#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/29/2012970.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_2012970
loop_
_publ_author_name
'Vázquez García, Rosa A.'
'Bernès, Sylvain'
'Gutiérrez Pérez,  René'
'Martínez García, Marcos'
_publ_section_title
;
 2-Methyl-1,4,5-triphenyl-1H-imidazole
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o619
_journal_page_last               o620
_journal_paper_doi               10.1107/S0108270102016220
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_chemical_melting_point          533
_chemical_name_systematic        2-Methyl-1,4,5-triphenyl-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
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.288(6)
_cell_angle_beta                 92.042(4)
_cell_angle_gamma                106.338(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5768(5)
_cell_length_b                   9.8285(9)
_cell_length_c                   10.7315(7)
_cell_measurement_reflns_used    78
_cell_measurement_temperature    299.0(10)
_cell_measurement_theta_max      15.01
_cell_measurement_theta_min      4.52
_cell_volume                     860.79(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1998)'
_diffrn_ambient_temperature      299.0(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5916
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       regular_prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.069
_refine_ls_R_factor_gt           0.050
_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)+(0.0582P)²+0.1152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.132
_refine_ls_wR_factor_ref         0.145
_reflns_number_gt                3642
_reflns_number_total             4985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1661.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2012970
_cod_database_fobs_code          2012970
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.47519(12) 0.26420(11) 0.39603(9) 0.0503(2) Uani d . 1 . . N
C2 0.39422(15) 0.31749(13) 0.48871(11) 0.0520(3) Uani d . 1 . . C
N3 0.46889(13) 0.32914(11) 0.59994(9) 0.0532(3) Uani d . 1 . . N
C4 0.60569(15) 0.28237(13) 0.58033(11) 0.0496(3) Uani d . 1 . . C
C5 0.61126(15) 0.24018(13) 0.45447(11) 0.0482(3) Uani d . 1 . . C
C6 0.42645(14) 0.23693(13) 0.26405(11) 0.0510(3) Uani d . 1 . . C
C7 0.42207(17) 0.34995(15) 0.19951(13) 0.0607(3) Uani d . 1 . . C
H7 0.4539 0.4429 0.2404 0.073 Uiso calc R 1 . . H
C8 0.36975(19) 0.32349(19) 0.07298(14) 0.0726(4) Uani d . 1 . . C
H8 0.3637 0.3987 0.0293 0.087 Uiso calc R 1 . . H
C9 0.32680(19) 0.1863(2) 0.01208(14) 0.0761(4) Uani d . 1 . . C
H9 0.2921 0.1691 -0.0728 0.091 Uiso calc R 1 . . H
C10 0.3350(2) 0.07479(19) 0.07588(14) 0.0763(4) Uani d . 1 . . C
H10 0.3076 -0.0175 0.0337 0.092 Uiso calc R 1 . . H
C11 0.38393(18) 0.09873(15) 0.20340(13) 0.0639(3) Uani d . 1 . . C
H11 0.3880 0.0230 0.2471 0.077 Uiso calc R 1 . . H
C12 0.23945(16) 0.35349(16) 0.46493(14) 0.0639(4) Uani d . 1 . . C
H12A 0.2049 0.3889 0.5430 0.096 Uiso calc PR 0.63(2) A 1 H
H12B 0.1572 0.2694 0.4274 0.096 Uiso calc PR 0.63(2) A 1 H
H12C 0.2564 0.4254 0.4091 0.096 Uiso calc PR 0.63(2) A 1 H
H12D 0.2230 0.3593 0.3769 0.096 Uiso d PR 0.37(2) A 2 H
H12E 0.2452 0.4438 0.5121 0.096 Uiso d PR 0.37(2) A 2 H
H12F 0.1503 0.2807 0.4904 0.096 Uiso d PR 0.37(2) A 2 H
C13 0.72423(16) 0.29509(13) 0.68670(11) 0.0518(3) Uani d . 1 . . C
C14 0.88829(18) 0.31270(17) 0.67127(13) 0.0660(4) Uani d . 1 . . C
H14 0.9251 0.3125 0.5908 0.079 Uiso calc R 1 . . H
C15 0.9983(2) 0.33053(19) 0.77360(15) 0.0749(4) Uani d . 1 . . C
H15 1.1076 0.3409 0.7613 0.090 Uiso calc R 1 . . H
C16 0.9462(2) 0.33292(19) 0.89336(15) 0.0789(5) Uani d . 1 . . C
H16 1.0200 0.3455 0.9622 0.095 Uiso calc R 1 . . H
C17 0.7844(2) 0.3166(2) 0.91031(14) 0.0813(5) Uani d . 1 . . C
H17 0.7489 0.3183 0.9912 0.098 Uiso calc R 1 . . H
C18 0.6738(2) 0.29779(17) 0.80862(13) 0.0668(4) Uani d . 1 . . C
H18 0.5645 0.2868 0.8217 0.080 Uiso calc R 1 . . H
C19 0.72545(15) 0.17892(13) 0.38347(10) 0.0503(3) Uani d . 1 . . C
C20 0.80897(18) 0.24451(19) 0.28823(13) 0.0689(4) Uani d . 1 . . C
H20 0.7947 0.3299 0.2676 0.083 Uiso calc R 1 . . H
C21 0.91500(19) 0.1822(2) 0.22297(14) 0.0847(5) Uani d . 1 . . C
H21 0.9705 0.2261 0.1585 0.102 Uiso calc R 1 . . H
C22 0.9376(2) 0.0571(2) 0.25327(16) 0.0823(5) Uani d . 1 . . C
H22 1.0084 0.0163 0.2096 0.099 Uiso calc R 1 . . H
C23 0.8569(2) -0.0069(2) 0.34668(18) 0.0854(5) Uani d . 1 . . C
H23 0.8732 -0.0915 0.3676 0.103 Uiso calc R 1 . . H
C24 0.7505(2) 0.05196(16) 0.41149(15) 0.0690(4) Uani d . 1 . . C
H24 0.6948 0.0058 0.4748 0.083 Uiso calc R 1 . . H
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 3 5
4 -1 5
1 1 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C5 107.14(10) y
C2 N1 C6 125.99(10) y
C5 N1 C6 126.87(10) y
N3 C2 N1 111.36(11) y
N3 C2 C12 124.87(11) y
N1 C2 C12 123.75(11) y
C2 N3 C4 106.25(10) y
C5 C4 N3 109.98(11) y
C5 C4 C13 130.35(11) y
N3 C4 C13 119.44(10) y
C4 C5 N1 105.28(10) y
C4 C5 C19 132.45(11) y
N1 C5 C19 122.27(10) y
C7 C6 C11 120.84(12) n
C7 C6 N1 119.17(11) n
C11 C6 N1 119.99(12) n
C6 C7 C8 119.33(13) n
C6 C7 H7 120.3 n
C8 C7 H7 120.3 n
C9 C8 C7 120.15(15) n
C9 C8 H8 119.9 n
C7 C8 H8 119.9 n
C10 C9 C8 120.29(14) n
C10 C9 H9 119.9 n
C8 C9 H9 119.9 n
C9 C10 C11 120.43(14) n
C9 C10 H10 119.8 n
C11 C10 H10 119.8 n
C6 C11 C10 118.92(15) n
C6 C11 H11 120.5 n
C10 C11 H11 120.5 n
C2 C12 H12A 109.5 n
C2 C12 H12B 109.5 n
H12A C12 H12B 109.5 n
C2 C12 H12C 109.5 n
H12A C12 H12C 109.5 n
H12B C12 H12C 109.5 n
C2 C12 H12D 109.5 n
H12A C12 H12D 138.1 n
H12B C12 H12D 70.8 n
C2 C12 H12E 109.5 n
H12B C12 H12E 138.1 n
H12C C12 H12E 70.8 n
H12D C12 H12E 109.5 n
C2 C12 H12F 109.5 n
H12A C12 H12F 70.8 n
H12C C12 H12F 138.1 n
H12D C12 H12F 109.5 n
H12E C12 H12F 109.5 n
C14 C13 C18 117.88(13) n
C14 C13 C4 122.39(11) n
C18 C13 C4 119.63(12) n
C15 C14 C13 121.16(14) n
C15 C14 H14 119.4 n
C13 C14 H14 119.4 n
C16 C15 C14 120.15(16) n
C16 C15 H15 119.9 n
C14 C15 H15 119.9 n
C17 C16 C15 119.42(15) n
C17 C16 H16 120.3 n
C15 C16 H16 120.3 n
C16 C17 C18 120.76(14) n
C16 C17 H17 119.6 n
C18 C17 H17 119.6 n
C17 C18 C13 120.63(15) n
C17 C18 H18 119.7 n
C13 C18 H18 119.7 n
C20 C19 C24 118.23(13) n
C20 C19 C5 121.82(12) n
C24 C19 C5 119.95(12) n
C19 C20 C21 119.85(16) n
C19 C20 H20 120.1 n
C21 C20 H20 120.1 n
C22 C21 C20 120.52(15) n
C22 C21 H21 119.7 n
C20 C21 H21 119.7 n
C23 C22 C21 119.81(15) n
C23 C22 H22 120.1 n
C21 C22 H22 120.1 n
C22 C23 C24 120.66(17) n
C22 C23 H23 119.7 n
C24 C23 H23 119.7 n
C23 C24 C19 120.93(15) n
C23 C24 H24 119.5 n
C19 C24 H24 119.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.3732(15) y
N1 C5 . 1.3950(16) y
N1 C6 . 1.4368(15) y
C2 N3 . 1.3123(16) y
C2 C12 . 1.4874(18) y
N3 C4 . 1.3900(15) y
C4 C5 . 1.3754(15) y
C4 C13 . 1.4721(17) y
C5 C19 . 1.4787(16) y
C6 C7 . 1.3803(19) n
C6 C11 . 1.3829(18) n
C7 C8 . 1.3880(19) n
C7 H7 . 0.9300 n
C8 C9 . 1.375(2) n
C8 H8 . 0.9300 n
C9 C10 . 1.371(2) n
C9 H9 . 0.9300 n
C10 C11 . 1.392(2) n
C10 H10 . 0.9300 n
C11 H11 . 0.9300 n
C12 H12A . 0.9600 n
C12 H12B . 0.9600 n
C12 H12C . 0.9600 n
C12 H12D . 0.9601 n
C12 H12E . 0.9600 n
C12 H12F . 0.9600 n
C13 C14 . 1.3868(19) n
C13 C18 . 1.3925(18) n
C14 C15 . 1.385(2) n
C14 H14 . 0.9300 n
C15 C16 . 1.375(2) n
C15 H15 . 0.9300 n
C16 C17 . 1.373(3) n
C16 H16 . 0.9300 n
C17 C18 . 1.382(2) n
C17 H17 . 0.9300 n
C18 H18 . 0.9300 n
C19 C20 . 1.3821(18) n
C19 C24 . 1.3863(19) n
C20 C21 . 1.399(2) n
C20 H20 . 0.9300 n
C21 C22 . 1.368(3) n
C21 H21 . 0.9300 n
C22 C23 . 1.350(3) n
C22 H22 . 0.9300 n
C23 C24 . 1.381(2) n
C23 H23 . 0.9300 n
C24 H24 . 0.9300 n
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_publ_flag
C5 N1 C2 N3 0.23(14) n
C6 N1 C2 N3 179.47(11) n
C5 N1 C2 C12 -178.35(12) n
C6 N1 C2 C12 0.89(19) n
N1 C2 N3 C4 0.33(14) n
C12 C2 N3 C4 178.89(12) n
C2 N3 C4 C5 -0.78(14) n
C2 N3 C4 C13 174.26(11) n
N3 C4 C5 N1 0.91(13) n
C13 C4 C5 N1 -173.43(12) n
N3 C4 C5 C19 -178.01(12) n
C13 C4 C5 C19 7.7(2) n
C2 N1 C5 C4 -0.69(13) n
C6 N1 C5 C4 -179.92(11) n
C2 N1 C5 C19 178.37(11) n
C6 N1 C5 C19 -0.86(19) n
C2 N1 C6 C7 63.99(17) n
C5 N1 C6 C7 -116.92(14) n
C2 N1 C6 C11 -115.71(15) n
C5 N1 C6 C11 63.38(17) n
C11 C6 C7 C8 1.9(2) n
N1 C6 C7 C8 -177.82(12) n
C6 C7 C8 C9 -1.7(2) n
C7 C8 C9 C10 0.2(3) n
C8 C9 C10 C11 1.2(3) n
C7 C6 C11 C10 -0.6(2) n
N1 C6 C11 C10 179.12(12) n
C9 C10 C11 C6 -1.0(2) n
C5 C4 C13 C14 23.2(2) n
N3 C4 C13 C14 -150.74(13) n
C5 C4 C13 C18 -160.56(14) n
N3 C4 C13 C18 25.55(18) n
C18 C13 C14 C15 0.8(2) n
C4 C13 C14 C15 177.19(14) n
C13 C14 C15 C16 -0.9(3) n
C14 C15 C16 C17 0.4(3) n
C15 C16 C17 C18 0.1(3) n
C16 C17 C18 C13 -0.1(3) n
C14 C13 C18 C17 -0.4(2) n
C4 C13 C18 C17 -176.84(14) n
C4 C5 C19 C20 -121.98(16) n
N1 C5 C19 C20 59.26(17) n
C4 C5 C19 C24 58.3(2) n
N1 C5 C19 C24 -120.45(14) n
C24 C19 C20 C21 0.2(2) n
C5 C19 C20 C21 -179.56(13) n
C19 C20 C21 C22 -0.5(2) n
C20 C21 C22 C23 0.1(3) n
C21 C22 C23 C24 0.5(3) n
C22 C23 C24 C19 -0.9(3) n
C20 C19 C24 C23 0.5(2) n
C5 C19 C24 C23 -179.78(14) n
