#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008528.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_2008528 loop_ _publ_author_name 'Britton, Doyle' _publ_section_title ; Naphthalene-2,3-dicarbaldehyde ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 978 _journal_page_last 980 _journal_paper_doi 10.1107/S0108270199000840 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C12 H8 O2' _chemical_formula_weight 184.18 _chemical_name_systematic ; naphthalene-2,3-dicarbaldehyde ; _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' _audit_creation_method 'SHELXL plus manual additions' _cell_angle_alpha 90.00 _cell_angle_beta 91.412(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 3.8724(2) _cell_length_b 12.0839(5) _cell_length_c 18.4079(6) _cell_measurement_reflns_used 2848 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.1 _cell_measurement_theta_min 2.0 _cell_volume 861.11(6) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'ASTRO (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 173(2) _diffrn_measurement_device 'Siemens SMART area-detector' _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 0.029 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 4396 _diffrn_reflns_theta_max 25.11 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% '< 1' _diffrn_standards_number 209 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996; Blessing, 1995) ' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.4210(10) _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut from needle' _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.17 _refine_diff_density_min -0.19 _refine_ls_extinction_coef 0.007(4) _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1995)' _refine_ls_goodness_of_fit_all 1.06 _refine_ls_goodness_of_fit_obs 1.08 _refine_ls_hydrogen_treatment 'H atoms: see below' _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 1530 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.047 _refine_ls_R_factor_obs .039 _refine_ls_shift/esd_max 0.01 _refine_ls_shift/esd_mean 0.00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(Fo^2^)+(0.056P)^2^+0.270P] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_wR_factor_all 0.108 _refine_ls_wR_factor_obs .101 _reflns_number_observed 1310 _reflns_number_total 1530 _reflns_observed_criterion I>2\s(I) _cod_data_source_file bk1446.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'N' changed to 'n' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15 times). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008528 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_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 .0668(9) .0335(7) .0387(7) .0040(6) -.0119(6) .0033(5) O2 .0626(8) .0361(7) .0359(7) .0115(6) .0084(6) -.0040(5) C1 .0246(7) .0208(7) .0332(8) -.0026(6) .0026(6) -.0004(6) C2 .0263(7) .0201(7) .0320(8) -.0032(6) .0033(6) -.0006(6) C3 .0287(8) .0181(7) .0355(8) -.0016(6) .0063(6) -.0027(6) C4 .0244(7) .0198(7) .0343(8) -.0020(6) .0047(6) .0022(6) C5 .0311(8) .0235(8) .0406(9) .0009(6) .0050(6) .0050(7) C6 .0309(8) .0328(8) .0386(9) .0006(7) .0009(6) .0105(7) C7 .0338(8) .0389(9) .0303(8) -.0043(7) -.0002(6) .0014(7) C8 .0312(8) .0274(8) .0356(8) -.0035(6) .0013(6) -.0033(7) C9 .0239(7) .0210(7) .0335(8) -.0031(5) .0029(6) -.0002(6) C10 .0264(7) .0181(7) .0361(8) -.0012(6) .0036(6) -.0024(6) C11 .0346(8) .0234(8) .0383(9) -.0003(6) -.0015(7) .0006(7) C12 .0395(9) .0259(8) .0365(9) .0001(7) .0014(7) -.0011(7) 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 .7368(4) .60415(10) .53429(6) .0465(4) Uani d . 1 . O O2 .2757(3) .88982(9) .57051(6) .0447(4) Uani d . 1 . O C1 .5495(4) .70240(11) .42786(8) .0262(3) Uani d . 1 . C C2 .4166(4) .80113(11) .46070(8) .0261(4) Uani d . 1 . C C3 .2568(4) .87865(12) .41754(9) .0273(4) Uani d . 1 . C C4 .2190(4) .86536(12) .34159(8) .0261(4) Uani d . 1 . C C5 .0553(4) .94599(13) .29709(9) .0317(4) Uani d . 1 . C C6 .0203(4) .92930(14) .22424(9) .0341(4) Uani d . 1 . C C7 .1475(4) .83299(14) .19187(9) .0344(4) Uani d . 1 . C C8 .3076(4) .75346(13) .23324(9) .0314(4) Uani d . 1 . C C9 .3477(4) .76777(11) .30901(8) .0261(4) Uani d . 1 . C C10 .5121(4) .68848(11) .35430(8) .0268(4) Uani d . 1 . C C11 .7133(4) .61150(12) .46897(9) .0321(4) Uani d . 1 . C C12 .4570(4) .82509(13) .53921(9) .0340(4) Uani d . 1 . C H3 .168(4) .9433(14) .4397(9) .029(4) Uiso d . 1 . H H5 -.038(5) 1.0124(16) .3213(10) .043(5) Uiso d . 1 . H H6 -.097(5) .9802(17) .1935(10) .051(5) Uiso d . 1 . H H7 .120(4) .8249(14) .1410(9) .033(4) Uiso d . 1 . H H8 .400(5) .6848(16) .2091(10) .043(5) Uiso d . 1 . H H10 .605(5) .6188(14) .3318(9) .034(4) Uiso d . 1 . H H11 .802(5) .5511(14) .4363(9) .033(4) Uiso d . 1 . H H12 .649(5) .7857(16) .5667(10) .048(5) Uiso d . 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' 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 C10 C1 C2 119.19(13) n C10 C1 C11 116.84(13) n C2 C1 C11 123.92(13) n C3 C2 C1 119.06(13) n C3 C2 C12 118.00(13) n C1 C2 C12 122.89(13) n C2 C3 C4 122.17(13) n C3 C4 C5 122.01(14) n C3 C4 C9 118.96(13) n C5 C4 C9 119.03(14) n C6 C5 C4 120.13(15) n C5 C6 C7 120.97(15) n C8 C7 C6 120.43(15) n C7 C8 C9 120.18(15) n C8 C9 C10 122.55(13) n C8 C9 C4 119.25(13) n C10 C9 C4 118.20(13) n C1 C10 C9 122.41(13) n O1 C11 C1 126.11(15) n O2 C12 C2 123.0(2) n 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 C11 . 1.207(2) n O2 C12 . 1.207(2) n C1 C10 . 1.369(2) n C1 C2 . 1.438(2) n C1 C11 . 1.469(2) n C2 C3 . 1.367(2) n C2 C12 . 1.478(2) n C3 C4 . 1.411(2) n C4 C5 . 1.413(2) n C4 C9 . 1.419(2) n C5 C6 . 1.360(2) n C6 C7 . 1.402(2) n C7 C8 . 1.366(2) n C8 C9 . 1.410(2) n C9 C10 . 1.412(2) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 87023 2 PubChem 96400