#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/40/4514020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4514020
loop_
_publ_author_name
'Huang, Yaodong'
'Li, Huimin'
'Li, Ziyan'
'Zhang, Yan'
'Cao, Wenwen'
'Wang, Luyuan'
'Liu, Shuxue'
_publ_section_title
;
 Unusual C-I···O Halogen Bonding in Triazole
 Derivatives: Gelation Solvents at Two Extremes of Polarity and Formation
 of Superorganogels.
;
_journal_issue                   1
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              311
_journal_page_last               321
_journal_paper_doi               10.1021/acs.langmuir.6b03691
_journal_volume                  33
_journal_year                    2017
_chemical_formula_sum            'C18 H16 I N3 O3'
_chemical_formula_weight         449.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.250(2)
_cell_length_b                   8.7012(17)
_cell_length_c                   16.867(3)
_cell_measurement_reflns_used    10268
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.00
_cell_volume                     1754.6(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16537
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.847
_exptl_absorpt_correction_T_max  0.7691
_exptl_absorpt_correction_T_min  0.6552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colummar
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0039(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3121
_reflns_number_total             4006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la6b03691_si_003.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4514020
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'
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
I1 I 0.227365(15) 0.744440(19) 0.185841(11) 0.04652(12) Uani 1 1 d .
N1 N 0.44738(17) 0.8034(3) 0.30309(13) 0.0384(5) Uani 1 1 d .
N2 N 0.5100(2) 0.7760(3) 0.37732(18) 0.0479(6) Uani 1 1 d .
N3 N 0.45165(17) 0.6892(3) 0.41594(14) 0.0453(5) Uani 1 1 d .
O1 O 0.77505(16) 0.5219(2) 0.09673(13) 0.0556(5) Uani 1 1 d .
O2 O -0.0433(2) 0.2445(2) 0.46662(17) 0.0560(7) Uani 1 1 d .
O3 O 0.0923(2) 0.2412(2) 0.57849(17) 0.0544(6) Uani 1 1 d .
C1 C 0.5318(3) 0.7430(3) 0.1272(2) 0.0451(7) Uani 1 1 d .
H1A H 0.4601 0.7699 0.0995 0.054 Uiso 1 1 calc R
C2 C 0.5977(2) 0.6512(3) 0.08793(16) 0.0455(6) Uani 1 1 d .
H2B H 0.5706 0.6186 0.0348 0.055 Uiso 1 1 calc R
C3 C 0.70328(19) 0.6100(3) 0.12941(16) 0.0402(6) Uani 1 1 d .
C4 C 0.7368(3) 0.4706(4) 0.0157(2) 0.0616(9) Uani 1 1 d .
H4A H 0.7940 0.4099 -0.0001 0.092 Uiso 1 1 calc R
H4B H 0.7199 0.5578 -0.0198 0.092 Uiso 1 1 calc R
H4C H 0.6707 0.4095 0.0120 0.092 Uiso 1 1 calc R
C5 C 0.7432(2) 0.6590(3) 0.20887(17) 0.0480(6) Uani 1 1 d .
H5A H 0.8141 0.6298 0.2370 0.058 Uiso 1 1 calc R
C6 C 0.6773(3) 0.7512(3) 0.2461(2) 0.0436(7) Uani 1 1 d .
H6A H 0.7048 0.7849 0.2990 0.052 Uiso 1 1 calc R
C7 C 0.5695(2) 0.7946(3) 0.20515(17) 0.0370(5) Uani 1 1 d .
C8 C 0.4971(2) 0.8925(3) 0.24621(16) 0.0418(6) Uani 1 1 d .
H8A H 0.5418 0.9751 0.2754 0.050 Uiso 1 1 calc R
H8B H 0.4380 0.9382 0.2053 0.050 Uiso 1 1 calc R
C9 C 0.3464(2) 0.7313(3) 0.29346(18) 0.0348(6) Uani 1 1 d .
C10 C 0.35001(18) 0.6578(3) 0.36623(14) 0.0348(5) Uani 1 1 d .
C11 C 0.26980(19) 0.5627(3) 0.39905(14) 0.0355(5) Uani 1 1 d .
C12 C 0.1599(2) 0.5348(4) 0.35774(16) 0.0493(7) Uani 1 1 d .
H12A H 0.1339 0.5772 0.3065 0.059 Uiso 1 1 calc R
C13 C 0.0895(2) 0.4455(3) 0.39173(16) 0.0503(7) Uani 1 1 d .
H13A H 0.0169 0.4272 0.3629 0.060 Uiso 1 1 calc R
C14 C 0.12558(19) 0.3827(3) 0.46835(15) 0.0381(6) Uani 1 1 d .
C15 C 0.2343(2) 0.4104(3) 0.50991(17) 0.0478(6) Uani 1 1 d .
H15A H 0.2597 0.3697 0.5616 0.057 Uiso 1 1 calc R
C16 C 0.3051(2) 0.4980(3) 0.47504(17) 0.0464(7) Uani 1 1 d .
H16A H 0.3783 0.5139 0.5034 0.056 Uiso 1 1 calc R
C17 C 0.0487(3) 0.2837(3) 0.5026(2) 0.0416(6) Uani 1 1 d .
C18 C 0.0244(2) 0.1403(4) 0.6170(2) 0.0617(8) Uani 1 1 d .
H18A H 0.0639 0.1175 0.6714 0.093 Uiso 1 1 calc R
H18B H 0.0095 0.0466 0.5866 0.093 Uiso 1 1 calc R
H18C H -0.0450 0.1904 0.6186 0.093 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C9 110.4(2)
N2 N1 C8 118.1(2)
C9 N1 C8 131.4(2)
N3 N2 N1 107.7(2)
N2 N3 C10 109.5(2)
C3 O1 C4 117.3(2)
C17 O3 C18 116.7(3)
C7 C1 C2 122.1(3)
C7 C1 H1A 118.9
C2 C1 H1A 118.9
C3 C2 C1 118.8(3)
C3 C2 H2B 120.6
C1 C2 H2B 120.6
O1 C3 C2 123.7(2)
O1 C3 C5 116.0(2)
C2 C3 C5 120.3(2)
O1 C4 H4A 109.5
O1 C4 H4B 109.5
H4A C4 H4B 109.5
O1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 C6 119.9(3)
C3 C5 H5A 120.0
C6 C5 H5A 120.0
C5 C6 C7 120.8(3)
C5 C6 H6A 119.6
C7 C6 H6A 119.6
C1 C7 C6 118.0(3)
C1 C7 C8 121.2(3)
C6 C7 C8 120.8(3)
N1 C8 C7 111.9(2)
N1 C8 H8A 109.2
C7 C8 H8A 109.2
N1 C8 H8B 109.2
C7 C8 H8B 109.2
H8A C8 H8B 107.9
N1 C9 C10 104.8(2)
N1 C9 I1 121.7(2)
C10 C9 I1 133.47(19)
N3 C10 C9 107.6(2)
N3 C10 C11 118.1(2)
C9 C10 C11 134.3(2)
C16 C11 C12 117.8(2)
C16 C11 C10 118.4(2)
C12 C11 C10 123.8(2)
C13 C12 C11 121.0(3)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C12 C13 C14 120.7(2)
C12 C13 H13A 119.6
C14 C13 H13A 119.6
C13 C14 C15 118.7(2)
C13 C14 C17 119.5(2)
C15 C14 C17 121.8(2)
C14 C15 C16 120.4(3)
C14 C15 H15A 119.8
C16 C15 H15A 119.8
C11 C16 C15 121.5(2)
C11 C16 H16A 119.3
C15 C16 H16A 119.3
O2 C17 O3 122.7(3)
O2 C17 C14 124.9(3)
O3 C17 C14 112.4(3)
O3 C18 H18A 109.5
O3 C18 H18B 109.5
H18A C18 H18B 109.5
O3 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C9 2.069(3)
N1 N2 1.340(4)
N1 C9 1.365(3)
N1 C8 1.466(3)
N2 N3 1.307(4)
N3 C10 1.368(3)
O1 C3 1.370(3)
O1 C4 1.417(4)
O2 C17 1.207(4)
O3 C17 1.328(4)
O3 C18 1.456(3)
C1 C7 1.370(4)
C1 C2 1.401(4)
C1 H1A 0.9300
C2 C3 1.377(3)
C2 H2B 0.9300
C3 C5 1.390(4)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C6 1.382(4)
C5 H5A 0.9300
C6 C7 1.402(4)
C6 H6A 0.9300
C7 C8 1.503(4)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.376(4)
C10 C11 1.481(3)
C11 C16 1.380(4)
C11 C12 1.396(3)
C12 C13 1.375(4)
C12 H12A 0.9300
C13 C14 1.384(4)
C13 H13A 0.9300
C14 C15 1.384(3)
C14 C17 1.483(4)
C15 C16 1.379(4)
C15 H15A 0.9300
C16 H16A 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C9 N1 N2 N3 -0.5(3)
C8 N1 N2 N3 -176.9(2)
N1 N2 N3 C10 0.7(3)
C7 C1 C2 C3 0.8(4)
C4 O1 C3 C2 -0.3(4)
C4 O1 C3 C5 -179.8(3)
C1 C2 C3 O1 -179.4(2)
C1 C2 C3 C5 0.1(4)
O1 C3 C5 C6 178.6(2)
C2 C3 C5 C6 -0.9(4)
C3 C5 C6 C7 0.9(4)
C2 C1 C7 C6 -0.8(4)
C2 C1 C7 C8 -179.7(2)
C5 C6 C7 C1 -0.1(4)
C5 C6 C7 C8 178.9(2)
N2 N1 C8 C7 81.5(3)
C9 N1 C8 C7 -94.0(3)
C1 C7 C8 N1 101.6(3)
C6 C7 C8 N1 -77.3(3)
N2 N1 C9 C10 0.2(3)
C8 N1 C9 C10 175.9(2)
N2 N1 C9 I1 -179.18(18)
C8 N1 C9 I1 -3.4(4)
N2 N3 C10 C9 -0.6(3)
N2 N3 C10 C11 -179.0(2)
N1 C9 C10 N3 0.3(3)
I1 C9 C10 N3 179.47(19)
N1 C9 C10 C11 178.3(2)
I1 C9 C10 C11 -2.5(4)
N3 C10 C11 C16 -6.2(3)
C9 C10 C11 C16 176.0(3)
N3 C10 C11 C12 173.5(3)
C9 C10 C11 C12 -4.3(4)
C16 C11 C12 C13 -0.2(4)
C10 C11 C12 C13 -179.9(3)
C11 C12 C13 C14 0.9(5)
C12 C13 C14 C15 -0.5(4)
C12 C13 C14 C17 -178.5(3)
C13 C14 C15 C16 -0.5(4)
C17 C14 C15 C16 177.4(3)
C12 C11 C16 C15 -0.9(4)
C10 C11 C16 C15 178.8(2)
C14 C15 C16 C11 1.2(4)
C18 O3 C17 O2 1.4(4)
C18 O3 C17 C14 -178.5(2)
C13 C14 C17 O2 4.6(4)
C15 C14 C17 O2 -173.3(3)
C13 C14 C17 O3 -175.5(2)
C15 C14 C17 O3 6.6(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132941394
