . . . ?
C017 C00O C00T N00A 178.9(5) . . . . ?
C017 C00O C00T C00Q -1.2(8) . . . . ?
C017 C00O C01B C00I -179.6(5) . . . . ?
C018 N008 C00E C00S 7.4(8) . . . . ?
C018 N008 C00E C00Y -173.7(4) . . . . ?
C018 N008 C00R O005 -3.5(8) . . . . ?
C018 N008 C00R C016 173.5(4) . . . . ?
C01A O002 C00F C00G -173.7(5) . . . . ?
C01A O002 C00F C00J 5.1(8) . . . . ?
C01B C00O C00T N00A -0.8(5) . . . . ?
C01B C00O C00T C00Q 179.1(5) . . . . ?
C01B C00O C017 C014 -179.4(6) . . . . ?
C01C O003 C00G C00F 171.2(6) . . . . ?
C01C O003 C00G C00U -7.2(8) . . . . ?
C01D O009 C00H C00C -3.0(8) . . . . ?
C01D O009 C00H C00D 175.3(5) . . . . ?
C01F O006 C00D C00H -173.7(5) . . . . ?
C01F O006 C00D C00L 4.6(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
