#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/63/2006379.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_2006379 loop_ _publ_author_name 'Batchelor, Rhys A.' 'Hunter, Christopher A.' 'Simpson, Jim' _publ_section_title ; 3-(1,8-Naphthalenedicarboximido)benzonitrile [or N-(3-Cyanophenyl)-1,8-naphthalimide], C~19~H~10~N~2~O~2~ ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1117 _journal_page_last 1119 _journal_paper_doi 10.1107/S0108270197003727 _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C19 H10 N2 O2' _chemical_formula_weight 298.29 _chemical_name_systematic ; 3-(1,8-naphthalenedicarboximido)benzonitrile, or N-(3-benzonitrile)-1,8-naphthalimide or strict IUPAC name 3-(1,3-dioxo-2,3-dihydro-1H-naphtho-[1,8-cd]- azin-2yl)benzonitrile ; _space_group_IT_number 60 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_space_group_name_H-M 'P b c n' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 14.997(6) _cell_length_b 12.898(9) _cell_length_c 14.743(14) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17.43 _cell_measurement_theta_min 12.05 _cell_volume 2852(4) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _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 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0803 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2520 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.08 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'truncated octahedron' _exptl_crystal_F_000 1232 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.176 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.926 _refine_ls_goodness_of_fit_obs 1.208 _refine_ls_hydrogen_treatment 'H atoms refined using AFIX in SHELXL93 (Sheldrick, 1993)' _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2520 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.926 _refine_ls_restrained_S_obs 1.208 _refine_ls_R_factor_all 0.1431 _refine_ls_R_factor_obs .0682 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0693P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1626 _refine_ls_wR_factor_obs .1373 _reflns_number_observed 1162 _reflns_number_total 2520 _reflns_observed_criterion >2sigma(I) _cod_data_source_file fg1259.cif _cod_data_source_block rhyb _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0693P)^2^] 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^)+(0.0693P)^2^] 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 2852.(4) _cod_database_code 2006379 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, 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 .049(2) .043(2) .112(3) -.001(2) -.010(2) -.002(2) C1 .040(3) .042(2) .052(3) -.002(2) -.001(2) .001(2) C2 .045(3) .031(2) .040(2) -.003(2) .006(2) .001(2) C3 .047(3) .038(2) .067(3) .005(2) .002(2) .005(2) C4 .063(3) .036(2) .069(3) .009(2) .006(3) .005(2) C5 .071(3) .029(2) .052(3) -.007(2) .009(3) -.001(2) C6 .056(3) .029(2) .039(2) -.002(2) .009(2) -.002(2) C7 .063(3) .037(2) .052(3) -.012(2) .001(2) -.011(2) C8 .053(3) .050(3) .063(3) -.013(2) -.010(2) -.008(2) C9 .056(3) .041(2) .058(3) .000(2) -.005(2) -.001(2) C10 .046(3) .039(2) .033(2) -.003(2) .001(2) -.002(2) C11 .044(2) .033(2) .028(2) -.001(2) .003(2) -.004(2) C12 .049(3) .035(2) .034(2) .004(2) .000(2) .001(2) O2 .059(2) .037(2) .074(2) .006(2) -.011(2) .003(2) N1 .045(2) .028(2) .047(2) -.003(2) -.003(2) .0018(14) C13 .040(2) .030(2) .042(2) -.004(2) -.004(2) .003(2) C14 .053(3) .037(2) .039(2) .003(2) -.002(2) .000(2) C15 .045(2) .032(2) .041(2) .002(2) .006(2) .003(2) C19 .064(3) .033(2) .060(3) -.002(2) .006(3) -.001(2) N2 .111(4) .046(2) .062(3) .001(2) .012(3) .012(2) C16 .043(3) .030(2) .061(3) -.003(2) -.004(2) -.005(2) C17 .054(3) .040(2) .044(2) -.003(2) .003(2) -.006(2) C18 .051(3) .040(2) .043(2) -.005(2) -.001(2) .007(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 -.1960(2) .3119(2) .0600(2) .0682(10) Uani d . 1 . O C1 -.1209(3) .3358(3) .0828(3) .0446(10) Uani d . 1 . C C2 -.0906(3) .4436(3) .0934(2) .0386(10) Uani d . 1 . C C3 -.1487(3) .5236(3) .0760(3) .0505(11) Uani d . 1 . C H3 -.2061(3) .5091(3) .0557(3) .050 Uiso calc R 1 . H C4 -.1221(3) .6266(3) .0885(3) .0559(12) Uani d . 1 . C H4 -.1620(3) .6803(3) .0772(3) .050 Uiso calc R 1 . H C5 -.0376(3) .6484(3) .1174(3) .0508(12) Uani d . 1 . C H5 -.0208(3) .7171(3) .1261(3) .050 Uiso calc R 1 . H C6 .0247(3) .5690(3) .1343(3) .0410(10) Uani d . 1 . C C7 .1129(3) .5884(3) .1629(3) .0506(11) Uani d . 1 . C H7 .1323(3) .6563(3) .1709(3) .050 Uiso calc R 1 . H C8 .1694(3) .5088(3) .1785(3) .0554(12) Uani d . 1 . C H8 .2275(3) .5229(3) .1969(3) .050 Uiso calc R 1 . H C9 .1424(3) .4055(3) .1677(3) .0516(11) Uani d . 1 . C H9 .1824(3) .3519(3) .1788(3) .050 Uiso calc R 1 . H C10 .0578(3) .3838(3) .1412(2) .0393(10) Uani d . 1 . C C11 -.0031(3) .4648(3) .1229(2) .0351(9) Uani d . 1 . C C12 .0303(3) .2753(3) .1288(3) .0394(10) Uani d . 1 . C O2 .0798(2) .2020(2) .1422(2) .0564(8) Uani d . 1 . O N1 -.0576(2) .2579(2) .1000(2) .0400(8) Uani d . 1 . N C13 -.0837(2) .1514(3) .0836(3) .0373(10) Uani d . 1 . C C14 -.0919(3) .0829(3) .1547(3) .0432(10) Uani d . 1 . C H14 -.0852(3) .1054(3) .2143(3) .050 Uiso calc R 1 . H C15 -.1102(3) -.0200(3) .1360(3) .0391(10) Uani d . 1 . C C19 -.1189(3) -.0925(3) .2101(3) .0522(12) Uani d . 1 . C N2 -.1250(3) -.1483(3) .2696(3) .0729(13) Uani d . 1 . N C16 -.1216(3) -.0547(3) .0476(3) .0446(11) Uani d . 1 . C H16 -.1334(3) -.1242(3) .0360(3) .050 Uiso calc R 1 . H C17 -.1152(3) .0159(3) -.0231(3) .0459(11) Uani d . 1 . C H17 -.1238(3) -.0057(3) -.0826(3) .050 Uiso calc R 1 . H C18 -.0959(3) .1182(3) -.0048(3) .0449(11) Uani d . 1 . C H18 -.0910(3) .1653(3) -.0522(3) .050 Uiso calc R 1 . H 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 _geom_angle_publ_flag O1 C1 N1 119.6(4) yes O1 C1 C2 123.8(4) yes N1 C1 C2 116.6(4) yes C3 C2 C11 120.1(3) no C3 C2 C1 119.5(4) no C11 C2 C1 120.3(3) yes C2 C3 C4 120.4(4) no C5 C4 C3 120.1(4) no C4 C5 C6 121.4(4) no C5 C6 C7 123.0(4) no C5 C6 C11 118.3(4) no C7 C6 C11 118.7(4) no C8 C7 C6 120.2(4) no C7 C8 C9 121.5(4) no C10 C9 C8 119.9(4) no C9 C10 C11 120.4(3) no C9 C10 C12 119.7(4) no C11 C10 C12 119.9(4) yes C2 C11 C10 121.1(3) yes C2 C11 C6 119.7(3) no C10 C11 C6 119.3(4) no O2 C12 N1 119.8(3) yes O2 C12 C10 123.2(4) yes N1 C12 C10 117.0(3) yes C12 N1 C1 125.0(3) yes C12 N1 C13 117.1(3) yes C1 N1 C13 117.8(3) yes C14 C13 C18 120.4(4) no C14 C13 N1 120.4(3) yes C18 C13 N1 119.1(3) yes C13 C14 C15 118.8(4) no C14 C15 C16 121.4(3) no C14 C15 C19 119.3(4) no C16 C15 C19 119.3(3) yes N2 C19 C15 178.6(5) yes C17 C16 C15 119.0(4) no C18 C17 C16 119.7(4) no C17 C18 C13 120.6(4) no 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 C1 . 1.216(4) yes C1 N1 . 1.405(5) yes C1 C2 . 1.471(5) yes C2 C3 . 1.375(5) yes C2 C11 . 1.409(5) yes C3 C4 . 1.400(5) yes C4 C5 . 1.367(6) yes C5 C6 . 1.409(5) yes C6 C7 . 1.411(5) yes C6 C11 . 1.416(5) yes C7 C8 . 1.351(5) yes C8 C9 . 1.401(5) yes C9 C10 . 1.357(6) yes C10 C11 . 1.414(5) yes C10 C12 . 1.470(5) yes C12 O2 . 1.219(4) yes C12 N1 . 1.403(5) yes N1 C13 . 1.448(4) yes C13 C14 . 1.376(5) no C13 C18 . 1.385(5) no C14 C15 . 1.383(5) no C15 C16 . 1.388(5) no C15 C19 . 1.444(6) yes C19 N2 . 1.138(5) yes C16 C17 . 1.388(5) no C17 C18 . 1.377(5) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137607 2 PubChem 45029752