#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014393.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_2014393 loop_ _publ_author_name 'Rodrigues, V. H.' 'Matos Beja, A.' 'Paix\~ao, J. A.' 'Costa, M. M. R. R.' _publ_section_title ; Glycinium trichloroacetate ; _journal_coeditor_code SK1890 _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o71 _journal_page_last o72 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C2 H6 N O2 + , C2 Cl3 O2 -' _chemical_formula_moiety 'C2 H6 N O2 + , C2 Cl3 O2 -' _chemical_formula_sum 'C4 H6 Cl3 N O4' _chemical_formula_weight 238.45 _chemical_name_common 'glycine trichloroacetate' _chemical_name_systematic ; Glycinium trichloroacetate ; _space_group_IT_number 76 _symmetry_cell_setting tetragonal _symmetry_space_group_name_Hall 'P 4w' _symmetry_space_group_name_H-M 'P 41' _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 8 _cell_length_a 9.4416(9) _cell_length_b 9.4416(9) _cell_length_c 20.213(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.16 _cell_measurement_theta_min 9.59 _cell_volume 1801.9(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'PLATON (Spek, 2003)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method 'Profile data from \w/2\q' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 2596 _diffrn_reflns_theta_full 27.62 _diffrn_reflns_theta_max 27.62 _diffrn_reflns_theta_min 2.95 _diffrn_standards_decay_% 59 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_T_max 0.8174 _exptl_absorpt_correction_T_min 0.7223 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.332 _refine_diff_density_min -0.316 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, with 24 Friedel pairs.' _refine_ls_abs_structure_Flack 0.03(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 249 _refine_ls_number_reflns 2106 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.087 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0451 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.9874P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1247 _refine_ls_wR_factor_ref 0.1454 _reflns_number_gt 1493 _reflns_number_total 2106 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1890.cif _[local]_cod_data_source_block I _cod_database_code 2014393 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z+1/4' '-x, -y, z+1/2' 'y, -x, z-1/4' 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 O3 0.0569(5) 0.2286(6) 0.7501(2) 0.0468(12) Uani d . 1 . . O O4 0.1275(5) 0.1834(5) 0.6459(2) 0.0472(11) Uani d . 1 . . O C3 0.1277(6) 0.2469(6) 0.6997(3) 0.0350(12) Uani d . 1 . . C C4 0.2438(7) 0.3659(6) 0.7037(3) 0.0377(13) Uani d . 1 . . C Cl1 0.2524(2) 0.4636(2) 0.62889(9) 0.0572(5) Uani d . 1 . . Cl Cl2 0.2175(3) 0.4845(3) 0.76836(10) 0.0855(9) Uani d . 1 . . Cl Cl3 0.4063(2) 0.2754(3) 0.71384(17) 0.0891(9) Uani d . 1 . . Cl O3' 0.0524(5) 0.3364(5) 0.1480(2) 0.0495(12) Uani d . 1 . . O O4' 0.0901(6) 0.2940(5) 0.2541(2) 0.0507(12) Uani d . 1 . . O C3' 0.1123(7) 0.3561(6) 0.2012(3) 0.0351(13) Uani d . 1 . . C C4' 0.2366(7) 0.4651(7) 0.2016(4) 0.0455(15) Uani d . 1 . . C Cl1' 0.1949(16) 0.6061(10) 0.1467(7) 0.065(3) Uani d P 0.53(5) . . Cl Cl2' 0.272(3) 0.531(3) 0.2780(8) 0.114(6) Uani d P 0.53(5) . . Cl Cl3' 0.3812(15) 0.3735(16) 0.1654(10) 0.097(4) Uani d P 0.53(5) . . Cl Cl4' 0.237(4) 0.590(2) 0.1396(9) 0.104(6) Uani d P 0.47(5) . . Cl Cl5' 0.242(2) 0.5598(15) 0.2774(9) 0.073(4) Uani d P 0.47(5) . . Cl Cl6' 0.3921(15) 0.3668(18) 0.202(2) 0.123(8) Uani d P 0.47(5) . . Cl O1 0.1163(7) 0.3896(5) 0.0231(2) 0.0554(14) Uani d . 1 . . O H1 0.0988 0.3763 0.0624 0.083 Uiso calc R 1 . . H O2 0.0589(6) 0.1641(5) 0.0137(2) 0.0526(13) Uani d . 1 . . O C1 0.1015(7) 0.2714(6) -0.0093(3) 0.0327(13) Uani d . 1 . . C C2 0.1370(8) 0.2875(7) -0.0823(3) 0.0402(14) Uani d . 1 . . C H2A 0.0764 0.3592 -0.1018 0.048 Uiso calc R 1 . . H H2B 0.2345 0.3184 -0.0869 0.048 Uiso calc R 1 . . H N1 0.1174(5) 0.1530(5) -0.1173(2) 0.0346(11) Uani d . 1 . . N H1A 0.1916 0.0971 -0.1100 0.052 Uiso calc R 1 . . H H1B 0.1094 0.1695 -0.1605 0.052 Uiso calc R 1 . . H H1C 0.0391 0.1107 -0.1027 0.052 Uiso calc R 1 . . H O1' 0.0408(7) 0.3709(5) 0.3801(3) 0.0554(13) Uani d . 1 . . O H1' 0.0609 0.3525 0.3416 0.083 Uiso calc R 1 . . H O2' 0.0151(6) 0.1379(5) 0.3896(2) 0.0502(12) Uani d . 1 . . O C1' 0.0228(6) 0.2534(6) 0.4129(3) 0.0310(12) Uani d . 1 . . C C2' 0.0215(8) 0.2771(7) 0.4864(3) 0.0386(14) Uani d . 1 . . C H2A' 0.1096 0.3214 0.4999 0.046 Uiso calc R 1 . . H H2B' -0.0556 0.3404 0.4979 0.046 Uiso calc R 1 . . H N1' 0.0040(6) 0.1413(5) 0.5217(2) 0.0355(11) Uani d . 1 . . N H1A' -0.0848 0.1112 0.5172 0.053 Uiso calc R 1 . . H H1B' 0.0233 0.1535 0.5644 0.053 Uiso calc R 1 . . H H1C' 0.0630 0.0773 0.5047 0.053 Uiso calc R 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 O3 0.053(3) 0.061(3) 0.027(2) -0.010(2) 0.004(2) 0.000(2) O4 0.067(3) 0.049(3) 0.026(2) -0.013(2) -0.005(2) -0.008(2) C3 0.041(3) 0.043(3) 0.021(3) -0.003(3) -0.001(2) 0.002(3) C4 0.048(3) 0.041(3) 0.024(2) -0.006(3) 0.003(3) 0.001(3) Cl1 0.0851(13) 0.0479(10) 0.0387(9) -0.0091(9) 0.0095(9) 0.0062(8) Cl2 0.148(2) 0.0673(13) 0.0414(11) -0.0408(14) 0.0230(13) -0.0259(10) Cl3 0.0468(11) 0.0981(17) 0.122(2) 0.0019(11) -0.0232(14) 0.0200(17) O3' 0.060(3) 0.063(3) 0.025(2) -0.019(2) -0.005(2) -0.004(2) O4' 0.076(3) 0.048(3) 0.028(2) -0.022(3) 0.004(2) 0.006(2) C3' 0.049(3) 0.033(3) 0.024(3) 0.003(2) 0.000(3) 0.005(2) C4' 0.051(4) 0.050(4) 0.036(3) -0.005(3) 0.001(3) -0.003(3) Cl1' 0.107(6) 0.030(4) 0.058(4) -0.008(4) -0.001(4) 0.007(2) Cl2' 0.145(12) 0.161(12) 0.034(5) -0.098(10) -0.030(5) 0.014(6) Cl3' 0.052(4) 0.100(5) 0.138(9) 0.019(3) 0.026(5) -0.004(6) Cl4' 0.166(16) 0.103(10) 0.043(5) -0.085(8) -0.022(7) 0.026(6) Cl5' 0.118(8) 0.057(5) 0.043(6) -0.030(4) -0.003(5) -0.021(3) Cl6' 0.046(4) 0.100(6) 0.22(2) 0.001(3) 0.018(9) -0.006(11) O1 0.098(4) 0.042(3) 0.026(2) -0.018(3) 0.005(3) -0.007(2) O2 0.089(4) 0.039(3) 0.029(2) -0.015(2) 0.002(2) 0.001(2) C1 0.043(3) 0.033(3) 0.021(3) 0.003(3) -0.005(2) 0.002(2) C2 0.052(4) 0.040(3) 0.028(3) -0.003(3) 0.006(3) 0.002(3) N1 0.041(3) 0.042(3) 0.021(2) -0.001(2) 0.001(2) -0.003(2) O1' 0.097(4) 0.038(2) 0.031(3) -0.005(2) 0.010(3) 0.005(2) O2' 0.086(4) 0.041(3) 0.024(2) -0.004(2) -0.006(2) -0.0031(19) C1' 0.036(3) 0.028(3) 0.029(3) 0.002(2) -0.004(2) 0.003(2) C2' 0.060(4) 0.035(3) 0.021(3) 0.005(3) -0.001(3) -0.001(2) N1' 0.053(3) 0.037(3) 0.016(2) 0.005(2) -0.003(2) 0.0018(19) 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 O3 C3 . 1.230(8) ? O4 C3 . 1.242(7) ? C3 C4 . 1.572(9) ? C4 Cl2 . 1.739(7) ? C4 Cl3 . 1.769(7) ? C4 Cl1 . 1.773(7) ? O3' C3' . 1.228(8) ? O4' C3' . 1.238(7) ? C3' C4' . 1.560(9) ? C4' Cl2' . 1.697(17) ? C4' Cl4' . 1.721(18) ? C4' Cl6' . 1.737(17) ? C4' Cl3' . 1.773(14) ? C4' Cl5' . 1.776(15) ? C4' Cl1' . 1.776(14) ? Cl2' Cl6' . 2.46(2) ? Cl3' Cl6' . 0.74(3) ? O1 C1 . 1.302(7) ? O1 H1 . 0.8200 ? O2 C1 . 1.184(7) ? C1 C2 . 1.521(8) ? C2 N1 . 1.466(8) ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? N1 H1A . 0.8900 ? N1 H1B . 0.8900 ? N1 H1C . 0.8900 ? O1' C1' . 1.304(7) ? O1' H1' . 0.8200 ? O2' C1' . 1.190(7) ? C1' C2' . 1.502(8) ? C2' N1' . 1.477(8) ? C2' H2A' . 0.9700 ? C2' H2B' . 0.9700 ? N1' H1A' . 0.8900 ? N1' H1B' . 0.8900 ? N1' H1C' . 0.8900 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 O3 C3 C4 115.9(5) O4 C3 C4 113.0(5) C3 C4 Cl2 113.5(4) C3 C4 Cl3 105.4(4) Cl2 C4 Cl3 110.3(4) C3 C4 Cl1 111.1(4) Cl2 C4 Cl1 108.2(3) Cl3 C4 Cl1 108.1(4) O3' C3' O4' 127.3(6) O3' C3' C4' 116.8(6) O4' C3' C4' 115.8(6) C3' C4' Cl2' 113.1(8) C3' C4' Cl4' 116.8(10) Cl2' C4' Cl4' 114.4(9) C3' C4' Cl6' 106.5(7) Cl2' C4' Cl6' 91.7(10) Cl4' C4' Cl6' 111.3(9) C3' C4' Cl3' 104.8(7) Cl2' C4' Cl3' 113.8(10) Cl4' C4' Cl3' 91.8(11) Cl6' C4' Cl3' 24.3(11) C3' C4' Cl5' 111.1(8) Cl2' C4' Cl5' 12.6(15) Cl4' C4' Cl5' 106.5(10) Cl6' C4' Cl5' 104.1(15) Cl3' C4' Cl5' 125.2(10) C3' C4' Cl1' 108.9(7) Cl2' C4' Cl1' 109.7(11) Cl4' C4' Cl1' 14.7(14) Cl6' C4' Cl1' 126.0(13) Cl3' C4' Cl1' 106.2(7) Cl5' C4' Cl1' 99.7(8) C1 O1 H1 109.5 O2 C1 O1 125.0(6) O2 C1 C2 122.7(6) O1 C1 C2 112.2(5) N1 C2 C1 110.8(5) N1 C2 H2A 109.5 C1 C2 H2A 109.5 N1 C2 H2B 109.5 C1 C2 H2B 109.5 H2A C2 H2B 108.1 C2 N1 H1A 109.5 C2 N1 H1B 109.5 H1A N1 H1B 109.5 C2 N1 H1C 109.5 H1A N1 H1C 109.5 H1B N1 H1C 109.5 C1' O1' H1' 109.5 O2' C1' O1' 125.8(6) O2' C1' C2' 121.9(5) O1' C1' C2' 112.2(5) N1' C2' C1' 110.4(5) N1' C2' H2A' 109.6 C1' C2' H2A' 109.6 N1' C2' H2B' 109.6 C1' C2' H2B' 109.6 H2A' C2' H2B' 108.1 C2' N1' H1A' 109.5 C2' N1' H1B' 109.5 H1A' N1' H1B' 109.5 C2' N1' H1C' 109.5 H1A' N1' H1C' 109.5 H1B' N1' H1C' 109.5 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 O3' . 0.82 1.83 2.644(7) 176 N1 H1A O3' 4 0.89 1.97 2.852(7) 170 N1 H1B O3 1_554 0.89 1.96 2.832(7) 168 N1 H1C O4 2_554 0.89 2.11 2.862(7) 142 N1 H1C O2' 3_554 0.89 2.41 3.021(7) 126 O1' H1' O4' . 0.82 1.87 2.689(7) 173 N1' H1A' O4' 2 0.89 2.00 2.877(8) 167 N1' H1B' O4 . 0.89 1.94 2.797(7) 161 N1' H1B' O2' 2 0.89 2.52 2.982(7) 113 N1' H1C' O3 4 0.89 2.02 2.862(7) 158 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 O3 C3 C4 Cl2 -18.2(8) O4 C3 C4 Cl2 164.4(5) O3 C3 C4 Cl3 102.7(6) O4 C3 C4 Cl3 -74.7(6) O3 C3 C4 Cl1 -140.4(5) O4 C3 C4 Cl1 42.2(7) O3' C3' C4' Cl2' 158.6(14) O4' C3' C4' Cl2' -24.9(15) O3' C3' C4' Cl4' 22.8(16) O4' C3' C4' Cl4' -160.7(15) O3' C3' C4' Cl6' -102.1(18) O4' C3' C4' Cl6' 74.4(18) O3' C3' C4' Cl3' -76.9(10) O4' C3' C4' Cl3' 99.5(10) O3' C3' C4' Cl5' 145.2(9) O4' C3' C4' Cl5' -38.3(10) O3' C3' C4' Cl1' 36.3(9) O4' C3' C4' Cl1' -147.2(7) O2 C1 C2 N1 -2.6(9) O1 C1 C2 N1 -179.2(5) O2' C1' C2' N1' -2.3(10) O1' C1' C2' N1' -178.8(5)