#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/00/2200004.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_2200004 loop_ _publ_author_name 'J. Suresh' 'R. V. Krishnakumar' 'S. Natarajan' _publ_section_title ; L-Phenylalanine--benzoic acid (1/1) ; _journal_coeditor_code AT6033 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3625 _journal_page_last o3627 _journal_paper_doi 10.1107/S1600536805031661 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C9 H11 N O2, C7 H6 O2' _chemical_formula_moiety 'C9 H11 N O2, C7 H6 O2' _chemical_formula_sum 'C16 H17 N O4' _chemical_formula_weight 287.31 _chemical_name_systematic ; L-Phenylalanine benzoic acid solvate ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.94(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 5.419(2) _cell_length_b 7.438(2) _cell_length_c 17.814(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.1 _cell_measurement_theta_min 9.6 _cell_volume 717.1(3) _computing_cell_refinement 'XCAD4 (Harms & Wocadlo, 1996)' _computing_data_collection 'CAD-4 EXPRESS (Enraf--Nonius, 1994)' _computing_data_reduction XCAD4 _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Nonius MACH3' _diffrn_measurement_method \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 0.039 _diffrn_reflns_av_sigmaI/netI 0.048 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 1749 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 2.3 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas 1.32(2) _exptl_crystal_density_method flotation _exptl_crystal_description block _exptl_crystal_F_000 304 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.502 _refine_diff_density_min -0.360 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 1364 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.12 _refine_ls_R_factor_all 0.112 _refine_ls_R_factor_gt 0.071 _refine_ls_shift/su_max 0.0 _refine_ls_shift/su_mean 0.0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1183P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.164 _refine_ls_wR_factor_ref 0.187 _reflns_number_gt 925 _reflns_number_total 1364 _reflns_threshold_expression I>2\s(I) _cod_data_source_file at6033.cif _cod_data_source_block I _cod_original_sg_symbol_H-M P21 _cod_database_code 2200004 _cod_database_fobs_code 2200004 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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_type_symbol O1 0.6823(7) 0.8790(7) 0.4908(2) 0.0445(11) Uani d . 1 O O2 0.3197(8) 0.8994(9) 0.5437(2) 0.0537(13) Uani d . 1 O O3 0.4874(8) 0.8877(7) 0.6784(2) 0.0473(12) Uani d . 1 O H3 0.4277 0.8892 0.6352 0.071 Uiso calc R 1 H O4 0.1611(10) 0.7170(8) 0.6975(2) 0.0633(15) Uani d . 1 O N1 0.1086(8) 1.0826(7) 0.4278(3) 0.0324(12) Uani d . 1 N H1A 0.0404 1.1182 0.3838 0.049 Uiso calc R 1 H H1B 0.1563 1.1783 0.4548 0.049 Uiso calc R 1 H H1C -0.0013 1.0201 0.4525 0.049 Uiso calc R 1 H C1 0.4567(10) 0.9131(8) 0.4900(3) 0.0337(13) Uani d . 1 C C2 0.3279(10) 0.9668(8) 0.4149(3) 0.0306(13) Uani d . 1 C H2 0.4443 1.0343 0.3853 0.037 Uiso calc R 1 H C3 0.2499(13) 0.7955(8) 0.3718(3) 0.0417(15) Uani d . 1 C H3A 0.3872 0.7117 0.3756 0.050 Uiso calc R 1 H H3B 0.1145 0.7412 0.3973 0.050 Uiso calc R 1 H C4 0.1717(10) 0.8143(7) 0.2909(3) 0.0326(13) Uani d . 1 C C5 0.3201(10) 0.9008(9) 0.2408(3) 0.0378(14) Uani d . 1 C H5 0.4666 0.9541 0.2589 0.045 Uiso calc R 1 H C6 0.2560(12) 0.9095(10) 0.1651(3) 0.0451(16) Uani d . 1 C H6 0.3593 0.9672 0.1326 0.054 Uiso calc R 1 H C7 0.0399(12) 0.8330(9) 0.1377(4) 0.0465(17) Uani d . 1 C H7 -0.0042 0.8387 0.0866 0.056 Uiso calc R 1 H C8 -0.1127(12) 0.7472(9) 0.1862(4) 0.0482(17) Uani d . 1 C H8 -0.2586 0.6935 0.1679 0.058 Uiso calc R 1 H C9 -0.0476(12) 0.7417(9) 0.2615(4) 0.0426(15) Uani d . 1 C H9 -0.1543 0.6874 0.2939 0.051 Uiso calc R 1 H C10 0.3386(11) 0.8041(9) 0.7214(3) 0.0374(14) Uani d . 1 C C11 0.4033(10) 0.8198(8) 0.8028(3) 0.0319(12) Uani d . 1 C C12 0.6119(10) 0.9067(9) 0.8312(3) 0.0394(14) Uani d . 1 C H12 0.7185 0.9609 0.7987 0.047 Uiso calc R 1 H C13 0.6627(13) 0.9134(11) 0.9075(4) 0.0506(17) Uani d . 1 C H13 0.8081 0.9671 0.9262 0.061 Uiso calc R 1 H C14 0.5020(14) 0.8419(11) 0.9563(3) 0.054(2) Uani d . 1 C H14 0.5351 0.8503 1.0079 0.064 Uiso calc R 1 H C15 0.2917(13) 0.7578(10) 0.9282(3) 0.0496(18) Uani d . 1 C H15 0.1817 0.7086 0.9610 0.060 Uiso calc R 1 H C16 0.2435(12) 0.7462(9) 0.8528(3) 0.0436(16) Uani d . 1 C H16 0.1011 0.6879 0.8344 0.052 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 O1 0.038(2) 0.032(3) 0.063(3) 0.003(2) -0.0050(18) 0.015(2) O2 0.061(3) 0.061(3) 0.039(2) 0.009(3) 0.0002(19) 0.010(3) O3 0.063(3) 0.042(3) 0.036(2) -0.011(3) -0.003(2) 0.005(2) O4 0.082(4) 0.057(4) 0.049(3) -0.032(3) -0.015(2) 0.001(3) N1 0.040(3) 0.019(3) 0.037(3) 0.004(2) -0.005(2) -0.003(2) C1 0.043(3) 0.018(3) 0.040(3) -0.003(3) -0.002(2) 0.001(3) C2 0.037(3) 0.015(3) 0.040(3) 0.001(2) 0.004(2) -0.003(2) C3 0.065(4) 0.011(3) 0.049(3) -0.003(3) 0.003(3) -0.003(3) C4 0.044(3) 0.015(3) 0.039(3) 0.003(3) 0.004(2) -0.009(3) C5 0.039(3) 0.028(3) 0.046(3) -0.007(3) 0.003(2) -0.005(3) C6 0.060(4) 0.035(4) 0.041(3) 0.006(4) 0.008(3) -0.003(3) C7 0.060(4) 0.030(4) 0.048(4) 0.010(3) -0.012(3) -0.009(3) C8 0.042(4) 0.028(4) 0.074(5) 0.003(3) -0.010(3) -0.012(4) C9 0.052(4) 0.021(3) 0.055(4) -0.003(3) 0.010(3) -0.001(3) C10 0.041(3) 0.026(3) 0.044(3) 0.004(3) -0.001(3) -0.001(3) C11 0.037(3) 0.016(3) 0.042(3) 0.002(3) -0.001(2) 0.000(3) C12 0.046(3) 0.027(3) 0.046(3) -0.007(3) 0.003(3) 0.001(3) C13 0.060(4) 0.041(4) 0.050(4) 0.000(4) -0.009(3) -0.008(4) C14 0.075(4) 0.054(5) 0.031(3) 0.011(4) -0.006(3) -0.003(3) C15 0.061(4) 0.045(4) 0.043(4) 0.002(4) 0.010(3) 0.005(3) C16 0.049(4) 0.027(4) 0.054(4) -0.002(3) -0.002(3) 0.006(3) 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' 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 C10 O3 H3 109.5 ? 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 ? O2 C1 O1 126.6(5) y O2 C1 C2 115.5(5) y O1 C1 C2 117.8(5) y N1 C2 C1 110.2(4) y N1 C2 C3 110.7(5) y C1 C2 C3 108.8(5) y N1 C2 H2 109.0 ? C1 C2 H2 109.0 ? C3 C2 H2 109.0 ? C4 C3 C2 117.6(5) y C4 C3 H3A 107.9 ? C2 C3 H3A 107.9 ? C4 C3 H3B 107.9 ? C2 C3 H3B 107.9 ? H3A C3 H3B 107.2 ? C9 C4 C5 116.9(5) ? C9 C4 C3 121.7(5) y C5 C4 C3 121.4(5) y C6 C5 C4 121.7(6) ? C6 C5 H5 119.1 ? C4 C5 H5 119.1 ? C7 C6 C5 119.8(6) ? C7 C6 H6 120.1 ? C5 C6 H6 120.1 ? C6 C7 C8 119.8(6) ? C6 C7 H7 120.1 ? C8 C7 H7 120.1 ? C9 C8 C7 119.6(6) ? C9 C8 H8 120.2 ? C7 C8 H8 120.2 ? C8 C9 C4 122.1(6) ? C8 C9 H9 118.9 ? C4 C9 H9 118.9 ? O4 C10 O3 123.5(5) y O4 C10 C11 121.8(6) y O3 C10 C11 114.7(5) y C12 C11 C16 118.6(5) y C12 C11 C10 123.1(5) y C16 C11 C10 118.3(5) y C13 C12 C11 120.0(6) ? C13 C12 H12 120.0 ? C11 C12 H12 120.0 ? C14 C13 C12 120.8(7) ? C14 C13 H13 119.6 ? C12 C13 H13 119.6 ? C13 C14 C15 119.3(6) ? C13 C14 H14 120.4 ? C15 C14 H14 120.4 ? C16 C15 C14 120.2(6) ? C16 C15 H15 119.9 ? C14 C15 H15 119.9 ? C15 C16 C11 121.0(6) ? C15 C16 H16 119.5 ? C11 C16 H16 119.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.248(7) y O2 C1 1.245(7) y O3 C10 1.298(7) y O3 H3 0.8200 ? O4 C10 1.218(7) y N1 C2 1.495(7) y N1 H1A 0.8900 ? N1 H1B 0.8900 ? N1 H1C 0.8900 ? C1 C2 1.530(8) y C2 C3 1.535(8) y C2 H2 0.9800 ? C3 C4 1.489(9) y C3 H3A 0.9700 ? C3 H3B 0.9700 ? C4 C9 1.384(8) ? C4 C5 1.389(8) ? C5 C6 1.377(8) ? C5 H5 0.9300 ? C6 C7 1.369(9) ? C6 H6 0.9300 ? C7 C8 1.383(10) ? C7 H7 0.9300 ? C8 C9 1.369(9) ? C8 H8 0.9300 ? C9 H9 0.9300 ? C10 C11 1.479(8) y C11 C12 1.376(8) ? C11 C16 1.386(8) ? C12 C13 1.374(8) ? C12 H12 0.9300 ? C13 C14 1.369(10) ? C13 H13 0.9300 ? C14 C15 1.372(10) ? C14 H14 0.9300 ? C15 C16 1.358(9) ? C15 H15 0.9300 ? C16 H16 0.9300 ? 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 O3 H3 O2 . 0.82 1.71 2.524(5) 176 N1 H1A O4 2_556 0.89 1.92 2.790(6) 167 N1 H1B O1 2_656 0.89 1.96 2.842(6) 170 N1 H1C O1 1_455 0.89 2.15 3.026(6) 168 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 O2 C1 C2 N1 30.5(7) y O1 C1 C2 N1 -153.1(5) y O2 C1 C2 C3 -91.2(7) y O1 C1 C2 C3 85.3(6) y N1 C2 C3 C4 71.9(7) y C1 C2 C3 C4 -166.8(5) y C2 C3 C4 C9 -129.4(6) y C2 C3 C4 C5 52.8(8) y C9 C4 C5 C6 -1.8(9) ? C3 C4 C5 C6 176.1(6) ? C4 C5 C6 C7 0.6(10) ? C5 C6 C7 C8 -0.1(10) ? C6 C7 C8 C9 0.9(10) ? C7 C8 C9 C4 -2.3(10) ? C5 C4 C9 C8 2.7(9) ? C3 C4 C9 C8 -175.2(6) ? O4 C10 C11 C12 175.4(7) ? O3 C10 C11 C12 -3.7(9) ? O4 C10 C11 C16 -5.8(9) ? O3 C10 C11 C16 175.1(6) ? C16 C11 C12 C13 2.4(10) ? C10 C11 C12 C13 -178.9(6) ? C11 C12 C13 C14 -3.1(11) ? C12 C13 C14 C15 2.0(11) ? C13 C14 C15 C16 -0.2(11) ? C14 C15 C16 C11 -0.6(11) ? C12 C11 C16 C15 -0.5(10) ? C10 C11 C16 C15 -179.4(6) ?