#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/56/4505618.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_4505618
loop_
_publ_author_name
'Nath, Bhaskar'
'Baruah, Jubaraj B.'
_publ_section_title
;
 An Imidazole-Based Bisphenol
 2-((2-Hydroxy-3,5-dimethylphenyl)(imidazol-4-yl)methyl)-4,6-dimethylphenol:
 A Versatile Host for Anions
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1671
_journal_paper_doi               10.1021/cg2017215
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.928(2)
_cell_angle_beta                 102.486(2)
_cell_angle_gamma                103.478(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0009(3)
_cell_length_b                   9.2227(3)
_cell_length_c                   13.6691(5)
_cell_measurement_reflns_used    6121
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.65
_cell_volume                     955.31(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11746
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.926
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                2943
_reflns_number_total             3424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2017215_si_005.cif
_cod_data_source_block           nbpfumrcacd_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4505618
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C6 C 0.9592(2) 0.80201(16) 0.21500(12) 0.0298(4) Uani 1 1 d .
C10 C 1.0793(2) 1.05456(16) 0.14820(12) 0.0297(4) Uani 1 1 d .
C1 C 0.8089(2) 0.68262(17) 0.19505(12) 0.0318(4) Uani 1 1 d .
C9 C 0.9356(2) 0.95770(16) 0.19033(12) 0.0303(4) Uani 1 1 d .
H9 H 0.8266 0.9431 0.1382 0.036 Uiso 1 1 calc R
C2 C 0.8203(2) 0.53911(17) 0.22311(13) 0.0353(4) Uani 1 1 d .
C18 C 1.0484(2) 1.10870(18) 0.35852(12) 0.0357(4) Uani 1 1 d .
H18 H 1.1613 1.1042 0.3536 0.043 Uiso 1 1 calc R
C13 C 0.9055(2) 1.03934(16) 0.28143(12) 0.0316(4) Uani 1 1 d .
C14 C 0.7361(2) 1.04203(17) 0.29072(13) 0.0359(4) Uani 1 1 d .
C17 C 1.0288(2) 1.18419(19) 0.44230(13) 0.0393(4) Uani 1 1 d .
C5 C 1.1208(2) 0.77555(18) 0.26082(12) 0.0343(4) Uani 1 1 d .
H5 H 1.2209 0.8545 0.2735 0.041 Uiso 1 1 calc R
C3 C 0.9850(2) 0.51897(18) 0.27036(13) 0.0379(4) Uani 1 1 d .
H3 H 0.9934 0.4247 0.2907 0.045 Uiso 1 1 calc R
C4 C 1.1370(2) 0.63365(19) 0.28833(13) 0.0370(4) Uani 1 1 d .
C15 C 0.7121(2) 1.11921(19) 0.37401(14) 0.0416(4) Uani 1 1 d .
C7 C 0.6596(3) 0.4112(2) 0.20057(18) 0.0514(5) Uani 1 1 d .
H7A H 0.5718 0.4333 0.2325 0.077 Uiso 1 1 calc R
H7B H 0.6907 0.3221 0.2255 0.077 Uiso 1 1 calc R
H7C H 0.6133 0.3964 0.1293 0.077 Uiso 1 1 calc R
C16 C 0.8576(3) 1.1879(2) 0.44770(14) 0.0439(4) Uani 1 1 d .
H16 H 0.8411 1.2384 0.5030 0.053 Uiso 1 1 calc R
C19 C 0.5280(3) 1.1249(3) 0.38159(19) 0.0619(6) Uani 1 1 d .
H19A H 0.4674 1.0296 0.3988 0.093 Uiso 1 1 calc R
H19B H 0.4648 1.1485 0.3182 0.093 Uiso 1 1 calc R
H19C H 0.5350 1.2004 0.4325 0.093 Uiso 1 1 calc R
C20 C 1.1851(3) 1.2579(3) 0.52479(15) 0.0559(5) Uani 1 1 d .
H20A H 1.2107 1.1864 0.5725 0.084 Uiso 1 1 calc R
H20B H 1.1587 1.3396 0.5578 0.084 Uiso 1 1 calc R
H20C H 1.2856 1.2947 0.4966 0.084 Uiso 1 1 calc R
C8 C 1.3154(3) 0.6067(2) 0.33547(17) 0.0542(5) Uani 1 1 d .
H8A H 1.3274 0.6023 0.4067 0.081 Uiso 1 1 calc R
H8B H 1.4067 0.6869 0.3223 0.081 Uiso 1 1 calc R
H8C H 1.3255 0.5139 0.3074 0.081 Uiso 1 1 calc R
O1 O 0.65263(15) 0.71502(12) 0.14938(10) 0.0426(3) Uani 1 1 d .
H1 H 0.5775 0.6370 0.1300 0.064 Uiso 1 1 calc R
O2 O 0.58608(16) 0.97776(15) 0.21919(11) 0.0525(4) Uani 1 1 d .
H2 H 0.5966 0.8992 0.1952 0.079 Uiso 1 1 calc R
N1 N 1.19374(17) 1.00589(14) 0.10039(10) 0.0318(3) Uani 1 1 d .
N2 N 1.24190(19) 1.24387(15) 0.08783(11) 0.0366(3) Uani 1 1 d .
C12 C 1.1110(2) 1.20413(17) 0.13938(13) 0.0364(4) Uani 1 1 d .
H12 H 1.0537 1.2686 0.1641 0.044 Uiso 1 1 calc R
C11 C 1.2908(2) 1.12233(17) 0.06601(13) 0.0347(4) Uani 1 1 d .
H11 H 1.3790 1.1188 0.0321 0.042 Uiso 1 1 calc R
C22 C 0.2400(2) 0.62357(16) 0.04817(12) 0.0310(4) Uani 1 1 d .
C21 C 0.0439(2) 0.56347(17) 0.02634(12) 0.0321(4) Uani 1 1 d .
H21 H -0.0214 0.6199 0.0518 0.038 Uiso 1 1 calc R
O3 O 0.33979(15) 0.53382(12) 0.05727(10) 0.0392(3) Uani 1 1 d .
O4 O 0.29683(16) 0.76262(12) 0.05502(10) 0.0457(3) Uani 1 1 d .
H2A H 1.280(3) 1.337(3) 0.0709(15) 0.052(6) Uiso 1 1 d .
H1A H 1.206(3) 0.906(3) 0.0892(17) 0.064(6) Uiso 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'
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
C5 C6 C1 119.06(14) .
C5 C6 C9 122.77(14) .
C1 C6 C9 118.08(14) .
C12 C10 N1 105.58(14) .
C12 C10 C9 127.57(14) .
N1 C10 C9 126.50(13) .
O1 C1 C2 122.71(14) .
O1 C1 C6 116.62(13) .
C2 C1 C6 120.65(15) .
C10 C9 C6 115.57(13) .
C10 C9 C13 110.81(12) .
C6 C9 C13 110.73(13) .
C3 C2 C1 118.02(15) .
C3 C2 C7 121.44(15) .
C1 C2 C7 120.53(16) .
C17 C18 C13 122.53(16) .
C14 C13 C18 118.55(15) .
C14 C13 C9 121.27(15) .
C18 C13 C9 120.14(14) .
O2 C14 C13 123.43(15) .
O2 C14 C15 116.25(15) .
C13 C14 C15 120.24(16) .
C18 C17 C16 117.26(17) .
C18 C17 C20 121.59(17) .
C16 C17 C20 121.15(16) .
C6 C5 C4 121.69(15) .
C4 C3 C2 122.71(15) .
C3 C4 C5 117.82(15) .
C3 C4 C8 121.49(16) .
C5 C4 C8 120.69(17) .
C16 C15 C14 119.07(16) .
C16 C15 C19 121.27(17) .
C14 C15 C19 119.66(17) .
C15 C16 C17 122.30(16) .
C11 N1 C10 109.07(13) .
C11 N2 C12 108.24(14) .
C10 C12 N2 108.20(14) .
N2 C11 N1 108.90(15) .
O4 C22 O3 123.16(15) .
O4 C22 C21 117.18(14) .
O3 C22 C21 119.66(13) .
C21 C21 C22 125.26(18) 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C6 C5 1.387(2) .
C6 C1 1.402(2) .
C6 C9 1.525(2) .
C10 C12 1.355(2) .
C10 N1 1.381(2) .
C10 C9 1.508(2) .
C1 O1 1.373(2) .
C1 C2 1.402(2) .
C9 C13 1.536(2) .
C2 C3 1.393(2) .
C2 C7 1.500(2) .
C18 C17 1.387(2) .
C18 C13 1.394(2) .
C13 C14 1.394(2) .
C14 O2 1.375(2) .
C14 C15 1.404(2) .
C17 C16 1.396(3) .
C17 C20 1.505(3) .
C5 C4 1.395(2) .
C3 C4 1.386(3) .
C4 C8 1.512(2) .
C15 C16 1.378(3) .
C15 C19 1.511(3) .
N1 C11 1.328(2) .
N2 C11 1.320(2) .
N2 C12 1.370(2) .
C22 O4 1.2513(19) .
C22 O3 1.2675(19) .
C22 C21 1.498(2) .
C21 C21 1.324(3) 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145838
