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

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

data_8febb_0m
_database_code_depnum_ccdc_archive 'CCDC 2401333'
loop_
_audit_author_name
_audit_author_address
'Ramesh Singh'
;IIT Kanpur
India
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_audit_creation_date             2024-09-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        shweta
_chemical_formula_moiety         'C16 H12 Br F3 N2 O3'
_chemical_formula_sum            'C16 H12 Br F3 N2 O3'
_chemical_formula_weight         417.19
_chemical_absolute_configuration ad
_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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   10.4398(3)
_cell_length_b                   10.4398(3)
_cell_length_c                   28.3533(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3090.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4663
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0822 after correction.
The Ratio of minimum to maximum transmission is 0.6254.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull yellowish yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1664
_exptl_crystal_preparation       'pentane slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            64032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.423
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6762
_reflns_number_total             7099
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 3092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7099
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.051
_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)+(0.0407P)²+2.5701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0829
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00Q(H00Q), C00V(H00V), C00X(H00X), C010(H010), C013(H013),
 C016(H016), C01A(H01D)
1.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C), C00Z(H00D,H00E,H00F), C019(H01A,H01B,H01C), C01B(H01E,
 H01F,H01G)
1.c Idealised tetrahedral OH refined as rotating group:
 C20(H20A), C01D(H01H)
;
_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
Br01 Br 0.24180(4) -0.24706(4) 0.67921(2) 0.02114(13) Uani 1 1 d . . . . .
Br02 Br 0.25570(4) 0.25586(5) 0.58013(2) 0.02248(14) Uani 1 1 d . . . . .
F4 F 0.2597(2) 0.1132(2) 0.80168(8) 0.0161(5) Uani 1 1 d . . . . .
F6 F 0.0898(2) 0.2286(2) 0.79914(9) 0.0177(5) Uani 1 1 d . . . . .
F5 F 0.2743(3) 0.3174(2) 0.81076(9) 0.0202(5) Uani 1 1 d . . . . .
F1 F 0.8170(2) 0.2678(2) 0.44318(9) 0.0179(5) Uani 1 1 d . . . . .
F2 F 0.7256(2) 0.0882(2) 0.46018(9) 0.0155(5) Uani 1 1 d . . . . .
F3 F 0.6127(2) 0.2590(2) 0.45317(9) 0.0177(5) Uani 1 1 d . . . . .
O009 O 0.6921(3) 0.3666(3) 0.65054(11) 0.0204(7) Uani 1 1 d . . . . .
O00A O 0.9348(3) 0.2905(2) 0.56537(10) 0.0099(5) Uani 1 1 d . . . . .
O00B O 0.2701(3) 0.4354(3) 0.68921(10) 0.0112(5) Uani 1 1 d . . . . .
O00C O 0.8555(3) 0.7136(3) 0.59761(11) 0.0165(6) Uani 1 1 d . . . . .
O00D O 0.4906(3) 0.0812(3) 0.74717(11) 0.0160(6) Uani 1 1 d . . . . .
O00E O 0.5745(3) 0.4954(3) 0.50429(11) 0.0170(6) Uani 1 1 d . . . . .
N00F N 0.7186(3) 0.6029(3) 0.55036(12) 0.0110(6) Uani 1 1 d . . . . .
N00G N 0.5910(3) 0.2289(3) 0.70122(12) 0.0124(7) Uani 1 1 d . . . . .
N00H N 0.4818(3) 0.4048(3) 0.66761(12) 0.0118(6) Uani 1 1 d . . . . .
N00I N 0.9012(3) 0.5038(3) 0.58213(11) 0.0092(6) Uani 1 1 d . . . . .
C00J C 0.8262(4) 0.6139(4) 0.57793(14) 0.0117(7) Uani 1 1 d . . . . .
C00K C 0.5957(4) 0.3348(4) 0.67142(14) 0.0128(7) Uani 1 1 d . . . . .
C00L C 0.1805(4) 0.3762(4) 0.71935(13) 0.0096(7) Uani 1 1 d . . . . .
C00M C 0.0535(4) -0.0653(4) 0.65292(14) 0.0144(8) Uani 1 1 d . . . . .
H00M H 0.018456 -0.131116 0.634995 0.017 Uiso 1 1 calc R U . . .
C00N C 0.7103(4) 0.1565(5) 0.70550(17) 0.0207(9) Uani 1 1 d . . . . .
H00A H 0.734513 0.123849 0.675122 0.031 Uiso 1 1 calc R U . . .
H00B H 0.698058 0.086391 0.726955 0.031 Uiso 1 1 calc R U . . .
H00C H 0.776654 0.211585 0.717225 0.031 Uiso 1 1 calc R U . . .
C00O C 0.1628(4) -0.0845(4) 0.67953(14) 0.0130(7) Uani 1 1 d . . . . .
C00P C 0.4818(4) 0.1800(4) 0.72437(14) 0.0122(7) Uani 1 1 d . . . . .
C00Q C 0.2195(4) 0.0124(4) 0.70608(13) 0.0113(7) Uani 1 1 d . . . . .
H00Q H 0.293692 -0.003326 0.723291 0.014 Uiso 1 1 calc R U . . .
C00R C 0.4197(4) 0.1771(4) 0.57931(15) 0.0144(8) Uani 1 1 d . . . . .
C00S C 0.2137(4) 0.2255(4) 0.78658(14) 0.0109(7) Uani 1 1 d . . . . .
C00T C 0.8624(3) 0.3967(3) 0.56004(13) 0.0086(7) Uani 1 1 d . . . . .
C00U C 0.3783(4) 0.3650(3) 0.69161(13) 0.0099(7) Uani 1 1 d . . . . .
C00V C 0.6569(4) 0.0647(4) 0.57735(14) 0.0134(8) Uani 1 1 d . . . . .
H00V H 0.736669 0.025085 0.576383 0.016 Uiso 1 1 calc R U . . .
C00W C 0.1627(4) 0.1340(3) 0.70636(13) 0.0093(7) Uani 1 1 d . . . . .
C00X C 0.5141(4) 0.2316(4) 0.55151(13) 0.0119(7) Uani 1 1 d . . . . .
H00X H 0.497238 0.304394 0.533642 0.014 Uiso 1 1 calc R U . . .
C00Y C 0.8769(4) 0.1950(4) 0.53708(13) 0.0099(7) Uani 1 1 d . . . . .
C00Z C 0.6391(4) 0.7179(4) 0.54794(17) 0.0197(9) Uani 1 1 d . . . . .
H00D H 0.598675 0.731833 0.577903 0.030 Uiso 1 1 calc R U . . .
H00E H 0.574786 0.706973 0.524090 0.030 Uiso 1 1 calc R U . . .
H00F H 0.691753 0.790310 0.540235 0.030 Uiso 1 1 calc R U . . .
C010 C 0.0514(4) 0.1544(4) 0.68024(14) 0.0129(7) Uani 1 1 d . . . . .
H010 H 0.012550 0.234516 0.680400 0.016 Uiso 1 1 calc R U . . .
C011 C 0.6732(4) 0.4913(4) 0.52677(14) 0.0111(7) Uani 1 1 d . . . . .
C20 C 0.0753(4) 0.4392(4) 0.73081(14) 0.0143(8) Uani 1 1 d . . . . .
H20A H 0.074979 0.509066 0.717595 0.021 Uiso 1 1 calc R U . . .
C013 C -0.0020(4) 0.0546(4) 0.65380(14) 0.0147(8) Uani 1 1 d . . . . .
H013 H -0.076212 0.069431 0.636501 0.018 Uiso 1 1 calc R U . . .
C014 C 0.3701(4) 0.2572(4) 0.71829(13) 0.0082(7) Uani 1 1 d . . . . .
C015 C 0.2299(4) 0.2430(3) 0.73320(15) 0.0085(7) Uani 1 1 d . . . . .
C016 C 0.5600(4) 0.0131(4) 0.60527(15) 0.0175(8) Uani 1 1 d . . . . .
H016 H 0.576243 -0.059495 0.623303 0.021 Uiso 1 1 calc R U . . .
C017 C 0.7429(3) 0.2406(3) 0.52178(16) 0.0076(8) Uani 1 1 d . . . . .
C018 C 0.7239(4) 0.2147(4) 0.46945(14) 0.0096(7) Uani 1 1 d . . . . .
C019 C 0.4814(4) 0.5211(4) 0.63846(16) 0.0188(9) Uani 1 1 d . . . . .
H01A H 0.497050 0.594465 0.658048 0.028 Uiso 1 1 calc R U . . .
H01B H 0.399629 0.529941 0.623322 0.028 Uiso 1 1 calc R U . . .
H01C H 0.547301 0.514931 0.614954 0.028 Uiso 1 1 calc R U . . .
C01A C 0.4399(4) 0.0687(4) 0.60647(15) 0.0181(9) Uani 1 1 d . . . . .
H01D H 0.374792 0.034466 0.624939 0.022 Uiso 1 1 calc R U . . .
C01B C 1.0186(4) 0.5067(4) 0.61059(15) 0.0156(8) Uani 1 1 d . . . . .
H01E H 1.091931 0.505228 0.590148 0.023 Uiso 1 1 calc R U . . .
H01F H 1.020678 0.433253 0.630970 0.023 Uiso 1 1 calc R U . . .
H01G H 1.020105 0.583344 0.629267 0.023 Uiso 1 1 calc R U . . .
C01C C 0.6356(4) 0.1747(4) 0.55091(13) 0.0099(7) Uani 1 1 d . . . . .
C01D C 0.9422(4) 0.0896(4) 0.52842(15) 0.0149(8) Uani 1 1 d . . . . .
H01H H 1.010544 0.091942 0.542661 0.022 Uiso 1 1 calc R U . . .
C01E C 0.7554(3) 0.3827(3) 0.53400(13) 0.0084(7) Uani 1 1 d . . . . .
H20B H 0.011(5) 0.395(5) 0.7514(19) 0.021(13) Uiso 1 1 d . . . . .
H01I H 0.906(6) 0.023(7) 0.512(2) 0.041(18) 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
Br01 C00O 1.887(4) . ?
Br02 C00R 1.899(4) . ?
F4 C00S 1.337(4) . ?
F6 C00S 1.342(5) . ?
F5 C00S 1.338(5) . ?
F1 C018 1.344(5) . ?
F2 C018 1.347(5) . ?
F3 C018 1.332(4) . ?
O009 C00K 1.214(5) . ?
O00A C00T 1.350(5) . ?
O00A C00Y 1.415(4) . ?
O00B C00L 1.409(4) . ?
O00B C00U 1.349(4) . ?
O00C C00J 1.220(5) . ?
O00D C00P 1.221(5) . ?
O00E C011 1.212(5) . ?
N00F C00J 1.373(5) . ?
N00F C00Z 1.460(5) . ?
N00F C011 1.424(5) . ?
N00G C00K 1.392(5) . ?
N00G C00N 1.462(5) . ?
N00G C00P 1.411(5) . ?
N00H C00K 1.400(5) . ?
N00H C00U 1.343(5) . ?
N00H C019 1.469(5) . ?
N00I C00J 1.396(5) . ?
N00I C00T 1.345(5) . ?
N00I C01B 1.468(5) . ?
C00L C20 1.321(6) . ?
C00L C015 1.534(5) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.383(6) . ?
C00M C013 1.379(6) . ?
C00N H00A 0.9600 . ?
C00N H00B 0.9600 . ?
C00N H00C 0.9600 . ?
C00O C00Q 1.393(5) . ?
C00P C014 1.428(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C00W 1.402(5) . ?
C00R C00X 1.385(6) . ?
C00R C01A 1.385(6) . ?
C00S C015 1.534(6) . ?
C00T C01E 1.347(5) . ?
C00U C014 1.359(5) . ?
C00V H00V 0.9300 . ?
C00V C016 1.393(6) . ?
C00V C01C 1.390(6) . ?
C00W C010 1.394(5) . ?
C00W C015 1.538(5) . ?
C00X H00X 0.9300 . ?
C00X C01C 1.400(5) . ?
C00Y C017 1.540(5) . ?
C00Y C01D 1.318(6) . ?
C00Z H00D 0.9600 . ?
C00Z H00E 0.9600 . ?
C00Z H00F 0.9600 . ?
C010 H010 0.9300 . ?
C010 C013 1.399(6) . ?
C011 C01E 1.437(5) . ?
C20 H20A 0.8200 . ?
C20 H20B 1.00(6) . ?
C013 H013 0.9300 . ?
C014 C015 1.531(5) . ?
C016 H016 0.9300 . ?
C016 C01A 1.381(6) . ?
C017 C018 1.521(6) . ?
C017 C01C 1.553(5) . ?
C017 C01E 1.529(5) . ?
C019 H01A 0.9600 . ?
C019 H01B 0.9600 . ?
C019 H01C 0.9600 . ?
C01A H01D 0.9300 . ?
C01B H01E 0.9600 . ?
C01B H01F 0.9600 . ?
C01B H01G 0.9600 . ?
C01D H01H 0.8200 . ?
C01D H01I 0.91(7) . ?

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
C00T O00A C00Y 106.0(3) . . ?
C00U O00B C00L 106.6(3) . . ?
C00J N00F C00Z 115.0(3) . . ?
C00J N00F C011 127.4(3) . . ?
C011 N00F C00Z 117.4(3) . . ?
C00K N00G C00N 115.5(3) . . ?
C00K N00G C00P 126.7(3) . . ?
C00P N00G C00N 117.5(3) . . ?
C00K N00H C019 118.5(3) . . ?
C00U N00H C00K 118.9(3) . . ?
C00U N00H C019 122.6(3) . . ?
C00J N00I C01B 119.9(3) . . ?
C00T N00I C00J 118.4(3) . . ?
C00T N00I C01B 121.6(3) . . ?
O00C C00J N00F 122.5(4) . . ?
O00C C00J N00I 121.5(4) . . ?
N00F C00J N00I 116.0(3) . . ?
O009 C00K N00G 122.8(4) . . ?
O009 C00K N00H 121.6(4) . . ?
N00G C00K N00H 115.6(3) . . ?
O00B C00L C015 109.3(3) . . ?
C20 C00L O00B 118.9(3) . . ?
C20 C00L C015 131.9(4) . . ?
C00O C00M H00M 121.0 . . ?
C013 C00M H00M 121.0 . . ?
C013 C00M C00O 117.9(4) . . ?
N00G C00N H00A 109.5 . . ?
N00G C00N H00B 109.5 . . ?
N00G C00N H00C 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00B C00N H00C 109.5 . . ?
C00M C00O Br01 119.2(3) . . ?
C00M C00O C00Q 122.7(4) . . ?
C00Q C00O Br01 118.0(3) . . ?
O00D C00P N00G 119.4(3) . . ?
O00D C00P C014 127.0(4) . . ?
N00G C00P C014 113.5(3) . . ?
C00O C00Q H00Q 120.6 . . ?
C00O C00Q C00W 118.8(4) . . ?
C00W C00Q H00Q 120.6 . . ?
C00X C00R Br02 118.1(3) . . ?
C00X C00R C01A 122.9(4) . . ?
C01A C00R Br02 119.0(3) . . ?
F4 C00S F6 106.4(3) . . ?
F4 C00S F5 107.2(3) . . ?
F4 C00S C015 112.4(3) . . ?
F6 C00S C015 111.4(3) . . ?
F5 C00S F6 107.6(3) . . ?
F5 C00S C015 111.6(3) . . ?
N00I C00T O00A 117.5(3) . . ?
N00I C00T C01E 126.5(4) . . ?
C01E C00T O00A 115.9(3) . . ?
O00B C00U C014 115.3(3) . . ?
N00H C00U O00B 118.7(3) . . ?
N00H C00U C014 126.0(4) . . ?
C016 C00V H00V 119.7 . . ?
C01C C00V H00V 119.7 . . ?
C01C C00V C016 120.6(4) . . ?
C00Q C00W C015 118.7(3) . . ?
C010 C00W C00Q 119.2(3) . . ?
C010 C00W C015 122.0(3) . . ?
C00R C00X H00X 120.7 . . ?
C00R C00X C01C 118.5(4) . . ?
C01C C00X H00X 120.7 . . ?
O00A C00Y C017 109.3(3) . . ?
C01D C00Y O00A 118.2(4) . . ?
C01D C00Y C017 132.5(4) . . ?
N00F C00Z H00D 109.5 . . ?
N00F C00Z H00E 109.5 . . ?
N00F C00Z H00F 109.5 . . ?
H00D C00Z H00E 109.5 . . ?
H00D C00Z H00F 109.5 . . ?
H00E C00Z H00F 109.5 . . ?
C00W C010 H010 119.9 . . ?
C00W C010 C013 120.2(4) . . ?
C013 C010 H010 119.9 . . ?
O00E C011 N00F 120.1(3) . . ?
O00E C011 C01E 127.6(4) . . ?
N00F C011 C01E 112.3(3) . . ?
C00L C20 H20A 109.5 . . ?
C00L C20 H20B 118(3) . . ?
H20A C20 H20B 132.5 . . ?
C00M C013 C010 121.2(4) . . ?
C00M C013 H013 119.4 . . ?
C010 C013 H013 119.4 . . ?
C00P C014 C015 133.9(3) . . ?
C00U C014 C00P 118.9(4) . . ?
C00U C014 C015 107.1(3) . . ?
C00L C015 C00W 113.0(3) . . ?
C00S C015 C00L 108.9(3) . . ?
C00S C015 C00W 110.5(3) . . ?
C014 C015 C00L 99.4(3) . . ?
C014 C015 C00S 112.9(3) . . ?
C014 C015 C00W 111.8(3) . . ?
C00V C016 H016 119.7 . . ?
C01A C016 C00V 120.7(4) . . ?
C01A C016 H016 119.7 . . ?
C00Y C017 C01C 111.6(3) . . ?
C018 C017 C00Y 109.8(3) . . ?
C018 C017 C01C 110.2(3) . . ?
C018 C017 C01E 113.9(3) . . ?
C01E C017 C00Y 99.1(3) . . ?
C01E C017 C01C 111.7(3) . . ?
F1 C018 F2 106.6(3) . . ?
F1 C018 C017 111.9(3) . . ?
F2 C018 C017 111.3(3) . . ?
F3 C018 F1 107.2(3) . . ?
F3 C018 F2 106.5(3) . . ?
F3 C018 C017 113.0(3) . . ?
N00H C019 H01A 109.5 . . ?
N00H C019 H01B 109.5 . . ?
N00H C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?
C00R C01A H01D 121.0 . . ?
C016 C01A C00R 117.9(4) . . ?
C016 C01A H01D 121.0 . . ?
N00I C01B H01E 109.5 . . ?
N00I C01B H01F 109.5 . . ?
N00I C01B H01G 109.5 . . ?
H01E C01B H01F 109.5 . . ?
H01E C01B H01G 109.5 . . ?
H01F C01B H01G 109.5 . . ?
C00V C01C C00X 119.3(4) . . ?
C00V C01C C017 122.5(3) . . ?
C00X C01C C017 118.2(3) . . ?
C00Y C01D H01H 109.5 . . ?
C00Y C01D H01I 121(4) . . ?
H01H C01D H01I 128.9 . . ?
C00T C01E C011 119.2(3) . . ?
C00T C01E C017 107.4(3) . . ?
C011 C01E C017 133.1(3) . . ?

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
Br01 C00O C00Q C00W 179.4(3) . . . . ?
Br02 C00R C00X C01C 179.6(3) . . . . ?
Br02 C00R C01A C016 180.0(3) . . . . ?
F4 C00S C015 C00L -177.4(3) . . . . ?
F4 C00S C015 C00W 57.9(4) . . . . ?
F4 C00S C015 C014 -68.0(4) . . . . ?
F6 C00S C015 C00L 63.3(4) . . . . ?
F6 C00S C015 C00W -61.4(4) . . . . ?
F6 C00S C015 C014 172.7(3) . . . . ?
F5 C00S C015 C00L -57.0(4) . . . . ?
F5 C00S C015 C00W 178.4(3) . . . . ?
F5 C00S C015 C014 52.4(4) . . . . ?
O00A C00T C01E C011 179.9(3) . . . . ?
O00A C00T C01E C017 5.3(5) . . . . ?
O00A C00Y C017 C018 134.5(3) . . . . ?
O00A C00Y C017 C01C -103.0(3) . . . . ?
O00A C00Y C017 C01E 14.9(4) . . . . ?
O00B C00L C015 C00S 133.7(3) . . . . ?
O00B C00L C015 C00W -103.2(4) . . . . ?
O00B C00L C015 C014 15.4(4) . . . . ?
O00B C00U C014 C00P -177.4(3) . . . . ?
O00B C00U C014 C015 6.3(5) . . . . ?
O00D C00P C014 C00U 179.8(4) . . . . ?
O00D C00P C014 C015 -5.0(7) . . . . ?
O00E C011 C01E C00T 179.6(4) . . . . ?
O00E C011 C01E C017 -7.4(7) . . . . ?
N00F C011 C01E C00T -1.3(5) . . . . ?
N00F C011 C01E C017 171.7(4) . . . . ?
N00G C00P C014 C00U 0.7(5) . . . . ?
N00G C00P C014 C015 175.9(4) . . . . ?
N00H C00U C014 C00P 3.7(6) . . . . ?
N00H C00U C014 C015 -172.7(3) . . . . ?
N00I C00T C01E C011 2.1(6) . . . . ?
N00I C00T C01E C017 -172.5(4) . . . . ?
C00J N00F C011 O00E 178.5(4) . . . . ?
C00J N00F C011 C01E -0.7(5) . . . . ?
C00J N00I C00T O00A -178.6(3) . . . . ?
C00J N00I C00T C01E -0.8(6) . . . . ?
C00K N00G C00P O00D 175.4(4) . . . . ?
C00K N00G C00P C014 -5.4(5) . . . . ?
C00K N00H C00U O00B 177.6(3) . . . . ?
C00K N00H C00U C014 -3.5(6) . . . . ?
C00L O00B C00U N00H -176.9(3) . . . . ?
C00L O00B C00U C014 4.1(4) . . . . ?
C00M C00O C00Q C00W 0.8(6) . . . . ?
C00N N00G C00K O009 -0.7(6) . . . . ?
C00N N00G C00K N00H -179.5(3) . . . . ?
C00N N00G C00P O00D 0.7(6) . . . . ?
C00N N00G C00P C014 179.9(3) . . . . ?
C00O C00M C013 C010 0.8(6) . . . . ?
C00O C00Q C00W C010 0.1(5) . . . . ?
C00O C00Q C00W C015 -176.3(3) . . . . ?
C00P N00G C00K O009 -175.5(4) . . . . ?
C00P N00G C00K N00H 5.7(5) . . . . ?
C00P C014 C015 C00L 171.7(4) . . . . ?
C00P C014 C015 C00S 56.5(6) . . . . ?
C00P C014 C015 C00W -68.8(6) . . . . ?
C00Q C00W C010 C013 -0.5(6) . . . . ?
C00Q C00W C015 C00L 163.5(3) . . . . ?
C00Q C00W C015 C00S -74.2(4) . . . . ?
C00Q C00W C015 C014 52.4(5) . . . . ?
C00R C00X C01C C00V 1.2(5) . . . . ?
C00R C00X C01C C017 -176.8(3) . . . . ?
C00T O00A C00Y C017 -12.8(4) . . . . ?
C00T O00A C00Y C01D 166.7(4) . . . . ?
C00T N00I C00J O00C 179.1(3) . . . . ?
C00T N00I C00J N00F -1.2(5) . . . . ?
C00U O00B C00L C20 166.7(4) . . . . ?
C00U O00B C00L C015 -12.8(4) . . . . ?
C00U N00H C00K O009 -179.9(4) . . . . ?
C00U N00H C00K N00G -1.1(5) . . . . ?
C00U C014 C015 C00L -12.7(4) . . . . ?
C00U C014 C015 C00S -127.9(3) . . . . ?
C00U C014 C015 C00W 106.8(4) . . . . ?
C00V C016 C01A C00R -0.3(6) . . . . ?
C00W C010 C013 C00M 0.1(6) . . . . ?
C00X C00R C01A C016 -0.3(6) . . . . ?
C00Y O00A C00T N00I -177.2(3) . . . . ?
C00Y O00A C00T C01E 4.8(4) . . . . ?
C00Y C017 C018 F1 -55.1(4) . . . . ?
C00Y C017 C018 F2 64.1(4) . . . . ?
C00Y C017 C018 F3 -176.2(3) . . . . ?
C00Y C017 C01C C00V -16.6(5) . . . . ?
C00Y C017 C01C C00X 161.3(3) . . . . ?
C00Y C017 C01E C00T -11.8(4) . . . . ?
C00Y C017 C01E C011 174.6(4) . . . . ?
C00Z N00F C00J O00C -2.4(5) . . . . ?
C00Z N00F C00J N00I 177.8(3) . . . . ?
C00Z N00F C011 O00E 2.7(6) . . . . ?
C00Z N00F C011 C01E -176.5(3) . . . . ?
C010 C00W C015 C00L -12.8(5) . . . . ?
C010 C00W C015 C00S 109.5(4) . . . . ?
C010 C00W C015 C014 -123.9(4) . . . . ?
C011 N00F C00J O00C -178.3(4) . . . . ?
C011 N00F C00J N00I 2.0(6) . . . . ?
C20 C00L C015 C00S -45.8(6) . . . . ?
C20 C00L C015 C00W 77.4(5) . . . . ?
C20 C00L C015 C014 -164.1(4) . . . . ?
C013 C00M C00O Br01 -179.9(3) . . . . ?
C013 C00M C00O C00Q -1.3(6) . . . . ?
C015 C00W C010 C013 175.7(4) . . . . ?
C016 C00V C01C C00X -1.8(6) . . . . ?
C016 C00V C01C C017 176.0(4) . . . . ?
C018 C017 C01C C00V 105.7(4) . . . . ?
C018 C017 C01C C00X -76.4(4) . . . . ?
C018 C017 C01E C00T -128.3(3) . . . . ?
C018 C017 C01E C011 58.1(5) . . . . ?
C019 N00H C00K O009 -1.5(6) . . . . ?
C019 N00H C00K N00G 177.3(3) . . . . ?
C019 N00H C00U O00B -0.7(5) . . . . ?
C019 N00H C00U C014 178.2(4) . . . . ?
C01A C00R C00X C01C -0.1(6) . . . . ?
C01B N00I C00J O00C -0.2(6) . . . . ?
C01B N00I C00J N00F 179.5(3) . . . . ?
C01B N00I C00T O00A 0.7(5) . . . . ?
C01B N00I C00T C01E 178.5(4) . . . . ?
C01C C00V C016 C01A 1.4(6) . . . . ?
C01C C017 C018 F1 -178.5(3) . . . . ?
C01C C017 C018 F2 -59.3(4) . . . . ?
C01C C017 C018 F3 60.5(4) . . . . ?
C01C C017 C01E C00T 106.0(4) . . . . ?
C01C C017 C01E C011 -67.6(6) . . . . ?
C01D C00Y C017 C018 -44.9(6) . . . . ?
C01D C00Y C017 C01C 77.7(6) . . . . ?
C01D C00Y C017 C01E -164.5(4) . . . . ?
C01E C017 C018 F1 55.0(4) . . . . ?
C01E C017 C018 F2 174.2(3) . . . . ?
C01E C017 C018 F3 -66.0(4) . . . . ?
C01E C017 C01C C00V -126.6(4) . . . . ?
C01E C017 C01C C00X 51.3(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_20jana_o_0m
_database_code_depnum_ccdc_archive 'CCDC 2420279'
loop_
_audit_author_name
_audit_author_address
'Ramesh Singh '
;IIT Kanpur
India
;
_audit_update_record             
;
2025-01-29 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_audit_creation_date             2025-01-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 F3 N2 O3'
_chemical_formula_sum            'C16 H17 F3 N2 O3'
_chemical_formula_weight         342.31
_chemical_absolute_configuration ad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9229(4)
_cell_length_b                   7.0647(3)
_cell_length_c                   13.8678(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.798(2)
_cell_angle_gamma                90
_cell_volume                     775.30(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7181
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4244
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1652 before and 0.0674 after correction.
The Ratio of minimum to maximum transmission is 0.5691.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             356
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13050
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3669
_reflns_number_total             3883
_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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip  (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.025
_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)+(0.0446P)²+0.2031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00H(H00H)
1.b Secondary CH2 refined with riding coordinates:
 C00J(H00B,H00C)
1.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00E(H00E), C00F(H00F), C00I(H00I), C00K(H00K)
1.d Idealised Me refined as rotating group:
 C00M(H00D,H00G,H00J), C00N(H00L,H00M,H00N), C00O(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F001 F 0.24404(17) 0.29181(19) 0.09819(10) 0.0198(3) Uani 1 1 d . . . . .
F002 F 0.05289(17) 0.23313(19) 0.19950(10) 0.0208(3) Uani 1 1 d . . . . .
F003 F 0.01266(18) 0.4471(2) 0.09020(10) 0.0240(3) Uani 1 1 d . . . . .
O004 O 0.0851(2) 0.3786(2) 0.40154(12) 0.0181(3) Uani 1 1 d . . . . .
O005 O 0.5672(2) 0.0849(3) 0.50086(12) 0.0222(4) Uani 1 1 d . . . . .
O006 O -0.0720(2) 0.6286(3) 0.24678(12) 0.0216(4) Uani 1 1 d . . . . .
N007 N 0.3123(2) 0.1926(3) 0.43826(13) 0.0142(4) Uani 1 1 d . . . . .
N008 N 0.5530(2) 0.1982(3) 0.34715(13) 0.0155(4) Uani 1 1 d . . . . .
C009 C 0.1285(3) 0.3735(3) 0.15284(16) 0.0166(4) Uani 1 1 d . . . . .
C00A C 0.4939(3) 0.6811(3) 0.18266(15) 0.0152(4) Uani 1 1 d . . . . .
H00A H 0.550227 0.611056 0.231048 0.018 Uiso 1 1 calc R U . . .
C00B C 0.4870(3) 0.1545(3) 0.43206(16) 0.0150(4) Uani 1 1 d . . . . .
C00C C 0.3195(3) 0.6570(3) 0.16535(15) 0.0136(4) Uani 1 1 d . . . . .
C00D C 0.2256(3) 0.3280(3) 0.38314(15) 0.0137(4) Uani 1 1 d . . . . .
C00E C 0.2380(3) 0.7697(3) 0.09395(16) 0.0164(4) Uani 1 1 d . . . . .
H00E H 0.121662 0.759543 0.082609 0.020 Uiso 1 1 calc R U . . .
C00F C 0.5840(3) 0.8085(3) 0.12839(16) 0.0172(4) Uani 1 1 d . . . . .
H00F H 0.699972 0.821240 0.140233 0.021 Uiso 1 1 calc R U . . .
C00G C 0.0759(3) 0.6402(3) 0.27162(15) 0.0160(4) Uani 1 1 d . . . . .
C00H C 0.3248(3) 0.4098(3) 0.30116(15) 0.0125(4) Uani 1 1 d . . . . .
H00H H 0.399783 0.505628 0.331182 0.015 Uiso 1 1 calc R U . . .
C00I C 0.5020(3) 0.9169(3) 0.05653(16) 0.0176(4) Uani 1 1 d . . . . .
H00I H 0.562296 1.001764 0.020182 0.021 Uiso 1 1 calc R U . . .
C00J C 0.4415(3) 0.2547(3) 0.26535(15) 0.0145(4) Uani 1 1 d . . . . .
H00B H 0.375623 0.147299 0.241510 0.017 Uiso 1 1 calc R U . . .
H00C H 0.507206 0.302426 0.213362 0.017 Uiso 1 1 calc R U . . .
C00K C 0.3286(3) 0.8963(3) 0.04007(16) 0.0184(4) Uani 1 1 d . . . . .
H00K H 0.272594 0.968149 -0.007678 0.022 Uiso 1 1 calc R U . . .
C00L C 0.2135(3) 0.5173(3) 0.22346(14) 0.0122(4) Uani 1 1 d . . . . .
C00M C 0.2338(3) 0.1252(3) 0.52538(16) 0.0204(5) Uani 1 1 d . . . . .
H00D H 0.282284 0.005650 0.544504 0.031 Uiso 1 1 calc R U . . .
H00G H 0.114405 0.110314 0.512274 0.031 Uiso 1 1 calc R U . . .
H00J H 0.253163 0.215506 0.576458 0.031 Uiso 1 1 calc R U . . .
C00N C 0.1416(3) 0.7893(3) 0.34178(17) 0.0201(5) Uani 1 1 d . . . . .
H00L H 0.176539 0.898515 0.306718 0.030 Uiso 1 1 calc R U . . .
H00M H 0.236123 0.739750 0.379663 0.030 Uiso 1 1 calc R U . . .
H00N H 0.053737 0.824542 0.383595 0.030 Uiso 1 1 calc R U . . .
C00O C 0.7300(3) 0.1560(4) 0.33148(18) 0.0220(5) Uani 1 1 d . . . . .
H00O H 0.790230 0.139209 0.392635 0.033 Uiso 1 1 calc R U . . .
H00P H 0.779037 0.258915 0.297352 0.033 Uiso 1 1 calc R U . . .
H00Q H 0.737069 0.042086 0.294143 0.033 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
F001 C009 1.346(3) . ?
F002 C009 1.341(3) . ?
F003 C009 1.338(2) . ?
O004 C00D 1.209(3) . ?
O005 C00B 1.223(3) . ?
O006 C00G 1.208(3) . ?
N007 C00B 1.417(3) . ?
N007 C00D 1.385(3) . ?
N007 C00M 1.465(3) . ?
N008 C00B 1.348(3) . ?
N008 C00J 1.459(3) . ?
N008 C00O 1.460(3) . ?
C009 C00L 1.543(3) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.401(3) . ?
C00A C00F 1.392(3) . ?
C00C C00E 1.404(3) . ?
C00C C00L 1.547(3) . ?
C00D C00H 1.527(3) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.388(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.392(3) . ?
C00G C00L 1.568(3) . ?
C00G C00N 1.509(3) . ?
C00H H00H 0.9800 . ?
C00H C00J 1.532(3) . ?
C00H C00L 1.556(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.389(3) . ?
C00J H00B 0.9700 . ?
C00J H00C 0.9700 . ?
C00K H00K 0.9300 . ?
C00M H00D 0.9600 . ?
C00M H00G 0.9600 . ?
C00M H00J 0.9600 . ?
C00N H00L 0.9600 . ?
C00N H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00O H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 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
C00B N007 C00M 116.33(18) . . ?
C00D N007 C00B 123.84(18) . . ?
C00D N007 C00M 117.43(18) . . ?
C00B N008 C00J 119.72(17) . . ?
C00B N008 C00O 119.99(19) . . ?
C00J N008 C00O 119.31(18) . . ?
F001 C009 C00L 110.61(17) . . ?
F002 C009 F001 106.66(18) . . ?
F002 C009 C00L 111.84(17) . . ?
F003 C009 F001 105.36(17) . . ?
F003 C009 F002 106.97(17) . . ?
F003 C009 C00L 114.87(18) . . ?
C00C C00A H00A 119.6 . . ?
C00F C00A H00A 119.6 . . ?
C00F C00A C00C 120.9(2) . . ?
O005 C00B N007 120.1(2) . . ?
O005 C00B N008 124.4(2) . . ?
N008 C00B N007 115.57(18) . . ?
C00A C00C C00E 117.9(2) . . ?
C00A C00C C00L 122.95(18) . . ?
C00E C00C C00L 119.11(18) . . ?
O004 C00D N007 121.6(2) . . ?
O004 C00D C00H 123.9(2) . . ?
N007 C00D C00H 114.42(18) . . ?
C00C C00E H00E 119.6 . . ?
C00K C00E C00C 120.8(2) . . ?
C00K C00E H00E 119.6 . . ?
C00A C00F H00F 119.7 . . ?
C00A C00F C00I 120.6(2) . . ?
C00I C00F H00F 119.7 . . ?
O006 C00G C00L 121.7(2) . . ?
O006 C00G C00N 122.0(2) . . ?
C00N C00G C00L 115.86(18) . . ?
C00D C00H H00H 105.6 . . ?
C00D C00H C00J 108.13(17) . . ?
C00D C00H C00L 113.94(17) . . ?
C00J C00H H00H 105.6 . . ?
C00J C00H C00L 117.07(17) . . ?
C00L C00H H00H 105.6 . . ?
C00F C00I H00I 120.6 . . ?
C00K C00I C00F 118.9(2) . . ?
C00K C00I H00I 120.6 . . ?
N008 C00J C00H 107.21(16) . . ?
N008 C00J H00B 110.3 . . ?
N008 C00J H00C 110.3 . . ?
C00H C00J H00B 110.3 . . ?
C00H C00J H00C 110.3 . . ?
H00B C00J H00C 108.5 . . ?
C00E C00K C00I 120.9(2) . . ?
C00E C00K H00K 119.6 . . ?
C00I C00K H00K 119.6 . . ?
C009 C00L C00C 108.69(17) . . ?
C009 C00L C00G 110.11(17) . . ?
C009 C00L C00H 109.46(17) . . ?
C00C C00L C00G 105.97(17) . . ?
C00C C00L C00H 111.61(17) . . ?
C00H C00L C00G 110.93(17) . . ?
N007 C00M H00D 109.5 . . ?
N007 C00M H00G 109.5 . . ?
N007 C00M H00J 109.5 . . ?
H00D C00M H00G 109.5 . . ?
H00D C00M H00J 109.5 . . ?
H00G C00M H00J 109.5 . . ?
C00G C00N H00L 109.5 . . ?
C00G C00N H00M 109.5 . . ?
C00G C00N H00N 109.5 . . ?
H00L C00N H00M 109.5 . . ?
H00L C00N H00N 109.5 . . ?
H00M C00N H00N 109.5 . . ?
N008 C00O H00O 109.5 . . ?
N008 C00O H00P 109.5 . . ?
N008 C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 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
F001 C009 C00L C00C 53.0(2) . . . . ?
F001 C009 C00L C00G 168.66(17) . . . . ?
F001 C009 C00L C00H -69.1(2) . . . . ?
F002 C009 C00L C00C 171.72(17) . . . . ?
F002 C009 C00L C00G -72.6(2) . . . . ?
F002 C009 C00L C00H 49.6(2) . . . . ?
F003 C009 C00L C00C -66.1(2) . . . . ?
F003 C009 C00L C00G 49.6(2) . . . . ?
F003 C009 C00L C00H 171.76(18) . . . . ?
O004 C00D C00H C00J -150.1(2) . . . . ?
O004 C00D C00H C00L -18.0(3) . . . . ?
O006 C00G C00L C009 -6.3(3) . . . . ?
O006 C00G C00L C00C 111.0(2) . . . . ?
O006 C00G C00L C00H -127.7(2) . . . . ?
N007 C00D C00H C00J 32.0(2) . . . . ?
N007 C00D C00H C00L 163.96(17) . . . . ?
C00A C00C C00E C00K 2.2(3) . . . . ?
C00A C00C C00L C009 -121.1(2) . . . . ?
C00A C00C C00L C00G 120.6(2) . . . . ?
C00A C00C C00L C00H -0.3(3) . . . . ?
C00A C00F C00I C00K 0.2(3) . . . . ?
C00B N007 C00D O004 -167.3(2) . . . . ?
C00B N007 C00D C00H 10.7(3) . . . . ?
C00B N008 C00J C00H 50.1(3) . . . . ?
C00C C00A C00F C00I 1.0(3) . . . . ?
C00C C00E C00K C00I -1.1(3) . . . . ?
C00D N007 C00B O005 155.3(2) . . . . ?
C00D N007 C00B N008 -25.2(3) . . . . ?
C00D C00H C00J N008 -59.5(2) . . . . ?
C00D C00H C00L C009 -80.9(2) . . . . ?
C00D C00H C00L C00C 158.74(17) . . . . ?
C00D C00H C00L C00G 40.8(2) . . . . ?
C00E C00C C00L C009 61.0(2) . . . . ?
C00E C00C C00L C00G -57.3(2) . . . . ?
C00E C00C C00L C00H -178.21(18) . . . . ?
C00F C00A C00C C00E -2.1(3) . . . . ?
C00F C00A C00C C00L 180.0(2) . . . . ?
C00F C00I C00K C00E -0.1(3) . . . . ?
C00J N008 C00B O005 171.1(2) . . . . ?
C00J N008 C00B N007 -8.3(3) . . . . ?
C00J C00H C00L C009 46.6(2) . . . . ?
C00J C00H C00L C00C -73.7(2) . . . . ?
C00J C00H C00L C00G 168.34(17) . . . . ?
C00L C00C C00E C00K -179.8(2) . . . . ?
C00L C00H C00J N008 170.19(18) . . . . ?
C00M N007 C00B O005 -6.6(3) . . . . ?
C00M N007 C00B N008 172.87(19) . . . . ?
C00M N007 C00D O004 -5.6(3) . . . . ?
C00M N007 C00D C00H 172.48(18) . . . . ?
C00N C00G C00L C009 -179.23(18) . . . . ?
C00N C00G C00L C00C -61.9(2) . . . . ?
C00N C00G C00L C00H 59.4(2) . . . . ?
C00O N008 C00B O005 2.4(3) . . . . ?
C00O N008 C00B N007 -177.00(19) . . . . ?
C00O N008 C00J C00H -141.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
