#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008568.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_2008568 loop_ _publ_author_name 'Fitzgerald, Lawrence J.' 'Gerkin, Roger E.' _publ_section_title ; Network of C---H···O interactions in 1,2-naphthalenedicarboxylic anhydride ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 937 _journal_page_last 940 _journal_paper_doi 10.1107/S0108270199002577 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C12 H16 O3 ' _chemical_formula_sum 'C12 H6 O3' _chemical_formula_weight 198.18 _chemical_name_common 'naphthalene-1,2-dicarboxylic anhydride' _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' _cell_angle_alpha 90 _cell_angle_beta 107.34(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.714(2) _cell_length_b 17.848(2) _cell_length_c 6.910(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.9 _cell_measurement_theta_min 14.2 _cell_volume 908.1(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN (Molecular Structure Corporation, 1995) ; _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990) ' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type AFC5S _diffrn_measurement_method '\w scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 2328 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+- 2.4 (average maximum relative intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method none _exptl_crystal_description 'uncut column' _exptl_crystal_F_000 408 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.34 _refine_diff_density_min -0.32 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.62 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2080 _refine_ls_R_factor_gt 0.045 _refine_ls_shift/su_max 0.0002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/ \s^2^(F^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.052 _reflns_number_gt 1141 _reflns_number_total 2083 _reflns_threshold_expression 'I > 2\sI' _cod_data_source_file fr1187.cif _cod_data_source_block 1 _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 The following automatic conversions were performed: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 15 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/ \s^2^(F^2^)' 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^(F^2^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 908.0(4) _cod_original_sg_symbol_H-M 'P 21/c' _cod_original_formula_sum 'C12 H6 O3 ' _cod_database_code 2008568 loop_ _symmetry_equiv_pos_as_xyz x,y,z '-x, 1/2 +y, 1/2 -z' '-x, -y, -z' '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_calc_attached_atom O1 .64720(10) .14931(7) .3429(2) .0728(5) Uani ? ? O2 .4274(2) .06223(6) .2861(2) .0623(4) Uani ? ? O3 .1550(2) .00545(7) .2187(2) .0904(5) Uani ? ? C1 .3282(2) .18559(8) .2584(3) .0394(5) Uani ? ? C2 .1783(2) .14121(9) .2199(2) .0440(5) Uani ? ? C3 .0037(3) .17070(10) .1743(3) .0580(7) Uani ? ? C4 -.0119(3) .24650(10) .1695(3) .0618(7) Uani ? ? C5 .1219(3) .37380(10) .2030(3) .0716(8) Uani ? ? C6 .2692(4) .41910(10) .2411(3) .0824(9) Uani ? ? C7 .4434(4) .38880(10) .2870(3) .0746(9) Uani ? ? C8 .4691(3) .31290(10) .2940(3) .0571(7) Uani ? ? C9 .3180(2) .26440(8) .2550(3) .0418(5) Uani ? ? C10 .1408(3) .29505(9) .2080(3) .0498(6) Uani ? ? C11 .4887(2) .13618(10) .3012(3) .0512(6) Uani ? ? C12 .2378(3) .06247(10) .2378(3) .0587(7) Uani ? ? H3 -.100(2) .1364(9) .147(3) .084(6) Uiso ? ? H4 -.123(2) .2715(8) .138(2) .072(6) Uiso ? ? H5 .002(2) .3966(9) .173(2) .072(6) Uiso ? ? H6 .251(2) .4750(10) .240(3) .110(8) Uiso ? ? H7 .546(2) .4222(9) .312(3) .088(7) Uiso ? ? H8 .590(2) .2915(7) .325(2) .056(5) Uiso ? ? 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 .0443(8) .0791(9) .0950(10) .0053(8) .0207(8) .0001(9) O2 .0677(9) .0401(7) .0790(10) .0055(7) .0217(7) .0004(7) O3 .1100(10) .0504(8) .1060(10) -.0323(9) .0258(9) -.0013(9) C1 .0368(9) .0431(9) .0400(10) .0014(8) .0140(8) -.0002(9) C2 .0410(10) .0480(10) .0440(10) -.0036(9) .0149(8) .0026(9) C3 .0470(10) .074(2) .0550(10) -.0100(10) .0180(10) .0030(10) C4 .0460(10) .087(2) .0540(10) .0190(10) .0170(10) .0080(10) C5 .101(2) .0590(10) .058(2) .0280(10) .0280(10) .0050(10) C6 .148(3) .0400(10) .060(2) .0140(10) .032(2) .0010(10) C7 .115(2) .0460(10) .063(2) -.0240(10) .026(2) -.0020(10) C8 .068(2) .0510(10) .0530(10) -.0090(10) .0190(10) .0000(10) C9 .0510(10) .0388(9) .0380(10) -.0036(9) .0165(8) -.0008(9) C10 .0640(10) .0490(10) .0390(10) .0130(10) .0190(10) .0022(9) C11 .0540(10) .0480(10) .0530(10) -.0010(10) .0180(10) -.0008(10) C12 .0730(10) .0480(10) .0540(10) -.0110(10) .0190(10) .0000(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C 0.003 0.002 'Creagh & McAuley (1992)' O 0.011 0.006 'Creagh & McAuley (1992)' 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 C11 O2 C12 108.80(10) yes C2 C1 C9 122.5(2) no C2 C1 C11 107.70(10) no C9 C1 C11 129.7(2) no C1 C2 C3 122.2(2) no C1 C2 C12 108.3(2) no C3 C2 C12 129.5(2) no C2 C3 C4 117.1(2) no C2 C3 H3 119.1(9) no C4 C3 H3 123.8(9) no C3 C4 C10 122.7(2) no C3 C4 H4 123.4(10) no C10 C4 H4 113.9(9) no C6 C5 C10 121.0(2) no C6 C5 H5 118.0(10) no C10 C5 H5 120.0(10) no C5 C6 C7 120.5(2) no C5 C6 H6 119.1(10) no C7 C6 H6 120.4(10) no C6 C7 C8 120.8(2) no C6 C7 H7 119.1(10) no C8 C7 H7 120.0(10) no C7 C8 C9 119.8(2) no C7 C8 H8 121.2(9) no C9 C8 H8 119.0(9) no C1 C9 C8 124.8(2) no C1 C9 C10 115.7(2) no C8 C9 C10 119.5(2) no C4 C10 C5 121.9(2) no C4 C10 C9 119.8(2) no C5 C10 C9 118.4(2) no O1 C11 O2 120.3(2) yes O1 C11 C1 132.0(2) yes O2 C11 C1 107.70(10) yes O2 C12 O3 120.9(2) yes O2 C12 C2 107.50(10) yes O3 C12 C2 131.7(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C11 ? ? 1.192(2) yes O2 C11 ? ? 1.395(2) yes O2 C12 ? ? 1.400(2) yes O3 C12 ? ? 1.188(2) yes C1 C2 ? ? 1.361(2) yes C1 C9 ? ? 1.409(2) no C1 C11 ? ? 1.476(2) yes C2 C3 ? ? 1.392(2) no C2 C12 ? ? 1.472(2) yes C3 C4 ? ? 1.358(3) no C3 H3 ? ? .980(10) no C4 C10 ? ? 1.421(2) no C4 H4 ? ? .930(10) no C5 C6 ? ? 1.355(3) no C5 C10 ? ? 1.413(2) no C5 H5 ? ? .980(10) no C6 C7 ? ? 1.395(3) no C6 H6 ? ? 1.01(2) no C7 C8 ? ? 1.368(2) no C7 H7 ? ? .97(2) no C8 C9 ? ? 1.412(2) no C8 H8 ? ? .970(10) no C9 C10 ? ? 1.418(2) no 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 _geom_hbond_publ_flag C3 H3 O1 1_455 0.980(10) 2.69(2) 3.313(2) 122.0(10) yes C4 H4 O1 4_454 0.930(10) 2.67(2) 3.453(2) 142.0(10) yes C5 H5 O3 2_555 0.980(10) 2.52(2) 3.326(2) 140.0(10) yes C7 H7 O2 2_655 0.97(2) 2.61(2) 3.336(2) 132.0(10) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 21437