# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_WD-LY687-ORTH_a
_database_code_depnum_ccdc_archive 'CCDC 2242965'
loop_
_audit_author_name
_audit_author_address
WD-LY-azaMBH
;Ocean University of China
China
;
_audit_update_record             
;
2023-02-18 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2022,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        WD-LY-6-87
_chemical_name_common            ?
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_moiety         ?
_chemical_formula_weight         277.31
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8982(5)
_cell_length_b                   12.1235(7)
_cell_length_c                   13.0719(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1410.16(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9763
_cell_measurement_theta_min      6.02
_cell_measurement_theta_max      66.94
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   0.906
_exptl_transmission_factor_max   0.934
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            13582
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_theta_min         6.016
_diffrn_reflns_theta_max         67.487
_diffrn_reflns_theta_full        67.487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2449
_reflns_number_gt                2374
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.959
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1889
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.646
_refine_ls_restrained_S_all      1.646
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.05(11)
_refine_ls_abs_structure_details 
;
 Flack x determined using 948 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.6755(3) 0.6592(2) 0.40305(19) 0.0228(7) Uani 1 1 d . . . . .
O2 O 0.5824(3) 0.4228(2) 0.4868(2) 0.0239(7) Uani 1 1 d . . . . .
N1 N 0.4064(3) 0.6800(2) 0.5344(2) 0.0182(7) Uani 1 1 d . . . . .
H1 H 0.360284 0.741795 0.518157 0.022 Uiso 1 1 calc R U . . .
C1 C 0.5769(5) 0.7471(3) 0.2562(3) 0.0289(9) Uani 1 1 d . . . . .
H1A H 0.543656 0.710420 0.193335 0.043 Uiso 1 1 calc R U . . .
H1B H 0.680567 0.772838 0.247660 0.043 Uiso 1 1 calc R U . . .
H1C H 0.511335 0.810129 0.270487 0.043 Uiso 1 1 calc R U . . .
C2 C 0.2519(4) 0.5154(3) 0.4906(2) 0.0166(8) Uani 1 1 d . . . . .
C3 C 0.1185(4) 0.5734(3) 0.4999(3) 0.0221(8) Uani 1 1 d . . . . .
H3 H 0.121025 0.651738 0.499338 0.027 Uiso 1 1 calc R U . . .
C4 C -0.0187(4) 0.5202(3) 0.5100(3) 0.0240(8) Uani 1 1 d . . . . .
H4 H -0.108362 0.562008 0.517368 0.029 Uiso 1 1 calc R U . . .
C5 C -0.0248(5) 0.4064(3) 0.5093(3) 0.0251(9) Uani 1 1 d . . . . .
H5 H -0.118421 0.369541 0.516189 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1065(4) 0.3465(3) 0.4984(3) 0.0235(8) Uani 1 1 d . . . . .
H6 H 0.102305 0.268225 0.497819 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2452(4) 0.3994(3) 0.4882(3) 0.0212(8) Uani 1 1 d . . . . .
H7 H 0.334425 0.357362 0.479753 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4013(4) 0.5764(3) 0.4744(2) 0.0174(8) Uani 1 1 d . . . . .
C9 C 0.5312(4) 0.5086(3) 0.5229(3) 0.0174(8) Uani 1 1 d . . . . .
C10 C 0.5730(4) 0.5649(3) 0.6167(3) 0.0221(8) Uani 1 1 d . . . . .
C11 C 0.4956(4) 0.6642(3) 0.6204(2) 0.0195(8) Uani 1 1 d . . . . .
C12 C 0.4309(4) 0.6007(3) 0.3617(3) 0.0187(8) Uani 1 1 d . . . . .
C13 C 0.5697(4) 0.6671(3) 0.3437(3) 0.0202(8) Uani 1 1 d . . . . .
C14 C 0.6752(4) 0.5359(4) 0.6933(3) 0.0255(9) Uani 1 1 d . . . . .
H14 H 0.728893 0.468310 0.690004 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6961(4) 0.6076(4) 0.7738(3) 0.0324(10) Uani 1 1 d . . . . .
H15 H 0.763525 0.589238 0.827494 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6177(5) 0.7077(4) 0.7761(3) 0.0333(11) Uani 1 1 d . . . . .
H16 H 0.634844 0.756823 0.831537 0.040 Uiso 1 1 calc R U . . .
C17 C 0.5169(5) 0.7378(3) 0.7014(3) 0.0268(9) Uani 1 1 d . . . . .
H17 H 0.463993 0.805747 0.704666 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3468(5) 0.5639(3) 0.2848(3) 0.0247(9) Uani 1 1 d . . . . .
H18A H 0.374486 0.579667 0.216178 0.030 Uiso 1 1 calc R U . . .
H18B H 0.259015 0.521808 0.298561 0.030 Uiso 1 1 calc R U . . .


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 C13 1.224(5) . ?
O2 C9 1.230(4) . ?
N1 C11 1.390(4) . ?
N1 C8 1.482(4) . ?
C1 C13 1.500(5) . ?
C2 C3 1.385(5) . ?
C2 C7 1.408(5) . ?
C2 C8 1.536(5) . ?
C3 C4 1.387(5) . ?
C4 C5 1.381(6) . ?
C5 C6 1.383(6) . ?
C6 C7 1.397(6) . ?
C8 C12 1.524(4) . ?
C8 C9 1.554(5) . ?
C9 C10 1.451(5) . ?
C10 C11 1.387(5) . ?
C10 C14 1.398(5) . ?
C11 C17 1.398(5) . ?
C12 C18 1.331(5) . ?
C12 C13 1.493(5) . ?
C14 C15 1.377(6) . ?
C15 C16 1.400(7) . ?
C16 C17 1.376(6) . ?

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
C11 N1 C8 109.2(3) . . ?
C3 C2 C7 118.2(3) . . ?
C3 C2 C8 120.6(3) . . ?
C7 C2 C8 121.0(3) . . ?
C2 C3 C4 121.8(3) . . ?
C5 C4 C3 119.9(4) . . ?
C4 C5 C6 119.5(4) . . ?
C5 C6 C7 121.0(3) . . ?
C6 C7 C2 119.6(4) . . ?
N1 C8 C12 110.0(3) . . ?
N1 C8 C2 111.2(3) . . ?
C12 C8 C2 112.1(3) . . ?
N1 C8 C9 102.1(3) . . ?
C12 C8 C9 111.6(3) . . ?
C2 C8 C9 109.5(3) . . ?
O2 C9 C10 128.9(3) . . ?
O2 C9 C8 124.4(3) . . ?
C10 C9 C8 106.7(3) . . ?
C11 C10 C14 121.0(4) . . ?
C11 C10 C9 108.1(3) . . ?
C14 C10 C9 130.8(4) . . ?
C10 C11 N1 112.0(3) . . ?
C10 C11 C17 120.9(3) . . ?
N1 C11 C17 127.0(3) . . ?
C18 C12 C13 121.8(3) . . ?
C18 C12 C8 124.6(3) . . ?
C13 C12 C8 113.6(3) . . ?
O1 C13 C12 119.6(3) . . ?
O1 C13 C1 120.1(3) . . ?
C12 C13 C1 120.3(3) . . ?
C15 C14 C10 118.5(4) . . ?
C14 C15 C16 119.8(4) . . ?
C17 C16 C15 122.6(4) . . ?
C16 C17 C11 117.2(4) . . ?

####################################################################### 
# 
# 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_LY929_a
_database_code_depnum_ccdc_archive 'CCDC 2256137'
loop_
_audit_author_name
_audit_author_address
WDLY
;Ocean University of China
China
;
_audit_update_record             
;
2023-04-13 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        WD-LY-9-29
_chemical_name_common            ?
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_moiety         ?
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4311(17)
_cell_length_b                   11.3052(17)
_cell_length_c                   12.2205(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1441.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3192
_cell_measurement_theta_min      5.576
_cell_measurement_theta_max      66.3695
_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5246
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          ?
_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 ?
_diffrn_detector_type            ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?
_diffrn_reflns_number            12864
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_theta_min         5.330
_diffrn_reflns_theta_max         68.068
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2506
_reflns_number_gt                1973
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.947
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2022.1-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.8301P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2506
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_abs_structure_details 
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.7371(3) 0.3174(3) 0.0638(3) 0.0362(8) Uani 1 1 d . . . . .
O2 O 0.5505(3) 0.5880(3) 0.3701(3) 0.0318(8) Uani 1 1 d . . . . .
O3 O 0.0300(3) 0.5440(3) 0.2872(3) 0.0363(9) Uani 1 1 d . . . . .
N1 N 0.5023(3) 0.3645(3) 0.1704(3) 0.0260(8) Uani 1 1 d . . . . .
H1 H 0.521505 0.312675 0.119276 0.039 Uiso 1 1 calc R U . . .
C1 C 0.6643(4) 0.3414(4) 0.3180(4) 0.0240(10) Uani 1 1 d . . . . .
C2 C 0.5953(4) 0.2553(4) 0.3731(4) 0.0283(10) Uani 1 1 d . . . . .
H2 H 0.505019 0.251053 0.363474 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6552(5) 0.1755(4) 0.4420(4) 0.0323(11) Uani 1 1 d . . . . .
H3 H 0.605938 0.117701 0.479612 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7872(5) 0.1796(4) 0.4565(4) 0.0344(12) Uani 1 1 d . . . . .
H4 H 0.829159 0.123878 0.502395 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8561(5) 0.2659(4) 0.4030(4) 0.0340(12) Uani 1 1 d . . . . .
H5 H 0.946267 0.269761 0.413009 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7970(4) 0.3470(4) 0.3350(4) 0.0284(11) Uani 1 1 d . . . . .
H6 H 0.846284 0.406535 0.299782 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5966(4) 0.4259(3) 0.2391(4) 0.0230(10) Uani 1 1 d . . . . .
C8 C 0.5096(4) 0.5132(4) 0.3060(4) 0.0235(10) Uani 1 1 d . . . . .
C9 C 0.3784(4) 0.4888(3) 0.2750(4) 0.0244(10) Uani 1 1 d . . . . .
C10 C 0.3792(4) 0.3992(3) 0.1970(4) 0.0247(10) Uani 1 1 d . . . . .
C11 C 0.6898(4) 0.4927(4) 0.1654(4) 0.0269(10) Uani 1 1 d . . . . .
C12 C 0.7505(4) 0.4232(4) 0.0770(4) 0.0302(10) Uani 1 1 d . . . . .
H12 H 0.803943 0.464216 0.026799 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2630(4) 0.5419(3) 0.3114(4) 0.0263(10) Uani 1 1 d . . . . .
H13 H 0.262708 0.602298 0.365470 0.032 Uiso 1 1 calc R U . . .
C14 C 0.1512(4) 0.5015(4) 0.2642(4) 0.0268(10) Uani 1 1 d . . . . .
C15 C 0.1531(4) 0.4127(4) 0.1844(4) 0.0308(11) Uani 1 1 d . . . . .
H15 H 0.074300 0.387814 0.152904 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2652(4) 0.3601(4) 0.1498(4) 0.0281(10) Uani 1 1 d . . . . .
H16 H 0.264835 0.299634 0.095825 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7246(4) 0.6043(4) 0.1744(4) 0.0330(11) Uani 1 1 d . . . . .
H17A H 0.786000 0.636546 0.125391 0.040 Uiso 1 1 calc R U . . .
H17B H 0.688204 0.652564 0.229994 0.040 Uiso 1 1 calc R U . . .
C18 C 0.0217(4) 0.6298(4) 0.3721(4) 0.0366(12) Uani 1 1 d . . . . .
H18A H -0.068593 0.648211 0.386403 0.055 Uiso 1 1 calc R U . . .
H18B H 0.066614 0.701970 0.349574 0.055 Uiso 1 1 calc R U . . .
H18C H 0.061269 0.598446 0.438772 0.055 Uiso 1 1 calc R U . . .


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 C12 1.214(5) . ?
O2 C8 1.230(5) . ?
O3 C14 1.381(5) . ?
O3 C18 1.423(6) . ?
N1 C10 1.382(5) . ?
N1 C7 1.467(5) . ?
C1 C2 1.385(6) . ?
C1 C6 1.400(6) . ?
C1 C7 1.531(6) . ?
C2 C3 1.384(6) . ?
C3 C4 1.389(7) . ?
C4 C5 1.377(7) . ?
C5 C6 1.383(6) . ?
C7 C11 1.526(6) . ?
C7 C8 1.570(6) . ?
C8 C9 1.446(6) . ?
C9 C10 1.390(6) . ?
C9 C13 1.417(6) . ?
C10 C16 1.393(6) . ?
C11 C17 1.317(6) . ?
C11 C12 1.479(6) . ?
C13 C14 1.379(6) . ?
C14 C15 1.400(6) . ?
C15 C16 1.378(6) . ?

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
C14 O3 C18 116.2(3) . . ?
C10 N1 C7 110.8(3) . . ?
C2 C1 C6 118.3(4) . . ?
C2 C1 C7 120.3(4) . . ?
C6 C1 C7 121.4(4) . . ?
C3 C2 C1 121.2(4) . . ?
C2 C3 C4 120.3(5) . . ?
C5 C4 C3 118.7(5) . . ?
C4 C5 C6 121.5(5) . . ?
C5 C6 C1 119.9(4) . . ?
N1 C7 C11 108.9(3) . . ?
N1 C7 C1 112.0(3) . . ?
C11 C7 C1 112.8(3) . . ?
N1 C7 C8 102.0(3) . . ?
C11 C7 C8 111.4(3) . . ?
C1 C7 C8 109.3(4) . . ?
O2 C8 C9 128.7(4) . . ?
O2 C8 C7 124.3(4) . . ?
C9 C8 C7 106.9(4) . . ?
C10 C9 C13 121.9(4) . . ?
C10 C9 C8 108.2(4) . . ?
C13 C9 C8 129.9(4) . . ?
N1 C10 C9 111.9(4) . . ?
N1 C10 C16 127.3(4) . . ?
C9 C10 C16 120.7(4) . . ?
C17 C11 C12 116.9(4) . . ?
C17 C11 C7 126.9(4) . . ?
C12 C11 C7 116.1(4) . . ?
O1 C12 C11 124.8(4) . . ?
C14 C13 C9 116.5(4) . . ?
C13 C14 O3 125.0(4) . . ?
C13 C14 C15 121.1(4) . . ?
O3 C14 C15 113.9(4) . . ?
C16 C15 C14 122.3(4) . . ?
C15 C16 C10 117.4(4) . . ?

