# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2024514'
loop_
_audit_author_name
_audit_author_address
'Anindita Das'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2020-08-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 F4 I N O'
_chemical_formula_sum            'C15 H6 F4 I N O'
_chemical_formula_weight         419.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.6686(18)
_cell_length_b                   4.5292(7)
_cell_length_c                   25.933(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.908(5)
_cell_angle_gamma                90
_cell_volume                     1335.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    161(2)
_cell_measurement_reflns_used    12588
_cell_measurement_theta_min      2.663
_cell_measurement_theta_max      27.233

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.084
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.445
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      161(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Micro-focus
_diffrn_measurement_device_type  'Bruker D8VENTURE with PHOTON II Detector'
_diffrn_measurement_method       'phi, omega and kappa scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12588
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         27.233
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2953
_reflns_number_gt                2529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+58.3568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0930
_refine_ls_wR_factor_ref         0.2430
_refine_ls_wR_factor_gt          0.2381
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.249
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.25414(8) 0.0421(2) 0.91450(3) 0.0294(3) Uani 1 1 d . . . . .
F1 F 0.0863(7) 0.780(2) 0.7508(3) 0.035(2) Uani 1 1 d . . . . .
F2 F 0.0788(8) 0.489(2) 0.8414(3) 0.041(2) Uani 1 1 d . . . . .
O1 O 0.2701(9) 0.679(2) 0.7020(3) 0.031(2) Uani 1 1 d . . . . .
F4 F 0.4271(7) 0.239(2) 0.7405(3) 0.035(2) Uani 1 1 d . . . . .
F3 F 0.4206(7) -0.042(2) 0.8315(3) 0.038(2) Uani 1 1 d . . . . .
N1 N 0.2795(11) 0.697(3) 0.5172(4) 0.033(3) Uani 1 1 d . . . . .
C1 C 0.2521(12) 0.227(3) 0.8399(5) 0.026(3) Uani 1 1 d . . . . .
C2 C 0.1668(11) 0.425(3) 0.8185(5) 0.024(3) Uani 1 1 d . . . . .
C3 C 0.1703(12) 0.573(3) 0.7708(5) 0.026(3) Uani 1 1 d . . . . .
C4 C 0.2603(14) 0.522(3) 0.7434(5) 0.032(3) Uani 1 1 d . . . . .
C5 C 0.2242(13) 0.565(3) 0.6507(5) 0.029(3) Uani 1 1 d . . . . .
C6 C 0.2784(12) 0.686(3) 0.6115(5) 0.026(3) Uani 1 1 d . . . . .
C7 C 0.3698(12) 0.886(3) 0.6215(5) 0.029(3) Uani 1 1 d . . . . .
H7 H 0.401066 0.952380 0.656586 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4145(13) 0.987(4) 0.5811(6) 0.033(3) Uani 1 1 d . . . . .
H8 H 0.477031 1.125936 0.587149 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3650(13) 0.878(4) 0.5285(6) 0.035(3) Uani 1 1 d . . . . .
H9 H 0.398353 0.945969 0.500448 0.042 Uiso 1 1 calc R U . . .
C11 C 0.2331(12) 0.587(3) 0.5592(5) 0.029(3) Uani 1 1 d . . . . .
C12 C 0.1380(13) 0.386(4) 0.5474(6) 0.036(3) Uani 1 1 d . . . . .
H12 H 0.107393 0.325029 0.511949 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0909(13) 0.280(4) 0.5871(6) 0.036(3) Uani 1 1 d . . . . .
H13 H 0.027191 0.144112 0.579118 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1351(13) 0.368(3) 0.6399(6) 0.034(3) Uani 1 1 d . . . . .
H14 H 0.102764 0.289490 0.667564 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3410(11) 0.300(3) 0.7657(5) 0.025(3) Uani 1 1 d . . . . .
C16 C 0.3383(11) 0.162(3) 0.8128(5) 0.025(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.103(13) . ?
F1 C3 1.369(15) . ?
F2 C2 1.329(14) . ?
O1 C4 1.312(15) . ?
O1 C5 1.413(15) . ?
F4 C15 1.344(14) . ?
F3 C16 1.344(15) . ?
N1 C9 1.27(2) . ?
N1 C11 1.409(18) . ?
C1 C2 1.364(19) . ?
C1 C16 1.380(18) . ?
C2 C3 1.415(19) . ?
C3 C4 1.412(19) . ?
C4 C15 1.41(2) . ?
C5 C14 1.35(2) . ?
C5 C6 1.423(19) . ?
C6 C7 1.38(2) . ?
C6 C11 1.413(18) . ?
C7 C8 1.35(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.44(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C11 C12 1.42(2) . ?
C12 C13 1.36(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.41(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.378(18) . ?

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
C4 O1 C5 119.2(12) . . ?
C9 N1 C11 117.7(12) . . ?
C2 C1 C16 118.7(12) . . ?
C2 C1 I1 119.6(10) . . ?
C16 C1 I1 121.6(10) . . ?
F2 C2 C1 121.9(13) . . ?
F2 C2 C3 117.6(11) . . ?
C1 C2 C3 120.5(12) . . ?
F1 C3 C4 118.1(12) . . ?
F1 C3 C2 119.7(11) . . ?
C4 C3 C2 122.1(12) . . ?
O1 C4 C3 122.3(14) . . ?
O1 C4 C15 123.3(13) . . ?
C3 C4 C15 114.4(11) . . ?
C14 C5 O1 123.2(13) . . ?
C14 C5 C6 123.3(13) . . ?
O1 C5 C6 113.4(12) . . ?
C7 C6 C11 119.8(13) . . ?
C7 C6 C5 124.4(12) . . ?
C11 C6 C5 115.8(13) . . ?
C8 C7 C6 119.5(13) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 118.4(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
N1 C9 C8 124.3(13) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N1 C11 C6 120.2(13) . . ?
N1 C11 C12 118.6(13) . . ?
C6 C11 C12 121.2(13) . . ?
C13 C12 C11 119.7(14) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.9(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C5 C14 C13 119.1(14) . . ?
C5 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
F4 C15 C16 120.4(12) . . ?
F4 C15 C4 116.7(12) . . ?
C16 C15 C4 122.8(12) . . ?
F3 C16 C15 118.4(12) . . ?
F3 C16 C1 120.4(12) . . ?
C15 C16 C1 121.3(12) . . ?

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
C16 C1 C2 F2 177.3(12) . . . . ?
I1 C1 C2 F2 -5.4(18) . . . . ?
C16 C1 C2 C3 -3(2) . . . . ?
I1 C1 C2 C3 174.0(10) . . . . ?
F2 C2 C3 F1 1.8(19) . . . . ?
C1 C2 C3 F1 -177.7(12) . . . . ?
F2 C2 C3 C4 179.8(13) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C5 O1 C4 C3 -98.1(17) . . . . ?
C5 O1 C4 C15 85.0(18) . . . . ?
F1 C3 C4 O1 5(2) . . . . ?
C2 C3 C4 O1 -173.3(13) . . . . ?
F1 C3 C4 C15 -178.2(12) . . . . ?
C2 C3 C4 C15 4(2) . . . . ?
C4 O1 C5 C14 26(2) . . . . ?
C4 O1 C5 C6 -156.2(13) . . . . ?
C14 C5 C6 C7 -179.6(14) . . . . ?
O1 C5 C6 C7 2(2) . . . . ?
C14 C5 C6 C11 0(2) . . . . ?
O1 C5 C6 C11 -177.9(12) . . . . ?
C11 C6 C7 C8 0(2) . . . . ?
C5 C6 C7 C8 -179.8(14) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
C11 N1 C9 C8 -2(2) . . . . ?
C7 C8 C9 N1 2(2) . . . . ?
C9 N1 C11 C6 2(2) . . . . ?
C9 N1 C11 C12 180.0(14) . . . . ?
C7 C6 C11 N1 -1(2) . . . . ?
C5 C6 C11 N1 179.1(13) . . . . ?
C7 C6 C11 C12 -178.9(14) . . . . ?
C5 C6 C11 C12 1(2) . . . . ?
N1 C11 C12 C13 -179.3(15) . . . . ?
C6 C11 C12 C13 -1(2) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
O1 C5 C14 C13 176.5(14) . . . . ?
C6 C5 C14 C13 -1(2) . . . . ?
C12 C13 C14 C5 1(2) . . . . ?
O1 C4 C15 F4 -4(2) . . . . ?
C3 C4 C15 F4 178.7(12) . . . . ?
O1 C4 C15 C16 171.8(14) . . . . ?
C3 C4 C15 C16 -5(2) . . . . ?
F4 C15 C16 F3 -2.7(19) . . . . ?
C4 C15 C16 F3 -178.5(13) . . . . ?
F4 C15 C16 C1 178.6(13) . . . . ?
C4 C15 C16 C1 3(2) . . . . ?
C2 C1 C16 F3 -176.9(12) . . . . ?
I1 C1 C16 F3 5.9(18) . . . . ?
C2 C1 C16 C15 2(2) . . . . ?
I1 C1 C16 C15 -175.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8 F3 0.95 2.65 3.382(17) 134.5 2_666 yes
C14 H14 F2 0.95 2.48 3.153(17) 127.4 2_546 yes

_refine_diff_density_max         2.333
_refine_diff_density_min         -2.214
_refine_diff_density_rms         0.290

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2024515'
loop_
_audit_author_name
_audit_author_address
'Anindita Das'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2020-08-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 F4 I N O'
_chemical_formula_sum            'C15 H6 F4 I N O'
_chemical_formula_weight         419.11

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   14.522(3)
_cell_length_b                   12.084(3)
_cell_length_c                   8.162(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1432.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11866
_cell_measurement_theta_min      2.805
_cell_measurement_theta_max      27.124

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.944
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.280
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Micro-focus
_diffrn_measurement_device_type  'Bruker D8VENTURE with PHOTON II Detector'
_diffrn_measurement_method       'phi, omega and kappa scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11866
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         27.124
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3104
_reflns_number_gt                2897
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I -0.21829(2) 0.93471(3) 0.46215(12) 0.03284(19) Uani 1 1 d . . . . .
F2 F -0.2336(3) 0.6858(4) 0.3306(7) 0.0439(11) Uani 1 1 d . . . . .
F4 F 0.0865(3) 0.7173(3) 0.6697(6) 0.0397(10) Uani 1 1 d . . . . .
F1 F -0.1231(2) 0.5134(3) 0.3447(5) 0.0321(8) Uani 1 1 d . . . . .
F3 F -0.0204(3) 0.8960(3) 0.6423(6) 0.0404(10) Uani 1 1 d . . . . .
O1 O 0.0476(3) 0.5265(3) 0.5088(5) 0.0266(9) Uani 1 1 d . . . . .
N1 N 0.1650(3) 0.3675(4) 0.4203(6) 0.0284(12) Uani 1 1 d . . . . .
C7 C -0.0578(4) 0.3917(5) 0.6275(9) 0.0305(13) Uani 1 1 d . . . . .
H6 H -0.097975 0.446936 0.661943 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0077(4) 0.7092(6) 0.5862(8) 0.0273(13) Uani 1 1 d . . . . .
C14 C -0.0482(4) 0.8009(5) 0.5704(8) 0.0266(12) Uani 1 1 d . . . . .
C4 C 0.0645(5) 0.2242(5) 0.5343(9) 0.0315(13) Uani 1 1 d . . . . .
C10 C -0.0164(4) 0.6099(4) 0.5109(7) 0.0218(11) Uani 1 1 d . . . . .
C9 C 0.0858(4) 0.3359(5) 0.4968(7) 0.0242(13) Uani 1 1 d . . . . .
C5 C -0.0195(6) 0.1976(6) 0.6150(10) 0.0403(17) Uani 1 1 d . . . . .
H4 H -0.034139 0.124230 0.637224 0.048 Uiso 1 1 calc R U . . .
C12 C -0.1542(4) 0.6976(5) 0.4151(8) 0.0283(13) Uani 1 1 d . . . . .
C11 C -0.0974(4) 0.6051(5) 0.4251(7) 0.0263(13) Uani 1 1 d . . . . .
C13 C -0.1310(4) 0.7976(5) 0.4877(9) 0.0287(14) Uani 1 1 d . . . . .
C2 C 0.2087(5) 0.1747(6) 0.4100(11) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.251965 0.122344 0.377395 0.051 Uiso 1 1 calc R U . . .
C6 C -0.0781(5) 0.2792(6) 0.6594(10) 0.0375(16) Uani 1 1 d . . . . .
H5 H -0.132833 0.261021 0.711943 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0210(4) 0.4188(5) 0.5460(8) 0.0235(12) Uani 1 1 d . . . . .
C1 C 0.2240(4) 0.2875(7) 0.3799(12) 0.0396(18) Uani 1 1 d . . . . .
H1 H 0.278680 0.307729 0.328669 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1307(5) 0.1426(5) 0.4867(10) 0.0397(17) Uani 1 1 d . . . . .
H3 H 0.120165 0.068154 0.508397 0.048 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
I1 C13 2.097(6) . ?
F2 C12 1.351(6) . ?
F4 C15 1.335(7) . ?
F1 C11 1.340(7) . ?
F3 C14 1.352(7) . ?
O1 C10 1.371(7) . ?
O1 C8 1.392(7) . ?
N1 C1 1.333(8) . ?
N1 C9 1.364(7) . ?
C7 C8 1.363(9) . ?
C7 C6 1.416(9) . ?
C7 H6 0.9300 . ?
C15 C14 1.380(10) . ?
C15 C10 1.392(8) . ?
C14 C13 1.380(9) . ?
C4 C9 1.419(8) . ?
C4 C5 1.423(10) . ?
C4 C3 1.431(9) . ?
C10 C11 1.370(8) . ?
C9 C8 1.432(8) . ?
C5 C6 1.351(11) . ?
C5 H4 0.9300 . ?
C12 C13 1.387(8) . ?
C12 C11 1.392(8) . ?
C2 C3 1.351(11) . ?
C2 C1 1.403(11) . ?
C2 H2 0.9300 . ?
C6 H5 0.9300 . ?
C1 H1 0.9300 . ?
C3 H3 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
C10 O1 C8 119.8(5) . . ?
C1 N1 C9 116.9(5) . . ?
C8 C7 C6 119.7(6) . . ?
C8 C7 H6 120.2 . . ?
C6 C7 H6 120.2 . . ?
F4 C15 C14 119.5(6) . . ?
F4 C15 C10 120.2(5) . . ?
C14 C15 C10 120.2(5) . . ?
F3 C14 C13 119.8(5) . . ?
F3 C14 C15 117.8(5) . . ?
C13 C14 C15 122.4(6) . . ?
C9 C4 C5 120.1(6) . . ?
C9 C4 C3 116.7(6) . . ?
C5 C4 C3 123.2(6) . . ?
C11 C10 O1 123.0(5) . . ?
C11 C10 C15 118.6(5) . . ?
O1 C10 C15 117.9(5) . . ?
N1 C9 C4 123.4(5) . . ?
N1 C9 C8 119.1(5) . . ?
C4 C9 C8 117.5(5) . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H4 120.0 . . ?
C4 C5 H4 120.0 . . ?
F2 C12 C13 121.2(5) . . ?
F2 C12 C11 116.8(5) . . ?
C13 C12 C11 122.0(5) . . ?
F1 C11 C10 121.6(5) . . ?
F1 C11 C12 118.1(5) . . ?
C10 C11 C12 120.3(5) . . ?
C14 C13 C12 116.5(5) . . ?
C14 C13 I1 123.6(5) . . ?
C12 C13 I1 119.9(4) . . ?
C3 C2 C1 119.5(6) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C5 C6 C7 121.4(6) . . ?
C5 C6 H5 119.3 . . ?
C7 C6 H5 119.3 . . ?
C7 C8 O1 124.3(6) . . ?
C7 C8 C9 121.4(5) . . ?
O1 C8 C9 114.3(5) . . ?
N1 C1 C2 124.1(6) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?

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
F4 C15 C14 F3 -0.5(9) . . . . ?
C10 C15 C14 F3 -178.3(6) . . . . ?
F4 C15 C14 C13 -179.1(6) . . . . ?
C10 C15 C14 C13 3.1(10) . . . . ?
C8 O1 C10 C11 -53.1(8) . . . . ?
C8 O1 C10 C15 135.5(6) . . . . ?
F4 C15 C10 C11 -179.4(6) . . . . ?
C14 C15 C10 C11 -1.6(9) . . . . ?
F4 C15 C10 O1 -7.7(9) . . . . ?
C14 C15 C10 O1 170.2(6) . . . . ?
C1 N1 C9 C4 0.1(9) . . . . ?
C1 N1 C9 C8 178.7(6) . . . . ?
C5 C4 C9 N1 179.8(6) . . . . ?
C3 C4 C9 N1 -0.4(9) . . . . ?
C5 C4 C9 C8 1.1(9) . . . . ?
C3 C4 C9 C8 -179.0(6) . . . . ?
C9 C4 C5 C6 -1.5(11) . . . . ?
C3 C4 C5 C6 178.6(7) . . . . ?
O1 C10 C11 F1 6.2(8) . . . . ?
C15 C10 C11 F1 177.5(5) . . . . ?
O1 C10 C11 C12 -171.8(5) . . . . ?
C15 C10 C11 C12 -0.5(8) . . . . ?
F2 C12 C11 F1 3.0(8) . . . . ?
C13 C12 C11 F1 -176.8(6) . . . . ?
F2 C12 C11 C10 -178.9(5) . . . . ?
C13 C12 C11 C10 1.2(9) . . . . ?
F3 C14 C13 C12 179.1(6) . . . . ?
C15 C14 C13 C12 -2.3(10) . . . . ?
F3 C14 C13 I1 1.0(9) . . . . ?
C15 C14 C13 I1 179.6(5) . . . . ?
F2 C12 C13 C14 -179.7(6) . . . . ?
C11 C12 C13 C14 0.2(9) . . . . ?
F2 C12 C13 I1 -1.5(8) . . . . ?
C11 C12 C13 I1 178.3(5) . . . . ?
C4 C5 C6 C7 -0.1(12) . . . . ?
C8 C7 C6 C5 2.0(12) . . . . ?
C6 C7 C8 O1 -179.8(6) . . . . ?
C6 C7 C8 C9 -2.4(11) . . . . ?
C10 O1 C8 C7 -18.8(10) . . . . ?
C10 O1 C8 C9 163.6(5) . . . . ?
N1 C9 C8 C7 -177.9(6) . . . . ?
C4 C9 C8 C7 0.8(9) . . . . ?
N1 C9 C8 O1 -0.2(8) . . . . ?
C4 C9 C8 O1 178.5(5) . . . . ?
C9 N1 C1 C2 0.7(12) . . . . ?
C3 C2 C1 N1 -1.1(14) . . . . ?
C1 C2 C3 C4 0.7(12) . . . . ?
C9 C4 C3 C2 -0.1(10) . . . . ?
C5 C4 C3 C2 179.8(7) . . . . ?

_refine_diff_density_max         0.856
_refine_diff_density_min         -1.503
_refine_diff_density_rms         0.223

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2024516'
loop_
_audit_author_name
_audit_author_address
'Anindita Das'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2020-08-21 deposited with the CCDC.	2021-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 F5 N O'
_chemical_formula_sum            'C15 H6 F5 N O'
_chemical_formula_weight         311.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.293(5)
_cell_length_b                   7.170(3)
_cell_length_c                   23.932(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.238(11)
_cell_angle_gamma                90
_cell_volume                     2450.7(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    20015
_cell_measurement_theta_min      2.264
_cell_measurement_theta_max      24.999

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.159
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Micro-focus
_diffrn_measurement_device_type  'Bruker D8VENTURE with PHOTON II Detector'
_diffrn_measurement_method       'phi, omega and kappa scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20015
_diffrn_reflns_av_unetI/netI     0.1371
_diffrn_reflns_av_R_equivalents  0.1587
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4304
_reflns_number_gt                2465
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0715P)²+1.0840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0141(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.1946
_refine_ls_wR_factor_gt          0.1691
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.5927(2) 0.3447(4) 0.50169(12) 0.0317(8) Uani 1 1 d . . . . .
F002 F 0.9213(2) 0.4700(4) 0.77474(12) 0.0338(8) Uani 1 1 d . . . . .
F003 F 0.9559(2) 0.2413(4) 0.68938(13) 0.0342(8) Uani 1 1 d . . . . .
F004 F 0.9325(2) 0.3591(4) 0.58276(12) 0.0360(9) Uani 1 1 d . . . . .
F005 F 0.7639(2) 0.2357(4) 0.53745(13) 0.0354(9) Uani 1 1 d . . . . .
F006 F 0.8412(2) 0.9487(4) 0.64612(13) 0.0370(9) Uani 1 1 d . . . . .
F007 F 0.8640(2) 0.8305(4) 0.75330(13) 0.0386(9) Uani 1 1 d . . . . .
F008 F 0.9118(2) 0.2583(5) 0.46759(14) 0.0396(9) Uani 1 1 d . . . . .
F009 F 0.7096(2) 0.4977(4) 0.32608(12) 0.0373(9) Uani 1 1 d . . . . .
F00A F 0.8808(2) 0.3835(5) 0.36209(14) 0.0412(9) Uani 1 1 d . . . . .
O00B O 0.5614(2) 0.4976(5) 0.39885(15) 0.0303(10) Uani 1 1 d . . . . .
O00C O 0.8733(2) 0.7099(5) 0.55769(15) 0.0311(10) Uani 1 1 d . . . . .
N00D N 0.6895(3) 0.9206(6) 0.39833(18) 0.0250(11) Uani 1 1 d . . . . .
N00E N 0.3004(3) 0.5706(6) 0.26947(18) 0.0265(11) Uani 1 1 d . . . . .
C00F C 0.6640(4) 0.3583(7) 0.4668(2) 0.0233(13) Uani 1 1 d . . . . .
C00G C 0.9274(4) 0.4180(7) 0.6786(2) 0.0211(12) Uani 1 1 d . . . . .
C00H C 0.8831(4) 0.6552(7) 0.6120(2) 0.0213(12) Uani 1 1 d . . . . .
C00I C 0.9141(4) 0.4765(7) 0.6242(2) 0.0217(13) Uani 1 1 d . . . . .
C00J C 0.9115(4) 0.5332(7) 0.7218(2) 0.0236(13) Uani 1 1 d . . . . .
C00K C 0.6966(4) 0.8644(7) 0.4529(2) 0.0223(13) Uani 1 1 d . . . . .
C00L C 0.7227(4) 0.4325(7) 0.3784(2) 0.0264(13) Uani 1 1 d . . . . .
C00M C 0.7845(4) 0.7562(7) 0.5364(2) 0.0216(12) Uani 1 1 d . . . . .
C00N C 0.4340(4) 0.5332(7) 0.3354(2) 0.0205(12) Uani 1 1 d . . . . .
C00O C 0.8697(4) 0.7716(7) 0.6573(2) 0.0254(13) Uani 1 1 d . . . . .
C00P C 0.7045(4) 0.7429(7) 0.5649(2) 0.0235(13) Uani 1 1 d . . . . .
H00P H 0.705843 0.697961 0.602261 0.028 Uiso 1 1 calc R U . . .
C00Q C 0.6475(4) 0.4235(8) 0.4131(2) 0.0251(13) Uani 1 1 d . . . . .
C00R C 0.7837(4) 0.8154(7) 0.4797(2) 0.0228(13) Uani 1 1 d . . . . .
C00S C 0.7510(4) 0.3026(7) 0.4850(2) 0.0248(13) Uani 1 1 d . . . . .
C00T C 0.8821(4) 0.7143(7) 0.7112(2) 0.0238(13) Uani 1 1 d . . . . .
C00U C 0.4159(4) 0.7115(7) 0.3576(2) 0.0254(13) Uani 1 1 d . . . . .
H00U H 0.454780 0.760842 0.387118 0.030 Uiso 1 1 calc R U . . .
C00V C 0.6194(4) 0.7971(7) 0.5379(2) 0.0251(13) Uani 1 1 d . . . . .
H00V H 0.563367 0.791199 0.557864 0.030 Uiso 1 1 calc R U . . .
C00W C 0.3733(4) 0.4661(7) 0.2915(2) 0.0234(13) Uani 1 1 d . . . . .
C00X C 0.5241(4) 0.2473(7) 0.3324(2) 0.0255(13) Uani 1 1 d . . . . .
H00X H 0.574648 0.172231 0.346189 0.031 Uiso 1 1 calc R U . . .
C00Y C 0.5085(4) 0.4201(7) 0.3541(2) 0.0238(13) Uani 1 1 d . . . . .
C00Z C 0.8551(4) 0.8746(7) 0.3932(2) 0.0251(13) Uani 1 1 d . . . . .
H00Z H 0.908290 0.877833 0.370615 0.030 Uiso 1 1 calc R U . . .
C010 C 0.8086(4) 0.3756(7) 0.3967(2) 0.0274(14) Uani 1 1 d . . . . .
C011 C 0.6152(4) 0.8574(7) 0.4842(2) 0.0229(13) Uani 1 1 d . . . . .
H011 H 0.556923 0.895249 0.467495 0.028 Uiso 1 1 calc R U . . .
C012 C 0.8639(4) 0.8222(7) 0.4471(2) 0.0281(14) Uani 1 1 d . . . . .
H012 H 0.923619 0.790134 0.463160 0.034 Uiso 1 1 calc R U . . .
C013 C 0.3907(4) 0.2876(8) 0.2688(2) 0.0285(14) Uani 1 1 d . . . . .
H013 H 0.351336 0.241007 0.239101 0.034 Uiso 1 1 calc R U . . .
C014 C 0.2875(4) 0.7367(8) 0.2917(2) 0.0298(14) Uani 1 1 d . . . . .
H014 H 0.237548 0.810584 0.276506 0.036 Uiso 1 1 calc R U . . .
C015 C 0.4627(4) 0.1837(8) 0.2890(2) 0.0282(14) Uani 1 1 d . . . . .
H015 H 0.472542 0.063693 0.273426 0.034 Uiso 1 1 calc R U . . .
C016 C 0.3420(4) 0.8120(8) 0.3362(2) 0.0287(14) Uani 1 1 d . . . . .
H016 H 0.327733 0.930947 0.351095 0.034 Uiso 1 1 calc R U . . .
C017 C 0.7665(4) 0.9242(8) 0.3705(2) 0.0283(14) Uani 1 1 d . . . . .
H017 H 0.762186 0.962994 0.332525 0.034 Uiso 1 1 calc R U . . .
C018 C 0.8242(4) 0.3103(8) 0.4506(2) 0.0264(14) 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
F001 C00F 1.347(6) . ?
F002 C00J 1.349(6) . ?
F003 C00G 1.352(6) . ?
F004 C00I 1.334(5) . ?
F005 C00S 1.350(6) . ?
F006 C00O 1.357(6) . ?
F007 C00T 1.340(6) . ?
F008 C018 1.353(6) . ?
F009 C00L 1.343(6) . ?
F00A C010 1.349(6) . ?
O00B C00Q 1.371(6) . ?
O00B C00Y 1.403(6) . ?
O00C C00H 1.358(6) . ?
O00C C00M 1.390(6) . ?
N00D C017 1.309(7) . ?
N00D C00K 1.368(6) . ?
N00E C014 1.321(7) . ?
N00E C00W 1.372(6) . ?
C00F C00S 1.362(7) . ?
C00F C00Q 1.379(7) . ?
C00G C00J 1.349(7) . ?
C00G C00I 1.374(7) . ?
C00H C00I 1.383(7) . ?
C00H C00O 1.388(7) . ?
C00J C00T 1.385(7) . ?
C00K C011 1.408(8) . ?
C00K C00R 1.422(7) . ?
C00L C010 1.351(7) . ?
C00L C00Q 1.384(8) . ?
C00M C00P 1.357(7) . ?
C00M C00R 1.422(7) . ?
C00N C00Y 1.398(7) . ?
C00N C00U 1.412(7) . ?
C00N C00W 1.420(7) . ?
C00O C00T 1.359(7) . ?
C00P C00V 1.410(7) . ?
C00P H00P 0.9500 . ?
C00R C012 1.412(8) . ?
C00S C018 1.357(8) . ?
C00U C016 1.361(7) . ?
C00U H00U 0.9500 . ?
C00V C011 1.354(7) . ?
C00V H00V 0.9500 . ?
C00W C013 1.417(7) . ?
C00X C00Y 1.365(7) . ?
C00X C015 1.410(7) . ?
C00X H00X 0.9500 . ?
C00Z C012 1.346(7) . ?
C00Z C017 1.403(7) . ?
C00Z H00Z 0.9500 . ?
C010 C018 1.383(8) . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 C015 1.344(7) . ?
C013 H013 0.9500 . ?
C014 C016 1.403(8) . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00Q O00B C00Y 119.3(4) . . ?
C00H O00C C00M 118.5(4) . . ?
C017 N00D C00K 117.4(5) . . ?
C014 N00E C00W 117.0(4) . . ?
F001 C00F C00S 118.9(5) . . ?
F001 C00F C00Q 119.8(5) . . ?
C00S C00F C00Q 121.2(5) . . ?
C00J C00G F003 119.0(5) . . ?
C00J C00G C00I 121.2(5) . . ?
F003 C00G C00I 119.8(5) . . ?
O00C C00H C00I 119.3(5) . . ?
O00C C00H C00O 124.2(5) . . ?
C00I C00H C00O 116.4(4) . . ?
F004 C00I C00G 119.2(5) . . ?
F004 C00I C00H 119.9(5) . . ?
C00G C00I C00H 121.0(5) . . ?
F002 C00J C00G 120.0(5) . . ?
F002 C00J C00T 120.4(5) . . ?
C00G C00J C00T 119.6(5) . . ?
N00D C00K C011 119.1(5) . . ?
N00D C00K C00R 122.3(5) . . ?
C011 C00K C00R 118.6(5) . . ?
F009 C00L C010 119.9(5) . . ?
F009 C00L C00Q 119.4(5) . . ?
C010 C00L C00Q 120.6(5) . . ?
C00P C00M O00C 125.0(5) . . ?
C00P C00M C00R 121.7(5) . . ?
O00C C00M C00R 113.2(4) . . ?
C00Y C00N C00U 123.6(5) . . ?
C00Y C00N C00W 118.4(4) . . ?
C00U C00N C00W 118.0(5) . . ?
F006 C00O C00T 119.8(5) . . ?
F006 C00O C00H 117.3(5) . . ?
C00T C00O C00H 122.9(5) . . ?
C00M C00P C00V 118.6(5) . . ?
C00M C00P H00P 120.7 . . ?
C00V C00P H00P 120.7 . . ?
O00B C00Q C00F 118.8(5) . . ?
O00B C00Q C00L 122.9(5) . . ?
C00F C00Q C00L 117.8(5) . . ?
C012 C00R C00M 124.1(5) . . ?
C012 C00R C00K 117.3(5) . . ?
C00M C00R C00K 118.5(5) . . ?
F005 C00S C018 119.9(5) . . ?
F005 C00S C00F 119.5(5) . . ?
C018 C00S C00F 120.7(5) . . ?
F007 C00T C00O 120.3(5) . . ?
F007 C00T C00J 120.8(5) . . ?
C00O C00T C00J 118.9(5) . . ?
C016 C00U C00N 119.2(5) . . ?
C016 C00U H00U 120.4 . . ?
C00N C00U H00U 120.4 . . ?
C011 C00V C00P 121.9(5) . . ?
C011 C00V H00V 119.1 . . ?
C00P C00V H00V 119.1 . . ?
N00E C00W C013 119.2(5) . . ?
N00E C00W C00N 122.2(5) . . ?
C013 C00W C00N 118.6(5) . . ?
C00Y C00X C015 117.9(5) . . ?
C00Y C00X H00X 121.1 . . ?
C015 C00X H00X 121.1 . . ?
C00X C00Y C00N 122.6(5) . . ?
C00X C00Y O00B 124.0(5) . . ?
C00N C00Y O00B 113.3(4) . . ?
C012 C00Z C017 119.4(5) . . ?
C012 C00Z H00Z 120.3 . . ?
C017 C00Z H00Z 120.3 . . ?
F00A C010 C00L 119.8(5) . . ?
F00A C010 C018 119.2(5) . . ?
C00L C010 C018 121.1(5) . . ?
C00V C011 C00K 120.6(5) . . ?
C00V C011 H011 119.7 . . ?
C00K C011 H011 119.7 . . ?
C00Z C012 C00R 119.4(5) . . ?
C00Z C012 H012 120.3 . . ?
C00R C012 H012 120.3 . . ?
C015 C013 C00W 120.4(5) . . ?
C015 C013 H013 119.8 . . ?
C00W C013 H013 119.8 . . ?
N00E C014 C016 124.8(5) . . ?
N00E C014 H014 117.6 . . ?
C016 C014 H014 117.6 . . ?
C013 C015 C00X 122.1(5) . . ?
C013 C015 H015 119.0 . . ?
C00X C015 H015 119.0 . . ?
C00U C016 C014 118.8(5) . . ?
C00U C016 H016 120.6 . . ?
C014 C016 H016 120.6 . . ?
N00D C017 C00Z 124.2(5) . . ?
N00D C017 H017 117.9 . . ?
C00Z C017 H017 117.9 . . ?
F008 C018 C00S 122.2(5) . . ?
F008 C018 C010 119.2(5) . . ?
C00S C018 C010 118.7(5) . . ?

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.084

