#------------------------------------------------------------------------------ #$Date: 2011-01-02 22:00:31 +0200 (Sun, 02 Jan 2011) $ #$Revision: 5310 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2216635.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_2216635 loop_ _publ_author_name 'Maliha, Bushra' 'Hussain, Ishtiaq' 'Siddiqui, Hamid Latif' 'Tariq, Muhammad Ilyas' 'Parvez, Masood' _publ_section_title ; 1-Oxo-N-phenylisoindoline-2-carboxamide ; _journal_coeditor_code LH2558 _journal_issue 12 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o4728 _journal_page_last o4728 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C15 H12 N2 O2' _chemical_formula_moiety 'C15 H12 N2 O2' _chemical_formula_sum 'C15 H12 N2 O2' _chemical_formula_weight 252.27 _chemical_name_common ; ? ; _chemical_name_systematic ; 1-Oxo-N-phenylisoindoline-2-carboxamide ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 102.228(17) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.905(4) _cell_length_b 5.6190(10) _cell_length_c 17.161(6) _cell_measurement_reflns_used 5034 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 2.62 _cell_volume 1216.2(6) _computing_cell_refinement 'HKL DENZO (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SAPI91 (Fan, 1991)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Nonius KappaCCD' _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 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 5034 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 2.62 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_T_max 0.9944 _exptl_absorpt_correction_T_min 0.9680 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SORTAV; Blessing, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.165 _refine_diff_density_min -0.160 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 2768 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0384 _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^)+(0.038P)^2^+0.39P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.0972 _reflns_number_gt 2119 _reflns_number_total 2768 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh2558.cif _[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 ; _cod_database_code 2216635 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_type_symbol _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 O O1 0.92562(7) -0.27832(16) 0.39885(5) 0.0328(2) Uani d . 1 O O2 0.89390(8) 0.31349(17) 0.24855(6) 0.0406(3) Uani d . 1 N N1 0.97796(8) 0.07840(18) 0.34984(6) 0.0263(2) Uani d . 1 N N2 0.80821(8) -0.01677(19) 0.28210(6) 0.0297(3) Uani d . 1 H H2N 0.8169 -0.1366 0.3159 0.036 Uiso calc R 1 C C1 1.09874(10) -0.1015(2) 0.44905(7) 0.0268(3) Uani d . 1 C C2 1.14801(11) -0.2514(2) 0.51004(8) 0.0315(3) Uani d . 1 H H2 1.1139 -0.3908 0.5234 0.038 Uiso calc R 1 C C3 1.24880(11) -0.1894(3) 0.55062(8) 0.0356(3) Uani d . 1 H H3 1.2846 -0.2866 0.5932 0.043 Uiso calc R 1 C C4 1.29830(11) 0.0143(3) 0.52972(8) 0.0380(3) Uani d . 1 H H4 1.3676 0.0532 0.5584 0.046 Uiso calc R 1 C C5 1.24877(11) 0.1619(2) 0.46793(8) 0.0346(3) Uani d . 1 H H5 1.2834 0.2991 0.4535 0.041 Uiso calc R 1 C C6 1.14717(10) 0.1021(2) 0.42818(7) 0.0281(3) Uani d . 1 C C7 1.07353(10) 0.2269(2) 0.36116(8) 0.0296(3) Uani d . 1 H H7A 1.0587 0.3916 0.3761 0.036 Uiso calc R 1 H H7B 1.1030 0.2308 0.3124 0.036 Uiso calc R 1 C C8 0.99162(10) -0.1207(2) 0.39860(7) 0.0263(3) Uani d . 1 C C9 0.89044(10) 0.1374(2) 0.28902(7) 0.0284(3) Uani d . 1 C C10 0.71058(10) -0.0067(2) 0.22699(8) 0.0301(3) Uani d . 1 C C11 0.68394(11) 0.1681(3) 0.16870(8) 0.0360(3) Uani d . 1 H H11 0.7324 0.2927 0.1648 0.043 Uiso calc R 1 C C12 0.58577(11) 0.1588(3) 0.11620(9) 0.0419(4) Uani d . 1 H H12 0.5675 0.2784 0.0765 0.050 Uiso calc R 1 C C13 0.51455(12) -0.0206(3) 0.12064(9) 0.0452(4) Uani d . 1 H H13 0.4481 -0.0259 0.0840 0.054 Uiso calc R 1 C C14 0.54067(12) -0.1927(3) 0.17890(10) 0.0480(4) Uani d . 1 H H14 0.4916 -0.3158 0.1828 0.058 Uiso calc R 1 C C15 0.63785(11) -0.1869(3) 0.23162(9) 0.0401(3) Uani d . 1 H H15 0.6552 -0.3067 0.2713 0.048 Uiso calc R 1 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 0.0361(5) 0.0257(5) 0.0383(5) -0.0031(4) 0.0116(4) 0.0042(4) O2 0.0453(6) 0.0332(5) 0.0402(6) -0.0068(4) 0.0016(4) 0.0125(4) N1 0.0310(6) 0.0215(5) 0.0280(5) -0.0004(4) 0.0093(4) 0.0015(4) N2 0.0330(6) 0.0276(5) 0.0290(6) -0.0025(4) 0.0080(4) 0.0037(4) C1 0.0315(6) 0.0226(6) 0.0286(6) 0.0032(5) 0.0119(5) -0.0018(5) C2 0.0375(7) 0.0267(6) 0.0328(7) 0.0051(5) 0.0131(6) 0.0026(5) C3 0.0383(7) 0.0360(7) 0.0333(7) 0.0105(6) 0.0094(6) 0.0028(6) C4 0.0322(7) 0.0410(8) 0.0398(8) 0.0035(6) 0.0054(6) -0.0033(6) C5 0.0349(7) 0.0296(7) 0.0403(8) -0.0023(6) 0.0105(6) -0.0016(6) C6 0.0330(7) 0.0237(6) 0.0296(7) 0.0019(5) 0.0113(5) -0.0023(5) C7 0.0336(7) 0.0223(6) 0.0336(7) -0.0033(5) 0.0084(5) 0.0006(5) C8 0.0340(7) 0.0200(6) 0.0281(6) 0.0025(5) 0.0139(5) -0.0004(5) C9 0.0347(7) 0.0248(6) 0.0272(6) 0.0002(5) 0.0097(5) -0.0012(5) C10 0.0314(7) 0.0302(6) 0.0302(7) 0.0011(5) 0.0100(5) -0.0036(5) C11 0.0335(7) 0.0347(7) 0.0406(8) -0.0003(6) 0.0092(6) 0.0050(6) C12 0.0356(7) 0.0448(8) 0.0444(8) 0.0033(6) 0.0067(6) 0.0085(7) C13 0.0339(8) 0.0493(9) 0.0494(9) -0.0019(7) 0.0024(7) 0.0009(7) C14 0.0407(8) 0.0425(8) 0.0583(10) -0.0122(7) 0.0048(7) 0.0028(7) C15 0.0419(8) 0.0341(7) 0.0434(8) -0.0063(6) 0.0070(7) 0.0043(6) 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 C8 N1 C9 128.19(10) C8 N1 C7 112.54(10) C9 N1 C7 118.99(10) C9 N2 C10 127.29(11) C9 N2 H2N 116.4 C10 N2 H2N 116.4 C6 C1 C2 122.40(12) C6 C1 C8 109.11(11) C2 C1 C8 128.47(12) C3 C2 C1 117.27(12) C3 C2 H2 121.4 C1 C2 H2 121.4 C2 C3 C4 120.69(13) C2 C3 H3 119.7 C4 C3 H3 119.7 C5 C4 C3 121.61(13) C5 C4 H4 119.2 C3 C4 H4 119.2 C6 C5 C4 117.71(13) C6 C5 H5 121.1 C4 C5 H5 121.1 C5 C6 C1 120.30(12) C5 C6 C7 130.05(12) C1 C6 C7 109.66(11) N1 C7 C6 102.34(10) N1 C7 H7A 111.3 C6 C7 H7A 111.3 N1 C7 H7B 111.3 C6 C7 H7B 111.3 H7A C7 H7B 109.2 O1 C8 N1 125.74(12) O1 C8 C1 128.03(11) N1 C8 C1 106.22(10) O2 C9 N2 126.40(12) O2 C9 N1 119.71(12) N2 C9 N1 113.89(11) C11 C10 C15 119.12(13) C11 C10 N2 124.12(12) C15 C10 N2 116.75(12) C12 C11 C10 119.41(13) C12 C11 H11 120.3 C10 C11 H11 120.3 C13 C12 C11 121.24(14) C13 C12 H12 119.4 C11 C12 H12 119.4 C12 C13 C14 119.29(14) C12 C13 H13 120.4 C14 C13 H13 120.4 C13 C14 C15 120.41(14) C13 C14 H14 119.8 C15 C14 H14 119.8 C14 C15 C10 120.52(14) C14 C15 H15 119.7 C10 C15 H15 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C8 1.2293(15) O2 C9 1.2148(16) N1 C8 1.3859(15) N1 C9 1.4057(17) N1 C7 1.4676(16) N2 C9 1.3556(16) N2 C10 1.4073(17) N2 H2N 0.8800 C1 C6 1.3865(17) C1 C2 1.3883(18) C1 C8 1.4715(18) C2 C3 1.384(2) C2 H2 0.9500 C3 C4 1.394(2) C3 H3 0.9500 C4 C5 1.391(2) C4 H4 0.9500 C5 C6 1.3851(19) C5 H5 0.9500 C6 C7 1.5016(18) C7 H7A 0.9900 C7 H7B 0.9900 C10 C11 1.3921(19) C10 C15 1.3944(19) C11 C12 1.391(2) C11 H11 0.9500 C12 C13 1.377(2) C12 H12 0.9500 C13 C14 1.380(2) C13 H13 0.9500 C14 C15 1.383(2) C14 H14 0.9500 C15 H15 0.9500 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 C2 H2 O1 3_746 0.95 2.41 3.3105(17) 159.1 C7 H7B O2 2_745 0.99 2.57 3.0746(17) 111.5 C7 H7B N2 2_755 0.99 2.60 3.4695(18) 147.1 C11 H11 O2 . 0.95 2.27 2.8833(19) 121.5 N2 H2N O1 . 0.88 1.95 2.6803(15) 140.0 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 C6 C1 C2 C3 0.42(18) C8 C1 C2 C3 -177.84(12) C1 C2 C3 C4 -0.79(19) C2 C3 C4 C5 0.1(2) C3 C4 C5 C6 1.0(2) C4 C5 C6 C1 -1.35(19) C4 C5 C6 C7 178.64(13) C2 C1 C6 C5 0.67(19) C8 C1 C6 C5 179.23(11) C2 C1 C6 C7 -179.32(11) C8 C1 C6 C7 -0.76(13) C8 N1 C7 C6 -3.79(13) C9 N1 C7 C6 -178.24(10) C5 C6 C7 N1 -177.34(13) C1 C6 C7 N1 2.65(13) C9 N1 C8 O1 -3.3(2) C7 N1 C8 O1 -177.10(12) C9 N1 C8 C1 177.28(11) C7 N1 C8 C1 3.46(13) C6 C1 C8 O1 178.97(12) C2 C1 C8 O1 -2.6(2) C6 C1 C8 N1 -1.61(13) C2 C1 C8 N1 176.84(12) C10 N2 C9 O2 0.3(2) C10 N2 C9 N1 -179.59(11) C8 N1 C9 O2 -175.71(12) C7 N1 C9 O2 -2.24(17) C8 N1 C9 N2 4.20(17) C7 N1 C9 N2 177.67(10) C9 N2 C10 C11 0.9(2) C9 N2 C10 C15 -179.93(12) C15 C10 C11 C12 -0.3(2) N2 C10 C11 C12 178.82(13) C10 C11 C12 C13 -0.2(2) C11 C12 C13 C14 0.8(2) C12 C13 C14 C15 -0.8(3) C13 C14 C15 C10 0.3(2) C11 C10 C15 C14 0.2(2) N2 C10 C15 C14 -178.95(13)