# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_umt_ob112
_database_code_depnum_ccdc_archive 'CCDC 2023091'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2023-01-29
_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         'C25 H10 F9 I2 N'
_chemical_formula_sum            'C25 H10 F9 I2 N'
_chemical_formula_weight         749.14
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.0483(14)
_cell_length_b                   4.7023(4)
_cell_length_c                   30.687(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.370(2)
_cell_angle_gamma                90
_cell_volume                     2393.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    105
_cell_measurement_theta_max      27.366
_cell_measurement_theta_min      3.074
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.368
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0760 before and 0.0603 after correction. The Ratio of minimum to maximum transmission is 0.7828. 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    2.079
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            51830
_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         27.536
_diffrn_reflns_theta_min         3.073
_diffrn_ambient_temperature      105
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4239
_reflns_number_total             5489
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.080
_refine_diff_density_min         -0.810
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5489
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+4.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0805
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C11(H11), C12(H12), C14(H14), C19(H19), C20(H20), C22(H22)
;
_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
I1 I 0.26855(2) 0.05619(6) 0.72956(2) 0.02395(8) Uani 1 1 d . . . . .
I2 I 0.52649(2) 0.85644(7) 0.69852(2) 0.02903(9) Uani 1 1 d . . . . .
F1 F 0.09374(15) 1.2162(5) 0.46767(8) 0.0292(6) Uani 1 1 d . . . . .
F2 F 0.13530(16) 0.8481(6) 0.43908(8) 0.0321(6) Uani 1 1 d . . . . .
F3 F 0.02898(14) 0.8237(6) 0.46436(8) 0.0337(7) Uani 1 1 d . . . . .
F4 F -0.13099(14) -0.3048(5) 0.69116(8) 0.0266(6) Uani 1 1 d . . . . .
F5 F -0.09508(14) -0.7023(5) 0.66833(8) 0.0261(6) Uani 1 1 d . . . . .
F6 F -0.12421(14) -0.3521(6) 0.62255(8) 0.0315(6) Uani 1 1 d . . . . .
F7 F 0.59235(18) 1.7643(7) 0.53045(10) 0.0494(8) Uani 1 1 d . . . . .
F8 F 0.6683(3) 1.4272(8) 0.52209(14) 0.0847(14) Uani 1 1 d . . . . .
F9 F 0.7103(2) 1.7539(9) 0.57010(12) 0.0742(12) Uani 1 1 d . . . . .
N1 N 0.3043(2) 0.5916(8) 0.63766(11) 0.0193(8) Uani 1 1 d D . . . .
H1A H 0.3514(15) 0.656(10) 0.6451(15) 0.031(13) Uiso 1 1 d D . . . .
H1B H 0.293(3) 0.453(7) 0.6522(13) 0.025(13) Uiso 1 1 d D . . . .
C1 C 0.2553(2) 0.6769(8) 0.59844(12) 0.0158(8) Uani 1 1 d . . . . .
C2 C 0.1761(2) 0.5675(8) 0.58436(12) 0.0151(8) Uani 1 1 d . . . . .
C3 C 0.1263(2) 0.6572(8) 0.54422(12) 0.0151(8) Uani 1 1 d . . . . .
H3 H 0.073044 0.584548 0.535209 0.018 Uiso 1 1 calc R . . . .
C4 C 0.1538(2) 0.8518(9) 0.51717(12) 0.0154(8) Uani 1 1 d . . . . .
C5 C 0.2312(2) 0.9616(9) 0.53051(13) 0.0180(8) Uani 1 1 d . . . . .
H5 H 0.249697 1.095644 0.511999 0.022 Uiso 1 1 calc R . . . .
C6 C 0.2821(2) 0.8768(8) 0.57092(13) 0.0165(8) Uani 1 1 d . . . . .
C7 C 0.1495(2) 0.3621(8) 0.61231(13) 0.0152(8) Uani 1 1 d . . . . .
C8 C 0.1321(2) 0.1893(8) 0.63721(13) 0.0161(8) Uani 1 1 d . . . . .
C9 C 0.1053(2) -0.0176(8) 0.66450(12) 0.0149(8) Uani 1 1 d . . . . .
C10 C 0.1539(2) -0.1127(8) 0.70516(12) 0.0140(8) Uani 1 1 d . . . . .
C11 C 0.1257(2) -0.3146(9) 0.73054(13) 0.0180(8) Uani 1 1 d . . . . .
H11 H 0.159648 -0.380842 0.757667 0.022 Uiso 1 1 calc R . . . .
C12 C 0.0480(2) -0.4208(9) 0.71660(13) 0.0171(8) Uani 1 1 d . . . . .
H12 H 0.028675 -0.559443 0.734072 0.021 Uiso 1 1 calc R . . . .
C13 C -0.0010(2) -0.3236(8) 0.67717(13) 0.0159(8) Uani 1 1 d . . . . .
C14 C 0.0275(2) -0.1282(8) 0.65100(12) 0.0156(8) Uani 1 1 d . . . . .
H14 H -0.006276 -0.068225 0.623422 0.019 Uiso 1 1 calc R . . . .
C15 C 0.3627(2) 0.9853(9) 0.58459(14) 0.0207(9) Uani 1 1 d . . . . .
C16 C 0.4305(2) 1.0643(10) 0.59798(13) 0.0214(9) Uani 1 1 d . . . . .
C17 C 0.5120(2) 1.1605(9) 0.60911(13) 0.0191(8) Uani 1 1 d . . . . .
C18 C 0.5662(2) 1.0885(9) 0.64935(13) 0.0209(9) Uani 1 1 d . . . . .
C19 C 0.6463(3) 1.1713(11) 0.65783(15) 0.0307(11) Uani 1 1 d . . . . .
H19 H 0.682746 1.115392 0.684815 0.037 Uiso 1 1 calc R . . . .
C20 C 0.6732(3) 1.3372(11) 0.62652(16) 0.0317(11) Uani 1 1 d . . . . .
H20 H 0.728012 1.395280 0.632170 0.038 Uiso 1 1 calc R . . . .
C21 C 0.6202(2) 1.4167(10) 0.58737(14) 0.0237(9) Uani 1 1 d . . . . .
C22 C 0.5402(2) 1.3301(10) 0.57884(14) 0.0236(9) Uani 1 1 d . . . . .
H22 H 0.504062 1.387774 0.551854 0.028 Uiso 1 1 calc R . . . .
C23 C 0.1031(2) 0.9353(9) 0.47262(13) 0.0205(9) Uani 1 1 d . . . . .
C24 C -0.0873(2) -0.4203(9) 0.66410(13) 0.0182(9) Uani 1 1 d . . . . .
C25 C 0.6484(3) 1.5858(11) 0.55281(17) 0.0351(12) 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 C10 2.083(4) . ?
I2 C18 2.097(4) . ?
F1 C23 1.335(5) . ?
F2 C23 1.338(5) . ?
F3 C23 1.337(5) . ?
F4 C24 1.351(4) . ?
F5 C24 1.342(5) . ?
F6 C24 1.324(4) . ?
F7 C25 1.336(6) . ?
F8 C25 1.308(6) . ?
F9 C25 1.328(6) . ?
N1 C1 1.358(5) . ?
C1 C2 1.416(5) . ?
C1 C6 1.409(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.433(5) . ?
C3 C4 1.387(5) . ?
C4 C5 1.388(5) . ?
C4 C23 1.491(5) . ?
C5 C6 1.397(5) . ?
C6 C15 1.435(5) . ?
C7 C8 1.199(5) . ?
C8 C9 1.426(5) . ?
C9 C10 1.401(5) . ?
C9 C14 1.396(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.387(5) . ?
C12 C13 1.380(5) . ?
C13 C14 1.381(5) . ?
C13 C24 1.503(5) . ?
C15 C16 1.193(6) . ?
C16 C17 1.427(5) . ?
C17 C18 1.402(6) . ?
C17 C22 1.391(6) . ?
C18 C19 1.386(6) . ?
C19 C20 1.395(7) . ?
C20 C21 1.378(6) . ?
C21 C22 1.388(6) . ?
C21 C25 1.491(6) . ?

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
N1 C1 C2 120.8(4) . . ?
N1 C1 C6 120.7(4) . . ?
C6 C1 C2 118.6(3) . . ?
C1 C2 C7 118.3(3) . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 C7 121.5(3) . . ?
C4 C3 C2 120.6(4) . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 C23 121.2(3) . . ?
C5 C4 C23 118.8(4) . . ?
C4 C5 C6 120.6(4) . . ?
C1 C6 C15 118.9(4) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 C15 121.0(4) . . ?
C8 C7 C2 175.9(4) . . ?
C7 C8 C9 175.5(4) . . ?
C10 C9 C8 122.5(3) . . ?
C14 C9 C8 119.4(3) . . ?
C14 C9 C10 118.0(3) . . ?
C9 C10 I1 120.7(3) . . ?
C11 C10 I1 118.6(3) . . ?
C11 C10 C9 120.7(4) . . ?
C10 C11 C12 120.3(4) . . ?
C13 C12 C11 119.5(4) . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 C24 119.4(4) . . ?
C14 C13 C24 120.1(3) . . ?
C13 C14 C9 120.9(4) . . ?
C16 C15 C6 176.2(5) . . ?
C15 C16 C17 173.9(4) . . ?
C18 C17 C16 122.8(4) . . ?
C22 C17 C16 119.3(4) . . ?
C22 C17 C18 117.9(4) . . ?
C17 C18 I2 120.2(3) . . ?
C19 C18 I2 118.6(3) . . ?
C19 C18 C17 121.2(4) . . ?
C18 C19 C20 119.6(4) . . ?
C21 C20 C19 119.9(4) . . ?
C20 C21 C22 120.2(4) . . ?
C20 C21 C25 120.7(4) . . ?
C22 C21 C25 119.1(4) . . ?
C21 C22 C17 121.2(4) . . ?
F1 C23 F2 106.0(3) . . ?
F1 C23 F3 106.5(3) . . ?
F1 C23 C4 113.2(3) . . ?
F2 C23 C4 111.7(3) . . ?
F3 C23 F2 105.8(3) . . ?
F3 C23 C4 113.1(3) . . ?
F4 C24 C13 111.0(3) . . ?
F5 C24 F4 104.9(3) . . ?
F5 C24 C13 112.7(3) . . ?
F6 C24 F4 106.7(3) . . ?
F6 C24 F5 107.3(3) . . ?
F6 C24 C13 113.7(3) . . ?
F7 C25 C21 113.0(4) . . ?
F8 C25 F7 105.2(4) . . ?
F8 C25 F9 108.2(4) . . ?
F8 C25 C21 112.9(4) . . ?
F9 C25 F7 103.8(4) . . ?
F9 C25 C21 113.0(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_umt_ob162
_database_code_depnum_ccdc_archive 'CCDC 2023092'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H12 F9 N'
_chemical_formula_sum            'C25 H12 F9 N'
_chemical_formula_weight         497.36
_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'

_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                   7.9820(4)
_cell_length_b                   7.9889(4)
_cell_length_c                   17.3963(9)
_cell_angle_alpha                84.337(2)
_cell_angle_beta                 89.492(2)
_cell_angle_gamma                70.559(2)
_cell_volume                     1040.62(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.442
_cell_measurement_theta_min      2.707
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0502 before and 0.0463 after correction. The Ratio of minimum to maximum transmission is 0.9480. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0252
_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       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47574
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.707
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3649
_reflns_number_total             4794
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4794
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.020
_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)+(0.0440P)²+0.5914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F8-C25 \\sim F9B-C25
 with sigma of 0.02
 F9-C25 \\sim F7B-C25
 with sigma of 0.02
 F7-C25 \\sim F8B-C25
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F9 \\sim F9B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
F8 \\sim F8B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C12(H12), C13(H13), C14(H14), C18(H18), C20(H20),
 C21(H21), C22(H22)
;
_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
F1 F 0.17744(13) 0.97515(12) 0.68610(5) 0.0264(2) Uani 1 1 d . . . . .
F2 F 0.16348(14) 1.00485(13) 0.56208(6) 0.0332(3) Uani 1 1 d . . . . .
F3 F 0.36014(14) 1.07613(13) 0.62137(7) 0.0362(3) Uani 1 1 d . . . . .
F4 F 0.85770(17) 0.62064(16) 0.12985(6) 0.0433(3) Uani 1 1 d . . . . .
F5 F 1.13841(15) 0.57900(14) 0.12168(6) 0.0384(3) Uani 1 1 d . . . . .
F6 F 0.97206(14) 0.78561(12) 0.18530(6) 0.0315(3) Uani 1 1 d . . . . .
F7 F 0.1886(6) -0.1431(12) 0.9017(11) 0.066(3) Uani 0.57(3) 1 d D . P A 1
F8 F 0.3362(10) -0.3197(9) 0.9937(5) 0.0330(13) Uani 0.57(3) 1 d D U P A 1
F9 F 0.3909(14) -0.3959(13) 0.8795(5) 0.056(2) Uani 0.57(3) 1 d D U P A 1
N1 N 0.77460(19) 0.25874(17) 0.61448(9) 0.0192(3) Uani 1 1 d . . . . .
H1A H 0.801(3) 0.192(3) 0.6569(12) 0.026(5) Uiso 1 1 d . . . . .
H1B H 0.854(3) 0.247(3) 0.5798(13) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.65492(19) 0.42628(19) 0.61752(8) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.63633(19) 0.55977(19) 0.55499(8) 0.0129(3) Uani 1 1 d . . . . .
C3 C 0.51109(19) 0.72891(19) 0.55776(8) 0.0138(3) Uani 1 1 d . . . . .
H3 H 0.497732 0.817614 0.515486 0.017 Uiso 1 1 calc R . . . .
C4 C 0.40543(19) 0.76889(19) 0.62194(8) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.42085(19) 0.63918(19) 0.68345(8) 0.0140(3) Uani 1 1 d . . . . .
H5 H 0.347889 0.667329 0.727002 0.017 Uiso 1 1 calc R . . . .
C6 C 0.54332(19) 0.46746(19) 0.68146(8) 0.0138(3) Uani 1 1 d . . . . .
C7 C 0.7481(2) 0.51669(19) 0.48986(8) 0.0148(3) Uani 1 1 d . . . . .
C8 C 0.8447(2) 0.47170(19) 0.43721(9) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.95477(19) 0.42131(19) 0.37185(8) 0.0144(3) Uani 1 1 d . . . . .
C10 C 0.92885(19) 0.53911(19) 0.30465(8) 0.0148(3) Uani 1 1 d . . . . .
H10 H 0.838690 0.652814 0.302098 0.018 Uiso 1 1 calc R . . . .
C11 C 1.0354(2) 0.48932(19) 0.24158(8) 0.0153(3) Uani 1 1 d . . . . .
C12 C 1.1672(2) 0.3234(2) 0.24398(9) 0.0165(3) Uani 1 1 d . . . . .
H12 H 1.239376 0.290841 0.200527 0.020 Uiso 1 1 calc R . . . .
C13 C 1.1925(2) 0.2055(2) 0.31047(9) 0.0182(3) Uani 1 1 d . . . . .
H13 H 1.281824 0.091401 0.312333 0.022 Uiso 1 1 calc R . . . .
C14 C 1.0881(2) 0.2534(2) 0.37419(9) 0.0169(3) Uani 1 1 d . . . . .
H14 H 1.106891 0.172335 0.419592 0.020 Uiso 1 1 calc R . . . .
C15 C 0.5574(2) 0.32925(19) 0.74302(8) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.5736(2) 0.20735(19) 0.79154(9) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.5926(2) 0.06078(19) 0.85003(8) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.4633(2) -0.0222(2) 0.85633(9) 0.0186(3) Uani 1 1 d . . . . .
H18 H 0.362210 0.018233 0.822354 0.022 Uiso 1 1 calc R . . . .
C19 C 0.4837(2) -0.1647(2) 0.91278(9) 0.0202(3) Uani 1 1 d . . . . .
C20 C 0.6309(2) -0.2254(2) 0.96257(9) 0.0224(4) Uani 1 1 d . . . . .
H20 H 0.643363 -0.322131 1.001044 0.027 Uiso 1 1 calc R . . . .
C21 C 0.7596(2) -0.1442(2) 0.95584(9) 0.0238(4) Uani 1 1 d . . . . .
H21 H 0.861035 -0.185913 0.989668 0.029 Uiso 1 1 calc R . . . .
C22 C 0.7415(2) -0.0021(2) 0.89991(9) 0.0207(3) Uani 1 1 d . . . . .
H22 H 0.830682 0.052593 0.895582 0.025 Uiso 1 1 calc R . . . .
C23 C 0.2779(2) 0.9535(2) 0.62342(9) 0.0185(3) Uani 1 1 d . . . . .
C24 C 1.0022(2) 0.6165(2) 0.16963(9) 0.0222(3) Uani 1 1 d . . . . .
C25 C 0.3483(2) -0.2576(2) 0.91750(11) 0.0293(4) Uani 1 1 d D . . . .
F7B F 0.2051(9) -0.1828(10) 0.8636(8) 0.0439(18) Uani 0.43(3) 1 d D . P A 2
F8B F 0.286(3) -0.289(2) 0.9818(8) 0.060(3) Uani 0.43(3) 1 d D U P A 2
F9B F 0.4115(13) -0.4197(11) 0.8884(7) 0.039(2) Uani 0.43(3) 1 d D U P A 2


_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
F1 C23 1.3385(17) . ?
F2 C23 1.3501(18) . ?
F3 C23 1.3466(19) . ?
F4 C24 1.339(2) . ?
F5 C24 1.3359(18) . ?
F6 C24 1.3464(19) . ?
F7 C25 1.310(5) . ?
F8 C25 1.384(7) . ?
F9 C25 1.290(8) . ?
N1 C1 1.3670(19) . ?
C1 C2 1.418(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.433(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.390(2) . ?
C4 C23 1.490(2) . ?
C5 C6 1.398(2) . ?
C6 C15 1.437(2) . ?
C7 C8 1.196(2) . ?
C8 C9 1.436(2) . ?
C9 C10 1.397(2) . ?
C9 C14 1.405(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.388(2) . ?
C11 C24 1.498(2) . ?
C12 C13 1.389(2) . ?
C13 C14 1.387(2) . ?
C15 C16 1.197(2) . ?
C16 C17 1.442(2) . ?
C17 C18 1.399(2) . ?
C17 C22 1.397(2) . ?
C18 C19 1.395(2) . ?
C19 C20 1.386(2) . ?
C19 C25 1.499(2) . ?
C20 C21 1.385(2) . ?
C21 C22 1.390(2) . ?
C25 F7B 1.412(7) . ?
C25 F8B 1.258(11) . ?
C25 F9B 1.371(8) . ?

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
N1 C1 C2 120.28(13) . . ?
N1 C1 C6 120.73(13) . . ?
C6 C1 C2 118.95(13) . . ?
C1 C2 C7 118.75(13) . . ?
C3 C2 C1 119.92(13) . . ?
C3 C2 C7 121.33(13) . . ?
C4 C3 C2 120.49(13) . . ?
C3 C4 C23 118.51(13) . . ?
C5 C4 C3 120.34(13) . . ?
C5 C4 C23 121.14(13) . . ?
C4 C5 C6 120.26(13) . . ?
C1 C6 C15 118.65(13) . . ?
C5 C6 C1 120.01(13) . . ?
C5 C6 C15 121.34(13) . . ?
C8 C7 C2 176.57(16) . . ?
C7 C8 C9 177.66(16) . . ?
C10 C9 C8 120.06(13) . . ?
C10 C9 C14 119.17(13) . . ?
C14 C9 C8 120.77(13) . . ?
C11 C10 C9 119.76(13) . . ?
C10 C11 C24 118.67(13) . . ?
C12 C11 C10 121.01(14) . . ?
C12 C11 C24 120.30(13) . . ?
C11 C12 C13 119.39(14) . . ?
C14 C13 C12 120.38(14) . . ?
C13 C14 C9 120.28(14) . . ?
C16 C15 C6 176.37(16) . . ?
C15 C16 C17 179.8(2) . . ?
C18 C17 C16 120.09(14) . . ?
C22 C17 C16 120.56(14) . . ?
C22 C17 C18 119.33(14) . . ?
C19 C18 C17 119.63(15) . . ?
C18 C19 C25 119.48(15) . . ?
C20 C19 C18 120.79(15) . . ?
C20 C19 C25 119.69(14) . . ?
C21 C20 C19 119.54(14) . . ?
C20 C21 C22 120.43(15) . . ?
C21 C22 C17 120.27(15) . . ?
F1 C23 F2 105.98(12) . . ?
F1 C23 F3 106.36(13) . . ?
F1 C23 C4 113.55(12) . . ?
F2 C23 C4 112.68(13) . . ?
F3 C23 F2 105.25(12) . . ?
F3 C23 C4 112.38(13) . . ?
F4 C24 F6 105.47(13) . . ?
F4 C24 C11 112.07(13) . . ?
F5 C24 F4 107.57(14) . . ?
F5 C24 F6 105.99(13) . . ?
F5 C24 C11 113.20(13) . . ?
F6 C24 C11 112.04(13) . . ?
F7 C25 F8 102.6(7) . . ?
F7 C25 C19 110.6(3) . . ?
F8 C25 C19 108.8(4) . . ?
F9 C25 F7 115.0(7) . . ?
F9 C25 F8 106.0(6) . . ?
F9 C25 C19 113.0(4) . . ?
F7B C25 C19 114.1(3) . . ?
F8B C25 C19 119.7(7) . . ?
F8B C25 F7B 108.0(7) . . ?
F8B C25 F9B 105.0(8) . . ?
F9B C25 C19 111.3(5) . . ?
F9B C25 F7B 95.7(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_umt_ob229f
_database_code_depnum_ccdc_archive 'CCDC 2238835'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2021-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H13 F6 I2 N'
_chemical_formula_sum            'C25 H13 F6 I2 N'
_chemical_formula_weight         695.16
_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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.182(4)
_cell_length_b                   4.5894(10)
_cell_length_c                   29.337(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.945(4)
_cell_angle_gamma                90
_cell_volume                     2341.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9068
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.032
_cell_measurement_theta_min      2.757
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.399
_exptl_absorpt_coefficient_mu    2.747
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0853 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.7166. 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    1.972
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19640
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.078
_diffrn_reflns_theta_max         25.078
_diffrn_reflns_theta_min         2.757
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3377
_reflns_number_total             4155
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.377
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.178
_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)+(0.0054P)²+13.3860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
3.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
I1 I 0.82942(2) 0.45732(9) 0.29402(2) 0.02518(12) Uani 1 1 d . . . . .
I2 I 0.51525(3) -0.25839(10) 0.27207(2) 0.02606(12) Uani 1 1 d . . . . .
F1 F 1.1256(2) 1.3486(10) 0.42952(14) 0.0444(12) Uani 1 1 d . . . . .
F2 F 1.1238(2) 1.0112(9) 0.47984(14) 0.0428(11) Uani 1 1 d . . . . .
F3 F 1.0490(2) 1.3780(9) 0.47285(14) 0.0386(10) Uani 1 1 d . . . . .
F4 F 0.2264(2) -0.8198(8) 0.35997(16) 0.0437(11) Uani 1 1 d . . . . .
F5 F 0.1711(2) -0.4305(9) 0.32646(13) 0.0379(10) Uani 1 1 d . . . . .
F6 F 0.2445(2) -0.4184(9) 0.39827(13) 0.0359(10) Uani 1 1 d . . . . .
N1 N 0.6584(3) 0.2704(13) 0.36134(18) 0.0230(12) Uani 1 1 d D . . . .
C1 C 0.9117(3) 0.7008(13) 0.3455(2) 0.0203(14) Uani 1 1 d . . . . .
C2 C 0.9802(3) 0.7643(15) 0.3369(2) 0.0245(14) Uani 1 1 d . . . . .
H2 H 0.990525 0.693212 0.308982 0.029 Uiso 1 1 calc R . . . .
C3 C 1.0342(4) 0.9338(15) 0.3694(2) 0.0263(15) Uani 1 1 d . . . . .
H3 H 1.081325 0.984004 0.363471 0.032 Uiso 1 1 calc R . . . .
C4 C 1.0187(3) 1.0286(14) 0.4105(2) 0.0217(14) Uani 1 1 d . . . . .
C5 C 0.9501(3) 0.9634(14) 0.4192(2) 0.0210(14) Uani 1 1 d . . . . .
H5 H 0.940083 1.033847 0.447252 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8947(3) 0.7928(14) 0.3866(2) 0.0217(14) Uani 1 1 d . . . . .
C7 C 0.8250(3) 0.7267(15) 0.3975(2) 0.0227(14) Uani 1 1 d . . . . .
C8 C 0.7699(4) 0.6762(14) 0.4108(2) 0.0238(15) Uani 1 1 d . . . . .
C9 C 0.7035(3) 0.6140(14) 0.4258(2) 0.0210(14) Uani 1 1 d . . . . .
C10 C 0.6486(3) 0.4116(13) 0.4001(2) 0.0195(14) Uani 1 1 d . . . . .
C11 C 0.6929(3) 0.7594(14) 0.4655(2) 0.0219(14) Uani 1 1 d . . . . .
H11 H 0.730701 0.895058 0.482122 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6287(3) 0.7106(14) 0.4811(2) 0.0200(14) Uani 1 1 d . . . . .
C13 C 0.5742(3) 0.5147(13) 0.45539(19) 0.0183(13) Uani 1 1 d . . . . .
H13 H 0.529673 0.480062 0.465250 0.022 Uiso 1 1 calc R . . . .
C14 C 0.5824(3) 0.3648(13) 0.4151(2) 0.0205(14) Uani 1 1 d . . . . .
C15 C 0.5254(3) 0.1638(14) 0.3900(2) 0.0194(14) Uani 1 1 d . . . . .
C16 C 0.4789(3) -0.0082(14) 0.3679(2) 0.0194(14) Uani 1 1 d . . . . .
C17 C 0.4222(3) -0.2111(13) 0.34306(19) 0.0168(13) Uani 1 1 d . . . . .
C18 C 0.4252(3) -0.3488(13) 0.3008(2) 0.0203(14) Uani 1 1 d . . . . .
C19 C 0.3690(3) -0.5468(14) 0.2779(2) 0.0227(14) Uani 1 1 d . . . . .
H19 H 0.371933 -0.638950 0.249484 0.027 Uiso 1 1 calc R . . . .
C20 C 0.3090(4) -0.6109(13) 0.2959(2) 0.0228(15) Uani 1 1 d . . . . .
H20 H 0.270885 -0.747792 0.280151 0.027 Uiso 1 1 calc R . . . .
C21 C 0.3044(3) -0.4748(14) 0.3373(2) 0.0223(14) Uani 1 1 d . . . . .
C22 C 0.3601(3) -0.2800(13) 0.3609(2) 0.0193(13) Uani 1 1 d . . . . .
H22 H 0.356734 -0.190961 0.389417 0.023 Uiso 1 1 calc R . . . .
C23 C 1.0789(4) 1.1960(15) 0.4478(2) 0.0270(16) Uani 1 1 d . . . . .
C24 C 0.6189(4) 0.8648(15) 0.5242(2) 0.0268(16) Uani 1 1 d . . . . .
H24A H 0.572665 0.986864 0.514783 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.663917 0.987363 0.538258 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.613589 0.720597 0.547710 0.040 Uiso 1 1 calc GR . . . .
C25 C 0.2373(4) -0.5373(14) 0.3560(2) 0.0242(14) Uani 1 1 d . . . . .
H1A H 0.7034(18) 0.256(15) 0.358(2) 0.03(2) Uiso 1 1 d D . . . .
H1B H 0.631(4) 0.120(11) 0.351(3) 0.05(3) Uiso 1 1 d 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 2.111(6) . ?
I2 C18 2.091(6) . ?
F1 C23 1.329(7) . ?
F2 C23 1.350(8) . ?
F3 C23 1.329(7) . ?
F4 C25 1.322(8) . ?
F5 C25 1.354(7) . ?
F6 C25 1.326(7) . ?
N1 C10 1.365(8) . ?
C1 C2 1.372(8) . ?
C1 C6 1.393(8) . ?
C2 C3 1.391(9) . ?
C3 C4 1.387(8) . ?
C4 C5 1.378(8) . ?
C4 C23 1.512(9) . ?
C5 C6 1.407(8) . ?
C6 C7 1.426(8) . ?
C7 C8 1.200(8) . ?
C8 C9 1.429(8) . ?
C9 C10 1.411(8) . ?
C9 C11 1.402(8) . ?
C10 C14 1.413(8) . ?
C11 C12 1.392(8) . ?
C12 C13 1.386(8) . ?
C12 C24 1.506(8) . ?
C13 C14 1.411(8) . ?
C14 C15 1.423(9) . ?
C15 C16 1.199(8) . ?
C16 C17 1.422(8) . ?
C17 C18 1.406(8) . ?
C17 C22 1.411(8) . ?
C18 C19 1.386(9) . ?
C19 C20 1.376(9) . ?
C20 C21 1.390(8) . ?
C21 C22 1.376(8) . ?
C21 C25 1.503(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 118.2(4) . . ?
C2 C1 C6 122.5(6) . . ?
C6 C1 I1 119.3(5) . . ?
C1 C2 C3 119.4(6) . . ?
C4 C3 C2 119.3(6) . . ?
C3 C4 C23 120.1(6) . . ?
C5 C4 C3 121.2(6) . . ?
C5 C4 C23 118.7(5) . . ?
C4 C5 C6 120.2(5) . . ?
C1 C6 C5 117.4(5) . . ?
C1 C6 C7 124.4(6) . . ?
C5 C6 C7 118.2(5) . . ?
C8 C7 C6 174.2(6) . . ?
C7 C8 C9 179.0(7) . . ?
C10 C9 C8 119.7(5) . . ?
C11 C9 C8 119.6(6) . . ?
C11 C9 C10 120.7(5) . . ?
N1 C10 C9 120.9(5) . . ?
N1 C10 C14 121.2(6) . . ?
C9 C10 C14 117.8(5) . . ?
C12 C11 C9 121.9(6) . . ?
C11 C12 C24 121.2(6) . . ?
C13 C12 C11 117.4(5) . . ?
C13 C12 C24 121.4(5) . . ?
C12 C13 C14 122.6(5) . . ?
C10 C14 C15 119.6(5) . . ?
C13 C14 C10 119.6(6) . . ?
C13 C14 C15 120.8(5) . . ?
C16 C15 C14 177.9(6) . . ?
C15 C16 C17 177.8(6) . . ?
C18 C17 C16 122.5(5) . . ?
C18 C17 C22 117.8(5) . . ?
C22 C17 C16 119.7(5) . . ?
C17 C18 I2 120.1(4) . . ?
C19 C18 I2 119.2(4) . . ?
C19 C18 C17 120.7(6) . . ?
C20 C19 C18 120.5(6) . . ?
C19 C20 C21 119.8(6) . . ?
C20 C21 C25 119.7(6) . . ?
C22 C21 C20 120.5(6) . . ?
C22 C21 C25 119.9(6) . . ?
C21 C22 C17 120.7(5) . . ?
F1 C23 F2 106.5(5) . . ?
F1 C23 C4 112.9(5) . . ?
F2 C23 C4 110.3(5) . . ?
F3 C23 F1 107.7(5) . . ?
F3 C23 F2 105.7(5) . . ?
F3 C23 C4 113.2(5) . . ?
F4 C25 F5 106.4(5) . . ?
F4 C25 F6 107.3(5) . . ?
F4 C25 C21 112.2(5) . . ?
F5 C25 C21 111.2(5) . . ?
F6 C25 F5 106.0(5) . . ?
F6 C25 C21 113.2(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_umt_ob220
_database_code_depnum_ccdc_archive 'CCDC 2238834'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2021-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H12 F3 I2 N'
_chemical_formula_sum            'C23 H12 F3 I2 N'
_chemical_formula_weight         613.14
_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'
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'

_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                   8.4061(3)
_cell_length_b                   20.5959(7)
_cell_length_c                   12.3043(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.6440(10)
_cell_angle_gamma                90
_cell_volume                     2018.47(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.491
_cell_measurement_theta_min      2.639
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    3.152
_exptl_absorpt_correction_T_max  0.6032
_exptl_absorpt_correction_T_min  0.5161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0682 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8556. 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    2.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            75201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.557
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8540
_reflns_number_total             9280
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.708
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.381(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     540
_refine_ls_number_reflns         9280
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.086
_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)+(0.0300P)²+0.6391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0579
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
# start Validation Reply Form
_vrf_PLAT094_umt_ob220           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.78 Report
RESPONSE: The alert is due to residual electron density peaks near 
the iodine atoms (< 1 ang.). These peaks, dispersed symmetrically around the iodine
atoms, are Fourier truncation ripples. Various absorption correction methods were 
attempted and were ultimately unsuccessful in the elimination of these artifacts. 
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.619(19)
 0.381(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N9B-H9BB = N9B-H9BA = N1A-H1AA = N1A-H1AB
 0.87 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C4B(H4B), C5B(H5B), C11B(H11B), C13B(H13B), C19B(H19B),
 C20B(H20B), C21B(H21B), C22B(H22B), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
 C11A(H11A), C13A(H13A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
;
_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
I1B I 0.56764(5) 0.29699(2) 0.43249(3) 0.02072(12) Uani 1 1 d . . . . .
I2B I 0.23654(4) 0.41014(2) 0.74397(3) 0.01916(9) Uani 1 1 d . . . . .
F9B F 0.3319(5) 0.69771(17) 0.1464(3) 0.0304(8) Uani 1 1 d . . . . .
F10B F 0.2624(5) 0.74770(16) 0.2788(3) 0.0350(9) Uani 1 1 d . . . . .
F11B F 0.0753(5) 0.69547(18) 0.1451(3) 0.0307(8) Uani 1 1 d . . . . .
N9B N 0.3406(6) 0.4611(2) 0.4736(4) 0.0183(10) Uani 1 1 d D . . . .
H9BA H 0.375(6) 0.4263(17) 0.449(4) 0.001(12) Uiso 1 1 d D . . . .
H9BB H 0.312(10) 0.455(4) 0.534(4) 0.04(2) Uiso 1 1 d D . . . .
C1B C 0.5744(7) 0.3009(3) 0.2636(5) 0.0166(11) Uani 1 1 d . . . . .
C2B C 0.6390(7) 0.2480(3) 0.2213(5) 0.0199(11) Uani 1 1 d . . . . .
H2B H 0.682463 0.211739 0.269243 0.024 Uiso 1 1 calc R . . . .
C3B C 0.6398(7) 0.2485(3) 0.1089(5) 0.0223(12) Uani 1 1 d . . . . .
H3B H 0.686147 0.212833 0.080285 0.027 Uiso 1 1 calc R . . . .
C4B C 0.5729(7) 0.3011(3) 0.0376(5) 0.0191(12) Uani 1 1 d . . . . .
H4B H 0.571844 0.300894 -0.039809 0.023 Uiso 1 1 calc R . . . .
C5B C 0.5080(7) 0.3535(3) 0.0799(5) 0.0188(11) Uani 1 1 d . . . . .
H5B H 0.461110 0.389031 0.030836 0.023 Uiso 1 1 calc R . . . .
C6B C 0.5109(7) 0.3546(3) 0.1946(5) 0.0154(11) Uani 1 1 d . . . . .
C7B C 0.4511(6) 0.4119(3) 0.2361(4) 0.0171(10) Uani 1 1 d . . . . .
C8B C 0.4060(7) 0.4624(3) 0.2653(5) 0.0176(11) Uani 1 1 d . . . . .
C9B C 0.3514(7) 0.5198(3) 0.3069(4) 0.0153(10) Uani 1 1 d . . . . .
C10B C 0.3173(6) 0.5169(3) 0.4131(4) 0.0137(10) Uani 1 1 d . . . . .
C11B C 0.3298(7) 0.5782(3) 0.2458(4) 0.0156(11) Uani 1 1 d . . . . .
H11B H 0.354487 0.580264 0.175760 0.019 Uiso 1 1 calc R . . . .
C12B C 0.2727(7) 0.6330(2) 0.2871(4) 0.0153(10) Uani 1 1 d . . . . .
C13B C 0.2373(7) 0.6307(2) 0.3897(4) 0.0158(11) Uani 1 1 d . . . . .
H13B H 0.197892 0.668574 0.417005 0.019 Uiso 1 1 calc R . . . .
C14B C 0.2589(7) 0.5737(3) 0.4530(4) 0.0147(11) Uani 1 1 d . . . . .
C15B C 0.2219(6) 0.5697(3) 0.5590(4) 0.0141(10) Uani 1 1 d . . . . .
C16B C 0.1915(7) 0.5613(3) 0.6467(5) 0.0161(11) Uani 1 1 d . . . . .
C17B C 0.1552(6) 0.5547(3) 0.7518(5) 0.0145(11) Uani 1 1 d . . . . .
C18B C 0.1741(7) 0.4954(2) 0.8115(5) 0.0148(10) Uani 1 1 d . . . . .
C19B C 0.1439(7) 0.4913(3) 0.9167(5) 0.0200(11) Uani 1 1 d . . . . .
H19B H 0.159756 0.451308 0.957115 0.024 Uiso 1 1 calc R . . . .
C20B C 0.0909(7) 0.5457(3) 0.9620(5) 0.0207(12) Uani 1 1 d . . . . .
H20B H 0.069022 0.542719 1.032956 0.025 Uiso 1 1 calc R . . . .
C21B C 0.0699(7) 0.6045(3) 0.9041(5) 0.0215(12) Uani 1 1 d . . . . .
H21B H 0.033955 0.641774 0.935415 0.026 Uiso 1 1 calc R . . . .
C22B C 0.1014(7) 0.6089(3) 0.8000(5) 0.0173(11) Uani 1 1 d . . . . .
H22B H 0.086190 0.649275 0.760813 0.021 Uiso 1 1 calc R . . . .
C23B C 0.2356(7) 0.6932(3) 0.2157(5) 0.0216(12) Uani 1 1 d . . . . .
I1A I 1.05717(5) 0.30939(2) 0.42992(3) 0.01991(12) Uani 1 1 d . . . . .
I2A I 0.73053(4) 0.40767(2) 0.75188(3) 0.02033(9) Uani 1 1 d . . . . .
F1A F 0.7212(5) 0.71222(16) 0.1553(3) 0.0313(8) Uani 1 1 d . . . . .
F2A F 0.9087(5) 0.74446(15) 0.3088(3) 0.0267(8) Uani 1 1 d . . . . .
F3A F 0.6485(4) 0.75288(15) 0.2939(3) 0.0290(8) Uani 1 1 d . . . . .
N1A N 0.8150(7) 0.4666(2) 0.4807(4) 0.0211(10) Uani 1 1 d D . . . .
H1AA H 0.790(9) 0.459(3) 0.541(4) 0.028(19) Uiso 1 1 d D . . . .
H1AB H 0.860(9) 0.436(3) 0.456(6) 0.04(2) Uiso 1 1 d D . . . .
C1A C 1.0614(6) 0.3177(3) 0.2615(4) 0.0159(10) Uani 1 1 d . . . . .
C2A C 1.1267(7) 0.2668(3) 0.2160(5) 0.0201(12) Uani 1 1 d . . . . .
H2A H 1.170696 0.229778 0.261718 0.024 Uiso 1 1 calc R . . . .
C3A C 1.1281(7) 0.2697(3) 0.1038(5) 0.0203(11) Uani 1 1 d . . . . .
H3A H 1.173252 0.234743 0.072681 0.024 Uiso 1 1 calc R . . . .
C4A C 1.0630(7) 0.3244(3) 0.0361(5) 0.0196(12) Uani 1 1 d . . . . .
H4A H 1.063004 0.326397 -0.040995 0.024 Uiso 1 1 calc R . . . .
C5A C 0.9996(7) 0.3746(3) 0.0818(5) 0.0194(11) Uani 1 1 d . . . . .
H5A H 0.955014 0.411274 0.035267 0.023 Uiso 1 1 calc R . . . .
C6A C 0.9981(7) 0.3736(2) 0.1963(5) 0.0160(10) Uani 1 1 d . . . . .
C7A C 0.9363(7) 0.4287(2) 0.2417(4) 0.0159(11) Uani 1 1 d . . . . .
C8A C 0.8880(7) 0.4773(3) 0.2753(5) 0.0172(11) Uani 1 1 d . . . . .
C9A C 0.8321(7) 0.5330(3) 0.3238(5) 0.0169(11) Uani 1 1 d . . . . .
C10A C 0.7971(6) 0.5255(3) 0.4280(5) 0.0171(12) Uani 1 1 d . . . . .
C11A C 0.8173(7) 0.5942(2) 0.2722(5) 0.0170(11) Uani 1 1 d . . . . .
H11A H 0.842918 0.599450 0.202928 0.020 Uiso 1 1 calc R . . . .
C12A C 0.7649(7) 0.6476(2) 0.3222(5) 0.0190(11) Uani 1 1 d . . . . .
C13A C 0.7286(7) 0.6403(3) 0.4233(5) 0.0175(11) Uani 1 1 d . . . . .
H13A H 0.694026 0.676951 0.456938 0.021 Uiso 1 1 calc R . . . .
C14A C 0.7418(7) 0.5801(3) 0.4766(5) 0.0184(11) Uani 1 1 d . . . . .
C15A C 0.7074(7) 0.5719(3) 0.5818(5) 0.0190(12) Uani 1 1 d . . . . .
C16A C 0.6809(7) 0.5611(3) 0.6703(5) 0.0175(11) Uani 1 1 d . . . . .
C17A C 0.6545(6) 0.5513(3) 0.7788(5) 0.0164(11) Uani 1 1 d . . . . .
C18A C 0.6710(7) 0.4900(2) 0.8309(5) 0.0168(11) Uani 1 1 d . . . . .
C19A C 0.6477(7) 0.4819(3) 0.9370(5) 0.0195(11) Uani 1 1 d . . . . .
H19A H 0.659971 0.440202 0.971567 0.023 Uiso 1 1 calc R . . . .
C20A C 0.6066(7) 0.5349(3) 0.9923(5) 0.0228(12) Uani 1 1 d . . . . .
H20A H 0.589898 0.529269 1.064482 0.027 Uiso 1 1 calc R . . . .
C21A C 0.5898(7) 0.5959(3) 0.9428(5) 0.0242(12) Uani 1 1 d . . . . .
H21A H 0.563185 0.632185 0.981375 0.029 Uiso 1 1 calc R . . . .
C22A C 0.6119(7) 0.6039(3) 0.8367(5) 0.0216(12) Uani 1 1 d . . . . .
H22A H 0.597985 0.645745 0.802524 0.026 Uiso 1 1 calc R . . . .
C23A C 0.7591(7) 0.7132(3) 0.2699(5) 0.0212(13) 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
I1B C1B 2.098(5) . ?
I2B C18B 2.080(5) . ?
F9B C23B 1.353(6) . ?
F10B C23B 1.343(7) . ?
F11B C23B 1.351(7) . ?
N9B C10B 1.350(7) . ?
C1B C2B 1.391(7) . ?
C1B C6B 1.392(7) . ?
C2B C3B 1.385(8) . ?
C3B C4B 1.394(8) . ?
C4B C5B 1.384(7) . ?
C5B C6B 1.404(7) . ?
C6B C7B 1.439(7) . ?
C7B C8B 1.200(8) . ?
C8B C9B 1.421(8) . ?
C9B C10B 1.425(7) . ?
C9B C11B 1.398(7) . ?
C10B C14B 1.415(7) . ?
C11B C12B 1.385(7) . ?
C12B C13B 1.387(7) . ?
C12B C23B 1.494(7) . ?
C13B C14B 1.389(7) . ?
C14B C15B 1.437(7) . ?
C15B C16B 1.198(8) . ?
C16B C17B 1.427(7) . ?
C17B C18B 1.409(7) . ?
C17B C22B 1.404(7) . ?
C18B C19B 1.399(7) . ?
C19B C20B 1.387(8) . ?
C20B C21B 1.388(8) . ?
C21B C22B 1.390(8) . ?
I1A C1A 2.090(5) . ?
I2A C18A 2.094(5) . ?
F1A C23A 1.343(6) . ?
F2A C23A 1.356(7) . ?
F3A C23A 1.340(6) . ?
N1A C10A 1.362(7) . ?
C1A C2A 1.382(8) . ?
C1A C6A 1.407(7) . ?
C2A C3A 1.386(8) . ?
C3A C4A 1.403(8) . ?
C4A C5A 1.364(8) . ?
C5A C6A 1.413(7) . ?
C6A C7A 1.433(7) . ?
C7A C8A 1.201(8) . ?
C8A C9A 1.441(8) . ?
C9A C10A 1.412(8) . ?
C9A C11A 1.397(8) . ?
C10A C14A 1.420(8) . ?
C11A C12A 1.398(7) . ?
C12A C13A 1.381(8) . ?
C12A C23A 1.492(8) . ?
C13A C14A 1.391(7) . ?
C14A C15A 1.423(8) . ?
C15A C16A 1.200(8) . ?
C16A C17A 1.436(8) . ?
C17A C18A 1.403(7) . ?
C17A C22A 1.404(7) . ?
C18A C19A 1.391(8) . ?
C19A C20A 1.386(8) . ?
C20A C21A 1.384(8) . ?
C21A C22A 1.385(8) . ?

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
C2B C1B I1B 118.6(4) . . ?
C2B C1B C6B 120.9(5) . . ?
C6B C1B I1B 120.6(4) . . ?
C3B C2B C1B 119.7(5) . . ?
C2B C3B C4B 120.2(5) . . ?
C5B C4B C3B 119.9(5) . . ?
C4B C5B C6B 120.5(5) . . ?
C1B C6B C5B 118.7(5) . . ?
C1B C6B C7B 122.9(5) . . ?
C5B C6B C7B 118.3(5) . . ?
C8B C7B C6B 175.0(6) . . ?
C7B C8B C9B 175.8(6) . . ?
C8B C9B C10B 118.6(5) . . ?
C11B C9B C8B 121.5(5) . . ?
C11B C9B C10B 119.9(5) . . ?
N9B C10B C9B 120.3(5) . . ?
N9B C10B C14B 121.2(5) . . ?
C14B C10B C9B 118.5(5) . . ?
C12B C11B C9B 120.3(5) . . ?
C11B C12B C13B 120.4(5) . . ?
C11B C12B C23B 119.5(5) . . ?
C13B C12B C23B 119.9(5) . . ?
C12B C13B C14B 120.7(5) . . ?
C10B C14B C15B 117.9(5) . . ?
C13B C14B C10B 120.1(5) . . ?
C13B C14B C15B 121.9(5) . . ?
C16B C15B C14B 174.9(6) . . ?
C15B C16B C17B 177.2(6) . . ?
C18B C17B C16B 122.3(5) . . ?
C22B C17B C16B 119.9(5) . . ?
C22B C17B C18B 117.8(5) . . ?
C17B C18B I2B 121.7(4) . . ?
C19B C18B I2B 117.6(4) . . ?
C19B C18B C17B 120.7(5) . . ?
C20B C19B C18B 120.1(5) . . ?
C19B C20B C21B 120.2(5) . . ?
C20B C21B C22B 119.9(5) . . ?
C21B C22B C17B 121.4(5) . . ?
F9B C23B C12B 112.0(5) . . ?
F10B C23B F9B 106.5(5) . . ?
F10B C23B F11B 106.9(5) . . ?
F10B C23B C12B 112.9(5) . . ?
F11B C23B F9B 105.5(5) . . ?
F11B C23B C12B 112.6(5) . . ?
C2A C1A I1A 118.3(4) . . ?
C2A C1A C6A 121.1(5) . . ?
C6A C1A I1A 120.6(4) . . ?
C1A C2A C3A 120.1(5) . . ?
C2A C3A C4A 120.0(5) . . ?
C5A C4A C3A 119.6(5) . . ?
C4A C5A C6A 122.0(5) . . ?
C1A C6A C5A 117.2(5) . . ?
C1A C6A C7A 122.9(5) . . ?
C5A C6A C7A 119.8(5) . . ?
C8A C7A C6A 175.9(5) . . ?
C7A C8A C9A 175.6(6) . . ?
C10A C9A C8A 118.6(5) . . ?
C11A C9A C8A 121.6(5) . . ?
C11A C9A C10A 119.8(5) . . ?
N1A C10A C9A 120.5(5) . . ?
N1A C10A C14A 120.4(5) . . ?
C9A C10A C14A 119.2(5) . . ?
C9A C11A C12A 120.3(5) . . ?
C11A C12A C23A 119.6(5) . . ?
C13A C12A C11A 120.2(5) . . ?
C13A C12A C23A 120.1(5) . . ?
C12A C13A C14A 121.0(5) . . ?
C10A C14A C15A 118.6(5) . . ?
C13A C14A C10A 119.6(5) . . ?
C13A C14A C15A 121.7(5) . . ?
C16A C15A C14A 176.0(6) . . ?
C15A C16A C17A 176.8(6) . . ?
C18A C17A C16A 121.9(5) . . ?
C18A C17A C22A 117.8(5) . . ?
C22A C17A C16A 120.3(5) . . ?
C17A C18A I2A 121.4(4) . . ?
C19A C18A I2A 117.7(4) . . ?
C19A C18A C17A 120.9(5) . . ?
C20A C19A C18A 119.9(5) . . ?
C21A C20A C19A 120.3(5) . . ?
C20A C21A C22A 119.8(5) . . ?
C21A C22A C17A 121.3(5) . . ?
F1A C23A F2A 105.1(5) . . ?
F1A C23A C12A 113.8(5) . . ?
F2A C23A C12A 112.3(5) . . ?
F3A C23A F1A 107.0(5) . . ?
F3A C23A F2A 105.3(5) . . ?
F3A C23A C12A 112.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.619(19)
2 0.381(19)

####################################################################### 
# 
# 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_umt_ob227
_database_code_depnum_ccdc_archive 'CCDC 2238836'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2021-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H10 F7 I2 N'
_chemical_formula_sum            'C24 H10 F7 I2 N'
_chemical_formula_weight         699.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.3702(7)
_cell_length_b                   18.1535(18)
_cell_length_c                   34.027(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.009(2)
_cell_angle_gamma                90
_cell_volume                     4541.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.023
_cell_measurement_theta_min      2.545
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.614
_exptl_absorpt_coefficient_mu    2.840
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0666 before and 0.0559 after correction. The Ratio of minimum to maximum transmission is 0.8786. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            47545
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.099
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.545
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3412
_reflns_number_total             4043
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0089P)²+41.5815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0667
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
;
_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
I1 I 0.49328(5) 0.53996(2) 0.66979(2) 0.02359(10) Uani 1 1 d . . . . .
I2 I -0.01085(5) 0.27593(2) 0.91341(2) 0.02803(11) Uani 1 1 d . . . . .
F1 F 0.2404(5) 0.11149(16) 0.75519(9) 0.0402(9) Uani 1 1 d . . . . .
F2 F 0.5570(5) 0.27638(16) 0.52087(8) 0.0321(8) Uani 1 1 d . . . . .
F3 F 0.4136(5) 0.36337(18) 0.48930(9) 0.0399(9) Uani 1 1 d . . . . .
F4 F 0.7055(5) 0.36513(19) 0.49658(10) 0.0444(10) Uani 1 1 d . . . . .
F5 F -0.0216(9) 0.6499(2) 0.86498(15) 0.0932(19) Uani 1 1 d . . . . .
F6 F 0.0882(7) 0.6541(2) 0.9239(2) 0.116(2) Uani 1 1 d . . . . .
F7 F -0.1886(6) 0.6511(2) 0.91182(15) 0.0730(14) Uani 1 1 d . . . . .
N1 N 0.2544(7) 0.4146(2) 0.74587(14) 0.0226(10) Uani 1 1 d D . . . .
H1A H 0.289(6) 0.436(2) 0.7255(10) 0.013(14) Uiso 1 1 d D . . . .
H1B H 0.225(9) 0.437(3) 0.7666(12) 0.06(2) Uiso 1 1 d D . . . .
C1 C 0.5110(7) 0.4761(3) 0.61906(14) 0.0165(11) Uani 1 1 d . . . . .
C2 C 0.5626(7) 0.5093(3) 0.58511(14) 0.0182(11) Uani 1 1 d . . . . .
H2 H 0.586741 0.560683 0.584858 0.022 Uiso 1 1 calc R . . . .
C3 C 0.5792(7) 0.4681(3) 0.55164(15) 0.0186(11) Uani 1 1 d . . . . .
H3 H 0.613860 0.491020 0.528223 0.022 Uiso 1 1 calc R . . . .
C4 C 0.5449(7) 0.3924(3) 0.55210(14) 0.0160(11) Uani 1 1 d . . . . .
C5 C 0.4943(6) 0.3581(3) 0.58605(14) 0.0157(11) Uani 1 1 d . . . . .
H5 H 0.472129 0.306549 0.586130 0.019 Uiso 1 1 calc R . . . .
C6 C 0.4757(6) 0.3999(3) 0.62052(14) 0.0144(11) Uani 1 1 d . . . . .
C7 C 0.4172(6) 0.3637(3) 0.65474(14) 0.0142(11) Uani 1 1 d . . . . .
C8 C 0.3679(7) 0.3310(3) 0.68239(14) 0.0159(11) Uani 1 1 d . . . . .
C9 C 0.3057(7) 0.2955(3) 0.71678(14) 0.0172(11) Uani 1 1 d . . . . .
C10 C 0.2516(7) 0.3393(3) 0.74817(14) 0.0160(11) Uani 1 1 d . . . . .
C11 C 0.3002(7) 0.2185(3) 0.71923(15) 0.0208(12) Uani 1 1 d . . . . .
H11 H 0.334086 0.188821 0.697949 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2451(8) 0.1870(3) 0.75289(16) 0.0236(12) Uani 1 1 d . . . . .
C13 C 0.1921(7) 0.2273(3) 0.78429(15) 0.0219(12) Uani 1 1 d . . . . .
H13 H 0.154987 0.203319 0.807211 0.026 Uiso 1 1 calc R . . . .
C14 C 0.1937(7) 0.3038(3) 0.78195(14) 0.0167(11) Uani 1 1 d . . . . .
C15 C 0.1352(7) 0.3470(3) 0.81390(14) 0.0181(11) Uani 1 1 d . . . . .
C16 C 0.0848(6) 0.3826(3) 0.84061(15) 0.0154(11) Uani 1 1 d . . . . .
C17 C 0.0264(7) 0.4240(3) 0.87315(14) 0.0173(11) Uani 1 1 d . . . . .
C18 C -0.0160(7) 0.3898(3) 0.90845(15) 0.0174(11) Uani 1 1 d . . . . .
C19 C -0.0652(7) 0.4319(3) 0.94023(15) 0.0228(12) Uani 1 1 d . . . . .
H19 H -0.093795 0.408275 0.963930 0.027 Uiso 1 1 calc R . . . .
C20 C -0.0726(7) 0.5076(3) 0.93757(17) 0.0263(13) Uani 1 1 d . . . . .
H20 H -0.104882 0.536237 0.959395 0.032 Uiso 1 1 calc R . . . .
C21 C -0.0327(7) 0.5416(3) 0.90273(17) 0.0244(12) Uani 1 1 d . . . . .
C22 C 0.0163(7) 0.5008(3) 0.87085(16) 0.0211(12) Uani 1 1 d . . . . .
H22 H 0.043164 0.525093 0.847220 0.025 Uiso 1 1 calc R . . . .
C23 C 0.5553(8) 0.3490(3) 0.51520(15) 0.0239(13) Uani 1 1 d . . . . .
C24 C -0.0367(9) 0.6232(3) 0.8997(2) 0.0364(16) 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 2.091(5) . ?
I2 C18 2.074(5) . ?
F1 C12 1.374(6) . ?
F2 C23 1.332(6) . ?
F3 C23 1.344(6) . ?
F4 C23 1.346(6) . ?
F5 C24 1.291(8) . ?
F6 C24 1.317(7) . ?
F7 C24 1.320(7) . ?
N1 C10 1.368(6) . ?
C1 C2 1.380(7) . ?
C1 C6 1.408(7) . ?
C2 C3 1.376(7) . ?
C3 C4 1.397(7) . ?
C4 C5 1.386(7) . ?
C4 C23 1.488(7) . ?
C5 C6 1.412(7) . ?
C6 C7 1.430(7) . ?
C7 C8 1.191(7) . ?
C8 C9 1.439(7) . ?
C9 C10 1.412(7) . ?
C9 C11 1.401(7) . ?
C10 C14 1.410(7) . ?
C11 C12 1.367(7) . ?
C12 C13 1.374(7) . ?
C13 C14 1.391(7) . ?
C14 C15 1.430(7) . ?
C15 C16 1.196(7) . ?
C16 C17 1.429(7) . ?
C17 C18 1.407(7) . ?
C17 C22 1.398(7) . ?
C18 C19 1.393(7) . ?
C19 C20 1.378(8) . ?
C20 C21 1.386(8) . ?
C21 C22 1.382(7) . ?
C21 C24 1.484(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.1(4) . . ?
C2 C1 C6 121.4(5) . . ?
C6 C1 I1 119.5(4) . . ?
C3 C2 C1 120.1(5) . . ?
C2 C3 C4 120.0(5) . . ?
C3 C4 C23 119.4(5) . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 C23 119.9(5) . . ?
C4 C5 C6 119.9(5) . . ?
C1 C6 C5 118.0(4) . . ?
C1 C6 C7 123.2(4) . . ?
C5 C6 C7 118.8(4) . . ?
C8 C7 C6 177.4(5) . . ?
C7 C8 C9 176.7(5) . . ?
C10 C9 C8 119.0(4) . . ?
C11 C9 C8 120.5(4) . . ?
C11 C9 C10 120.4(5) . . ?
N1 C10 C9 120.9(5) . . ?
N1 C10 C14 120.6(5) . . ?
C14 C10 C9 118.5(4) . . ?
C12 C11 C9 118.6(5) . . ?
F1 C12 C13 118.5(5) . . ?
C11 C12 F1 118.4(5) . . ?
C11 C12 C13 123.1(5) . . ?
C12 C13 C14 118.9(5) . . ?
C10 C14 C15 119.6(5) . . ?
C13 C14 C10 120.5(5) . . ?
C13 C14 C15 119.9(5) . . ?
C16 C15 C14 179.3(6) . . ?
C15 C16 C17 178.7(5) . . ?
C18 C17 C16 121.7(5) . . ?
C22 C17 C16 119.9(5) . . ?
C22 C17 C18 118.3(5) . . ?
C17 C18 I2 120.4(4) . . ?
C19 C18 I2 119.2(4) . . ?
C19 C18 C17 120.4(5) . . ?
C20 C19 C18 120.5(5) . . ?
C19 C20 C21 119.4(5) . . ?
C20 C21 C24 119.9(5) . . ?
C22 C21 C20 121.0(5) . . ?
C22 C21 C24 119.1(5) . . ?
C21 C22 C17 120.4(5) . . ?
F2 C23 F3 106.6(4) . . ?
F2 C23 F4 106.5(4) . . ?
F2 C23 C4 113.7(4) . . ?
F3 C23 F4 106.0(4) . . ?
F3 C23 C4 111.5(4) . . ?
F4 C23 C4 112.0(4) . . ?
F5 C24 F6 108.1(6) . . ?
F5 C24 F7 105.7(6) . . ?
F5 C24 C21 115.8(5) . . ?
F6 C24 F7 102.3(5) . . ?
F6 C24 C21 111.9(5) . . ?
F7 C24 C21 112.0(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_umt_ob218
_database_code_depnum_ccdc_archive 'CCDC 2238833'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H9 F9 I2'
_chemical_formula_sum            'C25 H9 F9 I2'
_chemical_formula_weight         734.12
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.7496(16)
_cell_length_b                   4.7821(4)
_cell_length_c                   25.949(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.215(2)
_cell_angle_gamma                90
_cell_volume                     2320.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.933
_cell_measurement_theta_min      2.780
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.360
_exptl_absorpt_coefficient_mu    2.796
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0690 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.7790. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.101
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1384
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15943
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.059
_diffrn_reflns_theta_max         25.059
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2932
_reflns_number_total             4089
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.023
_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)+(0.0270P)²+2.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F4-C24 \\sim F4B-C24
 with sigma of 0.02
 F6-C24 \\sim F6B-C24
 with sigma of 0.02
 F5-C24 \\sim F5B-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F4 \\sim F4B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
F5 \\sim F5B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
F6 \\sim F6B: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C11(H11), C13(H13), C19(H19), C20(H20),
 C22(H22)
;
_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
I1 I 0.19915(2) 1.47879(9) 0.59008(2) 0.02642(13) Uani 1 1 d . . . . .
I2 I 0.07846(2) -0.09477(9) 0.24640(2) 0.02255(13) Uani 1 1 d . . . . .
F1 F 0.5693(2) 1.6269(8) 0.58539(17) 0.0448(12) Uani 1 1 d . . . . .
F2 F 0.5629(2) 1.2217(8) 0.61935(16) 0.0417(11) Uani 1 1 d . . . . .
F3 F 0.5560(2) 1.2665(8) 0.53705(15) 0.0387(11) Uani 1 1 d . . . . .
F4 F -0.0224(4) 0.682(2) 0.4597(3) 0.051(3) Uani 0.691(17) 1 d D U P A 1
F5 F -0.0321(4) 0.708(3) 0.3785(4) 0.070(5) Uani 0.691(17) 1 d D U P A 1
F6 F -0.0057(3) 1.0696(14) 0.4249(4) 0.055(4) Uani 0.691(17) 1 d D U P A 1
F7 F 0.4434(2) -0.3429(9) 0.2533(2) 0.0641(16) Uani 1 1 d . . . . .
F8 F 0.4091(2) -0.7027(12) 0.21241(17) 0.0744(18) Uani 1 1 d . . . . .
F9 F 0.4152(2) -0.7014(9) 0.29368(16) 0.0417(11) Uani 1 1 d . . . . .
C1 C 0.3096(3) 1.4512(13) 0.5850(2) 0.0218(15) Uani 1 1 d . . . . .
C2 C 0.3548(4) 1.6128(13) 0.6177(3) 0.0237(16) Uani 1 1 d . . . . .
H2 H 0.335419 1.737034 0.641599 0.028 Uiso 1 1 calc R . . . .
C3 C 0.4281(4) 1.5922(13) 0.6155(2) 0.0248(16) Uani 1 1 d . . . . .
H3 H 0.458928 1.702917 0.637819 0.030 Uiso 1 1 calc R . . . .
C4 C 0.4563(3) 1.4139(13) 0.5813(2) 0.0203(15) Uani 1 1 d . . . . .
C5 C 0.4116(4) 1.2516(12) 0.5482(2) 0.0248(17) Uani 1 1 d . . . . .
H5 H 0.431798 1.127702 0.524619 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3373(4) 1.2691(12) 0.5492(2) 0.0183(15) Uani 1 1 d . . . . .
C7 C 0.2926(3) 1.1004(12) 0.5152(3) 0.0211(15) Uani 1 1 d . . . . .
C8 C 0.2547(3) 0.9618(12) 0.4863(2) 0.0220(15) Uani 1 1 d . . . . .
C9 C 0.2049(3) 0.8084(12) 0.4526(2) 0.0184(15) Uani 1 1 d . . . . .
C10 C 0.2287(3) 0.6049(12) 0.4196(2) 0.0174(14) Uani 1 1 d . . . . .
H10 H 0.278243 0.563097 0.420195 0.021 Uiso 1 1 calc R . . . .
C11 C 0.1318(3) 0.8648(12) 0.4523(2) 0.0175(15) Uani 1 1 d . . . . .
H11 H 0.115012 0.998833 0.475615 0.021 Uiso 1 1 calc R . . . .
C12 C 0.0837(3) 0.7269(14) 0.4184(2) 0.0219(16) Uani 1 1 d . . . . .
C13 C 0.1068(3) 0.5274(13) 0.3855(2) 0.0222(16) Uani 1 1 d . . . . .
H13 H 0.073222 0.433194 0.362355 0.027 Uiso 1 1 calc R . . . .
C14 C 0.1803(3) 0.4613(12) 0.3858(2) 0.0173(15) Uani 1 1 d . . . . .
C15 C 0.2026(3) 0.2528(13) 0.3511(2) 0.0179(15) Uani 1 1 d . . . . .
C16 C 0.2177(3) 0.0757(12) 0.3213(2) 0.0167(14) Uani 1 1 d . . . . .
C17 C 0.2348(3) -0.1371(11) 0.2856(2) 0.0139(14) Uani 1 1 d . . . . .
C18 C 0.1834(3) -0.2479(12) 0.2491(2) 0.0160(15) Uani 1 1 d . . . . .
C19 C 0.2005(3) -0.4554(12) 0.2153(2) 0.0171(15) Uani 1 1 d . . . . .
H19 H 0.164773 -0.530175 0.191334 0.021 Uiso 1 1 calc R . . . .
C20 C 0.2695(3) -0.5539(12) 0.2163(2) 0.0175(15) Uani 1 1 d . . . . .
H20 H 0.281575 -0.696410 0.192913 0.021 Uiso 1 1 calc R . . . .
C21 C 0.3214(3) -0.4447(12) 0.2514(2) 0.0173(15) Uani 1 1 d . . . . .
C22 C 0.3045(3) -0.2404(12) 0.2859(2) 0.0151(14) Uani 1 1 d . . . . .
H22 H 0.340569 -0.169179 0.310020 0.018 Uiso 1 1 calc R . . . .
C23 C 0.5360(4) 1.3811(14) 0.5807(3) 0.0279(17) Uani 1 1 d . . . . .
C24 C 0.0060(4) 0.7948(16) 0.4182(3) 0.0305(18) Uani 1 1 d D . . . .
C25 C 0.3969(4) -0.5494(14) 0.2530(3) 0.0257(17) Uani 1 1 d . . . . .
F4B F -0.0329(7) 0.549(3) 0.4145(10) 0.060(8) Uani 0.309(17) 1 d D U P A 2
F5B F -0.0182(9) 0.921(5) 0.3753(6) 0.043(7) Uani 0.309(17) 1 d D U P A 2
F6B F -0.0169(8) 0.909(6) 0.4572(6) 0.055(8) Uani 0.309(17) 1 d D U P A 2


_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 2.090(6) . ?
I2 C18 2.096(6) . ?
F1 C23 1.332(7) . ?
F2 C23 1.328(7) . ?
F3 C23 1.337(7) . ?
F4 C24 1.348(10) . ?
F5 C24 1.279(9) . ?
F6 C24 1.346(9) . ?
F7 C25 1.316(7) . ?
F8 C25 1.317(7) . ?
F9 C25 1.308(7) . ?
C1 C2 1.389(9) . ?
C1 C6 1.400(8) . ?
C2 C3 1.382(9) . ?
C3 C4 1.364(8) . ?
C4 C5 1.392(8) . ?
C4 C23 1.505(9) . ?
C5 C6 1.397(8) . ?
C6 C7 1.423(9) . ?
C7 C8 1.195(8) . ?
C8 C9 1.433(8) . ?
C9 C10 1.390(8) . ?
C9 C11 1.398(8) . ?
C10 C14 1.396(8) . ?
C11 C12 1.381(8) . ?
C12 C13 1.372(8) . ?
C12 C24 1.492(9) . ?
C13 C14 1.415(8) . ?
C14 C15 1.426(8) . ?
C15 C16 1.194(8) . ?
C16 C17 1.428(8) . ?
C17 C18 1.405(8) . ?
C17 C22 1.396(8) . ?
C18 C19 1.378(8) . ?
C19 C20 1.375(8) . ?
C20 C21 1.386(8) . ?
C21 C22 1.377(8) . ?
C21 C25 1.499(8) . ?
C24 F4B 1.383(14) . ?
C24 F5B 1.317(13) . ?
C24 F6B 1.252(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.3(5) . . ?
C2 C1 C6 120.8(6) . . ?
C6 C1 I1 119.9(5) . . ?
C3 C2 C1 119.8(6) . . ?
C4 C3 C2 120.4(6) . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 C23 120.3(6) . . ?
C5 C4 C23 119.3(6) . . ?
C4 C5 C6 120.7(6) . . ?
C1 C6 C7 122.2(6) . . ?
C5 C6 C1 118.0(6) . . ?
C5 C6 C7 119.8(6) . . ?
C8 C7 C6 179.1(7) . . ?
C7 C8 C9 175.8(7) . . ?
C10 C9 C8 120.7(6) . . ?
C10 C9 C11 119.4(6) . . ?
C11 C9 C8 119.9(6) . . ?
C9 C10 C14 120.7(6) . . ?
C12 C11 C9 120.4(6) . . ?
C11 C12 C24 119.3(6) . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 C24 120.1(6) . . ?
C12 C13 C14 120.3(6) . . ?
C10 C14 C13 118.7(6) . . ?
C10 C14 C15 122.3(6) . . ?
C13 C14 C15 118.9(6) . . ?
C16 C15 C14 176.6(7) . . ?
C15 C16 C17 179.4(7) . . ?
C18 C17 C16 122.0(6) . . ?
C22 C17 C16 120.3(5) . . ?
C22 C17 C18 117.7(6) . . ?
C17 C18 I2 119.1(4) . . ?
C19 C18 I2 119.5(4) . . ?
C19 C18 C17 121.4(6) . . ?
C20 C19 C18 119.9(6) . . ?
C19 C20 C21 119.8(6) . . ?
C20 C21 C25 120.5(6) . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 C25 118.8(6) . . ?
C21 C22 C17 120.5(6) . . ?
F1 C23 F3 106.3(6) . . ?
F1 C23 C4 111.4(5) . . ?
F2 C23 F1 106.8(6) . . ?
F2 C23 F3 106.9(5) . . ?
F2 C23 C4 111.9(6) . . ?
F3 C23 C4 113.0(6) . . ?
F4 C24 C12 110.7(6) . . ?
F5 C24 F4 106.5(9) . . ?
F5 C24 F6 109.5(9) . . ?
F5 C24 C12 114.9(7) . . ?
F6 C24 F4 102.1(8) . . ?
F6 C24 C12 112.3(6) . . ?
F4B C24 C12 109.0(8) . . ?
F5B C24 C12 112.2(9) . . ?
F5B C24 F4B 100.6(14) . . ?
F6B C24 C12 119.0(9) . . ?
F6B C24 F4B 102.3(14) . . ?
F6B C24 F5B 111.4(15) . . ?
F7 C25 F8 105.6(6) . . ?
F7 C25 C21 111.9(5) . . ?
F8 C25 C21 112.6(6) . . ?
F9 C25 F7 106.1(6) . . ?
F9 C25 F8 106.6(5) . . ?
F9 C25 C21 113.5(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_ob148_sq
_database_code_depnum_ccdc_archive 'CCDC 2238838'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C23 H12 F3 I2 N, C21 H43 N, 1.25(Cl), C6 H12.69 N0.25'
_chemical_formula_sum            'C50 H67.69 Cl1.25 F3 I2 N2.25'
_chemical_formula_weight         1055.37
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   36.9115(18)
_cell_length_b                   36.9115(18)
_cell_length_c                   8.3724(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11407.0(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.982
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.201
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1149 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.7676. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             4302
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            86060
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.468
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                9215
_reflns_number_total             10071
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 4004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         10071
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0237P)²+43.3286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0736
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT315_ob148_sq            
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).        C44 Check 
RESPONSE: This alert is due to the treatment of the remaining alkyl chain 
of the cation with SQUEEZE. Please see experimental write-up in the 
supplementary information for further details.
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H49,H49A,H49B} of C49, All C(H,H) groups
 At 1.5 times of:
  {H41A,H41B,H41C} of C41, {H35A,H35B,H35C} of C35, {H29A,H29B,H29C} of C29,
  {H50D,H50E,H50F} of C50A, {H50A,H50B,H50C} of C50
2. Restrained distances
 N1-H1B = N1-H1A
 0.87 with sigma of 0.02
 F1-C23 \\sim F3A-C23 \\sim F3-C23 \\sim F2A-C23 \\sim F2-C23 \\sim F1A-C23
 with sigma of 0.02
 C50-C49 \\sim C50A-C49
 with sigma of 0.02
3. Restrained planarity
 N1, H1A, H1B, C9, C14
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 F1, F2, F3, C23, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C43
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(H49A)=Sof(H49B)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(2)
 Sof(H49)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B),
 C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C12(H12), C19(H19), C20(H20),
 C21(H21), C22(H22), C49(H49)
7.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C35(H35A,H35B,H35C), C41(H41A,H41B,H41C), C50(H50A,H50B,
 H50C), C50A(H50D,H50E,H50F)
;
_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
I1 I 0.70802(2) 0.44272(2) -0.28550(5) 0.03202(11) Uani 1 1 d . . . . .
I2 I 0.84300(2) 0.50867(2) -0.18597(5) 0.02877(10) Uani 1 1 d . . . . .
F1 F 0.6751(5) 0.6895(3) -0.421(3) 0.141(8) Uani 0.61(3) 1 d D U . A 1
F2 F 0.6720(4) 0.6652(3) -0.658(2) 0.123(8) Uani 0.61(3) 1 d D U . A 1
F3 F 0.7180(3) 0.6919(3) -0.5786(19) 0.071(4) Uani 0.61(3) 1 d D U . A 1
N1 N 0.74669(15) 0.53760(14) -0.2833(7) 0.0319(12) Uani 1 1 d D . . . .
H1A H 0.7683(12) 0.534(3) -0.247(8) 0.13(5) Uiso 1 1 d D . . . .
H1B H 0.7340(19) 0.5179(14) -0.278(11) 0.07(3) Uiso 1 1 d D . . . .
N2 N 0.5881(2) 0.78438(17) -0.2777(8) 0.0544(18) Uani 1 1 d . . . . .
C1 C 0.65238(17) 0.44646(16) -0.3408(7) 0.0272(14) Uani 1 1 d . . . . .
C2 C 0.63090(18) 0.41560(17) -0.3329(8) 0.0342(16) Uani 1 1 d . . . . .
H2 H 0.641358 0.393099 -0.302821 0.041 Uiso 1 1 calc R . . . .
C3 C 0.59454(19) 0.41746(19) -0.3686(9) 0.0390(18) Uani 1 1 d . . . . .
H3 H 0.579995 0.396260 -0.363115 0.047 Uiso 1 1 calc R . . . .
C4 C 0.57905(18) 0.45038(19) -0.4126(8) 0.0333(16) Uani 1 1 d . . . . .
H4 H 0.553929 0.451709 -0.436517 0.040 Uiso 1 1 calc R . . . .
C5 C 0.60019(18) 0.48088(19) -0.4214(8) 0.0320(15) Uani 1 1 d . . . . .
H5 H 0.589572 0.503203 -0.452918 0.038 Uiso 1 1 calc R . . . .
C6 C 0.63714(17) 0.47962(17) -0.3845(7) 0.0264(14) Uani 1 1 d . . . . .
C7 C 0.65834(17) 0.51210(17) -0.3925(8) 0.0273(14) Uani 1 1 d . . . . .
C8 C 0.67533(17) 0.53947(18) -0.3975(7) 0.0276(14) Uani 1 1 d . . . . .
C9 C 0.69758(18) 0.57174(17) -0.3991(8) 0.0306(15) Uani 1 1 d . . . . .
C10 C 0.68456(19) 0.60424(18) -0.4570(9) 0.0379(17) Uani 1 1 d . . . . .
H10 H 0.660608 0.605593 -0.498136 0.045 Uiso 1 1 calc R . . . .
C11 C 0.7062(2) 0.63492(19) -0.4556(10) 0.0425(19) Uani 1 1 d . . . . .
C12 C 0.74113(19) 0.63281(18) -0.3972(9) 0.0393(17) Uani 1 1 d . . . . .
H12 H 0.755836 0.653935 -0.398009 0.047 Uiso 1 1 calc R . . . .
C13 C 0.75531(17) 0.60102(17) -0.3378(8) 0.0307(15) Uani 1 1 d . . . . .
C14 C 0.73333(16) 0.56906(16) -0.3370(7) 0.0263(14) Uani 1 1 d . . . . .
C15 C 0.79194(17) 0.59838(15) -0.2870(8) 0.0307(14) Uani 1 1 d . . . . .
C16 C 0.82288(17) 0.59408(15) -0.2455(7) 0.0266(14) Uani 1 1 d . . . . .
C17 C 0.86081(17) 0.58966(15) -0.2041(8) 0.0282(13) Uani 1 1 d . . . . .
C18 C 0.87510(16) 0.55585(16) -0.1729(8) 0.0282(14) Uani 1 1 d . . . . .
C19 C 0.91167(18) 0.55255(19) -0.1372(8) 0.0346(16) Uani 1 1 d . . . . .
H19 H 0.921650 0.529359 -0.115108 0.042 Uiso 1 1 calc R . . . .
C20 C 0.93364(18) 0.5829(2) -0.1337(8) 0.0398(18) Uani 1 1 d . . . . .
H20 H 0.958739 0.580459 -0.110911 0.048 Uiso 1 1 calc R . . . .
C21 C 0.91905(18) 0.61709(19) -0.1635(8) 0.0373(16) Uani 1 1 d . . . . .
H21 H 0.934083 0.637963 -0.159659 0.045 Uiso 1 1 calc R . . . .
C22 C 0.88275(17) 0.62046(16) -0.1985(8) 0.0319(14) Uani 1 1 d . . . . .
H22 H 0.872661 0.643678 -0.218894 0.038 Uiso 1 1 calc R . . . .
C23 C 0.6926(2) 0.6699(2) -0.5229(14) 0.075(3) Uani 1 1 d D U . . .
C24 C 0.5943(3) 0.7514(2) -0.1742(10) 0.057(2) Uani 1 1 d . . . . .
H24A H 0.577743 0.752735 -0.081532 0.069 Uiso 1 1 calc R . . . .
H24B H 0.619405 0.752346 -0.132433 0.069 Uiso 1 1 calc R . . . .
C25 C 0.5888(3) 0.7146(2) -0.2562(9) 0.055(2) Uani 1 1 d . . . . .
H25A H 0.562787 0.711060 -0.279627 0.066 Uiso 1 1 calc R . . . .
H25B H 0.602187 0.714253 -0.358788 0.066 Uiso 1 1 calc R . . . .
C26 C 0.6022(3) 0.6841(2) -0.1509(10) 0.061(2) Uani 1 1 d . . . . .
H26A H 0.588989 0.684826 -0.048028 0.073 Uiso 1 1 calc R . . . .
H26B H 0.628249 0.687818 -0.127971 0.073 Uiso 1 1 calc R . . . .
C27 C 0.5970(2) 0.6469(2) -0.2272(10) 0.054(2) Uani 1 1 d . . . . .
H27A H 0.571085 0.643402 -0.252646 0.065 Uiso 1 1 calc R . . . .
H27B H 0.610800 0.645911 -0.328596 0.065 Uiso 1 1 calc R . . . .
C28 C 0.6096(3) 0.6165(2) -0.1190(12) 0.072(3) Uani 1 1 d . . . . .
H28A H 0.636039 0.618418 -0.100863 0.087 Uiso 1 1 calc R . . . .
H28B H 0.597239 0.618217 -0.014366 0.087 Uiso 1 1 calc R . . . .
C29 C 0.6011(3) 0.5816(3) -0.1949(19) 0.110(4) Uani 1 1 d . . . . .
H29A H 0.613833 0.579821 -0.297274 0.165 Uiso 1 1 calc GR . . . .
H29B H 0.574909 0.579908 -0.213081 0.165 Uiso 1 1 calc GR . . . .
H29C H 0.608828 0.561763 -0.124904 0.165 Uiso 1 1 calc GR . . . .
C30 C 0.5950(2) 0.8172(2) -0.1699(9) 0.0472(19) Uani 1 1 d . . . . .
H30A H 0.577865 0.816141 -0.079008 0.057 Uiso 1 1 calc R . . . .
H30B H 0.619801 0.815303 -0.125820 0.057 Uiso 1 1 calc R . . . .
C31 C 0.5910(2) 0.8536(2) -0.2512(9) 0.052(2) Uani 1 1 d . . . . .
H31A H 0.565733 0.856911 -0.287492 0.063 Uiso 1 1 calc R . . . .
H31B H 0.607061 0.854672 -0.345939 0.063 Uiso 1 1 calc R . . . .
C32 C 0.6012(2) 0.8838(2) -0.1337(9) 0.048(2) Uani 1 1 d . . . . .
H32A H 0.584422 0.883126 -0.041592 0.058 Uiso 1 1 calc R . . . .
H32B H 0.626007 0.879364 -0.092858 0.058 Uiso 1 1 calc R . . . .
C33 C 0.5998(2) 0.92106(19) -0.2086(10) 0.0500(19) Uani 1 1 d . . . . .
H33A H 0.574816 0.925822 -0.245481 0.060 Uiso 1 1 calc R . . . .
H33B H 0.615828 0.921333 -0.303561 0.060 Uiso 1 1 calc R . . . .
C34 C 0.6113(3) 0.9513(2) -0.0967(10) 0.056(2) Uani 1 1 d . . . . .
H34A H 0.636013 0.946168 -0.056522 0.067 Uiso 1 1 calc R . . . .
H34B H 0.594720 0.951788 -0.003818 0.067 Uiso 1 1 calc R . . . .
C35 C 0.6110(3) 0.9883(2) -0.1777(11) 0.068(3) Uani 1 1 d . . . . .
H35A H 0.625901 0.987367 -0.274559 0.102 Uiso 1 1 calc GR . . . .
H35B H 0.620901 1.006477 -0.104408 0.102 Uiso 1 1 calc GR . . . .
H35C H 0.586105 0.994772 -0.206093 0.102 Uiso 1 1 calc GR . . . .
C36 C 0.5498(3) 0.7851(2) -0.3429(9) 0.061(3) Uani 1 1 d . . . . .
H36A H 0.547439 0.806213 -0.414809 0.073 Uiso 1 1 calc R . . . .
H36B H 0.546089 0.763022 -0.408212 0.073 Uiso 1 1 calc R . . . .
C37 C 0.5201(2) 0.7870(3) -0.2202(10) 0.060(2) Uani 1 1 d . . . . .
H37A H 0.521155 0.810494 -0.163739 0.072 Uiso 1 1 calc R . . . .
H37B H 0.523338 0.767393 -0.140555 0.072 Uiso 1 1 calc R . . . .
C38 C 0.4836(3) 0.7828(3) -0.3036(11) 0.074(3) Uani 1 1 d . . . . .
H38A H 0.482036 0.800546 -0.391970 0.089 Uiso 1 1 calc R . . . .
H38B H 0.482005 0.758239 -0.350672 0.089 Uiso 1 1 calc R . . . .
C39 C 0.4518(3) 0.7884(3) -0.1930(13) 0.084(3) Uani 1 1 d . . . . .
H39A H 0.453172 0.813100 -0.147552 0.101 Uiso 1 1 calc R . . . .
H39B H 0.453691 0.770968 -0.103359 0.101 Uiso 1 1 calc R . . . .
C40 C 0.4147(3) 0.7835(3) -0.2748(11) 0.079(3) Uani 1 1 d . . . . .
H40A H 0.413579 0.799506 -0.369511 0.095 Uiso 1 1 calc R . . . .
H40B H 0.412557 0.758179 -0.312644 0.095 Uiso 1 1 calc R . . . .
C41 C 0.3834(3) 0.7917(4) -0.1698(15) 0.108(5) Uani 1 1 d . . . . .
H41A H 0.360814 0.787029 -0.227632 0.162 Uiso 1 1 calc GR . . . .
H41B H 0.384299 0.817219 -0.137631 0.162 Uiso 1 1 calc GR . . . .
H41C H 0.384456 0.776292 -0.074558 0.162 Uiso 1 1 calc GR . . . .
C42 C 0.6125(3) 0.7845(2) -0.4224(11) 0.069(3) Uani 1 1 d . . . . .
H42A H 0.607577 0.806695 -0.485324 0.083 Uiso 1 1 calc R . . . .
H42B H 0.606390 0.763432 -0.490146 0.083 Uiso 1 1 calc R . . . .
C43 C 0.6528(3) 0.7832(3) -0.3833(16) 0.092(4) Uani 1 1 d . U . . .
H43A H 0.658411 0.802720 -0.306062 0.110 Uiso 1 1 calc R . . . .
H43B H 0.658236 0.759787 -0.330938 0.110 Uiso 1 1 calc R . . . .
C44 C 0.6754(6) 0.7871(6) -0.517(2) 0.211(11) Uani 1 1 d . . . . .
F1A F 0.6579(3) 0.6722(5) -0.524(3) 0.083(9) Uani 0.39(3) 1 d D U . A 2
F2A F 0.7050(10) 0.6751(8) -0.664(3) 0.151(15) Uani 0.39(3) 1 d D U . A 2
F3A F 0.7039(9) 0.6978(4) -0.441(4) 0.132(15) Uani 0.39(3) 1 d D U . A 2
Cl1 Cl 0.79136(4) 0.43982(4) -0.2137(2) 0.0361(4) Uani 1 1 d . . . . .
Cl2 Cl 0.500000 0.500000 0.500000 0.0386(8) Uani 1 4 d S T P . .
N3 N 0.500000 0.500000 0.000000 0.038(3) Uani 1 4 d S T P . .
C45 C 0.53316(18) 0.4995(2) 0.1082(8) 0.0366(16) Uani 1 1 d . . . . .
H45A H 0.530381 0.479665 0.186598 0.044 Uiso 1 1 calc R . . . .
H45B H 0.533996 0.522598 0.168544 0.044 Uiso 1 1 calc R . . . .
C46 C 0.5693(2) 0.4946(2) 0.0207(8) 0.0398(17) Uani 1 1 d . . . . .
H46A H 0.571634 0.469139 -0.014796 0.048 Uiso 1 1 calc R . . . .
H46B H 0.569716 0.510280 -0.075271 0.048 Uiso 1 1 calc R . . . .
C47 C 0.60101(19) 0.5043(2) 0.1289(8) 0.0381(17) Uani 1 1 d . . . . .
H47A H 0.598853 0.529987 0.161267 0.046 Uiso 1 1 calc R . . . .
H47B H 0.599743 0.489293 0.226826 0.046 Uiso 1 1 calc R . . . .
C48 C 0.6376(2) 0.4985(3) 0.0497(9) 0.057(2) Uani 1 1 d . . . . .
H48A H 0.640440 0.472405 0.025797 0.068 Uiso 1 1 calc R . . . .
H48B H 0.637834 0.511721 -0.053200 0.068 Uiso 1 1 calc R . . . .
C49 C 0.6696(2) 0.5108(3) 0.1484(12) 0.071(3) Uani 1 1 d D . . . .
H49 H 0.666608 0.511206 0.261121 0.086 Uiso 0.305(18) 1 calc R . . B 1
H49A H 0.664967 0.504936 0.261963 0.086 Uiso 0.695(18) 1 calc R . . B 2
H49B H 0.691359 0.497242 0.114317 0.086 Uiso 0.695(18) 1 calc R . . B 2
C50 C 0.7017(6) 0.5213(8) 0.091(3) 0.050(9) Uani 0.305(18) 1 d D . . B 1
H50A H 0.698014 0.536606 -0.003546 0.076 Uiso 0.305(18) 1 calc GR . . B 1
H50B H 0.715871 0.499871 0.060559 0.076 Uiso 0.305(18) 1 calc GR . . B 1
H50C H 0.714822 0.534998 0.172507 0.076 Uiso 0.305(18) 1 calc GR . . B 1
C50A C 0.6765(4) 0.5478(4) 0.1350(19) 0.073(5) Uani 0.695(18) 1 d D . . B 2
H50D H 0.656036 0.561443 0.179022 0.109 Uiso 0.695(18) 1 calc GR . . B 2
H50E H 0.679726 0.554084 0.022256 0.109 Uiso 0.695(18) 1 calc GR . . B 2
H50F H 0.698564 0.553768 0.194408 0.109 Uiso 0.695(18) 1 calc GR . . B 2


_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 2.110(6) . ?
I2 C18 2.109(6) . ?
F1 C23 1.295(14) . ?
F2 C23 1.371(14) . ?
F3 C23 1.325(12) . ?
N1 C14 1.340(8) . ?
N2 C24 1.512(9) . ?
N2 C30 1.530(10) . ?
N2 C36 1.517(11) . ?
N2 C42 1.509(11) . ?
C1 C2 1.389(9) . ?
C1 C6 1.396(9) . ?
C2 C3 1.377(10) . ?
C3 C4 1.393(10) . ?
C4 C5 1.372(9) . ?
C5 C6 1.399(9) . ?
C6 C7 1.433(9) . ?
C7 C8 1.190(9) . ?
C8 C9 1.447(9) . ?
C9 C10 1.380(10) . ?
C9 C14 1.422(9) . ?
C10 C11 1.386(10) . ?
C11 C12 1.381(10) . ?
C11 C23 1.495(12) . ?
C12 C13 1.378(9) . ?
C13 C14 1.432(8) . ?
C13 C15 1.421(9) . ?
C15 C16 1.204(8) . ?
C16 C17 1.452(9) . ?
C17 C18 1.380(8) . ?
C17 C22 1.397(8) . ?
C18 C19 1.388(9) . ?
C19 C20 1.384(10) . ?
C20 C21 1.394(10) . ?
C21 C22 1.377(9) . ?
C23 F1A 1.285(14) . ?
C23 F2A 1.284(18) . ?
C23 F3A 1.305(16) . ?
C24 C25 1.534(11) . ?
C25 C26 1.513(11) . ?
C26 C27 1.526(11) . ?
C27 C28 1.515(12) . ?
C28 C29 1.471(15) . ?
C30 C31 1.514(10) . ?
C31 C32 1.535(11) . ?
C32 C33 1.511(10) . ?
C33 C34 1.516(11) . ?
C34 C35 1.525(11) . ?
C36 C37 1.503(12) . ?
C37 C38 1.528(12) . ?
C38 C39 1.508(14) . ?
C39 C40 1.543(12) . ?
C40 C41 1.482(15) . ?
C42 C43 1.523(16) . ?
C43 C44 1.401(17) . ?
N3 C45 1.523(7) 3_565 ?
N3 C45 1.523(7) 4_655 ?
N3 C45 1.523(7) 2_665 ?
N3 C45 1.523(7) . ?
C45 C46 1.532(10) . ?
C46 C47 1.524(10) . ?
C47 C48 1.519(11) . ?
C48 C49 1.512(11) . ?
C49 C50 1.34(2) . ?
C49 C50A 1.391(15) . ?

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
C24 N2 C30 105.9(6) . . ?
C24 N2 C36 111.1(7) . . ?
C36 N2 C30 110.7(6) . . ?
C42 N2 C24 111.9(6) . . ?
C42 N2 C30 111.8(7) . . ?
C42 N2 C36 105.5(7) . . ?
C2 C1 I1 119.4(5) . . ?
C2 C1 C6 120.1(6) . . ?
C6 C1 I1 120.5(4) . . ?
C3 C2 C1 120.4(6) . . ?
C2 C3 C4 120.1(6) . . ?
C5 C4 C3 119.8(6) . . ?
C4 C5 C6 121.0(7) . . ?
C1 C6 C5 118.7(6) . . ?
C1 C6 C7 121.7(6) . . ?
C5 C6 C7 119.6(6) . . ?
C8 C7 C6 178.6(7) . . ?
C7 C8 C9 176.9(7) . . ?
C10 C9 C8 121.4(6) . . ?
C10 C9 C14 120.8(6) . . ?
C14 C9 C8 117.8(6) . . ?
C9 C10 C11 120.4(7) . . ?
C10 C11 C23 120.6(7) . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 C23 119.7(6) . . ?
C13 C12 C11 122.0(6) . . ?
C12 C13 C14 119.2(6) . . ?
C12 C13 C15 121.9(6) . . ?
C15 C13 C14 118.8(6) . . ?
N1 C14 C9 121.6(5) . . ?
N1 C14 C13 120.5(6) . . ?
C9 C14 C13 117.8(6) . . ?
C16 C15 C13 176.3(6) . . ?
C15 C16 C17 176.9(7) . . ?
C18 C17 C16 121.0(5) . . ?
C18 C17 C22 120.5(6) . . ?
C22 C17 C16 118.4(5) . . ?
C17 C18 I2 121.5(5) . . ?
C17 C18 C19 119.5(6) . . ?
C19 C18 I2 119.0(5) . . ?
C20 C19 C18 120.2(7) . . ?
C19 C20 C21 120.2(6) . . ?
C22 C21 C20 119.7(6) . . ?
C21 C22 C17 119.9(6) . . ?
F1 C23 F2 109.6(13) . . ?
F1 C23 F3 104.1(10) . . ?
F1 C23 C11 113.7(11) . . ?
F2 C23 C11 112.8(8) . . ?
F3 C23 F2 100.4(11) . . ?
F3 C23 C11 115.1(8) . . ?
F1A C23 C11 113.3(10) . . ?
F1A C23 F3A 105.6(18) . . ?
F2A C23 C11 111.0(13) . . ?
F2A C23 F1A 109.8(19) . . ?
F2A C23 F3A 105(2) . . ?
F3A C23 C11 112.0(11) . . ?
N2 C24 C25 115.9(7) . . ?
C26 C25 C24 110.7(7) . . ?
C25 C26 C27 112.6(7) . . ?
C28 C27 C26 112.2(7) . . ?
C29 C28 C27 109.0(9) . . ?
C31 C30 N2 114.9(6) . . ?
C30 C31 C32 109.5(6) . . ?
C33 C32 C31 112.7(6) . . ?
C32 C33 C34 113.7(7) . . ?
C33 C34 C35 112.5(7) . . ?
C37 C36 N2 115.8(6) . . ?
C36 C37 C38 109.1(7) . . ?
C39 C38 C37 113.1(7) . . ?
C38 C39 C40 113.7(8) . . ?
C41 C40 C39 113.9(8) . . ?
N2 C42 C43 114.2(8) . . ?
C44 C43 C42 114.0(16) . . ?
C45 N3 C45 107.0(5) 3_565 4_655 ?
C45 N3 C45 110.7(3) 3_565 2_665 ?
C45 N3 C45 110.7(3) 4_655 2_665 ?
C45 N3 C45 110.7(3) 3_565 . ?
C45 N3 C45 110.7(3) 4_655 . ?
C45 N3 C45 107.0(5) 2_665 . ?
N3 C45 C46 114.6(5) . . ?
C47 C46 C45 110.9(6) . . ?
C48 C47 C46 113.0(6) . . ?
C49 C48 C47 114.4(7) . . ?
C50 C49 C48 125.6(15) . . ?
C50A C49 C48 113.2(10) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 0.366 208 41 ' '
2 0.250 0.750 0.538 413 83 ' '
3 0.250 0.250 0.657 412 83 ' '
4 0.500 1.000 0.522 208 41 ' '
5 0.750 0.250 0.038 413 83 ' '
6 0.750 0.750 0.157 412 83 ' '

_platon_squeeze_void_probe_radius 1.20
_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_umt_ob144
_database_code_depnum_ccdc_archive 'CCDC 2023093'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H12 F9 N'
_chemical_formula_sum            'C25 H12 F9 N'
_chemical_formula_weight         497.36
_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'

_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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   37.842(3)
_cell_length_b                   50.545(4)
_cell_length_c                   8.9837(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     17183(2)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    9626
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.186
_cell_measurement_theta_min      2.626
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0667 before and 0.0633 after correction. The Ratio of minimum to maximum transmission is 0.9398. 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    1.538
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             8000
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            130424
_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         26.468
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.875
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7881
_reflns_number_total             8847
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 3275 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         8847
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.057
_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)+(0.0751P)²+63.5185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1475
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT213_umt_ob144           
;
PROBLEM: Atom F8A             has ADP max/min Ratio .....        4.1 prolat
RESPONSE: The fluorine atoms in question are part of a CF3 group that is 
likely disordered. Attempts at producing a suitable model were unsuccessful.
Contributing to the difficulty of finding was suitable model was the lack of
observable secondary sites for the other fluorine atoms in the CF3 group 
containing fluorine F8A.   The other alerts arise from a CF3 disorder that is
likely dynamic in nature, there was no improvement in the model by modeling 
this disorder of this group over 3 or more sites.  As such a model of 
simplicity was chosen for both cases as a more complex disorder model does 
not significantly enhance the results and would necessitate several 
geometrical  and thermal constraints.  Furthermore, the elongated ellipsoids
provide a more immediate  (visual) statement regarding the disorder of these
CF3 sites. 
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 F4A, F5A, F6A, C24A, F4AA, F5AA, F6AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F4BB)=Sof(F5BB)=Sof(F6BB)=1-FVAR(1)
 Sof(F4B)=Sof(F5B)=Sof(F6B)=FVAR(1)
 Sof(F4AA)=Sof(F5AA)=Sof(F6AA)=1-FVAR(2)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C5A(H5A), C10A(H10A), C12A(H12A), C13A(H13A), C14A(H14A),
 C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C3B(H3B), C5B(H5B), C11B(H11B),
  C13B(H13B), C14B(H14B), C15B(H15B), C19B(H19B), C21B(H21B), C22B(H22B),
 C23B(H23B)
;
_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
F1A F -0.55236(8) -0.60285(8) -0.9017(3) 0.0505(9) Uani 1 1 d . . . . .
F2A F -0.59342(11) -0.63030(6) -0.9368(3) 0.0555(9) Uani 1 1 d . . . . .
F3A F -0.60595(7) -0.58916(5) -0.9055(3) 0.0341(6) Uani 1 1 d . . . . .
F4A F -0.5461(3) -0.68078(15) -2.0756(7) 0.047(3) Uani 0.57(2) 1 d . U P A 1
F5A F -0.5460(5) -0.72113(15) -2.0483(13) 0.092(6) Uani 0.57(2) 1 d . U P A 1
F6A F -0.4993(3) -0.7025(5) -2.1183(10) 0.104(7) Uani 0.57(2) 1 d . U P A 1
F7A F -0.67805(10) -0.54963(7) -2.0268(4) 0.0556(9) Uani 1 1 d . . . . .
F8A F -0.69677(14) -0.51174(9) -2.0873(4) 0.0953(19) Uani 1 1 d . . . . .
F9A F -0.64145(11) -0.52097(7) -2.0963(4) 0.0639(11) Uani 1 1 d . . . . .
N1A N -0.57307(10) -0.59315(8) -1.5936(4) 0.0234(8) Uani 1 1 d . . . . .
H1AA H -0.5789(12) -0.5795(10) -1.629(6) 0.018(12) Uiso 1 1 d . . . . .
H1AB H -0.5594(14) -0.6043(11) -1.635(6) 0.032(14) Uiso 1 1 d . . . . .
C1A C -0.57503(10) -0.59541(8) -1.4439(4) 0.0162(8) Uani 1 1 d . . . . .
C2A C -0.55958(9) -0.61764(7) -1.3713(4) 0.0152(7) Uani 1 1 d . . . . .
C3A C -0.56257(10) -0.62008(8) -1.2184(4) 0.0163(8) Uani 1 1 d . . . . .
H3A H -0.552018 -0.634768 -1.169565 0.020 Uiso 1 1 calc R . . . .
C4A C -0.58067(10) -0.60148(8) -1.1359(4) 0.0173(8) Uani 1 1 d . . . . .
C5A C -0.59628(10) -0.57979(8) -1.2043(4) 0.0171(8) Uani 1 1 d . . . . .
H5A H -0.608764 -0.567129 -1.146560 0.021 Uiso 1 1 calc R . . . .
C6A C -0.59356(9) -0.57667(7) -1.3578(4) 0.0154(7) Uani 1 1 d . . . . .
C7A C -0.54336(10) -0.63764(8) -1.4594(4) 0.0177(8) Uani 1 1 d . . . . .
C8A C -0.53223(10) -0.65484(7) -1.5392(4) 0.0178(8) Uani 1 1 d . . . . .
C9A C -0.51858(10) -0.67574(7) -1.6311(4) 0.0172(8) Uani 1 1 d . . . . .
C10A C -0.52896(10) -0.67759(8) -1.7794(5) 0.0200(8) Uani 1 1 d . . . . .
H10A H -0.545390 -0.665302 -1.819607 0.024 Uiso 1 1 calc R . . . .
C11A C -0.51500(11) -0.69768(7) -1.8684(5) 0.0198(8) Uani 1 1 d . . . . .
C12A C -0.49123(11) -0.71593(7) -1.8109(5) 0.0212(8) Uani 1 1 d . . . . .
H12A H -0.481726 -0.729463 -1.872415 0.025 Uiso 1 1 calc R . . . .
C13A C -0.48155(11) -0.71414(8) -1.6624(5) 0.0231(8) Uani 1 1 d . . . . .
H13A H -0.465512 -0.726681 -1.621920 0.028 Uiso 1 1 calc R . . . .
C14A C -0.49490(10) -0.69435(8) -1.5725(4) 0.0216(8) Uani 1 1 d . . . . .
H14A H -0.488048 -0.693365 -1.470919 0.026 Uiso 1 1 calc R . . . .
C15A C -0.61094(10) -0.55571(8) -1.4354(4) 0.0167(7) Uani 1 1 d . . . . .
C16A C -0.62557(10) -0.53989(8) -1.5128(4) 0.0192(8) Uani 1 1 d . . . . .
C17A C -0.64389(9) -0.52255(8) -1.6136(4) 0.0170(8) Uani 1 1 d . . . . .
C18A C -0.64883(11) -0.53066(8) -1.7605(5) 0.0218(8) Uani 1 1 d . . . . .
H18A H -0.639967 -0.547299 -1.792520 0.026 Uiso 1 1 calc R . . . .
C19A C -0.66658(11) -0.51452(8) -1.8596(5) 0.0231(8) Uani 1 1 d . . . . .
C20A C -0.67944(10) -0.48999(8) -1.8155(4) 0.0201(8) Uani 1 1 d . . . . .
H20A H -0.691453 -0.478931 -1.884376 0.024 Uiso 1 1 calc R . . . .
C21A C -0.67450(10) -0.48188(8) -1.6696(5) 0.0195(8) Uani 1 1 d . . . . .
H21A H -0.683248 -0.465159 -1.638328 0.023 Uiso 1 1 calc R . . . .
C22A C -0.65694(10) -0.49790(8) -1.5692(4) 0.0181(8) Uani 1 1 d . . . . .
H22A H -0.653732 -0.492143 -1.469432 0.022 Uiso 1 1 calc R . . . .
C23A C -0.58365(12) -0.60577(9) -0.9717(5) 0.0260(9) Uani 1 1 d . . . . .
C24A C -0.52647(13) -0.70019(8) -2.0273(5) 0.0310(10) Uani 1 1 d . U . . .
C25A C -0.67115(15) -0.52390(10) -2.0172(5) 0.0388(12) Uani 1 1 d . . . . .
F4AA F -0.5605(3) -0.7049(5) -2.0397(13) 0.096(9) Uani 0.43(2) 1 d . U P A 2
F5AA F -0.5131(6) -0.7192(3) -2.0991(13) 0.072(6) Uani 0.43(2) 1 d . U P A 2
F6AA F -0.5210(7) -0.6786(2) -2.1039(13) 0.076(7) Uani 0.43(2) 1 d . U P A 2
F1B F -0.53539(9) -0.50874(7) -0.8976(4) 0.0510(8) Uani 1 1 d . . . . .
F2B F -0.56329(10) -0.54450(8) -0.9132(4) 0.0600(9) Uani 1 1 d . . . . .
F3B F -0.50675(10) -0.54512(8) -0.8925(4) 0.0587(10) Uani 1 1 d . . . . .
F4B F -0.4808(3) -0.6178(3) -2.0568(9) 0.078(5) Uani 0.546(18) 1 d . . P B 1
F5B F -0.4520(4) -0.65413(16) -2.0610(11) 0.087(5) Uani 0.546(18) 1 d . . P B 1
F6B F -0.4257(3) -0.6181(3) -2.0635(10) 0.084(5) Uani 0.546(18) 1 d . . P B 1
F7B F -0.61809(14) -0.46821(9) -2.0641(5) 0.0884(15) Uani 1 1 d . . . . .
F8B F -0.62224(13) -0.42692(9) -2.1027(5) 0.0880(16) Uani 1 1 d . . . . .
F9B F -0.57270(10) -0.44599(9) -2.0817(5) 0.0754(13) Uani 1 1 d . . . . .
N1B N -0.52396(11) -0.53132(9) -1.5839(5) 0.0298(9) Uani 1 1 d . . . . .
H1BA H -0.5327(14) -0.5188(11) -1.624(6) 0.028(14) Uiso 1 1 d . . . . .
H1BB H -0.513(2) -0.5457(17) -1.624(11) 0.10(3) Uiso 1 1 d . . . . .
C1B C -0.52542(10) -0.53140(8) -1.4339(5) 0.0211(8) Uani 1 1 d . . . . .
C3B C -0.51086(11) -0.55191(9) -1.1973(5) 0.0253(9) Uani 1 1 d . . . . .
H3B H -0.499498 -0.565541 -1.142474 0.030 Uiso 1 1 calc R . . . .
C4B C -0.52935(11) -0.53225(9) -1.1231(5) 0.0275(10) Uani 1 1 d . . . . .
C5B C -0.54602(11) -0.51232(9) -1.2024(5) 0.0256(9) Uani 1 1 d . . . . .
H5B H -0.558888 -0.499057 -1.150608 0.031 Uiso 1 1 calc R . . . .
C6B C -0.54414(10) -0.51153(8) -1.3561(5) 0.0244(9) Uani 1 1 d . . . . .
C7B C -0.50892(10) -0.55173(8) -1.3517(5) 0.0221(9) Uani 1 1 d . . . . .
C8B C -0.49146(11) -0.57236(8) -1.4326(5) 0.0240(9) Uani 1 1 d . . . . .
C9B C -0.47826(11) -0.58922(8) -1.5099(5) 0.0262(9) Uani 1 1 d . . . . .
C10B C -0.46315(10) -0.60991(8) -1.5976(5) 0.0259(9) Uani 1 1 d . . . . .
C11B C -0.46631(11) -0.60961(8) -1.7533(6) 0.0271(9) Uani 1 1 d . . . . .
H11B H -0.478663 -0.595689 -1.801665 0.033 Uiso 1 1 calc R . . . .
C12B C -0.45125(12) -0.62979(9) -1.8354(6) 0.0297(10) Uani 1 1 d . . . . .
C13B C -0.43345(11) -0.65036(9) -1.7674(6) 0.0328(11) Uani 1 1 d . . . . .
H13B H -0.423192 -0.664072 -1.825392 0.039 Uiso 1 1 calc R . . . .
C14B C -0.43071(12) -0.65077(9) -1.6132(6) 0.0336(11) Uani 1 1 d . . . . .
H14B H -0.418779 -0.664973 -1.565561 0.040 Uiso 1 1 calc R . . . .
C15B C -0.44522(11) -0.63067(9) -1.5287(6) 0.0292(10) Uani 1 1 d . . . . .
H15B H -0.442968 -0.630998 -1.423391 0.035 Uiso 1 1 calc R . . . .
C16B C -0.56071(11) -0.49118(8) -1.4416(5) 0.0253(9) Uani 1 1 d . . . . .
C17B C -0.57352(11) -0.47477(8) -1.5221(6) 0.0274(9) Uani 1 1 d . . . . .
C18B C -0.58964(10) -0.45536(8) -1.6166(6) 0.0276(10) Uani 1 1 d . . . . .
C19B C -0.58940(10) -0.45883(8) -1.7703(6) 0.0277(10) Uani 1 1 d . . . . .
H19B H -0.578365 -0.473935 -1.812729 0.033 Uiso 1 1 calc R . . . .
C20B C -0.60542(11) -0.44005(9) -1.8618(6) 0.0323(11) Uani 1 1 d . . . . .
C21B C -0.62148(11) -0.41781(9) -1.8004(6) 0.0337(11) Uani 1 1 d . . . . .
H21B H -0.632320 -0.404994 -1.862758 0.040 Uiso 1 1 calc R . . . .
C22B C -0.62148(12) -0.41462(9) -1.6492(7) 0.0370(12) Uani 1 1 d . . . . .
H22B H -0.632456 -0.399418 -1.607544 0.044 Uiso 1 1 calc R . . . .
C23B C -0.60593(11) -0.43289(9) -1.5553(6) 0.0334(11) Uani 1 1 d . . . . .
H23B H -0.606269 -0.430289 -1.450577 0.040 Uiso 1 1 calc R . . . .
C24B C -0.53271(14) -0.53295(10) -0.9584(6) 0.0354(11) Uani 1 1 d . . . . .
C25B C -0.45472(14) -0.62964(10) -2.0011(6) 0.0406(12) Uani 1 1 d . . . . .
C26B C -0.60494(13) -0.44447(10) -2.0251(7) 0.0399(12) Uani 1 1 d . . . . .
F4BB F -0.4569(6) -0.60441(18) -2.0523(11) 0.090(7) Uani 0.454(18) 1 d . . P B
2
F5BB F -0.4863(3) -0.6400(4) -2.0390(11) 0.095(6) Uani 0.454(18) 1 d . . P B 2
F6BB F -0.4322(4) -0.6407(4) -2.0745(10) 0.084(7) Uani 0.454(18) 1 d . . P B 2


_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
F1A C23A 1.349(5) . ?
F2A C23A 1.331(5) . ?
F3A C23A 1.331(5) . ?
F4A C24A 1.305(7) . ?
F5A C24A 1.304(10) . ?
F6A C24A 1.318(9) . ?
F7A C25A 1.329(6) . ?
F8A C25A 1.310(6) . ?
F9A C25A 1.338(7) . ?
N1A C1A 1.352(5) . ?
C1A C2A 1.425(5) . ?
C1A C6A 1.409(5) . ?
C2A C3A 1.384(5) . ?
C2A C7A 1.424(5) . ?
C3A C4A 1.379(5) . ?
C4A C5A 1.388(5) . ?
C4A C23A 1.496(5) . ?
C5A C6A 1.392(5) . ?
C6A C15A 1.429(5) . ?
C7A C8A 1.203(6) . ?
C8A C9A 1.437(5) . ?
C9A C10A 1.392(6) . ?
C9A C14A 1.402(6) . ?
C10A C11A 1.397(5) . ?
C11A C12A 1.388(6) . ?
C11A C24A 1.497(6) . ?
C12A C13A 1.386(6) . ?
C13A C14A 1.381(6) . ?
C15A C16A 1.195(6) . ?
C16A C17A 1.439(5) . ?
C17A C18A 1.395(6) . ?
C17A C22A 1.398(5) . ?
C18A C19A 1.382(6) . ?
C19A C20A 1.390(6) . ?
C19A C25A 1.502(6) . ?
C20A C21A 1.386(6) . ?
C21A C22A 1.383(6) . ?
C24A F4AA 1.315(10) . ?
C24A F5AA 1.265(10) . ?
C24A F6AA 1.307(10) . ?
F1B C24B 1.344(6) . ?
F2B C24B 1.358(6) . ?
F3B C24B 1.302(6) . ?
F4B C25B 1.260(9) . ?
F5B C25B 1.354(9) . ?
F6B C25B 1.365(9) . ?
F7B C26B 1.345(7) . ?
F8B C26B 1.305(6) . ?
F9B C26B 1.324(6) . ?
N1B C1B 1.348(6) . ?
C1B C6B 1.414(6) . ?
C1B C7B 1.411(6) . ?
C3B C4B 1.386(7) . ?
C3B C7B 1.389(6) . ?
C4B C5B 1.386(7) . ?
C4B C24B 1.485(7) . ?
C5B C6B 1.383(6) . ?
C6B C16B 1.429(6) . ?
C7B C8B 1.433(6) . ?
C8B C9B 1.207(6) . ?
C9B C10B 1.429(6) . ?
C10B C11B 1.404(7) . ?
C10B C15B 1.394(6) . ?
C11B C12B 1.382(6) . ?
C12B C13B 1.381(7) . ?
C12B C25B 1.495(8) . ?
C13B C14B 1.389(8) . ?
C14B C15B 1.382(7) . ?
C16B C17B 1.203(6) . ?
C17B C18B 1.434(6) . ?
C18B C19B 1.392(7) . ?
C18B C23B 1.405(6) . ?
C19B C20B 1.394(6) . ?
C20B C21B 1.392(7) . ?
C20B C26B 1.484(8) . ?
C21B C22B 1.368(8) . ?
C22B C23B 1.382(7) . ?
C25B F4BB 1.358(10) . ?
C25B F5BB 1.349(11) . ?
C25B F6BB 1.213(9) . ?

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
N1A C1A C2A 120.0(4) . . ?
N1A C1A C6A 121.1(4) . . ?
C6A C1A C2A 118.9(3) . . ?
C3A C2A C1A 119.4(3) . . ?
C3A C2A C7A 121.6(4) . . ?
C7A C2A C1A 118.9(3) . . ?
C4A C3A C2A 120.8(4) . . ?
C3A C4A C5A 120.8(3) . . ?
C3A C4A C23A 117.9(4) . . ?
C5A C4A C23A 121.3(4) . . ?
C4A C5A C6A 119.8(3) . . ?
C1A C6A C15A 117.4(3) . . ?
C5A C6A C1A 120.2(3) . . ?
C5A C6A C15A 122.3(3) . . ?
C8A C7A C2A 174.8(4) . . ?
C7A C8A C9A 178.5(4) . . ?
C10A C9A C8A 119.9(4) . . ?
C10A C9A C14A 119.7(3) . . ?
C14A C9A C8A 120.5(4) . . ?
C9A C10A C11A 119.3(4) . . ?
C10A C11A C24A 119.9(4) . . ?
C12A C11A C10A 121.0(4) . . ?
C12A C11A C24A 119.1(3) . . ?
C13A C12A C11A 119.1(4) . . ?
C14A C13A C12A 120.9(4) . . ?
C13A C14A C9A 120.0(4) . . ?
C16A C15A C6A 173.2(4) . . ?
C15A C16A C17A 175.5(4) . . ?
C18A C17A C16A 118.8(4) . . ?
C18A C17A C22A 119.0(4) . . ?
C22A C17A C16A 122.2(4) . . ?
C19A C18A C17A 120.1(4) . . ?
C18A C19A C20A 120.8(4) . . ?
C18A C19A C25A 118.5(4) . . ?
C20A C19A C25A 120.7(4) . . ?
C21A C20A C19A 119.1(4) . . ?
C22A C21A C20A 120.6(4) . . ?
C21A C22A C17A 120.4(4) . . ?
F1A C23A C4A 112.2(4) . . ?
F2A C23A F1A 103.7(4) . . ?
F2A C23A C4A 112.9(4) . . ?
F3A C23A F1A 106.2(4) . . ?
F3A C23A F2A 107.8(4) . . ?
F3A C23A C4A 113.4(4) . . ?
F4A C24A F6A 107.7(8) . . ?
F4A C24A C11A 114.7(4) . . ?
F5A C24A F4A 103.9(7) . . ?
F5A C24A F6A 106.2(9) . . ?
F5A C24A C11A 111.8(5) . . ?
F6A C24A C11A 111.9(6) . . ?
F4AA C24A C11A 112.4(6) . . ?
F5AA C24A C11A 115.7(6) . . ?
F5AA C24A F4AA 102.1(10) . . ?
F5AA C24A F6AA 107.7(10) . . ?
F6AA C24A C11A 112.7(5) . . ?
F6AA C24A F4AA 105.2(11) . . ?
F7A C25A F9A 103.8(4) . . ?
F7A C25A C19A 113.1(4) . . ?
F8A C25A F7A 106.4(5) . . ?
F8A C25A F9A 108.3(5) . . ?
F8A C25A C19A 112.9(4) . . ?
F9A C25A C19A 111.6(5) . . ?
N1B C1B C6B 120.8(4) . . ?
N1B C1B C7B 120.5(4) . . ?
C7B C1B C6B 118.7(4) . . ?
C4B C3B C7B 120.2(4) . . ?
C3B C4B C24B 120.3(4) . . ?
C5B C4B C3B 120.2(4) . . ?
C5B C4B C24B 119.4(4) . . ?
C6B C5B C4B 120.7(4) . . ?
C1B C6B C16B 117.7(4) . . ?
C5B C6B C1B 119.9(4) . . ?
C5B C6B C16B 122.3(4) . . ?
C1B C7B C8B 117.9(4) . . ?
C3B C7B C1B 120.3(4) . . ?
C3B C7B C8B 121.7(4) . . ?
C9B C8B C7B 175.1(5) . . ?
C8B C9B C10B 177.8(5) . . ?
C11B C10B C9B 120.5(4) . . ?
C15B C10B C9B 120.0(4) . . ?
C15B C10B C11B 119.5(4) . . ?
C12B C11B C10B 119.3(4) . . ?
C11B C12B C25B 119.5(5) . . ?
C13B C12B C11B 121.4(5) . . ?
C13B C12B C25B 119.2(4) . . ?
C12B C13B C14B 119.3(4) . . ?
C15B C14B C13B 120.5(4) . . ?
C14B C15B C10B 120.2(5) . . ?
C17B C16B C6B 175.5(5) . . ?
C16B C17B C18B 178.6(5) . . ?
C19B C18B C17B 119.9(4) . . ?
C19B C18B C23B 119.6(4) . . ?
C23B C18B C17B 120.5(5) . . ?
C18B C19B C20B 119.8(4) . . ?
C19B C20B C26B 118.4(4) . . ?
C21B C20B C19B 120.4(5) . . ?
C21B C20B C26B 121.3(4) . . ?
C22B C21B C20B 119.3(4) . . ?
C21B C22B C23B 121.8(5) . . ?
C22B C23B C18B 119.2(5) . . ?
F1B C24B F2B 101.9(4) . . ?
F1B C24B C4B 112.9(4) . . ?
F2B C24B C4B 112.4(4) . . ?
F3B C24B F1B 107.6(4) . . ?
F3B C24B F2B 107.7(4) . . ?
F3B C24B C4B 113.6(5) . . ?
F4B C25B F5B 109.8(9) . . ?
F4B C25B F6B 105.3(9) . . ?
F4B C25B C12B 117.8(6) . . ?
F5B C25B F6B 99.6(9) . . ?
F5B C25B C12B 112.6(6) . . ?
F6B C25B C12B 109.9(6) . . ?
F4BB C25B C12B 110.3(6) . . ?
F5BB C25B C12B 109.1(6) . . ?
F5BB C25B F4BB 102.9(12) . . ?
F6BB C25B C12B 118.5(7) . . ?
F6BB C25B F4BB 106.9(11) . . ?
F6BB C25B F5BB 107.9(11) . . ?
F7B C26B C20B 112.8(4) . . ?
F8B C26B F7B 106.4(5) . . ?
F8B C26B F9B 107.2(5) . . ?
F8B C26B C20B 114.8(5) . . ?
F9B C26B F7B 100.9(5) . . ?
F9B C26B C20B 113.6(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_umt_ob219
_database_code_depnum_ccdc_archive 'CCDC 2238840'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H11 F6 I2 N, Cl, C24 H52 N'
_chemical_formula_sum            'C48 H63 Cl F6 I2 N2'
_chemical_formula_weight         1071.25
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.2189(5)
_cell_length_b                   22.0601(14)
_cell_length_c                   26.8587(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.235(2)
_cell_angle_gamma                90
_cell_volume                     4862.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.547
_cell_measurement_theta_min      2.648
_shelx_estimated_absorpt_T_max   0.766
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0589 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.9387. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            181343
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12637
_reflns_number_total             14933
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         14933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+5.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0707
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,
 H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B),
  C41(H41A,H41B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,
 H46B), C47(H47A,H47B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C19(H19), C20(H20),
 C22(H22)
3.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C36(H36A,H36B,H36C), C42(H42A,H42B,H42C), C48(H48A,H48B,
 H48C)
;
_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
I1 I 0.63234(2) 0.42360(2) 0.28711(2) 0.01667(3) Uani 1 1 d . . . . .
I2 I 0.46578(2) 0.51953(2) 0.10178(2) 0.01774(3) Uani 1 1 d . . . . .
Cl1 Cl 0.57876(6) 0.41130(2) 0.17019(2) 0.01880(9) Uani 1 1 d . . . . .
F1 F 0.9024(3) 0.42751(14) 0.53802(7) 0.0966(10) Uani 1 1 d . U . A 1
F2 F 0.7504(4) 0.50693(10) 0.53863(7) 0.0861(9) Uani 1 1 d . U . B 1
F3 F 0.6542(3) 0.42217(13) 0.54648(7) 0.0822(8) Uani 1 1 d . U . C 1
F4 F 0.41502(19) 0.78555(7) -0.03756(6) 0.0372(4) Uani 1 1 d . . . . .
F5 F 0.15930(18) 0.76837(7) -0.03632(6) 0.0354(3) Uani 1 1 d . . . . .
F6 F 0.29838(19) 0.72660(7) -0.09219(5) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.5240(2) 0.57599(8) 0.23229(7) 0.0205(4) Uani 1 1 d . . . . .
H1A H 0.515(4) 0.5726(13) 0.2037(12) 0.033(8) Uiso 1 1 d . . . . .
H1B H 0.549(3) 0.5490(14) 0.2507(11) 0.030(8) Uiso 1 1 d . . . . .
C1 C 0.6737(2) 0.43398(9) 0.36452(7) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.7217(3) 0.38407(10) 0.39336(8) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.732928 0.345637 0.377974 0.027 Uiso 1 1 calc R . . . .
C3 C 0.7533(3) 0.38995(11) 0.44444(8) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.786441 0.355819 0.464056 0.031 Uiso 1 1 calc R . . . .
C4 C 0.7357(3) 0.44639(11) 0.46656(8) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.6891(3) 0.49650(10) 0.43840(8) 0.0223(4) Uani 1 1 d . . . . .
H5 H 0.678394 0.534757 0.454121 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6574(2) 0.49118(9) 0.38674(7) 0.0174(4) Uani 1 1 d . . . . .
C7 C 0.6123(2) 0.54379(9) 0.35803(7) 0.0174(4) Uani 1 1 d . . . . .
C8 C 0.5762(2) 0.58909(9) 0.33533(7) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.5317(2) 0.64031(9) 0.30503(7) 0.0141(3) Uani 1 1 d . . . . .
C10 C 0.5080(2) 0.63180(9) 0.25277(7) 0.0144(3) Uani 1 1 d . . . . .
C11 C 0.5094(2) 0.69758(9) 0.32566(7) 0.0161(4) Uani 1 1 d . . . . .
H11 H 0.526477 0.702846 0.360669 0.019 Uiso 1 1 calc R . . . .
C12 C 0.4627(2) 0.74703(9) 0.29622(7) 0.0164(4) Uani 1 1 d . . . . .
H12 H 0.445361 0.785504 0.310893 0.020 Uiso 1 1 calc R . . . .
C13 C 0.4419(2) 0.73926(9) 0.24494(7) 0.0153(3) Uani 1 1 d . . . . .
H13 H 0.411354 0.773031 0.224544 0.018 Uiso 1 1 calc R . . . .
C14 C 0.4649(2) 0.68284(9) 0.22264(7) 0.0147(3) Uani 1 1 d . . . . .
C15 C 0.4430(2) 0.67489(9) 0.16996(7) 0.0163(4) Uani 1 1 d . . . . .
C16 C 0.4249(2) 0.66452(9) 0.12607(7) 0.0176(4) Uani 1 1 d . . . . .
C17 C 0.3974(2) 0.65254(9) 0.07394(7) 0.0167(4) Uani 1 1 d . . . . .
C18 C 0.4043(2) 0.59325(9) 0.05472(7) 0.0170(4) Uani 1 1 d . . . . .
C19 C 0.3751(3) 0.58291(9) 0.00390(7) 0.0198(4) Uani 1 1 d . . . . .
H19 H 0.377944 0.542648 -0.008571 0.024 Uiso 1 1 calc R . . . .
C20 C 0.3418(3) 0.63053(10) -0.02880(7) 0.0199(4) Uani 1 1 d . . . . .
H20 H 0.323187 0.623228 -0.063514 0.024 Uiso 1 1 calc R . . . .
C21 C 0.3362(2) 0.68910(9) -0.00997(7) 0.0176(4) Uani 1 1 d . . . . .
C22 C 0.3630(2) 0.70034(9) 0.04061(7) 0.0178(4) Uani 1 1 d . . . . .
H22 H 0.358114 0.740708 0.052751 0.021 Uiso 1 1 calc R . . . .
C23 C 0.7686(4) 0.45257(13) 0.52172(9) 0.0360(6) Uani 1 1 d . . . . .
C24 C 0.3026(3) 0.74182(10) -0.04395(8) 0.0216(4) Uani 1 1 d . . . . .
N2 N 0.90786(18) 0.65827(7) 0.80144(6) 0.0136(3) Uani 1 1 d . . . . .
C25 C 0.7966(2) 0.65975(9) 0.84450(7) 0.0161(4) Uani 1 1 d . . . . .
H25A H 0.717374 0.626090 0.840167 0.019 Uiso 1 1 calc R . . . .
H25B H 0.734117 0.698129 0.842729 0.019 Uiso 1 1 calc R . . . .
C26 C 0.8807(2) 0.65470(10) 0.89598(8) 0.0202(4) Uani 1 1 d . . . . .
H26A H 0.963612 0.687057 0.900729 0.024 Uiso 1 1 calc R . . . .
H26B H 0.936388 0.615021 0.899631 0.024 Uiso 1 1 calc R . . . .
C27 C 0.7533(3) 0.66083(11) 0.93513(8) 0.0242(4) Uani 1 1 d . . . . .
H27A H 0.707011 0.702243 0.933283 0.029 Uiso 1 1 calc R . . . .
H27B H 0.663589 0.631904 0.927079 0.029 Uiso 1 1 calc R . . . .
C28 C 0.8209(3) 0.64909(11) 0.98816(8) 0.0264(5) Uani 1 1 d . . . . .
H28A H 0.915364 0.676155 0.995463 0.032 Uiso 1 1 calc R . . . .
H28B H 0.736453 0.659504 1.011592 0.032 Uiso 1 1 calc R . . . .
C29 C 0.8741(4) 0.58398(12) 0.99724(9) 0.0371(6) Uani 1 1 d . . . . .
H29A H 0.781494 0.556715 0.988133 0.044 Uiso 1 1 calc R . . . .
H29B H 0.963179 0.574270 0.975229 0.044 Uiso 1 1 calc R . . . .
C30 C 0.9321(4) 0.57192(15) 1.05069(10) 0.0441(7) Uani 1 1 d . . . . .
H30A H 0.845286 0.582133 1.072783 0.066 Uiso 1 1 calc GR . . . .
H30B H 1.028345 0.596839 1.059319 0.066 Uiso 1 1 calc GR . . . .
H30C H 0.960443 0.528969 1.054631 0.066 Uiso 1 1 calc GR . . . .
C31 C 1.0265(2) 0.71121(8) 0.80453(8) 0.0159(4) Uani 1 1 d . . . . .
H31A H 1.088743 0.711242 0.774032 0.019 Uiso 1 1 calc R . . . .
H31B H 1.105216 0.704411 0.833264 0.019 Uiso 1 1 calc R . . . .
C32 C 0.9502(2) 0.77355(9) 0.81008(9) 0.0209(4) Uani 1 1 d . . . . .
H32A H 0.887248 0.774391 0.840424 0.025 Uiso 1 1 calc R . . . .
H32B H 0.874203 0.781848 0.780968 0.025 Uiso 1 1 calc R . . . .
C33 C 1.0817(2) 0.82231(9) 0.81379(8) 0.0175(4) Uani 1 1 d . . . . .
H33A H 1.135733 0.824246 0.781804 0.021 Uiso 1 1 calc R . . . .
H33B H 1.165057 0.810776 0.840133 0.021 Uiso 1 1 calc R . . . .
C34 C 1.0154(2) 0.88497(9) 0.82563(8) 0.0190(4) Uani 1 1 d . . . . .
H34A H 0.933695 0.897071 0.798974 0.023 Uiso 1 1 calc R . . . .
H34B H 0.959884 0.883105 0.857368 0.023 Uiso 1 1 calc R . . . .
C35 C 1.1496(2) 0.93250(9) 0.83001(8) 0.0188(4) Uani 1 1 d . . . . .
H35A H 1.230976 0.920271 0.856721 0.023 Uiso 1 1 calc R . . . .
H35B H 1.205464 0.933973 0.798320 0.023 Uiso 1 1 calc R . . . .
C36 C 1.0865(3) 0.99550(10) 0.84156(9) 0.0248(4) Uani 1 1 d . . . . .
H36A H 1.009109 1.008595 0.814607 0.037 Uiso 1 1 calc GR . . . .
H36B H 1.178022 1.023997 0.844487 0.037 Uiso 1 1 calc GR . . . .
H36C H 1.031758 0.994474 0.873031 0.037 Uiso 1 1 calc GR . . . .
C37 C 0.7983(2) 0.66142(9) 0.75391(7) 0.0158(3) Uani 1 1 d . . . . .
H37A H 0.717394 0.628236 0.754761 0.019 Uiso 1 1 calc R . . . .
H37B H 0.737471 0.700163 0.753959 0.019 Uiso 1 1 calc R . . . .
C38 C 0.8832(2) 0.65696(9) 0.70520(7) 0.0171(4) Uani 1 1 d . . . . .
H38A H 0.937914 0.617124 0.703206 0.020 Uiso 1 1 calc R . . . .
H38B H 0.967261 0.688982 0.704032 0.020 Uiso 1 1 calc R . . . .
C39 C 0.7594(2) 0.66423(10) 0.66104(8) 0.0201(4) Uani 1 1 d . . . . .
H39A H 0.702871 0.703577 0.663989 0.024 Uiso 1 1 calc R . . . .
H39B H 0.676685 0.631739 0.662351 0.024 Uiso 1 1 calc R . . . .
C40 C 0.8369(2) 0.66158(10) 0.61073(8) 0.0198(4) Uani 1 1 d . . . . .
H40A H 0.920477 0.693794 0.609656 0.024 Uiso 1 1 calc R . . . .
H40B H 0.892649 0.622081 0.607756 0.024 Uiso 1 1 calc R . . . .
C41 C 0.7154(3) 0.66934(15) 0.56651(9) 0.0373(6) Uani 1 1 d . . . . .
H41A H 0.659111 0.708725 0.569541 0.045 Uiso 1 1 calc R . . . .
H41B H 0.632290 0.636947 0.567379 0.045 Uiso 1 1 calc R . . . .
C42 C 0.7938(3) 0.66709(15) 0.51659(9) 0.0411(7) Uani 1 1 d . . . . .
H42A H 0.848266 0.627944 0.513029 0.062 Uiso 1 1 calc GR . . . .
H42B H 0.873885 0.699835 0.514996 0.062 Uiso 1 1 calc GR . . . .
H42C H 0.709626 0.672043 0.489561 0.062 Uiso 1 1 calc GR . . . .
C43 C 1.0090(2) 0.60070(8) 0.80286(8) 0.0157(3) Uani 1 1 d . . . . .
H43A H 1.084670 0.602098 0.832854 0.019 Uiso 1 1 calc R . . . .
H43B H 1.076086 0.600511 0.773383 0.019 Uiso 1 1 calc R . . . .
C44 C 0.9150(2) 0.54130(9) 0.80358(8) 0.0189(4) Uani 1 1 d . . . . .
H44A H 0.842948 0.537551 0.772938 0.023 Uiso 1 1 calc R . . . .
H44B H 0.846516 0.540259 0.832722 0.023 Uiso 1 1 calc R . . . .
C45 C 1.0371(2) 0.48901(9) 0.80661(8) 0.0196(4) Uani 1 1 d . . . . .
H45A H 1.093633 0.487185 0.775048 0.023 Uiso 1 1 calc R . . . .
H45B H 1.120189 0.497287 0.833898 0.023 Uiso 1 1 calc R . . . .
C46 C 0.9591(3) 0.42764(9) 0.81573(8) 0.0191(4) Uani 1 1 d . . . . .
H46A H 0.876952 0.418853 0.788300 0.023 Uiso 1 1 calc R . . . .
H46B H 0.902209 0.429210 0.847233 0.023 Uiso 1 1 calc R . . . .
C47 C 1.0852(3) 0.37674(9) 0.81891(9) 0.0240(4) Uani 1 1 d . . . . .
H47A H 1.132379 0.372111 0.786015 0.029 Uiso 1 1 calc R . . . .
H47B H 1.174547 0.388211 0.843357 0.029 Uiso 1 1 calc R . . . .
C48 C 1.0147(3) 0.31612(10) 0.83422(10) 0.0329(5) Uani 1 1 d . . . . .
H48A H 0.928973 0.303644 0.809487 0.049 Uiso 1 1 calc GR . . . .
H48B H 0.968482 0.320221 0.866906 0.049 Uiso 1 1 calc GR . . . .
H48C H 1.101166 0.285493 0.836132 0.049 Uiso 1 1 calc GR . . . .


_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 2.100(2) . ?
I2 C18 2.104(2) . ?
F1 C23 1.285(3) . ?
F2 C23 1.294(3) . ?
F3 C23 1.359(4) . ?
F4 C24 1.340(2) . ?
F5 C24 1.341(3) . ?
F6 C24 1.337(2) . ?
N1 C10 1.358(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.381(3) . ?
C4 C23 1.497(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.431(3) . ?
C7 C8 1.199(3) . ?
C8 C9 1.428(3) . ?
C9 C10 1.419(3) . ?
C9 C11 1.396(3) . ?
C10 C14 1.420(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.389(3) . ?
C13 C14 1.399(3) . ?
C14 C15 1.427(3) . ?
C15 C16 1.202(3) . ?
C16 C17 1.430(3) . ?
C17 C18 1.409(3) . ?
C17 C22 1.402(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.387(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.386(3) . ?
C21 C24 1.494(3) . ?
N2 C25 1.515(2) . ?
N2 C31 1.521(2) . ?
N2 C37 1.522(2) . ?
N2 C43 1.517(2) . ?
C25 C26 1.515(3) . ?
C26 C27 1.531(3) . ?
C27 C28 1.522(3) . ?
C28 C29 1.517(4) . ?
C29 C30 1.510(4) . ?
C31 C32 1.522(3) . ?
C32 C33 1.524(3) . ?
C33 C34 1.526(3) . ?
C34 C35 1.522(3) . ?
C35 C36 1.521(3) . ?
C37 C38 1.520(3) . ?
C38 C39 1.527(3) . ?
C39 C40 1.527(3) . ?
C40 C41 1.517(3) . ?
C41 C42 1.521(4) . ?
C43 C44 1.522(3) . ?
C44 C45 1.528(3) . ?
C45 C46 1.524(3) . ?
C46 C47 1.527(3) . ?
C47 C48 1.523(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.35(16) . . ?
C2 C1 C6 120.34(19) . . ?
C6 C1 I1 120.28(14) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 119.2(2) . . ?
C3 C4 C23 119.1(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 C23 119.9(2) . . ?
C4 C5 C6 120.3(2) . . ?
C1 C6 C7 121.84(18) . . ?
C5 C6 C1 118.58(19) . . ?
C5 C6 C7 119.57(19) . . ?
C8 C7 C6 177.8(2) . . ?
C7 C8 C9 175.7(2) . . ?
C10 C9 C8 118.40(17) . . ?
C11 C9 C8 121.68(17) . . ?
C11 C9 C10 119.92(17) . . ?
N1 C10 C9 120.65(18) . . ?
N1 C10 C14 121.00(17) . . ?
C9 C10 C14 118.35(17) . . ?
C12 C11 C9 121.55(18) . . ?
C11 C12 C13 118.84(18) . . ?
C12 C13 C14 121.49(18) . . ?
C10 C14 C15 118.76(17) . . ?
C13 C14 C10 119.81(17) . . ?
C13 C14 C15 121.42(18) . . ?
C16 C15 C14 176.1(2) . . ?
C15 C16 C17 178.0(2) . . ?
C18 C17 C16 121.53(18) . . ?
C22 C17 C16 120.09(18) . . ?
C22 C17 C18 118.38(18) . . ?
C17 C18 I2 120.74(14) . . ?
C19 C18 I2 119.01(15) . . ?
C19 C18 C17 120.23(18) . . ?
C20 C19 C18 120.95(19) . . ?
C19 C20 C21 118.90(18) . . ?
C20 C21 C24 120.68(18) . . ?
C22 C21 C20 121.10(19) . . ?
C22 C21 C24 118.22(18) . . ?
C21 C22 C17 120.43(19) . . ?
F1 C23 F2 113.1(3) . . ?
F1 C23 F3 102.9(3) . . ?
F1 C23 C4 113.6(2) . . ?
F2 C23 F3 100.9(3) . . ?
F2 C23 C4 114.4(2) . . ?
F3 C23 C4 110.4(2) . . ?
F4 C24 F5 105.73(18) . . ?
F4 C24 C21 112.31(17) . . ?
F5 C24 C21 112.35(17) . . ?
F6 C24 F4 106.55(17) . . ?
F6 C24 F5 106.42(17) . . ?
F6 C24 C21 112.96(18) . . ?
C25 N2 C31 110.78(15) . . ?
C25 N2 C37 106.58(14) . . ?
C25 N2 C43 110.63(14) . . ?
C31 N2 C37 110.98(14) . . ?
C43 N2 C31 107.02(14) . . ?
C43 N2 C37 110.91(15) . . ?
N2 C25 C26 115.54(15) . . ?
C25 C26 C27 109.02(17) . . ?
C28 C27 C26 113.60(18) . . ?
C29 C28 C27 113.46(19) . . ?
C30 C29 C28 113.1(2) . . ?
N2 C31 C32 115.64(15) . . ?
C31 C32 C33 110.47(16) . . ?
C32 C33 C34 113.11(16) . . ?
C35 C34 C33 111.97(16) . . ?
C36 C35 C34 113.01(17) . . ?
C38 C37 N2 116.12(15) . . ?
C37 C38 C39 110.10(16) . . ?
C38 C39 C40 113.00(17) . . ?
C41 C40 C39 113.57(18) . . ?
C40 C41 C42 113.2(2) . . ?
N2 C43 C44 116.32(15) . . ?
C43 C44 C45 108.57(16) . . ?
C46 C45 C44 113.45(17) . . ?
C45 C46 C47 111.82(17) . . ?
C48 C47 C46 113.15(19) . . ?

_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_umt_ob196
_database_code_depnum_ccdc_archive 'CCDC 2238839'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 F3 I2 N, C16 H36 N, Cl'
_chemical_formula_sum            'C41 H52 Cl F3 I2 N2'
_chemical_formula_weight         919.09
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   12.2702(5)
_cell_length_b                   13.0397(5)
_cell_length_c                   14.4541(6)
_cell_angle_alpha                107.965(2)
_cell_angle_beta                 108.3600(10)
_cell_angle_gamma                93.925(2)
_cell_volume                     2052.49(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.683
_cell_measurement_theta_min      2.655
_shelx_estimated_absorpt_T_max   0.840
_shelx_estimated_absorpt_T_min   0.350
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0735 before and 0.0444 after correction. The Ratio of minimum to maximum transmission is 0.7482. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prisim
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            119487
_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         27.483
_diffrn_reflns_theta_min         2.654
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8469
_reflns_number_total             9379
_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-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.38A (BRUKER-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.374
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         9379
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0232
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+3.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0590
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F3A-C24 \\sim F2-C24 \\sim F2AA-C24 \\sim F2A-C24 \\sim F3-C24 \\sim F0AA-C24
\\sim F1A-C24 \\sim F1-C24
 \\sim F1AA-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C29 \\sim C29A: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
4. Rigid body (RIGU) restrains
 F1, F2, F3, C24, F1A, F2A, F3A, F0AA, F1AA, F2AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 1*[Sof(F1A)+Sof(F2A)+Sof(F3A)]+1*[Sof(F1)+Sof(F2)+Sof(F3)]+1*[Sof(F0AA)+
 Sof(F1AA)+Sof(F2AA)]=1 with esd of 0.0001
 Sof(F1A)=Sof(F2A)=Sof(F3A)=FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
 Sof(F0AA)=Sof(F1AA)=Sof(F2AA)=FVAR(3)
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(4)
 Sof(H28A)=Sof(H28B)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C28(H28C,H28D), C30(H30A,
 H30B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C33(H33A,H33B,
 H33C), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C29A(H29D,H29E,H29F)
;
_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
I1 I 0.82898(2) 0.89546(2) 0.18204(2) 0.01887(4) Uani 1 1 d . . . . .
I2 I 0.76514(2) 1.35122(2) 0.26660(2) 0.01973(4) Uani 1 1 d . . . . .
F1 F 1.5605(11) 1.3139(11) 0.4849(10) 0.059(3) Uani 0.437(3) 1 d D U P A 1
F2 F 1.5244(19) 1.4403(8) 0.5944(13) 0.047(3) Uani 0.437(3) 1 d D U P A 1
F3 F 1.529(2) 1.2821(13) 0.6088(12) 0.064(5) Uani 0.437(3) 1 d D U P A 1
N1 N 1.00881(16) 1.19303(16) 0.30784(15) 0.0189(4) Uani 1 1 d . . . . .
H1A H 0.968(3) 1.238(3) 0.308(2) 0.030(8) Uiso 1 1 d . . . . .
H1B H 0.981(2) 1.131(2) 0.290(2) 0.018(6) Uiso 1 1 d . . . . .
C1 C 0.94447(19) 0.78372(17) 0.18972(16) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.9029(2) 0.67101(18) 0.14249(18) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.821567 0.644100 0.106431 0.027 Uiso 1 1 calc R . . . .
C3 C 0.9798(2) 0.59806(18) 0.14792(18) 0.0243(5) Uani 1 1 d . . . . .
H3 H 0.950394 0.521531 0.114588 0.029 Uiso 1 1 calc R . . . .
C4 C 1.0997(2) 0.63523(18) 0.20165(18) 0.0216(4) Uani 1 1 d . . . . .
C5 C 1.14035(19) 0.74774(17) 0.24995(16) 0.0181(4) Uani 1 1 d . . . . .
H5 H 1.221426 0.774172 0.288008 0.022 Uiso 1 1 calc R . . . .
C6 C 1.06405(18) 0.82334(16) 0.24374(15) 0.0162(4) Uani 1 1 d . . . . .
C7 C 1.11043(18) 0.93857(17) 0.29195(16) 0.0162(4) Uani 1 1 d . . . . .
C8 C 1.15173(17) 1.03498(17) 0.33121(16) 0.0157(4) Uani 1 1 d . . . . .
C9 C 1.19901(18) 1.14996(16) 0.37651(16) 0.0155(4) Uani 1 1 d . . . . .
C10 C 1.12400(18) 1.22665(16) 0.36235(15) 0.0155(4) Uani 1 1 d . . . . .
C11 C 1.31755(18) 1.18655(17) 0.43573(17) 0.0194(4) Uani 1 1 d . . . . .
H11 H 1.366530 1.134778 0.446482 0.023 Uiso 1 1 calc R . . . .
C12 C 1.36483(18) 1.29784(18) 0.47920(18) 0.0216(4) Uani 1 1 d . . . . .
C13 C 1.29344(18) 1.37396(17) 0.46410(17) 0.0206(4) Uani 1 1 d . . . . .
H13 H 1.326285 1.449942 0.493113 0.025 Uiso 1 1 calc R . . . .
C14 C 1.17449(18) 1.34015(16) 0.40699(16) 0.0168(4) Uani 1 1 d . . . . .
C15 C 1.10000(19) 1.41881(17) 0.39546(16) 0.0182(4) Uani 1 1 d . . . . .
C16 C 1.03383(18) 1.48129(17) 0.38589(16) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.95481(18) 1.55645(17) 0.37569(16) 0.0166(4) Uani 1 1 d . . . . .
C18 C 0.83402(18) 1.51951(17) 0.32349(16) 0.0181(4) Uani 1 1 d . . . . .
C19 C 0.76041(19) 1.59457(18) 0.31323(17) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.678882 1.569368 0.276783 0.025 Uiso 1 1 calc R . . . .
C20 C 0.8052(2) 1.70662(18) 0.35599(17) 0.0210(4) Uani 1 1 d . . . . .
H20 H 0.754024 1.757219 0.347506 0.025 Uiso 1 1 calc R . . . .
C21 C 0.92431(19) 1.74536(17) 0.41114(16) 0.0186(4) Uani 1 1 d . . . . .
C22 C 0.99795(19) 1.66984(17) 0.41967(16) 0.0183(4) Uani 1 1 d . . . . .
H22 H 1.079422 1.695483 0.456101 0.022 Uiso 1 1 calc R . . . .
C23 C 1.1830(2) 0.55604(19) 0.2087(2) 0.0305(5) Uani 1 1 d . . . . .
H23A H 1.263547 0.596627 0.239598 0.046 Uiso 1 1 calc GR . . . .
H23B H 1.169907 0.504541 0.138847 0.046 Uiso 1 1 calc GR . . . .
H23C H 1.169850 0.515373 0.252173 0.046 Uiso 1 1 calc GR . . . .
C24 C 1.4918(2) 1.33427(19) 0.5431(2) 0.0342(6) Uani 1 1 d D U . . .
C25 C 0.9724(2) 1.86646(17) 0.46130(17) 0.0209(4) Uani 1 1 d . . . . .
H25A H 1.057672 1.878251 0.493018 0.031 Uiso 1 1 calc GR . . . .
H25B H 0.939632 1.898734 0.515025 0.031 Uiso 1 1 calc GR . . . .
H25C H 0.951296 1.901273 0.408519 0.031 Uiso 1 1 calc GR . . . .
F1A F 1.5594(15) 1.2630(16) 0.531(3) 0.060(6) Uani 0.112(3) 1 d D U P A 2
F2A F 1.5037(15) 1.348(3) 0.6451(12) 0.055(5) Uani 0.112(3) 1 d D U P A 2
F3A F 1.538(4) 1.4334(15) 0.555(3) 0.052(8) Uani 0.112(3) 1 d D U P A 2
F0AA F 1.5373(19) 1.2628(13) 0.5857(12) 0.043(2) Uani 0.451(3) 1 d D U P A 3
F1AA F 1.5544(11) 1.3464(10) 0.4836(11) 0.061(3) Uani 0.451(3) 1 d D U P A 3
F2AA F 1.513(2) 1.4291(8) 0.6201(13) 0.067(5) Uani 0.451(3) 1 d D U P A 3
Cl1 Cl 0.69456(4) 1.09342(4) 0.18542(4) 0.01877(10) Uani 1 1 d . . . . .
N2 N 0.66507(15) 1.07167(14) -0.11481(13) 0.0158(3) Uani 1 1 d . . . . .
C26 C 0.61998(17) 0.97419(17) -0.09139(16) 0.0170(4) Uani 1 1 d . . . . .
H26A H 0.656356 0.989094 -0.015818 0.020 Uiso 1 1 calc R . . . .
H26B H 0.534712 0.969170 -0.107760 0.020 Uiso 1 1 calc R . . . .
C27 C 0.6421(2) 0.8637(2) -0.1491(2) 0.0360(6) Uani 1 1 d . . . . .
H27A H 0.727164 0.865480 -0.130800 0.043 Uiso 1 1 calc R . . . .
H27B H 0.606984 0.847274 -0.225008 0.043 Uiso 1 1 calc R . . . .
C28 C 0.5887(2) 0.7751(2) -0.1200(2) 0.0333(6) Uani 1 1 d . . . . .
H28A H 0.506428 0.780731 -0.127959 0.040 Uiso 0.68(3) 1 calc R . P B 1
H28B H 0.632150 0.784738 -0.046526 0.040 Uiso 0.68(3) 1 calc R . P B 1
H28C H 0.608571 0.804884 -0.043711 0.040 Uiso 0.32(3) 1 calc R . P B 2
H28D H 0.502892 0.766920 -0.151546 0.040 Uiso 0.32(3) 1 calc R . P B 2
C29 C 0.5946(7) 0.6592(6) -0.1931(13) 0.048(2) Uani 0.68(3) 1 d . U P B 1
H29A H 0.545508 0.647392 -0.265011 0.071 Uiso 0.68(3) 1 calc GR . P B 1
H29B H 0.566311 0.602046 -0.170952 0.071 Uiso 0.68(3) 1 calc GR . P B 1
H29C H 0.675513 0.656127 -0.188844 0.071 Uiso 0.68(3) 1 calc GR . P B 1
C30 C 0.79663(17) 1.08968(17) -0.08439(16) 0.0177(4) Uani 1 1 d . . . . .
H30A H 0.821712 1.155045 -0.098894 0.021 Uiso 1 1 calc R . . . .
H30B H 0.817142 1.025915 -0.129692 0.021 Uiso 1 1 calc R . . . .
C31 C 0.86614(17) 1.10555(17) 0.02796(16) 0.0173(4) Uani 1 1 d . . . . .
H31A H 0.855355 1.035594 0.040290 0.021 Uiso 1 1 calc R . . . .
H31B H 0.837877 1.160801 0.074866 0.021 Uiso 1 1 calc R . . . .
C32 C 0.99612(18) 1.14407(18) 0.05115(17) 0.0199(4) Uani 1 1 d . . . . .
H32A H 1.043329 1.127067 0.112224 0.024 Uiso 1 1 calc R . . . .
H32B H 1.016895 1.102677 -0.008953 0.024 Uiso 1 1 calc R . . . .
C33 C 1.0272(2) 1.2665(2) 0.0728(2) 0.0295(5) Uani 1 1 d . . . . .
H33A H 0.980710 1.283990 0.012672 0.044 Uiso 1 1 calc GR . . . .
H33B H 1.110432 1.285997 0.085307 0.044 Uiso 1 1 calc GR . . . .
H33C H 1.010388 1.308117 0.134278 0.044 Uiso 1 1 calc GR . . . .
C34 C 0.62660(18) 1.17045(17) -0.05333(16) 0.0176(4) Uani 1 1 d . . . . .
H34A H 0.651446 1.174639 0.020080 0.021 Uiso 1 1 calc R . . . .
H34B H 0.540211 1.158927 -0.080693 0.021 Uiso 1 1 calc R . . . .
C35 C 0.6747(2) 1.27988(19) -0.0565(2) 0.0269(5) Uani 1 1 d . . . . .
H35A H 0.671662 1.270291 -0.127959 0.032 Uiso 1 1 calc R . . . .
H35B H 0.757388 1.304015 -0.009615 0.032 Uiso 1 1 calc R . . . .
C36 C 0.6048(2) 1.3682(2) -0.0232(2) 0.0306(5) Uani 1 1 d . . . . .
H36A H 0.594553 1.367009 0.041732 0.037 Uiso 1 1 calc R . . . .
H36B H 0.650088 1.441026 -0.007941 0.037 Uiso 1 1 calc R . . . .
C37 C 0.4858(3) 1.3536(2) -0.1045(2) 0.0435(7) Uani 1 1 d . . . . .
H37A H 0.494973 1.352614 -0.169683 0.065 Uiso 1 1 calc GR . . . .
H37B H 0.447377 1.414564 -0.080239 0.065 Uiso 1 1 calc GR . . . .
H37C H 0.438151 1.284281 -0.116091 0.065 Uiso 1 1 calc GR . . . .
C38 C 0.61526(19) 1.05244(19) -0.23034(16) 0.0208(4) Uani 1 1 d . . . . .
H38A H 0.636544 0.984173 -0.268075 0.025 Uiso 1 1 calc R . . . .
H38B H 0.653099 1.113497 -0.243254 0.025 Uiso 1 1 calc R . . . .
C39 C 0.48369(19) 1.0431(2) -0.27605(17) 0.0238(5) Uani 1 1 d . . . . .
H39A H 0.445631 1.002734 -0.243241 0.029 Uiso 1 1 calc R . . . .
H39B H 0.464084 1.117474 -0.260182 0.029 Uiso 1 1 calc R . . . .
C40 C 0.4373(2) 0.9848(3) -0.39159(19) 0.0382(7) Uani 1 1 d . . . . .
H40A H 0.461207 0.912224 -0.407403 0.046 Uiso 1 1 calc R . . . .
H40B H 0.472298 1.027489 -0.424464 0.046 Uiso 1 1 calc R . . . .
C41 C 0.3055(2) 0.9688(3) -0.4381(2) 0.0369(6) Uani 1 1 d . . . . .
H41A H 0.279006 0.924565 -0.512272 0.055 Uiso 1 1 calc GR . . . .
H41B H 0.281798 1.040379 -0.429724 0.055 Uiso 1 1 calc GR . . . .
H41C H 0.270351 0.931040 -0.402491 0.055 Uiso 1 1 calc GR . . . .
C29A C 0.615(2) 0.6645(13) -0.145(2) 0.039(4) Uani 0.32(3) 1 d . U P B 2
H29D H 0.604429 0.634429 -0.218881 0.059 Uiso 0.32(3) 1 calc GR . P B 2
H29E H 0.562671 0.617612 -0.129387 0.059 Uiso 0.32(3) 1 calc GR . P B 2
H29F H 0.696316 0.667135 -0.103039 0.059 Uiso 0.32(3) 1 calc GR . P B 2


_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 2.104(2) . ?
I2 C18 2.098(2) . ?
F1 C24 1.351(9) . ?
F2 C24 1.314(10) . ?
F3 C24 1.319(10) . ?
N1 C10 1.346(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.392(3) . ?
C4 C23 1.505(3) . ?
C5 C6 1.409(3) . ?
C6 C7 1.433(3) . ?
C7 C8 1.204(3) . ?
C8 C9 1.431(3) . ?
C9 C10 1.422(3) . ?
C9 C11 1.395(3) . ?
C10 C14 1.423(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.390(3) . ?
C12 C24 1.493(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.433(3) . ?
C15 C16 1.197(3) . ?
C16 C17 1.432(3) . ?
C17 C18 1.404(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.386(3) . ?
C19 C20 1.392(3) . ?
C20 C21 1.394(3) . ?
C21 C22 1.388(3) . ?
C21 C25 1.505(3) . ?
C24 F1A 1.296(12) . ?
C24 F2A 1.388(13) . ?
C24 F3A 1.313(14) . ?
C24 F0AA 1.330(10) . ?
C24 F1AA 1.356(9) . ?
C24 F2AA 1.328(9) . ?
N2 C26 1.524(3) . ?
N2 C30 1.514(2) . ?
N2 C34 1.521(3) . ?
N2 C38 1.517(3) . ?
C26 C27 1.516(3) . ?
C27 C28 1.520(4) . ?
C28 C29 1.576(9) . ?
C28 C29A 1.461(16) . ?
C30 C31 1.518(3) . ?
C31 C32 1.536(3) . ?
C32 C33 1.525(3) . ?
C34 C35 1.526(3) . ?
C35 C36 1.532(3) . ?
C36 C37 1.513(4) . ?
C38 C39 1.520(3) . ?
C39 C40 1.500(3) . ?
C40 C41 1.514(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 120.76(16) . . ?
C2 C1 C6 119.9(2) . . ?
C6 C1 I1 119.37(15) . . ?
C3 C2 C1 120.3(2) . . ?
C2 C3 C4 121.1(2) . . ?
C3 C4 C23 121.1(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C23 120.6(2) . . ?
C4 C5 C6 121.6(2) . . ?
C1 C6 C5 118.89(19) . . ?
C1 C6 C7 121.58(19) . . ?
C5 C6 C7 119.53(19) . . ?
C8 C7 C6 178.2(2) . . ?
C7 C8 C9 178.9(2) . . ?
C10 C9 C8 119.62(18) . . ?
C11 C9 C8 120.16(19) . . ?
C11 C9 C10 120.22(18) . . ?
N1 C10 C9 121.10(19) . . ?
N1 C10 C14 120.89(19) . . ?
C9 C10 C14 118.01(18) . . ?
C12 C11 C9 120.8(2) . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 C24 119.4(2) . . ?
C13 C12 C24 120.8(2) . . ?
C12 C13 C14 120.76(19) . . ?
C10 C14 C15 118.85(19) . . ?
C13 C14 C10 120.37(19) . . ?
C13 C14 C15 120.74(19) . . ?
C16 C15 C14 177.0(2) . . ?
C15 C16 C17 179.3(2) . . ?
C18 C17 C16 121.49(19) . . ?
C22 C17 C16 119.77(19) . . ?
C22 C17 C18 118.73(19) . . ?
C17 C18 I2 119.75(15) . . ?
C19 C18 I2 120.30(16) . . ?
C19 C18 C17 119.91(19) . . ?
C18 C19 C20 120.4(2) . . ?
C19 C20 C21 120.7(2) . . ?
C20 C21 C25 120.88(19) . . ?
C22 C21 C20 118.65(19) . . ?
C22 C21 C25 120.5(2) . . ?
C21 C22 C17 121.5(2) . . ?
F1 C24 C12 112.7(7) . . ?
F2 C24 F1 103.0(8) . . ?
F2 C24 F3 108.6(12) . . ?
F2 C24 C12 114.7(10) . . ?
F3 C24 F1 103.6(10) . . ?
F3 C24 C12 113.2(11) . . ?
F1A C24 C12 117.7(9) . . ?
F1A C24 F2A 98.0(19) . . ?
F1A C24 F3A 114(2) . . ?
F2A C24 C12 107.3(7) . . ?
F3A C24 C12 116(2) . . ?
F3A C24 F2A 100.2(19) . . ?
F0AA C24 C12 113.4(10) . . ?
F0AA C24 F1AA 105.5(9) . . ?
F1AA C24 C12 110.7(7) . . ?
F2AA C24 C12 111.9(10) . . ?
F2AA C24 F0AA 106.9(12) . . ?
F2AA C24 F1AA 108.0(9) . . ?
C30 N2 C26 111.37(15) . . ?
C30 N2 C34 111.10(16) . . ?
C30 N2 C38 106.53(15) . . ?
C34 N2 C26 106.25(15) . . ?
C38 N2 C26 110.91(16) . . ?
C38 N2 C34 110.75(16) . . ?
C27 C26 N2 116.11(18) . . ?
C26 C27 C28 109.7(2) . . ?
C27 C28 C29 109.1(6) . . ?
C29A C28 C27 122.9(7) . . ?
N2 C30 C31 116.18(16) . . ?
C30 C31 C32 109.50(17) . . ?
C33 C32 C31 113.04(18) . . ?
N2 C34 C35 114.67(17) . . ?
C34 C35 C36 111.5(2) . . ?
C37 C36 C35 113.4(2) . . ?
N2 C38 C39 115.63(17) . . ?
C40 C39 C38 111.65(19) . . ?
C39 C40 C41 112.6(2) . . ?

_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_umt_ob129
_database_code_depnum_ccdc_archive 'CCDC 2238837'
loop_
_audit_author_name
_audit_author_address
'Dan Decato'
;University of Montana
United States of America
;
_audit_update_record             
;
2023-01-30 deposited with the CCDC.	2023-07-20 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H10 F9 I2 N, Cl, C16 H36 N'
_chemical_formula_sum            'C41 H46 Cl F9 I2 N2'
_chemical_formula_weight         1027.05
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.0763(5)
_cell_length_b                   15.6429(11)
_cell_length_c                   17.8668(12)
_cell_angle_alpha                73.593(2)
_cell_angle_beta                 87.048(2)
_cell_angle_gamma                88.270(2)
_cell_volume                     2162.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    105
_cell_measurement_theta_max      30.460
_cell_measurement_theta_min      3.066
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.584
_exptl_absorpt_coefficient_mu    1.586
_exptl_absorpt_correction_T_max  0.6044
_exptl_absorpt_correction_T_min  0.4016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1091 before and 0.0787 after correction. The Ratio of minimum to maximum transmission is 0.6645. 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    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            134813
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.018
_diffrn_ambient_temperature      105
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8293
_reflns_number_total             9902
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.366
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         9902
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.146
_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)+(0.0403P)²+15.1372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
# start Validation Reply Form
_vrf_PLAT910_umt_ob129           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         14 Note  
RESPONSE: The reflections were observed, however their proximity to
the beamstop inhibited accurate intensity measurement and these reflections
have been excluded from the data used for refinement. The reflections 010, 
001,and 011 are the exceptions and were not observed, hidden by the beamstop.
;
# end Validation Reply Form
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C11(H11), C13(H13), C19(H19), C20(H20), C22(H22)
3.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C37(H37A,H37B,H37C), C41(H41A,H41B,
 H41C)
;
_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
I1 I 0.47423(4) 0.71622(2) 0.06585(2) 0.02537(10) Uani 1 1 d . . . . .
I2 I 0.45686(4) 0.47739(2) 0.37631(2) 0.02476(9) Uani 1 1 d . . . . .
Cl1 Cl 0.50100(15) 0.67790(8) 0.25748(7) 0.0238(2) Uani 1 1 d . . . . .
F1 F 0.1647(5) 0.8447(3) -0.3016(2) 0.0631(13) Uani 1 1 d . . . . .
F2 F 0.4176(4) 0.8528(2) -0.34301(18) 0.0367(8) Uani 1 1 d . . . . .
F3 F 0.2930(5) 0.7284(3) -0.3184(2) 0.0494(10) Uani 1 1 d . . . . .
F4 F -0.0539(4) 0.1595(2) 0.11571(18) 0.0331(7) Uani 1 1 d . . . . .
F5 F 0.1624(4) 0.1610(2) 0.0416(2) 0.0355(8) Uani 1 1 d . . . . .
F6 F -0.0457(4) 0.2450(2) -0.00212(18) 0.0319(7) Uani 1 1 d . . . . .
F7 F 0.2174(6) 0.0440(3) 0.5786(3) 0.0666(14) Uani 1 1 d . . . . .
F8 F 0.4803(6) 0.0278(2) 0.5721(2) 0.0580(12) Uani 1 1 d . . . . .
F9 F 0.3633(5) 0.0667(2) 0.66672(18) 0.0418(9) Uani 1 1 d . . . . .
N1 N 0.3524(7) 0.4761(3) 0.1650(3) 0.0370(12) Uani 1 1 d D . . . .
H1A H 0.375(7) 0.527(2) 0.132(3) 0.023(15) Uiso 1 1 d D . . . .
H1B H 0.389(11) 0.464(6) 0.211(2) 0.08(3) Uiso 1 1 d D . . . .
C1 C 0.4335(6) 0.7405(3) -0.0535(3) 0.0225(10) Uani 1 1 d . . . . .
C2 C 0.4704(6) 0.8231(4) -0.1048(3) 0.0269(11) Uani 1 1 d . . . . .
H2 H 0.520860 0.866843 -0.086234 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4344(6) 0.8422(3) -0.1827(3) 0.0271(11) Uani 1 1 d . . . . .
H3 H 0.459489 0.899034 -0.217452 0.033 Uiso 1 1 calc R . . . .
C4 C 0.3614(6) 0.7781(4) -0.2100(3) 0.0257(11) Uani 1 1 d . . . . .
C5 C 0.3264(6) 0.6948(4) -0.1603(3) 0.0258(11) Uani 1 1 d . . . . .
H5 H 0.278876 0.651005 -0.179804 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3614(6) 0.6749(3) -0.0805(3) 0.0222(10) Uani 1 1 d . . . . .
C7 C 0.3175(6) 0.5893(4) -0.0301(3) 0.0232(10) Uani 1 1 d . . . . .
C8 C 0.2750(6) 0.5169(4) 0.0085(3) 0.0245(10) Uani 1 1 d . . . . .
C9 C 0.2325(6) 0.4323(3) 0.0611(3) 0.0210(9) Uani 1 1 d . . . . .
C10 C 0.2733(6) 0.4151(3) 0.1403(3) 0.0232(10) Uani 1 1 d . . . . .
C11 C 0.1542(6) 0.3680(3) 0.0362(3) 0.0197(9) Uani 1 1 d . . . . .
H11 H 0.127873 0.379938 -0.017072 0.024 Uiso 1 1 calc R . . . .
C12 C 0.1140(6) 0.2862(3) 0.0885(3) 0.0185(9) Uani 1 1 d . . . . .
C13 C 0.1499(6) 0.2693(3) 0.1667(3) 0.0198(9) Uani 1 1 d . . . . .
H13 H 0.120450 0.213837 0.202473 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2280(6) 0.3321(3) 0.1932(3) 0.0217(10) Uani 1 1 d . . . . .
C15 C 0.2661(7) 0.3145(3) 0.2732(3) 0.0243(10) Uani 1 1 d . . . . .
C16 C 0.3047(7) 0.3039(3) 0.3393(3) 0.0238(10) Uani 1 1 d . . . . .
C17 C 0.3514(6) 0.2836(3) 0.4181(3) 0.0219(10) Uani 1 1 d . . . . .
C18 C 0.4200(6) 0.3476(3) 0.4486(3) 0.0213(9) Uani 1 1 d . . . . .
C19 C 0.4636(6) 0.3236(4) 0.5262(3) 0.0260(11) Uani 1 1 d . . . . .
H19 H 0.508050 0.367076 0.547102 0.031 Uiso 1 1 calc R . . . .
C20 C 0.4431(6) 0.2374(4) 0.5735(3) 0.0255(10) Uani 1 1 d . . . . .
H20 H 0.474158 0.221676 0.626255 0.031 Uiso 1 1 calc R . . . .
C21 C 0.3767(6) 0.1740(3) 0.5430(3) 0.0232(10) Uani 1 1 d . . . . .
C22 C 0.3308(7) 0.1972(3) 0.4661(3) 0.0249(10) Uani 1 1 d . . . . .
H22 H 0.284720 0.153527 0.445874 0.030 Uiso 1 1 calc R . . . .
C23 C 0.3093(7) 0.8001(4) -0.2926(3) 0.0328(12) Uani 1 1 d . . . . .
C24 C 0.0432(6) 0.2144(3) 0.0612(3) 0.0219(10) Uani 1 1 d . . . . .
C25 C 0.3583(8) 0.0786(4) 0.5896(3) 0.0306(12) Uani 1 1 d . . . . .
N2 N 0.9983(5) 0.7835(3) 0.2440(3) 0.0310(10) Uani 1 1 d . . . . .
C26 C 0.8473(7) 0.8346(4) 0.2050(4) 0.0370(14) Uani 1 1 d . . . . .
H26A H 0.766500 0.790638 0.199588 0.044 Uiso 1 1 calc R . . . .
H26B H 0.794849 0.866730 0.240791 0.044 Uiso 1 1 calc R . . . .
C27 C 0.8753(8) 0.9012(5) 0.1260(4) 0.0412(14) Uani 1 1 d . . . . .
H27A H 0.927131 0.870413 0.089089 0.049 Uiso 1 1 calc R . . . .
H27B H 0.952617 0.947228 0.130447 0.049 Uiso 1 1 calc R . . . .
C28 C 0.7139(8) 0.9458(4) 0.0939(5) 0.0475(17) Uani 1 1 d . . . . .
H28A H 0.639577 0.899919 0.086562 0.057 Uiso 1 1 calc R . . . .
H28B H 0.658576 0.972781 0.132728 0.057 Uiso 1 1 calc R . . . .
C29 C 0.7379(9) 1.0170(5) 0.0174(5) 0.0492(17) Uani 1 1 d . . . . .
H29A H 0.804495 1.064907 0.025087 0.074 Uiso 1 1 calc GR . . . .
H29B H 0.629598 1.041086 -0.001520 0.074 Uiso 1 1 calc GR . . . .
H29C H 0.795173 0.991163 -0.020962 0.074 Uiso 1 1 calc GR . . . .
C30 C 1.1390(7) 0.8456(4) 0.2433(3) 0.0291(11) Uani 1 1 d . . . . .
H30A H 1.169338 0.877979 0.188417 0.035 Uiso 1 1 calc R . . . .
H30B H 1.236788 0.809397 0.265508 0.035 Uiso 1 1 calc R . . . .
C31 C 1.1001(8) 0.9137(4) 0.2887(4) 0.0347(13) Uani 1 1 d . . . . .
H31A H 0.990955 0.942343 0.274062 0.042 Uiso 1 1 calc R . . . .
H31B H 1.093352 0.882804 0.345330 0.042 Uiso 1 1 calc R . . . .
C32 C 1.2314(7) 0.9847(4) 0.2723(4) 0.0334(12) Uani 1 1 d . . . . .
H32A H 1.228090 1.020901 0.217074 0.040 Uiso 1 1 calc R . . . .
H32B H 1.342302 0.955799 0.280330 0.040 Uiso 1 1 calc R . . . .
C33 C 1.2044(8) 1.0451(4) 0.3252(4) 0.0399(14) Uani 1 1 d . . . . .
H33A H 1.290532 1.090404 0.313070 0.060 Uiso 1 1 calc GR . . . .
H33B H 1.210028 1.009591 0.379815 0.060 Uiso 1 1 calc GR . . . .
H33C H 1.095146 1.074364 0.316813 0.060 Uiso 1 1 calc GR . . . .
C34 C 0.9430(7) 0.7348(4) 0.3267(4) 0.0374(14) Uani 1 1 d . . . . .
H34A H 0.852827 0.694181 0.324501 0.045 Uiso 1 1 calc R . . . .
H34B H 0.895202 0.779185 0.352072 0.045 Uiso 1 1 calc R . . . .
C35 C 1.0737(8) 0.6808(5) 0.3784(3) 0.0406(15) Uani 1 1 d . . . . .
H35A H 1.165771 0.719518 0.382229 0.049 Uiso 1 1 calc R . . . .
H35B H 1.119073 0.633024 0.356534 0.049 Uiso 1 1 calc R . . . .
C36 C 0.9910(12) 0.6409(6) 0.4582(4) 0.063(2) Uani 1 1 d . . . . .
H36A H 0.929178 0.688798 0.474521 0.076 Uiso 1 1 calc R . . . .
H36B H 0.909343 0.596748 0.453986 0.076 Uiso 1 1 calc R . . . .
C37 C 1.1010(11) 0.5989(8) 0.5170(5) 0.076(3) Uani 1 1 d . . . . .
H37A H 1.177552 0.559363 0.497569 0.114 Uiso 1 1 calc GR . . . .
H37B H 1.037670 0.563884 0.563179 0.114 Uiso 1 1 calc GR . . . .
H37C H 1.164182 0.644175 0.531003 0.114 Uiso 1 1 calc GR . . . .
C38 C 1.0670(7) 0.7189(4) 0.1990(4) 0.0325(12) Uani 1 1 d . . . . .
H38A H 1.103746 0.754889 0.146055 0.039 Uiso 1 1 calc R . . . .
H38B H 1.166953 0.689229 0.225157 0.039 Uiso 1 1 calc R . . . .
C39 C 0.9548(9) 0.6468(5) 0.1897(4) 0.0456(16) Uani 1 1 d . . . . .
H39A H 0.839826 0.670943 0.186226 0.055 Uiso 1 1 calc R . . . .
H39B H 0.985982 0.635200 0.139113 0.055 Uiso 1 1 calc R . . . .
C40 C 0.9541(11) 0.5620(6) 0.2495(5) 0.059(2) Uani 1 1 d . . . . .
H40A H 0.891364 0.568066 0.296895 0.071 Uiso 1 1 calc R . . . .
H40B H 1.069209 0.543256 0.263715 0.071 Uiso 1 1 calc R . . . .
C41 C 0.8713(10) 0.4898(5) 0.2180(7) 0.069(3) Uani 1 1 d . . . . .
H41A H 0.756117 0.507560 0.205993 0.103 Uiso 1 1 calc GR . . . .
H41B H 0.873738 0.432089 0.257913 0.103 Uiso 1 1 calc GR . . . .
H41C H 0.932638 0.484894 0.170610 0.103 Uiso 1 1 calc GR . . . .


_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 2.100(5) . ?
I2 C18 2.096(5) . ?
F1 C23 1.335(7) . ?
F2 C23 1.341(6) . ?
F3 C23 1.339(7) . ?
F4 C24 1.338(6) . ?
F5 C24 1.352(6) . ?
F6 C24 1.335(6) . ?
F7 C25 1.323(7) . ?
F8 C25 1.328(7) . ?
F9 C25 1.339(6) . ?
N1 C10 1.349(7) . ?
C1 C2 1.387(7) . ?
C1 C6 1.403(7) . ?
C2 C3 1.383(8) . ?
C3 C4 1.390(8) . ?
C4 C5 1.382(7) . ?
C4 C23 1.497(7) . ?
C5 C6 1.413(7) . ?
C6 C7 1.430(7) . ?
C7 C8 1.197(7) . ?
C8 C9 1.429(7) . ?
C9 C10 1.418(6) . ?
C9 C11 1.390(7) . ?
C10 C14 1.418(7) . ?
C11 C12 1.391(7) . ?
C12 C13 1.390(6) . ?
C12 C24 1.484(7) . ?
C13 C14 1.385(7) . ?
C14 C15 1.425(7) . ?
C15 C16 1.203(7) . ?
C16 C17 1.421(7) . ?
C17 C18 1.407(7) . ?
C17 C22 1.390(7) . ?
C18 C19 1.392(7) . ?
C19 C20 1.383(8) . ?
C20 C21 1.391(7) . ?
C21 C22 1.386(7) . ?
C21 C25 1.497(7) . ?
N2 C26 1.526(7) . ?
N2 C30 1.515(7) . ?
N2 C34 1.510(8) . ?
N2 C38 1.534(7) . ?
C26 C27 1.510(10) . ?
C27 C28 1.520(9) . ?
C28 C29 1.506(11) . ?
C30 C31 1.528(7) . ?
C31 C32 1.516(8) . ?
C32 C33 1.518(8) . ?
C34 C35 1.511(10) . ?
C35 C36 1.515(9) . ?
C36 C37 1.413(13) . ?
C38 C39 1.518(8) . ?
C39 C40 1.449(11) . ?
C40 C41 1.576(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 119.7(4) . . ?
C2 C1 C6 120.3(5) . . ?
C6 C1 I1 120.0(4) . . ?
C3 C2 C1 120.5(5) . . ?
C2 C3 C4 119.9(5) . . ?
C3 C4 C23 120.5(5) . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 C23 118.7(5) . . ?
C4 C5 C6 119.9(5) . . ?
C1 C6 C5 118.8(5) . . ?
C1 C6 C7 122.7(4) . . ?
C5 C6 C7 118.4(5) . . ?
C8 C7 C6 175.9(5) . . ?
C7 C8 C9 174.1(5) . . ?
C10 C9 C8 118.1(4) . . ?
C11 C9 C8 121.7(4) . . ?
C11 C9 C10 120.3(4) . . ?
N1 C10 C9 121.0(5) . . ?
N1 C10 C14 120.6(4) . . ?
C14 C10 C9 118.4(4) . . ?
C9 C11 C12 120.5(4) . . ?
C11 C12 C24 120.8(4) . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 C24 119.4(4) . . ?
C14 C13 C12 121.1(4) . . ?
C10 C14 C15 118.9(4) . . ?
C13 C14 C10 120.0(4) . . ?
C13 C14 C15 121.0(4) . . ?
C16 C15 C14 176.0(6) . . ?
C15 C16 C17 175.1(5) . . ?
C18 C17 C16 122.1(5) . . ?
C22 C17 C16 118.7(5) . . ?
C22 C17 C18 119.2(4) . . ?
C17 C18 I2 119.6(3) . . ?
C19 C18 I2 121.0(4) . . ?
C19 C18 C17 119.4(5) . . ?
C20 C19 C18 121.0(5) . . ?
C19 C20 C21 119.4(5) . . ?
C20 C21 C25 122.3(5) . . ?
C22 C21 C20 120.3(5) . . ?
C22 C21 C25 117.4(5) . . ?
C21 C22 C17 120.7(5) . . ?
F1 C23 F2 105.5(5) . . ?
F1 C23 F3 107.2(5) . . ?
F1 C23 C4 111.5(5) . . ?
F2 C23 C4 112.4(5) . . ?
F3 C23 F2 106.0(4) . . ?
F3 C23 C4 113.7(5) . . ?
F4 C24 F5 104.9(4) . . ?
F4 C24 C12 113.1(4) . . ?
F5 C24 C12 112.0(4) . . ?
F6 C24 F4 107.1(4) . . ?
F6 C24 F5 105.6(4) . . ?
F6 C24 C12 113.4(4) . . ?
F7 C25 F8 107.1(5) . . ?
F7 C25 F9 106.1(5) . . ?
F7 C25 C21 113.1(5) . . ?
F8 C25 F9 105.4(5) . . ?
F8 C25 C21 111.5(4) . . ?
F9 C25 C21 113.1(5) . . ?
C26 N2 C38 110.7(4) . . ?
C30 N2 C26 111.4(4) . . ?
C30 N2 C38 105.6(4) . . ?
C34 N2 C26 106.9(4) . . ?
C34 N2 C30 110.8(4) . . ?
C34 N2 C38 111.6(5) . . ?
C27 C26 N2 117.5(5) . . ?
C26 C27 C28 111.6(6) . . ?
C29 C28 C27 113.2(6) . . ?
N2 C30 C31 114.6(4) . . ?
C32 C31 C30 111.6(5) . . ?
C31 C32 C33 111.3(5) . . ?
N2 C34 C35 116.8(5) . . ?
C34 C35 C36 107.2(6) . . ?
C37 C36 C35 114.6(8) . . ?
C39 C38 N2 118.6(5) . . ?
C40 C39 C38 118.0(6) . . ?
C39 C40 C41 109.4(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
