# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_zh-a1409
_database_code_depnum_ccdc_archive 'CCDC 2326391'
loop_
_audit_author_name
_audit_author_address
'Hao Zhang'
;Southwest University
China
;
_audit_update_record             
;
2024-01-18 deposited with the CCDC.	2024-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   5.9905(4)
_cell_length_b                   8.0684(5)
_cell_length_c                   16.5496(9)
_cell_angle_alpha                96.029(5)
_cell_angle_beta                 98.627(5)
_cell_angle_gamma                92.934(5)
_cell_volume                     784.65(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    453(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      453(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14056
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.443
_diffrn_reflns_theta_max         72.547
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.767
_diffrn_reflns_point_group_measured_fraction_full 0.793
_reflns_number_total             4770
_reflns_number_gt                4507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_max     0.558
_reflns_Friedel_fraction_full    0.587

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1612P)²+0.6616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4770
_refine_ls_number_parameters     399
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.2314
_refine_ls_wR_factor_gt          0.2273
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7642(8) 0.8475(7) 0.6868(3) 0.0377(12) Uani 1 1 d . U . . .
O2 O 0.5023(8) 0.8160(5) 0.5735(3) 0.0297(10) Uani 1 1 d . . . . .
N1 N 0.5856(9) 1.0703(7) 0.6372(3) 0.0251(11) Uani 1 1 d . . . . .
H1 H 0.6644 1.1511 0.6684 0.030 Uiso 1 1 calc R U . . .
C1 C 0.6308(10) 0.9108(8) 0.6382(4) 0.0238(12) Uani 1 1 d . U . . .
C2 C 0.3800(12) 0.9267(8) 0.5226(4) 0.0287(14) Uani 1 1 d . . . . .
H2A H 0.2250 0.8824 0.5042 0.034 Uiso 1 1 calc R U . . .
H2B H 0.4516 0.9409 0.4747 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3867(9) 1.0938(7) 0.5770(3) 0.0183(11) Uani 1 1 d . . . . .
C4 C 0.1814(11) 1.1111(9) 0.6190(4) 0.0305(14) Uani 1 1 d . . . . .
H4A H 0.1461 1.0084 0.6403 0.046 Uiso 1 1 calc R U . . .
H4B H 0.0553 1.1358 0.5800 0.046 Uiso 1 1 calc R U . . .
H4C H 0.2118 1.2000 0.6633 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4338(10) 1.2480(7) 0.5323(3) 0.0199(11) Uani 1 1 d . . . . .
H5A H 0.4624 1.3458 0.5727 0.024 Uiso 1 1 calc R U . . .
H5B H 0.5704 1.2332 0.5082 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2452(9) 1.2810(7) 0.4653(3) 0.0186(11) Uani 1 1 d . . . . .
C7 C 0.2022(9) 1.1520(7) 0.3924(3) 0.0178(11) Uani 1 1 d . . . . .
C8 C 0.3596(10) 1.1270(8) 0.3396(3) 0.0234(12) Uani 1 1 d . . . . .
H8 H 0.4936 1.1945 0.3487 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3204(13) 1.0028(9) 0.2732(4) 0.0344(16) Uani 1 1 d . . . . .
H9 H 0.4279 0.9870 0.2385 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1187(13) 0.9018(9) 0.2589(4) 0.0368(16) Uani 1 1 d . . . . .
H10 H 0.0903 0.8189 0.2144 0.044 Uiso 1 1 calc R U . . .
C11 C -0.0372(12) 0.9263(9) 0.3112(4) 0.0330(15) Uani 1 1 d . . . . .
H11 H -0.1701 0.8577 0.3026 0.040 Uiso 1 1 calc R U . . .
C12 C 0.0007(10) 1.0511(8) 0.3763(4) 0.0236(12) Uani 1 1 d . . . . .
H12 H -0.1092 1.0682 0.4099 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1261(10) 1.4152(7) 0.4737(3) 0.0224(12) Uani 1 1 d . . . . .
H13 H 0.1659 1.4853 0.5226 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0622(10) 1.4662(7) 0.4146(3) 0.0193(11) Uani 1 1 d . U . . .
C15 C -0.0705(10) 1.4377(8) 0.3300(3) 0.0221(12) Uani 1 1 d . . . . .
H15 H 0.0470 1.3871 0.3083 0.027 Uiso 1 1 calc R U . . .
C16 C -0.2553(11) 1.4848(8) 0.2773(3) 0.0246(13) Uani 1 1 d . . . . .
H16 H -0.2611 1.4643 0.2207 0.030 Uiso 1 1 calc R U . . .
C17 C -0.4285(11) 1.5612(8) 0.3088(4) 0.0257(13) Uani 1 1 d . . . . .
H17 H -0.5528 1.5900 0.2735 0.031 Uiso 1 1 calc R U . . .
C18 C -0.4181(11) 1.5948(8) 0.3920(4) 0.0244(12) Uani 1 1 d . . . . .
H18 H -0.5343 1.6483 0.4131 0.029 Uiso 1 1 calc R U . . .
C19 C -0.2348(11) 1.5495(8) 0.4454(3) 0.0242(12) Uani 1 1 d . . . . .
H19 H -0.2277 1.5751 0.5019 0.029 Uiso 1 1 calc R U . . .
O3 O 0.6903(8) 1.3423(6) 0.7596(3) 0.0392(12) Uani 1 1 d . . . . .
O4 O 1.0588(7) 1.3544(5) 0.8139(3) 0.0266(9) Uani 1 1 d . U . . .
N2 N 0.9163(8) 1.5875(6) 0.7780(3) 0.0189(10) Uani 1 1 d . . . . .
H2 H 0.8136 1.6563 0.7676 0.023 Uiso 1 1 calc R U . . .
C20 C 0.8730(10) 1.4255(8) 0.7815(4) 0.0215(12) Uani 1 1 d . . . . .
C21 C 1.2408(10) 1.4868(7) 0.8387(4) 0.0210(11) Uani 1 1 d . . . . .
H21A H 1.3811 1.4513 0.8222 0.025 Uiso 1 1 calc R U . . .
H21B H 1.2650 1.5164 0.8979 0.025 Uiso 1 1 calc R U . . .
C22 C 1.1585(9) 1.6351(7) 0.7941(3) 0.0169(11) Uani 1 1 d . . . . .
C23 C 1.2506(11) 1.6339(9) 0.7131(4) 0.0284(14) Uani 1 1 d . . . . .
H23A H 1.2244 1.5240 0.6835 0.043 Uiso 1 1 calc R U . . .
H23B H 1.4101 1.6643 0.7240 0.043 Uiso 1 1 calc R U . . .
H23C H 1.1752 1.7125 0.6807 0.043 Uiso 1 1 calc R U . . .
C24 C 1.2122(9) 1.8090(7) 0.8441(3) 0.0190(11) Uani 1 1 d . . . . .
H24A H 1.3712 1.8182 0.8678 0.023 Uiso 1 1 calc R U . . .
H24B H 1.1903 1.8927 0.8062 0.023 Uiso 1 1 calc R U . . .
C25 C 1.0779(9) 1.8518(7) 0.9122(3) 0.0150(11) Uani 1 1 d . . . . .
C26 C 1.1024(9) 1.7471(7) 0.9805(3) 0.0149(10) Uani 1 1 d . . . . .
C27 C 1.3145(9) 1.7436(7) 1.0309(3) 0.0185(11) Uani 1 1 d . . . . .
H27 H 1.4363 1.8137 1.0237 0.022 Uiso 1 1 calc R U . . .
C28 C 1.3412(11) 1.6362(8) 1.0909(3) 0.0253(13) Uani 1 1 d . . . . .
H28 H 1.4803 1.6359 1.1244 0.030 Uiso 1 1 calc R U . . .
C29 C 1.1623(11) 1.5288(8) 1.1015(4) 0.0283(13) Uani 1 1 d . U . . .
H29 H 1.1823 1.4557 1.1415 0.034 Uiso 1 1 calc R U . . .
C30 C 0.9533(11) 1.5306(8) 1.0523(4) 0.0254(13) Uani 1 1 d . . . . .
H30 H 0.8329 1.4588 1.0592 0.031 Uiso 1 1 calc R U . . .
C31 C 0.9247(10) 1.6402(7) 0.9928(3) 0.0216(12) Uani 1 1 d . . . . .
H31 H 0.7838 1.6419 0.9606 0.026 Uiso 1 1 calc R U . . .
C32 C 0.9434(10) 1.9803(7) 0.9080(3) 0.0216(12) Uani 1 1 d . . . . .
H32 H 0.9322 2.0310 0.8598 0.026 Uiso 1 1 calc R U . . .
C33 C 0.8121(10) 2.0503(7) 0.9699(3) 0.0186(11) Uani 1 1 d . . . . .
C34 C 0.8724(10) 2.0487(7) 1.0550(3) 0.0200(11) Uani 1 1 d . . . . .
H34 H 1.0058 2.0023 1.0749 0.024 Uiso 1 1 calc R U . . .
C35 C 0.7395(10) 2.1141(8) 1.1099(4) 0.0255(13) Uani 1 1 d . . . . .
H35 H 0.7831 2.1106 1.1660 0.031 Uiso 1 1 calc R U . . .
C36 C 0.5406(11) 2.1851(7) 1.0817(4) 0.0271(13) Uani 1 1 d . . . . .
H36 H 0.4489 2.2277 1.1184 0.032 Uiso 1 1 calc R U . . .
C37 C 0.4809(10) 2.1915(8) 0.9978(4) 0.0265(13) Uani 1 1 d . . . . .
H37 H 0.3485 2.2397 0.9783 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6136(11) 2.1281(8) 0.9435(4) 0.0241(12) Uani 1 1 d . . . . .
H38 H 0.5719 2.1366 0.8877 0.029 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 1.217(7) . ?
O2 C1 1.359(8) . ?
O2 C2 1.443(7) . ?
N1 C1 1.330(8) . ?
N1 C3 1.468(7) . ?
C2 C3 1.536(8) . ?
C3 C4 1.506(8) . ?
C3 C5 1.547(7) . ?
C5 C6 1.514(7) . ?
C6 C13 1.333(8) . ?
C6 C7 1.491(8) . ?
C7 C8 1.386(7) . ?
C7 C12 1.396(8) . ?
C8 C9 1.391(9) . ?
C9 C10 1.397(11) . ?
C10 C11 1.374(10) . ?
C11 C12 1.380(9) . ?
C13 C14 1.483(8) . ?
C14 C15 1.388(7) . ?
C14 C19 1.393(8) . ?
C15 C16 1.397(8) . ?
C16 C17 1.374(9) . ?
C17 C18 1.366(9) . ?
C18 C19 1.392(9) . ?
O3 C20 1.239(8) . ?
O4 C20 1.344(7) . ?
O4 C21 1.467(7) . ?
N2 C20 1.328(8) . ?
N2 C22 1.459(7) . ?
C21 C22 1.536(8) . ?
C22 C23 1.523(7) . ?
C22 C24 1.545(8) . ?
C24 C25 1.502(7) . ?
C25 C32 1.346(8) . ?
C25 C26 1.475(7) . ?
C26 C31 1.388(8) . ?
C26 C27 1.415(7) . ?
C27 C28 1.381(8) . ?
C28 C29 1.386(9) . ?
C29 C30 1.389(9) . ?
C30 C31 1.389(8) . ?
C32 C33 1.466(7) . ?
C33 C34 1.402(7) . ?
C33 C38 1.406(9) . ?
C34 C35 1.378(8) . ?
C35 C36 1.387(9) . ?
C36 C37 1.388(10) . ?
C37 C38 1.364(9) . ?

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
C1 O2 C2 108.1(5) . . ?
C1 N1 C3 112.8(5) . . ?
O1 C1 N1 129.2(6) . . ?
O1 C1 O2 120.8(6) . . ?
N1 C1 O2 110.0(5) . . ?
O2 C2 C3 105.8(4) . . ?
N1 C3 C4 110.1(5) . . ?
N1 C3 C2 98.1(5) . . ?
C4 C3 C2 112.9(5) . . ?
N1 C3 C5 109.7(5) . . ?
C4 C3 C5 111.6(5) . . ?
C2 C3 C5 113.6(4) . . ?
C6 C5 C3 115.0(5) . . ?
C13 C6 C7 123.8(5) . . ?
C13 C6 C5 121.0(5) . . ?
C7 C6 C5 115.2(5) . . ?
C8 C7 C12 118.3(5) . . ?
C8 C7 C6 121.6(5) . . ?
C12 C7 C6 120.1(5) . . ?
C7 C8 C9 121.1(6) . . ?
C8 C9 C10 119.7(6) . . ?
C11 C10 C9 119.3(6) . . ?
C10 C11 C12 120.9(6) . . ?
C11 C12 C7 120.7(6) . . ?
C6 C13 C14 127.9(5) . . ?
C15 C14 C19 118.7(5) . . ?
C15 C14 C13 122.7(5) . . ?
C19 C14 C13 118.5(5) . . ?
C14 C15 C16 120.1(5) . . ?
C17 C16 C15 120.4(5) . . ?
C18 C17 C16 120.0(6) . . ?
C17 C18 C19 120.5(6) . . ?
C18 C19 C14 120.3(5) . . ?
C20 O4 C21 107.7(4) . . ?
C20 N2 C22 112.1(5) . . ?
O3 C20 N2 127.8(6) . . ?
O3 C20 O4 121.0(6) . . ?
N2 C20 O4 111.3(5) . . ?
O4 C21 C22 104.9(4) . . ?
N2 C22 C23 109.9(5) . . ?
N2 C22 C21 99.1(4) . . ?
C23 C22 C21 110.1(5) . . ?
N2 C22 C24 112.1(5) . . ?
C23 C22 C24 109.7(5) . . ?
C21 C22 C24 115.6(5) . . ?
C25 C24 C22 117.2(4) . . ?
C32 C25 C26 123.8(5) . . ?
C32 C25 C24 119.4(5) . . ?
C26 C25 C24 116.8(5) . . ?
C31 C26 C27 118.4(5) . . ?
C31 C26 C25 121.2(5) . . ?
C27 C26 C25 120.2(5) . . ?
C28 C27 C26 120.1(5) . . ?
C27 C28 C29 120.6(6) . . ?
C28 C29 C30 119.9(5) . . ?
C31 C30 C29 119.7(5) . . ?
C26 C31 C30 121.3(6) . . ?
C25 C32 C33 128.2(5) . . ?
C34 C33 C38 116.6(5) . . ?
C34 C33 C32 124.6(5) . . ?
C38 C33 C32 118.8(5) . . ?
C35 C34 C33 121.8(5) . . ?
C34 C35 C36 120.1(5) . . ?
C35 C36 C37 118.9(6) . . ?
C38 C37 C36 120.9(6) . . ?
C37 C38 C33 121.6(5) . . ?

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.096

_shelxl_version_number           2014-1



