# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ov_akimoto-byproduct_autored
_database_code_depnum_ccdc_archive 'CCDC 2388516'
loop_
_audit_author_name
_audit_author_address
'Shuta Akimoro'
;Okayama University
Japan
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_audit_creation_date             2024-09-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_chemical_melting_point          ?
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'

_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      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                   8.1083(5)
_cell_length_b                   9.6805(5)
_cell_length_c                   10.8014(5)
_cell_angle_alpha                84.851(4)
_cell_angle_beta                 69.482(5)
_cell_angle_gamma                67.945(5)
_cell_volume                     735.08(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4656
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      29.5670
_cell_measurement_theta_min      4.0240
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9424
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.658
_diffrn_reflns_theta_min         4.033
_diffrn_ambient_temperature      173.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2982
_reflns_number_total             3513
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.065
_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)+(0.0474P)²+0.1979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C6(H6), C5(H5), C17(H17), C3(H3), C2(H2), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O10 O -0.05726(11) 0.29223(8) 1.02230(7) 0.02003(18) Uani 1 1 d . . . . .
O13 O 0.19047(11) 0.12082(8) 0.87213(8) 0.02278(18) Uani 1 1 d . . . . .
O14 O 0.30268(12) 0.25076(9) 0.20624(8) 0.0267(2) Uani 1 1 d . . . . .
N7 N 0.27588(12) 0.34825(10) 0.71636(9) 0.0180(2) Uani 1 1 d . . . . .
N16 N 0.77969(14) 0.24427(12) 0.80021(11) 0.0279(2) Uani 1 1 d . . . . .
C19 C 0.43993(15) 0.31368(11) 0.74395(10) 0.0178(2) Uani 1 1 d . . . . .
C4 C 0.29601(15) 0.26544(12) 0.33294(10) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.08510(14) 0.24769(12) 0.90596(10) 0.0176(2) Uani 1 1 d . . . . .
C8 C 0.09617(14) 0.38193(12) 0.82369(10) 0.0179(2) Uani 1 1 d . . . . .
H8A H -0.007565 0.416613 0.786638 0.021 Uiso 1 1 calc R U . . .
H8B H 0.077684 0.464058 0.881620 0.021 Uiso 1 1 calc R U . . .
C18 C 0.62029(15) 0.25271(12) 0.64604(11) 0.0205(2) Uani 1 1 d . . . . .
H18 H 0.631984 0.233729 0.557977 0.025 Uiso 1 1 calc R U . . .
C20 C 0.43748(16) 0.33890(13) 0.87101(11) 0.0216(2) Uani 1 1 d . . . . .
H20 H 0.320482 0.379716 0.941555 0.026 Uiso 1 1 calc R U . . .
C1 C 0.28293(14) 0.31810(12) 0.58626(10) 0.0179(2) Uani 1 1 d . . . . .
C6 C 0.29883(16) 0.17964(12) 0.54845(11) 0.0225(2) Uani 1 1 d . . . . .
H6 H 0.305070 0.102344 0.609405 0.027 Uiso 1 1 calc R U . . .
C5 C 0.30581(17) 0.15219(13) 0.42169(11) 0.0233(2) Uani 1 1 d . . . . .
H5 H 0.317190 0.056651 0.396339 0.028 Uiso 1 1 calc R U . . .
C17 C 0.78009(16) 0.22079(13) 0.67946(12) 0.0249(2) Uani 1 1 d . . . . .
H17 H 0.899719 0.178890 0.611560 0.030 Uiso 1 1 calc R U . . .
C3 C 0.27835(18) 0.40539(13) 0.37119(11) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.270535 0.483296 0.310838 0.032 Uiso 1 1 calc R U . . .
C15 C 0.34646(18) 0.10363(14) 0.15834(12) 0.0277(3) Uani 1 1 d . . . . .
H15A H 0.353227 0.106208 0.065821 0.042 Uiso 1 1 calc R U . . .
H15B H 0.247422 0.066678 0.211891 0.042 Uiso 1 1 calc R U . . .
H15C H 0.468721 0.037214 0.164491 0.042 Uiso 1 1 calc R U . . .
C11 C -0.09915(16) 0.17491(13) 1.10699(11) 0.0238(2) Uani 1 1 d . . . . .
H11A H 0.018900 0.087510 1.097174 0.029 Uiso 1 1 calc R U . . .
H11B H -0.186265 0.142612 1.082355 0.029 Uiso 1 1 calc R U . . .
C2 C 0.27218(17) 0.43110(13) 0.49709(11) 0.0244(2) Uani 1 1 d . . . . .
H2 H 0.260508 0.526643 0.522657 0.029 Uiso 1 1 calc R U . . .
C21 C 0.60685(17) 0.30375(14) 0.89217(12) 0.0260(3) Uani 1 1 d . . . . .
H21 H 0.600505 0.323207 0.978708 0.031 Uiso 1 1 calc R U . . .
C12 C -0.1902(2) 0.23837(16) 1.24769(13) 0.0382(3) Uani 1 1 d . . . . .
H12A H -0.303707 0.327354 1.255270 0.057 Uiso 1 1 calc R U . . .
H12B H -0.100424 0.265410 1.272322 0.057 Uiso 1 1 calc R U . . .
H12C H -0.225612 0.163582 1.306950 0.057 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
O10 C9 1.3431(12) . ?
O10 C11 1.4586(13) . ?
O13 C9 1.2023(13) . ?
O14 C4 1.3687(13) . ?
O14 C15 1.4304(14) . ?
N7 C19 1.3769(13) . ?
N7 C8 1.4493(13) . ?
N7 C1 1.4380(13) . ?
N16 C17 1.3426(16) . ?
N16 C21 1.3428(16) . ?
C19 C18 1.4090(15) . ?
C19 C20 1.4074(15) . ?
C4 C5 1.3881(16) . ?
C4 C3 1.3928(16) . ?
C9 C8 1.5202(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C17 1.3827(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.3817(15) . ?
C1 C6 1.3827(15) . ?
C1 C2 1.3892(15) . ?
C6 H6 0.9500 . ?
C6 C5 1.3957(15) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.3847(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5075(17) . ?
C2 H2 0.9500 . ?
C21 H21 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 O10 C11 116.59(8) . . ?
C4 O14 C15 116.82(9) . . ?
C19 N7 C8 119.86(9) . . ?
C19 N7 C1 120.77(9) . . ?
C1 N7 C8 117.78(8) . . ?
C17 N16 C21 114.81(10) . . ?
N7 C19 C18 121.88(9) . . ?
N7 C19 C20 122.05(10) . . ?
C20 C19 C18 116.06(10) . . ?
O14 C4 C5 124.49(10) . . ?
O14 C4 C3 115.67(10) . . ?
C5 C4 C3 119.84(10) . . ?
O10 C9 C8 109.97(9) . . ?
O13 C9 O10 125.28(10) . . ?
O13 C9 C8 124.73(9) . . ?
N7 C8 C9 112.35(8) . . ?
N7 C8 H8A 109.1 . . ?
N7 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.30(10) . . ?
C17 C18 H18 120.3 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.37(10) . . ?
C21 C20 H20 120.3 . . ?
C6 C1 N7 121.46(9) . . ?
C6 C1 C2 119.38(10) . . ?
C2 C1 N7 119.16(9) . . ?
C1 C6 H6 119.6 . . ?
C1 C6 C5 120.72(10) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 119.54(10) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N16 C17 C18 125.22(11) . . ?
N16 C17 H17 117.4 . . ?
C18 C17 H17 117.4 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.07(10) . . ?
C2 C3 H3 120.0 . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O10 C11 H11A 110.2 . . ?
O10 C11 H11B 110.2 . . ?
O10 C11 C12 107.41(9) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.44(10) . . ?
C3 C2 H2 119.8 . . ?
N16 C21 C20 125.23(11) . . ?
N16 C21 H21 117.4 . . ?
C20 C21 H21 117.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O10 C9 C8 N7 163.23(8) . . . . ?
O13 C9 C8 N7 -15.75(14) . . . . ?
O14 C4 C5 C6 179.59(10) . . . . ?
O14 C4 C3 C2 -179.39(10) . . . . ?
N7 C19 C18 C17 179.74(10) . . . . ?
N7 C19 C20 C21 -179.13(10) . . . . ?
N7 C1 C6 C5 -179.89(10) . . . . ?
N7 C1 C2 C3 -179.91(10) . . . . ?
C19 N7 C8 C9 -66.02(12) . . . . ?
C19 N7 C1 C6 85.05(13) . . . . ?
C19 N7 C1 C2 -95.40(12) . . . . ?
C19 C18 C17 N16 -0.58(18) . . . . ?
C19 C20 C21 N16 -0.76(18) . . . . ?
C4 C3 C2 C1 -0.19(18) . . . . ?
C9 O10 C11 C12 154.38(10) . . . . ?
C8 N7 C19 C18 167.57(9) . . . . ?
C8 N7 C19 C20 -13.28(15) . . . . ?
C8 N7 C1 C6 -80.57(13) . . . . ?
C8 N7 C1 C2 98.98(12) . . . . ?
C18 C19 C20 C21 0.07(15) . . . . ?
C20 C19 C18 C17 0.54(15) . . . . ?
C1 N7 C19 C18 2.25(15) . . . . ?
C1 N7 C19 C20 -178.61(9) . . . . ?
C1 N7 C8 C9 99.74(10) . . . . ?
C1 C6 C5 C4 -0.22(17) . . . . ?
C6 C1 C2 C3 -0.36(17) . . . . ?
C5 C4 C3 C2 0.54(18) . . . . ?
C17 N16 C21 C20 0.74(18) . . . . ?
C3 C4 C5 C6 -0.33(17) . . . . ?
C15 O14 C4 C5 -8.16(16) . . . . ?
C15 O14 C4 C3 171.76(10) . . . . ?
C11 O10 C9 O13 -7.28(14) . . . . ?
C11 O10 C9 C8 173.76(8) . . . . ?
C2 C1 C6 C5 0.57(17) . . . . ?
C21 N16 C17 C18 -0.06(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_akimoto-product_autored
_database_code_depnum_ccdc_archive 'CCDC 2389158'
loop_
_audit_author_name
_audit_author_address
'Shuta Akimoro'
;Okayama University
Japan
;
_audit_update_record             
;
2024-10-07 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_audit_creation_date             2024-09-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     check1
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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.4927(6)
_cell_length_b                   18.0971(12)
_cell_length_c                   11.2308(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.978(7)
_cell_angle_gamma                90
_cell_volume                     1477.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      29.1510
_cell_measurement_theta_min      3.5980
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 -15 0.1012
9 -14 -3 0.3345
-1 7 15 0.1018
-9 12 0 0.2923
0 -15 -13 0.1205
6 19 -8 0.2062
-1 14 13 0.0931
-6 -20 6 0.1682

_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.22
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3719 -6.0352 -14.7702 -0.2663 0.0012 0.9639
8.9375 -13.6438 -2.8361 0.9419 -0.0042 0.3358
-0.5940 7.4199 14.8744 0.1614 -0.0007 -0.9869
-8.9599 12.3365 -0.1814 -0.9904 0.0044 -0.1380
0.3649 -14.9424 -12.5417 0.0016 0.2859 0.9583
5.7904 19.3575 -7.5014 -0.0044 -0.9894 0.1452
-0.5399 14.4200 12.8150 -0.0014 -0.2574 -0.9663
-5.6539 -20.4096 6.1982 0.0044 0.9986 -0.0532

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11009
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.768
_diffrn_reflns_theta_min         3.595
_diffrn_ambient_temperature      180.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -33.00   0.50    1.01    --    5.00  18.00-120.00   54
  2  ω    -91.00  78.00   0.50    1.01    --  -11.30  55.00   0.00  338
  3  ω     27.00  74.00   0.50    1.01    --  -11.30  18.00  60.00   94
  4  ω    -77.00 -28.00   0.50    1.01    --  -11.30  18.00  60.00   98
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0863936000
_diffrn_orient_matrix_UB_12      -0.0172008000
_diffrn_orient_matrix_UB_13      0.0228829000
_diffrn_orient_matrix_UB_21      -0.0450355000
_diffrn_orient_matrix_UB_22      -0.0321424000
_diffrn_orient_matrix_UB_23      0.0141870000
_diffrn_orient_matrix_UB_31      -0.0033251000
_diffrn_orient_matrix_UB_32      -0.0144698000
_diffrn_orient_matrix_UB_33      -0.0592626000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2442
_reflns_number_total             3575
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0928P)²+0.2791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1765
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N7(H7), C18(H18), C6(H6), C5(H5), C17(H17), C20(H20), C2(H2), C3(H3), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O10 O -0.00422(19) 0.65613(7) 0.20904(11) 0.0402(3) Uani 1 1 d . . . . .
O13 O -0.0606(2) 0.58044(8) 0.04602(12) 0.0482(4) Uani 1 1 d . . . . .
O14 O 0.0474(2) 0.20406(8) 0.48507(13) 0.0505(4) Uani 1 1 d . . . . .
N7 N -0.0459(2) 0.46023(8) 0.19762(13) 0.0349(4) Uani 1 1 d . . . . .
H7 H -0.110335 0.458699 0.120953 0.042 Uiso 1 1 calc R U . . .
N16 N 0.6299(2) 0.53734(9) 0.36071(15) 0.0430(4) Uani 1 1 d . . . . .
C1 C -0.0189(2) 0.39566(10) 0.26955(16) 0.0320(4) Uani 1 1 d . . . . .
C9 C -0.0186(2) 0.59018(10) 0.15526(16) 0.0349(4) Uani 1 1 d . . . . .
C4 C 0.0233(2) 0.26469(11) 0.40821(17) 0.0368(4) Uani 1 1 d . . . . .
C8 C 0.0331(2) 0.52906(10) 0.25071(15) 0.0328(4) Uani 1 1 d . . . . .
H8 H -0.019376 0.541308 0.322165 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2444(2) 0.52953(9) 0.29367(15) 0.0313(4) Uani 1 1 d . . . . .
C18 C 0.3511(2) 0.48456(10) 0.23773(17) 0.0362(4) Uani 1 1 d . . . . .
H18 H 0.294938 0.450298 0.175906 0.043 Uiso 1 1 calc R U . . .
C6 C 0.0261(3) 0.39741(11) 0.39783(17) 0.0395(4) Uani 1 1 d . . . . .
H6 H 0.043448 0.443608 0.439200 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0455(3) 0.33274(10) 0.46510(17) 0.0403(5) Uani 1 1 d . . . . .
H5 H 0.074625 0.335204 0.552162 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5411(2) 0.49075(11) 0.27404(18) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.612560 0.460003 0.234921 0.048 Uiso 1 1 calc R U . . .
C11 C -0.0274(3) 0.72058(11) 0.12829(19) 0.0441(5) Uani 1 1 d . . . . .
H11A H -0.153760 0.721858 0.075175 0.053 Uiso 1 1 calc R U . . .
H11B H 0.060576 0.718443 0.075268 0.053 Uiso 1 1 calc R U . . .
C20 C 0.3349(3) 0.57718(11) 0.38470(16) 0.0381(4) Uani 1 1 d . . . . .
H20 H 0.267334 0.608381 0.425909 0.046 Uiso 1 1 calc R U . . .
C2 C -0.0421(3) 0.32689(11) 0.21362(17) 0.0422(5) Uani 1 1 d . . . . .
H2 H -0.072848 0.324248 0.126559 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0218(3) 0.26174(11) 0.28084(19) 0.0445(5) Uani 1 1 d . . . . .
H3 H -0.038697 0.215393 0.239946 0.053 Uiso 1 1 calc R U . . .
C21 C 0.5253(3) 0.57876(12) 0.41493(18) 0.0433(5) Uani 1 1 d . . . . .
H21 H 0.585161 0.611408 0.478292 0.052 Uiso 1 1 calc R U . . .
C15 C 0.0376(3) 0.13321(12) 0.4308(2) 0.0535(6) Uani 1 1 d . . . . .
H15A H -0.085445 0.125626 0.377505 0.080 Uiso 1 1 calc R U . . .
H15B H 0.062070 0.095425 0.495170 0.080 Uiso 1 1 calc R U . . .
H15C H 0.129457 0.129480 0.381972 0.080 Uiso 1 1 calc R U . . .
C12 C 0.0076(4) 0.78779(12) 0.2079(2) 0.0558(6) Uani 1 1 d . . . . .
H12A H -0.007476 0.832101 0.156317 0.084 Uiso 1 1 calc R U . . .
H12B H 0.133292 0.786077 0.259621 0.084 Uiso 1 1 calc R U . . .
H12C H -0.079987 0.789237 0.260090 0.084 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
O10 C9 1.330(2) . ?
O10 C11 1.462(2) . ?
O13 C9 1.204(2) . ?
O14 C4 1.381(2) . ?
O14 C15 1.414(3) . ?
N7 H7 0.8800 . ?
N7 C1 1.407(2) . ?
N7 C8 1.445(2) . ?
N16 C17 1.337(3) . ?
N16 C21 1.333(3) . ?
C1 C6 1.399(3) . ?
C1 C2 1.386(2) . ?
C9 C8 1.524(2) . ?
C4 C5 1.379(3) . ?
C4 C3 1.389(3) . ?
C8 H8 1.0000 . ?
C8 C19 1.540(2) . ?
C19 C18 1.393(2) . ?
C19 C20 1.383(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.387(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.495(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C21 H21 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 O10 C11 116.72(14) . . ?
C4 O14 C15 117.75(16) . . ?
C1 N7 H7 120.3 . . ?
C1 N7 C8 119.43(13) . . ?
C8 N7 H7 120.3 . . ?
C21 N16 C17 116.31(16) . . ?
C6 C1 N7 122.55(16) . . ?
C2 C1 N7 120.04(15) . . ?
C2 C1 C6 117.38(17) . . ?
O10 C9 C8 110.66(14) . . ?
O13 C9 O10 124.53(17) . . ?
O13 C9 C8 124.76(17) . . ?
O14 C4 C3 125.16(17) . . ?
C5 C4 O14 115.92(16) . . ?
C5 C4 C3 118.91(18) . . ?
N7 C8 C9 109.04(14) . . ?
N7 C8 H8 108.7 . . ?
N7 C8 C19 114.95(14) . . ?
C9 C8 H8 108.7 . . ?
C9 C8 C19 106.49(13) . . ?
C19 C8 H8 108.7 . . ?
C18 C19 C8 120.96(15) . . ?
C20 C19 C8 121.21(15) . . ?
C20 C19 C18 117.75(16) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.71(17) . . ?
C17 C18 H18 120.6 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.76(17) . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 121.22(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
N16 C17 C18 124.02(17) . . ?
N16 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
O10 C11 H11A 110.2 . . ?
O10 C11 H11B 110.2 . . ?
O10 C11 C12 107.49(17) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.08(17) . . ?
C21 C20 H20 120.5 . . ?
C1 C2 H2 119.0 . . ?
C1 C2 C3 122.06(17) . . ?
C3 C2 H2 119.0 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.66(18) . . ?
C2 C3 H3 120.2 . . ?
N16 C21 C20 124.12(18) . . ?
N16 C21 H21 117.9 . . ?
C20 C21 H21 117.9 . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O10 C9 C8 N7 159.08(14) . . . . ?
O10 C9 C8 C19 -76.34(16) . . . . ?
O13 C9 C8 N7 -23.3(2) . . . . ?
O13 C9 C8 C19 101.3(2) . . . . ?
O14 C4 C5 C6 179.56(16) . . . . ?
O14 C4 C3 C2 -179.95(18) . . . . ?
N7 C1 C6 C5 177.85(16) . . . . ?
N7 C1 C2 C3 -178.24(17) . . . . ?
N7 C8 C19 C18 28.3(2) . . . . ?
N7 C8 C19 C20 -154.99(16) . . . . ?
C1 N7 C8 C9 -179.04(13) . . . . ?
C1 N7 C8 C19 61.5(2) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C9 O10 C11 C12 -175.97(16) . . . . ?
C9 C8 C19 C18 -92.58(18) . . . . ?
C9 C8 C19 C20 84.15(18) . . . . ?
C8 N7 C1 C6 21.7(2) . . . . ?
C8 N7 C1 C2 -160.20(16) . . . . ?
C8 C19 C18 C17 175.58(16) . . . . ?
C8 C19 C20 C21 -176.06(17) . . . . ?
C19 C18 C17 N16 0.4(3) . . . . ?
C19 C20 C21 N16 0.7(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C17 N16 C21 C20 -1.6(3) . . . . ?
C11 O10 C9 O13 -5.0(3) . . . . ?
C11 O10 C9 C8 172.63(14) . . . . ?
C20 C19 C18 C17 -1.3(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C21 N16 C17 C18 1.0(3) . . . . ?
C15 O14 C4 C5 -176.03(17) . . . . ?
C15 O14 C4 C3 4.5(3) . . . . ?

_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 1.699
_oxdiff_exptl_absorpt_empirical_full_min 0.593
