# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2304676'
loop_
_audit_author_name
_audit_author_address
'Elies Molins'
;ICMAB CSIC
Spain
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_date             2024-04-16T16:20:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C13 H8 F4 I2 N4 O2'
_chemical_formula_moiety         'C7 H8 N4 O2, C6 F4 I2'
_chemical_formula_weight         582.03

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   19.924(8)
_cell_length_b                   4.4267(18)
_cell_length_c                   20.419(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.293(9)
_cell_angle_gamma                90
_cell_volume                     1654.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5504
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      24.7
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            colourless
_exptl_crystal_description       'flat prism'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    2.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10
;
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.411
_shelx_estimated_absorpt_T_max   0.927

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.000546
_diffrn_orient_matrix_ub_12      0.223173
_diffrn_orient_matrix_ub_13      0.007785
_diffrn_orient_matrix_ub_21      0.049063
_diffrn_orient_matrix_ub_22      -0.017383
_diffrn_orient_matrix_ub_23      0.040161
_diffrn_orient_matrix_ub_31      0.024053
_diffrn_orient_matrix_ub_32      0.030391
_diffrn_orient_matrix_ub_33      -0.034197
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_number            32965
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         28.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3979
_reflns_number_gt                3083
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V6.45A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+1.5962P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3979
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.58369(2) 0.23432(6) 0.69950(2) 0.05286(9) Uani 1 1 d . . . . .
I2 I 0.76258(2) -0.20394(7) 0.48331(2) 0.06162(11) Uani 1 1 d . . . . .
F1 F 0.53586(13) -0.1921(6) 0.56159(13) 0.0656(7) Uani 1 1 d . . . . .
F2 F 0.60410(14) -0.3595(6) 0.47885(13) 0.0736(7) Uani 1 1 d . . . . .
F3 F 0.81013(13) 0.2116(6) 0.62096(13) 0.0633(6) Uani 1 1 d . . . . .
F4 F 0.74054(13) 0.3889(6) 0.70111(12) 0.0635(6) Uani 1 1 d . . . . .
O2 O 0.31924(14) 1.1024(6) 0.71904(13) 0.0518(6) Uani 1 1 d . . . . .
O6 O 0.41564(15) 0.7935(6) 0.95074(14) 0.0517(7) Uani 1 1 d . . . . .
N1 N 0.36875(14) 0.9461(6) 0.83479(14) 0.0382(6) Uani 1 1 d . . . . .
N3 N 0.41003(16) 0.7546(6) 0.74885(15) 0.0409(7) Uani 1 1 d . . . . .
N7 N 0.52031(15) 0.4047(7) 0.90894(15) 0.0440(7) Uani 1 1 d . . . . .
H7 H 0.536226 0.364669 0.95375 0.053 Uiso 1 1 calc R U . . .
N9 N 0.50930(16) 0.3933(7) 0.79589(16) 0.0460(7) Uani 1 1 d . . . . .
C1 C 0.3152(2) 1.1360(8) 0.8485(2) 0.0493(9) Uani 1 1 d . . . . .
H1A H 0.270188 1.026735 0.836002 0.074 Uiso 1 1 calc R U . . .
H1B H 0.306541 1.316532 0.820266 0.074 Uiso 1 1 calc R U . . .
H1C H 0.333793 1.188818 0.898096 0.074 Uiso 1 1 calc R U . . .
C2 C 0.36366(18) 0.9448(8) 0.76419(18) 0.0400(8) Uani 1 1 d . . . . .
C3 C 0.4046(2) 0.7321(9) 0.6757(2) 0.0557(10) Uani 1 1 d . . . . .
H3A H 0.452687 0.719333 0.67572 0.083 Uiso 1 1 calc R U . . .
H3B H 0.38015 0.907572 0.649404 0.083 Uiso 1 1 calc R U . . .
H3C H 0.377281 0.554521 0.653737 0.083 Uiso 1 1 calc R U . . .
C4 C 0.46029(18) 0.5875(8) 0.80252(17) 0.0382(7) Uani 1 1 d . . . . .
C5 C 0.46455(18) 0.6018(8) 0.87096(17) 0.0379(7) Uani 1 1 d . . . . .
C6 C 0.41705(19) 0.7804(7) 0.89115(19) 0.0405(8) Uani 1 1 d . . . . .
C8 C 0.5443(2) 0.2896(8) 0.8617(2) 0.0481(9) Uani 1 1 d . . . . .
H8 H 0.582118 0.149575 0.873836 0.058 Uiso 1 1 calc R U . . .
C10 C 0.6362(2) 0.1020(8) 0.63403(18) 0.0435(8) Uani 1 1 d . . . . .
C11 C 0.6036(2) -0.0882(9) 0.5769(2) 0.0468(9) Uani 1 1 d . . . . .
C12 C 0.6383(2) -0.1745(9) 0.5338(2) 0.0502(9) Uani 1 1 d . . . . .
C13 C 0.7088(2) -0.0771(9) 0.54748(18) 0.0456(8) Uani 1 1 d . . . . .
C14 C 0.7417(2) 0.1116(9) 0.60481(19) 0.0445(8) Uani 1 1 d . . . . .
C15 C 0.7058(2) 0.1996(8) 0.64698(19) 0.0439(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C10 2.081(3) . ?
I2 C13 2.072(4) . ?
F1 C11 1.341(4) . ?
F2 C12 1.337(4) . ?
F3 C14 1.344(4) . ?
F4 C15 1.341(4) . ?
O2 C2 1.214(4) . ?
O6 C6 1.230(4) . ?
N1 C6 1.383(4) . ?
N1 C2 1.405(4) . ?
N1 C1 1.470(4) . ?
N3 C4 1.372(4) . ?
N3 C2 1.375(4) . ?
N3 C3 1.458(4) . ?
N7 C8 1.336(4) . ?
N7 C5 1.384(4) . ?
N9 C8 1.328(5) . ?
N9 C4 1.348(4) . ?
C4 C5 1.368(4) . ?
C5 C6 1.414(5) . ?
C10 C15 1.375(5) . ?
C10 C11 1.376(5) . ?
C11 C12 1.371(5) . ?
C12 C13 1.387(5) . ?
C13 C14 1.375(5) . ?
C14 C15 1.375(5) . ?

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
C6 N1 C2 126.6(3) . . ?
C6 N1 C1 117.6(3) . . ?
C2 N1 C1 115.7(3) . . ?
C4 N3 C2 119.5(3) . . ?
C4 N3 C3 121.1(3) . . ?
C2 N3 C3 119.4(3) . . ?
C8 N7 C5 105.9(3) . . ?
C8 N9 C4 103.3(3) . . ?
O2 C2 N3 122.2(3) . . ?
O2 C2 N1 120.8(3) . . ?
N3 C2 N1 117.0(3) . . ?
N9 C4 C5 112.2(3) . . ?
N9 C4 N3 126.4(3) . . ?
C5 C4 N3 121.5(3) . . ?
C4 C5 N7 104.8(3) . . ?
C4 C5 C6 123.1(3) . . ?
N7 C5 C6 132.1(3) . . ?
O6 C6 N1 121.2(3) . . ?
O6 C6 C5 126.5(3) . . ?
N1 C6 C5 112.3(3) . . ?
N9 C8 N7 113.8(3) . . ?
C15 C10 C11 117.2(3) . . ?
C15 C10 I1 120.9(3) . . ?
C11 C10 I1 121.9(3) . . ?
F1 C11 C12 118.2(3) . . ?
F1 C11 C10 120.1(3) . . ?
C12 C11 C10 121.7(4) . . ?
F2 C12 C11 119.3(4) . . ?
F2 C12 C13 119.9(3) . . ?
C11 C12 C13 120.7(3) . . ?
C14 C13 C12 117.7(3) . . ?
C14 C13 I2 120.7(3) . . ?
C12 C13 I2 121.6(3) . . ?
F3 C14 C15 118.7(3) . . ?
F3 C14 C13 120.3(3) . . ?
C15 C14 C13 120.9(3) . . ?
F4 C15 C10 120.5(3) . . ?
F4 C15 C14 117.8(3) . . ?
C10 C15 C14 121.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N7 H7 O6 0.86 1.93 2.778(4) 167.3 3_667 yes
C1 H1A O2 0.96 2.53 3.425(5) 155.9 2_546 yes
C1 H1B O2 0.96 2.63 3.227(5) 120.4 2_556 yes
C3 H3A I1 0.96 3.35 4.067(4) 132.8 1_565 yes
C3 H3B I2 0.96 3.33 4.176(4) 148.9 3_666 yes

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

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2304677'
loop_
_audit_author_name
_audit_author_address
'Elies Molins'
;ICMAB CSIC
Spain
;
_audit_update_record             
;
2024-04-25 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_date             2024-04-16T16:28:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H16 F4 I2 N8 O4'
_chemical_formula_moiety         '2(C7 H8 N4 O2), C6 F4 I2'
_chemical_formula_weight         762.21

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0269(18)
_cell_length_b                   7.451(3)
_cell_length_c                   20.660(9)
_cell_angle_alpha                82.022(8)
_cell_angle_beta                 88.669(8)
_cell_angle_gamma                80.671(9)
_cell_volume                     605.8(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2689
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      18.62
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            colorless
_exptl_crystal_description       'flat prism'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    2.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS - Bruker Nonius area detector scaling and absorption correction -
;
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.74
_shelx_estimated_absorpt_T_max   0.835

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.146578
_diffrn_orient_matrix_ub_12      -0.096406
_diffrn_orient_matrix_ub_13      0.000402
_diffrn_orient_matrix_ub_21      0.036884
_diffrn_orient_matrix_ub_22      -0.000106
_diffrn_orient_matrix_ub_23      -0.048028
_diffrn_orient_matrix_ub_31      0.201215
_diffrn_orient_matrix_ub_32      -0.097766
_diffrn_orient_matrix_ub_33      0.009051
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_number            12902
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.991
_diffrn_reflns_theta_max         28.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3074
_reflns_number_gt                2106
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V6.45A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.141
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.199
_refine_diff_density_min         -1.623
_refine_diff_density_rms         0.143

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.58701(9) 0.14864(7) 0.63715(2) 0.0552(2) Uani 1 1 d . . . . .
F1 F 0.7647(16) 0.3562(6) 0.5001(3) 0.1033(19) Uani 1 1 d . . . . .
F2 F 1.0897(16) 0.2467(7) 0.3959(2) 0.0992(19) Uani 1 1 d . . . . .
O2 O 0.6963(13) 0.7420(7) 0.8363(2) 0.0611(13) Uani 1 1 d . . . . .
O6 O 0.3265(12) 0.3097(6) 0.9830(2) 0.0499(10) Uani 1 1 d . . . . .
N1 N 0.5077(12) 0.5212(7) 0.9070(2) 0.0411(11) Uani 1 1 d . . . . .
H1 H 0.563791 0.57482 0.938425 0.049 Uiso 1 1 calc R U . . .
N3 N 0.4909(12) 0.5184(7) 0.7944(2) 0.0434(11) Uani 1 1 d . . . . .
N7 N 0.1653(12) 0.1282(7) 0.8640(2) 0.0399(11) Uani 1 1 d . . . . .
N9 N 0.2695(13) 0.2592(7) 0.7632(2) 0.0437(11) Uani 1 1 d . . . . .
C2 C 0.5711(15) 0.6043(9) 0.8444(3) 0.0446(14) Uani 1 1 d . . . . .
C3 C 0.5483(19) 0.5984(10) 0.7272(3) 0.0590(17) Uani 1 1 d . . . . .
H3A H 0.738286 0.525899 0.709349 0.089 Uiso 1 1 calc R U . . .
H3B H 0.592054 0.72146 0.726796 0.089 Uiso 1 1 calc R U . . .
H3C H 0.352359 0.600464 0.701366 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3583(13) 0.3615(8) 0.8075(3) 0.0382(12) Uani 1 1 d . . . . .
C5 C 0.2966(13) 0.2853(8) 0.8701(3) 0.0371(12) Uani 1 1 d . . . . .
C6 C 0.3671(14) 0.3645(8) 0.9258(3) 0.0404(13) Uani 1 1 d . . . . .
C7 C 0.0710(17) -0.0031(9) 0.9162(3) 0.0498(15) Uani 1 1 d . . . . .
H7A H -0.019914 -0.096783 0.898215 0.075 Uiso 1 1 calc R U . . .
H7B H -0.095476 0.057943 0.943236 0.075 Uiso 1 1 calc R U . . .
H7C H 0.265656 -0.057913 0.942099 0.075 Uiso 1 1 calc R U . . .
C8 C 0.1560(15) 0.1195(9) 0.8002(3) 0.0448(14) Uani 1 1 d . . . . .
H8 H 0.078007 0.025317 0.782891 0.054 Uiso 1 1 calc R U . . .
C9 C 0.8259(13) 0.0600(9) 0.5553(3) 0.0446(14) Uani 1 1 d . . . . .
C10 C 0.8837(18) 0.1795(10) 0.5005(4) 0.0576(17) Uani 1 1 d . . . . .
C11 C 1.0454(18) 0.1196(10) 0.4476(3) 0.0554(17) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C9 2.062(6) . ?
F1 C10 1.325(8) . ?
F2 C11 1.354(8) . ?
O2 C2 1.204(8) . ?
O6 C6 1.211(7) . ?
N1 C6 1.384(8) . ?
N1 C2 1.390(8) . ?
N3 C4 1.354(8) . ?
N3 C2 1.360(7) . ?
N3 C3 1.462(8) . ?
N7 C8 1.331(8) . ?
N7 C5 1.382(7) . ?
N7 C7 1.440(8) . ?
N9 C8 1.339(8) . ?
N9 C4 1.356(7) . ?
C4 C5 1.373(8) . ?
C5 C6 1.419(7) . ?
C9 C11 1.363(10) 2_756 ?
C9 C10 1.380(10) . ?
C10 C11 1.351(10) . ?

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
C6 N1 C2 129.1(5) . . ?
C4 N3 C2 119.8(5) . . ?
C4 N3 C3 121.2(5) . . ?
C2 N3 C3 119.1(5) . . ?
C8 N7 C5 105.9(5) . . ?
C8 N7 C7 127.1(5) . . ?
C5 N7 C7 126.9(5) . . ?
C8 N9 C4 103.7(5) . . ?
O2 C2 N3 123.1(6) . . ?
O2 C2 N1 120.9(5) . . ?
N3 C2 N1 116.0(6) . . ?
N3 C4 N9 126.7(5) . . ?
N3 C4 C5 122.3(5) . . ?
N9 C4 C5 111.0(5) . . ?
C4 C5 N7 105.7(5) . . ?
C4 C5 C6 122.7(5) . . ?
N7 C5 C6 131.6(6) . . ?
O6 C6 N1 121.1(5) . . ?
O6 C6 C5 128.7(6) . . ?
N1 C6 C5 110.2(5) . . ?
N7 C8 N9 113.6(5) . . ?
C11 C9 C10 114.8(6) 2_756 . ?
C11 C9 I1 122.7(5) 2_756 . ?
C10 C9 I1 122.4(5) . . ?
F1 C10 C11 120.3(7) . . ?
F1 C10 C9 117.9(6) . . ?
C11 C10 C9 121.7(7) . . ?
C10 C11 F2 117.7(7) . . ?
C10 C11 C9 123.4(7) . 2_756 ?
F2 C11 C9 118.9(6) . 2_756 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O6 0.86 2.03 2.887(6) 175.7 2_667 yes
C7 H7A O2 0.96 2.31 3.245(8) 165.1 1_445 yes
C7 H7C O6 0.96 2.63 3.544(8) 158.8 2_657 yes

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

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2304678'
loop_
_audit_author_name
_audit_author_address
'Elies Molins'
;ICMAB CSIC
Spain
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;

_audit_creation_date             2024-05-16T09:45:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C19 H20 F2 I N8 O4'
_chemical_formula_moiety         '2(C8 H10 N4 O2), 0.5(C6 F4 I2)'
_chemical_formula_weight         589.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   21.904(18)
_cell_length_b                   4.044(4)
_cell_length_c                   25.87(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.90(2)
_cell_angle_gamma                90
_cell_volume                     2140(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    493
_cell_measurement_theta_min      6.69
_cell_measurement_theta_max      13.14
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_description       needle
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10
;
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.635
_shelx_estimated_absorpt_T_max   0.912

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.017438
_diffrn_orient_matrix_ub_12      0.071834
_diffrn_orient_matrix_ub_13      0.026964
_diffrn_orient_matrix_ub_21      -0.030134
_diffrn_orient_matrix_ub_22      0.003628
_diffrn_orient_matrix_ub_23      0.005808
_diffrn_orient_matrix_ub_31      0.007073
_diffrn_orient_matrix_ub_32      -0.16164
_diffrn_orient_matrix_ub_33      0.012113
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.3691
_diffrn_reflns_av_unetI/netI     0.1599
_diffrn_reflns_number            58277
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.623
_diffrn_reflns_theta_max         28.944
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_coverage         0
_reflns_number_total             5576
_reflns_number_gt                2720
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V6.45A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5576
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_restrained_S_all      0.97
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.125

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.33766(2) 0.75834(12) 0.46539(2) 0.04324(17) Uani 1 1 d . . . . .
F1 F 0.4623(2) 0.6997(13) 0.5759(2) 0.0687(15) Uani 1 1 d . . . . .
F2 F 0.5848(2) 0.8905(12) 0.60264(19) 0.0623(14) Uani 1 1 d . . . . .
O11 O 0.7846(3) 0.6125(15) 0.9008(3) 0.0671(18) Uani 1 1 d . . . . .
O13 O 0.5798(3) 1.0271(16) 0.8166(3) 0.0689(18) Uani 1 1 d . . . . .
O31 O 0.0897(3) -0.0225(13) 0.2888(2) 0.0533(15) Uani 1 1 d . . . . .
O33 O -0.0045(3) 0.2143(17) 0.4149(3) 0.0673(17) Uani 1 1 d . . . . .
N1 N 0.6831(3) 0.8303(14) 0.8591(3) 0.0437(16) Uani 1 1 d . . . . .
N3 N 0.7664(3) 0.9032(16) 0.8226(3) 0.0446(16) Uani 1 1 d . . . . .
N7 N 0.6274(3) 1.2887(16) 0.7300(3) 0.0556(18) Uani 1 1 d . . . . .
N9 N 0.7343(4) 1.2024(17) 0.7378(3) 0.060(2) Uani 1 1 d . . . . .
N21 N 0.0430(3) 0.1019(15) 0.3518(3) 0.0417(15) Uani 1 1 d . . . . .
N23 N 0.1496(3) 0.2770(15) 0.3626(3) 0.0400(14) Uani 1 1 d . . . . .
N27 N 0.1240(3) 0.5710(16) 0.4788(3) 0.0457(16) Uani 1 1 d . . . . .
N29 N 0.2049(3) 0.5829(15) 0.4461(3) 0.0422(15) Uani 1 1 d . . . . .
C2 C 0.7472(4) 0.774(2) 0.8629(3) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.7217(4) 1.0729(18) 0.7792(3) 0.0402(18) Uani 1 1 d . . . . .
C5 C 0.6596(4) 1.1139(19) 0.7770(3) 0.0411(18) Uani 1 1 d . . . . .
C6 C 0.6357(4) 0.9941(19) 0.8164(3) 0.048(2) Uani 1 1 d . . . . .
C8 C 0.6747(5) 1.336(2) 0.7082(4) 0.068(3) Uani 1 1 d . . . . .
H8 H 0.667036 1.451107 0.675339 0.082 Uiso 1 1 calc R U . . .
C10 C 0.8327(4) 0.852(2) 0.8250(4) 0.069(3) Uani 1 1 d . . . . .
H10A H 0.862509 0.904667 0.861471 0.104 Uiso 1 1 calc R U . . .
H10B H 0.84121 0.992633 0.798467 0.104 Uiso 1 1 calc R U . . .
H10C H 0.83828 0.625218 0.816774 0.104 Uiso 1 1 calc R U . . .
C12 C 0.6640(5) 0.691(2) 0.9037(4) 0.062(3) Uani 1 1 d . . . . .
H12A H 0.689322 0.792988 0.938235 0.093 Uiso 1 1 calc R U . . .
H12B H 0.671866 0.456897 0.906099 0.093 Uiso 1 1 calc R U . . .
H12C H 0.618439 0.73212 0.895898 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5613(5) 1.386(2) 0.7063(4) 0.079(3) Uani 1 1 d . . . . .
H14A H 0.538235 1.23464 0.677307 0.119 Uiso 1 1 calc R U . . .
H14B H 0.558828 1.60478 0.691218 0.119 Uiso 1 1 calc R U . . .
H14C H 0.541872 1.385042 0.734192 0.119 Uiso 1 1 calc R U . . .
C15 C 0.4347(3) 0.9009(17) 0.4862(3) 0.0357(16) Uani 1 1 d . . . . .
C16 C 0.4800(4) 0.8509(17) 0.5372(3) 0.0440(19) Uani 1 1 d . . . . .
C17 C 0.5436(4) 0.9454(18) 0.5510(3) 0.0383(17) Uani 1 1 d . . . . .
C22 C 0.0940(4) 0.1083(18) 0.3320(3) 0.0413(18) Uani 1 1 d . . . . .
C24 C 0.1533(3) 0.4138(17) 0.4114(3) 0.0381(17) Uani 1 1 d . . . . .
C25 C 0.1031(4) 0.3995(18) 0.4298(3) 0.0365(16) Uani 1 1 d . . . . .
C26 C 0.0444(4) 0.242(2) 0.4019(4) 0.054(2) Uani 1 1 d . . . . .
C28 C 0.1828(4) 0.6749(17) 0.4858(3) 0.047(2) Uani 1 1 d . . . . .
H28 H 0.207305 0.802483 0.515962 0.057 Uiso 1 1 calc R U . . .
C30 C -0.0157(4) -0.070(2) 0.3173(4) 0.057(2) Uani 1 1 d . . . . .
H30A H -0.042694 0.078429 0.289613 0.085 Uiso 1 1 calc R U . . .
H30B H -0.039366 -0.146955 0.33986 0.085 Uiso 1 1 calc R U . . .
H30C H -0.003731 -0.25518 0.299709 0.085 Uiso 1 1 calc R U . . .
C32 C 0.2020(4) 0.3134(19) 0.3407(4) 0.055(2) Uani 1 1 d . . . . .
H32A H 0.242945 0.256908 0.368836 0.083 Uiso 1 1 calc R U . . .
H32B H 0.203477 0.538163 0.329259 0.083 Uiso 1 1 calc R U . . .
H32C H 0.194014 0.168981 0.309494 0.083 Uiso 1 1 calc R U . . .
C34 C 0.0877(4) 0.634(2) 0.5155(4) 0.059(2) Uani 1 1 d . . . . .
H34A H 0.113943 0.764717 0.546361 0.089 Uiso 1 1 calc R U . . .
H34B H 0.077246 0.427095 0.528626 0.089 Uiso 1 1 calc R U . . .
H34C H 0.048114 0.750297 0.49556 0.089 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C15 2.079(7) . ?
F1 C16 1.341(9) . ?
F2 C17 1.338(8) . ?
O11 C2 1.218(9) . ?
O13 C6 1.232(10) . ?
O31 C22 1.211(9) . ?
O33 C26 1.235(10) . ?
N1 C6 1.386(10) . ?
N1 C2 1.391(11) . ?
N1 C12 1.472(10) . ?
N3 C2 1.362(10) . ?
N3 C4 1.381(9) . ?
N3 C10 1.444(10) . ?
N7 C8 1.357(12) . ?
N7 C5 1.365(10) . ?
N7 C14 1.413(11) . ?
N9 C4 1.305(10) . ?
N9 C8 1.368(12) . ?
N21 C22 1.385(10) . ?
N21 C26 1.405(11) . ?
N21 C30 1.453(9) . ?
N23 C24 1.354(9) . ?
N23 C22 1.374(9) . ?
N23 C32 1.457(10) . ?
N27 C28 1.304(10) . ?
N27 C25 1.373(9) . ?
N27 C34 1.461(10) . ?
N29 C28 1.335(10) . ?
N29 C24 1.350(9) . ?
C4 C5 1.351(11) . ?
C5 C6 1.390(11) . ?
C15 C16 1.354(10) . ?
C15 C17 1.364(10) 3_676 ?
C16 C17 1.364(10) . ?
C24 C25 1.346(10) . ?
C25 C26 1.386(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C2 125.9(7) . . ?
C6 N1 C12 117.7(7) . . ?
C2 N1 C12 116.3(7) . . ?
C2 N3 C4 119.4(7) . . ?
C2 N3 C10 119.4(7) . . ?
C4 N3 C10 121.1(7) . . ?
C8 N7 C5 102.4(7) . . ?
C8 N7 C14 126.6(8) . . ?
C5 N7 C14 130.9(9) . . ?
C4 N9 C8 100.3(8) . . ?
C22 N21 C26 125.3(7) . . ?
C22 N21 C30 115.8(7) . . ?
C26 N21 C30 118.8(7) . . ?
C24 N23 C22 119.1(7) . . ?
C24 N23 C32 121.8(6) . . ?
C22 N23 C32 119.0(7) . . ?
C28 N27 C25 106.2(7) . . ?
C28 N27 C34 126.4(7) . . ?
C25 N27 C34 127.4(7) . . ?
C28 N29 C24 101.9(7) . . ?
O11 C2 N3 121.3(8) . . ?
O11 C2 N1 121.2(8) . . ?
N3 C2 N1 117.5(7) . . ?
N9 C4 C5 114.8(7) . . ?
N9 C4 N3 124.7(8) . . ?
C5 C4 N3 120.4(7) . . ?
C4 C5 N7 107.0(7) . . ?
C4 C5 C6 124.3(7) . . ?
N7 C5 C6 128.6(7) . . ?
O13 C6 N1 120.8(8) . . ?
O13 C6 C5 126.9(8) . . ?
N1 C6 C5 112.3(7) . . ?
N7 C8 N9 115.4(8) . . ?
C16 C15 C17 115.9(7) . 3_676 ?
C16 C15 I1 122.4(6) . . ?
C17 C15 I1 121.7(5) 3_676 . ?
F1 C16 C15 119.3(7) . . ?
F1 C16 C17 118.3(7) . . ?
C15 C16 C17 122.5(7) . . ?
F2 C17 C15 119.9(7) . 3_676 ?
F2 C17 C16 118.4(7) . . ?
C15 C17 C16 121.6(7) 3_676 . ?
O31 C22 N23 120.6(8) . . ?
O31 C22 N21 121.7(7) . . ?
N23 C22 N21 117.6(7) . . ?
C25 C24 N29 112.5(7) . . ?
C25 C24 N23 121.7(7) . . ?
N29 C24 N23 125.8(7) . . ?
C24 C25 N27 105.0(7) . . ?
C24 C25 C26 124.1(8) . . ?
N27 C25 C26 130.9(7) . . ?
O33 C26 C25 129.3(9) . . ?
O33 C26 N21 118.6(8) . . ?
C25 C26 N21 112.1(7) . . ?
N27 C28 N29 114.5(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C14 H14C O13 0.96 2.46 3.097(13) 123.4 . yes
C28 H28 O11 0.93 2.44 3.279(10) 149.7 2_656 yes
C30 H30A O31 0.96 2.51 3.448(10) 166.5 2 yes
C30 H30C O31 0.96 2.62 3.215(10) 120.2 2_545 yes
C32 H32A I1 0.96 3.31 3.954(8) 126.3 . yes
C34 H34A O11 0.96 2.57 3.455(10) 153 2_656 yes

