# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

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

data_cu_2023946_0m
_database_code_depnum_ccdc_archive 'CCDC 2268989'
loop_
_audit_author_name
_audit_author_address
'Qiuyu Li'
;China Pharmacetical University
China
;
_audit_update_record             
;
2023-06-10 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4028(2)
_cell_length_b                   10.9104(3)
_cell_length_c                   17.5842(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1612.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.484
_cell_measurement_theta_min      5.030
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.925
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1520 before and 0.0973 after correction.
The Ratio of minimum to maximum transmission is 0.6731.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23262
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.470
_diffrn_reflns_theta_min         4.770
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3100
_reflns_number_total             3295
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.035
_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)+(0.0401P)²+0.2589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0865
_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)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C17(H17), C6(H6), C15(H15), C9(H9), C8(H8), C5(H5),
 C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56627(17) 0.61720(13) 0.57320(8) 0.0240(3) Uani 1 1 d . . . . .
O3 O 0.4309(2) 0.27571(14) 0.60035(10) 0.0336(4) Uani 1 1 d . . . . .
O2 O 0.6809(2) 0.34003(15) 0.61811(11) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.3020(2) 0.44883(15) 0.68727(9) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.2844(2) 0.56781(17) 0.58053(11) 0.0198(4) Uani 1 1 d . . . . .
C18 C 0.1999(2) 0.49861(17) 0.63493(11) 0.0197(4) Uani 1 1 d . . . . .
C12 C 0.4523(2) 0.56241(17) 0.59974(10) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.2050(2) 0.62919(17) 0.52193(11) 0.0213(4) Uani 1 1 d . . . . .
H14 H 0.262334 0.675693 0.485395 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4657(2) 0.46607(17) 0.66460(11) 0.0210(4) Uani 1 1 d . . . . .
C20 C 0.1361(2) 0.43814(18) 0.80314(11) 0.0225(4) Uani 1 1 d . . . . .
C16 C -0.0421(3) 0.55196(18) 0.57287(11) 0.0237(4) Uani 1 1 d . . . . .
H16 H -0.154849 0.547806 0.569643 0.028 Uiso 1 1 calc R U . . .
C17 C 0.0342(2) 0.49001(18) 0.63120(11) 0.0221(4) Uani 1 1 d . . . . .
H17 H -0.024065 0.443383 0.667345 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2576(3) 0.37373(18) 0.75226(11) 0.0230(4) Uani 1 1 d . . . . .
H7 H 0.212846 0.293988 0.734115 0.028 Uiso 1 1 calc R U . . .
C19 C 0.5404(3) 0.35269(18) 0.62640(11) 0.0237(4) Uani 1 1 d . . . . .
C6 C 0.0235(3) 0.36957(19) 0.84237(11) 0.0257(4) Uani 1 1 d . . . . .
H6 H 0.014602 0.284071 0.833077 0.031 Uiso 1 1 calc R U . . .
C15 C 0.0412(3) 0.62059(18) 0.51842(11) 0.0236(4) Uani 1 1 d . . . . .
H15 H -0.015243 0.661283 0.479006 0.028 Uiso 1 1 calc R U . . .
C10 C 0.5687(3) 0.5029(2) 0.73207(11) 0.0269(4) Uani 1 1 d . . . . .
H10A H 0.682472 0.502705 0.717502 0.032 Uiso 1 1 calc R U . . .
H10B H 0.539938 0.586195 0.749649 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5389(3) 0.4107(2) 0.79412(12) 0.0292(5) Uani 1 1 d . . . . .
H9 H 0.621012 0.395117 0.829980 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4025(3) 0.35023(18) 0.80075(12) 0.0280(5) Uani 1 1 d . . . . .
H8 H 0.395744 0.288123 0.838480 0.034 Uiso 1 1 calc R U . . .
C5 C -0.0760(3) 0.4253(2) 0.89513(12) 0.0293(5) Uani 1 1 d . . . . .
H5 H -0.151571 0.377587 0.922282 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0654(3) 0.5503(2) 0.90829(12) 0.0319(5) Uani 1 1 d . . . . .
H4 H -0.133185 0.588094 0.944620 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1456(3) 0.56425(19) 0.81638(12) 0.0282(4) Uani 1 1 d . . . . .
H2 H 0.221819 0.612109 0.789711 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0442(3) 0.6199(2) 0.86831(13) 0.0323(5) Uani 1 1 d . . . . .
H3 H 0.050082 0.705911 0.876452 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4929(3) 0.1714(2) 0.55799(17) 0.0421(6) Uani 1 1 d . . . . .
H21A H 0.574549 0.199513 0.522250 0.063 Uiso 1 1 calc R U . . .
H21B H 0.406092 0.132172 0.529795 0.063 Uiso 1 1 calc R U . . .
H21C H 0.539714 0.112175 0.593447 0.063 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 C12 1.222(2) . ?
O3 C19 1.327(3) . ?
O3 C21 1.457(3) . ?
O2 C19 1.198(3) . ?
N1 C18 1.370(3) . ?
N1 C11 1.444(3) . ?
N1 C7 1.455(2) . ?
C13 C18 1.410(3) . ?
C13 C12 1.452(3) . ?
C13 C14 1.398(3) . ?
C18 C17 1.397(3) . ?
C12 C11 1.555(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C11 C19 1.541(3) . ?
C11 C10 1.522(3) . ?
C20 C7 1.529(3) . ?
C20 C6 1.389(3) . ?
C20 C2 1.398(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C16 C15 1.403(3) . ?
C17 H17 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.509(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.389(3) . ?
C15 H15 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.505(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.327(3) . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O3 C21 115.02(18) . . ?
C18 N1 C11 111.04(15) . . ?
C18 N1 C7 126.17(17) . . ?
C11 N1 C7 122.31(16) . . ?
C18 C13 C12 108.02(16) . . ?
C14 C13 C18 121.08(18) . . ?
C14 C13 C12 130.88(17) . . ?
N1 C18 C13 110.67(17) . . ?
N1 C18 C17 128.96(19) . . ?
C17 C18 C13 120.36(18) . . ?
O1 C12 C13 130.79(17) . . ?
O1 C12 C11 123.64(18) . . ?
C13 C12 C11 105.57(16) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.41(18) . . ?
C15 C14 H14 120.8 . . ?
N1 C11 C12 102.80(15) . . ?
N1 C11 C19 113.80(16) . . ?
N1 C11 C10 111.13(16) . . ?
C19 C11 C12 104.62(15) . . ?
C10 C11 C12 115.75(16) . . ?
C10 C11 C19 108.65(17) . . ?
C6 C20 C7 119.85(17) . . ?
C6 C20 C2 119.11(19) . . ?
C2 C20 C7 120.78(18) . . ?
C17 C16 H16 118.8 . . ?
C17 C16 C15 122.32(19) . . ?
C15 C16 H16 118.8 . . ?
C18 C17 H17 121.2 . . ?
C16 C17 C18 117.60(19) . . ?
C16 C17 H17 121.2 . . ?
N1 C7 C20 111.85(16) . . ?
N1 C7 H7 109.6 . . ?
N1 C7 C8 109.42(17) . . ?
C20 C7 H7 109.6 . . ?
C8 C7 C20 106.65(16) . . ?
C8 C7 H7 109.6 . . ?
O3 C19 C11 112.08(17) . . ?
O2 C19 O3 124.65(19) . . ?
O2 C19 C11 123.16(19) . . ?
C20 C6 H6 119.8 . . ?
C20 C6 C5 120.37(19) . . ?
C5 C6 H6 119.8 . . ?
C14 C15 C16 120.22(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C9 C10 C11 107.11(17) . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
C10 C9 H9 118.7 . . ?
C8 C9 C10 122.6(2) . . ?
C8 C9 H9 118.7 . . ?
C7 C8 H8 117.9 . . ?
C9 C8 C7 124.26(19) . . ?
C9 C8 H8 117.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C20 C2 H2 119.8 . . ?
C3 C2 C20 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C12 C11 N1 167.66(17) . . . . ?
O1 C12 C11 C19 -73.2(2) . . . . ?
O1 C12 C11 C10 46.3(3) . . . . ?
N1 C18 C17 C16 178.48(18) . . . . ?
N1 C11 C19 O3 19.5(2) . . . . ?
N1 C11 C19 O2 -164.1(2) . . . . ?
N1 C11 C10 C9 51.8(2) . . . . ?
N1 C7 C8 C9 13.6(3) . . . . ?
C13 C18 C17 C16 -0.3(3) . . . . ?
C13 C12 C11 N1 -13.00(18) . . . . ?
C13 C12 C11 C19 106.14(17) . . . . ?
C13 C12 C11 C10 -134.33(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C18 N1 C11 C12 13.4(2) . . . . ?
C18 N1 C11 C19 -99.12(19) . . . . ?
C18 N1 C11 C10 137.84(17) . . . . ?
C18 N1 C7 C20 -55.3(2) . . . . ?
C18 N1 C7 C8 -173.23(18) . . . . ?
C18 C13 C12 O1 -172.24(19) . . . . ?
C18 C13 C12 C11 8.48(19) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C18 N1 -0.3(2) . . . . ?
C12 C13 C18 C17 178.65(18) . . . . ?
C12 C13 C14 C15 -178.26(19) . . . . ?
C12 C11 C19 O3 -91.88(19) . . . . ?
C12 C11 C19 O2 84.5(3) . . . . ?
C12 C11 C10 C9 168.53(17) . . . . ?
C14 C13 C18 N1 -178.96(17) . . . . ?
C14 C13 C18 C17 0.0(3) . . . . ?
C14 C13 C12 O1 6.2(3) . . . . ?
C14 C13 C12 C11 -173.08(19) . . . . ?
C11 N1 C18 C13 -8.9(2) . . . . ?
C11 N1 C18 C17 172.25(19) . . . . ?
C11 N1 C7 C20 133.38(19) . . . . ?
C11 N1 C7 C8 15.4(2) . . . . ?
C11 C10 C9 C8 -27.8(3) . . . . ?
C20 C7 C8 C9 -107.5(2) . . . . ?
C20 C6 C5 C4 0.9(3) . . . . ?
C20 C2 C3 C4 1.0(4) . . . . ?
C17 C16 C15 C14 -0.5(3) . . . . ?
C7 N1 C18 C13 178.96(17) . . . . ?
C7 N1 C18 C17 0.1(3) . . . . ?
C7 N1 C11 C12 -174.08(16) . . . . ?
C7 N1 C11 C19 73.4(2) . . . . ?
C7 N1 C11 C10 -49.6(2) . . . . ?
C7 C20 C6 C5 172.88(18) . . . . ?
C7 C20 C2 C3 -173.8(2) . . . . ?
C19 C11 C10 C9 -74.2(2) . . . . ?
C6 C20 C7 N1 148.01(18) . . . . ?
C6 C20 C7 C8 -92.4(2) . . . . ?
C6 C20 C2 C3 0.3(3) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C10 C11 C19 O3 143.93(18) . . . . ?
C10 C11 C19 O2 -39.7(3) . . . . ?
C10 C9 C8 C7 -5.6(3) . . . . ?
C5 C4 C3 C2 -1.4(4) . . . . ?
C2 C20 C7 N1 -38.0(3) . . . . ?
C2 C20 C7 C8 81.6(2) . . . . ?
C2 C20 C6 C5 -1.2(3) . . . . ?
C21 O3 C19 O2 -1.1(3) . . . . ?
C21 O3 C19 C11 175.17(19) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20232069_0m
_database_code_depnum_ccdc_archive 'CCDC 2321211'
loop_
_audit_author_name
_audit_author_address
'Qiuyu Li'
;China Pharmacetical University
China
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H40 N2 O5'
_chemical_formula_weight         604.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.3057(4)
_cell_length_b                   6.32680(10)
_cell_length_c                   16.4984(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.234(2)
_cell_angle_gamma                90
_cell_volume                     1597.27(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(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    1.257
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.665
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32890
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.679
_diffrn_reflns_theta_max         74.691
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6435
_reflns_number_gt                5877
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.995

_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-2019/2 (Sheldrick, 2019)'
_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)+(0.0433P)²+0.3862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6435
_refine_ls_number_parameters     417
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.004
_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 0.42420(12) 1.0289(3) 0.58608(11) 0.0290(4) Uani 1 1 d . . . . .
H3 H 0.434875 0.908681 0.567052 0.044 Uiso 1 1 calc R U . . .
O2 O -0.28041(12) 0.4737(3) 0.53647(11) 0.0284(4) Uani 1 1 d . . . . .
H2 H -0.327350 0.413481 0.548316 0.043 Uiso 1 1 calc R U . . .
O1 O -0.33878(14) 0.8799(3) 0.50917(12) 0.0354(5) Uani 1 1 d . . . . .
H1 H -0.340024 0.752855 0.494348 0.053 Uiso 1 1 calc R U . . .
O4 O 0.42416(12) 0.5955(3) 0.61058(11) 0.0294(4) Uani 1 1 d D . . . .
O5 O 0.56189(13) 1.3187(4) 0.57187(14) 0.0403(5) Uani 1 1 d G . . . .
H5A H 0.529764 1.206064 0.566120 0.060 Uiso 1 1 d G U . . .
H5B H 0.525540 1.416708 0.586372 0.060 Uiso 1 1 d G U . . .
N1 N -0.17390(13) 0.8223(3) 0.68086(13) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.33833(14) 0.8561(3) 0.78684(13) 0.0268(5) Uani 1 1 d . . . . .
C38 C 0.40763(17) 0.7348(4) 0.81808(16) 0.0267(5) Uani 1 1 d . . . . .
C14 C -0.13880(16) 0.5438(4) 0.59945(15) 0.0243(5) Uani 1 1 d . . . . .
C19 C -0.10516(17) 0.7139(4) 0.64475(15) 0.0244(5) Uani 1 1 d . . . . .
C11 C -0.25532(16) 0.7710(4) 0.63383(15) 0.0240(5) Uani 1 1 d . . . . .
C32 C 0.37858(17) 0.6220(4) 0.68450(15) 0.0257(5) Uani 1 1 d . . . . .
H32 H 0.328618 0.520335 0.685827 0.031 Uiso 1 1 calc R U . . .
C18 C -0.01502(17) 0.7446(5) 0.65027(16) 0.0295(6) Uani 1 1 d . . . . .
H18 H 0.009322 0.859977 0.679857 0.035 Uiso 1 1 calc R U . . .
C13 C -0.23663(16) 0.5408(4) 0.60832(15) 0.0231(5) Uani 1 1 d . . . . .
H13 H -0.251877 0.443610 0.653670 0.028 Uiso 1 1 calc R U . . .
C33 C 0.43581(17) 0.5919(4) 0.75944(15) 0.0257(5) Uani 1 1 d . . . . .
C10 C -0.33383(17) 0.7934(4) 0.68874(17) 0.0298(6) Uani 1 1 d . . . . .
H10A H -0.388109 0.800419 0.655116 0.036 Uiso 1 1 calc R U . . .
H10B H -0.337547 0.667916 0.724337 0.036 Uiso 1 1 calc R U . . .
C15 C -0.08575(18) 0.4056(4) 0.55947(16) 0.0285(5) Uani 1 1 d . . . . .
H15 H -0.110173 0.293102 0.528283 0.034 Uiso 1 1 calc R U . . .
C2 C -0.07674(19) 0.8979(5) 0.83459(17) 0.0339(6) Uani 1 1 d . . . . .
H2A H -0.107945 0.768264 0.831581 0.041 Uiso 1 1 calc R U . . .
C7 C -0.25269(19) 1.0973(5) 0.74979(17) 0.0336(6) Uani 1 1 d . . . . .
H7 H -0.254317 1.222073 0.781757 0.040 Uiso 1 1 calc R U . . .
C31 C 0.41233(16) 1.0126(4) 0.67113(15) 0.0254(5) Uani 1 1 d . . . . .
H31A H 0.395095 1.153082 0.691854 0.031 Uiso 1 1 calc R U . . .
H31B H 0.469128 0.975542 0.697226 0.031 Uiso 1 1 calc R U . . .
C20 C 0.34392(16) 0.8498(4) 0.69721(15) 0.0255(5) Uani 1 1 d . . . . .
C8 C -0.16595(17) 1.0360(4) 0.71368(16) 0.0275(5) Uani 1 1 d . . . . .
H8 H -0.152820 1.135589 0.668480 0.033 Uiso 1 1 calc R U . . .
C1 C -0.09499(17) 1.0563(4) 0.77894(16) 0.0284(5) Uani 1 1 d . . . . .
C23 C 0.2411(2) 1.1560(5) 0.77137(19) 0.0393(7) Uani 1 1 d . . . . .
H23 H 0.214580 1.281280 0.790884 0.047 Uiso 1 1 calc R U . . .
C25 C 0.27460(18) 1.0175(5) 0.90847(17) 0.0338(6) Uani 1 1 d . . . . .
C37 C 0.44758(19) 0.7404(5) 0.89467(16) 0.0348(6) Uani 1 1 d . . . . .
H37 H 0.428697 0.837014 0.934757 0.042 Uiso 1 1 calc R U . . .
C34 C 0.50434(18) 0.4546(4) 0.77595(17) 0.0309(6) Uani 1 1 d . . . . .
H34 H 0.523695 0.358721 0.735835 0.037 Uiso 1 1 calc R U . . .
C16 C 0.00473(19) 0.4327(5) 0.56534(18) 0.0339(6) Uani 1 1 d . . . . .
H16 H 0.042788 0.338200 0.538601 0.041 Uiso 1 1 calc R U . . .
C35 C 0.54437(19) 0.4600(5) 0.85262(19) 0.0373(6) Uani 1 1 d . . . . .
H35 H 0.591422 0.366723 0.865081 0.045 Uiso 1 1 calc R U . . .
C9 C -0.32597(19) 0.9898(5) 0.73999(18) 0.0352(6) Uani 1 1 d . . . . .
H9 H -0.376494 1.038839 0.766671 0.042 Uiso 1 1 calc R U . . .
C36 C 0.5158(2) 0.6009(5) 0.91083(18) 0.0392(7) Uani 1 1 d . . . . .
H36 H 0.543552 0.601913 0.962893 0.047 Uiso 1 1 calc R U . . .
C4 C 0.0319(2) 1.1158(6) 0.90073(19) 0.0446(8) Uani 1 1 d . . . . .
H4A H 0.075031 1.135679 0.942306 0.053 Uiso 1 1 calc R U . . .
C12 C -0.26223(18) 0.9163(4) 0.55880(16) 0.0295(6) Uani 1 1 d . . . . .
H12A H -0.262245 1.065314 0.577156 0.035 Uiso 1 1 calc R U . . .
H12B H -0.209898 0.895238 0.525503 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0488(2) 1.2454(5) 0.78476(19) 0.0358(6) Uani 1 1 d . . . . .
H6 H -0.060172 1.354942 0.746588 0.043 Uiso 1 1 calc R U . . .
C5 C 0.0137(2) 1.2754(5) 0.8457(2) 0.0430(7) Uani 1 1 d . . . . .
H5 H 0.044162 1.406039 0.849649 0.052 Uiso 1 1 calc R U . . .
C24 C 0.31111(18) 1.0534(4) 0.82423(17) 0.0303(6) Uani 1 1 d . . . . .
H24 H 0.362529 1.150532 0.828775 0.036 Uiso 1 1 calc R U . . .
C17 C 0.03823(18) 0.5999(5) 0.61085(17) 0.0343(6) Uani 1 1 d . . . . .
H17 H 0.099835 0.616509 0.615320 0.041 Uiso 1 1 calc R U . . .
C21 C 0.25376(18) 0.8940(5) 0.66055(18) 0.0334(6) Uani 1 1 d . . . . .
H21A H 0.258484 0.919533 0.601603 0.040 Uiso 1 1 calc R U . . .
H21B H 0.215588 0.769627 0.668248 0.040 Uiso 1 1 calc R U . . .
C22 C 0.21430(19) 1.0836(6) 0.70010(19) 0.0398(7) Uani 1 1 d . . . . .
H22 H 0.167825 1.154960 0.672556 0.048 Uiso 1 1 calc R U . . .
C3 C -0.0132(2) 0.9272(6) 0.89476(18) 0.0422(7) Uani 1 1 d . . . . .
H3A H -0.000538 0.816580 0.932147 0.051 Uiso 1 1 calc R U . . .
C26 C 0.2814(2) 1.1799(6) 0.96495(19) 0.0422(7) Uani 1 1 d . . . . .
H26 H 0.309921 1.307758 0.951014 0.051 Uiso 1 1 calc R U . . .
C30 C 0.2326(2) 0.8323(6) 0.9287(2) 0.0459(8) Uani 1 1 d . . . . .
H30 H 0.226688 0.721571 0.890050 0.055 Uiso 1 1 calc R U . . .
C29 C 0.1987(2) 0.8084(7) 1.0064(2) 0.0572(10) Uani 1 1 d . . . . .
H29 H 0.170930 0.680235 1.021166 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2468(2) 1.1568(7) 1.0417(2) 0.0543(10) Uani 1 1 d . . . . .
H27 H 0.251512 1.268488 1.080067 0.065 Uiso 1 1 calc R U . . .
C28 C 0.2060(3) 0.9726(8) 1.0616(2) 0.0596(11) Uani 1 1 d . . . . .
H28 H 0.182250 0.956888 1.113965 0.072 Uiso 1 1 calc R U . . .
H4 H 0.392(2) 0.523(6) 0.578(2) 0.052(11) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C31 1.422(3) . ?
O3 H3 0.8400 . ?
O2 C13 1.414(3) . ?
O2 H2 0.8400 . ?
O1 C12 1.434(3) . ?
O1 H1 0.8400 . ?
O4 C32 1.428(3) . ?
O4 H4 0.85(2) . ?
O5 H5A 0.8700 . ?
O5 H5B 0.8700 . ?
N1 C19 1.400(3) . ?
N1 C8 1.460(3) . ?
N1 C11 1.490(3) . ?
N2 C38 1.399(3) . ?
N2 C24 1.457(4) . ?
N2 C20 1.484(3) . ?
C38 C37 1.392(4) . ?
C38 C33 1.399(4) . ?
C14 C15 1.372(4) . ?
C14 C19 1.402(3) . ?
C14 C13 1.508(3) . ?
C19 C18 1.394(4) . ?
C11 C10 1.527(4) . ?
C11 C12 1.544(3) . ?
C11 C13 1.544(3) . ?
C32 C33 1.512(3) . ?
C32 C20 1.552(4) . ?
C32 H32 1.0000 . ?
C18 C17 1.395(4) . ?
C18 H18 0.9500 . ?
C13 H13 1.0000 . ?
C33 C34 1.384(4) . ?
C10 C9 1.506(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 C16 1.397(4) . ?
C15 H15 0.9500 . ?
C2 C1 1.383(4) . ?
C2 C3 1.387(4) . ?
C2 H2A 0.9500 . ?
C7 C9 1.319(4) . ?
C7 C8 1.517(4) . ?
C7 H7 0.9500 . ?
C31 C20 1.537(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C20 C21 1.521(4) . ?
C8 C1 1.518(4) . ?
C8 H8 1.0000 . ?
C1 C6 1.393(4) . ?
C23 C22 1.319(5) . ?
C23 C24 1.513(4) . ?
C23 H23 0.9500 . ?
C25 C30 1.380(5) . ?
C25 C26 1.390(5) . ?
C25 C24 1.526(4) . ?
C37 C36 1.389(4) . ?
C37 H37 0.9500 . ?
C34 C35 1.394(4) . ?
C34 H34 0.9500 . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C35 C36 1.388(5) . ?
C35 H35 0.9500 . ?
C9 H9 0.9500 . ?
C36 H36 0.9500 . ?
C4 C3 1.381(5) . ?
C4 C5 1.383(5) . ?
C4 H4A 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C6 C5 1.386(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C24 H24 1.0000 . ?
C17 H17 0.9500 . ?
C21 C22 1.499(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22 0.9500 . ?
C3 H3A 0.9500 . ?
C26 C27 1.391(5) . ?
C26 H26 0.9500 . ?
C30 C29 1.402(5) . ?
C30 H30 0.9500 . ?
C29 C28 1.383(7) . ?
C29 H29 0.9500 . ?
C27 C28 1.366(7) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

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
C31 O3 H3 109.5 . . ?
C13 O2 H2 109.5 . . ?
C12 O1 H1 109.5 . . ?
C32 O4 H4 108(3) . . ?
H5A O5 H5B 104.5 . . ?
C19 N1 C8 123.7(2) . . ?
C19 N1 C11 107.43(19) . . ?
C8 N1 C11 117.2(2) . . ?
C38 N2 C24 122.4(2) . . ?
C38 N2 C20 107.0(2) . . ?
C24 N2 C20 117.9(2) . . ?
C37 C38 N2 129.4(3) . . ?
C37 C38 C33 120.6(3) . . ?
N2 C38 C33 110.0(2) . . ?
C15 C14 C19 122.1(2) . . ?
C15 C14 C13 129.7(2) . . ?
C19 C14 C13 108.2(2) . . ?
C18 C19 N1 131.0(2) . . ?
C18 C19 C14 119.5(2) . . ?
N1 C19 C14 109.4(2) . . ?
N1 C11 C10 109.3(2) . . ?
N1 C11 C12 109.2(2) . . ?
C10 C11 C12 112.3(2) . . ?
N1 C11 C13 100.95(19) . . ?
C10 C11 C13 113.7(2) . . ?
C12 C11 C13 110.7(2) . . ?
O4 C32 C33 113.5(2) . . ?
O4 C32 C20 113.5(2) . . ?
C33 C32 C20 101.6(2) . . ?
O4 C32 H32 109.3 . . ?
C33 C32 H32 109.3 . . ?
C20 C32 H32 109.3 . . ?
C19 C18 C17 117.7(2) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
O2 C13 C14 112.1(2) . . ?
O2 C13 C11 115.1(2) . . ?
C14 C13 C11 101.83(19) . . ?
O2 C13 H13 109.2 . . ?
C14 C13 H13 109.2 . . ?
C11 C13 H13 109.2 . . ?
C34 C33 C38 120.9(2) . . ?
C34 C33 C32 131.5(2) . . ?
C38 C33 C32 107.6(2) . . ?
C9 C10 C11 110.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C14 C15 C16 119.0(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C9 C7 C8 124.7(3) . . ?
C9 C7 H7 117.7 . . ?
C8 C7 H7 117.7 . . ?
O3 C31 C20 115.3(2) . . ?
O3 C31 H31A 108.5 . . ?
C20 C31 H31A 108.5 . . ?
O3 C31 H31B 108.5 . . ?
C20 C31 H31B 108.5 . . ?
H31A C31 H31B 107.5 . . ?
N2 C20 C21 108.7(2) . . ?
N2 C20 C31 108.4(2) . . ?
C21 C20 C31 112.5(2) . . ?
N2 C20 C32 100.77(19) . . ?
C21 C20 C32 115.3(2) . . ?
C31 C20 C32 110.3(2) . . ?
N1 C8 C7 108.4(2) . . ?
N1 C8 C1 113.2(2) . . ?
C7 C8 C1 108.6(2) . . ?
N1 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C1 C8 H8 108.9 . . ?
C2 C1 C6 118.8(3) . . ?
C2 C1 C8 122.7(2) . . ?
C6 C1 C8 118.4(2) . . ?
C22 C23 C24 124.6(3) . . ?
C22 C23 H23 117.7 . . ?
C24 C23 H23 117.7 . . ?
C30 C25 C26 119.6(3) . . ?
C30 C25 C24 121.9(3) . . ?
C26 C25 C24 118.5(3) . . ?
C36 C37 C38 118.1(3) . . ?
C36 C37 H37 120.9 . . ?
C38 C37 H37 120.9 . . ?
C33 C34 C35 118.7(3) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C7 C9 C10 123.5(3) . . ?
C7 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C35 C36 C37 121.5(3) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
O1 C12 C11 113.8(2) . . ?
O1 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
O1 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N2 C24 C23 109.2(2) . . ?
N2 C24 C25 111.8(2) . . ?
C23 C24 C25 108.7(2) . . ?
N2 C24 H24 109.0 . . ?
C23 C24 H24 109.0 . . ?
C25 C24 H24 109.0 . . ?
C16 C17 C18 122.6(3) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 H17 118.7 . . ?
C22 C21 C20 110.2(2) . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 123.1(3) . . ?
C23 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C25 C30 C29 119.7(4) . . ?
C25 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C28 C29 C30 119.7(4) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C28 C27 C26 119.5(4) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.9(3) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?

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
C24 N2 C38 C37 17.4(4) . . . . ?
C20 N2 C38 C37 158.2(3) . . . . ?
C24 N2 C38 C33 -162.8(2) . . . . ?
C20 N2 C38 C33 -22.1(3) . . . . ?
C8 N1 C19 C18 19.9(4) . . . . ?
C11 N1 C19 C18 161.6(3) . . . . ?
C8 N1 C19 C14 -163.0(2) . . . . ?
C11 N1 C19 C14 -21.3(3) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C13 C14 C19 C18 176.5(2) . . . . ?
C15 C14 C19 N1 -177.9(2) . . . . ?
C13 C14 C19 N1 -1.0(3) . . . . ?
C19 N1 C11 C10 153.7(2) . . . . ?
C8 N1 C11 C10 -61.8(3) . . . . ?
C19 N1 C11 C12 -83.1(2) . . . . ?
C8 N1 C11 C12 61.5(3) . . . . ?
C19 N1 C11 C13 33.6(2) . . . . ?
C8 N1 C11 C13 178.1(2) . . . . ?
N1 C19 C18 C17 175.8(3) . . . . ?
C14 C19 C18 C17 -1.0(4) . . . . ?
C15 C14 C13 O2 -38.4(4) . . . . ?
C19 C14 C13 O2 145.1(2) . . . . ?
C15 C14 C13 C11 -161.9(3) . . . . ?
C19 C14 C13 C11 21.5(2) . . . . ?
N1 C11 C13 O2 -153.8(2) . . . . ?
C10 C11 C13 O2 89.3(3) . . . . ?
C12 C11 C13 O2 -38.2(3) . . . . ?
N1 C11 C13 C14 -32.3(2) . . . . ?
C10 C11 C13 C14 -149.2(2) . . . . ?
C12 C11 C13 C14 83.3(2) . . . . ?
C37 C38 C33 C34 -0.6(4) . . . . ?
N2 C38 C33 C34 179.7(2) . . . . ?
C37 C38 C33 C32 178.8(2) . . . . ?
N2 C38 C33 C32 -1.0(3) . . . . ?
O4 C32 C33 C34 -36.5(4) . . . . ?
C20 C32 C33 C34 -158.7(3) . . . . ?
O4 C32 C33 C38 144.3(2) . . . . ?
C20 C32 C33 C38 22.0(3) . . . . ?
N1 C11 C10 C9 42.9(3) . . . . ?
C12 C11 C10 C9 -78.5(3) . . . . ?
C13 C11 C10 C9 154.9(2) . . . . ?
C19 C14 C15 C16 1.2(4) . . . . ?
C13 C14 C15 C16 -174.9(3) . . . . ?
C38 N2 C20 C21 156.1(2) . . . . ?
C24 N2 C20 C21 -61.1(3) . . . . ?
C38 N2 C20 C31 -81.3(2) . . . . ?
C24 N2 C20 C31 61.5(3) . . . . ?
C38 N2 C20 C32 34.6(2) . . . . ?
C24 N2 C20 C32 177.3(2) . . . . ?
O3 C31 C20 N2 -178.8(2) . . . . ?
O3 C31 C20 C21 -58.6(3) . . . . ?
O3 C31 C20 C32 71.7(3) . . . . ?
O4 C32 C20 N2 -155.50(19) . . . . ?
C33 C32 C20 N2 -33.3(2) . . . . ?
O4 C32 C20 C21 87.7(3) . . . . ?
C33 C32 C20 C21 -150.1(2) . . . . ?
O4 C32 C20 C31 -41.1(3) . . . . ?
C33 C32 C20 C31 81.1(2) . . . . ?
C19 N1 C8 C7 -178.3(2) . . . . ?
C11 N1 C8 C7 43.4(3) . . . . ?
C19 N1 C8 C1 -57.8(3) . . . . ?
C11 N1 C8 C1 163.9(2) . . . . ?
C9 C7 C8 N1 -10.8(4) . . . . ?
C9 C7 C8 C1 -134.1(3) . . . . ?
C3 C2 C1 C6 -0.3(4) . . . . ?
C3 C2 C1 C8 -177.8(3) . . . . ?
N1 C8 C1 C2 -36.3(4) . . . . ?
C7 C8 C1 C2 84.1(3) . . . . ?
N1 C8 C1 C6 146.2(3) . . . . ?
C7 C8 C1 C6 -93.4(3) . . . . ?
N2 C38 C37 C36 179.7(3) . . . . ?
C33 C38 C37 C36 0.1(4) . . . . ?
C38 C33 C34 C35 0.6(4) . . . . ?
C32 C33 C34 C35 -178.6(3) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C33 C34 C35 C36 -0.1(4) . . . . ?
C8 C7 C9 C10 -2.1(5) . . . . ?
C11 C10 C9 C7 -14.9(4) . . . . ?
C34 C35 C36 C37 -0.4(5) . . . . ?
C38 C37 C36 C35 0.4(5) . . . . ?
N1 C11 C12 O1 -179.9(2) . . . . ?
C10 C11 C12 O1 -58.5(3) . . . . ?
C13 C11 C12 O1 69.8(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C8 C1 C6 C5 176.9(3) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C1 C6 C5 C4 1.1(5) . . . . ?
C38 N2 C24 C23 174.3(2) . . . . ?
C20 N2 C24 C23 37.6(3) . . . . ?
C38 N2 C24 C25 -65.4(3) . . . . ?
C20 N2 C24 C25 157.9(2) . . . . ?
C22 C23 C24 N2 -4.4(4) . . . . ?
C22 C23 C24 C25 -126.6(3) . . . . ?
C30 C25 C24 N2 -30.2(4) . . . . ?
C26 C25 C24 N2 152.3(3) . . . . ?
C30 C25 C24 C23 90.4(3) . . . . ?
C26 C25 C24 C23 -87.1(3) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C19 C18 C17 C16 1.7(4) . . . . ?
N2 C20 C21 C22 47.7(3) . . . . ?
C31 C20 C21 C22 -72.3(3) . . . . ?
C32 C20 C21 C22 159.9(2) . . . . ?
C24 C23 C22 C21 -3.2(5) . . . . ?
C20 C21 C22 C23 -19.7(4) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C30 C25 C26 C27 0.4(5) . . . . ?
C24 C25 C26 C27 178.1(3) . . . . ?
C26 C25 C30 C29 -1.2(5) . . . . ?
C24 C25 C30 C29 -178.8(3) . . . . ?
C25 C30 C29 C28 1.5(5) . . . . ?
C25 C26 C27 C28 0.1(5) . . . . ?
C26 C27 C28 C29 0.1(5) . . . . ?
C30 C29 C28 C27 -0.9(5) . . . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039



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

data_cu_20232096_0m
_database_code_depnum_ccdc_archive 'CCDC 2321444'
loop_
_audit_author_name
_audit_author_address
'Qiuyu Li'
;China Pharmacetical University
China
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2026-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-22
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4981(6)
_cell_length_b                   12.7136(8)
_cell_length_c                   15.5146(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1873.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.260
_cell_measurement_theta_min      4.495
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1686 before and 0.1194 after correction.
The Ratio of minimum to maximum transmission is 0.6244.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.765
_diffrn_reflns_theta_min         4.496
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3415
_reflns_number_total             3823
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.6024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1090
_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)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C8(H8), C2(H2), C22(H22), C20(H20), C6(H6), C4(H4), C5(H5), C9(H9),
 C21(H21), C3(H3A), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6767(2) 0.29672(18) 0.05863(12) 0.0463(5) Uani 1 1 d . . . . .
O2 O 0.7037(2) 0.14920(16) 0.23600(12) 0.0443(5) Uani 1 1 d . . . . .
N1 N 0.6206(2) 0.34319(18) 0.28310(14) 0.0361(5) Uani 1 1 d . . . . .
O1 O 0.8989(2) 0.2054(2) 0.17016(17) 0.0630(7) Uani 1 1 d . . . . .
C23 C 0.4911(3) 0.3091(2) 0.25203(17) 0.0344(6) Uani 1 1 d . . . . .
C18 C 0.4895(3) 0.3154(2) 0.16165(17) 0.0360(6) Uani 1 1 d . . . . .
C1 C 0.5827(3) 0.3896(2) 0.43566(17) 0.0361(6) Uani 1 1 d . . . . .
C19 C 0.3699(3) 0.2888(2) 0.11594(19) 0.0416(7) Uani 1 1 d . . . . .
H19 H 0.368507 0.294077 0.054865 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6305(3) 0.3562(2) 0.13119(17) 0.0387(6) Uani 1 1 d . . . . .
C8 C 0.8184(3) 0.3480(2) 0.38203(19) 0.0440(7) Uani 1 1 d . . . . .
H8 H 0.860844 0.332355 0.435969 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6652(3) 0.3237(2) 0.37150(16) 0.0377(6) Uani 1 1 d . . . . .
H7 H 0.649708 0.247644 0.385044 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5504(3) 0.4938(2) 0.41885(18) 0.0434(7) Uani 1 1 d . . . . .
H2 H 0.578813 0.524622 0.365848 0.052 Uiso 1 1 calc R U . . .
C22 C 0.3735(3) 0.2742(2) 0.29706(19) 0.0388(6) Uani 1 1 d . . . . .
H22 H 0.374431 0.269150 0.358149 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7870(3) 0.2237(2) 0.20384(18) 0.0424(6) Uani 1 1 d . . . . .
C20 C 0.2519(3) 0.2541(2) 0.1602(2) 0.0433(7) Uani 1 1 d . . . . .
H20 H 0.169255 0.235409 0.129360 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5442(3) 0.3470(3) 0.51437(18) 0.0420(7) Uani 1 1 d . . . . .
H6 H 0.567981 0.276127 0.527092 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7240(3) 0.3356(2) 0.21329(17) 0.0393(6) Uani 1 1 d . . . . .
C4 C 0.4376(3) 0.5089(3) 0.5568(2) 0.0458(7) Uani 1 1 d . . . . .
H4 H 0.386986 0.549476 0.597894 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4718(3) 0.4059(3) 0.57477(19) 0.0465(7) Uani 1 1 d . . . . .
H5 H 0.445763 0.375527 0.628390 0.056 Uiso 1 1 calc R U . . .
C10 C 0.8461(3) 0.4097(3) 0.2319(2) 0.0491(8) Uani 1 1 d . . . . .
H10A H 0.922890 0.397685 0.189865 0.059 Uiso 1 1 calc R U . . .
H10B H 0.814561 0.483639 0.226510 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6225(4) 0.4732(2) 0.10683(19) 0.0453(7) Uani 1 1 d . . . . .
H15A H 0.589119 0.513940 0.157227 0.054 Uiso 1 1 calc R U . . .
H15B H 0.717942 0.498642 0.091909 0.054 Uiso 1 1 calc R U . . .
C9 C 0.8985(3) 0.3897(3) 0.3215(2) 0.0506(8) Uani 1 1 d . . . . .
H9 H 0.992942 0.407641 0.335241 0.061 Uiso 1 1 calc R U . . .
C21 C 0.2539(3) 0.2466(2) 0.2498(2) 0.0444(7) Uani 1 1 d . . . . .
H21 H 0.172489 0.222358 0.279286 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7508(4) 0.0420(2) 0.2222(2) 0.0533(8) Uani 1 1 d . . . . .
H14A H 0.754313 0.027469 0.160181 0.080 Uiso 1 1 calc R U . . .
H14B H 0.684985 -0.006767 0.249912 0.080 Uiso 1 1 calc R U . . .
H14C H 0.844799 0.032956 0.247078 0.080 Uiso 1 1 calc R U . . .
C3 C 0.4770(3) 0.5537(2) 0.4787(2) 0.0455(7) Uani 1 1 d . . . . .
H3A H 0.453759 0.624746 0.466286 0.055 Uiso 1 1 calc R U . . .
C16 C 0.5263(4) 0.4923(3) 0.0327(2) 0.0500(8) Uani 1 1 d . . . . .
H16 H 0.552373 0.464398 -0.021821 0.060 Uiso 1 1 calc R U . . .
C17 C 0.4079(4) 0.5450(3) 0.0376(2) 0.0580(9) Uani 1 1 d . . . . .
H17A H 0.378647 0.573943 0.091132 0.070 Uiso 1 1 calc R U . . .
H17B H 0.351443 0.554227 -0.012357 0.070 Uiso 1 1 calc R U . . .
H3 H 0.759(5) 0.324(4) 0.041(3) 0.106(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C13 1.425(3) . ?
O3 H3 0.90(5) . ?
O2 C12 1.331(4) . ?
O2 C14 1.450(4) . ?
N1 C23 1.390(4) . ?
N1 C7 1.457(3) . ?
N1 C11 1.465(3) . ?
O1 C12 1.207(4) . ?
C23 C18 1.405(4) . ?
C23 C22 1.391(4) . ?
C18 C19 1.381(4) . ?
C18 C13 1.512(4) . ?
C1 C7 1.519(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.385(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(4) . ?
C13 C11 1.574(4) . ?
C13 C15 1.537(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.496(4) . ?
C8 C9 1.320(4) . ?
C7 H7 1.0000 . ?
C2 H2 0.9500 . ?
C2 C3 1.388(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.396(4) . ?
C12 C11 1.551(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.393(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.383(4) . ?
C11 C10 1.522(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(5) . ?
C4 C3 1.390(4) . ?
C5 H5 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.498(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.489(5) . ?
C9 H9 0.9500 . ?
C21 H21 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C3 H3A 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.311(5) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?

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
C13 O3 H3 107(3) . . ?
C12 O2 C14 115.5(2) . . ?
C23 N1 C7 122.1(2) . . ?
C23 N1 C11 108.4(2) . . ?
C7 N1 C11 119.3(2) . . ?
N1 C23 C18 109.8(2) . . ?
N1 C23 C22 129.5(2) . . ?
C22 C23 C18 120.7(3) . . ?
C23 C18 C13 108.8(2) . . ?
C19 C18 C23 120.5(3) . . ?
C19 C18 C13 130.7(2) . . ?
C2 C1 C7 121.2(3) . . ?
C6 C1 C7 119.9(3) . . ?
C6 C1 C2 118.8(3) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.2(3) . . ?
C20 C19 H19 120.4 . . ?
O3 C13 C18 109.7(2) . . ?
O3 C13 C11 112.2(2) . . ?
O3 C13 C15 109.5(2) . . ?
C18 C13 C11 100.9(2) . . ?
C18 C13 C15 111.4(2) . . ?
C15 C13 C11 112.8(2) . . ?
C7 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C9 C8 C7 124.5(3) . . ?
N1 C7 C1 111.9(2) . . ?
N1 C7 C8 110.5(2) . . ?
N1 C7 H7 108.6 . . ?
C1 C7 H7 108.6 . . ?
C8 C7 C1 108.4(2) . . ?
C8 C7 H7 108.6 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C23 C22 H22 121.0 . . ?
C23 C22 C21 118.0(3) . . ?
C21 C22 H22 121.0 . . ?
O2 C12 C11 112.8(2) . . ?
O1 C12 O2 123.3(3) . . ?
O1 C12 C11 123.9(3) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
N1 C11 C13 102.1(2) . . ?
N1 C11 C12 112.9(2) . . ?
N1 C11 C10 109.3(2) . . ?
C12 C11 C13 107.1(2) . . ?
C10 C11 C13 118.7(2) . . ?
C10 C11 C12 107.0(2) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C9 C10 C11 108.9(3) . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C13 C15 H15A 109.2 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 112.2(3) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C8 C9 C10 122.5(3) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C22 C21 H21 119.4 . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C15 C16 H16 117.8 . . ?
C17 C16 C15 124.4(3) . . ?
C17 C16 H16 117.8 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

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
O3 C13 C11 N1 -145.5(2) . . . . ?
O3 C13 C11 C12 -26.7(3) . . . . ?
O3 C13 C11 C10 94.4(3) . . . . ?
O3 C13 C15 C16 58.1(3) . . . . ?
O2 C12 C11 N1 23.3(3) . . . . ?
O2 C12 C11 C13 -88.2(3) . . . . ?
O2 C12 C11 C10 143.5(2) . . . . ?
N1 C23 C18 C19 -178.0(3) . . . . ?
N1 C23 C18 C13 0.6(3) . . . . ?
N1 C23 C22 C21 178.4(3) . . . . ?
N1 C11 C10 C9 51.3(3) . . . . ?
O1 C12 C11 N1 -157.4(3) . . . . ?
O1 C12 C11 C13 91.1(3) . . . . ?
O1 C12 C11 C10 -37.2(4) . . . . ?
C23 N1 C7 C1 -71.0(3) . . . . ?
C23 N1 C7 C8 168.0(2) . . . . ?
C23 N1 C11 C13 31.2(3) . . . . ?
C23 N1 C11 C12 -83.4(3) . . . . ?
C23 N1 C11 C10 157.7(2) . . . . ?
C23 C18 C19 C20 -0.9(4) . . . . ?
C23 C18 C13 O3 136.5(2) . . . . ?
C23 C18 C13 C11 17.9(3) . . . . ?
C23 C18 C13 C15 -102.1(3) . . . . ?
C23 C22 C21 C20 -0.2(5) . . . . ?
C18 C23 C22 C21 -0.6(4) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C18 C13 C11 N1 -28.7(3) . . . . ?
C18 C13 C11 C12 90.1(2) . . . . ?
C18 C13 C11 C10 -148.8(3) . . . . ?
C18 C13 C15 C16 -63.5(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C6 C5 C4 -0.3(5) . . . . ?
C19 C18 C13 O3 -45.1(4) . . . . ?
C19 C18 C13 C11 -163.7(3) . . . . ?
C19 C18 C13 C15 76.3(4) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C13 C18 C19 C20 -179.2(3) . . . . ?
C13 C11 C10 C9 167.6(3) . . . . ?
C13 C15 C16 C17 113.9(4) . . . . ?
C7 N1 C23 C18 -165.8(2) . . . . ?
C7 N1 C23 C22 15.1(4) . . . . ?
C7 N1 C11 C13 177.2(2) . . . . ?
C7 N1 C11 C12 62.6(3) . . . . ?
C7 N1 C11 C10 -56.3(3) . . . . ?
C7 C1 C2 C3 -178.9(3) . . . . ?
C7 C1 C6 C5 178.6(3) . . . . ?
C7 C8 C9 C10 -4.9(5) . . . . ?
C2 C1 C7 N1 -41.1(4) . . . . ?
C2 C1 C7 C8 81.1(3) . . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C22 C23 C18 C19 1.2(4) . . . . ?
C22 C23 C18 C13 179.7(3) . . . . ?
C12 C11 C10 C9 -71.2(3) . . . . ?
C6 C1 C7 N1 142.0(3) . . . . ?
C6 C1 C7 C8 -95.8(3) . . . . ?
C6 C1 C2 C3 -2.0(4) . . . . ?
C11 N1 C23 C18 -21.0(3) . . . . ?
C11 N1 C23 C22 160.0(3) . . . . ?
C11 N1 C7 C1 147.7(2) . . . . ?
C11 N1 C7 C8 26.8(3) . . . . ?
C11 C13 C15 C16 -176.2(2) . . . . ?
C11 C10 C9 C8 -24.4(5) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C15 C13 C11 N1 90.2(3) . . . . ?
C15 C13 C11 C12 -151.0(2) . . . . ?
C15 C13 C11 C10 -29.9(4) . . . . ?
C9 C8 C7 N1 5.3(4) . . . . ?
C9 C8 C7 C1 -117.7(3) . . . . ?
C14 O2 C12 O1 -4.6(4) . . . . ?
C14 O2 C12 C11 174.7(2) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
