#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003798.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003798 loop_ _publ_author_name 'Kolev, T.' 'Preut, H.' 'Koniczek, L.' 'Bleckmann, P.' 'Juchnovski, I.' 'Mladenova, M.' _publ_section_title ; L-(+)-\a-Bromobenzeneacetic Acid ({-})-Menthyl Ester ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1634 _journal_page_last 1636 _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C18 H25 Br1 O2' _chemical_formula_sum 'C18 H25 Br O2' _chemical_formula_weight 353.30 _chemical_melting_point 351.5(5) _chemical_name_systematic 'L-(+)-\a-Bromobenzeneacetic acid, (-)-Menthyl ester' _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method ; text program nroff under UNIX ; _cell_angle_alpha 90.0 _cell_angle_beta 92.68(7) _cell_angle_gamma 90.0 _cell_formula_units_Z 2 _cell_length_a 5.522(5) _cell_length_b 19.389(17) _cell_length_c 8.208(6) _cell_measurement_reflns_used 30 _cell_measurement_temperature 293(1) _cell_measurement_theta_max 30.31 _cell_measurement_theta_min 15.42 _cell_volume 877.8(13) _computing_cell_refinement 'Nicolet R3m/V Software' _computing_data_collection 'Nicolet R3m/V Software, Release 4.11' _computing_data_reduction 'Nicolet R3m/V Software' _computing_publication_material 'PARST (Nardelli, 1983), PLATON (Spek, 1982) and MISSYM (Le Page, 1987)' _computing_structure_refinement 'SHELXTL-Plus and SHELX76 (Sheldrick, 1976)' _computing_structure_solution 'SHELXTL-Plus and SHELX76 (Sheldrick, 1976)' _diffrn_ambient_temperature 293.0(10) _diffrn_measurement_device 'Nicolet R3m/V' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0452 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2606 _diffrn_reflns_reduction_process ; Lorentz-polarization correction, data averaged ; _diffrn_reflns_theta_max 22.5 _diffrn_reflns_theta_min 1.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 2.32 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.336 _exptl_crystal_description 'approximately quadratic column' _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.3 _refine_diff_density_min -0.3 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 0.68 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 190 _refine_ls_number_reflns 1001 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_obs 0.0292 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean 0.0005 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme unit _refine_ls_wR_factor_all 0.0401 _refine_ls_wR_factor_obs 0.0299 _reflns_limit_h_max 6 _reflns_limit_h_min -6 _reflns_limit_k_max 21 _reflns_limit_k_min -1 _reflns_limit_l_max 9 _reflns_limit_l_min 0 _reflns_number_observed 1001 _reflns_number_total 1272 _reflns_observed_criterion refl_observed_if_F>_4.0_sigma(F) _[local]_cod_data_source_file ka1107.cif _[local]_cod_data_source_block global _[local]_cod_cif_authors_sg_H-M 'P 21' _[local]_cod_cif_authors_sg_Hall 'P 2y1' _[local]_cod_chemical_formula_sum_orig 'C18 H25 Br1 O2' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '351-352' was changed to '351.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 878.0(10) _cod_database_code 2003798 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,1/2+y,-z loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C International_Tables_Vol_IV_Table_2.2B 0.002 0.002 H International_Tables_Vol_IV_Table_2.2B 0 0 O International_Tables_Vol_IV_Table_2.2B 0.008 0.006 International_Tables_Vol_IV_Table_2.2B 2.456 2 -0.374 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_calc_attached_atom Br(1) 0.1989(2) 0.0 0.07376(9) .0885 Uani ? ? O(1) -0.2872(9) 0.0765(3) -0.1618(6) .0691 Uani ? ? O(2) -0.0389(8) 0.1447(2) -0.0115(5) .0406 Uani ? ? C(1) -0.091(1) 0.0898(4) -0.1059(7) .0412 Uani ? ? C(2) 0.135(1) 0.0485(4) -0.1331(7) .0413 Uani ? ? H(2a) 0.265(1) 0.0802(4) -0.1495(7) .0600 Uiso calc C(2) C(3) 0.1197(9) -0.0011(5) -0.2731(6) .0369 Uani ? ? C(4) 0.297(1) -0.0010(6) -0.3847(6) .0459 Uani ? ? H(4a) 0.424(1) 0.0327(6) -0.3735(6) .0600 Uiso calc C(4) C(5) 0.292(1) -0.0452(4) -0.5143(8) .0534 Uani ? ? H(5a) 0.418(1) -0.0457(4) -0.5908(8) .0600 Uiso calc C(5) C(6) 0.109(1) -0.0916(4) -0.5333(8) .0543 Uani ? ? H(6a) 0.104(1) -0.1240(4) -0.6219(8) .0600 Uiso calc C(6) C(7) -0.071(1) -0.0934(4) -0.4250(9) .0558 Uani ? ? H(7a) -0.205(1) -0.1246(4) -0.4416(9) .0600 Uiso calc C(7) C(8) -0.067(1) -0.0485(4) -0.2942(8) .0481 Uani ? ? H(8a) -0.191(1) -0.0510(4) -0.2164(8) .0600 Uiso calc C(8) C(9) -0.247(1) 0.1834(4) 0.0428(8) .0391 Uani ? ? H(9a) -0.380(1) 0.1524(4) 0.0576(8) .0600 Uiso calc C(9) C(10) -0.323(1) 0.2369(4) -0.0838(9) .0482 Uani ? ? H(10a) -0.365(1) 0.2148(4) -0.1858(9) .0600 Uiso calc C(10) H(10b) -0.188(1) 0.2670(4) -0.0996(9) .0600 Uiso calc C(10) C(11) -0.533(1) 0.2788(4) -0.028(1) .0551 Uani ? ? H(11a) -0.666(1) 0.2475(4) -0.014(1) .0600 Uiso calc C(11) C(12) -0.470(1) 0.3109(4) 0.1370(9) .0602 Uani ? ? H(12a) -0.610(1) 0.3345(4) 0.1751(9) .0600 Uiso calc C(12) H(12b) -0.344(1) 0.3442(4) 0.1255(9) .0600 Uiso calc C(12) C(13) -0.387(1) 0.2574(4) 0.2619(9) .0540 Uani ? ? H(13a) -0.519(1) 0.2269(4) 0.2817(9) .0600 Uiso calc C(13) H(13b) -0.340(1) 0.2798(4) 0.3628(9) .0600 Uiso calc C(13) C(14) -0.171(1) 0.2149(4) 0.2056(8) .0406 Uani ? ? H(14a) -0.042(1) 0.2464(4) 0.1852(8) .0600 Uiso calc C(14) C(15) -0.077(1) 0.1620(4) 0.3332(8) .0475 Uani ? ? H(15a) 0.058(1) 0.1392(4) 0.2859(8) .0600 Uiso calc C(15) C(16) 0.022(2) 0.1957(4) 0.4895(9) .0668 Uani ? ? H(16a) 0.083(2) 0.1616(4) 0.5657(9) .0600 Uiso calc C(16) H(16b) 0.151(2) 0.2265(4) 0.4640(9) .0600 Uiso calc C(16) H(16c) -0.106(2) 0.2213(4) 0.5367(9) .0600 Uiso calc C(16) C(17) -0.258(2) 0.1060(4) 0.371(1) .0805 Uani ? ? H(17a) -0.187(2) 0.0741(4) 0.449(1) .0600 Uiso calc C(17) H(17b) -0.398(2) 0.1273(4) 0.415(1) .0600 Uiso calc C(17) H(17c) -0.306(2) 0.0819(4) 0.273(1) .0600 Uiso calc C(17) C(18) -0.619(2) 0.3313(5) -0.156(1) .0740 Uani ? ? H(18a) -0.658(2) 0.3093(5) -0.258(1) .0600 Uiso calc C(18) H(18b) -0.760(2) 0.3542(5) -0.118(1) .0600 Uiso calc C(18) H(18c) -0.492(2) 0.3644(5) -0.169(1) .0600 Uiso calc C(18) loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Br(1) 1.365(8) -.005(6) -.243(4) .766(5) .409(8) .497(4) O(1) .371(29) -.462(34) -.080(27) .761(39) .047(20) .931(37) O(2) .387(27) -.102(22) .063(21) .369(26) .010(20) .466(25) C(1) .430(46) -.012(33) -.016(32) .443(42) -.027(30) .359(34) C(2) .361(41) .008(32) .014(31) .415(40) .016(30) .463(37) H(2a) .600(45) .0 .0 .0 .0 .0 C(3) .351(33) -.047(46) -.048(26) .340(32) .107(40) .411(30) C(4) .450(37) .022(53) -.033(27) .505(36) -.075(40) .416(31) H(4a) .600(45) .0 .0 .0 .0 .0 C(5) .427(45) -.135(39) .036(33) .770(54) .015(40) .407(38) H(5a) .600(45) .0 .0 .0 .0 .0 C(6) .622(52) -.185(38) .010(38) .554(49) .036(40) .453(40) H(6a) .600(45) .0 .0 .0 .0 .0 C(7) .591(52) -.117(40) -.072(43) .383(44) -.100(30) .690(49) H(7a) .600(45) .0 .0 .0 .0 .0 C(8) .479(45) -.017(36) .096(34) .415(42) -.075(30) .558(43) H(8a) .600(45) .0 .0 .0 .0 .0 C(9) .412(46) -.001(32) .115(34) .377(39) -.006(30) .392(38) H(9a) .600(45) .0 .0 .0 .0 .0 C(10) .421(42) -.039(37) .075(35) .465(41) -.035(30) .565(44) H(10a) .600(45) .0 .0 .0 .0 .0 H(10b) .600(45) .0 .0 .0 .0 .0 C(11) .441(54) .011(42) .059(42) .443(48) -.030(40) .772(57) H(11a) .600(45) .0 .0 .0 .0 .0 C(12) .565(56) -.101(44) .126(44) .489(48) .145(40) .761(54) H(12a) .600(45) .0 .0 .0 .0 .0 H(12b) .600(45) .0 .0 .0 .0 .0 C(13) .620(55) -.058(38) .153(39) .463(46) .061(40) .549(44) H(13a) .600(45) .0 .0 .0 .0 .0 H(13b) .600(45) .0 .0 .0 .0 .0 C(14) .388(42) -.029(33) .112(32) .434(42) -.049(30) .405(39) H(14a) .600(45) .0 .0 .0 .0 .0 C(15) .462(45) .024(36) .048(34) .480(44) -.034(30) .485(42) H(15a) .600(45) .0 .0 .0 .0 .0 C(16) .774(58) .018(42) .006(40) .809(60) .036(50) .419(42) H(16a) .600(45) .0 .0 .0 .0 .0 H(16b) .600(45) .0 .0 .0 .0 .0 H(16c) .600(45) .0 .0 .0 .0 .0 C(17) .824(67) .271(51) -.038(51) .723(62) -.151(50) .861(63) H(17a) .600(45) .0 .0 .0 .0 .0 H(17b) .600(45) .0 .0 .0 .0 .0 H(17c) .600(45) .0 .0 .0 .0 .0 C(18) .647(61) .067(53) -.117(50) .673(60) .144(50) .885(64) H(18a) .600(45) .0 .0 .0 .0 .0 H(18b) .600(45) .0 .0 .0 .0 .0 H(18c) .600(45) .0 .0 .0 .0 .0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 0 0 0 4 0 0 0 2 -2 0 0 0 -4 0 0 0 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C(1) O(2) C(9) 115.6(5) yes O(1) C(1) O(2) 124.5(7) yes O(2) C(1) C(2) 110.5(6) yes O(1) C(1) C(2) 125.0(6) yes Br(1) C(2) C(1) 104.1(4) yes C(1) C(2) C(3) 116.0(5) yes Br(1) C(2) C(3) 110.9(5) yes C(2) C(3) C(8) 122.4(6) yes C(2) C(3) C(4) 119.8(6) yes C(4) C(3) C(8) 117.9(6) yes C(3) C(4) C(5) 122.2(6) yes C(4) C(5) C(6) 119.5(7) yes C(5) C(6) C(7) 120.2(7) yes C(6) C(7) C(8) 120.3(7) yes C(3) C(8) C(7) 120.0(7) yes O(2) C(9) C(14) 106.6(6) yes O(2) C(9) C(10) 109.9(6) yes C(10) C(9) C(14) 112.8(6) yes C(9) C(10) C(11) 110.8(6) yes C(10) C(11) C(18) 111.8(7) yes C(10) C(11) C(12) 110.1(7) yes C(12) C(11) C(18) 113.1(7) yes C(11) C(12) C(13) 112.0(6) yes C(12) C(13) C(14) 112.3(6) yes C(9) C(14) C(13) 107.1(6) yes C(13) C(14) C(15) 113.3(6) yes C(9) C(14) C(15) 113.8(6) yes C(14) C(15) C(17) 114.2(6) yes C(14) C(15) C(16) 112.6(6) yes C(16) C(15) C(17) 110.5(6) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Br(1) C(2) 1.959(6) yes O(1) C(1) 1.184(8) yes O(2) C(1) 1.339(8) yes O(2) C(9) 1.461(8) yes C(1) C(2) 1.507(9) yes C(2) C(3) 1.499(9) yes C(3) C(4) 1.370(8) yes C(3) C(8) 1.380(10) yes C(4) C(5) 1.370(10) yes C(5) C(6) 1.360(10) yes C(6) C(7) 1.370(10) yes C(7) C(8) 1.380(10) yes C(9) C(10) 1.510(10) yes C(9) C(14) 1.511(9) yes C(10) C(11) 1.510(10) yes C(11) C(12) 1.520(10) yes C(11) C(18) 1.520(10) yes C(12) C(13) 1.510(10) yes C(13) C(14) 1.540(10) yes C(14) C(15) 1.539(9) yes C(15) C(16) 1.520(10) yes C(15) C(17) 1.520(10) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O(1) C(1) C(2) C(3) 16.4(10) yes C(10) C(9) C(14) C(13) 57.9(8) yes C(14) C(9) C(10) C(11) -59.6(8) yes C(9) C(10) C(11) C(12) 55.4(8) yes C(10) C(11) C(12) C(13) -54.3(9) yes C(11) C(12) C(13) C(14) 55.8(9) yes C(12) C(13) C(14) C(9) -55.7(8) yes _journal_paper_doi 10.1107/S0108270195001430