#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/41/2104168.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_2104168 loop_ _publ_author_name 'Rychlewska, Urszula' 'Wa\'scinska, Natalia' 'War\.zajtis, Beata' 'Gawro\'nski, Jacek' _publ_contact_author ; Urszula Rychlewska Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 60-780 Pozna\'n Poland ; _publ_section_title ; Role of the gauche effect and local 1,3-dipole--dipole interactions in stabilizing an unusual conformation of tartarodinitriles ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 497 _journal_page_last 503 _journal_paper_doi 10.1107/S0108768108018272 _journal_volume 64 _journal_year 2008 _chemical_formula_sum 'C18 H12 N2 O4' _chemical_formula_weight 320.30 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 106.26(2) _cell_angle_beta 105.30(2) _cell_angle_gamma 96.55(2) _cell_formula_units_Z 1 _cell_length_a 5.7840(14) _cell_length_b 7.3241(18) _cell_length_c 10.229(3) _cell_measurement_reflns_used 690 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 26.02 _cell_measurement_theta_min 2.18 _cell_volume 392.90(19) _computing_cell_refinement 'CrysAlisPRO v.1.171 (Oxford Diffraction,2007)' _computing_data_collection 'CrysAlis CCD v.1.171 (Oxford Diffraction,2007)' _computing_data_reduction 'CrysAlisPRO v.1.171 (Oxford Diffraction,2007)' _computing_molecular_graphics ; Simens Analytical X-Ray Instruments (1989), Mercury (Bruno, et al. 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Kuma KM4CCD \k-geometry diffractometer' _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 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3310 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 2.18 _diffrn_standards_interval_count 'every 50 dc frames' _diffrn_standards_number '2 reference frames' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 166 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.138 _refine_diff_density_min -0.176 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.865 _refine_ls_hydrogen_treatment riding _refine_ls_matrix_type full _refine_ls_number_parameters 109 _refine_ls_number_reflns 1526 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.865 _refine_ls_R_factor_all 0.0931 _refine_ls_R_factor_gt 0.0412 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0959 _refine_ls_wR_factor_ref 0.1126 _reflns_number_gt 720 _reflns_number_total 1526 _reflns_threshold_expression >2sigma(I) _cod_data_source_file bs5062.cif _cod_data_source_block 1c _cod_original_cell_volume 392.90(18) _cod_original_sg_symbol_H-M P-1 _cod_database_code 2104168 _cod_database_fobs_code 2104168 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _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_refinement_flags _atom_site_occupancy N N1 0.7067(4) 0.3356(4) -0.0651(2) 0.1004(8) Uani d . 1 C C1 0.6776(4) 0.2093(4) -0.0243(2) 0.0733(7) Uani d . 1 C C2 0.6353(3) 0.0443(3) 0.02731(18) 0.0582(6) Uani d . 1 H H2A 0.7299 -0.0526 -0.0042 0.070 Uiso calc R 1 O O2 0.6942(2) 0.10852(19) 0.17988(12) 0.0571(4) Uani d . 1 C C20 0.9385(4) 0.1618(3) 0.25485(18) 0.0484(5) Uani d . 1 O O20 1.0897(3) 0.1597(2) 0.19460(14) 0.0721(5) Uani d . 1 C C21 0.9803(3) 0.2197(2) 0.41001(17) 0.0425(5) Uani d . 1 C C22 1.2117(4) 0.3173(3) 0.4994(2) 0.0521(5) Uani d . 1 H H22A 1.3350 0.3450 0.4609 0.063 Uiso calc R 1 C C23 1.2594(4) 0.3735(3) 0.6457(2) 0.0634(6) Uani d . 1 H H23A 1.4145 0.4408 0.7060 0.076 Uiso calc R 1 C C24 1.0797(5) 0.3305(3) 0.7026(2) 0.0649(6) Uani d . 1 H H24A 1.1132 0.3679 0.8014 0.078 Uiso calc R 1 C C25 0.8507(4) 0.2327(3) 0.6147(2) 0.0601(6) Uani d . 1 H H25A 0.7290 0.2033 0.6539 0.072 Uiso calc R 1 C C26 0.8002(4) 0.1778(3) 0.4680(2) 0.0516(5) Uani d . 1 H H26A 0.6440 0.1123 0.4083 0.062 Uiso calc R 1 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 N1 0.0971(17) 0.126(2) 0.0553(13) -0.0152(16) 0.0036(12) 0.0280(13) C1 0.0633(16) 0.103(2) 0.0341(12) -0.0084(15) 0.0072(11) 0.0106(12) C2 0.0433(11) 0.0877(16) 0.0270(10) 0.0052(12) 0.0070(9) -0.0002(10) O2 0.0389(8) 0.0883(10) 0.0280(7) 0.0079(7) 0.0046(6) 0.0016(6) C20 0.0393(12) 0.0567(12) 0.0397(12) 0.0105(10) 0.0074(10) 0.0054(9) O20 0.0454(9) 0.1107(13) 0.0463(9) 0.0106(8) 0.0160(7) 0.0042(8) C21 0.0386(11) 0.0491(11) 0.0328(10) 0.0124(9) 0.0047(9) 0.0069(9) C22 0.0433(12) 0.0538(12) 0.0481(12) 0.0083(10) 0.0044(10) 0.0093(10) C23 0.0570(15) 0.0632(14) 0.0458(13) 0.0070(12) -0.0088(11) 0.0059(11) C24 0.0811(18) 0.0686(14) 0.0352(11) 0.0196(14) 0.0069(12) 0.0105(10) C25 0.0656(15) 0.0707(15) 0.0449(13) 0.0155(13) 0.0190(12) 0.0176(11) C26 0.0439(12) 0.0593(12) 0.0427(12) 0.0065(11) 0.0063(10) 0.0112(10) 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle N1 C1 C2 . . 179.0(3) O2 C2 C1 . . 110.77(16) O2 C2 C2 . 2_655 104.71(17) C1 C2 C2 . 2_655 109.1(2) O2 C2 H2A . . 110.7 C1 C2 H2A . . 110.7 C2 C2 H2A 2_655 . 110.7 C20 O2 C2 . . 115.70(13) O20 C20 O2 . . 121.10(16) O20 C20 C21 . . 127.29(18) O2 C20 C21 . . 111.61(15) C26 C21 C22 . . 119.61(16) C26 C21 C20 . . 122.50(17) C22 C21 C20 . . 117.89(17) C23 C22 C21 . . 119.84(18) C23 C22 H22A . . 120.1 C21 C22 H22A . . 120.1 C24 C23 C22 . . 120.20(19) C24 C23 H23A . . 119.9 C22 C23 H23A . . 119.9 C23 C24 C25 . . 120.29(19) C23 C24 H24A . . 119.9 C25 C24 H24A . . 119.9 C24 C25 C26 . . 119.98(19) C24 C25 H25A . . 120.0 C26 C25 H25A . . 120.0 C21 C26 C25 . . 120.07(18) C21 C26 H26A . . 120.0 C25 C26 H26A . . 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N1 C1 . 1.130(3) C1 C2 . 1.468(3) C2 O2 . 1.430(2) C2 C2 2_655 1.512(4) C2 H2A . 0.9800 O2 C20 . 1.368(2) C20 O20 . 1.195(2) C20 C21 . 1.468(2) C21 C26 . 1.373(2) C21 C22 . 1.382(2) C22 C23 . 1.377(2) C22 H22A . 0.9300 C23 C24 . 1.365(3) C23 H23A . 0.9300 C24 C25 . 1.367(3) C24 H24A . 0.9300 C25 C26 . 1.380(2) C25 H25A . 0.9300 C26 H26A . 0.9300 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 C1 C2 O2 C20 . -74.2(2) C2 C2 O2 C20 2_655 168.31(19) C2 O2 C20 O20 . 2.3(3) C2 O2 C20 C21 . -178.29(15) O20 C20 C21 C26 . -165.4(2) O2 C20 C21 C26 . 15.2(2) O20 C20 C21 C22 . 13.5(3) O2 C20 C21 C22 . -165.85(16) C26 C21 C22 C23 . -0.7(3) C20 C21 C22 C23 . -179.67(16) C21 C22 C23 C24 . 1.0(3) C22 C23 C24 C25 . -0.5(3) C23 C24 C25 C26 . -0.3(3) C22 C21 C26 C25 . -0.1(3) C20 C21 C26 C25 . 178.87(17) C24 C25 C26 C21 . 0.6(3) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 102473792