# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_RS039_280_1
_database_code_depnum_ccdc_archive 'CCDC 2207097'
loop_
_audit_author_name
_audit_author_address
Haoliqiang
;School of Pharmacy, East China University of Science and Technology
China
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         371.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0236(4)
_cell_length_b                   9.6327(7)
_cell_length_c                   17.0316(12)
_cell_angle_alpha                79.749(3)
_cell_angle_beta                 89.873(3)
_cell_angle_gamma                74.604(3)
_cell_volume                     936.50(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7364
_cell_measurement_theta_min      4.8445
_cell_measurement_theta_max      68.2926
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392

_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       Bruker
_diffrn_measurement_device_type  D8
_diffrn_measurement_method       'phi and omi'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11105
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_theta_min         4.84
_diffrn_reflns_theta_max         68.33
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             3350
_reflns_number_gt                2957
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1761
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+2.4185P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.228
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0274(19)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O001 0.7349(4) 0.5126(2) 0.42064(12) 0.0290(5) Uani d . . . 1 . .
O O002 0.0277(4) 0.4288(2) 0.30165(13) 0.0309(5) Uani d . . . 1 . .
H H002 -0.042(6) 0.468(3) 0.344(2) 0.046000 Uiso calc U . R 1 . .
O O003 0.0108(3) 0.6578(2) 0.23720(12) 0.0299(5) Uani d . . . 1 . .
N N004 0.4278(4) 0.6451(3) 0.30466(15) 0.0268(6) Uani d . . . 1 . .
H H1 0.549(6) 0.644(4) 0.336(2) 0.040000 Uiso d U . . 1 . .
C C005 0.2722(5) 0.4484(3) 0.19454(17) 0.0251(6) Uani d . . . 1 . .
C C006 0.1664(5) 0.5132(3) 0.26583(17) 0.0255(6) Uani d . . . 1 . .
C C007 0.4404(5) 0.4135(3) 0.38662(16) 0.0257(6) Uani d . . . 1 . .
H H007 0.369522 0.335694 0.398999 0.031000 Uiso calc U . R 1 . .
C C008 0.6380(5) 0.4099(3) 0.43400(17) 0.0256(6) Uani d . . . 1 . .
C C009 0.1196(5) 0.7641(3) 0.20731(18) 0.0287(7) Uani d . . . 1 . .
C C00A 0.5064(5) 0.3952(3) 0.18773(19) 0.0315(7) Uani d . . . 1 . .
H H00A 0.610862 0.399491 0.228362 0.038000 Uiso calc U . R 1 . .
C C00B 0.3495(5) 0.5253(3) 0.32394(17) 0.0249(6) Uani d . . . 1 . .
C C00C 0.3306(5) 0.7600(3) 0.24217(17) 0.0273(7) Uani d . . . 1 . .
C C00D 0.1238(6) 0.4417(4) 0.13427(19) 0.0341(7) Uani d . . . 1 . .
H H00D -0.037875 0.478865 0.137924 0.041000 Uiso calc U . R 1 . .
C C00E 0.4437(6) 0.3285(3) 0.06070(19) 0.0347(8) Uani d . . . 1 . .
C C00F 0.7438(5) 0.2817(3) 0.49735(17) 0.0265(6) Uani d . . . 1 . .
C C00G 0.9530(5) 0.2749(3) 0.53421(18) 0.0309(7) Uani d . . . 1 . .
H H00G 1.023888 0.352143 0.518956 0.037000 Uiso calc U . R 1 . .
C C00H 0.4340(6) 0.8714(3) 0.2165(2) 0.0346(7) Uani d . . . 1 . .
H H00H 0.577221 0.869511 0.240559 0.042000 Uiso calc U . R 1 . .
C C00I 1.0588(6) 0.1570(3) 0.59276(19) 0.0336(7) Uani d . . . 1 . .
H H00I 1.201217 0.155316 0.617277 0.040000 Uiso calc U . R 1 . .
C C00J 0.2088(6) 0.3815(4) 0.06866(19) 0.0369(8) Uani d . . . 1 . .
H H00J 0.104114 0.376391 0.028327 0.044000 Uiso calc U . R 1 . .
C C00K 0.6444(6) 0.1661(3) 0.52185(19) 0.0326(7) Uani d . . . 1 . .
H H00K 0.501176 0.168172 0.497792 0.039000 Uiso calc U . R 1 . .
C C00L 0.5900(6) 0.3352(4) 0.1211(2) 0.0355(8) Uani d . . . 1 . .
H H00L 0.751573 0.298152 0.117388 0.043000 Uiso calc U . R 1 . .
C C00M 0.7526(6) 0.0490(4) 0.58073(19) 0.0360(8) Uani d . . . 1 . .
H H00M 0.681291 -0.027779 0.596852 0.043000 Uiso calc U . R 1 . .
C C00N 0.0144(6) 0.8772(4) 0.14597(19) 0.0350(8) Uani d . . . 1 . .
H H00N -0.128138 0.878890 0.121534 0.042000 Uiso calc U . R 1 . .
C C00O 0.9636(6) 0.0412(3) 0.61686(18) 0.0336(7) Uani d . . . 1 . .
C C00P 0.3273(6) 0.9857(4) 0.1556(2) 0.0402(8) Uani d . . . 1 . .
H H00P 0.397403 1.062513 0.137849 0.048000 Uiso calc U . R 1 . .
C C00Q 0.1191(6) 0.9882(4) 0.1205(2) 0.0398(8) Uani d . . . 1 . .
H H00Q 0.047198 1.066617 0.078676 0.048000 Uiso calc U . R 1 . .
C C00R 1.0833(7) -0.0874(4) 0.6804(2) 0.0439(9) Uani d . . . 1 . .
H H00B 1.025991 -0.171956 0.675857 0.066000 Uiso calc U . R 1 . .
H H00C 1.051786 -0.061946 0.733292 0.066000 Uiso calc U . R 1 . .
H H00E 1.249834 -0.111821 0.673350 0.066000 Uiso calc U . R 1 . .
C C00S 0.5343(8) 0.2642(4) -0.0113(2) 0.0512(10) Uani d . . . 1 . .
H H00F 0.404785 0.269097 -0.047419 0.077000 Uiso calc U . R 1 . .
H H00O 0.634692 0.319884 -0.039287 0.077000 Uiso calc U . R 1 . .
H H00R 0.622266 0.161732 0.005861 0.077000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O001 C008 . 1.264(3) ?
O002 C006 . 1.383(3) ?
O003 C009 . 1.381(4) ?
O003 C006 . 1.457(3) ?
N004 C00B . 1.348(4) ?
N004 C00C . 1.393(4) ?
C005 C00A . 1.379(4) ?
C005 C00D . 1.384(4) ?
C005 C006 . 1.525(4) ?
C006 C00B . 1.524(4) ?
C007 C00B . 1.371(4) ?
C007 C008 . 1.428(4) ?
C008 C00F . 1.486(4) ?
C009 C00N . 1.383(4) ?
C009 C00C . 1.392(4) ?
C00A C00L . 1.397(4) ?
C00C C00H . 1.385(4) ?
C00D C00J . 1.385(5) ?
C00E C00L . 1.377(5) ?
C00E C00J . 1.386(5) ?
C00E C00S . 1.508(4) ?
C00F C00G . 1.390(4) ?
C00F C00K . 1.399(4) ?
C00G C00I . 1.380(4) ?
C00H C00P . 1.387(5) ?
C00I C00O . 1.385(5) ?
C00K C00M . 1.383(4) ?
C00M C00O . 1.391(5) ?
C00N C00Q . 1.385(5) ?
C00O C00R . 1.509(4) ?
C00P C00Q . 1.383(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C009 O003 C006 . . 114.5(2) ?
C00B N004 C00C . . 123.1(3) ?
C00A C005 C00D . . 118.8(3) ?
C00A C005 C006 . . 123.4(3) ?
C00D C005 C006 . . 117.8(3) ?
O002 C006 O003 . . 105.3(2) ?
O002 C006 C00B . . 112.5(2) ?
O003 C006 C00B . . 109.6(2) ?
O002 C006 C005 . . 108.0(2) ?
O003 C006 C005 . . 109.2(2) ?
C00B C006 C005 . . 112.0(2) ?
C00B C007 C008 . . 122.4(3) ?
O001 C008 C007 . . 120.9(3) ?
O001 C008 C00F . . 117.9(3) ?
C007 C008 C00F . . 121.1(3) ?
O003 C009 C00N . . 120.2(3) ?
O003 C009 C00C . . 119.3(3) ?
C00N C009 C00C . . 120.4(3) ?
C005 C00A C00L . . 120.0(3) ?
N004 C00B C007 . . 123.5(3) ?
N004 C00B C006 . . 115.3(3) ?
C007 C00B C006 . . 120.9(3) ?
C00H C00C C009 . . 119.9(3) ?
C00H C00C N004 . . 121.7(3) ?
C009 C00C N004 . . 118.3(3) ?
C005 C00D C00J . . 120.6(3) ?
C00L C00E C00J . . 117.7(3) ?
C00L C00E C00S . . 121.5(3) ?
C00J C00E C00S . . 120.8(3) ?
C00G C00F C00K . . 117.9(3) ?
C00G C00F C008 . . 118.6(3) ?
C00K C00F C008 . . 123.4(3) ?
C00I C00G C00F . . 120.6(3) ?
C00C C00H C00P . . 119.6(3) ?
C00G C00I C00O . . 122.0(3) ?
C00D C00J C00E . . 121.3(3) ?
C00M C00K C00F . . 120.7(3) ?
C00E C00L C00A . . 121.6(3) ?
C00K C00M C00O . . 121.4(3) ?
C009 C00N C00Q . . 119.3(3) ?
C00I C00O C00M . . 117.3(3) ?
C00I C00O C00R . . 121.2(3) ?
C00M C00O C00R . . 121.5(3) ?
C00Q C00P C00H . . 120.2(3) ?
C00P C00Q C00N . . 120.6(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C009 O003 C006 O002 . . . . 172.9(2) ?
C009 O003 C006 C00B . . . . 51.7(3) ?
C009 O003 C006 C005 . . . . -71.3(3) ?
C00A C005 C006 O002 . . . . -119.1(3) ?
C00D C005 C006 O002 . . . . 60.3(3) ?
C00A C005 C006 O003 . . . . 126.9(3) ?
C00D C005 C006 O003 . . . . -53.7(3) ?
C00A C005 C006 C00B . . . . 5.4(4) ?
C00D C005 C006 C00B . . . . -175.2(3) ?
C00B C007 C008 O001 . . . . 1.4(4) ?
C00B C007 C008 C00F . . . . -175.0(3) ?
C006 O003 C009 C00N . . . . 148.1(3) ?
C006 O003 C009 C00C . . . . -35.0(4) ?
C00D C005 C00A C00L . . . . -0.4(5) ?
C006 C005 C00A C00L . . . . 178.9(3) ?
C00C N004 C00B C007 . . . . -178.3(3) ?
C00C N004 C00B C006 . . . . 7.9(4) ?
C008 C007 C00B N004 . . . . -4.4(4) ?
C008 C007 C00B C006 . . . . 169.2(3) ?
O002 C006 C00B N004 . . . . -155.1(2) ?
O003 C006 C00B N004 . . . . -38.3(3) ?
C005 C006 C00B N004 . . . . 83.0(3) ?
O002 C006 C00B C007 . . . . 30.9(4) ?
O003 C006 C00B C007 . . . . 147.7(3) ?
C005 C006 C00B C007 . . . . -91.1(3) ?
O003 C009 C00C C00H . . . . -175.5(3) ?
C00N C009 C00C C00H . . . . 1.4(4) ?
O003 C009 C00C N004 . . . . 2.1(4) ?
C00N C009 C00C N004 . . . . 178.9(3) ?
C00B N004 C00C C00H . . . . -170.7(3) ?
C00B N004 C00C C009 . . . . 11.8(4) ?
C00A C005 C00D C00J . . . . 0.7(5) ?
C006 C005 C00D C00J . . . . -178.7(3) ?
O001 C008 C00F C00G . . . . -5.2(4) ?
C007 C008 C00F C00G . . . . 171.4(3) ?
O001 C008 C00F C00K . . . . 175.2(3) ?
C007 C008 C00F C00K . . . . -8.3(4) ?
C00K C00F C00G C00I . . . . 0.4(5) ?
C008 C00F C00G C00I . . . . -179.3(3) ?
C009 C00C C00H C00P . . . . -0.7(5) ?
N004 C00C C00H C00P . . . . -178.2(3) ?
C00F C00G C00I C00O . . . . 0.4(5) ?
C005 C00D C00J C00E . . . . -1.1(5) ?
C00L C00E C00J C00D . . . . 1.2(5) ?
C00S C00E C00J C00D . . . . -179.5(3) ?
C00G C00F C00K C00M . . . . -0.2(5) ?
C008 C00F C00K C00M . . . . 179.4(3) ?
C00J C00E C00L C00A . . . . -1.0(5) ?
C00S C00E C00L C00A . . . . 179.8(3) ?
C005 C00A C00L C00E . . . . 0.6(5) ?
C00F C00K C00M C00O . . . . -0.6(5) ?
O003 C009 C00N C00Q . . . . 175.6(3) ?
C00C C009 C00N C00Q . . . . -1.2(5) ?
C00G C00I C00O C00M . . . . -1.3(5) ?
C00G C00I C00O C00R . . . . 179.4(3) ?
C00K C00M C00O C00I . . . . 1.4(5) ?
C00K C00M C00O C00R . . . . -179.2(3) ?
C00C C00H C00P C00Q . . . . -0.1(5) ?
C00H C00P C00Q C00N . . . . 0.2(5) ?
C009 C00N C00Q C00P . . . . 0.4(5) ?

