# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_PZA_TFIB
_database_code_depnum_ccdc_archive 'CCDC 1550372'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H5 N3 O), C6 F4 I2'
_chemical_formula_sum            'C16 H10 F4 I2 N6 O2'
_chemical_formula_weight         648.10
_chemical_melting_point          440.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.6157(3)
_cell_length_b                   5.8013(3)
_cell_length_c                   15.5403(8)
_cell_angle_alpha                85.616(2)
_cell_angle_beta                 89.138(2)
_cell_angle_gamma                80.700(2)
_cell_volume                     498.16(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4865
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.535
_cell_measurement_theta_min      3.569
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.699
_exptl_absorpt_coefficient_mu    3.220
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0986 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.6923.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8448
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_min         2.629
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2009
_reflns_number_total             2295
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.109
_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)+(0.0156P)²+0.3377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2896(5) 0.3589(5) 0.0725(2) 0.0667(8) Uani 1 1 d . . . . .
N1 N 1.2777(6) 0.7434(7) 0.0329(2) 0.0658(10) Uani 1 1 d . . . . .
H1A H 1.4049 0.7181 0.0013 0.079 Uiso 1 1 calc R . . . .
H1B H 1.2043 0.8842 0.0370 0.079 Uiso 1 1 calc R . . . .
N2 N 0.8705(6) 0.8529(5) 0.1247(2) 0.0529(7) Uani 1 1 d . . . . .
N3 N 0.6886(5) 0.5110(5) 0.22987(19) 0.0481(7) Uani 1 1 d . . . . .
C1 C 1.1952(6) 0.5665(7) 0.0749(2) 0.0481(8) Uani 1 1 d . . . . .
C2 C 0.9737(6) 0.6284(6) 0.1289(2) 0.0403(7) Uani 1 1 d . . . . .
C3 C 0.6733(7) 0.9021(7) 0.1727(3) 0.0571(9) Uani 1 1 d . . . . .
H3 H 0.5930 1.0557 0.1712 0.069 Uiso 1 1 calc R . . . .
C4 C 0.5848(7) 0.7320(7) 0.2245(2) 0.0516(9) Uani 1 1 d . . . . .
H4 H 0.4465 0.7747 0.2570 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8829(6) 0.4605(6) 0.1809(2) 0.0453(8) Uani 1 1 d . . . . .
H5 H 0.9604 0.3060 0.1817 0.054 Uiso 1 1 calc R . . . .
I1 I 0.38069(4) 0.27845(4) 0.36228(2) 0.04695(10) Uani 1 1 d . . . . .
F1 F 0.2397(4) 0.3204(4) 0.56222(15) 0.0658(6) Uani 1 1 d . . . . .
F2 F -0.0420(4) 0.0992(4) 0.66724(13) 0.0609(6) Uani 1 1 d . . . . .
C6 C 0.1502(5) 0.1160(5) 0.4448(2) 0.0363(7) Uani 1 1 d . . . . .
C7 C 0.1217(6) 0.1627(6) 0.5299(2) 0.0411(7) Uani 1 1 d . . . . .
C8 C -0.0248(6) 0.0487(6) 0.5842(2) 0.0391(7) 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
O1 C1 1.238(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.318(5) . ?
N2 C2 1.334(5) . ?
N2 C3 1.330(5) . ?
N3 C4 1.317(5) . ?
N3 C5 1.328(4) . ?
C1 C2 1.500(5) . ?
C2 C5 1.374(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
I1 C6 2.090(3) . ?
F1 C7 1.344(4) . ?
F2 C8 1.344(4) . ?
C6 C7 1.372(5) . ?
C6 C8 1.380(5) 2_556 ?
C7 C8 1.377(4) . ?
C8 C6 1.380(5) 2_556 ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C3 N2 C2 115.8(3) . . ?
C4 N3 C5 115.8(3) . . ?
O1 C1 N1 124.2(3) . . ?
O1 C1 C2 119.8(3) . . ?
N1 C1 C2 116.1(3) . . ?
N2 C2 C1 117.2(3) . . ?
N2 C2 C5 121.7(3) . . ?
C5 C2 C1 121.1(3) . . ?
N2 C3 H3 119.1 . . ?
N2 C3 C4 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
N3 C4 C3 122.5(3) . . ?
N3 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
N3 C5 C2 122.3(3) . . ?
N3 C5 H5 118.8 . . ?
C2 C5 H5 118.8 . . ?
C7 C6 I1 122.0(2) . . ?
C7 C6 C8 117.2(3) . 2_556 ?
C8 C6 I1 120.8(2) 2_556 . ?
F1 C7 C6 120.2(3) . . ?
F1 C7 C8 118.5(3) . . ?
C6 C7 C8 121.3(3) . . ?
F2 C8 C6 120.0(3) . 2_556 ?
F2 C8 C7 118.5(3) . . ?
C7 C8 C6 121.5(3) . 2_556 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.06 2.916(4) 177.3 2_865
C3 H3 O1 0.93 2.65 3.423(5) 140.4 1_465
C4 H4 F2 0.93 2.57 3.495(4) 174.4 2_566

_shelx_SHELXL_version_number     2014/7

_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_LDC_TFIB
_database_code_depnum_ccdc_archive 'CCDC 1550374'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N2 O, 0.5(C6 I2 F4)'
_chemical_formula_sum            'C17 H22 F2 I N2 O'
_chemical_formula_weight         435.26
_chemical_melting_point          354.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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        P2(1)/n
_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                   8.3275(15)
_cell_length_b                   15.183(3)
_cell_length_c                   15.170(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.678(6)
_cell_angle_gamma                90
_cell_volume                     1884.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.743
_cell_measurement_theta_min      5.405
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.559
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.3046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1675 before and 0.0803 after correction.
The Ratio of minimum to maximum transmission is 0.3525.
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    1.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15877
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.582
_diffrn_reflns_theta_max         66.582
_diffrn_reflns_theta_min         5.936
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             3308
_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       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.070
_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)+(0.0719P)²+1.0635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7391(7) 0.5291(2) 0.7091(3) 0.1091(16) Uani 1 1 d . . . . .
N1 N 0.8615(5) 0.5629(3) 0.8500(3) 0.0770(10) Uani 1 1 d . . . . .
H1 H 0.8853 0.6051 0.8879 0.092 Uiso 1 1 calc R . . . .
N2 N 0.7913(7) 0.7359(3) 0.8293(4) 0.1030(15) Uani 1 1 d . . . . .
C1 C 0.9118(6) 0.4754(3) 0.8787(3) 0.0740(12) Uani 1 1 d . . . . .
C2 C 1.0604(8) 0.4447(5) 0.8641(5) 0.1009(17) Uani 1 1 d . . . . .
C3 C 1.1736(12) 0.4980(9) 0.8210(7) 0.152(3) Uani 1 1 d . . . . .
H3A H 1.2729 0.4657 0.8216 0.228 Uiso 1 1 calc GR . . . .
H3B H 1.1978 0.5522 0.8532 0.228 Uiso 1 1 calc GR . . . .
H3C H 1.1233 0.5105 0.7601 0.228 Uiso 1 1 calc GR . . . .
C4 C 1.1038(9) 0.3596(6) 0.8960(5) 0.119(2) Uani 1 1 d . . . . .
H4 H 1.2038 0.3367 0.8882 0.143 Uiso 1 1 calc R . . . .
C5 C 1.0058(12) 0.3096(4) 0.9378(5) 0.118(2) Uani 1 1 d . . . . .
H5 H 1.0390 0.2537 0.9585 0.142 Uiso 1 1 calc R . . . .
C6 C 0.8620(11) 0.3410(4) 0.9489(4) 0.111(2) Uani 1 1 d . . . . .
H6 H 0.7952 0.3061 0.9774 0.133 Uiso 1 1 calc R . . . .
C7 C 0.8085(7) 0.4245(4) 0.9192(4) 0.0901(15) Uani 1 1 d . . . . .
C8 C 0.6439(12) 0.4580(5) 0.9290(9) 0.142(3) Uani 1 1 d . . . . .
H8A H 0.6566 0.5084 0.9678 0.213 Uiso 1 1 calc GR . . . .
H8B H 0.5860 0.4126 0.9543 0.213 Uiso 1 1 calc GR . . . .
H8C H 0.5833 0.4744 0.8712 0.213 Uiso 1 1 calc GR . . . .
C9 C 0.7806(6) 0.5825(3) 0.7685(4) 0.0821(13) Uani 1 1 d . . . . .
C10 C 0.7414(9) 0.6791(4) 0.7519(4) 0.1040(19) Uani 1 1 d . . . . .
H10A H 0.7944 0.6994 0.7038 0.125 Uiso 1 1 calc R . . . .
H10B H 0.6244 0.6852 0.7317 0.125 Uiso 1 1 calc R . . . .
C11 C 0.6492(14) 0.7815(7) 0.8600(8) 0.161(4) Uani 1 1 d . . . . .
H11A H 0.6910 0.8225 0.9078 0.193 Uiso 1 1 calc R . . . .
H11B H 0.5877 0.8149 0.8105 0.193 Uiso 1 1 calc R . . . .
C12 C 0.5422(18) 0.7196(12) 0.8917(11) 0.217(6) Uani 1 1 d . . . . .
H12A H 0.4983 0.6798 0.8441 0.326 Uiso 1 1 calc GR . . . .
H12B H 0.4544 0.7507 0.9109 0.326 Uiso 1 1 calc GR . . . .
H12C H 0.6024 0.6868 0.9411 0.326 Uiso 1 1 calc GR . . . .
C13 C 0.9001(14) 0.8058(5) 0.8151(6) 0.145(3) Uani 1 1 d . . . . .
H13A H 0.9163 0.8452 0.8663 0.173 Uiso 1 1 calc R . . . .
H13B H 0.8513 0.8394 0.7626 0.173 Uiso 1 1 calc R . . . .
C14 C 1.0589(14) 0.7709(7) 0.8024(7) 0.159(4) Uani 1 1 d . . . . .
H14A H 1.0418 0.7235 0.7598 0.239 Uiso 1 1 calc GR . . . .
H14B H 1.1184 0.7496 0.8587 0.239 Uiso 1 1 calc GR . . . .
H14C H 1.1202 0.8168 0.7804 0.239 Uiso 1 1 calc GR . . . .
I1 I 0.40148(4) 0.53391(2) 0.61138(2) 0.0868(2) Uani 1 1 d . . . . .
F1 F 0.2301(4) 0.3766(2) 0.4898(3) 0.1050(10) Uani 1 1 d . . . . .
F2 F -0.0747(4) 0.3503(2) 0.4047(3) 0.1115(11) Uani 1 1 d . . . . .
C15 C 0.1621(6) 0.5142(3) 0.5441(3) 0.0757(12) Uani 1 1 d . . . . .
C16 C 0.1165(7) 0.4394(3) 0.4953(4) 0.0797(13) Uani 1 1 d . . . . .
C17 C -0.0399(7) 0.4256(3) 0.4527(4) 0.0852(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.213(6) . ?
N1 H1 0.8600 . ?
N1 C1 1.435(6) . ?
N1 C9 1.328(6) . ?
N2 C10 1.455(7) . ?
N2 C11 1.517(12) . ?
N2 C13 1.437(10) . ?
C1 C2 1.378(8) . ?
C1 C7 1.383(8) . ?
C2 C3 1.483(11) . ?
C2 C4 1.403(11) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.355(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.328(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(9) . ?
C7 C8 1.495(10) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.513(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.437(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.470(13) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
I1 C15 2.086(5) . ?
F1 C16 1.356(6) . ?
F2 C17 1.357(6) . ?
C15 C16 1.371(7) . ?
C15 C17 1.375(8) 3_566 ?
C16 C17 1.358(8) . ?
C17 C15 1.375(8) 3_566 ?

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
C1 N1 H1 118.0 . . ?
C9 N1 H1 118.0 . . ?
C9 N1 C1 124.0(4) . . ?
C10 N2 C11 113.3(6) . . ?
C13 N2 C10 114.2(6) . . ?
C13 N2 C11 105.0(7) . . ?
C2 C1 N1 119.0(5) . . ?
C2 C1 C7 122.2(5) . . ?
C7 C1 N1 118.8(5) . . ?
C1 C2 C3 123.3(7) . . ?
C1 C2 C4 116.0(7) . . ?
C4 C2 C3 120.7(8) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4 118.7 . . ?
C5 C4 C2 122.6(7) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.1 . . ?
C5 C6 C7 121.8(7) . . ?
C7 C6 H6 119.1 . . ?
C1 C7 C6 117.7(6) . . ?
C1 C7 C8 120.8(6) . . ?
C6 C7 C8 121.5(7) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 124.5(5) . . ?
O1 C9 C10 120.1(5) . . ?
N1 C9 C10 115.4(5) . . ?
N2 C10 C9 114.8(5) . . ?
N2 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 N2 111.8(10) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
N2 C13 C14 111.2(8) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 I1 121.8(4) . . ?
C16 C15 C17 115.9(5) . 3_566 ?
C17 C15 I1 122.3(4) 3_566 . ?
F1 C16 C15 119.2(5) . . ?
F1 C16 C17 118.7(4) . . ?
C17 C16 C15 122.0(5) . . ?
F2 C17 C15 119.5(5) . 3_566 ?
F2 C17 C16 118.4(5) . . ?
C16 C17 C15 122.1(5) . 3_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 2.26 2.697(6) 111.9 .

_shelx_SHELXL_version_number     2014/7

_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_PZA_TFBB
_database_code_depnum_ccdc_archive 'CCDC 1550373'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H5 N3 O), Br2 C6 F4'
_chemical_formula_sum            'C16 H10 Br2 F4 N6 O2'
_chemical_formula_weight         554.12
_chemical_melting_point          380.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.2164(8)
_cell_length_b                   5.7379(10)
_cell_length_c                   16.463(3)
_cell_angle_alpha                98.285(5)
_cell_angle_beta                 90.049(5)
_cell_angle_gamma                102.844(5)
_cell_volume                     475.15(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.236
_cell_measurement_theta_min      2.502
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.582
_exptl_absorpt_coefficient_mu    4.331
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0812 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.6769.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         2.502
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1464
_reflns_number_total             2091
_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       'Bruker Apex3, 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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.038
_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)+(0.0363P)²+0.6071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.2774(6) 0.6475(5) 0.06337(19) 0.0499(8) Uani 1 1 d . . . . .
N1 N 1.2738(7) 0.2494(6) 0.0404(2) 0.0465(9) Uani 1 1 d . . . . .
H1A H 1.4030 0.2694 0.0078 0.056 Uiso 1 1 calc R . . . .
H1B H 1.2023 0.1069 0.0506 0.056 Uiso 1 1 calc R . . . .
N2 N 0.8624(7) 0.1565(6) 0.1398(2) 0.0443(9) Uani 1 1 d . . . . .
N3 N 0.6720(7) 0.5327(6) 0.2262(2) 0.0461(9) Uani 1 1 d . . . . .
C1 C 1.1850(8) 0.4381(7) 0.0750(2) 0.0374(9) Uani 1 1 d . . . . .
C2 C 0.9638(7) 0.3862(6) 0.1319(2) 0.0320(8) Uani 1 1 d . . . . .
C3 C 0.6645(9) 0.1181(7) 0.1904(3) 0.0480(11) Uani 1 1 d . . . . .
H3 H 0.5860 -0.0399 0.1971 0.058 Uiso 1 1 calc R . . . .
C4 C 0.5719(9) 0.3049(7) 0.2332(3) 0.0442(10) Uani 1 1 d . . . . .
H4 H 0.4338 0.2691 0.2683 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8671(9) 0.5711(7) 0.1744(3) 0.0436(10) Uani 1 1 d . . . . .
H5 H 0.9411 0.7290 0.1666 0.052 Uiso 1 1 calc R . . . .
Br1 Br 0.34590(10) 0.75822(8) 0.35967(3) 0.0582(2) Uani 1 1 d . . . . .
F1 F 0.0164(6) 1.1286(5) 0.34781(17) 0.0644(7) Uani 1 1 d . . . . .
F2 F -0.2637(5) 1.3294(5) 0.46220(18) 0.0625(7) Uani 1 1 d . . . . .
C6 C 0.1458(8) 0.8947(7) 0.4399(3) 0.0405(10) Uani 1 1 d . . . . .
C7 C 0.0111(8) 1.0637(7) 0.4233(2) 0.0418(10) Uani 1 1 d . . . . .
C8 C -0.1329(8) 1.1675(7) 0.4824(3) 0.0436(10) 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
O1 C1 1.233(5) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.326(5) . ?
N2 C2 1.332(5) . ?
N2 C3 1.328(5) . ?
N3 C4 1.317(5) . ?
N3 C5 1.329(5) . ?
C1 C2 1.492(5) . ?
C2 C5 1.376(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
Br1 C6 1.875(4) . ?
F1 C7 1.347(5) . ?
F2 C8 1.345(5) . ?
C6 C7 1.373(6) . ?
C6 C8 1.375(6) 2_576 ?
C7 C8 1.378(6) . ?
C8 C6 1.375(6) 2_576 ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
C3 N2 C2 116.1(3) . . ?
C4 N3 C5 115.8(3) . . ?
O1 C1 N1 123.7(4) . . ?
O1 C1 C2 120.2(3) . . ?
N1 C1 C2 116.1(3) . . ?
N2 C2 C1 118.1(3) . . ?
N2 C2 C5 121.3(3) . . ?
C5 C2 C1 120.7(3) . . ?
N2 C3 H3 119.0 . . ?
N2 C3 C4 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
N3 C4 C3 122.3(4) . . ?
N3 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
N3 C5 C2 122.5(4) . . ?
N3 C5 H5 118.7 . . ?
C2 C5 H5 118.7 . . ?
C7 C6 Br1 121.0(3) . . ?
C7 C6 C8 117.8(4) . 2_576 ?
C8 C6 Br1 121.2(3) 2_576 . ?
F1 C7 C6 119.9(4) . . ?
F1 C7 C8 118.8(4) . . ?
C6 C7 C8 121.3(4) . . ?
F2 C8 C6 120.5(4) . 2_576 ?
F2 C8 C7 118.6(4) . . ?
C6 C8 C7 120.9(4) 2_576 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.05 2.904(4) 174.1 2_865

_shelx_SHELXL_version_number     2014/7

_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_PXF_TFBB
_database_code_depnum_ccdc_archive 'CCDC 1550377'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2017-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H18 N4 O3), Br2 C6 F4'
_chemical_formula_sum            'C32 H36 Br2 F4 N8 O6'
_chemical_formula_weight         864.51
_chemical_melting_point          360.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.0832(6)
_cell_length_b                   11.3132(14)
_cell_length_c                   16.794(2)
_cell_angle_alpha                107.353(7)
_cell_angle_beta                 96.484(7)
_cell_angle_gamma                90.132(7)
_cell_volume                     915.3(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.769
_shelx_estimated_absorpt_T_min   0.702
_exptl_absorpt_coefficient_mu    3.463
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0975 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.7438.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13571
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.849
_diffrn_reflns_theta_max         66.849
_diffrn_reflns_theta_min         2.776
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1949
_reflns_number_total             3221
_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       'Bruker Apex3, 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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0051(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.049
_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)+(0.0638P)²+0.3834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1467
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0232(9) 0.1142(4) 0.2000(4) 0.1443(18) Uani 1 1 d . . . . .
O2 O 0.4508(7) 0.7247(3) 0.2550(3) 0.1027(11) Uani 1 1 d . . . . .
O3 O 0.7361(7) 0.5888(3) 0.4804(3) 0.1051(11) Uani 1 1 d . . . . .
N1 N 0.5987(7) 0.6566(3) 0.3670(3) 0.0844(11) Uani 1 1 d . . . . .
N2 N 0.8108(8) 0.8249(4) 0.3398(3) 0.0903(11) Uani 1 1 d . . . . .
N3 N 1.1995(8) 0.9143(4) 0.4364(3) 0.0872(11) Uani 1 1 d . . . . .
N4 N 1.1753(8) 0.7907(4) 0.5201(3) 0.0914(12) Uani 1 1 d . . . . .
C1 C 0.3890(8) 0.5566(4) 0.3388(3) 0.0889(14) Uani 1 1 d . . . . .
H1A H 0.2290 0.5882 0.3165 0.107 Uiso 1 1 calc R . . . .
H1B H 0.3492 0.5313 0.3866 0.107 Uiso 1 1 calc R . . . .
C2 C 0.4723(8) 0.4460(4) 0.2723(3) 0.0871(14) Uani 1 1 d . . . . .
H2A H 0.6404 0.4187 0.2928 0.104 Uiso 1 1 calc R . . . .
H2B H 0.4971 0.4696 0.2226 0.104 Uiso 1 1 calc R . . . .
C3 C 0.2672(8) 0.3402(4) 0.2493(3) 0.0850(13) Uani 1 1 d . . . . .
H3A H 0.1008 0.3673 0.2276 0.102 Uiso 1 1 calc R . . . .
H3B H 0.2386 0.3189 0.2996 0.102 Uiso 1 1 calc R . . . .
C4 C 0.3487(10) 0.2255(4) 0.1842(4) 0.0952(15) Uani 1 1 d . . . . .
H4A H 0.3551 0.2449 0.1319 0.114 Uiso 1 1 calc R . . . .
H4B H 0.5266 0.2062 0.2028 0.114 Uiso 1 1 calc R . . . .
C5 C 0.1733(12) 0.1131(5) 0.1670(4) 0.1034(17) Uani 1 1 d . . . . .
C6 C 0.2564(15) -0.0023(6) 0.1059(5) 0.156(3) Uani 1 1 d . . . . .
H6A H 0.4308 -0.0219 0.1254 0.234 Uiso 1 1 calc GR . . . .
H6B H 0.2576 0.0105 0.0520 0.234 Uiso 1 1 calc GR . . . .
H6C H 0.1341 -0.0695 0.1012 0.234 Uiso 1 1 calc GR . . . .
C7 C 0.6053(10) 0.7352(5) 0.3159(4) 0.0864(14) Uani 1 1 d . . . . .
C8 C 0.8358(12) 0.9106(5) 0.2885(4) 0.1068(17) Uani 1 1 d . . . . .
H8A H 0.6861 0.9628 0.2925 0.160 Uiso 1 1 calc GR . . . .
H8B H 0.8416 0.8632 0.2309 0.160 Uiso 1 1 calc GR . . . .
H8C H 0.9956 0.9609 0.3091 0.160 Uiso 1 1 calc GR . . . .
C9 C 0.9863(9) 0.8311(4) 0.4097(3) 0.0791(12) Uani 1 1 d . . . . .
C10 C 0.9668(9) 0.7561(4) 0.4589(3) 0.0840(13) Uani 1 1 d . . . . .
C11 C 0.7653(9) 0.6598(5) 0.4390(4) 0.0876(14) Uani 1 1 d . . . . .
C12 C 1.3030(10) 0.8846(5) 0.5036(4) 0.0906(15) Uani 1 1 d . . . . .
H12 H 1.4536 0.9256 0.5372 0.109 Uiso 1 1 calc R . . . .
C13 C 1.2427(11) 0.7342(5) 0.5868(4) 0.1037(16) Uani 1 1 d . . . . .
H13A H 1.1243 0.7614 0.6287 0.156 Uiso 1 1 calc GR . . . .
H13B H 1.4216 0.7583 0.6118 0.156 Uiso 1 1 calc GR . . . .
H13C H 1.2267 0.6456 0.5637 0.156 Uiso 1 1 calc GR . . . .
Br1 Br 0.00962(10) 0.60758(6) 0.14088(4) 0.1002(3) Uani 1 1 d . . . . .
F1 F -0.3605(6) 0.7436(3) 0.0459(2) 0.1142(10) Uani 1 1 d . . . . .
F2 F -0.7788(6) 0.6564(3) -0.0681(2) 0.1141(10) Uani 1 1 d . . . . .
C14 C -0.2812(9) 0.5453(5) 0.0610(3) 0.0843(13) Uani 1 1 d . . . . .
C15 C -0.4273(10) 0.6217(5) 0.0241(3) 0.0899(14) Uani 1 1 d . . . . .
C16 C -0.6403(10) 0.5772(5) -0.0352(3) 0.0884(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.195(6) . ?
O2 C7 1.193(6) . ?
O3 C11 1.229(6) . ?
N1 C1 1.483(5) . ?
N1 C7 1.410(7) . ?
N1 C11 1.387(7) . ?
N2 C7 1.393(6) . ?
N2 C8 1.489(6) . ?
N2 C9 1.376(6) . ?
N3 C9 1.377(6) . ?
N3 C12 1.324(6) . ?
N4 C10 1.359(6) . ?
N4 C12 1.357(6) . ?
N4 C13 1.456(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.506(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.516(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.487(7) . ?
C5 C6 1.495(8) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.359(7) . ?
C10 C11 1.431(6) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
Br1 C14 1.862(5) . ?
F1 C15 1.349(5) . ?
F2 C16 1.348(6) . ?
C14 C15 1.379(7) . ?
C14 C16 1.366(7) 2_465 ?
C15 C16 1.368(7) . ?
C16 C14 1.366(7) 2_465 ?

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
C7 N1 C1 115.5(4) . . ?
C11 N1 C1 116.3(4) . . ?
C11 N1 C7 128.3(4) . . ?
C7 N2 C8 119.1(5) . . ?
C9 N2 C7 119.0(5) . . ?
C9 N2 C8 121.9(4) . . ?
C12 N3 C9 100.2(4) . . ?
C10 N4 C13 125.8(5) . . ?
C12 N4 C10 105.0(5) . . ?
C12 N4 C13 129.2(5) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.7(3) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.4(4) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 112.8(4) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 C3 115.4(4) . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
O1 C5 C4 122.2(5) . . ?
O1 C5 C6 121.4(5) . . ?
C4 C5 C6 116.3(5) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N1 123.0(5) . . ?
O2 C7 N2 121.5(5) . . ?
N2 C7 N1 115.5(5) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N3 122.9(5) . . ?
C10 C9 N2 123.5(4) . . ?
C10 C9 N3 113.5(5) . . ?
N4 C10 C9 105.5(4) . . ?
N4 C10 C11 132.7(6) . . ?
C9 C10 C11 121.7(5) . . ?
O3 C11 N1 122.9(4) . . ?
O3 C11 C10 125.2(6) . . ?
N1 C11 C10 111.9(5) . . ?
N3 C12 N4 115.8(5) . . ?
N3 C12 H12 122.1 . . ?
N4 C12 H12 122.1 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 Br1 121.0(4) . . ?
C16 C14 Br1 122.4(4) 2_465 . ?
C16 C14 C15 116.6(5) 2_465 . ?
F1 C15 C14 120.0(5) . . ?
F1 C15 C16 118.3(5) . . ?
C16 C15 C14 121.7(5) . . ?
F2 C16 C14 119.1(5) . 2_465 ?
F2 C16 C15 119.2(5) . . ?
C14 C16 C15 121.7(5) 2_465 . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT431_PXF_TFBB            
;
PROBLEM: Short Inter HL..A  Contact Br1    ..  O2      ..       2.82 Ang.  
RESPONSE:  This short contact is a result of halogen bonding
;
# end Validation Reply Form
####################################################################### 
# 
# 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_LDC_TFBB
_database_code_depnum_ccdc_archive 'CCDC 1550375'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N2 O, 0.5(C6 Br2 F4)'
_chemical_formula_sum            'C17 H22 Br F2 N2 O'
_chemical_formula_weight         388.27
_chemical_melting_point          333.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P2(1)/n
_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                   8.1092(4)
_cell_length_b                   14.9953(7)
_cell_length_c                   15.2066(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.158(2)
_cell_angle_gamma                90
_cell_volume                     1814.17(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.378
_cell_measurement_theta_min      2.731
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.290
_exptl_absorpt_correction_T_max  0.0949
_exptl_absorpt_correction_T_min  0.0340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1370 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.3583.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.731
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             3686
_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       'Bruker Apex3, 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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.055(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3686
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+1.0108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1589
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C13, C14, C11, C12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7631(5) 0.47307(17) 0.6995(2) 0.0914(10) Uani 1 1 d . . . . .
N1 N 0.8631(3) 0.43885(18) 0.84466(18) 0.0560(6) Uani 1 1 d . . . . .
H1 H 0.8770 0.3963 0.8833 0.067 Uiso 1 1 calc R . . . .
N2 N 0.7772(5) 0.2655(2) 0.8234(2) 0.0746(9) Uani 1 1 d . . . . .
C1 C 0.9226(4) 0.5255(2) 0.8743(2) 0.0544(7) Uani 1 1 d . . . . .
C2 C 0.8267(5) 0.5770(2) 0.9219(2) 0.0660(9) Uani 1 1 d . . . . .
C3 C 0.6604(8) 0.5441(3) 0.9384(5) 0.1033(16) Uani 1 1 d . . . . .
H3A H 0.5899 0.5282 0.8824 0.155 Uiso 1 1 calc GR . . . .
H3B H 0.6071 0.5904 0.9665 0.155 Uiso 1 1 calc GR . . . .
H3C H 0.6779 0.4929 0.9769 0.155 Uiso 1 1 calc GR . . . .
C4 C 0.8891(7) 0.6603(3) 0.9525(3) 0.0854(13) Uani 1 1 d . . . . .
H4 H 0.8271 0.6958 0.9843 0.103 Uiso 1 1 calc R . . . .
C5 C 1.0373(8) 0.6906(3) 0.9371(3) 0.0938(15) Uani 1 1 d . . . . .
H5 H 1.0773 0.7460 0.9591 0.113 Uiso 1 1 calc R . . . .
C6 C 1.1290(6) 0.6401(3) 0.8892(3) 0.0937(14) Uani 1 1 d . . . . .
H6 H 1.2303 0.6621 0.8781 0.112 Uiso 1 1 calc R . . . .
C7 C 1.0733(5) 0.5561(3) 0.8566(3) 0.0754(10) Uani 1 1 d . . . . .
C8 C 1.1751(7) 0.5011(5) 0.8037(5) 0.1143(19) Uani 1 1 d . . . . .
H8A H 1.2069 0.4461 0.8346 0.171 Uiso 1 1 calc GR . . . .
H8B H 1.2742 0.5335 0.7974 0.171 Uiso 1 1 calc GR . . . .
H8C H 1.1090 0.4887 0.7455 0.171 Uiso 1 1 calc GR . . . .
C9 C 0.7875(5) 0.4196(2) 0.7611(2) 0.0624(9) Uani 1 1 d . . . . .
C10 C 0.7330(6) 0.3231(2) 0.7458(3) 0.0769(11) Uani 1 1 d . . . . .
H10A H 0.6120 0.3216 0.7257 0.092 Uiso 1 1 calc R . . . .
H10B H 0.7831 0.2991 0.6978 0.092 Uiso 1 1 calc R . . . .
C11 C 0.8933(10) 0.1926(4) 0.8116(4) 0.1223(19) Uani 1 1 d . U . . .
H11A H 0.9109 0.1545 0.8641 0.147 Uiso 1 1 calc R . . . .
H11B H 0.8431 0.1567 0.7602 0.147 Uiso 1 1 calc R . . . .
C12 C 1.0506(10) 0.2260(5) 0.7985(6) 0.150(3) Uani 1 1 d . U . . .
H12A H 1.0325 0.2690 0.7507 0.224 Uiso 1 1 calc GR . . . .
H12B H 1.1176 0.1778 0.7832 0.224 Uiso 1 1 calc GR . . . .
H12C H 1.1079 0.2540 0.8526 0.224 Uiso 1 1 calc GR . . . .
C13 C 0.6340(8) 0.2192(4) 0.8499(5) 0.126(2) Uani 1 1 d . U . . .
H13A H 0.6758 0.1749 0.8952 0.151 Uiso 1 1 calc R . . . .
H13B H 0.5697 0.1885 0.7983 0.151 Uiso 1 1 calc R . . . .
C14 C 0.5232(10) 0.2823(6) 0.8856(7) 0.160(3) Uani 1 1 d . U . . .
H14A H 0.4764 0.3241 0.8397 0.241 Uiso 1 1 calc GR . . . .
H14B H 0.5872 0.3138 0.9358 0.241 Uiso 1 1 calc GR . . . .
H14C H 0.4341 0.2499 0.9046 0.241 Uiso 1 1 calc GR . . . .
Br1 Br 0.39217(5) 0.46743(3) 0.59890(3) 0.0796(3) Uani 1 1 d . . . . .
F2 F 0.2337(3) 0.62584(15) 0.48894(17) 0.0850(7) Uani 1 1 d . . . . .
F3 F 0.0840(3) 0.34733(15) 0.59170(18) 0.0913(7) Uani 1 1 d . . . . .
C15 C 0.1676(5) 0.4858(2) 0.5419(2) 0.0616(8) Uani 1 1 d . . . . .
C16 C 0.1203(5) 0.5624(2) 0.4944(2) 0.0632(9) Uani 1 1 d . . . . .
C17 C 0.0440(5) 0.4238(2) 0.5463(2) 0.0643(9) 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
O1 C9 1.220(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.428(4) . ?
N1 C9 1.331(4) . ?
N2 C10 1.451(5) . ?
N2 C11 1.476(7) . ?
N2 C13 1.474(7) . ?
C1 C2 1.394(5) . ?
C1 C7 1.379(5) . ?
C2 C3 1.502(6) . ?
C2 C4 1.394(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.347(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.397(6) . ?
C7 C8 1.505(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.518(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.420(9) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.478(10) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
Br1 C15 1.880(4) . ?
F2 C16 1.337(4) . ?
F3 C17 1.346(4) . ?
C15 C16 1.372(5) . ?
C15 C17 1.377(5) . ?
C16 C17 1.372(5) 3_566 ?
C17 C16 1.372(5) 3_566 ?

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
C1 N1 H1 117.9 . . ?
C9 N1 H1 117.9 . . ?
C9 N1 C1 124.3(3) . . ?
C10 N2 C11 113.9(4) . . ?
C10 N2 C13 114.8(4) . . ?
C11 N2 C13 103.9(4) . . ?
C2 C1 N1 118.7(3) . . ?
C7 C1 N1 120.0(3) . . ?
C7 C1 C2 121.3(3) . . ?
C1 C2 C3 120.9(3) . . ?
C4 C2 C1 117.9(4) . . ?
C4 C2 C3 121.2(4) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4 119.3 . . ?
C5 C4 C2 121.5(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.1(5) . . ?
C7 C6 H6 119.4 . . ?
C1 C7 C6 118.0(4) . . ?
C1 C7 C8 121.3(4) . . ?
C6 C7 C8 120.7(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 124.6(3) . . ?
O1 C9 C10 120.6(3) . . ?
N1 C9 C10 114.8(3) . . ?
N2 C10 C9 115.1(3) . . ?
N2 C10 H10A 108.5 . . ?
N2 C10 H10B 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 H11A 109.3 . . ?
N2 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 N2 111.5(5) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
N2 C13 C14 111.5(5) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 Br1 120.8(3) . . ?
C16 C15 C17 117.3(3) . . ?
C17 C15 Br1 121.9(3) . . ?
F2 C16 C15 120.2(3) . . ?
F2 C16 C17 119.0(3) . 3_566 ?
C15 C16 C17 120.8(3) . 3_566 ?
F3 C17 C15 119.6(3) . . ?
F3 C17 C16 118.4(3) . 3_566 ?
C16 C17 C15 121.9(3) 3_566 . ?

_shelx_SHELXL_version_number     2014/7

_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_PXF_TFIB
_database_code_depnum_ccdc_archive 'CCDC 1550376'
_audit_update_record             
;
2017-07-26 deposited with the CCDC.
2017-08-02 downloaded from the CCDC.
;
_audit_creation_date             2017-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 N4 O3, C6 F4 I2'
_chemical_formula_sum            'C19 H18 F4 I2 N4 O3'
_chemical_formula_weight         680.17
_chemical_absolute_configuration ad
_chemical_melting_point          388.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           33
_space_group_name_H-M_alt        Pna2(1)
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   16.5437(5)
_cell_length_b                   31.4061(9)
_cell_length_c                   4.48440(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2329.97(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.129
_cell_measurement_theta_min      2.814
_shelx_estimated_absorpt_T_max   0.275
_shelx_estimated_absorpt_T_min   0.220
_exptl_absorpt_coefficient_mu    21.754
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1192 before and 0.0888 after correction. The Ratio of minimum to maximum transmission is 0.6494. 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    1.939
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            39935
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.697
_diffrn_reflns_theta_max         66.697
_diffrn_reflns_theta_min         2.814
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2529
_reflns_number_total             4107
_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       'Bruker Apex3, 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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(9)
_refine_ls_extinction_coef       0.00045(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4107
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.031
_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)+(0.0851P)²+1.0111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1613
_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.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_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
O1 O -0.1133(10) 0.6349(6) 0.305(4) 0.125(6) Uani 1 1 d . . . . .
N1 N 0.1136(9) 0.7485(4) 0.219(3) 0.069(3) Uani 1 1 d . . . . .
C1 C 0.0918(9) 0.7124(4) 0.025(6) 0.075(4) Uani 1 1 d . . . . .
H1A H 0.1392 0.7029 -0.0832 0.090 Uiso 1 1 calc R . . . .
H1B H 0.0517 0.7215 -0.1191 0.090 Uiso 1 1 calc R . . . .
O2 O -0.0125(8) 0.7752(4) 0.171(3) 0.095(4) Uani 1 1 d . . . . .
N2 N 0.0729(8) 0.8102(4) 0.478(4) 0.072(4) Uani 1 1 d . . . . .
C2 C 0.0575(12) 0.6750(5) 0.212(4) 0.080(5) Uani 1 1 d . . . . .
H2A H 0.0972 0.6661 0.3586 0.096 Uiso 1 1 calc R . . . .
H2B H 0.0095 0.6843 0.3182 0.096 Uiso 1 1 calc R . . . .
O3 O 0.2403(8) 0.7199(3) 0.274(3) 0.081(3) Uani 1 1 d . . . . .
N3 N 0.1733(9) 0.8401(4) 0.804(4) 0.081(4) Uani 1 1 d . . . . .
C3 C 0.0363(9) 0.6378(3) 0.013(6) 0.064(3) Uani 1 1 d . . . . .
H3A H 0.0833 0.6303 -0.1052 0.077 Uiso 1 1 calc R . . . .
H3B H -0.0062 0.6463 -0.1230 0.077 Uiso 1 1 calc R . . . .
N4 N 0.2719(8) 0.7921(4) 0.710(4) 0.071(4) Uani 1 1 d . . . . .
C4 C 0.0085(12) 0.5986(6) 0.186(5) 0.094(6) Uani 1 1 d . . . . .
H4A H 0.0480 0.5924 0.3398 0.113 Uiso 1 1 calc R . . . .
H4B H 0.0072 0.5744 0.0508 0.113 Uiso 1 1 calc R . . . .
C5 C -0.0761(16) 0.6032(8) 0.334(5) 0.102(7) Uani 1 1 d . . . . .
C6 C -0.1058(18) 0.5644(9) 0.479(8) 0.167(14) Uani 1 1 d . . . . .
H6A H -0.1354 0.5719 0.6556 0.250 Uiso 1 1 calc GR . . . .
H6B H -0.0609 0.5466 0.5319 0.250 Uiso 1 1 calc GR . . . .
H6C H -0.1407 0.5493 0.3445 0.250 Uiso 1 1 calc GR . . . .
C7 C 0.0536(11) 0.7781(5) 0.289(4) 0.075(5) Uani 1 1 d . . . . .
C8 C 0.0115(11) 0.8429(5) 0.549(8) 0.106(6) Uani 1 1 d . . . . .
H8A H -0.0386 0.8358 0.4528 0.160 Uiso 1 1 calc GR . . . .
H8B H 0.0297 0.8702 0.4788 0.160 Uiso 1 1 calc GR . . . .
H8C H 0.0034 0.8441 0.7606 0.160 Uiso 1 1 calc GR . . . .
C9 C 0.1476(10) 0.8110(4) 0.600(4) 0.070(5) Uani 1 1 d . . . . .
C10 C 0.2058(8) 0.7812(4) 0.542(5) 0.060(3) Uani 1 1 d . . . . .
C11 C 0.1919(11) 0.7474(5) 0.338(4) 0.067(4) Uani 1 1 d . . . . .
C12 C 0.2482(12) 0.8267(5) 0.864(4) 0.081(5) Uani 1 1 d . . . . .
H12 H 0.2814 0.8403 1.0017 0.097 Uiso 1 1 calc R . . . .
C13 C 0.3485(11) 0.7707(6) 0.726(6) 0.103(7) Uani 1 1 d . . . . .
H13A H 0.3419 0.7440 0.8270 0.154 Uiso 1 1 calc GR . . . .
H13B H 0.3861 0.7881 0.8342 0.154 Uiso 1 1 calc GR . . . .
H13C H 0.3686 0.7658 0.5283 0.154 Uiso 1 1 calc GR . . . .
I1 I 0.28989(7) 0.63695(3) 1.0350(4) 0.0883(4) Uani 1 1 d . . . . .
F1 F 0.4307(6) 0.5677(3) 1.122(3) 0.104(5) Uani 1 1 d . . . . .
I2 I 0.33579(7) 0.42886(3) 0.5159(4) 0.0844(4) Uani 1 1 d . . . . .
F2 F 0.4474(6) 0.4886(3) 0.934(3) 0.099(4) Uani 1 1 d . . . . .
F3 F 0.2007(7) 0.5004(4) 0.419(3) 0.118(5) Uani 1 1 d . . . . .
F4 F 0.1811(7) 0.5776(3) 0.618(3) 0.114(5) Uani 1 1 d . . . . .
C14 C 0.3041(11) 0.5753(5) 0.878(4) 0.075(5) Uani 1 1 d . . . . .
C15 C 0.3728(12) 0.5509(5) 0.949(4) 0.081(6) Uani 1 1 d . . . . .
C16 C 0.3818(11) 0.5106(5) 0.844(5) 0.079(5) Uani 1 1 d . . . . .
C17 C 0.3250(10) 0.4921(5) 0.665(5) 0.077(5) Uani 1 1 d . . . . .
C18 C 0.2602(11) 0.5157(5) 0.591(5) 0.085(6) Uani 1 1 d . . . . .
C19 C 0.2474(11) 0.5563(6) 0.697(4) 0.077(5) 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
O1 C5 1.18(3) . ?
N1 C1 1.47(2) . ?
N1 C7 1.40(2) . ?
N1 C11 1.40(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.55(2) . ?
O2 C7 1.22(2) . ?
N2 C7 1.36(2) . ?
N2 C8 1.48(2) . ?
N2 C9 1.35(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.51(2) . ?
O3 C11 1.212(19) . ?
N3 C9 1.36(2) . ?
N3 C12 1.34(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.53(3) . ?
N4 C10 1.37(2) . ?
N4 C12 1.35(2) . ?
N4 C13 1.43(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.56(3) . ?
C5 C6 1.46(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.37(2) . ?
C10 C11 1.42(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
I1 C14 2.072(16) . ?
F1 C15 1.34(2) . ?
I2 C17 2.102(15) . ?
F2 C16 1.35(2) . ?
F3 C18 1.34(2) . ?
F4 C19 1.332(19) . ?
C14 C15 1.41(3) . ?
C14 C19 1.38(2) . ?
C15 C16 1.36(2) . ?
C16 C17 1.37(2) . ?
C17 C18 1.35(2) . ?
C18 C19 1.38(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 118.1(14) . . ?
C7 N1 C11 126.0(14) . . ?
C11 N1 C1 115.6(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.6(17) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C7 N2 C8 119.3(16) . . ?
C9 N2 C7 118.8(14) . . ?
C9 N2 C8 122.0(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.5(16) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C12 N3 C9 102.4(14) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.2(19) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C10 N4 C13 128.0(14) . . ?
C12 N4 C10 104.5(14) . . ?
C12 N4 C13 127.5(16) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 C5 114.4(16) . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
O1 C5 C4 120(2) . . ?
O1 C5 C6 125(3) . . ?
C6 C5 C4 114(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N1 119.3(17) . . ?
O2 C7 N2 122.7(17) . . ?
N2 C7 N1 118.0(15) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N3 124.7(15) . . ?
N2 C9 C10 123.7(15) . . ?
N3 C9 C10 111.5(16) . . ?
N4 C10 C11 132.0(14) . . ?
C9 C10 N4 106.7(15) . . ?
C9 C10 C11 121.3(15) . . ?
N1 C11 C10 112.2(14) . . ?
O3 C11 N1 122.6(15) . . ?
O3 C11 C10 125.3(17) . . ?
N3 C12 N4 114.9(16) . . ?
N3 C12 H12 122.6 . . ?
N4 C12 H12 122.6 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 I1 121.6(13) . . ?
C19 C14 I1 121.9(13) . . ?
C19 C14 C15 116.5(15) . . ?
F1 C15 C14 119.6(15) . . ?
F1 C15 C16 119.2(17) . . ?
C16 C15 C14 121.2(17) . . ?
F2 C16 C15 117.6(17) . . ?
F2 C16 C17 120.7(15) . . ?
C15 C16 C17 121.7(17) . . ?
C16 C17 I2 122.1(12) . . ?
C18 C17 I2 120.7(13) . . ?
C18 C17 C16 117.2(15) . . ?
F3 C18 C17 121.9(16) . . ?
F3 C18 C19 114.7(16) . . ?
C17 C18 C19 123.3(17) . . ?
F4 C19 C14 119.9(15) . . ?
F4 C19 C18 120.0(16) . . ?
C18 C19 C14 120.1(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT342_px_tfib_thp         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02615 Ang.  
RESPONSE:  
This Alert is due to the small crystal size and the quality of the measured
crystal
;
# end Validation Reply Form
