# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_TRY1_a
_database_code_depnum_ccdc_archive 'CCDC 2181379'
_audit_update_record             
;
2022-06-23 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_weight         318.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.321(2)
_cell_length_b                   6.8496(11)
_cell_length_c                   18.783(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.77
_cell_angle_gamma                90
_cell_volume                     1602.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    8709
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.85

_exptl_crystal_description       hexagonal
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   0.938
_exptl_transmission_factor_max   0.969
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37763
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         26.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3472
_reflns_number_gt                2396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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+0.5373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.53739(13) 1.1463(3) 0.73087(10) 0.0610(5) Uani 1 1 d . . . . .
O2 O 0.46412(13) 0.6364(3) 0.56565(9) 0.0606(5) Uani 1 1 d . . . . .
O3 O 0.07903(12) 1.2386(3) 0.46854(10) 0.0649(5) Uani 1 1 d . . . . .
N2 N 0.47534(13) 0.9159(2) 0.63507(10) 0.0438(5) Uani 1 1 d . . . . .
C8 C 0.62172(15) 0.7039(3) 0.67921(11) 0.0385(5) Uani 1 1 d . . . . .
C5 C 0.68707(16) 0.5328(3) 0.68096(12) 0.0396(5) Uani 1 1 d . . . . .
N1 N 0.79868(18) 0.9465(3) 0.84654(13) 0.0685(6) Uani 1 1 d . . . . .
C10 C 0.63922(16) 0.8579(3) 0.72667(12) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.51245(17) 0.7395(3) 0.61867(12) 0.0433(5) Uani 1 1 d . . . . .
C13 C 0.37337(16) 1.0007(3) 0.59109(12) 0.0431(5) Uani 1 1 d . . . . .
C12 C 0.54747(17) 0.9963(3) 0.70136(13) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.66594(17) 0.4109(3) 0.61794(13) 0.0471(5) Uani 1 1 d . . . . .
H4 H 0.607294 0.436435 0.574001 0.057 Uiso 1 1 calc R U . . .
C16 C 0.17876(16) 1.1657(3) 0.50797(13) 0.0481(6) Uani 1 1 d . . . . .
C11 C 0.72870(18) 0.9031(3) 0.79372(14) 0.0481(5) Uani 1 1 d . . . . .
C6 C 0.77464(18) 0.4871(3) 0.74610(13) 0.0514(6) Uani 1 1 d . . . . .
H6 H 0.789777 0.564231 0.789392 0.062 Uiso 1 1 calc R U . . .
C14 C 0.27931(18) 0.9027(3) 0.58355(14) 0.0506(6) Uani 1 1 d . . . . .
H14 H 0.281573 0.781907 0.606667 0.061 Uiso 1 1 calc R U . . .
C15 C 0.18269(17) 0.9857(4) 0.54159(14) 0.0531(6) Uani 1 1 d . . . . .
H15 H 0.119214 0.919885 0.535794 0.064 Uiso 1 1 calc R U . . .
C7 C 0.83874(19) 0.3296(4) 0.74706(15) 0.0565(6) Uani 1 1 d . . . . .
H7 H 0.896955 0.302513 0.791093 0.068 Uiso 1 1 calc R U . . .
C18 C 0.37001(17) 1.1778(3) 0.55693(14) 0.0530(6) Uani 1 1 d . . . . .
H18 H 0.433637 1.241879 0.561760 0.064 Uiso 1 1 calc R U . . .
C2 C 0.81898(19) 0.2102(4) 0.68429(15) 0.0570(6) Uani 1 1 d . . . . .
C3 C 0.7310(2) 0.2528(4) 0.61999(14) 0.0572(6) Uani 1 1 d . . . . .
H3 H 0.715474 0.173246 0.577303 0.069 Uiso 1 1 calc R U . . .
C17 C 0.27294(18) 1.2622(3) 0.51536(14) 0.0544(6) Uani 1 1 d . . . . .
H17 H 0.270901 1.383218 0.492452 0.065 Uiso 1 1 calc R U . . .
C19 C 0.0730(2) 1.4280(4) 0.4363(2) 0.0808(9) Uani 1 1 d . . . . .
H19A H 0.107451 1.520457 0.475830 0.121 Uiso 1 1 calc R U . . .
H19B H -0.000973 1.463813 0.411549 0.121 Uiso 1 1 calc R U . . .
H19C H 0.108296 1.427519 0.399774 0.121 Uiso 1 1 calc R U . . .
C1 C 0.8915(3) 0.0400(5) 0.6860(2) 0.0864(10) Uani 1 1 d . . . . .
H1A H 0.848924 -0.075217 0.668221 0.130 Uiso 1 1 calc R U . . .
H1B H 0.939993 0.019460 0.737242 0.130 Uiso 1 1 calc R U . . .
H1C H 0.931786 0.067258 0.653739 0.130 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 C12 1.197(3) . ?
O2 C9 1.204(3) . ?
O3 C16 1.366(3) . ?
O3 C19 1.421(3) . ?
N2 C9 1.381(3) . ?
N2 C12 1.389(3) . ?
N2 C13 1.438(3) . ?
C8 C10 1.347(3) . ?
C8 C5 1.453(3) . ?
C8 C9 1.516(3) . ?
C5 C4 1.393(3) . ?
C5 C6 1.394(3) . ?
N1 C11 1.134(3) . ?
C10 C11 1.428(3) . ?
C10 C12 1.485(3) . ?
C13 C18 1.366(3) . ?
C13 C14 1.384(3) . ?
C4 C3 1.379(3) . ?
C4 H4 0.9300 . ?
C16 C15 1.378(3) . ?
C16 C17 1.381(3) . ?
C6 C7 1.372(3) . ?
C6 H6 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C7 C2 1.381(4) . ?
C7 H7 0.9300 . ?
C18 C17 1.378(3) . ?
C18 H18 0.9300 . ?
C2 C3 1.383(3) . ?
C2 C1 1.507(3) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O3 C19 117.5(2) . . ?
C9 N2 C12 111.00(18) . . ?
C9 N2 C13 124.40(18) . . ?
C12 N2 C13 124.55(18) . . ?
C10 C8 C5 130.91(19) . . ?
C10 C8 C9 105.36(18) . . ?
C5 C8 C9 123.73(18) . . ?
C4 C5 C6 117.7(2) . . ?
C4 C5 C8 121.68(19) . . ?
C6 C5 C8 120.61(19) . . ?
C8 C10 C11 130.4(2) . . ?
C8 C10 C12 111.01(18) . . ?
C11 C10 C12 118.61(19) . . ?
O2 C9 N2 124.7(2) . . ?
O2 C9 C8 128.0(2) . . ?
N2 C9 C8 107.35(17) . . ?
C18 C13 C14 120.3(2) . . ?
C18 C13 N2 119.70(18) . . ?
C14 C13 N2 120.0(2) . . ?
O1 C12 N2 126.9(2) . . ?
O1 C12 C10 127.9(2) . . ?
N2 C12 C10 105.25(18) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O3 C16 C15 116.6(2) . . ?
O3 C16 C17 123.6(2) . . ?
C15 C16 C17 119.8(2) . . ?
N1 C11 C10 177.3(3) . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C6 C7 C2 121.7(2) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C13 C18 C17 120.4(2) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C7 C2 C3 117.8(2) . . ?
C7 C2 C1 120.9(3) . . ?
C3 C2 C1 121.3(3) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_1831RKM_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2182549'
_audit_update_record             
;
2022-06-28 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 N2 O3'
_chemical_formula_sum            'C18 H12 N2 O3'
_chemical_formula_weight         304.11

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9737(17)
_cell_length_b                   7.6375(12)
_cell_length_c                   17.770(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.947(5)
_cell_angle_gamma                90
_cell_volume                     1451.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    164(2)
_cell_measurement_reflns_used    8831
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.57

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             632.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      164(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13814
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.915
_diffrn_reflns_theta_max         25.827
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2800
_reflns_number_gt                2389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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+0.8979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2800
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1756
_refine_ls_wR_factor_gt          0.1642
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.51267(14) 0.6742(2) 0.64009(9) 0.0505(4) Uani 1 1 d . . . . .
O2 O 0.89808(15) 0.4692(3) 0.75937(9) 0.0555(5) Uani 1 1 d . . . . .
O3 O 0.86568(16) 0.6578(3) 0.40335(9) 0.0581(5) Uani 1 1 d . . . . .
N1 N 0.71828(16) 0.5837(3) 0.68083(10) 0.0418(4) Uani 1 1 d . . . . .
C2 C 0.7075(2) 0.5085(3) 0.80423(12) 0.0419(5) Uani 1 1 d . . . . .
C12 C 0.7589(2) 0.6069(3) 0.61025(12) 0.0402(5) Uani 1 1 d . . . . .
C11 C 0.7911(2) 0.5149(3) 0.74864(12) 0.0419(5) Uani 1 1 d . . . . .
C10 C 0.59653(19) 0.6166(3) 0.68909(12) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.59326(19) 0.5678(3) 0.77091(12) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.7893(2) 0.3833(4) 0.94007(13) 0.0667(7) Uani 1 1 d . . . . .
C15 C 0.8360(2) 0.6458(3) 0.47368(12) 0.0435(5) Uani 1 1 d . . . . .
C1 C 0.7521(2) 0.4388(3) 0.88006(14) 0.0479(6) Uani 1 1 d . . . . .
C4 C 0.4822(2) 0.5829(3) 0.80304(13) 0.0428(5) Uani 1 1 d . . . . .
C13 C 0.8692(2) 0.6933(3) 0.60984(13) 0.0455(5) Uani 1 1 d . . . . .
H13 H 0.918307 0.739469 0.656535 0.055 Uiso 1 1 calc R U . . .
C17 C 0.6869(2) 0.5402(3) 0.54264(13) 0.0461(5) Uani 1 1 d . . . . .
H17 H 0.610826 0.481177 0.542975 0.055 Uiso 1 1 calc R U . . .
C14 C 0.9084(2) 0.7127(3) 0.54192(13) 0.0460(5) Uani 1 1 d . . . . .
H14 H 0.984578 0.771501 0.541714 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7259(2) 0.5594(3) 0.47469(13) 0.0485(6) Uani 1 1 d . . . . .
H16 H 0.676622 0.512889 0.428127 0.058 Uiso 1 1 calc R U . . .
C5 C 0.3628(2) 0.5596(3) 0.75651(15) 0.0535(6) Uani 1 1 d . . . . .
H5 H 0.352277 0.541856 0.702520 0.064 Uiso 1 1 calc R U . . .
C9 C 0.4950(2) 0.6116(3) 0.88196(14) 0.0530(6) Uani 1 1 d . . . . .
H9 H 0.575675 0.628940 0.914238 0.064 Uiso 1 1 calc R U . . .
C18 C 0.9849(2) 0.7290(4) 0.40074(15) 0.0575(7) Uani 1 1 d . . . . .
H18A H 0.988698 0.851832 0.417030 0.086 Uiso 1 1 calc R U . . .
H18B H 0.997239 0.721476 0.347890 0.086 Uiso 1 1 calc R U . . .
H18C H 1.050682 0.662511 0.435495 0.086 Uiso 1 1 calc R U . . .
C8 C 0.3911(3) 0.6148(4) 0.91308(17) 0.0658(8) Uani 1 1 d . . . . .
H8 H 0.400363 0.634877 0.966829 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2741(3) 0.5892(4) 0.8671(2) 0.0703(8) Uani 1 1 d . . . . .
H7 H 0.202868 0.590120 0.889264 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2598(2) 0.5624(4) 0.78940(19) 0.0673(8) Uani 1 1 d . . . . .
H6 H 0.178580 0.545547 0.757816 0.081 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 C10 1.200(3) . ?
O2 C11 1.198(3) . ?
O3 C15 1.363(3) . ?
O3 C18 1.427(3) . ?
N1 C11 1.391(3) . ?
N1 C10 1.399(3) . ?
N1 C12 1.433(3) . ?
C2 C3 1.339(3) . ?
C2 C1 1.429(3) . ?
C2 C11 1.492(3) . ?
C12 C13 1.380(3) . ?
C12 C17 1.379(3) . ?
C10 C3 1.509(3) . ?
C3 C4 1.461(3) . ?
N2 C1 1.135(3) . ?
C15 C16 1.380(3) . ?
C15 C14 1.390(3) . ?
C4 C9 1.395(3) . ?
C4 C5 1.395(3) . ?
C13 C14 1.377(3) . ?
C17 C16 1.376(3) . ?
C5 C6 1.384(4) . ?
C9 C8 1.375(4) . ?
C8 C7 1.373(5) . ?
C7 C6 1.371(5) . ?

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
C15 O3 C18 117.69(18) . . ?
C11 N1 C10 110.71(18) . . ?
C11 N1 C12 125.03(18) . . ?
C10 N1 C12 124.13(17) . . ?
C3 C2 C1 129.2(2) . . ?
C3 C2 C11 110.46(19) . . ?
C1 C2 C11 120.31(19) . . ?
C13 C12 C17 120.3(2) . . ?
C13 C12 N1 120.60(19) . . ?
C17 C12 N1 119.14(19) . . ?
O2 C11 N1 126.9(2) . . ?
O2 C11 C2 127.7(2) . . ?
N1 C11 C2 105.46(18) . . ?
O1 C10 N1 125.8(2) . . ?
O1 C10 C3 127.6(2) . . ?
N1 C10 C3 106.63(17) . . ?
C2 C3 C4 129.3(2) . . ?
C2 C3 C10 106.71(19) . . ?
C4 C3 C10 123.97(19) . . ?
O3 C15 C16 115.7(2) . . ?
O3 C15 C14 124.6(2) . . ?
C16 C15 C14 119.7(2) . . ?
N2 C1 C2 179.0(3) . . ?
C9 C4 C5 119.0(2) . . ?
C9 C4 C3 120.0(2) . . ?
C5 C4 C3 120.9(2) . . ?
C12 C13 C14 120.2(2) . . ?
C16 C17 C12 119.7(2) . . ?
C13 C14 C15 119.7(2) . . ?
C17 C16 C15 120.5(2) . . ?
C6 C5 C4 119.7(3) . . ?
C8 C9 C4 120.1(3) . . ?
C7 C8 C9 120.5(3) . . ?
C8 C7 C6 120.1(3) . . ?
C7 C6 C5 120.6(3) . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054

