#------------------------------------------------------------------------------ #$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $ #$Revision: 180387 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/56/7205664.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_7205664 loop_ _publ_author_name 'Braga, Dario' 'Grepioni, Fabrizia' 'Lampronti, Giulio I.' _publ_section_title ; Supramolecular metathesis: co-former exchange in co-crystals of pyrazine with (R,R)-, (S,S)-, (R,S)- and (S,S/R,R)-tartaric acid ; _journal_issue 9 _journal_name_full CrystEngComm _journal_page_first 3122 _journal_paper_doi 10.1039/c0ce00576b _journal_volume 13 _journal_year 2011 _chemical_formula_moiety 'C12 H16 N2 O12' _chemical_formula_sum 'C6 H8 N O6' _chemical_formula_weight 190.13 _chemical_name_systematic ; ? ; _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_date 2010-05-12T11:09:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 81.199(8) _cell_angle_beta 83.738(8) _cell_angle_gamma 88.135(8) _cell_formula_units_Z 2 _cell_length_a 4.9168(5) _cell_length_b 5.4373(5) _cell_length_c 14.7869(14) _cell_measurement_reflns_used 0 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 0 _cell_measurement_theta_min 0 _cell_volume 388.28(7) _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.831 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_unetI/netI 0.0531 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 2909 _diffrn_reflns_theta_full 25 _diffrn_reflns_theta_max 29.03 _diffrn_reflns_theta_min 2.8 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.626 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 198 _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.6 _refine_diff_density_max 0.294 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.075 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.826 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 134 _refine_ls_number_reflns 1726 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.826 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0568 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0918P)^2^+1.0599P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1808 _reflns_number_gt 1098 _reflns_number_total 1726 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c0ce00576b.txt _cod_data_source_block rac2py1 _cod_original_cell_volume 388.28(6) _cod_database_code 7205664 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 0.5566(7) 0.1392(6) 0.2186(2) 0.0276(7) Uani d . 1 . . C C2 0.7433(7) 0.2257(6) 0.2815(2) 0.0269(7) Uani d . 1 . . C H2 0.8633 0.0874 0.3039 0.032 Uiso calc R 1 . . H C3 0.5573(6) 0.3045(6) 0.3633(2) 0.0245(7) Uani d . 1 . . C H3 0.4638 0.1562 0.397 0.029 Uiso calc R 1 . . H C4 0.7355(6) 0.4000(6) 0.4271(2) 0.0238(7) Uani d . 1 . . C O1 0.4162(6) -0.0420(4) 0.24402(17) 0.0418(7) Uani d . 1 . . O O2 0.5532(6) 0.2758(5) 0.13764(17) 0.0399(7) Uani d . 1 . . O O3 0.9037(5) 0.4260(5) 0.23499(16) 0.0367(6) Uani d . 1 . . O O4 0.3563(5) 0.4814(4) 0.33470(17) 0.0293(6) Uani d . 1 . . O O5 0.7553(5) 0.6204(4) 0.43203(16) 0.0307(6) Uani d . 1 . . O O6 0.8705(5) 0.2205(4) 0.47284(18) 0.0360(6) Uani d . 1 . . O H200 0.432(11) 0.198(10) 0.100(3) 0.076(16) Uiso d . 1 . . H H300 1.075(9) 0.418(8) 0.264(3) 0.048(12) Uiso d . 1 . . H H400 0.441(9) 0.609(8) 0.308(3) 0.046(12) Uiso d . 1 . . H H600 0.987(11) 0.267(10) 0.513(4) 0.077(16) Uiso d . 1 . . H C5 0.0776(8) -0.1134(7) 0.0796(3) 0.0397(9) Uani d . 1 . . C H5 0.1274 -0.1962 0.1353 0.048 Uiso calc R 1 . . H C6 0.1191(8) 0.2134(7) -0.0372(2) 0.0371(9) Uani d . 1 . . C H6 0.1983 0.3632 -0.0647 0.045 Uiso calc R 1 . . H N1 0.1985(6) 0.1000(6) 0.0422(2) 0.0357(7) Uani d . 1 . . N 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 C1 0.0270(17) 0.0287(16) 0.0298(17) -0.0020(13) -0.0109(14) -0.0068(13) C2 0.0229(17) 0.0298(16) 0.0291(17) -0.0036(13) -0.0113(14) -0.0013(13) C3 0.0221(16) 0.0258(16) 0.0271(16) -0.0041(12) -0.0107(13) -0.0018(12) C4 0.0201(16) 0.0289(16) 0.0221(15) -0.0028(12) -0.0022(13) -0.0026(12) O1 0.0521(17) 0.0316(13) 0.0443(15) -0.0178(12) -0.0220(13) 0.0018(11) O2 0.0466(16) 0.0465(15) 0.0289(13) -0.0217(12) -0.0175(12) 0.0009(11) O3 0.0265(13) 0.0515(16) 0.0326(13) -0.0168(11) -0.0108(11) 0.0009(11) O4 0.0200(12) 0.0295(12) 0.0390(14) -0.0012(10) -0.0125(10) 0.0000(10) O5 0.0292(13) 0.0294(12) 0.0358(13) -0.0014(9) -0.0125(11) -0.0059(10) O6 0.0384(15) 0.0300(13) 0.0437(15) 0.0024(10) -0.0257(13) -0.0042(10) C5 0.047(2) 0.042(2) 0.0309(18) -0.0081(17) -0.0156(17) -0.0007(15) C6 0.041(2) 0.0347(18) 0.0351(19) -0.0129(16) -0.0068(17) 0.0000(15) N1 0.0374(17) 0.0402(17) 0.0316(15) -0.0137(13) -0.0103(13) -0.0045(12) 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 0 '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 0.006 '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_3 _geom_angle_publ_flag O1 C1 O2 123.5(3) . . ? O1 C1 C2 120.7(3) . . ? O2 C1 C2 115.8(3) . . ? O3 C2 C1 110.9(3) . . ? O3 C2 C3 111.0(3) . . ? C1 C2 C3 106.6(3) . . ? O4 C3 C4 111.8(2) . . ? O4 C3 C2 112.3(2) . . ? C4 C3 C2 108.5(2) . . ? O5 C4 O6 124.7(3) . . ? O5 C4 C3 123.2(3) . . ? O6 C4 C3 112.1(3) . . ? N1 C5 C6 121.3(3) . 2 ? N1 C6 C5 121.4(3) . 2 ? C6 N1 C5 117.3(3) . . ? 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 C1 O1 . 1.209(4) ? C1 O2 . 1.310(4) ? C1 C2 . 1.509(4) ? C2 O3 . 1.410(4) ? C2 C3 . 1.542(5) ? C3 O4 . 1.409(4) ? C3 C4 . 1.512(4) ? C4 O5 . 1.219(4) ? C4 O6 . 1.306(4) ? C5 N1 . 1.335(5) ? C5 C6 2 1.376(5) ? C6 N1 . 1.332(5) ? C6 C5 2 1.376(5) ?