#------------------------------------------------------------------------------ #$Date: 2008-11-20 20:58:43 +0100 (Thu, 20 Nov 2008) $ #$Revision: 481 $ #$URL: svn://www.crystallography.net/cod/cif/2/2009070.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_2009070 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1999 _journal_volume 55 _publ_section_title ; Methyl (SR)-8,10-dichloro-1,2,3,4,5,6-hexahydro-6-hydroxy-1-methyl- 1,9-phenanthroline-6-carboxylate ; loop_ _publ_author_name 'Sarkar, Tarun Kumar' 'Basak, Sankar' 'Ghosh, Sunil Kumar' 'Nigam, Gur Dayal' 'Razak, Ibrahim Abdul' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' ? _chemical_formula_sum 'C15 H16 Cl2 N2 O3' _chemical_formula_weight 343.20 _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 9.99210(10) _cell_length_b 13.2646(2) _cell_length_c 12.1386(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.4700(10) _cell_angle_gamma 90.00 _cell_volume 1608.81(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.417 _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_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 Cl1 .43218(5) .91832(3) .30303(4) .05230(15) Uani d . 1 . . Cl Cl2 .32579(5) .57368(3) .12787(4) .05663(16) Uani d . 1 . . Cl O1 .67051(10) .73625(8) -.13595(8) .0406(3) Uani d . 1 . . O H1A .7238 .7483 -.1852 .061 Uiso calc R 1 . . H O2 .93475(10) .82297(10) -.04886(11) .0559(3) Uani d . 1 . . O O3 .84768(11) .71866(11) .07601(11) .0579(4) Uani d . 1 . . O N1 .40040(11) .74971(9) .20170(9) .0343(3) Uani d . 1 . . N N2 .70591(13) .99110(10) .22458(10) .0418(3) Uani d . 1 . . N C1 .47829(14) .83148(10) .20314(11) .0322(3) Uani d . 1 . . C C2 .42333(13) .68221(10) .12405(11) .0337(3) Uani d . 1 . . C C3 .51657(13) .69385(10) .04110(11) .0320(3) Uani d . 1 . . C H3A .5255 .6461 -.0145 .038 Uiso calc R 1 . . H C4 .59555(12) .77891(10) .04420(10) .0274(3) Uani d . 1 . . C C5 .69475(12) .80231(10) -.04583(10) .0291(3) Uani d . 1 . . C C6 .67673(14) .91276(11) -.07583(11) .0352(3) Uani d . 1 . . C H6A .7384 .9310 -.1338 .042 Uiso calc R 1 . . H H6B .5863 .9242 -.1026 .042 Uiso calc R 1 . . H C7 .70312(13) .97649(10) .02455(11) .0331(3) Uani d . 1 . . C C8 .76917(17) 1.07748(11) .00827(15) .0452(4) Uani d . 1 . . C H8A .8629 1.0678 -.0092 .054 Uiso calc R 1 . . H H8B .7268 1.1123 -.0530 .054 Uiso calc R 1 . . H C9 .75760(18) 1.14032(13) .11095(17) .0545(5) Uani d . 1 . . C H9A .8155 1.1988 .1058 .065 Uiso calc R 1 . . H H9B .6662 1.1637 .1190 .065 Uiso calc R 1 . . H C10 .79732(18) 1.07761(13) .20888(16) .0523(4) Uani d . 1 . . C H10A .8877 1.0528 .1989 .063 Uiso calc R 1 . . H H10B .7967 1.1194 .2744 .063 Uiso calc R 1 . . H C11 .67008(13) .94220(10) .12557(11) .0309(3) Uani d . 1 . . C C12 .58268(12) .85096(9) .12935(10) .0278(3) Uani d . 1 . . C C13 .84040(13) .78464(11) -.00578(12) .0345(3) Uani d . 1 . . C C14 .9817(2) .6923(2) .1138(2) .0876(8) Uani d . 1 . . C H14A .9766 .6369 .1646 .131 Uiso calc R 1 . . H H14B 1.0217 .7493 .1500 .131 Uiso calc R 1 . . H H14C 1.0352 .6732 .0519 .131 Uiso calc R 1 . . H C15 .7588(2) .92517(16) .31039(16) .0646(5) Uani d . 1 . . C H15A .7669 .9621 .3781 .097 Uiso calc R 1 . . H H15B .8452 .9006 .2891 .097 Uiso calc R 1 . . H H15C .6991 .8693 .3205 .097 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 Cl1 .0679(3) .0428(2) .0467(2) .00070(17) .0326(2) -.00683(15) Cl2 .0607(3) .0600(3) .0494(3) -.03286(19) .0159(2) -.00407(18) O1 .0391(5) .0558(6) .0271(5) -.0100(4) .0114(4) -.0115(4) O2 .0290(5) .0778(8) .0609(8) -.0107(5) .0091(5) .0097(6) O3 .0343(5) .0810(9) .0585(8) .0090(5) .0034(5) .0304(7) N1 .0337(5) .0411(6) .0283(6) .0001(5) .0102(4) .0055(5) N2 .0464(7) .0454(7) .0337(6) -.0062(5) .0008(5) -.0082(5) C1 .0368(6) .0359(6) .0241(6) .0032(5) .0098(5) .0029(5) C2 .0310(6) .0398(7) .0303(6) -.0067(5) .0044(5) .0042(5) C3 .0311(6) .0377(7) .0272(6) -.0044(5) .0054(5) -.0023(5) C4 .0242(5) .0363(6) .0218(6) .0000(5) .0038(4) .0021(5) C5 .0259(5) .0396(7) .0218(6) -.0039(5) .0058(4) -.0016(5) C6 .0351(6) .0455(7) .0249(6) -.0044(5) .0046(5) .0075(5) C7 .0307(6) .0343(6) .0345(7) -.0021(5) .0042(5) .0045(5) C8 .0438(8) .0415(8) .0502(9) -.0110(6) .0024(7) .0083(6) C9 .0461(9) .0389(8) .0789(13) -.0095(7) .0134(8) -.0072(8) C10 .0462(9) .0557(10) .0552(11) -.0135(7) .0044(8) -.0203(8) C11 .0305(6) .0333(6) .0289(6) .0000(5) .0027(5) -.0010(5) C12 .0290(6) .0320(6) .0225(6) .0010(5) .0042(4) .0031(5) C13 .0283(6) .0442(7) .0311(7) -.0008(5) .0049(5) -.0033(6) C14 .0444(10) .127(2) .0913(17) .0229(12) -.0061(11) .0424(16) C15 .0765(13) .0795(14) .0373(9) -.0032(10) -.0148(9) -.0015(8) 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 Cl1 C1 . 1.7374(13) ? Cl2 C2 . 1.7393(13) ? O1 C5 . 1.4208(15) ? O2 C13 . 1.1954(17) ? O3 C13 . 1.3250(18) ? O3 C14 . 1.454(2) ? N1 C2 . 1.3215(18) yes N1 C1 . 1.3349(18) yes N2 C11 . 1.4094(18) ? N2 C15 . 1.456(2) ? N2 C10 . 1.480(2) ? C1 C12 . 1.4045(16) yes C2 C3 . 1.3860(17) yes C3 C4 . 1.3772(18) yes C4 C12 . 1.4143(17) yes C4 C5 . 1.5136(16) ? C5 C6 . 1.5200(19) ? C5 C13 . 1.5484(18) ? C6 C7 . 1.505(2) ? C7 C11 . 1.3513(19) ? C7 C8 . 1.5071(19) ? C8 C9 . 1.505(3) ? C9 C10 . 1.502(3) ? C11 C12 . 1.4934(17) ?