data_2011156
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  884
_journal_page_last  887
_publ_section_title
;
Red, orange, and yellow crystals of
4,5-bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole
;
loop_
_publ_author_name
  'Inouye, Yoshinobu'
  'Sakaino, Yoshiko'
_chemical_formula_moiety  'C23 H19 N3 O4, C6 H6'
_chemical_formula_sum  'C29 H25 N3 O4'
_chemical_formula_weight  479.52
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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'
_cell_length_a  9.614(2)
_cell_length_b  29.011(5)
_cell_length_c  8.984(2)
_cell_angle_alpha  90.00
_cell_angle_beta  91.933(10)
_cell_angle_gamma  90.00
_cell_volume  2504.3(9)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.272
_exptl_crystal_density_meas  1.25(2)
_diffrn_ambient_temperature  293(2)
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 1.2600(4)  .29055(13)  .4503(4)  .1100(13) Uani d . 1 . O
  O2 1.3138(4)  .36117(12)  .4164(4)  .1102(12) Uani d . 1 . O
  N3 1.2496(3)  .32663(13)  .3815(4)  .0727(9) Uani d . 1 . N
  C4 1.1534(3)  .32837(12)  .2514(4)  .0533(8) Uani d . 1 . C
  C5 1.0837(3)  .28899(12)  .2090(3)  .0454(7) Uani d . 1 . C
  H5 1.102(4)  .2602(11)  .258(4)  .054(9) Uiso d . 1 . H
  C6  .9888(3)  .29083(10)  .0887(3)  .0413(6) Uani d . 1 . C
  C7  .9691(4)  .33270(12)  .0139(4)  .0539(8) Uani d . 1 . C
  H7  .901(4)  .3347(12)  -.070(5)  .069(11) Uiso d . 1 . H
  C8 1.0433(4)  .37141(14)  .0580(4)  .0649(9) Uani d . 1 . C
  H8 1.027(4)  .4000(14)  .005(4)  .071(11) Uiso d . 1 . H
  C9 1.1361(4)  .37001(14)  .1781(4)  .0645(10) Uani d . 1 . C
  H9 1.177(4)  .3962(12)  .209(4)  .053(9) Uiso d . 1 . H
  C10  .9088(3)  .25018(10)  .0449(3)  .0403(6) Uani d . 1 . C
  N11  .8322(2)  .24673(9)  -.0847(2)  .0411(5) Uani d . 1 . N
  H11  .844(4)  .2666(12)  -.164(4)  .055(9) Uiso d . 1 . H
  C12  .7682(3)  .20464(10)  -.0883(3)  .0402(6) Uani d . 1 . C
  C13  .8078(3)  .18359(10)  .0449(3)  .0414(6) Uani d . 1 . C
  N14  .8952(2)  .21240(8)  .1267(2)  .0425(6) Uani d . 1 . N
  C15  .6785(3)  .19088(10)  -.2162(3)  .0420(6) Uani d . 1 . C
  C16  .5968(3)  .22335(11)  -.2910(3)  .0483(7) Uani d . 1 . C
  H16  .596(4)  .2571(11)  -.258(4)  .053(9) Uiso d . 1 . H
  C17  .5112(3)  .21159(13)  -.4142(3)  .0538(8) Uani d . 1 . C
  H17  .462(4)  .2368(14)  -.468(5)  .076(12) Uiso d . 1 . H
  C18  .5089(3)  .16645(13)  -.4624(3)  .0567(8) Uani d . 1 . C
  C19  .5909(4)  .13363(14)  -.3909(4)  .0644(9) Uani d . 1 . C
  H19  .588(4)  .1021(15)  -.426(5)  .081(12) Uiso d . 1 . H
  C20  .6745(4)  .14554(12)  -.2687(4)  .0549(8) Uani d . 1 . C
  H20  .734(4)  .1217(12)  -.219(4)  .054(9) Uiso d . 1 . H
  O21  .4266(3)  .15068(10)  -.5796(3)  .0805(8) Uani d . 1 . O
  C22  .3376(5)  .1824(2)  -.6548(5)  .0851(14) Uani d . 1 . C
  H22A  .2713  .1942  -.5870  .128 Uiso calc R 1 . H
  H22B  .2892  .1671  -.7360  .128 Uiso calc R 1 . H
  H22C  .3916  .2073  -.6927  .128 Uiso calc R 1 . H
  C23  .7713(3)  .13789(10)  .1029(3)  .0422(6) Uani d . 1 . C
  C24  .6373(3)  .12022(12)  .0922(4)  .0541(8) Uani d . 1 . C
  H24  .565(4)  .1382(12)  .044(4)  .064(10) Uiso d . 1 . H
  C25  .6075(4)  .07666(14)  .1436(4)  .0613(9) Uani d . 1 . C
  H25  .514(4)  .0669(12)  .134(4)  .064(10) Uiso d . 1 . H
  C26  .7108(3)  .04969(11)  .2081(3)  .0518(7) Uani d . 1 . C
  C27  .8447(3)  .06687(12)  .2235(4)  .0545(8) Uani d . 1 . C
  H27  .918(3)  .0473(11)  .266(4)  .047(8) Uiso d . 1 . H
  C28  .8743(3)  .11028(12)  .1707(3)  .0495(7) Uani d . 1 . C
  H28  .971(4)  .1197(12)  .181(4)  .063(10) Uiso d . 1 . H
  O29  .6941(3)  .00510(9)  .2561(3)  .0725(8) Uani d . 1 . O
  C30  .5607(5)  -.0154(2)  .2366(8)  .113(2) Uani d . 1 . C
  H30A  .5655  -.0472  .2658  .169 Uiso calc R 1 . H
  H30B  .5308  -.0133  .1338  .169 Uiso calc R 1 . H
  H30C  .4956  .0005  .2969  .169 Uiso calc R 1 . H
  C31A  .7978(6)  .5126(3)  .1027(3)  .078(2) Uani d PG  .70 1 C
  H31A  .7901  .5106  -.0006  .093 Uiso calc PR  .70 1 H
  C32A  .7641(5)  .5535(2)  .1737(9)  .072(2) Uani d PG  .70 1 C
  H32A  .7340  .5788  .1179  .086 Uiso calc PR  .70 1 H
  C33A  .7755(6)  .5565(2)  .3280(10)  .071(2) Uani d PG  .70 1 C
  H33A  .7530  .5838  .3755  .085 Uiso calc PR  .70 1 H
  C34A  .8206(7)  .5186(3)  .4113(3)  .077(2) Uani d PG  .70 1 C
  H34A  .8282  .5207  .5146  .092 Uiso calc PR  .70 1 H
  C35A  .8543(6)  .4778(2)  .3403(10)  .083(2) Uani d PG  .70 1 C
  H35A  .8844  .4524  .3961  .100 Uiso calc PR  .70 1 H
  C36A  .8428(6)  .4747(2)  .1860(10)  .081(2) Uani d PG  .70 1 C
  H36A  .8654  .4474  .1385  .097 Uiso calc PR  .70 1 H
  C31B  .7736(14)  .5330(7)  .1102(14)  .073(5) Uiso d PG  .30 2 C
  H31B  .7484  .5449  .0169  .088 Uiso calc PR  .30 2 H
  C32B  .7578(12)  .5597(3)  .237(3)  .067(5) Uiso d PG  .30 2 C
  H32B  .7220  .5894  .2286  .080 Uiso calc PR  .30 2 H
  C33B  .7954(14)  .5420(6)  .3764(16)  .067(5) Uiso d PG  .30 2 C
  H33B  .7848  .5599  .4612  .081 Uiso calc PR  .30 2 H
  C34B  .8489(13)  .4976(7)  .3889(12)  .063(4) Uiso d PG  .30 2 C
  H34B  .8741  .4858  .4821  .075 Uiso calc PR  .30 2 H
  C35B  .8648(13)  .4709(3)  .262(2)  .075(5) Uiso d PG  .30 2 C
  H35B  .9006  .4412  .2705  .090 Uiso calc PR  .30 2 H
  C36B  .8271(15)  .4887(6)  .1227(15)  .076(5) Uiso d PG  .30 2 C
  H36B  .8377  .4708  .0379  .092 Uiso calc PR  .30 2 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1  .127(3)  .104(3)  .094(2)  -.005(2)  -.068(2)  .004(2)
  O2  .101(2)  .112(3)  .114(3)  -.029(2)  -.051(2)  -.025(2)
  N3  .061(2)  .088(2)  .067(2)  -.004(2)  -.023(2)  -.017(2)
  C4  .045(2)  .066(2)  .048(2)  -.0030(14)  -.0071(13)  -.0109(15)
  C5  .045(2)  .053(2)  .0376(14)  -.0005(13)  -.0066(11)  -.0002(13)
  C6  .0400(14)  .052(2)  .0321(12)  -.0016(12)  -.0019(10)  -.0025(11)
  C7  .055(2)  .061(2)  .044(2)  -.002(2)  -.0086(14)  .0013(14)
  C8  .070(2)  .055(2)  .068(2)  -.006(2)  -.009(2)  .003(2)
  C9  .063(2)  .059(2)  .071(2)  -.012(2)  -.008(2)  -.009(2)
  C10  .0412(14)  .050(2)  .0293(12)  -.0004(12)  -.0023(10)  -.0004(11)
  N11  .0448(12)  .0501(14)  .0280(10)  -.0022(11)  -.0045(9)  -.0002(10)
  C12  .0403(14)  .047(2)  .0332(12)  .0001(12)  -.0011(10)  -.0023(11)
  C13  .0387(13)  .052(2)  .0331(13)  .0006(12)  -.0035(10)  -.0015(12)
  N14  .0460(13)  .0508(14)  .0304(11)  -.0009(10)  -.0052(9)  -.0001(10)
  C15  .0412(14)  .054(2)  .0302(12)  -.0031(12)  -.0031(10)  -.0013(12)
  C16  .051(2)  .051(2)  .0415(15)  -.0017(13)  -.0104(12)  -.0038(13)
  C17  .052(2)  .063(2)  .045(2)  -.004(2)  -.0132(13)  .0015(15)
  C18  .054(2)  .074(2)  .041(2)  -.014(2)  -.0119(13)  -.0091(15)
  C19  .074(2)  .060(2)  .058(2)  -.006(2)  -.011(2)  -.014(2)
  C20  .061(2)  .051(2)  .052(2)  .001(2)  -.0092(15)  -.0066(15)
  O21  .081(2)  .094(2)  .064(2)  -.0130(15)  -.0315(14)  -.0176(14)
  C22  .083(3)  .106(3)  .063(2)  -.030(2)  -.039(2)  .012(2)
  C23  .0439(15)  .049(2)  .0330(13)  .0003(12)  -.0040(11)  -.0019(12)
  C24  .043(2)  .062(2)  .057(2)  .0001(14)  -.0039(14)  .015(2)
  C25  .043(2)  .074(2)  .066(2)  -.008(2)  -.002(2)  .016(2)
  C26  .057(2)  .052(2)  .046(2)  -.0041(14)  -.0023(13)  .0083(13)
  C27  .051(2)  .059(2)  .052(2)  .0038(15)  -.0129(14)  .006(2)
  C28  .044(2)  .057(2)  .046(2)  -.0023(14)  -.0108(13)  .0005(14)
  O29  .070(2)  .065(2)  .082(2)  -.0119(13)  -.0070(13)  .0243(13)
  C30  .083(3)  .085(3)  .169(6)  -.027(3)  -.008(3)  .050(3)
  C31A  .082(4)  .085(5)  .064(4)  .012(4)  -.008(3)  -.006(3)
  C32A  .081(4)  .071(4)  .063(4)  .008(3)  .006(3)  .000(3)
  C33A  .067(3)  .074(4)  .073(5)  -.010(3)  .008(3)  -.004(4)
  C34A  .089(4)  .075(5)  .065(4)  -.010(4)  .004(3)  .001(3)
  C35A  .103(5)  .072(4)  .074(5)  -.007(4)  -.004(4)  .014(4)
  C36A  .095(5)  .063(4)  .084(5)  .004(3)  -.009(4)  -.003(4)
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 . 1.218(5) ?
  O2 N3 . 1.212(4) ?
  N3 C4 . 1.467(4) ?
  C4 C5 . 1.372(4) ?
  C4 C9 . 1.383(5) ?
  C5 C6 . 1.392(4) ?
  C5 H5 .  .95(3) ?
  C6 C7 . 1.398(4) ?
  C6 C10 . 1.455(4) ?
  C7 C8 . 1.381(5) ?
  C7 H7 .  .99(4) ?
  C8 C9 . 1.378(5) ?
  C8 H8 .  .97(4) ?
  C9 H9 .  .89(3) ?
  C10 N14 . 1.328(4) ?
  C10 N11 . 1.361(3) ?
  N11 C12 . 1.367(4) ?
  N11 H11 .  .92(4) ?
  C12 C13 . 1.385(4) ?
  C12 C15 . 1.468(4) ?
  C13 N14 . 1.380(4) ?
  C13 C23 . 1.471(4) ?
  C15 C16 . 1.386(4) ?
  C15 C20 . 1.397(4) ?
  C16 C17 . 1.399(4) ?
  C16 H16 . 1.02(3) ?
  C17 C18 . 1.379(5) ?
  C17 H17 .  .99(4) ?
  C18 O21 . 1.374(4) ?
  C18 C19 . 1.381(5) ?
  C19 C20 . 1.382(5) ?
  C19 H19 .  .97(4) ?
  C20 H20 .  .99(3) ?
  O21 C22 . 1.412(5) ?
  C22 H22A .  .96 ?
  C22 H22B .  .96 ?
  C22 H22C .  .96 ?
  C23 C24 . 1.387(4) ?
  C23 C28 . 1.397(4) ?
  C24 C25 . 1.379(5) ?
  C24 H24 .  .96(4) ?
  C25 C26 . 1.377(5) ?
  C25 H25 .  .94(4) ?
  C26 O29 . 1.375(4) ?
  C26 C27 . 1.383(5) ?
  C27 C28 . 1.379(5) ?
  C27 H27 .  .97(3) ?
  C28 H28 .  .97(4) ?
  O29 C30 . 1.419(5) ?
  C30 H30A .  .96 ?
  C30 H30B .  .96 ?
  C30 H30C .  .96 ?
  C31A C32A . 1.39 ?
  C31A C36A . 1.39 ?
  C31A H31A .  .93 ?
  C32A C33A . 1.39 ?
  C32A H32A .  .93 ?
  C33A C34A . 1.39 ?
  C33A H33A .  .93 ?
  C34A C35A . 1.39 ?
  C34A H34A .  .93 ?
  C35A C36A . 1.39 ?
  C35A H35A .  .93 ?
  C36A H36A .  .93 ?
  C31B C32B . 1.39 ?
  C31B C36B . 1.39 ?
  C31B H31B .  .93 ?
  C32B C33B . 1.39 ?
  C32B H32B .  .93 ?
  C33B C34B . 1.39 ?
  C33B H33B .  .93 ?
  C34B C35B . 1.39 ?
  C34B H34B .  .93 ?
  C35B C36B . 1.39 ?
  C35B H35B .  .93 ?
  C36B H36B .  .93 ?