#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008156.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_2008156 loop_ _publ_author_name 'Kundu, Nitya G.' 'Khan, M. Wahab' 'Guha, Subhadra' 'Mukherjee, Alok K.' _publ_section_title ; Two (Z)-3-aryl(alkyl)ideneisoindolin-1-ones ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 239 _journal_page_last 241 _journal_volume 55 _journal_year 1999 _chemical_formula_analytical 'C19 H19 N O2' _chemical_formula_moiety 'C19 H19 N O2' _chemical_formula_structural 'C19 H19 N O2' _chemical_formula_sum 'C19 H19 N O2' _chemical_formula_weight 293.35 _chemical_melting_point 413.0(10) _chemical_name_common '(Z)-3-(2'-hydroxy-2'-methyl)propylidene-N-p-tolyl isoindolin-1-one' _chemical_name_systematic ; (Z)-3-(2'-hydroxy-2'-methyl)propylidene-N-p-tolyl isoindolin-1-one ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 68.70(2) _cell_angle_beta 81.17(2) _cell_angle_gamma 70.00(2) _cell_formula_units_Z 2 _cell_length_a 9.426(2) _cell_length_b 9.795(2) _cell_length_c 9.909(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16 _cell_measurement_theta_min 8 _cell_volume 800.5(3) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'MULTAN88 (Debaerdemaeker et al., 1988)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _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_sigmaI/netI 0.3284 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 2771 _diffrn_reflns_theta_max 24.92 _diffrn_reflns_theta_min 3.13 _diffrn_standards_decay_% 3 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 312 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.194 _refine_diff_density_min -0.225 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.771 _refine_ls_goodness_of_fit_obs 1.272 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 2771 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.771 _refine_ls_restrained_S_obs 1.272 _refine_ls_R_factor_all 0.240 _refine_ls_R_factor_obs 0.055 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0496P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.125 _refine_ls_wR_factor_obs 0.104 _reflns_number_observed 848 _reflns_number_total 2771 _reflns_observed_criterion I>2\s(I) _[local]_cod_data_source_file ha1225.cif _[local]_cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 ; _cod_database_code 2008156 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 0.0319(15) 0.060(2) 0.113(3) -0.0191(14) -0.007(2) -0.025(2) O2 0.0263(14) 0.059(2) 0.128(3) -0.0185(13) -0.004(2) -0.024(2) N 0.019(2) 0.037(2) 0.069(3) -0.0044(15) -0.009(2) -0.015(2) C1 0.027(2) 0.041(2) 0.051(3) -0.009(2) -0.010(2) -0.013(2) C2 0.033(2) 0.055(3) 0.076(3) -0.008(2) -0.012(2) -0.022(2) C3 0.035(2) 0.055(3) 0.082(4) 0.000(2) -0.016(2) -0.021(2) C4 0.056(3) 0.043(2) 0.063(3) -0.006(2) -0.014(2) -0.014(2) C5 0.040(2) 0.044(2) 0.054(3) -0.011(2) -0.003(2) -0.017(2) C6 0.029(2) 0.039(2) 0.042(3) -0.007(2) -0.007(2) -0.012(2) C7 0.032(2) 0.041(2) 0.040(3) -0.011(2) -0.005(2) -0.015(2) C8 0.029(2) 0.049(3) 0.059(3) -0.012(2) -0.006(2) -0.012(2) C9 0.024(2) 0.045(2) 0.041(3) -0.013(2) -0.004(2) -0.009(2) C10 0.052(3) 0.060(3) 0.042(3) -0.021(2) -0.005(2) -0.021(3) C11 0.054(3) 0.052(3) 0.075(4) -0.019(2) 0.004(2) -0.038(3) C12 0.046(3) 0.041(3) 0.071(4) -0.008(2) 0.003(3) -0.013(3) C13 0.072(3) 0.056(3) 0.054(4) 0.005(3) -0.008(3) -0.008(3) C14 0.053(3) 0.056(3) 0.052(3) -0.006(2) 0.001(2) -0.024(2) C15 0.093(4) 0.048(3) 0.129(5) -0.014(3) -0.005(3) -0.020(3) C16 0.029(2) 0.046(2) 0.058(3) -0.014(2) -0.004(2) -0.016(2) C17 0.024(2) 0.039(2) 0.090(4) -0.009(2) -0.001(2) -0.022(2) C18 0.069(3) 0.067(3) 0.092(4) -0.016(2) -0.034(3) -0.002(3) C19 0.043(3) 0.079(3) 0.156(5) -0.014(2) 0.015(3) -0.069(3) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 0.2236(3) 0.4952(3) 0.2347(3) 0.0674(9) Uani d . 1 . O O2 0.9094(2) 0.6333(3) 0.1788(3) 0.0715(10) Uani d . 1 . O H20 0.9993 0.5831 0.1872 0.084 Uiso calc . 1 . H N 0.4577(3) 0.5203(3) 0.2337(3) 0.0429(9) Uani d . 1 . N C1 0.2598(4) 0.7424(4) 0.1852(4) 0.0400(10) Uani d . 1 . C C2 0.1185(4) 0.8536(5) 0.1646(5) 0.0550(12) Uani d . 1 . C H2 0.0316 0.8267 0.1707 0.061 Uiso calc . 1 . H C3 0.1108(4) 1.0030(5) 0.1353(5) 0.0599(13) Uani d . 1 . C H3 0.0173 1.0792 0.1202 0.074 Uiso calc . 1 . H C4 0.2398(5) 1.0432(4) 0.1277(4) 0.0565(12) Uani d . 1 . C H4 0.2316 1.1460 0.1074 0.071 Uiso calc . 1 . H C5 0.3797(4) 0.9338(4) 0.1495(4) 0.0461(11) Uani d . 1 . C H5 0.4662 0.9614 0.1432 0.058 Uiso calc . 1 . H C6 0.3887(4) 0.7828(4) 0.1809(4) 0.0375(10) Uani d . 1 . C C7 0.5203(4) 0.6396(4) 0.2112(4) 0.0370(10) Uani d . 1 . C C8 0.3023(4) 0.5765(5) 0.2198(4) 0.0469(11) Uani d . 1 . C C9 0.5343(3) 0.3571(4) 0.2814(5) 0.0372(10) Uani d . 1 . C C10 0.5712(4) 0.2780(5) 0.1844(4) 0.0485(11) Uani d . 1 . C H10 0.5450 0.3291 0.0880 0.067 Uiso calc . 1 . H C11 0.6476(4) 0.1221(5) 0.2323(5) 0.0553(12) Uani d . 1 . C H11 0.6738 0.0689 0.1666 0.078 Uiso calc . 1 . H C12 0.6861(4) 0.0428(4) 0.3757(6) 0.0566(13) Uani d . 1 . C C13 0.6448(5) 0.1250(5) 0.4689(5) 0.0697(14) Uani d . 1 . C H13 0.6699 0.0741 0.5657 0.081 Uiso calc . 1 . H C14 0.5671(4) 0.2810(4) 0.4244(5) 0.0550(12) Uani d . 1 . C H14 0.5376 0.3334 0.4908 0.071 Uiso calc . 1 . H C15 0.7724(5) -0.1269(5) 0.4250(6) 0.095(2) Uani d . 1 . C H15A 0.8617 -0.1455 0.3644 0.106 Uiso calc . 1 . H H15B 0.7099 -0.1836 0.4183 0.106 Uiso calc . 1 . H H15C 0.8004 -0.1598 0.5237 0.106 Uiso calc . 1 . H C16 0.6612(4) 0.6412(4) 0.2126(4) 0.0440(11) Uani d . 1 . C C17 0.8192(4) 0.5305(4) 0.2407(5) 0.0509(12) Uani d . 1 . C C18 0.8459(5) 0.4531(5) 0.4025(5) 0.080(2) Uani d . 1 . C H18A 0.7899 0.3810 0.4431 0.103 Uiso calc . 1 . H H18B 0.8129 0.5299 0.4490 0.103 Uiso calc . 1 . H H18C 0.9516 0.3996 0.4175 0.103 Uiso calc . 1 . H C19 0.8650(4) 0.4135(5) 0.1646(6) 0.088(2) Uani d . 1 . C H19A 0.8156 0.3364 0.2117 0.108 Uiso calc . 1 . H H19B 0.9725 0.3657 0.1681 0.108 Uiso calc . 1 . H H19C 0.8361 0.4637 0.0654 0.108 Uiso calc . 1 . H H16 0.6629 0.7396 0.1881 0.042 Uiso calc . 1 . H 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 O1 C8 . 1.221(4) yes O2 C17 . 1.445(4) yes O2 H20 . 0.820(2) no N C8 . 1.387(4) yes N C7 . 1.417(4) yes N C9 . 1.437(4) yes C1 C2 . 1.390(4) no C1 C6 . 1.391(4) no C1 C8 . 1.453(5) yes C2 C3 . 1.362(5) no C2 H2 . 0.930(4) no C3 C4 . 1.385(5) no C3 H3 . 0.930(3) no C4 C5 . 1.374(5) no C4 H4 . 0.930(4) no C5 C6 . 1.370(4) no C5 H5 . 0.930(4) no C6 C7 . 1.488(4) no C7 C16 . 1.336(4) yes C9 C14 . 1.367(5) no C9 C10 . 1.378(5) no C10 C11 . 1.379(5) no C10 H10 . 0.930(4) no C11 C12 . 1.385(5) no C11 H11 . 0.930(4) no C12 C13 . 1.366(5) no C12 C15 . 1.507(5) no C13 C14 . 1.382(5) no C13 H13 . 0.930(4) no C14 H14 . 0.930(4) no C15 H15A . 0.960(5) no C15 H15B . 0.960(5) no C15 H15C . 0.960(5) no C16 C17 . 1.507(4) yes C17 C19 . 1.503(5) no C17 C18 . 1.523(6) no C18 H18A . 0.960(4) no C18 H18B . 0.960(5) no C18 H18C . 0.960(4) no C19 H19A . 0.960(5) no C19 H19B . 0.960(4) no C19 H19C . 0.960(5) no 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' 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' H H 0.0000 0.0000 '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 C17 O2 H20 109.5(3) no C8 N C7 111.9(3) yes C8 N C9 120.5(3) no C7 N C9 127.3(3) no C2 C1 C6 120.5(3) no C2 C1 C8 130.4(3) no C6 C1 C8 109.0(3) no C3 C2 C1 118.2(3) no C3 C2 H2 120.9(4) no C1 C2 H2 120.9(4) no C2 C3 C4 121.1(3) no C2 C3 H3 119.5(4) no C4 C3 H3 119.5(4) no C5 C4 C3 121.1(4) no C5 C4 H4 119.5(4) no C3 C4 H4 119.5(4) no C6 C5 C4 118.4(3) no C6 C5 H5 120.8(3) no C4 C5 H5 120.8(4) no C5 C6 C1 120.7(3) no C5 C6 C7 131.4(3) no C1 C6 C7 107.9(3) no C16 C7 N 133.1(3) no C16 C7 C6 122.2(3) no N C7 C6 104.7(3) no O1 C8 N 123.7(3) no O1 C8 C1 129.8(3) no N C8 C1 106.5(3) yes C14 C9 C10 120.5(3) no C14 C9 N 119.3(4) no C10 C9 N 120.2(4) no C11 C10 C9 119.1(4) no C11 C10 H10 120.4(4) no C9 C10 H10 120.4(4) no C10 C11 C12 121.6(4) no C10 C11 H11 119.2(5) no C12 C11 H11 119.2(4) no C13 C12 C11 117.4(4) no C13 C12 C15 121.9(5) no C11 C12 C15 120.7(5) no C12 C13 C14 122.3(4) no C12 C13 H13 118.9(4) no C14 C13 H13 118.9(5) no C9 C14 C13 119.0(4) no C9 C14 H14 120.5(4) no C13 C14 H14 120.5(5) no C12 C15 H15A 109.5(4) no C12 C15 H15B 109.5(4) no H15A C15 H15B 109.5(5) no C12 C15 H15C 109.5(4) no H15A C15 H15C 109.5(5) no H15B C15 H15C 109.5(5) no C7 C16 C17 139.7(3) yes O2 C17 C16 101.7(3) yes O2 C17 C19 107.9(3) no C16 C17 C19 115.0(3) no O2 C17 C18 109.3(3) no C16 C17 C18 111.3(3) no C19 C17 C18 111.1(4) no C17 C18 H18A 109.5(4) no C17 C18 H18B 109.5(4) no H18A C18 H18B 109.5(5) no C17 C18 H18C 109.5(4) no H18A C18 H18C 109.5(4) no H18B C18 H18C 109.5(4) no C17 C19 H19A 109.5(4) no C17 C19 H19B 109.5(4) no H19A C19 H19B 109.5(4) no C17 C19 H19C 109.5(4) no H19A C19 H19C 109.5(4) no H19B C19 H19C 109.5(5) no 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 C6 C1 C2 C3 2.2(6) no C8 C1 C2 C3 178.8(4) no C1 C2 C3 C4 -0.7(7) no C2 C3 C4 C5 -0.1(7) no C3 C4 C5 C6 -0.7(6) no C4 C5 C6 C1 2.3(6) no C4 C5 C6 C7 -179.3(4) no C2 C1 C6 C5 -3.1(6) no C8 C1 C6 C5 179.6(3) no C2 C1 C6 C7 178.1(3) no C8 C1 C6 C7 0.9(4) no C8 N C7 C16 -179.5(4) no C9 N C7 C16 7.4(7) yes C8 N C7 C6 0.1(4) no C9 N C7 C6 -173.0(4) no C5 C6 C7 C16 0.5(6) no C1 C6 C7 C16 179.1(4) no C5 C6 C7 N -179.2(4) no C1 C6 C7 N -0.6(4) no C7 N C8 O1 -179.8(4) no C9 N C8 O1 -6.2(6) yes C7 N C8 C1 0.4(4) no C9 N C8 C1 174.1(3) no C2 C1 C8 O1 2.5(7) no C6 C1 C8 O1 179.5(4) no C2 C1 C8 N -177.7(4) no C6 C1 C8 N -0.8(4) no C8 N C9 C14 -96.5(4) no C7 N C9 C14 76.1(5) no C8 N C9 C10 82.1(5) no C7 N C9 C10 -105.2(4) no C14 C9 C10 C11 -2.7(5) no N C9 C10 C11 178.6(3) no C9 C10 C11 C12 0.9(6) no C10 C11 C12 C13 0.3(6) no C10 C11 C12 C15 -178.7(4) no C11 C12 C13 C14 0.2(7) no C15 C12 C13 C14 179.3(4) no C10 C9 C14 C13 3.3(6) no N C9 C14 C13 -178.1(3) no C12 C13 C14 C9 -2.0(6) no N C7 C16 C17 -2.7(8) yes C6 C7 C16 C17 177.8(5) no C7 C16 C17 O2 164.5(5) yes C7 C16 C17 C19 48.2(7) yes C7 C16 C17 C18 -79.2(6) yes