data_2010527 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 107 _journal_page_last 109 _publ_section_title ; Racemic isopropyl 1,4-dihydro-2,6-dimethyl-3-nitro-4- (6-methyl-2-pyridyl)-pyridine-5-carboxylate hemibenzene solvate ; loop_ _publ_author_name 'Parrish, Jonathan C.' 'Shan, Rudong' 'Knaus, Edward E.' 'James, Michael N. G.' _chemical_formula_moiety 'C17 H21 N3 O4, 0.5C6 H6' _chemical_formula_sum 'C20 H24 N3 O4' _chemical_formula_weight 370.42 _chemical_melting_point '462-463' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9436(6) _cell_length_b 15.1440(11) _cell_length_c 16.3075(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.2083(13) _cell_angle_gamma 90.00 _cell_volume 1917.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _exptl_crystal_density_diffrn 1.283 _diffrn_ambient_temperature 193(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_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 .82201(16) .53883(8) -.04080(8) .0305(3) Uani d . 1 . . N C2 .74440(18) .45837(10) -.04234(9) .0281(3) Uani d . 1 . . C C3 .69611(18) .43084(9) .02875(9) .0272(3) Uani d . 1 . . C C4 .72940(19) .48098(9) .11071(9) .0262(3) Uani d . 1 . . C C5 .80353(19) .57202(9) .09917(9) .0281(3) Uani d . 1 . . C C6 .84404(18) .59662(9) .02617(10) .0293(3) Uani d . 1 . . C N7 1.00486(17) .41198(8) .17727(8) .0329(3) Uani d . 1 . . N C8 .84202(19) .42896(9) .18283(9) .0270(3) Uani d . 1 . . C C9 .7761(2) .40134(11) .25073(10) .0345(4) Uani d . 1 . . C C10 .8807(2) .35444(11) .31458(11) .0372(4) Uani d . 1 . . C C11 1.0469(2) .33625(11) .30856(11) .0379(4) Uani d . 1 . . C C12 1.1061(2) .36582(11) .23976(11) .0390(4) Uani d . 1 . . C H1 .872(2) .5518(11) -.0856(11) .042(5) Uiso d . 1 . . H C21 .7172(2) .41275(13) -.12586(11) .0371(4) Uani d . 1 . . C H21 .595(3) .3994(12) -.1474(12) .051(5) Uiso d . 1 . . H H22 .779(3) .3573(15) -.1221(13) .066(6) Uiso d . 1 . . H H23 .763(3) .4496(14) -.1631(13) .060(6) Uiso d . 1 . . H N31 .59848(17) .35154(8) .02884(8) .0332(3) Uani d . 1 . . N O31 .5829(2) .29810(8) -.02987(8) .0584(4) Uani d . 1 . . O O32 .53097(15) .33836(7) .08920(7) .0394(3) Uani d . 1 . . O H4 .6201(19) .4886(9) .1286(9) .021(4) Uiso d . 1 . . H C51 .8293(2) .63298(10) .17129(10) .0340(4) Uani d . 1 . . C O51 .92116(17) .69786(8) .18058(9) .0536(4) Uani d . 1 . . O O52 .73982(15) .60756(7) .22847(7) .0369(3) Uani d . 1 . . O C52 .7710(3) .65554(12) .30875(11) .0470(5) Uani d . 1 . . C H54 .800(2) .7144(14) .2960(12) .056(6) Uiso d . 1 . . H C53 .9283(3) .61592(14) .36600(14) .0702(7) Uani d . 1 . . C H51 1.0292 .6244 .3412 .105 Uiso calc R 1 . . H H52 .9096 .5526 .3730 .105 Uiso calc R 1 . . H H53 .9477 .6451 .4208 .105 Uiso calc R 1 . . H C54 .6099(3) .64728(14) .34124(13) .0647(6) Uani d . 1 . . C H55 .5142 .6746 .3015 .097 Uiso calc R 1 . . H H56 .6250 .6771 .3956 .097 Uiso calc R 1 . . H H57 .5845 .5847 .3480 .097 Uiso calc R 1 . . H C61 .9013(2) .68701(10) .00459(11) .0395(4) Uani d . 1 . . C H61 .8026 .7193 -.0280 .059 Uiso calc R 1 . . H H62 .9901 .6810 -.0286 .059 Uiso calc R 1 . . H H63 .9485 .7194 .0563 .059 Uiso calc R 1 . . H H9 .653(2) .4149(11) .2517(11) .040(5) Uiso d . 1 . . H H10 .839(2) .3364(11) .3623(11) .041(5) Uiso d . 1 . . H H11 1.125(3) .3052(13) .3520(12) .055(5) Uiso d . 1 . . H C121 1.2871(3) .34766(18) .23127(14) .0746(8) Uani d . 1 . . C H121 1.2858 .3226 .1757 .112 Uiso calc R 1 . . H H122 1.3410 .3056 .2746 .112 Uiso calc R 1 . . H H123 1.3530 .4029 .2379 .112 Uiso calc R 1 . . H C97 -.1339(3) .94261(15) -.00152(15) .0715(7) Uani d . 1 . . C H97 -.2269 .9028 -.0028 .086 Uiso calc R 1 . . H C98 .0215(4) .92562(16) .04835(16) .0730(7) Uani d . 1 . . C C99 .1577(4) .98253(16) .05038(16) .0752(7) Uani d . 1 . . C H98 .028(3) .8737(17) .0844(15) .085(8) Uiso d . 1 . . H H99 .277(3) .9693(16) .0840(16) .089(8) Uiso d . 1 . . 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 N1 .0309(7) .0313(7) .0293(7) .0019(6) .0065(6) .0051(5) C2 .0227(7) .0290(8) .0307(8) .0047(6) .0014(6) .0002(6) C3 .0250(7) .0242(7) .0309(8) .0010(6) .0026(6) -.0018(6) C4 .0257(7) .0243(7) .0290(8) .0006(6) .0071(6) -.0018(6) C5 .0261(7) .0226(7) .0344(9) .0021(6) .0041(6) -.0002(6) C6 .0250(8) .0249(7) .0364(9) .0037(6) .0032(7) .0024(6) N7 .0319(7) .0359(7) .0311(7) .0061(6) .0071(6) .0071(6) C8 .0297(8) .0222(7) .0282(8) -.0022(6) .0043(6) -.0027(6) C9 .0343(9) .0374(9) .0331(9) -.0053(7) .0097(7) -.0009(7) C10 .0479(10) .0353(9) .0292(9) -.0108(8) .0101(8) .0023(7) C11 .0456(10) .0330(9) .0324(9) .0024(7) .0026(8) .0073(7) C12 .0380(9) .0420(10) .0355(9) .0086(8) .0042(7) .0077(7) C21 .0357(10) .0444(10) .0305(9) -.0009(8) .0051(8) -.0042(8) N31 .0353(7) .0296(7) .0333(8) -.0025(6) .0042(6) -.0020(6) O31 .0911(11) .0418(7) .0465(8) -.0254(7) .0241(7) -.0209(6) O32 .0416(7) .0400(7) .0380(7) -.0110(5) .0119(6) -.0010(5) C51 .0302(8) .0276(8) .0429(10) .0037(7) .0046(7) -.0027(7) O51 .0536(8) .0415(7) .0688(9) -.0173(6) .0196(7) -.0225(6) O52 .0477(7) .0311(6) .0317(6) .0003(5) .0076(5) -.0057(5) C52 .0739(14) .0305(9) .0336(10) .0060(9) .0046(9) -.0072(7) C53 .0929(17) .0529(12) .0504(13) .0159(12) -.0177(12) -.0113(10) C54 .0973(17) .0575(13) .0461(12) .0123(12) .0303(12) -.0037(10) C61 .0407(9) .0291(8) .0483(10) .0004(7) .0087(8) .0068(7) C121 .0480(12) .120(2) .0576(14) .0380(13) .0162(11) .0396(13) C97 .0826(17) .0581(14) .0688(16) -.0093(12) .0048(13) -.0037(12) C98 .098(2) .0479(13) .0611(15) -.0027(13) -.0102(14) .0046(11) C99 .0777(17) .0568(14) .0779(17) .0016(13) -.0134(14) -.0004(12) 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 . 1.3634(19) yes C2 C3 . 1.361(2) yes C3 C4 . 1.511(2) yes C4 C5 . 1.5263(19) yes C5 C6 . 1.350(2) yes C6 N1 . 1.381(2) yes C3 N31 . 1.4297(19) yes N31 O31 . 1.2397(17) yes N31 O32 . 1.2327(17) yes N1 H1 . .923(18) no C2 C21 . 1.502(2) no C4 C8 . 1.536(2) no C4 H4 . .980(15) no C5 C51 . 1.475(2) no C6 C61 . 1.507(2) no N7 C8 . 1.3406(19) no N7 C12 . 1.352(2) no C8 C9 . 1.386(2) no C9 C10 . 1.383(2) no C9 H9 . 1.000(18) no C10 C11 . 1.373(3) no C10 H10 . .949(18) no C11 C12 . 1.380(2) no C11 H11 . .96(2) no C12 C121 . 1.499(3) no C21 H21 . .98(2) no C21 H22 . .97(2) no C21 H23 . .95(2) no C51 O51 . 1.2139(18) no C51 O52 . 1.3430(19) no O52 C52 . 1.472(2) no C52 C54 . 1.490(3) no C52 C53 . 1.516(3) no C52 H54 . .95(2) no C53 H51 . .9800 no C53 H52 . .9800 no C53 H53 . .9800 no C54 H55 . .9800 no C54 H56 . .9800 no C54 H57 . .9800 no C61 H61 . .9800 no C61 H62 . .9800 no C61 H63 . .9800 no C121 H121 . .9800 no C121 H122 . .9800 no C121 H123 . .9800 no C97 C98 . 1.352(3) no C97 C99 3_575 1.376(3) no C97 H97 . .9500 no C98 C99 . 1.378(3) no C98 H98 . .98(3) no C99 C97 3_575 1.375(3) no C99 H99 . 1.01(3) no