#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/20/2012002.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_2012002 loop_ _publ_author_name 'Peri\'c, Berislav' 'Koji\'c-Prodi\'c, Biserka' 'Makarevi\'c, Janja' 'Joki\'c, Milan' '\meso-N,N'-Oxalyldivaline ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 747 _journal_page_last 748 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H20 N2 O6' _chemical_formula_structural 'C12 H20 N2 O6' _chemical_formula_sum 'C12 H20 N2 O6' _chemical_formula_weight 288.30 _chemical_melting_point 513 _chemical_name_systematic ; meso-N,N'-oxalyl-bis-valine ; _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 90.00 _cell_angle_beta 119.635(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.6058(8) _cell_length_b 10.3780(2) _cell_length_c 10.6950(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 46.0 _cell_measurement_theta_min 40.0 _cell_volume 733.76(12) _computing_cell_refinement 'CAD-4 Express' _computing_data_collection 'CAD-4 Express (Enraf Nonius, 1992)' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1999)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293(3) _diffrn_measured_fraction_theta_full .945 _diffrn_measured_fraction_theta_max .945 _diffrn_measurement_device_type 'Enraf-Nonius CAD4 diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .0245 _diffrn_reflns_av_sigmaI/netI .0273 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 1597 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 74.02 _diffrn_reflns_theta_max 74.02 _diffrn_reflns_theta_min 6.39 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .889 _exptl_absorpt_correction_T_max .94079 _exptl_absorpt_correction_T_min .81910 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details 'PLATON (Spek, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_description prism _exptl_crystal_F_000 308 _exptl_crystal_size_max .27 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .07 _refine_diff_density_max .360 _refine_diff_density_min -.344 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1485 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all .0841 _refine_ls_R_factor_gt .0626 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1404P)^2^+0.0375P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1944 _reflns_number_gt 1132 _reflns_number_total 1485 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file av1074.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 733.76(10) _cod_database_code 2012002 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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 .4589(3) -.06329(19) .33627(16) .0578(6) Uani d . 1.000 O O2 .1925(3) .1954(2) .03707(18) .0688(7) Uani d . 1.000 O O3 .3670(3) .27478(19) .25763(17) .0591(6) Uani d . 1.000 O N1 .2775(2) .08487(17) .37605(16) .0373(5) Uani d . 1.000 N C1 .4294(3) .0030(2) .41814(17) .0358(5) Uani d . 1.000 C C2 .1379(3) .10772(19) .22368(18) .0356(5) Uani d . 1.000 C C3 .2342(3) .1964(2) .1613(2) .0401(6) Uani d . 1.000 C C4 -.0629(3) .1622(2) .2032(2) .0432(6) Uani d . 1.000 C C5 -.2113(4) .1921(4) .0466(3) .0726(12) Uani d . 1.000 C C6 -.1577(4) .0672(3) .2607(4) .0752(11) Uani d . 1.000 C H1 .278(4) .140(3) .441(3) .059(8) Uiso d . 1.000 H H2 .10968 .02490 .17334 .0427 Uiso calc R 1.000 H H3 .412(5) .328(3) .212(3) .075(9) Uiso d . 1.000 H H4 -.03400 .24227 .25855 .0518 Uiso calc R 1.000 H H51 -.22966 .11685 -.01087 .1089 Uiso calc R 1.000 H H52 -.15932 .26111 .01450 .1089 Uiso calc R 1.000 H H53 -.33889 .21714 .03706 .1089 Uiso calc R 1.000 H H61 -.19161 -.01078 .20523 .1133 Uiso calc R 1.000 H H62 -.27803 .10413 .25358 .1133 Uiso calc R 1.000 H H63 -.06337 .04815 .35956 .1133 Uiso calc R 1.000 H 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 .0543(10) .0770(12) .0347(8) .0273(9) .0164(7) .0001(7) O2 .0744(12) .0943(15) .0319(8) -.0222(11) .0218(8) .0029(8) O3 .0590(10) .0759(12) .0370(9) -.0252(9) .0196(8) -.0012(8) N1 .0356(8) .0462(9) .0264(8) .0094(7) .0126(7) .0061(7) C1 .0319(9) .0437(10) .0292(9) .0052(7) .0132(8) .0070(7) C2 .0317(9) .0426(10) .0252(9) .0033(7) .0086(7) .0014(7) C3 .0331(9) .0528(12) .0273(9) .0041(8) .0094(7) .0060(8) C4 .0306(9) .0545(12) .0370(10) .0052(8) .0109(8) -.0020(8) C5 .0415(12) .111(3) .0447(13) .0240(15) .0056(11) .0047(14) C6 .0486(14) .096(2) .085(2) -.0044(14) .0360(15) .0106(17) 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 C1 . . 1.218(3) no O2 C3 . . 1.204(3) no O3 C3 . . 1.309(3) no O3 H3 . . .91(4) no N1 C2 . . 1.459(2) no N1 C1 . . 1.321(3) no N1 H1 . . .90(3) no C1 C1 . 3_656 1.537(2) no C2 C3 . . 1.520(3) no C2 C4 . . 1.539(3) no C4 C6 . . 1.519(4) no C4 C5 . . 1.518(3) no C2 H2 . . .9800 no C4 H4 . . .9801 no C5 H51 . . .9604 no C5 H52 . . .9598 no C5 H53 . . .9601 no C6 H61 . . .9602 no C6 H62 . . .9599 no C6 H63 . . .9600 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -2 -9 5 0 2 1 -9 0 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 O3 H3 . 107.7(18) no C1 N1 C2 . 121.07(16) no C2 N1 H1 . 118.9(19) no C1 N1 H1 . 119(2) no O1 C1 C1 3_656 121.5(2) no O1 C1 N1 . 123.99(17) no N1 C1 C1 3_656 114.53(17) no N1 C2 C3 . 110.25(17) no N1 C2 C4 . 109.97(16) no C3 C2 C4 . 112.00(17) no O3 C3 C2 . 112.48(17) no O2 C3 O3 . 123.6(2) no O2 C3 C2 . 123.9(2) no C2 C4 C5 . 112.1(2) no C2 C4 C6 . 109.9(2) no C5 C4 C6 . 109.7(2) no N1 C2 H2 . 108.17 no C3 C2 H2 . 108.18 no C4 C2 H2 . 108.16 no C2 C4 H4 . 108.36 no C5 C4 H4 . 108.38 no C6 C4 H4 . 108.38 no C4 C5 H51 . 109.47 no C4 C5 H52 . 109.51 no C4 C5 H53 . 109.48 no H51 C5 H52 . 109.46 no H51 C5 H53 . 109.43 no H52 C5 H53 . 109.48 no C4 C6 H61 . 109.45 no C4 C6 H62 . 109.48 no C4 C6 H63 . 109.49 no H61 C6 H62 . 109.46 no H61 C6 H63 . 109.45 no H62 C6 H63 . 109.49 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 N1 H1 O1 3_656 .90(3) 2.37(3) 2.727(2) 104(2) yes N1 H1 O2 4_555 .90(3) 2.25(3) 3.112(3) 161(3) yes O3 H3 O1 2_655 .91(4) 1.73(4) 2.627(3) 167(3) yes C6 H63 N1 . .9600 2.5388 2.911(4) 103.12 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 C2 N1 C1 O1 . . . -3.9(3) no C1 C1 N1 C2 3_656 . . 175.99(18) yes C1 N1 C2 C3 . . . -77.8(2) yes C1 N1 C2 C4 . . . 158.21(19) no O1 C1 C1 O1 . 3_656 3_656 -180.0(2) no N1 C1 C1 N1 . 3_656 3_656 180.0(4) no O1 C1 C1 N1 . 3_656 3_656 -.2(3) no N1 C1 C1 O1 . 3_656 3_656 .2(3) no N1 C2 C3 O3 . . . -28.4(3) yes C4 C2 C3 O2 . . . -85.2(3) no N1 C2 C3 O2 . . . 152.0(2) no N1 C2 C4 C5 . . . 178.0(2) yes N1 C2 C4 C6 . . . -59.8(2) no C4 C2 C3 O3 . . . 94.4(2) no C3 C2 C4 C5 . . . 55.1(3) no C3 C2 C4 C6 . . . 177.3(2) no _cod_database_fobs_code 2012002 _journal_paper_doi 10.1107/S0108270101004590