# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_OSM-V-7
_database_code_depnum_ccdc_archive 'CCDC 2073434'
loop_
_audit_author_name
_audit_author_address
'Ji-Eun Lee'
;Gyeongsang National University
South Korea
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2021-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8503(3)
_cell_length_b                   8.8759(2)
_cell_length_c                   19.9348(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.1887(12)
_cell_angle_gamma                90
_cell_volume                     1889.57(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.46

_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             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.371
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.324
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7249
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SHELXL-2014/7 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(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            33546
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4337
_reflns_number_gt                3884
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0564P)²+0.7216P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0139(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4337
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.20489(9) 0.06843(10) 0.39157(4) 0.0331(2) Uani 1 1 d . . . . .
O2 O 0.06539(9) 0.39301(10) 0.20369(4) 0.0299(2) Uani 1 1 d . . . . .
O3 O 0.28094(10) 0.59283(10) 0.41326(5) 0.0373(2) Uani 1 1 d . . . . .
H3 H 0.3083 0.5668 0.4537 0.056 Uiso 1 1 calc R U . . .
N1 N 0.43571(9) 0.24886(11) 0.57328(5) 0.0238(2) Uani 1 1 d . . . . .
H1A H 0.5049 0.2245 0.6013 0.029 Uiso 1 1 calc R U . . .
C1 C 0.42550(11) 0.26931(12) 0.50374(5) 0.0212(2) Uani 1 1 d . . . . .
C2 C 0.30298(10) 0.30331(13) 0.47651(5) 0.0217(2) Uani 1 1 d . . . . .
C3 C 0.23530(11) 0.30704(13) 0.53234(6) 0.0248(2) Uani 1 1 d . . . . .
C4 C 0.11064(12) 0.33835(16) 0.53714(7) 0.0345(3) Uani 1 1 d . . . . .
H4A H 0.0510 0.3613 0.4975 0.041 Uiso 1 1 calc R U . . .
C5 C 0.07607(14) 0.3353(2) 0.60036(8) 0.0451(4) Uani 1 1 d . . . . .
H5A H -0.0080 0.3575 0.6043 0.054 Uiso 1 1 calc R U . . .
C6 C 0.16327(16) 0.2996(2) 0.65893(8) 0.0464(4) Uani 1 1 d . . . . .
H6A H 0.1366 0.2975 0.7018 0.056 Uiso 1 1 calc R U . . .
C7 C 0.28633(14) 0.26769(16) 0.65600(7) 0.0362(3) Uani 1 1 d . . . . .
H7A H 0.3449 0.2435 0.6959 0.043 Uiso 1 1 calc R U . . .
C8 C 0.32149(11) 0.27241(13) 0.59195(6) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.53586(10) 0.25010(13) 0.47124(5) 0.0215(2) Uani 1 1 d . . . . .
C10 C 0.55843(12) 0.34714(14) 0.41943(6) 0.0273(3) Uani 1 1 d . . . . .
H10A H 0.5008 0.4258 0.4043 0.033 Uiso 1 1 calc R U . . .
C11 C 0.66419(13) 0.32942(16) 0.39006(7) 0.0336(3) Uani 1 1 d . . . . .
H11A H 0.6782 0.3967 0.3551 0.040 Uiso 1 1 calc R U . . .
C12 C 0.75026(12) 0.21486(16) 0.41081(7) 0.0333(3) Uani 1 1 d . . . . .
C13 C 0.72864(11) 0.11970(15) 0.46288(6) 0.0304(3) Uani 1 1 d . . . . .
H13A H 0.7868 0.0417 0.4781 0.036 Uiso 1 1 calc R U . . .
C14 C 0.62355(11) 0.13669(13) 0.49300(6) 0.0248(2) Uani 1 1 d . . . . .
H14A H 0.6110 0.0707 0.5287 0.030 Uiso 1 1 calc R U . . .
C15 C 0.86293(15) 0.1935(2) 0.37698(9) 0.0534(4) Uani 1 1 d . . . . .
H15A H 0.8627 0.2704 0.3417 0.080 Uiso 1 1 calc R U . . .
H15B H 0.9395 0.2028 0.4111 0.080 Uiso 1 1 calc R U . . .
H15C H 0.8598 0.0932 0.3561 0.080 Uiso 1 1 calc R U . . .
C16 C 0.24545(10) 0.32624(13) 0.40400(5) 0.0213(2) Uani 1 1 d . . . . .
C17 C 0.19334(10) 0.20689(13) 0.36181(6) 0.0224(2) Uani 1 1 d . . . . .
C18 C 0.13480(11) 0.23167(13) 0.29495(6) 0.0238(2) Uani 1 1 d . . . . .
H18A H 0.1014 0.1498 0.2668 0.029 Uiso 1 1 calc R U . . .
C19 C 0.12575(10) 0.37828(13) 0.26982(5) 0.0227(2) Uani 1 1 d . . . . .
C20 C 0.17546(11) 0.49895(13) 0.30938(6) 0.0258(3) Uani 1 1 d . . . . .
H20A H 0.1699 0.5985 0.2916 0.031 Uiso 1 1 calc R U . . .
C21 C 0.23400(11) 0.46985(13) 0.37623(6) 0.0241(2) Uani 1 1 d . . . . .
C22 C 0.14943(13) -0.05694(14) 0.35264(7) 0.0347(3) Uani 1 1 d . . . . .
H22A H 0.1647 -0.1490 0.3800 0.052 Uiso 1 1 calc R U . . .
H22B H 0.0590 -0.0405 0.3397 0.052 Uiso 1 1 calc R U . . .
H22C H 0.1865 -0.0674 0.3115 0.052 Uiso 1 1 calc R U . . .
C23 C 0.02474(13) 0.54128(15) 0.18201(6) 0.0328(3) Uani 1 1 d . . . . .
H23A H -0.0169 0.5383 0.1342 0.049 Uiso 1 1 calc R U . . .
H23B H -0.0340 0.5785 0.2103 0.049 Uiso 1 1 calc R U . . .
H23C H 0.0973 0.6087 0.1867 0.049 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 C17 1.3607(14) . ?
O1 C22 1.4274(15) . ?
O2 C19 1.3706(13) . ?
O2 C23 1.4303(15) . ?
O3 C21 1.3649(14) . ?
N1 C8 1.3716(16) . ?
N1 C1 1.3829(14) . ?
C1 C2 1.3776(15) . ?
C1 C9 1.4687(16) . ?
C2 C3 1.4382(16) . ?
C2 C16 1.4837(14) . ?
C3 C4 1.4005(17) . ?
C3 C8 1.4099(16) . ?
C4 C5 1.377(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.3964(17) . ?
C9 C10 1.3993(16) . ?
C9 C14 1.4002(16) . ?
C10 C11 1.3863(18) . ?
C11 C12 1.393(2) . ?
C12 C13 1.390(2) . ?
C12 C15 1.5090(19) . ?
C13 C14 1.3876(17) . ?
C16 C21 1.3865(16) . ?
C16 C17 1.4075(16) . ?
C17 C18 1.3889(15) . ?
C18 C19 1.3916(16) . ?
C19 C20 1.3818(16) . ?
C20 C21 1.3953(15) . ?

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
C17 O1 C22 118.01(9) . . ?
C19 O2 C23 116.60(9) . . ?
C8 N1 C1 109.63(10) . . ?
C2 C1 N1 108.92(10) . . ?
C2 C1 C9 131.06(10) . . ?
N1 C1 C9 120.00(10) . . ?
C1 C2 C3 106.82(10) . . ?
C1 C2 C16 128.63(10) . . ?
C3 C2 C16 124.50(10) . . ?
C4 C3 C8 119.37(11) . . ?
C4 C3 C2 133.54(11) . . ?
C8 C3 C2 107.09(10) . . ?
C5 C4 C3 118.75(13) . . ?
C4 C5 C6 120.89(13) . . ?
C7 C6 C5 121.85(13) . . ?
C6 C7 C8 117.17(13) . . ?
N1 C8 C7 130.52(12) . . ?
N1 C8 C3 107.52(10) . . ?
C7 C8 C3 121.96(12) . . ?
C10 C9 C14 118.23(11) . . ?
C10 C9 C1 121.13(10) . . ?
C14 C9 C1 120.61(10) . . ?
C11 C10 C9 120.53(12) . . ?
C10 C11 C12 121.26(12) . . ?
C13 C12 C11 118.19(12) . . ?
C13 C12 C15 120.96(14) . . ?
C11 C12 C15 120.85(14) . . ?
C14 C13 C12 121.15(12) . . ?
C13 C14 C9 120.63(11) . . ?
C21 C16 C17 117.08(10) . . ?
C21 C16 C2 120.51(10) . . ?
C17 C16 C2 122.29(10) . . ?
O1 C17 C18 123.55(10) . . ?
O1 C17 C16 115.02(10) . . ?
C18 C17 C16 121.43(10) . . ?
C17 C18 C19 119.00(10) . . ?
O2 C19 C20 123.15(10) . . ?
O2 C19 C18 115.26(10) . . ?
C20 C19 C18 121.59(10) . . ?
C19 C20 C21 117.87(11) . . ?
O3 C21 C16 121.39(10) . . ?
O3 C21 C20 115.58(10) . . ?
C16 C21 C20 123.03(10) . . ?

_refine_diff_density_max         0.364
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043



