# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_bud_ks_a_57_fr8_16_0m
_database_code_depnum_ccdc_archive 'CCDC 2336800'
loop_
_audit_author_name
_audit_author_address
'Kamil Ivshin'
;Arbuzov Institute of Organic and Physical Chemistry
Russia
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-08-21 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         'C9 H8 F3 N O'
_chemical_formula_sum            'C9 H8 F3 N O'
_chemical_formula_weight         203.16

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.7728(4)
_cell_length_b                   13.3728(12)
_cell_length_c                   13.9438(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.480(3)
_cell_angle_gamma                90
_cell_volume                     889.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    8968
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.57

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7012
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32558
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.111
_diffrn_reflns_theta_max         28.739
_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             2312
_reflns_number_gt                1931
_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       'APEX3 v2018.1-0'
_computing_cell_refinement       'APEX3 v2018.1-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 2020.1'
_computing_publication_material  'enCIFer 2020.1'
_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)+(0.0355P)²+0.3978P] 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         2312
_refine_ls_number_parameters     132
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
F001 F 0.09883(16) 0.20905(6) 0.60795(6) 0.02387(19) Uani 1 1 d . . . . .
F002 F 0.49414(17) 0.15205(6) 0.66147(6) 0.0269(2) Uani 1 1 d . . . . .
F003 F 0.2807(2) 0.08156(6) 0.54072(7) 0.0371(2) Uani 1 1 d . . . . .
O004 O 0.91155(18) 0.42127(7) 0.68432(7) 0.0231(2) Uani 1 1 d . . . . .
N005 N 0.4751(2) 0.37655(7) 0.62972(7) 0.0145(2) Uani 1 1 d D . . . .
H005 H 0.299(3) 0.3789(12) 0.6413(11) 0.023(4) Uiso 1 1 d D . . . .
C006 C 0.6572(2) 0.42078(9) 0.69378(9) 0.0159(2) Uani 1 1 d . . . . .
C007 C 0.5613(2) 0.33571(9) 0.54132(8) 0.0144(2) Uani 1 1 d . . . . .
C008 C 0.4925(3) 0.23802(9) 0.51383(8) 0.0158(2) Uani 1 1 d . . . . .
C009 C 0.7169(3) 0.39462(9) 0.48076(9) 0.0181(2) Uani 1 1 d . . . . .
H009 H 0.765827 0.460979 0.499152 0.022 Uiso 1 1 calc R U . . .
C00A C 0.3412(3) 0.17059(9) 0.58010(9) 0.0183(3) Uani 1 1 d . . . . .
C00B C 0.5295(3) 0.47046(10) 0.77823(9) 0.0207(3) Uani 1 1 d . . . . .
H00A H 0.598879 0.438062 0.837659 0.031 Uiso 1 1 calc R U . . .
H00B H 0.324872 0.464348 0.772309 0.031 Uiso 1 1 calc R U . . .
H00C H 0.581565 0.541350 0.779743 0.031 Uiso 1 1 calc R U . . .
C00C C 0.5757(3) 0.20120(10) 0.42604(9) 0.0215(3) Uani 1 1 d . . . . .
H00D H 0.527737 0.134875 0.407237 0.026 Uiso 1 1 calc R U . . .
C00D C 0.8010(3) 0.35719(10) 0.39384(9) 0.0233(3) Uani 1 1 d . . . . .
H00E H 0.908877 0.397646 0.353302 0.028 Uiso 1 1 calc R U . . .
C00E C 0.7280(3) 0.26092(10) 0.36605(9) 0.0255(3) Uani 1 1 d . . . . .
H00F H 0.782365 0.235845 0.305885 0.031 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
F001 C00A 1.3388(14) . ?
F002 C00A 1.3452(15) . ?
F003 C00A 1.3374(14) . ?
O004 C006 1.2270(15) . ?
N005 C006 1.3549(16) . ?
N005 C007 1.4251(15) . ?
N005 H005 0.865(13) . ?
C006 C00B 1.5036(17) . ?
C007 C009 1.3928(16) . ?
C007 C008 1.3965(16) . ?
C008 C00C 1.3931(17) . ?
C008 C00A 1.4987(16) . ?
C009 C00D 1.3867(17) . ?
C009 H009 0.9500 . ?
C00B H00A 0.9800 . ?
C00B H00B 0.9800 . ?
C00B H00C 0.9800 . ?
C00C C00E 1.3852(18) . ?
C00C H00D 0.9500 . ?
C00D C00E 1.3846(19) . ?
C00D H00E 0.9500 . ?
C00E H00F 0.9500 . ?

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
C006 N005 C007 122.46(10) . . ?
C006 N005 H005 117.6(11) . . ?
C007 N005 H005 119.7(11) . . ?
O004 C006 N005 122.74(11) . . ?
O004 C006 C00B 121.21(11) . . ?
N005 C006 C00B 116.04(10) . . ?
C009 C007 C008 119.20(11) . . ?
C009 C007 N005 119.28(10) . . ?
C008 C007 N005 121.52(10) . . ?
C00C C008 C007 119.95(11) . . ?
C00C C008 C00A 119.50(11) . . ?
C007 C008 C00A 120.49(10) . . ?
C00D C009 C007 120.52(12) . . ?
C00D C009 H009 119.7 . . ?
C007 C009 H009 119.7 . . ?
F003 C00A F001 106.68(10) . . ?
F003 C00A F002 106.37(10) . . ?
F001 C00A F002 105.68(10) . . ?
F003 C00A C008 112.56(10) . . ?
F001 C00A C008 113.14(10) . . ?
F002 C00A C008 111.89(10) . . ?
C006 C00B H00A 109.5 . . ?
C006 C00B H00B 109.5 . . ?
H00A C00B H00B 109.5 . . ?
C006 C00B H00C 109.5 . . ?
H00A C00B H00C 109.5 . . ?
H00B C00B H00C 109.5 . . ?
C00E C00C C008 120.25(12) . . ?
C00E C00C H00D 119.9 . . ?
C008 C00C H00D 119.9 . . ?
C00E C00D C009 120.09(12) . . ?
C00E C00D H00E 120.0 . . ?
C009 C00D H00E 120.0 . . ?
C00D C00E C00C 119.96(12) . . ?
C00D C00E H00F 120.0 . . ?
C00C C00E H00F 120.0 . . ?

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
C007 N005 C006 O004 -6.44(18) . . . . ?
C007 N005 C006 C00B 173.29(11) . . . . ?
C006 N005 C007 C009 -51.97(16) . . . . ?
C006 N005 C007 C008 128.24(13) . . . . ?
C009 C007 C008 C00C -1.02(18) . . . . ?
N005 C007 C008 C00C 178.77(11) . . . . ?
C009 C007 C008 C00A 176.08(11) . . . . ?
N005 C007 C008 C00A -4.13(18) . . . . ?
C008 C007 C009 C00D 0.49(18) . . . . ?
N005 C007 C009 C00D -179.31(11) . . . . ?
C00C C008 C00A F003 -5.79(17) . . . . ?
C007 C008 C00A F003 177.09(11) . . . . ?
C00C C008 C00A F001 -126.83(12) . . . . ?
C007 C008 C00A F001 56.06(15) . . . . ?
C00C C008 C00A F002 113.93(13) . . . . ?
C007 C008 C00A F002 -63.19(15) . . . . ?
C007 C008 C00C C00E 0.4(2) . . . . ?
C00A C008 C00C C00E -176.73(12) . . . . ?
C007 C009 C00D C00E 0.7(2) . . . . ?
C009 C00D C00E C00C -1.3(2) . . . . ?
C008 C00C C00E C00D 0.8(2) . . . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_ks_55_t5
_database_code_depnum_ccdc_archive 'CCDC 2336823'
loop_
_audit_author_name
_audit_author_address
'Kamil Ivshin'
;Arbuzov Institute of Organic and Physical Chemistry
Russia
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-08-21 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         'C9 H9 Cl N2 O3'
_chemical_formula_sum            'C9 H9 Cl N2 O3'
_chemical_formula_weight         228.63

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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.8609(7)
_cell_length_b                   4.8745(5)
_cell_length_c                   17.4671(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.312(4)
_cell_angle_gamma                90
_cell_volume                     498.18(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    4804
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.75

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.623
_exptl_crystal_size_mid          0.488
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.371
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.570774
_exptl_absorpt_correction_T_max  0.745757
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2686
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         28.806
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2686
_reflns_number_gt                2574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.888
_reflns_Friedel_fraction_full    0.971

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 v2018.1-0'
_computing_cell_refinement       'APEX3 v2018.1-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury 2020.1'
_computing_publication_material  'enCIFer 2020.1'
_refine_special_details          
;
 Refined as a 2-component twin
 Twin fractions are equal to 0.67/0.33
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0951P)²+0.2512P] 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 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1426
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cl1 Cl -0.0365(3) 0.0291(3) 0.23223(8) 0.0196(3) Uani 1 1 d . . . . .
O1 O 0.6123(8) 0.9574(9) 0.4128(2) 0.0225(10) Uani 1 1 d . . . . .
O2 O 0.3206(7) 0.9706(9) 0.4839(2) 0.0210(9) Uani 1 1 d . . . . .
O3 O 0.4958(8) 0.7369(8) 0.1584(2) 0.0223(10) Uani 1 1 d . . . . .
N1 N 0.4210(8) 0.8811(9) 0.4288(3) 0.0157(11) Uani 1 1 d . . . . .
N7 N 0.4032(9) 0.3095(9) 0.1990(3) 0.0137(10) Uani 1 1 d . . . . .
C1 C 0.4122(9) 0.5910(10) 0.3146(3) 0.0118(11) Uani 1 1 d . . . . .
H1 H 0.553270 0.670073 0.301931 0.014 Uiso 1 1 calc R U . . .
C2 C 0.3068(10) 0.6690(11) 0.3807(3) 0.0125(11) Uani 1 1 d . . . . .
C3 C 0.1052(10) 0.5597(13) 0.4027(3) 0.0178(12) Uani 1 1 d . . . . .
H3 H 0.038102 0.620440 0.447961 0.021 Uiso 1 1 calc R U . . .
C4 C 0.0021(10) 0.3567(11) 0.3565(3) 0.0167(12) Uani 1 1 d . . . . .
H4 H -0.135467 0.272866 0.370848 0.020 Uiso 1 1 calc R U . . .
C5 C 0.1002(10) 0.2769(11) 0.2896(3) 0.0155(11) Uani 1 1 d . . . . .
C6 C 0.3047(10) 0.3943(10) 0.2678(3) 0.0125(11) Uani 1 1 d . . . . .
C8 C 0.4955(10) 0.4867(11) 0.1497(3) 0.0150(11) Uani 1 1 d . . . . .
C9 C 0.5956(12) 0.3592(11) 0.0804(3) 0.0209(13) Uani 1 1 d . . . . .
H9A H 0.485449 0.379250 0.035621 0.025 Uiso 1 1 calc R U . . .
H9B H 0.619192 0.160625 0.089815 0.025 Uiso 1 1 calc R U . . .
C10 C 0.8224(12) 0.4893(17) 0.0618(4) 0.0317(17) Uani 1 1 d . . . . .
H10A H 0.942034 0.431256 0.099876 0.048 Uiso 1 1 calc R U . . .
H10B H 0.808047 0.689558 0.062875 0.048 Uiso 1 1 calc R U . . .
H10C H 0.862897 0.430759 0.010641 0.048 Uiso 1 1 calc R U . . .
H7 H 0.397(10) 0.140(13) 0.188(4) 0.011(16) 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
Cl1 C5 1.735(6) . ?
O1 N1 1.229(7) . ?
O2 N1 1.236(6) . ?
O3 C8 1.229(7) . ?
N1 C2 1.469(7) . ?
N7 C8 1.354(7) . ?
N7 C6 1.425(7) . ?
N7 H7 0.85(7) . ?
C1 C6 1.387(7) . ?
C1 C2 1.394(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(8) . ?
C3 C4 1.392(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(8) . ?
C8 C9 1.509(8) . ?
C9 C10 1.525(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O1 N1 O2 123.6(5) . . ?
O1 N1 C2 118.3(5) . . ?
O2 N1 C2 118.1(5) . . ?
C8 N7 C6 123.2(5) . . ?
C8 N7 H7 120(4) . . ?
C6 N7 H7 117(4) . . ?
C6 C1 C2 117.9(5) . . ?
C6 C1 H1 121.0 . . ?
C2 C1 H1 121.0 . . ?
C3 C2 C1 123.8(5) . . ?
C3 C2 N1 119.0(5) . . ?
C1 C2 N1 117.2(5) . . ?
C2 C3 C4 117.8(5) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 Cl1 118.8(5) . . ?
C6 C5 Cl1 120.1(5) . . ?
C1 C6 C5 119.3(5) . . ?
C1 C6 N7 120.3(5) . . ?
C5 C6 N7 120.4(5) . . ?
O3 C8 N7 123.5(5) . . ?
O3 C8 C9 120.7(5) . . ?
N7 C8 C9 115.8(5) . . ?
C8 C9 C10 112.6(5) . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C6 C1 C2 C3 1.0(8) . . . . ?
C6 C1 C2 N1 -178.9(4) . . . . ?
O1 N1 C2 C3 172.8(5) . . . . ?
O2 N1 C2 C3 -6.3(8) . . . . ?
O1 N1 C2 C1 -7.3(7) . . . . ?
O2 N1 C2 C1 173.6(5) . . . . ?
C1 C2 C3 C4 0.8(9) . . . . ?
N1 C2 C3 C4 -179.3(5) . . . . ?
C2 C3 C4 C5 -1.8(9) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C3 C4 C5 Cl1 -178.5(4) . . . . ?
C2 C1 C6 C5 -1.8(8) . . . . ?
C2 C1 C6 N7 179.2(5) . . . . ?
C4 C5 C6 C1 0.9(8) . . . . ?
Cl1 C5 C6 C1 -179.7(4) . . . . ?
C4 C5 C6 N7 179.9(5) . . . . ?
Cl1 C5 C6 N7 -0.7(7) . . . . ?
C8 N7 C6 C1 -43.1(8) . . . . ?
C8 N7 C6 C5 137.9(6) . . . . ?
C6 N7 C8 O3 -2.5(9) . . . . ?
C6 N7 C8 C9 179.0(5) . . . . ?
O3 C8 C9 C10 43.4(8) . . . . ?
N7 C8 C9 C10 -138.1(6) . . . . ?

_refine_diff_density_max         0.602
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.088



