#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2011359.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_2011359 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first e398 _journal_page_last e399 _publ_section_title ; Clarithromycin hydrochloride 3.5-hydrate ; loop_ _publ_author_name 'Parvez, Masood' 'Arayne, M. Saeed' 'Sabri, Rizwana' 'Sultana, Najma' '6-O-Methylerythromycin A Hydrochloride 3.5 Hydrate' _chemical_name_common 'Clarithromycin Hydrochloride 3.5 Hydrate' _chemical_formula_moiety 'C38 H70 N O13 1+, Cl 1-, 3.5H2 O' _chemical_formula_sum 'C38 H77 Cl N O16.50' _chemical_formula_iupac 'C38 H70 N O13 1+, Cl 1-, 3.5H2 O' _chemical_formula_weight 847.46 _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.409(2) _cell_length_b 16.489(3) _cell_length_c 19.267(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4577.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.228 _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 .25061(11) .87642(10) -.04179(7) .0837(4) Uani d . 1 . . Cl O1 .55650(18) .60759(17) .34796(16) .0475(7) Uani d . 1 . . O O2 .4746(2) .5024(2) .38923(18) .0618(9) Uani d . 1 . . O O3 .23968(18) .63278(17) .31443(14) .0427(7) Uani d . 1 . . O O4 .1304(2) .53247(17) .34298(16) .0492(7) Uani d . 1 . . O O5 .0660(2) .71118(18) .26086(18) .0577(8) Uani d . 1 . . O O6 -.0778(2) .6117(2) .25741(18) .0659(10) Uani d . 1 . . O H6 -.1188 .5777 .2621 .099 Uiso calc R 1 . . H O7 .27955(19) .58293(17) .12528(15) .0467(7) Uani d . 1 . . O O8 .13238(19) .54420(17) .10599(15) .0471(7) Uani d . 1 . . O O9 .2349(4) .7438(2) .0862(3) .1074(17) Uani d . 1 . . O H9 .2632 .7642 .0537 .161 Uiso calc R 1 . . H O10 .4043(2) .42754(18) .21812(16) .0554(8) Uani d . 1 . . O O11 .5730(3) .3296(2) .1690(2) .0791(12) Uani d . 1 . . O O12 .6457(3) .40473(19) .28939(18) .0640(9) Uani d . 1 . . O H12 .6314 .3646 .2667 .096 Uiso calc R 1 . . H O13 .77492(19) .5218(2) .28931(18) .0590(9) Uani d . 1 . . O H13 .7778 .4770 .3076 .089 Uiso calc R 1 . . H N1 .0855(3) .7581(2) -.01075(19) .0543(10) Uani d . 1 . . N H1 .1353 .7913 -.0047 .065 Uiso calc R 1 . . H C1 .4783(3) .5701(3) .3690(2) .0436(10) Uani d . 1 . . C C2 .3962(3) .6274(3) .3636(2) .0452(10) Uani d . 1 . . C H2 .4183 .6787 .3438 .054 Uiso calc R 1 . . H C3 .3265(3) .5898(3) .3124(2) .0392(10) Uani d . 1 . . C H3 .3157 .5331 .3255 .047 Uiso calc R 1 . . H C4 .3626(3) .5926(2) .2380(2) .0414(10) Uani d . 1 . . C H4 .4245 .5680 .2393 .050 Uiso calc R 1 . . H C5 .3046(3) .5394(2) .1877(2) .0405(9) Uani d . 1 . . C H5 .2477 .5222 .2114 .049 Uiso calc R 1 . . H C6 .3560(3) .4635(3) .1608(2) .0430(10) Uani d . 1 . . C C7 .4333(3) .4885(3) .1105(2) .0469(11) Uani d . 1 . . C H7A .4686 .5321 .1316 .056 Uiso calc R 1 . . H H7B .4049 .5098 .0687 .056 Uiso calc R 1 . . H C8 .5013(3) .4204(3) .0896(2) .0532(12) Uani d . 1 . . C H8 .4648 .3719 .0788 .064 Uiso calc R 1 . . H C9 .5687(4) .3988(3) .1467(3) .0555(12) Uani d . 1 . . C C10 .6362(3) .4622(3) .1721(2) .0509(11) Uani d . 1 . . C H10 .6222 .5132 .1481 .061 Uiso calc R 1 . . H C11 .6237(3) .4763(3) .2508(2) .0479(11) Uani d . 1 . . C H11 .5580 .4885 .2589 .058 Uiso calc R 1 . . H C12 .6802(3) .5453(3) .2825(2) .0472(11) Uani d . 1 . . C C13 .6450(3) .5657(3) .3558(2) .0495(11) Uani d . 1 . . C H13A .6354 .5154 .3819 .059 Uiso calc R 1 . . H C14 .7063(3) .6221(4) .3974(3) .0694(15) Uani d . 1 . . C H14A .7667 .5969 .4029 .083 Uiso calc R 1 . . H H14B .7151 .6717 .3712 .083 Uiso calc R 1 . . H C15 .6699(4) .6436(5) .4675(3) .102(2) Uani d . 1 . . C H15A .6124 .6725 .4627 .153 Uiso calc R 1 . . H H15B .7142 .6771 .4912 .153 Uiso calc R 1 . . H H15C .6596 .5949 .4938 .153 Uiso calc R 1 . . H C16 .3631(3) .6439(4) .4380(3) .0772(18) Uani d . 1 . . C H16A .3407 .5944 .4583 .116 Uiso calc R 1 . . H H16B .3140 .6833 .4372 .116 Uiso calc R 1 . . H H16C .4138 .6644 .4651 .116 Uiso calc R 1 . . H C17 .1752(3) .6043(3) .3643(2) .0444(10) Uani d . 1 . . C H17 .2098 .5920 .4068 .053 Uiso calc R 1 . . H C18 .1080(3) .6718(3) .3807(2) .0535(12) Uani d . 1 . . C H18A .1428 .7219 .3856 .064 Uiso calc R 1 . . H H18B .0790 .6603 .4250 .064 Uiso calc R 1 . . H C19 .0320(3) .6850(3) .3269(2) .0506(12) Uani d . 1 . . C C20 -.0115(3) .6029(3) .3116(2) .0498(11) Uani d . 1 . . C H20 -.0431 .5833 .3534 .060 Uiso calc R 1 . . H C21 .0602(3) .5412(3) .2897(2) .0478(11) Uani d . 1 . . C H21 .0897 .5591 .2465 .057 Uiso calc R 1 . . H C22 -.0414(4) .7430(3) .3550(3) .0789(17) Uani d . 1 . . C H22A -.0129 .7939 .3663 .118 Uiso calc R 1 . . H H22B -.0689 .7202 .3960 .118 Uiso calc R 1 . . H H22C -.0885 .7513 .3205 .118 Uiso calc R 1 . . H C23 .1196(4) .7839(3) .2608(3) .0789(18) Uani d . 1 . . C H23A .0887 .8244 .2881 .118 Uiso calc R 1 . . H H23B .1263 .8031 .2140 .118 Uiso calc R 1 . . H H23C .1797 .7731 .2801 .118 Uiso calc R 1 . . H C24 .0213(4) .4574(3) .2797(3) .0706(15) Uani d . 1 . . C H24A .0689 .4222 .2621 .106 Uiso calc R 1 . . H H24B -.0292 .4594 .2472 .106 Uiso calc R 1 . . H H24C -.0007 .4369 .3234 .106 Uiso calc R 1 . . H C25 .3768(4) .6790(3) .2114(2) .0562(13) Uani d . 1 . . C H25A .3193 .7083 .2145 .084 Uiso calc R 1 . . H H25B .3969 .6774 .1639 .084 Uiso calc R 1 . . H H25C .4230 .7057 .2391 .084 Uiso calc R 1 . . H C26 .1886(3) .6116(3) .1213(2) .0443(10) Uani d . 1 . . C H26 .1698 .6367 .1652 .053 Uiso calc R 1 . . H C27 .1875(3) .6733(3) .0630(3) .0523(12) Uani d . 1 . . C H27 .2170 .6512 .0212 .063 Uiso calc R 1 . . H C28 .0882(3) .6968(3) .0485(2) .0464(11) Uani d . 1 . . C H28 .0641 .7238 .0901 .056 Uiso calc R 1 . . H C29 .0293(3) .6238(3) .0354(2) .0541(12) Uani d . 1 . . C H29A .0500 .5965 -.0064 .065 Uiso calc R 1 . . H H29B -.0348 .6400 .0290 .065 Uiso calc R 1 . . H C30 .0368(3) .5666(3) .0969(2) .0471(11) Uani d . 1 . . C H30 .0135 .5932 .1389 .056 Uiso calc R 1 . . H C31 .0947(4) .7225(4) -.0815(2) .0742(16) Uani d . 1 . . C H31A .0399 .6921 -.0924 .111 Uiso calc R 1 . . H H31B .1478 .6874 -.0828 .111 Uiso calc R 1 . . H H31C .1025 .7653 -.1148 .111 Uiso calc R 1 . . H C32 .0014(4) .8109(3) -.0067(3) .0803(18) Uani d . 1 . . C H32A .0012 .8480 -.0451 .120 Uiso calc R 1 . . H H32B .0023 .8408 .0361 .120 Uiso calc R 1 . . H H32C -.0533 .7777 -.0085 .120 Uiso calc R 1 . . H C33 -.0156(3) .4895(3) .0842(3) .0666(14) Uani d . 1 . . C H33A .0076 .4638 .0431 .100 Uiso calc R 1 . . H H33B -.0803 .5016 .0784 .100 Uiso calc R 1 . . H H33C -.0078 .4538 .1232 .100 Uiso calc R 1 . . H C34 .2885(3) .4059(3) .1252(3) .0660(15) Uani d . 1 . . C H34A .3191 .3553 .1159 .099 Uiso calc R 1 . . H H34B .2679 .4295 .0823 .099 Uiso calc R 1 . . H H34C .2361 .3966 .1549 .099 Uiso calc R 1 . . H C35 .3594(5) .3714(4) .2612(3) .108(2) Uani d . 1 . . C H35A .2962 .3879 .2681 .163 Uiso calc R 1 . . H H35B .3907 .3691 .3051 .163 Uiso calc R 1 . . H H35C .3607 .3189 .2398 .163 Uiso calc R 1 . . H C36 .5544(4) .4450(4) .0240(2) .0729(16) Uani d . 1 . . C H36A .5894 .4934 .0330 .109 Uiso calc R 1 . . H H36B .5112 .4548 -.0130 .109 Uiso calc R 1 . . H H36C .5959 .4021 .0109 .109 Uiso calc R 1 . . H C37 .7349(4) .4357(4) .1514(3) .0835(18) Uani d . 1 . . C H37A .7494 .3851 .1735 .125 Uiso calc R 1 . . H H37B .7786 .4763 .1659 .125 Uiso calc R 1 . . H H37C .7381 .4293 .1019 .125 Uiso calc R 1 . . H C38 .6798(3) .6209(3) .2365(3) .0599(13) Uani d . 1 . . C H38A .7153 .6631 .2583 .090 Uiso calc R 1 . . H H38B .6171 .6391 .2300 .090 Uiso calc R 1 . . H H38C .7067 .6081 .1923 .090 Uiso calc R 1 . . H O14 .3813(3) .7691(3) -.1486(2) .0993(14) Uani d . 1 . . O O15 .1859(3) .3791(3) .4090(3) .1119(16) Uani d . 1 . . O O16 .1777(3) .9109(3) .1089(2) .0964(13) Uani d . 1 . . O O17 .3762(5) .8302(5) .0820(4) .090(2) Uani d P .50 . . O 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 .0881(10) .0997(11) .0634(8) -.0169(9) .0078(8) .0186(8) O1 .0307(15) .0522(17) .0595(18) -.0041(14) -.0042(14) .0062(15) O2 .0428(18) .064(2) .079(2) -.0029(16) .0019(17) .0277(19) O3 .0302(15) .0475(16) .0503(16) .0025(13) .0007(13) .0045(14) O4 .0412(17) .0476(17) .0589(18) -.0045(14) -.0063(15) .0087(14) O5 .052(2) .0515(18) .070(2) -.0066(16) .0039(17) .0098(16) O6 .0378(19) .087(3) .073(2) -.0110(17) -.0182(17) .022(2) O7 .0384(16) .0559(18) .0459(17) .0019(14) -.0075(13) .0068(14) O8 .0398(16) .0429(15) .0586(18) .0010(14) -.0104(14) -.0011(14) O9 .120(4) .065(2) .137(4) -.040(3) -.074(3) .047(3) O10 .056(2) .0550(18) .0552(19) .0042(16) -.0058(16) .0174(15) O11 .098(3) .0432(19) .097(3) .018(2) -.010(2) .0025(19) O12 .068(2) .0556(19) .068(2) -.0017(19) -.0076(19) .0177(17) O13 .0250(16) .076(2) .076(2) .0042(15) -.0017(15) .0205(19) N1 .055(2) .055(2) .053(2) .0082(19) -.007(2) .0029(19) C1 .030(2) .057(3) .044(2) -.005(2) -.0015(19) .003(2) C2 .032(2) .055(3) .048(2) .002(2) -.0043(19) -.007(2) C3 .026(2) .046(2) .046(2) .0020(18) -.0025(18) -.001(2) C4 .038(2) .043(2) .043(2) -.0023(19) -.005(2) -.0031(18) C5 .040(2) .041(2) .041(2) -.0023(19) -.0064(19) .0050(19) C6 .041(2) .045(2) .043(2) -.003(2) -.003(2) .0055(19) C7 .054(3) .046(2) .041(2) .005(2) -.003(2) .0004(19) C8 .060(3) .048(3) .051(3) .004(2) .003(2) -.007(2) C9 .064(3) .045(3) .057(3) .014(2) .008(2) -.003(2) C10 .044(3) .056(3) .053(3) .013(2) .005(2) .006(2) C11 .034(2) .053(3) .056(3) .003(2) .000(2) .011(2) C12 .025(2) .058(3) .059(3) .008(2) -.002(2) .011(2) C13 .030(2) .062(3) .056(3) -.001(2) -.004(2) .006(2) C14 .040(3) .100(4) .068(3) -.016(3) -.010(2) -.009(3) C15 .075(4) .159(7) .072(4) -.040(4) -.005(3) -.022(4) C16 .041(3) .130(5) .061(3) -.001(3) -.007(3) -.040(3) C17 .038(2) .056(3) .039(2) -.006(2) -.0025(19) -.001(2) C18 .038(3) .068(3) .054(3) .001(2) .001(2) -.011(2) C19 .041(3) .053(3) .057(3) .002(2) .005(2) -.003(2) C20 .034(2) .062(3) .053(3) .001(2) -.002(2) .011(2) C21 .048(3) .051(2) .044(2) -.011(2) -.009(2) .007(2) C22 .051(3) .075(4) .110(5) .013(3) .013(3) -.013(3) C23 .062(4) .045(3) .129(5) -.007(3) .009(4) .015(3) C24 .070(4) .056(3) .086(4) -.022(3) -.009(3) -.001(3) C25 .061(3) .053(3) .055(3) -.021(2) .000(2) -.003(2) C26 .038(2) .042(2) .052(3) .003(2) -.009(2) .000(2) C27 .046(3) .049(3) .061(3) -.004(2) -.013(2) .007(2) C28 .049(3) .050(3) .040(2) .009(2) -.004(2) .003(2) C29 .042(3) .069(3) .051(3) .007(2) -.004(2) .005(2) C30 .031(2) .057(3) .053(3) .003(2) -.008(2) .003(2) C31 .091(4) .087(4) .044(3) .002(3) .000(3) .005(3) C32 .075(4) .070(4) .096(4) .035(3) -.006(3) .018(3) C33 .049(3) .074(4) .076(4) -.015(3) -.010(3) .005(3) C34 .061(3) .052(3) .085(4) -.013(2) -.007(3) -.014(3) C35 .136(6) .094(5) .095(5) -.028(5) -.010(5) .052(4) C36 .074(4) .094(4) .051(3) .013(3) .011(3) -.011(3) C37 .052(3) .116(5) .082(4) .023(3) .013(3) .001(4) C38 .051(3) .060(3) .068(3) -.003(3) .000(3) .016(3) O14 .109(3) .085(3) .103(3) -.012(3) .001(3) .017(2) O15 .108(3) .092(3) .135(4) -.004(3) -.047(3) .023(3) O16 .108(3) .102(3) .080(3) -.020(3) -.002(3) -.020(2) O17 .073(5) .094(6) .103(6) .006(5) .006(5) .002(5) 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 C1 . 1.348(5) y O1 C13 . 1.458(5) y O2 C1 . 1.184(5) y O3 C17 . 1.416(5) y O3 C3 . 1.438(5) y O4 C17 . 1.410(5) y O4 C21 . 1.448(5) y O5 C23 . 1.426(5) y O5 C19 . 1.431(5) y O6 C20 . 1.422(5) y O6 H6 . .8200 n O7 C26 . 1.396(5) y O7 C5 . 1.446(5) y O8 C26 . 1.407(5) y O8 C30 . 1.437(5) y O9 C27 . 1.421(5) y O9 H9 . .8200 n O10 C35 . 1.400(6) y O10 C6 . 1.434(5) y O11 C9 . 1.220(5) y O12 C11 . 1.431(5) y O12 H12 . .8200 n O13 C12 . 1.424(5) y O13 H13 . .8200 n N1 C31 . 1.490(6) y N1 C32 . 1.493(6) y N1 C28 . 1.525(5) y N1 H1 . .9100 n C1 C2 . 1.517(6) n C2 C16 . 1.536(6) n C2 C3 . 1.538(5) n C2 H2 . .9800 n C3 C4 . 1.526(6) n C3 H3 . .9800 n C4 C25 . 1.528(6) n C4 C5 . 1.552(5) n C4 H4 . .9800 n C5 C6 . 1.544(6) n C5 H5 . .9800 n C6 C34 . 1.522(6) n C6 C7 . 1.534(6) n C7 C8 . 1.544(6) n C7 H7A . .9700 n C7 H7B . .9700 n C8 C9 . 1.509(7) n C8 C36 . 1.533(6) n C8 H8 . .9800 n C9 C10 . 1.509(7) n C10 C37 . 1.540(6) n C10 C11 . 1.545(6) n C10 H10 . .9800 n C11 C12 . 1.526(6) n C11 H11 . .9800 n C12 C38 . 1.531(6) n C12 C13 . 1.538(6) n C13 C14 . 1.512(6) n C13 H13A . .9800 n C14 C15 . 1.492(7) n C14 H14A . .9700 n C14 H14B . .9700 n C15 H15A . .9600 n C15 H15B . .9600 n C15 H15C . .9600 n C16 H16A . .9600 n C16 H16B . .9600 n C16 H16C . .9600 n C17 C18 . 1.509(6) n C17 H17 . .9800 n C18 C19 . 1.523(6) n C18 H18A . .9700 n C18 H18B . .9700 n C19 C20 . 1.520(6) n C19 C22 . 1.525(6) n C20 C21 . 1.512(6) n C20 H20 . .9800 n C21 C24 . 1.504(6) n C21 H21 . .9800 n C22 H22A . .9600 n C22 H22B . .9600 n C22 H22C . .9600 n C23 H23A . .9600 n C23 H23B . .9600 n C23 H23C . .9600 n C24 H24A . .9600 n C24 H24B . .9600 n C24 H24C . .9600 n C25 H25A . .9600 n C25 H25B . .9600 n C25 H25C . .9600 n C26 C27 . 1.516(6) n C26 H26 . .9800 n C27 C28 . 1.509(6) n C27 H27 . .9800 n C28 C29 . 1.495(6) n C28 H28 . .9800 n C29 C30 . 1.517(6) n C29 H29A . .9700 n C29 H29B . .9700 n C30 C33 . 1.498(6) n C30 H30 . .9800 n C31 H31A . .9600 n C31 H31B . .9600 n C31 H31C . .9600 n C32 H32A . .9600 n C32 H32B . .9600 n C32 H32C . .9600 n C33 H33A . .9600 n C33 H33B . .9600 n C33 H33C . .9600 n C34 H34A . .9600 n C34 H34B . .9600 n C34 H34C . .9600 n C35 H35A . .9600 n C35 H35B . .9600 n C35 H35C . .9600 n C36 H36A . .9600 n C36 H36B . .9600 n C36 H36C . .9600 n C37 H37A . .9600 n C37 H37B . .9600 n C37 H37C . .9600 n C38 H38A . .9600 n C38 H38B . .9600 n C38 H38C . .9600 n