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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_agml_661_0m
_database_code_depnum_ccdc_archive 'CCDC 2243514'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_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         'C22 H16 F3 N O'
_chemical_formula_sum            'C22 H16 F3 N O'
_chemical_formula_weight         367.36
_chemical_absolute_configuration ?
_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'
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'

_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   6.8883(9)
_cell_length_b                   15.522(2)
_cell_length_c                   16.668(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1782.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.7916.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11776
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.774
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2903
_reflns_number_total             3526
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3526
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.2864(3) 0.69823(13) 0.53651(12) 0.0512(5) Uani 1 1 d . . . . .
N1 N 0.4916(4) 0.78458(17) 0.61252(14) 0.0487(6) Uani 1 1 d . . . . .
F3 F 0.1273(5) 0.54591(14) 0.60730(18) 0.1036(9) Uani 1 1 d . . . . .
F2 F 0.3410(5) 0.60449(19) 0.6773(2) 0.1188(11) Uani 1 1 d . . . . .
F1 F 0.0453(6) 0.6171(2) 0.70874(19) 0.1351(14) Uani 1 1 d . . . . .
C17 C 0.7175(4) 0.82445(17) 0.51445(17) 0.0421(7) Uani 1 1 d . . . . .
C11 C 0.4418(4) 0.81349(17) 0.41007(16) 0.0408(6) Uani 1 1 d . . . . .
C5 C 0.6693(4) 0.68790(18) 0.43791(18) 0.0435(7) Uani 1 1 d . . . . .
C16 C 0.4508(5) 0.9014(2) 0.3979(2) 0.0525(8) Uani 1 1 d . . . . .
C6 C 0.7071(5) 0.6158(2) 0.4835(2) 0.0537(8) Uani 1 1 d . . . . .
C3 C 0.4441(4) 0.74866(17) 0.54675(18) 0.0432(6) Uani 1 1 d . . . . .
C4 C 0.5682(4) 0.76751(17) 0.47262(16) 0.0417(6) Uani 1 1 d . . . . .
C12 C 0.3111(4) 0.7654(2) 0.36376(19) 0.0505(7) Uani 1 1 d . . . . .
C22 C 0.6642(4) 0.83153(18) 0.59481(18) 0.0453(7) Uani 1 1 d . . . . .
C18 C 0.8857(5) 0.8628(2) 0.4874(2) 0.0505(7) Uani 1 1 d . . . . .
C13 C 0.2007(5) 0.8053(2) 0.30517(19) 0.0549(8) Uani 1 1 d . . . . .
C15 C 0.3377(5) 0.9407(3) 0.3394(2) 0.0624(9) Uani 1 1 d . . . . .
C1 C 0.1655(6) 0.6158(2) 0.6480(2) 0.0619(9) Uani 1 1 d . . . . .
C14 C 0.2154(5) 0.8922(2) 0.2929(2) 0.0608(9) Uani 1 1 d . . . . .
C20 C 0.9427(5) 0.9181(2) 0.6204(2) 0.0606(9) Uani 1 1 d . . . . .
C19 C 0.9977(5) 0.9104(2) 0.5410(2) 0.0568(8) Uani 1 1 d . . . . .
C21 C 0.7752(5) 0.8775(2) 0.6486(2) 0.0560(8) Uani 1 1 d . . . . .
C2 C 0.1485(5) 0.6965(2) 0.6016(2) 0.0557(8) Uani 1 1 d . . . . .
C10 C 0.7368(6) 0.6897(3) 0.3593(2) 0.0621(9) Uani 1 1 d . . . . .
C8 C 0.8764(5) 0.5491(3) 0.3751(3) 0.0717(11) Uani 1 1 d . . . . .
C7 C 0.8098(6) 0.5468(2) 0.4527(3) 0.0678(10) Uani 1 1 d . . . . .
C9 C 0.8387(6) 0.6202(3) 0.3282(3) 0.0757(12) Uani 1 1 d . . . . .
H18 H 0.930(5) 0.858(2) 0.433(2) 0.059(9) Uiso 1 1 d . . . . .
H21 H 0.734(5) 0.881(2) 0.707(3) 0.061(9) Uiso 1 1 d . . . . .
H20 H 1.025(5) 0.952(2) 0.658(2) 0.068(10) Uiso 1 1 d . . . . .
H19 H 1.127(5) 0.943(2) 0.523(2) 0.074(11) Uiso 1 1 d . . . . .
H2A H 0.184(5) 0.748(2) 0.638(2) 0.068(11) Uiso 1 1 d . . . . .
H12 H 0.301(4) 0.702(2) 0.3726(19) 0.046(8) Uiso 1 1 d . . . . .
H16 H 0.531(5) 0.936(2) 0.428(2) 0.054(9) Uiso 1 1 d . . . . .
H10 H 0.705(5) 0.738(2) 0.327(2) 0.071(11) Uiso 1 1 d . . . . .
H15 H 0.344(6) 0.999(3) 0.333(3) 0.078(12) Uiso 1 1 d . . . . .
H7 H 0.836(7) 0.494(4) 0.485(3) 0.106(15) Uiso 1 1 d . . . . .
H13 H 0.107(6) 0.773(2) 0.269(2) 0.068(10) Uiso 1 1 d . . . . .
H9 H 0.880(6) 0.621(2) 0.274(3) 0.077(12) Uiso 1 1 d . . . . .
H6 H 0.660(5) 0.614(2) 0.539(3) 0.068(11) Uiso 1 1 d . . . . .
H8 H 0.948(6) 0.498(3) 0.352(3) 0.092(13) Uiso 1 1 d . . . . .
H2B H 0.017(6) 0.696(3) 0.577(2) 0.085(13) Uiso 1 1 d . . . . .
H14 H 0.138(6) 0.921(3) 0.253(3) 0.076(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.350(3) . ?
O1 C2 1.443(4) . ?
N1 C3 1.273(4) . ?
N1 C22 1.426(4) . ?
F3 C1 1.306(4) . ?
F2 C1 1.315(4) . ?
F1 C1 1.308(4) . ?
C17 C4 1.525(4) . ?
C17 C22 1.393(4) . ?
C17 C18 1.378(4) . ?
C11 C16 1.382(4) . ?
C11 C4 1.534(4) . ?
C11 C12 1.402(4) . ?
C5 C6 1.378(5) . ?
C5 C4 1.532(4) . ?
C5 C10 1.390(5) . ?
C16 C15 1.388(5) . ?
C16 H16 0.92(3) . ?
C6 C7 1.383(5) . ?
C6 H6 0.98(4) . ?
C3 C4 1.531(4) . ?
C12 C13 1.384(5) . ?
C12 H12 1.00(3) . ?
C22 C21 1.377(4) . ?
C18 C19 1.392(5) . ?
C18 H18 0.96(4) . ?
C13 C14 1.369(5) . ?
C13 H13 1.02(4) . ?
C15 C14 1.370(5) . ?
C15 H15 0.92(4) . ?
C1 C2 1.476(5) . ?
C14 H14 0.96(4) . ?
C20 C19 1.382(5) . ?
C20 C21 1.397(5) . ?
C20 H20 1.00(4) . ?
C19 H19 1.06(4) . ?
C21 H21 1.02(4) . ?
C2 H2A 1.03(4) . ?
C2 H2B 1.00(4) . ?
C10 C9 1.388(5) . ?
C10 H10 0.95(4) . ?
C8 C7 1.373(6) . ?
C8 C9 1.377(6) . ?
C8 H8 1.01(5) . ?
C7 H7 0.99(5) . ?
C9 H9 0.95(5) . ?

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
C3 O1 C2 116.5(2) . . ?
C3 N1 C22 105.1(2) . . ?
C22 C17 C4 107.9(2) . . ?
C18 C17 C4 131.9(3) . . ?
C18 C17 C22 120.1(3) . . ?
C16 C11 C4 122.3(3) . . ?
C16 C11 C12 118.3(3) . . ?
C12 C11 C4 119.4(2) . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 C10 118.2(3) . . ?
C10 C5 C4 119.4(3) . . ?
C11 C16 C15 120.8(3) . . ?
C11 C16 H16 121(2) . . ?
C15 C16 H16 118(2) . . ?
C5 C6 C7 121.4(4) . . ?
C5 C6 H6 119(2) . . ?
C7 C6 H6 120(2) . . ?
O1 C3 C4 117.3(2) . . ?
N1 C3 O1 124.7(3) . . ?
N1 C3 C4 117.9(2) . . ?
C17 C4 C11 115.1(2) . . ?
C17 C4 C5 109.5(2) . . ?
C17 C4 C3 96.8(2) . . ?
C5 C4 C11 112.1(2) . . ?
C3 C4 C11 108.7(2) . . ?
C3 C4 C5 113.9(2) . . ?
C11 C12 H12 119.2(18) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 120.5(18) . . ?
C17 C22 N1 112.2(2) . . ?
C21 C22 N1 126.3(3) . . ?
C21 C22 C17 121.4(3) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 123(2) . . ?
C19 C18 H18 118(2) . . ?
C12 C13 H13 123(2) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 117(2) . . ?
C16 C15 H15 120(3) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120(3) . . ?
F3 C1 F2 105.5(3) . . ?
F3 C1 F1 106.7(3) . . ?
F3 C1 C2 114.7(3) . . ?
F2 C1 C2 112.3(3) . . ?
F1 C1 F2 107.2(4) . . ?
F1 C1 C2 110.0(3) . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 121(2) . . ?
C15 C14 H14 118(2) . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 120(2) . . ?
C21 C20 H20 119(2) . . ?
C18 C19 H19 122(2) . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 117(2) . . ?
C22 C21 C20 118.2(3) . . ?
C22 C21 H21 120(2) . . ?
C20 C21 H21 122(2) . . ?
O1 C2 C1 110.9(3) . . ?
O1 C2 H2A 105(2) . . ?
O1 C2 H2B 107(2) . . ?
C1 C2 H2A 110(2) . . ?
C1 C2 H2B 106(2) . . ?
H2A C2 H2B 118(3) . . ?
C5 C10 H10 119(2) . . ?
C9 C10 C5 120.4(4) . . ?
C9 C10 H10 121(2) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120(3) . . ?
C9 C8 H8 121(3) . . ?
C6 C7 H7 122(3) . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 118(3) . . ?
C10 C9 H9 120(2) . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 H9 120(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
O1 C3 C4 C17 179.5(2) . . . . ?
O1 C3 C4 C11 60.1(3) . . . . ?
O1 C3 C4 C5 -65.7(3) . . . . ?
N1 C3 C4 C17 2.6(3) . . . . ?
N1 C3 C4 C11 -116.8(3) . . . . ?
N1 C3 C4 C5 117.5(3) . . . . ?
N1 C22 C21 C20 178.6(3) . . . . ?
F3 C1 C2 O1 -62.5(4) . . . . ?
F2 C1 C2 O1 57.9(4) . . . . ?
F1 C1 C2 O1 177.3(3) . . . . ?
C17 C22 C21 C20 0.7(5) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C11 C16 C15 C14 -0.1(5) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C5 C10 C9 C8 -0.9(6) . . . . ?
C16 C11 C4 C17 -5.6(4) . . . . ?
C16 C11 C4 C5 -131.6(3) . . . . ?
C16 C11 C4 C3 101.6(3) . . . . ?
C16 C11 C12 C13 2.7(4) . . . . ?
C16 C15 C14 C13 1.6(5) . . . . ?
C6 C5 C4 C17 83.7(3) . . . . ?
C6 C5 C4 C11 -147.3(3) . . . . ?
C6 C5 C4 C3 -23.4(4) . . . . ?
C6 C5 C10 C9 0.3(5) . . . . ?
C3 O1 C2 C1 -104.0(3) . . . . ?
C3 N1 C22 C17 1.6(3) . . . . ?
C3 N1 C22 C21 -176.5(3) . . . . ?
C4 C17 C22 N1 0.0(3) . . . . ?
C4 C17 C22 C21 178.2(3) . . . . ?
C4 C17 C18 C19 -178.3(3) . . . . ?
C4 C11 C16 C15 178.5(3) . . . . ?
C4 C11 C12 C13 -177.8(3) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C4 C5 C10 C9 176.2(3) . . . . ?
C12 C11 C16 C15 -2.1(5) . . . . ?
C12 C11 C4 C17 174.9(3) . . . . ?
C12 C11 C4 C5 48.9(3) . . . . ?
C12 C11 C4 C3 -77.9(3) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C22 N1 C3 O1 -179.3(3) . . . . ?
C22 N1 C3 C4 -2.7(3) . . . . ?
C22 C17 C4 C11 113.0(3) . . . . ?
C22 C17 C4 C5 -119.6(3) . . . . ?
C22 C17 C4 C3 -1.3(3) . . . . ?
C22 C17 C18 C19 -1.8(4) . . . . ?
C18 C17 C4 C11 -70.2(4) . . . . ?
C18 C17 C4 C5 57.2(4) . . . . ?
C18 C17 C4 C3 175.5(3) . . . . ?
C18 C17 C22 N1 -177.2(3) . . . . ?
C18 C17 C22 C21 0.9(4) . . . . ?
C19 C20 C21 C22 -1.5(5) . . . . ?
C21 C20 C19 C18 0.7(5) . . . . ?
C2 O1 C3 N1 9.9(4) . . . . ?
C2 O1 C3 C4 -166.7(2) . . . . ?
C10 C5 C6 C7 0.2(5) . . . . ?
C10 C5 C4 C17 -92.0(3) . . . . ?
C10 C5 C4 C11 37.0(4) . . . . ?
C10 C5 C4 C3 160.9(3) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C9 C8 C7 C6 -0.5(6) . . . . ?

_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_agml_868_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2257366'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_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         'C22 H15 F4 N S'
_chemical_formula_sum            'C22 H15 F4 N S'
_chemical_formula_weight         401.41
_chemical_absolute_configuration ?
_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'
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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   6.8631(3)
_cell_length_b                   16.0474(5)
_cell_length_c                   16.9025(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1861.56(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5820
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1546 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.6654.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9025
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_min         2.724
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3446
_reflns_number_total             3786
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.045
_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)+(0.0509P)²+0.2850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1112
_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:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C12(H12), C21(H21), C20(H20), C18(H18), C15(H15),
 C10(H10), C9(H9), C8(H8), C7(H7), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78892(13) 0.68610(5) 0.50428(5) 0.0432(2) Uani 1 1 d . . . . .
F2 F 0.6675(6) 0.5999(2) 0.6621(2) 0.0975(11) Uani 1 1 d . . . . .
F3 F 0.9029(6) 0.53571(17) 0.60886(18) 0.0979(12) Uani 1 1 d . . . . .
F1 F 0.9483(8) 0.6050(2) 0.7143(2) 0.1200(16) Uani 1 1 d . . . . .
F4 F -0.1382(4) 0.94170(16) 0.53177(16) 0.0656(7) Uani 1 1 d . . . . .
N1 N 0.5435(4) 0.77614(19) 0.59489(15) 0.0397(7) Uani 1 1 d . . . . .
C17 C 0.2991(5) 0.82169(17) 0.5084(2) 0.0330(6) Uani 1 1 d . . . . .
C16 C 0.5564(6) 0.9049(2) 0.3958(2) 0.0420(8) Uani 1 1 d . . . . .
C14 C 0.7727(6) 0.9048(3) 0.2842(2) 0.0541(10) Uani 1 1 d . . . . .
H14 H 0.846282 0.933570 0.246976 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7696(6) 0.8197(3) 0.2838(2) 0.0514(10) Uani 1 1 d . . . . .
H13 H 0.840360 0.790511 0.245910 0.062 Uiso 1 1 calc R U . . .
C12 C 0.6615(6) 0.7766(2) 0.3397(2) 0.0447(8) Uani 1 1 d . . . . .
H12 H 0.661818 0.718645 0.339346 0.054 Uiso 1 1 calc R U . . .
C11 C 0.5527(5) 0.81885(19) 0.39604(18) 0.0334(7) Uani 1 1 d . . . . .
C4 C 0.4400(5) 0.76967(18) 0.45933(17) 0.0313(6) Uani 1 1 d . . . . .
C3 C 0.5833(5) 0.74613(19) 0.52623(17) 0.0335(7) Uani 1 1 d . . . . .
C2 C 0.9047(6) 0.6816(2) 0.5993(2) 0.0466(9) Uani 1 1 d . . . . .
H2A H 1.044719 0.683880 0.591876 0.056 Uiso 1 1 calc R U . . .
H2B H 0.866881 0.730350 0.629574 0.056 Uiso 1 1 calc R U . . .
C1 C 0.8563(8) 0.6057(3) 0.6460(3) 0.0617(12) Uani 1 1 d . . . . .
C22 C 0.3679(6) 0.8223(2) 0.58615(19) 0.0370(7) Uani 1 1 d . . . . .
C21 C 0.2677(6) 0.8631(2) 0.6454(2) 0.0467(9) Uani 1 1 d . . . . .
H21 H 0.314264 0.863458 0.697105 0.056 Uiso 1 1 calc R U . . .
C20 C 0.0954(6) 0.9038(2) 0.6259(2) 0.0490(9) Uani 1 1 d . . . . .
H20 H 0.024693 0.931841 0.664519 0.059 Uiso 1 1 calc R U . . .
C19 C 0.0304(6) 0.9021(2) 0.5491(2) 0.0439(8) Uani 1 1 d . . . . .
C18 C 0.1266(5) 0.8606(2) 0.48858(19) 0.0394(8) Uani 1 1 d . . . . .
H18 H 0.077302 0.858984 0.437348 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6663(7) 0.9480(3) 0.3401(3) 0.0541(10) Uani 1 1 d . . . . .
H15 H 0.668167 1.005966 0.340490 0.065 Uiso 1 1 calc R U . . .
C5 C 0.3302(5) 0.6947(2) 0.42484(18) 0.0337(7) Uani 1 1 d . . . . .
C10 C 0.2388(7) 0.7016(3) 0.3521(2) 0.0522(10) Uani 1 1 d . . . . .
H10 H 0.249804 0.750699 0.323195 0.063 Uiso 1 1 calc R U . . .
C9 C 0.1307(7) 0.6357(3) 0.3223(3) 0.0664(13) Uani 1 1 d . . . . .
H9 H 0.071199 0.640640 0.273091 0.080 Uiso 1 1 calc R U . . .
C8 C 0.1106(7) 0.5631(3) 0.3646(3) 0.0681(14) Uani 1 1 d . . . . .
H8 H 0.037760 0.519124 0.344267 0.082 Uiso 1 1 calc R U . . .
C7 C 0.1985(7) 0.5560(3) 0.4367(3) 0.0615(12) Uani 1 1 d . . . . .
H7 H 0.184435 0.507089 0.465651 0.074 Uiso 1 1 calc R U . . .
C6 C 0.3090(5) 0.6212(2) 0.4677(2) 0.0441(8) Uani 1 1 d . . . . .
H6 H 0.368547 0.615524 0.516797 0.053 Uiso 1 1 calc R U . . .
H16 H 0.474(7) 0.929(2) 0.431(2) 0.049(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.748(3) . ?
S1 C2 1.794(4) . ?
F2 C1 1.327(6) . ?
F3 C1 1.326(5) . ?
F1 C1 1.316(5) . ?
F4 C19 1.353(5) . ?
N1 C3 1.286(4) . ?
N1 C22 1.422(5) . ?
C17 C4 1.523(4) . ?
C17 C22 1.396(5) . ?
C17 C18 1.380(5) . ?
C16 C11 1.382(5) . ?
C16 C15 1.390(5) . ?
C16 H16 0.91(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.367(6) . ?
C14 C15 1.380(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.388(5) . ?
C11 C4 1.538(4) . ?
C4 C3 1.546(4) . ?
C4 C5 1.534(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.489(6) . ?
C22 C21 1.381(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.373(5) . ?
C19 C18 1.388(5) . ?
C18 H18 0.9300 . ?
C15 H15 0.9300 . ?
C5 C10 1.384(5) . ?
C5 C6 1.392(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.388(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(8) . ?
C8 H8 0.9300 . ?
C8 C7 1.365(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.393(5) . ?
C6 H6 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
C3 S1 C2 100.93(16) . . ?
C3 N1 C22 106.4(3) . . ?
C22 C17 C4 107.6(3) . . ?
C18 C17 C4 131.3(3) . . ?
C18 C17 C22 121.0(3) . . ?
C11 C16 C15 120.6(4) . . ?
C11 C16 H16 114(3) . . ?
C15 C16 H16 125(3) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C13 C12 H12 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 C4 121.6(3) . . ?
C12 C11 C4 119.8(3) . . ?
C17 C4 C11 114.6(3) . . ?
C17 C4 C3 98.0(2) . . ?
C17 C4 C5 109.0(3) . . ?
C11 C4 C3 108.3(3) . . ?
C5 C4 C11 112.6(2) . . ?
C5 C4 C3 113.5(3) . . ?
N1 C3 S1 124.7(3) . . ?
N1 C3 C4 115.7(3) . . ?
C4 C3 S1 119.5(2) . . ?
S1 C2 H2A 108.7 . . ?
S1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C1 C2 S1 114.1(3) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
F2 C1 C2 112.6(4) . . ?
F3 C1 F2 105.8(4) . . ?
F3 C1 C2 112.8(4) . . ?
F1 C1 F2 106.8(5) . . ?
F1 C1 F3 107.0(4) . . ?
F1 C1 C2 111.4(4) . . ?
C17 C22 N1 112.4(3) . . ?
C21 C22 N1 126.4(3) . . ?
C21 C22 C17 121.2(3) . . ?
C22 C21 H21 120.9 . . ?
C22 C21 C20 118.3(3) . . ?
C20 C21 H21 120.9 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
F4 C19 C20 118.2(3) . . ?
F4 C19 C18 118.3(3) . . ?
C20 C19 C18 123.5(3) . . ?
C17 C18 C19 116.5(3) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.0(4) . . ?
C14 C15 H15 120.0 . . ?
C10 C5 C4 119.8(3) . . ?
C10 C5 C6 118.8(3) . . ?
C6 C5 C4 121.2(3) . . ?
C5 C10 H10 119.9 . . ?
C5 C10 C9 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C9 C8 H8 120.3 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C6 120.9(4) . . ?
C6 C7 H7 119.5 . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?

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
S1 C2 C1 F2 -61.4(5) . . . . ?
S1 C2 C1 F3 58.3(5) . . . . ?
S1 C2 C1 F1 178.7(4) . . . . ?
F4 C19 C18 C17 179.3(3) . . . . ?
N1 C22 C21 C20 -178.6(3) . . . . ?
C17 C4 C3 S1 -178.3(2) . . . . ?
C17 C4 C3 N1 -1.0(4) . . . . ?
C17 C4 C5 C10 89.3(4) . . . . ?
C17 C4 C5 C6 -86.2(4) . . . . ?
C17 C22 C21 C20 0.1(5) . . . . ?
C16 C11 C4 C17 13.3(5) . . . . ?
C16 C11 C4 C3 -95.0(4) . . . . ?
C16 C11 C4 C5 138.6(3) . . . . ?
C14 C13 C12 C11 0.9(6) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C13 C12 C11 C16 -0.7(6) . . . . ?
C13 C12 C11 C4 -177.7(3) . . . . ?
C12 C11 C4 C17 -169.8(3) . . . . ?
C12 C11 C4 C3 81.9(4) . . . . ?
C12 C11 C4 C5 -44.5(4) . . . . ?
C11 C16 C15 C14 0.2(6) . . . . ?
C11 C4 C3 S1 -59.0(3) . . . . ?
C11 C4 C3 N1 118.3(3) . . . . ?
C11 C4 C5 C10 -39.1(4) . . . . ?
C11 C4 C5 C6 145.4(3) . . . . ?
C4 C17 C22 N1 0.4(4) . . . . ?
C4 C17 C22 C21 -178.4(3) . . . . ?
C4 C17 C18 C19 178.6(3) . . . . ?
C4 C5 C10 C9 -176.7(4) . . . . ?
C4 C5 C6 C7 176.1(3) . . . . ?
C3 S1 C2 C1 95.2(3) . . . . ?
C3 N1 C22 C17 -1.1(4) . . . . ?
C3 N1 C22 C21 177.7(4) . . . . ?
C3 C4 C5 C10 -162.6(3) . . . . ?
C3 C4 C5 C6 21.8(4) . . . . ?
C2 S1 C3 N1 0.6(3) . . . . ?
C2 S1 C3 C4 177.7(2) . . . . ?
C22 N1 C3 S1 178.4(2) . . . . ?
C22 N1 C3 C4 1.3(4) . . . . ?
C22 C17 C4 C11 -114.2(3) . . . . ?
C22 C17 C4 C3 0.3(3) . . . . ?
C22 C17 C4 C5 118.6(3) . . . . ?
C22 C17 C18 C19 2.1(5) . . . . ?
C22 C21 C20 C19 0.1(6) . . . . ?
C21 C20 C19 F4 179.6(3) . . . . ?
C21 C20 C19 C18 0.9(6) . . . . ?
C20 C19 C18 C17 -2.0(5) . . . . ?
C18 C17 C4 C11 69.0(4) . . . . ?
C18 C17 C4 C3 -176.6(3) . . . . ?
C18 C17 C4 C5 -58.2(4) . . . . ?
C18 C17 C22 N1 177.6(3) . . . . ?
C18 C17 C22 C21 -1.2(5) . . . . ?
C15 C16 C11 C12 0.2(6) . . . . ?
C15 C16 C11 C4 177.1(3) . . . . ?
C15 C14 C13 C12 -0.6(7) . . . . ?
C5 C4 C3 S1 66.9(3) . . . . ?
C5 C4 C3 N1 -115.8(3) . . . . ?
C5 C10 C9 C8 0.8(7) . . . . ?
C10 C5 C6 C7 0.5(5) . . . . ?
C10 C9 C8 C7 -0.1(8) . . . . ?
C9 C8 C7 C6 -0.4(7) . . . . ?
C8 C7 C6 C5 0.2(6) . . . . ?
C6 C5 C10 C9 -1.0(6) . . . . ?

_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_momo_a
_database_code_depnum_ccdc_archive 'CCDC 2269435'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-06-13 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-06-13
_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         'C10 H6 Br F3 N O'
_chemical_formula_sum            'C10 H6 Br F3 N O'
_chemical_formula_weight         293.07
_chemical_absolute_configuration ?
_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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   17.093(12)
_cell_length_b                   10.057(10)
_cell_length_c                   6.991(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.89(3)
_cell_angle_gamma                90
_cell_volume                     1098.8(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2839
_cell_measurement_temperature    298
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.694
_shelx_estimated_absorpt_T_min   0.499
_exptl_absorpt_coefficient_mu    3.759
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5500
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_min         2.408
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.930
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                1790
_reflns_number_total             2145
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 693 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1132
_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:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C8(H8), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.60748(4) 0.96935(6) 0.85743(10) 0.0893(3) Uani 1 1 d . . . . .
F1 F 0.3047(3) 0.0326(6) 0.5548(9) 0.1083(15) Uani 1 1 d . . . . .
O2 O 0.4128(2) 0.3413(5) 0.6625(6) 0.0650(11) Uani 1 1 d . . . . .
F3 F 0.2735(3) 0.2101(6) 0.3709(6) 0.1097(17) Uani 1 1 d . . . . .
F4 F 0.2737(3) 0.2104(6) 0.6767(8) 0.1088(17) Uani 1 1 d . . . . .
N1 N 0.5627(3) 0.3228(6) 0.8133(8) 0.0672(13) Uani 1 1 d . . . . .
C6 C 0.4937(3) 0.3935(7) 0.7434(8) 0.0519(12) Uani 1 1 d . . . . .
C10 C 0.5927(3) 0.5579(7) 0.8428(7) 0.0502(12) Uani 1 1 d . . . . .
C9 C 0.6250(3) 0.6851(7) 0.8754(7) 0.0552(12) Uani 1 1 d . . . . .
H9 H 0.683699 0.700404 0.934533 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4467(3) 0.6402(7) 0.6964(7) 0.0588(13) Uani 1 1 d . . . . .
H7 H 0.388097 0.624440 0.637573 0.071 Uiso 1 1 calc R U . . .
C8 C 0.4791(3) 0.7711(7) 0.7289(8) 0.0634(12) Uani 1 1 d . . . . .
H8 H 0.442137 0.843596 0.691950 0.076 Uiso 1 1 calc R U . . .
C1 C 0.3152(4) 0.1650(8) 0.5659(10) 0.0731(17) Uani 1 1 d . . . . .
C2 C 0.4076(4) 0.1998(8) 0.6576(10) 0.0716(16) Uani 1 1 d . . . . .
H2A H 0.435412 0.163789 0.797907 0.086 Uiso 1 1 calc R U . . .
H2B H 0.435519 0.163644 0.572689 0.086 Uiso 1 1 calc R U . . .
C3 C 0.5035(3) 0.5377(7) 0.7533(7) 0.0520(13) Uani 1 1 d . . . . .
C4 C 0.5671(4) 0.7898(7) 0.8170(7) 0.0602(13) Uani 1 1 d . . . . .
C5 C 0.6329(4) 0.4228(7) 0.8819(10) 0.0667(14) Uani 1 1 d . . . . .
H5 H 0.691221 0.404612 0.938803 0.080 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
Br1 C4 1.913(7) . ?
F1 C1 1.341(10) . ?
O2 C6 1.370(6) . ?
O2 C2 1.426(9) . ?
F3 C1 1.336(8) . ?
F4 C1 1.325(8) . ?
N1 C6 1.291(8) . ?
N1 C5 1.488(9) . ?
C6 C3 1.458(8) . ?
C10 C9 1.375(10) . ?
C10 C3 1.409(7) . ?
C10 C5 1.497(10) . ?
C9 H9 0.9300 . ?
C9 C4 1.389(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.410(10) . ?
C7 C3 1.360(9) . ?
C8 H8 0.9300 . ?
C8 C4 1.388(8) . ?
C1 C2 1.487(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5 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
C6 O2 C2 115.8(5) . . ?
C6 N1 C5 104.1(6) . . ?
O2 C6 C3 118.5(5) . . ?
N1 C6 O2 124.0(6) . . ?
N1 C6 C3 117.4(5) . . ?
C9 C10 C3 119.9(7) . . ?
C9 C10 C5 133.6(5) . . ?
C3 C10 C5 106.5(6) . . ?
C10 C9 H9 121.1 . . ?
C10 C9 C4 117.7(5) . . ?
C4 C9 H9 121.1 . . ?
C8 C7 H7 120.9 . . ?
C3 C7 H7 120.9 . . ?
C3 C7 C8 118.3(5) . . ?
C7 C8 H8 120.6 . . ?
C4 C8 C7 118.8(6) . . ?
C4 C8 H8 120.6 . . ?
F1 C1 C2 110.6(7) . . ?
F3 C1 F1 106.0(5) . . ?
F3 C1 C2 113.2(5) . . ?
F4 C1 F1 106.6(5) . . ?
F4 C1 F3 106.8(6) . . ?
F4 C1 C2 113.2(5) . . ?
O2 C2 C1 106.8(6) . . ?
O2 C2 H2A 110.4 . . ?
O2 C2 H2B 110.4 . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C10 C3 C6 104.3(5) . . ?
C7 C3 C6 133.3(5) . . ?
C7 C3 C10 122.4(7) . . ?
C9 C4 Br1 120.1(4) . . ?
C8 C4 Br1 117.0(5) . . ?
C8 C4 C9 122.9(6) . . ?
N1 C5 C10 107.7(5) . . ?
N1 C5 H5 126.2 . . ?
C10 C5 H5 126.2 . . ?

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
F1 C1 C2 O2 179.7(6) . . . . ?
O2 C6 C3 C10 179.9(4) . . . . ?
O2 C6 C3 C7 -0.1(9) . . . . ?
F3 C1 C2 O2 61.0(8) . . . . ?
F4 C1 C2 O2 -60.7(7) . . . . ?
N1 C6 C3 C10 0.3(7) . . . . ?
N1 C6 C3 C7 -179.7(5) . . . . ?
C6 O2 C2 C1 179.8(4) . . . . ?
C6 N1 C5 C10 0.9(7) . . . . ?
C10 C9 C4 Br1 -180.0(3) . . . . ?
C10 C9 C4 C8 0.2(7) . . . . ?
C9 C10 C3 C6 180.0(5) . . . . ?
C9 C10 C3 C7 0.0(6) . . . . ?
C9 C10 C5 N1 179.7(5) . . . . ?
C7 C8 C4 Br1 180.0(4) . . . . ?
C7 C8 C4 C9 -0.2(7) . . . . ?
C8 C7 C3 C6 -180.0(6) . . . . ?
C8 C7 C3 C10 0.0(7) . . . . ?
C2 O2 C6 N1 -0.3(8) . . . . ?
C2 O2 C6 C3 -179.9(5) . . . . ?
C3 C10 C9 C4 -0.1(6) . . . . ?
C3 C10 C5 N1 -0.8(5) . . . . ?
C3 C7 C8 C4 0.1(7) . . . . ?
C5 N1 C6 O2 179.7(5) . . . . ?
C5 N1 C6 C3 -0.7(7) . . . . ?
C5 C10 C9 C4 179.4(5) . . . . ?
C5 C10 C3 C6 0.3(5) . . . . ?
C5 C10 C3 C7 -179.7(5) . . . . ?

_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_agml_1104_0m
_database_code_depnum_ccdc_archive 'CCDC 2288102'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-08-11 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H13 F3 N O)'
_chemical_formula_sum            'C34 H26 F6 N2 O2'
_chemical_formula_weight         608.57
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0648(8)
_cell_length_b                   11.6308(8)
_cell_length_c                   13.8611(10)
_cell_angle_alpha                68.976(2)
_cell_angle_beta                 87.671(3)
_cell_angle_gamma                69.921(2)
_cell_volume                     1416.21(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.360
_cell_measurement_theta_min      2.541
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0974 after correction.
The Ratio of minimum to maximum transmission is 0.6324.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18765
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.004
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4679
_reflns_number_total             5794
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5794
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0626
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1047P)²+0.3412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1917
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2'(H2'A,H2'B)
2.b Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C8(H8), C7(H7), C5(H5), C11(H11), C13(H13), C16(H16),
 C15(H15), C14(H14), C9(H9), C10(H10), C8'(H8'), C7'(H7'), C5'(H5'), C11'(H11'),
  C13'(H13'), C14'(H14'), C16'(H16'), C9'(H9'), C10'(H10'), C15'(H15')
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.4264(2) 0.33581(19) 0.55918(11) 0.1028(6) Uani 1 1 d . . . . .
F1' F 0.0874(2) 0.54545(15) 0.59791(13) 0.0941(5) Uani 1 1 d . . . . .
F3 F 0.25577(19) 0.3633(2) 0.45434(16) 0.1035(6) Uani 1 1 d . . . . .
F2' F 0.22902(18) 0.64859(19) 0.54459(15) 0.0993(6) Uani 1 1 d . . . . .
F3' F 0.0529(2) 0.68291(18) 0.44253(11) 0.0933(5) Uani 1 1 d . . . . .
F1 F 0.3893(2) 0.47493(15) 0.40493(12) 0.0956(6) Uani 1 1 d . . . . .
O1' O 0.03630(17) 0.74057(15) 0.67729(10) 0.0548(4) Uani 1 1 d . . . . .
O1 O 0.45546(16) 0.27839(14) 0.32379(10) 0.0535(4) Uani 1 1 d . . . . .
N1' N 0.14889(18) 0.89589(17) 0.63603(11) 0.0499(4) Uani 1 1 d . . . . .
H1' H 0.147713 0.916470 0.569876 0.060 Uiso 1 1 calc R U . . .
N1 N 0.34376(17) 0.12260(16) 0.36618(11) 0.0468(4) Uani 1 1 d . . . . .
H1 H 0.336975 0.108910 0.431110 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5307(2) 0.3995(2) -0.15548(15) 0.0585(5) Uani 1 1 d . . . . .
H8 H 0.602196 0.426022 -0.190461 0.070 Uiso 1 1 calc R U . . .
C7 C 0.5319(2) 0.36781(18) -0.04992(14) 0.0460(4) Uani 1 1 d . . . . .
H7 H 0.602838 0.375580 -0.014427 0.055 Uiso 1 1 calc R U . . .
C5 C 0.43449(19) 0.29311(17) 0.11692(13) 0.0407(4) Uani 1 1 d . . . . .
H5 H 0.479480 0.337857 0.139551 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3195(2) 0.31889(18) -0.05144(14) 0.0459(4) Uani 1 1 d . . . . .
H11 H 0.247694 0.292354 -0.017020 0.055 Uiso 1 1 calc R U . . .
C4 C 0.38645(18) 0.21057(17) 0.19292(13) 0.0390(4) Uani 1 1 d . . . . .
C12 C 0.32517(18) 0.10962(17) 0.20230(13) 0.0396(4) Uani 1 1 d . . . . .
C13 C 0.3030(2) 0.04970(19) 0.13732(15) 0.0499(5) Uani 1 1 d . . . . .
H13 H 0.321941 0.077944 0.068191 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3906(3) 0.3570(2) 0.46149(16) 0.0623(6) Uani 1 1 d . . . . .
C6' C 0.07412(17) 0.68739(17) 0.99832(13) 0.0372(4) Uani 1 1 d . . . . .
C3 C 0.39504(19) 0.20267(18) 0.30110(13) 0.0427(4) Uani 1 1 d . . . . .
C2 C 0.4881(2) 0.2507(2) 0.43019(15) 0.0584(5) Uani 1 1 d . . . . .
H2A H 0.585540 0.243614 0.441591 0.070 Uiso 1 1 calc R U . . .
H2B H 0.478771 0.167365 0.472214 0.070 Uiso 1 1 calc R U . . .
C16 C 0.2457(2) -0.0387(2) 0.34644(15) 0.0564(5) Uani 1 1 d . . . . .
H16 H 0.225467 -0.067075 0.415261 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2218(3) -0.0953(2) 0.27919(18) 0.0665(6) Uani 1 1 d . . . . .
H15 H 0.184938 -0.162695 0.303382 0.080 Uiso 1 1 calc R U . . .
C14 C 0.2518(3) -0.0534(2) 0.17727(17) 0.0622(6) Uani 1 1 d . . . . .
H14 H 0.237523 -0.094759 0.134382 0.075 Uiso 1 1 calc R U . . .
C17 C 0.30067(19) 0.06151(18) 0.30769(13) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.4239(3) 0.3920(2) -0.20992(16) 0.0651(6) Uani 1 1 d . . . . .
H9 H 0.423455 0.413360 -0.281340 0.078 Uiso 1 1 calc R U . . .
C10 C 0.3178(2) 0.3528(2) -0.15788(15) 0.0580(5) Uani 1 1 d . . . . .
H10 H 0.244949 0.349094 -0.194510 0.070 Uiso 1 1 calc R U . . .
C8' C 0.1022(2) 0.5326(2) 1.17454(14) 0.0514(5) Uani 1 1 d . . . . .
H8' H 0.124542 0.446330 1.220873 0.062 Uiso 1 1 calc R U . . .
C7' C 0.10462(19) 0.55902(17) 1.06930(13) 0.0433(4) Uani 1 1 d . . . . .
H7' H 0.126971 0.490134 1.045288 0.052 Uiso 1 1 calc R U . . .
C5' C 0.0762(2) 0.71011(18) 0.88731(13) 0.0427(4) Uani 1 1 d . . . . .
H5' H 0.044830 0.655322 0.866628 0.051 Uiso 1 1 calc R U . . .
C11' C 0.03550(19) 0.78924(18) 1.03634(14) 0.0437(4) Uani 1 1 d . . . . .
H11' H 0.012033 0.875876 0.990415 0.052 Uiso 1 1 calc R U . . .
C4' C 0.11659(19) 0.79798(17) 0.81079(13) 0.0399(4) Uani 1 1 d . . . . .
C3' C 0.1017(2) 0.81206(19) 0.70091(13) 0.0450(4) Uani 1 1 d . . . . .
C2' C 0.0018(2) 0.7706(2) 0.57070(14) 0.0547(5) Uani 1 1 d . . . . .
H2'A H 0.017209 0.851093 0.528875 0.066 Uiso 1 1 calc R U . . .
H2'B H -0.097661 0.783818 0.558883 0.066 Uiso 1 1 calc R U . . .
C13' C 0.23775(19) 0.93065(17) 0.87401(14) 0.0437(4) Uani 1 1 d . . . . .
H13' H 0.228107 0.894889 0.944478 0.052 Uiso 1 1 calc R U . . .
C14' C 0.3053(2) 1.02248(19) 0.83735(17) 0.0523(5) Uani 1 1 d . . . . .
H14' H 0.340278 1.048494 0.883961 0.063 Uiso 1 1 calc R U . . .
C16' C 0.2728(2) 1.0377(2) 0.66114(16) 0.0543(5) Uani 1 1 d . . . . .
H16' H 0.286175 1.071579 0.591202 0.065 Uiso 1 1 calc R U . . .
C1' C 0.0920(3) 0.6607(2) 0.54005(16) 0.0600(5) Uani 1 1 d . . . . .
C17' C 0.20349(19) 0.94721(18) 0.69726(14) 0.0444(4) Uani 1 1 d . . . . .
C9' C 0.0665(2) 0.6342(2) 1.21114(14) 0.0530(5) Uani 1 1 d . . . . .
H9' H 0.065858 0.616458 1.282102 0.064 Uiso 1 1 calc R U . . .
C10' C 0.0319(2) 0.7622(2) 1.14193(15) 0.0482(4) Uani 1 1 d . . . . .
H10' H 0.005874 0.830848 1.166429 0.058 Uiso 1 1 calc R U . . .
C12' C 0.18521(18) 0.89362(16) 0.80346(13) 0.0393(4) Uani 1 1 d . . . . .
C15' C 0.3211(2) 1.0755(2) 0.73312(17) 0.0564(5) Uani 1 1 d . . . . .
H15' H 0.365120 1.137752 0.710616 0.068 Uiso 1 1 calc R U . . .
C6 C 0.42770(18) 0.32403(16) 0.00495(13) 0.0384(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
F2 C1 1.328(2) . ?
F1' C1' 1.308(3) . ?
F3 C1 1.340(3) . ?
F2' C1' 1.339(3) . ?
F3' C1' 1.331(2) . ?
F1 C1 1.309(3) . ?
O1' C3' 1.349(2) . ?
O1' C2' 1.419(2) . ?
O1 C3 1.351(2) . ?
O1 C2 1.419(2) . ?
N1' H1' 0.8600 . ?
N1' C3' 1.280(2) . ?
N1' C17' 1.416(2) . ?
N1 H1 0.8600 . ?
N1 C3 1.279(2) . ?
N1 C17 1.415(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.374(2) . ?
C8 C9 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.348(2) . ?
C5 C6 1.461(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.383(3) . ?
C11 C6 1.395(2) . ?
C4 C12 1.469(2) . ?
C4 C3 1.473(2) . ?
C12 C13 1.386(2) . ?
C12 C17 1.410(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(3) . ?
C1 C2 1.482(3) . ?
C6' C7' 1.395(2) . ?
C6' C5' 1.465(2) . ?
C6' C11' 1.395(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C15 1.388(3) . ?
C16 C17 1.387(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C8' H8' 0.9300 . ?
C8' C7' 1.380(2) . ?
C8' C9' 1.381(3) . ?
C7' H7' 0.9300 . ?
C5' H5' 0.9300 . ?
C5' C4' 1.344(2) . ?
C11' H11' 0.9300 . ?
C11' C10' 1.384(2) . ?
C4' C3' 1.480(2) . ?
C4' C12' 1.472(2) . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C2' C1' 1.482(3) . ?
C13' H13' 0.9300 . ?
C13' C14' 1.394(3) . ?
C13' C12' 1.386(2) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.379(3) . ?
C16' H16' 0.9300 . ?
C16' C17' 1.394(3) . ?
C16' C15' 1.388(3) . ?
C17' C12' 1.410(2) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.380(3) . ?
C10' H10' 0.9300 . ?
C15' H15' 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
C3' O1' C2' 117.60(15) . . ?
C3 O1 C2 117.41(15) . . ?
C3' N1' H1' 127.6 . . ?
C3' N1' C17' 104.75(15) . . ?
C17' N1' H1' 127.6 . . ?
C3 N1 H1 127.6 . . ?
C3 N1 C17 104.74(14) . . ?
C17 N1 H1 127.6 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.34(19) . . ?
C9 C8 H8 119.8 . . ?
C8 C7 H7 119.5 . . ?
C8 C7 C6 120.91(18) . . ?
C6 C7 H7 119.5 . . ?
C4 C5 H5 114.6 . . ?
C4 C5 C6 130.79(16) . . ?
C6 C5 H5 114.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C6 120.80(17) . . ?
C6 C11 H11 119.6 . . ?
C5 C4 C12 136.80(16) . . ?
C5 C4 C3 121.44(16) . . ?
C12 C4 C3 101.70(14) . . ?
C13 C12 C4 135.22(16) . . ?
C13 C12 C17 119.35(17) . . ?
C17 C12 C4 105.05(15) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.85(18) . . ?
C14 C13 H13 120.6 . . ?
F2 C1 F3 108.0(2) . . ?
F2 C1 C2 110.2(2) . . ?
F3 C1 C2 111.46(19) . . ?
F1 C1 F2 107.05(19) . . ?
F1 C1 F3 105.5(2) . . ?
F1 C1 C2 114.3(2) . . ?
C7' C6' C5' 118.83(15) . . ?
C11' C6' C7' 118.15(15) . . ?
C11' C6' C5' 122.94(16) . . ?
O1 C3 C4 118.56(15) . . ?
N1 C3 O1 125.54(16) . . ?
N1 C3 C4 115.89(16) . . ?
O1 C2 C1 109.97(18) . . ?
O1 C2 H2A 109.7 . . ?
O1 C2 H2B 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C17 C16 C15 117.88(19) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C12 C17 N1 112.50(15) . . ?
C16 C17 N1 125.95(16) . . ?
C16 C17 C12 121.50(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.73(18) . . ?
C10 C9 H9 120.1 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.23(19) . . ?
C9 C10 H10 119.9 . . ?
C7' C8' H8' 120.0 . . ?
C7' C8' C9' 120.08(18) . . ?
C9' C8' H8' 120.0 . . ?
C6' C7' H7' 119.5 . . ?
C8' C7' C6' 121.07(17) . . ?
C8' C7' H7' 119.5 . . ?
C6' C5' H5' 115.0 . . ?
C4' C5' C6' 129.93(16) . . ?
C4' C5' H5' 115.0 . . ?
C6' C11' H11' 119.8 . . ?
C10' C11' C6' 120.45(17) . . ?
C10' C11' H11' 119.8 . . ?
C5' C4' C3' 121.94(16) . . ?
C5' C4' C12' 136.32(16) . . ?
C12' C4' C3' 101.69(14) . . ?
O1' C3' C4' 118.24(15) . . ?
N1' C3' O1' 125.91(16) . . ?
N1' C3' C4' 115.80(16) . . ?
O1' C2' H2'A 109.8 . . ?
O1' C2' H2'B 109.8 . . ?
O1' C2' C1' 109.52(18) . . ?
H2'A C2' H2'B 108.2 . . ?
C1' C2' H2'A 109.8 . . ?
C1' C2' H2'B 109.8 . . ?
C14' C13' H13' 120.6 . . ?
C12' C13' H13' 120.6 . . ?
C12' C13' C14' 118.74(17) . . ?
C13' C14' H14' 119.4 . . ?
C15' C14' C13' 121.14(19) . . ?
C15' C14' H14' 119.4 . . ?
C17' C16' H16' 121.1 . . ?
C15' C16' H16' 121.1 . . ?
C15' C16' C17' 117.71(18) . . ?
F1' C1' F2' 106.0(2) . . ?
F1' C1' F3' 107.40(19) . . ?
F1' C1' C2' 114.35(19) . . ?
F2' C1' C2' 111.53(19) . . ?
F3' C1' F2' 107.12(19) . . ?
F3' C1' C2' 110.1(2) . . ?
C16' C17' N1' 125.79(17) . . ?
C16' C17' C12' 121.40(18) . . ?
C12' C17' N1' 112.78(16) . . ?
C8' C9' H9' 120.2 . . ?
C10' C9' C8' 119.69(17) . . ?
C10' C9' H9' 120.2 . . ?
C11' C10' H10' 119.7 . . ?
C9' C10' C11' 120.51(17) . . ?
C9' C10' H10' 119.7 . . ?
C13' C12' C4' 135.25(16) . . ?
C13' C12' C17' 119.64(17) . . ?
C17' C12' C4' 104.96(15) . . ?
C14' C15' C16' 121.33(19) . . ?
C14' C15' H15' 119.3 . . ?
C16' C15' H15' 119.3 . . ?
C7 C6 C5 118.10(16) . . ?
C11 C6 C7 117.95(16) . . ?
C11 C6 C5 123.87(16) . . ?

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
F2 C1 C2 O1 -176.07(17) . . . . ?
F3 C1 C2 O1 64.0(2) . . . . ?
F1 C1 C2 O1 -55.5(3) . . . . ?
O1' C2' C1' F1' 54.1(3) . . . . ?
O1' C2' C1' F2' -66.1(2) . . . . ?
O1' C2' C1' F3' 175.09(17) . . . . ?
N1' C17' C12' C4' 1.5(2) . . . . ?
N1' C17' C12' C13' 177.72(16) . . . . ?
C8 C7 C6 C5 -179.49(18) . . . . ?
C8 C7 C6 C11 -2.7(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C5 C4 C12 C13 6.9(4) . . . . ?
C5 C4 C12 C17 179.5(2) . . . . ?
C5 C4 C3 O1 -1.4(3) . . . . ?
C5 C4 C3 N1 178.77(17) . . . . ?
C4 C5 C6 C7 -153.90(19) . . . . ?
C4 C5 C6 C11 29.5(3) . . . . ?
C4 C12 C13 C14 174.2(2) . . . . ?
C4 C12 C17 N1 -1.0(2) . . . . ?
C4 C12 C17 C16 -178.43(18) . . . . ?
C12 C4 C3 O1 176.24(16) . . . . ?
C12 C4 C3 N1 -3.6(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C12 C17 N1 173.06(17) . . . . ?
C13 C12 C17 C16 -4.4(3) . . . . ?
C6' C5' C4' C3' -175.72(18) . . . . ?
C6' C5' C4' C12' 7.6(4) . . . . ?
C6' C11' C10' C9' 0.1(3) . . . . ?
C3 O1 C2 C1 -109.2(2) . . . . ?
C3 N1 C17 C12 -1.2(2) . . . . ?
C3 N1 C17 C16 176.1(2) . . . . ?
C3 C4 C12 C13 -170.2(2) . . . . ?
C3 C4 C12 C17 2.40(18) . . . . ?
C2 O1 C3 N1 12.0(3) . . . . ?
C2 O1 C3 C4 -167.79(17) . . . . ?
C16 C15 C14 C13 -2.0(4) . . . . ?
C15 C16 C17 N1 -174.0(2) . . . . ?
C15 C16 C17 C12 3.1(3) . . . . ?
C17 N1 C3 O1 -176.78(18) . . . . ?
C17 N1 C3 C4 3.0(2) . . . . ?
C17 C12 C13 C14 2.4(3) . . . . ?
C17 C16 C15 C14 0.0(4) . . . . ?
C9 C8 C7 C6 1.8(3) . . . . ?
C10 C11 C6 C7 1.7(3) . . . . ?
C10 C11 C6 C5 178.32(18) . . . . ?
C8' C9' C10' C11' -1.4(3) . . . . ?
C7' C6' C5' C4' -145.1(2) . . . . ?
C7' C6' C11' C10' 1.8(3) . . . . ?
C7' C8' C9' C10' 0.7(3) . . . . ?
C5' C6' C7' C8' -179.12(17) . . . . ?
C5' C6' C11' C10' 178.32(17) . . . . ?
C5' C4' C3' O1' 4.8(3) . . . . ?
C5' C4' C3' N1' -177.52(18) . . . . ?
C5' C4' C12' C13' 0.9(4) . . . . ?
C5' C4' C12' C17' 176.2(2) . . . . ?
C11' C6' C7' C8' -2.5(3) . . . . ?
C11' C6' C5' C4' 38.5(3) . . . . ?
C3' O1' C2' C1' 111.0(2) . . . . ?
C3' N1' C17' C16' 176.63(19) . . . . ?
C3' N1' C17' C12' -1.4(2) . . . . ?
C3' C4' C12' C13' -176.3(2) . . . . ?
C3' C4' C12' C17' -0.96(18) . . . . ?
C2' O1' C3' N1' -7.6(3) . . . . ?
C2' O1' C3' C4' 169.83(17) . . . . ?
C13' C14' C15' C16' -1.2(3) . . . . ?
C14' C13' C12' C4' 176.06(19) . . . . ?
C14' C13' C12' C17' 1.2(3) . . . . ?
C16' C17' C12' C4' -176.62(17) . . . . ?
C16' C17' C12' C13' -0.4(3) . . . . ?
C17' N1' C3' O1' 178.20(19) . . . . ?
C17' N1' C3' C4' 0.7(2) . . . . ?
C17' C16' C15' C14' 2.0(3) . . . . ?
C9' C8' C7' C6' 1.2(3) . . . . ?
C12' C4' C3' O1' -177.54(17) . . . . ?
C12' C4' C3' N1' 0.2(2) . . . . ?
C12' C13' C14' C15' -0.5(3) . . . . ?
C15' C16' C17' N1' -179.04(19) . . . . ?
C15' C16' C17' C12' -1.2(3) . . . . ?
C6 C5 C4 C12 8.3(4) . . . . ?
C6 C5 C4 C3 -174.99(17) . . . . ?
C6 C11 C10 C9 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_agml_1127_0m
_database_code_depnum_ccdc_archive 'CCDC 2285990'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 Br F3 N O'
_chemical_formula_sum            'C28 H26 Br F3 N O'
_chemical_formula_weight         529.41
_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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9716(2)
_cell_length_b                   10.9315(3)
_cell_length_c                   15.7731(4)
_cell_angle_alpha                75.9800(10)
_cell_angle_beta                 78.6930(10)
_cell_angle_gamma                81.3380(10)
_cell_volume                     1299.96(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.432
_cell_measurement_theta_min      2.622
_shelx_estimated_absorpt_T_max   0.823
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1367 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.5678.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.125
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35476
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.452
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5278
_reflns_number_total             6457
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.000
_refine_diff_density_min         -1.424
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         6457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+1.7545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C27(H27), C15(H15), C8(H8), C24(H24), C21(H21), C2(H2), C11(H11)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C23(H23A,H23B,
 H23C), C20(H20A,H20B,H20C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19044(6) 0.04679(3) 0.60688(2) 0.06905(18) Uani 1 1 d . . . . .
O1 O 0.3059(4) 0.4983(3) 0.14775(17) 0.0716(8) Uani 1 1 d . . . . .
N1 N 0.3601(4) 0.4630(2) 0.28951(18) 0.0496(6) Uani 1 1 d . . . . .
H1 H 0.411403 0.530284 0.278596 0.060 Uiso 1 1 calc R U . . .
C28 C 0.3337(4) 0.3785(3) 0.3697(2) 0.0416(6) Uani 1 1 d . . . . .
F3 F 0.3533(5) 0.6327(4) -0.0190(2) 0.1209(13) Uani 1 1 d . . . . .
C4 C 0.2198(4) 0.3107(3) 0.26719(18) 0.0395(6) Uani 1 1 d . . . . .
C3 C 0.2906(4) 0.4218(3) 0.2297(2) 0.0461(7) Uani 1 1 d . . . . .
C14 C 0.2476(4) 0.2819(3) 0.35770(19) 0.0400(6) Uani 1 1 d . . . . .
C18 C 0.3672(4) 0.2813(3) 0.6126(2) 0.0441(6) Uani 1 1 d . . . . .
C5 C 0.1380(3) 0.2297(3) 0.22758(17) 0.0368(5) Uani 1 1 d . . . . .
C17 C 0.3324(4) 0.2811(3) 0.5225(2) 0.0443(6) Uani 1 1 d . . . . .
C6 C -0.0429(4) 0.2347(3) 0.23982(19) 0.0397(6) Uani 1 1 d . . . . .
C27 C 0.3752(4) 0.3795(3) 0.4507(2) 0.0458(7) Uani 1 1 d . . . . .
H27 H 0.430871 0.444984 0.456895 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2052(4) 0.1824(3) 0.4295(2) 0.0469(7) Uani 1 1 d . . . . .
H15 H 0.148696 0.117126 0.423596 0.056 Uiso 1 1 calc R U . . .
C8 C -0.1159(4) 0.1563(3) 0.2037(2) 0.0451(7) Uani 1 1 d . . . . .
H8 H -0.235168 0.161272 0.211157 0.054 Uiso 1 1 calc R U . . .
C25 C 0.2356(5) 0.3254(3) 0.6735(2) 0.0557(8) Uani 1 1 d . . . . .
C24 C 0.2665(6) 0.3176(4) 0.7588(3) 0.0623(9) Uani 1 1 d . . . . .
H24 H 0.178764 0.347410 0.799569 0.075 Uiso 1 1 calc R U . . .
C9 C -0.0185(4) 0.0710(3) 0.1572(2) 0.0480(7) Uani 1 1 d . . . . .
C16 C 0.2495(5) 0.1835(3) 0.5095(2) 0.0481(7) Uani 1 1 d . . . . .
C21 C 0.5514(5) 0.2281(3) 0.7229(2) 0.0590(9) Uani 1 1 d . . . . .
H21 H 0.658352 0.196332 0.738962 0.071 Uiso 1 1 calc R U . . .
C19 C 0.5277(5) 0.2342(3) 0.6366(2) 0.0525(7) Uani 1 1 d . . . . .
C22 C 0.4215(6) 0.2676(3) 0.7847(2) 0.0601(9) Uani 1 1 d . . . . .
F2 F 0.1507(7) 0.5659(5) -0.0512(3) 0.169(2) Uani 1 1 d . . . . .
C2 C 0.2178(6) 0.4744(4) 0.0871(2) 0.0677(11) Uani 1 1 d . . . . .
H2 H 0.172505 0.399354 0.090661 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2382(4) 0.1433(3) 0.1809(2) 0.0468(7) Uani 1 1 d . . . . .
C11 C 0.1584(4) 0.0663(3) 0.1459(2) 0.0532(8) Uani 1 1 d . . . . .
H11 H 0.226158 0.010217 0.114011 0.064 Uiso 1 1 calc R U . . .
C7 C -0.1578(5) 0.3231(4) 0.2923(3) 0.0657(10) Uani 1 1 d . . . . .
H7A H -0.131205 0.304762 0.351176 0.098 Uiso 1 1 calc R U . . .
H7B H -0.275998 0.311517 0.295258 0.098 Uiso 1 1 calc R U . . .
H7C H -0.139344 0.409316 0.263852 0.098 Uiso 1 1 calc R U . . .
C13 C 0.4328(5) 0.1292(5) 0.1695(4) 0.0776(13) Uani 1 1 d . . . . .
H13A H 0.473194 0.211366 0.149001 0.116 Uiso 1 1 calc R U . . .
H13B H 0.480086 0.078136 0.127011 0.116 Uiso 1 1 calc R U . . .
H13C H 0.468418 0.089000 0.225341 0.116 Uiso 1 1 calc R U . . .
C10 C -0.1045(6) -0.0147(5) 0.1217(3) 0.0774(12) Uani 1 1 d . . . . .
H10A H -0.187804 -0.056213 0.168054 0.116 Uiso 1 1 calc R U . . .
H10B H -0.019661 -0.077113 0.100214 0.116 Uiso 1 1 calc R U . . .
H10C H -0.161076 0.034668 0.074036 0.116 Uiso 1 1 calc R U . . .
C23 C 0.4452(9) 0.2538(5) 0.8798(3) 0.0919(16) Uani 1 1 d . . . . .
H23A H 0.426866 0.335911 0.893981 0.138 Uiso 1 1 calc R U . . .
H23B H 0.559922 0.216203 0.886698 0.138 Uiso 1 1 calc R U . . .
H23C H 0.363790 0.200682 0.918817 0.138 Uiso 1 1 calc R U . . .
C1 C 0.2089(6) 0.5905(5) 0.0153(3) 0.0759(13) Uani 1 1 d . . . . .
C20 C 0.6732(7) 0.1861(6) 0.5719(3) 0.0919(16) Uani 1 1 d . . . . .
H20A H 0.635072 0.124096 0.548167 0.138 Uiso 1 1 calc R U . . .
H20B H 0.768367 0.148057 0.601817 0.138 Uiso 1 1 calc R U . . .
H20C H 0.708707 0.255562 0.524548 0.138 Uiso 1 1 calc R U . . .
C26 C 0.0593(6) 0.3762(6) 0.6496(4) 0.0887(15) Uani 1 1 d . . . . .
H26A H 0.069280 0.448747 0.601110 0.133 Uiso 1 1 calc R U . . .
H26B H -0.015240 0.400424 0.699896 0.133 Uiso 1 1 calc R U . . .
H26C H 0.012139 0.311618 0.632695 0.133 Uiso 1 1 calc R U . . .
F1 F 0.1116(9) 0.6801(5) 0.0384(4) 0.228(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
Br1 C16 1.906(3) . ?
O1 C3 1.353(4) . ?
O1 C2 1.385(4) . ?
N1 H1 0.8600 . ?
N1 C28 1.373(4) . ?
N1 C3 1.373(4) . ?
C28 C14 1.410(4) . ?
C28 C27 1.384(4) . ?
F3 C1 1.275(5) . ?
C4 C3 1.367(4) . ?
C4 C14 1.439(4) . ?
C4 C5 1.484(4) . ?
C14 C15 1.394(4) . ?
C18 C17 1.500(4) . ?
C18 C25 1.391(5) . ?
C18 C19 1.394(5) . ?
C5 C6 1.411(4) . ?
C5 C12 1.396(4) . ?
C17 C27 1.387(4) . ?
C17 C16 1.410(4) . ?
C6 C8 1.384(4) . ?
C6 C7 1.511(5) . ?
C27 H27 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(5) . ?
C25 C24 1.395(5) . ?
C25 C26 1.516(6) . ?
C24 H24 0.9300 . ?
C24 C22 1.371(6) . ?
C9 C11 1.381(5) . ?
C9 C10 1.504(5) . ?
C21 H21 0.9300 . ?
C21 C19 1.395(5) . ?
C21 C22 1.372(6) . ?
C19 C20 1.508(6) . ?
C22 C23 1.517(5) . ?
F2 C1 1.323(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.486(5) . ?
C12 C11 1.393(4) . ?
C12 C13 1.514(5) . ?
C11 H11 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C1 F1 1.237(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C3 O1 C2 118.1(3) . . ?
C28 N1 H1 125.8 . . ?
C3 N1 H1 125.8 . . ?
C3 N1 C28 108.4(2) . . ?
N1 C28 C14 107.0(2) . . ?
N1 C28 C27 130.6(3) . . ?
C27 C28 C14 122.4(3) . . ?
C3 C4 C14 104.4(2) . . ?
C3 C4 C5 130.6(3) . . ?
C14 C4 C5 125.0(2) . . ?
O1 C3 N1 114.3(3) . . ?
O1 C3 C4 134.0(3) . . ?
C4 C3 N1 111.7(3) . . ?
C28 C14 C4 108.5(2) . . ?
C15 C14 C28 119.0(3) . . ?
C15 C14 C4 132.5(3) . . ?
C25 C18 C17 119.3(3) . . ?
C25 C18 C19 119.8(3) . . ?
C19 C18 C17 120.8(3) . . ?
C6 C5 C4 120.4(3) . . ?
C12 C5 C4 120.7(2) . . ?
C12 C5 C6 118.8(3) . . ?
C27 C17 C18 120.8(3) . . ?
C27 C17 C16 118.4(3) . . ?
C16 C17 C18 120.8(3) . . ?
C5 C6 C7 121.2(3) . . ?
C8 C6 C5 119.2(3) . . ?
C8 C6 C7 119.5(3) . . ?
C28 C27 C17 118.8(3) . . ?
C28 C27 H27 120.6 . . ?
C17 C27 H27 120.6 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.0(3) . . ?
C16 C15 H15 121.0 . . ?
C6 C8 H8 118.8 . . ?
C9 C8 C6 122.5(3) . . ?
C9 C8 H8 118.8 . . ?
C18 C25 C24 118.7(3) . . ?
C18 C25 C26 121.1(3) . . ?
C24 C25 C26 120.2(4) . . ?
C25 C24 H24 118.8 . . ?
C22 C24 C25 122.3(4) . . ?
C22 C24 H24 118.8 . . ?
C8 C9 C11 117.8(3) . . ?
C8 C9 C10 120.3(3) . . ?
C11 C9 C10 121.9(3) . . ?
C17 C16 Br1 119.2(2) . . ?
C15 C16 Br1 117.4(2) . . ?
C15 C16 C17 123.4(3) . . ?
C19 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C22 C21 C19 121.9(3) . . ?
C18 C19 C21 119.0(3) . . ?
C18 C19 C20 121.1(3) . . ?
C21 C19 C20 119.8(3) . . ?
C24 C22 C21 118.1(3) . . ?
C24 C22 C23 120.3(4) . . ?
C21 C22 C23 121.6(4) . . ?
O1 C2 H2 126.3 . . ?
O1 C2 C1 107.5(3) . . ?
C1 C2 H2 126.3 . . ?
C5 C12 C13 121.2(3) . . ?
C11 C12 C5 119.7(3) . . ?
C11 C12 C13 119.2(3) . . ?
C9 C11 C12 121.9(3) . . ?
C9 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F3 C1 F2 105.1(4) . . ?
F3 C1 C2 114.7(4) . . ?
F2 C1 C2 109.7(4) . . ?
F1 C1 F3 106.4(6) . . ?
F1 C1 F2 106.7(6) . . ?
F1 C1 C2 113.7(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C1 F3 52.0(6) . . . . ?
O1 C2 C1 F2 170.0(5) . . . . ?
O1 C2 C1 F1 -70.7(7) . . . . ?
N1 C28 C14 C4 -0.7(4) . . . . ?
N1 C28 C14 C15 179.8(3) . . . . ?
N1 C28 C27 C17 179.6(3) . . . . ?
C28 N1 C3 O1 179.1(3) . . . . ?
C28 N1 C3 C4 -0.8(4) . . . . ?
C28 C14 C15 C16 0.2(5) . . . . ?
C4 C14 C15 C16 -179.3(3) . . . . ?
C4 C5 C6 C8 -178.7(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C5 C12 C11 178.7(3) . . . . ?
C4 C5 C12 C13 0.2(5) . . . . ?
C3 O1 C2 C1 162.3(4) . . . . ?
C3 N1 C28 C14 0.9(4) . . . . ?
C3 N1 C28 C27 -178.1(3) . . . . ?
C3 C4 C14 C28 0.2(3) . . . . ?
C3 C4 C14 C15 179.7(4) . . . . ?
C3 C4 C5 C6 -101.2(4) . . . . ?
C3 C4 C5 C12 81.5(4) . . . . ?
C14 C28 C27 C17 0.8(5) . . . . ?
C14 C4 C3 O1 -179.5(4) . . . . ?
C14 C4 C3 N1 0.3(4) . . . . ?
C14 C4 C5 C6 81.7(4) . . . . ?
C14 C4 C5 C12 -95.5(4) . . . . ?
C14 C15 C16 Br1 180.0(2) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
C18 C17 C27 C28 -177.1(3) . . . . ?
C18 C17 C16 Br1 -2.7(4) . . . . ?
C18 C17 C16 C15 176.1(3) . . . . ?
C18 C25 C24 C22 -0.2(5) . . . . ?
C5 C4 C3 O1 2.9(7) . . . . ?
C5 C4 C3 N1 -177.2(3) . . . . ?
C5 C4 C14 C28 177.9(3) . . . . ?
C5 C4 C14 C15 -2.6(5) . . . . ?
C5 C6 C8 C9 1.2(4) . . . . ?
C5 C12 C11 C9 -1.2(5) . . . . ?
C17 C18 C25 C24 176.0(3) . . . . ?
C17 C18 C25 C26 -1.5(5) . . . . ?
C17 C18 C19 C21 -175.7(3) . . . . ?
C17 C18 C19 C20 2.2(5) . . . . ?
C6 C5 C12 C11 1.4(4) . . . . ?
C6 C5 C12 C13 -177.0(3) . . . . ?
C6 C8 C9 C11 -0.9(5) . . . . ?
C6 C8 C9 C10 178.2(3) . . . . ?
C27 C28 C14 C4 178.4(3) . . . . ?
C27 C28 C14 C15 -1.2(5) . . . . ?
C27 C17 C16 Br1 179.6(2) . . . . ?
C27 C17 C16 C15 -1.6(5) . . . . ?
C8 C9 C11 C12 0.9(5) . . . . ?
C25 C18 C17 C27 96.9(4) . . . . ?
C25 C18 C17 C16 -80.7(4) . . . . ?
C25 C18 C19 C21 2.3(5) . . . . ?
C25 C18 C19 C20 -179.8(4) . . . . ?
C25 C24 C22 C21 2.2(5) . . . . ?
C25 C24 C22 C23 -176.2(4) . . . . ?
C16 C17 C27 C28 0.6(5) . . . . ?
C19 C18 C17 C27 -85.1(4) . . . . ?
C19 C18 C17 C16 97.4(4) . . . . ?
C19 C18 C25 C24 -2.0(5) . . . . ?
C19 C18 C25 C26 -179.5(4) . . . . ?
C19 C21 C22 C24 -1.9(5) . . . . ?
C19 C21 C22 C23 176.5(4) . . . . ?
C22 C21 C19 C18 -0.3(5) . . . . ?
C22 C21 C19 C20 -178.3(4) . . . . ?
C2 O1 C3 N1 -170.7(4) . . . . ?
C2 O1 C3 C4 9.2(7) . . . . ?
C12 C5 C6 C8 -1.4(4) . . . . ?
C12 C5 C6 C7 177.9(3) . . . . ?
C7 C6 C8 C9 -178.2(3) . . . . ?
C13 C12 C11 C9 177.3(4) . . . . ?
C10 C9 C11 C12 -178.2(4) . . . . ?
C26 C25 C24 C22 177.3(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_agml_867_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2257371'
loop_
_audit_author_name
_audit_author_address
'KAMLESH SATPUTE'
;INDIAN INSTITUTE OF TECHNOLOGY ROPAR
India
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 F3 N S'
_chemical_formula_sum            'C23 H18 F3 N S'
_chemical_formula_weight         397.44
_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'
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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.0705(6)
_cell_length_b                   16.8461(16)
_cell_length_c                   32.575(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3880.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9789
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1667 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.8213.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            55828
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.722
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_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                3623
_reflns_number_total             3971
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+2.1881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1296
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C12(H12), C16(H16), C6(H6), C21(H21), C22(H22), C15(H15), C14(H14),
 C13(H13), C10(H10), C7(H7), C8(H8), C9(H9)
1.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21744(8) 0.42876(3) 0.34034(2) 0.04698(17) Uani 1 1 d . . . . .
N1 N 0.4539(2) 0.33815(9) 0.38438(5) 0.0394(4) Uani 1 1 d . . . . .
F2 F 0.0981(4) 0.32071(11) 0.26784(5) 0.1006(7) Uani 1 1 d . . . . .
F1 F 0.3278(3) 0.26798(13) 0.29927(7) 0.1032(7) Uani 1 1 d . . . . .
C17 C 0.6955(3) 0.42271(10) 0.40674(6) 0.0331(4) Uani 1 1 d . . . . .
C4 C 0.5617(3) 0.47348(11) 0.38088(6) 0.0335(4) Uani 1 1 d . . . . .
C23 C 0.6249(3) 0.34553(11) 0.40710(6) 0.0357(4) Uani 1 1 d . . . . .
C11 C 0.4588(3) 0.53937(10) 0.40463(6) 0.0343(4) Uani 1 1 d . . . . .
C5 C 0.6694(3) 0.50621(12) 0.34358(6) 0.0378(4) Uani 1 1 d . . . . .
C3 C 0.4183(3) 0.40708(11) 0.36971(6) 0.0348(4) Uani 1 1 d . . . . .
C18 C 0.8626(3) 0.44060(12) 0.42671(6) 0.0384(4) Uani 1 1 d . . . . .
H18 H 0.911527 0.491815 0.425873 0.046 Uiso 1 1 calc R U . . .
F3 F 0.0527(4) 0.21707(11) 0.30340(7) 0.1224(9) Uani 1 1 d . . . . .
C12 C 0.3363(3) 0.58998(12) 0.38366(7) 0.0445(5) Uani 1 1 d . . . . .
H12 H 0.323795 0.585293 0.355346 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4779(3) 0.54923(11) 0.44671(6) 0.0395(4) Uani 1 1 d . . . . .
H16 H 0.560866 0.516865 0.461213 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6965(3) 0.46027(14) 0.30862(6) 0.0471(5) Uani 1 1 d . . . . .
H6 H 0.641070 0.410325 0.306805 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9571(3) 0.38056(13) 0.44825(6) 0.0408(4) Uani 1 1 d . . . . .
C21 C 0.8841(3) 0.30404(12) 0.44795(7) 0.0447(5) Uani 1 1 d . . . . .
H21 H 0.948399 0.264144 0.461896 0.054 Uiso 1 1 calc R U . . .
C22 C 0.7182(3) 0.28544(12) 0.42749(7) 0.0437(5) Uani 1 1 d . . . . .
H22 H 0.671134 0.233897 0.427511 0.052 Uiso 1 1 calc R U . . .
C15 C 0.3750(3) 0.60659(13) 0.46741(7) 0.0483(5) Uani 1 1 d . . . . .
H15 H 0.389342 0.612407 0.495630 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2512(3) 0.65520(13) 0.44636(8) 0.0503(5) Uani 1 1 d . . . . .
H14 H 0.180556 0.693113 0.460342 0.060 Uiso 1 1 calc R U . . .
C13 C 0.2332(3) 0.64702(13) 0.40436(8) 0.0508(5) Uani 1 1 d . . . . .
H13 H 0.151325 0.680039 0.389951 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1018(3) 0.33373(14) 0.33949(7) 0.0503(5) Uani 1 1 d . . . . .
H2A H 0.138822 0.304147 0.363743 0.060 Uiso 1 1 calc R U . . .
H2B H -0.033841 0.341917 0.340810 0.060 Uiso 1 1 calc R U . . .
C20 C 1.1360(3) 0.39867(16) 0.47173(8) 0.0598(6) Uani 1 1 d . . . . .
H20A H 1.222470 0.426799 0.454283 0.090 Uiso 1 1 calc R U . . .
H20B H 1.193121 0.349947 0.480662 0.090 Uiso 1 1 calc R U . . .
H20C H 1.106115 0.430796 0.495196 0.090 Uiso 1 1 calc R U . . .
C10 C 0.7544(4) 0.58036(14) 0.34558(8) 0.0558(6) Uani 1 1 d . . . . .
H10 H 0.738943 0.611603 0.368882 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8061(4) 0.48866(19) 0.27633(7) 0.0636(7) Uani 1 1 d . . . . .
H7 H 0.824205 0.457379 0.253141 0.076 Uiso 1 1 calc R U . . .
C1 C 0.1463(4) 0.28552(15) 0.30249(8) 0.0628(7) Uani 1 1 d . . . . .
C8 C 0.8872(4) 0.56215(19) 0.27843(9) 0.0695(8) Uani 1 1 d . . . . .
H8 H 0.959087 0.581057 0.256605 0.083 Uiso 1 1 calc R U . . .
C9 C 0.8623(4) 0.60820(17) 0.31300(10) 0.0722(8) Uani 1 1 d . . . . .
H9 H 0.918074 0.658119 0.314515 0.087 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
S1 C3 1.7507(19) . ?
S1 C2 1.798(2) . ?
N1 C23 1.423(2) . ?
N1 C3 1.281(2) . ?
F2 C1 1.320(3) . ?
F1 C1 1.321(3) . ?
C17 C4 1.528(2) . ?
C17 C23 1.393(3) . ?
C17 C18 1.382(3) . ?
C4 C11 1.536(2) . ?
C4 C5 1.536(3) . ?
C4 C3 1.553(3) . ?
C23 C22 1.379(3) . ?
C11 C12 1.394(3) . ?
C11 C16 1.387(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.401(3) . ?
F3 C1 1.330(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(3) . ?
C19 C21 1.389(3) . ?
C19 C20 1.509(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.381(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.487(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.389(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C9 H9 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
C3 S1 C2 101.04(10) . . ?
C3 N1 C23 106.39(16) . . ?
C23 C17 C4 107.79(16) . . ?
C18 C17 C4 131.79(17) . . ?
C18 C17 C23 120.40(17) . . ?
C17 C4 C11 114.83(15) . . ?
C17 C4 C5 109.30(15) . . ?
C17 C4 C3 97.48(14) . . ?
C11 C4 C3 109.19(15) . . ?
C5 C4 C11 111.95(15) . . ?
C5 C4 C3 113.36(15) . . ?
C17 C23 N1 112.44(16) . . ?
C22 C23 N1 126.37(18) . . ?
C22 C23 C17 121.19(18) . . ?
C12 C11 C4 119.31(17) . . ?
C16 C11 C4 122.55(17) . . ?
C16 C11 C12 118.11(18) . . ?
C6 C5 C4 121.10(18) . . ?
C10 C5 C4 120.02(19) . . ?
C10 C5 C6 118.7(2) . . ?
N1 C3 S1 123.55(15) . . ?
N1 C3 C4 115.90(16) . . ?
C4 C3 S1 120.50(13) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.10(18) . . ?
C19 C18 H18 120.4 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 120.91(19) . . ?
C15 C16 H16 119.5 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(2) . . ?
C7 C6 H6 119.8 . . ?
C18 C19 C20 120.5(2) . . ?
C21 C19 C18 119.29(18) . . ?
C21 C19 C20 120.19(19) . . ?
C19 C21 H21 119.1 . . ?
C22 C21 C19 121.90(19) . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 118.10(19) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
S1 C2 H2A 108.8 . . ?
S1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 S1 113.75(17) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C5 C10 H10 119.8 . . ?
C5 C10 C9 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.7 . . ?
F2 C1 F1 106.4(3) . . ?
F2 C1 F3 106.3(2) . . ?
F2 C1 C2 113.2(2) . . ?
F1 C1 F3 106.9(3) . . ?
F1 C1 C2 113.1(2) . . ?
F3 C1 C2 110.5(2) . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?

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
S1 C2 C1 F2 -59.4(3) . . . . ?
S1 C2 C1 F1 61.7(3) . . . . ?
S1 C2 C1 F3 -178.5(2) . . . . ?
N1 C23 C22 C21 179.81(19) . . . . ?
C17 C4 C11 C12 178.78(17) . . . . ?
C17 C4 C11 C16 -3.4(3) . . . . ?
C17 C4 C5 C6 81.7(2) . . . . ?
C17 C4 C5 C10 -93.1(2) . . . . ?
C17 C4 C3 S1 178.00(13) . . . . ?
C17 C4 C3 N1 0.2(2) . . . . ?
C17 C23 C22 C21 0.4(3) . . . . ?
C17 C18 C19 C21 2.0(3) . . . . ?
C17 C18 C19 C20 -177.68(19) . . . . ?
C4 C17 C23 N1 -0.7(2) . . . . ?
C4 C17 C23 C22 178.75(18) . . . . ?
C4 C17 C18 C19 -179.48(18) . . . . ?
C4 C11 C12 C13 176.33(19) . . . . ?
C4 C11 C16 C15 -176.50(18) . . . . ?
C4 C5 C6 C7 -175.25(19) . . . . ?
C4 C5 C10 C9 175.8(2) . . . . ?
C23 N1 C3 S1 -178.33(14) . . . . ?
C23 N1 C3 C4 -0.6(2) . . . . ?
C23 C17 C4 C11 115.51(17) . . . . ?
C23 C17 C4 C5 -117.73(17) . . . . ?
C23 C17 C4 C3 0.29(18) . . . . ?
C23 C17 C18 C19 -1.7(3) . . . . ?
C11 C4 C5 C6 -149.88(18) . . . . ?
C11 C4 C5 C10 35.3(3) . . . . ?
C11 C4 C3 S1 58.38(19) . . . . ?
C11 C4 C3 N1 -119.38(18) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C11 C16 C15 C14 0.0(3) . . . . ?
C5 C4 C11 C12 53.4(2) . . . . ?
C5 C4 C11 C16 -128.76(19) . . . . ?
C5 C4 C3 S1 -67.17(19) . . . . ?
C5 C4 C3 N1 115.06(19) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C5 C10 C9 C8 -0.5(4) . . . . ?
C3 S1 C2 C1 -95.15(19) . . . . ?
C3 N1 C23 C17 0.8(2) . . . . ?
C3 N1 C23 C22 -178.6(2) . . . . ?
C3 C4 C11 C12 -73.0(2) . . . . ?
C3 C4 C11 C16 104.9(2) . . . . ?
C3 C4 C5 C6 -25.8(2) . . . . ?
C3 C4 C5 C10 159.33(19) . . . . ?
C18 C17 C4 C11 -66.5(3) . . . . ?
C18 C17 C4 C5 60.2(3) . . . . ?
C18 C17 C4 C3 178.3(2) . . . . ?
C18 C17 C23 N1 -178.94(17) . . . . ?
C18 C17 C23 C22 0.5(3) . . . . ?
C18 C19 C21 C22 -1.1(3) . . . . ?
C12 C11 C16 C15 1.4(3) . . . . ?
C16 C11 C12 C13 -1.6(3) . . . . ?
C16 C15 C14 C13 -1.1(3) . . . . ?
C6 C5 C10 C9 0.8(4) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C19 C21 C22 C23 -0.1(3) . . . . ?
C15 C14 C13 C12 0.9(4) . . . . ?
C2 S1 C3 N1 0.4(2) . . . . ?
C2 S1 C3 C4 -177.18(15) . . . . ?
C20 C19 C21 C22 178.6(2) . . . . ?
C10 C5 C6 C7 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
