# Electronic Supplementary Material (ESI) for Green 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_kui1417_21
_database_code_depnum_ccdc_archive 'CCDC 2115159'
loop_
_audit_author_name
_audit_author_address
'Sebastian Dechert'
;Institute of Inorganic Chemistry  Georg August University of Gottingen
Germany
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2023-12-06 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 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32

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                   7.985(2)
_cell_length_b                   8.521(2)
_cell_length_c                   21.601(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.717(9)
_cell_angle_gamma                90
_cell_volume                     1459.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    365
_cell_measurement_theta_min      1.9099
_cell_measurement_theta_max      22.2987

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            35121
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.568
_diffrn_reflns_theta_max         27.824
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3462
_reflns_number_gt                2967
_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 Instrument Service vV6.2.10'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0374P)²+0.7008P] 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         3462
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0883
_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 0.30156(11) 0.89785(11) 0.43486(4) 0.0275(2) Uani 1 1 d . . . . .
O2 O 1.05450(10) 0.29894(9) 0.43759(4) 0.01956(19) Uani 1 1 d . . . . .
N1 N 0.72679(11) 0.93479(11) 0.31156(4) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.53610(14) 0.90669(13) 0.37858(5) 0.0162(2) Uani 1 1 d . . . . .
C2 C 0.68289(14) 0.84188(13) 0.35930(5) 0.0155(2) Uani 1 1 d . . . . .
C3 C 0.86092(14) 0.91877(14) 0.27646(5) 0.0178(2) Uani 1 1 d . . . . .
H3 H 0.937354 0.833644 0.284142 0.021 Uiso 1 1 calc R U . . .
C4 C 0.88263(15) 1.02451(14) 0.23132(5) 0.0203(2) Uani 1 1 d . . . . .
H4 H 0.974953 1.013584 0.207620 0.024 Uiso 1 1 calc R U . . .
C5 C 0.76718(15) 1.15318(14) 0.21894(5) 0.0211(2) Uani 1 1 d . . . . .
H5 H 0.783203 1.226867 0.187150 0.025 Uiso 1 1 calc R U . . .
C6 C 0.63497(14) 1.16925(14) 0.25281(5) 0.0188(2) Uani 1 1 d . . . . .
H6 H 0.559250 1.254797 0.244768 0.023 Uiso 1 1 calc R U . . .
C7 C 0.60923(14) 1.05870(13) 0.30026(5) 0.0162(2) Uani 1 1 d . . . . .
C8 C 0.48861(14) 1.04180(13) 0.34122(5) 0.0168(2) Uani 1 1 d . . . . .
C9 C 0.34075(15) 1.14983(15) 0.34356(6) 0.0235(3) Uani 1 1 d . . . . .
H9A H 0.356923 1.244576 0.319232 0.035 Uiso 1 1 calc R U . . .
H9B H 0.331666 1.178924 0.386931 0.035 Uiso 1 1 calc R U . . .
H9C H 0.237224 1.096447 0.326030 0.035 Uiso 1 1 calc R U . . .
C10 C 0.44525(14) 0.85238(13) 0.43068(5) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.52989(16) 0.74377(17) 0.47997(6) 0.0283(3) Uani 1 1 d . . . . .
H11A H 0.520173 0.635252 0.464941 0.043 Uiso 1 1 calc R U . . .
H11B H 0.475185 0.753624 0.518094 0.043 Uiso 1 1 calc R U . . .
H11C H 0.649282 0.771910 0.488860 0.043 Uiso 1 1 calc R U . . .
C12 C 0.77913(14) 0.69815(13) 0.37821(5) 0.0159(2) Uani 1 1 d . . . . .
C13 C 0.70397(14) 0.55057(14) 0.36977(5) 0.0189(2) Uani 1 1 d . . . . .
H13 H 0.591260 0.543082 0.350295 0.023 Uiso 1 1 calc R U . . .
C14 C 0.79070(15) 0.41381(13) 0.38931(5) 0.0189(2) Uani 1 1 d . . . . .
H14 H 0.737033 0.314454 0.383808 0.023 Uiso 1 1 calc R U . . .
C15 C 0.95745(14) 0.42464(13) 0.41706(5) 0.0160(2) Uani 1 1 d . . . . .
C16 C 1.03563(14) 0.57112(13) 0.42484(5) 0.0168(2) Uani 1 1 d . . . . .
H16 H 1.149328 0.578288 0.443314 0.020 Uiso 1 1 calc R U . . .
C17 C 0.94753(14) 0.70584(13) 0.40566(5) 0.0164(2) Uani 1 1 d . . . . .
H17 H 1.001643 0.804997 0.411123 0.020 Uiso 1 1 calc R U . . .
C18 C 0.97568(16) 0.14805(14) 0.43356(6) 0.0240(3) Uani 1 1 d . . . . .
H18A H 0.937422 0.123847 0.389833 0.036 Uiso 1 1 calc R U . . .
H18B H 0.878754 0.148537 0.457511 0.036 Uiso 1 1 calc R U . . .
H18C H 1.056820 0.068347 0.450566 0.036 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 1.2243(14) . ?
O2 C15 1.3652(13) . ?
O2 C18 1.4296(15) . ?
N1 C2 1.3776(14) . ?
N1 C3 1.3894(15) . ?
N1 C7 1.4149(14) . ?
C1 C2 1.4023(16) . ?
C1 C8 1.4313(16) . ?
C1 C10 1.4826(16) . ?
C2 C12 1.4778(15) . ?
C3 C4 1.3536(17) . ?
C4 C5 1.4373(17) . ?
C5 C6 1.3598(17) . ?
C6 C7 1.4246(16) . ?
C7 C8 1.3896(16) . ?
C8 C9 1.5026(16) . ?
C10 C11 1.5093(17) . ?
C12 C13 1.3961(16) . ?
C12 C17 1.4062(16) . ?
C13 C14 1.3955(16) . ?
C14 C15 1.3979(16) . ?
C15 C16 1.3968(16) . ?
C16 C17 1.3843(16) . ?

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 O2 C18 117.17(9) . . ?
C2 N1 C3 129.19(10) . . ?
C2 N1 C7 109.65(9) . . ?
C3 N1 C7 121.16(9) . . ?
C2 C1 C8 108.96(10) . . ?
C2 C1 C10 127.06(10) . . ?
C8 C1 C10 123.93(10) . . ?
N1 C2 C1 106.90(10) . . ?
N1 C2 C12 120.90(10) . . ?
C1 C2 C12 132.07(10) . . ?
C4 C3 N1 119.97(11) . . ?
C3 C4 C5 120.56(11) . . ?
C6 C5 C4 119.87(11) . . ?
C5 C6 C7 120.46(11) . . ?
C8 C7 N1 107.94(9) . . ?
C8 C7 C6 134.09(11) . . ?
N1 C7 C6 117.96(10) . . ?
C7 C8 C1 106.54(10) . . ?
C7 C8 C9 124.32(10) . . ?
C1 C8 C9 129.14(10) . . ?
O1 C10 C1 120.20(11) . . ?
O1 C10 C11 119.23(11) . . ?
C1 C10 C11 120.55(10) . . ?
C13 C12 C17 118.18(10) . . ?
C13 C12 C2 120.57(10) . . ?
C17 C12 C2 121.24(10) . . ?
C14 C13 C12 121.47(10) . . ?
C13 C14 C15 119.25(11) . . ?
O2 C15 C16 115.67(10) . . ?
O2 C15 C14 124.29(10) . . ?
C16 C15 C14 120.03(10) . . ?
C17 C16 C15 120.04(10) . . ?
C16 C17 C12 121.00(10) . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.222
_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_kui1366_21
_database_code_depnum_ccdc_archive 'CCDC 2115160'
loop_
_audit_author_name
_audit_author_address
'Sebastian Dechert'
;Institute of Inorganic Chemistry  Georg August University of Gottingen
Germany
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2023-12-06 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         'C13 H15 N O'
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   7.5190(13)
_cell_length_b                   12.050(2)
_cell_length_c                   11.678(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.317(6)
_cell_angle_gamma                90
_cell_volume                     1041.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    155
_cell_measurement_theta_min      2.4498
_cell_measurement_theta_max      22.1858

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.124
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            31200
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.449
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2483
_reflns_number_gt                1762
_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 Instrument Service vV6.2.10'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0516P)²+0.5691P] 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         2483
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.32576(18) 0.25470(11) 0.65553(11) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.31888(19) 0.59003(13) 0.55837(12) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.2636(2) 0.40909(15) 0.53121(14) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.3477(2) 0.48875(15) 0.61072(14) 0.0229(4) Uani 1 1 d . . . . .
C3 C 0.3715(2) 0.69489(15) 0.60042(15) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.439430 0.703304 0.676750 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3259(2) 0.78529(16) 0.53247(16) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.361634 0.857017 0.561634 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2245(3) 0.77365(16) 0.41736(16) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.194310 0.837314 0.369881 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1715(2) 0.67164(16) 0.37611(16) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.103424 0.664202 0.299709 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2163(2) 0.57628(15) 0.44535(14) 0.0217(4) Uani 1 1 d . . . . .
C8 C 0.1824(2) 0.46483(15) 0.42699(14) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.4520(2) 0.47696(16) 0.73133(15) 0.0274(4) Uani 1 1 d . . . . .
H9A H 0.526483 0.409796 0.736334 0.041 Uiso 1 1 calc R U . . .
H9B H 0.368013 0.471450 0.786291 0.041 Uiso 1 1 calc R U . . .
H9C H 0.530095 0.541897 0.750631 0.041 Uiso 1 1 calc R U . . .
C10 C 0.0738(2) 0.42077(16) 0.31614(15) 0.0291(4) Uani 1 1 d . . . . .
H10A H 0.026617 0.482855 0.265485 0.044 Uiso 1 1 calc R U . . .
H10B H -0.027099 0.376426 0.333861 0.044 Uiso 1 1 calc R U . . .
H10C H 0.150944 0.374219 0.276578 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2649(2) 0.28977(16) 0.55752(15) 0.0255(4) Uani 1 1 d . . . . .
C12 C 0.1886(2) 0.20884(16) 0.46222(15) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.245688 0.222749 0.393496 0.033 Uiso 1 1 calc R U . . .
H12B H 0.057211 0.222398 0.438859 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2183(3) 0.08828(16) 0.49852(16) 0.0338(5) Uani 1 1 d . . . . .
H13A H 0.164897 0.040005 0.433914 0.051 Uiso 1 1 calc R U . . .
H13B H 0.160987 0.073581 0.566029 0.051 Uiso 1 1 calc R U . . .
H13C H 0.348286 0.073443 0.519047 0.051 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 C11 1.229(2) . ?
N1 C2 1.365(2) . ?
N1 C3 1.387(2) . ?
N1 C7 1.414(2) . ?
C1 C2 1.405(2) . ?
C1 C8 1.428(2) . ?
C1 C11 1.470(3) . ?
C2 C9 1.491(2) . ?
C3 C4 1.355(3) . ?
C4 C5 1.429(3) . ?
C5 C6 1.354(3) . ?
C6 C7 1.411(3) . ?
C7 C8 1.377(3) . ?
C8 C10 1.498(2) . ?
C11 C12 1.513(3) . ?
C12 C13 1.519(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
C2 N1 C3 130.06(15) . . ?
C2 N1 C7 109.24(14) . . ?
C3 N1 C7 120.69(15) . . ?
C2 C1 C8 108.36(16) . . ?
C2 C1 C11 123.02(16) . . ?
C8 C1 C11 128.61(16) . . ?
N1 C2 C1 107.37(15) . . ?
N1 C2 C9 121.52(15) . . ?
C1 C2 C9 131.12(16) . . ?
C4 C3 N1 119.91(16) . . ?
C3 C4 C5 120.56(18) . . ?
C6 C5 C4 119.83(17) . . ?
C5 C6 C7 120.72(17) . . ?
C8 C7 C6 133.38(16) . . ?
C8 C7 N1 108.33(15) . . ?
C6 C7 N1 118.28(16) . . ?
C7 C8 C1 106.69(15) . . ?
C7 C8 C10 122.50(16) . . ?
C1 C8 C10 130.79(17) . . ?
O1 C11 C1 121.23(17) . . ?
O1 C11 C12 119.48(17) . . ?
C1 C11 C12 119.29(15) . . ?
C11 C12 C13 113.18(16) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052

