# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_nt0076_celine_pys3-i3f3
_database_code_depnum_ccdc_archive 'CCDC 1854279'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        
'1,3,5-trifluoro-2,4,6-triiodobenzene; 2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol'
_chemical_name_common            
'1,3,5-trifluoro-2,4,6-triiodobenzene; 2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol 1:1 cocrystal'
_chemical_melting_point          402
_chemical_formula_moiety         'C12 H10 N2 O, C6 F3 I3'
_chemical_formula_sum            'C18 H10 F3 I3 N2 O'
_chemical_formula_weight         707.98

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   24.1738(4)
_cell_length_b                   9.45562(19)
_cell_length_c                   17.8360(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4076.92(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10964
_cell_measurement_theta_min      3.3180
_cell_measurement_theta_max      32.0860

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.307
_exptl_crystal_F_000             2608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    4.637
_shelx_estimated_absorpt_T_min   0.264
_shelx_estimated_absorpt_T_max   0.567
_exptl_absorpt_correction_T_min  0.273
_exptl_absorpt_correction_T_max  0.586
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_detector_area_resol_mean 10.3712
_diffrn_reflns_number            22942
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6209
_reflns_number_gt                5069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0206P)²+1.1708P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00162(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6209
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0501
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.57095(2) 0.40412(2) 0.47265(2) 0.04523(6) Uani 1 1 d . . . . .
I2 I 0.36817(2) 0.11131(2) 0.34686(2) 0.04459(6) Uani 1 1 d . . . . .
I3 I 0.43405(2) 0.01673(2) 0.66770(2) 0.05209(6) Uani 1 1 d . . . . .
F1 F 0.47612(6) 0.30065(17) 0.36088(9) 0.0518(4) Uani 1 1 d . . . . .
F2 F 0.37264(6) -0.00453(17) 0.51223(9) 0.0518(4) Uani 1 1 d . . . . .
F3 F 0.52961(6) 0.21766(19) 0.60943(9) 0.0575(4) Uani 1 1 d . . . . .
C13 C 0.50541(9) 0.2607(3) 0.48467(14) 0.0375(5) Uani 1 1 d . . . . .
C14 C 0.49502(9) 0.1941(3) 0.55165(14) 0.0376(5) Uani 1 1 d . . . . .
C15 C 0.45060(9) 0.1053(3) 0.56342(14) 0.0361(5) Uani 1 1 d . . . . .
C16 C 0.41604(9) 0.0824(2) 0.50306(14) 0.0358(5) Uani 1 1 d . . . . .
C17 C 0.42363(9) 0.1456(3) 0.43418(14) 0.0354(5) Uani 1 1 d . . . . .
C18 C 0.46858(9) 0.2354(2) 0.42661(13) 0.0371(5) Uani 1 1 d . . . . .
O1 O 0.71901(7) 1.0513(2) 0.27104(11) 0.0472(4) Uani 1 1 d . . . . .
H1O H 0.7156(13) 0.985(4) 0.298(2) 0.071 Uiso 1 1 d . U . . .
N1 N 0.74565(8) 0.8485(2) 0.36198(12) 0.0369(4) Uani 1 1 d . . . . .
N2 N 0.66188(9) 0.6019(2) 0.47082(14) 0.0466(5) Uani 1 1 d . . . . .
C1 C 0.81174(10) 0.9607(3) 0.28219(14) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.86678(11) 0.9724(3) 0.26065(17) 0.0487(6) Uani 1 1 d . . . . .
H2 H 0.892438 0.908087 0.279273 0.058 Uiso 1 1 calc R U . . .
C3 C 0.88418(13) 1.0763(3) 0.21269(18) 0.0581(8) Uani 1 1 d . . . . .
H3 H 0.921191 1.083010 0.198937 0.070 Uiso 1 1 calc R U . . .
C4 C 0.84556(13) 1.1714(3) 0.18500(17) 0.0580(8) Uani 1 1 d . . . . .
H4 H 0.857149 1.243046 0.152902 0.070 Uiso 1 1 calc R U . . .
C5 C 0.79090(12) 1.1622(3) 0.20380(15) 0.0508(6) Uani 1 1 d . . . . .
H5 H 0.765607 1.226423 0.184179 0.061 Uiso 1 1 calc R U . . .
C6 C 0.77324(10) 1.0566(3) 0.25233(13) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.79534(10) 0.8555(3) 0.33734(14) 0.0381(5) Uani 1 1 d . . . . .
H7 H 0.821556 0.791872 0.355161 0.046 Uiso 1 1 calc R U . . .
C8 C 0.73232(9) 0.7508(2) 0.41928(13) 0.0338(5) Uani 1 1 d . . . . .
C9 C 0.76812(10) 0.7120(3) 0.47642(15) 0.0431(6) Uani 1 1 d . . . . .
H9 H 0.803915 0.747914 0.478294 0.052 Uiso 1 1 calc R U . . .
C10 C 0.74956(12) 0.6195(3) 0.53026(16) 0.0486(6) Uani 1 1 d . . . . .
H10 H 0.772603 0.591884 0.569361 0.058 Uiso 1 1 calc R U . . .
C11 C 0.69687(11) 0.5686(3) 0.52552(16) 0.0475(6) Uani 1 1 d . . . . .
H11 H 0.684725 0.507156 0.562742 0.057 Uiso 1 1 calc R U . . .
C12 C 0.67970(9) 0.6928(3) 0.41892(14) 0.0383(5) Uani 1 1 d . . . . .
H12 H 0.655603 0.718551 0.380631 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C13 2.096(2) . ?
I2 C17 2.080(2) . ?
I3 C15 2.079(2) . ?
F1 C18 1.337(3) . ?
F2 C16 1.343(3) . ?
F3 C14 1.346(3) . ?
C13 C14 1.374(3) . ?
C13 C18 1.386(3) . ?
C14 C15 1.379(3) . ?
C15 C16 1.380(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.386(3) . ?
O1 C6 1.354(3) . ?
O1 H1O 0.80(3) . ?
N1 C7 1.281(3) . ?
N1 C8 1.415(3) . ?
N2 C11 1.329(4) . ?
N2 C12 1.335(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.405(4) . ?
C1 C7 1.454(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.385(3) . ?
C8 C9 1.386(3) . ?
C9 C10 1.375(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C13 C18 116.9(2) . . ?
C14 C13 I1 121.58(17) . . ?
C18 C13 I1 121.37(18) . . ?
F3 C14 C13 118.5(2) . . ?
F3 C14 C15 117.9(2) . . ?
C13 C14 C15 123.6(2) . . ?
C14 C15 C16 116.6(2) . . ?
C14 C15 I3 122.10(18) . . ?
C16 C15 I3 121.22(17) . . ?
F2 C16 C17 118.6(2) . . ?
F2 C16 C15 118.3(2) . . ?
C17 C16 C15 123.1(2) . . ?
C16 C17 C18 117.2(2) . . ?
C16 C17 I2 120.91(17) . . ?
C18 C17 I2 121.87(18) . . ?
F1 C18 C17 118.4(2) . . ?
F1 C18 C13 119.2(2) . . ?
C17 C18 C13 122.4(2) . . ?
C6 O1 H1O 106(2) . . ?
C7 N1 C8 119.7(2) . . ?
C11 N2 C12 117.1(2) . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 C7 120.2(2) . . ?
C6 C1 C7 121.2(2) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
O1 C6 C5 118.6(2) . . ?
O1 C6 C1 121.6(2) . . ?
C5 C6 C1 119.8(2) . . ?
N1 C7 C1 121.6(2) . . ?
N1 C7 H7 119.2 . . ?
C1 C7 H7 119.2 . . ?
C12 C8 C9 118.2(2) . . ?
C12 C8 N1 117.6(2) . . ?
C9 C8 N1 124.2(2) . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N2 C11 C10 123.8(3) . . ?
N2 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N2 C12 C8 123.2(2) . . ?
N2 C12 H12 118.4 . . ?
C8 C12 H12 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 C13 C14 F3 -179.2(2) . . . . ?
I1 C13 C14 F3 -3.0(3) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
I1 C13 C14 C15 176.15(19) . . . . ?
F3 C14 C15 C16 -179.6(2) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
F3 C14 C15 I3 3.0(3) . . . . ?
C13 C14 C15 I3 -176.20(19) . . . . ?
C14 C15 C16 F2 179.3(2) . . . . ?
I3 C15 C16 F2 -3.2(3) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
I3 C15 C16 C17 176.10(18) . . . . ?
F2 C16 C17 C18 179.6(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
F2 C16 C17 I2 1.5(3) . . . . ?
C15 C16 C17 I2 -177.86(18) . . . . ?
C16 C17 C18 F1 -178.5(2) . . . . ?
I2 C17 C18 F1 -0.3(3) . . . . ?
C16 C17 C18 C13 0.9(4) . . . . ?
I2 C17 C18 C13 179.09(18) . . . . ?
C14 C13 C18 F1 178.3(2) . . . . ?
I1 C13 C18 F1 2.1(3) . . . . ?
C14 C13 C18 C17 -1.1(4) . . . . ?
I1 C13 C18 C17 -177.28(18) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C7 C1 C2 C3 -175.6(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 O1 178.9(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C2 C1 C6 O1 -179.9(2) . . . . ?
C7 C1 C6 O1 -3.0(4) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C7 C1 C6 C5 175.4(2) . . . . ?
C8 N1 C7 C1 -175.8(2) . . . . ?
C2 C1 C7 N1 175.3(2) . . . . ?
C6 C1 C7 N1 -1.6(4) . . . . ?
C7 N1 C8 C12 -147.7(2) . . . . ?
C7 N1 C8 C9 33.7(4) . . . . ?
C12 C8 C9 C10 -0.7(4) . . . . ?
N1 C8 C9 C10 177.9(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C12 N2 C11 C10 -1.5(4) . . . . ?
C9 C10 C11 N2 0.9(5) . . . . ?
C11 N2 C12 C8 1.0(4) . . . . ?
C9 C8 C12 N2 0.1(4) . . . . ?
N1 C8 C12 N2 -178.6(2) . . . . ?

_refine_diff_density_max         0.601
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_salan_14tfib
_database_code_depnum_ccdc_archive 'CCDC 1854281'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 F4 I2 N O'
_chemical_formula_sum            'C19 H11 F4 I2 N O'
_chemical_formula_weight         599.09

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3298(5)
_cell_length_b                   5.9839(4)
_cell_length_c                   15.276(2)
_cell_angle_alpha                90.196(8)
_cell_angle_beta                 93.824(9)
_cell_angle_gamma                100.428(7)
_cell_volume                     478.01(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    295
_cell_measurement_reflns_used    1449
_cell_measurement_theta_min      4.5680
_cell_measurement_theta_max      26.3640

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_F_000             282
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.335
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3426
_diffrn_reflns_number            3293
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.206
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2079
_reflns_number_gt                1592
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2079
_refine_ls_number_parameters     190
_refine_ls_number_restraints     92
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.420(4) 0.934(6) 0.4854(17) 0.063(7) Uani 0.5 1 d . U P A -1
O1 O 0.594(2) 0.6584(15) 0.5900(7) 0.098(3) Uani 0.5 1 d . . P A -1
H1 H 0.4939 0.6998 0.5531 0.147 Uiso 0.5 1 calc R U P A -1
C7 C 0.603(7) 1.085(6) 0.516(3) 0.089(14) Uani 0.5 1 d . . P A -1
H7 H 0.6145 1.2305 0.4932 0.107 Uiso 0.5 1 calc R U P A -1
C1 C 0.776(7) 1.052(7) 0.577(3) 0.052(7) Uani 0.5 1 d D U P A -1
C2 C 0.782(8) 0.850(6) 0.621(3) 0.061(7) Uani 0.5 1 d D U P A -1
C3 C 0.963(5) 0.844(3) 0.6899(19) 0.066(5) Uani 0.5 1 d D U P A -1
H3 H 0.9360 0.7274 0.7300 0.079 Uiso 0.5 1 calc R U P A -1
C4 C 1.181(6) 1.009(5) 0.701(2) 0.066(8) Uani 0.5 1 d D U P A -1
H4 H 1.3197 0.9895 0.7380 0.079 Uiso 0.5 1 calc R U P A -1
C5 C 1.180(5) 1.203(5) 0.6520(15) 0.058(6) Uani 0.5 1 d D U P A -1
H5 H 1.3194 1.3223 0.6572 0.069 Uiso 0.5 1 calc R U P A -1
C6 C 0.970(8) 1.220(8) 0.596(3) 0.077(11) Uani 0.5 1 d D U P A -1
H6 H 0.9653 1.3588 0.5691 0.092 Uiso 0.5 1 calc R U P A -1
C8 C 0.213(8) 0.981(7) 0.413(3) 0.058(8) Uani 0.5 1 d D U P A -1
C9 C 0.227(9) 1.191(6) 0.373(4) 0.079(11) Uani 0.5 1 d D U P A -1
H9 H 0.3673 1.3070 0.3847 0.095 Uiso 0.5 1 calc R U P A -1
C10 C 0.022(6) 1.222(3) 0.3168(19) 0.063(5) Uani 0.5 1 d D U P A -1
H10 H 0.0049 1.3670 0.2983 0.075 Uiso 0.5 1 calc R U P A -1
C11 C -0.156(6) 1.035(4) 0.288(3) 0.059(7) Uani 0.5 1 d D U P A -1
H11 H -0.2752 1.0525 0.2425 0.071 Uiso 0.5 1 calc R U P A -1
C12 C -0.166(5) 0.822(5) 0.3246(15) 0.061(6) Uani 0.5 1 d D U P A -1
H12 H -0.2907 0.7010 0.3038 0.073 Uiso 0.5 1 calc R U P A -1
C13 C 0.010(9) 0.789(7) 0.392(3) 0.058(7) Uani 0.5 1 d D U P A -1
H13 H -0.0016 0.6524 0.4218 0.069 Uiso 0.5 1 calc R U P A -1
C14 C 0.6337(9) 0.3870(8) 0.9437(4) 0.0505(12) Uani 1 1 d . . . . .
C15 C 0.5044(10) 0.5532(9) 0.9133(4) 0.0555(13) Uani 1 1 d . . . . .
C16 C 0.3720(10) 0.6643(9) 0.9689(4) 0.0558(13) Uani 1 1 d . . . . .
F1 F 0.5000(8) 0.6078(6) 0.8276(2) 0.0819(10) Uani 1 1 d . . . . .
F2 F 0.2453(8) 0.8231(6) 0.9348(3) 0.0847(11) Uani 1 1 d . . . . .
I1 I 0.83182(7) 0.21984(6) 0.85925(3) 0.0711(2) 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
N1 C7 1.27(2) . ?
N1 C8 1.58(4) . ?
O1 C2 1.44(3) . ?
O1 H1 0.8200 . ?
C7 C1 1.31(5) . ?
C7 H7 0.9300 . ?
C1 C2 1.386(10) . ?
C1 C6 1.32(5) . ?
C2 C3 1.386(10) . ?
C3 C4 1.380(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C13 1.45(5) . ?
C8 C9 1.386(10) . ?
C9 C10 1.385(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C16 1.371(7) 2_667 ?
C14 C15 1.374(7) . ?
C14 I1 2.082(5) . ?
C15 F1 1.349(6) . ?
C15 C16 1.382(7) . ?
C16 F2 1.349(6) . ?
C16 C14 1.371(7) 2_667 ?

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 C8 123(3) . . ?
C2 O1 H1 109.5 . . ?
N1 C7 C1 125(2) . . ?
N1 C7 H7 117.6 . . ?
C1 C7 H7 117.6 . . ?
C7 C1 C2 126(3) . . ?
C7 C1 C6 118(3) . . ?
C2 C1 C6 117(2) . . ?
C3 C2 C1 119.6(17) . . ?
C3 C2 O1 124(3) . . ?
C1 C2 O1 116(2) . . ?
C4 C3 C2 121(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 116(2) . . ?
C3 C4 H4 122.0 . . ?
C5 C4 H4 122.0 . . ?
C6 C5 C4 119.4(18) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 125(3) . . ?
C5 C6 H6 117.7 . . ?
C1 C6 H6 117.7 . . ?
C13 C8 C9 124(2) . . ?
C13 C8 N1 114(3) . . ?
C9 C8 N1 122(3) . . ?
C10 C9 C8 117(2) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C11 C10 C9 119.1(15) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 123(2) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C13 C12 C11 120(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C8 C13 C12 115(3) . . ?
C8 C13 H13 122.4 . . ?
C12 C13 H13 122.4 . . ?
C16 C14 C15 117.9(5) 2_667 . ?
C16 C14 I1 121.4(4) 2_667 . ?
C15 C14 I1 120.7(4) . . ?
F1 C15 C14 120.4(5) . . ?
F1 C15 C16 118.6(5) . . ?
C14 C15 C16 121.0(5) . . ?
F2 C16 C14 120.7(5) . 2_667 ?
F2 C16 C15 118.2(5) . . ?
C14 C16 C15 121.1(5) 2_667 . ?

_refine_diff_density_max         0.928
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_sal_3AP_135tfib_2to1
_database_code_depnum_ccdc_archive 'CCDC 1854280'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H10 N2 O), C6 F3 I3'
_chemical_formula_sum            'C30 H20 F3 I3 N4 O2'
_chemical_formula_weight         906.20

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.1899(3)
_cell_length_b                   29.106(2)
_cell_length_c                   24.6798(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.834(7)
_cell_angle_gamma                90
_cell_volume                     3006.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      4.1940
_cell_measurement_theta_max      25.3110

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.173
_shelx_estimated_absorpt_T_min   0.274
_shelx_estimated_absorpt_T_max   0.808
_exptl_absorpt_correction_T_min  0.87727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11822
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.306
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             4955
_reflns_number_gt                3884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/8 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3960(14) 0.2386(3) 0.9125(3) 0.0415(17) Uani 1 1 d . . . . .
C2 C 0.3946(16) 0.2833(3) 0.9311(3) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.3093 0.2893 0.9645 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5138(18) 0.3190(3) 0.9025(4) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.5064 0.3489 0.9157 0.074 Uiso 1 1 calc R U . . .
C4 C 0.6462(18) 0.3097(3) 0.8533(4) 0.066(2) Uani 1 1 d . . . . .
H4 H 0.7265 0.3337 0.8331 0.079 Uiso 1 1 calc R U . . .
C5 C 0.6605(17) 0.2655(3) 0.8337(3) 0.061(2) Uani 1 1 d . . . . .
H5 H 0.7563 0.2597 0.8012 0.073 Uiso 1 1 calc R U . . .
C6 C 0.5306(15) 0.2292(3) 0.8628(3) 0.0446(18) Uani 1 1 d . . . . .
C7 C 0.2537(15) 0.2023(3) 0.9440(3) 0.0468(18) Uani 1 1 d . . . . .
H7 H 0.1724 0.2095 0.9773 0.056 Uiso 1 1 calc R U . . .
C8 C 0.1035(14) 0.1263(2) 0.9597(3) 0.0397(17) Uani 1 1 d . . . . .
C9 C -0.0812(15) 0.0931(3) 0.9344(3) 0.0449(18) Uani 1 1 d . . . . .
H9 H -0.1265 0.0941 0.8972 0.054 Uiso 1 1 calc R U . . .
C10 C -0.1988(15) 0.0582(3) 0.9656(3) 0.0478(19) Uani 1 1 d . . . . .
H10 H -0.3272 0.0354 0.9496 0.057 Uiso 1 1 calc R U . . .
C11 C -0.1240(15) 0.0575(3) 1.0205(3) 0.0496(19) Uani 1 1 d . . . . .
H11 H -0.2038 0.0337 1.0410 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1675(15) 0.1224(3) 1.0155(3) 0.0477(19) Uani 1 1 d . . . . .
H12 H 0.2968 0.1446 1.0324 0.057 Uiso 1 1 calc R U . . .
N1 N 0.2379(12) 0.1608(2) 0.9270(2) 0.0445(14) Uani 1 1 d . . . . .
N2 N 0.0562(13) 0.0892(2) 1.0457(2) 0.0498(15) Uani 1 1 d . . . . .
O1 O 0.5390(14) 0.1873(2) 0.8415(2) 0.0656(16) Uani 1 1 d . . . . .
H1O H 0.452(17) 0.169(3) 0.864(3) 0.07(3) Uiso 1 1 d . . . . .
C14 C 0.0636(13) 0.0242(2) 0.7048(2) 0.0330(15) Uani 1 1 d . . . . .
C15 C 0.1718(13) -0.0198(2) 0.6963(2) 0.0348(16) Uani 1 1 d . . . . .
C16 C 0.3481(14) -0.0402(2) 0.7380(3) 0.0343(15) Uani 1 1 d . . . . .
C17 C 0.4148(12) -0.0186(2) 0.7876(2) 0.0315(15) Uani 1 1 d . . . . .
C18 C 0.2997(13) 0.0251(2) 0.7936(2) 0.0330(15) Uani 1 1 d . . . . .
C19 C 0.1198(13) 0.0479(2) 0.7534(3) 0.0353(16) Uani 1 1 d . . . . .
F1 F -0.1125(8) 0.04569(14) 0.66522(14) 0.0504(10) Uani 1 1 d . . . . .
F2 F 0.4553(8) -0.08312(14) 0.73102(15) 0.0506(10) Uani 1 1 d . . . . .
F3 F 0.3563(8) 0.04646(14) 0.84121(14) 0.0497(10) Uani 1 1 d . . . . .
I1 I 0.06836(9) -0.05314(2) 0.62171(2) 0.04326(14) Uani 1 1 d . . . . .
I2 I 0.65488(9) -0.05286(2) 0.85251(2) 0.04002(14) Uani 1 1 d . . . . .
I3 I -0.05661(10) 0.11352(2) 0.76523(2) 0.04755(15) Uani 1 1 d . . . . .
C21 C 0.0785(15) 0.2428(3) 0.6467(3) 0.0472(18) Uani 1 1 d . . . . .
C22 C 0.1861(17) 0.2573(3) 0.6982(3) 0.061(2) Uani 1 1 d . . . . .
H22 H 0.3084 0.2373 0.7200 0.074 Uiso 1 1 calc R U . . .
C23 C 0.1176(18) 0.3003(3) 0.7180(3) 0.061(2) Uani 1 1 d . . . . .
H23 H 0.1904 0.3090 0.7527 0.074 Uiso 1 1 calc R U . . .
C24 C -0.0633(18) 0.3304(3) 0.6849(3) 0.061(2) Uani 1 1 d . . . . .
H24 H -0.1123 0.3595 0.6975 0.073 Uiso 1 1 calc R U . . .
C25 C -0.1677(18) 0.3173(3) 0.6344(3) 0.064(2) Uani 1 1 d . . . . .
H25 H -0.2860 0.3378 0.6127 0.077 Uiso 1 1 calc R U . . .
C26 C -0.1022(17) 0.2741(3) 0.6146(3) 0.0511(19) Uani 1 1 d . . . . .
C27 C 0.1635(16) 0.1989(3) 0.6274(3) 0.053(2) Uani 1 1 d . . . . .
H27 H 0.2945 0.1804 0.6498 0.064 Uiso 1 1 calc R U . . .
C28 C 0.1555(14) 0.1396(3) 0.5621(3) 0.0409(17) Uani 1 1 d . . . . .
C29 C 0.3438(17) 0.1066(3) 0.5896(3) 0.054(2) Uani 1 1 d . . . . .
H29 H 0.4296 0.1125 0.6244 0.065 Uiso 1 1 calc R U . . .
C30 C 0.3993(17) 0.0661(3) 0.5649(3) 0.058(2) Uani 1 1 d . . . . .
H30 H 0.5206 0.0436 0.5830 0.069 Uiso 1 1 calc R U . . .
C31 C 0.2771(17) 0.0582(3) 0.5133(3) 0.054(2) Uani 1 1 d . . . . .
H31 H 0.3223 0.0304 0.4968 0.064 Uiso 1 1 calc R U . . .
C32 C 0.0391(15) 0.1278(3) 0.5098(3) 0.0487(19) Uani 1 1 d . . . . .
H32 H -0.0877 0.1492 0.4908 0.058 Uiso 1 1 calc R U . . .
N3 N 0.0687(12) 0.1831(2) 0.5804(2) 0.0463(15) Uani 1 1 d . . . . .
N4 N 0.0965(13) 0.0886(2) 0.4857(2) 0.0529(16) Uani 1 1 d . . . . .
O2 O -0.2147(16) 0.2629(2) 0.5638(2) 0.0789(18) Uani 1 1 d . . . . .
H2A H -0.1397 0.2381 0.5551 0.118 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(10) . ?
C1 C6 1.401(10) . ?
C1 C7 1.457(10) . ?
C2 C3 1.366(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(10) . ?
C5 H5 0.9300 . ?
C6 O1 1.331(9) . ?
C7 N1 1.279(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(9) . ?
C8 C12 1.394(9) . ?
C8 N1 1.423(9) . ?
C9 C10 1.379(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(9) . ?
C10 H10 0.9300 . ?
C11 N2 1.327(9) . ?
C11 H11 0.9300 . ?
C12 N2 1.320(9) . ?
C12 H12 0.9300 . ?
O1 H1O 0.87(8) . ?
C14 F1 1.348(6) . ?
C14 C15 1.380(9) . ?
C14 C19 1.392(8) . ?
C15 C16 1.372(8) . ?
C15 I1 2.107(6) . ?
C16 F2 1.341(7) . ?
C16 C17 1.392(8) . ?
C17 C18 1.370(9) . ?
C17 I2 2.102(6) . ?
C18 F3 1.339(7) . ?
C18 C19 1.385(8) . ?
C19 I3 2.075(7) . ?
C21 C22 1.394(9) . ?
C21 C26 1.405(10) . ?
C21 C27 1.415(10) . ?
C22 C23 1.378(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.353(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(11) . ?
C25 H25 0.9300 . ?
C26 O2 1.359(8) . ?
C27 N3 1.291(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.397(9) . ?
C28 C32 1.398(9) . ?
C28 N3 1.401(9) . ?
C29 C30 1.354(10) . ?
C29 H29 0.9300 . ?
C30 C31 1.368(9) . ?
C30 H30 0.9300 . ?
C31 N4 1.330(9) . ?
C31 H31 0.9300 . ?
C32 N4 1.316(9) . ?
C32 H32 0.9300 . ?
O2 H2A 0.8200 . ?

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 C6 119.0(7) . . ?
C2 C1 C7 119.8(7) . . ?
C6 C1 C7 121.2(7) . . ?
C3 C2 C1 122.5(8) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 118.4(8) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 121.1(8) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.9(8) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
O1 C6 C1 123.0(7) . . ?
O1 C6 C5 118.0(7) . . ?
C1 C6 C5 119.0(7) . . ?
N1 C7 C1 121.7(7) . . ?
N1 C7 H7 119.1 . . ?
C1 C7 H7 119.1 . . ?
C9 C8 C12 118.0(7) . . ?
C9 C8 N1 118.1(6) . . ?
C12 C8 N1 123.7(6) . . ?
C8 C9 C10 118.4(7) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 119.3(7) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N2 C11 C10 123.3(7) . . ?
N2 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N2 C12 C8 124.2(7) . . ?
N2 C12 H12 117.9 . . ?
C8 C12 H12 117.9 . . ?
C7 N1 C8 119.8(6) . . ?
C12 N2 C11 116.8(6) . . ?
C6 O1 H1O 108(6) . . ?
F1 C14 C15 119.6(6) . . ?
F1 C14 C19 117.2(6) . . ?
C15 C14 C19 123.2(6) . . ?
C16 C15 C14 117.2(6) . . ?
C16 C15 I1 122.4(5) . . ?
C14 C15 I1 120.3(4) . . ?
F2 C16 C15 118.6(6) . . ?
F2 C16 C17 118.7(5) . . ?
C15 C16 C17 122.7(6) . . ?
C18 C17 C16 117.4(6) . . ?
C18 C17 I2 121.0(5) . . ?
C16 C17 I2 121.5(5) . . ?
F3 C18 C17 118.6(5) . . ?
F3 C18 C19 118.3(6) . . ?
C17 C18 C19 123.2(6) . . ?
C18 C19 C14 116.4(6) . . ?
C18 C19 I3 121.6(5) . . ?
C14 C19 I3 122.0(5) . . ?
C22 C21 C26 117.3(7) . . ?
C22 C21 C27 120.3(7) . . ?
C26 C21 C27 122.3(7) . . ?
C23 C22 C21 122.3(8) . . ?
C23 C22 H22 118.8 . . ?
C21 C22 H22 118.8 . . ?
C22 C23 C24 118.6(7) . . ?
C22 C23 H23 120.7 . . ?
C24 C23 H23 120.7 . . ?
C25 C24 C23 120.2(8) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 121.4(8) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
O2 C26 C25 118.8(7) . . ?
O2 C26 C21 121.1(7) . . ?
C25 C26 C21 120.1(7) . . ?
N3 C27 C21 123.4(7) . . ?
N3 C27 H27 118.3 . . ?
C21 C27 H27 118.3 . . ?
C29 C28 C32 116.4(7) . . ?
C29 C28 N3 127.8(6) . . ?
C32 C28 N3 115.8(6) . . ?
C30 C29 C28 118.9(7) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C29 C30 C31 120.1(7) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
N4 C31 C30 122.9(7) . . ?
N4 C31 H31 118.5 . . ?
C30 C31 H31 118.5 . . ?
N4 C32 C28 124.5(6) . . ?
N4 C32 H32 117.7 . . ?
C28 C32 H32 117.7 . . ?
C27 N3 C28 122.6(6) . . ?
C32 N4 C31 117.2(6) . . ?
C26 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(10) . . . . ?
C7 C1 C2 C3 -177.6(6) . . . . ?
C1 C2 C3 C4 -1.2(11) . . . . ?
C2 C3 C4 C5 -0.6(12) . . . . ?
C3 C4 C5 C6 2.1(11) . . . . ?
C2 C1 C6 O1 -179.2(6) . . . . ?
C7 C1 C6 O1 -0.2(10) . . . . ?
C2 C1 C6 C5 0.1(10) . . . . ?
C7 C1 C6 C5 179.1(6) . . . . ?
C4 C5 C6 O1 177.5(6) . . . . ?
C4 C5 C6 C1 -1.9(10) . . . . ?
C2 C1 C7 N1 177.0(6) . . . . ?
C6 C1 C7 N1 -2.0(10) . . . . ?
C12 C8 C9 C10 1.2(10) . . . . ?
N1 C8 C9 C10 176.8(6) . . . . ?
C8 C9 C10 C11 -0.8(10) . . . . ?
C9 C10 C11 N2 0.4(11) . . . . ?
C9 C8 C12 N2 -1.3(10) . . . . ?
N1 C8 C12 N2 -176.7(6) . . . . ?
C1 C7 N1 C8 178.6(5) . . . . ?
C9 C8 N1 C7 141.6(6) . . . . ?
C12 C8 N1 C7 -43.0(9) . . . . ?
C8 C12 N2 C11 0.9(10) . . . . ?
C10 C11 N2 C12 -0.5(10) . . . . ?
F1 C14 C15 C16 -179.6(5) . . . . ?
C19 C14 C15 C16 -1.3(9) . . . . ?
F1 C14 C15 I1 0.8(8) . . . . ?
C19 C14 C15 I1 179.1(4) . . . . ?
C14 C15 C16 F2 179.7(5) . . . . ?
I1 C15 C16 F2 -0.7(8) . . . . ?
C14 C15 C16 C17 1.0(9) . . . . ?
I1 C15 C16 C17 -179.4(4) . . . . ?
F2 C16 C17 C18 -179.4(5) . . . . ?
C15 C16 C17 C18 -0.8(9) . . . . ?
F2 C16 C17 I2 -3.6(7) . . . . ?
C15 C16 C17 I2 175.1(5) . . . . ?
C16 C17 C18 F3 179.0(5) . . . . ?
I2 C17 C18 F3 3.1(7) . . . . ?
C16 C17 C18 C19 0.8(9) . . . . ?
I2 C17 C18 C19 -175.1(4) . . . . ?
F3 C18 C19 C14 -179.3(5) . . . . ?
C17 C18 C19 C14 -1.1(9) . . . . ?
F3 C18 C19 I3 0.5(8) . . . . ?
C17 C18 C19 I3 178.7(5) . . . . ?
F1 C14 C19 C18 179.7(5) . . . . ?
C15 C14 C19 C18 1.4(9) . . . . ?
F1 C14 C19 I3 -0.1(7) . . . . ?
C15 C14 C19 I3 -178.4(5) . . . . ?
C26 C21 C22 C23 0.8(11) . . . . ?
C27 C21 C22 C23 177.9(7) . . . . ?
C21 C22 C23 C24 -0.7(12) . . . . ?
C22 C23 C24 C25 -0.1(11) . . . . ?
C23 C24 C25 C26 0.7(12) . . . . ?
C24 C25 C26 O2 179.7(7) . . . . ?
C24 C25 C26 C21 -0.5(12) . . . . ?
C22 C21 C26 O2 179.6(7) . . . . ?
C27 C21 C26 O2 2.5(11) . . . . ?
C22 C21 C26 C25 -0.2(11) . . . . ?
C27 C21 C26 C25 -177.3(7) . . . . ?
C22 C21 C27 N3 179.1(6) . . . . ?
C26 C21 C27 N3 -3.9(11) . . . . ?
C32 C28 C29 C30 -0.5(10) . . . . ?
N3 C28 C29 C30 179.6(7) . . . . ?
C28 C29 C30 C31 1.3(12) . . . . ?
C29 C30 C31 N4 -1.4(12) . . . . ?
C29 C28 C32 N4 -0.3(10) . . . . ?
N3 C28 C32 N4 179.7(7) . . . . ?
C21 C27 N3 C28 180.0(6) . . . . ?
C29 C28 N3 C27 1.2(11) . . . . ?
C32 C28 N3 C27 -178.7(6) . . . . ?
C28 C32 N4 C31 0.2(11) . . . . ?
C30 C31 N4 C32 0.6(11) . . . . ?

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
O1 H1O N1 0.87(8) 1.85(8) 2.628(8) 148(8) .
C30 H30 F1 0.93 2.48 3.188(7) 132.5 1_655
O2 H2A N3 0.82 1.91 2.630(8) 145.7 .

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_nt0179_Andrea_PYS3_mI2F4
_database_code_depnum_ccdc_archive 'CCDC 1854282'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
1,2,3,5-tetrafluoro-4,6-diiodobenzene; 
2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol
;
_chemical_name_common            
;
1,2,3,5-tetrafluoro-4,6-diiodobenzene 
2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol 1:1 cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O, C6 F4 I2'
_chemical_formula_sum            'C18 H10 F4 I2 N2 O'
_chemical_formula_weight         600.08

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2968(5)
_cell_length_b                   15.2068(12)
_cell_length_c                   19.3646(15)
_cell_angle_alpha                110.783(7)
_cell_angle_beta                 91.701(6)
_cell_angle_gamma                100.999(6)
_cell_volume                     1960.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    7481
_cell_measurement_theta_min      2.2050
_cell_measurement_theta_max      31.0830

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.033
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.254
_shelx_estimated_absorpt_T_min   0.272
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_T_min  0.276
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_reflns_number            19759
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9739
_reflns_number_gt                7450
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0276P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00679(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9739
_refine_ls_number_parameters     490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.07873(3) 0.30413(2) 0.61404(2) 0.05637(8) Uani 1 1 d . . . . .
I2A I 0.02779(3) 0.71278(2) 0.80460(2) 0.06156(8) Uani 1 1 d . . . . .
F1A F -0.0461(3) 0.28444(13) 0.76358(12) 0.0725(6) Uani 1 1 d . . . . .
F2A F -0.1177(3) 0.40995(16) 0.89140(12) 0.0825(7) Uani 1 1 d . . . . .
F3A F -0.0881(3) 0.59560(15) 0.91070(12) 0.0719(6) Uani 1 1 d . . . . .
F4A F 0.0928(3) 0.53247(14) 0.67004(11) 0.0627(5) Uani 1 1 d . . . . .
C13A C 0.0202(4) 0.4049(2) 0.71209(16) 0.0437(7) Uani 1 1 d . . . . .
C14A C -0.0327(4) 0.3769(2) 0.77031(19) 0.0495(7) Uani 1 1 d . . . . .
C15A C -0.0701(5) 0.4407(3) 0.8360(2) 0.0551(8) Uani 1 1 d . . . . .
C16A C -0.0528(4) 0.5351(2) 0.84562(18) 0.0506(7) Uani 1 1 d . . . . .
C17A C 0.0015(4) 0.5681(2) 0.78965(18) 0.0465(7) Uani 1 1 d . . . . .
C18A C 0.0357(4) 0.5012(2) 0.72462(17) 0.0440(7) Uani 1 1 d . . . . .
I1B I 0.63165(3) 0.23158(2) 0.39052(2) 0.06522(8) Uani 1 1 d . . . . .
I2B I 0.55067(3) -0.20090(2) 0.23565(2) 0.06856(9) Uani 1 1 d . . . . .
F1B F 0.4688(3) 0.19144(15) 0.22486(13) 0.0814(7) Uani 1 1 d . . . . .
F2B F 0.3863(3) 0.03214(18) 0.10129(13) 0.0895(7) Uani 1 1 d . . . . .
F3B F 0.4201(3) -0.13826(16) 0.10591(13) 0.0815(6) Uani 1 1 d . . . . .
F4B F 0.6435(3) 0.01099(14) 0.35877(11) 0.0649(5) Uani 1 1 d . . . . .
C13B C 0.5609(4) 0.1056(2) 0.29549(19) 0.0513(8) Uani 1 1 d . . . . .
C14B C 0.4933(5) 0.1076(2) 0.2287(2) 0.0562(9) Uani 1 1 d . . . . .
C15B C 0.4485(5) 0.0268(3) 0.1652(2) 0.0589(9) Uani 1 1 d . . . . .
C16B C 0.4675(5) -0.0597(2) 0.1679(2) 0.0549(8) Uani 1 1 d . . . . .
C17B C 0.5304(4) -0.0674(2) 0.2334(2) 0.0515(8) Uani 1 1 d . . . . .
C18B C 0.5774(4) 0.0163(2) 0.29488(18) 0.0490(8) Uani 1 1 d . . . . .
O1A O -0.0482(4) 0.08818(16) 0.19566(14) 0.0682(7) Uani 1 1 d . . . . .
H1A H -0.011241 0.089056 0.236357 0.102 Uiso 1 1 calc R U . . .
N1A N 0.0627(3) 0.02155(18) 0.29231(14) 0.0459(6) Uani 1 1 d . . . . .
N2A N 0.1682(4) 0.1492(2) 0.49208(17) 0.0690(8) Uani 1 1 d . . . . .
C1A C -0.0225(4) -0.0759(2) 0.16387(17) 0.0455(7) Uani 1 1 d . . . . .
C2A C -0.0456(5) -0.1667(2) 0.1089(2) 0.0649(9) Uani 1 1 d . . . . .
H2A H -0.015458 -0.216756 0.120724 0.078 Uiso 1 1 calc R U . . .
C3A C -0.1122(6) -0.1836(3) 0.0373(2) 0.0774(11) Uani 1 1 d . . . . .
H3A H -0.126100 -0.244498 0.000665 0.093 Uiso 1 1 calc R U . . .
C4A C -0.1581(6) -0.1099(3) 0.0202(2) 0.0770(11) Uani 1 1 d . . . . .
H4A H -0.205145 -0.121791 -0.028211 0.092 Uiso 1 1 calc R U . . .
C5A C -0.1365(5) -0.0195(3) 0.0724(2) 0.0651(10) Uani 1 1 d . . . . .
H5A H -0.167364 0.029576 0.059452 0.078 Uiso 1 1 calc R U . . .
C6A C -0.0683(4) -0.0011(2) 0.14491(19) 0.0515(8) Uani 1 1 d . . . . .
C7A C 0.0420(4) -0.0606(2) 0.23979(18) 0.0479(7) Uani 1 1 d . . . . .
H7A H 0.068994 -0.112016 0.250486 0.057 Uiso 1 1 calc R U . . .
C8A C 0.1237(4) 0.0359(2) 0.36654(18) 0.0460(7) Uani 1 1 d . . . . .
C9A C 0.1930(5) -0.0292(2) 0.38982(19) 0.0580(8) Uani 1 1 d . . . . .
H9A H 0.201765 -0.089051 0.355862 0.070 Uiso 1 1 calc R U . . .
C10A C 0.2480(5) -0.0033(3) 0.4638(2) 0.0694(10) Uani 1 1 d . . . . .
H10A H 0.295296 -0.045520 0.480704 0.083 Uiso 1 1 calc R U . . .
C11A C 0.2331(5) 0.0847(3) 0.5126(2) 0.0698(10) Uani 1 1 d . . . . .
H11A H 0.270021 0.100662 0.562735 0.084 Uiso 1 1 calc R U . . .
C12A C 0.1148(5) 0.1229(2) 0.4199(2) 0.0579(8) Uani 1 1 d . . . . .
H12A H 0.068213 0.166520 0.404575 0.069 Uiso 1 1 calc R U . . .
O1B O 0.4556(4) 0.39898(17) 0.77737(14) 0.0675(7) Uani 1 1 d . . . . .
H1B H 0.491305 0.410633 0.741158 0.101 Uiso 1 1 calc R U . . .
N1B N 0.5611(3) 0.50030(18) 0.69912(14) 0.0466(6) Uani 1 1 d . . . . .
N2B N 0.6991(4) 0.4099(2) 0.51260(17) 0.0681(8) Uani 1 1 d . . . . .
C1B C 0.4799(4) 0.5703(2) 0.82213(18) 0.0480(7) Uani 1 1 d . . . . .
C2B C 0.4628(5) 0.6527(3) 0.8795(2) 0.0635(9) Uani 1 1 d . . . . .
H2B H 0.488834 0.711439 0.873030 0.076 Uiso 1 1 calc R U . . .
C3B C 0.4078(6) 0.6495(4) 0.9462(2) 0.0832(12) Uani 1 1 d . . . . .
H3B H 0.397977 0.705592 0.984778 0.100 Uiso 1 1 calc R U . . .
C4B C 0.3680(6) 0.5626(4) 0.9549(2) 0.0856(14) Uani 1 1 d . . . . .
H4B H 0.329147 0.560216 0.999666 0.103 Uiso 1 1 calc R U . . .
C5B C 0.3840(5) 0.4783(4) 0.8989(2) 0.0746(12) Uani 1 1 d . . . . .
H5B H 0.357049 0.420015 0.905993 0.090 Uiso 1 1 calc R U . . .
C6B C 0.4407(5) 0.4817(3) 0.83193(19) 0.0543(8) Uani 1 1 d . . . . .
C7B C 0.5359(4) 0.5751(2) 0.75243(18) 0.0462(7) Uani 1 1 d . . . . .
H7B H 0.554158 0.633802 0.745968 0.055 Uiso 1 1 calc R U . . .
C8B C 0.6266(4) 0.5048(2) 0.63243(17) 0.0448(7) Uani 1 1 d . . . . .
C9B C 0.6878(5) 0.5878(3) 0.6185(2) 0.0620(9) Uani 1 1 d . . . . .
H9B H 0.685394 0.647788 0.653824 0.074 Uiso 1 1 calc R U . . .
C10B C 0.7528(5) 0.5796(3) 0.5507(2) 0.0700(10) Uani 1 1 d . . . . .
H10B H 0.794644 0.634350 0.539669 0.084 Uiso 1 1 calc R U . . .
C11B C 0.7552(5) 0.4909(3) 0.5003(2) 0.0685(10) Uani 1 1 d . . . . .
H11B H 0.798427 0.486757 0.454785 0.082 Uiso 1 1 calc R U . . .
C12B C 0.6351(5) 0.4182(3) 0.5777(2) 0.0578(8) Uani 1 1 d . . . . .
H12B H 0.593435 0.362156 0.587005 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1A C13A 2.090(3) . ?
I2A C17A 2.084(3) . ?
F1A C14A 1.349(3) . ?
F2A C15A 1.343(3) . ?
F3A C16A 1.337(4) . ?
F4A C18A 1.351(3) . ?
C13A C18A 1.378(4) . ?
C13A C14A 1.380(4) . ?
C14A C15A 1.371(5) . ?
C15A C16A 1.362(4) . ?
C16A C17A 1.385(4) . ?
C17A C18A 1.375(4) . ?
I1B C13B 2.095(3) . ?
I2B C17B 2.080(3) . ?
F1B C14B 1.347(3) . ?
F2B C15B 1.341(4) . ?
F3B C16B 1.337(4) . ?
F4B C18B 1.350(3) . ?
C13B C18B 1.381(4) . ?
C13B C14B 1.383(4) . ?
C14B C15B 1.371(5) . ?
C15B C16B 1.368(4) . ?
C16B C17B 1.386(4) . ?
C17B C18B 1.374(5) . ?
O1A C6A 1.341(4) . ?
O1A H1A 0.8200 . ?
N1A C7A 1.278(4) . ?
N1A C8A 1.419(4) . ?
N2A C12A 1.333(4) . ?
N2A C11A 1.337(4) . ?
C1A C2A 1.387(4) . ?
C1A C6A 1.405(4) . ?
C1A C7A 1.453(4) . ?
C2A C3A 1.374(5) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.370(5) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.363(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.387(5) . ?
C5A H5A 0.9300 . ?
C7A H7A 0.9300 . ?
C8A C12A 1.374(4) . ?
C8A C9A 1.391(4) . ?
C9A C10A 1.369(5) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.364(5) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
O1B C6B 1.351(4) . ?
O1B H1B 0.8200 . ?
N1B C7B 1.285(4) . ?
N1B C8B 1.410(4) . ?
N2B C11B 1.328(5) . ?
N2B C12B 1.330(4) . ?
C1B C2B 1.378(5) . ?
C1B C6B 1.405(4) . ?
C1B C7B 1.444(4) . ?
C2B C3B 1.380(5) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.369(6) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.383(6) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.388(5) . ?
C5B H5B 0.9300 . ?
C7B H7B 0.9300 . ?
C8B C9B 1.378(4) . ?
C8B C12B 1.380(4) . ?
C9B C10B 1.380(5) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.360(5) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
C12B H12B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18A C13A C14A 115.8(3) . . ?
C18A C13A I1A 124.2(2) . . ?
C14A C13A I1A 120.0(2) . . ?
F1A C14A C15A 118.3(3) . . ?
F1A C14A C13A 119.7(3) . . ?
C15A C14A C13A 122.0(3) . . ?
F2A C15A C16A 120.5(3) . . ?
F2A C15A C14A 119.6(3) . . ?
C16A C15A C14A 119.9(3) . . ?
F3A C16A C15A 118.3(3) . . ?
F3A C16A C17A 120.7(3) . . ?
C15A C16A C17A 120.9(3) . . ?
C18A C17A C16A 116.9(3) . . ?
C18A C17A I2A 122.3(2) . . ?
C16A C17A I2A 120.8(2) . . ?
F4A C18A C17A 117.7(3) . . ?
F4A C18A C13A 117.9(3) . . ?
C17A C18A C13A 124.4(3) . . ?
C18B C13B C14B 115.9(3) . . ?
C18B C13B I1B 123.2(2) . . ?
C14B C13B I1B 121.0(2) . . ?
F1B C14B C15B 117.8(3) . . ?
F1B C14B C13B 119.7(3) . . ?
C15B C14B C13B 122.4(3) . . ?
F2B C15B C16B 120.3(4) . . ?
F2B C15B C14B 120.6(3) . . ?
C16B C15B C14B 119.1(3) . . ?
F3B C16B C15B 118.5(3) . . ?
F3B C16B C17B 120.1(3) . . ?
C15B C16B C17B 121.4(3) . . ?
C18B C17B C16B 116.9(3) . . ?
C18B C17B I2B 122.9(2) . . ?
C16B C17B I2B 120.2(3) . . ?
F4B C18B C17B 117.9(3) . . ?
F4B C18B C13B 117.9(3) . . ?
C17B C18B C13B 124.2(3) . . ?
C6A O1A H1A 109.5 . . ?
C7A N1A C8A 121.7(3) . . ?
C12A N2A C11A 116.4(3) . . ?
C2A C1A C6A 118.7(3) . . ?
C2A C1A C7A 119.9(3) . . ?
C6A C1A C7A 121.4(3) . . ?
C3A C2A C1A 120.9(3) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
C4A C3A C2A 119.4(4) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C5A C4A C3A 121.5(4) . . ?
C5A C4A H4A 119.2 . . ?
C3A C4A H4A 119.2 . . ?
C4A C5A C6A 119.8(3) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
O1A C6A C5A 119.0(3) . . ?
O1A C6A C1A 121.3(3) . . ?
C5A C6A C1A 119.6(3) . . ?
N1A C7A C1A 121.9(3) . . ?
N1A C7A H7A 119.0 . . ?
C1A C7A H7A 119.0 . . ?
C12A C8A C9A 117.4(3) . . ?
C12A C8A N1A 116.5(3) . . ?
C9A C8A N1A 126.1(3) . . ?
C10A C9A C8A 118.6(3) . . ?
C10A C9A H9A 120.7 . . ?
C8A C9A H9A 120.7 . . ?
C11A C10A C9A 119.7(3) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
N2A C11A C10A 123.3(4) . . ?
N2A C11A H11A 118.4 . . ?
C10A C11A H11A 118.4 . . ?
N2A C12A C8A 124.7(3) . . ?
N2A C12A H12A 117.6 . . ?
C8A C12A H12A 117.6 . . ?
C6B O1B H1B 109.5 . . ?
C7B N1B C8B 122.4(3) . . ?
C11B N2B C12B 116.8(3) . . ?
C2B C1B C6B 119.4(3) . . ?
C2B C1B C7B 120.2(3) . . ?
C6B C1B C7B 120.4(3) . . ?
C1B C2B C3B 121.1(4) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B H2B 119.5 . . ?
C4B C3B C2B 119.1(4) . . ?
C4B C3B H3B 120.5 . . ?
C2B C3B H3B 120.5 . . ?
C3B C4B C5B 121.6(4) . . ?
C3B C4B H4B 119.2 . . ?
C5B C4B H4B 119.2 . . ?
C4B C5B C6B 119.3(4) . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B H5B 120.4 . . ?
O1B C6B C5B 118.9(3) . . ?
O1B C6B C1B 121.5(3) . . ?
C5B C6B C1B 119.5(4) . . ?
N1B C7B C1B 121.6(3) . . ?
N1B C7B H7B 119.2 . . ?
C1B C7B H7B 119.2 . . ?
C9B C8B C12B 117.8(3) . . ?
C9B C8B N1B 125.7(3) . . ?
C12B C8B N1B 116.5(3) . . ?
C8B C9B C10B 118.3(3) . . ?
C8B C9B H9B 120.8 . . ?
C10B C9B H9B 120.8 . . ?
C11B C10B C9B 119.4(4) . . ?
C11B C10B H10B 120.3 . . ?
C9B C10B H10B 120.3 . . ?
N2B C11B C10B 123.5(4) . . ?
N2B C11B H11B 118.3 . . ?
C10B C11B H11B 118.3 . . ?
N2B C12B C8B 124.2(3) . . ?
N2B C12B H12B 117.9 . . ?
C8B C12B H12B 117.9 . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.084

####################################################################### 
# 
# 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_nt0336_Andrea_PYS2_I2F4_re
_database_code_depnum_ccdc_archive 'CCDC 1854283'
_audit_update_record             
;
2018-07-06 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
;
1,2,4,5-tetrafluoro-3,6-diiodobenzene; 
bis(2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol)
;
_chemical_name_common            
;
1,2,4,5-tetrafluoro-3,6-diiodobenzene 
2-[(1E)-[(pyridin-3-yl)imino]methyl]phenol 1:2 cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N2 O, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C15 H10 F2 I N2 O'
_chemical_formula_weight         399.15

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.3516(5)
_cell_length_b                   5.75781(16)
_cell_length_c                   16.8675(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.671(3)
_cell_angle_gamma                90
_cell_volume                     1435.53(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3711
_cell_measurement_theta_min      2.7530
_cell_measurement_theta_max      30.7590

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    2.252
_shelx_estimated_absorpt_T_min   0.381
_shelx_estimated_absorpt_T_max   0.524
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.592
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_reflns_number            8967
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.508
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3999
_reflns_number_gt                3169
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.1797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3999
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C 0.05028(15) 0.0549(4) 0.08075(14) 0.0431(5) Uani 1 1 d . . . . .
C16 C 0.05058(17) 0.1965(4) 0.01497(16) 0.0463(6) Uani 1 1 d . . . . .
C17 C -0.00093(18) -0.1437(4) 0.06368(16) 0.0465(6) Uani 1 1 d . . . . .
F1 F 0.10001(12) 0.3937(2) 0.02741(11) 0.0681(5) Uani 1 1 d . . . . .
F2 F -0.00433(12) -0.2908(3) 0.12474(10) 0.0654(4) Uani 1 1 d . . . . .
I1 I 0.11985(2) 0.15115(3) 0.20076(2) 0.05544(8) Uani 1 1 d . . . . .
C1 C 0.47378(16) 0.5193(4) 0.34763(14) 0.0409(5) Uani 1 1 d . . . . .
C2 C 0.43487(18) 0.3730(4) 0.28179(17) 0.0483(6) Uani 1 1 d . . . . .
H2 H 0.461675 0.229987 0.278144 0.058 Uiso 1 1 calc R U . . .
C3 C 0.35873(18) 0.4335(5) 0.22267(17) 0.0547(6) Uani 1 1 d . . . . .
H3 H 0.334786 0.334270 0.178681 0.066 Uiso 1 1 calc R U . . .
C4 C 0.31673(19) 0.6462(4) 0.22853(18) 0.0541(6) Uani 1 1 d . . . . .
H4 H 0.264222 0.687915 0.188789 0.065 Uiso 1 1 calc R U . . .
C5 C 0.35328(19) 0.7931(4) 0.29316(17) 0.0499(6) Uani 1 1 d . . . . .
H5 H 0.325082 0.934028 0.296933 0.060 Uiso 1 1 calc R U . . .
C6 C 0.43150(17) 0.7340(4) 0.35270(15) 0.0448(5) Uani 1 1 d . . . . .
C7 C 0.55659(16) 0.4508(4) 0.40732(15) 0.0445(5) Uani 1 1 d . . . . .
H7 H 0.579374 0.302697 0.403761 0.053 Uiso 1 1 calc R U . . .
C8 C 0.68165(16) 0.5163(4) 0.52046(15) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.7290(2) 0.3115(4) 0.51825(18) 0.0594(7) Uani 1 1 d . . . . .
H9 H 0.708011 0.204388 0.476132 0.071 Uiso 1 1 calc R U . . .
C10 C 0.8067(2) 0.2699(5) 0.57887(19) 0.0626(7) Uani 1 1 d . . . . .
H10 H 0.838953 0.133053 0.578969 0.075 Uiso 1 1 calc R U . . .
C11 C 0.83676(18) 0.4333(5) 0.63981(18) 0.0561(6) Uani 1 1 d . . . . .
H11 H 0.889788 0.403645 0.680743 0.067 Uiso 1 1 calc R U . . .
C12 C 0.71815(19) 0.6696(4) 0.58386(17) 0.0501(6) Uani 1 1 d . . . . .
H12 H 0.687827 0.808798 0.585180 0.060 Uiso 1 1 calc R U . . .
N1 N 0.59931(14) 0.5847(3) 0.46426(13) 0.0466(5) Uani 1 1 d . . . . .
N2 N 0.79331(16) 0.6312(3) 0.64267(15) 0.0573(6) Uani 1 1 d . . . . .
O1 O 0.46505(15) 0.8850(3) 0.41477(12) 0.0581(5) Uani 1 1 d . . . . .
H1O H 0.518(2) 0.832(5) 0.442(2) 0.070 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 C17 1.373(3) . ?
C15 C16 1.378(3) . ?
C15 I1 2.092(2) . ?
C16 F1 1.351(3) . ?
C16 C17 1.374(3) 3 ?
C17 F2 1.345(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.447(3) . ?
C2 C3 1.361(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 O1 1.351(3) . ?
C7 N1 1.267(3) . ?
C7 H7 0.9300 . ?
C8 C12 1.383(3) . ?
C8 C9 1.391(3) . ?
C8 N1 1.416(3) . ?
C9 C10 1.367(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 N2 1.328(3) . ?
C11 H11 0.9300 . ?
C12 N2 1.321(3) . ?
C12 H12 0.9300 . ?
O1 H1O 0.87(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
C17 C15 C16 116.7(2) . . ?
C17 C15 I1 122.49(18) . . ?
C16 C15 I1 120.69(17) . . ?
F1 C16 C17 118.6(2) . 3 ?
F1 C16 C15 119.8(2) . . ?
C17 C16 C15 121.7(2) 3 . ?
F2 C17 C16 118.3(2) . 3 ?
F2 C17 C15 120.1(2) . . ?
C16 C17 C15 121.6(2) 3 . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 C7 119.8(2) . . ?
C6 C1 C7 121.9(2) . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O1 C6 C5 118.6(2) . . ?
O1 C6 C1 121.7(2) . . ?
C5 C6 C1 119.7(2) . . ?
N1 C7 C1 122.6(2) . . ?
N1 C7 H7 118.7 . . ?
C1 C7 H7 118.7 . . ?
C12 C8 C9 117.2(2) . . ?
C12 C8 N1 116.2(2) . . ?
C9 C8 N1 126.6(2) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
N2 C11 C10 122.9(3) . . ?
N2 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
N2 C12 C8 124.2(2) . . ?
N2 C12 H12 117.9 . . ?
C8 C12 H12 117.9 . . ?
C7 N1 C8 121.6(2) . . ?
C12 N2 C11 117.5(2) . . ?
C6 O1 H1O 106.7(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C15 C16 F1 -179.6(2) . . . . ?
I1 C15 C16 F1 3.4(3) . . . . ?
C17 C15 C16 C17 1.0(4) . . . 3 ?
I1 C15 C16 C17 -175.97(19) . . . 3 ?
C16 C15 C17 F2 179.8(2) . . . . ?
I1 C15 C17 F2 -3.3(3) . . . . ?
C16 C15 C17 C16 -1.0(4) . . . 3 ?
I1 C15 C17 C16 175.91(19) . . . 3 ?
C6 C1 C2 C3 0.8(4) . . . . ?
C7 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 O1 179.6(2) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C2 C1 C6 O1 179.9(2) . . . . ?
C7 C1 C6 O1 -1.6(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C7 C1 C6 C5 178.8(2) . . . . ?
C2 C1 C7 N1 173.7(2) . . . . ?
C6 C1 C7 N1 -4.8(4) . . . . ?
C12 C8 C9 C10 1.5(4) . . . . ?
N1 C8 C9 C10 -178.4(3) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C9 C10 C11 N2 0.1(5) . . . . ?
C9 C8 C12 N2 -1.5(4) . . . . ?
N1 C8 C12 N2 178.4(2) . . . . ?
C1 C7 N1 C8 -178.1(2) . . . . ?
C12 C8 N1 C7 -174.9(2) . . . . ?
C9 C8 N1 C7 5.0(4) . . . . ?
C8 C12 N2 C11 0.8(4) . . . . ?
C10 C11 N2 C12 0.0(4) . . . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.061


# start Validation Reply Form
_vrf_PLAT911_nt0336_Andrea_PYS2_I2F4_re 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
RESPONSE: These reflection are missing because of the instrument geometry 
limitations.
;
# end Validation Reply Form
