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

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

data_e3344
_database_code_depnum_ccdc_archive 'CCDC 2076758'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F4 I2 N2'
_chemical_formula_weight         662.19

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8990(6)
_cell_length_b                   9.0065(8)
_cell_length_c                   10.5354(9)
_cell_angle_alpha                67.043(2)
_cell_angle_beta                 74.8130(19)
_cell_angle_gamma                69.918(2)
_cell_volume                     559.89(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3737
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      30.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    2.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7256
_exptl_absorpt_correction_T_max  0.8943
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5755
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         29.46
_reflns_number_total             3002
_reflns_number_gt                2766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1290P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3002
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0668
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1560
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4872(6) 0.9657(5) 0.2423(5) 0.0280(9) Uani 1 1 d . . .
C1 C 0.3452(7) 0.9622(6) 0.1799(5) 0.0279(9) Uani 1 1 d . . .
H1 H 0.3274 1.0396 0.0888 0.033 Uiso 1 1 calc R . .
C2 C 0.2216(7) 0.8518(6) 0.2402(4) 0.0247(9) Uani 1 1 d . . .
H2 H 0.1228 0.8541 0.1910 0.030 Uiso 1 1 calc R . .
C3 C 0.2439(6) 0.7380(5) 0.3736(4) 0.0214(8) Uani 1 1 d . . .
C4 C 0.3942(8) 0.7398(7) 0.4393(5) 0.0302(10) Uani 1 1 d . . .
H4 H 0.4161 0.6638 0.5303 0.036 Uiso 1 1 calc R . .
C5 C 0.5116(7) 0.8552(7) 0.3692(6) 0.0340(11) Uani 1 1 d . . .
H5 H 0.6143 0.8548 0.4143 0.041 Uiso 1 1 calc R . .
C6 C 0.1190(6) 0.6183(5) 0.4397(4) 0.0199(8) Uani 1 1 d . . .
C7 C 0.1424(6) 0.4961(6) 0.3823(4) 0.0235(8) Uani 1 1 d . . .
H7 H 0.2405 0.4941 0.3003 0.028 Uiso 1 1 calc R . .
C8 C 0.0294(6) 0.3765(5) 0.4387(4) 0.0219(8) Uani 1 1 d . . .
C9 C 0.0742(7) 0.2412(6) 0.3772(5) 0.0296(10) Uani 1 1 d . . .
H9A H 0.1816 0.2579 0.2950 0.044 Uiso 1 1 calc R . .
H9B H -0.0536 0.2457 0.3499 0.044 Uiso 1 1 calc R . .
H9C H 0.1238 0.1316 0.4464 0.044 Uiso 1 1 calc R . .
C10 C 0.1258(7) 0.6124(6) 0.9517(5) 0.0239(9) Uani 1 1 d . . .
I1 I 0.30213(4) 0.78752(3) 0.87177(3) 0.02603(16) Uani 1 1 d . . .
C11 C 0.1741(6) 0.4797(6) 0.9029(5) 0.0254(9) Uani 1 1 d . . .
F1 F 0.3428(5) 0.4552(4) 0.8071(3) 0.0342(7) Uani 1 1 d . . .
C12 C -0.0508(6) 0.6287(6) 1.0503(5) 0.0234(8) Uani 1 1 d . . .
F2 F -0.1077(4) 0.7562(4) 1.1014(3) 0.0313(6) 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 C1 1.330(6) . ?
N1 C5 1.330(7) . ?
C1 C2 1.387(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(6) . ?
C3 C6 1.458(6) . ?
C4 C5 1.395(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.397(6) . ?
C6 C8 1.421(5) 2_566 ?
C7 C8 1.398(7) . ?
C7 H7 0.9500 . ?
C8 C6 1.421(5) 2_566 ?
C8 C9 1.501(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.385(6) . ?
C10 C11 1.386(7) . ?
C10 I1 2.103(5) . ?
C11 F1 1.343(4) . ?
C11 C12 1.376(7) 2_567 ?
C12 F2 1.350(5) . ?
C12 C11 1.376(7) 2_567 ?

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 C5 117.3(5) . . ?
N1 C1 C2 123.7(5) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 117.4(4) . . ?
C2 C3 C6 120.8(4) . . ?
C4 C3 C6 121.7(4) . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 123.5(5) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C8 118.5(4) . 2_566 ?
C7 C6 C3 119.9(4) . . ?
C8 C6 C3 121.7(4) 2_566 . ?
C6 C7 C8 123.7(4) . . ?
C6 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C6 117.8(4) . 2_566 ?
C7 C8 C9 120.6(4) . . ?
C6 C8 C9 121.5(4) 2_566 . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C11 116.6(5) . . ?
C12 C10 I1 121.7(4) . . ?
C11 C10 I1 121.6(3) . . ?
F1 C11 C12 118.5(4) . 2_567 ?
F1 C11 C10 120.2(4) . . ?
C12 C11 C10 121.3(4) 2_567 . ?
F2 C12 C11 118.2(4) . 2_567 ?
F2 C12 C10 119.6(4) . . ?
C11 C12 C10 122.1(4) 2_567 . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        29.46
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         2.920
_refine_diff_density_min         -2.764
_refine_diff_density_rms         0.332
####################################################################### 
# 
# 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_e3324b
_database_code_depnum_ccdc_archive 'CCDC 2076761'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H28 F10 I2 N2'
_chemical_formula_weight         1028.48

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.68540(10)
_cell_length_b                   9.3757(2)
_cell_length_c                   14.3001(3)
_cell_angle_alpha                78.9336(8)
_cell_angle_beta                 76.5682(8)
_cell_angle_gamma                76.3666(7)
_cell_volume                     963.67(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8205
_exptl_absorpt_correction_T_max  0.9040
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19292
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         29.51
_reflns_number_total             5188
_reflns_number_gt                4772
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0212P)²+1.0276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5188
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0549
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1330(3) 0.95403(18) 0.25360(13) 0.0301(4) Uani 1 1 d . . .
C1 C -0.1743(3) 0.9230(2) 0.17500(16) 0.0291(4) Uani 1 1 d . . .
H1 H -0.2649 0.9925 0.1457 0.035 Uiso 1 1 calc R . .
C2 C -0.0922(3) 0.7952(2) 0.13363(14) 0.0250(4) Uani 1 1 d . . .
H2 H -0.1284 0.7778 0.0783 0.030 Uiso 1 1 calc R . .
C3 C 0.0436(3) 0.69253(19) 0.17390(13) 0.0200(3) Uani 1 1 d . . .
C4 C 0.0861(3) 0.7248(2) 0.25618(14) 0.0244(4) Uani 1 1 d . . .
H4 H 0.1769 0.6582 0.2869 0.029 Uiso 1 1 calc R . .
C5 C -0.0049(3) 0.8545(2) 0.29293(15) 0.0286(4) Uani 1 1 d . . .
H5 H 0.0257 0.8737 0.3494 0.034 Uiso 1 1 calc R . .
C6 C 0.1384(2) 0.55227(19) 0.13475(13) 0.0191(3) Uani 1 1 d . . .
C7 C 0.1998(2) 0.54246(19) 0.03509(13) 0.0194(3) Uani 1 1 d . . .
C8 C 0.1798(3) 0.6718(2) -0.04590(14) 0.0253(4) Uani 1 1 d . . .
H8A H 0.2901 0.6618 -0.0969 0.038 Uiso 1 1 calc R . .
H8B H 0.1625 0.7648 -0.0201 0.038 Uiso 1 1 calc R . .
H8C H 0.0737 0.6726 -0.0732 0.038 Uiso 1 1 calc R . .
C9 C 0.2896(3) 0.4042(2) 0.00905(13) 0.0208(4) Uani 1 1 d . . .
H9 H 0.3327 0.3970 -0.0581 0.025 Uiso 1 1 calc R . .
C10 C 0.3199(2) 0.27573(19) 0.07566(13) 0.0185(3) Uani 1 1 d . . .
C11 C 0.2626(2) 0.28618(19) 0.17572(13) 0.0193(3) Uani 1 1 d . . .
C12 C 0.2998(3) 0.1585(2) 0.25511(14) 0.0262(4) Uani 1 1 d . . .
H12A H 0.2958 0.1969 0.3148 0.039 Uiso 1 1 calc R . .
H12B H 0.4208 0.0976 0.2352 0.039 Uiso 1 1 calc R . .
H12C H 0.2069 0.0978 0.2669 0.039 Uiso 1 1 calc R . .
C13 C 0.1736(3) 0.42401(19) 0.20163(13) 0.0200(4) Uani 1 1 d . . .
H13 H 0.1342 0.4318 0.2689 0.024 Uiso 1 1 calc R . .
C14 C 0.4122(2) 0.13327(19) 0.03834(13) 0.0195(3) Uani 1 1 d . . .
C15 C 0.3502(3) 0.0017(2) 0.07537(14) 0.0226(4) Uani 1 1 d . . .
H15 H 0.2468 0.0014 0.1269 0.027 Uiso 1 1 calc R . .
C16 C 0.4367(3) -0.1292(2) 0.03839(14) 0.0217(4) Uani 1 1 d . . .
H16 H 0.3925 -0.2176 0.0657 0.026 Uiso 1 1 calc R . .
I1 I 0.756510(18) 0.225544(14) 0.328701(9) 0.02801(5) Uani 1 1 d . . .
C17 C 0.6998(3) 0.4348(2) 0.37390(14) 0.0253(4) Uani 1 1 d . . .
C18 C 0.7562(3) 0.4564(2) 0.45433(15) 0.0315(4) Uani 1 1 d . . .
F1 F 0.8436(2) 0.34084(17) 0.50846(10) 0.0480(4) Uani 1 1 d . . .
C19 C 0.7221(3) 0.5943(3) 0.48250(16) 0.0380(5) Uani 1 1 d . . .
F2 F 0.7770(3) 0.6099(2) 0.56169(11) 0.0614(5) Uani 1 1 d . . .
C20 C 0.6292(3) 0.7151(2) 0.43089(17) 0.0388(6) Uani 1 1 d . . .
F3 F 0.5959(2) 0.84917(16) 0.45761(12) 0.0588(5) Uani 1 1 d . . .
C21 C 0.5690(3) 0.6970(2) 0.35110(17) 0.0345(5) Uani 1 1 d . . .
F4 F 0.4733(2) 0.81247(15) 0.30179(12) 0.0522(4) Uani 1 1 d . . .
C22 C 0.6059(3) 0.5582(2) 0.32350(15) 0.0285(4) Uani 1 1 d . . .
F5 F 0.5454(2) 0.54512(15) 0.24511(10) 0.0417(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.334(3) . ?
N1 C1 1.335(3) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(3) . ?
C3 C6 1.488(2) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C13 1.400(2) . ?
C6 C7 1.407(2) . ?
C7 C9 1.393(2) . ?
C7 C8 1.514(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.394(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(2) . ?
C10 C14 1.491(2) . ?
C11 C13 1.387(2) . ?
C11 C12 1.507(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 C16 1.399(3) 2_655 ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C14 1.399(3) 2_655 ?
C16 H16 0.9500 . ?
I1 C17 2.100(2) . ?
C17 C22 1.381(3) . ?
C17 C18 1.383(3) . ?
C18 F1 1.342(2) . ?
C18 C19 1.376(3) . ?
C19 F2 1.340(3) . ?
C19 C20 1.372(4) . ?
C20 F3 1.334(2) . ?
C20 C21 1.379(4) . ?
C21 F4 1.336(3) . ?
C21 C22 1.378(3) . ?
C22 F5 1.345(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
C5 N1 C1 116.67(17) . . ?
N1 C1 C2 123.78(18) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.45(19) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 116.68(16) . . ?
C2 C3 C6 123.17(17) . . ?
C4 C3 C6 120.13(16) . . ?
C5 C4 C3 119.70(18) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.71(19) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C13 C6 C7 118.41(15) . . ?
C13 C6 C3 117.66(15) . . ?
C7 C6 C3 123.89(16) . . ?
C9 C7 C6 117.61(16) . . ?
C9 C7 C8 117.51(16) . . ?
C6 C7 C8 124.86(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 C10 123.88(16) . . ?
C7 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 118.54(15) . . ?
C9 C10 C14 118.70(15) . . ?
C11 C10 C14 122.75(15) . . ?
C13 C11 C10 117.53(16) . . ?
C13 C11 C12 118.61(16) . . ?
C10 C11 C12 123.81(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C6 123.98(16) . . ?
C11 C13 H13 118.0 . . ?
C6 C13 H13 118.0 . . ?
C15 C14 C16 117.52(15) . 2_655 ?
C15 C14 C10 122.25(16) . . ?
C16 C14 C10 120.20(16) 2_655 . ?
C16 C15 C14 121.21(17) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C14 121.26(17) . 2_655 ?
C15 C16 H16 119.4 . . ?
C14 C16 H16 119.4 2_655 . ?
C22 C17 C18 116.81(19) . . ?
C22 C17 I1 121.22(15) . . ?
C18 C17 I1 121.96(15) . . ?
F1 C18 C19 118.1(2) . . ?
F1 C18 C17 120.12(19) . . ?
C19 C18 C17 121.8(2) . . ?
F2 C19 C20 119.9(2) . . ?
F2 C19 C18 119.8(2) . . ?
C20 C19 C18 120.2(2) . . ?
F3 C20 C19 120.6(2) . . ?
F3 C20 C21 120.0(2) . . ?
C19 C20 C21 119.4(2) . . ?
F4 C21 C22 120.2(2) . . ?
F4 C21 C20 120.3(2) . . ?
C22 C21 C20 119.5(2) . . ?
F5 C22 C21 117.74(18) . . ?
F5 C22 C17 120.00(18) . . ?
C21 C22 C17 122.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        29.51
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_e3335a
_database_code_depnum_ccdc_archive 'CCDC 2076759'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 F10 I2 N2'
_chemical_formula_weight         848.25

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.02020(10)
_cell_length_b                   27.0920(11)
_cell_length_c                   13.0226(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8344(10)
_cell_angle_gamma                90.00
_cell_volume                     1415.18(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8835
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      30.07

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7687
_exptl_absorpt_correction_T_max  0.8737
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17279
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         30.09
_reflns_number_total             3933
_reflns_number_gt                3680
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0042P)²+2.6795P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3933
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_restrained_S_all      1.252
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3672(7) 0.55991(9) 0.91605(17) 0.0263(5) Uani 1 1 d . . .
C1 C 0.4995(8) 0.59009(10) 0.8488(2) 0.0258(6) Uani 1 1 d . . .
H1 H 0.5733 0.6217 0.8724 0.031 Uiso 1 1 calc R . .
C2 C 0.5357(7) 0.57819(9) 0.74679(19) 0.0224(5) Uani 1 1 d . . .
H2 H 0.6316 0.6013 0.7025 0.027 Uiso 1 1 calc R . .
C3 C 0.4314(7) 0.53234(9) 0.70933(18) 0.0184(5) Uani 1 1 d . . .
C4 C 0.2993(7) 0.50025(9) 0.77971(19) 0.0218(5) Uani 1 1 d . . .
H4 H 0.2285 0.4681 0.7587 0.026 Uiso 1 1 calc R . .
C5 C 0.2717(8) 0.51533(10) 0.8805(2) 0.0243(6) Uani 1 1 d . . .
H5 H 0.1800 0.4928 0.9269 0.029 Uiso 1 1 calc R . .
C6 C 0.4624(7) 0.51706(9) 0.60041(18) 0.0176(5) Uani 1 1 d . . .
C7 C 0.3649(7) 0.54753(9) 0.51683(19) 0.0194(5) Uani 1 1 d . . .
C8 C 0.2082(8) 0.59777(10) 0.5277(2) 0.0265(6) Uani 1 1 d . . .
H8A H 0.0851 0.5985 0.5901 0.040 Uiso 1 1 calc R . .
H8B H 0.0548 0.6044 0.4676 0.040 Uiso 1 1 calc R . .
H8C H 0.3831 0.6230 0.5324 0.040 Uiso 1 1 calc R . .
C9 C 0.4061(7) 0.52956(9) 0.41817(19) 0.0193(5) Uani 1 1 d . . .
H9 H 0.3417 0.5500 0.3609 0.023 Uiso 1 1 calc R . .
I1 I 1.17586(5) 0.623435(7) 0.076420(14) 0.02555(6) Uani 1 1 d . . .
C10 C 1.0361(7) 0.67966(10) 0.1757(2) 0.0225(5) Uani 1 1 d . . .
C11 C 0.8869(7) 0.66934(9) 0.2658(2) 0.0234(5) Uani 1 1 d . . .
F1 F 0.8222(5) 0.62258(6) 0.29137(13) 0.0361(4) Uani 1 1 d . . .
C12 C 0.7960(8) 0.70587(11) 0.3321(2) 0.0300(6) Uani 1 1 d . . .
F2 F 0.6491(6) 0.69463(8) 0.41823(15) 0.0492(6) Uani 1 1 d . . .
C13 C 0.8537(10) 0.75448(11) 0.3088(3) 0.0390(8) Uani 1 1 d . . .
F3 F 0.7615(7) 0.79019(8) 0.37183(19) 0.0620(7) Uani 1 1 d . . .
C14 C 1.0009(10) 0.76598(11) 0.2197(3) 0.0419(8) Uani 1 1 d . . .
F4 F 1.0571(8) 0.81330(7) 0.1967(2) 0.0752(9) Uani 1 1 d . . .
C15 C 1.0909(9) 0.72883(11) 0.1540(2) 0.0330(7) Uani 1 1 d . . .
F5 F 1.2374(6) 0.74175(8) 0.06867(17) 0.0542(6) 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 C1 1.334(4) . ?
N1 C5 1.340(3) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 C6 1.491(3) . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.401(3) . ?
C6 C9 1.397(3) 3_666 ?
C7 C9 1.394(3) . ?
C7 C8 1.510(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C6 1.397(3) 3_666 ?
C9 H9 0.9500 . ?
I1 C10 2.099(3) . ?
C10 C11 1.382(4) . ?
C10 C15 1.382(4) . ?
C11 F1 1.340(3) . ?
C11 C12 1.379(4) . ?
C12 F2 1.337(4) . ?
C12 C13 1.375(4) . ?
C13 F3 1.337(3) . ?
C13 C14 1.373(5) . ?
C14 F4 1.339(4) . ?
C14 C15 1.385(5) . ?
C15 F5 1.339(4) . ?

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 C5 116.3(2) . . ?
N1 C1 C2 124.0(2) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 116.5(2) . . ?
C2 C3 C6 122.7(2) . . ?
C4 C3 C6 120.8(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 123.6(3) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C7 C6 C9 119.2(2) . 3_666 ?
C7 C6 C3 122.6(2) . . ?
C9 C6 C3 118.2(2) 3_666 . ?
C9 C7 C6 117.8(2) . . ?
C9 C7 C8 118.5(2) . . ?
C6 C7 C8 123.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 C6 123.0(2) . 3_666 ?
C7 C9 H9 118.5 . . ?
C6 C9 H9 118.5 3_666 . ?
C11 C10 C15 116.9(3) . . ?
C11 C10 I1 121.71(19) . . ?
C15 C10 I1 121.4(2) . . ?
F1 C11 C10 120.3(2) . . ?
F1 C11 C12 117.3(3) . . ?
C10 C11 C12 122.4(3) . . ?
F2 C12 C13 119.6(3) . . ?
F2 C12 C11 120.8(3) . . ?
C13 C12 C11 119.6(3) . . ?
F3 C13 C14 120.5(3) . . ?
F3 C13 C12 120.0(3) . . ?
C14 C13 C12 119.5(3) . . ?
F4 C14 C13 119.7(3) . . ?
F4 C14 C15 120.2(3) . . ?
C13 C14 C15 120.2(3) . . ?
F5 C15 C10 120.4(3) . . ?
F5 C15 C14 118.1(3) . . ?
C10 C15 C14 121.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_theta_full        30.09
_diffrn_measured_fraction_theta_full 0.943
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.950
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_e3423a
_database_code_depnum_ccdc_archive 'CCDC 2076764'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F3 I3 N2'
_chemical_formula_weight         770.09

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.4200(4)
_cell_length_b                   17.8302(10)
_cell_length_c                   35.8919(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4748.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6420
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.65

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2880
_exptl_absorpt_coefficient_mu    3.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6912
_exptl_absorpt_correction_T_max  0.7959
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29156
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         30.01
_reflns_number_total             6814
_reflns_number_gt                5450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0210P)²+16.8515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6814
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7728(5) 0.7158(2) 0.15195(10) 0.0339(8) Uani 1 1 d . . .
C1 C 0.8916(6) 0.6600(3) 0.15370(11) 0.0328(10) Uani 1 1 d . . .
H1 H 0.9811 0.6616 0.1726 0.039 Uiso 1 1 calc R . .
C2 C 0.8915(6) 0.5991(2) 0.12926(11) 0.0280(9) Uani 1 1 d . . .
H2 H 0.9789 0.5605 0.1317 0.034 Uiso 1 1 calc R . .
C3 C 0.7630(5) 0.5955(2) 0.10141(10) 0.0215(7) Uani 1 1 d . . .
C4 C 0.6407(6) 0.6539(2) 0.09924(12) 0.0308(9) Uani 1 1 d . . .
H4 H 0.5511 0.6543 0.0803 0.037 Uiso 1 1 calc R . .
C5 C 0.6498(7) 0.7118(3) 0.12485(13) 0.0373(11) Uani 1 1 d . . .
H5 H 0.5635 0.7510 0.1231 0.045 Uiso 1 1 calc R . .
C6 C 0.7552(5) 0.5334(2) 0.07368(10) 0.0202(7) Uani 1 1 d . . .
C7 C 0.7565(5) 0.4577(2) 0.08404(10) 0.0202(7) Uani 1 1 d . . .
C8 C 0.7609(6) 0.4318(2) 0.12397(10) 0.0262(8) Uani 1 1 d . . .
H8A H 0.8859 0.4309 0.1328 0.039 Uiso 1 1 calc R . .
H8B H 0.7094 0.3813 0.1257 0.039 Uiso 1 1 calc R . .
H8C H 0.6903 0.4664 0.1394 0.039 Uiso 1 1 calc R . .
C9 C 0.7478(5) 0.4042(2) 0.05561(10) 0.0217(8) Uani 1 1 d . . .
H9 H 0.7471 0.3527 0.0623 0.026 Uiso 1 1 calc R . .
C10 C 0.7401(5) 0.4226(2) 0.01797(10) 0.0202(7) Uani 1 1 d . . .
C11 C 0.7391(5) 0.4989(2) 0.00745(9) 0.0202(7) Uani 1 1 d . . .
C12 C 0.7278(6) 0.5261(2) -0.03225(10) 0.0255(8) Uani 1 1 d . . .
H12A H 0.6737 0.5762 -0.0327 0.038 Uiso 1 1 calc R . .
H12B H 0.6533 0.4915 -0.0468 0.038 Uiso 1 1 calc R . .
H12C H 0.8491 0.5282 -0.0430 0.038 Uiso 1 1 calc R . .
C13 C 0.7439(5) 0.5519(2) 0.03562(10) 0.0201(7) Uani 1 1 d . . .
H13 H 0.7392 0.6034 0.0289 0.024 Uiso 1 1 calc R . .
C14 C 0.7306(5) 0.3598(2) -0.00932(10) 0.0200(7) Uani 1 1 d . . .
C15 C 0.6257(6) 0.2966(2) -0.00206(10) 0.0242(8) Uani 1 1 d . . .
H15 H 0.5527 0.2948 0.0197 0.029 Uiso 1 1 calc R . .
C16 C 0.6278(6) 0.2366(2) -0.02645(11) 0.0270(9) Uani 1 1 d . . .
H16 H 0.5555 0.1942 -0.0207 0.032 Uiso 1 1 calc R . .
N2 N 0.7261(5) 0.23509(19) -0.05765(9) 0.0267(7) Uani 1 1 d . . .
C17 C 0.8248(6) 0.2960(2) -0.06495(11) 0.0264(8) Uani 1 1 d . . .
H17 H 0.8949 0.2964 -0.0871 0.032 Uiso 1 1 calc R . .
C18 C 0.8313(5) 0.3587(2) -0.04219(10) 0.0230(8) Uani 1 1 d . . .
H18 H 0.9037 0.4006 -0.0489 0.028 Uiso 1 1 calc R . .
C19 C 0.8679(6) 0.5135(2) 0.28385(11) 0.0282(9) Uani 1 1 d . . .
I1 I 0.93865(6) 0.625551(16) 0.277436(10) 0.04821(10) Uani 1 1 d . . .
C20 C 0.8410(6) 0.4836(2) 0.31906(11) 0.0262(8) Uani 1 1 d . . .
F1 F 0.8540(4) 0.52921(14) 0.34895(7) 0.0380(6) Uani 1 1 d . . .
C21 C 0.8035(5) 0.4087(2) 0.32495(10) 0.0230(8) Uani 1 1 d . . .
I2 I 0.77017(4) 0.362186(16) 0.377810(7) 0.02847(7) Uani 1 1 d . . .
C22 C 0.7909(6) 0.3636(2) 0.29380(10) 0.0222(8) Uani 1 1 d . . .
F2 F 0.7603(4) 0.29032(13) 0.29863(6) 0.0310(6) Uani 1 1 d . . .
C23 C 0.8113(5) 0.3899(2) 0.25771(10) 0.0227(8) Uani 1 1 d . . .
I3 I 0.77928(4) 0.317878(14) 0.212215(6) 0.02467(7) Uani 1 1 d . . .
C24 C 0.8505(6) 0.4651(2) 0.25366(11) 0.0251(8) Uani 1 1 d . . .
F3 F 0.8745(4) 0.49334(14) 0.21932(7) 0.0372(6) 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 C1 1.331(6) . ?
N1 C5 1.336(6) . ?
C1 C2 1.395(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(6) . ?
C3 C6 1.491(5) . ?
C4 C5 1.383(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.401(5) . ?
C6 C13 1.408(5) . ?
C7 C9 1.398(5) . ?
C7 C8 1.506(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(5) . ?
C10 C14 1.489(5) . ?
C11 C13 1.385(5) . ?
C11 C12 1.507(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 C15 1.395(5) . ?
C14 C18 1.397(5) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 N2 1.337(5) . ?
C16 H16 0.9500 . ?
N2 C17 1.336(5) . ?
C17 C18 1.386(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.385(6) . ?
C19 C24 1.391(5) . ?
C19 I1 2.079(4) . ?
C20 F1 1.350(4) . ?
C20 C21 1.380(6) . ?
C21 C22 1.381(5) . ?
C21 I2 2.085(4) . ?
C22 F2 1.337(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.379(5) . ?
C23 I3 2.091(4) . ?
C24 F3 1.343(4) . ?

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 C5 116.5(4) . . ?
N1 C1 C2 123.5(4) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 C6 119.8(3) . . ?
C2 C3 C6 122.9(4) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C13 118.9(3) . . ?
C7 C6 C3 122.6(3) . . ?
C13 C6 C3 118.4(3) . . ?
C6 C7 C9 117.6(3) . . ?
C6 C7 C8 123.2(3) . . ?
C9 C7 C8 119.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C7 123.4(3) . . ?
C10 C9 H9 118.3 . . ?
C7 C9 H9 118.3 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 C14 117.6(3) . . ?
C11 C10 C14 123.2(3) . . ?
C13 C11 C10 117.5(3) . . ?
C13 C11 C12 118.2(3) . . ?
C10 C11 C12 124.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C6 123.4(3) . . ?
C11 C13 H13 118.3 . . ?
C6 C13 H13 118.3 . . ?
C15 C14 C18 116.4(3) . . ?
C15 C14 C10 120.7(3) . . ?
C18 C14 C10 122.8(3) . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N2 C16 C15 123.6(4) . . ?
N2 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C17 N2 C16 116.5(3) . . ?
N2 C17 C18 124.0(4) . . ?
N2 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
C17 C18 C14 119.4(4) . . ?
C17 C18 H18 120.3 . . ?
C14 C18 H18 120.3 . . ?
C20 C19 C24 117.3(4) . . ?
C20 C19 I1 120.4(3) . . ?
C24 C19 I1 122.2(3) . . ?
F1 C20 C21 118.4(4) . . ?
F1 C20 C19 118.9(4) . . ?
C21 C20 C19 122.7(4) . . ?
C20 C21 C22 117.0(3) . . ?
C20 C21 I2 123.3(3) . . ?
C22 C21 I2 119.8(3) . . ?
F2 C22 C21 118.4(3) . . ?
F2 C22 C23 118.1(3) . . ?
C21 C22 C23 123.5(4) . . ?
C24 C23 C22 116.8(3) . . ?
C24 C23 I3 122.6(3) . . ?
C22 C23 I3 120.6(3) . . ?
F3 C24 C23 119.3(3) . . ?
F3 C24 C19 118.0(4) . . ?
C23 C24 C19 122.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.769
_refine_diff_density_min         -1.797
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_e3412a
_database_code_depnum_ccdc_archive 'CCDC 2076762'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F3 I3 N2'
_chemical_formula_weight         770.09

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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

loop_
_symmetry_equiv_pos_as_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                   5.5110(3)
_cell_length_b                   18.5899(11)
_cell_length_c                   23.7423(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2432.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4423
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      29.37

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    3.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6523
_exptl_absorpt_correction_T_max  0.8599
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14054
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         30.04
_reflns_number_total             3509
_reflns_number_gt                2656
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0177P)²+6.4413P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3509
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3110(7) 0.23801(16) 0.39983(14) 0.0462(8) Uani 1 1 d . . .
C1 C 0.4299(8) 0.2677(2) 0.4418(2) 0.0559(11) Uani 1 1 d . . .
H1 H 0.5704 0.2438 0.4555 0.067 Uiso 1 1 calc R . .
C2 C 0.3625(8) 0.3319(2) 0.46735(19) 0.0524(11) Uani 1 1 d . . .
H2 H 0.4539 0.3504 0.4980 0.063 Uiso 1 1 calc R . .
C3 C 0.1628(7) 0.36844(16) 0.44789(14) 0.0323(7) Uani 1 1 d . . .
C4 C 0.0366(8) 0.3381(2) 0.40404(18) 0.0496(10) Uani 1 1 d . . .
H4 H -0.1036 0.3611 0.3892 0.059 Uiso 1 1 calc R . .
C5 C 0.1178(8) 0.2732(2) 0.38174(19) 0.0543(11) Uani 1 1 d . . .
H5 H 0.0283 0.2528 0.3515 0.065 Uiso 1 1 calc R . .
C6 C 0.0822(6) 0.43739(16) 0.47437(13) 0.0301(7) Uani 1 1 d . . .
C7 C 0.1794(7) 0.50335(17) 0.45734(15) 0.0348(7) Uani 1 1 d . . .
C8 C 0.3716(8) 0.5082(2) 0.41251(17) 0.0509(11) Uani 1 1 d . . .
H8A H 0.4079 0.5589 0.4048 0.076 Uiso 1 1 calc R . .
H8B H 0.3130 0.4851 0.3780 0.076 Uiso 1 1 calc R . .
H8C H 0.5190 0.4839 0.4255 0.076 Uiso 1 1 calc R . .
C9 C -0.0911(7) 0.43512(16) 0.51648(14) 0.0349(7) Uani 1 1 d . . .
H9 H -0.1524 0.3897 0.5280 0.042 Uiso 1 1 calc R . .
C10 C 1.0000 -0.0346(2) 0.2500 0.0411(12) Uani 1 2 d S . .
I1 I 1.0000 -0.146629(19) 0.2500 0.07406(16) Uani 1 2 d S . .
C11 C 0.8368(7) 0.00399(18) 0.28229(15) 0.0375(8) Uani 1 1 d . . .
F1 F 0.6754(5) -0.03184(12) 0.31396(10) 0.0529(6) Uani 1 1 d . . .
C12 C 0.8334(6) 0.07863(17) 0.28372(14) 0.0327(7) Uani 1 1 d . . .
I2 I 0.59323(5) 0.137599(12) 0.334333(10) 0.03988(8) Uani 1 1 d . . .
C13 C 1.0000 0.1133(2) 0.2500 0.0331(10) Uani 1 2 d S . .
F2 F 1.0000 0.18584(13) 0.2500 0.0403(7) Uani 1 2 d S . .


_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 C1 1.314(5) . ?
N1 C5 1.321(5) . ?
C1 C2 1.390(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(5) . ?
C3 C6 1.495(4) . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C9 1.383(5) . ?
C6 C7 1.398(4) . ?
C7 C9 1.390(4) 5_566 ?
C7 C8 1.504(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C7 1.390(4) 5_566 ?
C9 H9 0.9500 . ?
C10 C11 1.382(4) 3_755 ?
C10 C11 1.382(4) . ?
C10 I1 2.083(5) . ?
C11 F1 1.342(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.378(4) . ?
C12 I2 2.097(3) . ?
C13 F2 1.348(5) . ?
C13 C12 1.378(4) 3_755 ?

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 C5 116.1(3) . . ?
N1 C1 C2 124.0(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 117.3(3) . . ?
C2 C3 C6 121.4(3) . . ?
C4 C3 C6 121.3(3) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 124.4(4) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C9 C6 C7 120.0(3) . . ?
C9 C6 C3 118.9(3) . . ?
C7 C6 C3 121.1(3) . . ?
C9 C7 C6 117.3(3) 5_566 . ?
C9 C7 C8 120.9(3) 5_566 . ?
C6 C7 C8 121.8(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 C7 122.7(3) . 5_566 ?
C6 C9 H9 118.7 . . ?
C7 C9 H9 118.7 5_566 . ?
C11 C10 C11 117.5(4) 3_755 . ?
C11 C10 I1 121.2(2) 3_755 . ?
C11 C10 I1 121.2(2) . . ?
F1 C11 C12 118.3(3) . . ?
F1 C11 C10 119.0(3) . . ?
C12 C11 C10 122.7(3) . . ?
C11 C12 C13 116.4(3) . . ?
C11 C12 I2 123.0(3) . . ?
C13 C12 I2 120.6(2) . . ?
F2 C13 C12 117.9(2) . . ?
F2 C13 C12 117.9(2) . 3_755 ?
C12 C13 C12 124.2(4) . 3_755 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        30.04
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.274
_refine_diff_density_min         -1.258
_refine_diff_density_rms         0.102
####################################################################### 
# 
# 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_e3407a
_database_code_depnum_ccdc_archive 'CCDC 2076763'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H28 F6 I6 N2'
_chemical_formula_weight         1460.08

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.7820(3)
_cell_length_b                   33.4952(14)
_cell_length_c                   9.1815(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.9896(11)
_cell_angle_gamma                90.00
_cell_volume                     2169.20(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1356
_exptl_absorpt_coefficient_mu    4.357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6229
_exptl_absorpt_correction_T_max  0.8450
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22232
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         30.05
_reflns_number_total             6291
_reflns_number_gt                5454
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0398P)²+4.6704P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6291
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0863
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0589(5) 0.10416(9) 0.3728(4) 0.0299(7) Uani 1 1 d . . .
C1 C -0.1482(5) 0.07505(11) 0.4124(4) 0.0287(7) Uani 1 1 d . . .
H1 H -0.2621 0.0648 0.3312 0.034 Uiso 1 1 calc R . .
C2 C -0.0841(5) 0.05896(10) 0.5654(4) 0.0259(7) Uani 1 1 d . . .
H2 H -0.1525 0.0380 0.5869 0.031 Uiso 1 1 calc R . .
C3 C 0.0810(5) 0.07369(9) 0.6872(4) 0.0206(6) Uani 1 1 d . . .
C4 C 0.1777(5) 0.10332(10) 0.6451(4) 0.0245(7) Uani 1 1 d . . .
H4 H 0.2942 0.1136 0.7228 0.029 Uiso 1 1 calc R . .
C5 C 0.1027(6) 0.11752(11) 0.4897(4) 0.0306(8) Uani 1 1 d . . .
H5 H 0.1696 0.1380 0.4640 0.037 Uiso 1 1 calc R . .
C6 C 0.1575(5) 0.05785(9) 0.8540(4) 0.0211(6) Uani 1 1 d . . .
C7 C 0.2072(5) 0.08345(9) 0.9869(4) 0.0217(6) Uani 1 1 d . . .
C8 C 0.1700(6) 0.12752(10) 0.9743(4) 0.0295(8) Uani 1 1 d . . .
H8A H 0.1032 0.1348 1.0401 0.044 Uiso 1 1 calc R . .
H8B H 0.0917 0.1346 0.8619 0.044 Uiso 1 1 calc R . .
H8C H 0.2907 0.1419 1.0125 0.044 Uiso 1 1 calc R . .
C9 C 0.2883(5) 0.06638(10) 1.1389(4) 0.0232(6) Uani 1 1 d . . .
H9 H 0.3251 0.0835 1.2296 0.028 Uiso 1 1 calc R . .
C10 C 0.3186(5) 0.02551(10) 1.1658(4) 0.0219(6) Uani 1 1 d . . .
C11 C 0.2600(5) -0.00050(9) 1.0322(4) 0.0223(6) Uani 1 1 d . . .
C12 C 0.2726(6) -0.04544(10) 1.0442(4) 0.0305(8) Uani 1 1 d . . .
H12A H 0.1704 -0.0572 0.9495 0.046 Uiso 1 1 calc R . .
H12B H 0.2602 -0.0541 1.1413 0.046 Uiso 1 1 calc R . .
H12C H 0.3954 -0.0542 1.0497 0.046 Uiso 1 1 calc R . .
C13 C 0.1797(5) 0.01679(9) 0.8800(4) 0.0215(6) Uani 1 1 d . . .
H13 H 0.1378 -0.0003 0.7890 0.026 Uiso 1 1 calc R . .
C14 C 0.4098(5) 0.01135(10) 1.3359(4) 0.0211(6) Uani 1 1 d . . .
C15 C 0.5533(5) -0.01720(10) 1.3887(4) 0.0232(6) Uani 1 1 d . . .
H15 H 0.5922 -0.0291 1.3136 0.028 Uiso 1 1 calc R . .
C16 C 0.3595(5) 0.02863(10) 1.4513(4) 0.0229(6) Uani 1 1 d . . .
H16 H 0.2638 0.0486 1.4194 0.027 Uiso 1 1 calc R . .
C17 C 0.3683(5) 0.25116(11) 0.7959(4) 0.0235(7) Uani 1 1 d . . .
I1 I 0.13605(3) 0.245134(9) 0.57585(3) 0.03619(8) Uani 1 1 d . . .
C18 C 0.4278(5) 0.28809(11) 0.8634(4) 0.0260(7) Uani 1 1 d . . .
F1 F 0.3353(4) 0.32067(7) 0.7843(3) 0.0396(6) Uani 1 1 d . . .
C19 C 0.5770(5) 0.29313(11) 1.0139(4) 0.0259(7) Uani 1 1 d . . .
I2 I 0.66467(5) 0.349857(9) 1.10487(4) 0.04440(9) Uani 1 1 d . . .
C20 C 0.6634(5) 0.25909(11) 1.0964(4) 0.0258(7) Uani 1 1 d . . .
F2 F 0.8014(3) 0.26318(8) 1.2457(3) 0.0374(5) Uani 1 1 d . . .
C21 C 0.6131(5) 0.22106(11) 1.0348(4) 0.0249(7) Uani 1 1 d . . .
I3 I 0.74876(4) 0.170143(8) 1.16435(3) 0.03283(7) Uani 1 1 d . . .
C22 C 0.4648(5) 0.21842(10) 0.8832(4) 0.0239(6) Uani 1 1 d . . .
F3 F 0.4093(4) 0.18216(7) 0.8187(3) 0.0374(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
N1 C1 1.334(5) . ?
N1 C5 1.339(5) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(5) . ?
C3 C6 1.487(4) . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C13 1.394(4) . ?
C6 C7 1.405(4) . ?
C7 C9 1.389(4) . ?
C7 C8 1.499(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.393(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.414(4) . ?
C10 C14 1.494(4) . ?
C11 C13 1.393(4) . ?
C11 C12 1.510(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C14 C15 1.393(5) . ?
C14 C16 1.400(4) . ?
C15 C16 1.387(4) 3_658 ?
C15 H15 0.9500 . ?
C16 C15 1.387(4) 3_658 ?
C16 H16 0.9500 . ?
C17 C18 1.374(5) . ?
C17 C22 1.379(5) . ?
C17 I1 2.075(3) . ?
C18 F1 1.340(4) . ?
C18 C19 1.389(5) . ?
C19 C20 1.377(5) . ?
C19 I2 2.072(4) . ?
C20 F2 1.344(4) . ?
C20 C21 1.381(5) . ?
C21 C22 1.385(5) . ?
C21 I3 2.092(3) . ?
C22 F3 1.340(4) . ?

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 C5 116.5(3) . . ?
N1 C1 C2 123.7(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 116.9(3) . . ?
C2 C3 C6 122.3(3) . . ?
C4 C3 C6 120.7(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.9(3) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C13 C6 C7 119.0(3) . . ?
C13 C6 C3 119.7(3) . . ?
C7 C6 C3 121.3(3) . . ?
C9 C7 C6 117.6(3) . . ?
C9 C7 C8 118.3(3) . . ?
C6 C7 C8 124.1(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 C10 123.6(3) . . ?
C7 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 C14 117.9(3) . . ?
C11 C10 C14 123.2(3) . . ?
C13 C11 C10 117.2(3) . . ?
C13 C11 C12 118.4(3) . . ?
C10 C11 C12 124.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C6 123.5(3) . . ?
C11 C13 H13 118.2 . . ?
C6 C13 H13 118.2 . . ?
C15 C14 C16 117.4(3) . . ?
C15 C14 C10 122.6(3) . . ?
C16 C14 C10 119.9(3) . . ?
C16 C15 C14 121.3(3) 3_658 . ?
C16 C15 H15 119.3 3_658 . ?
C14 C15 H15 119.3 . . ?
C15 C16 C14 121.3(3) 3_658 . ?
C15 C16 H16 119.4 3_658 . ?
C14 C16 H16 119.4 . . ?
C18 C17 C22 117.2(3) . . ?
C18 C17 I1 121.1(2) . . ?
C22 C17 I1 121.7(3) . . ?
F1 C18 C17 119.2(3) . . ?
F1 C18 C19 118.2(3) . . ?
C17 C18 C19 122.6(3) . . ?
C20 C19 C18 117.1(3) . . ?
C20 C19 I2 122.4(3) . . ?
C18 C19 I2 120.5(3) . . ?
F2 C20 C19 118.1(3) . . ?
F2 C20 C21 118.5(3) . . ?
C19 C20 C21 123.4(3) . . ?
C22 C21 C20 116.2(3) . . ?
C22 C21 I3 121.7(3) . . ?
C20 C21 I3 122.1(2) . . ?
F3 C22 C17 118.0(3) . . ?
F3 C22 C21 118.6(3) . . ?
C17 C22 C21 123.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.500
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.125
####################################################################### 
# 
# 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_e3586a_a
_database_code_depnum_ccdc_archive 'CCDC 2076760'
loop_
_audit_author_name
_audit_author_address
'Veronique Bulach'
;University of Strasbourg 
France
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N4, C6 F4 I2'
_chemical_formula_sum            'C28 H16 F4 I2 N4'
_chemical_formula_weight         738.25

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'
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/n'
_space_group_name_Hall           '-P 2yn'

_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'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3957(5)
_cell_length_b                   17.8774(6)
_cell_length_c                   13.0708(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.9150(10)
_cell_angle_gamma                90
_cell_volume                     2605.26(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    25000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.468
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25438
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         30.083
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7479
_reflns_number_gt                6262
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0478P)²+2.8941P] 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         7479
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
C1 C 0.1565(3) 0.41182(16) 0.0353(2) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.1979(3) 0.43353(17) -0.0437(2) 0.0266(6) Uani 1 1 d . . . . .
H2 H 0.2812 0.4411 -0.0205 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1174(3) 0.44390(17) -0.1554(2) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.1478 0.4583 -0.2078 0.035 Uiso 1 1 calc R U . . .
N1 N -0.0014(2) 0.43493(15) -0.1948(2) 0.0299(5) Uani 1 1 d . . . . .
C4 C -0.0417(3) 0.41422(19) -0.1196(3) 0.0313(6) Uani 1 1 d . . . . .
H4 H -0.1255 0.4068 -0.1458 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0328(3) 0.40297(18) -0.0050(2) 0.0285(6) Uani 1 1 d . . . . .
H5 H -0.0002 0.3893 0.0456 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2394(2) 0.39724(16) 0.1560(2) 0.0236(5) Uani 1 1 d . . . . .
C7 C 0.3492(3) 0.36268(16) 0.1842(2) 0.0246(5) Uani 1 1 d . . . . .
H7 H 0.3709 0.3491 0.1254 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4283(2) 0.34755(16) 0.2972(2) 0.0231(5) Uani 1 1 d . . . . .
C9 C 0.4005(3) 0.37024(16) 0.3861(2) 0.0244(5) Uani 1 1 d . . . . .
C10 C 0.2894(3) 0.40395(19) 0.3564(2) 0.0299(6) Uani 1 1 d . . . . .
H10 H 0.2680 0.4185 0.4149 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2091(3) 0.41698(18) 0.2439(2) 0.0278(6) Uani 1 1 d . . . . .
H11 H 0.1336 0.4393 0.2265 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4843(3) 0.36238(16) 0.5085(2) 0.0237(5) Uani 1 1 d . . . . .
C13 C 0.5510(3) 0.29815(18) 0.5564(3) 0.0319(6) Uani 1 1 d . . . . .
H13 H 0.5463 0.2561 0.5101 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6241(3) 0.2963(2) 0.6721(3) 0.0351(7) Uani 1 1 d . . . . .
H14 H 0.6681 0.2518 0.7032 0.042 Uiso 1 1 calc R U . . .
N2 N 0.6367(3) 0.35297(16) 0.7425(2) 0.0335(6) Uani 1 1 d . . . . .
C15 C 0.5740(3) 0.41457(19) 0.6969(2) 0.0316(6) Uani 1 1 d . . . . .
H15 H 0.5824 0.4560 0.7454 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4973(3) 0.42142(18) 0.5827(2) 0.0289(6) Uani 1 1 d . . . . .
H16 H 0.4534 0.4664 0.5547 0.035 Uiso 1 1 calc R U . . .
N3 N 0.5414(2) 0.31207(14) 0.32766(19) 0.0251(5) Uani 1 1 d . . . . .
N4 N 0.5463(2) 0.27630(14) 0.2477(2) 0.0264(5) Uani 1 1 d . . . . .
C17 C 0.6579(3) 0.24030(16) 0.2749(2) 0.0246(5) Uani 1 1 d . . . . .
C18 C 0.7545(3) 0.23925(17) 0.3829(3) 0.0275(6) Uani 1 1 d . . . . .
H18 H 0.7493 0.2642 0.4447 0.033 Uiso 1 1 calc R U . . .
C19 C 0.8582(3) 0.20124(19) 0.3986(3) 0.0350(7) Uani 1 1 d . . . . .
H19 H 0.9247 0.2001 0.4715 0.042 Uiso 1 1 calc R U . . .
C20 C 0.8647(3) 0.1646(2) 0.3069(3) 0.0411(8) Uani 1 1 d . . . . .
H20 H 0.9357 0.1384 0.3183 0.049 Uiso 1 1 calc R U . . .
C21 C 0.7699(3) 0.1660(2) 0.2009(3) 0.0414(8) Uani 1 1 d . . . . .
H21 H 0.7758 0.1412 0.1392 0.050 Uiso 1 1 calc R U . . .
C22 C 0.6646(3) 0.20386(18) 0.1837(3) 0.0321(6) Uani 1 1 d . . . . .
H22 H 0.5984 0.2047 0.1105 0.038 Uiso 1 1 calc R U . . .
C23 C 0.7640(3) 0.38319(18) 0.1539(2) 0.0270(6) Uani 1 1 d . . . . .
I1 I 0.71353(2) 0.35922(2) -0.01774(2) 0.03204(7) Uani 1 1 d . . . . .
C24 C 0.8770(3) 0.36540(18) 0.2359(2) 0.0274(6) Uani 1 1 d . . . . .
F1 F 0.95522(17) 0.32947(12) 0.20680(16) 0.0372(4) Uani 1 1 d . . . . .
C25 C 0.9123(3) 0.38221(18) 0.3489(2) 0.0267(6) Uani 1 1 d . . . . .
F2 F 1.02281(17) 0.36108(12) 0.42443(15) 0.0375(4) Uani 1 1 d . . . . .
C26 C 0.8372(3) 0.41745(17) 0.3863(2) 0.0267(6) Uani 1 1 d . . . . .
I2 I 0.88777(2) 0.43216(2) 0.55963(2) 0.03190(7) Uani 1 1 d . . . . .
C27 C 0.7240(3) 0.43697(17) 0.3030(3) 0.0275(6) Uani 1 1 d . . . . .
F3 F 0.64583(18) 0.47219(12) 0.33218(17) 0.0384(4) Uani 1 1 d . . . . .
C28 C 0.6882(3) 0.42000(18) 0.1895(2) 0.0278(6) Uani 1 1 d . . . . .
F4 F 0.57736(18) 0.43982(13) 0.11364(17) 0.0426(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
C1 C5 1.395(4) . ?
C1 C2 1.395(4) . ?
C1 C6 1.481(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 N1 1.340(4) . ?
C3 H3 0.9500 . ?
N1 C4 1.334(4) . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.389(4) . ?
C6 C11 1.401(4) . ?
C7 C8 1.396(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.408(4) . ?
C8 N3 1.428(4) . ?
C9 C10 1.394(4) . ?
C9 C12 1.485(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C12 C16 1.394(4) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 N2 1.332(4) . ?
C14 H14 0.9500 . ?
N2 C15 1.329(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N3 N4 1.249(3) . ?
N4 C17 1.424(4) . ?
C17 C22 1.392(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.398(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.399(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.379(4) . ?
C23 C28 1.384(4) . ?
C23 I1 2.093(3) . ?
C24 F1 1.349(3) . ?
C24 C25 1.377(4) . ?
C25 F2 1.346(3) . ?
C25 C26 1.378(4) . ?
C26 C27 1.393(4) . ?
C26 I2 2.086(3) . ?
C27 F3 1.344(3) . ?
C27 C28 1.384(4) . ?
C28 F4 1.344(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
C5 C1 C2 116.8(3) . . ?
C5 C1 C6 121.3(3) . . ?
C2 C1 C6 121.9(3) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N1 C3 C2 123.9(3) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
C4 N1 C3 116.9(3) . . ?
N1 C4 C5 123.2(3) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C1 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C1 C5 H5 120.2 . . ?
C7 C6 C11 118.5(3) . . ?
C7 C6 C1 120.3(2) . . ?
C11 C6 C1 121.2(3) . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 N3 122.1(2) . . ?
C9 C8 N3 117.5(2) . . ?
C10 C9 C8 117.6(3) . . ?
C10 C9 C12 118.8(2) . . ?
C8 C9 C12 123.6(3) . . ?
C11 C10 C9 122.1(3) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C13 C12 C16 116.5(3) . . ?
C13 C12 C9 124.1(3) . . ?
C16 C12 C9 119.5(3) . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
N2 C14 C13 124.1(3) . . ?
N2 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C15 N2 C14 116.8(3) . . ?
N2 C15 C16 123.3(3) . . ?
N2 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C15 C16 C12 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C12 C16 H16 120.0 . . ?
N4 N3 C8 113.3(2) . . ?
N3 N4 C17 114.8(2) . . ?
C22 C17 C18 120.9(3) . . ?
C22 C17 N4 114.4(3) . . ?
C18 C17 N4 124.7(3) . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 119.3(3) . . ?
C17 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C24 C23 C28 117.2(3) . . ?
C24 C23 I1 120.9(2) . . ?
C28 C23 I1 121.9(2) . . ?
F1 C24 C25 118.4(3) . . ?
F1 C24 C23 120.1(3) . . ?
C25 C24 C23 121.5(3) . . ?
F2 C25 C24 118.0(3) . . ?
F2 C25 C26 119.8(2) . . ?
C24 C25 C26 122.2(3) . . ?
C25 C26 C27 116.3(3) . . ?
C25 C26 I2 120.9(2) . . ?
C27 C26 I2 122.6(2) . . ?
F3 C27 C28 118.3(3) . . ?
F3 C27 C26 120.0(3) . . ?
C28 C27 C26 121.7(3) . . ?
F4 C28 C27 118.6(3) . . ?
F4 C28 C23 120.2(3) . . ?
C27 C28 C23 121.2(3) . . ?

_refine_diff_density_max         2.703
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.109

_shelxl_version_number           2014/6



