# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_ydg_lcf_1_300k_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2l5f6f
_database_code_depnum_ccdc_archive 'CCDC 2388494'
loop_
_audit_author_name
_audit_author_address
'Changfu Li'
;Sichuan University
China
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2024-03-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N O3'
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.29
_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      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                   9.4468(15)
_cell_length_b                   12.9259(17)
_cell_length_c                   11.0202(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.606(5)
_cell_angle_gamma                90
_cell_volume                     1326.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3424
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      26.224
_cell_measurement_theta_min      2.450
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1936 before and 0.0952 after correction.
The Ratio of minimum to maximum transmission is 0.5063.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.449
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1607
_reflns_number_total             2325
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.010
_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)+(0.0849P)²+0.2507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1687
_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:
 C2(H2A,H2B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), 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
O1 O 0.77559(15) 0.26014(12) 0.40394(16) 0.0392(5) Uani 1 1 d . . . . .
O2 O 0.94654(18) 0.38095(14) 0.4298(2) 0.0606(7) Uani 1 1 d . . . . .
O3 O 0.51531(17) 0.33168(13) 0.27475(19) 0.0466(5) Uani 1 1 d . . . . .
N1 N 0.64810(19) 0.61138(14) 0.43196(19) 0.0349(5) Uani 1 1 d . . . . .
C1 C 0.8156(3) 0.0798(2) 0.4209(3) 0.0558(8) Uani 1 1 d . . . . .
H1A H 0.7474 0.0759 0.4763 0.084 Uiso 1 1 calc R U . . .
H1B H 0.8860 0.0261 0.4405 0.084 Uiso 1 1 calc R U . . .
H1C H 0.7669 0.0711 0.3379 0.084 Uiso 1 1 calc R U . . .
C2 C 0.8880(3) 0.18258(18) 0.4335(3) 0.0453(7) Uani 1 1 d . . . . .
H2A H 0.9385 0.1922 0.5169 0.054 Uiso 1 1 calc R U . . .
H2B H 0.9566 0.1879 0.3774 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8209(2) 0.35775(18) 0.4080(2) 0.0371(6) Uani 1 1 d . . . . .
C4 C 0.7033(2) 0.43524(17) 0.3861(2) 0.0320(6) Uani 1 1 d . . . . .
C5 C 0.5588(2) 0.41492(17) 0.3235(2) 0.0321(6) Uani 1 1 d . . . . .
C6 C 0.4605(2) 0.50492(17) 0.3188(2) 0.0314(6) Uani 1 1 d . . . . .
C7 C 0.3167(2) 0.49366(19) 0.2621(2) 0.0375(6) Uani 1 1 d . . . . .
H7 H 0.2862 0.4301 0.2276 0.045 Uiso 1 1 calc R U . . .
C8 C 0.2188(2) 0.5739(2) 0.2557(3) 0.0399(6) Uani 1 1 d . . . . .
C9 C 0.0634(3) 0.5596(2) 0.1989(3) 0.0585(9) Uani 1 1 d . . . . .
H9A H 0.0149 0.5214 0.2544 0.088 Uiso 1 1 calc R U . . .
H9B H 0.0577 0.5222 0.1229 0.088 Uiso 1 1 calc R U . . .
H9C H 0.0187 0.6260 0.1831 0.088 Uiso 1 1 calc R U . . .
C10 C 0.7391(2) 0.53092(18) 0.4351(2) 0.0350(6) Uani 1 1 d . . . . .
H10 H 0.8334 0.5411 0.4734 0.042 Uiso 1 1 calc R U . . .
C11 C 0.6990(3) 0.70822(18) 0.4981(3) 0.0399(6) Uani 1 1 d . . . . .
H11A H 0.7860 0.6936 0.5558 0.048 Uiso 1 1 calc R U . . .
H11B H 0.6268 0.7319 0.5448 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7290(3) 0.7932(2) 0.4118(3) 0.0549(8) Uani 1 1 d . . . . .
H12A H 0.7990 0.7698 0.3642 0.082 Uiso 1 1 calc R U . . .
H12B H 0.7651 0.8530 0.4588 0.082 Uiso 1 1 calc R U . . .
H12C H 0.6418 0.8109 0.3577 0.082 Uiso 1 1 calc R U . . .
C13 C 0.5054(2) 0.60047(17) 0.3724(2) 0.0328(6) Uani 1 1 d . . . . .
C14 C 0.4067(3) 0.68216(18) 0.3664(3) 0.0394(6) Uani 1 1 d . . . . .
H14 H 0.4356 0.7457 0.4017 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2673(3) 0.66835(19) 0.3085(3) 0.0414(7) Uani 1 1 d . . . . .
H15 H 0.2035 0.7235 0.3044 0.050 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 C2 1.457(3) . ?
O1 C3 1.331(3) . ?
O2 C3 1.209(3) . ?
O3 C5 1.242(3) . ?
N1 C10 1.346(3) . ?
N1 C11 1.487(3) . ?
N1 C13 1.404(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.490(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(3) . ?
C4 C5 1.447(3) . ?
C4 C10 1.369(3) . ?
C5 C6 1.484(3) . ?
C6 C7 1.406(3) . ?
C6 C13 1.404(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(3) . ?
C8 C9 1.508(3) . ?
C8 C15 1.396(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.510(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.403(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?

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
C3 O1 C2 115.25(17) . . ?
C10 N1 C11 119.02(18) . . ?
C10 N1 C13 119.55(19) . . ?
C13 N1 C11 121.34(18) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 106.67(19) . . ?
O1 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
O1 C3 C4 113.96(19) . . ?
O2 C3 O1 122.8(2) . . ?
O2 C3 C4 123.2(2) . . ?
C5 C4 C3 125.2(2) . . ?
C10 C4 C3 114.6(2) . . ?
C10 C4 C5 120.2(2) . . ?
O3 C5 C4 125.5(2) . . ?
O3 C5 C6 120.3(2) . . ?
C4 C5 C6 114.2(2) . . ?
C7 C6 C5 119.2(2) . . ?
C13 C6 C5 122.1(2) . . ?
C13 C6 C7 118.7(2) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.2(2) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 C15 117.7(2) . . ?
C15 C8 C9 120.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C4 125.0(2) . . ?
N1 C10 H10 117.5 . . ?
C4 C10 H10 117.5 . . ?
N1 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
N1 C11 C12 112.5(2) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
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 . . ?
C6 C13 N1 118.95(19) . . ?
C14 C13 N1 121.7(2) . . ?
C14 C13 C6 119.4(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 120.0 . . ?
C8 C15 H15 119.0 . . ?
C14 C15 C8 121.9(2) . . ?
C14 C15 H15 119.0 . . ?

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
O1 C3 C4 C5 -21.7(4) . . . . ?
O1 C3 C4 C10 155.8(2) . . . . ?
O2 C3 C4 C5 159.6(3) . . . . ?
O2 C3 C4 C10 -23.0(4) . . . . ?
O3 C5 C6 C7 2.1(4) . . . . ?
O3 C5 C6 C13 -179.8(2) . . . . ?
N1 C13 C14 C15 -179.3(2) . . . . ?
C2 O1 C3 O2 2.8(4) . . . . ?
C2 O1 C3 C4 -175.9(2) . . . . ?
C3 O1 C2 C1 -178.7(2) . . . . ?
C3 C4 C5 O3 -3.6(4) . . . . ?
C3 C4 C5 C6 177.5(2) . . . . ?
C3 C4 C10 N1 -176.6(2) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C13 -0.8(3) . . . . ?
C5 C4 C10 N1 1.0(4) . . . . ?
C5 C6 C7 C8 179.2(2) . . . . ?
C5 C6 C13 N1 0.3(4) . . . . ?
C5 C6 C13 C14 -179.0(2) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
C6 C7 C8 C15 -0.2(4) . . . . ?
C6 C13 C14 C15 0.0(4) . . . . ?
C7 C6 C13 N1 178.4(2) . . . . ?
C7 C6 C13 C14 -0.9(4) . . . . ?
C7 C8 C15 C14 -0.7(4) . . . . ?
C9 C8 C15 C14 176.7(3) . . . . ?
C10 N1 C11 C12 104.8(3) . . . . ?
C10 N1 C13 C6 0.9(3) . . . . ?
C10 N1 C13 C14 -179.8(2) . . . . ?
C10 C4 C5 O3 179.1(3) . . . . ?
C10 C4 C5 C6 0.2(3) . . . . ?
C11 N1 C10 C4 175.0(2) . . . . ?
C11 N1 C13 C6 -175.6(2) . . . . ?
C11 N1 C13 C14 3.7(4) . . . . ?
C13 N1 C10 C4 -1.6(4) . . . . ?
C13 N1 C11 C12 -78.7(3) . . . . ?
C13 C6 C7 C8 1.0(4) . . . . ?
C13 C14 C15 C8 0.8(4) . . . . ?

_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_mo_ydg_lcf_15_300k_2_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2l5f7g
_database_code_depnum_ccdc_archive 'CCDC 2388495'
loop_
_audit_author_name
_audit_author_address
'LI Changfu'
;Sichuan University
China
;
_audit_update_record             
;
2024-10-03 deposited with the CCDC.	2025-04-14 downloaded from the CCDC.
;
_audit_creation_date             2023-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H7 N O4'
_chemical_formula_sum            'C10 H7 N O4'
_chemical_formula_weight         205.17
_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      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                   3.7486(2)
_cell_length_b                   17.9200(11)
_cell_length_c                   12.7162(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.790(2)
_cell_angle_gamma                90
_cell_volume                     853.20(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3028
_cell_measurement_temperature    279(2)
_cell_measurement_theta_max      27.282
_cell_measurement_theta_min      2.273
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0938 before and 0.0625 after correction.
The Ratio of minimum to maximum transmission is 0.9174.
The λ/2 correction factor is Not present.
;
_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    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17046
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.965
_diffrn_ambient_temperature      279.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1316
_reflns_number_total             1945
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.044
_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)+(0.0500P)²+0.2675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C9(H9)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_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
O1 O 0.2280(4) 0.24618(8) 0.47769(11) 0.0499(4) Uani 1 1 d . . . . .
O4 O 0.5109(4) 0.37655(8) 0.50731(11) 0.0469(4) Uani 1 1 d . . . . .
H4 H 0.4114 0.3429 0.4734 0.070 Uiso 1 1 calc R U . . .
O3 O 0.5713(4) 0.19366(7) 0.77636(11) 0.0444(4) Uani 1 1 d . . . . .
N1 N 0.7994(4) 0.30896(8) 0.80555(12) 0.0339(4) Uani 1 1 d . . . . .
H1 H 0.8696 0.2951 0.8679 0.041 Uiso 1 1 calc R U . . .
O2 O 0.2697(4) 0.16193(8) 0.60438(12) 0.0520(4) Uani 1 1 d . . . . .
H2 H 0.3506 0.1589 0.6653 0.078 Uiso 1 1 calc R U . . .
C1 C 0.3309(5) 0.22852(10) 0.56797(15) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.5203(4) 0.28170(9) 0.63784(13) 0.0297(4) Uani 1 1 d . . . . .
C3 C 0.6295(5) 0.25840(10) 0.74260(14) 0.0314(4) Uani 1 1 d . . . . .
C4 C 0.8681(4) 0.38172(10) 0.77615(14) 0.0312(4) Uani 1 1 d . . . . .
C5 C 1.0359(5) 0.43089(11) 0.84797(16) 0.0410(5) Uani 1 1 d . . . . .
H5 H 1.1035 0.4151 0.9157 0.049 Uiso 1 1 calc R U . . .
C6 C 1.0996(5) 0.50294(12) 0.81702(19) 0.0479(5) Uani 1 1 d . . . . .
H6 H 1.2096 0.5360 0.8647 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7687(4) 0.40547(10) 0.67433(14) 0.0315(4) Uani 1 1 d . . . . .
C8 C 0.8398(5) 0.47963(10) 0.64501(17) 0.0405(5) Uani 1 1 d . . . . .
H8 H 0.7756 0.4961 0.5774 0.049 Uiso 1 1 calc R U . . .
C9 C 1.0035(5) 0.52731(11) 0.71622(19) 0.0474(5) Uani 1 1 d . . . . .
H9 H 1.0503 0.5763 0.6969 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5935(5) 0.35293(10) 0.60397(14) 0.0312(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.234(2) . ?
O4 H4 0.8200 . ?
O4 C10 1.322(2) . ?
O3 C3 1.260(2) . ?
N1 H1 0.8600 . ?
N1 C3 1.348(2) . ?
N1 C4 1.384(2) . ?
O2 H2 0.8200 . ?
O2 C1 1.304(2) . ?
C1 C2 1.463(2) . ?
C2 C3 1.436(2) . ?
C2 C10 1.379(2) . ?
C4 C5 1.396(3) . ?
C4 C7 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C9 1.385(3) . ?
C7 C8 1.409(2) . ?
C7 C10 1.436(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(3) . ?
C9 H9 0.9300 . ?

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
C10 O4 H4 109.5 . . ?
C3 N1 H1 117.9 . . ?
C3 N1 C4 124.15(15) . . ?
C4 N1 H1 117.9 . . ?
C1 O2 H2 109.5 . . ?
O1 C1 O2 120.82(17) . . ?
O1 C1 C2 121.22(17) . . ?
O2 C1 C2 117.96(17) . . ?
C3 C2 C1 118.81(16) . . ?
C10 C2 C1 120.75(16) . . ?
C10 C2 C3 120.44(16) . . ?
O3 C3 N1 120.08(16) . . ?
O3 C3 C2 122.51(16) . . ?
N1 C3 C2 117.41(16) . . ?
N1 C4 C5 120.10(17) . . ?
N1 C4 C7 119.53(16) . . ?
C7 C4 C5 120.37(17) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.99(19) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C9 121.34(19) . . ?
C9 C6 H6 119.3 . . ?
C4 C7 C8 119.17(17) . . ?
C4 C7 C10 118.13(16) . . ?
C8 C7 C10 122.70(17) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C6 C9 H9 119.9 . . ?
C8 C9 C6 120.25(19) . . ?
C8 C9 H9 119.9 . . ?
O4 C10 C2 123.06(16) . . ?
O4 C10 C7 116.66(16) . . ?
C2 C10 C7 120.28(16) . . ?

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
O1 C1 C2 C3 179.14(17) . . . . ?
O1 C1 C2 C10 -0.9(3) . . . . ?
N1 C4 C5 C6 -179.70(17) . . . . ?
N1 C4 C7 C8 -179.96(16) . . . . ?
N1 C4 C7 C10 0.7(2) . . . . ?
O2 C1 C2 C3 0.0(3) . . . . ?
O2 C1 C2 C10 179.92(17) . . . . ?
C1 C2 C3 O3 0.7(3) . . . . ?
C1 C2 C3 N1 -179.17(15) . . . . ?
C1 C2 C10 O4 -2.4(3) . . . . ?
C1 C2 C10 C7 177.88(16) . . . . ?
C3 N1 C4 C5 177.92(17) . . . . ?
C3 N1 C4 C7 -2.1(3) . . . . ?
C3 C2 C10 O4 177.49(17) . . . . ?
C3 C2 C10 C7 -2.2(3) . . . . ?
C4 N1 C3 O3 -178.56(16) . . . . ?
C4 N1 C3 C2 1.3(3) . . . . ?
C4 C5 C6 C9 -0.5(3) . . . . ?
C4 C7 C8 C9 -0.2(3) . . . . ?
C4 C7 C10 O4 -178.34(16) . . . . ?
C4 C7 C10 C2 1.4(3) . . . . ?
C5 C4 C7 C8 0.0(3) . . . . ?
C5 C4 C7 C10 -179.32(16) . . . . ?
C5 C6 C9 C8 0.3(3) . . . . ?
C7 C4 C5 C6 0.3(3) . . . . ?
C7 C8 C9 C6 0.0(3) . . . . ?
C8 C7 C10 O4 2.4(3) . . . . ?
C8 C7 C10 C2 -177.93(17) . . . . ?
C10 C2 C3 O3 -179.26(16) . . . . ?
C10 C2 C3 N1 0.9(3) . . . . ?
C10 C7 C8 C9 179.10(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
