# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 2243178'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-20 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3899(2)
_cell_length_b                   17.2182(5)
_cell_length_c                   11.7013(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.7210(10)
_cell_angle_gamma                90
_cell_volume                     1678.74(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      74.34
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3134
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            32515
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.453
_diffrn_reflns_theta_min         4.590
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3219
_reflns_number_total             3418
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         0.249
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+0.2465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1400
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 C12, C13
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 0.61333(12) 0.42746(8) 0.86889(9) 0.0792(4) Uani 1 1 d . . . . .
O2 O 0.62329(10) 0.43370(6) 0.62683(8) 0.0608(3) Uani 1 1 d . . . . .
N1 N 0.48758(13) 0.43235(7) 0.68411(10) 0.0608(3) Uani 1 1 d . . . . .
C1 C 0.49382(15) 0.42845(8) 0.79948(11) 0.0553(3) Uani 1 1 d . . . . .
C2 C 0.32209(16) 0.42814(7) 0.81894(13) 0.0585(3) Uani 1 1 d . . . . .
C3 C 0.22695(15) 0.43232(7) 0.71411(14) 0.0605(4) Uani 1 1 d . . . . .
C4 C 0.33052(15) 0.43259(7) 0.61713(12) 0.0561(3) Uani 1 1 d . . . . .
H4 H 0.315418 0.481696 0.574919 0.067 Uiso 1 1 calc R U . . .
C5 C 0.31348(16) 0.36384(8) 0.53016(12) 0.0582(3) Uani 1 1 d . . . . .
C6 C 0.46901(17) 0.36295(7) 0.47010(11) 0.0574(3) Uani 1 1 d . . . . .
H6 H 0.468572 0.410234 0.423443 0.069 Uiso 1 1 calc R U . . .
C7 C 0.61908(16) 0.36516(8) 0.55542(11) 0.0587(3) Uani 1 1 d . . . . .
H7A H 0.622747 0.319268 0.603741 0.070 Uiso 1 1 calc R U . . .
H7B H 0.712797 0.364505 0.514112 0.070 Uiso 1 1 calc R U . . .
C8 C 0.4815(2) 0.29336(10) 0.38830(14) 0.0765(5) Uani 1 1 d . . . . .
H8A H 0.501695 0.246555 0.433817 0.092 Uiso 1 1 calc R U . . .
H8B H 0.379564 0.286911 0.340845 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6123(2) 0.30271(9) 0.31120(12) 0.0689(4) Uani 1 1 d . . . . .
C10 C 0.7507(2) 0.25829(10) 0.32706(13) 0.0767(4) Uani 1 1 d . . . . .
H10 H 0.762958 0.222121 0.386470 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8706(2) 0.26636(12) 0.25699(16) 0.0864(5) Uani 1 1 d . . . . .
H11 H 0.962610 0.235972 0.269898 0.104 Uiso 1 1 calc R U . . .
C12 C 0.8554(3) 0.31850(12) 0.16901(17) 0.0963(6) Uani 1 1 d . U . . .
H12 H 0.936602 0.323790 0.121826 0.116 Uiso 1 1 calc R U . . .
C13 C 0.7196(3) 0.36317(11) 0.15043(15) 0.0940(6) Uani 1 1 d . U . . .
H13 H 0.708482 0.398575 0.089996 0.113 Uiso 1 1 calc R U . . .
C14 C 0.5979(3) 0.35593(10) 0.22155(14) 0.0820(5) Uani 1 1 d . . . . .
H14 H 0.506817 0.386925 0.208778 0.098 Uiso 1 1 calc R U . . .
C15 C 0.1693(2) 0.38103(13) 0.44073(17) 0.0937(6) Uani 1 1 d . . . . .
H15A H 0.189130 0.427674 0.399728 0.141 Uiso 1 1 calc R U . . .
H15B H 0.074931 0.387695 0.478889 0.141 Uiso 1 1 calc R U . . .
H15C H 0.153415 0.338499 0.387569 0.141 Uiso 1 1 calc R U . . .
C16 C 0.2885(2) 0.28746(9) 0.59221(15) 0.0740(4) Uani 1 1 d . . . . .
H16A H 0.284805 0.245332 0.538230 0.111 Uiso 1 1 calc R U . . .
H16B H 0.189355 0.289607 0.625534 0.111 Uiso 1 1 calc R U . . .
H16C H 0.375732 0.279481 0.651840 0.111 Uiso 1 1 calc R U . . .
C17 C 0.06099(18) 0.43674(10) 0.71208(19) 0.0835(5) Uani 1 1 d . . . . .
H17 H -0.005092 0.441008 0.642790 0.100 Uiso 1 1 calc R U . . .
C18 C -0.0031(2) 0.43464(11) 0.8153(2) 0.0993(7) Uani 1 1 d . . . . .
H18 H -0.113814 0.437247 0.815128 0.119 Uiso 1 1 calc R U . . .
C19 C 0.0932(3) 0.42877(10) 0.9189(2) 0.0927(6) Uani 1 1 d . . . . .
H19 H 0.046319 0.426488 0.987021 0.111 Uiso 1 1 calc R U . . .
C20 C 0.2591(2) 0.42621(9) 0.92280(16) 0.0763(5) Uani 1 1 d . . . . .
H20 H 0.325004 0.423323 0.992336 0.092 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 C1 1.2144(17) . ?
O2 N1 1.3874(13) . ?
O2 C7 1.4441(16) . ?
N1 C1 1.3465(18) . ?
N1 C4 1.4522(16) . ?
C1 C2 1.4848(18) . ?
C2 C3 1.385(2) . ?
C2 C20 1.381(2) . ?
C3 C4 1.508(2) . ?
C3 C17 1.3919(19) . ?
C4 H4 0.9800 . ?
C4 C5 1.5567(19) . ?
C5 C6 1.553(2) . ?
C5 C15 1.533(2) . ?
C5 C16 1.5284(19) . ?
C6 H6 0.9800 . ?
C6 C7 1.5130(19) . ?
C6 C8 1.5447(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.509(2) . ?
C9 C10 1.384(3) . ?
C9 C14 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9300 . ?

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
N1 O2 C7 107.46(9) . . ?
O2 N1 C4 118.90(11) . . ?
C1 N1 O2 123.19(10) . . ?
C1 N1 C4 117.88(11) . . ?
O1 C1 N1 127.12(12) . . ?
O1 C1 C2 129.60(13) . . ?
N1 C1 C2 103.26(11) . . ?
C3 C2 C1 109.45(12) . . ?
C20 C2 C1 127.81(15) . . ?
C20 C2 C3 122.71(14) . . ?
C2 C3 C4 110.10(11) . . ?
C2 C3 C17 119.32(16) . . ?
C17 C3 C4 130.58(16) . . ?
N1 C4 C3 99.22(11) . . ?
N1 C4 H4 109.3 . . ?
N1 C4 C5 111.02(11) . . ?
C3 C4 H4 109.3 . . ?
C3 C4 C5 118.22(11) . . ?
C5 C4 H4 109.3 . . ?
C6 C5 C4 106.60(10) . . ?
C15 C5 C4 107.71(13) . . ?
C15 C5 C6 109.32(13) . . ?
C16 C5 C4 110.54(12) . . ?
C16 C5 C6 112.06(12) . . ?
C16 C5 C15 110.45(13) . . ?
C5 C6 H6 107.2 . . ?
C7 C6 C5 112.30(10) . . ?
C7 C6 H6 107.2 . . ?
C7 C6 C8 108.47(12) . . ?
C8 C6 C5 114.18(11) . . ?
C8 C6 H6 107.2 . . ?
O2 C7 C6 111.37(11) . . ?
O2 C7 H7A 109.4 . . ?
O2 C7 H7B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C6 C8 H8A 108.9 . . ?
C6 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C6 113.24(12) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C10 C9 C8 121.21(14) . . ?
C10 C9 C14 117.63(16) . . ?
C14 C9 C8 121.16(17) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.59(16) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.52(19) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.50(17) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.30(19) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C17 H17 120.8 . . ?
C18 C17 C3 118.37(19) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.58(16) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.87(18) . . ?
C20 C19 H19 119.6 . . ?
C2 C20 C19 117.1(2) . . ?
C2 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?

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 C1 C2 C3 177.97(14) . . . . ?
O1 C1 C2 C20 -0.4(2) . . . . ?
O2 N1 C1 O1 1.9(2) . . . . ?
O2 N1 C1 C2 -179.74(11) . . . . ?
O2 N1 C4 C3 -179.02(10) . . . . ?
O2 N1 C4 C5 55.84(15) . . . . ?
N1 O2 C7 C6 59.00(13) . . . . ?
N1 C1 C2 C3 -0.34(14) . . . . ?
N1 C1 C2 C20 -178.70(14) . . . . ?
N1 C4 C5 C6 -46.51(14) . . . . ?
N1 C4 C5 C15 -163.73(13) . . . . ?
N1 C4 C5 C16 75.52(15) . . . . ?
C1 N1 C4 C3 2.95(15) . . . . ?
C1 N1 C4 C5 -122.19(13) . . . . ?
C1 C2 C3 C4 2.17(15) . . . . ?
C1 C2 C3 C17 -176.81(12) . . . . ?
C1 C2 C20 C19 178.07(14) . . . . ?
C2 C3 C4 N1 -2.92(13) . . . . ?
C2 C3 C4 C5 117.06(12) . . . . ?
C2 C3 C17 C18 -1.7(2) . . . . ?
C3 C2 C20 C19 -0.1(2) . . . . ?
C3 C4 C5 C6 -160.15(11) . . . . ?
C3 C4 C5 C15 82.62(15) . . . . ?
C3 C4 C5 C16 -38.13(16) . . . . ?
C3 C17 C18 C19 0.4(3) . . . . ?
C4 N1 C1 O1 179.83(14) . . . . ?
C4 N1 C1 C2 -1.80(15) . . . . ?
C4 C3 C17 C18 179.51(15) . . . . ?
C4 C5 C6 C7 50.45(14) . . . . ?
C4 C5 C6 C8 174.48(11) . . . . ?
C5 C6 C7 O2 -59.03(14) . . . . ?
C5 C6 C8 C9 166.95(13) . . . . ?
C6 C8 C9 C10 109.13(16) . . . . ?
C6 C8 C9 C14 -71.14(19) . . . . ?
C7 O2 N1 C1 117.66(13) . . . . ?
C7 O2 N1 C4 -60.27(14) . . . . ?
C7 C6 C8 C9 -66.99(17) . . . . ?
C8 C6 C7 O2 173.83(10) . . . . ?
C8 C9 C10 C11 179.91(14) . . . . ?
C8 C9 C14 C13 -179.36(14) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C15 C5 C6 C7 166.61(13) . . . . ?
C15 C5 C6 C8 -69.37(16) . . . . ?
C16 C5 C6 C7 -70.61(14) . . . . ?
C16 C5 C6 C8 53.42(16) . . . . ?
C17 C3 C4 N1 175.92(14) . . . . ?
C17 C3 C4 C5 -64.11(19) . . . . ?
C17 C18 C19 C20 1.2(3) . . . . ?
C18 C19 C20 C2 -1.3(2) . . . . ?
C20 C2 C3 C4 -179.37(12) . . . . ?
C20 C2 C3 C17 1.6(2) . . . . ?

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

data_cu_0203_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2244762'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9121(3)
_cell_length_b                   9.1248(3)
_cell_length_c                   11.9813(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4770(10)
_cell_angle_gamma                90
_cell_volume                     847.71(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.66
_cell_measurement_theta_min      4.85
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1032 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.1365.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14417
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.655
_diffrn_reflns_theta_min         6.142
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3352
_reflns_number_total             3392
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.091
_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)+(0.1117P)²+0.0304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00K(H00P), C00L(H00Q)
1.b Secondary CH2 refined with riding coordinates:
 C00B(H00E,H00F), C00H(H00M,H00N), C00M(H00R,H00S)
1.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C00A(H00D), C00C(H00G), C00D(H00H), C00E(H00I),
 C00J(H00O), C00N(H00T), C00O(H00U)
1.d Idealised Me refined as rotating group:
 C006(H00A,H00B,H00C), C00F(H00J,H00K,H00L)
;
_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 0.6227(2) 0.4847(2) 0.63515(14) 0.0554(4) Uani 1 1 d . . . . .
O002 O 0.6038(2) 0.3539(2) 0.43598(15) 0.0553(4) Uani 1 1 d . . . . .
N003 N 0.4599(2) 0.3613(2) 0.48772(17) 0.0494(5) Uani 1 1 d . . . . .
C004 C 0.4826(3) 0.4408(3) 0.58594(19) 0.0489(5) Uani 1 1 d . . . . .
C005 C 0.3213(3) 0.4662(3) 0.63079(19) 0.0477(5) Uani 1 1 d . . . . .
C006 C 0.2144(3) 0.6018(3) 0.3575(2) 0.0534(5) Uani 1 1 d . . . . .
H00A H 0.196678 0.674422 0.296056 0.080 Uiso 1 1 calc R U . . .
H00B H 0.306335 0.635243 0.419617 0.080 Uiso 1 1 calc R U . . .
H00C H 0.107387 0.589624 0.385964 0.080 Uiso 1 1 calc R U . . .
C007 C 0.3318(3) 0.5528(3) 0.7270(2) 0.0511(5) Uani 1 1 d . . . . .
H007 H 0.439575 0.592930 0.763333 0.061 Uiso 1 1 calc R U . . .
C008 C 0.7129(4) 0.6900(3) 0.1346(2) 0.0602(6) Uani 1 1 d . . . . .
H008 H 0.717035 0.761333 0.192883 0.072 Uiso 1 1 calc R U . . .
C009 C 0.1626(3) 0.4070(3) 0.5751(2) 0.0485(5) Uani 1 1 d . . . . .
C00A C 0.0276(3) 0.5220(3) 0.7157(2) 0.0543(6) Uani 1 1 d . . . . .
H00D H -0.073280 0.540580 0.745058 0.065 Uiso 1 1 calc R U . . .
C00B C 0.1545(3) 0.3098(3) 0.4730(2) 0.0522(5) Uani 1 1 d . . . . .
H00E H 0.041949 0.325052 0.420971 0.063 Uiso 1 1 calc R U . . .
H00F H 0.158884 0.206429 0.498597 0.063 Uiso 1 1 calc R U . . .
C00C C 0.8414(4) 0.6876(4) 0.0713(2) 0.0660(7) Uani 1 1 d . . . . .
H00G H 0.932309 0.757402 0.085775 0.079 Uiso 1 1 calc R U . . .
C00D C 0.0168(3) 0.4364(3) 0.6188(2) 0.0516(5) Uani 1 1 d . . . . .
H00H H -0.091536 0.397658 0.582165 0.062 Uiso 1 1 calc R U . . .
C00E C 0.1847(3) 0.5809(3) 0.7703(2) 0.0549(5) Uani 1 1 d . . . . .
H00I H 0.191212 0.639706 0.836455 0.066 Uiso 1 1 calc R U . . .
C00F C 0.1203(4) 0.3998(3) 0.2170(2) 0.0609(6) Uani 1 1 d . . . . .
H00J H 0.012423 0.395479 0.245311 0.091 Uiso 1 1 calc R U . . .
H00K H 0.148827 0.301784 0.192833 0.091 Uiso 1 1 calc R U . . .
H00L H 0.106537 0.467098 0.152055 0.091 Uiso 1 1 calc R U . . .
C00G C 0.2659(3) 0.4546(3) 0.3120(2) 0.0507(5) Uani 1 1 d . . . . .
C00H C 0.5947(3) 0.4757(3) 0.3584(2) 0.0556(6) Uani 1 1 d . . . . .
H00M H 0.698986 0.476335 0.324425 0.067 Uiso 1 1 calc R U . . .
H00N H 0.592485 0.568452 0.400969 0.067 Uiso 1 1 calc R U . . .
C00I C 0.5788(3) 0.5905(3) 0.1147(2) 0.0564(6) Uani 1 1 d . . . . .
C00J C 0.5766(4) 0.4856(4) 0.0300(2) 0.0674(7) Uani 1 1 d . . . . .
H00O H 0.485778 0.415875 0.015268 0.081 Uiso 1 1 calc R U . . .
C00K C 0.2982(3) 0.3344(3) 0.4061(2) 0.0496(5) Uani 1 1 d . . . . .
H00P H 0.313112 0.239788 0.367097 0.059 Uiso 1 1 calc R U . . .
C00L C 0.4344(3) 0.4667(3) 0.2637(2) 0.0525(5) Uani 1 1 d . . . . .
H00Q H 0.444155 0.375039 0.219687 0.063 Uiso 1 1 calc R U . . .
C00M C 0.4349(3) 0.5961(3) 0.1818(2) 0.0581(6) Uani 1 1 d . . . . .
H00R H 0.322749 0.598568 0.127611 0.070 Uiso 1 1 calc R U . . .
H00S H 0.445456 0.688324 0.226268 0.070 Uiso 1 1 calc R U . . .
C00N C 0.7059(4) 0.4820(4) -0.0332(2) 0.0736(8) Uani 1 1 d . . . . .
H00T H 0.703812 0.409452 -0.090310 0.088 Uiso 1 1 calc R U . . .
C00O C 0.8372(4) 0.5838(4) -0.0129(2) 0.0680(7) Uani 1 1 d . . . . .
H00U H 0.924787 0.582457 -0.056839 0.082 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
O001 C004 1.215(3) . ?
O002 N003 1.402(2) . ?
O002 C00H 1.441(3) . ?
N003 C004 1.364(3) . ?
N003 C00K 1.468(3) . ?
C004 C005 1.498(3) . ?
C005 C007 1.387(3) . ?
C005 C009 1.407(3) . ?
C006 H00A 0.9800 . ?
C006 H00B 0.9800 . ?
C006 H00C 0.9800 . ?
C006 C00G 1.535(3) . ?
C007 H007 0.9500 . ?
C007 C00E 1.389(3) . ?
C008 H008 0.9500 . ?
C008 C00C 1.385(4) . ?
C008 C00I 1.380(4) . ?
C009 C00B 1.502(3) . ?
C009 C00D 1.385(3) . ?
C00A H00D 0.9500 . ?
C00A C00D 1.387(4) . ?
C00A C00E 1.392(4) . ?
C00B H00E 0.9900 . ?
C00B H00F 0.9900 . ?
C00B C00K 1.532(3) . ?
C00C H00G 0.9500 . ?
C00C C00O 1.379(5) . ?
C00D H00H 0.9500 . ?
C00E H00I 0.9500 . ?
C00F H00J 0.9800 . ?
C00F H00K 0.9800 . ?
C00F H00L 0.9800 . ?
C00F C00G 1.533(3) . ?
C00G C00K 1.557(3) . ?
C00G C00L 1.560(3) . ?
C00H H00M 0.9900 . ?
C00H H00N 0.9900 . ?
C00H C00L 1.527(3) . ?
C00I C00J 1.393(4) . ?
C00I C00M 1.520(3) . ?
C00J H00O 0.9500 . ?
C00J C00N 1.388(4) . ?
C00K H00P 1.0000 . ?
C00L H00Q 1.0000 . ?
C00L C00M 1.535(4) . ?
C00M H00R 0.9900 . ?
C00M H00S 0.9900 . ?
C00N H00T 0.9500 . ?
C00N C00O 1.379(5) . ?
C00O H00U 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
N003 O002 C00H 107.89(16) . . ?
O002 N003 C00K 111.99(17) . . ?
C004 N003 O002 115.34(18) . . ?
C004 N003 C00K 127.66(18) . . ?
O001 C004 N003 123.0(2) . . ?
O001 C004 C005 122.4(2) . . ?
N003 C004 C005 114.62(19) . . ?
C007 C005 C004 118.16(19) . . ?
C007 C005 C009 120.9(2) . . ?
C009 C005 C004 121.0(2) . . ?
H00A C006 H00B 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?
C00G C006 H00A 109.5 . . ?
C00G C006 H00B 109.5 . . ?
C00G C006 H00C 109.5 . . ?
C005 C007 H007 120.0 . . ?
C005 C007 C00E 120.0(2) . . ?
C00E C007 H007 120.0 . . ?
C00C C008 H008 119.4 . . ?
C00I C008 H008 119.4 . . ?
C00I C008 C00C 121.2(3) . . ?
C005 C009 C00B 120.16(19) . . ?
C00D C009 C005 118.6(2) . . ?
C00D C009 C00B 121.2(2) . . ?
C00D C00A H00D 119.6 . . ?
C00D C00A C00E 120.8(2) . . ?
C00E C00A H00D 119.6 . . ?
C009 C00B H00E 108.5 . . ?
C009 C00B H00F 108.5 . . ?
C009 C00B C00K 115.04(19) . . ?
H00E C00B H00F 107.5 . . ?
C00K C00B H00E 108.5 . . ?
C00K C00B H00F 108.5 . . ?
C008 C00C H00G 120.1 . . ?
C00O C00C C008 119.9(3) . . ?
C00O C00C H00G 120.1 . . ?
C009 C00D C00A 120.5(2) . . ?
C009 C00D H00H 119.8 . . ?
C00A C00D H00H 119.8 . . ?
C007 C00E C00A 119.3(2) . . ?
C007 C00E H00I 120.4 . . ?
C00A C00E H00I 120.4 . . ?
H00J C00F H00K 109.5 . . ?
H00J C00F H00L 109.5 . . ?
H00K C00F H00L 109.5 . . ?
C00G C00F H00J 109.5 . . ?
C00G C00F H00K 109.5 . . ?
C00G C00F H00L 109.5 . . ?
C006 C00G C00K 112.06(19) . . ?
C006 C00G C00L 112.11(19) . . ?
C00F C00G C006 109.6(2) . . ?
C00F C00G C00K 107.4(2) . . ?
C00F C00G C00L 108.62(19) . . ?
C00K C00G C00L 106.85(18) . . ?
O002 C00H H00M 109.3 . . ?
O002 C00H H00N 109.3 . . ?
O002 C00H C00L 111.5(2) . . ?
H00M C00H H00N 108.0 . . ?
C00L C00H H00M 109.3 . . ?
C00L C00H H00N 109.3 . . ?
C008 C00I C00J 118.4(2) . . ?
C008 C00I C00M 121.1(2) . . ?
C00J C00I C00M 120.5(2) . . ?
C00I C00J H00O 119.7 . . ?
C00N C00J C00I 120.7(3) . . ?
C00N C00J H00O 119.7 . . ?
N003 C00K C00B 108.36(18) . . ?
N003 C00K C00G 111.12(18) . . ?
N003 C00K H00P 106.7 . . ?
C00B C00K C00G 116.77(19) . . ?
C00B C00K H00P 106.7 . . ?
C00G C00K H00P 106.7 . . ?
C00G C00L H00Q 107.3 . . ?
C00H C00L C00G 111.89(18) . . ?
C00H C00L H00Q 107.3 . . ?
C00H C00L C00M 109.1(2) . . ?
C00M C00L C00G 113.73(19) . . ?
C00M C00L H00Q 107.3 . . ?
C00I C00M C00L 114.1(2) . . ?
C00I C00M H00R 108.7 . . ?
C00I C00M H00S 108.7 . . ?
C00L C00M H00R 108.7 . . ?
C00L C00M H00S 108.7 . . ?
H00R C00M H00S 107.6 . . ?
C00J C00N H00T 120.0 . . ?
C00O C00N C00J 119.9(3) . . ?
C00O C00N H00T 120.0 . . ?
C00C C00O C00N 120.0(2) . . ?
C00C C00O H00U 120.0 . . ?
C00N C00O H00U 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
O001 C004 C005 C007 5.3(3) . . . . ?
O001 C004 C005 C009 -176.4(2) . . . . ?
O002 N003 C004 O001 -10.4(3) . . . . ?
O002 N003 C004 C005 171.43(18) . . . . ?
O002 N003 C00K C00B 167.28(18) . . . . ?
O002 N003 C00K C00G -63.1(2) . . . . ?
O002 C00H C00L C00G 55.1(3) . . . . ?
O002 C00H C00L C00M -178.16(18) . . . . ?
N003 O002 C00H C00L -62.5(2) . . . . ?
N003 C004 C005 C007 -176.6(2) . . . . ?
N003 C004 C005 C009 1.7(3) . . . . ?
C004 N003 C00K C00B -39.2(3) . . . . ?
C004 N003 C00K C00G 90.3(3) . . . . ?
C004 C005 C007 C00E 179.0(2) . . . . ?
C004 C005 C009 C00B 3.5(3) . . . . ?
C004 C005 C009 C00D -178.6(2) . . . . ?
C005 C007 C00E C00A -0.4(4) . . . . ?
C005 C009 C00B C00K -25.7(3) . . . . ?
C005 C009 C00D C00A -0.2(3) . . . . ?
C006 C00G C00K N003 -72.5(2) . . . . ?
C006 C00G C00K C00B 52.5(3) . . . . ?
C006 C00G C00L C00H 75.8(3) . . . . ?
C006 C00G C00L C00M -48.4(3) . . . . ?
C007 C005 C009 C00B -178.2(2) . . . . ?
C007 C005 C009 C00D -0.4(3) . . . . ?
C008 C00C C00O C00N -0.5(5) . . . . ?
C008 C00I C00J C00N -0.4(4) . . . . ?
C008 C00I C00M C00L -111.2(3) . . . . ?
C009 C005 C007 C00E 0.7(4) . . . . ?
C009 C00B C00K N003 39.4(3) . . . . ?
C009 C00B C00K C00G -87.0(2) . . . . ?
C00B C009 C00D C00A 177.6(2) . . . . ?
C00C C008 C00I C00J 0.9(4) . . . . ?
C00C C008 C00I C00M -178.1(3) . . . . ?
C00D C009 C00B C00K 156.5(2) . . . . ?
C00D C00A C00E C007 -0.2(4) . . . . ?
C00E C00A C00D C009 0.5(4) . . . . ?
C00F C00G C00K N003 167.09(19) . . . . ?
C00F C00G C00K C00B -67.9(2) . . . . ?
C00F C00G C00L C00H -163.0(2) . . . . ?
C00F C00G C00L C00M 72.9(3) . . . . ?
C00G C00L C00M C00I -167.3(2) . . . . ?
C00H O002 N003 C004 -89.7(2) . . . . ?
C00H O002 N003 C00K 67.3(2) . . . . ?
C00H C00L C00M C00I 67.0(3) . . . . ?
C00I C008 C00C C00O -0.5(4) . . . . ?
C00I C00J C00N C00O -0.6(5) . . . . ?
C00J C00I C00M C00L 69.8(3) . . . . ?
C00J C00N C00O C00C 1.0(5) . . . . ?
C00K N003 C004 O001 -163.2(2) . . . . ?
C00K N003 C004 C005 18.7(3) . . . . ?
C00K C00G C00L C00H -47.4(2) . . . . ?
C00K C00G C00L C00M -171.5(2) . . . . ?
C00L C00G C00K N003 50.7(2) . . . . ?
C00L C00G C00K C00B 175.67(19) . . . . ?
C00M C00I C00J C00N 178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/PE(2:1)'
####################################################################### 
# 
# 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_0203_5_0m
_database_code_depnum_ccdc_archive 'CCDC 2244761'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8205(2)
_cell_length_b                   15.6904(4)
_cell_length_c                   11.3118(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.9190(10)
_cell_angle_gamma                90
_cell_volume                     1696.97(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.76
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0441 after correction.
The Ratio of minimum to maximum transmission is 0.1273.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17442
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.749
_diffrn_reflns_theta_min         4.625
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3287
_reflns_number_total             3457
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.054
_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)+(0.1398P)²+0.1293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1827
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00C(H00H), C00K(H00P), C00N(H00S)
1.b Secondary CH2 refined with riding coordinates:
 C00F(H00K,H00L)
1.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C00B(H00G), C00D(H00I), C00E(H00J), C00G(H00M), C00H(H00N),
 C00J(H00O), C00L(H00Q), C00M(H00R)
1.d Idealised Me refined as rotating group:
 C006(H00A,H00B,H00C), C008(H00D,H00E,H00F), C00O(H00T,H00U,H00V)
;
_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 0.33549(10) 0.53251(6) 0.76209(10) 0.0571(3) Uani 1 1 d . . . . .
O002 O 0.21985(10) 0.65070(6) 0.54711(10) 0.0537(3) Uani 1 1 d . . . . .
N003 N 0.34152(13) 0.66097(8) 0.66577(12) 0.0536(3) Uani 1 1 d . . . . .
C004 C 0.38878(14) 0.60126(9) 0.76401(13) 0.0499(3) Uani 1 1 d . . . . .
C005 C 0.60999(14) 0.60658(9) 0.99394(14) 0.0528(3) Uani 1 1 d . . . . .
H005 H 0.595847 0.551244 1.019516 0.063 Uiso 1 1 calc R U . . .
C006 C 0.39338(16) 0.89920(9) 0.67224(16) 0.0554(4) Uani 1 1 d . . . . .
H00A H 0.332883 0.948152 0.661869 0.083 Uiso 1 1 calc R U . . .
H00B H 0.411932 0.896256 0.595445 0.083 Uiso 1 1 calc R U . . .
H00C H 0.481898 0.905662 0.754639 0.083 Uiso 1 1 calc R U . . .
C007 C 0.51803(14) 0.64070(9) 0.87039(13) 0.0494(3) Uani 1 1 d . . . . .
C008 C 0.29316(15) 0.82000(10) 0.80125(14) 0.0533(3) Uani 1 1 d . . . . .
H00D H 0.379969 0.834512 0.881562 0.080 Uiso 1 1 calc R U . . .
H00E H 0.260079 0.764127 0.813210 0.080 Uiso 1 1 calc R U . . .
H00F H 0.221940 0.863194 0.786473 0.080 Uiso 1 1 calc R U . . .
C009 C 0.53712(14) 0.72151(9) 0.82982(14) 0.0505(3) Uani 1 1 d . . . . .
C00A C -0.01058(15) 0.90316(8) 0.37855(14) 0.0526(3) Uani 1 1 d . . . . .
C00B C 0.72321(15) 0.65608(10) 1.07873(15) 0.0575(4) Uani 1 1 d . . . . .
H00G H 0.787341 0.634812 1.164416 0.069 Uiso 1 1 calc R U . . .
C00C C 0.41855(14) 0.74085(9) 0.69263(13) 0.0498(3) Uani 1 1 d . . . . .
H00H H 0.456198 0.748175 0.627643 0.060 Uiso 1 1 calc R U . . .
C00D C 0.65205(15) 0.77022(9) 0.91458(16) 0.0561(4) Uani 1 1 d . . . . .
H00I H 0.667606 0.824934 0.888065 0.067 Uiso 1 1 calc R U . . .
C00E C 0.74375(16) 0.73681(10) 1.03928(16) 0.0592(4) Uani 1 1 d . . . . .
H00J H 0.821991 0.769705 1.098788 0.071 Uiso 1 1 calc R U . . .
C00F C 0.07175(15) 0.87397(9) 0.52237(14) 0.0519(3) Uani 1 1 d . . . . .
H00K H 0.005330 0.851757 0.552273 0.062 Uiso 1 1 calc R U . . .
H00L H 0.119211 0.924056 0.578617 0.062 Uiso 1 1 calc R U . . .
C00G C -0.15625(16) 0.90608(9) 0.31488(15) 0.0569(4) Uani 1 1 d . . . . .
H00M H -0.205235 0.887430 0.361275 0.068 Uiso 1 1 calc R U . . .
C00H C 0.05823(17) 0.93113(10) 0.30742(16) 0.0591(4) Uani 1 1 d . . . . .
H00N H 0.157528 0.930221 0.349066 0.071 Uiso 1 1 calc R U . . .
C00I C 0.32057(14) 0.81714(8) 0.67971(13) 0.0482(3) Uani 1 1 d . . . . .
C00J C -0.1611(2) 0.96292(10) 0.11462(16) 0.0679(4) Uani 1 1 d . . . . .
H00O H -0.211990 0.983009 0.025293 0.082 Uiso 1 1 calc R U . . .
C00K C 0.18309(14) 0.80439(8) 0.54707(13) 0.0487(3) Uani 1 1 d . . . . .
H00P H 0.207961 0.808939 0.472576 0.058 Uiso 1 1 calc R U . . .
C00L C -0.23111(18) 0.93600(10) 0.18405(17) 0.0646(4) Uani 1 1 d . . . . .
H00Q H -0.330371 0.937957 0.142295 0.078 Uiso 1 1 calc R U . . .
C00M C -0.0167(2) 0.96025(10) 0.17657(18) 0.0661(4) Uani 1 1 d . . . . .
H00R H 0.031768 0.978437 0.129428 0.079 Uiso 1 1 calc R U . . .
C00N C 0.11972(14) 0.71577(9) 0.53711(14) 0.0509(3) Uani 1 1 d . . . . .
H00S H 0.095214 0.708178 0.611431 0.061 Uiso 1 1 calc R U . . .
C00O C -0.00663(15) 0.69616(9) 0.40529(15) 0.0567(4) Uani 1 1 d . . . . .
H00T H 0.017471 0.703134 0.332443 0.085 Uiso 1 1 calc R U . . .
H00U H -0.082769 0.735269 0.391709 0.085 Uiso 1 1 calc R U . . .
H00V H -0.036638 0.637328 0.406145 0.085 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
O001 C004 1.2184(18) . ?
O002 N003 1.3805(15) . ?
O002 C00N 1.4540(17) . ?
N003 C004 1.3573(18) . ?
N003 C00C 1.4563(18) . ?
C004 C007 1.4870(19) . ?
C005 H005 0.9500 . ?
C005 C007 1.3883(19) . ?
C005 C00B 1.387(2) . ?
C006 H00A 0.9800 . ?
C006 H00B 0.9800 . ?
C006 H00C 0.9800 . ?
C006 C00I 1.5322(18) . ?
C007 C009 1.396(2) . ?
C008 H00D 0.9800 . ?
C008 H00E 0.9800 . ?
C008 H00F 0.9800 . ?
C008 C00I 1.5369(18) . ?
C009 C00C 1.5106(19) . ?
C009 C00D 1.391(2) . ?
C00A C00F 1.5143(19) . ?
C00A C00G 1.394(2) . ?
C00A C00H 1.398(2) . ?
C00B H00G 0.9500 . ?
C00B C00E 1.395(2) . ?
C00C H00H 1.0000 . ?
C00C C00I 1.5598(18) . ?
C00D H00I 0.9500 . ?
C00D C00E 1.392(2) . ?
C00E H00J 0.9500 . ?
C00F H00K 0.9900 . ?
C00F H00L 0.9900 . ?
C00F C00K 1.5512(18) . ?
C00G H00M 0.9500 . ?
C00G C00L 1.394(2) . ?
C00H H00N 0.9500 . ?
C00H C00M 1.390(2) . ?
C00I C00K 1.5538(18) . ?
C00J H00O 0.9500 . ?
C00J C00L 1.388(3) . ?
C00J C00M 1.382(3) . ?
C00K H00P 1.0000 . ?
C00K C00N 1.5311(19) . ?
C00L H00Q 0.9500 . ?
C00M H00R 0.9500 . ?
C00N H00S 1.0000 . ?
C00N C00O 1.5093(19) . ?
C00O H00T 0.9800 . ?
C00O H00U 0.9800 . ?
C00O H00V 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
N003 O002 C00N 109.29(10) . . ?
O002 N003 C00C 119.70(11) . . ?
C004 N003 O002 122.52(11) . . ?
C004 N003 C00C 117.64(12) . . ?
O001 C004 N003 127.07(13) . . ?
O001 C004 C007 129.85(13) . . ?
N003 C004 C007 103.08(12) . . ?
C007 C005 H005 121.1 . . ?
C00B C005 H005 121.1 . . ?
C00B C005 C007 117.71(14) . . ?
H00A C006 H00B 109.5 . . ?
H00A C006 H00C 109.5 . . ?
H00B C006 H00C 109.5 . . ?
C00I C006 H00A 109.5 . . ?
C00I C006 H00B 109.5 . . ?
C00I C006 H00C 109.5 . . ?
C005 C007 C004 127.84(13) . . ?
C005 C007 C009 122.30(13) . . ?
C009 C007 C004 109.86(12) . . ?
H00D C008 H00E 109.5 . . ?
H00D C008 H00F 109.5 . . ?
H00E C008 H00F 109.5 . . ?
C00I C008 H00D 109.5 . . ?
C00I C008 H00E 109.5 . . ?
C00I C008 H00F 109.5 . . ?
C007 C009 C00C 109.57(12) . . ?
C00D C009 C007 119.65(13) . . ?
C00D C009 C00C 130.77(13) . . ?
C00G C00A C00F 121.28(13) . . ?
C00G C00A C00H 118.06(14) . . ?
C00H C00A C00F 120.61(13) . . ?
C005 C00B H00G 119.7 . . ?
C005 C00B C00E 120.58(14) . . ?
C00E C00B H00G 119.7 . . ?
N003 C00C C009 99.74(10) . . ?
N003 C00C H00H 109.6 . . ?
N003 C00C C00I 110.09(11) . . ?
C009 C00C H00H 109.6 . . ?
C009 C00C C00I 117.61(11) . . ?
C00I C00C H00H 109.6 . . ?
C009 C00D H00I 120.8 . . ?
C009 C00D C00E 118.34(14) . . ?
C00E C00D H00I 120.8 . . ?
C00B C00E H00J 119.3 . . ?
C00D C00E C00B 121.42(14) . . ?
C00D C00E H00J 119.3 . . ?
C00A C00F H00K 108.5 . . ?
C00A C00F H00L 108.5 . . ?
C00A C00F C00K 115.03(11) . . ?
H00K C00F H00L 107.5 . . ?
C00K C00F H00K 108.5 . . ?
C00K C00F H00L 108.5 . . ?
C00A C00G H00M 119.5 . . ?
C00A C00G C00L 120.93(15) . . ?
C00L C00G H00M 119.5 . . ?
C00A C00H H00N 119.5 . . ?
C00M C00H C00A 120.90(16) . . ?
C00M C00H H00N 119.5 . . ?
C006 C00I C008 110.14(11) . . ?
C006 C00I C00C 107.79(11) . . ?
C006 C00I C00K 109.85(11) . . ?
C008 C00I C00C 110.24(11) . . ?
C008 C00I C00K 111.65(11) . . ?
C00K C00I C00C 107.04(10) . . ?
C00L C00J H00O 120.3 . . ?
C00M C00J H00O 120.3 . . ?
C00M C00J C00L 119.41(15) . . ?
C00F C00K C00I 113.27(11) . . ?
C00F C00K H00P 106.9 . . ?
C00I C00K H00P 106.9 . . ?
C00N C00K C00F 110.04(11) . . ?
C00N C00K C00I 112.42(11) . . ?
C00N C00K H00P 106.9 . . ?
C00G C00L H00Q 119.9 . . ?
C00J C00L C00G 120.21(16) . . ?
C00J C00L H00Q 119.9 . . ?
C00H C00M H00R 119.8 . . ?
C00J C00M C00H 120.48(16) . . ?
C00J C00M H00R 119.8 . . ?
O002 C00N C00K 109.89(11) . . ?
O002 C00N H00S 109.4 . . ?
O002 C00N C00O 103.36(10) . . ?
C00K C00N H00S 109.4 . . ?
C00O C00N C00K 115.16(12) . . ?
C00O C00N H00S 109.4 . . ?
C00N C00O H00T 109.5 . . ?
C00N C00O H00U 109.5 . . ?
C00N C00O H00V 109.5 . . ?
H00T C00O H00U 109.5 . . ?
H00T C00O H00V 109.5 . . ?
H00U C00O H00V 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 C004 C007 C005 0.8(2) . . . . ?
O001 C004 C007 C009 -178.69(14) . . . . ?
O002 N003 C004 O001 1.2(2) . . . . ?
O002 N003 C004 C007 -178.79(11) . . . . ?
O002 N003 C00C C009 179.25(11) . . . . ?
O002 N003 C00C C00I 54.95(15) . . . . ?
N003 O002 C00N C00K 57.24(14) . . . . ?
N003 O002 C00N C00O -179.35(11) . . . . ?
N003 C004 C007 C005 -179.17(13) . . . . ?
N003 C004 C007 C009 1.35(14) . . . . ?
N003 C00C C00I C006 -165.44(11) . . . . ?
N003 C00C C00I C008 74.30(14) . . . . ?
N003 C00C C00I C00K -47.32(13) . . . . ?
C004 N003 C00C C009 3.49(15) . . . . ?
C004 N003 C00C C00I -120.81(13) . . . . ?
C004 C007 C009 C00C 0.70(15) . . . . ?
C004 C007 C009 C00D 179.84(12) . . . . ?
C005 C007 C009 C00C -178.81(12) . . . . ?
C005 C007 C009 C00D 0.3(2) . . . . ?
C005 C00B C00E C00D 0.0(2) . . . . ?
C006 C00I C00K C00F -65.42(13) . . . . ?
C006 C00I C00K C00N 169.07(11) . . . . ?
C007 C005 C00B C00E -0.8(2) . . . . ?
C007 C009 C00C N003 -2.29(13) . . . . ?
C007 C009 C00C C00I 116.59(13) . . . . ?
C007 C009 C00D C00E -1.1(2) . . . . ?
C008 C00I C00K C00F 57.07(15) . . . . ?
C008 C00I C00K C00N -68.44(14) . . . . ?
C009 C00C C00I C006 81.31(14) . . . . ?
C009 C00C C00I C008 -38.94(16) . . . . ?
C009 C00C C00I C00K -160.57(11) . . . . ?
C009 C00D C00E C00B 0.9(2) . . . . ?
C00A C00F C00K C00I 141.02(12) . . . . ?
C00A C00F C00K C00N -92.21(14) . . . . ?
C00A C00G C00L C00J 0.4(2) . . . . ?
C00A C00H C00M C00J 0.7(2) . . . . ?
C00B C005 C007 C004 -178.79(13) . . . . ?
C00B C005 C007 C009 0.6(2) . . . . ?
C00C N003 C004 O001 176.88(13) . . . . ?
C00C N003 C004 C007 -3.15(16) . . . . ?
C00C C009 C00D C00E 177.84(13) . . . . ?
C00C C00I C00K C00F 177.81(10) . . . . ?
C00C C00I C00K C00N 52.30(13) . . . . ?
C00D C009 C00C N003 178.70(14) . . . . ?
C00D C009 C00C C00I -62.41(19) . . . . ?
C00F C00A C00G C00L 177.62(13) . . . . ?
C00F C00A C00H C00M -178.20(14) . . . . ?
C00F C00K C00N O002 174.40(10) . . . . ?
C00F C00K C00N C00O 58.21(15) . . . . ?
C00G C00A C00F C00K 129.41(14) . . . . ?
C00G C00A C00H C00M -0.6(2) . . . . ?
C00H C00A C00F C00K -53.05(18) . . . . ?
C00H C00A C00G C00L 0.0(2) . . . . ?
C00I C00K C00N O002 -58.35(14) . . . . ?
C00I C00K C00N C00O -174.54(11) . . . . ?
C00L C00J C00M C00H -0.2(2) . . . . ?
C00M C00J C00L C00G -0.4(2) . . . . ?
C00N O002 N003 C004 116.26(14) . . . . ?
C00N O002 N003 C00C -59.28(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/PE(2:1)'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2244760'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O2'
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5000(10)
_cell_length_b                   14.8211(17)
_cell_length_c                   13.0677(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.708(5)
_cell_angle_gamma                90
_cell_volume                     1645.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9768
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      70.00
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.1584
_exptl_absorpt_correction_type   multi-scan
_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   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.1584
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14313
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.188
_diffrn_reflns_theta_min         4.512
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2544
_reflns_number_total             3002
_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 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         0.229
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0072(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.096
_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)+(0.1376P)²+0.1752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2064
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
1.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C20(H20A,H20B)
1.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17)
1.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_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 0.37937(14) 0.44366(8) 0.37832(13) 0.0553(4) Uani 1 1 d . . . . .
O2 O 0.44086(17) 0.58153(10) 0.23154(14) 0.0675(5) Uani 1 1 d . . . . .
N1 N 0.52500(17) 0.47883(10) 0.35337(14) 0.0506(5) Uani 1 1 d . . . . .
C1 C 0.2682(5) 0.06664(17) 0.5607(2) 0.0905(10) Uani 1 1 d . . . . .
H1 H 0.291310 0.005307 0.560062 0.109 Uiso 1 1 calc R U . . .
C2 C 0.3839(3) 0.12902(15) 0.5367(2) 0.0684(6) Uani 1 1 d . . . . .
H2 H 0.483812 0.109351 0.519998 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3499(2) 0.22052(13) 0.53771(15) 0.0507(5) Uani 1 1 d . . . . .
C4 C 0.2006(3) 0.24706(16) 0.56338(18) 0.0646(6) Uani 1 1 d . . . . .
H4 H 0.175883 0.308174 0.564767 0.078 Uiso 1 1 calc R U . . .
C5 C 0.0875(3) 0.1845(2) 0.5870(2) 0.0869(9) Uani 1 1 d . . . . .
H5 H -0.012411 0.203841 0.604222 0.104 Uiso 1 1 calc R U . . .
C6 C 0.1202(4) 0.0950(2) 0.5854(3) 0.0941(10) Uani 1 1 d . . . . .
H6 H 0.043011 0.053119 0.600861 0.113 Uiso 1 1 calc R U . . .
C7 C 0.4752(3) 0.28822(15) 0.51294(17) 0.0608(6) Uani 1 1 d . . . . .
H7A H 0.572775 0.271142 0.548092 0.073 Uiso 1 1 calc R U . . .
H7B H 0.444549 0.346891 0.538533 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5038(2) 0.29573(11) 0.39762(15) 0.0461(5) Uani 1 1 d . . . . .
H8 H 0.498096 0.234466 0.369549 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6672(2) 0.33481(11) 0.37002(15) 0.0449(5) Uani 1 1 d . . . . .
C10 C 0.6668(2) 0.43676(11) 0.39702(15) 0.0431(4) Uani 1 1 d . . . . .
H10 H 0.672288 0.445101 0.471434 0.052 Uiso 1 1 calc R U . . .
C11 C 0.7894(2) 0.49384(11) 0.34684(15) 0.0450(5) Uani 1 1 d . . . . .
C12 C 0.7179(2) 0.55256(11) 0.27754(16) 0.0477(5) Uani 1 1 d . . . . .
C13 C 0.5443(2) 0.54190(11) 0.28024(16) 0.0489(5) Uani 1 1 d . . . . .
C14 C 0.8044(3) 0.61064(13) 0.21837(19) 0.0596(6) Uani 1 1 d . . . . .
H14 H 0.755057 0.649218 0.171332 0.072 Uiso 1 1 calc R U . . .
C15 C 0.9662(3) 0.60956(15) 0.2313(2) 0.0656(6) Uani 1 1 d . . . . .
H15 H 1.026941 0.647684 0.192062 0.079 Uiso 1 1 calc R U . . .
C16 C 1.0388(2) 0.55280(15) 0.3015(2) 0.0619(6) Uani 1 1 d . . . . .
H16 H 1.147919 0.553779 0.309542 0.074 Uiso 1 1 calc R U . . .
C17 C 0.9522(2) 0.49419(13) 0.36057(18) 0.0556(5) Uani 1 1 d . . . . .
H17 H 1.001789 0.456142 0.408056 0.067 Uiso 1 1 calc R U . . .
C18 C 0.8000(3) 0.28856(14) 0.4313(2) 0.0643(6) Uani 1 1 d . . . . .
H18A H 0.898906 0.302061 0.401137 0.096 Uiso 1 1 calc R U . . .
H18B H 0.783423 0.224495 0.430753 0.096 Uiso 1 1 calc R U . . .
H18C H 0.801313 0.310065 0.500651 0.096 Uiso 1 1 calc R U . . .
C19 C 0.6938(3) 0.31963(14) 0.25627(18) 0.0582(6) Uani 1 1 d . . . . .
H19A H 0.618927 0.354403 0.216463 0.087 Uiso 1 1 calc R U . . .
H19B H 0.680732 0.256781 0.240422 0.087 Uiso 1 1 calc R U . . .
H19C H 0.798521 0.338172 0.240402 0.087 Uiso 1 1 calc R U . . .
C20 C 0.3722(2) 0.34983(12) 0.34523(16) 0.0507(5) Uani 1 1 d . . . . .
H20A H 0.382271 0.346713 0.271573 0.061 Uiso 1 1 calc R U . . .
H20B H 0.271156 0.324224 0.362051 0.061 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 N1 1.391(2) . ?
O1 C20 1.457(2) . ?
O2 C13 1.220(2) . ?
N1 C10 1.458(2) . ?
N1 C13 1.350(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.392(4) . ?
C1 C6 1.374(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C3 C4 1.380(3) . ?
C3 C7 1.505(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.355(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.538(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.557(3) . ?
C8 C20 1.522(3) . ?
C9 C10 1.552(2) . ?
C9 C18 1.527(3) . ?
C9 C19 1.527(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.507(2) . ?
C11 C12 1.383(3) . ?
C11 C17 1.391(3) . ?
C12 C13 1.486(3) . ?
C12 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 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
N1 O1 C20 108.54(13) . . ?
O1 N1 C10 118.64(15) . . ?
C13 N1 O1 123.57(15) . . ?
C13 N1 C10 117.16(15) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.5(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C7 120.1(2) . . ?
C4 C3 C2 118.3(2) . . ?
C4 C3 C7 121.60(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C3 C7 H7A 109.0 . . ?
C3 C7 H7B 109.0 . . ?
C3 C7 C8 113.12(17) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8 107.0 . . ?
C7 C8 C9 114.98(16) . . ?
C9 C8 H8 107.0 . . ?
C20 C8 C7 110.08(17) . . ?
C20 C8 H8 107.0 . . ?
C20 C8 C9 110.40(15) . . ?
C10 C9 C8 107.56(13) . . ?
C18 C9 C8 111.24(16) . . ?
C18 C9 C10 108.91(15) . . ?
C19 C9 C8 109.26(16) . . ?
C19 C9 C10 111.48(16) . . ?
C19 C9 C18 108.42(16) . . ?
N1 C10 C9 109.55(14) . . ?
N1 C10 H10 110.4 . . ?
N1 C10 C11 99.42(14) . . ?
C9 C10 H10 110.4 . . ?
C11 C10 C9 116.21(14) . . ?
C11 C10 H10 110.4 . . ?
C12 C11 C10 110.02(15) . . ?
C12 C11 C17 119.89(18) . . ?
C17 C11 C10 130.10(18) . . ?
C11 C12 C13 109.56(16) . . ?
C14 C12 C11 121.80(18) . . ?
C14 C12 C13 128.64(19) . . ?
O2 C13 N1 126.99(18) . . ?
O2 C13 C12 129.56(19) . . ?
N1 C13 C12 103.41(15) . . ?
C12 C14 H14 121.0 . . ?
C15 C14 C12 117.9(2) . . ?
C15 C14 H14 121.0 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.19(19) . . ?
C17 C16 H16 119.4 . . ?
C11 C17 H17 120.9 . . ?
C16 C17 C11 118.2(2) . . ?
C16 C17 H17 120.9 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 C8 110.21(15) . . ?
O1 C20 H20A 109.6 . . ?
O1 C20 H20B 109.6 . . ?
C8 C20 H20A 109.6 . . ?
C8 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?

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 N1 C10 C9 55.8(2) . . . . ?
O1 N1 C10 C11 178.13(15) . . . . ?
O1 N1 C13 O2 5.7(3) . . . . ?
O1 N1 C13 C12 -176.33(15) . . . . ?
N1 O1 C20 C8 59.3(2) . . . . ?
N1 C10 C11 C12 -5.33(18) . . . . ?
N1 C10 C11 C17 174.91(19) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C7 179.3(2) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C7 C8 77.3(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C7 C8 C9 -158.09(17) . . . . ?
C3 C7 C8 C20 76.5(2) . . . . ?
C4 C3 C7 C8 -103.7(2) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C7 C3 C4 C5 -179.3(2) . . . . ?
C7 C8 C9 C10 -71.0(2) . . . . ?
C7 C8 C9 C18 48.2(2) . . . . ?
C7 C8 C9 C19 167.83(16) . . . . ?
C7 C8 C20 O1 67.75(19) . . . . ?
C8 C9 C10 N1 -49.4(2) . . . . ?
C8 C9 C10 C11 -161.07(16) . . . . ?
C9 C8 C20 O1 -60.3(2) . . . . ?
C9 C10 C11 C12 112.04(18) . . . . ?
C9 C10 C11 C17 -67.7(3) . . . . ?
C10 N1 C13 O2 176.45(19) . . . . ?
C10 N1 C13 C12 -5.6(2) . . . . ?
C10 C11 C12 C13 2.6(2) . . . . ?
C10 C11 C12 C14 -177.83(17) . . . . ?
C10 C11 C17 C16 178.17(18) . . . . ?
C11 C12 C13 O2 179.4(2) . . . . ?
C11 C12 C13 N1 1.5(2) . . . . ?
C11 C12 C14 C15 -0.9(3) . . . . ?
C12 C11 C17 C16 -1.6(3) . . . . ?
C12 C14 C15 C16 -0.5(3) . . . . ?
C13 N1 C10 C9 -115.38(18) . . . . ?
C13 N1 C10 C11 6.9(2) . . . . ?
C13 C12 C14 C15 178.51(19) . . . . ?
C14 C12 C13 O2 0.0(3) . . . . ?
C14 C12 C13 N1 -177.9(2) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C11 0.2(3) . . . . ?
C17 C11 C12 C13 -177.57(16) . . . . ?
C17 C11 C12 C14 2.0(3) . . . . ?
C18 C9 C10 N1 -170.11(17) . . . . ?
C18 C9 C10 C11 78.3(2) . . . . ?
C19 C9 C10 N1 70.3(2) . . . . ?
C19 C9 C10 C11 -41.3(2) . . . . ?
C20 O1 N1 C10 -59.9(2) . . . . ?
C20 O1 N1 C13 110.74(19) . . . . ?
C20 C8 C9 C10 54.2(2) . . . . ?
C20 C8 C9 C18 173.43(15) . . . . ?
C20 C8 C9 C19 -66.91(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/PE(2:1)'
####################################################################### 
# 
# 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_0919_6_0m
_database_code_depnum_ccdc_archive 'CCDC 2244763'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1681(4)
_cell_length_b                   16.0212(8)
_cell_length_c                   11.4696(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.233(2)
_cell_angle_gamma                90
_cell_volume                     1682.02(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      77.62
_cell_measurement_theta_min      4.83
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.0891
_exptl_absorpt_correction_T_min  0.0112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.1257.
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    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34118
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.801
_diffrn_reflns_theta_min         4.831
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3278
_reflns_number_total             3563
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0656
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1248P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1709
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00A(H00I), C00K(H00R)
1.b Secondary CH2 refined with riding coordinates:
 C008(H00G,H00H), C00C(H00J,H00K), C00M(H00T,H00U)
1.c Aromatic/amide H refined with riding coordinates:
 C00D(H00L), C00E(H00M), C00F(H00N), C00G(H00O), C00I(H00P), C00J(H00Q),
 C00L(H00S), C00N(H00V), C00O(H00W)
1.d Idealised Me refined as rotating group:
 C005(H00A,H00B,H00C), C006(H00D,H00E,H00F)
;
_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 0.82554(9) 0.53878(6) 0.51013(8) 0.0570(3) Uani 1 1 d . . . . .
O002 O 0.67117(11) 0.43038(6) 0.62633(8) 0.0624(3) Uani 1 1 d . . . . .
N003 N 0.81505(11) 0.45487(7) 0.47509(9) 0.0535(3) Uani 1 1 d . . . . .
C004 C 0.72364(13) 0.40647(8) 0.53648(11) 0.0536(3) Uani 1 1 d . . . . .
C005 C 0.58762(13) 0.45295(8) 0.26960(11) 0.0559(3) Uani 1 1 d . . . . .
H00A H 0.521759 0.484052 0.215145 0.084 Uiso 1 1 calc R U . . .
H00B H 0.551277 0.455833 0.348231 0.084 Uiso 1 1 calc R U . . .
H00C H 0.591803 0.394513 0.244769 0.084 Uiso 1 1 calc R U . . .
C006 C 0.79128(16) 0.48798(9) 0.14541(11) 0.0605(3) Uani 1 1 d . . . . .
H00D H 0.771621 0.432364 0.112598 0.091 Uiso 1 1 calc R U . . .
H00E H 0.896274 0.499542 0.145902 0.091 Uiso 1 1 calc R U . . .
H00F H 0.737866 0.529903 0.097681 0.091 Uiso 1 1 calc R U . . .
C007 C 0.74133(13) 0.49131(8) 0.27062(11) 0.0531(3) Uani 1 1 d . . . . .
C008 C 0.87063(15) 0.35004(9) 0.33056(12) 0.0590(3) Uani 1 1 d . . . . .
H00G H 0.863066 0.340354 0.245184 0.071 Uiso 1 1 calc R U . . .
H00H H 0.970159 0.333402 0.359547 0.071 Uiso 1 1 calc R U . . .
C009 C 0.69452(13) 0.32159(8) 0.48655(11) 0.0545(3) Uani 1 1 d . . . . .
C00A C 0.85145(13) 0.44331(8) 0.35318(11) 0.0537(3) Uani 1 1 d . . . . .
H00I H 0.949077 0.469855 0.345068 0.064 Uiso 1 1 calc R U . . .
C00B C 0.85188(13) 0.72762(8) 0.31400(11) 0.0555(3) Uani 1 1 d . . . . .
C00C C 0.71171(14) 0.58498(8) 0.44583(11) 0.0553(3) Uani 1 1 d . . . . .
H00J H 0.711830 0.643510 0.473503 0.066 Uiso 1 1 calc R U . . .
H00K H 0.615464 0.560246 0.460376 0.066 Uiso 1 1 calc R U . . .
C00D C 0.92353(15) 0.76493(9) 0.41076(12) 0.0624(3) Uani 1 1 d . . . . .
H00L H 0.983166 0.731746 0.462909 0.075 Uiso 1 1 calc R U . . .
C00E C 0.59442(15) 0.27036(9) 0.53940(12) 0.0598(3) Uani 1 1 d . . . . .
H00M H 0.549284 0.289048 0.607233 0.072 Uiso 1 1 calc R U . . .
C00F C 0.90950(18) 0.84947(10) 0.43240(13) 0.0697(4) Uani 1 1 d . . . . .
H00N H 0.958665 0.873657 0.499265 0.084 Uiso 1 1 calc R U . . .
C00G C 0.76488(14) 0.77817(9) 0.23913(12) 0.0597(3) Uani 1 1 d . . . . .
H00O H 0.713719 0.754133 0.173056 0.072 Uiso 1 1 calc R U . . .
C00H C 0.76183(14) 0.29478(8) 0.38656(11) 0.0560(3) Uani 1 1 d . . . . .
C00I C 0.62946(18) 0.16503(9) 0.39501(13) 0.0692(4) Uani 1 1 d . . . . .
H00P H 0.607961 0.111158 0.363988 0.083 Uiso 1 1 calc R U . . .
C00J C 0.56065(16) 0.19251(9) 0.49345(14) 0.0671(4) Uani 1 1 d . . . . .
H00Q H 0.491189 0.158014 0.528596 0.081 Uiso 1 1 calc R U . . .
C00K C 0.73481(13) 0.58336(8) 0.31528(11) 0.0541(3) Uani 1 1 d . . . . .
H00R H 0.647738 0.610361 0.274606 0.065 Uiso 1 1 calc R U . . .
C00L C 0.72871(17) 0.21561(9) 0.34225(12) 0.0639(4) Uani 1 1 d . . . . .
H00S H 0.774717 0.196200 0.275204 0.077 Uiso 1 1 calc R U . . .
C00M C 0.87033(15) 0.63599(9) 0.28815(13) 0.0611(3) Uani 1 1 d . . . . .
H00T H 0.956285 0.614551 0.335011 0.073 Uiso 1 1 calc R U . . .
H00U H 0.889826 0.629188 0.204659 0.073 Uiso 1 1 calc R U . . .
C00N C 0.75238(16) 0.86315(9) 0.26023(14) 0.0663(4) Uani 1 1 d . . . . .
H00V H 0.694172 0.896928 0.207838 0.080 Uiso 1 1 calc R U . . .
C00O C 0.82401(18) 0.89878(10) 0.35684(15) 0.0707(4) Uani 1 1 d . . . . .
H00W H 0.814668 0.956860 0.371387 0.085 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
O001 N003 1.4048(14) . ?
O001 C00C 1.4471(16) . ?
O002 C004 1.2232(15) . ?
N003 C004 1.3660(16) . ?
N003 C00A 1.4675(16) . ?
C004 C009 1.4938(18) . ?
C005 H00A 0.9800 . ?
C005 H00B 0.9800 . ?
C005 H00C 0.9800 . ?
C005 C007 1.5368(17) . ?
C006 H00D 0.9800 . ?
C006 H00E 0.9800 . ?
C006 H00F 0.9800 . ?
C006 C007 1.5327(17) . ?
C007 C00A 1.5490(17) . ?
C007 C00K 1.5635(17) . ?
C008 H00G 0.9900 . ?
C008 H00H 0.9900 . ?
C008 C00A 1.5285(18) . ?
C008 C00H 1.5045(19) . ?
C009 C00E 1.3949(19) . ?
C009 C00H 1.4002(18) . ?
C00A H00I 1.0000 . ?
C00B C00D 1.3922(19) . ?
C00B C00G 1.3972(19) . ?
C00B C00M 1.5091(19) . ?
C00C H00J 0.9900 . ?
C00C H00K 0.9900 . ?
C00C C00K 1.5242(17) . ?
C00D H00L 0.9500 . ?
C00D C00F 1.384(2) . ?
C00E H00M 0.9500 . ?
C00E C00J 1.382(2) . ?
C00F H00N 0.9500 . ?
C00F C00O 1.383(2) . ?
C00G H00O 0.9500 . ?
C00G C00N 1.389(2) . ?
C00H C00L 1.394(2) . ?
C00I H00P 0.9500 . ?
C00I C00J 1.395(2) . ?
C00I C00L 1.383(2) . ?
C00J H00Q 0.9500 . ?
C00K H00R 1.0000 . ?
C00K C00M 1.5475(18) . ?
C00L H00S 0.9500 . ?
C00M H00T 0.9900 . ?
C00M H00U 0.9900 . ?
C00N H00V 0.9500 . ?
C00N C00O 1.380(2) . ?
C00O H00W 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
N003 O001 C00C 107.93(9) . . ?
O001 N003 C00A 112.20(9) . . ?
C004 N003 O001 115.46(9) . . ?
C004 N003 C00A 126.77(11) . . ?
O002 C004 N003 122.57(12) . . ?
O002 C004 C009 122.54(12) . . ?
N003 C004 C009 114.89(10) . . ?
H00A C005 H00B 109.5 . . ?
H00A C005 H00C 109.5 . . ?
H00B C005 H00C 109.5 . . ?
C007 C005 H00A 109.5 . . ?
C007 C005 H00B 109.5 . . ?
C007 C005 H00C 109.5 . . ?
H00D C006 H00E 109.5 . . ?
H00D C006 H00F 109.5 . . ?
H00E C006 H00F 109.5 . . ?
C007 C006 H00D 109.5 . . ?
C007 C006 H00E 109.5 . . ?
C007 C006 H00F 109.5 . . ?
C005 C007 C00A 111.83(10) . . ?
C005 C007 C00K 109.13(10) . . ?
C006 C007 C005 107.53(10) . . ?
C006 C007 C00A 109.67(10) . . ?
C006 C007 C00K 111.02(10) . . ?
C00A C007 C00K 107.68(10) . . ?
H00G C008 H00H 107.6 . . ?
C00A C008 H00G 108.6 . . ?
C00A C008 H00H 108.6 . . ?
C00H C008 H00G 108.6 . . ?
C00H C008 H00H 108.6 . . ?
C00H C008 C00A 114.68(10) . . ?
C00E C009 C004 118.48(11) . . ?
C00E C009 C00H 120.44(12) . . ?
C00H C009 C004 121.05(11) . . ?
N003 C00A C007 110.14(9) . . ?
N003 C00A C008 108.64(10) . . ?
N003 C00A H00I 106.7 . . ?
C007 C00A H00I 106.7 . . ?
C008 C00A C007 117.31(11) . . ?
C008 C00A H00I 106.7 . . ?
C00D C00B C00G 117.93(13) . . ?
C00D C00B C00M 121.41(12) . . ?
C00G C00B C00M 120.63(12) . . ?
O001 C00C H00J 109.5 . . ?
O001 C00C H00K 109.5 . . ?
O001 C00C C00K 110.84(10) . . ?
H00J C00C H00K 108.1 . . ?
C00K C00C H00J 109.5 . . ?
C00K C00C H00K 109.5 . . ?
C00B C00D H00L 119.4 . . ?
C00F C00D C00B 121.24(14) . . ?
C00F C00D H00L 119.4 . . ?
C009 C00E H00M 119.9 . . ?
C00J C00E C009 120.26(13) . . ?
C00J C00E H00M 119.9 . . ?
C00D C00F H00N 119.9 . . ?
C00O C00F C00D 120.11(14) . . ?
C00O C00F H00N 119.9 . . ?
C00B C00G H00O 119.6 . . ?
C00N C00G C00B 120.73(13) . . ?
C00N C00G H00O 119.6 . . ?
C009 C00H C008 120.17(12) . . ?
C00L C00H C008 121.06(12) . . ?
C00L C00H C009 118.74(13) . . ?
C00J C00I H00P 119.7 . . ?
C00L C00I H00P 119.7 . . ?
C00L C00I C00J 120.52(14) . . ?
C00E C00J C00I 119.44(14) . . ?
C00E C00J H00Q 120.3 . . ?
C00I C00J H00Q 120.3 . . ?
C007 C00K H00R 107.4 . . ?
C00C C00K C007 110.35(10) . . ?
C00C C00K H00R 107.4 . . ?
C00C C00K C00M 110.24(11) . . ?
C00M C00K C007 113.71(10) . . ?
C00M C00K H00R 107.4 . . ?
C00H C00L H00S 119.7 . . ?
C00I C00L C00H 120.59(14) . . ?
C00I C00L H00S 119.7 . . ?
C00B C00M C00K 112.98(11) . . ?
C00B C00M H00T 109.0 . . ?
C00B C00M H00U 109.0 . . ?
C00K C00M H00T 109.0 . . ?
C00K C00M H00U 109.0 . . ?
H00T C00M H00U 107.8 . . ?
C00G C00N H00V 119.8 . . ?
C00O C00N C00G 120.36(14) . . ?
C00O C00N H00V 119.8 . . ?
C00F C00O H00W 120.2 . . ?
C00N C00O C00F 119.62(14) . . ?
C00N C00O H00W 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 N003 C004 O002 -10.43(17) . . . . ?
O001 N003 C004 C009 170.50(9) . . . . ?
O001 N003 C00A C007 -62.71(12) . . . . ?
O001 N003 C00A C008 167.53(9) . . . . ?
O001 C00C C00K C007 56.85(13) . . . . ?
O001 C00C C00K C00M -69.57(13) . . . . ?
O002 C004 C009 C00E 5.28(19) . . . . ?
O002 C004 C009 C00H -176.96(12) . . . . ?
N003 O001 C00C C00K -63.57(12) . . . . ?
N003 C004 C009 C00E -175.64(11) . . . . ?
N003 C004 C009 C00H 2.12(17) . . . . ?
C004 N003 C00A C007 89.48(14) . . . . ?
C004 N003 C00A C008 -40.27(16) . . . . ?
C004 C009 C00E C00J 177.76(11) . . . . ?
C004 C009 C00H C008 2.79(18) . . . . ?
C004 C009 C00H C00L -178.77(11) . . . . ?
C005 C007 C00A N003 -67.89(13) . . . . ?
C005 C007 C00A C008 57.05(14) . . . . ?
C005 C007 C00K C00C 71.72(13) . . . . ?
C005 C007 C00K C00M -163.82(11) . . . . ?
C006 C007 C00A N003 172.92(10) . . . . ?
C006 C007 C00A C008 -62.15(14) . . . . ?
C006 C007 C00K C00C -169.93(10) . . . . ?
C006 C007 C00K C00M -45.47(15) . . . . ?
C007 C00K C00M C00B 170.68(11) . . . . ?
C008 C00H C00L C00I 179.44(13) . . . . ?
C009 C00E C00J C00I 1.1(2) . . . . ?
C009 C00H C00L C00I 1.0(2) . . . . ?
C00A N003 C004 O002 -161.84(12) . . . . ?
C00A N003 C004 C009 19.08(17) . . . . ?
C00A C007 C00K C00C -49.86(13) . . . . ?
C00A C007 C00K C00M 74.60(13) . . . . ?
C00A C008 C00H C009 -25.51(17) . . . . ?
C00A C008 C00H C00L 156.09(12) . . . . ?
C00B C00D C00F C00O -0.5(2) . . . . ?
C00B C00G C00N C00O -1.1(2) . . . . ?
C00C O001 N003 C004 -88.33(12) . . . . ?
C00C O001 N003 C00A 67.22(11) . . . . ?
C00C C00K C00M C00B -64.80(15) . . . . ?
C00D C00B C00G C00N 0.87(18) . . . . ?
C00D C00B C00M C00K 106.12(14) . . . . ?
C00D C00F C00O C00N 0.3(2) . . . . ?
C00E C009 C00H C008 -179.49(11) . . . . ?
C00E C009 C00H C00L -1.06(19) . . . . ?
C00G C00B C00D C00F -0.08(19) . . . . ?
C00G C00B C00M C00K -75.64(15) . . . . ?
C00G C00N C00O C00F 0.5(2) . . . . ?
C00H C008 C00A N003 40.18(15) . . . . ?
C00H C008 C00A C007 -85.50(14) . . . . ?
C00H C009 C00E C00J 0.0(2) . . . . ?
C00J C00I C00L C00H 0.1(2) . . . . ?
C00K C007 C00A N003 52.00(12) . . . . ?
C00K C007 C00A C008 176.93(10) . . . . ?
C00L C00I C00J C00E -1.2(2) . . . . ?
C00M C00B C00D C00F 178.20(12) . . . . ?
C00M C00B C00G C00N -177.43(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/PE(2:1)'
####################################################################### 
# 
# 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_0203_4_0ma
_database_code_depnum_ccdc_archive 'CCDC 2244764'
loop_
_audit_author_name
_audit_author_address
'Yuanxiang He'
;Sichuan University of Science  Engineering
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-08-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O2'
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.8140(4)
_cell_length_b                   9.0568(3)
_cell_length_c                   30.5543(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3545.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7267
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.54
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.885
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0939 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.1273.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            41144
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.533
_diffrn_reflns_theta_min         2.892
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3158
_reflns_number_total             3621
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1277P)²+0.0965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1736
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C007(H007)
1.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C00E(H00L,H00M), C00H(H00O,H00P)
1.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00G(H00N), C00I(H00Q), C00J(H00R), C00K(H00S), C00M(H00T),
 C00N(H00U), C00O(H00V), C00P(H00W)
1.d Idealised Me refined as rotating group:
 C008(H00C,H00D,H00E), C00B(H00F,H00G,H00H), C00C(H00I,H00J,H00K)
;
_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 0.74895(7) 0.09705(10) 0.61043(3) 0.0584(3) Uani 1 1 d . . . . .
O002 O 0.85390(8) 0.23251(12) 0.67295(3) 0.0651(3) Uani 1 1 d . . . . .
N003 N 0.70806(9) 0.10779(13) 0.65287(4) 0.0573(3) Uani 1 1 d . . . . .
C004 C 0.76625(11) 0.18745(15) 0.68177(5) 0.0577(3) Uani 1 1 d . . . . .
C005 C 0.59119(11) 0.35735(14) 0.50629(4) 0.0569(3) Uani 1 1 d . . . . .
C006 C 0.55538(11) 0.34918(15) 0.55342(4) 0.0571(3) Uani 1 1 d . . . . .
H00A H 0.478171 0.352999 0.553868 0.069 Uiso 1 1 calc R U . . .
H00B H 0.581223 0.437907 0.568936 0.069 Uiso 1 1 calc R U . . .
C007 C 0.59432(10) 0.08603(15) 0.65349(5) 0.0577(3) Uani 1 1 d . . . . .
H007 H 0.580581 -0.010277 0.638557 0.069 Uiso 1 1 calc R U . . .
C008 C 0.54414(11) 0.35792(15) 0.64909(4) 0.0588(3) Uani 1 1 d . . . . .
H00C H 0.517629 0.348577 0.679047 0.088 Uiso 1 1 calc R U . . .
H00D H 0.501773 0.429857 0.633019 0.088 Uiso 1 1 calc R U . . .
H00E H 0.616847 0.391397 0.649879 0.088 Uiso 1 1 calc R U . . .
C009 C 0.77024(13) 0.29231(18) 0.75692(5) 0.0671(4) Uani 1 1 d . . . . .
H009 H 0.839003 0.326029 0.750985 0.080 Uiso 1 1 calc R U . . .
C00A C 0.59094(10) 0.21049(14) 0.57931(4) 0.0548(3) Uani 1 1 d . . . . .
C00B C 0.56546(11) 0.07016(15) 0.55299(5) 0.0604(3) Uani 1 1 d . . . . .
H00F H 0.490286 0.066124 0.547222 0.091 Uiso 1 1 calc R U . . .
H00G H 0.586389 -0.017055 0.569828 0.091 Uiso 1 1 calc R U . . .
H00H H 0.603489 0.072045 0.525170 0.091 Uiso 1 1 calc R U . . .
C00C C 0.42243(11) 0.16248(18) 0.62252(5) 0.0648(4) Uani 1 1 d . . . . .
H00I H 0.417321 0.057881 0.614597 0.097 Uiso 1 1 calc R U . . .
H00J H 0.388326 0.222551 0.600004 0.097 Uiso 1 1 calc R U . . .
H00K H 0.388009 0.178818 0.650751 0.097 Uiso 1 1 calc R U . . .
C00D C 0.53814(10) 0.20678(14) 0.62600(4) 0.0561(3) Uani 1 1 d . . . . .
C00E C 0.70981(10) 0.21945(14) 0.58505(5) 0.0564(3) Uani 1 1 d . . . . .
H00L H 0.743595 0.219420 0.555912 0.068 Uiso 1 1 calc R U . . .
H00M H 0.727992 0.313182 0.599872 0.068 Uiso 1 1 calc R U . . .
C00F C 0.71625(11) 0.21168(15) 0.72539(5) 0.0593(3) Uani 1 1 d . . . . .
C00G C 0.68365(11) 0.42976(17) 0.49559(5) 0.0642(4) Uani 1 1 d . . . . .
H00N H 0.725098 0.471032 0.518278 0.077 Uiso 1 1 calc R U . . .
C00H C 0.55844(11) 0.06788(17) 0.70085(5) 0.0642(4) Uani 1 1 d . . . . .
H00O H 0.483323 0.092897 0.702433 0.077 Uiso 1 1 calc R U . . .
H00P H 0.565689 -0.037397 0.709022 0.077 Uiso 1 1 calc R U . . .
C00I C 0.53183(11) 0.29891(15) 0.47223(5) 0.0602(3) Uani 1 1 d . . . . .
H00Q H 0.467962 0.250251 0.478646 0.072 Uiso 1 1 calc R U . . .
C00J C 0.72420(15) 0.3236(2) 0.79687(5) 0.0737(4) Uani 1 1 d . . . . .
H00R H 0.760720 0.380046 0.818137 0.088 Uiso 1 1 calc R U . . .
C00K C 0.71645(13) 0.4429(2) 0.45253(5) 0.0709(4) Uani 1 1 d . . . . .
H00S H 0.779346 0.493722 0.445915 0.085 Uiso 1 1 calc R U . . .
C00L C 0.61558(12) 0.15935(16) 0.73414(5) 0.0614(3) Uani 1 1 d . . . . .
C00M C 0.65727(12) 0.38155(19) 0.41909(5) 0.0687(4) Uani 1 1 d . . . . .
H00T H 0.680244 0.388211 0.389592 0.082 Uiso 1 1 calc R U . . .
C00N C 0.56461(13) 0.31069(17) 0.42902(5) 0.0650(4) Uani 1 1 d . . . . .
H00U H 0.523244 0.269946 0.406222 0.078 Uiso 1 1 calc R U . . .
C00O C 0.57094(13) 0.18992(19) 0.77473(5) 0.0693(4) Uani 1 1 d . . . . .
H00V H 0.503050 0.154018 0.781272 0.083 Uiso 1 1 calc R U . . .
C00P C 0.62456(15) 0.27208(19) 0.80562(5) 0.0743(4) Uani 1 1 d . . . . .
H00W H 0.592815 0.293278 0.833003 0.089 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
O001 N003 1.4019(15) . ?
O001 C00E 1.4428(16) . ?
O002 C004 1.2249(18) . ?
N003 C004 1.3625(18) . ?
N003 C007 1.4709(17) . ?
C004 C00F 1.495(2) . ?
C005 C006 1.5131(19) . ?
C005 C00G 1.393(2) . ?
C005 C00I 1.3936(19) . ?
C006 H00A 0.9900 . ?
C006 H00B 0.9900 . ?
C006 C00A 1.5528(18) . ?
C007 H007 1.0000 . ?
C007 C00D 1.5554(18) . ?
C007 C00H 1.5271(19) . ?
C008 H00C 0.9800 . ?
C008 H00D 0.9800 . ?
C008 H00E 0.9800 . ?
C008 C00D 1.5419(18) . ?
C009 H009 0.9500 . ?
C009 C00F 1.393(2) . ?
C009 C00J 1.385(2) . ?
C00A C00B 1.5389(18) . ?
C00A C00D 1.5794(19) . ?
C00A C00E 1.5353(18) . ?
C00B H00F 0.9800 . ?
C00B H00G 0.9800 . ?
C00B H00H 0.9800 . ?
C00C H00I 0.9800 . ?
C00C H00J 0.9800 . ?
C00C H00K 0.9800 . ?
C00C C00D 1.5397(18) . ?
C00E H00L 0.9900 . ?
C00E H00M 0.9900 . ?
C00F C00L 1.400(2) . ?
C00G H00N 0.9500 . ?
C00G C00K 1.386(2) . ?
C00H H00O 0.9900 . ?
C00H H00P 0.9900 . ?
C00H C00L 1.502(2) . ?
C00I H00Q 0.9500 . ?
C00I C00N 1.389(2) . ?
C00J H00R 0.9500 . ?
C00J C00P 1.385(3) . ?
C00K H00S 0.9500 . ?
C00K C00M 1.388(2) . ?
C00L C00O 1.394(2) . ?
C00M H00T 0.9500 . ?
C00M C00N 1.383(2) . ?
C00N H00U 0.9500 . ?
C00O H00V 0.9500 . ?
C00O C00P 1.384(3) . ?
C00P H00W 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
N003 O001 C00E 108.30(9) . . ?
O001 N003 C007 111.90(10) . . ?
C004 N003 O001 115.58(11) . . ?
C004 N003 C007 127.22(12) . . ?
O002 C004 N003 122.38(13) . . ?
O002 C004 C00F 122.70(13) . . ?
N003 C004 C00F 114.90(12) . . ?
C00G C005 C006 120.29(12) . . ?
C00G C005 C00I 117.88(13) . . ?
C00I C005 C006 121.78(13) . . ?
C005 C006 H00A 108.3 . . ?
C005 C006 H00B 108.3 . . ?
C005 C006 C00A 115.80(11) . . ?
H00A C006 H00B 107.4 . . ?
C00A C006 H00A 108.3 . . ?
C00A C006 H00B 108.3 . . ?
N003 C007 H007 106.6 . . ?
N003 C007 C00D 110.94(11) . . ?
N003 C007 C00H 108.96(11) . . ?
C00D C007 H007 106.6 . . ?
C00H C007 H007 106.6 . . ?
C00H C007 C00D 116.61(11) . . ?
H00C C008 H00D 109.5 . . ?
H00C C008 H00E 109.5 . . ?
H00D C008 H00E 109.5 . . ?
C00D C008 H00C 109.5 . . ?
C00D C008 H00D 109.5 . . ?
C00D C008 H00E 109.5 . . ?
C00F C009 H009 119.8 . . ?
C00J C009 H009 119.8 . . ?
C00J C009 C00F 120.35(16) . . ?
C006 C00A C00D 110.59(10) . . ?
C00B C00A C006 109.86(11) . . ?
C00B C00A C00D 111.32(11) . . ?
C00E C00A C006 107.86(11) . . ?
C00E C00A C00B 108.29(11) . . ?
C00E C00A C00D 108.84(11) . . ?
C00A C00B H00F 109.5 . . ?
C00A C00B H00G 109.5 . . ?
C00A C00B H00H 109.5 . . ?
H00F C00B H00G 109.5 . . ?
H00F C00B H00H 109.5 . . ?
H00G C00B H00H 109.5 . . ?
H00I C00C H00J 109.5 . . ?
H00I C00C H00K 109.5 . . ?
H00J C00C H00K 109.5 . . ?
C00D C00C H00I 109.5 . . ?
C00D C00C H00J 109.5 . . ?
C00D C00C H00K 109.5 . . ?
C007 C00D C00A 107.73(10) . . ?
C008 C00D C007 110.74(11) . . ?
C008 C00D C00A 111.90(11) . . ?
C00C C00D C007 107.44(11) . . ?
C00C C00D C008 108.12(11) . . ?
C00C C00D C00A 110.83(11) . . ?
O001 C00E C00A 111.45(11) . . ?
O001 C00E H00L 109.3 . . ?
O001 C00E H00M 109.3 . . ?
C00A C00E H00L 109.3 . . ?
C00A C00E H00M 109.3 . . ?
H00L C00E H00M 108.0 . . ?
C009 C00F C004 118.72(13) . . ?
C009 C00F C00L 120.21(14) . . ?
C00L C00F C004 121.02(13) . . ?
C005 C00G H00N 119.3 . . ?
C00K C00G C005 121.40(14) . . ?
C00K C00G H00N 119.3 . . ?
C007 C00H H00O 108.3 . . ?
C007 C00H H00P 108.3 . . ?
H00O C00H H00P 107.4 . . ?
C00L C00H C007 115.81(12) . . ?
C00L C00H H00O 108.3 . . ?
C00L C00H H00P 108.3 . . ?
C005 C00I H00Q 119.5 . . ?
C00N C00I C005 121.03(14) . . ?
C00N C00I H00Q 119.5 . . ?
C009 C00J H00R 120.2 . . ?
C009 C00J C00P 119.58(16) . . ?
C00P C00J H00R 120.2 . . ?
C00G C00K H00S 120.0 . . ?
C00G C00K C00M 119.91(15) . . ?
C00M C00K H00S 120.0 . . ?
C00F C00L C00H 120.43(13) . . ?
C00O C00L C00F 118.74(15) . . ?
C00O C00L C00H 120.81(14) . . ?
C00K C00M H00T 120.2 . . ?
C00N C00M C00K 119.53(14) . . ?
C00N C00M H00T 120.2 . . ?
C00I C00N H00U 119.9 . . ?
C00M C00N C00I 120.24(14) . . ?
C00M C00N H00U 119.9 . . ?
C00L C00O H00V 119.7 . . ?
C00P C00O C00L 120.65(16) . . ?
C00P C00O H00V 119.7 . . ?
C00J C00P H00W 119.8 . . ?
C00O C00P C00J 120.46(15) . . ?
C00O C00P H00W 119.8 . . ?

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 N003 C004 O002 -8.0(2) . . . . ?
O001 N003 C004 C00F 173.67(10) . . . . ?
O001 N003 C007 C00D -61.69(14) . . . . ?
O001 N003 C007 C00H 168.62(10) . . . . ?
O002 C004 C00F C009 1.8(2) . . . . ?
O002 C004 C00F C00L 179.55(14) . . . . ?
N003 O001 C00E C00A -64.80(13) . . . . ?
N003 C004 C00F C009 -179.87(13) . . . . ?
N003 C004 C00F C00L -2.17(19) . . . . ?
N003 C007 C00D C008 -70.67(14) . . . . ?
N003 C007 C00D C00A 51.99(14) . . . . ?
N003 C007 C00D C00C 171.45(11) . . . . ?
N003 C007 C00H C00L 35.91(17) . . . . ?
C004 N003 C007 C00D 91.14(16) . . . . ?
C004 N003 C007 C00H -38.56(18) . . . . ?
C004 C00F C00L C00H 4.4(2) . . . . ?
C004 C00F C00L C00O -177.50(13) . . . . ?
C005 C006 C00A C00B -50.35(16) . . . . ?
C005 C006 C00A C00D -173.61(11) . . . . ?
C005 C006 C00A C00E 67.48(14) . . . . ?
C005 C00G C00K C00M -0.8(2) . . . . ?
C005 C00I C00N C00M -0.2(2) . . . . ?
C006 C005 C00G C00K -177.91(14) . . . . ?
C006 C005 C00I C00N 178.34(13) . . . . ?
C006 C00A C00D C007 -168.10(10) . . . . ?
C006 C00A C00D C008 -46.15(14) . . . . ?
C006 C00A C00D C00C 74.62(14) . . . . ?
C006 C00A C00E O001 177.69(10) . . . . ?
C007 N003 C004 O002 -160.02(13) . . . . ?
C007 N003 C004 C00F 21.7(2) . . . . ?
C007 C00H C00L C00F -22.86(19) . . . . ?
C007 C00H C00L C00O 159.12(13) . . . . ?
C009 C00F C00L C00H -177.89(13) . . . . ?
C009 C00F C00L C00O 0.2(2) . . . . ?
C009 C00J C00P C00O -0.1(2) . . . . ?
C00B C00A C00D C007 69.48(13) . . . . ?
C00B C00A C00D C008 -168.57(11) . . . . ?
C00B C00A C00D C00C -47.80(15) . . . . ?
C00B C00A C00E O001 -63.47(14) . . . . ?
C00D C007 C00H C00L -90.60(15) . . . . ?
C00D C00A C00E O001 57.68(13) . . . . ?
C00E O001 N003 C004 -89.75(13) . . . . ?
C00E O001 N003 C007 66.47(13) . . . . ?
C00E C00A C00D C007 -49.79(13) . . . . ?
C00E C00A C00D C008 72.15(13) . . . . ?
C00E C00A C00D C00C -167.08(11) . . . . ?
C00F C009 C00J C00P 1.1(2) . . . . ?
C00F C00L C00O C00P 0.8(2) . . . . ?
C00G C005 C006 C00A -92.31(16) . . . . ?
C00G C005 C00I C00N 0.9(2) . . . . ?
C00G C00K C00M C00N 1.5(2) . . . . ?
C00H C007 C00D C008 54.84(15) . . . . ?
C00H C007 C00D C00A 177.51(11) . . . . ?
C00H C007 C00D C00C -63.03(15) . . . . ?
C00H C00L C00O C00P 178.87(14) . . . . ?
C00I C005 C006 C00A 90.31(16) . . . . ?
C00I C005 C00G C00K -0.4(2) . . . . ?
C00J C009 C00F C004 176.61(14) . . . . ?
C00J C009 C00F C00L -1.1(2) . . . . ?
C00K C00M C00N C00I -1.0(2) . . . . ?
C00L C00O C00P C00J -0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/PE(2:1)'
