#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2208241.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_2208241 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _[local]_cod_cif_authors_sg_H-M 'P 21/n ' loop_ _publ_author_name 'Madeleine Helliwell' 'You Yun' 'John A. Joule' _publ_section_title ; Surprising orientation in ring synthesis of 3,5-dimethylpyrazin-2(1H)-one ; _journal_coeditor_code AT6083 _journal_issue 3 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o955 _journal_page_last o956 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C6 H8 N2 O' _chemical_formula_moiety 'C6 H8 N2 O' _chemical_formula_sum 'C6 H8 N2 O' _chemical_formula_weight 124.14 _chemical_melting_point .144E-143 _chemical_name_systematic ; 3,5-dimethylpyrazin-2(1H)-one ; _symmetry_cell_setting monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 105.25(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.009(10) _cell_length_b 14.59(3) _cell_length_c 11.59(3) _cell_measurement_reflns_used 12419 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.93 _cell_measurement_theta_min 2.29 _cell_volume 654(3) _computing_cell_refinement 'DENZO (Otwinowski, 1988)' _computing_data_collection 'MSC RAXIS11 Control software' _computing_data_reduction DENZO _computing_publication_material 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.732 _diffrn_measured_fraction_theta_max 0.732 _diffrn_measurement_device 'Rigaku R-AXIS' _diffrn_measurement_method '5 and 6\% \f' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.05 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12419 _diffrn_reflns_theta_full 24.93 _diffrn_reflns_theta_max 24.93 _diffrn_reflns_theta_min 2.29 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 264 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.176 _refine_diff_density_min -0.153 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 88 _refine_ls_number_reflns 839 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0505P)^2^+0.2114P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1040 _refine_ls_wR_factor_ref 0.1102 _reflns_number_gt 724 _reflns_number_total 839 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file at6083.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_ _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 -0.2141(4) 0.49078(10) 0.34750(14) 0.0615(5) Uani d . 1 O N1 0.1332(5) 0.60752(11) 0.44190(16) 0.0458(5) Uani d . 1 N H1 0.171(6) 0.5743(16) 0.518(2) 0.076(8) Uiso d . 1 H N2 0.0425(4) 0.69612(11) 0.22727(14) 0.0439(5) Uani d . 1 N C1 -0.0691(5) 0.56613(13) 0.34268(18) 0.0435(5) Uani d . 1 C C2 -0.1047(5) 0.61644(14) 0.23166(18) 0.0412(5) Uani d . 1 C C3 0.2395(5) 0.73534(13) 0.33210(19) 0.0423(6) Uani d . 1 C C4 0.2850(5) 0.69143(14) 0.4374(2) 0.0462(6) Uani d . 1 C H4 0.4194 0.7180 0.5072 0.055 Uiso calc R 1 H C5 -0.3181(6) 0.57375(15) 0.11869(19) 0.0549(6) Uani d . 1 C H5A -0.3500 0.6171 0.0544 0.082 Uiso calc R 1 H H5B -0.5392 0.5564 0.1292 0.082 Uiso calc R 1 H H5C -0.2018 0.5204 0.1001 0.082 Uiso calc R 1 H C6 0.3903(6) 0.82800(14) 0.3194(2) 0.0572(6) Uani d . 1 C H6A 0.5251 0.8245 0.2623 0.086 Uiso calc R 1 H H6B 0.5352 0.8471 0.3954 0.086 Uiso calc R 1 H H6C 0.2067 0.8716 0.2925 0.086 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 0.0870(12) 0.0459(10) 0.0492(10) -0.0219(9) 0.0141(8) -0.0030(7) N1 0.0606(11) 0.0384(10) 0.0363(11) -0.0041(8) 0.0093(9) -0.0023(8) N2 0.0501(10) 0.0378(10) 0.0429(11) 0.0010(8) 0.0107(8) -0.0001(8) C1 0.0540(13) 0.0377(12) 0.0390(13) -0.0027(10) 0.0126(10) -0.0055(10) C2 0.0459(12) 0.0387(12) 0.0383(13) 0.0007(9) 0.0101(10) -0.0043(9) C3 0.0457(12) 0.0354(11) 0.0440(13) 0.0006(9) 0.0086(10) -0.0038(10) C4 0.0508(13) 0.0390(12) 0.0449(13) -0.0036(10) 0.0055(10) -0.0074(10) C5 0.0664(15) 0.0532(14) 0.0409(13) -0.0086(11) 0.0066(11) -0.0043(10) C6 0.0612(15) 0.0424(13) 0.0652(16) -0.0074(11) 0.0119(12) 0.0002(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.251(3) N1 C1 1.362(4) N1 C4 1.374(3) N1 H1 0.98(3) N2 C2 1.310(3) N2 C3 1.387(4) C1 C2 1.456(4) C2 C5 1.498(4) C3 C4 1.348(4) C3 C6 1.503(4) C4 H4 0.9300 C5 H5A 0.9600 C5 H5B 0.9600 C5 H5C 0.9600 C6 H6A 0.9600 C6 H6B 0.9600 C6 H6C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C4 122.3(2) C1 N1 H1 117.2(14) C4 N1 H1 120.5(14) C2 N2 C3 119.4(2) O1 C1 N1 122.1(2) O1 C1 C2 122.9(2) N1 C1 C2 114.9(2) N2 C2 C1 122.8(2) N2 C2 C5 119.6(2) C1 C2 C5 117.6(2) C4 C3 N2 120.5(2) C4 C3 C6 123.6(2) N2 C3 C6 115.9(2) C3 C4 N1 120.1(2) C3 C4 H4 119.9 N1 C4 H4 119.9 C2 C5 H5A 109.5 C2 C5 H5B 109.5 H5A C5 H5B 109.5 C2 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C3 C6 H6A 109.5 C3 C6 H6B 109.5 H6A C6 H6B 109.5 C3 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 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 C4 N1 C1 O1 -178.15(19) C4 N1 C1 C2 1.5(3) C3 N2 C2 C1 -0.4(3) C3 N2 C2 C5 179.96(18) O1 C1 C2 N2 178.72(19) N1 C1 C2 N2 -0.9(3) O1 C1 C2 C5 -1.6(3) N1 C1 C2 C5 178.76(18) C2 N2 C3 C4 1.2(3) C2 N2 C3 C6 -178.28(18) N2 C3 C4 N1 -0.6(3) C6 C3 C4 N1 178.79(18) C1 N1 C4 C3 -0.8(3) _cod_database_code 2208241