#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200899.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2200899 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2002 _journal_volume 58 _journal_page_first o338 _journal_page_last o340 _publ_section_title ; 4,4'-Methylenediantipyrine monohydrate ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Merz, Klaus' _chemical_formula_moiety 'C23 H24 N4 O2, H2 O' _chemical_formula_sum 'C23 H26 N4 O3' _chemical_formula_iupac 'C23 H24 N4 O2, H2 O' _chemical_formula_weight 406.48 _symmetry_cell_setting monoclinic 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 11.937(3) _cell_length_b 14.740(4) _cell_length_c 12.085(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.436(5) _cell_angle_gamma 90.00 _cell_volume 2124.4(10) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _exptl_crystal_density_diffrn 1.271 _diffrn_ambient_temperature 203(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 O1 .70112(12) .61762(9) .36296(11) .0475(4) Uani d . 1 . . O C1 .83082(13) .36051(11) .88481(14) .0314(4) Uani d . 1 . . C N1 .70776(12) .40512(10) .72856(13) .0393(4) Uani d . 1 . . N O2 .96615(10) .50286(9) .78919(11) .0445(3) Uani d . 1 . . O N2 .79887(12) .42539(9) .80164(12) .0354(4) Uani d . 1 . . N C2 .80865(15) .26890(12) .86868(15) .0377(4) Uani d . 1 . . C H2A .7725 .2488 .8026 .045 Uiso calc R 1 . . H H26 .786(3) .525(2) .310(3) .105(10) Uiso d . 1 . . H H27 .892(3) .482(2) .262(2) .097(10) Uiso d . 1 . . H N3 .74879(13) .79490(9) .54638(12) .0373(4) Uani d . 1 . . N C3 .84015(17) .20756(12) .95055(17) .0450(5) Uani d . 1 . . C H3A .8250 .1455 .9401 .054 Uiso calc R 1 . . H O3 .81822(14) .46905(10) .28413(14) .0571(4) Uani d . 1 . . O N4 .70539(12) .75850(9) .44667(12) .0357(4) Uani d . 1 . . N C4 .89373(17) .23663(13) 1.04763(17) .0481(5) Uani d . 1 . . C H4A .9146 .1946 1.1032 .058 Uiso calc R 1 . . H C5 .91646(17) .32759(13) 1.06275(16) .0458(5) Uani d . 1 . . C H5A .9536 .3473 1.1286 .055 Uiso calc R 1 . . H C6 .88513(15) .38982(11) .98195(15) .0377(4) Uani d . 1 . . C H6A .9005 .4518 .9927 .045 Uiso calc R 1 . . H C7 .87284(14) .48218(11) .74848(14) .0315(4) Uani d . 1 . . C C8 .81876(14) .50457(11) .64333(14) .0323(4) Uani d . 1 . . C C9 .72036(14) .45879(12) .63677(15) .0372(4) Uani d . 1 . . C C10 .63024(18) .45903(17) .54749(19) .0580(6) Uani d . 1 . . C H10A .5648 .4902 .5734 .087 Uiso calc R 1 . . H H10B .6105 .3970 .5281 .087 Uiso calc R 1 . . H H10C .6569 .4900 .4828 .087 Uiso calc R 1 . . H C11 .59944(17) .39928(17) .7809(2) .0602(6) Uani d . 1 . . C H11A .5412 .3850 .7252 .090 Uiso calc R 1 . . H H11B .5828 .4569 .8152 .090 Uiso calc R 1 . . H H11C .6026 .3521 .8368 .090 Uiso calc R 1 . . H C12 .87121(14) .56322(12) .55738(15) .0355(4) Uani d . 1 . . C H12A .9487 .5763 .5823 .043 Uiso calc R 1 . . H H12B .8739 .5285 .4884 .043 Uiso calc R 1 . . H C13 .81259(14) .65181(11) .53251(14) .0317(4) Uani d . 1 . . C C14 .82012(14) .73021(11) .59169(14) .0343(4) Uani d . 1 . . C C15 .73695(14) .66817(11) .43858(14) .0343(4) Uani d . 1 . . C C16 .89230(17) .75129(14) .69192(17) .0479(5) Uani d . 1 . . C H16A .9238 .6955 .7224 .072 Uiso calc R 1 . . H H16B .8476 .7806 .7468 .072 Uiso calc R 1 . . H H16C .9525 .7915 .6719 .072 Uiso calc R 1 . . H C17 .7821(2) .89059(13) .5405(2) .0649(7) Uani d . 1 . . C H17A .8062 .9116 .6138 .097 Uiso calc R 1 . . H H17B .7188 .9266 .5131 .097 Uiso calc R 1 . . H H17C .8433 .8968 .4908 .097 Uiso calc R 1 . . H C18 .60641(14) .79685(11) .39530(15) .0366(4) Uani d . 1 . . C C19 .59687(19) .80375(17) .28303(18) .0590(6) Uani d . 1 . . C H19A .6553 .7837 .2394 .071 Uiso calc R 1 . . H C20 .5007(2) .84037(19) .2336(2) .0757(8) Uani d . 1 . . C H20A .4944 .8451 .1560 .091 Uiso calc R 1 . . H C21 .4151(2) .86964(16) .2948(3) .0729(8) Uani d . 1 . . C H21A .3497 .8941 .2605 .087 Uiso calc R 1 . . H C22 .4261(2) .8627(3) .4063(3) .1027(12) Uani d . 1 . . C H22A .3676 .8830 .4498 .123 Uiso calc R 1 . . H C23 .5213(2) .8264(2) .4576(2) .0856(9) Uani d . 1 . . C H23A .5274 .8220 .5353 .103 Uiso calc R 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 O1 .0611(9) .0396(7) .0405(8) .0122(6) -.0125(6) -.0073(6) C1 .0288(8) .0305(8) .0347(9) .0002(6) -.0004(7) .0033(7) N1 .0279(8) .0447(8) .0445(9) -.0063(6) -.0085(6) .0096(7) O2 .0381(7) .0479(7) .0464(8) -.0139(6) -.0113(6) .0077(6) N2 .0313(8) .0359(8) .0384(9) -.0048(6) -.0077(6) .0070(6) C2 .0394(10) .0357(9) .0377(10) -.0077(7) -.0015(8) -.0024(8) N3 .0418(8) .0322(7) .0375(9) .0033(6) -.0006(7) -.0025(6) C3 .0537(12) .0288(9) .0523(12) -.0051(8) .0020(9) .0042(8) O3 .0508(9) .0428(8) .0784(11) -.0049(7) .0103(8) -.0080(8) N4 .0399(8) .0340(7) .0330(8) .0082(6) -.0018(6) .0012(6) C4 .0583(12) .0406(10) .0448(12) .0033(9) -.0048(9) .0131(9) C5 .0551(12) .0451(11) .0361(10) -.0010(9) -.0113(9) .0002(8) C6 .0422(10) .0301(8) .0403(10) .0005(7) -.0053(8) -.0017(7) C7 .0305(9) .0274(8) .0361(10) -.0016(6) -.0033(7) .0008(7) C8 .0318(9) .0290(8) .0358(10) .0046(7) -.0019(7) .0020(7) C9 .0321(9) .0387(9) .0402(10) .0031(7) -.0070(7) .0050(8) C10 .0400(11) .0754(15) .0568(14) -.0049(10) -.0184(10) .0157(11) C11 .0328(11) .0800(16) .0675(15) -.0063(10) -.0016(10) .0243(12) C12 .0329(9) .0376(9) .0358(10) .0063(7) -.0001(7) .0040(7) C13 .0304(9) .0344(9) .0306(9) .0022(7) .0048(7) .0043(7) C14 .0316(9) .0382(9) .0331(10) -.0005(7) .0034(7) .0043(7) C15 .0365(9) .0331(9) .0335(10) .0060(7) .0031(7) .0015(7) C16 .0466(11) .0521(11) .0443(12) -.0015(9) -.0061(9) -.0039(9) C17 .0802(16) .0326(10) .0801(17) .0009(10) -.0182(13) -.0016(10) C18 .0336(9) .0321(9) .0441(11) .0054(7) .0017(8) .0064(8) C19 .0551(13) .0754(15) .0463(13) .0222(11) -.0005(10) .0074(11) C20 .0814(18) .0794(17) .0635(16) .0205(14) -.0292(14) .0071(13) C21 .0485(14) .0529(13) .115(2) .0122(11) -.0278(14) .0032(14) C22 .0581(17) .146(3) .106(3) .0536(19) .0194(16) .025(2) C23 .0655(16) .130(2) .0626(16) .0497(16) .0213(13) .0251(16) 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 C15 . 1.241(2) yes C1 C6 . 1.386(2) no C1 C2 . 1.388(2) no C1 N2 . 1.427(2) yes N1 C9 . 1.376(2) yes N1 N2 . 1.404(2) yes N1 C11 . 1.466(3) yes O2 C7 . 1.237(2) yes N2 C7 . 1.393(2) yes C2 C3 . 1.381(3) no C2 H2A . .9400 no N3 C14 . 1.376(2) yes N3 N4 . 1.398(2) yes N3 C17 . 1.468(2) yes C3 C4 . 1.380(3) no C3 H3A . .9400 no O3 H26 . .96(3) yes O3 H27 . .96(3) yes N4 C15 . 1.388(2) yes N4 C18 . 1.428(2) yes C4 C5 . 1.379(3) no C4 H4A . .9400 no C5 C6 . 1.380(3) no C5 H5A . .9400 no C6 H6A . .9400 no C7 C8 . 1.439(2) yes C8 C9 . 1.354(2) yes C8 C12 . 1.508(2) yes C9 C10 . 1.491(3) yes C10 H10A . .9700 no C10 H10B . .9700 no C10 H10C . .9700 no C11 H11A . .9700 no C11 H11B . .9700 no C11 H11C . .9700 no C12 C13 . 1.506(2) yes C12 H12A . .9800 no C12 H12B . .9800 no C13 C14 . 1.360(2) yes C13 C15 . 1.440(2) yes C14 C16 . 1.489(3) yes C16 H16A . .9700 no C16 H16B . .9700 no C16 H16C . .9700 no C17 H17A . .9700 no C17 H17B . .9700 no C17 H17C . .9700 no C18 C19 . 1.361(3) no C18 C23 . 1.362(3) no C19 C20 . 1.381(3) no C19 H19A . .9400 no C20 C21 . 1.357(4) no C20 H20A . .9400 no C21 C22 . 1.353(4) no C21 H21A . .9400 no C22 C23 . 1.379(4) no C22 H22A . .9400 no C23 H23A . .9400 no