# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 2089632'
loop_
_audit_author_name
_audit_author_address
'ling ling li'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-06-13 deposited with the CCDC.	2021-10-07 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         'C15 H13 N O'
_chemical_formula_sum            'C15 H13 N O'
_chemical_formula_weight         223.26

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'

_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                   5.47530(10)
_cell_length_b                   13.6812(3)
_cell_length_c                   15.3625(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1150.78(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7225
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      68.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   0.6727
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9754
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.327
_diffrn_reflns_theta_max         68.254
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2109
_reflns_number_gt                2052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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)+(0.0549P)²+0.1254P] 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_abs_structure_details 
;
 Flack x determined using 813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(12)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2109
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.6203(3) 0.07333(9) 0.21765(9) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.3556(3) 0.31629(12) 0.20628(11) 0.0246(4) Uani 1 1 d . . . . .
N1 N 0.4939(3) 0.36059(10) 0.26977(9) 0.0268(3) Uani 1 1 d . . . . .
H1 H 0.530321 0.423194 0.267816 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0705(4) 0.22346(15) 0.07823(12) 0.0368(5) Uani 1 1 d . . . . .
H4 H -0.026977 0.192440 0.035164 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0394(4) 0.32294(15) 0.09666(12) 0.0340(4) Uani 1 1 d . . . . .
H3 H -0.079228 0.359533 0.065417 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1780(3) 0.36838(14) 0.15932(11) 0.0290(4) Uani 1 1 d . . . . .
H2 H 0.153485 0.435848 0.171025 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2441(4) 0.17120(14) 0.12335(11) 0.0327(4) Uani 1 1 d . . . . .
H5 H 0.266688 0.103815 0.110803 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3877(3) 0.21569(13) 0.18735(11) 0.0273(4) Uani 1 1 d . . . . .
C7 C 0.5782(3) 0.15943(12) 0.23317(11) 0.0281(4) Uani 1 1 d . . . . .
C8 C 0.7248(4) 0.21408(13) 0.30064(12) 0.0296(4) Uani 1 1 d . . . . .
H8A H 0.874022 0.241020 0.273257 0.036 Uiso 1 1 calc R U . . .
H8B H 0.775922 0.168258 0.347073 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5768(3) 0.29740(12) 0.34079(11) 0.0260(4) Uani 1 1 d . . . . .
H9 H 0.429317 0.268429 0.369209 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7145(3) 0.35526(12) 0.40878(11) 0.0265(4) Uani 1 1 d . . . . .
C11 C 0.6284(4) 0.35723(14) 0.49353(12) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.485475 0.321580 0.508380 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7493(4) 0.41087(15) 0.55686(13) 0.0397(5) Uani 1 1 d . . . . .
H12 H 0.688362 0.412322 0.614748 0.048 Uiso 1 1 calc R U . . .
C13 C 0.9590(4) 0.46234(14) 0.53566(14) 0.0410(5) Uani 1 1 d . . . . .
H13 H 1.042106 0.499117 0.578941 0.049 Uiso 1 1 calc R U . . .
C14 C 1.0467(4) 0.45999(14) 0.45134(15) 0.0384(5) Uani 1 1 d . . . . .
H14 H 1.191079 0.494908 0.436818 0.046 Uiso 1 1 calc R U . . .
C15 C 0.9256(4) 0.40713(13) 0.38811(13) 0.0327(4) Uani 1 1 d . . . . .
H15 H 0.986503 0.406139 0.330212 0.039 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 1.224(2) . ?
C1 N1 1.375(2) . ?
C1 C2 1.405(3) . ?
C1 C6 1.418(2) . ?
N1 C9 1.464(2) . ?
C4 C5 1.377(3) . ?
C4 C3 1.401(3) . ?
C3 C2 1.375(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.475(3) . ?
C7 C8 1.509(3) . ?
C8 C9 1.529(2) . ?
C9 C10 1.512(2) . ?
C10 C11 1.385(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.381(3) . ?

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
N1 C1 C2 121.43(15) . . ?
N1 C1 C6 120.34(16) . . ?
C2 C1 C6 118.23(16) . . ?
C1 N1 C9 116.04(13) . . ?
C5 C4 C3 119.13(18) . . ?
C2 C3 C4 120.91(18) . . ?
C3 C2 C1 120.83(17) . . ?
C4 C5 C6 121.09(17) . . ?
C5 C6 C1 119.80(17) . . ?
C5 C6 C7 120.40(16) . . ?
C1 C6 C7 119.76(16) . . ?
O1 C7 C6 122.85(17) . . ?
O1 C7 C8 120.71(17) . . ?
C6 C7 C8 116.44(15) . . ?
C7 C8 C9 111.39(15) . . ?
N1 C9 C10 111.12(13) . . ?
N1 C9 C8 107.70(13) . . ?
C10 C9 C8 113.88(15) . . ?
C11 C10 C15 119.14(17) . . ?
C11 C10 C9 119.33(16) . . ?
C15 C10 C9 121.54(16) . . ?
C10 C11 C12 120.49(19) . . ?
C13 C12 C11 119.96(19) . . ?
C14 C13 C12 119.78(19) . . ?
C15 C14 C13 120.30(19) . . ?
C14 C15 C10 120.34(19) . . ?

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
C2 C1 N1 C9 150.59(16) . . . . ?
C6 C1 N1 C9 -28.7(2) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
N1 C1 C2 C3 -179.32(17) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 -178.08(17) . . . . ?
N1 C1 C6 C5 179.26(16) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
N1 C1 C6 C7 -2.8(2) . . . . ?
C2 C1 C6 C7 177.89(14) . . . . ?
C5 C6 C7 O1 0.4(3) . . . . ?
C1 C6 C7 O1 -177.49(17) . . . . ?
C5 C6 C7 C8 179.56(16) . . . . ?
C1 C6 C7 C8 1.7(2) . . . . ?
O1 C7 C8 C9 -152.49(17) . . . . ?
C6 C7 C8 C9 28.3(2) . . . . ?
C1 N1 C9 C10 -176.86(15) . . . . ?
C1 N1 C9 C8 57.78(19) . . . . ?
C7 C8 C9 N1 -56.07(18) . . . . ?
C7 C8 C9 C10 -179.78(14) . . . . ?
N1 C9 C10 C11 120.02(17) . . . . ?
C8 C9 C10 C11 -118.15(18) . . . . ?
N1 C9 C10 C15 -59.6(2) . . . . ?
C8 C9 C10 C15 62.2(2) . . . . ?
C15 C10 C11 C12 0.6(3) . . . . ?
C9 C10 C11 C12 -179.07(17) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C10 -0.3(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C9 C10 C15 C14 179.50(17) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2090799'
loop_
_audit_author_name
_audit_author_address
'ling ling li'
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2021-06-18 deposited with the CCDC.	2021-10-07 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         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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'

_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                   5.4718(3)
_cell_length_b                   13.1212(7)
_cell_length_c                   16.6256(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1193.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      4.29
_cell_measurement_theta_max      68.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.6723
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.615
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22057
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.292
_diffrn_reflns_theta_max         68.413
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2196
_reflns_number_gt                2093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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)+(0.0510P)²+0.0643P] 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_abs_structure_details 
;
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2196
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.2718(3) 0.90399(9) 0.80184(8) 0.0605(4) Uani 1 1 d . . . . .
H1 H 0.171903 0.867986 0.825174 0.091 Uiso 1 1 calc R U . . .
C1 C 0.6491(3) 0.67404(12) 0.78527(9) 0.0416(3) Uani 1 1 d . . . . .
N1 N 0.5367(3) 0.62950(10) 0.71887(8) 0.0459(3) Uani 1 1 d . . . . .
H6 H 0.604(4) 0.5740(16) 0.7015(11) 0.053(5) Uiso 1 1 d . . . . .
C4 C 0.8645(4) 0.76025(15) 0.92213(11) 0.0630(5) Uani 1 1 d . . . . .
H4 H 0.934299 0.788812 0.967878 0.076 Uiso 1 1 calc R U . . .
C3 C 0.9197(4) 0.66109(15) 0.89981(11) 0.0610(5) Uani 1 1 d . . . . .
H3 H 1.028587 0.623006 0.930471 0.073 Uiso 1 1 calc R U . . .
C2 C 0.8138(3) 0.61858(13) 0.83233(10) 0.0516(4) Uani 1 1 d . . . . .
H2 H 0.852744 0.552038 0.817945 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7051(3) 0.81567(14) 0.87567(11) 0.0551(4) Uani 1 1 d . . . . .
H5 H 0.668663 0.882274 0.890576 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5961(3) 0.77538(11) 0.80693(9) 0.0440(4) Uani 1 1 d . . . . .
C7 C 0.4321(3) 0.84113(11) 0.75498(9) 0.0474(4) Uani 1 1 d . . . . .
H7 H 0.538676 0.886971 0.724396 0.057 Uiso 1 1 calc R U . . .
C8 C 0.2898(3) 0.77823(12) 0.69415(10) 0.0516(4) Uani 1 1 d . . . . .
H8A H 0.224221 0.822802 0.652907 0.062 Uiso 1 1 calc R U . . .
H8AB H 0.153691 0.745079 0.720828 0.062 Uiso 1 1 calc R U . . .
C9 C 0.4526(3) 0.69780(11) 0.65513(9) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.595115 0.731880 0.631627 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3221(3) 0.63963(12) 0.58946(9) 0.0431(3) Uani 1 1 d . . . . .
C11 C 0.1112(3) 0.58410(14) 0.60524(11) 0.0547(4) Uani 1 1 d . . . . .
H11 H 0.050912 0.580823 0.657478 0.066 Uiso 1 1 calc R U . . .
C12 C -0.0098(4) 0.53379(14) 0.54419(12) 0.0592(5) Uani 1 1 d . . . . .
H12 H -0.152454 0.497912 0.555291 0.071 Uiso 1 1 calc R U . . .
C13 C 0.0806(4) 0.53657(14) 0.46652(12) 0.0599(5) Uani 1 1 d . . . . .
H13 H 0.000266 0.501782 0.425578 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2897(4) 0.59097(15) 0.44997(11) 0.0576(4) Uani 1 1 d . . . . .
H14 H 0.350901 0.592992 0.397806 0.069 Uiso 1 1 calc R U . . .
C15 C 0.4091(3) 0.64275(13) 0.51114(10) 0.0494(4) Uani 1 1 d . . . . .
H15 H 0.549311 0.680032 0.499511 0.059 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 1.4342(19) . ?
C1 N1 1.392(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.408(2) . ?
N1 C9 1.4621(19) . ?
C4 C5 1.373(3) . ?
C4 C3 1.386(3) . ?
C3 C2 1.380(3) . ?
C5 C6 1.393(2) . ?
C6 C7 1.515(2) . ?
C7 C8 1.520(2) . ?
C8 C9 1.526(2) . ?
C9 C10 1.511(2) . ?
C10 C15 1.387(2) . ?
C10 C11 1.390(2) . ?
C11 C12 1.380(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.387(2) . ?

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
N1 C1 C2 120.66(14) . . ?
N1 C1 C6 120.57(14) . . ?
C2 C1 C6 118.77(15) . . ?
C1 N1 C9 117.15(13) . . ?
C5 C4 C3 118.99(18) . . ?
C2 C3 C4 120.36(18) . . ?
C3 C2 C1 121.00(16) . . ?
C4 C5 C6 122.16(16) . . ?
C5 C6 C1 118.69(15) . . ?
C5 C6 C7 120.33(14) . . ?
C1 C6 C7 120.93(14) . . ?
O1 C7 C6 112.33(13) . . ?
O1 C7 C8 111.13(14) . . ?
C6 C7 C8 111.93(12) . . ?
C7 C8 C9 111.06(14) . . ?
N1 C9 C10 111.27(12) . . ?
N1 C9 C8 107.43(12) . . ?
C10 C9 C8 112.36(13) . . ?
C15 C10 C11 118.53(16) . . ?
C15 C10 C9 120.07(14) . . ?
C11 C10 C9 121.38(15) . . ?
C12 C11 C10 120.69(17) . . ?
C11 C12 C13 120.16(17) . . ?
C14 C13 C12 119.84(17) . . ?
C13 C14 C15 119.95(18) . . ?
C14 C15 C10 120.82(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C9 -155.21(14) . . . . ?
C6 C1 N1 C9 25.7(2) . . . . ?
C5 C4 C3 C2 -0.6(3) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
N1 C1 C2 C3 -177.80(16) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -176.67(16) . . . . ?
N1 C1 C6 C5 177.46(14) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
N1 C1 C6 C7 -5.0(2) . . . . ?
C2 C1 C6 C7 175.89(14) . . . . ?
C5 C6 C7 O1 -41.9(2) . . . . ?
C1 C6 C7 O1 140.57(15) . . . . ?
C5 C6 C7 C8 -167.77(15) . . . . ?
C1 C6 C7 C8 14.7(2) . . . . ?
O1 C7 C8 C9 -169.65(13) . . . . ?
C6 C7 C8 C9 -43.15(18) . . . . ?
C1 N1 C9 C10 -176.75(13) . . . . ?
C1 N1 C9 C8 -53.37(18) . . . . ?
C7 C8 C9 N1 61.97(17) . . . . ?
C7 C8 C9 C10 -175.32(13) . . . . ?
N1 C9 C10 C15 -120.45(16) . . . . ?
C8 C9 C10 C15 119.03(16) . . . . ?
N1 C9 C10 C11 61.0(2) . . . . ?
C8 C9 C10 C11 -59.50(19) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 178.13(16) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -0.5(2) . . . . ?
C9 C10 C15 C14 -179.11(15) . . . . ?

_refine_diff_density_max         0.086
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033

