#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2008589.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_2008589 _journal_name_full 'Acta Crystallographica' _journal_year 1999 _journal_volume C55 _journal_page_first 1025 _journal_page_last 1027 _publ_section_title ; Absolute configuration of the active stereoisomer of new rice fungicide Carpropamid: (1S,3R)- N-[(R)-1-(4-chlorophenyl)ethyl] 2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxamide ; loop_ _publ_author_name 'Koketsu, Mamoru' 'Kagabu, Shinzo' 'Matsuoka, Masashi' _chemical_name_common (1S,3R)-Carpropamide _chemical_formula_moiety 'C15 H18 Cl3 N O' _chemical_formula_sum 'C15 H18 Cl3 N O' _chemical_formula_weight 334.67 _chemical_melting_point 136 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z _cell_length_a 13.6977(5) _cell_length_b 19.8307(8) _cell_length_c 12.7594(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3465.9(2) _cell_formula_units_Z 8 _cell_measurement_temperature 296.2 _exptl_crystal_density_diffrn 1.283 _diffrn_ambient_temperature 296.2 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 Cl(1) -.59180(10) -.40454(9) -.48850(10) .0981(6) Uani d . 1.00 . . Cl Cl(2) -.42940(10) -.31750(10) -.54200(10) .1014(6) Uani d . 1.00 . . Cl Cl(3) -.00370(10) -.25890(10) -.8089(2) .1520(10) Uani d . 1.00 . . Cl Cl(4) -.80120(10) -.14369(9) -.73650(10) .0884(6) Uani d . 1.00 . . Cl Cl(5) -.67790(10) -.08481(9) -.57720(10) .0810(5) Uani d . 1.00 . . Cl Cl(6) -.3977(2) -.00240(10) -.2427(2) .1371(9) Uani d . 1.00 . . Cl O(1) -.5245(2) -.23160(10) -.7637(3) .0578(10) Uani d . 1.00 . . O O(2) -.5222(2) .0201(2) -.7327(3) .0620(10) Uani d . 1.00 . . O N(1) -.4853(3) -.3375(2) -.8104(3) .0440(10) Uani d . 1.00 . . N N(2) -.4787(3) -.0880(2) -.7404(3) .0510(10) Uani d . 1.00 . . N C(1) -.1278(4) -.2749(3) -.8350(6) .083(2) Uani d . 1.00 . . C C(2) -.1784(4) -.3111(3) -.7624(5) .077(2) Uani d . 1.00 . . C C(3) -.2779(4) -.3256(3) -.7828(5) .0620(10) Uani d . 1.00 . . C C(4) -.3207(4) -.3026(2) -.8730(4) .0490(10) Uani d . 1.00 . . C C(5) -.2656(4) -.2657(3) -.9439(4) .066(2) Uani d . 1.00 . . C C(6) -.1674(5) -.2511(4) -.9245(5) .093(2) Uani d . 1.00 . . C C(7) -.4274(3) -.3185(2) -.9010(4) .0470(10) Uani d . 1.00 . . C C(8) -.4335(4) -.3742(3) -.9810(4) .063(2) Uani d . 1.00 . . C C(9) -.5316(3) -.2921(2) -.7508(4) .0390(10) Uani d . 1.00 . . C C(10) -.5980(3) -.3216(2) -.6671(4) .0430(10) Uani d . 1.00 . . C C(11) -.5543(3) -.3345(3) -.5604(4) .0620(10) Uani d . 1.00 . . C C(12) -.6203(4) -.2770(3) -.5758(4) .063(2) Uani d . 1.00 . . C C(13) -.6754(3) -.3683(2) -.7096(4) .0560(10) Uani d . 1.00 . . C C(14) -.7385(4) -.3344(3) -.7922(5) .080(2) Uani d . 1.00 . . C C(15) -.7197(4) -.2735(3) -.5229(5) .082(2) Uani d . 1.00 . . C C(16) -.3895(4) -.0257(4) -.3748(5) .084(2) Uani d . 1.00 . . C C(17) -.4339(4) -.0830(4) -.4070(5) .084(2) Uani d . 1.00 . . C C(18) -.4296(4) -.0994(3) -.5122(5) .069(2) Uani d . 1.00 . . C C(19) -.3820(3) -.0591(2) -.5832(4) .0520(10) Uani d . 1.00 . . C C(20) -.3358(4) -.0021(3) -.5471(5) .071(2) Uani d . 1.00 . . C C(21) -.3396(5) .0156(3) -.4416(5) .083(2) Uani d . 1.00 . . C C(22) -.3793(4) -.0762(3) -.6997(4) .0570(10) Uani d . 1.00 . . C C(23) -.3159(4) -.1375(3) -.7253(5) .074(2) Uani d . 1.00 . . C C(24) -.5434(3) -.0387(2) -.7519(4) .0480(10) Uani d . 1.00 . . C C(25) -.6434(4) -.0596(2) -.7913(4) .0500(10) Uani d . 1.00 . . C C(26) -.7163(4) -.0813(3) -.7088(4) .0610(10) Uani d . 1.00 . . C C(27) -.7261(4) -.0136(3) -.7566(5) .064(2) Uani d . 1.00 . . C C(28) -.6437(4) -.0933(3) -.8973(4) .063(2) Uani d . 1.00 . . C C(29) -.5971(5) -.0510(4) -.9813(5) .099(2) Uani d . 1.00 . . C C(30) -.8121(4) .0069(3) -.8254(5) .089(2) Uani d . 1.00 . . C H(1) -.1489 -.3272 -.6967 .0928 Uiso calc . 1.00 . . H H(2) -.3157 -.3545 -.7359 .0740 Uiso calc . 1.00 . . H H(3) -.2971 -.2464 -1.0053 .0781 Uiso calc . 1.00 . . H H(4) -.1300 -.2275 -.9763 .1079 Uiso calc . 1.00 . . H H(5) -.4561 -.2783 -.9300 .0553 Uiso calc . 1.00 . . H H(6) -.3990 -.3618 -1.0427 .0812 Uiso calc . 1.00 . . H H(7) -.4101 -.4145 -.9536 .0812 Uiso calc . 1.00 . . H H(8) -.5019 -.3802 -1.0009 .0812 Uiso calc . 1.00 . . H H(9) -.4910 -.3817 -.7723 .0538 Uiso calc . 1.00 . . H H(10) -.6478 -.4081 -.7388 .0643 Uiso calc . 1.00 . . H H(11) -.7199 -.3827 -.6538 .0643 Uiso calc . 1.00 . . H H(12) -.7869 -.3652 -.8189 .0913 Uiso calc . 1.00 . . H H(13) -.7696 -.2962 -.7647 .0913 Uiso calc . 1.00 . . H H(14) -.6974 -.3215 -.8498 .0913 Uiso calc . 1.00 . . H H(15) -.5875 -.2333 -.5800 .0757 Uiso calc . 1.00 . . H H(16) -.7230 -.2415 -.4695 .1046 Uiso calc . 1.00 . . H H(17) -.7702 -.2608 -.5758 .1046 Uiso calc . 1.00 . . H H(18) -.7387 -.3168 -.4980 .1046 Uiso calc . 1.00 . . H H(19) -.4681 -.1120 -.3551 .0996 Uiso calc . 1.00 . . H H(20) -.4607 -.1423 -.5337 .0848 Uiso calc . 1.00 . . H H(21) -.2965 .0260 -.5955 .0900 Uiso calc . 1.00 . . H H(22) -.3116 .0564 -.4132 .0979 Uiso calc . 1.00 . . H H(23) -.3516 -.0373 -.7364 .0709 Uiso calc . 1.00 . . H H(24) -.2495 -.1303 -.7000 .0873 Uiso calc . 1.00 . . H H(25) -.3121 -.1449 -.7987 .0873 Uiso calc . 1.00 . . H H(26) -.3408 -.1762 -.6917 .0873 Uiso calc . 1.00 . . H H(27) -.4989 -.1316 -.7470 .0611 Uiso calc . 1.00 . . H H(28) -.7096 -.1042 -.9179 .0775 Uiso calc . 1.00 . . H H(29) -.6084 -.1349 -.8916 .0775 Uiso calc . 1.00 . . H H(30) -.5980 -.0741 -1.0461 .1279 Uiso calc . 1.00 . . H H(31) -.5327 -.0403 -.9618 .1279 Uiso calc . 1.00 . . H H(32) -.6340 -.0099 -.9884 .1279 Uiso calc . 1.00 . . H H(33) -.7039 .0232 -.7114 .0758 Uiso calc . 1.00 . . H H(34) -.8066 .0523 -.8476 .0993 Uiso calc . 1.00 . . H H(35) -.8717 .0018 -.7865 .0993 Uiso calc . 1.00 . . H H(36) -.8147 -.0220 -.8848 .0993 Uiso calc . 1.00 . . 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 Cl(1) .0930(10) .1140(10) .0870(10) .0120(10) .0243(10) .0540(10) Cl(2) .0519(8) .178(2) .0740(10) -.0190(10) -.0152(8) .0060(10) Cl(3) .0640(10) .203(3) .189(2) -.0500(10) -.0220(10) .058(2) Cl(4) .0810(10) .0900(10) .0940(10) -.0322(9) -.0177(10) .0138(10) Cl(5) .0860(10) .1070(10) .0500(7) .0060(10) -.0093(8) .0023(8) Cl(6) .122(2) .212(3) .0780(10) .052(2) -.0220(10) -.056(2) O(1) .065(2) .0310(10) .078(2) -.007(2) .028(2) .000(2) O(2) .069(2) .036(2) .082(3) -.001(2) -.022(2) -.008(2) N(1) .043(2) .032(2) .056(2) .002(2) .016(2) .010(2) N(2) .059(2) .034(2) .060(2) -.004(2) -.021(2) -.003(2) C(1) .055(2) .095(5) .099(4) -.018(3) .006(3) .009(4) C(2) .056(2) .101(5) .075(4) .007(3) -.015(3) .015(3) C(3) .056(2) .057(3) .074(3) -.005(3) .005(2) .022(3) C(4) .047(2) .040(3) .059(3) .003(2) .013(2) -.008(2) C(5) .061(3) .077(4) .061(3) -.010(3) .015(3) .020(3) C(6) .066(3) .123(6) .090(4) -.036(4) .009(3) .023(4) C(7) .046(2) .042(3) .053(3) .007(2) .012(2) .010(2) C(8) .064(3) .074(4) .052(3) -.009(3) .016(3) -.009(2) C(9) .032(2) .031(2) .055(3) -.006(2) .002(2) .004(2) C(10) .036(2) .040(2) .054(2) .003(2) .005(2) .007(2) C(11) .042(2) .089(3) .055(3) -.009(2) .001(2) .002(2) C(12) .063(3) .067(3) .059(3) -.007(2) .020(3) -.013(2) C(13) .044(3) .047(3) .075(3) -.013(2) .015(2) -.001(2) C(14) .058(3) .092(5) .090(4) -.003(3) -.018(3) .013(3) C(15) .072(3) .094(5) .082(4) .018(3) .046(3) -.011(4) C(16) .058(4) .122(5) .073(2) .035(3) -.023(3) -.026(3) C(17) .051(3) .135(5) .066(3) -.003(4) -.008(3) -.004(4) C(18) .064(3) .075(4) .069(3) -.018(3) -.011(3) -.009(3) C(19) .046(3) .048(3) .062(2) .023(2) -.014(2) -.004(2) C(20) .077(4) .055(3) .082(3) .003(3) -.022(3) -.005(3) C(21) .104(5) .056(4) .088(3) .021(3) -.051(4) -.029(3) C(22) .056(2) .052(3) .064(2) -.010(2) -.010(2) -.002(3) C(23) .063(3) .078(4) .081(4) .018(3) -.012(3) -.019(3) C(24) .060(2) .036(2) .048(3) -.002(2) -.017(2) -.006(2) C(25) .060(2) .036(2) .054(2) -.002(2) -.021(2) -.003(2) C(26) .068(3) .066(3) .050(2) .001(2) -.015(2) .002(2) C(27) .059(3) .059(3) .075(4) .010(2) -.017(3) -.005(3) C(28) .070(3) .058(3) .061(3) -.006(3) -.023(3) -.020(2) C(29) .110(5) .131(6) .055(4) -.028(5) .003(4) .004(3) C(30) .087(4) .084(4) .095(5) .024(4) -.056(4) .001(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl(1) C(11) 1_555 1_555 1.742(7) no Cl(2) C(11) 1_555 1_555 1.760(6) no Cl(3) C(1) 1_555 1_555 1.761(7) no Cl(4) C(26) 1_555 1_555 1.734(7) no Cl(5) C(26) 1_555 1_555 1.762(6) no Cl(6) C(16) 1_555 1_555 1.751(8) no O(1) C(9) 1_555 1_555 1.214(6) no O(2) C(24) 1_555 1_555 1.226(6) no N(1) C(7) 1_555 1_555 1.452(7) no N(1) C(9) 1_555 1_555 1.337(6) no N(2) C(22) 1_555 1_555 1.475(7) no N(2) C(24) 1_555 1_555 1.328(7) no C(1) C(2) 1_555 1_555 1.362(10) no C(1) C(6) 1_555 1_555 1.350(10) no C(2) C(3) 1_555 1_555 1.417(9) no C(3) C(4) 1_555 1_555 1.369(9) no C(4) C(5) 1_555 1_555 1.388(8) no C(4) C(7) 1_555 1_555 1.537(8) no C(5) C(6) 1_555 1_555 1.397(10) no C(7) C(8) 1_555 1_555 1.506(8) no C(9) C(10) 1_555 1_555 1.519(7) no C(10) C(11) 1_555 1_555 1.509(8) no C(10) C(12) 1_555 1_555 1.493(8) no C(10) C(13) 1_555 1_555 1.510(8) no C(11) C(12) 1_555 1_555 1.469(9) no C(12) C(15) 1_555 1_555 1.521(8) no C(13) C(14) 1_555 1_555 1.520(9) no C(16) C(17) 1_555 1_555 1.350(10) no C(16) C(21) 1_555 1_555 1.370(10) no C(17) C(18) 1_555 1_555 1.383(10) no C(18) C(19) 1_555 1_555 1.372(9) no C(19) C(20) 1_555 1_555 1.376(8) no C(19) C(22) 1_555 1_555 1.524(9) no C(20) C(21) 1_555 1_555 1.390(10) no C(22) C(23) 1_555 1_555 1.530(9) no C(24) C(25) 1_555 1_555 1.516(8) no C(25) C(26) 1_555 1_555 1.513(9) no C(25) C(27) 1_555 1_555 1.520(8) no C(25) C(28) 1_555 1_555 1.509(8) no C(26) C(27) 1_555 1_555 1.480(9) no C(27) C(30) 1_555 1_555 1.524(8) no C(28) C(29) 1_555 1_555 1.503(10) no