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#$Date: 2018-10-25 05:48:53 +0300 (Thu, 25 Oct 2018) $
#$Revision: 211629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021313.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_2021313
loop_
_publ_author_name
'Macías, Mario A.'
'Elejalde, Nerith-Rocio'
'Butassi, Estefanía'
'Zacchino, Susana'
'Portilla, Jaime'
_publ_section_title
;
 Studies via X-ray analysis on intermolecular interactions and
 energy frameworks based on the effects of substituents of three
 4-aryl-2-methyl-1H-imidazoles of different electronic nature and
 their in vitro antifungal evaluation
;
_journal_coeditor_code           CU3134
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618014109
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C10 H10 N2'
_chemical_formula_moiety         'C10 H10 N2'
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20
_chemical_name_systematic
;
2-Methyl-4-phenyl-1H-imidazole
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   29.196(4)
_cell_length_b                   29.196(4)
_cell_length_c                   5.4212(10)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.3780
_cell_measurement_theta_min      3.6820
_cell_volume                     4002.0(11)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
PLATON (Spek, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source
diffractometer with an Atlas
detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            26163
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.656
_diffrn_reflns_theta_min         3.693
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.154
_refine_ls_extinction_coef       0.0037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2016/6 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0813P)²+4.7247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                1204
_reflns_number_total             1684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cu3134sup1.cif
_cod_data_source_block           3a
_cod_original_cell_volume        4002.0(15)
_cod_database_code               2021313
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x+y, -z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'-y, x-y, z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
N N1 0.37637(8) 0.52807(8) 0.2334(4) 0.0611(6) Uani d 1
H H1 0.342851 0.506392 0.228755 0.073 Uiso calc 1
C C2 0.41220(9) 0.52466(9) 0.3885(5) 0.0574(7) Uani d 1
C C3 0.39702(9) 0.48283(9) 0.5727(4) 0.0575(7) Uani d 1
C C4 0.43513(12) 0.48439(12) 0.7313(5) 0.0791(9) Uani d 1
H H4 0.469997 0.511551 0.715987 0.095 Uiso calc 1
C C5 0.42230(14) 0.44658(14) 0.9105(6) 0.0885(10) Uani d 1
H H5 0.448488 0.448290 1.014161 0.106 Uiso calc 1
C C6 0.37103(13) 0.40632(12) 0.9372(5) 0.0765(8) Uani d 1
H H6 0.362301 0.381106 1.060336 0.092 Uiso calc 1
C C7 0.33288(11) 0.40354(11) 0.7814(5) 0.0722(8) Uani d 1
H H7 0.298198 0.376028 0.797580 0.087 Uiso calc 1
C C8 0.34546(10) 0.44133(10) 0.5999(5) 0.0655(7) Uani d 1
H H8 0.319143 0.438925 0.494990 0.079 Uiso calc 1
C C9 0.45979(11) 0.56739(11) 0.3292(6) 0.0737(8) Uani d 1
H H9 0.491684 0.575792 0.404289 0.088 Uiso calc 1
N N10 0.45442(9) 0.59640(9) 0.1440(5) 0.0783(8) Uani d 1
C C11 0.40323(11) 0.57134(10) 0.0910(5) 0.0682(8) Uani d 1
C C12 0.37762(15) 0.58749(14) -0.0996(6) 0.0941(10) Uani d 1
H H12A 0.389955 0.584686 -0.259961 0.141 Uiso calc 1
H H12B 0.386383 0.623422 -0.070974 0.141 Uiso calc 1
H H12C 0.339957 0.564820 -0.091209 0.141 Uiso calc 1
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 N1 C2 108.0(2)
C11 N1 H1 126.0
C2 N1 H1 126.0
C9 C2 N1 104.6(2)
C9 C2 C3 132.0(2)
N1 C2 C3 123.4(2)
C4 C3 C8 117.6(2)
C4 C3 C2 119.4(2)
C8 C3 C2 122.9(2)
C5 C4 C3 121.3(3)
C5 C4 H4 119.4
C3 C4 H4 119.4
C6 C5 C4 120.3(3)
C6 C5 H5 119.8
C4 C5 H5 119.8
C7 C6 C5 119.5(3)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C8 120.5(3)
C6 C7 H7 119.7
C8 C7 H7 119.7
C7 C8 C3 120.7(3)
C7 C8 H8 119.7
C3 C8 H8 119.7
C2 C9 N10 111.0(2)
C2 C9 H9 124.5
N10 C9 H9 124.5
C11 N10 C9 105.2(2)
N10 C11 N1 111.1(2)
N10 C11 C12 125.7(3)
N1 C11 C12 123.2(3)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.348(3)
N1 C2 1.384(3)
N1 H1 0.8600
C2 C9 1.363(4)
C2 C3 1.464(3)
C3 C4 1.389(4)
C3 C8 1.390(3)
C4 C5 1.375(4)
C4 H4 0.9300
C5 C6 1.372(4)
C5 H5 0.9300
C6 C7 1.368(4)
C6 H6 0.9300
C7 C8 1.384(4)
C7 H7 0.9300
C8 H8 0.9300
C9 N10 1.372(4)
C9 H9 0.9300
N10 C11 1.326(4)
C11 C12 1.484(4)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
N1 H1 N10 5_455 0.86 2.04 2.877(3) 162.6
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
C11 N1 C2 C9 0.2(3)
C11 N1 C2 C3 179.0(2)
C9 C2 C3 C4 2.5(4)
N1 C2 C3 C4 -175.9(2)
C9 C2 C3 C8 -178.4(3)
N1 C2 C3 C8 3.2(4)
C8 C3 C4 C5 -0.6(4)
C2 C3 C4 C5 178.5(3)
C3 C4 C5 C6 -0.3(5)
C4 C5 C6 C7 1.1(5)
C5 C6 C7 C8 -0.9(4)
C6 C7 C8 C3 -0.1(4)
C4 C3 C8 C7 0.9(4)
C2 C3 C8 C7 -178.2(2)
N1 C2 C9 N10 -0.3(3)
C3 C2 C9 N10 -179.0(3)
C2 C9 N10 C11 0.3(3)
C9 N10 C11 N1 -0.1(3)
C9 N10 C11 C12 -179.8(3)
C2 N1 C11 N10 -0.1(3)
C2 N1 C11 C12 179.6(3)

_cod_database_fobs_code 2021313
