# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc206hc3
_database_code_depnum_ccdc_archive 'CCDC 1853284'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2018-07-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C18 H12 F3 N O4'
_chemical_formula_weight         363.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.104(3)
_cell_length_b                   8.342(3)
_cell_length_c                   12.247(4)
_cell_angle_alpha                90.274(13)
_cell_angle_beta                 90.434(16)
_cell_angle_gamma                110.909(15)
_cell_volume                     773.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2584
_cell_measurement_theta_min      3.009
_cell_measurement_theta_max      27.465

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4502
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.009
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3440
_reflns_number_gt                2584
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0834P)²+0.0947P] 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         3440
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.6448(2) 0.3267(2) 0.39888(14) 0.0427(4) Uani 1 1 d . . . . .
H1 H 0.5575 0.2209 0.3836 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7596(2) 0.4096(2) 0.31919(14) 0.0414(4) Uani 1 1 d . . . . .
H2 H 0.7493 0.3593 0.2503 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8930(2) 0.5695(2) 0.33899(13) 0.0345(3) Uani 1 1 d . . . . .
C4 C 1.0223(2) 0.6675(2) 0.26184(13) 0.0366(4) Uani 1 1 d . . . . .
C5 C 1.0188(2) 0.6006(2) 0.14731(14) 0.0437(4) Uani 1 1 d . . . . .
F6 F 1.02910(16) 0.44511(14) 0.14562(9) 0.0586(3) Uani 1 1 d . . . . .
F7 F 1.15109(17) 0.70058(15) 0.08792(9) 0.0643(4) Uani 1 1 d . . . . .
F8 F 0.86904(16) 0.58619(19) 0.09557(9) 0.0694(4) Uani 1 1 d . . . . .
C9 C 1.1443(2) 0.8185(2) 0.29023(14) 0.0421(4) Uani 1 1 d . . . . .
H9 H 1.2252 0.8806 0.2386 0.051 Uiso 1 1 calc R U . . .
C10 C 1.1530(2) 0.8871(2) 0.39940(15) 0.0424(4) Uani 1 1 d . . . . .
O11 O 1.26180(18) 1.02001(18) 0.43193(12) 0.0623(4) Uani 1 1 d . . . . .
O12 O 1.02902(15) 0.79433(15) 0.47159(9) 0.0406(3) Uani 1 1 d . . . . .
C13 C 0.90122(19) 0.63833(19) 0.44378(13) 0.0335(3) Uani 1 1 d . . . . .
C14 C 0.7861(2) 0.5578(2) 0.52596(13) 0.0364(4) Uani 1 1 d . . . . .
H14 H 0.7948 0.6087 0.5945 0.044 Uiso 1 1 calc R U . . .
C15 C 0.6568(2) 0.3989(2) 0.50348(13) 0.0362(4) Uani 1 1 d . . . . .
N16 N 0.53508(19) 0.30163(19) 0.58037(12) 0.0404(3) Uani 1 1 d . . . . .
H16 H 0.457(3) 0.210(3) 0.5532(16) 0.048 Uiso 1 1 d . U . . .
C17 C 0.5270(2) 0.3355(2) 0.68899(14) 0.0400(4) Uani 1 1 d . . . . .
O18 O 0.62892(18) 0.46506(18) 0.73228(11) 0.0564(4) Uani 1 1 d . . . . .
C19 C 0.3899(2) 0.2007(2) 0.75267(14) 0.0389(4) Uani 1 1 d . . . . .
C20 C 0.2500(2) 0.0683(2) 0.70609(15) 0.0443(4) Uani 1 1 d . . . . .
H20 H 0.2383 0.0571 0.6306 0.053 Uiso 1 1 calc R U . . .
C21 C 0.1275(2) -0.0474(2) 0.77280(16) 0.0487(4) Uani 1 1 d . . . . .
H21 H 0.0326 -0.1352 0.7416 0.058 Uiso 1 1 calc R U . . .
C22 C 0.1446(3) -0.0342(2) 0.88439(16) 0.0500(5) Uani 1 1 d . . . . .
H22 H 0.0620 -0.1129 0.9284 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2856(3) 0.0972(2) 0.93126(14) 0.0478(4) Uani 1 1 d . . . . .
C24 C 0.4077(2) 0.2148(2) 0.86560(14) 0.0444(4) Uani 1 1 d . . . . .
H24 H 0.5017 0.3032 0.8971 0.053 Uiso 1 1 calc R U . . .
O25 O 0.2911(2) 0.1001(2) 1.04254(11) 0.0702(5) Uani 1 1 d . . . . .
C26 C 0.4256(4) 0.2360(4) 1.0955(2) 0.1039(12) Uani 1 1 d . . . . .
H26A H 0.5389 0.2363 1.0731 0.156 Uiso 1 1 calc R U . . .
H26B H 0.4148 0.2210 1.1731 0.156 Uiso 1 1 calc R U . . .
H26C H 0.4143 0.3431 1.0763 0.156 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
C1 C2 1.363(2) . ?
C1 C15 1.401(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.403(2) . ?
C2 H2 0.9300 . ?
C3 C13 1.395(2) . ?
C3 C4 1.439(2) . ?
C4 C9 1.336(2) . ?
C4 C5 1.503(2) . ?
C5 F7 1.324(2) . ?
C5 F6 1.329(2) . ?
C5 F8 1.331(2) . ?
C9 C10 1.443(2) . ?
C9 H9 0.9300 . ?
C10 O11 1.208(2) . ?
C10 O12 1.362(2) . ?
O12 C13 1.3822(18) . ?
C13 C14 1.381(2) . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C15 N16 1.403(2) . ?
N16 C17 1.365(2) . ?
N16 H16 0.86(2) . ?
C17 O18 1.218(2) . ?
C17 C19 1.496(2) . ?
C19 C20 1.386(2) . ?
C19 C24 1.389(2) . ?
C20 C21 1.385(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(3) . ?
C22 H22 0.9300 . ?
C23 O25 1.363(2) . ?
C23 C24 1.384(2) . ?
C24 H24 0.9300 . ?
O25 C26 1.412(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C2 C1 C15 120.79(15) . . ?
C2 C1 H1 119.6 . . ?
C15 C1 H1 119.6 . . ?
C1 C2 C3 121.30(15) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.4 . . ?
C13 C3 C2 116.59(14) . . ?
C13 C3 C4 117.26(14) . . ?
C2 C3 C4 126.14(15) . . ?
C9 C4 C3 120.86(15) . . ?
C9 C4 C5 119.49(15) . . ?
C3 C4 C5 119.64(14) . . ?
F7 C5 F6 106.82(15) . . ?
F7 C5 F8 107.60(15) . . ?
F6 C5 F8 106.22(15) . . ?
F7 C5 C4 112.47(14) . . ?
F6 C5 C4 111.91(14) . . ?
F8 C5 C4 111.46(15) . . ?
C4 C9 C10 121.32(15) . . ?
C4 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
O11 C10 O12 117.38(16) . . ?
O11 C10 C9 125.18(16) . . ?
O12 C10 C9 117.43(14) . . ?
C10 O12 C13 122.16(13) . . ?
C14 C13 O12 115.65(14) . . ?
C14 C13 C3 123.41(14) . . ?
O12 C13 C3 120.94(14) . . ?
C13 C14 C15 118.29(15) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C1 119.61(15) . . ?
C14 C15 N16 123.99(15) . . ?
C1 C15 N16 116.39(14) . . ?
C17 N16 C15 128.14(15) . . ?
C17 N16 H16 118.4(14) . . ?
C15 N16 H16 113.5(14) . . ?
O18 C17 N16 122.07(16) . . ?
O18 C17 C19 121.86(16) . . ?
N16 C17 C19 116.04(15) . . ?
C20 C19 C24 119.83(16) . . ?
C20 C19 C17 124.25(16) . . ?
C24 C19 C17 115.92(15) . . ?
C21 C20 C19 119.57(17) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 120.84(17) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 119.71(17) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
O25 C23 C24 124.50(17) . . ?
O25 C23 C22 115.46(16) . . ?
C24 C23 C22 120.03(17) . . ?
C23 C24 C19 120.00(16) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C23 O25 C26 118.35(17) . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc206hd4
_database_code_depnum_ccdc_archive 'CCDC 1853285'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2018-07-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C18 H12 F3 N O4'
_chemical_formula_weight         363.29

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.5811(8)
_cell_length_b                   9.2382(7)
_cell_length_c                   12.4900(11)
_cell_angle_alpha                81.347(7)
_cell_angle_beta                 81.425(8)
_cell_angle_gamma                66.299(8)
_cell_volume                     788.04(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2742
_cell_measurement_theta_min      2.420
_cell_measurement_theta_max      32.316

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5857
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         32.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4696
_reflns_number_gt                2742
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0706P)²+0.1140P] 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         4696
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1692
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.9924(3) -0.1618(2) 0.32540(16) 0.0406(4) Uani 1 1 d . . . . .
H1 H 1.0932 -0.2560 0.3075 0.049 Uiso 1 1 calc R U . . .
C2 C 0.9216(3) -0.0420(2) 0.24550(15) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.9751 -0.0563 0.1739 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7700(2) 0.10210(19) 0.26868(14) 0.0324(4) Uani 1 1 d . . . . .
C4 C 0.6834(2) 0.2366(2) 0.19138(15) 0.0345(4) Uani 1 1 d . . . . .
C5 C 0.7617(3) 0.2308(2) 0.07363(17) 0.0484(5) Uani 1 1 d . . . . .
F6 F 0.95161(19) 0.20118(16) 0.06036(11) 0.0650(4) Uani 1 1 d . . . . .
F7 F 0.7440(2) 0.11462(18) 0.03007(11) 0.0731(5) Uani 1 1 d . . . . .
F8 F 0.6771(2) 0.36550(16) 0.01343(11) 0.0854(5) Uani 1 1 d . . . . .
C9 C 0.5338(3) 0.3664(2) 0.22356(16) 0.0400(4) Uani 1 1 d . . . . .
H9 H 0.4783 0.4510 0.1721 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4572(3) 0.3775(2) 0.33661(16) 0.0386(4) Uani 1 1 d . . . . .
O11 O 0.3234(2) 0.49074(15) 0.37140(12) 0.0522(4) Uani 1 1 d . . . . .
O12 O 0.54556(18) 0.25243(14) 0.40963(10) 0.0419(3) Uani 1 1 d . . . . .
C13 C 0.6951(2) 0.11538(19) 0.37793(15) 0.0328(4) Uani 1 1 d . . . . .
C14 C 0.7637(3) -0.0036(2) 0.46045(15) 0.0371(4) Uani 1 1 d . . . . .
H14 H 0.7096 0.0102 0.5320 0.045 Uiso 1 1 calc R U . . .
C15 C 0.9152(2) -0.1448(2) 0.43476(15) 0.0344(4) Uani 1 1 d . . . . .
N16 N 0.9995(2) -0.27299(17) 0.51065(13) 0.0397(4) Uani 1 1 d . . . . .
H16 H 1.096(3) -0.348(2) 0.4841(18) 0.048 Uiso 1 1 d . U . . .
C17 C 0.9474(3) -0.2889(2) 0.62066(16) 0.0381(4) Uani 1 1 d . . . . .
O18 O 0.8060(2) -0.18855(16) 0.66452(12) 0.0582(4) Uani 1 1 d . . . . .
C19 C 1.0724(3) -0.4361(2) 0.68273(15) 0.0361(4) Uani 1 1 d . . . . .
C20 C 1.0150(3) -0.4594(2) 0.79385(16) 0.0424(5) Uani 1 1 d . . . . .
H20 H 0.9016 -0.3852 0.8248 0.051 Uiso 1 1 calc R U . . .
C21 C 1.1242(3) -0.5904(2) 0.85752(16) 0.0450(5) Uani 1 1 d . . . . .
H21 H 1.0839 -0.6038 0.9311 0.054 Uiso 1 1 calc R U . . .
C22 C 1.2938(3) -0.7030(2) 0.81359(15) 0.0390(4) Uani 1 1 d . . . . .
C23 C 1.3532(3) -0.6822(2) 0.70361(16) 0.0431(5) Uani 1 1 d . . . . .
H23 H 1.4666 -0.7566 0.6729 0.052 Uiso 1 1 calc R U . . .
C24 C 1.2420(3) -0.5496(2) 0.64042(16) 0.0420(5) Uani 1 1 d . . . . .
H24 H 1.2826 -0.5362 0.5669 0.050 Uiso 1 1 calc R U . . .
O25 O 1.3904(2) -0.82872(16) 0.88318(11) 0.0525(4) Uani 1 1 d . . . . .
C26 C 1.5588(3) -0.9521(2) 0.84005(19) 0.0543(6) Uani 1 1 d . . . . .
H26A H 1.5267 -0.9917 0.7821 0.081 Uiso 1 1 calc R U . . .
H26B H 1.6067 -1.0368 0.8964 0.081 Uiso 1 1 calc R U . . .
H26C H 1.6565 -0.9110 0.8126 0.081 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
C1 C2 1.363(2) . ?
C1 C15 1.409(3) . ?
C2 C3 1.401(2) . ?
C3 C13 1.401(2) . ?
C3 C4 1.442(2) . ?
C4 C9 1.343(2) . ?
C4 C5 1.502(3) . ?
C5 F8 1.321(2) . ?
C5 F7 1.334(2) . ?
C5 F6 1.342(3) . ?
C9 C10 1.447(3) . ?
C10 O11 1.2100(19) . ?
C10 O12 1.363(2) . ?
O12 C13 1.3814(18) . ?
C13 C14 1.379(2) . ?
C14 C15 1.391(2) . ?
C15 N16 1.394(2) . ?
N16 C17 1.375(2) . ?
C17 O18 1.220(2) . ?
C17 C19 1.488(2) . ?
C19 C24 1.382(2) . ?
C19 C20 1.403(3) . ?
C20 C21 1.372(3) . ?
C21 C22 1.386(3) . ?
C22 O25 1.358(2) . ?
C22 C23 1.390(3) . ?
C23 C24 1.383(3) . ?
O25 C26 1.424(2) . ?

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 C15 120.95(16) . . ?
C1 C2 C3 121.52(16) . . ?
C13 C3 C2 116.32(16) . . ?
C13 C3 C4 117.18(14) . . ?
C2 C3 C4 126.49(16) . . ?
C9 C4 C3 120.72(16) . . ?
C9 C4 C5 119.79(16) . . ?
C3 C4 C5 119.49(15) . . ?
F8 C5 F7 107.98(19) . . ?
F8 C5 F6 106.18(18) . . ?
F7 C5 F6 105.55(16) . . ?
F8 C5 C4 112.98(15) . . ?
F7 C5 C4 111.89(17) . . ?
F6 C5 C4 111.80(17) . . ?
C4 C9 C10 121.33(17) . . ?
O11 C10 O12 117.66(17) . . ?
O11 C10 C9 124.90(17) . . ?
O12 C10 C9 117.42(14) . . ?
C10 O12 C13 122.21(14) . . ?
C14 C13 O12 115.52(15) . . ?
C14 C13 C3 123.46(15) . . ?
O12 C13 C3 121.02(15) . . ?
C13 C14 C15 118.75(16) . . ?
C14 C15 N16 124.39(16) . . ?
C14 C15 C1 118.99(16) . . ?
N16 C15 C1 116.62(15) . . ?
C17 N16 C15 128.15(15) . . ?
O18 C17 N16 121.80(17) . . ?
O18 C17 C19 122.06(17) . . ?
N16 C17 C19 116.13(15) . . ?
C24 C19 C20 117.54(17) . . ?
C24 C19 C17 125.40(17) . . ?
C20 C19 C17 117.04(16) . . ?
C21 C20 C19 120.79(17) . . ?
C20 C21 C22 120.83(18) . . ?
O25 C22 C21 116.27(17) . . ?
O25 C22 C23 124.44(17) . . ?
C21 C22 C23 119.29(17) . . ?
C24 C23 C22 119.29(17) . . ?
C19 C24 C23 122.26(17) . . ?
C22 O25 C26 118.11(16) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_1_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc28bp4g
_database_code_depnum_ccdc_archive 'CCDC 2095635'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C11 H10 Cl2 F2 N O'
_chemical_formula_weight         281.10

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'
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                   7.6209(12)
_cell_length_b                   25.581(2)
_cell_length_c                   9.0607(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.036(16)
_cell_angle_gamma                90
_cell_volume                     1613.2(4)
_cell_formula_units_Z            14
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    4.051
_exptl_crystal_F_000             2002
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.427
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8860
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.587
_diffrn_reflns_theta_max         32.302
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5103
_reflns_number_gt                3902
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0512P)²+4.0871P] 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         5103
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0794
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.2030
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.5995(5) 0.34915(13) 0.5998(4) 0.0370(7) Uani 1 1 d . . . . .
H1 H 0.6803 0.3574 0.7058 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5013(5) 0.38827(13) 0.4936(4) 0.0365(7) Uani 1 1 d . . . . .
H2 H 0.5160 0.4227 0.5292 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3796(4) 0.37697(12) 0.3331(4) 0.0291(6) Uani 1 1 d . . . . .
C4 C 0.2696(5) 0.41460(13) 0.2098(4) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.2908(6) 0.47200(14) 0.2486(5) 0.0459(9) Uani 1 1 d . . . . .
F6 F 0.2423(5) 0.48423(10) 0.3694(4) 0.0671(8) Uani 1 1 d . . . . .
F7 F 0.4715(4) 0.48790(10) 0.2939(4) 0.0668(8) Uani 1 1 d . . . . .
F8 F 0.1849(5) 0.50111(10) 0.1240(4) 0.0877(12) Uani 1 1 d . . . . .
C9 C 0.1556(5) 0.39886(14) 0.0613(4) 0.0373(7) Uani 1 1 d . . . . .
H9 H 0.0820 0.4235 -0.0139 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1430(5) 0.34408(14) 0.0133(4) 0.0356(7) Uani 1 1 d . . . . .
O11 O 0.0545(4) 0.32759(11) -0.1208(3) 0.0496(7) Uani 1 1 d . . . . .
O12 O 0.2438(4) 0.30912(9) 0.1320(3) 0.0380(6) Uani 1 1 d . . . . .
C13 C 0.3594(4) 0.32477(12) 0.2871(3) 0.0291(6) Uani 1 1 d . . . . .
C14 C 0.4541(5) 0.28479(12) 0.3913(4) 0.0317(6) Uani 1 1 d . . . . .
H14 H 0.4352 0.2502 0.3567 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5783(5) 0.29715(12) 0.5487(4) 0.0306(6) Uani 1 1 d . . . . .
N16 N 0.6808(4) 0.25816(11) 0.6603(3) 0.0328(6) Uani 1 1 d . . . . .
H16 H 0.700(6) 0.2615(16) 0.768(5) 0.039 Uiso 1 1 d . U . . .
C17 C 0.7486(5) 0.21364(13) 0.6218(4) 0.0317(6) Uani 1 1 d . . . . .
O18 O 0.7319(5) 0.20277(11) 0.4855(3) 0.0481(7) Uani 1 1 d . . . . .
C19 C 0.8485(5) 0.17764(12) 0.7614(4) 0.0299(6) Uani 1 1 d . . . . .
C20 C 0.8131(5) 0.12361(13) 0.7483(4) 0.0356(7) Uani 1 1 d . . . . .
C21 C 0.9070(6) 0.09058(14) 0.8778(5) 0.0414(8) Uani 1 1 d . . . . .
H21 H 0.8796 0.0550 0.8691 0.050 Uiso 1 1 calc R U . . .
C22 C 1.0407(6) 0.11087(14) 1.0189(4) 0.0393(8) Uani 1 1 d . . . . .
C23 C 1.0802(5) 0.16381(14) 1.0380(4) 0.0390(7) Uani 1 1 d . . . . .
H23 H 1.1696 0.1770 1.1351 0.047 Uiso 1 1 calc R U . . .
C24 C 0.9835(5) 0.19670(13) 0.9089(4) 0.0349(7) Uani 1 1 d . . . . .
H24 H 1.0088 0.2324 0.9205 0.042 Uiso 1 1 calc R U . . .
Cl25 Cl 0.64759(18) 0.09591(5) 0.57248(14) 0.0593(3) Uani 1 1 d . . . . .
Cl26 Cl 1.1635(2) 0.06876(5) 1.17873(13) 0.0643(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 1.379(5) . ?
C1 C15 1.396(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.400(4) . ?
C2 H2 0.9300 . ?
C3 C13 1.388(4) . ?
C3 C4 1.454(4) . ?
C4 C9 1.333(5) . ?
C4 C5 1.503(5) . ?
C5 F8 1.319(4) . ?
C5 F6 1.327(5) . ?
C5 F7 1.330(5) . ?
C9 C10 1.459(5) . ?
C9 H9 0.9300 . ?
C10 O11 1.200(4) . ?
C10 O12 1.369(4) . ?
O12 C13 1.380(3) . ?
C13 C14 1.379(4) . ?
C14 C15 1.390(4) . ?
C14 H14 0.9300 . ?
C15 N16 1.409(4) . ?
N16 C17 1.354(4) . ?
N16 H16 0.92(4) . ?
C17 O18 1.221(4) . ?
C17 C19 1.498(4) . ?
C19 C24 1.401(5) . ?
C19 C20 1.404(5) . ?
C20 C21 1.385(5) . ?
C20 Cl25 1.730(4) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(5) . ?
C22 Cl26 1.740(3) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9300 . ?
C24 H24 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 C15 120.3(3) . . ?
C2 C1 H1 119.9 . . ?
C15 C1 H1 119.9 . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C13 C3 C2 117.1(3) . . ?
C13 C3 C4 116.6(3) . . ?
C2 C3 C4 126.3(3) . . ?
C9 C4 C3 120.7(3) . . ?
C9 C4 C5 119.7(3) . . ?
C3 C4 C5 119.6(3) . . ?
F8 C5 F6 107.1(4) . . ?
F8 C5 F7 106.7(4) . . ?
F6 C5 F7 105.9(3) . . ?
F8 C5 C4 112.4(3) . . ?
F6 C5 C4 112.5(3) . . ?
F7 C5 C4 111.7(3) . . ?
C4 C9 C10 121.9(3) . . ?
C4 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
O11 C10 O12 118.0(3) . . ?
O11 C10 C9 125.5(3) . . ?
O12 C10 C9 116.5(3) . . ?
C10 O12 C13 122.1(3) . . ?
C14 C13 O12 114.9(3) . . ?
C14 C13 C3 123.0(3) . . ?
O12 C13 C3 122.1(3) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C1 119.7(3) . . ?
C14 C15 N16 121.5(3) . . ?
C1 C15 N16 118.8(3) . . ?
C17 N16 C15 124.7(3) . . ?
C17 N16 H16 116(3) . . ?
C15 N16 H16 120(3) . . ?
O18 C17 N16 124.0(3) . . ?
O18 C17 C19 121.5(3) . . ?
N16 C17 C19 114.6(3) . . ?
C24 C19 C20 117.7(3) . . ?
C24 C19 C17 121.0(3) . . ?
C20 C19 C17 121.3(3) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 Cl25 117.5(3) . . ?
C19 C20 Cl25 121.6(3) . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.9(3) . . ?
C21 C22 Cl26 119.0(3) . . ?
C23 C22 Cl26 119.1(3) . . ?
C22 C23 C24 118.4(3) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C23 C24 C19 121.7(3) . . ?
C23 C24 H24 119.1 . . ?
C19 C24 H24 119.1 . . ?

_refine_diff_density_max         0.459
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.076



####################################################################### 
# 
# 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_1_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc28bp2d
_database_code_depnum_ccdc_archive 'CCDC 2095633'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C18 H12 F3 N O3'
_chemical_formula_weight         347.29

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/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0555(13)
_cell_length_b                   23.627(4)
_cell_length_c                   9.2407(18)
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 89.525(11)
_cell_angle_gamma                90.000(11)
_cell_volume                     1540.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4573
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.363
_diffrn_reflns_theta_max         27.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             3192
_reflns_number_gt                2298
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1087P)²+0.1218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3192
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1835
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.3709(4) 0.41915(9) 0.3050(2) 0.0483(6) Uani 1 1 d . . . . .
H1 H 0.3921 0.4119 0.2073 0.058 Uiso 1 1 calc R U . . .
C2 C 0.4197(3) 0.37941(9) 0.4049(2) 0.0472(5) Uani 1 1 d . . . . .
H2 H 0.4717 0.3452 0.3741 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3931(3) 0.38914(8) 0.5531(2) 0.0379(4) Uani 1 1 d . . . . .
C4 C 0.4370(3) 0.35039(9) 0.6680(2) 0.0393(5) Uani 1 1 d . . . . .
C5 C 0.5037(4) 0.29173(10) 0.6337(2) 0.0530(6) Uani 1 1 d . . . . .
F6 F 0.3776(3) 0.26390(6) 0.55362(19) 0.0826(6) Uani 1 1 d . . . . .
F7 F 0.6639(2) 0.29125(7) 0.55933(18) 0.0766(5) Uani 1 1 d . . . . .
F8 F 0.5327(3) 0.26065(7) 0.75090(17) 0.0843(6) Uani 1 1 d . . . . .
C9 C 0.4148(3) 0.36564(9) 0.8066(2) 0.0428(5) Uani 1 1 d . . . . .
H9 H 0.4419 0.3398 0.8795 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3497(3) 0.42139(9) 0.8441(2) 0.0423(5) Uani 1 1 d . . . . .
O11 O 0.3394(3) 0.43986(7) 0.96622(15) 0.0571(5) Uani 1 1 d . . . . .
O12 O 0.2951(2) 0.45642(6) 0.73472(14) 0.0439(4) Uani 1 1 d . . . . .
C13 C 0.3179(3) 0.44133(8) 0.59126(19) 0.0364(4) Uani 1 1 d . . . . .
C14 C 0.2643(3) 0.48209(9) 0.4928(2) 0.0395(5) Uani 1 1 d . . . . .
H14 H 0.2126 0.5163 0.5236 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2894(3) 0.47076(8) 0.3470(2) 0.0388(5) Uani 1 1 d . . . . .
N16 N 0.2416(3) 0.50836(8) 0.23671(18) 0.0457(5) Uani 1 1 d . . . . .
H16 H 0.2612 0.4965 0.1499 0.055 Uiso 1 1 calc R U . . .
C17 C 0.1675(3) 0.56169(9) 0.2490(2) 0.0408(5) Uani 1 1 d . . . . .
O18 O 0.1343(3) 0.58369(7) 0.36508(16) 0.0574(5) Uani 1 1 d . . . . .
C19 C 0.1313(3) 0.59216(9) 0.1094(2) 0.0411(5) Uani 1 1 d . . . . .
C20 C 0.0690(3) 0.64763(9) 0.1195(3) 0.0505(6) Uani 1 1 d . . . . .
H20 H 0.0525 0.6643 0.2099 0.061 Uiso 1 1 calc R U . . .
C21 C 0.0313(4) 0.67823(10) -0.0041(3) 0.0577(6) Uani 1 1 d . . . . .
H21 H -0.0116 0.7153 0.0045 0.069 Uiso 1 1 calc R U . . .
C22 C 0.0559(3) 0.65509(10) -0.1404(3) 0.0527(6) Uani 1 1 d . . . . .
C23 C 0.1180(4) 0.60019(12) -0.1491(3) 0.0604(7) Uani 1 1 d . . . . .
H23 H 0.1351 0.5837 -0.2397 0.072 Uiso 1 1 calc R U . . .
C24 C 0.1558(4) 0.56874(10) -0.0261(2) 0.0561(6) Uani 1 1 d . . . . .
H24 H 0.1980 0.5316 -0.0350 0.067 Uiso 1 1 calc R U . . .
C25 C 0.0169(4) 0.68972(13) -0.2743(3) 0.0720(8) Uani 1 1 d . . . . .
H25A H -0.1046 0.7077 -0.2648 0.108 Uiso 1 1 calc R U . . .
H25B H 0.0170 0.6654 -0.3575 0.108 Uiso 1 1 calc R U . . .
H25C H 0.1134 0.7180 -0.2857 0.108 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
C1 C2 1.363(3) . ?
C1 C15 1.402(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.400(3) . ?
C2 H2 0.9300 . ?
C3 C13 1.387(3) . ?
C3 C4 1.438(3) . ?
C4 C9 1.338(3) . ?
C4 C5 1.497(3) . ?
C5 F7 1.318(3) . ?
C5 F8 1.326(3) . ?
C5 F6 1.335(3) . ?
C9 C10 1.436(3) . ?
C9 H9 0.9300 . ?
C10 O11 1.212(2) . ?
C10 O12 1.364(2) . ?
O12 C13 1.381(2) . ?
C13 C14 1.380(3) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 N16 1.395(2) . ?
N16 C17 1.369(3) . ?
N16 H16 0.8600 . ?
C17 O18 1.213(3) . ?
C17 C19 1.501(3) . ?
C19 C24 1.378(3) . ?
C19 C20 1.385(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(4) . ?
C22 C25 1.510(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C2 C1 C15 121.13(18) . . ?
C2 C1 H1 119.4 . . ?
C15 C1 H1 119.4 . . ?
C1 C2 C3 121.12(19) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C13 C3 C2 116.29(18) . . ?
C13 C3 C4 117.57(17) . . ?
C2 C3 C4 126.14(19) . . ?
C9 C4 C3 120.73(19) . . ?
C9 C4 C5 119.09(18) . . ?
C3 C4 C5 120.16(18) . . ?
F7 C5 F8 106.5(2) . . ?
F7 C5 F6 106.2(2) . . ?
F8 C5 F6 106.8(2) . . ?
F7 C5 C4 112.6(2) . . ?
F8 C5 C4 112.96(19) . . ?
F6 C5 C4 111.3(2) . . ?
C4 C9 C10 120.82(18) . . ?
C4 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O11 C10 O12 117.15(19) . . ?
O11 C10 C9 124.87(18) . . ?
O12 C10 C9 117.99(17) . . ?
C10 O12 C13 121.55(16) . . ?
C14 C13 O12 115.00(17) . . ?
C14 C13 C3 124.00(18) . . ?
O12 C13 C3 120.99(17) . . ?
C13 C14 C15 118.27(19) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 N16 123.94(18) . . ?
C14 C15 C1 119.15(18) . . ?
N16 C15 C1 116.90(17) . . ?
C17 N16 C15 128.32(18) . . ?
C17 N16 H16 115.8 . . ?
C15 N16 H16 115.8 . . ?
O18 C17 N16 122.60(19) . . ?
O18 C17 C19 121.42(18) . . ?
N16 C17 C19 115.98(18) . . ?
C24 C19 C20 118.6(2) . . ?
C24 C19 C17 124.54(18) . . ?
C20 C19 C17 116.90(19) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 121.5(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C23 C22 C21 117.7(2) . . ?
C23 C22 C25 121.6(2) . . ?
C21 C22 C25 120.6(2) . . ?
C22 C23 C24 121.5(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 C24 C23 120.4(2) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_1_CCDC4
_audit_block_doi                 10.5517/ccdc.csd.cc28bp5h
_database_code_depnum_ccdc_archive 'CCDC 2095636'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C11 H10 F0.25 N O'
_chemical_formula_weight         176.95

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2408(6)
_cell_length_b                   8.8756(8)
_cell_length_c                   13.3042(9)
_cell_angle_alpha                98.204(7)
_cell_angle_beta                 96.304(6)
_cell_angle_gamma                114.400(8)
_cell_volume                     861.61(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             373
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6414
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.726
_diffrn_reflns_theta_max         32.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5134
_reflns_number_gt                3340
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0624P)²+0.1801P] 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         5134
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 -0.1357(2) -0.2423(2) 0.20826(12) 0.0447(4) Uani 1 1 d . . . . .
H1 H -0.2324 -0.3305 0.2245 0.054 Uiso 1 1 calc R U . . .
C2 C -0.0358(2) -0.0985(2) 0.28175(12) 0.0445(4) Uani 1 1 d . . . . .
H2 H -0.0655 -0.0903 0.3471 0.053 Uiso 1 1 calc R U . . .
C3 C 0.1111(2) 0.03732(19) 0.26019(11) 0.0337(3) Uani 1 1 d . . . . .
C4 C 0.2272(2) 0.1944(2) 0.33089(11) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.2002(3) 0.2242(2) 0.44053(13) 0.0494(5) Uani 1 1 d . . . . .
F6 F 0.3170(2) 0.37540(16) 0.49503(9) 0.0858(5) Uani 1 1 d . . . . .
F7 F 0.2178(2) 0.11100(17) 0.49082(9) 0.0737(4) Uani 1 1 d . . . . .
F8 F 0.03614(18) 0.21270(18) 0.44613(9) 0.0726(4) Uani 1 1 d . . . . .
C9 C 0.3608(2) 0.3164(2) 0.30040(12) 0.0409(4) Uani 1 1 d . . . . .
H9 H 0.4332 0.4177 0.3470 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3945(2) 0.2935(2) 0.19630(12) 0.0370(4) Uani 1 1 d . . . . .
O11 O 0.51262(17) 0.39756(15) 0.16376(9) 0.0493(3) Uani 1 1 d . . . . .
O12 O 0.28621(16) 0.14321(13) 0.13066(8) 0.0384(3) Uani 1 1 d . . . . .
C13 C 0.1458(2) 0.01711(18) 0.16033(11) 0.0313(3) Uani 1 1 d . . . . .
C14 C 0.0470(2) -0.12702(19) 0.08448(11) 0.0351(3) Uani 1 1 d . . . . .
H14 H 0.0754 -0.1348 0.0188 0.042 Uiso 1 1 calc R U . . .
C15 C -0.0956(2) -0.25974(19) 0.10878(11) 0.0348(3) Uani 1 1 d . . . . .
N16 N -0.2039(2) -0.41284(17) 0.03950(10) 0.0407(3) Uani 1 1 d . . . . .
H16 H -0.290(3) -0.481(2) 0.0646(15) 0.049 Uiso 1 1 d . U . . .
C17 C -0.1866(2) -0.4642(2) -0.05904(12) 0.0387(4) Uani 1 1 d . . . . .
O18 O -0.07365(19) -0.37095(16) -0.10148(10) 0.0581(4) Uani 1 1 d . . . . .
C19 C -0.3153(2) -0.64026(19) -0.11294(12) 0.0362(3) Uani 1 1 d . . . . .
C20 C -0.3075(2) -0.6874(2) -0.21636(12) 0.0383(4) Uani 1 1 d . . . . .
H20 H -0.2249 -0.6098 -0.2474 0.046 Uiso 1 1 calc R U . . .
C21 C -0.4205(2) -0.8475(2) -0.27307(12) 0.0388(4) Uani 1 1 d . . . . .
C22 C -0.5439(2) -0.9653(2) -0.22618(13) 0.0392(4) Uani 1 1 d . . . . .
C23 C -0.5514(3) -0.9189(2) -0.12411(13) 0.0454(4) Uani 1 1 d . . . . .
H23 H -0.6334 -0.9965 -0.0927 0.054 Uiso 1 1 calc R U . . .
C24 C -0.4379(3) -0.7576(2) -0.06779(13) 0.0448(4) Uani 1 1 d . . . . .
H24 H -0.4442 -0.7281 0.0011 0.054 Uiso 1 1 calc R U . . .
O25 O -0.42200(19) -0.90348(15) -0.37419(9) 0.0527(4) Uani 1 1 d . . . . .
C26 C -0.3103(3) -0.7841(3) -0.42713(14) 0.0606(6) Uani 1 1 d . . . . .
H26A H -0.3414 -0.6907 -0.4233 0.091 Uiso 1 1 calc R U . . .
H26B H -0.3287 -0.8370 -0.4982 0.091 Uiso 1 1 calc R U . . .
H26C H -0.1854 -0.7438 -0.3957 0.091 Uiso 1 1 calc R U . . .
O27 O -0.64879(19) -1.12087(15) -0.28739(10) 0.0542(4) Uani 1 1 d . . . . .
C28 C -0.7897(3) -1.2382(2) -0.24609(18) 0.0572(5) Uani 1 1 d . . . . .
H28A H -0.7372 -1.2650 -0.1872 0.086 Uiso 1 1 calc R U . . .
H28B H -0.8586 -1.3396 -0.2978 0.086 Uiso 1 1 calc R U . . .
H28C H -0.8680 -1.1889 -0.2255 0.086 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
C1 C2 1.365(2) . ?
C1 C15 1.402(2) . ?
C2 C3 1.403(2) . ?
C3 C13 1.392(2) . ?
C3 C4 1.439(2) . ?
C4 C9 1.337(2) . ?
C4 C5 1.502(2) . ?
C5 F8 1.325(2) . ?
C5 F6 1.3248(19) . ?
C5 F7 1.330(2) . ?
C9 C10 1.445(2) . ?
C10 O11 1.2051(18) . ?
C10 O12 1.3604(18) . ?
O12 C13 1.3797(17) . ?
C13 C14 1.381(2) . ?
C14 C15 1.386(2) . ?
C15 N16 1.3972(19) . ?
N16 C17 1.368(2) . ?
C17 O18 1.2177(19) . ?
C17 C19 1.491(2) . ?
C19 C24 1.382(2) . ?
C19 C20 1.396(2) . ?
C20 C21 1.379(2) . ?
C21 O25 1.3629(19) . ?
C21 C22 1.401(2) . ?
C22 O27 1.3623(19) . ?
C22 C23 1.377(2) . ?
C23 C24 1.385(2) . ?
O25 C26 1.420(2) . ?
O27 C28 1.428(2) . ?

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 C15 121.32(14) . . ?
C1 C2 C3 121.01(14) . . ?
C13 C3 C2 116.29(13) . . ?
C13 C3 C4 117.39(13) . . ?
C2 C3 C4 126.32(14) . . ?
C9 C4 C3 120.76(14) . . ?
C9 C4 C5 118.81(14) . . ?
C3 C4 C5 120.44(14) . . ?
F8 C5 F6 106.45(17) . . ?
F8 C5 F7 105.81(15) . . ?
F6 C5 F7 106.88(16) . . ?
F8 C5 C4 112.37(16) . . ?
F6 C5 C4 112.86(14) . . ?
F7 C5 C4 111.99(17) . . ?
C4 C9 C10 121.10(14) . . ?
O11 C10 O12 117.70(14) . . ?
O11 C10 C9 124.62(14) . . ?
O12 C10 C9 117.68(13) . . ?
C10 O12 C13 121.96(12) . . ?
O12 C13 C14 115.01(13) . . ?
O12 C13 C3 121.09(13) . . ?
C14 C13 C3 123.90(13) . . ?
C13 C14 C15 118.32(14) . . ?
C14 C15 N16 123.80(14) . . ?
C14 C15 C1 119.14(13) . . ?
N16 C15 C1 117.06(13) . . ?
C17 N16 C15 128.32(14) . . ?
O18 C17 N16 122.00(14) . . ?
O18 C17 C19 121.39(14) . . ?
N16 C17 C19 116.60(14) . . ?
C24 C19 C20 118.76(14) . . ?
C24 C19 C17 124.85(14) . . ?
C20 C19 C17 116.39(14) . . ?
C21 C20 C19 120.95(15) . . ?
O25 C21 C20 124.68(15) . . ?
O25 C21 C22 115.66(14) . . ?
C20 C21 C22 119.66(14) . . ?
O27 C22 C23 124.79(15) . . ?
O27 C22 C21 115.81(14) . . ?
C23 C22 C21 119.40(14) . . ?
C22 C23 C24 120.59(16) . . ?
C19 C24 C23 120.65(15) . . ?
C21 O25 C26 117.45(13) . . ?
C22 O27 C28 117.42(14) . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_1_CCDC5
_audit_block_doi                 10.5517/ccdc.csd.cc206hf5
_database_code_depnum_ccdc_archive 'CCDC 1853286'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2018-07-03 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C17 H9 Cl F3 N O3'
_chemical_formula_weight         367.70

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4758(11)
_cell_length_b                   24.455(3)
_cell_length_c                   8.7630(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.813(17)
_cell_angle_gamma                90
_cell_volume                     1487.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2201
_cell_measurement_theta_min      2.638
_cell_measurement_theta_max      32.708

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.309
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11220
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.638
_diffrn_reflns_theta_max         32.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5035
_reflns_number_gt                2201
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0546P)²+0.2711P] 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         5035
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1760
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.4062(4) 0.64754(10) 0.4775(3) 0.0443(6) Uani 1 1 d . . . . .
H1 H 0.3173 0.6385 0.3740 0.053 Uiso 1 1 calc R U . . .
C2 C 0.4962(4) 0.60728(10) 0.5840(3) 0.0425(6) Uani 1 1 d . . . . .
H2 H 0.4666 0.5710 0.5536 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6325(3) 0.61944(10) 0.7388(3) 0.0366(6) Uani 1 1 d . . . . .
C4 C 0.7292(3) 0.58128(9) 0.8638(3) 0.0391(6) Uani 1 1 d . . . . .
C5 C 0.6858(4) 0.52220(11) 0.8379(3) 0.0530(8) Uani 1 1 d . . . . .
F6 F 0.7248(3) 0.50233(7) 0.7155(2) 0.0851(7) Uani 1 1 d . . . . .
F7 F 0.5035(3) 0.51203(7) 0.8079(3) 0.0814(6) Uani 1 1 d . . . . .
F8 F 0.7831(3) 0.49272(7) 0.9678(2) 0.0793(6) Uani 1 1 d . . . . .
C9 C 0.8574(4) 0.59791(11) 1.0064(3) 0.0489(7) Uani 1 1 d . . . . .
H9 H 0.9178 0.5722 1.0875 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9046(4) 0.65392(11) 1.0382(3) 0.0503(7) Uani 1 1 d . . . . .
O11 O 1.0214(3) 0.67162(9) 1.1610(2) 0.0776(8) Uani 1 1 d . . . . .
O12 O 0.8091(2) 0.69003(7) 0.91977(19) 0.0455(5) Uani 1 1 d . . . . .
C13 C 0.6733(3) 0.67375(10) 0.7730(3) 0.0358(6) Uani 1 1 d . . . . .
C14 C 0.5841(3) 0.71498(10) 0.6686(3) 0.0381(6) Uani 1 1 d . . . . .
H14 H 0.6172 0.7512 0.6973 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4444(3) 0.70190(10) 0.5203(3) 0.0378(6) Uani 1 1 d . . . . .
N16 N 0.3356(3) 0.74035(9) 0.4080(3) 0.0439(6) Uani 1 1 d . . . . .
H16 H 0.254(4) 0.7260(11) 0.323(3) 0.053 Uiso 1 1 d . U . . .
C17 C 0.3331(4) 0.79454(11) 0.4283(3) 0.0495(7) Uani 1 1 d . . . . .
O18 O 0.4404(4) 0.81702(9) 0.5498(3) 0.0958(10) Uani 1 1 d . . . . .
C19 C 0.1963(4) 0.82627(10) 0.2900(3) 0.0416(6) Uani 1 1 d . . . . .
C20 C 0.2031(4) 0.88192(11) 0.3083(3) 0.0498(7) Uani 1 1 d . . . . .
H20 H 0.2880 0.8975 0.4048 0.060 Uiso 1 1 calc R U . . .
C21 C 0.0860(4) 0.91456(12) 0.1860(4) 0.0559(8) Uani 1 1 d . . . . .
H21 H 0.0906 0.9523 0.1988 0.067 Uiso 1 1 calc R U . . .
C22 C -0.0368(4) 0.89174(12) 0.0458(3) 0.0505(7) Uani 1 1 d . . . . .
C23 C -0.0474(4) 0.83652(12) 0.0253(3) 0.0529(7) Uani 1 1 d . . . . .
H23 H -0.1335 0.8212 -0.0711 0.063 Uiso 1 1 calc R U . . .
C24 C 0.0699(4) 0.80400(11) 0.1481(3) 0.0486(7) Uani 1 1 d . . . . .
H24 H 0.0637 0.7662 0.1351 0.058 Uiso 1 1 calc R U . . .
Cl25 Cl -0.18244(13) 0.93268(4) -0.10920(10) 0.0773(3) 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 1.351(3) . ?
C1 C15 1.382(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C13 1.371(3) . ?
C3 C4 1.416(3) . ?
C4 C9 1.325(3) . ?
C4 C5 1.479(4) . ?
C5 F6 1.306(3) . ?
C5 F7 1.313(3) . ?
C5 F8 1.315(3) . ?
C9 C10 1.416(4) . ?
C9 H9 0.9300 . ?
C10 O11 1.187(3) . ?
C10 O12 1.348(3) . ?
O12 C13 1.369(3) . ?
C13 C14 1.358(3) . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C15 N16 1.385(3) . ?
N16 C17 1.338(3) . ?
N16 H16 0.84(3) . ?
C17 O18 1.202(3) . ?
C17 C19 1.482(3) . ?
C19 C24 1.364(3) . ?
C19 C20 1.369(4) . ?
C20 C21 1.362(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.351(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.361(4) . ?
C22 Cl25 1.713(3) . ?
C23 C24 1.363(3) . ?
C23 H23 0.9300 . ?
C24 H24 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 C15 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C15 C1 H1 119.5 . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C13 C3 C2 116.3(2) . . ?
C13 C3 C4 117.5(2) . . ?
C2 C3 C4 126.3(2) . . ?
C9 C4 C3 120.7(2) . . ?
C9 C4 C5 119.0(2) . . ?
C3 C4 C5 120.3(2) . . ?
F6 C5 F7 107.3(2) . . ?
F6 C5 F8 106.6(2) . . ?
F7 C5 F8 105.6(2) . . ?
F6 C5 C4 112.7(2) . . ?
F7 C5 C4 111.6(3) . . ?
F8 C5 C4 112.6(2) . . ?
C4 C9 C10 121.5(2) . . ?
C4 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
O11 C10 O12 117.4(2) . . ?
O11 C10 C9 125.2(2) . . ?
O12 C10 C9 117.4(2) . . ?
C10 O12 C13 121.93(19) . . ?
C14 C13 O12 115.1(2) . . ?
C14 C13 C3 123.9(2) . . ?
O12 C13 C3 121.0(2) . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C14 C15 C1 119.3(2) . . ?
C14 C15 N16 123.7(2) . . ?
C1 C15 N16 116.9(2) . . ?
C17 N16 C15 127.7(2) . . ?
C17 N16 H16 119.2(19) . . ?
C15 N16 H16 112.7(19) . . ?
O18 C17 N16 122.2(2) . . ?
O18 C17 C19 121.0(3) . . ?
N16 C17 C19 116.7(2) . . ?
C24 C19 C20 119.1(2) . . ?
C24 C19 C17 124.8(2) . . ?
C20 C19 C17 116.1(2) . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.1(3) . . ?
C21 C22 Cl25 119.8(2) . . ?
C23 C22 Cl25 119.1(2) . . ?
C22 C23 C24 119.1(3) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C19 120.7(3) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_1_CCDC6
_audit_block_doi                 10.5517/ccdc.csd.cc28bp3f
_database_code_depnum_ccdc_archive 'CCDC 2095634'
loop_
_audit_author_name
_audit_author_address
'Chethan Prathap K. N.'
;University of Mysore
India
;
_audit_update_record             
;
2021-07-10 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_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            'C11 H10 Br0 F0.14 N O'
_chemical_formula_weight         174.91

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'
Br Br -0.2901 2.4595 '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                   7.5703(14)
_cell_length_b                   24.984(3)
_cell_length_c                   9.0555(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.89(2)
_cell_angle_gamma                90
_cell_volume                     1577.8(5)
_cell_formula_units_Z            7
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             646
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6651
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         32.316
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4793
_reflns_number_gt                2679
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0580P)²+0.8280P] 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         4793
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.5908(5) 0.64881(14) 0.5067(4) 0.0390(8) Uani 1 1 d . . . . .
H1 H 0.6809 0.6398 0.6075 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5011(5) 0.60922(14) 0.3991(4) 0.0379(8) Uani 1 1 d . . . . .
H2 H 0.5333 0.5737 0.4271 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3619(5) 0.62130(13) 0.2479(4) 0.0317(7) Uani 1 1 d . . . . .
C4 C 0.2624(5) 0.58338(14) 0.1235(4) 0.0347(7) Uani 1 1 d . . . . .
C5 C 0.3103(6) 0.52494(15) 0.1463(5) 0.0460(9) Uani 1 1 d . . . . .
F6 F 0.2738(5) 0.50465(10) 0.2684(3) 0.0745(8) Uani 1 1 d . . . . .
F7 F 0.4937(4) 0.51574(10) 0.1769(3) 0.0678(7) Uani 1 1 d . . . . .
F8 F 0.2105(4) 0.49590(9) 0.0188(3) 0.0690(8) Uani 1 1 d . . . . .
C9 C 0.1318(5) 0.59992(15) -0.0175(4) 0.0433(9) Uani 1 1 d . . . . .
H9 H 0.0710 0.5748 -0.0970 0.052 Uiso 1 1 calc R U . . .
C10 C 0.0838(6) 0.65535(16) -0.0484(4) 0.0476(10) Uani 1 1 d . . . . .
O11 O -0.0341(5) 0.67296(12) -0.1703(4) 0.0789(11) Uani 1 1 d . . . . .
O12 O 0.1785(4) 0.69097(10) 0.0700(3) 0.0426(6) Uani 1 1 d . . . . .
C13 C 0.3173(5) 0.67490(13) 0.2152(4) 0.0322(7) Uani 1 1 d . . . . .
C14 C 0.4067(5) 0.71574(14) 0.3188(4) 0.0349(7) Uani 1 1 d . . . . .
H14 H 0.3734 0.7513 0.2909 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5481(5) 0.70262(14) 0.4663(4) 0.0346(8) Uani 1 1 d . . . . .
N16 N 0.6575(5) 0.74063(12) 0.5781(4) 0.0413(8) Uani 1 1 d . . . . .
H16 H 0.742(6) 0.7292(17) 0.653(5) 0.050 Uiso 1 1 d . U . . .
C17 C 0.6541(6) 0.79456(15) 0.5623(4) 0.0447(9) Uani 1 1 d . . . . .
O18 O 0.5397(6) 0.81731(12) 0.4454(4) 0.0878(13) Uani 1 1 d . . . . .
C19 C 0.7942(5) 0.82565(14) 0.6987(4) 0.0381(8) Uani 1 1 d . . . . .
C20 C 0.7933(6) 0.88067(15) 0.6804(5) 0.0452(9) Uani 1 1 d . . . . .
H20 H 0.7105 0.8961 0.5852 0.054 Uiso 1 1 calc R U . . .
C21 C 0.9140(6) 0.91292(16) 0.8019(5) 0.0488(10) Uani 1 1 d . . . . .
H21 H 0.9135 0.9498 0.7884 0.059 Uiso 1 1 calc R U . . .
C22 C 1.0339(5) 0.88997(15) 0.9418(5) 0.0426(9) Uani 1 1 d . . . . .
C23 C 1.0408(6) 0.83574(16) 0.9634(5) 0.0489(10) Uani 1 1 d . . . . .
H23 H 1.1253 0.8206 1.0585 0.059 Uiso 1 1 calc R U . . .
C24 C 0.9194(6) 0.80372(15) 0.8406(5) 0.0472(9) Uani 1 1 d . . . . .
H24 H 0.9225 0.7668 0.8543 0.057 Uiso 1 1 calc R U . . .
Br25 Br 1.19743(8) 0.93406(2) 1.10902(6) 0.0682(2) 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 1.369(5) . ?
C1 C15 1.398(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(4) . ?
C2 H2 0.9300 . ?
C3 C13 1.385(5) . ?
C3 C4 1.440(5) . ?
C4 C9 1.340(5) . ?
C4 C5 1.499(5) . ?
C5 F8 1.323(4) . ?
C5 F7 1.326(5) . ?
C5 F6 1.339(5) . ?
C9 C10 1.431(5) . ?
C9 H9 0.9300 . ?
C10 O11 1.201(4) . ?
C10 O12 1.363(4) . ?
O12 C13 1.385(4) . ?
C13 C14 1.373(4) . ?
C14 C15 1.387(5) . ?
C14 H14 0.9300 . ?
C15 N16 1.400(4) . ?
N16 C17 1.354(5) . ?
N16 H16 0.78(4) . ?
C17 O18 1.217(5) . ?
C17 C19 1.495(5) . ?
C19 C24 1.379(5) . ?
C19 C20 1.384(5) . ?
C20 C21 1.383(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(6) . ?
C22 Br25 1.893(4) . ?
C23 C24 1.388(5) . ?
C23 H23 0.9300 . ?
C24 H24 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 C15 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C15 C1 H1 119.7 . . ?
C1 C2 C3 121.2(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C13 C3 C2 116.5(3) . . ?
C13 C3 C4 117.3(3) . . ?
C2 C3 C4 126.1(3) . . ?
C9 C4 C3 120.7(3) . . ?
C9 C4 C5 118.7(3) . . ?
C3 C4 C5 120.5(3) . . ?
F8 C5 F7 106.5(3) . . ?
F8 C5 F6 106.4(3) . . ?
F7 C5 F6 107.3(3) . . ?
F8 C5 C4 112.8(3) . . ?
F7 C5 C4 112.0(3) . . ?
F6 C5 C4 111.5(3) . . ?
C4 C9 C10 121.4(3) . . ?
C4 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
O11 C10 O12 117.4(3) . . ?
O11 C10 C9 125.1(3) . . ?
O12 C10 C9 117.5(3) . . ?
C10 O12 C13 122.0(3) . . ?
C14 C13 O12 115.1(3) . . ?
C14 C13 C3 123.9(3) . . ?
O12 C13 C3 121.0(3) . . ?
C13 C14 C15 118.2(3) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C1 119.5(3) . . ?
C14 C15 N16 123.6(3) . . ?
C1 C15 N16 116.9(3) . . ?
C17 N16 C15 128.1(3) . . ?
C17 N16 H16 116(3) . . ?
C15 N16 H16 116(3) . . ?
O18 C17 N16 122.3(4) . . ?
O18 C17 C19 120.8(4) . . ?
N16 C17 C19 116.8(3) . . ?
C24 C19 C20 118.4(3) . . ?
C24 C19 C17 125.0(3) . . ?
C20 C19 C17 116.6(3) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 121.6(4) . . ?
C21 C22 Br25 119.3(3) . . ?
C23 C22 Br25 119.1(3) . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C19 C24 C23 121.2(4) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.086



