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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/90/7229088.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_7229088
loop_
_publ_author_name
'Zbačnik, Marija'
'Pajski, Matea'
'Stilinović, Vladimir'
'Vitković, Matea'
'Cinčić, Dominik'
_publ_section_title
;
 The halogen bonding proclivity of the ortho-methoxy--hydroxy group in
 cocrystals of o-vanillin imines and diiodotetrafluoro-benzenes
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01332A
_journal_year                    2017
_chemical_formula_moiety         (C18H23N1O2)2(C6F4I2)
_chemical_formula_sum            'C42 H46 F4 I2 N2 O4'
_chemical_formula_weight         972.63
_chemical_name_common
bis(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(14-diiodotetrafluorobenzene)
_chemical_name_systematic
bis(2-(Adamantan-1-yliminomethyl)-6-methoxy-phenol)(14-diiodotetrafluorobenzene)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-29 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                95.431(3)
_cell_angle_beta                 95.804(3)
_cell_angle_gamma                116.039(4)
_cell_formula_units_Z            1
_cell_length_a                   9.2260(4)
_cell_length_b                   10.0931(4)
_cell_length_c                   12.4702(4)
_cell_measurement_reflns_used    8560
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      40.7034
_cell_measurement_theta_min      3.8156
_cell_volume                     1025.36(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16969
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         4.063
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57679
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_description       plate
_exptl_crystal_F_000             486
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Diethyl ether'
_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.077
_refine_diff_density_max         1.896
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1152P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3369
_reflns_number_total             4442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01332a2.cif
_cod_data_source_block           shelx_CCDC4
_cod_database_code               7229088
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C8 C 0.5161(9) 0.7404(9) 0.6539(5) 0.0767(11) Uani 1 1 d . U
C9 C 0.4875(13) 0.8714(11) 0.6823(8) 0.1036(19) Uani 1 1 d . U
H12A H 0.4279 0.8855 0.6194 0.124 Uiso 1 1 calc R U
H12B H 0.5913 0.9603 0.7034 0.124 Uiso 1 1 calc R U
C10 C 0.3814(13) 0.8451(12) 0.7843(8) 0.111(2) Uani 1 1 d . U
H22 H 0.3541 0.9269 0.8040 0.133 Uiso 1 1 calc R U
C11 C 0.2228(15) 0.6918(13) 0.7244(10) 0.120(2) Uani 1 1 d . U
H24A H 0.1338 0.6734 0.7655 0.144 Uiso 1 1 calc R U
H24B H 0.1886 0.7067 0.6523 0.144 Uiso 1 1 calc R U
C12 C 0.2506(14) 0.5581(13) 0.7133(9) 0.1105(18) Uani 1 1 d . U
H23 H 0.1495 0.4645 0.6927 0.133 Uiso 1 1 calc R U
C13 C 0.3591(12) 0.5992(11) 0.6187(8) 0.1020(19) Uani 1 1 d . U
H11A H 0.3841 0.5177 0.5968 0.122 Uiso 1 1 calc R U
H11B H 0.2971 0.6109 0.5560 0.122 Uiso 1 1 calc R U
C14 C 0.6114(10) 0.7300(10) 0.7590(6) 0.0855(18) Uani 1 1 d . U
H13A H 0.7106 0.8226 0.7826 0.103 Uiso 1 1 calc R U
H13B H 0.6414 0.6497 0.7456 0.103 Uiso 1 1 calc R U
C15 C 0.4959(12) 0.6984(12) 0.8522(7) 0.102(2) Uani 1 1 d . U
H14 H 0.5528 0.6879 0.9191 0.123 Uiso 1 1 calc R U
C16 C 0.3508(14) 0.5618(10) 0.8123(8) 0.111(3) Uani 1 1 d . .
H21A H 0.2836 0.5390 0.8694 0.133 Uiso 1 1 calc R U
H21B H 0.3826 0.4826 0.7996 0.133 Uiso 1 1 calc R U
C17 C 0.4707(13) 0.8225(12) 0.8703(8) 0.107(3) Uani 1 1 d . U
H20A H 0.5763 0.9097 0.8891 0.129 Uiso 1 1 calc R U
H20B H 0.4149 0.8152 0.9330 0.129 Uiso 1 1 calc R U
C18 C 0.8600(10) 0.9282(12) 0.1125(6) 0.097(3) Uani 1 1 d . .
H15A H 0.9702 1.0037 0.1375 0.146 Uiso 1 1 calc R U
H15B H 0.8048 0.9655 0.0636 0.146 Uiso 1 1 calc R U
H15C H 0.8614 0.8413 0.0749 0.146 Uiso 1 1 calc R U
C101 C 0.1408(6) 0.5731(6) 0.0802(4) 0.0439(10) Uani 1 1 d . .
C102 C 0.0635(6) 0.4198(6) 0.0522(4) 0.0476(11) Uani 1 1 d . .
C103 C 0.0739(6) 0.6518(5) 0.0263(4) 0.0465(11) Uani 1 1 d . .
N1 N 0.6120(5) 0.7717(5) 0.5636(3) 0.0497(10) Uani 1 1 d . .
F1 F 0.1434(4) 0.8011(3) 0.0489(3) 0.0631(8) Uani 1 1 d . .
F2 F 0.1218(4) 0.3368(4) 0.1017(3) 0.0674(9) Uani 1 1 d . .
C1 C 0.7664(6) 0.8324(5) 0.3787(4) 0.0446(10) Uani 1 1 d . .
C2 C 0.8556(6) 0.8623(6) 0.2901(4) 0.0478(11) Uani 1 1 d . .
C3 C 1.0031(7) 0.8614(6) 0.2963(5) 0.0570(13) Uani 1 1 d . .
H3 H 1.0588 0.8800 0.2370 0.068 Uiso 1 1 calc R U
C4 C 1.0724(7) 0.8326(8) 0.3916(5) 0.0664(15) Uani 1 1 d . .
H4 H 1.1729 0.8314 0.3949 0.080 Uiso 1 1 calc R U
C5 C 0.9920(8) 0.8065(8) 0.4785(5) 0.0654(15) Uani 1 1 d . .
H5 H 1.0395 0.7905 0.5422 0.079 Uiso 1 1 calc R U
C6 C 0.8373(6) 0.8035(6) 0.4733(4) 0.0500(11) Uani 1 1 d . .
C7 C 0.7521(7) 0.7743(6) 0.5659(4) 0.0544(12) Uani 1 1 d . .
H8 H 0.8003 0.7570 0.6287 0.065 Uiso 1 1 calc R U
O1 O 0.6233(5) 0.8315(5) 0.3703(3) 0.0578(9) Uani 1 1 d . .
H1 H 0.5859 0.8120 0.4269 0.087 Uiso 1 1 calc R U
O2 O 0.7776(5) 0.8903(5) 0.2022(3) 0.0668(11) Uani 1 1 d . .
I1 I 0.35252(4) 0.68348(4) 0.19669(3) 0.05641(18) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 C8 C9 106.6(6) . .
N1 C8 C13 109.7(6) . .
C9 C8 C13 112.2(8) . .
N1 C8 C14 112.7(6) . .
C9 C8 C14 105.0(7) . .
C13 C8 C14 110.5(7) . .
C8 C9 C10 109.5(7) . .
C8 C9 H12A 109.8 . .
C10 C9 H12A 109.8 . .
C8 C9 H12B 109.8 . .
C10 C9 H12B 109.8 . .
H12A C9 H12B 108.2 . .
C17 C10 C11 112.9(10) . .
C17 C10 C9 107.1(9) . .
C11 C10 C9 97.2(8) . .
C17 C10 H22 112.9 . .
C11 C10 H22 112.8 . .
C9 C10 H22 112.9 . .
C12 C11 C10 114.7(10) . .
C12 C11 H24A 108.6 . .
C10 C11 H24A 108.6 . .
C12 C11 H24B 108.6 . .
C10 C11 H24B 108.6 . .
H24A C11 H24B 107.6 . .
C16 C12 C11 109.0(10) . .
C16 C12 C13 109.2(9) . .
C11 C12 C13 97.5(9) . .
C16 C12 H23 113.4 . .
C11 C12 H23 113.4 . .
C13 C12 H23 113.4 . .
C8 C13 C12 112.2(8) . .
C8 C13 H11A 109.2 . .
C12 C13 H11A 109.2 . .
C8 C13 H11B 109.2 . .
C12 C13 H11B 109.2 . .
H11A C13 H11B 107.9 . .
C8 C14 C15 108.3(6) . .
C8 C14 H13A 110.0 . .
C15 C14 H13A 110.0 . .
C8 C14 H13B 110.0 . .
C15 C14 H13B 110.0 . .
H13A C14 H13B 108.4 . .
C17 C15 C16 114.8(9) . .
C17 C15 C14 105.3(8) . .
C16 C15 C14 107.5(8) . .
C17 C15 H14 109.7 . .
C16 C15 H14 109.7 . .
C14 C15 H14 109.7 . .
C15 C16 C12 117.0(8) . .
C15 C16 H21A 108.0 . .
C12 C16 H21A 108.0 . .
C15 C16 H21B 108.0 . .
C12 C16 H21B 108.0 . .
H21A C16 H21B 107.3 . .
C15 C17 C10 115.8(9) . .
C15 C17 H20A 108.3 . .
C10 C17 H20A 108.3 . .
C15 C17 H20B 108.3 . .
C10 C17 H20B 108.3 . .
H20A C17 H20B 107.4 . .
O2 C18 H15A 109.5 . .
O2 C18 H15B 109.5 . .
H15A C18 H15B 109.5 . .
O2 C18 H15C 109.5 . .
H15A C18 H15C 109.5 . .
H15B C18 H15C 109.5 . .
C102 C101 C103 117.0(4) . .
C102 C101 I1 121.9(4) . .
C103 C101 I1 121.1(4) . .
F2 C102 C103 118.4(5) . 2_565
F2 C102 C101 120.0(4) . .
C103 C102 C101 121.6(5) 2_565 .
F1 C103 C102 118.4(4) . 2_565
F1 C103 C101 120.2(4) . .
C102 C103 C101 121.4(5) 2_565 .
C7 N1 C8 124.9(5) . .
O1 C1 C6 122.4(5) . .
O1 C1 C2 120.1(5) . .
C6 C1 C2 117.5(5) . .
C3 C2 O2 125.6(5) . .
C3 C2 C1 121.1(5) . .
O2 C2 C1 113.3(5) . .
C2 C3 C4 120.6(5) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C5 C4 C3 119.8(5) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C4 C5 C6 120.6(5) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C1 C6 C5 120.3(5) . .
C1 C6 C7 119.5(5) . .
C5 C6 C7 120.2(5) . .
N1 C7 C6 121.6(5) . .
N1 C7 H8 119.2 . .
C6 C7 H8 119.2 . .
C1 O1 H1 109.5 . .
C2 O2 C18 117.5(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C8 N1 1.475(7) .
C8 C9 1.476(12) .
C8 C13 1.505(12) .
C8 C14 1.541(10) .
C9 C10 1.653(13) .
C9 H12A 0.9700 .
C9 H12B 0.9700 .
C10 C17 1.384(14) .
C10 C11 1.632(16) .
C10 H22 0.9800 .
C11 C12 1.477(14) .
C11 H24A 0.9700 .
C11 H24B 0.9700 .
C12 C16 1.453(14) .
C12 C13 1.591(13) .
C12 H23 0.9800 .
C13 H11A 0.9700 .
C13 H11B 0.9700 .
C14 C15 1.615(11) .
C14 H13A 0.9700 .
C14 H13B 0.9700 .
C15 C17 1.375(13) .
C15 C16 1.433(14) .
C15 H14 0.9800 .
C16 H21A 0.9700 .
C16 H21B 0.9700 .
C17 H20A 0.9700 .
C17 H20B 0.9700 .
C18 O2 1.406(8) .
C18 H15A 0.9600 .
C18 H15B 0.9600 .
C18 H15C 0.9600 .
C101 C102 1.380(7) .
C101 C103 1.382(7) .
C101 I1 2.092(5) .
C102 F2 1.341(6) .
C102 C103 1.378(7) 2_565
C103 F1 1.340(6) .
C103 C102 1.377(7) 2_565
N1 C7 1.278(7) .
C1 O1 1.310(6) .
C1 C6 1.408(7) .
C1 C2 1.420(7) .
C2 C3 1.360(8) .
C2 O2 1.370(6) .
C3 C4 1.407(8) .
C3 H3 0.9300 .
C4 C5 1.356(9) .
C4 H4 0.9300 .
C5 C6 1.409(8) .
C5 H5 0.9300 .
C6 C7 1.443(7) .
C7 H8 0.9300 .
O1 H1 0.8200 .
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_4
N1 C8 C9 C10 -179.5(7) .
C13 C8 C9 C10 60.4(10) .
C14 C8 C9 C10 -59.7(9) .
C8 C9 C10 C17 58.2(11) .
C8 C9 C10 C11 -58.5(10) .
C17 C10 C11 C12 -38.8(13) .
C9 C10 C11 C12 73.2(11) .
C10 C11 C12 C16 39.7(13) .
C10 C11 C12 C13 -73.5(11) .
N1 C8 C13 C12 179.3(7) .
C9 C8 C13 C12 -62.3(10) .
C14 C8 C13 C12 54.4(10) .
C16 C12 C13 C8 -50.6(12) .
C11 C12 C13 C8 62.5(11) .
N1 C8 C14 C15 179.1(6) .
C9 C8 C14 C15 63.4(9) .
C13 C8 C14 C15 -57.8(9) .
C8 C14 C15 C17 -63.9(10) .
C8 C14 C15 C16 58.9(10) .
C17 C15 C16 C12 55.6(13) .
C14 C15 C16 C12 -61.1(12) .
C11 C12 C16 C15 -48.9(13) .
C13 C12 C16 C15 56.5(12) .
C16 C15 C17 C10 -51.8(13) .
C14 C15 C17 C10 66.2(12) .
C11 C10 C17 C15 43.0(13) .
C9 C10 C17 C15 -62.9(12) .
C103 C101 C102 F2 -179.8(5) .
I1 C101 C102 F2 1.4(7) .
C103 C101 C102 C103 0.2(8) 2_565
I1 C101 C102 C103 -178.6(4) 2_565
C102 C101 C103 F1 -179.5(4) .
I1 C101 C103 F1 -0.8(6) .
C102 C101 C103 C102 -0.2(8) 2_565
I1 C101 C103 C102 178.6(4) 2_565
C9 C8 N1 C7 121.9(7) .
C13 C8 N1 C7 -116.4(7) .
C14 C8 N1 C7 7.2(9) .
O1 C1 C2 C3 -178.9(5) .
C6 C1 C2 C3 0.6(7) .
O1 C1 C2 O2 1.0(7) .
C6 C1 C2 O2 -179.5(5) .
O2 C2 C3 C4 179.3(5) .
C1 C2 C3 C4 -0.8(8) .
C2 C3 C4 C5 -0.5(9) .
C3 C4 C5 C6 2.0(10) .
O1 C1 C6 C5 -179.7(5) .
C2 C1 C6 C5 0.8(7) .
O1 C1 C6 C7 -1.2(8) .
C2 C1 C6 C7 179.3(5) .
C4 C5 C6 C1 -2.1(9) .
C4 C5 C6 C7 179.4(6) .
C8 N1 C7 C6 179.0(6) .
C1 C6 C7 N1 1.2(8) .
C5 C6 C7 N1 179.6(5) .
C3 C2 O2 C18 -3.2(9) .
C1 C2 O2 C18 177.0(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203941
