#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008285.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_2008285 loop_ _publ_author_name 'Kumar, G. Biju' 'Shah, Amrish C.' 'Cardin, Christine J.' 'Trenkle, Markus' _publ_section_title ; A substituted isoindolin-1-one derived from (R)-(--)-2-amino-1-butanol ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900019 _journal_paper_doi 10.1107/S0108270199099758 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H15 N O2' _chemical_formula_sum 'C12 H15 N O2' _chemical_formula_weight 205.25 _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' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.776(8) _cell_length_b 12.599(5) _cell_length_c 15.288(5) _cell_measurement_reflns_used 5207 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.0 _cell_measurement_theta_min 2.0 _cell_volume 1112.5(16) _computing_cell_refinement 'MARXDS (Kabsch, 1993)' _computing_data_collection 'Mar image-plate scanner' _computing_data_reduction 'XDS (Kabsch, 1988)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device 'Mar 18cm image-plate scanner' _diffrn_measurement_method 'rotation method' _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 0.049 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 5762 _diffrn_reflns_theta_full 24.91 _diffrn_reflns_theta_max 24.91 _diffrn_reflns_theta_min 2.09 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_method 'not measured' _exptl_crystal_description rhomb _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.124 _refine_diff_density_min -0.123 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.8(18) _refine_ls_extinction_coef 0.152(11) _refine_ls_extinction_method SHELXL93 _refine_ls_goodness_of_fit_all 1.000 _refine_ls_goodness_of_fit_obs 1.018 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 197 _refine_ls_number_reflns 1908 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.382 _refine_ls_restrained_S_obs 1.018 _refine_ls_R_factor_all 0.056 _refine_ls_R_factor_obs 0.040 _refine_ls_shift/esd_max -0.014 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1912P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.135 _refine_ls_wR_factor_obs 0.092 _reflns_number_observed 1667 _reflns_number_total 1911 _reflns_observed_criterion I>2\s(I) _cod_data_source_file qa0083.cif _cod_data_source_block QA0083 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1912P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.1912P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1112.5(13) _cod_database_code 2008285 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_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 C1 0.3499(4) 0.12285(17) 0.62177(16) 0.0362(6) Uani d . 1 . . C C2 0.2662(5) 0.0527(2) 0.55793(19) 0.0484(7) Uani d . 1 . . C H2 0.120(5) 0.012(2) 0.5694(17) 0.045(7) Uiso d . 1 . . H C3 0.3925(6) 0.0426(2) 0.48083(19) 0.0561(8) Uani d . 1 . . C H3 0.346(6) -0.007(3) 0.435(2) 0.081(10) Uiso d . 1 . . H C4 0.5995(6) 0.0991(2) 0.4687(2) 0.0562(8) Uani d . 1 . . C H4 0.683(7) 0.089(3) 0.412(3) 0.085(11) Uiso d . 1 . . H C5 0.6826(5) 0.1685(2) 0.5330(2) 0.0501(7) Uani d . 1 . . C H5 0.836(6) 0.205(2) 0.5258(19) 0.058(8) Uiso d . 1 . . H C6 0.5524(4) 0.18045(18) 0.60913(16) 0.0376(6) Uani d . 1 . . C C7 0.5906(4) 0.2532(2) 0.68651(17) 0.0418(6) Uani d . 1 . . C H7A 0.609(4) 0.337(2) 0.6698(14) 0.031(6) Uiso d . 1 . . H H7B 0.749(5) 0.238(2) 0.7194(16) 0.044(7) Uiso d . 1 . . H C8 0.2518(4) 0.15082(19) 0.70938(17) 0.0370(6) Uani d . 1 . . C O2 0.0794(3) 0.11282(15) 0.74589(13) 0.0531(5) Uani d . 1 . . O N1 0.3931(3) 0.22783(15) 0.74332(13) 0.0373(5) Uani d . 1 . . N O1 0.0816(4) 0.40305(16) 0.76430(16) 0.0703(7) Uani d . 1 . . O H1 0.0458 0.4654 0.7571 0.105 Uiso calc R 1 . . H C9 0.2879(5) 0.3973(2) 0.8147(2) 0.0518(7) Uani d . 1 . . C H9A 0.255(6) 0.426(2) 0.876(2) 0.058(8) Uiso d . 1 . . H H9B 0.415(6) 0.438(2) 0.7800(19) 0.056(8) Uiso d . 1 . . H C10 0.3537(5) 0.2804(2) 0.82788(16) 0.0402(6) Uani d . 1 . . C H10 0.215(5) 0.243(2) 0.8526(17) 0.046(7) Uiso d . 1 . . H C11 0.5651(5) 0.2686(2) 0.8877(2) 0.0524(7) Uani d . 1 . . C H11A 0.526(6) 0.307(3) 0.939(2) 0.070(10) Uiso d . 1 . . H H11B 0.690(7) 0.301(3) 0.857(3) 0.075(11) Uiso d . 1 . . H C12 0.6267(8) 0.1531(3) 0.9076(3) 0.0769(11) Uani d . 1 . . C H12A 0.764(8) 0.146(4) 0.950(3) 0.103(14) Uiso d . 1 . . H H12B 0.491(9) 0.121(5) 0.940(3) 0.136(19) Uiso d . 1 . . H H12C 0.638(10) 0.110(5) 0.850(4) 0.137(19) 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 C1 0.0337(12) 0.0280(11) 0.0469(13) 0.0031(9) -0.0019(11) -0.0001(10) C2 0.0491(16) 0.0379(13) 0.0583(16) -0.0008(12) -0.0031(15) -0.0044(12) C3 0.069(2) 0.0487(16) 0.0507(15) 0.0083(15) -0.0050(16) -0.0111(13) C4 0.0632(19) 0.0524(16) 0.0529(16) 0.0095(15) 0.0120(15) -0.0001(13) C5 0.0471(15) 0.0472(16) 0.0561(16) 0.0032(13) 0.0092(13) 0.0066(13) C6 0.0349(12) 0.0337(12) 0.0443(13) 0.0040(9) 0.0005(11) 0.0034(10) C7 0.0347(13) 0.0410(14) 0.0497(14) -0.0084(11) 0.0049(12) -0.0023(11) C8 0.0290(11) 0.0317(11) 0.0502(13) -0.0002(10) 0.0014(11) 0.0017(10) O2 0.0430(10) 0.0487(10) 0.0675(12) -0.0145(9) 0.0132(10) -0.0094(9) N1 0.0331(10) 0.0330(9) 0.0458(11) -0.0036(8) 0.0028(9) -0.0043(9) O1 0.0695(14) 0.0500(11) 0.0914(16) 0.0178(11) -0.0294(13) -0.0100(11) C9 0.0572(17) 0.0406(15) 0.0575(17) 0.0066(13) -0.0061(15) -0.0089(13) C10 0.0393(12) 0.0373(13) 0.0440(14) 0.0013(11) 0.0011(11) -0.0039(10) C11 0.0526(16) 0.0587(16) 0.0460(15) 0.0024(15) -0.0055(14) -0.0053(14) C12 0.075(2) 0.074(2) 0.082(2) 0.011(2) -0.015(2) 0.021(2) 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 C6 C1 C2 121.5(2) C6 C1 C8 108.7(2) C2 C1 C8 129.8(2) C3 C2 C1 117.8(3) C2 C3 C4 120.8(3) C5 C4 C3 121.0(3) C6 C5 C4 118.0(3) C1 C6 C5 120.9(2) C1 C6 C7 109.3(2) C5 C6 C7 129.8(2) N1 C7 C6 102.55(18) O2 C8 N1 125.6(2) O2 C8 C1 128.1(2) N1 C8 C1 106.3(2) C8 N1 C7 113.12(19) C8 N1 C10 124.1(2) C7 N1 C10 122.8(2) O1 C9 C10 109.1(2) N1 C10 C9 110.8(2) N1 C10 C11 111.0(2) C9 C10 C11 111.6(2) C12 C11 C10 113.4(3) 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 C1 C6 . 1.390(3) ? C1 C2 . 1.402(4) ? C1 C8 . 1.496(4) ? C2 C3 . 1.392(4) ? C3 C4 . 1.404(5) ? C4 C5 . 1.400(4) ? C5 C6 . 1.394(4) ? C6 C7 . 1.512(3) ? C7 N1 . 1.469(3) ? C8 O2 . 1.238(3) ? C8 N1 . 1.370(3) ? N1 C10 . 1.470(3) ? O1 C9 . 1.421(4) ? C9 C10 . 1.534(4) ? C10 C11 . 1.533(4) ? C11 C12 . 1.529(5) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21183160 2 PubChem 57328329