#------------------------------------------------------------------------------ #$Date: 2015-02-25 13:01:53 +0000 (Wed, 25 Feb 2015) $ #$Revision: 132410 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/06/2200659.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_2200659 loop_ _publ_author_name 'Degen, Alexander' 'Bolte, Michael' _publ_section_title ; The twinned crystal structure of 3-indolylacetic acid ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o999 _journal_page_last o1000 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C10 H9 N O2' _chemical_formula_moiety 'C10 H9 N O2' _chemical_formula_sum 'C10 H9 N O2' _chemical_formula_weight 175.18 _chemical_name_systematic ? _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 105.700(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 17.848(2) _cell_length_b 5.2214(7) _cell_length_c 9.5680(10) _cell_measurement_reflns_used 10779 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.5 _cell_measurement_theta_min 1.7 _cell_volume 858.39(18) _computing_cell_refinement X-Area _computing_data_collection 'X-Area (Stoe & Cie, 2001)' _computing_data_reduction X-Area _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997) ' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990) ' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Stoe IPDS-II two-circle' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0501 _diffrn_reflns_av_sigmaI/netI .0294 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 11341 _diffrn_reflns_theta_full 26.39 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_theta_min 2.21 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .096 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 368 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .117 _refine_diff_density_min -.122 _refine_ls_extinction_coef .046(5) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1756 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.005 _refine_ls_R_factor_all .0380 _refine_ls_R_factor_gt .0286 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.0141P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0743 _reflns_number_gt 1476 _reflns_number_total 1756 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6058.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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_original_cell_volume 858.39(17) _cod_database_code 2200659 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y+1/2, z+1/2' '-x, -y, -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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 .78667(9) .2286(3) .31213(17) .0508(4) Uani d . 1 . . N H1 .8077(14) .099(5) .276(3) .087(8) Uiso d . 1 . . H C1 .71228(10) .3206(3) .2555(2) .0492(4) Uani d . 1 . . C H1A .6752 .2530 .1730 .059 Uiso calc R 1 . . H C2 .70028(9) .5233(3) .33589(18) .0421(4) Uani d . 1 . . C C3 .77160(8) .5603(3) .44932(16) .0356(3) Uani d . 1 . . C C4 .79686(9) .7378(3) .56268(19) .0428(4) Uani d . 1 . . C H4 .7625 .8676 .5775 .051 Uiso calc R 1 . . H C5 .87205(10) .7234(3) .6530(2) .0496(4) Uani d . 1 . . C H5 .8889 .8439 .7294 .060 Uiso calc R 1 . . H C6 .92328(9) .5336(3) .6329(2) .0522(4) Uani d . 1 . . C H6 .9745 .5264 .6961 .063 Uiso calc R 1 . . H C7 .90057(9) .3563(3) .5222(2) .0491(4) Uani d . 1 . . C H7 .9355 .2276 .5084 .059 Uiso calc R 1 . . H C8 .82467(9) .3714(3) .43107(19) .0405(4) Uani d . 1 . . C C9 .62743(9) .6794(3) .3094(2) .0500(4) Uani d . 1 . . C H9B .5993 .6681 .2051 .060 Uiso calc R 1 . . H H9A .6420 .8610 .3311 .060 Uiso calc R 1 . . H C10 .57321(8) .6008(3) .39668(18) .0395(3) Uani d . 1 . . C O1 .58057(7) .4048(2) .46829(14) .0512(3) Uani d . 1 . . O O2 .51619(7) .7638(2) .38738(15) .0548(3) Uani d . 1 . . O H2 .4854(14) .697(5) .444(3) .084(7) 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 .0638(9) .0389(7) .0580(9) -.0064(7) .0308(8) -.0095(6) C1 .0536(9) .0515(9) .0460(10) -.0176(7) .0192(9) -.0014(8) C2 .0411(8) .0452(8) .0453(9) -.0084(6) .0207(7) .0063(7) C3 .0362(7) .0326(7) .0442(8) -.0049(5) .0213(7) .0033(6) C4 .0470(8) .0353(7) .0546(10) -.0013(7) .0281(8) -.0027(7) C5 .0511(9) .0454(9) .0553(11) -.0147(8) .0197(8) -.0075(7) C6 .0379(8) .0556(10) .0629(11) -.0063(7) .0134(8) .0063(9) C7 .0423(8) .0414(8) .0700(12) .0062(7) .0263(9) .0061(8) C8 .0461(8) .0303(7) .0525(10) -.0047(6) .0259(7) -.0012(7) C9 .0401(8) .0579(10) .0551(11) -.0036(7) .0181(8) .0168(8) C10 .0331(7) .0454(8) .0397(8) -.0040(6) .0093(7) .0057(7) O1 .0438(6) .0571(7) .0582(7) .0055(5) .0233(6) .0199(6) O2 .0484(6) .0542(6) .0688(9) .0067(5) .0278(6) .0212(6) 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 N1 C8 . 1.376(2) ? N1 C1 . 1.378(2) ? N1 H1 . .89(3) ? C1 C2 . 1.359(2) ? C1 H1A . .9500 ? C2 C3 . 1.445(2) ? C2 C9 . 1.497(2) ? C3 C4 . 1.405(2) ? C3 C8 . 1.410(2) ? C4 C5 . 1.388(2) ? C4 H4 . .9500 ? C5 C6 . 1.396(2) ? C5 H5 . .9500 ? C6 C7 . 1.382(3) ? C6 H6 . .9500 ? C7 C8 . 1.401(2) ? C7 H7 . .9500 ? C9 C10 . 1.497(2) ? C9 H9B . .9900 ? C9 H9A . .9900 ? C10 O1 . 1.2187(18) ? C10 O2 . 1.3110(19) ? O2 H2 . .94(3) ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 C8 N1 C1 110.06(14) C8 N1 H1 124.9(17) C1 N1 H1 125.0(17) C2 C1 N1 109.37(16) C2 C1 H1A 125.3 N1 C1 H1A 125.3 C1 C2 C3 106.70(14) C1 C2 C9 126.21(16) C3 C2 C9 127.09(15) C4 C3 C8 118.09(14) C4 C3 C2 134.52(14) C8 C3 C2 107.36(14) C5 C4 C3 119.93(14) C5 C4 H4 120.0 C3 C4 H4 120.0 C4 C5 C6 120.77(16) C4 C5 H5 119.6 C6 C5 H5 119.6 C7 C6 C5 120.92(16) C7 C6 H6 119.5 C5 C6 H6 119.5 C6 C7 C8 118.21(14) C6 C7 H7 120.9 C8 C7 H7 120.9 N1 C8 C7 131.40(14) N1 C8 C3 106.51(14) C7 C8 C3 122.07(15) C2 C9 C10 114.78(13) C2 C9 H9B 108.6 C10 C9 H9B 108.6 C2 C9 H9A 108.6 C10 C9 H9A 108.6 H9B C9 H9A 107.5 O1 C10 O2 123.14(14) O1 C10 C9 123.81(14) O2 C10 C9 113.04(13) C10 O2 H2 106.4(14) 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 O2 H2 O1 3_666 .94(3) 1.70(3) 2.6372(16) 172(2) 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 C8 N1 C1 C2 -.17(18) N1 C1 C2 C3 .17(17) N1 C1 C2 C9 179.20(14) C1 C2 C3 C4 177.99(15) C9 C2 C3 C4 -1.0(3) C1 C2 C3 C8 -.11(15) C9 C2 C3 C8 -179.13(14) C8 C3 C4 C5 -.2(2) C2 C3 C4 C5 -178.18(16) C3 C4 C5 C6 -.1(2) C4 C5 C6 C7 .3(3) C5 C6 C7 C8 -.2(2) C1 N1 C8 C7 -178.52(16) C1 N1 C8 C3 .09(17) C6 C7 C8 N1 178.32(16) C6 C7 C8 C3 -.1(2) C4 C3 C8 N1 -178.45(12) C2 C3 C8 N1 .01(15) C4 C3 C8 C7 .3(2) C2 C3 C8 C7 178.78(14) C1 C2 C9 C10 96.2(2) C3 C2 C9 C10 -84.92(19) C2 C9 C10 O1 -10.3(2) C2 C9 C10 O2 170.32(15) _cod_database_fobs_code 2200659 _journal_paper_doi 10.1107/S160053680101532X