#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014313.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_2014313 loop_ _publ_author_name 'Bryndal, Iwona' 'Jaremko, Mariusz' 'Jaremko, \/Lukasz' 'Lis, Tadeusz' _publ_section_title ; Comparison of the methyl ester of L-tyrosine hydrochloride and its methanol monosolvate ; _journal_coeditor_code BM1620 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o111 _journal_page_last o114 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C10 H14 N O3 + , Cl - , C H4 O' _chemical_formula_moiety 'C10 H14 N O3 + , Cl - , C H4 O' _chemical_formula_sum 'C11 H18 Cl N O4' _chemical_formula_weight 263.71 _chemical_melting_point 463 _chemical_name_common 'L-tyrosine methyl ester hydrochloride methanol solvate' _chemical_name_systematic ; methyl 2-ammonio-3-(4-hydroxyphenyl)propionate chloride methanol solvate ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.424(2) _cell_length_b 11.080(3) _cell_length_c 21.647(5) _cell_measurement_reflns_used 11981 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 75.94 _cell_measurement_theta_min 4.08 _cell_volume 1300.9(7) _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_molecular_graphics 'XP (Bruker, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'Kuma KM4 CCD \k-geometry' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54180 _diffrn_reflns_av_R_equivalents 0.046 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 12812 _diffrn_reflns_theta_full 75.94 _diffrn_reflns_theta_max 75.94 _diffrn_reflns_theta_min 4.08 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.653 _exptl_absorpt_correction_T_max 0.8570 _exptl_absorpt_correction_T_min 0.3391 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(CrysAlis RED; Oxford Diffraction, 2003)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.48 _refine_diff_density_min -0.34 _refine_ls_abs_structure_details 'Flack (1983), with how many Friedel pairs' _refine_ls_abs_structure_Flack -0.02(2) _refine_ls_extinction_coef 0.0101(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2563 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.06 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0403 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0765P)^2^+0.4385P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.107 _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 2462 _reflns_number_total 2563 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1620.cif _[local]_cod_data_source_block II _cod_database_code 2014313 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_type_symbol _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 Cl Cl 0.49594(9) 0.66526(4) 0.90812(2) 0.01987(17) Uani d . 1 . . O O1 0.4936(3) 0.24977(13) 0.81774(7) 0.0258(3) Uani d . 1 . . H H1 0.5736 0.3034 0.8364 0.031 Uiso calc R 1 . . O O2 0.4029(3) 0.43158(14) 0.52895(7) 0.0217(3) Uani d . 1 . . O O3 0.2138(3) 0.60732(14) 0.55071(7) 0.0241(4) Uani d . 1 . . N N 0.0024(4) 0.29849(15) 0.55319(7) 0.0183(3) Uani d . 1 . . H H1N 0.0125 0.2836 0.5119 0.022 Uiso calc R 1 . . H H2N -0.1322 0.2604 0.5690 0.022 Uiso calc R 1 . . H H3N 0.1406 0.2706 0.5722 0.022 Uiso calc R 1 . . C C1 0.2246(4) 0.48728(19) 0.54612(9) 0.0179(4) Uani d . 1 . . C C2 -0.0202(4) 0.43061(18) 0.56370(9) 0.0188(4) Uani d . 1 . . H H2 -0.1488 0.4624 0.5349 0.023 Uiso calc R 1 . . C C3 -0.1041(4) 0.4575(2) 0.63007(10) 0.0209(5) Uani d . 1 . . H H31 -0.1095 0.5461 0.6359 0.025 Uiso calc R 1 . . H H32 -0.2738 0.4264 0.6355 0.025 Uiso calc R 1 . . C C4 0.0588(4) 0.4034(2) 0.67962(10) 0.0196(4) Uani d . 1 . . C C5 0.0094(5) 0.28870(18) 0.70304(9) 0.0211(4) Uani d . 1 . . H H5 -0.1287 0.2449 0.6880 0.025 Uiso calc R 1 . . C C6 0.1593(4) 0.2374(2) 0.74811(10) 0.0232(5) Uani d . 1 . . H H6 0.1250 0.1586 0.7632 0.028 Uiso calc R 1 . . C C7 0.3591(4) 0.3015(2) 0.77104(9) 0.0207(4) Uani d . 1 . . C C8 0.4124(4) 0.41596(19) 0.74803(9) 0.0201(5) Uani d . 1 . . H H8 0.5499 0.4597 0.7635 0.024 Uiso calc R 1 . . C C9 0.2634(4) 0.46629(19) 0.70221(10) 0.0201(4) Uani d . 1 . . H H9 0.3012 0.5440 0.6862 0.024 Uiso calc R 1 . . C C10 0.4393(4) 0.6708(2) 0.53444(11) 0.0263(5) Uani d . 1 . . H H101 0.4885 0.6488 0.4924 0.039 Uiso calc R 1 . . H H102 0.5705 0.6484 0.5634 0.039 Uiso calc R 1 . . H H103 0.4109 0.7581 0.5366 0.039 Uiso calc R 1 . . O O4 0.7358(3) 0.41512(14) 0.88760(7) 0.0261(4) Uani d . 1 . . H H4 0.6493 0.4767 0.8940 0.031 Uiso calc R 1 . . C C11 0.9791(5) 0.4510(2) 0.87049(12) 0.0325(5) Uani d . 1 . . H H11 0.9785 0.4797 0.8277 0.049 Uiso calc R 1 . . H H12 1.0909 0.3819 0.8742 0.049 Uiso calc R 1 . . H H13 1.0349 0.5160 0.8978 0.049 Uiso calc R 1 . . 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 0.0151(2) 0.0227(3) 0.0218(3) 0.0011(2) 0.0001(2) -0.00282(15) O1 0.0310(8) 0.0210(7) 0.0252(7) 0.0018(8) -0.0091(8) 0.0010(5) O2 0.0158(7) 0.0235(8) 0.0259(8) 0.0011(6) 0.0024(6) -0.0002(6) O3 0.0224(8) 0.0187(7) 0.0310(8) -0.0004(6) 0.0042(7) 0.0011(6) N 0.0140(7) 0.0223(8) 0.0188(8) -0.0025(8) -0.0001(8) -0.0006(6) C1 0.0174(10) 0.0177(9) 0.0185(9) -0.0003(8) -0.0037(8) 0.0010(7) C2 0.0128(9) 0.0224(10) 0.0213(9) -0.0013(9) 0.0005(9) 0.0001(7) C3 0.0167(9) 0.0249(11) 0.0211(10) 0.0011(8) 0.0007(8) 0.0000(8) C4 0.0160(11) 0.0234(10) 0.0195(9) 0.0012(7) 0.0034(7) -0.0029(8) C5 0.0195(9) 0.0239(10) 0.0198(9) -0.0032(10) 0.0011(9) -0.0023(7) C6 0.0264(11) 0.0226(11) 0.0205(10) -0.0032(9) 0.0011(9) 0.0007(8) C7 0.0200(10) 0.0226(10) 0.0194(10) 0.0027(8) -0.0009(8) 0.0004(8) C8 0.0177(10) 0.0221(11) 0.0205(10) -0.0011(8) -0.0002(8) -0.0026(9) C9 0.0168(9) 0.0204(10) 0.0232(10) 0.0002(8) 0.0028(8) 0.0000(8) C10 0.0233(11) 0.0224(10) 0.0331(11) -0.0057(8) 0.0022(9) 0.0011(9) O4 0.0243(8) 0.0219(8) 0.0321(8) 0.0023(7) -0.0010(7) -0.0026(6) C11 0.0268(12) 0.0355(12) 0.0351(12) 0.0034(12) 0.0053(11) -0.0003(10) 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 C7 . 1.372(3) yes O1 H1 . 0.8400 no O2 C1 . 1.206(3) yes O3 C1 . 1.335(3) yes O3 C10 . 1.454(3) yes N C2 . 1.487(2) yes N H1N . 0.9100 no N H2N . 0.9100 no N H3N . 0.9100 no C1 C2 . 1.517(3) yes C2 C3 . 1.536(3) yes C2 H2 . 1.0000 no C3 C4 . 1.513(3) yes C3 H31 . 0.9900 no C3 H32 . 0.9900 no C4 C5 . 1.394(3) no C4 C9 . 1.399(3) no C5 C6 . 1.392(3) no C5 H5 . 0.9500 no C6 C7 . 1.388(3) yes C6 H6 . 0.9500 no C7 C8 . 1.392(3) yes C8 C9 . 1.396(3) yes C8 H8 . 0.9500 no C9 H9 . 0.9500 no C10 H101 . 0.9800 no C10 H102 . 0.9800 no C10 H103 . 0.9800 no O4 C11 . 1.427(3) no O4 H4 . 0.8400 no C11 H11 . 0.9800 no C11 H12 . 0.9800 no C11 H13 . 0.9800 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C7 O1 H1 109.5 no C1 O3 C10 115.28(17) no C2 N H1N 109.5 no C2 N H2N 109.5 no H1N N H2N 109.5 no C2 N H3N 109.5 no H1N N H3N 109.5 no H2N N H3N 109.5 no O2 C1 O3 124.6(2) no O2 C1 C2 124.56(19) no O3 C1 C2 110.80(18) no N C2 C1 107.28(17) no N C2 C3 111.00(16) no C1 C2 C3 114.44(17) no N C2 H2 108.0 no C1 C2 H2 108.0 no C3 C2 H2 108.0 no C4 C3 C2 114.41(17) no C4 C3 H31 108.7 no C2 C3 H31 108.7 no C4 C3 H32 108.7 no C2 C3 H32 108.7 no H31 C3 H32 107.6 no C5 C4 C9 118.7(2) no C5 C4 C3 120.45(19) no C9 C4 C3 120.9(2) no C6 C5 C4 121.0(2) no C6 C5 H5 119.5 no C4 C5 H5 119.5 no C7 C6 C5 119.8(2) no C7 C6 H6 120.1 no C5 C6 H6 120.1 no O1 C7 C6 117.67(19) no O1 C7 C8 122.3(2) no C6 C7 C8 120.0(2) no C7 C8 C9 119.9(2) no C7 C8 H8 120.1 no C9 C8 H8 120.1 no C8 C9 C4 120.6(2) no C8 C9 H9 119.7 no C4 C9 H9 119.7 no O3 C10 H101 109.5 no O3 C10 H102 109.5 no H101 C10 H102 109.5 no O3 C10 H103 109.5 no H101 C10 H103 109.5 no H102 C10 H103 109.5 no C11 O4 H4 109.5 no O4 C11 H11 109.5 no O4 C11 H12 109.5 no H11 C11 H12 109.5 no O4 C11 H13 109.5 no H11 C11 H13 109.5 no H12 C11 H13 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O1 H1 O4 . 0.84 1.88 2.715(2) 173 O4 H4 Cl . 0.84 2.27 3.0938(18) 167 N H1N Cl 2_564 0.91 2.32 3.1659(18) 155 N H2N Cl 3_546 0.91 2.29 3.192(2) 170 N H3N Cl 3_646 0.91 2.33 3.207(2) 162 C2 H2 O2 1_455 1.00 2.46 3.219(3) 132 C9 H9 O1 3_656 0.95 2.54 3.434(3) 157 C10 H103 O4 3_656 0.98 2.52 3.328(3) 140 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 C10 O3 C1 O2 -1.2(3) yes C10 O3 C1 C2 -179.62(17) no N C2 C1 O2 -2.2(3) yes O3 C1 C2 N 176.15(16) no O2 C1 C2 C3 121.4(2) yes O3 C1 C2 C3 -60.2(2) no N C2 C3 C4 55.8(2) yes C1 C2 C3 C4 -65.8(2) no C2 C3 C4 C5 -90.8(2) yes C2 C3 C4 C9 88.3(2) yes C9 C4 C5 C6 0.2(3) no C3 C4 C5 C6 179.3(2) no C4 C5 C6 C7 1.0(3) no C5 C6 C7 O1 176.60(19) no C5 C6 C7 C8 -1.4(3) no O1 C7 C8 C9 -177.39(19) no C6 C7 C8 C9 0.5(3) no C7 C8 C9 C4 0.8(3) no C5 C4 C9 C8 -1.1(3) no C3 C4 C9 C8 179.83(19) no _journal_paper_doi 10.1107/S0108270106002137