# 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_jd131223_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2jqpgf
_database_code_depnum_ccdc_archive 'CCDC 2345505'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-04-03 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;
_audit_creation_date             2023-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32
_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      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                   10.103(3)
_cell_length_b                   12.796(4)
_cell_length_c                   11.589(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.527(11)
_cell_angle_gamma                90
_cell_volume                     1493.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7167
_cell_measurement_temperature    158.78
_cell_measurement_theta_max      33.56
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7047
_exptl_absorpt_correction_T_min  0.5564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.1202 after correction.
The Ratio of minimum to maximum transmission is 0.7896.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12046
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         3.028
_diffrn_ambient_temperature      158.78
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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           1.0
_diffrn_source_power             0.05
_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                2198
_reflns_number_total             2703
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.047
_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)+(0.1276P)²+0.7421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2182
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C2(H2A), C5(H5), C15(H15), C4(H4), C3(H3A)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
O1 O 0.63690(16) 0.65515(12) 0.68612(13) 0.0404(5) Uani 1 1 d . . . . .
O2 O 0.44053(17) 0.75743(13) 0.58907(13) 0.0428(5) Uani 1 1 d . . . . .
H2 H 0.494016 0.735633 0.642888 0.064 Uiso 1 1 calc R U . . .
O3 O 0.33834(17) 0.70594(15) 0.18672(13) 0.0490(5) Uani 1 1 d . . . . .
H3 H 0.276430 0.746250 0.201905 0.074 Uiso 1 1 calc R U . . .
N1 N 0.68291(18) 0.50565(14) 0.38060(16) 0.0367(5) Uani 1 1 d . . . . .
H1 H 0.692916 0.473067 0.314987 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5679(2) 0.63252(15) 0.48802(17) 0.0291(5) Uani 1 1 d . . . . .
C9 C 0.4654(2) 0.70921(16) 0.48882(18) 0.0318(5) Uani 1 1 d . . . . .
C7 C 0.6498(2) 0.60719(16) 0.59059(18) 0.0322(5) Uani 1 1 d . . . . .
C13 C 0.5865(2) 0.58151(16) 0.38135(18) 0.0309(5) Uani 1 1 d . . . . .
C10 C 0.3904(2) 0.73473(16) 0.38884(18) 0.0352(5) Uani 1 1 d . . . . .
H10 H 0.323875 0.787114 0.389518 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7503(2) 0.52703(18) 0.58248(18) 0.0358(5) Uani 1 1 d . . . . .
C11 C 0.4131(2) 0.68264(17) 0.28541(19) 0.0352(5) Uani 1 1 d . . . . .
C12 C 0.5089(2) 0.60499(18) 0.27904(18) 0.0361(5) Uani 1 1 d . . . . .
C1 C 0.7645(2) 0.47765(18) 0.4759(2) 0.0371(5) Uani 1 1 d . . . . .
C2 C 0.8621(2) 0.4007(2) 0.4668(2) 0.0470(6) Uani 1 1 d . . . . .
H2A H 0.871832 0.367322 0.394701 0.056 Uiso 1 1 calc R U . . .
C16 C 0.7254(2) 0.45421(19) 0.10148(19) 0.0431(6) Uani 1 1 d . . . . .
C5 C 0.8351(2) 0.4973(2) 0.6803(2) 0.0465(6) Uani 1 1 d . . . . .
H5 H 0.826221 0.529771 0.753051 0.056 Uiso 1 1 calc R U . . .
C15 C 0.6531(2) 0.5392(2) 0.12281(19) 0.0439(6) Uani 1 1 d . . . . .
H15 H 0.691289 0.605006 0.107115 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5183(2) 0.5412(2) 0.1688(2) 0.0461(6) Uani 1 1 d . . . . .
H14A H 0.491319 0.468461 0.184070 0.055 Uiso 1 1 calc R U . . .
H14B H 0.453923 0.569861 0.108050 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9300(3) 0.4219(2) 0.6702(3) 0.0578(8) Uani 1 1 d . . . . .
H4 H 0.986541 0.402147 0.735930 0.069 Uiso 1 1 calc R U . . .
C3 C 0.9436(3) 0.3738(2) 0.5631(3) 0.0577(8) Uani 1 1 d . . . . .
H3A H 1.010069 0.322024 0.556882 0.069 Uiso 1 1 calc R U . . .
C18 C 0.6880(3) 0.3436(2) 0.1207(3) 0.0619(8) Uani 1 1 d . . . . .
H18A H 0.755046 0.310689 0.174634 0.093 Uiso 1 1 calc R U . . .
H18B H 0.682810 0.305994 0.046781 0.093 Uiso 1 1 calc R U . . .
H18C H 0.601436 0.341142 0.153258 0.093 Uiso 1 1 calc R U . . .
C17 C 0.8563(3) 0.4665(2) 0.0503(3) 0.0580(7) Uani 1 1 d . . . . .
H17A H 0.852683 0.431780 -0.025237 0.087 Uiso 1 1 calc R U . . .
H17B H 0.926594 0.434859 0.102039 0.087 Uiso 1 1 calc R U . . .
H17C H 0.875267 0.541000 0.040670 0.087 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 C7 1.281(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.356(3) . ?
O3 H3 0.8400 . ?
O3 C11 1.353(3) . ?
N1 H1 0.8800 . ?
N1 C13 1.376(3) . ?
N1 C1 1.373(3) . ?
C8 C9 1.428(3) . ?
C8 C7 1.431(3) . ?
C8 C13 1.423(3) . ?
C9 C10 1.373(3) . ?
C7 C6 1.452(3) . ?
C13 C12 1.401(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.406(3) . ?
C6 C1 1.404(3) . ?
C6 C5 1.418(3) . ?
C11 C12 1.393(3) . ?
C12 C14 1.525(3) . ?
C1 C2 1.404(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.378(4) . ?
C16 C15 1.344(3) . ?
C16 C18 1.486(4) . ?
C16 C17 1.500(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.372(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.501(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C3 1.401(5) . ?
C3 H3A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 O2 H2 109.5 . . ?
C11 O3 H3 109.5 . . ?
C13 N1 H1 118.0 . . ?
C1 N1 H1 118.0 . . ?
C1 N1 C13 124.01(19) . . ?
C9 C8 C7 121.50(19) . . ?
C13 C8 C9 117.79(18) . . ?
C13 C8 C7 120.71(19) . . ?
O2 C9 C8 120.11(18) . . ?
O2 C9 C10 119.21(19) . . ?
C10 C9 C8 120.68(19) . . ?
O1 C7 C8 121.2(2) . . ?
O1 C7 C6 120.90(19) . . ?
C8 C7 C6 117.89(19) . . ?
N1 C13 C8 118.09(18) . . ?
N1 C13 C12 119.66(19) . . ?
C12 C13 C8 122.23(19) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.41(19) . . ?
C11 C10 H10 120.3 . . ?
C1 C6 C7 119.67(19) . . ?
C1 C6 C5 119.1(2) . . ?
C5 C6 C7 121.3(2) . . ?
O3 C11 C10 119.92(19) . . ?
O3 C11 C12 117.14(19) . . ?
C12 C11 C10 122.93(19) . . ?
C13 C12 C14 121.78(19) . . ?
C11 C12 C13 116.92(19) . . ?
C11 C12 C14 120.99(19) . . ?
N1 C1 C6 119.6(2) . . ?
N1 C1 C2 120.2(2) . . ?
C2 C1 C6 120.2(2) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2A 120.3 . . ?
C15 C16 C18 126.5(2) . . ?
C15 C16 C17 119.8(2) . . ?
C18 C16 C17 113.7(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C16 C15 H15 116.5 . . ?
C16 C15 C14 126.9(2) . . ?
C14 C15 H15 116.5 . . ?
C12 C14 H14A 108.5 . . ?
C12 C14 H14B 108.5 . . ?
C15 C14 C12 115.1(2) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C7 C6 C1 -178.36(19) . . . . ?
O1 C7 C6 C5 1.6(3) . . . . ?
O2 C9 C10 C11 -178.04(19) . . . . ?
O3 C11 C12 C13 179.69(19) . . . . ?
O3 C11 C12 C14 -6.5(3) . . . . ?
N1 C13 C12 C11 -179.93(19) . . . . ?
N1 C13 C12 C14 6.3(3) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C8 C7 C6 C1 0.2(3) . . . . ?
C8 C7 C6 C5 -179.85(19) . . . . ?
C8 C13 C12 C11 1.1(3) . . . . ?
C8 C13 C12 C14 -172.6(2) . . . . ?
C9 C8 C7 O1 -2.5(3) . . . . ?
C9 C8 C7 C6 179.01(18) . . . . ?
C9 C8 C13 N1 -178.38(17) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
C9 C10 C11 O3 178.92(19) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C7 C8 C9 O2 -2.3(3) . . . . ?
C7 C8 C9 C10 178.05(18) . . . . ?
C7 C8 C13 N1 1.6(3) . . . . ?
C7 C8 C13 C12 -179.45(18) . . . . ?
C7 C6 C1 N1 -0.1(3) . . . . ?
C7 C6 C1 C2 179.4(2) . . . . ?
C7 C6 C5 C4 -179.5(2) . . . . ?
C13 N1 C1 C6 0.8(3) . . . . ?
C13 N1 C1 C2 -178.8(2) . . . . ?
C13 C8 C9 O2 177.68(18) . . . . ?
C13 C8 C9 C10 -2.0(3) . . . . ?
C13 C8 C7 O1 177.60(18) . . . . ?
C13 C8 C7 C6 -0.9(3) . . . . ?
C13 C12 C14 C15 -59.6(3) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
C10 C11 C12 C14 172.2(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C6 C5 C4 C3 0.1(4) . . . . ?
C11 C12 C14 C15 126.9(2) . . . . ?
C1 N1 C13 C8 -1.5(3) . . . . ?
C1 N1 C13 C12 179.49(19) . . . . ?
C1 C6 C5 C4 0.4(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C16 C15 C14 C12 123.8(3) . . . . ?
C5 C6 C1 N1 179.95(19) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C5 C4 C3 C2 -0.5(4) . . . . ?
C18 C16 C15 C14 -1.0(4) . . . . ?
C17 C16 C15 C14 177.3(2) . . . . ?

_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_jd160223_0ma_a
_audit_block_doi                 10.5517/ccdc.csd.cc2jqplk
_database_code_depnum_ccdc_archive 'CCDC 2345509'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2024-04-03 deposited with the CCDC.	2024-12-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_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                   15.593(3)
_cell_length_b                   9.584(2)
_cell_length_c                   13.356(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.562(7)
_cell_angle_gamma                90
_cell_volume                     1913.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    169.91
_cell_measurement_theta_max      24.98
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1281 before and 0.0717 after correction.
The Ratio of minimum to maximum transmission is 0.7257.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12352
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.525
_diffrn_ambient_temperature      169.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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           1.0
_diffrn_source_power             0.05
_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                2001
_reflns_number_total             3344
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.020
_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)+(0.0623P)²+0.1302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1502
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C23(H23), C22(H22), C21(H21), C10(H10), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.20923(11) 0.59996(18) 0.25388(12) 0.0449(5) Uani 1 1 d . . . . .
O2 O 0.33438(12) 0.55778(19) 0.62040(12) 0.0499(5) Uani 1 1 d . . . . .
H2 H 0.375393 0.514186 0.663543 0.075 Uiso 1 1 calc R U . . .
O3 O 0.45862(11) 0.38107(18) 0.68835(12) 0.0465(5) Uani 1 1 d . . . . .
N1 N 0.44749(12) 0.2810(2) 0.38773(13) 0.0354(5) Uani 1 1 d . . . . .
H1 H 0.444257 0.256668 0.323224 0.043 Uiso 1 1 calc R U . . .
C18 C 0.51789(15) 0.2520(2) 0.57235(17) 0.0348(6) Uani 1 1 d . . . . .
C15 C 0.39279(15) 0.4170(2) 0.50724(17) 0.0339(6) Uani 1 1 d . . . . .
C17 C 0.45675(15) 0.3526(2) 0.59471(17) 0.0350(6) Uani 1 1 d . . . . .
C19 C 0.51112(15) 0.2173(2) 0.46792(17) 0.0328(6) Uani 1 1 d . . . . .
C14 C 0.38904(15) 0.3798(2) 0.40269(17) 0.0321(6) Uani 1 1 d . . . . .
C16 C 0.33179(16) 0.5188(2) 0.52280(18) 0.0372(6) Uani 1 1 d . . . . .
C7 C 0.26813(15) 0.5384(2) 0.33817(17) 0.0355(6) Uani 1 1 d . . . . .
C8 C 0.32597(15) 0.4414(2) 0.31670(17) 0.0340(6) Uani 1 1 d . . . . .
C6 C 0.26900(16) 0.5805(3) 0.43969(18) 0.0385(6) Uani 1 1 d . . . . .
C20 C 0.56729(16) 0.1156(3) 0.44599(19) 0.0395(6) Uani 1 1 d . . . . .
H20 H 0.562142 0.090882 0.375632 0.047 Uiso 1 1 calc R U . . .
C23 C 0.58446(17) 0.1870(3) 0.65252(18) 0.0412(6) Uani 1 1 d . . . . .
H23 H 0.591389 0.212416 0.723134 0.049 Uiso 1 1 calc R U . . .
C9 C 0.31765(16) 0.4003(3) 0.20492(17) 0.0412(6) Uani 1 1 d . . . . .
H9A H 0.296461 0.481539 0.158751 0.049 Uiso 1 1 calc R U . . .
H9B H 0.377304 0.373516 0.198896 0.049 Uiso 1 1 calc R U . . .
C22 C 0.63919(17) 0.0881(3) 0.63041(19) 0.0470(7) Uani 1 1 d . . . . .
H22 H 0.683426 0.044179 0.685342 0.056 Uiso 1 1 calc R U . . .
C21 C 0.62988(17) 0.0513(3) 0.52605(19) 0.0457(7) Uani 1 1 d . . . . .
H21 H 0.667326 -0.018874 0.510776 0.055 Uiso 1 1 calc R U . . .
C1 C 0.12620(17) 0.6600(3) 0.2653(2) 0.0505(7) Uani 1 1 d . . . . .
C10 C 0.25413(19) 0.2812(3) 0.1694(2) 0.0512(7) Uani 1 1 d . . . . .
H10 H 0.267944 0.198959 0.210573 0.061 Uiso 1 1 calc R U . . .
C5 C 0.20833(18) 0.6898(3) 0.4514(2) 0.0495(7) Uani 1 1 d . . . . .
H5 H 0.215659 0.732648 0.517407 0.059 Uiso 1 1 calc R U . . .
C4 C 0.14258(19) 0.7294(3) 0.3694(2) 0.0575(8) Uani 1 1 d . . . . .
H4 H 0.104790 0.804066 0.376895 0.069 Uiso 1 1 calc R U . . .
C11 C 0.18134(19) 0.2744(3) 0.0888(2) 0.0611(8) Uani 1 1 d . . . . .
C3 C 0.0595(2) 0.5406(4) 0.2543(3) 0.0800(10) Uani 1 1 d . . . . .
H3A H 0.052107 0.493519 0.187209 0.120 Uiso 1 1 calc R U . . .
H3B H 0.001747 0.577618 0.257275 0.120 Uiso 1 1 calc R U . . .
H3C H 0.081942 0.473762 0.311332 0.120 Uiso 1 1 calc R U . . .
C2 C 0.0978(2) 0.7616(3) 0.1748(2) 0.0769(10) Uani 1 1 d . . . . .
H2A H 0.142677 0.835726 0.183689 0.115 Uiso 1 1 calc R U . . .
H2B H 0.039883 0.802606 0.173133 0.115 Uiso 1 1 calc R U . . .
H2C H 0.092660 0.712065 0.109166 0.115 Uiso 1 1 calc R U . . .
C13 C 0.1491(2) 0.3929(4) 0.0125(3) 0.1005(13) Uani 1 1 d . . . . .
H13A H 0.183691 0.477196 0.038902 0.151 Uiso 1 1 calc R U . . .
H13B H 0.085569 0.410406 0.004550 0.151 Uiso 1 1 calc R U . . .
H13C H 0.157080 0.367764 -0.055414 0.151 Uiso 1 1 calc R U . . .
C12 C 0.1243(2) 0.1452(4) 0.0669(3) 0.0979(12) Uani 1 1 d . . . . .
H12A H 0.124090 0.106987 -0.001241 0.147 Uiso 1 1 calc R U . . .
H12B H 0.063022 0.168711 0.066326 0.147 Uiso 1 1 calc R U . . .
H12C H 0.148681 0.075597 0.121361 0.147 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 C7 1.367(3) . ?
O1 C1 1.464(3) . ?
O2 H2 0.8400 . ?
O2 C16 1.346(3) . ?
O3 C17 1.272(2) . ?
N1 H1 0.8800 . ?
N1 C19 1.378(3) . ?
N1 C14 1.368(3) . ?
C18 C17 1.446(3) . ?
C18 C19 1.408(3) . ?
C18 C23 1.407(3) . ?
C15 C17 1.441(3) . ?
C15 C14 1.426(3) . ?
C15 C16 1.419(3) . ?
C19 C20 1.397(3) . ?
C14 C8 1.411(3) . ?
C16 C6 1.386(3) . ?
C7 C8 1.381(3) . ?
C7 C6 1.411(3) . ?
C8 C9 1.513(3) . ?
C6 C5 1.449(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.371(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.363(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.496(4) . ?
C22 H22 0.9500 . ?
C22 C21 1.405(3) . ?
C21 H21 0.9500 . ?
C1 C4 1.496(4) . ?
C1 C3 1.525(4) . ?
C1 C2 1.516(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.325(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.325(4) . ?
C4 H4 0.9500 . ?
C11 C13 1.513(4) . ?
C11 C12 1.504(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C7 O1 C1 119.35(18) . . ?
C16 O2 H2 109.5 . . ?
C19 N1 H1 118.1 . . ?
C14 N1 H1 118.1 . . ?
C14 N1 C19 123.72(19) . . ?
C19 C18 C17 119.6(2) . . ?
C23 C18 C17 121.7(2) . . ?
C23 C18 C19 118.7(2) . . ?
C14 C15 C17 120.8(2) . . ?
C16 C15 C17 120.9(2) . . ?
C16 C15 C14 118.2(2) . . ?
O3 C17 C18 120.9(2) . . ?
O3 C17 C15 121.5(2) . . ?
C15 C17 C18 117.58(19) . . ?
N1 C19 C18 120.0(2) . . ?
N1 C19 C20 120.1(2) . . ?
C20 C19 C18 119.9(2) . . ?
N1 C14 C15 118.2(2) . . ?
N1 C14 C8 120.6(2) . . ?
C8 C14 C15 121.1(2) . . ?
O2 C16 C15 119.8(2) . . ?
O2 C16 C6 118.5(2) . . ?
C6 C16 C15 121.8(2) . . ?
O1 C7 C8 116.4(2) . . ?
O1 C7 C6 119.2(2) . . ?
C8 C7 C6 124.3(2) . . ?
C14 C8 C9 122.6(2) . . ?
C7 C8 C14 117.2(2) . . ?
C7 C8 C9 120.2(2) . . ?
C16 C6 C7 117.3(2) . . ?
C16 C6 C5 123.8(2) . . ?
C7 C6 C5 118.8(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 111.9(2) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.7(2) . . ?
C21 C22 H22 120.1 . . ?
C20 C21 C22 120.7(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
O1 C1 C4 110.5(2) . . ?
O1 C1 C3 107.1(2) . . ?
O1 C1 C2 103.6(2) . . ?
C4 C1 C3 110.8(2) . . ?
C4 C1 C2 112.9(3) . . ?
C2 C1 C3 111.7(3) . . ?
C9 C10 H10 115.4 . . ?
C11 C10 C9 129.2(3) . . ?
C11 C10 H10 115.4 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C1 C4 H4 119.1 . . ?
C5 C4 C1 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C10 C11 C13 123.6(3) . . ?
C10 C11 C12 121.4(3) . . ?
C12 C11 C13 115.0(3) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 C7 C8 C14 178.14(19) . . . . ?
O1 C7 C8 C9 -4.5(3) . . . . ?
O1 C7 C6 C16 -177.87(19) . . . . ?
O1 C7 C6 C5 -1.1(3) . . . . ?
O1 C1 C4 C5 -26.8(4) . . . . ?
O2 C16 C6 C7 179.6(2) . . . . ?
O2 C16 C6 C5 3.0(4) . . . . ?
N1 C19 C20 C21 -179.3(2) . . . . ?
N1 C14 C8 C7 178.8(2) . . . . ?
N1 C14 C8 C9 1.5(3) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C18 C23 C22 C21 0.7(4) . . . . ?
C15 C14 C8 C7 -0.2(3) . . . . ?
C15 C14 C8 C9 -177.5(2) . . . . ?
C15 C16 C6 C7 -0.2(3) . . . . ?
C15 C16 C6 C5 -176.8(2) . . . . ?
C17 C18 C19 N1 1.1(3) . . . . ?
C17 C18 C19 C20 -177.1(2) . . . . ?
C17 C18 C23 C22 177.2(2) . . . . ?
C17 C15 C14 N1 0.3(3) . . . . ?
C17 C15 C14 C8 179.3(2) . . . . ?
C17 C15 C16 O2 1.1(3) . . . . ?
C17 C15 C16 C6 -179.1(2) . . . . ?
C19 N1 C14 C15 -1.4(3) . . . . ?
C19 N1 C14 C8 179.5(2) . . . . ?
C19 C18 C17 O3 176.7(2) . . . . ?
C19 C18 C17 C15 -2.1(3) . . . . ?
C19 C18 C23 C22 -2.7(3) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C14 N1 C19 C18 0.7(3) . . . . ?
C14 N1 C19 C20 178.9(2) . . . . ?
C14 C15 C17 O3 -177.4(2) . . . . ?
C14 C15 C17 C18 1.4(3) . . . . ?
C14 C15 C16 O2 -179.1(2) . . . . ?
C14 C15 C16 C6 0.8(3) . . . . ?
C14 C8 C9 C10 88.7(3) . . . . ?
C16 C15 C17 O3 2.5(3) . . . . ?
C16 C15 C17 C18 -178.7(2) . . . . ?
C16 C15 C14 N1 -179.58(19) . . . . ?
C16 C15 C14 C8 -0.6(3) . . . . ?
C16 C6 C5 C4 -170.9(3) . . . . ?
C7 O1 C1 C4 38.2(3) . . . . ?
C7 O1 C1 C3 -82.5(3) . . . . ?
C7 O1 C1 C2 159.4(2) . . . . ?
C7 C8 C9 C10 -88.5(3) . . . . ?
C7 C6 C5 C4 12.6(4) . . . . ?
C8 C7 C6 C16 -0.6(4) . . . . ?
C8 C7 C6 C5 176.2(2) . . . . ?
C8 C9 C10 C11 123.0(3) . . . . ?
C6 C7 C8 C14 0.8(3) . . . . ?
C6 C7 C8 C9 178.2(2) . . . . ?
C6 C5 C4 C1 2.9(4) . . . . ?
C23 C18 C17 O3 -3.2(3) . . . . ?
C23 C18 C17 C15 178.0(2) . . . . ?
C23 C18 C19 N1 -179.0(2) . . . . ?
C23 C18 C19 C20 2.9(3) . . . . ?
C23 C22 C21 C20 1.1(4) . . . . ?
C9 C10 C11 C13 1.4(5) . . . . ?
C9 C10 C11 C12 -178.6(3) . . . . ?
C1 O1 C7 C8 156.8(2) . . . . ?
C1 O1 C7 C6 -25.7(3) . . . . ?
C3 C1 C4 C5 91.6(3) . . . . ?
C2 C1 C4 C5 -142.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
