#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/00/2230020.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230020
loop_
_publ_author_name
'Rosepriya, S.'
'Thiruvalluvar, A.'
'Jayabharathi, J.'
'Srinivasan, N.'
'Butcher, R. J.'
'Jasinski, J. P.'
'Golen, J. A.'
_publ_section_title
;
 1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole
;
_journal_coeditor_code           HG5018
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1065
_journal_paper_doi               10.1107/S1600536811012098
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H19 F N2'
_chemical_formula_moiety         'C19 H19 F N2'
_chemical_formula_structural     'C19 H19 F N2'
_chemical_formula_sum            'C19 H19 F N2'
_chemical_formula_weight         294.36
_chemical_melting_point          377
_chemical_name_common            1H-imidazole
_chemical_name_systematic
;
1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole
;
_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
_cell_angle_alpha                105.423(9)
_cell_angle_beta                 105.677(9)
_cell_angle_gamma                95.781(9)
_cell_formula_units_Z            2
_cell_length_a                   8.4226(10)
_cell_length_b                   9.5572(10)
_cell_length_c                   11.0351(11)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      71.19
_cell_measurement_theta_min      5.55
_cell_volume                     810.06(17)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 16.1500
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5121
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         71.32
_diffrn_reflns_theta_min         5.55
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.8578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0944P)²+0.1440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1586
_reflns_number_gt                2771
_reflns_number_total             3054
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5018.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        810.07(17)
_cod_database_code               2230020
_cod_database_fobs_code          2230020
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F4 0.29950(19) 0.53513(14) 0.86850(14) 0.0964(5) Uani d . 1.000
N N1 0.19985(15) -0.06005(14) 0.37504(12) 0.0449(4) Uani d . 1.000
N N3 0.32289(16) -0.11576(15) 0.55605(13) 0.0520(4) Uani d . 1.000
C C2 0.27033(18) -0.00885(17) 0.50979(14) 0.0453(4) Uani d . 1.000
C C4 0.2859(2) -0.23874(19) 0.44868(16) 0.0532(5) Uani d . 1.000
C C5 0.20944(19) -0.20827(17) 0.33550(15) 0.0488(5) Uani d . 1.000
C C11 0.14226(18) 0.02522(16) 0.28741(14) 0.0435(4) Uani d . 1.000
C C12 -0.02859(18) 0.01651(18) 0.23336(15) 0.0480(5) Uani d . 1.000
C C13 -0.08585(19) 0.10368(18) 0.15377(15) 0.0494(5) Uani d . 1.000
C C14 0.0323(2) 0.19566(17) 0.12941(14) 0.0515(5) Uani d . 1.000
C C15 0.2035(2) 0.20141(16) 0.17950(15) 0.0487(5) Uani d . 1.000
C C16 0.25852(18) 0.11506(16) 0.26059(14) 0.0464(4) Uani d . 1.000
C C17 -0.2713(2) 0.0990(2) 0.0987(2) 0.0692(7) Uani d . 1.000
C C18 0.3276(3) 0.2979(2) 0.1464(2) 0.0698(7) Uani d . 1.000
C C21 0.28022(18) 0.14031(17) 0.59540(15) 0.0472(5) Uani d . 1.000
C C22 0.1660(2) 0.2313(2) 0.56533(17) 0.0566(5) Uani d . 1.000
C C23 0.1740(3) 0.3655(2) 0.6562(2) 0.0654(6) Uani d . 1.000
C C24 0.2952(3) 0.4060(2) 0.77740(19) 0.0660(6) Uani d . 1.000
C C25 0.4109(2) 0.3201(2) 0.81121(19) 0.0655(6) Uani d . 1.000
C C26 0.4030(2) 0.1881(2) 0.71957(16) 0.0558(5) Uani d . 1.000
C C41 0.3314(3) -0.3824(2) 0.4636(2) 0.0787(8) Uani d . 1.000
C C51 0.1442(2) -0.3012(2) 0.19482(17) 0.0623(6) Uani d . 1.000
H H12 -0.10645 -0.04873 0.25055 0.0575 Uiso calc R 1.000
H H14 -0.00553 0.25686 0.07653 0.0618 Uiso calc R 1.000
H H16 0.37514 0.11800 0.29712 0.0556 Uiso calc R 1.000
H H17A -0.29302 0.13147 0.01961 0.1037 Uiso calc R 1.000
H H17B -0.30948 0.16460 0.16526 0.1037 Uiso calc R 1.000
H H17C -0.33197 -0.00229 0.07526 0.1037 Uiso calc R 1.000
H H18A 0.34608 0.24283 0.06431 0.1046 Uiso calc R 1.000
H H18B 0.43413 0.32742 0.21839 0.1046 Uiso calc R 1.000
H H18C 0.28339 0.38610 0.13490 0.1046 Uiso calc R 1.000
H H22 0.08176 0.20091 0.48163 0.0679 Uiso calc R 1.000
H H23 0.09729 0.42825 0.63510 0.0784 Uiso calc R 1.000
H H25 0.49398 0.35114 0.89552 0.0785 Uiso calc R 1.000
H H26 0.48261 0.12777 0.74092 0.0670 Uiso calc R 1.000
H H41A 0.45009 -0.38100 0.47068 0.1181 Uiso calc R 1.000
H H41B 0.26202 -0.46386 0.38633 0.1181 Uiso calc R 1.000
H H41C 0.31177 -0.39629 0.54360 0.1181 Uiso calc R 1.000
H H51A 0.14887 -0.40467 0.18925 0.0934 Uiso calc R 1.000
H H51B 0.21302 -0.26845 0.14515 0.0934 Uiso calc R 1.000
H H51C 0.02775 -0.29169 0.15728 0.0934 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 ' 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'
F F 0.0727 0.0534 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 ' 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 . . . 107.12(13) no
C2 N1 C11 . . . 127.30(14) no
C5 N1 C11 . . . 125.28(12) no
C2 N3 C4 . . . 106.09(13) no
N1 C2 N3 . . . 110.65(14) no
N1 C2 C21 . . . 126.33(14) no
N3 C2 C21 . . . 122.95(13) no
N3 C4 C5 . . . 110.80(16) no
N3 C4 C41 . . . 121.02(15) no
C5 C4 C41 . . . 128.18(16) no
N1 C5 C4 . . . 105.35(14) no
N1 C5 C51 . . . 122.36(14) no
C4 C5 C51 . . . 132.29(16) no
N1 C11 C12 . . . 119.20(14) no
N1 C11 C16 . . . 119.31(14) no
C12 C11 C16 . . . 121.49(15) no
C11 C12 C13 . . . 119.80(15) no
C12 C13 C14 . . . 118.19(15) no
C12 C13 C17 . . . 120.13(16) no
C14 C13 C17 . . . 121.67(16) no
C13 C14 C15 . . . 122.39(15) no
C14 C15 C16 . . . 118.59(15) no
C14 C15 C18 . . . 120.88(16) no
C16 C15 C18 . . . 120.54(16) no
C11 C16 C15 . . . 119.50(15) no
C2 C21 C22 . . . 123.84(14) no
C2 C21 C26 . . . 117.57(15) no
C22 C21 C26 . . . 118.34(16) no
C21 C22 C23 . . . 120.67(17) no
C22 C23 C24 . . . 118.6(2) no
F4 C24 C23 . . . 118.8(2) no
F4 C24 C25 . . . 118.53(18) no
C23 C24 C25 . . . 122.71(19) no
C24 C25 C26 . . . 118.09(17) no
C21 C26 C25 . . . 121.54(17) no
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C13 C14 H14 . . . 119.00 no
C15 C14 H14 . . . 119.00 no
C11 C16 H16 . . . 120.00 no
C15 C16 H16 . . . 120.00 no
C13 C17 H17A . . . 109.00 no
C13 C17 H17B . . . 109.00 no
C13 C17 H17C . . . 109.00 no
H17A C17 H17B . . . 110.00 no
H17A C17 H17C . . . 109.00 no
H17B C17 H17C . . . 110.00 no
C15 C18 H18A . . . 109.00 no
C15 C18 H18B . . . 109.00 no
C15 C18 H18C . . . 109.00 no
H18A C18 H18B . . . 109.00 no
H18A C18 H18C . . . 109.00 no
H18B C18 H18C . . . 110.00 no
C21 C22 H22 . . . 120.00 no
C23 C22 H22 . . . 120.00 no
C22 C23 H23 . . . 121.00 no
C24 C23 H23 . . . 121.00 no
C24 C25 H25 . . . 121.00 no
C26 C25 H25 . . . 121.00 no
C21 C26 H26 . . . 119.00 no
C25 C26 H26 . . . 119.00 no
C4 C41 H41A . . . 109.00 no
C4 C41 H41B . . . 109.00 no
C4 C41 H41C . . . 109.00 no
H41A C41 H41B . . . 109.00 no
H41A C41 H41C . . . 109.00 no
H41B C41 H41C . . . 109.00 no
C5 C51 H51A . . . 109.00 no
C5 C51 H51B . . . 109.00 no
C5 C51 H51C . . . 109.00 no
H51A C51 H51B . . . 109.00 no
H51A C51 H51C . . . 109.00 no
H51B C51 H51C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F4 C24 . . 1.359(2) no
N1 C2 . . 1.3713(19) no
N1 C5 . . 1.385(2) no
N1 C11 . . 1.442(2) no
N3 C2 . . 1.322(2) no
N3 C4 . . 1.367(2) no
C2 C21 . . 1.466(2) no
C4 C5 . . 1.362(2) no
C4 C41 . . 1.500(3) no
C5 C51 . . 1.486(2) no
C11 C12 . . 1.385(2) no
C11 C16 . . 1.381(2) no
C12 C13 . . 1.393(2) no
C13 C14 . . 1.389(2) no
C13 C17 . . 1.507(2) no
C14 C15 . . 1.387(2) no
C15 C16 . . 1.394(2) no
C15 C18 . . 1.506(3) no
C21 C22 . . 1.393(2) no
C21 C26 . . 1.401(2) no
C22 C23 . . 1.385(3) no
C23 C24 . . 1.374(3) no
C24 C25 . . 1.375(3) no
C25 C26 . . 1.374(3) no
C12 H12 . . 0.9500 no
C14 H14 . . 0.9500 no
C16 H16 . . 0.9500 no
C17 H17A . . 0.9800 no
C17 H17B . . 0.9800 no
C17 H17C . . 0.9800 no
C18 H18A . . 0.9800 no
C18 H18B . . 0.9800 no
C18 H18C . . 0.9800 no
C22 H22 . . 0.9500 no
C23 H23 . . 0.9500 no
C25 H25 . . 0.9500 no
C26 H26 . . 0.9500 no
C41 H41A . . 0.9800 no
C41 H41B . . 0.9800 no
C41 H41C . . 0.9800 no
C51 H51A . . 0.9800 no
C51 H51B . . 0.9800 no
C51 H51C . . 0.9800 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12 Cg3 2_556 0.95 2.86 3.7969(19) 169 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 N3 . . . . 0.02(19) no
C5 N1 C2 C21 . . . . -176.74(15) no
C11 N1 C2 N3 . . . . -173.88(14) no
C11 N1 C2 C21 . . . . 9.4(3) no
C2 N1 C5 C4 . . . . -0.20(18) no
C2 N1 C5 C51 . . . . 179.77(15) no
C11 N1 C5 C4 . . . . 173.87(15) no
C11 N1 C5 C51 . . . . -6.2(2) no
C2 N1 C11 C12 . . . . -105.84(19) no
C2 N1 C11 C16 . . . . 73.4(2) no
C5 N1 C11 C12 . . . . 81.3(2) no
C5 N1 C11 C16 . . . . -99.51(18) no
C4 N3 C2 N1 . . . . 0.16(18) no
C4 N3 C2 C21 . . . . 177.05(15) no
C2 N3 C4 C5 . . . . -0.3(2) no
C2 N3 C4 C41 . . . . 178.74(17) no
N1 C2 C21 C22 . . . . 27.5(3) no
N1 C2 C21 C26 . . . . -158.45(16) no
N3 C2 C21 C22 . . . . -148.95(17) no
N3 C2 C21 C26 . . . . 25.2(2) no
N3 C4 C5 N1 . . . . 0.30(19) no
N3 C4 C5 C51 . . . . -179.66(17) no
C41 C4 C5 N1 . . . . -178.63(19) no
C41 C4 C5 C51 . . . . 1.4(3) no
N1 C11 C12 C13 . . . . 176.87(14) no
C16 C11 C12 C13 . . . . -2.3(2) no
N1 C11 C16 C15 . . . . -177.86(14) no
C12 C11 C16 C15 . . . . 1.3(2) no
C11 C12 C13 C14 . . . . 1.1(2) no
C11 C12 C13 C17 . . . . -177.75(15) no
C12 C13 C14 C15 . . . . 1.1(2) no
C17 C13 C14 C15 . . . . 179.93(15) no
C13 C14 C15 C16 . . . . -2.1(2) no
C13 C14 C15 C18 . . . . 177.47(16) no
C14 C15 C16 C11 . . . . 0.9(2) no
C18 C15 C16 C11 . . . . -178.71(15) no
C2 C21 C22 C23 . . . . 174.03(18) no
C26 C21 C22 C23 . . . . 0.0(3) no
C2 C21 C26 C25 . . . . -173.55(16) no
C22 C21 C26 C25 . . . . 0.9(3) no
C21 C22 C23 C24 . . . . -1.0(3) no
C22 C23 C24 F4 . . . . -177.64(19) no
C22 C23 C24 C25 . . . . 1.3(3) no
F4 C24 C25 C26 . . . . 178.47(18) no
C23 C24 C25 C26 . . . . -0.5(3) no
C24 C25 C26 C21 . . . . -0.7(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656642
