# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_bettoni9_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2281290'
loop_
_audit_author_name
_audit_author_address
'Jean-Francois Lohier'
;CRISMAT ENSICAEN
France
;
_audit_update_record             
;
2024-04-16 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
3-(4-fluorophenyl)quinolin-2(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 F N O'
_chemical_formula_sum            'C15 H10 F N O'
_chemical_formula_weight         239.24

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'
F F 0.0171 0.0103 '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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.5169(8)
_cell_length_b                   5.7876(3)
_cell_length_c                   22.1074(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.879(2)
_cell_angle_gamma                90
_cell_volume                     2184.88(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7339
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      32.25

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   0.6613
_exptl_transmission_factor_max   0.7463
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.103
_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 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13357
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.385
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2714
_reflns_number_gt                2322
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0554P)²+2.0108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1106
_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

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
F1 F 0.12140(5) 0.60730(16) 0.24077(4) 0.0365(2) Uani 1 1 d . . . . .
O1 O 0.40930(5) 0.93959(15) 0.44333(4) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.46086(6) 0.74999(18) 0.53264(5) 0.0183(2) Uani 1 1 d . . . . .
C9 C 0.40738(7) 0.7704(2) 0.47750(5) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.41025(7) 0.3887(2) 0.56007(6) 0.0172(2) Uani 1 1 d . . . . .
C1 C 0.46370(7) 0.5722(2) 0.57479(5) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.35039(6) 0.5807(2) 0.46245(5) 0.0165(2) Uani 1 1 d . . . . .
C10 C 0.29075(6) 0.5905(2) 0.40307(5) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.35433(7) 0.3999(2) 0.50202(5) 0.0176(2) Uani 1 1 d . . . . .
H7 H 0.318549 0.275652 0.490781 0.021 Uiso 1 1 calc R U . . .
C11 C 0.28040(7) 0.4020(2) 0.36242(6) 0.0194(3) Uani 1 1 d . . . . .
H11 H 0.312354 0.268771 0.372599 0.023 Uiso 1 1 calc R U . . .
C3 C 0.41391(7) 0.2072(2) 0.60294(6) 0.0203(3) Uani 1 1 d . . . . .
H3 H 0.377927 0.082457 0.593811 0.024 Uiso 1 1 calc R U . . .
C15 C 0.24259(7) 0.7840(2) 0.38768(6) 0.0214(3) Uani 1 1 d . . . . .
H15 H 0.249586 0.913363 0.414804 0.026 Uiso 1 1 calc R U . . .
C6 C 0.51908(7) 0.5758(2) 0.63132(6) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.554341 0.701916 0.641442 0.026 Uiso 1 1 calc R U . . .
C4 C 0.46929(7) 0.2089(2) 0.65809(6) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.471900 0.084773 0.686593 0.029 Uiso 1 1 calc R U . . .
C12 C 0.22376(7) 0.4080(2) 0.30724(6) 0.0229(3) Uani 1 1 d . . . . .
H12 H 0.217214 0.281599 0.279139 0.027 Uiso 1 1 calc R U . . .
C14 C 0.18469(7) 0.7901(2) 0.33341(6) 0.0246(3) Uani 1 1 d . . . . .
H14 H 0.151125 0.920109 0.323464 0.029 Uiso 1 1 calc R U . . .
C5 C 0.52178(8) 0.3945(2) 0.67198(6) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.559793 0.394936 0.710073 0.029 Uiso 1 1 calc R U . . .
C13 C 0.17744(7) 0.6018(2) 0.29442(6) 0.0236(3) Uani 1 1 d . . . . .
H1 H 0.4967(10) 0.858(3) 0.5409(7) 0.030(4) Uiso 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
F1 C13 1.3610(14) . ?
O1 C9 1.2418(15) . ?
N1 C9 1.3668(15) . ?
N1 C1 1.3817(16) . ?
C9 C8 1.4712(15) . ?
C2 C1 1.4051(16) . ?
C2 C3 1.4067(17) . ?
C2 C7 1.4319(16) . ?
C1 C6 1.4010(16) . ?
C8 C7 1.3558(16) . ?
C8 C10 1.4855(16) . ?
C10 C15 1.3978(16) . ?
C10 C11 1.3991(16) . ?
C11 C12 1.3906(17) . ?
C3 C4 1.3786(17) . ?
C15 C14 1.3880(17) . ?
C6 C5 1.3760(18) . ?
C4 C5 1.4025(18) . ?
C12 C13 1.3762(19) . ?
C14 C13 1.3780(19) . ?

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 N1 C1 125.47(10) . . ?
O1 C9 N1 120.31(10) . . ?
O1 C9 C8 124.04(11) . . ?
N1 C9 C8 115.65(10) . . ?
C1 C2 C3 118.72(11) . . ?
C1 C2 C7 117.43(11) . . ?
C3 C2 C7 123.84(11) . . ?
N1 C1 C6 120.27(11) . . ?
N1 C1 C2 118.99(10) . . ?
C6 C1 C2 120.73(11) . . ?
C7 C8 C9 119.71(10) . . ?
C7 C8 C10 121.61(10) . . ?
C9 C8 C10 118.67(10) . . ?
C15 C10 C11 118.92(11) . . ?
C15 C10 C8 120.85(10) . . ?
C11 C10 C8 120.20(10) . . ?
C8 C7 C2 122.65(10) . . ?
C12 C11 C10 120.60(11) . . ?
C4 C3 C2 120.52(11) . . ?
C14 C15 C10 121.06(11) . . ?
C5 C6 C1 119.18(11) . . ?
C3 C4 C5 119.80(12) . . ?
C13 C12 C11 118.26(11) . . ?
C13 C14 C15 117.92(12) . . ?
C6 C5 C4 121.04(11) . . ?
F1 C13 C12 118.45(12) . . ?
F1 C13 C14 118.33(12) . . ?
C12 C13 C14 123.22(11) . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_bettoni8_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2348582'
loop_
_audit_author_name
_audit_author_address
'Jean-Francois Lohier'
;CRISMAT ENSICAEN
France
;
_audit_update_record             
;
2024-04-16 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
;
3-phenylquinolin-2(1H)-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   17.8048(14)
_cell_length_b                   5.7547(5)
_cell_length_c                   21.5754(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.736(3)
_cell_angle_gamma                90
_cell_volume                     2127.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9010
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      39.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   0.5643
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.087
_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 2016/2'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32875
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.377
_diffrn_reflns_theta_max         39.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6340
_reflns_number_gt                4220
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0793P)²+0.6013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6340
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.40693(4) 0.05347(11) 0.43925(3) 0.02169(13) Uani 1 1 d . . . . .
N1 N 0.46156(4) 0.25279(12) 0.53091(3) 0.01763(13) Uani 1 1 d . . . . .
C1 C 0.46530(5) 0.43346(14) 0.57366(4) 0.01674(13) Uani 1 1 d . . . . .
C10 C 0.28430(4) 0.39658(13) 0.39554(4) 0.01653(13) Uani 1 1 d . . . . .
C8 C 0.34661(4) 0.41080(13) 0.45702(4) 0.01603(13) Uani 1 1 d . . . . .
C2 C 0.40964(4) 0.61255(14) 0.55780(4) 0.01633(13) Uani 1 1 d . . . . .
C9 C 0.40554(4) 0.22560(14) 0.47384(4) 0.01659(13) Uani 1 1 d . . . . .
C7 C 0.35098(5) 0.59424(13) 0.49759(4) 0.01663(13) Uani 1 1 d . . . . .
H7 H 0.313587 0.715312 0.485499 0.020 Uiso 1 1 calc R U . . .
C11 C 0.27131(5) 0.58297(15) 0.35227(4) 0.01973(15) Uani 1 1 d . . . . .
H11 H 0.303608 0.716879 0.361770 0.024 Uiso 1 1 calc R U . . .
C4 C 0.47244(5) 0.80203(17) 0.65864(4) 0.02315(16) Uani 1 1 d . . . . .
H4 H 0.475277 0.927499 0.687799 0.028 Uiso 1 1 calc R U . . .
C15 C 0.23530(5) 0.20261(15) 0.38110(4) 0.02134(15) Uani 1 1 d . . . . .
H15 H 0.243979 0.073961 0.409763 0.026 Uiso 1 1 calc R U . . .
C6 C 0.52449(5) 0.43876(16) 0.63174(4) 0.02097(16) Uani 1 1 d . . . . .
H6 H 0.561933 0.317279 0.642256 0.025 Uiso 1 1 calc R U . . .
C5 C 0.52771(5) 0.62279(17) 0.67350(4) 0.02408(17) Uani 1 1 d . . . . .
H5 H 0.567905 0.627906 0.712794 0.029 Uiso 1 1 calc R U . . .
C3 C 0.41376(5) 0.79630(15) 0.60154(4) 0.01951(15) Uani 1 1 d . . . . .
H3 H 0.376037 0.917167 0.591810 0.023 Uiso 1 1 calc R U . . .
C14 C 0.17409(5) 0.19639(17) 0.32527(4) 0.02510(17) Uani 1 1 d . . . . .
H14 H 0.140046 0.066155 0.316637 0.030 Uiso 1 1 calc R U . . .
C12 C 0.21125(5) 0.57333(16) 0.29529(4) 0.02254(16) Uani 1 1 d . . . . .
H12 H 0.203642 0.698697 0.265585 0.027 Uiso 1 1 calc R U . . .
C13 C 0.16254(5) 0.38069(17) 0.28192(4) 0.02474(18) Uani 1 1 d . . . . .
H13 H 0.121397 0.374704 0.243244 0.030 Uiso 1 1 calc R U . . .
H1 H 0.5015(8) 0.149(2) 0.5399(6) 0.031(3) Uiso 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 C9 1.2444(10) . ?
N1 C9 1.3673(10) . ?
N1 C1 1.3794(11) . ?
C1 C6 1.4021(11) . ?
C1 C2 1.4063(11) . ?
C10 C15 1.3988(12) . ?
C10 C11 1.3994(11) . ?
C10 C8 1.4828(10) . ?
C8 C7 1.3599(11) . ?
C8 C9 1.4704(11) . ?
C2 C3 1.4058(11) . ?
C2 C7 1.4331(10) . ?
C11 C12 1.3947(11) . ?
C4 C3 1.3828(11) . ?
C4 C5 1.4015(13) . ?
C15 C14 1.3886(12) . ?
C6 C5 1.3815(13) . ?
C14 C13 1.3920(14) . ?
C12 C13 1.3887(14) . ?

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 N1 C1 125.42(7) . . ?
N1 C1 C6 120.15(7) . . ?
N1 C1 C2 119.12(7) . . ?
C6 C1 C2 120.72(7) . . ?
C15 C10 C11 118.87(7) . . ?
C15 C10 C8 120.89(7) . . ?
C11 C10 C8 120.17(7) . . ?
C7 C8 C9 119.43(7) . . ?
C7 C8 C10 121.13(7) . . ?
C9 C8 C10 119.43(7) . . ?
C3 C2 C1 118.87(7) . . ?
C3 C2 C7 123.81(7) . . ?
C1 C2 C7 117.32(7) . . ?
O1 C9 N1 120.19(7) . . ?
O1 C9 C8 123.91(7) . . ?
N1 C9 C8 115.90(7) . . ?
C8 C7 C2 122.75(7) . . ?
C12 C11 C10 120.40(8) . . ?
C3 C4 C5 120.02(8) . . ?
C14 C15 C10 120.61(8) . . ?
C5 C6 C1 119.19(8) . . ?
C6 C5 C4 120.83(8) . . ?
C4 C3 C2 120.35(8) . . ?
C15 C14 C13 120.09(8) . . ?
C13 C12 C11 120.08(8) . . ?
C12 C13 C14 119.90(8) . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061

