#------------------------------------------------------------------------------ #$Date: 2020-02-14 10:22:03 +0200 (Fri, 14 Feb 2020) $ #$Revision: 248151 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557317.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557317 loop_ _publ_author_name 'Butts, Craig P.' 'Eberson, Lennart' 'Hartshorn, Michael P.' 'Persson, Ola' 'Thompson, Rewi S.' 'Robinson, Ward T.' _publ_section_title ; Photochemical Nitration by Tetranitromethane. Part XLI. Addition Ipso to a Methoxy Group and the Effect of Methanol in the Photochemical Reaction between 1,4-Dimethoxynaphthalene and Tetranitromethane ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 1066 _journal_page_last 1077 _journal_paper_doi 10.3891/acta.chem.scand.51-1066 _journal_volume 51 _journal_year 1997 _chemical_formula_sum 'C12 H8 N2 O6' _chemical_formula_weight 276.20 _chemical_name_common ; 4-Methoxy-2-(dinitromethylene)-1(2H)-naphthalenone ; _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_formula_units_Z 4 _cell_length_a 19.104(4) _cell_length_b 10.799(3) _cell_length_c 5.419(3) _cell_volume 1118.0(7) _diffrn_ambient_temperature 158 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _exptl_absorpt_coefficient_mu 0.135 _exptl_crystal_density_diffrn 1.641 _refine_ls_number_reflns 630 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_gt 0.1150 _cod_data_source_file Acta-Chem-Scand-1997-51-1066-2.cif _cod_data_source_block 1 _cod_database_code 1557317 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,1/2+z 3 1/2-x,1/2+y,1/2+z 4 1/2+x,1/2-y,z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O Uiso 0.2864(2) 0.5995(5) -0.1110(10) 1.000 0.0240(10) . . . . O4 O Uiso 0.0583(2) 0.8555(4) 0.1552(11) 1.000 0.0230(10) . . . . O911 O Uiso 0.3580(3) 0.5478(5) 0.3405(11) 1.000 0.036(2) . . . . O912 O Uiso 0.4049(2) 0.7019(5) 0.1458(12) 1.000 0.036(2) . . . . O921 O Uiso 0.3737(2) 0.7958(5) 0.6212(11) 1.000 0.0310(10) . . . . O922 O Uiso 0.2672(2) 0.8665(5) 0.6363(11) 1.000 0.0270(10) . . . . N91 N Uiso 0.3578(3) 0.6537(7) 0.2636(11) 1.000 0.026(2) . . . . N92 N Uiso 0.3142(3) 0.8043(6) 0.5429(11) 1.000 0.021(2) . . . . C1 C Uiso 0.2336(4) 0.6478(6) -0.0319(13) 1.000 0.016(2) . . . . C2 C Uiso 0.2359(4) 0.7310(6) 0.1952(13) 1.000 0.018(2) . . . . C3 C Uiso 0.1763(4) 0.8042(7) 0.2477(14) 1.000 0.017(2) . . . . C4 C Uiso 0.1163(3) 0.7908(6) 0.1137(15) 1.000 0.018(2) . . . . C4A C Uiso 0.1083(3) 0.7014(6) -0.0853(14) 1.000 0.018(2) . . . . C5 C Uiso 0.0451(4) 0.6872(7) -0.2103(13) 1.000 0.023(2) . . . . C6 C Uiso 0.0406(4) 0.6013(7) -0.4013(14) 1.000 0.026(2) . . . . C7 C Uiso 0.0974(4) 0.5311(7) -0.4713(14) 1.000 0.027(2) . . . . C8 C Uiso 0.1607(3) 0.5461(6) -0.3485(15) 1.000 0.019(2) . . . . C8A C Uiso 0.1659(4) 0.6307(6) -0.1549(14) 1.000 0.019(2) . . . . C9 C Uiso 0.2970(4) 0.7315(6) 0.3264(14) 1.000 0.018(2) . . . . C10 C Uiso 0.0576(4) 0.9493(7) 0.3447(15) 1.000 0.026(2) . . . . 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' 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O4 C10 119.8(5) . . . yes O911 N91 O912 125.3(6) . . . yes O911 N91 C9 117.3(6) . . . yes O912 N91 C9 117.3(7) . . . yes O921 N92 O922 125.4(6) . . . yes O921 N92 C9 116.9(6) . . . yes O922 N92 C9 117.6(6) . . . yes O1 C1 C2 121.0(7) . . . yes O1 C1 C8A 121.2(6) . . . yes C2 C1 C8A 117.8(6) . . . no C1 C2 C3 117.9(6) . . . no C1 C2 C9 116.6(6) . . . no C3 C2 C9 125.5(7) . . . no C2 C3 C4 120.6(7) . . . no O4 C4 C3 123.7(7) . . . yes O4 C4 C4A 112.7(6) . . . yes C3 C4 C4A 123.6(6) . . . no C4 C4A C5 121.6(6) . . . no C4 C4A C8A 118.8(6) . . . no C5 C4A C8A 119.6(7) . . . no C4A C5 C6 119.2(7) . . . no C5 C6 C7 121.5(7) . . . no C6 C7 C8 119.3(7) . . . no C7 C8 C8A 119.9(6) . . . no C1 C8A C4A 120.3(6) . . . no C1 C8A C8 119.2(6) . . . no C4A C8A C8 120.5(7) . . . no N91 C9 N92 108.5(6) . . . yes N91 C9 C2 123.4(6) . . . yes N92 C9 C2 128.1(6) . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.214(9) . . yes O4 C4 1.329(7) . . yes O4 C10 1.443(9) . . yes O911 N91 1.217(9) . . yes O912 N91 1.220(8) . . yes O921 N92 1.217(7) . . yes O922 N92 1.230(8) . . yes N91 C9 1.473(10) . . yes N92 C9 1.450(10) . . yes C1 C2 1.524(10) . . no C1 C8A 1.467(11) . . no C2 C3 1.415(11) . . no C2 C9 1.367(11) . . no C3 C4 1.365(10) . . no C4 C4A 1.455(10) . . no C4A C5 1.393(10) . . no C4A C8A 1.391(10) . . no C5 C6 1.393(11) . . no C6 C7 1.377(11) . . no C7 C8 1.390(10) . . no C8 C8A 1.395(10) . . no 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10 O4 C4 C3 2.5(10) . . . . no C10 O4 C4 C4A -179.2(6) . . . . no O911 N91 C9 N92 95.9(7) . . . . no O911 N91 C9 C2 -84.1(9) . . . . no O912 N91 C9 N92 -81.8(8) . . . . no O912 N91 C9 C2 98.3(8) . . . . no O921 N92 C9 N91 4.6(9) . . . . no O921 N92 C9 C2 -175.4(7) . . . . no O922 N92 C9 N91 -173.3(6) . . . . no O922 N92 C9 C2 6.6(11) . . . . no O1 C1 C2 C3 167.2(7) . . . . no O1 C1 C2 C9 -10.5(10) . . . . no C8A C1 C2 C3 -11.3(9) . . . . no C8A C1 C2 C9 171.0(6) . . . . no O1 C1 C8A C4A -170.0(7) . . . . no O1 C1 C8A C8 7.6(10) . . . . no C2 C1 C8A C4A 8.4(10) . . . . no C2 C1 C8A C8 -174.0(6) . . . . no C1 C2 C3 C4 6.6(10) . . . . no C9 C2 C3 C4 -175.9(7) . . . . no C1 C2 C9 N91 -2.2(10) . . . . no C1 C2 C9 N92 177.8(6) . . . . no C3 C2 C9 N91 -179.8(7) . . . . no C3 C2 C9 N92 0.3(12) . . . . no C2 C3 C4 O4 179.2(7) . . . . no C2 C3 C4 C4A 1.1(11) . . . . no O4 C4 C4A C5 -1.1(10) . . . . no O4 C4 C4A C8A 177.5(6) . . . . no C3 C4 C4A C5 177.2(7) . . . . no C3 C4 C4A C8A -4.3(11) . . . . no C4 C4A C5 C6 179.2(7) . . . . no C8A C4A C5 C6 0.7(11) . . . . no C4 C4A C8A C1 -1.0(10) . . . . no C4 C4A C8A C8 -178.5(7) . . . . no C5 C4A C8A C1 177.6(7) . . . . no C5 C4A C8A C8 0.0(11) . . . . no C4A C5 C6 C7 -0.8(11) . . . . no C5 C6 C7 C8 0.1(11) . . . . no C6 C7 C8 C8A 0.7(11) . . . . no C7 C8 C8A C1 -178.3(7) . . . . no C7 C8 C8A C4A -0.7(11) . . . . no