# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_bb340
_database_code_depnum_ccdc_archive 'CCDC 2446156'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;Federal institute for materials research and testing (BAM)
Germany
;
_audit_update_record             
;
2025-10-31 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_audit_creation_date             2025-10-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 Cl N O2'
_chemical_formula_sum            'C12 H10 Cl N O2'
_chemical_formula_weight         235.66
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.959(4)
_cell_length_b                   5.3671(12)
_cell_length_c                   15.422(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.397(10)
_cell_angle_gamma                90
_cell_volume                     1174.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    300
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26958
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.784
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1674
_reflns_number_total             2245
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.1876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.18264(5) 0.97842(13) 0.62576(5) 0.1062(3) Uani 1 1 d . . . . .
O2 O 0.46503(10) 0.1984(3) 0.24441(8) 0.0761(4) Uani 1 1 d . . . . .
O1 O 0.50260(11) 0.0080(3) 0.37995(9) 0.0790(4) Uani 1 1 d . . . . .
N1 N 0.32251(12) 0.6746(3) 0.22476(10) 0.0777(5) Uani 1 1 d . . . . .
C8 C 0.40373(12) 0.3646(3) 0.35271(10) 0.0566(4) Uani 1 1 d . . . . .
C7 C 0.39542(12) 0.3643(3) 0.43682(11) 0.0587(4) Uani 1 1 d . . . . .
H7 H 0.4298 0.2401 0.4750 0.070 Uiso 1 1 calc R U . . .
C9 C 0.35784(13) 0.5386(3) 0.28196(11) 0.0611(5) Uani 1 1 d . . . . .
C10 C 0.46268(13) 0.1706(3) 0.32902(11) 0.0620(4) Uani 1 1 d . . . . .
C5 C 0.24301(15) 0.8724(4) 0.48322(13) 0.0722(5) Uani 1 1 d . . . . .
H5 H 0.2093 1.0122 0.4555 0.087 Uiso 1 1 calc R U . . .
C1 C 0.34238(12) 0.5233(3) 0.47867(11) 0.0577(4) Uani 1 1 d . . . . .
C4 C 0.24438(14) 0.8024(4) 0.56923(13) 0.0704(5) Uani 1 1 d . . . . .
C6 C 0.29203(14) 0.7335(4) 0.43871(12) 0.0674(5) Uani 1 1 d . . . . .
H6 H 0.2915 0.7811 0.3806 0.081 Uiso 1 1 calc R U . . .
C2 C 0.34239(15) 0.4598(4) 0.56639(12) 0.0701(5) Uani 1 1 d . . . . .
H2 H 0.3764 0.3213 0.5950 0.084 Uiso 1 1 calc R U . . .
C3 C 0.29349(17) 0.5968(4) 0.61132(13) 0.0785(6) Uani 1 1 d . . . . .
H3 H 0.2936 0.5509 0.6695 0.094 Uiso 1 1 calc R U . . .
C11 C 0.51749(18) 0.0138(5) 0.21139(15) 0.0884(7) Uani 1 1 d . . . . .
H11A H 0.5844 0.0506 0.2341 0.106 Uiso 1 1 calc R U . . .
H11B H 0.5074 -0.1507 0.2326 0.106 Uiso 1 1 calc R U . . .
C12 C 0.4845(2) 0.0217(6) 0.11227(17) 0.1267(12) Uani 1 1 d . . . . .
H12A H 0.5199 -0.0945 0.0888 0.190 Uiso 1 1 calc R U . . .
H12B H 0.4929 0.1867 0.0920 0.190 Uiso 1 1 calc R U . . .
H12C H 0.4189 -0.0217 0.0904 0.190 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
Cl1 C4 1.736(2) . ?
O2 C10 1.325(2) . ?
O2 C11 1.452(2) . ?
O1 C10 1.200(2) . ?
N1 C9 1.138(2) . ?
C8 C7 1.341(2) . ?
C8 C9 1.436(2) . ?
C8 C10 1.483(3) . ?
C7 H7 0.9300 . ?
C7 C1 1.448(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(3) . ?
C5 C6 1.372(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.395(2) . ?
C4 C3 1.370(3) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.451(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 116.99(15) . . ?
C7 C8 C9 124.59(17) . . ?
C7 C8 C10 118.77(15) . . ?
C9 C8 C10 116.63(15) . . ?
C8 C7 H7 114.3 . . ?
C8 C7 C1 131.39(16) . . ?
C1 C7 H7 114.3 . . ?
N1 C9 C8 178.6(2) . . ?
O2 C10 C8 111.49(15) . . ?
O1 C10 O2 124.35(17) . . ?
O1 C10 C8 124.15(16) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.17(19) . . ?
C6 C1 C7 125.30(15) . . ?
C6 C1 C2 117.58(18) . . ?
C2 C1 C7 117.12(17) . . ?
C5 C4 Cl1 119.22(17) . . ?
C3 C4 Cl1 119.41(15) . . ?
C3 C4 C5 121.37(19) . . ?
C5 C6 C1 121.35(17) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.53(19) . . ?
C3 C2 H2 119.2 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 118.99(18) . . ?
C2 C3 H3 120.5 . . ?
O2 C11 H11A 110.1 . . ?
O2 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 O2 107.9(2) . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Cl1 C4 C3 C2 -179.65(16) . . . . ?
C8 C7 C1 C6 -5.6(3) . . . . ?
C8 C7 C1 C2 174.64(19) . . . . ?
C7 C8 C10 O2 -178.96(16) . . . . ?
C7 C8 C10 O1 1.5(3) . . . . ?
C7 C1 C6 C5 179.45(17) . . . . ?
C7 C1 C2 C3 -179.25(17) . . . . ?
C9 C8 C7 C1 0.3(3) . . . . ?
C9 C8 C10 O2 2.1(2) . . . . ?
C9 C8 C10 O1 -177.38(18) . . . . ?
C10 O2 C11 C12 159.7(2) . . . . ?
C10 C8 C7 C1 -178.56(16) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C5 C4 Cl1 179.82(15) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C11 O2 C10 O1 1.9(3) . . . . ?
C11 O2 C10 C8 -177.60(17) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bb340_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2446157'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;Federal institute for materials research and testing (BAM)
Germany
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2025-11-25 downloaded from the CCDC.
;
_audit_creation_date             2025-11-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 Cl N O2'
_chemical_formula_sum            'C12 H10 Cl N O2'
_chemical_formula_weight         235.66
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.959(4)
_cell_length_b                   5.3671(12)
_cell_length_c                   15.422(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.397(10)
_cell_angle_gamma                90
_cell_volume                     1174.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    400
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16249
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         2.784
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1570
_reflns_number_total             2191
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+0.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C6(H6), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.18268(5) 0.97843(12) 0.62582(5) 0.1064(3) Uani 1 1 d . . . . .
O2 O 0.46506(10) 0.1983(2) 0.24441(8) 0.0760(4) Uani 1 1 d . . . . .
O1 O 0.50263(11) 0.0081(2) 0.37992(9) 0.0791(4) Uani 1 1 d . . . . .
N1 N 0.32250(12) 0.6743(3) 0.22477(10) 0.0778(5) Uani 1 1 d . . . . .
C8 C 0.40362(12) 0.3646(3) 0.35265(10) 0.0567(4) Uani 1 1 d . . . . .
C7 C 0.39550(12) 0.3641(3) 0.43690(10) 0.0591(4) Uani 1 1 d . . . . .
H7 H 0.4300 0.2399 0.4751 0.071 Uiso 1 1 calc R U . . .
C9 C 0.35783(13) 0.5384(3) 0.28206(11) 0.0614(4) Uani 1 1 d . . . . .
C10 C 0.46265(13) 0.1707(3) 0.32898(11) 0.0622(4) Uani 1 1 d . . . . .
C5 C 0.24292(14) 0.8723(4) 0.48315(12) 0.0727(5) Uani 1 1 d . . . . .
H5 H 0.2091 1.0120 0.4554 0.087 Uiso 1 1 calc R U . . .
C1 C 0.34237(12) 0.5232(3) 0.47874(11) 0.0579(4) Uani 1 1 d . . . . .
C4 C 0.24443(14) 0.8026(3) 0.56928(13) 0.0709(5) Uani 1 1 d . . . . .
C6 C 0.29188(14) 0.7337(3) 0.43851(11) 0.0675(5) Uani 1 1 d . . . . .
H6 H 0.2913 0.7813 0.3804 0.081 Uiso 1 1 calc R U . . .
C2 C 0.34247(15) 0.4596(4) 0.56644(11) 0.0700(5) Uani 1 1 d . . . . .
H2 H 0.3765 0.3210 0.5951 0.084 Uiso 1 1 calc R U . . .
C3 C 0.29356(16) 0.5970(4) 0.61135(12) 0.0784(6) Uani 1 1 d . . . . .
H3 H 0.2937 0.5513 0.6696 0.094 Uiso 1 1 calc R U . . .
C11 C 0.51764(18) 0.0140(4) 0.21150(14) 0.0878(6) Uani 1 1 d . . . . .
H11A H 0.5079 -0.1504 0.2330 0.105 Uiso 1 1 calc R U . . .
H11B H 0.5844 0.0517 0.2339 0.105 Uiso 1 1 calc R U . . .
C12 C 0.4840(2) 0.0211(6) 0.11207(17) 0.1275(11) Uani 1 1 d . . . . .
H12A H 0.5185 -0.0973 0.0885 0.191 Uiso 1 1 calc R U . . .
H12B H 0.4930 0.1852 0.0915 0.191 Uiso 1 1 calc R U . . .
H12C H 0.4181 -0.0199 0.0906 0.191 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
Cl1 C4 1.736(2) . ?
O2 C10 1.324(2) . ?
O2 C11 1.451(2) . ?
O1 C10 1.200(2) . ?
N1 C9 1.139(2) . ?
C8 C7 1.343(2) . ?
C8 C9 1.433(2) . ?
C8 C10 1.483(2) . ?
C7 H7 0.9300 . ?
C7 C1 1.450(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(3) . ?
C5 C6 1.372(3) . ?
C1 C6 1.391(2) . ?
C1 C2 1.394(2) . ?
C4 C3 1.370(3) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.456(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 117.01(15) . . ?
C7 C8 C9 124.69(16) . . ?
C7 C8 C10 118.64(14) . . ?
C9 C8 C10 116.66(14) . . ?
C8 C7 H7 114.4 . . ?
C8 C7 C1 131.24(16) . . ?
C1 C7 H7 114.4 . . ?
N1 C9 C8 178.48(19) . . ?
O2 C10 C8 111.54(14) . . ?
O1 C10 O2 124.29(17) . . ?
O1 C10 C8 124.17(15) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.29(18) . . ?
C6 C1 C7 125.21(15) . . ?
C6 C1 C2 117.76(17) . . ?
C2 C1 C7 117.03(16) . . ?
C5 C4 Cl1 119.26(16) . . ?
C3 C4 Cl1 119.41(15) . . ?
C3 C4 C5 121.34(18) . . ?
C5 C6 C1 121.14(16) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.40(18) . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.08(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O2 C11 H11A 110.2 . . ?
O2 C11 H11B 110.2 . . ?
O2 C11 C12 107.75(19) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Cl1 C4 C3 C2 -179.73(15) . . . . ?
C8 C7 C1 C6 -5.7(3) . . . . ?
C8 C7 C1 C2 174.59(18) . . . . ?
C7 C8 C10 O2 -178.88(16) . . . . ?
C7 C8 C10 O1 1.6(3) . . . . ?
C7 C1 C6 C5 179.47(17) . . . . ?
C7 C1 C2 C3 -179.32(16) . . . . ?
C9 C8 C7 C1 0.4(3) . . . . ?
C9 C8 C10 O2 2.1(2) . . . . ?
C9 C8 C10 O1 -177.42(17) . . . . ?
C10 O2 C11 C12 159.3(2) . . . . ?
C10 C8 C7 C1 -178.56(16) . . . . ?
C5 C4 C3 C2 0.4(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C5 C4 Cl1 179.86(14) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C11 O2 C10 O1 1.8(3) . . . . ?
C11 O2 C10 C8 -177.67(16) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
