# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_exp_2457
_audit_block_doi                 10.5517/ccdc.csd.cc2rdvgh
_database_code_depnum_ccdc_archive 'CCDC 2544587'
loop_
_audit_author_name
_audit_author_address
'Suckchang Hong'
;Seoul National University
South Korea
;
_audit_update_record             
;
2026-04-08 deposited with the CCDC.	2026-05-18 downloaded from the CCDC.
;
_audit_creation_date             2025-08-28
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O3'
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H19NO3
_chemical_oxdiff_usercomment     SB-22
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                   6.39809(16)
_cell_length_b                   11.3852(3)
_cell_length_c                   20.1220(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.180(2)
_cell_angle_gamma                90
_cell_volume                     1463.50(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    292.5(4)
_cell_measurement_theta_max      73.6500
_cell_measurement_theta_min      4.3880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_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  0.0156
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.793
_diffrn_reflns_theta_min         4.401
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -18.00   1.00    3.92    --  -41.24  38.00  90.00   48
  2  ω    -55.00  33.00   1.00    3.92    --  -41.24  38.00-180.00   88
  3  ω     62.00  87.00   1.00    3.92    --   41.24-125.00-150.00   25
  4  ω      6.00  62.00   1.00    3.92    --   41.24 -99.00 -90.00   56
  5  ω     95.00 178.00   1.00   15.66    --  106.19 125.00-120.00   83
  6  ω     68.00 131.00   1.00   15.66    --  106.19 -45.00  60.00   63
  7  ω     94.00 120.00   1.00   15.66    --  106.19 125.00-180.00   26
  8  ω    131.00 177.00   1.00   15.66    --  106.19 125.00  30.00   46
  9  ω     48.00 117.00   1.00   15.66    --  106.19-125.00  60.00   69
 10  ω     31.00 126.00   1.00   15.66    --  106.19 -30.00 150.00   95
 11  ω    145.00 171.00   1.00   15.66    --  106.19 125.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124476000
_diffrn_orient_matrix_UB_12      -0.1329163000
_diffrn_orient_matrix_UB_13      -0.0135503000
_diffrn_orient_matrix_UB_21      -0.1631776000
_diffrn_orient_matrix_UB_22      -0.0226729000
_diffrn_orient_matrix_UB_23      0.0520535000
_diffrn_orient_matrix_UB_31      -0.1771889000
_diffrn_orient_matrix_UB_32      0.0114358000
_diffrn_orient_matrix_UB_33      -0.0546200000
_diffrn_oxdiff_ac3_digest_frames 
;
01eb8ce647f2081d25f3bd63f056156cdb006536336
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01bce6eec8f21a8ac8ee0df6307efcf33ff5a4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2492
_reflns_number_total             2867
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.053
_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)+(0.0830P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00H(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C00B(H00C), C00C(H00D), C00E(H00E), C00G(H00I)
2.d Idealised Me refined as rotating group:
 C00F(H00F,H00G,H00H), C00I(H00L,H00M,H00N), C00J(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.0814(2) 0.62935(12) 0.44672(6) 0.0581(4) Uani 1 1 d . . . . .
O002 O 0.2725(2) 0.75032(11) 0.36083(8) 0.0679(4) Uani 1 1 d . . . . .
N003 N 0.1072(2) 0.46619(13) 0.42078(7) 0.0493(4) Uani 1 1 d . . . . .
H003 H 0.118011 0.436082 0.460020 0.059 Uiso 1 1 calc R . . . .
O004 O -0.0062(3) 0.79763(14) 0.29602(9) 0.0859(5) Uani 1 1 d . . . . .
C005 C 0.3904(2) 0.34245(13) 0.37786(8) 0.0423(4) Uani 1 1 d . . . . .
C006 C 0.0138(2) 0.56881(14) 0.40795(7) 0.0443(4) Uani 1 1 d . . . . .
C007 C 0.1896(2) 0.40907(14) 0.36309(7) 0.0434(4) Uani 1 1 d . . . . .
H007 H 0.083755 0.354544 0.344135 0.052 Uiso 1 1 calc R . . . .
C008 C 0.0361(2) 0.59802(15) 0.33425(7) 0.0451(4) Uani 1 1 d . . . . .
C009 C 0.0938(3) 0.72640(16) 0.32751(8) 0.0511(4) Uani 1 1 d . . . . .
C00A C 0.2084(3) 0.51308(15) 0.31522(8) 0.0477(4) Uani 1 1 d . . . . .
H00A H 0.345176 0.549583 0.321033 0.057 Uiso 1 1 calc R . . . .
H00B H 0.186356 0.487840 0.269324 0.057 Uiso 1 1 calc R . . . .
C00B C 0.5011(3) 0.34680(18) 0.43852(9) 0.0600(5) Uani 1 1 d . . . . .
H00C H 0.454391 0.394548 0.472137 0.072 Uiso 1 1 calc R . . . .
C00C C 0.4681(3) 0.27206(18) 0.32927(9) 0.0593(5) Uani 1 1 d . . . . .
H00D H 0.397435 0.268013 0.287683 0.071 Uiso 1 1 calc R . . . .
C00D C 0.7578(3) 0.20951(16) 0.40186(12) 0.0617(5) Uani 1 1 d . . . . .
C00E C 0.6815(3) 0.2806(2) 0.44989(11) 0.0689(5) Uani 1 1 d . . . . .
H00E H 0.752867 0.284545 0.491366 0.083 Uiso 1 1 calc R . . . .
C00F C -0.1748(3) 0.5723(2) 0.29710(10) 0.0674(5) Uani 1 1 d . . . . .
H00F H -0.208703 0.490711 0.301932 0.101 Uiso 1 1 calc GR . . . .
H00G H -0.165720 0.590492 0.250766 0.101 Uiso 1 1 calc GR . . . .
H00H H -0.281800 0.619555 0.315361 0.101 Uiso 1 1 calc GR . . . .
C00G C 0.6488(4) 0.20750(19) 0.34112(12) 0.0704(6) Uani 1 1 d . . . . .
H00I H 0.697993 0.161479 0.307142 0.085 Uiso 1 1 calc R . . . .
C00H C 0.3457(5) 0.8709(2) 0.36005(17) 0.0963(9) Uani 1 1 d . . . . .
H00J H 0.374085 0.893270 0.314928 0.116 Uiso 1 1 calc R . . . .
H00K H 0.238072 0.922646 0.375425 0.116 Uiso 1 1 calc R . . . .
C00I C 0.9510(4) 0.1352(2) 0.41604(18) 0.0938(9) Uani 1 1 d . . . . .
H00L H 1.036088 0.170072 0.451575 0.141 Uiso 1 1 calc GR . . . .
H00M H 1.029472 0.130822 0.376811 0.141 Uiso 1 1 calc GR . . . .
H00N H 0.910192 0.057628 0.428750 0.141 Uiso 1 1 calc GR . . . .
C00J C 0.5294(7) 0.8826(3) 0.4016(3) 0.1567(19) Uani 1 1 d . . . . .
H00O H 0.591013 0.958120 0.394569 0.235 Uiso 1 1 calc GR . . . .
H00P H 0.626880 0.822090 0.391175 0.235 Uiso 1 1 calc GR . . . .
H00Q H 0.495274 0.875454 0.447270 0.235 Uiso 1 1 calc GR . . . .


_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 C006 1.228(2) . ?
O002 C009 1.321(2) . ?
O002 C00H 1.450(3) . ?
N003 H003 0.8600 . ?
N003 C006 1.331(2) . ?
N003 C007 1.455(2) . ?
O004 C009 1.193(2) . ?
C005 C007 1.508(2) . ?
C005 C00B 1.378(2) . ?
C005 C00C 1.378(2) . ?
C006 C008 1.534(2) . ?
C007 H007 0.9800 . ?
C007 C00A 1.535(2) . ?
C008 C009 1.515(2) . ?
C008 C00A 1.531(2) . ?
C008 C00F 1.534(2) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00B H00C 0.9300 . ?
C00B C00E 1.387(3) . ?
C00C H00D 0.9300 . ?
C00C C00G 1.379(3) . ?
C00D C00E 1.371(3) . ?
C00D C00G 1.373(3) . ?
C00D C00I 1.512(3) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 0.9600 . ?
C00G H00I 0.9300 . ?
C00H H00J 0.9700 . ?
C00H H00K 0.9700 . ?
C00H C00J 1.410(4) . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00I H00N 0.9600 . ?
C00J H00O 0.9600 . ?
C00J H00P 0.9600 . ?
C00J H00Q 0.9600 . ?

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
C009 O002 C00H 117.40(17) . . ?
C006 N003 H003 122.7 . . ?
C006 N003 C007 114.59(13) . . ?
C007 N003 H003 122.7 . . ?
C00B C005 C007 123.17(15) . . ?
C00B C005 C00C 117.49(16) . . ?
C00C C005 C007 119.34(15) . . ?
O001 C006 N003 127.06(14) . . ?
O001 C006 C008 124.65(14) . . ?
N003 C006 C008 108.24(13) . . ?
N003 C007 C005 114.22(13) . . ?
N003 C007 H007 108.7 . . ?
N003 C007 C00A 101.56(13) . . ?
C005 C007 H007 108.7 . . ?
C005 C007 C00A 114.58(13) . . ?
C00A C007 H007 108.7 . . ?
C009 C008 C006 109.38(14) . . ?
C009 C008 C00A 113.86(13) . . ?
C009 C008 C00F 110.65(14) . . ?
C00A C008 C006 102.22(12) . . ?
C00A C008 C00F 112.55(15) . . ?
C00F C008 C006 107.65(14) . . ?
O002 C009 C008 111.20(13) . . ?
O004 C009 O002 123.56(18) . . ?
O004 C009 C008 125.24(17) . . ?
C007 C00A H00A 110.9 . . ?
C007 C00A H00B 110.9 . . ?
C008 C00A C007 104.34(12) . . ?
C008 C00A H00A 110.9 . . ?
C008 C00A H00B 110.9 . . ?
H00A C00A H00B 108.9 . . ?
C005 C00B H00C 119.7 . . ?
C005 C00B C00E 120.59(18) . . ?
C00E C00B H00C 119.7 . . ?
C005 C00C H00D 119.4 . . ?
C005 C00C C00G 121.27(18) . . ?
C00G C00C H00D 119.4 . . ?
C00E C00D C00G 117.00(18) . . ?
C00E C00D C00I 121.1(2) . . ?
C00G C00D C00I 121.9(2) . . ?
C00B C00E H00E 119.0 . . ?
C00D C00E C00B 122.02(19) . . ?
C00D C00E H00E 119.0 . . ?
C008 C00F H00F 109.5 . . ?
C008 C00F H00G 109.5 . . ?
C008 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 109.5 . . ?
C00C C00G H00I 119.2 . . ?
C00D C00G C00C 121.62(19) . . ?
C00D C00G H00I 119.2 . . ?
O002 C00H H00J 109.7 . . ?
O002 C00H H00K 109.7 . . ?
H00J C00H H00K 108.2 . . ?
C00J C00H O002 110.0(2) . . ?
C00J C00H H00J 109.7 . . ?
C00J C00H H00K 109.7 . . ?
C00D C00I H00L 109.5 . . ?
C00D C00I H00M 109.5 . . ?
C00D C00I H00N 109.5 . . ?
H00L C00I H00M 109.5 . . ?
H00L C00I H00N 109.5 . . ?
H00M C00I H00N 109.5 . . ?
C00H C00J H00O 109.5 . . ?
C00H C00J H00P 109.5 . . ?
C00H C00J H00Q 109.5 . . ?
H00O C00J H00P 109.5 . . ?
H00O C00J H00Q 109.5 . . ?
H00P C00J H00Q 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 C006 C008 C009 45.8(2) . . . . ?
O001 C006 C008 C00A 166.76(16) . . . . ?
O001 C006 C008 C00F -74.5(2) . . . . ?
N003 C006 C008 C009 -136.61(14) . . . . ?
N003 C006 C008 C00A -15.62(17) . . . . ?
N003 C006 C008 C00F 103.11(16) . . . . ?
N003 C007 C00A C008 -29.12(15) . . . . ?
C005 C007 C00A C008 -152.75(13) . . . . ?
C005 C00B C00E C00D 0.5(3) . . . . ?
C005 C00C C00G C00D 0.7(3) . . . . ?
C006 N003 C007 C005 144.82(14) . . . . ?
C006 N003 C007 C00A 20.94(18) . . . . ?
C006 C008 C009 O002 59.86(19) . . . . ?
C006 C008 C009 O004 -120.7(2) . . . . ?
C006 C008 C00A C007 27.39(16) . . . . ?
C007 N003 C006 O001 174.04(16) . . . . ?
C007 N003 C006 C008 -3.50(19) . . . . ?
C007 C005 C00B C00E 177.91(18) . . . . ?
C007 C005 C00C C00G -178.51(18) . . . . ?
C009 O002 C00H C00J 175.9(3) . . . . ?
C009 C008 C00A C007 145.22(13) . . . . ?
C00A C008 C009 O002 -53.77(19) . . . . ?
C00A C008 C009 O004 125.7(2) . . . . ?
C00B C005 C007 N003 -7.7(2) . . . . ?
C00B C005 C007 C00A 108.87(19) . . . . ?
C00B C005 C00C C00G 0.6(3) . . . . ?
C00C C005 C007 N003 171.38(15) . . . . ?
C00C C005 C007 C00A -72.05(19) . . . . ?
C00C C005 C00B C00E -1.2(3) . . . . ?
C00E C00D C00G C00C -1.3(3) . . . . ?
C00F C008 C009 O002 178.29(16) . . . . ?
C00F C008 C009 O004 -2.3(3) . . . . ?
C00F C008 C00A C007 -87.81(16) . . . . ?
C00G C00D C00E C00B 0.8(3) . . . . ?
C00H O002 C009 O004 1.8(3) . . . . ?
C00H O002 C009 C008 -178.8(2) . . . . ?
C00I C00D C00E C00B -178.1(2) . . . . ?
C00I C00D C00G C00C 177.5(2) . . . . ?

_shelx_SHELXL_version_number     2018/3
_olex2_date_sample_data_collection 2025-08-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.484
####################################################################### 
# 
# 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_exp_2426
_audit_block_doi                 10.5517/ccdc.csd.cc2rdvfg
_database_code_depnum_ccdc_archive 'CCDC 2544586'
loop_
_audit_author_name
_audit_author_address
'Suckchang Hong'
;Seoul National University
South Korea
;
_audit_update_record             
;
2026-04-08 deposited with the CCDC.	2026-05-18 downloaded from the CCDC.
;
_audit_creation_date             2025-07-02
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O3'
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H19NO3
_chemical_oxdiff_usercomment     LACTAM
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                   9.9009(3)
_cell_length_b                   6.2017(2)
_cell_length_c                   23.7192(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.975(3)
_cell_angle_gamma                90
_cell_volume                     1455.56(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    293.1(7)
_cell_measurement_theta_max      72.5990
_cell_measurement_theta_min      3.7140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5452
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.867
_diffrn_reflns_theta_min         3.729
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.1(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  38.00   1.00    4.00    --  -41.74   0.00 -30.00  120
  2  ω     33.00  82.00   1.00    4.00    --   41.74-125.00 -90.00   49
  3  ω     58.00  91.00   1.00    4.00    --   41.74-125.00  30.00   33
  4  ω    104.00 178.00   1.00   15.98    --  106.19 125.00 150.00   74
  5  ω     73.00 109.00   1.00   15.98    --  106.19 -94.00 -60.00   36
  6  ω     42.00  80.00   1.00   15.98    --  106.19-125.00-180.00   38
  7  ω     25.00  52.00   1.00   15.98    --  106.19 -94.00 -60.00   27
  8  ω     85.00 113.00   1.00   15.98    --  106.19-125.00-180.00   28
  9  ω     85.00 130.00   1.00   15.98    --  106.19  77.00-180.00   45
 10  ω     82.00 153.00   1.00   15.98    --  106.19  45.00 -30.00   71
 11  ω    110.00 170.00   1.00   15.98    --  106.19 125.00 -60.00   60
 12  ω     45.00 123.00   1.00   15.98    --  106.19 -45.00-120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0063167000
_diffrn_orient_matrix_UB_12      -0.1138553000
_diffrn_orient_matrix_UB_13      -0.0577501000
_diffrn_orient_matrix_UB_21      0.0356043000
_diffrn_orient_matrix_UB_22      0.2138056000
_diffrn_orient_matrix_UB_23      -0.0289962000
_diffrn_orient_matrix_UB_31      0.1514930000
_diffrn_orient_matrix_UB_32      -0.0550040000
_diffrn_orient_matrix_UB_33      0.0066962000
_diffrn_oxdiff_ac3_digest_frames 
;
01448a542fba85fab2b91edf5550dc9fa000689b8f9
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01e4c97233169ead8690c92fb595eb65c3db7a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2865
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.180
_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)+(0.0780P)²+2.7600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2785
_refine_ls_wR_factor_ref         0.2918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00I(H00L,H00M)
2.c Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C00A(H00C), C00D(H00D), C00F(H00F)
2.d Idealised Me refined as rotating group:
 C00G(H00E,H00G,H00H), C00H(H00I,H00J,H00K), C00J(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4037(3) -0.0689(5) 0.55782(14) 0.0615(9) Uani 1 1 d . . . . .
N002 N 0.3664(3) 0.2311(6) 0.50436(15) 0.0488(8) Uani 1 1 d . . . . .
H002 H 0.422106 0.200708 0.478489 0.059 Uiso 1 1 calc R . . . .
O003 O 0.3732(5) 0.4213(7) 0.63214(16) 0.0935(14) Uani 1 1 d . . . . .
C004 C 0.3446(4) 0.0993(7) 0.54696(19) 0.0483(10) Uani 1 1 d . . . . .
C005 C 0.2886(4) 0.4333(7) 0.50436(18) 0.0503(10) Uani 1 1 d . . . . .
H005 H 0.344658 0.546997 0.521759 0.060 Uiso 1 1 calc R . . . .
C006 C 0.2426(4) 0.5044(7) 0.44640(19) 0.0498(10) Uani 1 1 d . . . . .
C007 C 0.2760(5) 0.7059(7) 0.4260(2) 0.0602(11) Uani 1 1 d . . . . .
H007 H 0.328594 0.798149 0.448477 0.072 Uiso 1 1 calc R . . . .
C008 C 0.2275(4) 0.1896(7) 0.5812(2) 0.0552(11) Uani 1 1 d . . . . .
C009 C 0.1753(4) 0.3761(8) 0.5441(2) 0.0607(12) Uani 1 1 d . . . . .
H00A H 0.094661 0.332911 0.522585 0.073 Uiso 1 1 calc R . . . .
H00B H 0.153410 0.499457 0.567184 0.073 Uiso 1 1 calc R . . . .
C00A C 0.1651(4) 0.3709(8) 0.4109(2) 0.0616(12) Uani 1 1 d . . . . .
H00C H 0.142023 0.233636 0.423040 0.074 Uiso 1 1 calc R . . . .
C00B C 0.1559(5) 0.6396(9) 0.3374(2) 0.0673(13) Uani 1 1 d . . . . .
C00C C 0.2842(5) 0.2664(9) 0.6377(2) 0.0680(13) Uani 1 1 d . . . . .
C00D C 0.2330(5) 0.7723(9) 0.3729(2) 0.0708(13) Uani 1 1 d . . . . .
H00D H 0.256181 0.909336 0.360651 0.085 Uiso 1 1 calc R . . . .
O00E O 0.2576(6) 0.1932(10) 0.68200(19) 0.133(2) Uani 1 1 d . . . . .
C00F C 0.1222(5) 0.4391(10) 0.3581(2) 0.0707(14) Uani 1 1 d . . . . .
H00F H 0.068939 0.347566 0.335639 0.085 Uiso 1 1 calc R . . . .
C00G C 0.1239(5) 0.0110(10) 0.5902(3) 0.0842(18) Uani 1 1 d . . . . .
H00E H 0.095419 -0.048656 0.554348 0.126 Uiso 1 1 calc GR . . . .
H00G H 0.047104 0.069773 0.608455 0.126 Uiso 1 1 calc GR . . . .
H00H H 0.164102 -0.100226 0.613349 0.126 Uiso 1 1 calc GR . . . .
C00H C 0.1096(7) 0.7125(13) 0.2793(3) 0.099(2) Uani 1 1 d . . . . .
H00I H 0.139477 0.857617 0.273211 0.149 Uiso 1 1 calc GR . . . .
H00J H 0.012766 0.706933 0.276062 0.149 Uiso 1 1 calc GR . . . .
H00K H 0.147179 0.619236 0.251571 0.149 Uiso 1 1 calc GR . . . .
C00I C 0.4363(11) 0.5101(18) 0.6837(3) 0.158(5) Uani 1 1 d . . . . .
H00L H 0.366125 0.556216 0.708545 0.189 Uiso 1 1 calc R . . . .
H00M H 0.488132 0.397614 0.702837 0.189 Uiso 1 1 calc R . . . .
C00J C 0.5166(10) 0.6749(18) 0.6741(4) 0.147(4) Uani 1 1 d . . . . .
H00N H 0.566838 0.646878 0.640947 0.220 Uiso 1 1 calc GR . . . .
H00O H 0.578128 0.694595 0.705843 0.220 Uiso 1 1 calc GR . . . .
H00P H 0.463423 0.802949 0.668474 0.220 Uiso 1 1 calc GR . . . .


_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 1.219(5) . ?
N002 C004 1.323(5) . ?
N002 C005 1.472(5) . ?
O003 C00C 1.313(6) . ?
O003 C00I 1.461(8) . ?
C004 C008 1.543(5) . ?
C005 C006 1.500(6) . ?
C005 C009 1.531(6) . ?
C006 C007 1.384(6) . ?
C006 C00A 1.393(6) . ?
C007 C00D 1.376(7) . ?
C008 C009 1.532(7) . ?
C008 C00C 1.512(7) . ?
C008 C00G 1.529(7) . ?
C00A C00F 1.375(7) . ?
C00B C00D 1.388(7) . ?
C00B C00F 1.381(8) . ?
C00B C00H 1.507(7) . ?
C00C O00E 1.183(6) . ?
C00I C00J 1.319(12) . ?

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
C004 N002 C005 115.3(3) . . ?
C00C O003 C00I 117.5(5) . . ?
O001 C004 N002 126.9(4) . . ?
O001 C004 C008 124.3(4) . . ?
N002 C004 C008 108.8(3) . . ?
N002 C005 C006 113.2(3) . . ?
N002 C005 C009 101.4(3) . . ?
C006 C005 C009 115.2(3) . . ?
C007 C006 C005 121.2(4) . . ?
C007 C006 C00A 117.3(4) . . ?
C00A C006 C005 121.5(4) . . ?
C00D C007 C006 121.3(4) . . ?
C009 C008 C004 102.5(3) . . ?
C00C C008 C004 108.5(4) . . ?
C00C C008 C009 112.2(4) . . ?
C00C C008 C00G 109.6(4) . . ?
C00G C008 C004 109.3(4) . . ?
C00G C008 C009 114.4(4) . . ?
C005 C009 C008 106.8(3) . . ?
C00F C00A C006 121.0(5) . . ?
C00D C00B C00H 121.4(6) . . ?
C00F C00B C00D 116.9(5) . . ?
C00F C00B C00H 121.7(5) . . ?
O003 C00C C008 111.8(4) . . ?
O00E C00C O003 122.7(6) . . ?
O00E C00C C008 125.4(5) . . ?
C007 C00D C00B 121.6(5) . . ?
C00A C00F C00B 122.0(5) . . ?
C00J C00I O003 113.0(7) . . ?

_shelx_SHELXL_version_number     2018/3
_olex2_date_sample_data_collection 2025-07-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.439
_oxdiff_exptl_absorpt_empirical_full_min 0.225
