#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/52/2205247.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_2205247 loop_ _publ_author_name 'Xiao-Qing Cai' 'Mao-Lin Hu' 'Ya-Juan Zhao' 'Ya-Qian Cheng' 'Shun Wang' _publ_section_title ; 2,3,5,6-Tetramethylpyrazine--p-nitrophenol (1/2) ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o614 _journal_page_last o615 _journal_paper_doi 10.1107/S160053680500382X _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C8 H12 N2, 2C6 H5 N O3' _chemical_formula_moiety 'C8 H12 N2, 2C6 H5 N O3' _chemical_formula_sum 'C20 H22 N4 O6' _chemical_formula_weight 414.42 _chemical_name_systematic ; 2,3,5,6-Tetramethylpyrazine--p-nitrophenol (1/2) ; _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 73.916(2) _cell_angle_beta 81.771(2) _cell_angle_gamma 74.706(2) _cell_formula_units_Z 1 _cell_length_a 4.7521(2) _cell_length_b 8.8700(4) _cell_length_c 13.1941(6) _cell_measurement_reflns_used 1276 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.15 _cell_measurement_theta_min 2.46 _cell_volume 513.98(4) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP (Bruker, 2002)' _computing_publication_material 'SHELXTL (Bruker, 2002)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \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 0.0118 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2747 _diffrn_reflns_theta_full 25.23 _diffrn_reflns_theta_max 25.23 _diffrn_reflns_theta_min 1.61 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.9851 _exptl_absorpt_correction_T_min 0.9533 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 218 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.161 _refine_diff_density_min -0.174 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.273 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 1825 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.273 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0767 _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^)+(0.0532P)^2^+0.2196P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1667 _refine_ls_wR_factor_ref 0.1696 _reflns_number_gt 1720 _reflns_number_total 1825 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6456.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 'Triclinic' changed to 'triclinic' 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_original_sg_symbol_Hall -P1 _cod_database_code 2205247 _cod_database_fobs_code 2205247 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_type_symbol O1 0.4149(6) 0.9189(3) -0.0822(2) 0.1023(10) Uani d . 1 O O2 0.8091(6) 0.7312(3) -0.0677(2) 0.0962(9) Uani d . 1 O O3 0.0826(5) 0.4700(3) 0.34784(17) 0.0715(7) Uani d . 1 O H3 0.1788 0.3775 0.3689 0.107 Uiso calc R 1 H N1 0.5647(6) 0.7910(3) -0.0341(2) 0.0680(7) Uani d . 1 N N2 0.3737(5) 0.1525(2) 0.44480(17) 0.0481(6) Uani d . 1 N C1 0.4426(6) 0.7057(3) 0.0671(2) 0.0531(7) Uani d . 1 C C2 0.5856(7) 0.5500(4) 0.1141(2) 0.0607(8) Uani d . 1 C H2 0.7600 0.5004 0.0824 0.073 Uiso calc R 1 H C3 0.4678(6) 0.4691(3) 0.2080(2) 0.0586(8) Uani d . 1 C H3A 0.5626 0.3639 0.2399 0.070 Uiso calc R 1 H C4 0.2110(6) 0.5423(3) 0.2553(2) 0.0510(7) Uani d . 1 C C5 0.0702(7) 0.7000(3) 0.2077(2) 0.0604(8) Uani d . 1 C H5 -0.1021 0.7507 0.2399 0.073 Uiso calc R 1 H C6 0.1863(7) 0.7813(3) 0.1126(2) 0.0620(8) Uani d . 1 C H6 0.0917 0.8861 0.0800 0.074 Uiso calc R 1 H C7 0.1485(7) 0.0562(4) 0.3285(2) 0.0688(9) Uani d . 1 C H7A 0.0617 0.1697 0.3064 0.103 Uiso calc R 1 H H7B -0.0028 -0.0020 0.3507 0.103 Uiso calc R 1 H H7C 0.2689 0.0212 0.2705 0.103 Uiso calc R 1 H C8 0.3327(6) 0.0245(3) 0.41888(19) 0.0458(6) Uani d . 1 C C9 0.5373(6) 0.1317(3) 0.5245(2) 0.0467(7) Uani d . 1 C C10 0.5772(8) 0.2803(4) 0.5484(3) 0.0713(9) Uani d . 1 C H10A 0.7619 0.3013 0.5161 0.107 Uiso calc R 1 H H10B 0.5731 0.2640 0.6236 0.107 Uiso calc R 1 H H10C 0.4222 0.3707 0.5209 0.107 Uiso calc R 1 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 0.108(2) 0.0747(17) 0.0770(17) 0.0045(15) 0.0084(15) 0.0239(14) O2 0.0821(18) 0.098(2) 0.0781(17) -0.0051(15) 0.0169(14) 0.0011(14) O3 0.0751(15) 0.0488(12) 0.0667(13) -0.0035(10) 0.0038(11) 0.0091(10) N1 0.0734(18) 0.0607(17) 0.0579(15) -0.0118(14) -0.0009(13) -0.0012(13) N2 0.0550(13) 0.0327(11) 0.0472(12) -0.0076(9) 0.0016(10) -0.0004(9) C1 0.0596(17) 0.0458(15) 0.0507(16) -0.0119(13) -0.0100(13) -0.0047(13) C2 0.0572(17) 0.0502(17) 0.0647(18) -0.0015(14) -0.0039(14) -0.0091(14) C3 0.0590(17) 0.0410(15) 0.0646(18) 0.0003(13) -0.0130(14) -0.0025(13) C4 0.0592(17) 0.0374(14) 0.0529(15) -0.0100(12) -0.0120(13) -0.0032(12) C5 0.0614(18) 0.0462(16) 0.0593(17) 0.0021(13) -0.0022(14) -0.0052(14) C6 0.071(2) 0.0405(15) 0.0606(18) -0.0003(14) -0.0101(15) 0.0007(13) C7 0.077(2) 0.067(2) 0.0560(18) -0.0132(17) -0.0106(15) -0.0053(15) C8 0.0488(15) 0.0403(14) 0.0432(14) -0.0114(11) 0.0040(11) -0.0051(11) C9 0.0519(15) 0.0356(13) 0.0474(14) -0.0111(11) 0.0063(12) -0.0060(11) C10 0.087(2) 0.0457(17) 0.083(2) -0.0184(16) -0.0055(18) -0.0177(16) 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 _geom_angle_publ_flag C4 O3 H3 . . 109.5 yes O2 N1 O1 . . 122.7(3) yes O2 N1 C1 . . 118.8(3) yes O1 N1 C1 . . 118.5(3) yes C8 N2 C9 . . 120.3(2) yes C6 C1 C2 . . 121.3(3) ? C6 C1 N1 . . 119.3(3) ? C2 C1 N1 . . 119.4(3) ? C3 C2 C1 . . 119.3(3) ? C3 C2 H2 . . 120.3 ? C1 C2 H2 . . 120.3 ? C2 C3 C4 . . 120.5(3) ? C2 C3 H3A . . 119.7 ? C4 C3 H3A . . 119.7 ? O3 C4 C3 . . 123.7(2) ? O3 C4 C5 . . 116.6(3) ? C3 C4 C5 . . 119.7(3) ? C6 C5 C4 . . 120.0(3) ? C6 C5 H5 . . 120.0 ? C4 C5 H5 . . 120.0 ? C1 C6 C5 . . 119.2(3) ? C1 C6 H6 . . 120.4 ? C5 C6 H6 . . 120.4 ? C8 C7 H7A . . 109.5 ? C8 C7 H7B . . 109.5 ? H7A C7 H7B . . 109.5 ? C8 C7 H7C . . 109.5 ? H7A C7 H7C . . 109.5 ? H7B C7 H7C . . 109.5 ? N2 C8 C9 . 2_656 119.6(2) ? N2 C8 C7 . . 117.6(2) ? C9 C8 C7 2_656 . 122.8(3) ? N2 C9 C8 . 2_656 120.1(2) ? N2 C9 C10 . . 117.5(2) ? C8 C9 C10 2_656 . 122.4(3) ? C9 C10 H10A . . 109.5 ? C9 C10 H10B . . 109.5 ? H10A C10 H10B . . 109.5 ? C9 C10 H10C . . 109.5 ? H10A C10 H10C . . 109.5 ? H10B C10 H10C . . 109.5 ? 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 O1 N1 . 1.225(3) yes O2 N1 . 1.219(3) yes O3 C4 . 1.354(3) ? O3 H3 . 0.8200 ? N1 C1 . 1.464(4) yes N2 C8 . 1.339(3) yes N2 C9 . 1.340(3) yes C1 C6 . 1.370(4) ? C1 C2 . 1.380(4) ? C2 C3 . 1.373(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.374(4) ? C3 H3A . 0.9300 ? C4 C5 . 1.393(4) ? C5 C6 . 1.381(4) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 C8 . 1.500(4) ? C7 H7A . 0.9600 ? C7 H7B . 0.9600 ? C7 H7C . 0.9600 ? C8 C9 2_656 1.402(3) yes C9 C8 2_656 1.402(3) yes C9 C10 . 1.502(4) ? C10 H10A . 0.9600 ? C10 H10B . 0.9600 ? C10 H10C . 0.9600 ? 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 O3 H3 N2 . 0.82 2.01 2.818(3) 170 yes C6 H6 O1 2_575 0.93 2.57 3.335(4) 140 yes C2 H2 O2 2_765 0.93 2.52 3.380(4) 154 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 86063536