#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/56/4505624.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_4505624
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            'C20 H23 N3 O5'
_chemical_formula_weight         385.41
_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                 126.488(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0447(12)
_cell_length_b                   26.422(5)
_cell_length_c                   11.2878(18)
_cell_measurement_reflns_used    2281
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.37
_cell_volume                     1929.0(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      293(2)
_diffrn_measured_fraction_theta_full 0.920
_diffrn_measured_fraction_theta_max 0.920
_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  0.1339
_diffrn_reflns_av_sigmaI/netI    0.1494
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16106
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_gt           0.1063
_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)+(0.1000P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2578
_reflns_number_gt                1694
_reflns_number_total             3215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg2017215_si_011.cif
_cod_data_source_block           babu
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P21/c
_cod_database_code               4505624
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
O1 O 0.4169(6) 0.17299(16) 0.7359(4) 0.0528(11) Uani 1 1 d .
O2 O 0.7927(6) 0.14031(15) 0.9896(4) 0.0597(12) Uani 1 1 d .
H2 H 0.6889 0.1531 0.9166 0.089 Uiso 1 1 calc R
N2 N 0.3547(8) 0.20557(16) 1.2509(5) 0.0471(12) Uani 1 1 d .
N1 N 0.1717(7) 0.20068(15) 1.0161(5) 0.0420(11) Uani 1 1 d .
H1A H 0.0715 0.2045 0.9244 0.050 Uiso 1 1 calc R
C11 C 0.1741(9) 0.2169(2) 1.1278(6) 0.0495(15) Uani 1 1 d .
H11 H 0.0664 0.2334 1.1206 0.059 Uiso 1 1 calc R
C12 C 0.4721(9) 0.18030(19) 1.2173(6) 0.0467(15) Uani 1 1 d .
H12 H 0.6061 0.1683 1.2845 0.056 Uiso 1 1 calc R
C10 C 0.3587(8) 0.17628(17) 1.0711(5) 0.0380(13) Uani 1 1 d .
C18 C 0.5237(8) 0.07169(18) 1.1138(5) 0.0424(14) Uani 1 1 d .
H18 H 0.4053 0.0736 1.1101 0.051 Uiso 1 1 calc R
C13 C 0.5617(8) 0.11067(18) 1.0496(5) 0.0390(13) Uani 1 1 d .
C14 C 0.7349(9) 0.10520(19) 1.0509(5) 0.0444(14) Uani 1 1 d .
C15 C 0.8748(9) 0.0649(2) 1.1227(6) 0.0495(15) Uani 1 1 d .
C16 C 0.8281(9) 0.0283(2) 1.1861(6) 0.0508(16) Uani 1 1 d .
H16 H 0.9180 0.0011 1.2334 0.061 Uiso 1 1 calc R
C17 C 0.6523(9) 0.03050(18) 1.1825(6) 0.0456(15) Uani 1 1 d .
C20 C 0.6035(10) -0.0102(2) 1.2528(6) 0.0648(18) Uani 1 1 d .
H20A H 0.5980 0.0047 1.3280 0.097 Uiso 1 1 calc R
H20B H 0.7094 -0.0357 1.2958 0.097 Uiso 1 1 calc R
H20C H 0.4724 -0.0254 1.1790 0.097 Uiso 1 1 calc R
C19 C 1.0667(10) 0.0615(2) 1.1296(7) 0.0719(19) Uani 1 1 d .
H19A H 1.1474 0.0329 1.1885 0.108 Uiso 1 1 calc R
H19B H 1.1465 0.0919 1.1728 0.108 Uiso 1 1 calc R
H19C H 1.0288 0.0576 1.0318 0.108 Uiso 1 1 calc R
C9 C 0.4159(8) 0.15525(17) 0.9748(5) 0.0344(12) Uani 1 1 d .
H9 H 0.4917 0.1819 0.9648 0.041 Uiso 1 1 calc R
C6 C 0.2281(8) 0.14168(18) 0.8191(5) 0.0376(13) Uani 1 1 d .
C1 C 0.2377(9) 0.14998(18) 0.7008(5) 0.0424(14) Uani 1 1 d .
C2 C 0.0783(9) 0.1353(2) 0.5586(5) 0.0455(14) Uani 1 1 d .
C3 C -0.0901(9) 0.11058(19) 0.5356(6) 0.0493(15) Uani 1 1 d .
H3 H -0.1943 0.0992 0.4413 0.059 Uiso 1 1 calc R
C4 C -0.1087(8) 0.10229(18) 0.6481(6) 0.0449(14) Uani 1 1 d .
C8 C -0.2984(9) 0.0768(2) 0.6193(7) 0.0691(19) Uani 1 1 d .
H8A H -0.2964 0.0799 0.7049 0.104 Uiso 1 1 calc R
H8B H -0.2983 0.0416 0.5980 0.104 Uiso 1 1 calc R
H8C H -0.4207 0.0926 0.5368 0.104 Uiso 1 1 calc R
C7 C 0.0887(10) 0.1448(2) 0.4322(6) 0.0693(19) Uani 1 1 d .
H7A H 0.0914 0.1806 0.4189 0.104 Uiso 1 1 calc R
H7B H -0.0304 0.1303 0.3440 0.104 Uiso 1 1 calc R
H7C H 0.2117 0.1296 0.4527 0.104 Uiso 1 1 calc R
C5 C 0.0542(8) 0.11710(18) 0.7897(5) 0.0423(14) Uani 1 1 d .
H5 H 0.0468 0.1104 0.8672 0.051 Uiso 1 1 calc R
O5 O 0.7789(6) 0.21909(17) 0.7631(4) 0.0752(14) Uani 1 1 d .
O4 O 0.7683(7) 0.23574(19) 0.5734(6) 0.0891(16) Uani 1 1 d .
O3 O 0.4952(6) 0.21050(14) 0.5451(4) 0.0573(11) Uani 1 1 d .
N3 N 0.6832(8) 0.22186(17) 0.6287(6) 0.0507(13) Uani 1 1 d .
H2A H 0.418(11) 0.214(2) 1.356(8) 0.10(2) Uiso 1 1 d .
H1 H 0.457(16) 0.187(4) 0.689(11) 0.19(5) 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'
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'
H H 0.0000 0.0000 '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
C1 O1 H1 136(7)
C14 O2 H2 109.5
C11 N2 C12 109.0(5)
C11 N2 H2A 132(4)
C12 N2 H2A 119(4)
C11 N1 C10 108.9(4)
C11 N1 H1A 125.5
C10 N1 H1A 125.5
N2 C11 N1 108.3(5)
N2 C11 H11 125.8
N1 C11 H11 125.8
C10 C12 N2 107.5(5)
C10 C12 H12 126.2
N2 C12 H12 126.2
C12 C10 N1 106.1(5)
C12 C10 C9 129.9(5)
N1 C10 C9 123.7(4)
C17 C18 C13 123.5(5)
C17 C18 H18 118.2
C13 C18 H18 118.2
C14 C13 C18 116.4(5)
C14 C13 C9 121.6(5)
C18 C13 C9 121.8(5)
C13 C14 O2 123.6(5)
C13 C14 C15 122.6(5)
O2 C14 C15 113.7(5)
C16 C15 C14 117.2(6)
C16 C15 C19 121.4(5)
C14 C15 C19 121.4(5)
C15 C16 C17 122.8(5)
C15 C16 H16 118.6
C17 C16 H16 118.6
C18 C17 C16 117.3(5)
C18 C17 C20 120.8(5)
C16 C17 C20 121.9(5)
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C15 C19 H19A 109.5
C15 C19 H19B 109.5
H19A C19 H19B 109.5
C15 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C13 C9 C10 110.5(4)
C13 C9 C6 111.5(4)
C10 C9 C6 113.3(4)
C13 C9 H9 107.1
C10 C9 H9 107.1
C6 C9 H9 107.1
C5 C6 C1 117.6(5)
C5 C6 C9 123.4(4)
C1 C6 C9 118.8(5)
C2 C1 O1 122.8(5)
C2 C1 C6 121.5(5)
O1 C1 C6 115.7(4)
C3 C2 C1 118.6(5)
C3 C2 C7 120.2(5)
C1 C2 C7 121.2(6)
C2 C3 C4 122.1(5)
C2 C3 H3 118.9
C4 C3 H3 118.9
C3 C4 C5 117.9(5)
C3 C4 C8 121.2(5)
C5 C4 C8 120.9(5)
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C5 C6 122.2(5)
C4 C5 H5 118.9
C6 C5 H5 118.9
O4 N3 O5 121.1(6)
O4 N3 O3 118.5(5)
O5 N3 O3 120.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.388(7)
O1 H1 0.84(10)
O2 C14 1.392(6)
O2 H2 0.8200
N2 C11 1.315(7)
N2 C12 1.382(7)
N2 H2A 1.00(7)
N1 C11 1.321(7)
N1 C10 1.397(6)
N1 H1A 0.8600
C11 H11 0.9300
C12 C10 1.333(6)
C12 H12 0.9300
C10 C9 1.517(7)
C18 C17 1.379(7)
C18 C13 1.394(7)
C18 H18 0.9300
C13 C14 1.392(7)
C13 C9 1.516(6)
C14 C15 1.406(7)
C15 C16 1.380(8)
C15 C19 1.501(8)
C16 C17 1.391(8)
C16 H16 0.9300
C17 C20 1.520(8)
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C9 C6 1.530(6)
C9 H9 0.9800
C6 C5 1.391(7)
C6 C1 1.400(7)
C1 C2 1.387(7)
C2 C3 1.382(8)
C2 C7 1.499(8)
C3 C4 1.382(8)
C3 H3 0.9300
C4 C5 1.390(7)
C4 C8 1.516(8)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C5 H5 0.9300
O5 N3 1.229(6)
O4 N3 1.226(6)
O3 N3 1.253(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145844
