#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/33/2203306.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_2203306 loop_ _publ_author_name 'Chad Eller' 'Bradley W. Smucker' 'Robert Kirgan' 'David M. Eichhorn' 'D. Paul Rillema' _publ_section_title ; 5,5'-Dimethyl-2,2'-bipyrazine ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o433 _journal_page_last o434 _journal_paper_doi 10.1107/S1600536804000881 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C10 H10 N4' _chemical_formula_moiety 'C10 H10 N4' _chemical_formula_sum 'C10 H10 N4' _chemical_formula_weight 186.14 _chemical_melting_point 147 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 102.828(19) _cell_angle_beta 92.100(17) _cell_angle_gamma 91.27(2) _cell_formula_units_Z 1 _cell_length_a 3.9580(7) _cell_length_b 5.9476(16) _cell_length_c 10.107(2) _cell_measurement_reflns_used 24 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 10 _cell_volume 231.72(9) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _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_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method 'non-profiled \w/2\q' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 1613 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 2.07 _diffrn_standards_decay_% 10 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_correction_T_min 0.8021 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 98 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.163 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 67 _refine_ls_number_reflns 811 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.959 _refine_ls_R_factor_gt 0.0477 _refine_ls_shift/su_max 0.036 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.103P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1357 _reflns_number_gt 425 _reflns_number_total 811 _reflns_threshold_expression I>2\s(I) _cod_data_source_file lh6158.cif _cod_data_source_block I _cod_database_code 2203306 _cod_database_fobs_code 2203306 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 N2 0.9089(5) 0.0073(4) 0.20068(19) 0.0547(6) Uani d . 1 N N1 0.7843(5) 0.2425(3) 0.46271(18) 0.0489(6) Uani d . 1 N C1 0.9443(6) 0.0440(4) 0.4407(2) 0.0391(5) Uani d . 1 C C2 0.6948(6) 0.3227(4) 0.3549(2) 0.0513(7) Uani d . 1 C H2 0.5885 0.4632 0.3678 0.058(7) Uiso d R 1 H C3 0.7549(6) 0.2072(4) 0.2230(2) 0.0464(6) Uani d . 1 C C4 1.0010(7) -0.0700(4) 0.3092(2) 0.0514(7) Uani d . 1 C H4 1.1084 -0.2102 0.2963 0.058(7) Uiso d R 1 H C5 0.6486(7) 0.3041(5) 0.1031(3) 0.0625(8) Uani d . 1 C H5A 0.8175 0.2737 0.0361 0.094 Uiso calc R 1 H H5B 0.6236 0.4676 0.1321 0.094 Uiso calc R 1 H H5C 0.4368 0.2328 0.0644 0.094 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 N2 0.0665(14) 0.0630(14) 0.0349(12) 0.0148(11) 0.0038(10) 0.0099(10) N1 0.0616(14) 0.0472(13) 0.0377(12) 0.0131(10) 0.0047(9) 0.0078(9) C1 0.0386(11) 0.0404(12) 0.0384(12) 0.0016(9) 0.0030(9) 0.0084(9) C2 0.0601(16) 0.0472(15) 0.0466(14) 0.0129(12) 0.0011(12) 0.0098(12) C3 0.0452(14) 0.0522(15) 0.0431(14) 0.0011(11) -0.0014(11) 0.0140(11) C4 0.0625(16) 0.0528(15) 0.0389(13) 0.0180(12) 0.0061(11) 0.0085(11) C5 0.0700(18) 0.076(2) 0.0457(16) 0.0123(15) -0.0003(13) 0.0222(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 '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 0.006 0.003 '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_3 _geom_angle C4 N2 C3 . 116.5(2) C2 N1 C1 . 117.1(2) N1 C1 C4 . 119.5(2) N1 C1 C1 2_756 117.9(3) C4 C1 C1 2_756 122.6(3) N1 C2 C3 . 123.0(2) N1 C2 H2 . 118.7 C3 C2 H2 . 118.3 N2 C3 C2 . 120.1(2) N2 C3 C5 . 118.6(2) C2 C3 C5 . 121.4(2) N2 C4 C1 . 123.9(2) N2 C4 H4 . 118.2 C1 C4 H4 . 117.9 C3 C5 H5A . 109.5 C3 C5 H5B . 109.5 H5A C5 H5B . 109.5 C3 C5 H5C . 109.5 H5A C5 H5C . 109.5 H5B C5 H5C . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance N2 C4 . 1.323(3) N2 C3 . 1.326(3) N1 C2 . 1.323(3) N1 C1 . 1.331(3) C1 C4 . 1.380(3) C1 C1 2_756 1.467(4) C2 C3 . 1.389(3) C2 H2 . 0.9293 C3 C5 . 1.504(3) C4 H4 . 0.9299 C5 H5A . 0.96 C5 H5B . 0.96 C5 H5C . 0.96 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 23542803