#------------------------------------------------------------------------------
#$Date: 2023-11-07 00:56:45 +0200 (Tue, 07 Nov 2023) $
#$Revision: 287442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132306.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_7132306
loop_
_publ_author_name
'Mazars, François'
'Zaragoza, Guillermo'
'Delaude, Lionel'
_publ_section_title
;
 The facile alkylation and iodination of imidazol(in)ium salts in the
 presence of cesium carbonate
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04971J
_journal_year                    2023
_chemical_formula_moiety         'C23 H29 N2, C H Cl3, I'
_chemical_formula_sum            'C24 H30 Cl3 I N2'
_chemical_formula_weight         579.75
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2023-06-29T09:54:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-10-09 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.2342(15)
_cell_length_b                   10.1167(7)
_cell_length_c                   26.9285(17)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.73
_cell_measurement_wavelength     0.71073
_cell_volume                     5239.9(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'APPEX3v2022.1-1 (BRUKER AXS, 2021)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            53950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         2.397
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.542
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     278
_refine_ls_number_reflns         5778
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0257P)²+6.3575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0
_reflns_number_gt                4781
_reflns_number_total             5778
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04971j2.cif
_cod_data_source_block           DIBE063
_cod_database_code               7132306
_shelx_estimated_absorpt_t_min   0.874
_shelx_estimated_absorpt_t_max   0.913
_shelx_shelxl_version_number     2019/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
I1 I 0.48762(2) 0.27431(2) 0.40683(2) 0.02898(6) Uani 1 1 d . . . . .
N1 N 0.50526(10) 0.25458(19) 0.63229(8) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.59139(11) 0.2423(2) 0.58109(8) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.56148(12) 0.1834(2) 0.62041(8) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.49901(14) 0.3599(3) 0.59981(11) 0.0320(7) Uani 1 1 d . . . . .
H2 H 0.463657 0.425465 0.600073 0.038 Uiso 1 1 calc R U . . .
C3 C 0.55249(14) 0.3518(3) 0.56780(11) 0.0337(7) Uani 1 1 d . . . . .
H3 H 0.561835 0.410291 0.541034 0.04 Uiso 1 1 calc R U . . .
C4 C 0.45970(12) 0.2294(2) 0.67432(9) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.47296(12) 0.2966(2) 0.71859(10) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.42997(13) 0.2689(2) 0.75850(9) 0.0251(5) Uani 1 1 d . . . . .
H6 H 0.439018 0.310018 0.789544 0.03 Uiso 1 1 calc R U . . .
C7 C 0.37393(13) 0.1826(3) 0.75450(9) 0.0243(5) Uani 1 1 d . . . . .
C8 C 0.36153(12) 0.1221(2) 0.70884(9) 0.0217(5) Uani 1 1 d . . . . .
H8 H 0.322617 0.064916 0.705481 0.026 Uiso 1 1 calc R U . . .
C9 C 0.40455(12) 0.1430(2) 0.66805(9) 0.0185(5) Uani 1 1 d . . . . .
C10 C 0.53007(14) 0.3980(3) 0.72283(11) 0.0348(7) Uani 1 1 d . . . . .
H10A H 0.53859 0.417659 0.757939 0.052 Uiso 1 1 calc R U . . .
H10B H 0.516099 0.478999 0.705569 0.052 Uiso 1 1 calc R U . . .
H10C H 0.572669 0.363144 0.707741 0.052 Uiso 1 1 calc R U . . .
C11 C 0.32789(16) 0.1565(3) 0.79859(11) 0.0387(7) Uani 1 1 d . . . . .
H11A H 0.304284 0.071376 0.794269 0.058 Uiso 1 1 calc R U . . .
H11B H 0.293195 0.227007 0.801375 0.058 Uiso 1 1 calc R U . . .
H11C H 0.356194 0.153958 0.828831 0.058 Uiso 1 1 calc R U . . .
C12 C 0.39148(14) 0.0729(3) 0.61968(10) 0.0271(6) Uani 1 1 d . . . . .
H12A H 0.345515 0.031179 0.620547 0.041 Uiso 1 1 calc R U . . .
H12B H 0.427157 0.005071 0.61463 0.041 Uiso 1 1 calc R U . . .
H12C H 0.393251 0.136803 0.592358 0.041 Uiso 1 1 calc R U . . .
C13 C 0.65599(12) 0.2027(2) 0.55750(9) 0.0195(5) Uani 1 1 d . . . . .
C14 C 0.71649(13) 0.2712(2) 0.57027(9) 0.0213(5) Uani 1 1 d . . . . .
C15 C 0.77755(12) 0.2338(2) 0.54658(9) 0.0220(5) Uani 1 1 d . . . . .
H15 H 0.819674 0.277791 0.554727 0.026 Uiso 1 1 calc R U . . .
C16 C 0.77857(12) 0.1335(2) 0.51118(9) 0.0210(5) Uani 1 1 d . . . . .
C17 C 0.71705(13) 0.0680(2) 0.50020(9) 0.0219(5) Uani 1 1 d . . . . .
H17 H 0.717748 -0.001671 0.476538 0.026 Uiso 1 1 calc R U . . .
C18 C 0.65445(12) 0.1012(2) 0.52277(8) 0.0211(5) Uani 1 1 d . . . . .
C19 C 0.71594(15) 0.3815(3) 0.60800(10) 0.0301(6) Uani 1 1 d . . . . .
H19A H 0.76384 0.407555 0.615628 0.045 Uiso 1 1 calc R U . . .
H19B H 0.692969 0.351072 0.63841 0.045 Uiso 1 1 calc R U . . .
H19C H 0.690659 0.457509 0.594477 0.045 Uiso 1 1 calc R U . . .
C20 C 0.84490(14) 0.0986(3) 0.48436(10) 0.0306(6) Uani 1 1 d . . . . .
H20A H 0.847614 0.002524 0.480088 0.046 Uiso 1 1 calc R U . . .
H20B H 0.884846 0.129078 0.503838 0.046 Uiso 1 1 calc R U . . .
H20C H 0.845363 0.141481 0.451735 0.046 Uiso 1 1 calc R U . . .
C21 C 0.58775(14) 0.0328(3) 0.50915(9) 0.0287(6) Uani 1 1 d . . . . .
H21A H 0.598024 -0.043953 0.488176 0.043 Uiso 1 1 calc R U . . .
H21B H 0.557681 0.094196 0.490966 0.043 Uiso 1 1 calc R U . . .
H21C H 0.564053 0.003423 0.539423 0.043 Uiso 1 1 calc R U . . .
C22 C 0.58620(13) 0.0615(2) 0.64557(9) 0.0204(5) Uani 1 1 d . . . . .
H22A H 0.611063 0.005998 0.621027 0.024 Uiso 1 1 calc R U . . .
H22B H 0.545325 0.010808 0.657272 0.024 Uiso 1 1 calc R U . . .
C23 C 0.63357(18) 0.0863(3) 0.68893(12) 0.0480(9) Uani 1 1 d . . . . .
H23A H 0.649855 0.001735 0.702317 0.072 Uiso 1 1 calc R U . . .
H23B H 0.608213 0.134616 0.714765 0.072 Uiso 1 1 calc R U . . .
H23C H 0.673553 0.138871 0.678007 0.072 Uiso 1 1 calc R U . . .
C24 C 0.66185(14) 0.3298(3) 0.35277(10) 0.0274(6) Uani 1 1 d . . . . .
H24 H 0.611983 0.31232 0.360941 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.67153(4) 0.49938(7) 0.33901(3) 0.03844(17) Uani 1 1 d . . . . .
Cl2 Cl 0.71301(4) 0.28396(7) 0.40370(3) 0.03968(18) Uani 1 1 d . . . . .
Cl3 Cl 0.68506(4) 0.23371(7) 0.30032(3) 0.04004(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 0 '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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2 109.5(2) . . ?
C1 N1 C4 125.4(2) . . ?
C2 N1 C4 125.1(2) . . ?
C1 N2 C3 109.1(2) . . ?
C1 N2 C13 126.1(2) . . ?
C3 N2 C13 124.8(2) . . ?
N1 C1 N2 107.2(2) . . ?
N1 C1 C22 126.6(2) . . ?
N2 C1 C22 126.2(2) . . ?
C3 C2 N1 107.0(2) . . ?
C2 C3 N2 107.3(2) . . ?
C9 C4 C5 123.5(2) . . ?
C9 C4 N1 118.5(2) . . ?
C5 C4 N1 118.0(2) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 C10 120.9(2) . . ?
C4 C5 C10 122.0(2) . . ?
C5 C6 C7 122.0(2) . . ?
C6 C7 C8 118.4(2) . . ?
C6 C7 C11 120.3(2) . . ?
C8 C7 C11 121.2(2) . . ?
C9 C8 C7 121.8(2) . . ?
C4 C9 C8 117.1(2) . . ?
C4 C9 C12 122.1(2) . . ?
C8 C9 C12 120.8(2) . . ?
C18 C13 C14 123.4(2) . . ?
C18 C13 N2 118.7(2) . . ?
C14 C13 N2 117.9(2) . . ?
C15 C14 C13 117.1(2) . . ?
C15 C14 C19 121.1(2) . . ?
C13 C14 C19 121.8(2) . . ?
C14 C15 C16 121.7(2) . . ?
C17 C16 C15 118.8(2) . . ?
C17 C16 C20 120.5(2) . . ?
C15 C16 C20 120.7(2) . . ?
C16 C17 C18 122.0(2) . . ?
C13 C18 C17 117.1(2) . . ?
C13 C18 C21 121.5(2) . . ?
C17 C18 C21 121.4(2) . . ?
C1 C22 C23 114.2(2) . . ?
Cl2 C24 Cl1 111.28(15) . . ?
Cl2 C24 Cl3 109.71(14) . . ?
Cl1 C24 Cl3 109.85(14) . . ?
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
N1 C1 1.338(3) . ?
N1 C2 1.384(3) . ?
N1 C4 1.454(3) . ?
N2 C1 1.344(3) . ?
N2 C3 1.383(3) . ?
N2 C13 1.452(3) . ?
C1 C22 1.486(3) . ?
C2 C3 1.345(4) . ?
C4 C9 1.385(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.385(4) . ?
C5 C10 1.507(3) . ?
C6 C7 1.391(4) . ?
C7 C8 1.394(3) . ?
C7 C11 1.504(4) . ?
C8 C9 1.392(3) . ?
C9 C12 1.504(3) . ?
C13 C18 1.389(3) . ?
C13 C14 1.397(3) . ?
C14 C15 1.389(3) . ?
C14 C19 1.509(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.388(3) . ?
C16 C20 1.508(3) . ?
C17 C18 1.390(3) . ?
C18 C21 1.503(3) . ?
C22 C23 1.502(4) . ?
C24 Cl2 1.751(3) . ?
C24 Cl1 1.765(3) . ?
C24 Cl3 1.772(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
C2 H2 I1 0.95 3.18 3.714(3) 117.1 5_666 yes
C24 H24 I1 1 2.72 3.697(3) 165.6 . yes
