#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206890.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_2206890 loop_ _publ_author_name 'Xiu-Zhi Xu' 'Mei-Jin Lin' 'Jun-Dong Wang' 'Nai-Sheng Chen' 'Jin-Ling Huang' _publ_section_title ; 4-[(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phthalonitrile ; _journal_coeditor_code BV6027 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3145 _journal_page_last o3146 _journal_paper_doi 10.1107/S1600536805027443 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C17 H9 N3 O2' _chemical_formula_moiety 'C17 H9 N3 O2' _chemical_formula_sum 'C17 H9 N3 O2' _chemical_formula_weight 287.27 _chemical_melting_point 550 _chemical_name_common '4-Phthalimidomethyl Phthalonitrile' _chemical_name_systematic ; 4-[4-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]phthalonitrile ; _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 difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.0930(13) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9331(3) _cell_length_b 26.2490(13) _cell_length_c 10.4901(6) _cell_measurement_reflns_used 6576 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 54.87 _cell_measurement_theta_min 6.08 _cell_volume 1356.37(13) _computing_cell_refinement RAPID-AUTO _computing_data_collection 'RAPID-AUTO (Rigaku, 1998)' _computing_data_reduction RAPID-AUTO _computing_molecular_graphics 'ORTEX (McArdle, 1995)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11806 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 1.55 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.141 _refine_diff_density_min -0.231 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 3107 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0899 _refine_ls_R_factor_gt 0.0373 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.042P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.1169 _reflns_number_gt 1558 _reflns_number_total 3107 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bv6027.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2206890 _cod_database_fobs_code 2206890 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_occupancy _atom_site_type_symbol O1 0.2424(4) 0.45468(6) 0.53538(16) 0.0646(5) Uani d 1 O N3 0.6074(4) 0.43376(6) 0.67135(16) 0.0426(4) Uani d 1 N O2 0.9408(3) 0.43535(6) 0.83339(16) 0.0630(5) Uani d 1 O N2 -0.0776(5) 0.31120(8) 1.0056(2) 0.0745(7) Uani d 1 N N1 0.1309(5) 0.17509(8) 0.8964(2) 0.0818(8) Uani d 1 N H7 0.538(5) 0.6111(9) 0.953(2) 0.073(8) Uiso d 1 H H9 0.093(5) 0.5598(8) 0.641(2) 0.059(7) Uiso d 1 H H6 0.808(5) 0.5375(8) 0.950(2) 0.059(7) Uiso d 1 H H8 0.187(5) 0.6222(10) 0.795(2) 0.081(8) Uiso d 1 H H4 0.871(5) 0.3810(8) 0.612(2) 0.054(7) Uiso d 1 H H5 0.583(5) 0.3847(9) 0.525(3) 0.081(9) Uiso d 1 H H3 0.582(4) 0.2153(9) 0.675(2) 0.057(6) Uiso d 1 H H2 0.771(5) 0.2870(8) 0.580(2) 0.054(6) Uiso d 1 H H1 0.317(4) 0.3757(8) 0.7989(19) 0.044(6) Uiso d 1 H C1 0.3429(5) 0.25312(8) 0.7931(2) 0.0466(6) Uani d 1 C C2 0.2638(4) 0.30184(7) 0.83024(19) 0.0421(5) Uani d 1 C C3 0.3708(5) 0.34450(8) 0.7736(2) 0.0426(5) Uani d 1 C C4 0.5586(4) 0.33982(7) 0.6807(2) 0.0406(5) Uani d 1 C C5 0.6381(5) 0.29126(9) 0.6455(2) 0.0490(6) Uani d 1 C C6 0.5322(5) 0.24848(9) 0.7004(2) 0.0537(6) Uani d 1 C C7 0.2260(5) 0.20910(9) 0.8501(2) 0.0565(6) Uani d 1 C C8 0.0730(5) 0.30722(8) 0.9279(2) 0.0511(6) Uani d 1 C C9 0.6713(6) 0.38532(8) 0.6138(2) 0.0485(6) Uani d 1 C C10 0.4034(4) 0.51094(7) 0.70815(19) 0.0416(5) Uani d 1 C C11 0.6141(4) 0.50473(7) 0.80021(19) 0.0420(5) Uani d 1 C C12 0.6674(5) 0.54112(9) 0.8928(2) 0.0551(6) Uani d 1 C C13 0.5050(6) 0.58403(9) 0.8901(3) 0.0618(7) Uani d 1 C C14 0.2955(5) 0.59030(9) 0.7978(3) 0.0577(7) Uani d 1 C C15 0.2404(5) 0.55369(8) 0.7046(2) 0.0509(6) Uani d 1 C C16 0.3947(5) 0.46518(8) 0.6249(2) 0.0450(5) Uani d 1 C C17 0.7488(5) 0.45506(8) 0.7767(2) 0.0452(5) Uani d 1 C 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 0.0690(12) 0.0635(10) 0.0591(11) 0.0001(9) -0.0150(10) -0.0092(8) N3 0.0472(10) 0.0382(9) 0.0425(10) -0.0015(9) 0.0045(9) -0.0008(8) O2 0.0583(11) 0.0651(10) 0.0642(11) 0.0162(9) -0.0093(9) -0.0038(9) N2 0.0887(17) 0.0611(13) 0.0777(16) -0.0039(12) 0.0414(14) 0.0014(11) N1 0.105(2) 0.0569(13) 0.0849(18) -0.0153(14) 0.0165(15) 0.0083(13) C1 0.0510(13) 0.0399(12) 0.0490(13) -0.0011(10) 0.0045(11) -0.0004(10) C2 0.0424(12) 0.0428(12) 0.0415(13) -0.0004(10) 0.0053(10) 0.0008(9) C3 0.0470(13) 0.0386(12) 0.0427(13) 0.0048(11) 0.0072(10) -0.0027(10) C4 0.0415(12) 0.0402(12) 0.0400(12) 0.0000(10) 0.0022(10) -0.0026(9) C5 0.0522(14) 0.0462(13) 0.0500(14) 0.0037(11) 0.0157(12) -0.0058(11) C6 0.0643(16) 0.0392(13) 0.0588(16) 0.0045(12) 0.0134(13) -0.0065(11) C7 0.0671(17) 0.0448(13) 0.0583(15) -0.0030(13) 0.0086(13) 0.0006(12) C8 0.0570(15) 0.0434(13) 0.0543(15) -0.0022(11) 0.0148(13) 0.0017(11) C9 0.0534(16) 0.0426(12) 0.0508(15) -0.0008(12) 0.0140(12) -0.0033(11) C10 0.0431(13) 0.0399(11) 0.0422(13) -0.0052(10) 0.0062(10) 0.0025(9) C11 0.0436(13) 0.0408(11) 0.0419(13) -0.0042(10) 0.0063(11) 0.0001(10) C12 0.0558(16) 0.0591(16) 0.0497(15) -0.0042(13) -0.0038(13) -0.0066(12) C13 0.0754(18) 0.0484(14) 0.0617(17) -0.0015(14) 0.0057(15) -0.0138(13) C14 0.0634(17) 0.0422(13) 0.0679(17) 0.0046(13) 0.0071(14) -0.0020(12) C15 0.0521(14) 0.0475(13) 0.0532(15) 0.0026(12) 0.0042(12) 0.0059(11) C16 0.0466(13) 0.0457(12) 0.0429(13) -0.0063(11) 0.0049(11) 0.0035(10) C17 0.0445(13) 0.0484(12) 0.0432(13) -0.0016(11) 0.0065(11) 0.0032(10) 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 C17 N3 C16 111.94(17) C17 N3 C9 124.89(19) C16 N3 C9 123.16(19) C6 C1 C2 118.9(2) C6 C1 C7 121.4(2) C2 C1 C7 119.7(2) C3 C2 C1 120.1(2) C3 C2 C8 120.42(19) C1 C2 C8 119.50(19) C2 C3 C4 121.0(2) C2 C3 H1 118.8(13) C4 C3 H1 120.3(13) C3 C4 C5 118.5(2) C3 C4 C9 122.34(19) C5 C4 C9 119.1(2) C6 C5 C4 121.2(2) C6 C5 H2 118.8(13) C4 C5 H2 120.0(13) C5 C6 C1 120.4(2) C5 C6 H3 121.5(13) C1 C6 H3 118.1(13) N1 C7 C1 178.6(3) N2 C8 C2 179.6(3) N3 C9 C4 114.01(18) N3 C9 H4 110.2(13) C4 C9 H4 107.9(13) N3 C9 H5 107.9(14) C4 C9 H5 105.4(14) H4 C9 H5 111(2) C15 C10 C11 121.8(2) C15 C10 C16 130.1(2) C11 C10 C16 108.11(18) C12 C11 C10 121.0(2) C12 C11 C17 130.8(2) C10 C11 C17 108.11(18) C11 C12 C13 117.6(2) C11 C12 H6 120.6(15) C13 C12 H6 121.8(15) C12 C13 C14 121.4(2) C12 C13 H7 120.2(15) C14 C13 H7 118.4(14) C13 C14 C15 121.3(2) C13 C14 H8 120.0(15) C15 C14 H8 118.6(15) C10 C15 C14 116.9(2) C10 C15 H9 124.3(13) C14 C15 H9 118.7(13) O1 C16 N3 124.1(2) O1 C16 C10 130.0(2) N3 C16 C10 105.91(18) O2 C17 N3 124.4(2) O2 C17 C11 129.6(2) N3 C17 C11 105.92(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C16 1.202(2) N3 C17 1.391(3) N3 C16 1.401(3) N3 C9 1.450(3) O2 C17 1.207(3) N2 C8 1.137(3) N1 C7 1.130(3) C1 C6 1.390(3) C1 C2 1.398(3) C1 C7 1.436(3) C2 C3 1.386(3) C2 C8 1.435(3) C3 C4 1.386(3) C3 H1 0.91(2) C4 C5 1.390(3) C4 C9 1.507(3) C5 C6 1.378(3) C5 H2 0.98(2) C6 H3 0.95(2) C9 H4 0.99(2) C9 H5 1.01(3) C10 C15 1.380(3) C10 C11 1.390(3) C10 C16 1.484(3) C11 C12 1.377(3) C11 C17 1.490(3) C12 C13 1.382(3) C12 H6 0.89(2) C13 C14 1.387(4) C13 H7 0.98(2) C14 C15 1.388(3) C14 H8 0.99(3) C15 H9 0.97(2) 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 C3 H1 O2 1_455 0.91(2) 2.47(2) 3.275(3) 148.4(17) C6 H3 N2 2_654 0.95(2) 2.60(2) 3.280(3) 128.6(16) C15 H9 O1 3_566 0.97(2) 2.44(2) 3.378(3) 160.7(17) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21128830 2 PubChem 139068379