#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2012949.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_2012949 loop_ _publ_author_name 'H\"ubschle, Christian B.' 'Dittrich, Birger' 'Luger, Peter' _publ_section_title ; L-Tryptophan formic acid solvate at 183K ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o540 _journal_page_last o542 _journal_volume 58 _journal_year 2002 _chemical_formula_iupac 'C11 H12 N2 O2 , C H2 O2' _chemical_formula_moiety 'C11 H12 N2 O2 , C H2 O2' _chemical_formula_sum 'C12 H14 N2 O4' _chemical_formula_weight 250.25 _chemical_name_common 'L-Tryptophan formic acid solvate' _chemical_name_systematic ; L-2-Amino-3-(1H-indol-3-yl)-propionic acid formic acid 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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.3163(3) _cell_length_b 8.1348(4) _cell_length_c 27.259(2) _cell_measurement_reflns_used 5433 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 32.44 _cell_measurement_theta_min 2.11 _cell_volume 1178.87(12) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SMART _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996) and SCHAKAL99 (Keller & Pierrard, 1999)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_measured_fraction_theta_full 0.955 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_device_type 'Bruker AXS SMART CCD area-detector' _diffrn_measurement_method '\w and \f' _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 0.064 _diffrn_reflns_av_sigmaI/netI 0.049 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_number 14392 _diffrn_reflns_theta_full 33.12 _diffrn_reflns_theta_max 33.12 _diffrn_reflns_theta_min 2.61 _diffrn_standards_decay_% none _diffrn_standards_number no _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.761 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '(SADABS; Blessing, 1995; Siemens, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.37 _refine_diff_density_min -0.24 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2492 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.065 _refine_ls_R_factor_gt 0.051 _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^)+(0.0702P)^2^+0.0077P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.121 _refine_ls_wR_factor_ref 0.126 _reflns_number_gt 2104 _reflns_number_total 2492 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1566.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2012949 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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_occupancy _atom_site_type_symbol N1 0.8375(4) 0.1803(3) 0.95189(6) 0.0285(4) Uani d 1 N C2 0.7169(4) 0.0686(3) 0.92251(7) 0.0260(4) Uani d 1 C C3 0.5132(4) 0.1397(2) 0.90033(6) 0.0206(3) Uani d 1 C C4 0.3415(4) 0.4396(3) 0.91063(7) 0.0241(4) Uani d 1 C C5 0.3909(4) 0.5876(3) 0.93428(7) 0.0283(4) Uani d 1 C C6 0.6012(5) 0.6056(3) 0.96504(7) 0.0319(5) Uani d 1 C C7 0.7655(4) 0.4768(3) 0.97318(7) 0.0288(4) Uani d 1 C C8 0.7143(4) 0.3275(3) 0.94962(6) 0.0242(4) Uani d 1 C C9 0.5058(4) 0.3075(3) 0.91776(6) 0.0209(4) Uani d 1 C C10 0.3366(4) 0.0536(2) 0.86617(7) 0.0223(4) Uani d 1 C C11 0.3690(4) 0.0946(2) 0.81137(6) 0.0198(3) Uani d 1 C C12 0.2877(4) 0.2696(2) 0.79913(6) 0.0204(3) Uani d 1 C O13 0.0556(3) 0.29944(19) 0.80642(5) 0.0255(3) Uani d 1 O O14 0.4480(3) 0.36826(19) 0.78453(5) 0.0278(3) Uani d 1 O N15 0.6339(3) 0.0692(2) 0.79503(6) 0.0221(3) Uani d 1 N H1 0.968(6) 0.164(3) 0.9700(10) 0.035(7) Uiso d 1 H H2 0.795(6) -0.040(4) 0.9198(11) 0.039(8) Uiso d 1 H H4 0.208(5) 0.429(3) 0.8900(9) 0.026(6) Uiso d 1 H H5 0.283(6) 0.682(4) 0.9283(10) 0.035(7) Uiso d 1 H H6 0.635(5) 0.711(3) 0.9802(9) 0.029(7) Uiso d 1 H H7 0.902(5) 0.486(3) 0.9933(9) 0.021(6) Uiso d 1 H H11 0.273(6) 0.019(4) 0.7942(9) 0.031(7) Uiso d 1 H H10A 0.355(5) -0.070(3) 0.8708(9) 0.026(6) Uiso d 1 H H10B 0.167(5) 0.081(3) 0.8746(9) 0.027(6) Uiso d 1 H H15A 0.719(5) 0.162(3) 0.8003(9) 0.026(7) Uiso d 1 H H15B 0.713(7) -0.018(4) 0.8124(10) 0.041(8) Uiso d 1 H H15C 0.627(5) 0.040(3) 0.7663(10) 0.027(7) Uiso d 1 H O16 -0.2042(5) 0.7887(2) 0.84447(7) 0.0525(6) Uani d 1 O O17 -0.0386(4) 0.5973(2) 0.79702(6) 0.0362(4) Uani d 1 O C18 -0.1563(5) 0.6461(3) 0.83536(8) 0.0329(5) Uani d 1 C H17 -0.018(7) 0.478(4) 0.8008(11) 0.049(10) Uiso d 1 H H18 -0.195(6) 0.557(4) 0.8602(10) 0.037(8) 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 N1 0.0245(8) 0.0381(10) 0.0228(7) 0.0063(8) -0.0043(6) 0.0012(7) C2 0.0281(10) 0.0301(10) 0.0199(7) 0.0063(8) 0.0016(7) 0.0018(7) C3 0.0218(8) 0.0245(9) 0.0156(7) 0.0017(7) 0.0026(6) 0.0011(6) C4 0.0251(9) 0.0253(9) 0.0218(7) 0.0024(8) 0.0000(7) -0.0019(7) C5 0.0340(11) 0.0233(10) 0.0277(9) 0.0014(8) 0.0041(8) -0.0025(7) C6 0.0410(12) 0.0297(11) 0.0251(8) -0.0091(10) 0.0054(8) -0.0051(8) C7 0.0270(10) 0.0402(12) 0.0192(7) -0.0085(9) 0.0013(7) -0.0031(7) C8 0.0222(8) 0.0329(10) 0.0174(7) 0.0003(8) 0.0018(7) 0.0003(7) C9 0.0221(8) 0.0247(9) 0.0158(7) -0.0001(7) 0.0019(6) 0.0002(6) C10 0.0250(9) 0.0202(9) 0.0216(7) -0.0014(7) 0.0022(7) 0.0013(6) C11 0.0207(8) 0.0189(8) 0.0197(7) 0.0013(7) 0.0010(6) -0.0028(6) C12 0.0231(8) 0.0212(9) 0.0168(7) 0.0015(7) -0.0027(6) -0.0007(6) O13 0.0226(6) 0.0239(7) 0.0301(7) 0.0036(6) -0.0006(5) -0.0037(5) O14 0.0278(7) 0.0242(7) 0.0314(7) 0.0007(6) 0.0024(6) 0.0066(6) N15 0.0229(7) 0.0223(8) 0.0211(7) 0.0033(6) 0.0018(6) -0.0026(6) O16 0.0837(16) 0.0243(9) 0.0495(10) 0.0205(11) -0.0049(11) -0.0030(7) O17 0.0496(10) 0.0258(8) 0.0332(7) 0.0058(7) 0.0076(7) 0.0057(6) C18 0.0420(12) 0.0233(10) 0.0334(10) 0.0091(9) -0.0024(9) 0.0017(8) 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 C8 N1 C2 109.31(17) yes C8 N1 H1 123.1(19) ? C2 N1 H1 127.6(19) ? C3 C2 N1 110.36(19) yes C3 C2 H2 133.1(18) ? N1 C2 H2 116.4(18) ? C2 C3 C9 105.98(18) ? C2 C3 C10 125.00(19) ? C9 C3 C10 129.00(18) ? C5 C4 C9 118.88(19) ? C5 C4 H4 120.9(17) ? C9 C4 H4 120.1(17) ? C4 C5 C6 121.1(2) ? C4 C5 H5 119.7(18) ? C6 C5 H5 119.1(18) ? C7 C6 C5 121.3(2) ? C7 C6 H6 119.2(17) ? C5 C6 H6 119.5(17) ? C6 C7 C8 117.4(2) ? C6 C7 H7 122.4(16) ? C8 C7 H7 120.1(16) ? N1 C8 C7 130.23(19) yes N1 C8 C9 107.57(18) yes C7 C8 C9 122.2(2) yes C4 C9 C8 119.01(19) ? C4 C9 C3 134.19(18) ? C8 C9 C3 106.77(17) ? C3 C10 C11 115.58(16) ? C3 C10 H10A 108.9(15) ? C11 C10 H10A 108.9(14) ? C3 C10 H10B 109.4(16) ? C11 C10 H10B 106.7(15) ? H10A C10 H10B 107(2) ? N15 C11 C12 109.39(16) yes N15 C11 C10 111.42(15) ? C12 C11 C10 112.53(15) ? N15 C11 H11 105.9(19) ? C12 C11 H11 110.9(19) ? C10 C11 H11 106.5(17) ? O14 C12 O13 126.46(19) yes O14 C12 C11 118.74(17) ? O13 C12 C11 114.78(18) ? C11 N15 H15A 108.3(18) ? C11 N15 H15B 112(2) ? H15A N15 H15B 109(2) ? C11 N15 H15C 106(2) ? H15A N15 H15C 115(2) ? H15B N15 H15C 106(3) ? C18 O17 H17 106.0(18) ? O16 C18 O17 124.4(2) yes O16 C18 H18 120.4(17) ? O17 C18 H18 114.9(17) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C8 1.366(3) yes N1 C2 1.371(3) yes N1 H1 0.86(3) ? C2 C3 1.368(3) yes C2 H2 0.98(3) ? C3 C9 1.446(3) yes C3 C10 1.496(3) yes C4 C5 1.390(3) ? C4 C9 1.399(3) ? C4 H4 0.91(3) ? C5 C6 1.405(3) yes C5 H5 0.97(3) ? C6 C7 1.382(3) yes C6 H6 0.97(3) ? C7 C8 1.400(3) ? C7 H7 0.91(3) ? C8 C9 1.417(3) ? C10 C11 1.540(3) yes C10 H10A 1.01(3) ? C10 H10B 0.96(3) ? C11 N15 1.491(3) yes C11 C12 1.524(3) yes C11 H11 0.93(3) ? C12 O14 1.237(2) yes C12 O13 1.273(2) yes N15 H15A 0.89(3) ? N15 H15B 0.95(3) ? N15 H15C 0.82(3) ? O16 C18 1.213(3) yes O17 C18 1.281(3) yes O17 H17 0.99(4) ? C18 H18 1.01(3) ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O13 O17 2.487(2) . no O13 N15 2.938(2) 1_455 no O13 C4 3.418(2) . no O13 C18 3.137(3) . no O14 C18 3.384(3) 1_655 no O14 N15 2.750(2) 4_656 no O14 O17 3.206(3) . no O14 N15 2.641(2) . no O14 C11 3.342(2) 4_656 no O16 C2 3.144(3) 1_465 no O16 C10 3.310(3) 1_465 no O16 N15 2.786(2) 1_465 no O17 C12 3.254(2) 4_556 no O17 C12 3.181(3) . no O17 O13 2.487(2) . no O17 O14 3.206(3) . no O13 H17 1.51(3) . no O13 H4 2.64(2) . no O13 H18 2.88(3) . no O13 H15A 2.12(3) 1_455 no O13 H10B 2.64(2) . no O14 H15C 2.88(2) . no O14 H11 2.88(3) 4_656 no O14 H17 2.67(4) . no O14 H15A 2.25(3) . no O14 H15C 2.01(3) 4_656 no O16 H2 2.48(3) 1_465 no O16 H10A 2.71(3) 1_465 no O16 H15B 1.85(3) 1_465 no O17 H11 2.85(3) 4_556 no O17 H15C 2.83(3) 4_656 no N1 C7 3.314(3) 3_557 no N1 C8 3.350(3) 3_557 no N15 O16 2.786(2) 1_645 no N15 O13 2.938(2) 1_655 no N15 O14 2.750(2) 4_646 no N15 O14 2.641(2) . no N1 H10B 2.86(3) 1_655 no C2 O16 3.144(3) 1_645 no C4 C12 3.351(3) . no C4 O13 3.418(2) . no C4 C7 3.518(3) 1_455 no C7 C4 3.518(3) 1_655 no C7 N1 3.314(3) 3_457 no C8 N1 3.350(3) 3_457 no C9 C12 3.449(2) . no C10 O16 3.310(3) 1_645 no C11 O14 3.342(2) 4_646 no C12 O17 3.254(2) 4_546 no C12 C4 3.351(3) . no C12 C9 3.449(2) . no C12 O17 3.181(3) . no C18 O13 3.137(3) . no C18 O14 3.384(3) 1_455 no C2 H7 2.88(3) 3_457 no C2 H10B 2.73(3) 1_655 no C2 H15B 3.08(3) . no C3 H15B 2.92(3) . no C3 H15A 2.94(2) . no C4 H18 2.98(3) 1_655 no C5 H18 3.00(3) 1_655 no C6 H1 2.91(3) 3_457 no C6 H18 3.08(3) 1_655 no C7 H1 2.49(3) 3_457 no C8 H1 2.55(3) 3_457 no C9 H1 3.07(3) 3_457 no C9 H18 3.02(3) 1_655 no C12 H4 2.83(2) . no C12 H15C 2.87(3) 4_656 no C12 H17 2.35(3) . no C18 H4 3.01(3) . no C18 H15B 2.89(3) 1_465 no H1 C6 2.91(3) 3_557 no H1 C7 2.49(3) 3_557 no H1 C8 2.55(3) 3_557 no H1 C9 3.07(3) 3_557 no H2 O16 2.48(3) 1_645 no H4 O13 2.64(2) . no H4 C12 2.83(2) . no H4 C18 3.01(3) . no H7 C2 2.88(3) 3_557 no H10A O16 2.71(3) 1_645 no H10B O13 2.64(2) . no H10B N1 2.86(3) 1_455 no H10B H2 2.53(4) 1_455 no H10B C2 2.73(3) 1_455 no H11 O17 2.85(3) 4_546 no H11 O14 2.88(3) 4_646 no H15A O13 2.12(3) 1_655 no H15A O14 2.25(3) . no H15A C3 2.94(2) . no H15B O16 1.85(3) 1_645 no H15B C2 3.08(3) . no H15B C18 2.89(3) 1_645 no H15B C3 2.92(3) . no H15C O14 2.88(2) . no H15C O17 2.83(3) 4_646 no H15C C12 2.87(3) 4_646 no H15C O14 2.01(3) 4_646 no H17 O13 1.51(3) . no H17 O14 2.67(4) . no H17 C12 2.35(3) . no H18 O13 2.88(3) . no H18 C4 2.98(3) 1_455 no H18 C5 3.00(3) 1_455 no H18 C6 3.08(3) 1_455 no H18 C9 3.02(3) 1_455 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 N15 H15A O13 1_655 0.89(3) 2.12(3) 2.938(2) 153(2) N15 H15A O14 . 0.89(3) 2.25(3) 2.641(2) 106(2) N15 H15B O16 1_645 0.95(3) 1.85(3) 2.786(2) 167(3) N15 H15C O14 4_646 0.82(3) 2.01(3) 2.750(2) 151(2) O17 H17 O13 . 0.98(3) 1.51(3) 2.487(2) 171(4) 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 C8 N1 C2 C3 0.1(2) no N1 C2 C3 C9 -0.7(2) no C2 C3 C9 C8 1.0(2) no C2 C3 C10 C11 -104.4(2) no C5 C4 C9 C3 179.1(2) no C5 C6 C7 C8 0.0(3) no N1 C8 C9 C3 -0.9(2) no C7 C8 C9 C4 -1.8(3) no N15 C11 C12 O13 172.45(15) no C10 C11 C12 O14 115.27(19) no C2 N1 C8 C7 179.7(2) no N1 C2 C3 C10 -179.33(18) no C10 C3 C9 C4 1.6(4) no C9 C3 C10 C11 77.3(3) no C5 C4 C9 C8 1.3(3) no C6 C7 C8 N1 -177.9(2) no N1 C8 C9 C4 177.44(18) no C3 C10 C11 N15 53.5(2) no N15 C11 C12 O14 -9.1(2) no C2 N1 C8 C9 0.5(2) no C2 C3 C9 C4 -177.0(2) no C10 C3 C9 C8 179.54(18) no C9 C4 C5 C6 -0.2(3) no C4 C5 C6 C7 -0.4(3) no C6 C7 C8 C9 1.2(3) no C7 C8 C9 C3 179.83(18) no C3 C10 C11 C12 -69.8(2) no C10 C11 C12 O13 -63.2(2) no C8 N1 C2 H2 177(2) no H1 N1 C8 C7 1(2) no H15A N15 C11 C12 37.0(17) no H15B N15 C11 C12 157(2) no H15C N15 C11 C12 -87.1(18) no H2 C2 C3 C10 5(3) no C9 C3 C10 H10A -159.8(15) no H4 C4 C5 C6 -178.1(19) no H4 C4 C9 C8 179.2(19) no H5 C5 C6 H6 1(3) no H6 C6 C7 H7 2(3) no C3 C10 C11 H11 169(2) no H10A C10 C11 H11 46(3) no H10B C10 C11 H11 -69(3) no H1 N1 C2 C3 179(2) no H1 N1 C8 C9 -178(2) no H15A N15 C11 H11 156(3) no H15B N15 C11 H11 -83(3) no H15C N15 C11 H11 32(3) no C2 C3 C10 H10A 18.5(15) no C9 C3 C10 H10B -43.2(16) no H4 C4 C5 H5 -1(3) no C4 C5 C6 H6 177.8(17) no C5 C6 C7 H7 -179.3(18) no H7 C7 C8 N1 1.4(18) no H10A C10 C11 N15 -69.5(16) no H10B C10 C11 N15 175.4(15) no H11 C11 C12 O13 55.9(19) no H1 N1 C2 H2 -5(3) no H15A N15 C11 C10 -88.0(17) no H15B N15 C11 C10 32(2) no H15C N15 C11 C10 147.9(18) no H2 C2 C3 C9 -176(3) no C2 C3 C10 H10B 135.1(15) no C9 C4 C5 H5 177(2) no H4 C4 C9 C3 -3.0(19) no H5 C5 C6 C7 -178(2) no H6 C6 C7 C8 -178.3(17) no H7 C7 C8 C9 -179.5(18) no H10A C10 C11 C12 167.3(16) no H10B C10 C11 C12 52.2(15) no H11 C11 C12 O14 -125.7(19) no