#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/21/2202153.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_2202153 loop_ _publ_author_name 'Sema \"Ozt\"urk' 'B\"ulent B\"uy\"ukk\?idan' 'Ramazan Erenler ' 'Mehmet Akkurt' 'Osman \,Cakmak' 'Hoong-Kun Fun' _publ_section_title ; 3,5-Dinitroxytricyclo[2.2.1.0^2,6^]heptane ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o550 _journal_page_last o552 _journal_paper_doi 10.1107/S1600536803006524 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C7 H7 N2 O6' _chemical_formula_moiety 'C7 H7 N2 O6' _chemical_formula_sum 'C7 H7 N2 O6' _chemical_formula_weight 215.15 _space_group_IT_number 36 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'C 2c -2' _symmetry_space_group_name_H-M 'C m c 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.4146(9) _cell_length_b 6.6414(5) _cell_length_c 10.0118(6) _cell_measurement_reflns_used 2626 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26 _cell_measurement_theta_min 3 _cell_volume 891.97(10) _computing_cell_refinement 'SAINT (Siemens,1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2626 _diffrn_reflns_theta_max 25.98 _diffrn_reflns_theta_min 3.04 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 444 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.223 _refine_diff_density_min -0.255 _refine_ls_extinction_coef 0.023(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.128 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 74 _refine_ls_number_reflns 485 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.126 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0458 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0641P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1082 _refine_ls_wR_factor_ref 0.1120 _reflns_number_gt 423 _reflns_number_total 485 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6137.cif _cod_data_source_block 5 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202153 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z -x,y,z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2-y,1/2+z 1/2-x,1/2+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 0.0189(10) 0.0524(15) 0.0472(14) 0.0014(8) 0.0059(10) 0.0045(11) O2 0.0544(16) 0.084(2) 0.0507(17) 0.0037(14) 0.0209(13) 0.0039(16) O3 0.0330(14) 0.079(2) 0.080(2) 0.0200(13) 0.0061(15) 0.006(2) N1 0.0275(14) 0.0430(17) 0.058(2) 0.0007(11) 0.0117(13) -0.0039(14) C1 0.0207(14) 0.0418(18) 0.0407(19) 0.0025(12) -0.0038(13) -0.0010(14) C2 0.0354(18) 0.0394(18) 0.0427(19) 0.0083(13) 0.0002(15) 0.0001(14) C3 0.038(2) 0.055(3) 0.040(3) 0.0000 0.0000 0.011(2) C4 0.041(3) 0.054(3) 0.043(3) 0.0000 0.0000 -0.008(2) C5 0.030(2) 0.035(2) 0.044(3) 0.0000 0.0000 -0.0044(18) 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_type_symbol O1 0.09919(13) 0.3326(3) -0.1242(2) 0.0395(8) Uani . . 1.000 O O2 0.1928(2) 0.3300(5) -0.2994(3) 0.0630(10) Uani . . 1.000 O O3 0.2510(2) 0.1972(4) -0.1175(4) 0.0640(11) Uani . . 1.000 O N1 0.1888(2) 0.2810(4) -0.1851(3) 0.0428(10) Uani . . 1.000 N C1 0.0892(2) 0.2661(4) 0.0132(3) 0.0344(10) Uani . . 1.000 C C2 0.0559(2) 0.0535(5) 0.0289(4) 0.0392(11) Uani . . 1.000 C C3 0.00000 0.0464(8) 0.1590(5) 0.0443(16) Uani . . 1.000 C C4 0.00000 0.2629(7) 0.2134(6) 0.0460(17) Uani . . 1.000 C C5 0.00000 0.3707(7) 0.0772(5) 0.0363(14) Uani . . 1.000 C H1A 0.14888 0.29156 0.06311 0.0413 Uiso . . 1.000 H H2A 0.09476 -0.05742 -0.00351 0.0470 Uiso . . 1.000 H H3A 0.00000 -0.06945 0.21613 0.0533 Uiso . . 1.000 H H4A 0.05854 0.29235 0.26473 0.0552 Uiso . . 0.500 H H5A 0.00000 0.51504 0.07740 0.0436 Uiso . . 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 O1 C1 . . 114.9(2) yes O1 N1 O2 . . 113.1(3) yes O1 N1 O3 . . 117.7(3) yes O2 N1 O3 . . 129.2(3) yes O1 C1 C2 . . 114.6(3) yes O1 C1 C5 . . 109.4(3) yes C2 C1 C5 . . 98.8(3) yes C1 C2 C3 . . 105.7(3) yes C1 C2 C2 . 3_555 107.5(3) no C2 C2 C3 3_555 . 60.1(2) no C2 C3 C4 . . 106.1(4) yes C2 C3 C2 . 3_555 59.8(3) no C2 C3 C4 3_555 . 106.1(4) no C3 C4 C5 . . 97.0(4) yes C1 C5 C4 . . 99.2(3) yes C1 C5 C1 . 3_555 103.4(3) no C1 C5 C4 3_555 . 99.2(3) no O1 C1 H1A . . 111.30 no C2 C1 H1A . . 111.26 no C5 C1 H1A . . 110.85 no C1 C2 H2A . . 121.97 no C3 C2 H2A . . 122.69 no C2 C2 H2A 3_555 . 122.93 no C2 C3 H3A . . 122.82 no C4 C3 H3A . . 122.63 no C2 C3 H3A 3_555 . 122.82 no C3 C4 H4A . . 112.38 no C3 C4 H4A . 3_555 112.38 no C5 C4 H4A . . 112.32 no C5 C4 H4A . 3_555 112.32 no H4A C4 H4A . 3_555 110.00 no C1 C5 H5A . . 117.16 no C4 C5 H5A . . 117.58 no C1 C5 H5A 3_555 . 117.16 no 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 N1 . . 1.391(3) yes O1 C1 . . 1.451(4) yes O2 N1 . . 1.191(4) yes O3 N1 . . 1.210(4) yes C1 C2 . . 1.489(4) yes C1 C5 . . 1.525(4) yes C2 C3 . . 1.504(6) yes C2 C2 . 3_555 1.500(4) no C3 C4 . . 1.538(7) yes C4 C5 . . 1.540(8) yes C1 H1A . . 0.9588 no C2 H2A . . 0.9590 no C3 H3A . . 0.9587 no C4 H4A . . 0.9587 no C5 H5A . . 0.9586 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C4 3.410(5) 2_564 no O1 O1 2.661(2) 3_555 no O1 C4 3.410(5) 4_564 no O1 O3 3.147(3) 7_555 no O2 O3 3.136(5) 7_555 no O3 N1 2.958(4) 7_545 no O3 O1 3.147(3) 7_545 no O3 O2 3.136(5) 7_545 no O3 C2 3.148(4) . no O1 H3A 2.7167 2_554 no O1 H3A 2.7167 4_554 no O1 H4A 2.7818 4_564 no O2 H1A 2.6565 6_554 no O3 H1A 2.3535 . no O3 H4A 2.8147 6_554 no O3 H2A 2.8704 7_555 no N1 O3 2.958(4) 7_555 no C2 O3 3.148(4) . no C4 O1 3.410(5) 2_565 no C4 O1 3.410(5) 4_565 no H1A O3 2.3535 . no H1A H4A 2.3544 . no H1A O2 2.6565 6_555 no H2A O3 2.8704 7_545 no H3A O1 2.7167 2_555 no H3A O1 2.7167 4_555 no H4A H1A 2.3544 . no H4A O1 2.7818 4_565 no H4A O3 2.8147 6_555 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_site_symmetry_1 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C1 O1 N1 O2 . . . 176.9(3) yes C1 O1 N1 O3 . . . -3.9(4) yes N1 O1 C1 C2 . . . -82.8(3) yes N1 O1 C1 C5 . . . 167.4(2) yes O1 C1 C2 C2 . . 3_555 -87.9(3) no C5 C1 C2 C3 . . . -34.7(3) yes C5 C1 C2 C2 . . 3_555 28.3(4) no O1 C1 C5 C4 . . . 175.1(2) yes O1 C1 C5 C1 . . 3_555 73.3(3) no C2 C1 C5 C4 . . . 55.1(3) yes C2 C1 C5 C1 . . 3_555 -46.8(3) no O1 C1 C2 C3 . . . -150.8(2) yes C1 C2 C3 C2 . . 3_555 101.4(3) no C2 C2 C3 C4 3_555 . . -99.6(3) no C1 C2 C2 C3 . 3_555 . -98.4(4) no C1 C2 C2 C1 . 3_555 3_555 0.0(4) no C1 C2 C3 C4 . . . 1.8(3) yes C2 C3 C4 C5 . . . 31.27(18) yes C3 C4 C5 C1 . . . -52.7(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139065871