# Supplementary Information (SI) for RSC Advances.
# 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_ISSC218A
_database_code_depnum_ccdc_archive 'CCDC 2284931'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-07-27 deposited with the CCDC.	2025-09-03 downloaded from the CCDC.
;
_publcif_datablock.id            {901f636b-bce7-447d-a1e6-eaac92e6fa2c}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F3 O'
_chemical_formula_weight         250.21

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'
O O 0.0106 0.0060 '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'

_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                   12.821(5)
_cell_length_b                   8.643(3)
_cell_length_c                   10.145(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.224(12)
_cell_angle_gamma                90
_cell_volume                     1112.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2072
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      24.86

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5560
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS; Bruker, 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       '\ f and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11854
_diffrn_reflns_av_unetI/netI     0.0854
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.851
_diffrn_reflns_theta_max         26.996
_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             2426
_reflns_number_gt                1446
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0849P)²+0.0818P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2426
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1218
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1719
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.5883(2) 0.6509(3) 0.8073(3) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.7060(2) 0.6323(3) 0.8296(3) 0.0224(7) Uani 1 1 d . . . . .
C3 C 0.7637(2) 0.7093(3) 0.9350(3) 0.0263(7) Uani 1 1 d . . . . .
H3 H 0.7282 0.7696 0.9931 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8726(2) 0.6998(4) 0.9570(3) 0.0333(8) Uani 1 1 d . . . . .
H4 H 0.9116 0.7527 1.0301 0.040 Uiso 1 1 calc R U . . .
C5 C 0.9244(2) 0.6131(4) 0.8723(3) 0.0341(8) Uani 1 1 d . . . . .
H5 H 0.9992 0.6083 0.8859 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8678(2) 0.5330(4) 0.7674(3) 0.0332(8) Uani 1 1 d . . . . .
H6 H 0.9036 0.4716 0.7103 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7587(2) 0.5426(3) 0.7458(3) 0.0267(7) Uani 1 1 d . . . . .
H7 H 0.7198 0.4879 0.6738 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5280(2) 0.5782(3) 0.6839(3) 0.0218(6) Uani 1 1 d . . . . .
H8A H 0.5520 0.6250 0.6044 0.026 Uiso 1 1 calc R U . . .
H8B H 0.5447 0.4664 0.6836 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4107(2) 0.5974(3) 0.6736(3) 0.0200(6) Uani 1 1 d . . . . .
C10 C 0.3542(2) 0.5224(3) 0.7601(3) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.2466(2) 0.5272(3) 0.7546(3) 0.0250(7) Uani 1 1 d . . . . .
H11 H 0.2115 0.4718 0.8162 0.030 Uiso 1 1 calc R U . . .
C12 C 0.1927(2) 0.6160(3) 0.6559(3) 0.0264(7) Uani 1 1 d . . . . .
C13 C 0.2446(2) 0.6961(3) 0.5681(3) 0.0261(7) Uani 1 1 d . . . . .
C14 C 0.3529(2) 0.6880(3) 0.5759(3) 0.0231(7) Uani 1 1 d . . . . .
H14 H 0.3878 0.7442 0.5147 0.028 Uiso 1 1 calc R U . . .
F1 F 0.40920(12) 0.43267(18) 0.85733(15) 0.0283(5) Uani 1 1 d . . . . .
F2 F 0.08631(12) 0.6245(2) 0.64388(17) 0.0385(5) Uani 1 1 d . . . . .
F3 F 0.18728(13) 0.7816(2) 0.47226(17) 0.0390(5) Uani 1 1 d . . . . .
O1 O 0.54409(15) 0.7252(2) 0.88505(18) 0.0247(5) Uani 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
C1 O1 1.218(3) . ?
C1 C2 1.502(4) . ?
C1 C8 1.511(4) . ?
C2 C3 1.381(4) . ?
C2 C7 1.395(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.502(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.378(4) . ?
C9 C14 1.391(4) . ?
C10 F1 1.369(3) . ?
C10 C11 1.372(4) . ?
C11 C12 1.368(4) . ?
C11 H11 0.9500 . ?
C12 F2 1.354(3) . ?
C12 C13 1.373(4) . ?
C13 F3 1.352(3) . ?
C13 C14 1.381(4) . ?
C14 H14 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
O1 C1 C2 120.6(3) . . ?
O1 C1 C8 121.7(2) . . ?
C2 C1 C8 117.7(2) . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 118.7(2) . . ?
C7 C2 C1 122.2(3) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C1 113.6(2) . . ?
C9 C8 H8A 108.8 . . ?
C1 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C1 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 116.3(2) . . ?
C10 C9 C8 121.1(2) . . ?
C14 C9 C8 122.6(2) . . ?
F1 C10 C11 117.2(2) . . ?
F1 C10 C9 117.5(2) . . ?
C11 C10 C9 125.3(3) . . ?
C12 C11 C10 116.5(3) . . ?
C12 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
F2 C12 C11 119.6(2) . . ?
F2 C12 C13 119.3(3) . . ?
C11 C12 C13 121.1(3) . . ?
F3 C13 C12 118.6(3) . . ?
F3 C13 C14 120.5(2) . . ?
C12 C13 C14 120.9(3) . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.070


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_1ssc_276a
_database_code_depnum_ccdc_archive 'CCDC 2284933'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;
_audit_update_record             
;
2023-07-27 deposited with the CCDC.	2025-09-03 downloaded from the CCDC.
;
_audit_creation_date             2022-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Br F O'
_chemical_formula_sum            'C14 H10 Br F O'
_chemical_formula_weight         293.13
_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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.7831(18)
_cell_length_b                   10.6380(6)
_cell_length_c                   8.1073(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.183(2)
_cell_angle_gamma                90
_cell_volume                     2450.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.347
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0959 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.7595.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            66323
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.867
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1941
_reflns_number_total             2639
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.056
_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)+(0.0421P)²+3.4424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br1 Br 0.05228(2) 0.58587(5) 0.10671(6) 0.1096(3) Uani 1 1 d . . . . .
C1 C 0.29740(10) 0.5989(2) 0.2392(3) 0.0571(6) Uani 1 1 d . . . . .
C2 C 0.34875(10) 0.6139(2) 0.2938(3) 0.0555(6) Uani 1 1 d . . . . .
C3 C 0.37901(11) 0.5258(3) 0.2424(4) 0.0687(8) Uani 1 1 d . . . . .
H3 H 0.366672 0.459903 0.173599 0.082 Uiso 1 1 calc R U . . .
C4 C 0.42680(13) 0.5342(4) 0.2913(5) 0.0832(9) Uani 1 1 d . . . . .
H4 H 0.446871 0.474056 0.258112 0.100 Uiso 1 1 calc R U . . .
C5 C 0.44411(12) 0.6324(4) 0.3893(5) 0.0823(10) Uani 1 1 d . . . . .
C6 C 0.41604(13) 0.7222(3) 0.4435(5) 0.0811(9) Uani 1 1 d . . . . .
H6 H 0.429021 0.788313 0.510502 0.097 Uiso 1 1 calc R U . . .
C7 C 0.36811(11) 0.7121(3) 0.3962(4) 0.0680(7) Uani 1 1 d . . . . .
H7 H 0.348385 0.771537 0.433020 0.082 Uiso 1 1 calc R U . . .
C8 C 0.26465(11) 0.6833(3) 0.3163(4) 0.0655(7) Uani 1 1 d . . . . .
H8A H 0.271694 0.674545 0.436850 0.079 Uiso 1 1 calc R U . . .
H8B H 0.271083 0.769722 0.289407 0.079 Uiso 1 1 calc R U . . .
C9 C 0.21316(10) 0.6582(3) 0.2619(3) 0.0573(6) Uani 1 1 d . . . . .
C10 C 0.19145(11) 0.5578(3) 0.3257(4) 0.0628(7) Uani 1 1 d . . . . .
H10 H 0.209202 0.504272 0.401782 0.075 Uiso 1 1 calc R U . . .
C11 C 0.14403(11) 0.5351(3) 0.2792(4) 0.0659(7) Uani 1 1 d . . . . .
H11 H 0.130036 0.466396 0.322589 0.079 Uiso 1 1 calc R U . . .
C12 C 0.11761(11) 0.6147(3) 0.1684(4) 0.0663(7) Uani 1 1 d . . . . .
C13 C 0.13813(13) 0.7151(3) 0.1010(4) 0.0755(9) Uani 1 1 d . . . . .
H13 H 0.120210 0.768064 0.024613 0.091 Uiso 1 1 calc R U . . .
C14 C 0.18548(12) 0.7362(3) 0.1483(4) 0.0696(8) Uani 1 1 d . . . . .
H14 H 0.199388 0.804299 0.103213 0.084 Uiso 1 1 calc R U . . .
F1 F 0.49116(8) 0.6401(3) 0.4398(4) 0.1221(9) Uani 1 1 d . . . . .
O1 O 0.28231(8) 0.5187(2) 0.1388(3) 0.0860(7) Uani 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
Br1 C12 1.892(3) . ?
C1 C2 1.483(4) . ?
C1 C8 1.508(4) . ?
C1 O1 1.210(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(5) . ?
C5 C6 1.368(5) . ?
C5 F1 1.353(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.501(4) . ?
C9 C10 1.379(4) . ?
C9 C14 1.392(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(4) . ?
C12 C13 1.375(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.374(5) . ?
C14 H14 0.9300 . ?

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 C1 C8 118.1(2) . . ?
O1 C1 C2 120.7(3) . . ?
O1 C1 C8 121.2(3) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 C7 118.4(3) . . ?
C7 C2 C1 122.9(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 123.0(3) . . ?
F1 C5 C4 118.6(4) . . ?
F1 C5 C6 118.3(3) . . ?
C5 C6 H6 120.9 . . ?
C5 C6 C7 118.3(3) . . ?
C7 C6 H6 120.9 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C1 C8 H8A 108.5 . . ?
C1 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C1 115.2(2) . . ?
C9 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 C14 117.7(3) . . ?
C14 C9 C8 121.5(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 Br1 119.7(3) . . ?
C11 C12 C13 120.7(3) . . ?
C13 C12 Br1 119.5(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.6(3) . . ?
C13 C14 H14 119.2 . . ?

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
Br1 C12 C13 C14 179.2(2) . . . . ?
C1 C2 C3 C4 -179.0(3) . . . . ?
C1 C2 C7 C6 -179.9(3) . . . . ?
C1 C8 C9 C10 77.2(3) . . . . ?
C1 C8 C9 C14 -104.1(3) . . . . ?
C2 C1 C8 C9 -176.9(2) . . . . ?
C2 C3 C4 C5 -1.2(5) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C3 C4 C5 F1 179.1(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 C2 -0.9(5) . . . . ?
C7 C2 C3 C4 0.3(5) . . . . ?
C8 C1 C2 C3 170.9(3) . . . . ?
C8 C1 C2 C7 -8.4(4) . . . . ?
C8 C9 C10 C11 178.8(3) . . . . ?
C8 C9 C14 C13 -178.5(3) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C10 C11 C12 Br1 -178.9(2) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C9 0.3(5) . . . . ?
C14 C9 C10 C11 -0.1(4) . . . . ?
F1 C5 C6 C7 -178.0(3) . . . . ?
O1 C1 C2 C3 -7.1(4) . . . . ?
O1 C1 C2 C7 173.6(3) . . . . ?
O1 C1 C8 C9 1.1(4) . . . . ?

_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_issc_270a
_database_code_depnum_ccdc_archive 'CCDC 2284932'
loop_
_audit_author_name
_audit_author_address
'Gamidi Rama Krishna '
;CSIR National Chemical Laboratory Pune
India
;

_audit_update_record             
;
2023-07-27 deposited with the CCDC.	2025-09-03 downloaded from the CCDC.
;
_publcif_datablock.id            {78c6b92f-8a6a-4745-b690-4f46bdc118df}

# publcif _publ_body_element loop end
_audit_creation_date             2022-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 Cl3 O'
_chemical_formula_sum            'C14 H9 Cl3 O'
_chemical_formula_weight         299.56
_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'
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           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                   11.9460(3)
_cell_length_b                   8.9801(2)
_cell_length_c                   12.6848(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.6830(10)
_cell_angle_gamma                90
_cell_volume                     1341.39(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6427
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1234 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            65556
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.793
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2632
_reflns_number_total             2831
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.062
_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)+(0.0451P)²+0.5074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.46937(12) 0.65392(17) 0.10093(12) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.48755(14) 0.75320(18) 0.02163(12) 0.0463(4) Uani 1 1 d . . . . .
H2 H 0.545898 0.822795 0.034527 0.056 Uiso 1 1 calc R U . . .
C3 C 0.41768(15) 0.74696(19) -0.07657(13) 0.0496(4) Uani 1 1 d . . . . .
C4 C 0.32950(14) 0.64610(19) -0.09835(13) 0.0503(4) Uani 1 1 d . . . . .
H4 H 0.282359 0.644319 -0.164622 0.060 Uiso 1 1 calc R U . . .
C5 C 0.31391(13) 0.54858(19) -0.01871(13) 0.0473(4) Uani 1 1 d . . . . .
C6 C 0.38248(13) 0.54983(18) 0.08057(12) 0.0447(3) Uani 1 1 d . . . . .
H6 H 0.370595 0.481959 0.132961 0.054 Uiso 1 1 calc R U . . .
C7 C 0.54492(13) 0.66455(19) 0.20790(12) 0.0453(3) Uani 1 1 d . . . . .
C8 C 0.51970(15) 0.5627(2) 0.29576(13) 0.0521(4) Uani 1 1 d . . . . .
H8A H 0.440006 0.572601 0.301159 0.062 Uiso 1 1 calc R U . . .
H8B H 0.531984 0.460665 0.275270 0.062 Uiso 1 1 calc R U . . .
C9 C 0.58911(14) 0.59031(19) 0.40441(12) 0.0474(4) Uani 1 1 d . . . . .
C10 C 0.56071(17) 0.7033(2) 0.46833(15) 0.0603(4) Uani 1 1 d . . . . .
H10 H 0.500764 0.766469 0.442237 0.072 Uiso 1 1 calc R U . . .
C11 C 0.6199(2) 0.7244(3) 0.57087(17) 0.0749(6) Uani 1 1 d . . . . .
H11 H 0.600300 0.801135 0.613522 0.090 Uiso 1 1 calc R U . . .
C12 C 0.70779(19) 0.6303(3) 0.60828(14) 0.0718(7) Uani 1 1 d . . . . .
C13 C 0.73879(17) 0.5193(3) 0.54705(17) 0.0739(6) Uani 1 1 d . . . . .
H13 H 0.799244 0.457059 0.573544 0.089 Uiso 1 1 calc R U . . .
C14 C 0.67942(16) 0.4994(2) 0.44448(15) 0.0601(5) Uani 1 1 d . . . . .
H14 H 0.700733 0.423645 0.401943 0.072 Uiso 1 1 calc R U . . .
Cl1 Cl 0.43988(6) 0.87072(7) -0.17603(4) 0.0822(2) Uani 1 1 d . . . . .
Cl2 Cl 0.20443(5) 0.41933(7) -0.04249(4) 0.0749(2) Uani 1 1 d . . . . .
Cl3 Cl 0.77987(7) 0.65251(12) 0.73909(4) 0.1226(5) Uani 1.000(3) 1 d . . . . .
O1 O 0.62207(12) 0.75255(18) 0.22155(11) 0.0734(4) Uani 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
C1 C2 1.388(2) . ?
C1 C6 1.388(2) . ?
C1 C7 1.501(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(2) . ?
C3 C4 1.381(2) . ?
C3 Cl1 1.7350(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(2) . ?
C5 C6 1.382(2) . ?
C5 Cl2 1.7366(17) . ?
C6 H6 0.9300 . ?
C7 C8 1.511(2) . ?
C7 O1 1.204(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.505(2) . ?
C9 C10 1.376(3) . ?
C9 C14 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(4) . ?
C12 C13 1.353(4) . ?
C12 Cl3 1.7475(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?

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 C1 C6 120.05(14) . . ?
C2 C1 C7 118.08(13) . . ?
C6 C1 C7 121.87(14) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.93(15) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 122.18(15) . . ?
C2 C3 Cl1 119.18(14) . . ?
C4 C3 Cl1 118.64(12) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.66(14) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 122.16(15) . . ?
C4 C5 Cl2 119.33(12) . . ?
C6 C5 Cl2 118.51(13) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.01(15) . . ?
C5 C6 H6 120.5 . . ?
C1 C7 C8 117.65(13) . . ?
O1 C7 C1 120.07(14) . . ?
O1 C7 C8 122.28(14) . . ?
C7 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C7 115.35(13) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C10 C9 C8 120.58(16) . . ?
C10 C9 C14 118.29(17) . . ?
C14 C9 C8 121.06(17) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 Cl3 119.0(2) . . ?
C13 C12 C11 121.59(18) . . ?
C13 C12 Cl3 119.36(19) . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 C13 121.0(2) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?

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
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 Cl1 179.99(12) . . . . ?
C1 C7 C8 C9 -173.12(15) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C7 C8 176.17(15) . . . . ?
C2 C1 C7 O1 -3.5(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 Cl2 -179.80(12) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C7 C8 -3.1(2) . . . . ?
C6 C1 C7 O1 177.29(17) . . . . ?
C7 C1 C2 C3 -178.83(14) . . . . ?
C7 C1 C6 C5 178.21(14) . . . . ?
C7 C8 C9 C10 80.4(2) . . . . ?
C7 C8 C9 C14 -102.56(19) . . . . ?
C8 C9 C10 C11 176.24(17) . . . . ?
C8 C9 C14 C13 -175.94(17) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C10 C11 C12 Cl3 -177.93(15) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
Cl1 C3 C4 C5 179.60(12) . . . . ?
Cl2 C5 C6 C1 -179.19(12) . . . . ?
Cl3 C12 C13 C14 178.19(15) . . . . ?
O1 C7 C8 C9 6.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



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