#------------------------------------------------------------------------------ #$Date: 2008-04-05 11:48:19 +0300 (Sat, 05 Apr 2008) $ #$Revision: 342 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2200007.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_2200007 loop_ _publ_author_name 'Zhang, Ming-Hua' 'Zheng, Shu-Ling' 'Zhou, Jian' 'Liu, Shang-Yuan' 'Zhao, Zeng-Guo' _publ_section_title ; N-(2-Hydroxyethyl)pyrazine-2-carboxamide ; _journal_coeditor_code AT6037 _journal_issue 11 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o3568 _journal_page_last o3570 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C7 H9 N3 O2' _chemical_formula_moiety 'C7 H9 N3 O2' _chemical_formula_sum 'C7 H9 N3 O2' _chemical_formula_weight 167.17 _chemical_name_systematic ; N-(2-Hydroxyethyl)pyrazine-2-carboxamide ; _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 _cell_angle_alpha 86.953(4) _cell_angle_beta 87.262(4) _cell_angle_gamma 74.451(4) _cell_formula_units_Z 4 _cell_length_a 5.3054(12) _cell_length_b 7.8287(19) _cell_length_c 19.880(5) _cell_measurement_reflns_used 1336 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 25.60 _cell_measurement_theta_min 2.70 _cell_volume 793.9(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction 'SAINT (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device_type 'Bruker SMART CCD 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 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0525 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 4504 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_min 2.05 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.11 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_correction_T_min 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 352 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.24 _refine_diff_density_min -0.20 _refine_ls_extinction_coef 0.042(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3197 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.05 _refine_ls_R_factor_all 0.094 _refine_ls_R_factor_gt 0.049 _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^)+(0.0576P)^2^+0.0883P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.116 _refine_ls_wR_factor_ref 0.134 _reflns_number_gt 1895 _reflns_number_total 3197 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file at6037.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1 0.2083(4) 0.3372(2) 0.24175(9) 0.0409(5) Uani d . 1 N N2 -0.2735(4) 0.5184(3) 0.18822(11) 0.0518(6) Uani d . 1 N N3 0.3110(4) 0.3859(3) 0.36994(10) 0.0396(5) Uani d . 1 N H3 0.405(5) 0.316(3) 0.3424(12) 0.048(7) Uiso d . 1 H N4 0.2316(4) 0.8528(3) 0.26789(9) 0.0425(5) Uani d . 1 N N5 -0.2027(4) 1.0893(3) 0.32754(10) 0.0524(6) Uani d . 1 N N6 0.2069(4) 0.7568(3) 0.13834(10) 0.0436(5) Uani d . 1 N H6 0.326(5) 0.714(4) 0.1646(14) 0.066(9) Uiso d . 1 H O1 -0.0790(3) 0.5936(2) 0.38138(8) 0.0526(5) Uani d . 1 O O2 0.1559(4) 0.2186(3) 0.49932(9) 0.0631(6) Uani d . 1 O H2 0.1057 0.2740 0.5335 0.095 Uiso calc R 1 H O3 -0.1852(3) 0.9577(2) 0.12904(9) 0.0642(6) Uani d . 1 O O4 0.4084(5) 0.7642(3) -0.04072(9) 0.0779(6) Uani d . 1 O H4 0.3353 0.8474 -0.0658 0.117 Uiso calc R 1 H C1 0.0246(4) 0.4501(3) 0.27757(10) 0.0330(5) Uani d . 1 C C2 -0.2126(4) 0.5384(3) 0.25103(12) 0.0448(6) Uani d . 1 C H2A -0.3352 0.6151 0.2781 0.054 Uiso calc R 1 H C3 -0.0898(5) 0.4069(3) 0.15268(12) 0.0517(7) Uani d . 1 C H3A -0.1220 0.3889 0.1084 0.062 Uiso calc R 1 H C4 0.1471(5) 0.3168(3) 0.17885(12) 0.0484(6) Uani d . 1 C H4A 0.2684 0.2391 0.1518 0.058 Uiso calc R 1 H C5 0.0818(4) 0.4830(3) 0.34838(11) 0.0365(5) Uani d . 1 C C6 0.4113(5) 0.3926(3) 0.43607(11) 0.0450(6) Uani d . 1 C H6A 0.3057 0.4971 0.4580 0.054 Uiso calc R 1 H H6B 0.5891 0.4036 0.4310 0.054 Uiso calc R 1 H C7 0.4095(5) 0.2305(3) 0.48004(12) 0.0495(6) Uani d . 1 C H7A 0.4999 0.1257 0.4560 0.059 Uiso calc R 1 H H7B 0.5054 0.2321 0.5202 0.059 Uiso calc R 1 H C8 0.0132(4) 0.9250(3) 0.23437(11) 0.0359(5) Uani d . 1 C C9 -0.1990(4) 1.0409(3) 0.26423(12) 0.0471(6) Uani d . 1 C H9 -0.3468 1.0877 0.2390 0.057 Uiso calc R 1 H C10 0.0139(5) 1.0182(3) 0.36063(12) 0.0476(6) Uani d . 1 C H10 0.0220 1.0479 0.4050 0.057 Uiso calc R 1 H C11 0.2273(5) 0.9018(3) 0.33143(12) 0.0472(6) Uani d . 1 C H11 0.3746 0.8552 0.3569 0.057 Uiso calc R 1 H C12 0.0042(4) 0.8809(3) 0.16215(11) 0.0414(6) Uani d . 1 C C13 0.2332(5) 0.7071(3) 0.06827(11) 0.0468(6) Uani d . 1 C H13A 0.0609 0.7226 0.0506 0.056 Uiso calc R 1 H H13B 0.3277 0.5829 0.0657 0.056 Uiso calc R 1 H C14 0.3759(6) 0.8178(4) 0.02653(12) 0.0629(8) Uani d . 1 C H14A 0.2781 0.9416 0.0276 0.075 Uiso calc R 1 H H14B 0.5459 0.8057 0.0450 0.075 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 N1 0.0415(11) 0.0459(12) 0.0333(11) -0.0083(9) 0.0016(8) -0.0046(9) N2 0.0505(12) 0.0576(14) 0.0463(13) -0.0114(11) -0.0117(10) 0.0016(10) N3 0.0421(11) 0.0451(12) 0.0287(11) -0.0053(10) -0.0018(9) -0.0077(9) N4 0.0410(11) 0.0494(12) 0.0331(11) -0.0042(9) -0.0032(8) -0.0031(9) N5 0.0483(12) 0.0565(14) 0.0482(13) -0.0059(10) 0.0048(10) -0.0122(10) N6 0.0425(12) 0.0554(13) 0.0283(11) -0.0041(10) -0.0040(9) -0.0034(9) O1 0.0515(10) 0.0553(11) 0.0443(10) -0.0007(9) 0.0033(8) -0.0158(8) O2 0.0794(13) 0.0709(14) 0.0463(12) -0.0335(11) 0.0162(9) -0.0159(9) O3 0.0579(11) 0.0721(13) 0.0514(12) 0.0064(10) -0.0265(9) -0.0027(9) O4 0.1160(18) 0.0773(14) 0.0344(11) -0.0154(13) 0.0012(11) -0.0037(9) C1 0.0316(11) 0.0332(12) 0.0332(12) -0.0072(9) 0.0020(9) -0.0017(9) C2 0.0400(13) 0.0480(15) 0.0424(14) -0.0048(11) -0.0016(11) -0.0019(11) C3 0.0636(17) 0.0592(17) 0.0367(14) -0.0228(14) -0.0106(13) -0.0007(12) C4 0.0520(15) 0.0557(16) 0.0355(14) -0.0105(12) 0.0053(11) -0.0095(11) C5 0.0399(13) 0.0363(13) 0.0329(13) -0.0096(11) 0.0031(10) -0.0039(10) C6 0.0489(14) 0.0483(15) 0.0389(14) -0.0132(11) -0.0077(11) -0.0054(11) C7 0.0578(15) 0.0505(16) 0.0365(14) -0.0078(12) -0.0004(11) -0.0034(11) C8 0.0339(12) 0.0355(12) 0.0361(13) -0.0057(10) -0.0029(10) 0.0009(10) C9 0.0399(13) 0.0486(15) 0.0490(16) -0.0043(12) -0.0037(11) -0.0032(12) C10 0.0557(15) 0.0483(15) 0.0406(14) -0.0165(13) 0.0044(12) -0.0083(11) C11 0.0478(14) 0.0578(16) 0.0340(14) -0.0099(12) -0.0077(11) -0.0012(11) C12 0.0429(13) 0.0441(14) 0.0371(13) -0.0112(11) -0.0075(11) 0.0012(11) C13 0.0512(14) 0.0522(15) 0.0358(14) -0.0103(12) -0.0035(11) -0.0072(11) C14 0.086(2) 0.075(2) 0.0327(15) -0.0306(16) -0.0017(13) -0.0025(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C1 1.333(3) ? N1 C4 1.335(3) ? N2 C3 1.324(3) ? N2 C2 1.332(3) ? N3 C5 1.327(3) yes N3 C6 1.450(3) ? N3 H3 0.84(2) ? N4 C11 1.337(3) ? N4 C8 1.337(3) ? N5 C10 1.325(3) ? N5 C9 1.331(3) ? N6 C12 1.328(3) ? N6 C13 1.456(3) ? N6 H6 0.83(3) ? O1 C5 1.232(2) yes O2 C7 1.408(3) ? O2 H2 0.8200 ? O3 C12 1.226(3) ? O4 C14 1.411(3) ? O4 H4 0.8200 ? C1 C2 1.377(3) ? C1 C5 1.504(3) yes C2 H2A 0.9300 ? C3 C4 1.377(3) ? C3 H3A 0.9300 ? C4 H4A 0.9300 ? C6 C7 1.504(3) ? C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 C9 1.374(3) ? C8 C12 1.500(3) ? C9 H9 0.9300 ? C10 C11 1.375(3) ? C10 H10 0.9300 ? C11 H11 0.9300 ? C13 C14 1.492(4) ? C13 H13A 0.9700 ? C13 H13B 0.9700 ? C14 H14A 0.9700 ? C14 H14B 0.9700 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N1 C4 115.57(19) ? C3 N2 C2 115.3(2) ? C5 N3 C6 125.4(2) ? C5 N3 H3 116.5(16) ? C6 N3 H3 118.1(16) ? C11 N4 C8 115.4(2) ? C10 N5 C9 115.5(2) ? C12 N6 C13 122.7(2) ? C12 N6 H6 116.7(19) ? C13 N6 H6 120.4(19) ? C7 O2 H2 109.5 ? C14 O4 H4 109.5 ? N1 C1 C2 121.7(2) ? N1 C1 C5 118.59(18) ? C2 C1 C5 119.7(2) ? N2 C2 C1 122.7(2) ? N2 C2 H2A 118.6 ? C1 C2 H2A 118.6 ? N2 C3 C4 122.5(2) ? N2 C3 H3A 118.8 ? C4 C3 H3A 118.8 ? N1 C4 C3 122.2(2) ? N1 C4 H4A 118.9 ? C3 C4 H4A 118.9 ? O1 C5 N3 125.3(2) yes O1 C5 C1 119.93(19) yes N3 C5 C1 114.78(19) yes N3 C6 C7 112.40(19) ? N3 C6 H6A 109.1 ? C7 C6 H6A 109.1 ? N3 C6 H6B 109.1 ? C7 C6 H6B 109.1 ? H6A C6 H6B 107.9 ? O2 C7 C6 113.3(2) ? O2 C7 H7A 108.9 ? C6 C7 H7A 108.9 ? O2 C7 H7B 108.9 ? C6 C7 H7B 108.9 ? H7A C7 H7B 107.7 ? N4 C8 C9 121.4(2) ? N4 C8 C12 118.8(2) ? C9 C8 C12 119.8(2) ? N5 C9 C8 123.1(2) ? N5 C9 H9 118.5 ? C8 C9 H9 118.5 ? N5 C10 C11 122.0(2) ? N5 C10 H10 119.0 ? C11 C10 H10 119.0 ? N4 C11 C10 122.6(2) ? N4 C11 H11 118.7 ? C10 C11 H11 118.7 ? O3 C12 N6 124.0(2) ? O3 C12 C8 119.6(2) ? N6 C12 C8 116.42(19) ? N6 C13 C14 110.9(2) ? N6 C13 H13A 109.5 ? C14 C13 H13A 109.5 ? N6 C13 H13B 109.5 ? C14 C13 H13B 109.5 ? H13A C13 H13B 108.0 ? O4 C14 C13 110.4(2) ? O4 C14 H14A 109.6 ? C13 C14 H14A 109.6 ? O4 C14 H14B 109.6 ? C13 C14 H14B 109.6 ? H14A C14 H14B 108.1 ? 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 C2 0.3(3) C4 N1 C1 C5 -178.69(19) C3 N2 C2 C1 0.1(3) N1 C1 C2 N2 -0.5(3) C5 C1 C2 N2 178.5(2) C2 N2 C3 C4 0.5(4) C1 N1 C4 C3 0.3(3) N2 C3 C4 N1 -0.7(4) C6 N3 C5 O1 0.3(4) C6 N3 C5 C1 -179.90(19) N1 C1 C5 O1 176.2(2) C2 C1 C5 O1 -2.8(3) N1 C1 C5 N3 -3.6(3) C2 C1 C5 N3 177.3(2) C5 N3 C6 C7 107.9(3) N3 C6 C7 O2 -68.4(3) C11 N4 C8 C9 -0.2(3) C11 N4 C8 C12 178.4(2) C10 N5 C9 C8 0.1(4) N4 C8 C9 N5 0.1(4) C12 C8 C9 N5 -178.4(2) C9 N5 C10 C11 -0.2(4) C8 N4 C11 C10 0.0(3) N5 C10 C11 N4 0.2(4) C13 N6 C12 O3 4.3(4) C13 N6 C12 C8 -176.3(2) N4 C8 C12 O3 -173.6(2) C9 C8 C12 O3 4.9(3) N4 C8 C12 N6 7.0(3) C9 C8 C12 N6 -174.5(2) C12 N6 C13 C14 89.9(3) N6 C13 C14 O4 177.9(2) 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 O4 H4 O3 2_575 0.82 1.94 2.763(3) 176 O2 H2 O1 2_566 0.82 2.01 2.813(2) 166 N6 H6 N2 1_655 0.83(3) 2.31(3) 3.062(3) 151(3) N3 H3 N5 1_645 0.84(2) 2.36(2) 3.090(3) 145(2) N3 H3 N1 . 0.84(2) 2.28(2) 2.699(3) 111.0(19)