#------------------------------------------------------------------------------ #$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $ #$Revision: 19 $ #$URL: svn://www.crystallography.net/cod/cif/2/2007034.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_2007034 _journal_data_validation_number ? _journal_name_full 'Acta Crystalllographica' _journal_year 1998 _journal_volume C54 _publ_section_title ; 8-(2-Bromo-4-methylanilino)-9-hydroxy-4-methyl-7,8,9,10-tetrahydro-7,8- benzocoumarin ; loop_ _publ_author_name 'Kandasamy Chinnakali' 'Hoong-Kun Fun' 'Kamaraj Sriraghavan' 'Vayalakkavoor T.Ramakrishnan' _chemical_formula_moiety 'C21 H20 Br N O3' _chemical_formula_sum 'C21 H20 Br N O3' _chemical_formula_weight 414.29 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 19.8970(18) _cell_length_b 11.878(2) _cell_length_c 8.0208(12) _cell_angle_alpha 90.00 _cell_angle_beta 97.204(10) _cell_angle_gamma 90.00 _cell_volume 1880.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.463 _diffrn_ambient_temperature 293(2) _refine_ls_R_factor_obs .0437 _refine_ls_wR_factor_obs .1026 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol Br .16979(2) -.03046(3) .49627(7) .0949(2) Uani d . 1 . Br O1 .43772(10) .5801(2) .3165(3) .0578(6) Uani d . 1 . O C2 .4790(2) .6676(3) .2841(5) .0639(10) Uani d . 1 . C C3 .4552(2) .7801(3) .3107(6) .0709(12) Uani d . 1 . C C4 .3949(2) .8017(3) .3631(5) .0601(10) Uani d . 1 . C C5 .2879(2) .7170(3) .4485(6) .0671(11) Uani d . 1 . C C6 .2507(2) .6245(3) .4734(5) .0629(11) Uani d . 1 . C C7 .27412(15) .5157(3) .4471(4) .0492(8) Uani d . 1 . C C8 .33778(14) .5022(2) .3938(4) .0464(8) Uani d . 1 . C C9 .37494(14) .5985(3) .3702(4) .0491(8) Uani d . 1 . C C10 .3521(2) .7074(3) .3946(5) .0542(9) Uani d . 1 . C O11 .53234(12) .6414(2) .2363(4) .0892(9) Uani d . 1 . O C12 .3716(3) .9207(3) .3846(9) .0790(15) Uani d . 1 . C C13 .2307(2) .4156(3) .4773(6) .0560(10) Uani d . 1 . C C14 .2504(2) .3118(3) .3811(5) .0499(9) Uani d . 1 . C C15 .3261(2) .2936(3) .4325(5) .0487(8) Uani d . 1 . C C16 .3656(2) .3871(3) .3608(6) .0501(9) Uani d . 1 . C O17 .34392(13) .1852(2) .3763(4) .0671(8) Uani d . 1 . O N18 .21404(14) .2105(2) .4234(4) .0527(7) Uani d . 1 . N C19 .1494(2) .1872(3) .3460(4) .0485(8) Uani d . 1 . C C20 .1094(2) .2650(3) .2503(5) .0600(10) Uani d . 1 . C C21 .0440(2) .2408(4) .1783(6) .0697(11) Uani d . 1 . C C22 .0150(2) .1368(4) .1997(6) .0781(12) Uani d . 1 . C C23 .0534(2) .0581(4) .2972(6) .0770(13) Uani d . 1 . C C24 .1192(2) .0821(3) .3671(5) .0605(10) Uani d . 1 . C C25 -.0573(2) .1112(5) .1225(7) .120(2) Uani d . 1 . C H25A -.0653(7) .0316(6) .126(5) .181 Uiso calc R 1 . H H25B -.0638(6) .136(3) .0078(17) .181 Uiso calc R 1 . H H25C -.0886(2) .150(3) .185(3) .181 Uiso calc R 1 . H H3 .487(2) .838(4) .295(5) .107(15) Uiso d . 1 . H H5 .2701(16) .792(3) .464(4) .072(11) Uiso d . 1 . H H6 .2117(16) .633(3) .520(4) .062(10) Uiso d . 1 . H H12A .324(3) .937(4) .295(6) .123(16) Uiso d . 1 . H H12B .402(2) .957(4) .361(6) .090(16) Uiso d . 1 . H H12C .359(2) .937(4) .491(6) .091(17) Uiso d . 1 . H H13A .2336(18) .406(3) .586(5) .073(14) Uiso d . 1 . H H13B .178(2) .439(4) .435(5) .109(14) Uiso d . 1 . H H14 .2452(14) .324(3) .261(4) .049(9) Uiso d . 1 . H H15 .3360(14) .297(3) .556(4) .051(10) Uiso d . 1 . H H16A .4123(17) .382(3) .411(4) .061(10) Uiso d . 1 . H H16B .3618(15) .375(3) .233(5) .062(11) Uiso d . 1 . H H17 .382(2) .179(4) .363(6) .105(17) Uiso d . 1 . H H18 .2394(15) .154(3) .436(4) .053(10) Uiso d . 1 . H H20 .1279(15) .320(3) .222(4) .045(9) Uiso d . 1 . H H21 .0247(16) .287(3) .089(4) .059(11) Uiso d . 1 . H H23 .030(2) -.005(4) .320(6) .100(14) 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 Br .0900(3) .0405(2) .1589(5) -.0013(2) .0340(3) .0108(3) O1 .0446(11) .0376(11) .093(2) -.0084(10) .0148(12) .0013(13) C2 .053(2) .049(2) .090(3) -.012(2) .006(2) .002(2) C3 .063(2) .041(2) .109(4) -.017(2) .013(2) .008(2) C4 .067(2) .034(2) .076(3) -.005(2) -.002(2) .001(2) C5 .057(2) .037(2) .107(3) .009(2) .013(2) -.004(2) C6 .047(2) .045(2) .098(3) .003(2) .016(2) -.007(2) C7 .044(2) .038(2) .065(2) .0012(14) .007(2) .000(2) C8 .041(2) .0362(15) .061(2) .0004(12) .003(2) -.001(2) C9 .040(2) .041(2) .065(2) -.0028(14) .005(2) .001(2) C10 .053(2) .037(2) .070(3) -.0028(15) -.002(2) .003(2) O11 .0538(14) .0572(15) .163(3) -.0104(12) .040(2) .004(2) C12 .084(3) .031(2) .122(5) -.003(2) .013(4) .002(3) C13 .047(2) .045(2) .078(3) -.003(2) .017(2) -.002(2) C14 .045(2) .037(2) .070(3) -.0032(13) .014(2) .005(2) C15 .047(2) .035(2) .065(3) -.0020(14) .010(2) -.004(2) C16 .041(2) .0332(15) .077(3) -.0012(14) .011(2) -.001(2) O17 .0547(15) .0337(12) .117(2) .0019(11) .027(2) -.0020(13) N18 .050(2) .0388(14) .072(2) -.0085(13) .017(2) .001(2) C19 .047(2) .047(2) .055(2) -.005(2) .019(2) -.009(2) C20 .052(2) .054(2) .077(3) -.014(2) .018(2) .003(2) C21 .053(2) .083(3) .073(3) -.004(2) .008(2) .005(3) C22 .051(2) .095(3) .089(3) -.021(2) .011(2) -.012(3) C23 .067(3) .063(2) .108(4) -.026(2) .035(3) -.018(3) C24 .056(2) .042(2) .087(3) -.009(2) .025(2) -.008(2) C25 .066(3) .147(5) .147(5) -.043(3) .005(3) -.029(4) 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 Br C24 . 1.901(4) ? O1 C2 . 1.370(4) ? O1 C9 . 1.389(3) ? C2 O11 . 1.214(4) ? C2 C3 . 1.442(5) ? C3 C4 . 1.345(5) yes C4 C10 . 1.448(4) ? C4 C12 . 1.505(5) ? C5 C6 . 1.354(5) yes C5 C10 . 1.404(5) ? C6 C7 . 1.399(4) ? C7 C8 . 1.396(4) ? C7 C13 . 1.506(5) ? C8 C9 . 1.388(4) ? C8 C16 . 1.510(4) ? C9 C10 . 1.393(4) ? C13 C14 . 1.531(5) ? C14 N18 . 1.465(4) yes C14 C15 . 1.526(4) ? C15 O17 . 1.424(4) yes C15 C16 . 1.515(4) ? N18 C19 . 1.384(4) yes C19 C20 . 1.386(5) ? C19 C24 . 1.405(4) ? C20 C21 . 1.387(5) ? C21 C22 . 1.384(6) ? C22 C23 . 1.385(6) ? C22 C25 . 1.525(5) ? C23 C24 . 1.387(5) ?