# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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. 
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data_caf2_i2_2025cesar051
_database_code_depnum_ccdc_archive 'CCDC 2502143'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2026-02-09 deposited with the CCDC.	2026-02-20 downloaded from the CCDC.
;
_audit_creation_date             2026-02-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.92(C8 H10 N4 O2), (I2)'
_chemical_formula_sum            'C15.36 H19.20 I2 N7.68 O3.84'
_chemical_formula_weight         626.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1739(7)
_cell_length_b                   14.8378(11)
_cell_length_c                   16.1206(13)
_cell_angle_alpha                106.896(3)
_cell_angle_beta                 94.066(3)
_cell_angle_gamma                91.916(3)
_cell_volume                     2091.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.358
_cell_measurement_theta_min      2.618
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.549441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0794 before and 0.0581 after correction.
 The Ratio of minimum to maximum transmission is 0.74.

Final HKLF 4 output contains 65813 reflections, Rint = 0.0481
 (23622 with I > 3sig(I), Rint = 0.0396)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1207.4
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37770
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8857
_reflns_number_total             10371
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.153
_refine_diff_density_min         -0.909
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     569
_refine_ls_number_reflns         10371
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²+5.2431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          Twin,Twin
_olex2_refinement_description    
;
1. Restrained distances
 I4-I3 \\sim I4B-I3B
 with sigma of 0.02
2. Others
 Fixed Sof: I4(0.96) I3(0.96) I2(0.96) I1(0.96) N2(0.96) O5(0.96) N5(0.96)
 O8(0.96) O3(0.96) O6(0.96) N6(0.96) N8(0.96) O1(0.96) O2(0.96) N4(0.96)
 N7(0.96) O7(0.96) N9(0.96) N12(0.96) N11(0.96) C13(0.96) C9(0.96) H9(0.96)
 O4(0.96) C8(0.96) H8A(0.96) H8B(0.96) H8C(0.96) C22(0.96) H22A(0.96)
 H22B(0.96) H22C(0.96) N3(0.96) N10(0.96) C4(0.96) C16(0.96) H16A(0.96)
 H16B(0.96) H16C(0.96) C10(0.96) N16(0.96) N13(0.96) N15(0.96) C1(0.96)
 H1(0.96) C25(0.96) H25(0.96) C5(0.96) C24(0.96) H24A(0.96) H24B(0.96)
 H24C(0.96) N14(0.96) C6(0.96) H6A(0.96) H6B(0.96) H6C(0.96) C7(0.96) H7A(0.96)
 H7B(0.96) H7C(0.96) C2(0.96) C3(0.96) C27(0.96) C14(0.96) H14A(0.96)
 H14B(0.96) H14C(0.96) C20(0.96) C30(0.96) H30A(0.96) H30B(0.96) H30C(0.96)
 C29(0.96) C28(0.96) C21(0.96) C12(0.96) C32(0.96) H32A(0.96) H32B(0.96)
 H32C(0.96) C19(0.96) C15(0.96) H15A(0.96) H15B(0.96) H15C(0.96) C31(0.96)
 H31A(0.96) H31B(0.96) H31C(0.96) C11(0.96) C18(0.96) C26(0.96) C17(0.96)
 H17(0.96) C23(0.96) H23A(0.96) H23B(0.96) H23C(0.96) I1B(0.04) N1(0.96)
 I2B(0.04) I3B(0.04) I4B(0.04)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C1(H1), C25(H25), C17(H17)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C22(H22A,H22B,H22C), C16(H16A,H16B,H16C), C24(H24A,H24B,
 H24C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C), C15(H15A,H15B,H15C), C31(H31A,H31B,H31C), C23(H23A,
 H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I4 I 0.40081(2) 0.40162(2) 0.76478(2) 0.01493(6) Uani 0.96 1 d D . P A 1
I3 I 0.20347(2) 0.34504(2) 0.62434(2) 0.01571(6) Uani 0.96 1 d D . P A 1
I2 I 0.35088(2) 0.84078(2) 0.26492(2) 0.01594(6) Uani 0.96 1 d . . P B 1
I1 I 0.26692(2) 0.89682(2) 0.12413(2) 0.01530(6) Uani 0.96 1 d . . P B 1
N2 N 0.0066(4) 0.8948(3) -0.1455(2) 0.0159(7) Uani 0.96 1 d . . P C 1
O5 O -0.3346(3) 0.03953(17) 0.39001(18) 0.0215(6) Uani 0.96 1 d . . P D 1
N5 N 0.4535(3) 0.8022(2) 0.4186(2) 0.0187(6) Uani 0.96 1 d . . P E 1
O8 O 0.9461(3) 0.50139(18) 1.14547(17) 0.0203(5) Uani 0.96 1 d . . P F 1
O3 O 0.2760(3) 0.53838(18) 0.49299(18) 0.0217(5) Uani 0.96 1 d . . P E 1
O6 O -0.3037(3) 0.23363(19) 0.21705(18) 0.0234(6) Uani 0.96 1 d . . P D 1
N6 N 0.6217(3) 0.8479(2) 0.53264(19) 0.0161(6) Uani 0.96 1 d . . P E 1
N8 N 0.3545(3) 0.6621(2) 0.4499(2) 0.0162(6) Uani 0.96 1 d . . P E 1
O1 O 0.3455(3) 1.20691(18) -0.10268(18) 0.0237(6) Uani 0.96 1 d . . P C 1
O2 O 0.0104(3) 0.99399(18) -0.28960(17) 0.0212(5) Uani 0.96 1 d . . P C 1
N4 N 0.2691(3) 1.0816(2) -0.0608(2) 0.0175(6) Uani 0.96 1 d . . P C 1
N7 N 0.4651(3) 0.6345(2) 0.5768(2) 0.0152(6) Uani 0.96 1 d . . P E 1
O7 O 0.9233(3) 0.71104(19) 0.9872(2) 0.0265(6) Uani 0.96 1 d . . P F 1
N9 N 0.0118(3) 0.2959(2) 0.4667(2) 0.0213(7) Uani 0.96 1 d . . P D 1
N12 N -0.1630(3) 0.1610(2) 0.43352(19) 0.0165(6) Uani 0.96 1 d . . P D 1
N11 N -0.3178(3) 0.13755(19) 0.30465(18) 0.0135(6) Uani 0.96 1 d . . P D 1
C13 C 0.4469(4) 0.7416(2) 0.4669(2) 0.0141(6) Uani 0.96 1 d . . P E 1
C9 C 0.5591(4) 0.8655(2) 0.4616(2) 0.0160(7) Uani 0.96 1 d . . P E 1
H9 H 0.5877 0.9186 0.4437 0.019 Uiso 0.96 1 calc R U P E 1
O4 O 0.6531(3) 0.72982(19) 0.66164(18) 0.0235(6) Uani 0.96 1 d . . P E 1
C8 C 0.3668(4) 1.1133(3) 0.0197(2) 0.0251(8) Uani 0.96 1 d . . P C 1
H8A H 0.4682 1.1175 0.0051 0.038 Uiso 0.96 1 calc R U P C 1
H8B H 0.3573 1.0681 0.0531 0.038 Uiso 0.96 1 calc R U P C 1
H8C H 0.3399 1.1755 0.0545 0.038 Uiso 0.96 1 calc R U P C 1
C22 C -0.0574(4) 0.3998(3) 0.2896(3) 0.0205(7) Uani 0.96 1 d . . P D 1
H22A H -0.0425 0.3586 0.2315 0.031 Uiso 0.96 1 calc R U P D 1
H22B H 0.0211 0.4497 0.3079 0.031 Uiso 0.96 1 calc R U P D 1
H22C H -0.1520 0.4283 0.2880 0.031 Uiso 0.96 1 calc R U P D 1
N3 N 0.1771(3) 1.1003(2) -0.1950(2) 0.0180(6) Uani 0.96 1 d . . P C 1
N10 N -0.0556(3) 0.3450(2) 0.3508(2) 0.0178(6) Uani 0.96 1 d . . P D 1
C4 C 0.2681(4) 1.1341(2) -0.1182(2) 0.0180(7) Uani 0.96 1 d . . P C 1
C16 C 0.2460(4) 0.6358(3) 0.3742(2) 0.0219(8) Uani 0.96 1 d . . P E 1
H16A H 0.1480 0.6313 0.3938 0.033 Uiso 0.96 1 calc R U P E 1
H16B H 0.2678 0.5746 0.3350 0.033 Uiso 0.96 1 calc R U P E 1
H16C H 0.2498 0.6838 0.3435 0.033 Uiso 0.96 1 calc R U P E 1
C10 C 0.5474(4) 0.7661(2) 0.5373(2) 0.0140(6) Uani 0.96 1 d . . P E 1
N16 N 0.7587(3) 0.5859(2) 0.9453(2) 0.0182(6) Uani 0.96 1 d . . P F 1
N13 N 0.5974(3) 0.4452(2) 0.9124(2) 0.0161(6) Uani 0.96 1 d . . P F 1
N15 N 0.9234(3) 0.6099(2) 1.0701(2) 0.0172(6) Uani 0.96 1 d . . P F 1
C1 C 0.0559(4) 0.8820(2) -0.0701(2) 0.0167(7) Uani 0.96 1 d . . P C 1
H1 H 0.0201 0.8321 -0.0497 0.020 Uiso 0.96 1 calc R U P C 1
C25 C 0.5885(3) 0.3781(2) 0.9522(2) 0.0139(6) Uani 0.96 1 d . . P F 1
H25 H 0.5197 0.3255 0.9333 0.017 Uiso 0.96 1 calc R U P F 1
C5 C 0.1749(4) 1.0035(2) -0.0772(2) 0.0144(6) Uani 0.96 1 d . . P C 1
C24 C -0.1087(4) 0.1274(3) 0.5062(3) 0.0257(8) Uani 0.96 1 d . . P D 1
H24A H -0.1878 0.1259 0.5436 0.039 Uiso 0.96 1 calc R U P D 1
H24B H -0.0277 0.1701 0.5401 0.039 Uiso 0.96 1 calc R U P D 1
H24C H -0.0741 0.0638 0.4837 0.039 Uiso 0.96 1 calc R U P D 1
N14 N 0.6851(3) 0.3921(2) 1.02079(19) 0.0164(6) Uani 0.96 1 d . . P F 1
C6 C -0.1146(4) 0.8410(2) -0.2054(2) 0.0145(6) Uani 0.96 1 d . . P C 1
H6A H -0.1442 0.7860 -0.1873 0.022 Uiso 0.96 1 calc R U P C 1
H6B H -0.0829 0.8200 -0.2645 0.022 Uiso 0.96 1 calc R U P C 1
H6C H -0.1976 0.8811 -0.2045 0.022 Uiso 0.96 1 calc R U P C 1
C7 C 0.1838(5) 1.1541(3) -0.2586(3) 0.0236(8) Uani 0.96 1 d . . P C 1
H7A H 0.2215 1.2189 -0.2287 0.035 Uiso 0.96 1 calc R U P C 1
H7B H 0.0855 1.1550 -0.2863 0.035 Uiso 0.96 1 calc R U P C 1
H7C H 0.2489 1.1241 -0.3030 0.035 Uiso 0.96 1 calc R U P C 1
C2 C 0.0830(4) 0.9739(2) -0.1520(2) 0.0141(6) Uani 0.96 1 d . . P C 1
C3 C 0.0809(4) 1.0196(2) -0.2187(2) 0.0155(7) Uani 0.96 1 d . . P C 1
C27 C 0.8830(4) 0.5251(2) 1.0876(2) 0.0159(7) Uani 0.96 1 d . . P F 1
C14 C 0.7411(4) 0.9017(2) 0.5922(2) 0.0143(6) Uani 0.96 1 d . . P E 1
H14A H 0.7083 0.9240 0.6509 0.021 Uiso 0.96 1 calc R U P E 1
H14B H 0.7721 0.9559 0.5733 0.021 Uiso 0.96 1 calc R U P E 1
H14C H 0.8236 0.8615 0.5927 0.021 Uiso 0.96 1 calc R U P E 1
C20 C -0.2755(4) 0.1083(2) 0.3767(2) 0.0173(7) Uani 0.96 1 d . . P D 1
C30 C 0.7017(4) 0.3335(2) 1.0804(3) 0.0202(8) Uani 0.96 1 d . . P F 1
H30A H 0.6809 0.3705 1.1390 0.030 Uiso 0.96 1 calc R U P F 1
H30B H 0.8021 0.3131 1.0819 0.030 Uiso 0.96 1 calc R U P F 1
H30C H 0.6331 0.2780 1.0600 0.030 Uiso 0.96 1 calc R U P F 1
C29 C 0.7077(4) 0.5058(2) 0.9606(2) 0.0146(6) Uani 0.96 1 d . . P F 1
C28 C 0.8722(4) 0.6401(3) 1.0003(3) 0.0204(7) Uani 0.96 1 d . . P F 1
C21 C -0.0988(4) 0.2379(2) 0.4175(2) 0.0167(7) Uani 0.96 1 d . . P D 1
C12 C 0.3592(4) 0.6073(2) 0.5052(2) 0.0168(7) Uani 0.96 1 d . . P E 1
C32 C 0.7105(5) 0.6095(3) 0.8666(3) 0.0274(9) Uani 0.96 1 d . . P F 1
H32A H 0.7875 0.5967 0.8262 0.041 Uiso 0.96 1 calc R U P F 1
H32B H 0.6903 0.6765 0.8815 0.041 Uiso 0.96 1 calc R U P F 1
H32C H 0.6213 0.5712 0.8390 0.041 Uiso 0.96 1 calc R U P F 1
C19 C -0.2573(4) 0.2157(2) 0.2831(2) 0.0153(7) Uani 0.96 1 d . . P D 1
C15 C 0.4695(4) 0.5760(3) 0.6359(3) 0.0229(8) Uani 0.96 1 d . . P E 1
H15A H 0.4336 0.6110 0.6914 0.034 Uiso 0.96 1 calc R U P E 1
H15B H 0.5704 0.5596 0.6461 0.034 Uiso 0.96 1 calc R U P E 1
H15C H 0.4074 0.5182 0.6099 0.034 Uiso 0.96 1 calc R U P E 1
C31 C 1.0377(4) 0.6709(3) 1.1308(3) 0.0232(8) Uani 0.96 1 d . . P F 1
H31A H 1.0218 0.6711 1.1903 0.035 Uiso 0.96 1 calc R U P F 1
H31B H 1.0338 0.7352 1.1263 0.035 Uiso 0.96 1 calc R U P F 1
H31C H 1.1338 0.6469 1.1162 0.035 Uiso 0.96 1 calc R U P F 1
C11 C 0.5657(4) 0.7133(2) 0.5977(2) 0.0149(6) Uani 0.96 1 d . . P E 1
C18 C -0.1442(4) 0.2656(2) 0.3468(2) 0.0139(6) Uani 0.96 1 d . . P D 1
C26 C 0.7640(4) 0.4761(2) 1.0285(2) 0.0141(6) Uani 0.96 1 d . . P F 1
C17 C 0.0346(4) 0.3590(3) 0.4241(3) 0.0214(7) Uani 0.96 1 d . . P D 1
H17 H 0.1076 0.4092 0.4433 0.026 Uiso 0.96 1 calc R U P D 1
C23 C -0.4374(4) 0.0817(3) 0.2442(3) 0.0223(8) Uani 0.96 1 d . . P D 1
H23A H -0.4561 0.0222 0.2575 0.033 Uiso 0.96 1 calc R U P D 1
H23B H -0.4098 0.0683 0.1844 0.033 Uiso 0.96 1 calc R U P D 1
H23C H -0.5261 0.1173 0.2504 0.033 Uiso 0.96 1 calc R U P D 1
I1B I 0.1067(6) 0.3685(4) 0.4874(4) 0.0196(11) Uiso 0.04 1 d . . P G 2
N1 N 0.1600(4) 0.9459(3) -0.0266(2) 0.0180(8) Uani 0.96 1 d . . P C 1
I2B I 0.0293(6) 0.4207(4) 0.3441(4) 0.0197(11) Uiso 0.04 1 d . . P G 2
I3B I 0.1684(8) 0.9240(5) -0.0121(5) 0.0156(17) Uiso 0.04 1 d D . P H 2
I4B I -0.0342(7) 0.8680(5) -0.1535(4) 0.0136(15) Uiso 0.04 1 d D . P H 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I4 I3 2.7056(4) . ?
I2 I1 2.7070(3) . ?
N2 C1 1.334(5) . ?
N2 C6 1.464(5) . ?
N2 C2 1.381(5) . ?
O5 C20 1.220(4) . ?
N5 C13 1.352(4) . ?
N5 C9 1.330(5) . ?
O8 C27 1.208(4) . ?
O3 C12 1.215(4) . ?
O6 C19 1.221(4) . ?
N6 C9 1.341(4) . ?
N6 C10 1.395(4) . ?
N6 C14 1.452(4) . ?
N8 C13 1.377(4) . ?
N8 C16 1.468(4) . ?
N8 C12 1.370(4) . ?
O1 C4 1.225(4) . ?
O2 C3 1.223(4) . ?
N4 C8 1.470(4) . ?
N4 C4 1.371(5) . ?
N4 C5 1.372(4) . ?
N7 C12 1.409(4) . ?
N7 C15 1.463(4) . ?
N7 C11 1.410(4) . ?
O7 C28 1.217(4) . ?
N9 C21 1.353(4) . ?
N9 C17 1.331(5) . ?
N12 C24 1.464(5) . ?
N12 C20 1.383(4) . ?
N12 C21 1.366(4) . ?
N11 C20 1.388(4) . ?
N11 C19 1.412(4) . ?
N11 C23 1.469(4) . ?
C13 C10 1.363(5) . ?
C9 H9 0.9500 . ?
O4 C11 1.220(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 N10 1.450(4) . ?
N3 C4 1.396(5) . ?
N3 C7 1.472(4) . ?
N3 C3 1.405(4) . ?
N10 C18 1.391(4) . ?
N10 C17 1.352(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C10 C11 1.421(5) . ?
N16 C29 1.356(4) . ?
N16 C28 1.384(5) . ?
N16 C32 1.455(5) . ?
N13 C25 1.334(4) . ?
N13 C29 1.363(4) . ?
N15 C27 1.410(4) . ?
N15 C28 1.387(5) . ?
N15 C31 1.466(4) . ?
C1 H1 0.9500 . ?
C1 N1 1.327(5) . ?
C25 H25 0.9500 . ?
C25 N14 1.329(4) . ?
C5 C2 1.372(5) . ?
C5 N1 1.353(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N14 C30 1.475(4) . ?
N14 C26 1.390(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2 C3 1.426(5) . ?
C27 C26 1.423(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C29 C26 1.370(5) . ?
C21 C18 1.363(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C19 C18 1.427(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C17 H17 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
I1B I2B 2.699(8) . ?
I3B I4B 2.745(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C6 126.5(3) . . ?
C1 N2 C2 106.6(3) . . ?
C2 N2 C6 126.7(3) . . ?
C9 N5 C13 103.3(3) . . ?
C9 N6 C10 105.2(3) . . ?
C9 N6 C14 127.8(3) . . ?
C10 N6 C14 127.0(3) . . ?
C13 N8 C16 121.2(3) . . ?
C12 N8 C13 120.3(3) . . ?
C12 N8 C16 118.5(3) . . ?
C4 N4 C8 118.9(3) . . ?
C4 N4 C5 119.9(3) . . ?
C5 N4 C8 121.2(3) . . ?
C12 N7 C15 116.8(3) . . ?
C12 N7 C11 126.3(3) . . ?
C11 N7 C15 116.9(3) . . ?
C17 N9 C21 103.8(3) . . ?
C20 N12 C24 118.0(3) . . ?
C21 N12 C24 121.8(3) . . ?
C21 N12 C20 120.0(3) . . ?
C20 N11 C19 126.7(3) . . ?
C20 N11 C23 117.1(3) . . ?
C19 N11 C23 116.3(3) . . ?
N5 C13 N8 126.6(3) . . ?
N5 C13 C10 112.2(3) . . ?
C10 C13 N8 121.2(3) . . ?
N5 C9 N6 114.1(3) . . ?
N5 C9 H9 123.0 . . ?
N6 C9 H9 123.0 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N10 C22 H22A 109.5 . . ?
N10 C22 H22B 109.5 . . ?
N10 C22 H22C 109.5 . . ?
C4 N3 C7 116.7(3) . . ?
C4 N3 C3 126.8(3) . . ?
C3 N3 C7 116.5(3) . . ?
C18 N10 C22 127.9(3) . . ?
C17 N10 C22 127.5(3) . . ?
C17 N10 C18 104.6(3) . . ?
O1 C4 N4 121.0(3) . . ?
O1 C4 N3 121.8(3) . . ?
N4 C4 N3 117.2(3) . . ?
N8 C16 H16A 109.5 . . ?
N8 C16 H16B 109.5 . . ?
N8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N6 C10 C11 131.2(3) . . ?
C13 C10 N6 105.2(3) . . ?
C13 C10 C11 123.7(3) . . ?
C29 N16 C28 119.0(3) . . ?
C29 N16 C32 121.5(3) . . ?
C28 N16 C32 119.0(3) . . ?
C25 N13 C29 103.6(3) . . ?
C27 N15 C31 116.1(3) . . ?
C28 N15 C27 127.5(3) . . ?
C28 N15 C31 116.4(3) . . ?
N2 C1 H1 123.4 . . ?
N1 C1 N2 113.1(3) . . ?
N1 C1 H1 123.4 . . ?
N13 C25 H25 123.2 . . ?
N14 C25 N13 113.6(3) . . ?
N14 C25 H25 123.2 . . ?
C2 C5 N4 121.4(3) . . ?
N1 C5 N4 127.2(3) . . ?
N1 C5 C2 111.4(3) . . ?
N12 C24 H24A 109.5 . . ?
N12 C24 H24B 109.5 . . ?
N12 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 N14 C30 127.5(3) . . ?
C25 N14 C26 106.4(3) . . ?
C26 N14 C30 126.0(3) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C2 C3 132.1(3) . . ?
C5 C2 N2 104.8(3) . . ?
C5 C2 C3 123.1(3) . . ?
O2 C3 N3 121.4(3) . . ?
O2 C3 C2 127.1(3) . . ?
N3 C3 C2 111.5(3) . . ?
O8 C27 N15 121.7(3) . . ?
O8 C27 C26 127.7(3) . . ?
N15 C27 C26 110.6(3) . . ?
N6 C14 H14A 109.5 . . ?
N6 C14 H14B 109.5 . . ?
N6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C20 N12 121.0(3) . . ?
O5 C20 N11 122.0(3) . . ?
N12 C20 N11 117.0(3) . . ?
N14 C30 H30A 109.5 . . ?
N14 C30 H30B 109.5 . . ?
N14 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N16 C29 N13 126.0(3) . . ?
N16 C29 C26 122.6(3) . . ?
N13 C29 C26 111.4(3) . . ?
O7 C28 N16 120.8(4) . . ?
O7 C28 N15 122.2(3) . . ?
N16 C28 N15 116.9(3) . . ?
N9 C21 N12 126.8(3) . . ?
N9 C21 C18 111.6(3) . . ?
C18 C21 N12 121.6(3) . . ?
O3 C12 N8 121.6(3) . . ?
O3 C12 N7 121.5(3) . . ?
N8 C12 N7 116.9(3) . . ?
N16 C32 H32A 109.5 . . ?
N16 C32 H32B 109.5 . . ?
N16 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O6 C19 N11 120.3(3) . . ?
O6 C19 C18 128.2(3) . . ?
N11 C19 C18 111.5(3) . . ?
N7 C15 H15A 109.5 . . ?
N7 C15 H15B 109.5 . . ?
N7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N15 C31 H31A 109.5 . . ?
N15 C31 H31B 109.5 . . ?
N15 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N7 C11 C10 111.6(3) . . ?
O4 C11 N7 120.5(3) . . ?
O4 C11 C10 127.8(3) . . ?
N10 C18 C19 130.6(3) . . ?
C21 C18 N10 106.1(3) . . ?
C21 C18 C19 123.3(3) . . ?
N14 C26 C27 132.0(3) . . ?
C29 C26 N14 105.0(3) . . ?
C29 C26 C27 123.0(3) . . ?
N9 C17 N10 113.9(3) . . ?
N9 C17 H17 123.1 . . ?
N10 C17 H17 123.1 . . ?
N11 C23 H23A 109.5 . . ?
N11 C23 H23B 109.5 . . ?
N11 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C5 104.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C5 1.2(5) . . . . ?
N2 C2 C3 O2 -3.4(7) . . . . ?
N2 C2 C3 N3 178.7(4) . . . . ?
N5 C13 C10 N6 0.1(4) . . . . ?
N5 C13 C10 C11 -178.7(3) . . . . ?
O8 C27 C26 N14 2.0(7) . . . . ?
O8 C27 C26 C29 -174.7(4) . . . . ?
O6 C19 C18 N10 -1.4(7) . . . . ?
O6 C19 C18 C21 -178.5(4) . . . . ?
N6 C10 C11 N7 -179.9(3) . . . . ?
N6 C10 C11 O4 1.0(7) . . . . ?
N8 C13 C10 N6 178.9(3) . . . . ?
N8 C13 C10 C11 0.1(5) . . . . ?
N4 C5 C2 N2 180.0(3) . . . . ?
N4 C5 C2 C3 1.7(5) . . . . ?
N4 C5 N1 C1 179.8(4) . . . . ?
N9 C21 C18 N10 0.9(4) . . . . ?
N9 C21 C18 C19 178.6(3) . . . . ?
N12 C21 C18 N10 -179.8(3) . . . . ?
N12 C21 C18 C19 -2.1(6) . . . . ?
N11 C19 C18 N10 179.2(3) . . . . ?
N11 C19 C18 C21 2.1(5) . . . . ?
C13 N5 C9 N6 1.4(4) . . . . ?
C13 N8 C12 O3 177.8(3) . . . . ?
C13 N8 C12 N7 -2.2(5) . . . . ?
C13 C10 C11 N7 -1.5(5) . . . . ?
C13 C10 C11 O4 179.4(4) . . . . ?
C9 N5 C13 N8 -179.6(3) . . . . ?
C9 N5 C13 C10 -0.9(4) . . . . ?
C9 N6 C10 C13 0.7(4) . . . . ?
C9 N6 C10 C11 179.4(4) . . . . ?
C8 N4 C4 O1 -1.0(5) . . . . ?
C8 N4 C4 N3 178.2(3) . . . . ?
C8 N4 C5 C2 179.7(3) . . . . ?
C8 N4 C5 N1 -1.5(6) . . . . ?
C22 N10 C18 C21 178.5(3) . . . . ?
C22 N10 C18 C19 1.0(6) . . . . ?
C22 N10 C17 N9 -179.0(3) . . . . ?
C4 N4 C5 C2 2.7(5) . . . . ?
C4 N4 C5 N1 -178.5(4) . . . . ?
C4 N3 C3 O2 -176.7(3) . . . . ?
C4 N3 C3 C2 1.3(5) . . . . ?
C16 N8 C13 N5 -1.5(5) . . . . ?
C16 N8 C13 C10 179.9(3) . . . . ?
C16 N8 C12 O3 -0.2(5) . . . . ?
C16 N8 C12 N7 179.7(3) . . . . ?
C10 N6 C9 N5 -1.3(4) . . . . ?
N16 C29 C26 N14 -179.0(3) . . . . ?
N16 C29 C26 C27 -1.6(6) . . . . ?
N13 C25 N14 C30 178.0(3) . . . . ?
N13 C25 N14 C26 0.9(4) . . . . ?
N13 C29 C26 N14 0.8(4) . . . . ?
N13 C29 C26 C27 178.2(3) . . . . ?
N15 C27 C26 N14 -178.4(3) . . . . ?
N15 C27 C26 C29 4.9(5) . . . . ?
C1 N2 C2 C5 -0.3(4) . . . . ?
C1 N2 C2 C3 177.7(4) . . . . ?
C25 N13 C29 N16 179.6(3) . . . . ?
C25 N13 C29 C26 -0.2(4) . . . . ?
C25 N14 C26 C27 -178.1(4) . . . . ?
C25 N14 C26 C29 -1.0(4) . . . . ?
C5 N4 C4 O1 176.0(3) . . . . ?
C5 N4 C4 N3 -4.8(5) . . . . ?
C5 C2 C3 O2 174.3(4) . . . . ?
C5 C2 C3 N3 -3.6(5) . . . . ?
C24 N12 C20 O5 5.0(5) . . . . ?
C24 N12 C20 N11 -175.3(3) . . . . ?
C24 N12 C21 N9 -4.8(6) . . . . ?
C24 N12 C21 C18 176.0(3) . . . . ?
C6 N2 C1 N1 -175.3(3) . . . . ?
C6 N2 C2 C5 174.4(3) . . . . ?
C6 N2 C2 C3 -7.6(6) . . . . ?
C7 N3 C4 O1 2.9(5) . . . . ?
C7 N3 C4 N4 -176.3(3) . . . . ?
C7 N3 C3 O2 2.4(5) . . . . ?
C7 N3 C3 C2 -179.6(3) . . . . ?
C2 N2 C1 N1 -0.6(4) . . . . ?
C2 C5 N1 C1 -1.3(4) . . . . ?
C3 N3 C4 O1 -178.0(4) . . . . ?
C3 N3 C4 N4 2.7(5) . . . . ?
C27 N15 C28 O7 -173.6(4) . . . . ?
C27 N15 C28 N16 6.6(5) . . . . ?
C14 N6 C9 N5 178.6(3) . . . . ?
C14 N6 C10 C13 -179.3(3) . . . . ?
C14 N6 C10 C11 -0.6(6) . . . . ?
C20 N12 C21 N9 -179.9(4) . . . . ?
C20 N12 C21 C18 1.0(5) . . . . ?
C20 N11 C19 O6 179.3(3) . . . . ?
C20 N11 C19 C18 -1.2(5) . . . . ?
C30 N14 C26 C27 4.8(6) . . . . ?
C30 N14 C26 C29 -178.1(3) . . . . ?
C29 N16 C28 O7 178.1(3) . . . . ?
C29 N16 C28 N15 -2.1(5) . . . . ?
C29 N13 C25 N14 -0.5(4) . . . . ?
C28 N16 C29 N13 -179.8(3) . . . . ?
C28 N16 C29 C26 -0.1(5) . . . . ?
C28 N15 C27 O8 171.9(3) . . . . ?
C28 N15 C27 C26 -7.6(5) . . . . ?
C21 N9 C17 N10 0.4(4) . . . . ?
C21 N12 C20 O5 -179.8(3) . . . . ?
C21 N12 C20 N11 -0.1(5) . . . . ?
C12 N8 C13 N5 -179.5(3) . . . . ?
C12 N8 C13 C10 1.9(5) . . . . ?
C12 N7 C11 O4 -179.8(3) . . . . ?
C12 N7 C11 C10 1.0(5) . . . . ?
C32 N16 C29 N13 -7.9(6) . . . . ?
C32 N16 C29 C26 171.8(4) . . . . ?
C32 N16 C28 O7 6.0(6) . . . . ?
C32 N16 C28 N15 -174.2(3) . . . . ?
C19 N11 C20 O5 180.0(3) . . . . ?
C19 N11 C20 N12 0.3(5) . . . . ?
C15 N7 C12 O3 -0.3(5) . . . . ?
C15 N7 C12 N8 179.8(3) . . . . ?
C15 N7 C11 O4 1.2(5) . . . . ?
C15 N7 C11 C10 -178.0(3) . . . . ?
C31 N15 C27 O8 -5.0(5) . . . . ?
C31 N15 C27 C26 175.5(3) . . . . ?
C31 N15 C28 O7 3.3(5) . . . . ?
C31 N15 C28 N16 -176.6(3) . . . . ?
C11 N7 C12 O3 -179.3(3) . . . . ?
C11 N7 C12 N8 0.8(5) . . . . ?
C18 N10 C17 N9 0.1(4) . . . . ?
C17 N9 C21 N12 180.0(4) . . . . ?
C17 N9 C21 C18 -0.8(4) . . . . ?
C17 N10 C18 C21 -0.6(4) . . . . ?
C17 N10 C18 C19 -178.1(4) . . . . ?
C23 N11 C20 O5 -0.3(5) . . . . ?
C23 N11 C20 N12 -179.9(3) . . . . ?
C23 N11 C19 O6 -0.4(5) . . . . ?
C23 N11 C19 C18 179.0(3) . . . . ?
N1 C5 C2 N2 1.0(4) . . . . ?
N1 C5 C2 C3 -177.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hcaf_icl2
_database_code_depnum_ccdc_archive 'CCDC 2502144'
loop_
_audit_author_name
_audit_author_address
'Enrico Podda'
;University of Cagliari
Italy
;
_audit_update_record             
;
2025-11-11 deposited with the CCDC.	2026-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            'caffeinium iodine dichloride'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 Cl2 I N4 O2'
_chemical_formula_weight         393.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   8.770(3)
_cell_length_b                   10.790(2)
_cell_length_c                   14.274(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.77(3)
_cell_angle_gamma                90
_cell_volume                     1350.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.28
_cell_measurement_theta_max      13.03

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   0.810
_exptl_transmission_factor_max   1.000
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.764
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Psi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'A.C.T. North,D.C Phillips,F.S.Mathews,Acta Crystallogr A 1968, 24, 351-359'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Enraf Nonius CAD4 diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2372
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.286
_diffrn_reflns_theta_max         24.964
_diffrn_reflns_theta_full        24.964
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2372
_reflns_number_gt                1678
_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       'Enraf Nonius CAD4 software'
_computing_cell_refinement       'Enraf Nonius CAD4 software'
_computing_data_reduction        
'SDP package of crystallographic programs. B. Frenz'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0938P)²+0.9846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2372
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.02678(6) 0.08338(5) 0.30572(4) 0.0562(3) Uani 1 1 d . . . . .
Cl1 Cl -0.1583(3) 0.0916(2) 0.4320(2) 0.0818(8) Uani 1 1 d . . . . .
Cl2 Cl 0.2073(3) 0.0640(3) 0.16042(17) 0.0721(7) Uani 1 1 d . . . . .
O11 O 0.8699(7) 0.2745(6) 0.0063(4) 0.0652(17) Uani 1 1 d . . . . .
O13 O 0.9111(7) 0.4477(6) 0.2970(4) 0.0655(17) Uani 1 1 d . . . . .
N1 N 0.8948(7) 0.3532(6) 0.1536(4) 0.0470(16) Uani 1 1 d . . . . .
N3 N 0.6800(7) 0.2313(6) 0.1050(4) 0.0450(15) Uani 1 1 d . . . . .
N7 N 0.6036(7) 0.3260(6) 0.3339(4) 0.0427(15) Uani 1 1 d . . . . .
N9 N 0.4874(7) 0.2189(6) 0.2251(4) 0.0438(15) Uani 1 1 d . . . . .
H9 H 0.418754 0.175945 0.195507 0.053 Uiso 1 1 calc R U . . .
C2 C 0.8186(10) 0.2867(7) 0.0836(5) 0.0480(19) Uani 1 1 d . . . . .
C4 C 0.6253(8) 0.2547(7) 0.1923(4) 0.0357(15) Uani 1 1 d . . . . .
C5 C 0.6980(8) 0.3225(7) 0.2583(5) 0.0381(16) Uani 1 1 d . . . . .
C6 C 0.8413(10) 0.3814(7) 0.2427(6) 0.0477(19) Uani 1 1 d . . . . .
C8 C 0.4800(9) 0.2638(8) 0.3123(5) 0.0479(19) Uani 1 1 d . . . . .
H8 H 0.398659 0.252374 0.351705 0.057 Uiso 1 1 calc R U . . .
C10 C 1.0413(11) 0.4076(9) 0.1301(7) 0.065(3) Uani 1 1 d . . . . .
H10A H 1.102795 0.346286 0.100476 0.084 Uiso 1 1 calc R U . . .
H10B H 1.093017 0.436323 0.186277 0.084 Uiso 1 1 calc R U . . .
H10C H 1.024475 0.476105 0.088095 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5913(10) 0.1633(9) 0.0334(5) 0.056(2) Uani 1 1 d . . . . .
H12A H 0.545794 0.091755 0.061187 0.073 Uiso 1 1 calc R U . . .
H12B H 0.657166 0.137452 -0.015382 0.073 Uiso 1 1 calc R U . . .
H12C H 0.512580 0.216004 0.007411 0.073 Uiso 1 1 calc R U . . .
C14 C 0.6387(11) 0.3925(8) 0.4230(6) 0.056(2) Uani 1 1 d . . . . .
H14A H 0.558247 0.378497 0.465897 0.072 Uiso 1 1 calc R U . . .
H14B H 0.647268 0.479701 0.410835 0.072 Uiso 1 1 calc R U . . .
H14C H 0.733207 0.362365 0.450010 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I Cl1 2.464(3) . ?
I Cl2 2.656(3) . ?
O11 C2 1.212(9) . ?
O13 C6 1.208(10) . ?
N1 C2 1.385(10) . ?
N1 C6 1.402(10) . ?
N1 C10 1.462(10) . ?
N3 C4 1.372(8) . ?
N3 C2 1.397(10) . ?
N3 C12 1.463(10) . ?
N7 C8 1.304(10) . ?
N7 C5 1.380(9) . ?
N7 C14 1.485(9) . ?
N9 C8 1.340(9) . ?
N9 C4 1.366(9) . ?
C4 C5 1.339(10) . ?
C5 C6 1.431(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
Cl1 I Cl2 174.87(9) . . ?
C2 N1 C6 126.8(7) . . ?
C2 N1 C10 116.8(6) . . ?
C6 N1 C10 116.3(7) . . ?
C4 N3 C2 116.8(6) . . ?
C4 N3 C12 122.2(6) . . ?
C2 N3 C12 120.6(6) . . ?
C8 N7 C5 108.4(6) . . ?
C8 N7 C14 126.8(7) . . ?
C5 N7 C14 124.7(6) . . ?
C8 N9 C4 106.6(6) . . ?
O11 C2 N1 121.9(8) . . ?
O11 C2 N3 120.2(8) . . ?
N1 C2 N3 117.9(6) . . ?
C5 C4 N9 108.7(6) . . ?
C5 C4 N3 124.5(6) . . ?
N9 C4 N3 126.7(7) . . ?
C4 C5 N7 106.3(6) . . ?
C4 C5 C6 122.3(6) . . ?
N7 C5 C6 131.3(7) . . ?
O13 C6 N1 122.2(8) . . ?
O13 C6 C5 126.4(7) . . ?
N1 C6 C5 111.4(7) . . ?
N7 C8 N9 110.0(7) . . ?

_refine_diff_density_max         0.613
_refine_diff_density_min         -1.727
_refine_diff_density_rms         0.131

