#------------------------------------------------------------------------------
#$Date: 2025-09-05 04:00:22 +0300 (Fri, 05 Sep 2025) $
#$Revision: 302031 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/08/7250833.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_7250833
loop_
_publ_author_name
'Mandal, Koushik'
'Suresh, Ajay'
'Chopra, Deepak'
_publ_section_title
;
 Quantitative Insights into the Role of Halogen and Triel Bonds in the
 formation of Isostructural Co-crystals of 4-iodophenyl boronic acid
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP02460A
_journal_year                    2025
_chemical_formula_moiety         'C6 H4 I2, 8(C6 H6 B I O2)'
_chemical_formula_sum            'C54 H52 B8 I10 O16'
_chemical_formula_weight         2312.43
_chemical_name_systematic        CC2
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_audit_creation_date             2025-06-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-06-21 deposited with the CCDC.	2025-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.43(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   29.16(4)
_cell_length_b                   9.848(13)
_cell_length_c                   12.991(18)
_cell_measurement_reflns_used    4720
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.20
_cell_volume                     3629(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19353
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.159
_diffrn_reflns_theta_min         1.612
_exptl_absorpt_coefficient_mu    4.329
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4397
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0916 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.5894.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_description       needle
_exptl_crystal_F_000             2148
_exptl_crystal_preparation       'Slow evaporation'
_exptl_crystal_recrystallization_method 'Slow evaporation from nitromethane'
_exptl_crystal_size_max          0.563
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.114
_refine_diff_density_max         1.943
_refine_diff_density_min         -2.009
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         5568
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+18.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1102
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4114
_reflns_number_total             5568
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cp02460a2.cif
_cod_data_source_block           CC2
_cod_original_cell_volume        3628(9)
_cod_database_code               7250833
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.638
_shelx_estimated_absorpt_t_min   0.194
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C13, C14, C15, C16
 with sigma for 1-2 distances of 2 and sigma for 1-3 distances of 2
 C5, C6, C7, C8
 with sigma for 1-2 distances of 2 and sigma for 1-3 distances of 2
 C17, C18, C19
 with sigma for 1-2 distances of 2 and sigma for 1-3 distances of 2
3. Others
 Fixed Sof: C17(0.5) H17(0.5) C18(0.5) H18(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C2(H2), C3(H3), C6(H6), C7(H7), C10(H10), C11(H11),
 C14(H14), C15(H15)
4.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A), O3(H3A), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C17 C 0.4627(4) 0.0496(10) 0.4236(8) 0.038(3) Uani 0.5 1 d . . P A -1
H17 H 0.436961 0.084436 0.371552 0.045 Uiso 0.5 1 calc R U P A -1
C18 C 0.5071(4) 0.0476(10) 0.4051(8) 0.038(3) Uani 0.5 1 d . . P A -1
H18 H 0.511893 0.079582 0.339424 0.046 Uiso 0.5 1 calc R U P A -1
I1 I 0.82619(2) 0.000000 0.06133(4) 0.04076(16) Uani 1 2 d S T P . .
I2 I 0.26770(2) 0.000000 0.25361(5) 0.05434(19) Uani 1 2 d S T P . .
I3 I 0.75313(2) 0.500000 0.61908(4) 0.03896(15) Uani 1 2 d S T P . .
I4 I 0.60809(2) 0.500000 0.64425(3) 0.02882(13) Uani 1 2 d S T P . .
I5 I 0.61339(2) 0.000000 0.45305(4) 0.04293(16) Uani 1 2 d S T P A .
O1 O 0.58863(13) 0.1181(4) 0.1308(3) 0.0316(8) Uani 1 1 d . . . . .
H1 H 0.560344 0.101361 0.130469 0.07(2) Uiso 1 1 calc R . . . .
O2 O 0.49537(11) 0.1177(3) 0.1300(3) 0.0240(7) Uani 1 1 d . . . . .
H2A H 0.476351 0.182959 0.116869 0.036 Uiso 1 1 calc R U . . .
O3 O 0.59133(12) 0.3824(4) 0.0977(3) 0.0290(8) Uani 1 1 d . . . . .
H3A H 0.599922 0.315358 0.137439 0.13(4) Uiso 1 1 calc R . . . .
O4 O 0.46679(12) 0.3815(3) 0.1021(3) 0.0283(8) Uani 1 1 d . . . . .
H4 H 0.455611 0.398825 0.037822 0.21(7) Uiso 1 1 calc R . . . .
C1 C 0.7570(2) 0.000000 0.0845(5) 0.0279(16) Uani 1 2 d S T P . .
C2 C 0.73498(17) 0.1220(6) 0.0929(4) 0.0356(13) Uani 1 1 d . . . . .
H2 H 0.750842 0.205430 0.088773 0.043 Uiso 1 1 calc R U . . .
C3 C 0.68881(17) 0.1212(5) 0.1076(4) 0.0316(12) Uani 1 1 d . . . . .
H3 H 0.673541 0.205187 0.113052 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6646(2) 0.000000 0.1146(5) 0.0225(14) Uani 1 2 d S T P . .
C5 C 0.4196(2) 0.000000 0.1548(5) 0.0163(12) Uani 1 2 d S T P . .
C6 C 0.39683(18) 0.1186(5) 0.1668(5) 0.0424(15) Uani 1 1 d . . . . .
H6 H 0.411057 0.202525 0.155897 0.051 Uiso 1 1 calc R U . . .
C7 C 0.35335(19) 0.1198(6) 0.1944(6) 0.0517(18) Uani 1 1 d . . . . .
H7 H 0.338387 0.203544 0.202550 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3326(2) 0.000000 0.2097(5) 0.0255(15) Uani 1 2 d S T P . .
C9 C 0.6403(2) 0.500000 0.2665(5) 0.0211(13) Uani 1 2 d S T P . .
C10 C 0.65612(19) 0.3796(5) 0.3213(4) 0.0341(12) Uani 1 1 d . . . . .
H10 H 0.645445 0.295309 0.288891 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6872(2) 0.3782(6) 0.4225(4) 0.0371(13) Uani 1 1 d . . . . .
H11 H 0.697140 0.294677 0.457121 0.045 Uiso 1 1 calc R U . . .
C12 C 0.7030(2) 0.500000 0.4703(5) 0.0259(15) Uani 1 2 d S T P . .
C13 C 0.5132(2) 0.500000 0.2726(5) 0.0173(12) Uani 1 2 d S T P . .
C14 C 0.5274(3) 0.3824(6) 0.3281(5) 0.0519(19) Uani 1 1 d . . . . .
H14 H 0.518792 0.297954 0.293678 0.062 Uiso 1 1 calc R U . . .
C15 C 0.5540(3) 0.3813(6) 0.4334(5) 0.056(2) Uani 1 1 d . . . . .
H15 H 0.562840 0.297311 0.468275 0.068 Uiso 1 1 calc R U . . .
C16 C 0.5671(2) 0.500000 0.4855(5) 0.0211(13) Uani 1 2 d S T P . .
C19 C 0.5446(3) 0.000000 0.4803(6) 0.0360(18) Uani 1 2 d S T P . .
B1 B 0.6118(3) 0.000000 0.1254(6) 0.0222(15) Uani 1 2 d S T P . .
B2 B 0.4711(2) 0.000000 0.1357(6) 0.0184(14) Uani 1 2 d S T P . .
B3 B 0.6066(2) 0.500000 0.1518(6) 0.0204(15) Uani 1 2 d S T P . .
B4 B 0.4815(2) 0.500000 0.1556(6) 0.0197(14) Uani 1 2 d S T P . .
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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C18 C17 H17 120.1 . . ?
C18 C17 C19 119.8(10) . 2_656 ?
C19 C17 H17 120.1 2_656 . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.7(9) . . ?
C19 C18 H18 119.6 . . ?
B1 O1 H1 109.5 . . ?
B2 O2 H2A 109.5 . . ?
B3 O3 H3A 109.5 . . ?
B4 O4 H4 109.5 . . ?
C2 C1 I1 119.3(3) 6 . ?
C2 C1 I1 119.3(3) . . ?
C2 C1 C2 121.4(6) . 6 ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C3 117.0(6) . 6 ?
C3 C4 B1 121.5(3) 6 . ?
C3 C4 B1 121.5(3) . . ?
C6 C5 C6 116.9(6) . 6 ?
C6 C5 B2 121.5(3) . . ?
C6 C5 B2 121.5(3) 6 . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 122.0(5) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 I2 120.0(3) 6 . ?
C7 C8 I2 120.0(3) . . ?
C7 C8 C7 120.1(6) 6 . ?
C10 C9 C10 115.1(6) . 6_565 ?
C10 C9 B3 122.4(3) 6_565 . ?
C10 C9 B3 122.4(3) . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 123.0(5) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 I3 119.6(3) 6_565 . ?
C11 C12 I3 119.6(3) . . ?
C11 C12 C11 120.8(6) 6_565 . ?
C14 C13 C14 114.7(6) 6_565 . ?
C14 C13 B4 122.7(3) 6_565 . ?
C14 C13 B4 122.7(3) . . ?
C13 C14 H14 118.5 . . ?
C13 C14 C15 123.1(5) . . ?
C15 C14 H14 118.5 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(5) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 I4 120.8(3) . . ?
C15 C16 I4 120.8(3) 6_565 . ?
C15 C16 C15 118.5(7) 6_565 . ?
C18 C19 I5 120.8(7) . . ?
O1 B1 O1 118.2(6) 6 . ?
O1 B1 C4 120.9(3) . . ?
O1 B1 C4 120.9(3) 6 . ?
O2 B2 O2 115.7(6) 6 . ?
O2 B2 C5 122.1(3) 6 . ?
O2 B2 C5 122.1(3) . . ?
O3 B3 O3 114.8(6) . 6_565 ?
O3 B3 C9 122.6(3) 6_565 . ?
O3 B3 C9 122.6(3) . . ?
O4 B4 O4 116.1(6) . 6_565 ?
O4 B4 C13 121.9(3) 6_565 . ?
O4 B4 C13 121.9(3) . . ?
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
C17 H17 0.9500 . ?
C17 C18 1.371(16) . ?
C17 C19 1.402(13) 2_656 ?
C18 H18 0.9500 . ?
C18 C19 1.369(13) . ?
I1 C1 2.108(7) . ?
I2 C8 2.098(7) . ?
I3 C12 2.136(7) . ?
I4 C16 2.130(7) . ?
I5 C19 2.115(10) . ?
O1 H1 0.8400 . ?
O1 B1 1.355(5) . ?
O2 H2A 0.8400 . ?
O2 B2 1.369(5) . ?
O3 H3A 0.8400 . ?
O3 B3 1.374(5) . ?
O4 H4 0.8400 . ?
O4 B4 1.375(5) . ?
C1 C2 1.378(7) . ?
C1 C2 1.378(7) 6 ?
C2 H2 0.9500 . ?
C2 C3 1.403(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(6) . ?
C4 B1 1.577(10) . ?
C5 C6 1.370(6) . ?
C5 C6 1.370(6) 6 ?
C5 B2 1.576(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.362(7) . ?
C9 C10 1.405(6) 6_565 ?
C9 C10 1.405(6) . ?
C9 B3 1.582(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.413(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(7) . ?
C13 C14 1.376(7) 6_565 ?
C13 C14 1.376(6) . ?
C13 B4 1.585(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.407(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.360(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
O1 H1 O2 0.84 1.90 2.717(6) 163.9 . yes
O2 H2A O4 0.84 1.98 2.726(6) 147.9 . yes
O3 H3A O1 0.84 1.97 2.643(6) 136.6 . yes
O4 H4 O3 0.84 1.97 2.750(6) 154.2 2_655 yes
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
C17 C18 C19 I5 -178.9(7) . . . . ?
I1 C1 C2 C3 179.6(4) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C2 C1 C2 C3 -1.6(11) 6 . . . ?
C2 C3 C4 C3 0.9(10) . . . 6 ?
C2 C3 C4 B1 -176.9(5) . . . . ?
C3 C4 B1 O1 179.2(6) . . . 6 ?
C3 C4 B1 O1 -179.2(6) 6 . . . ?
C3 C4 B1 O1 1.6(9) 6 . . 6 ?
C3 C4 B1 O1 -1.6(9) . . . . ?
C5 C6 C7 C8 -0.3(11) . . . . ?
C6 C5 C6 C7 2.7(12) 6 . . . ?
C6 C5 B2 O2 -0.1(10) . . . . ?
C6 C5 B2 O2 -176.0(6) 6 . . . ?
C6 C5 B2 O2 176.0(6) . . . 6 ?
C6 C5 B2 O2 0.1(10) 6 . . 6 ?
C6 C7 C8 I2 179.1(5) . . . . ?
C6 C7 C8 C7 -2.3(13) . . . 6 ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C9 C10 C11 -2.4(10) 6_565 . . . ?
C10 C9 B3 O3 1.1(9) 6_565 . . 6_565 ?
C10 C9 B3 O3 -179.5(5) . . . 6_565 ?
C10 C9 B3 O3 -1.1(9) . . . . ?
C10 C9 B3 O3 179.5(5) 6_565 . . . ?
C10 C11 C12 I3 -176.4(4) . . . . ?
C10 C11 C12 C11 2.7(11) . . . 6_565 ?
C13 C14 C15 C16 -0.1(12) . . . . ?
C14 C13 C14 C15 0.3(13) 6_565 . . . ?
C14 C13 B4 O4 -0.9(10) . . . . ?
C14 C13 B4 O4 178.5(6) . . . 6_565 ?
C14 C13 B4 O4 0.9(10) 6_565 . . 6_565 ?
C14 C13 B4 O4 -178.5(6) 6_565 . . . ?
C14 C15 C16 I4 -179.2(6) . . . . ?
C14 C15 C16 C15 -0.2(14) . . . 6_565 ?
C19 C17 C18 C19 -1.2(14) 2_656 . . . ?
B2 C5 C6 C7 -173.3(6) . . . . ?
B3 C9 C10 C11 178.2(6) . . . . ?
B4 C13 C14 C15 -177.4(7) . . . . ?
