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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_LH0106
_database_code_depnum_ccdc_archive 'CCDC 2100009'
loop_
_audit_author_name
_audit_author_address
'Hao Li'
;Department of Medicinal Chemistry, School of Pharmacy, Southwest Medical University
China
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2022-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   15.223(3)
_cell_length_b                   10.344(2)
_cell_length_c                   19.924(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3137.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5037
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   0.985
_exptl_transmission_factor_max   0.988
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18409
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.044
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3611
_reflns_number_gt                2822
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1509
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69283(7) 0.87888(10) 0.65969(6) 0.0593(3) Uani 1 1 d . . . . .
O2 O 0.27604(6) 0.91748(11) 0.57257(6) 0.0566(3) Uani 1 1 d . . . . .
N1 N 0.59528(6) 0.71447(10) 0.65160(5) 0.0310(3) Uani 1 1 d . . . . .
N2 N 0.54596(8) 0.36871(11) 0.61933(6) 0.0424(3) Uani 1 1 d . . . . .
C1 C 0.56925(8) 0.58106(11) 0.66948(6) 0.0297(3) Uani 1 1 d . . . . .
C2 C 0.58606(9) 0.55663(13) 0.74457(6) 0.0376(3) Uani 1 1 d . . . . .
H2 H 0.586384 0.463621 0.753938 0.045 Uiso 1 1 calc R U . . .
C3 C 0.66885(10) 0.61996(15) 0.77268(8) 0.0482(4) Uani 1 1 d . . . . .
H3A H 0.702878 0.555969 0.796983 0.058 Uiso 1 1 calc R U . . .
H3B H 0.652336 0.687501 0.804010 0.058 Uiso 1 1 calc R U . . .
C4 C 0.72567(9) 0.67839(14) 0.71647(8) 0.0473(4) Uani 1 1 d . . . . .
H4A H 0.774156 0.726022 0.736123 0.057 Uiso 1 1 calc R U . . .
H4B H 0.749932 0.609446 0.689170 0.057 Uiso 1 1 calc R U . . .
C5 C 0.67221(8) 0.76733(13) 0.67305(7) 0.0389(3) Uani 1 1 d . . . . .
C6 C 0.52063(8) 0.78273(11) 0.62760(6) 0.0292(3) Uani 1 1 d . . . . .
C7 C 0.44440(8) 0.71459(12) 0.64445(6) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.36369(8) 0.76192(13) 0.62554(6) 0.0363(3) Uani 1 1 d . . . . .
H8 H 0.312646 0.717260 0.636509 0.044 Uiso 1 1 calc R U . . .
C9 C 0.35915(9) 0.87808(14) 0.58959(6) 0.0378(3) Uani 1 1 d . . . . .
C10 C 0.43474(8) 0.94542(13) 0.57424(6) 0.0374(3) Uani 1 1 d . . . . .
H10 H 0.430990 1.023194 0.551003 0.045 Uiso 1 1 calc R U . . .
C11 C 0.51677(8) 0.89777(12) 0.59330(6) 0.0344(3) Uani 1 1 d . . . . .
H11 H 0.567818 0.943002 0.582986 0.041 Uiso 1 1 calc R U . . .
C12 C 0.26805(12) 1.0222(2) 0.52730(9) 0.0726(6) Uani 1 1 d . . . . .
H12A H 0.297547 1.001340 0.486107 0.109 Uiso 1 1 calc R U . . .
H12B H 0.294141 1.097964 0.546668 0.109 Uiso 1 1 calc R U . . .
H12C H 0.207037 1.038201 0.518396 0.109 Uiso 1 1 calc R U . . .
C13 C 0.49382(9) 0.61437(13) 0.75893(6) 0.0391(3) Uani 1 1 d . . . . .
H13A H 0.495118 0.704180 0.772905 0.047 Uiso 1 1 calc R U . . .
H13B H 0.458660 0.562777 0.789448 0.047 Uiso 1 1 calc R U . . .
C14 C 0.46930(8) 0.59509(12) 0.68298(6) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.41723(9) 0.47186(13) 0.66867(7) 0.0414(3) Uani 1 1 d . . . . .
H15A H 0.418918 0.416462 0.707927 0.050 Uiso 1 1 calc R U . . .
H15B H 0.356366 0.494279 0.660173 0.050 Uiso 1 1 calc R U . . .
C16 C 0.45312(10) 0.39888(14) 0.60918(8) 0.0464(4) Uani 1 1 d . . . . .
H16A H 0.420246 0.319388 0.603137 0.056 Uiso 1 1 calc R U . . .
H16B H 0.446357 0.450675 0.568922 0.056 Uiso 1 1 calc R U . . .
C17 C 0.57787(13) 0.27508(16) 0.57037(9) 0.0636(5) Uani 1 1 d . . . . .
H17A H 0.570596 0.309349 0.525941 0.095 Uiso 1 1 calc R U . . .
H17B H 0.545068 0.196223 0.574533 0.095 Uiso 1 1 calc R U . . .
H17C H 0.638962 0.258029 0.578406 0.095 Uiso 1 1 calc R U . . .
C18 C 0.59785(8) 0.48627(12) 0.61590(6) 0.0358(3) Uani 1 1 d . . . . .
H18A H 0.590958 0.525498 0.571991 0.043 Uiso 1 1 calc R U . . .
H18B H 0.659467 0.465417 0.621979 0.043 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 C5 1.2250(16) . ?
O2 C9 1.3718(15) . ?
O2 C12 1.415(2) . ?
N1 C5 1.3613(16) . ?
N1 C6 1.4207(15) . ?
N1 C1 1.4792(15) . ?
N2 C18 1.4518(17) . ?
N2 C17 1.4578(19) . ?
N2 C16 1.461(2) . ?
C1 C18 1.5136(17) . ?
C1 C2 1.5388(17) . ?
C1 C14 1.5519(17) . ?
C2 C3 1.5268(19) . ?
C2 C13 1.5525(18) . ?
C2 H2 0.9800 . ?
C3 C4 1.539(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.5024(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C11 1.3736(17) . ?
C6 C7 1.3986(16) . ?
C7 C8 1.3752(17) . ?
C7 C14 1.5036(17) . ?
C8 C9 1.4005(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3794(19) . ?
C10 C11 1.3951(17) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.5714(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5279(17) . ?
C15 C16 1.508(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 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
C9 O2 C12 117.67(12) . . ?
C5 N1 C6 126.45(11) . . ?
C5 N1 C1 121.97(10) . . ?
C6 N1 C1 109.30(9) . . ?
C18 N2 C17 110.09(12) . . ?
C18 N2 C16 109.93(11) . . ?
C17 N2 C16 111.81(12) . . ?
N1 C1 C18 110.94(10) . . ?
N1 C1 C2 110.05(10) . . ?
C18 C1 C2 122.12(11) . . ?
N1 C1 C14 102.54(9) . . ?
C18 C1 C14 117.69(10) . . ?
C2 C1 C14 90.57(9) . . ?
C3 C2 C1 115.05(11) . . ?
C3 C2 C13 120.93(12) . . ?
C1 C2 C13 88.03(9) . . ?
C3 C2 H2 110.3 . . ?
C1 C2 H2 110.3 . . ?
C13 C2 H2 110.3 . . ?
C2 C3 C4 111.44(12) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 110.81(12) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
O1 C5 N1 122.04(13) . . ?
O1 C5 C4 124.28(12) . . ?
N1 C5 C4 113.62(11) . . ?
C11 C6 C7 121.37(11) . . ?
C11 C6 N1 129.22(11) . . ?
C7 C6 N1 109.41(10) . . ?
C8 C7 C6 119.74(12) . . ?
C8 C7 C14 131.13(11) . . ?
C6 C7 C14 109.13(10) . . ?
C7 C8 C9 119.32(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O2 C9 C10 124.37(13) . . ?
O2 C9 C8 115.26(12) . . ?
C10 C9 C8 120.36(12) . . ?
C9 C10 C11 120.53(13) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 118.67(12) . . ?
C6 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 C14 89.34(9) . . ?
C2 C13 H13A 113.8 . . ?
C14 C13 H13A 113.8 . . ?
C2 C13 H13B 113.8 . . ?
C14 C13 H13B 113.8 . . ?
H13A C13 H13B 111.0 . . ?
C7 C14 C15 117.38(11) . . ?
C7 C14 C1 103.63(9) . . ?
C15 C14 C1 113.47(10) . . ?
C7 C14 C13 116.56(10) . . ?
C15 C14 C13 114.13(10) . . ?
C1 C14 C13 86.90(9) . . ?
C16 C15 C14 112.11(11) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C15 110.39(12) . . ?
N2 C16 H16A 109.6 . . ?
C15 C16 H16A 109.6 . . ?
N2 C16 H16B 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C1 110.66(10) . . ?
N2 C18 H18A 109.5 . . ?
C1 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 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
C5 N1 C1 C18 -93.25(14) . . . . ?
C6 N1 C1 C18 102.87(11) . . . . ?
C5 N1 C1 C2 44.97(16) . . . . ?
C6 N1 C1 C2 -118.91(11) . . . . ?
C5 N1 C1 C14 140.25(12) . . . . ?
C6 N1 C1 C14 -23.63(12) . . . . ?
N1 C1 C2 C3 -37.17(15) . . . . ?
C18 C1 C2 C3 95.55(15) . . . . ?
C14 C1 C2 C3 -140.74(12) . . . . ?
N1 C1 C2 C13 86.30(11) . . . . ?
C18 C1 C2 C13 -140.98(12) . . . . ?
C14 C1 C2 C13 -17.27(9) . . . . ?
C1 C2 C3 C4 -8.71(17) . . . . ?
C13 C2 C3 C4 -112.34(14) . . . . ?
C2 C3 C4 C5 52.85(16) . . . . ?
C6 N1 C5 O1 -17.1(2) . . . . ?
C1 N1 C5 O1 -178.12(13) . . . . ?
C6 N1 C5 C4 160.18(12) . . . . ?
C1 N1 C5 C4 -0.80(18) . . . . ?
C3 C4 C5 O1 127.67(16) . . . . ?
C3 C4 C5 N1 -49.58(16) . . . . ?
C5 N1 C6 C11 31.6(2) . . . . ?
C1 N1 C6 C11 -165.41(12) . . . . ?
C5 N1 C6 C7 -148.01(12) . . . . ?
C1 N1 C6 C7 14.97(14) . . . . ?
C11 C6 C7 C8 1.09(19) . . . . ?
N1 C6 C7 C8 -179.25(11) . . . . ?
C11 C6 C7 C14 -178.63(11) . . . . ?
N1 C6 C7 C14 1.03(14) . . . . ?
C6 C7 C8 C9 -0.03(19) . . . . ?
C14 C7 C8 C9 179.62(12) . . . . ?
C12 O2 C9 C10 10.7(2) . . . . ?
C12 O2 C9 C8 -170.05(14) . . . . ?
C7 C8 C9 O2 179.67(12) . . . . ?
C7 C8 C9 C10 -1.04(19) . . . . ?
O2 C9 C10 C11 -179.71(12) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C7 C6 C11 C10 -1.06(19) . . . . ?
N1 C6 C11 C10 179.36(12) . . . . ?
C9 C10 C11 C6 0.0(2) . . . . ?
C3 C2 C13 C14 135.29(12) . . . . ?
C1 C2 C13 C14 17.05(9) . . . . ?
C8 C7 C14 C15 38.96(19) . . . . ?
C6 C7 C14 C15 -141.37(11) . . . . ?
C8 C7 C14 C1 164.91(13) . . . . ?
C6 C7 C14 C1 -15.42(13) . . . . ?
C8 C7 C14 C13 -101.71(16) . . . . ?
C6 C7 C14 C13 77.96(13) . . . . ?
N1 C1 C14 C7 22.96(11) . . . . ?
C18 C1 C14 C7 -99.06(12) . . . . ?
C2 C1 C14 C7 133.66(10) . . . . ?
N1 C1 C14 C15 151.36(10) . . . . ?
C18 C1 C14 C15 29.34(15) . . . . ?
C2 C1 C14 C15 -97.94(11) . . . . ?
N1 C1 C14 C13 -93.63(10) . . . . ?
C18 C1 C14 C13 144.35(11) . . . . ?
C2 C1 C14 C13 17.07(9) . . . . ?
C2 C13 C14 C7 -120.61(11) . . . . ?
C2 C13 C14 C15 97.47(12) . . . . ?
C2 C13 C14 C1 -16.92(9) . . . . ?
C7 C14 C15 C16 85.02(15) . . . . ?
C1 C14 C15 C16 -35.92(16) . . . . ?
C13 C14 C15 C16 -133.38(13) . . . . ?
C18 N2 C16 C15 -69.82(14) . . . . ?
C17 N2 C16 C15 167.59(13) . . . . ?
C14 C15 C16 N2 56.40(16) . . . . ?
C17 N2 C18 C1 -176.35(12) . . . . ?
C16 N2 C18 C1 60.05(14) . . . . ?
N1 C1 C18 N2 -158.38(10) . . . . ?
C2 C1 C18 N2 69.27(15) . . . . ?
C14 C1 C18 N2 -40.77(15) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.073

