#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011155.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_2011155
loop_
_publ_author_name
'Inouye, Yoshinobu'
'Sakaino, Yoshiko'
_publ_section_title
;
 Red, orange and yellow crystals of
 4,5-bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              884
_journal_page_last               887
_journal_paper_doi               10.1107/S0108270100005205
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C23 H19 N3 O4, 0.5C4 H8 O2'
_chemical_formula_sum            'C25 H23 N3 O5'
_chemical_formula_weight         445.46
_chemical_name_systematic
' 4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole 0.5-dioxane solvate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                104.651(13)
_cell_angle_beta                 92.624(15)
_cell_angle_gamma                85.83(2)
_cell_formula_units_Z            2
_cell_length_a                   9.510(2)
_cell_length_b                   13.236(4)
_cell_length_c                   9.168(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.78
_cell_measurement_theta_min      11.40
_cell_volume                     1113.1(5)
_computing_cell_refinement       'CAD4 Software'
_computing_data_collection       'CAD4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0397
_diffrn_reflns_av_sigmaI/netI    .0341
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7159
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        .9
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      1.32(2)
_exptl_crystal_density_method    flotation
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .10
_refine_diff_density_max         .243
_refine_diff_density_min         -.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.002
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         6768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_restrained_S_obs      1.061
_refine_ls_R_factor_all          .1035
_refine_ls_R_factor_gt           .0535
_refine_ls_shift/esd_mean        .000
_refine_ls_shift/su_max          0.001>
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0793P)²+0.2048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .1688
_refine_ls_wR_factor_ref         .1386
_reflns_number_gt                4190
_reflns_number_total             6768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            oa1099.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.2048P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0793P)^2^+0.2048P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2011155
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 .7080(2) .03857(14) .3587(3) .1119(7) Uani d . 1 . O
O2A .5404(15) -.0670(8) .3366(11) .116(3) Uani d P .50 1 O
O2B .5732(15) -.0837(8) .2657(11) .116(3) Uani d P .50 2 O
N3 .5937(2) .00989(14) .3067(3) .0902(6) Uani d . 1 . N
C4 .4992(2) .08102(13) .2424(2) .0604(5) Uani d . 1 . C
C5 .5297(2) .18459(13) .2704(2) .0510(4) Uani d . 1 . C
H5 .609(2) .2083(16) .335(2) .065(6) Uiso d . 1 . H
C6 .4412(2) .25230(12) .2098(2) .0455(3) Uani d . 1 . C
C7 .3250(2) .2123(2) .1225(3) .0690(5) Uani d . 1 . C
H7 .262(2) .2562(18) .083(3) .077(7) Uiso d . 1 . H
C8 .2966(3) .1084(2) .0973(3) .0852(7) Uani d . 1 . C
H8 .213(3) .0828(19) .036(3) .090(7) Uiso d . 1 . H
C9 .3838(2) .0413(2) .1580(3) .0769(6) Uani d . 1 . C
H9 .365(3) -.032(2) .137(3) .094(8) Uiso d . 1 . H
C10 .4703(2) .36281(11) .2414(2) .0416(3) Uani d . 1 . C
N11 .38083(15) .43603(10) .19920(15) .0442(3) Uani d . 1 . N
H11 .291(2) .4287(16) .155(2) .069(6) Uiso d . 1 . H
C12 .4389(2) .53124(11) .2493(2) .0421(3) Uani d . 1 . C
C13 .5659(2) .51096(11) .3184(2) .0414(3) Uani d . 1 . C
N14 .58447(13) .40494(9) .31231(14) .0423(3) Uani d . 1 . N
C15 .3609(2) .62678(12) .2255(2) .0424(3) Uani d . 1 . C
C16 .3551(2) .64835(13) .0846(2) .0494(4) Uani d . 1 . C
H16 .405(2) .6005(15) .002(2) .059(5) Uiso d . 1 . H
C17 .2781(2) .73542(14) .0611(2) .0553(4) Uani d . 1 . C
H17 .274(2) .7472(16) -.036(3) .071(6) Uiso d . 1 . H
C18 .2027(2) .80105(12) .1769(2) .0539(4) Uani d . 1 . C
C19 .2081(2) .78107(14) .3177(2) .0637(5) Uani d . 1 . C
H19 .163(3) .8215(19) .400(3) .084(7) Uiso d . 1 . H
C20 .2873(2) .69429(14) .3411(2) .0582(4) Uani d . 1 . C
H20 .297(2) .6793(18) .440(3) .083(7) Uiso d . 1 . H
O21 .1243(2) .88230(10) .1396(2) .0784(4) Uani d . 1 . O
C22 .0398(3) .9485(2) .2532(4) .1234(12) Uani d . 1 . C
H22A -.0121 1.0007 .2127 .185 Uiso calc R 1 . H
H22B .0991 .9820 .3363 .185 Uiso calc R 1 . H
H22C -.0249 .9077 .2874 .185 Uiso calc R 1 . H
C23 .6719(2) .58377(11) .3930(2) .0414(3) Uani d . 1 . C
C24 .6705(2) .68699(13) .3784(2) .0501(4) Uani d . 1 . C
H24 .600(2) .7104(15) .319(2) .062(5) Uiso d . 1 . H
C25 .7702(2) .75407(13) .4518(2) .0540(4) Uani d . 1 . C
H25 .766(2) .8269(16) .445(2) .061(5) Uiso d . 1 . H
C26 .8754(2) .72057(12) .5419(2) .0477(4) Uani d . 1 . C
C27 .8801(2) .61901(13) .5569(2) .0494(4) Uani d . 1 . C
H27 .953(2) .5911(15) .617(2) .060(5) Uiso d . 1 . H
C28 .7787(2) .55205(12) .4828(2) .0457(3) Uani d . 1 . C
H28 .7852(17) .4802(13) .4924(18) .045(4) Uiso d . 1 . H
O29 .96917(14) .79261(10) .6114(2) .0637(3) Uani d . 1 . O
C30 1.0656(2) .7656(2) .7200(3) .0707(6) Uani d . 1 . C
H30A 1.1219 .8237 .7636 .106 Uiso calc R 1 . H
H30B 1.1258 .7062 .6722 .106 Uiso calc R 1 . H
H30C 1.0145 .7487 .7976 .106 Uiso calc R 1 . H
O31 .09737(14) .44547(11) .07708(14) .0645(4) Uani d . 1 . O
C32 .0583(3) .4035(2) -.0768(2) .0692(5) Uani d . 1 . C
H32A -.027(3) .359(2) -.089(3) .118(10) Uiso d . 1 . H
H32B .147(3) .362(2) -.126(3) .095(8) Uiso d . 1 . H
C33 -.0156(3) .5123(2) .1526(2) .0777(7) Uani d . 1 . C
H33A .014(3) .543(2) .251(3) .094(8) Uiso d . 1 . H
H33B -.112(4) .468(3) .142(4) .129(11) Uiso d . 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O1 N3 O2B . . 120.5(7)
O1 N3 O2A . . 121.8(7)
O1 N3 C4 . . 118.8(2)
O2B N3 C4 . . 117.0(7)
O2A N3 C4 . . 117.3(7)
C9 C4 C5 . . 123.1(2)
C9 C4 N3 . . 118.2(2)
C5 C4 N3 . . 118.6(2)
C4 C5 C6 . . 119.0(2)
C4 C5 H5 . . 119.1(12)
C6 C5 H5 . . 121.8(12)
C5 C6 C7 . . 118.2(2)
C5 C6 C10 . . 119.67(15)
C7 C6 C10 . . 122.2(2)
C8 C7 C6 . . 121.5(2)
C8 C7 H7 . . 118.2(14)
C6 C7 H7 . . 120.3(14)
C9 C8 C7 . . 120.4(2)
C9 C8 H8 . . 120.1(14)
C7 C8 H8 . . 119.4(14)
C4 C9 C8 . . 117.8(2)
C4 C9 H9 . . 122.1(15)
C8 C9 H9 . . 120.1(15)
N14 C10 N11 . . 111.26(13)
N14 C10 C6 . . 125.65(13)
N11 C10 C6 . . 123.09(14)
C10 N11 C12 . . 107.83(13)
C10 N11 H11 . . 129.0(13)
C12 N11 H11 . . 122.9(13)
N11 C12 C13 . . 105.52(13)
N11 C12 C15 . . 119.82(14)
C13 C12 C15 . . 134.63(15)
C12 C13 N14 . . 109.75(13)
C12 C13 C23 . . 129.26(13)
N14 C13 C23 . . 120.98(13)
C10 N14 C13 . . 105.61(12)
C20 C15 C16 . . 118.51(15)
C20 C15 C12 . . 120.80(14)
C16 C15 C12 . . 120.64(14)
C17 C16 C15 . . 120.6(2)
C17 C16 H16 . . 120.2(11)
C15 C16 H16 . . 119.2(11)
C16 C17 C18 . . 120.2(2)
C16 C17 H17 . . 118.9(13)
C18 C17 H17 . . 120.8(13)
O21 C18 C19 . . 124.7(2)
O21 C18 C17 . . 115.5(2)
C19 C18 C17 . . 119.8(2)
C18 C19 C20 . . 119.7(2)
C18 C19 H19 . . 124.8(15)
C20 C19 H19 . . 115.5(15)
C15 C20 C19 . . 121.1(2)
C15 C20 H20 . . 116.9(14)
C19 C20 H20 . . 121.9(14)
C18 O21 C22 . . 117.3(2)
O21 C22 H22A . . 109.5
O21 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
O21 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
C28 C23 C24 . . 117.09(15)
C28 C23 C13 . . 120.21(13)
C24 C23 C13 . . 122.70(14)
C25 C24 C23 . . 121.4(2)
C25 C24 H24 . . 119.8(12)
C23 C24 H24 . . 118.9(12)
C24 C25 C26 . . 120.4(2)
C24 C25 H25 . . 120.9(12)
C26 C25 H25 . . 118.7(12)
O29 C26 C27 . . 124.10(15)
O29 C26 C25 . . 116.42(14)
C27 C26 C25 . . 119.5(2)
C26 C27 C28 . . 119.69(15)
C26 C27 H27 . . 122.9(12)
C28 C27 H27 . . 117.4(11)
C23 C28 C27 . . 121.99(14)
C23 C28 H28 . . 119.4(10)
C27 C28 H28 . . 118.6(10)
C26 O29 C30 . . 117.70(14)
O29 C30 H30A . . 109.5
O29 C30 H30B . . 109.5
H30A C30 H30B . . 109.5
O29 C30 H30C . . 109.5
H30A C30 H30C . . 109.5
H30B C30 H30C . . 109.5
C32 O31 C33 . . 110.0(2)
O31 C32 C33 . 2_565 111.2(2)
O31 C32 H32A . . 112.2(17)
C33 C32 H32A 2_565 . 105.2(16)
O31 C32 H32B . . 105.7(14)
C33 C32 H32B 2_565 . 109.8(14)
H32A C32 H32B . . 113(2)
O31 C33 C32 . 2_565 111.3(2)
O31 C33 H33A . . 108.9(16)
C32 C33 H33A 2_565 . 108.3(16)
O31 C33 H33B . . 109.8(17)
C32 C33 H33B 2_565 . 103.3(16)
H33A C33 H33B . . 115(2)
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
O1 N3 . 1.213(3) ?
O2A N3 . 1.264(11) ?
O2B N3 . 1.228(11) ?
N3 C4 . 1.467(3) ?
C4 C9 . 1.371(3) ?
C4 C5 . 1.379(2) ?
C5 C6 . 1.386(2) ?
C5 H5 . .96(2) ?
C6 C7 . 1.390(3) ?
C6 C10 . 1.462(2) ?
C7 C8 . 1.380(3) ?
C7 H7 . .93(2) ?
C8 C9 . 1.373(3) ?
C8 H8 . .98(3) ?
C9 H9 . .97(3) ?
C10 N14 . 1.323(2) ?
C10 N11 . 1.361(2) ?
N11 C12 . 1.374(2) ?
N11 H11 . .93(2) ?
C12 C13 . 1.379(2) ?
C12 C15 . 1.478(2) ?
C13 N14 . 1.389(2) ?
C13 C23 . 1.469(2) ?
C15 C20 . 1.382(2) ?
C15 C16 . 1.390(2) ?
C16 C17 . 1.378(2) ?
C16 H16 . .98(2) ?
C17 C18 . 1.381(3) ?
C17 H17 . .94(2) ?
C18 O21 . 1.370(2) ?
C18 C19 . 1.379(3) ?
C19 C20 . 1.385(3) ?
C19 H19 . .91(2) ?
C20 H20 . .97(2) ?
O21 C22 . 1.418(3) ?
C22 H22A . .96 ?
C22 H22B . .96 ?
C22 H22C . .96 ?
C23 C28 . 1.387(2) ?
C23 C24 . 1.405(2) ?
C24 C25 . 1.379(3) ?
C24 H24 . .93(2) ?
C25 C26 . 1.387(2) ?
C25 H25 . .98(2) ?
C26 O29 . 1.369(2) ?
C26 C27 . 1.383(2) ?
C27 C28 . 1.391(2) ?
C27 H27 . .97(2) ?
C28 H28 . .97(2) ?
O29 C30 . 1.417(2) ?
C30 H30A . .96 ?
C30 H30B . .96 ?
C30 H30C . .96 ?
O31 C32 . 1.422(2) ?
O31 C33 . 1.427(3) ?
C32 C33 2_565 1.480(3) ?
C32 H32A . 1.02(3) ?
C32 H32B . 1.03(3) ?
C33 C32 2_565 1.480(3) ?
C33 H33A . .93(3) ?
C33 H33B . 1.11(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N11 H11 O31 .93(2) 1.96(2) 2.878(2) 168(2) yes
