# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/181 # CIF for Compound 2 data_compound-2 _audit_creation_method SHELXL-97 _chemical_name_systematic 2-Methylpyrazine _chemical_name_common Methylpyrazine _chemical_formula_moiety 'C5 H6 N2' _chemical_formula_sum 'C5 H6 N2' _chemical_formula_weight 94.12 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' 0.0000 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' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 13.7248(19) _cell_length_b 13.7248(19) _cell_length_c 10.859(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2045.4(6) _cell_formula_units_Z 16 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description cylindric _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ;Nicolet R3 four circle diffractometer ; _diffrn_measurement_method 'Wyckoff scan mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1504 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0229 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 22.50 _reflns_number_total 1338 _reflns_number_gt 1302 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SIEMENS P3-PC diffractometer program, Vers. 4.24' _computing_cell_refinement 'SIEMENS P3-PC diffractometer program, Vers. 4.24' _computing_data_reduction 'SIEMENS XDISK V.4.20.2 PC' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version, Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version, Release 97-1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+0.4204P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -7(3) _refine_ls_number_reflns 1338 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.47305(18) 0.12767(18) -0.0958(2) 0.0424(6) Uani 1 1 d . . . C2 C 0.4476(2) 0.13110(19) 0.0229(2) 0.0350(7) Uani 1 1 d . . . C3 C 0.5175(2) 0.1265(2) 0.1143(2) 0.0369(7) Uani 1 1 d . . . H3 H 0.4965 0.1279 0.1986 0.044 Uiso 1 1 d R . . N4 N 0.61322(17) 0.11835(18) 0.0922(2) 0.0406(7) Uani 1 1 d . . . C5 C 0.6376(2) 0.1155(2) -0.0262(3) 0.0397(7) Uani 1 1 d . . . H5 H 0.7053 0.1115 -0.0478 0.048 Uiso 1 1 d R . . C6 C 0.5688(2) 0.1197(2) -0.1190(3) 0.0439(7) Uani 1 1 d . . . H6 H 0.5902 0.1158 -0.2030 0.053 Uiso 1 1 d R . . C7 C 0.3411(2) 0.1389(2) 0.0527(3) 0.0441(8) Uani 1 1 d . . . H7A H 0.3216 0.2076 0.0533 0.066 Uiso 1 1 d R . . H7B H 0.3287 0.1102 0.1339 0.066 Uiso 1 1 d R . . H7C H 0.3033 0.1037 -0.0097 0.066 Uiso 1 1 d R . . N11 N 0.01882(16) 0.13326(16) 0.15878(19) 0.0380(6) Uani 1 1 d . . . C12 C 0.0424(2) 0.13956(18) 0.2770(2) 0.0328(6) Uani 1 1 d . . . C13 C -0.02900(19) 0.1298(2) 0.3673(2) 0.0384(7) Uani 1 1 d . . . H13 H -0.0096 0.1351 0.4520 0.046 Uiso 1 1 d R . . N14 N -0.12234(17) 0.11438(19) 0.3430(2) 0.0440(7) Uani 1 1 d . . . C15 C -0.1455(2) 0.1091(2) 0.2233(3) 0.0431(7) Uani 1 1 d . . . H15 H -0.2123 0.1004 0.1998 0.052 Uiso 1 1 d R . . C16 C -0.0755(2) 0.1170(2) 0.1329(2) 0.0437(7) Uani 1 1 d . . . H16 H -0.0938 0.1106 0.0480 0.052 Uiso 1 1 d R . . C17 C 0.1464(2) 0.1574(2) 0.3092(3) 0.0437(8) Uani 1 1 d . . . H17A H 0.1871 0.1067 0.2719 0.066 Uiso 1 1 d R . . H17B H 0.1542 0.1558 0.3989 0.066 Uiso 1 1 d R . . H17C H 0.1663 0.2213 0.2780 0.066 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0581(17) 0.0430(14) 0.0262(13) -0.0060(11) -0.0033(11) 0.0038(12) C2 0.0430(16) 0.0301(14) 0.0319(16) -0.0032(12) -0.0004(13) -0.0067(13) C3 0.0502(17) 0.0380(16) 0.0224(14) 0.0010(12) 0.0009(12) -0.0020(14) N4 0.0416(15) 0.0454(14) 0.0349(13) -0.0020(11) -0.0014(11) -0.0024(12) C5 0.0429(15) 0.0366(15) 0.0395(17) -0.0032(14) 0.0104(15) 0.0019(14) C6 0.060(2) 0.0414(18) 0.0303(17) -0.0048(14) 0.0045(16) 0.0018(16) C7 0.0468(18) 0.0391(17) 0.0464(18) -0.0022(15) -0.0019(14) -0.0008(14) N11 0.0442(16) 0.0413(15) 0.0286(12) -0.0023(11) 0.0051(10) -0.0011(12) C12 0.0415(15) 0.0297(15) 0.0271(13) 0.0011(11) 0.0006(12) -0.0003(13) C13 0.0415(17) 0.0475(16) 0.0262(15) 0.0040(14) -0.0004(12) 0.0028(13) N14 0.0386(13) 0.0576(16) 0.0359(12) 0.0049(12) 0.0012(11) -0.0022(12) C15 0.0411(17) 0.0447(18) 0.0435(17) 0.0059(15) -0.0062(15) 0.0039(16) C16 0.061(2) 0.0458(17) 0.0243(15) 0.0005(14) -0.0079(14) 0.0004(15) C17 0.0381(16) 0.053(2) 0.0396(17) -0.0028(15) 0.0035(13) -0.0017(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.336(3) . ? N1 C6 1.343(4) . ? C2 C3 1.383(4) . ? C2 C7 1.501(4) . ? C3 N4 1.340(4) . ? C3 H3 0.9600 . ? N4 C5 1.329(3) . ? C5 C6 1.382(4) . ? C5 H5 0.9601 . ? C6 H6 0.9600 . ? C7 H7A 0.9799 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N11 C12 1.327(3) . ? N11 C16 1.343(4) . ? C12 C13 1.393(4) . ? C12 C17 1.489(4) . ? C13 N14 1.325(4) . ? C13 H13 0.9600 . ? N14 C15 1.340(3) . ? C15 C16 1.378(4) . ? C15 H15 0.9600 . ? C16 H16 0.9600 . ? C17 H17A 0.9800 . ? C17 H17B 0.9801 . ? C17 H17C 0.9799 . ? 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 C2 N1 C6 116.1(2) . . ? N1 C2 C3 120.6(3) . . ? N1 C2 C7 117.7(2) . . ? C3 C2 C7 121.6(2) . . ? N4 C3 C2 123.8(3) . . ? N4 C3 H3 117.8 . . ? C2 C3 H3 118.4 . . ? C5 N4 C3 115.0(3) . . ? N4 C5 C6 122.1(3) . . ? N4 C5 H5 118.8 . . ? C6 C5 H5 119.1 . . ? N1 C6 C5 122.4(3) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.9 . . ? C2 C7 H7A 109.6 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.3 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C12 N11 C16 116.7(2) . . ? N11 C12 C13 120.2(2) . . ? N11 C12 C17 118.2(2) . . ? C13 C12 C17 121.7(2) . . ? N14 C13 C12 123.8(3) . . ? N14 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C13 N14 C15 115.5(2) . . ? N14 C15 C16 121.5(3) . . ? N14 C15 H15 119.5 . . ? C16 C15 H15 119.1 . . ? N11 C16 C15 122.4(2) . . ? N11 C16 H16 118.0 . . ? C15 C16 H16 119.6 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.116 _refine_diff_density_min -0.105 _refine_diff_density_rms 0.032 #===END # CIF for Compound 3 data_compound-3 _audit_creation_method SHELXL-97 _chemical_name_systematic 2,3-Dimethylpyrazine _chemical_name_common 2,3-Dimethylpyrazine _chemical_formula_moiety 'C6 H8 N2' _chemical_formula_sum 'C6 H8 N2' _chemical_formula_weight 108.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8108(14) _cell_length_b 6.5509(14) _cell_length_c 12.164(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.613(14) _cell_angle_gamma 90.00 _cell_volume 589.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description cylindric _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ;Nicolet R3 four circle diffractometer ; _diffrn_measurement_method 'Wyckoff scan mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1790 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 29.99 _reflns_number_total 1714 _reflns_number_gt 1450 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SIEMENS P3-PC diffractometer program, Vers.4.24' _computing_cell_refinement 'SIEMENS P3-PC diffractometer program, Vers.4.24' _computing_data_reduction 'SIEMENS XDISK V.4.20.2 PC' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version, Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version, Release 97-1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0829P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.108(13) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1714 _refine_ls_number_parameters 74 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1204 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.19000(11) 0.03391(13) 0.36314(6) 0.0320(2) Uani 1 d . . . C2 C 0.26837(11) 0.07695(13) 0.47546(7) 0.0266(2) Uani 1 d . . . C3 C 0.25654(12) -0.05902(14) 0.56302(8) 0.0277(2) Uani 1 d . . . N4 N 0.16210(11) -0.23267(13) 0.53665(7) 0.0342(2) Uani 1 d . . . C5 C 0.08127(14) -0.27169(15) 0.42342(9) 0.0361(2) Uani 1 d . . . H5 H 0.0106 -0.3937 0.4013 0.043 Uiso 1 d R . . C6 C 0.09689(13) -0.14168(16) 0.33803(8) 0.0351(2) Uani 1 d . . . H6 H 0.0401 -0.1774 0.2590 0.042 Uiso 1 calc R . . C7 C 0.36865(14) 0.27525(15) 0.50484(9) 0.0353(2) Uani 1 d . . . H7A H 0.3693 0.3434 0.4333 0.053 Uiso 1 d R . . H7B H 0.4932 0.2488 0.5537 0.053 Uiso 1 d R . . H7C H 0.3089 0.3631 0.5467 0.053 Uiso 1 d R . . C8 C 0.35169(14) -0.01445(18) 0.68875(8) 0.0383(3) Uani 1 d . . . H8A H 0.3216 -0.1201 0.7366 0.057 Uiso 1 d R . . H8B H 0.3131 0.1190 0.7086 0.057 Uiso 1 d R . . H8C H 0.4825 -0.0131 0.7032 0.057 Uiso 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0354(4) 0.0331(4) 0.0245(4) 0.0009(3) 0.0053(3) 0.0056(3) C2 0.0270(4) 0.0260(4) 0.0251(4) 0.0013(3) 0.0061(3) 0.0055(3) C3 0.0268(4) 0.0298(4) 0.0259(4) 0.0020(3) 0.0074(3) 0.0050(3) N4 0.0350(4) 0.0314(4) 0.0370(4) 0.0027(3) 0.0124(3) 0.0013(3) C5 0.0336(5) 0.0311(5) 0.0421(5) -0.0070(4) 0.0099(4) -0.0017(4) C6 0.0340(5) 0.0371(5) 0.0301(4) -0.0067(4) 0.0044(3) 0.0038(4) C7 0.0416(5) 0.0283(4) 0.0334(5) 0.0006(3) 0.0084(4) -0.0009(4) C8 0.0391(5) 0.0485(6) 0.0239(4) 0.0046(4) 0.0055(3) -0.0002(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3369(11) . ? N1 C6 1.3429(13) . ? C2 C3 1.4139(12) . ? C2 C7 1.5000(13) . ? C3 N4 1.3380(12) . ? C3 C8 1.5003(13) . ? N4 C5 1.3439(13) . ? C5 C6 1.3784(15) . ? C5 H5 0.9600 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9799 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C2 N1 C6 116.82(8) . . ? N1 C2 C3 121.22(8) . . ? N1 C2 C7 117.39(8) . . ? C3 C2 C7 121.39(8) . . ? N4 C3 C2 121.24(8) . . ? N4 C3 C8 117.75(8) . . ? C2 C3 C8 121.00(9) . . ? C3 N4 C5 116.75(8) . . ? N4 C5 C6 121.95(9) . . ? N4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? N1 C6 C5 121.98(9) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.315 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.038 #===END # CIF for Compound 4 data_compound-4 _audit_creation_method SHELXL-97 _chemical_name_systematic 2,5-Dimethylpyrazine _chemical_name_common 2,5-Dimethylpyrazine _chemical_formula_moiety 'C6 H8 N2' _chemical_formula_sum 'C6 H8 N2' _chemical_formula_weight 108.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n 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' _cell_length_a 5.7021(10) _cell_length_b 5.048(2) _cell_length_c 10.6640(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.549(15) _cell_angle_gamma 90.00 _cell_volume 297.12(14) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description cylindric _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 116 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ;Nicolet R3m/V four circle diffractometer ; _diffrn_measurement_method 'Wyckoff scan mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 540 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0116 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 24.99 _reflns_number_total 513 _reflns_number_gt 475 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SIEMENS P3-PC diffractometer program, Vers.4.24' _computing_cell_refinement 'SIEMENS P3-PC diffractometer program, Vers.4.24' _computing_data_reduction 'SIEMENS XDISK V.4.20.2 PC' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version, Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version, Release 97-1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.0678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 513 _refine_ls_number_parameters 37 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0850 _refine_ls_wR_factor_gt 0.0833 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.79109(18) 0.1333(2) 0.43365(9) 0.0361(3) Uani 1 d . . . C2 C 0.8885(2) 0.1776(2) 0.56009(10) 0.0309(3) Uani 1 d . . . C3 C 1.0957(2) 0.0429(2) 0.62361(10) 0.0343(3) Uani 1 d . . . H3 H 1.1618 0.0784 0.7140 0.041 Uiso 1 d R . . C4 C 0.7677(2) 0.3740(3) 0.62832(12) 0.0406(4) Uani 1 d . . . H4A H 0.8565 0.3846 0.7197 0.061 Uiso 1 d R . . H4B H 0.6007 0.3176 0.6222 0.061 Uiso 1 d R . . H4C H 0.7667 0.5484 0.5878 0.061 Uiso 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0375(6) 0.0413(6) 0.0260(5) 0.0005(4) 0.0014(4) 0.0015(4) C2 0.0346(6) 0.0317(6) 0.0255(6) 0.0011(5) 0.0060(4) -0.0064(5) C3 0.0385(7) 0.0396(7) 0.0216(6) -0.0018(5) 0.0012(5) -0.0033(5) C4 0.0458(8) 0.0412(7) 0.0347(7) -0.0022(5) 0.0097(5) 0.0018(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.3338(16) 3_756 ? N1 C2 1.3417(15) . ? C2 C3 1.3840(17) . ? C2 C4 1.4963(16) . ? C3 N1 1.3338(16) 3_756 ? C3 H3 0.9600 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? 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 C3 N1 C2 116.45(10) 3_756 . ? N1 C2 C3 119.80(11) . . ? N1 C2 C4 118.31(10) . . ? C3 C2 C4 121.90(10) . . ? N1 C3 C2 123.75(10) 3_756 . ? N1 C3 H3 118.1 3_756 . ? C2 C3 H3 118.1 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.116 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033 #===END # CIF for Compound 5 data_compound-5 _audit_creation_method SHELXL-97 _chemical_name_systematic 2,6-Dimethylpyrazine _chemical_name_common 2,6-Dimethylpyrazine _chemical_formula_moiety 'C6 H8 N2' _chemical_formula_sum 'C6 H8 N2' _chemical_formula_weight 108.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.55680(10) _cell_length_b 10.85520(10) _cell_length_c 7.44510(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.5250(10) _cell_angle_gamma 90.00 _cell_volume 610.700(13) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 232 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type 'Siemens SADABS multi-scan' _exptl_absorpt_correction_T_min 0.580 _exptl_absorpt_correction_T_max 1.000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD area detector system' _diffrn_measurement_method ;Fullsphere data collection in five different runs. 1st run: \f is kept constant at 0\%, and 120 frames collected with an interval of 0.3\% in \w 2nd to 5th runs: \w kept constant at 135, 143, 156, 169\% and 600 frames in each run with an interval of 0.3\% in \f ; _diffrn_detector_area_resol_mean 512 _diffrn_standards_number ;area detector data,no standard reflections ; _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5124 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 28.34 _reflns_number_total 1431 _reflns_number_gt 1104 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'Siemens SMART CCD area detector system' _computing_cell_refinement 'Siemens SAINT program Vers.4.050' _computing_data_reduction 'Siemens SAINT program Vers.4.050' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version Release 97-1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1554P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1431 _refine_ls_number_parameters 73 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0809 _refine_ls_wR_factor_ref 0.2248 _refine_ls_wR_factor_gt 0.2060 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.86455(17) 0.25615(10) 0.19826(16) 0.0384(4) Uani 1 d . . . C2 C 0.7027(2) 0.23959(13) 0.12669(19) 0.0380(5) Uani 1 d . . . C3 C 0.6394(2) 0.12126(14) 0.0895(2) 0.0438(5) Uani 1 d . . . H3 H 0.5232 0.1125 0.0379 0.053 Uiso 1 d R . . N4 N 0.7348(2) 0.01925(12) 0.1233(2) 0.0499(5) Uani 1 d . . . C5 C 0.8948(2) 0.03726(14) 0.1948(2) 0.0470(5) Uani 1 d . . . H5 H 0.9673 -0.0332 0.2211 0.056 Uiso 1 d R . . C6 C 0.9623(2) 0.15527(14) 0.2335(2) 0.0410(5) Uani 1 d . . . C7 C 0.5928(2) 0.35181(14) 0.0875(2) 0.0479(5) Uani 1 d . . . H7A H 0.4770 0.3266 0.0400 0.072 Uiso 1 d R . . H7B H 0.6531 0.4030 -0.0014 0.072 Uiso 1 d R . . H7C H 0.5768 0.3991 0.1983 0.072 Uiso 1 d R . . C8 C 1.1430(3) 0.17199(17) 0.3142(3) 0.0547(5) Uani 1 d . . . H8A H 1.1681 0.2601 0.3273 0.082 Uiso 1 d R . . H8B H 1.2314 0.1344 0.2358 0.082 Uiso 1 d R . . H8C H 1.1477 0.1324 0.4324 0.082 Uiso 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0394(9) 0.0341(6) 0.0417(7) -0.0009(4) -0.0021(6) -0.0007(5) C2 0.0401(10) 0.0376(8) 0.0363(8) 0.0003(5) 0.0006(6) -0.0007(5) C3 0.0401(10) 0.0448(8) 0.0465(9) -0.0026(6) -0.0035(7) -0.0067(6) N4 0.0532(11) 0.0360(7) 0.0605(9) -0.0043(5) -0.0003(7) -0.0059(5) C5 0.0520(11) 0.0347(8) 0.0543(10) -0.0021(6) 0.0010(7) 0.0008(6) C6 0.0424(10) 0.0371(8) 0.0436(8) -0.0013(5) 0.0004(7) -0.0006(6) C7 0.0454(11) 0.0448(9) 0.0535(10) 0.0041(6) -0.0076(8) 0.0056(7) C8 0.0426(11) 0.0476(9) 0.0735(12) -0.0011(7) -0.0121(9) 0.0023(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.342(2) . ? N1 C6 1.3456(19) . ? C2 C3 1.397(2) . ? C2 C7 1.5015(19) . ? C3 N4 1.344(2) . ? C3 H3 0.9600 . ? N4 C5 1.331(2) . ? C5 C6 1.408(2) . ? C5 H5 0.9600 . ? C6 C8 1.498(2) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9799 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C2 N1 C6 117.73(13) . . ? N1 C2 C3 120.73(14) . . ? N1 C2 C7 117.97(12) . . ? C3 C2 C7 121.30(14) . . ? N4 C3 C2 122.57(15) . . ? N4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C5 N4 C3 115.95(13) . . ? N4 C5 C6 122.81(15) . . ? N4 C5 H5 118.6 . . ? C6 C5 H5 118.6 . . ? N1 C6 C5 120.22(15) . . ? N1 C6 C8 118.46(13) . . ? C5 C6 C8 121.33(14) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.4 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.654 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.083 #===END # CIF for Compound 6 data_compound-6 _audit_creation_method SHELXL-97 _chemical_name_systematic 2,3,5-Trimethylpyrazine _chemical_name_common 'Trimethylpyrazine' _chemical_formula_moiety 'C7 H10 N2' _chemical_formula_sum 'C7 H10 N2' _chemical_formula_weight 122.17 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.1439(17) _cell_length_b 10.243(2) _cell_length_c 15.212(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.546(14) _cell_angle_gamma 90.00 _cell_volume 1418.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 50 _cell_measurement_theta_min 20 _cell_measurement_theta_max 25 _exptl_crystal_description cylindric _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.144 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ;Nicolet R3m/V four circle diffractometer ; _diffrn_measurement_method 'Wyckoff scan mode' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3748 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.08 _reflns_number_total 2491 _reflns_number_gt 1967 _reflns_threshold_expression 2sigma(I) _computing_data_collection 'SIEMENS P3-PC diffractometer program, Vers. 4.24' _computing_cell_refinement 'SIEMENS P3-PC diffractometer program, Vers. 4.24' _computing_data_reduction 'SIEMENS XDISK V.4.20.2 PC' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXL-97 UNIX Version, Release 97-1' _computing_publication_material 'Siemens SHELXL-97 UNIX Version, Release 97-1' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.5321P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2491 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.63685(16) 0.13077(15) 0.43932(10) 0.0417(4) Uani 1 d . . . N4 N 0.42768(16) -0.01139(15) 0.33413(10) 0.0381(4) Uani 1 d . . . C2 C 0.67631(19) 0.03005(17) 0.39112(11) 0.0342(4) Uani 1 d . . . C3 C 0.57053(19) -0.04168(17) 0.33826(11) 0.0339(4) Uani 1 d . . . C5 C 0.38804(19) 0.08957(19) 0.38311(12) 0.0383(4) Uani 1 d . . . C6 C 0.4928(2) 0.15865(19) 0.43476(13) 0.0426(5) Uani 1 d . . . H6 H 0.4631 0.2338 0.4742 0.051 Uiso 1 d R . . C7 C 0.8366(2) -0.0032(2) 0.39532(14) 0.0464(5) Uani 1 d . . . H7A H 0.8928 0.0585 0.4345 0.070 Uiso 1 d R . . H7B H 0.8523 -0.0921 0.4182 0.070 Uiso 1 d R . . H7C H 0.8694 0.0024 0.3360 0.070 Uiso 1 d R . . C8 C 0.6132(2) -0.1551(2) 0.28423(14) 0.0493(5) Uani 1 d . . . H8A H 0.5262 -0.1887 0.2487 0.074 Uiso 1 d R . . H8B H 0.6554 -0.2241 0.3235 0.074 Uiso 1 d R . . H8C H 0.6861 -0.1267 0.2451 0.074 Uiso 1 d R . . C9 C 0.2267(2) 0.1222(2) 0.37840(15) 0.0563(6) Uani 0.50 d P A 1 H9A H 0.1722 0.0760 0.3292 0.084 Uiso 0.50 d PR A 1 H9B H 0.1886 0.0965 0.4339 0.084 Uiso 0.50 d PR A 1 H9C H 0.2148 0.2165 0.3699 0.084 Uiso 0.50 d PR A 1 C9' C 0.2267(2) 0.1222(2) 0.37840(15) 0.0563(6) Uani 0.50 d P A 2 H9D H 0.2272 0.1879 0.4195 0.084 Uiso 0.50 d PR A 2 H9E H 0.2101 0.1471 0.3174 0.084 Uiso 0.50 d PR A 2 H9F H 0.1899 0.0400 0.3918 0.084 Uiso 0.50 d PR A 2 N11 N -0.07728(17) -0.15008(16) 0.93697(10) 0.0416(4) Uani 1 d . . . N14 N 0.09581(15) 0.00514(15) 0.83808(9) 0.0361(4) Uani 1 d . . . C12 C -0.13195(18) -0.04295(18) 0.89644(11) 0.0354(4) Uani 1 d . . . C13 C -0.04470(19) 0.03548(17) 0.84673(11) 0.0340(4) Uani 1 d . . . C15 C 0.15052(19) -0.10286(18) 0.87906(11) 0.0354(4) Uani 1 d . . . C16 C 0.0638(2) -0.17852(19) 0.92780(12) 0.0415(5) Uani 1 d . . . H16 H 0.1053 -0.2582 0.9605 0.050 Uiso 1 d R . . C17 C -0.2897(2) -0.0098(2) 0.90504(14) 0.0502(5) Uani 1 d . . . H17A H -0.3308 -0.0726 0.9445 0.075 Uiso 1 d R . . H17B H -0.2959 0.0784 0.9294 0.075 Uiso 1 d R . . H17C H -0.3454 -0.0134 0.8467 0.075 Uiso 1 d R . . C18 C -0.1048(2) 0.1559(2) 0.80033(15) 0.0519(5) Uani 1 d . . . H18A H -0.0299 0.1941 0.7663 0.078 Uiso 1 d R . . H18B H -0.1324 0.2193 0.8441 0.078 Uiso 1 d R . . H18C H -0.1916 0.1330 0.7604 0.078 Uiso 1 d R . . C19 C 0.3077(2) -0.1363(2) 0.86898(14) 0.0501(5) Uani 0.50 d P B 1 H19A H 0.3348 -0.1067 0.8115 0.075 Uiso 0.50 d PR B 1 H19B H 0.3149 -0.2317 0.8723 0.075 Uiso 0.50 d PR B 1 H19C H 0.3745 -0.0975 0.9161 0.075 Uiso 0.50 d PR B 1 C19' C 0.3077(2) -0.1363(2) 0.86898(14) 0.0501(5) Uani 0.50 d P B 2 H19D H 0.3483 -0.1929 0.9089 0.075 Uiso 0.50 d PR B 2 H19E H 0.3708 -0.0427 0.8846 0.075 Uiso 0.50 d PR B 2 H19F H 0.3259 -0.1464 0.8080 0.075 Uiso 0.50 d PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0400(9) 0.0416(9) 0.0433(9) -0.0066(7) 0.0034(7) -0.0015(7) N4 0.0352(8) 0.0427(9) 0.0368(8) 0.0011(7) 0.0056(6) -0.0058(7) C2 0.0357(10) 0.0341(10) 0.0330(9) 0.0034(8) 0.0045(7) 0.0000(8) C3 0.0378(10) 0.0332(10) 0.0319(9) 0.0031(7) 0.0091(7) -0.0032(7) C5 0.0359(10) 0.0418(11) 0.0380(10) 0.0047(9) 0.0080(8) 0.0004(8) C6 0.0430(11) 0.0419(11) 0.0438(11) -0.0056(9) 0.0089(8) 0.0019(9) C7 0.0384(10) 0.0514(12) 0.0491(12) -0.0013(10) 0.0034(9) 0.0020(9) C8 0.0526(12) 0.0435(12) 0.0533(12) -0.0098(10) 0.0124(10) -0.0064(9) C9 0.0377(11) 0.0686(15) 0.0635(14) -0.0001(12) 0.0089(10) 0.0044(10) C9' 0.0377(11) 0.0686(15) 0.0635(14) -0.0001(12) 0.0089(10) 0.0044(10) N11 0.0410(9) 0.0437(10) 0.0400(9) 0.0030(7) 0.0036(7) -0.0075(7) N14 0.0347(8) 0.0385(9) 0.0349(8) 0.0004(7) 0.0021(6) -0.0016(7) C12 0.0331(9) 0.0392(10) 0.0335(9) -0.0065(8) 0.0006(7) -0.0055(8) C13 0.0344(9) 0.0328(10) 0.0340(9) -0.0044(8) -0.0008(7) -0.0035(7) C15 0.0359(9) 0.0369(10) 0.0328(9) -0.0035(8) 0.0009(7) 0.0004(8) C16 0.0440(11) 0.0384(11) 0.0409(11) 0.0062(9) -0.0015(8) 0.0003(9) C17 0.0355(11) 0.0615(14) 0.0540(13) -0.0065(11) 0.0065(9) -0.0042(10) C18 0.0479(12) 0.0430(12) 0.0638(14) 0.0097(10) 0.0005(10) 0.0038(9) C19 0.0387(11) 0.0584(13) 0.0534(12) 0.0031(10) 0.0054(9) 0.0102(9) C19' 0.0387(11) 0.0584(13) 0.0534(12) 0.0031(10) 0.0054(9) 0.0102(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.335(2) . ? N1 C6 1.343(2) . ? N4 C3 1.338(2) . ? N4 C5 1.345(2) . ? C2 C3 1.404(3) . ? C2 C7 1.500(2) . ? C3 C8 1.497(3) . ? C5 C6 1.375(3) . ? C5 C9' 1.508(3) . ? C5 C9 1.508(3) . ? C6 H6 1.0282 . ? C7 H7A 0.9799 . ? C7 H7B 0.9801 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9799 . ? C9 H9A 0.9801 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C9 H9D 0.9182 . ? C9 H9E 0.9600 . ? C9 H9F 0.9363 . ? C9' H9A 0.9801 . ? C9' H9B 0.9800 . ? C9' H9C 0.9800 . ? C9' H9D 0.9182 . ? C9' H9E 0.9600 . ? C9' H9F 0.9363 . ? N11 C12 1.332(2) . ? N11 C16 1.343(2) . ? N14 C13 1.341(2) . ? N14 C15 1.343(2) . ? C12 C13 1.404(3) . ? C12 C17 1.500(2) . ? C13 C18 1.499(3) . ? C15 C16 1.376(3) . ? C15 C19' 1.500(2) . ? C15 C19 1.500(2) . ? C16 H16 1.0102 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9801 . ? C19 H19C 0.9800 . ? C19 H19D 0.8931 . ? C19 H19E 1.1326 . ? C19 H19F 0.9633 . ? C19' H19A 0.9800 . ? C19' H19B 0.9801 . ? C19' H19C 0.9800 . ? C19' H19D 0.8931 . ? C19' H19E 1.1326 . ? C19' H19F 0.9633 . ? 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 C2 N1 C6 116.85(16) . . ? C3 N4 C5 117.81(15) . . ? N1 C2 C3 120.73(16) . . ? N1 C2 C7 117.84(16) . . ? C3 C2 C7 121.43(16) . . ? N4 C3 C2 121.39(16) . . ? N4 C3 C8 117.35(16) . . ? C2 C3 C8 121.27(16) . . ? N4 C5 C6 120.15(16) . . ? N4 C5 C9' 117.32(17) . . ? C6 C5 C9' 122.53(18) . . ? N4 C5 C9 117.32(17) . . ? C6 C5 C9 122.53(18) . . ? C9' C5 C9 0.0(3) . . ? N1 C6 C5 123.07(18) . . ? N1 C6 H6 116.2 . . ? C5 C6 H6 120.7 . . ? C2 C7 H7A 109.4 . . ? C2 C7 H7B 109.6 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.4 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C8 H8A 109.5 . . ? C3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C3 C8 H8C 109.4 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 110.6 . . ? C5 C9 H9B 109.1 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 108.7 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C5 C9 H9D 100.9 . . ? H9A C9 H9D 147.4 . . ? H9B C9 H9D 65.7 . . ? H9C C9 H9D 50.1 . . ? C5 C9 H9E 99.6 . . ? H9A C9 H9E 50.9 . . ? H9B C9 H9E 150.3 . . ? H9C C9 H9E 66.7 . . ? H9D C9 H9E 116.9 . . ? C5 C9 H9F 99.3 . . ? H9A C9 H9F 64.3 . . ? H9B C9 H9F 53.6 . . ? H9C C9 H9F 151.4 . . ? H9D C9 H9F 119.3 . . ? H9E C9 H9F 115.1 . . ? C5 C9' H9A 110.6 . . ? C5 C9' H9B 109.1 . . ? H9A C9' H9B 109.5 . . ? C5 C9' H9C 108.7 . . ? H9A C9' H9C 109.5 . . ? H9B C9' H9C 109.5 . . ? C5 C9' H9D 100.9 . . ? H9A C9' H9D 147.4 . . ? H9B C9' H9D 65.7 . . ? H9C C9' H9D 50.1 . . ? C5 C9' H9E 99.6 . . ? H9A C9' H9E 50.9 . . ? H9B C9' H9E 150.3 . . ? H9C C9' H9E 66.7 . . ? H9D C9' H9E 116.9 . . ? C5 C9' H9F 99.3 . . ? H9A C9' H9F 64.3 . . ? H9B C9' H9F 53.6 . . ? H9C C9' H9F 151.4 . . ? H9D C9' H9F 119.3 . . ? H9E C9' H9F 115.1 . . ? C12 N11 C16 116.86(16) . . ? C13 N14 C15 117.59(15) . . ? N11 C12 C13 120.89(16) . . ? N11 C12 C17 117.86(17) . . ? C13 C12 C17 121.25(17) . . ? N14 C13 C12 121.34(16) . . ? N14 C13 C18 117.13(16) . . ? C12 C13 C18 121.52(17) . . ? N14 C15 C16 120.41(16) . . ? N14 C15 C19' 117.30(17) . . ? C16 C15 C19' 122.28(17) . . ? N14 C15 C19 117.30(17) . . ? C16 C15 C19 122.28(17) . . ? C19' C15 C19 0.0(2) . . ? N11 C16 C15 122.90(18) . . ? N11 C16 H16 116.3 . . ? C15 C16 H16 120.8 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.4 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 110.3 . . ? C15 C19 H19B 106.4 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 111.6 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C15 C19 H19D 114.7 . . ? H19A C19 H19D 133.1 . . ? H19B C19 H19D 45.3 . . ? H19C C19 H19D 65.1 . . ? C15 C19 H19E 105.0 . . ? H19A C19 H19E 75.9 . . ? H19B C19 H19E 143.4 . . ? H19C C19 H19E 40.0 . . ? H19D C19 H19E 103.7 . . ? C15 C19 H19F 112.3 . . ? H19A C19 H19F 24.8 . . ? H19B C19 H19F 85.8 . . ? H19C C19 H19F 126.4 . . ? H19D C19 H19F 119.1 . . ? H19E C19 H19F 99.2 . . ? C15 C19' H19A 110.3 . . ? C15 C19' H19B 106.4 . . ? H19A C19' H19B 109.5 . . ? C15 C19' H19C 111.6 . . ? H19A C19' H19C 109.5 . . ? H19B C19' H19C 109.5 . . ? C15 C19' H19D 114.7 . . ? H19A C19' H19D 133.1 . . ? H19B C19' H19D 45.3 . . ? H19C C19' H19D 65.1 . . ? C15 C19' H19E 105.0 . . ? H19A C19' H19E 75.9 . . ? H19B C19' H19E 143.4 . . ? H19C C19' H19E 40.0 . . ? H19D C19' H19E 103.7 . . ? C15 C19' H19F 112.3 . . ? H19A C19' H19F 24.8 . . ? H19B C19' H19F 85.8 . . ? H19C C19' H19F 126.4 . . ? H19D C19' H19F 119.1 . . ? H19E C19' H19F 99.2 . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.08 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.181 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.039 #===END