# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_BB8
_database_code_depnum_ccdc_archive 'CCDC 2131405'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_audit_creation_date             2020-07-08
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl2 N2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O'
_chemical_formula_weight         281.13
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.5261(17)
_cell_length_b                   4.3104(5)
_cell_length_c                   20.361(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.088(5)
_cell_angle_gamma                90
_cell_volume                     1246.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    980
_cell_measurement_temperature    300.91
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      1.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  0.968
_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            Orange
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.755
_diffrn_reflns_theta_min         1.434
_diffrn_ambient_temperature      300.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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                1986
_reflns_number_total             2668
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.020
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1443
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.09181(4) 0.90157(17) 0.31696(3) 0.0591(2) Uani 1 1 d . . . . .
Cl2 Cl 0.46853(4) 0.95655(17) 0.39324(3) 0.0632(2) Uani 1 1 d . . . . .
O1 O 0.10446(10) 0.5120(4) 0.43536(8) 0.0489(4) Uani 1 1 d . . . . .
H1 H 0.111597 0.401719 0.468859 0.073 Uiso 1 1 calc R U . . .
N1 N 0.19470(11) 0.1956(4) 0.53596(8) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.27986(11) -0.1068(4) 0.62542(8) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.18795(13) 0.6073(5) 0.42640(10) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.19423(13) 0.7996(5) 0.37213(9) 0.0384(5) Uani 1 1 d . . . . .
C3 C 0.27893(14) 0.9059(5) 0.36174(10) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.281411 1.033924 0.325390 0.050 Uiso 1 1 calc R U . . .
C4 C 0.36111(14) 0.8196(5) 0.40632(11) 0.0422(5) Uani 1 1 d . . . . .
C5 C 0.35856(14) 0.6311(5) 0.45991(10) 0.0404(5) Uani 1 1 d . . . . .
H5 H 0.414232 0.577266 0.489392 0.048 Uiso 1 1 calc R U . . .
C6 C 0.27249(13) 0.5190(4) 0.47057(10) 0.0349(4) Uani 1 1 d . . . . .
C7 C 0.27170(14) 0.3111(5) 0.52544(10) 0.0380(4) Uani 1 1 d . . . . .
H7 H 0.328293 0.258849 0.554025 0.046 Uiso 1 1 calc R U . . .
C8 C 0.19641(14) -0.0141(5) 0.58968(10) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.11140(15) -0.1145(5) 0.60190(11) 0.0454(5) Uani 1 1 d . . . . .
H9 H 0.054822 -0.046217 0.575579 0.055 Uiso 1 1 calc R U . . .
C10 C 0.11250(15) -0.3176(6) 0.65385(12) 0.0501(6) Uani 1 1 d . . . . .
H10 H 0.056546 -0.390797 0.663452 0.060 Uiso 1 1 calc R U . . .
C11 C 0.19817(17) -0.4115(5) 0.69162(11) 0.0485(5) Uani 1 1 d . . . . .
H11 H 0.200510 -0.547319 0.727417 0.058 Uiso 1 1 calc R U . . .
C12 C 0.28039(14) -0.3028(5) 0.67606(10) 0.0410(5) Uani 1 1 d . . . . .
C13 C 0.37482(17) -0.4062(6) 0.71433(13) 0.0595(6) Uani 1 1 d . . . . .
H13A H 0.405927 -0.523056 0.685208 0.089 Uiso 1 1 calc R U . . .
H13B H 0.366984 -0.533892 0.751397 0.089 Uiso 1 1 calc R U . . .
H13C H 0.412133 -0.227934 0.730924 0.089 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 C2 1.723(2) . ?
Cl2 C4 1.740(2) . ?
O1 H1 0.8200 . ?
O1 C1 1.329(2) . ?
N1 C7 1.283(2) . ?
N1 C8 1.415(3) . ?
N2 C8 1.338(3) . ?
N2 C12 1.332(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.414(3) . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.367(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(3) . ?
C6 C7 1.434(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(3) . ?
C12 C13 1.496(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C1 O1 H1 109.5 . . ?
C7 N1 C8 120.14(17) . . ?
C12 N2 C8 117.93(17) . . ?
O1 C1 C2 120.25(17) . . ?
O1 C1 C6 121.72(18) . . ?
C2 C1 C6 118.03(17) . . ?
C1 C2 Cl1 118.41(15) . . ?
C3 C2 Cl1 119.64(16) . . ?
C3 C2 C1 121.95(18) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.05(19) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Cl2 118.95(16) . . ?
C5 C4 Cl2 119.92(16) . . ?
C5 C4 C3 121.13(18) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.23(18) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C7 121.07(17) . . ?
C5 C6 C1 119.59(19) . . ?
C5 C6 C7 119.33(18) . . ?
N1 C7 C6 121.47(18) . . ?
N1 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 N1 118.59(17) . . ?
N2 C8 C9 123.5(2) . . ?
C9 C8 N1 117.93(18) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.75(19) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
N2 C12 C11 121.87(19) . . ?
N2 C12 C13 116.62(18) . . ?
C11 C12 C13 121.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C2 C3 C4 -179.44(16) . . . . ?
Cl2 C4 C5 C6 -179.71(16) . . . . ?
O1 C1 C2 Cl1 -1.3(3) . . . . ?
O1 C1 C2 C3 179.11(18) . . . . ?
O1 C1 C6 C5 -178.53(17) . . . . ?
O1 C1 C6 C7 2.8(3) . . . . ?
N1 C8 C9 C10 180.00(19) . . . . ?
N2 C8 C9 C10 0.7(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C6 C7 N1 0.7(3) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
C2 C1 C6 C7 -177.13(17) . . . . ?
C2 C3 C4 Cl2 -179.68(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 177.37(18) . . . . ?
C5 C6 C7 N1 -177.98(18) . . . . ?
C6 C1 C2 Cl1 178.61(14) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C7 N1 C8 N2 -5.2(3) . . . . ?
C7 N1 C8 C9 175.43(19) . . . . ?
C8 N1 C7 C6 178.66(17) . . . . ?
C8 N2 C12 C11 0.5(3) . . . . ?
C8 N2 C12 C13 179.01(19) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 N2 0.4(3) . . . . ?
C10 C11 C12 C13 -178.1(2) . . . . ?
C12 N2 C8 N1 179.64(17) . . . . ?
C12 N2 C8 C9 -1.0(3) . . . . ?

_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_BB7
_database_code_depnum_ccdc_archive 'CCDC 2131406'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2023-02-13 downloaded from the CCDC.
;
_audit_creation_date             2021-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H10 Cl2 N2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O'
_chemical_formula_weight         281.13
_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'
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'
Cl Cl 0.1484 0.1585 '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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.3805(11)
_cell_length_b                   4.2807(3)
_cell_length_c                   20.0178(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.319(3)
_cell_angle_gamma                90
_cell_volume                     1208.30(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    980
_cell_measurement_temperature    100.91
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      1.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  0.968
_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            Orange
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Neddle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1562
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13587
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         1.444
_diffrn_ambient_temperature      100.91
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_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                2508
_reflns_number_total             2781
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.112
_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)+(0.0620P)²+1.0228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.09122(3) 0.07844(13) 0.31668(3) 0.01845(18) Uani 1 1 d . . . . .
Cl2 Cl 0.47182(3) 0.01985(13) 0.39189(3) 0.01931(18) Uani 1 1 d . . . . .
O1 O 0.10369(10) 0.4811(4) 0.43544(9) 0.0159(3) Uani 1 1 d . . . . .
H1 H 0.1109 0.6074 0.4682 0.024 Uiso 1 1 calc R U . . .
N1 N 0.19461(12) 0.8050(4) 0.53599(9) 0.0127(4) Uani 1 1 d . . . . .
N2 N 0.28038(12) 1.1122(4) 0.62588(10) 0.0134(4) Uani 1 1 d . . . . .
C1 C 0.18882(14) 0.3821(5) 0.42630(11) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.19449(14) 0.1842(5) 0.37168(11) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.28064(14) 0.0723(5) 0.36093(11) 0.0141(4) Uani 1 1 d . . . . .
H3 H 0.2833 -0.0629 0.3237 0.017 Uiso 1 1 calc R U . . .
C4 C 0.36316(14) 0.1608(5) 0.40541(11) 0.0139(4) Uani 1 1 d . . . . .
C5 C 0.36075(14) 0.3558(5) 0.45959(11) 0.0137(4) Uani 1 1 d . . . . .
H5 H 0.4179 0.4120 0.4897 0.016 Uiso 1 1 calc R U . . .
C6 C 0.27373(14) 0.4712(5) 0.47019(11) 0.0125(4) Uani 1 1 d . . . . .
C7 C 0.27278(14) 0.6864(5) 0.52603(10) 0.0132(4) Uani 1 1 d . . . . .
H7 H 0.3307 0.7402 0.5556 0.016 Uiso 1 1 calc R U . . .
C8 C 0.19667(15) 1.0206(5) 0.58986(11) 0.0124(4) Uani 1 1 d . . . . .
C9 C 0.11000(14) 1.1264(5) 0.60188(12) 0.0150(4) Uani 1 1 d . . . . .
H9 H 0.0520 1.0564 0.5747 0.018 Uiso 1 1 calc R U . . .
C10 C 0.11061(14) 1.3369(5) 0.65457(12) 0.0159(4) Uani 1 1 d . . . . .
H10 H 0.0529 1.4151 0.6643 0.019 Uiso 1 1 calc R U . . .
C11 C 0.19718(15) 1.4311(5) 0.69275(12) 0.0157(4) Uani 1 1 d . . . . .
H11 H 0.1994 1.5736 0.7294 0.019 Uiso 1 1 calc R U . . .
C12 C 0.28075(14) 1.3156(5) 0.67706(11) 0.0136(4) Uani 1 1 d . . . . .
C13 C 0.37631(15) 1.4171(6) 0.71546(12) 0.0186(5) Uani 1 1 d . . . . .
H13A H 0.4147 1.2326 0.7312 0.028 Uiso 1 1 calc R U . . .
H13B H 0.3685 1.5437 0.7548 0.028 Uiso 1 1 calc R U . . .
H13C H 0.4081 1.5413 0.6854 0.028 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 C2 1.727(2) . ?
Cl2 C4 1.745(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.342(2) . ?
N1 C7 1.284(3) . ?
N1 C8 1.415(3) . ?
N2 C8 1.335(3) . ?
N2 C12 1.344(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 C5 1.374(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.451(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(3) . ?
C12 C13 1.501(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C1 O1 H1 109.5 . . ?
C7 N1 C8 119.22(18) . . ?
C8 N2 C12 118.06(17) . . ?
O1 C1 C2 119.53(19) . . ?
O1 C1 C6 122.11(19) . . ?
C2 C1 C6 118.36(18) . . ?
C1 C2 Cl1 118.86(15) . . ?
C3 C2 Cl1 119.62(16) . . ?
C3 C2 C1 121.52(19) . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 Cl2 118.99(16) . . ?
C5 C4 Cl2 119.63(16) . . ?
C5 C4 C3 121.38(18) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 120.94(18) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 C7 119.0(2) . . ?
N1 C7 C6 120.78(19) . . ?
N1 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 C8 N1 119.01(18) . . ?
N2 C8 C9 123.7(2) . . ?
C9 C8 N1 117.32(19) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.63(19) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
N2 C12 C11 121.87(19) . . ?
N2 C12 C13 116.37(18) . . ?
C11 C12 C13 121.75(19) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 C2 C3 C4 179.68(16) . . . . ?
Cl2 C4 C5 C6 179.45(16) . . . . ?
O1 C1 C2 Cl1 1.0(3) . . . . ?
O1 C1 C2 C3 -178.94(19) . . . . ?
O1 C1 C6 C5 178.42(18) . . . . ?
O1 C1 C6 C7 -2.6(3) . . . . ?
N1 C8 C9 C10 179.81(19) . . . . ?
N2 C8 C9 C10 -0.5(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 N1 -1.3(3) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 177.37(19) . . . . ?
C2 C3 C4 Cl2 -179.98(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C4 C5 C6 C7 -177.62(19) . . . . ?
C5 C6 C7 N1 177.73(19) . . . . ?
C6 C1 C2 Cl1 -178.92(15) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C7 N1 C8 N2 4.8(3) . . . . ?
C7 N1 C8 C9 -175.57(19) . . . . ?
C8 N1 C7 C6 -178.32(18) . . . . ?
C8 N2 C12 C11 -0.2(3) . . . . ?
C8 N2 C12 C13 -178.92(19) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 N2 -0.5(3) . . . . ?
C10 C11 C12 C13 178.2(2) . . . . ?
C12 N2 C8 N1 -179.63(18) . . . . ?
C12 N2 C8 C9 0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
