Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'M. Bryce' 'A. Batsanov' 'Gregory Hughes' 'Figen Türksoy' _publ_contact_author_name 'Prof M Bryce' _publ_contact_author_address ; Department of Chemistry Durham University Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email M.R.BRYCE@DURHAM.AC.UK _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Phenylene-2,5-dimethylpyrazine co-oligomers: synthesis by Suzuki couplings, X-ray structures of neutral and diprotonated teraryl species and efficient blue emission ; data_(2) _database_code_CSD 207424 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(2-methoxyphenyl)-3,6-dimethylpyrazine ; _chemical_name_common ? _chemical_melting_point '232--236 C' _chemical_formula_moiety 'C20 H20 N2 O2' _chemical_formula_sum 'C20 H20 N2 O2' _chemical_formula_weight 320.38 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' _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 8.692(1) _cell_length_b 7.562(1) _cell_length_c 13.034(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.53(1) _cell_angle_gamma 90.00 _cell_volume 836.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 598 _cell_measurement_theta_min 10.32 _cell_measurement_theta_max 29.76 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 4 sets of \w scans; each set at different \f and/or 2\q angles and each scan (5 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.84 cm. ; _diffrn_ambient_temperature 120(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 'SMART 6K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8427 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1648 _reflns_number_gt 1276 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART version 5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL version 6.12 (Bruker, 2001)' _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. ; _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^)+(0.0917P)^2^+0.0794P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1648 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0604 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1360 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.003 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 0.27605(13) 0.20549(16) 0.13243(9) 0.0328(4) Uani 1 1 d . . . N N 0.42251(15) 0.55217(18) 0.07759(10) 0.0274(4) Uani 1 1 d . . . C1 C 0.53210(19) 0.3109(2) 0.19134(12) 0.0263(4) Uani 1 1 d . . . C2 C 0.40678(19) 0.2093(2) 0.21175(12) 0.0275(4) Uani 1 1 d . . . C3 C 0.4213(2) 0.1220(2) 0.30784(13) 0.0323(4) Uani 1 1 d . . . H3 H 0.334(2) 0.051(3) 0.3209(15) 0.037(5) Uiso 1 1 d . . . C4 C 0.5603(2) 0.1398(2) 0.38301(14) 0.0351(5) Uani 1 1 d . . . H4 H 0.569(2) 0.074(3) 0.4495(18) 0.053(6) Uiso 1 1 d . . . C5 C 0.6844(2) 0.2407(2) 0.36530(14) 0.0344(4) Uani 1 1 d . . . H5 H 0.781(2) 0.252(3) 0.4186(17) 0.039(5) Uiso 1 1 d . . . C6 C 0.6700(2) 0.3259(2) 0.26808(13) 0.0307(4) Uani 1 1 d . . . H6 H 0.757(2) 0.401(3) 0.2528(15) 0.040(5) Uiso 1 1 d . . . C7 C 0.1396(2) 0.1166(3) 0.15200(16) 0.0400(5) Uani 1 1 d . . . H71 H 0.103(2) 0.177(3) 0.2162(18) 0.047(6) Uiso 1 1 d . . . H72 H 0.055(3) 0.125(3) 0.0835(18) 0.054(6) Uiso 1 1 d . . . H73 H 0.161(2) -0.006(3) 0.1659(16) 0.041(5) Uiso 1 1 d . . . C8 C 0.51417(18) 0.4081(2) 0.08952(11) 0.0240(4) Uani 1 1 d . . . C9 C 0.59240(19) 0.3545(2) 0.01181(12) 0.0271(4) Uani 1 1 d . . . C10 C 0.6928(3) 0.1915(3) 0.02097(17) 0.0422(5) Uani 1 1 d . . . H101 H 0.783(4) 0.210(4) -0.015(3) 0.089(9) Uiso 1 1 d . . . H102 H 0.632(4) 0.096(5) -0.009(3) 0.112(12) Uiso 1 1 d . . . H103 H 0.738(4) 0.162(4) 0.090(3) 0.098(10) Uiso 1 1 d . . . 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 O 0.0323(7) 0.0370(7) 0.0294(6) 0.0043(5) 0.0074(5) -0.0065(5) N 0.0308(7) 0.0299(8) 0.0234(7) 0.0030(5) 0.0101(6) 0.0025(5) C1 0.0321(9) 0.0250(8) 0.0242(8) 0.0013(6) 0.0110(7) 0.0042(6) C2 0.0329(9) 0.0265(9) 0.0248(8) -0.0013(6) 0.0100(7) 0.0021(6) C3 0.0422(10) 0.0289(9) 0.0292(9) 0.0025(7) 0.0153(8) 0.0019(7) C4 0.0459(10) 0.0348(10) 0.0261(8) 0.0062(7) 0.0112(8) 0.0057(8) C5 0.0378(10) 0.0370(10) 0.0260(8) 0.0035(7) 0.0020(7) 0.0066(8) C6 0.0330(9) 0.0328(9) 0.0263(8) 0.0023(7) 0.0064(7) 0.0032(7) C7 0.0367(10) 0.0444(12) 0.0401(11) 0.0022(9) 0.0108(9) -0.0102(8) C8 0.0248(8) 0.0252(8) 0.0218(8) 0.0013(6) 0.0046(6) -0.0022(6) C9 0.0295(8) 0.0280(9) 0.0249(8) 0.0032(6) 0.0083(7) 0.0013(6) C10 0.0537(13) 0.0400(12) 0.0381(11) 0.0108(9) 0.0214(10) 0.0183(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 O C2 1.361(2) . ? O C7 1.434(2) . ? N C8 1.339(2) . ? N C9 1.344(2) 3_665 ? C1 C6 1.389(2) . ? C1 C2 1.405(2) . ? C1 C8 1.495(2) . ? C2 C3 1.397(2) . ? C3 C4 1.388(3) . ? C3 H3 0.973(19) . ? C4 C5 1.380(3) . ? C4 H4 0.99(2) . ? C5 C6 1.403(2) . ? C5 H5 0.97(2) . ? C6 H6 1.00(2) . ? C7 H71 1.06(2) . ? C7 H72 1.03(2) . ? C7 H73 0.96(2) . ? C8 C9 1.397(2) . ? C9 N 1.344(2) 3_665 ? C9 C10 1.500(2) . ? C10 H101 1.01(3) . ? C10 H102 0.93(4) . ? C10 H103 0.92(4) . ? 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 O C7 117.50(14) . . ? C8 N C9 118.09(13) . 3_665 ? C6 C1 C2 119.45(15) . . ? C6 C1 C8 120.43(15) . . ? C2 C1 C8 120.07(14) . . ? O C2 C3 124.68(15) . . ? O C2 C1 114.96(14) . . ? C3 C2 C1 120.36(16) . . ? C4 C3 C2 118.83(17) . . ? C4 C3 H3 121.5(11) . . ? C2 C3 H3 119.6(11) . . ? C5 C4 C3 121.88(16) . . ? C5 C4 H4 120.9(13) . . ? C3 C4 H4 117.2(13) . . ? C4 C5 C6 119.03(17) . . ? C4 C5 H5 120.8(12) . . ? C6 C5 H5 120.2(12) . . ? C1 C6 C5 120.43(17) . . ? C1 C6 H6 118.3(11) . . ? C5 C6 H6 121.2(11) . . ? O C7 H71 109.9(11) . . ? O C7 H72 106.3(12) . . ? H71 C7 H72 112.2(16) . . ? O C7 H73 111.0(12) . . ? H71 C7 H73 110.4(17) . . ? H72 C7 H73 107.1(17) . . ? N C8 C9 121.51(14) . . ? N C8 C1 116.61(13) . . ? C9 C8 C1 121.86(14) . . ? N C9 C8 120.40(15) 3_665 . ? N C9 C10 116.44(15) 3_665 . ? C8 C9 C10 123.14(15) . . ? C9 C10 H101 110.3(17) . . ? C9 C10 H102 110(2) . . ? H101 C10 H102 110(3) . . ? C9 C10 H103 113(2) . . ? H101 C10 H103 105(3) . . ? H102 C10 H103 108(3) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 C2 O C7 5.0(2) . . . . ? C2 C1 C8 N 73.20(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.260 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.048 #================================================END data_(3) _database_code_CSD 207425 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(2-methoxyphenyl)-3,6-dimethylpyrazinium bis(tetrafluoroborate) salt ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 N2 O2 2+,2(B F4 1-)' _chemical_formula_sum 'C20 H22 B2 F8 N2 O2' _chemical_formula_weight 496.02 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.863(1) _cell_length_b 8.088(1) _cell_length_c 10.548(2) _cell_angle_alpha 67.82(1) _cell_angle_beta 80.11(1) _cell_angle_gamma 80.11(1) _cell_volume 530.43(14) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 284 _cell_measurement_theta_min 10.26 _cell_measurement_theta_max 22.42 _exptl_crystal_description shapeless _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured ' _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 254 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (31.5 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 5636 _diffrn_reflns_av_R_equivalents 0.0774 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.56 _reflns_number_total 2440 _reflns_number_gt 1666 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. Pyrimidinium H atom - refall, methyl group C(7)H~3~ - rigid body, methyl group C(10)H~3~ - ideally disordered, other H atoms - riding. ; _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^)+(0.0215P)^2^+0.5098P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2440 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1068 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 0.3277(3) 0.7207(2) -0.34269(17) 0.0243(4) Uani 1 1 d . . . N N 0.3293(3) 0.5686(3) -0.04858(19) 0.0146(4) Uani 1 1 d . . . H1 H 0.210(5) 0.610(4) -0.075(3) 0.030(8) Uiso 1 1 d . . . C1 C 0.3793(3) 0.4141(3) -0.2126(2) 0.0190(5) Uani 1 1 d . . . C2 C 0.3129(3) 0.5501(3) -0.3306(2) 0.0208(5) Uani 1 1 d . . . C3 C 0.2415(4) 0.5023(4) -0.4271(3) 0.0264(6) Uani 1 1 d . . . H3 H 0.1990 0.5928 -0.5086 0.032 Uiso 1 1 d R . . C4 C 0.2341(4) 0.3245(4) -0.4037(3) 0.0287(6) Uani 1 1 d . . . H4 H 0.1842 0.2937 -0.4692 0.034 Uiso 1 1 d R . . C5 C 0.2979(4) 0.1880(4) -0.2855(3) 0.0271(6) Uani 1 1 d . . . H5 H 0.2909 0.0658 -0.2703 0.033 Uiso 1 1 d R . . C6 C 0.3717(3) 0.2343(3) -0.1910(2) 0.0192(5) Uani 1 1 d . . . H6 H 0.4172 0.1430 -0.1107 0.023 Uiso 1 1 d R . . C7 C 0.2706(4) 0.8621(4) -0.4674(3) 0.0279(6) Uani 1 1 d . . . H71 H 0.3506 0.8408 -0.5472 0.034(4) Uiso 1 1 d R . . H72 H 0.2932 0.9778 -0.4666 0.034(4) Uiso 1 1 d R . . H73 H 0.1296 0.8636 -0.4731 0.034(4) Uiso 1 1 d R . . C8 C 0.4501(3) 0.4610(3) -0.1065(2) 0.0157(5) Uani 1 1 d . . . C9 C 0.6346(3) 0.3895(3) -0.0558(2) 0.0160(5) Uani 1 1 d . . . C10 C 0.7934(4) 0.2759(4) -0.1111(3) 0.0269(6) Uani 1 1 d . . . H101 H 0.9226 0.2854 -0.0884 0.022(6) Uiso 0.50 1 d PR . . H102 H 0.7964 0.3172 -0.2115 0.022(6) Uiso 0.50 1 d PR . . H103 H 0.7658 0.1504 -0.0700 0.022(6) Uiso 0.50 1 d PR . . H104 H 0.7339 0.2166 -0.1582 0.022(6) Uiso 0.50 1 d PR . . H105 H 0.8601 0.1848 -0.0351 0.022(6) Uiso 0.50 1 d PR . . H106 H 0.8907 0.3516 -0.1766 0.022(6) Uiso 0.50 1 d PR . . B B -0.1675(4) 0.8125(4) -0.2030(3) 0.0167(6) Uani 1 1 d . . . F1 F -0.0522(2) 0.6798(2) -0.10197(15) 0.0298(4) Uani 1 1 d . . . F2 F -0.3562(2) 0.8424(2) -0.13787(15) 0.0282(4) Uani 1 1 d . . . F3 F -0.1772(2) 0.7460(2) -0.30319(16) 0.0354(4) Uani 1 1 d . . . F4 F -0.0762(2) 0.9671(2) -0.25579(16) 0.0308(4) Uani 1 1 d . . . 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 O 0.0310(10) 0.0206(9) 0.0201(9) -0.0050(7) -0.0102(7) 0.0017(8) N 0.0091(9) 0.0159(10) 0.0175(10) -0.0045(8) -0.0044(8) 0.0016(8) C1 0.0136(11) 0.0259(13) 0.0217(12) -0.0138(11) -0.0035(9) 0.0007(10) C2 0.0154(11) 0.0259(14) 0.0233(13) -0.0129(11) -0.0029(10) 0.0020(10) C3 0.0194(12) 0.0399(17) 0.0256(13) -0.0184(12) -0.0091(10) 0.0037(11) C4 0.0225(13) 0.0412(17) 0.0343(15) -0.0255(14) -0.0116(11) 0.0015(12) C5 0.0226(13) 0.0324(16) 0.0371(15) -0.0240(13) -0.0047(11) -0.0027(11) C6 0.0188(12) 0.0206(13) 0.0216(12) -0.0120(10) -0.0055(10) 0.0020(10) C7 0.0293(14) 0.0277(15) 0.0205(13) -0.0032(11) -0.0073(11) 0.0039(11) C8 0.0147(11) 0.0186(12) 0.0148(11) -0.0058(10) -0.0034(9) -0.0036(9) C9 0.0146(11) 0.0178(12) 0.0186(12) -0.0085(10) -0.0049(9) -0.0018(9) C10 0.0173(12) 0.0369(16) 0.0342(15) -0.0230(13) -0.0053(11) 0.0026(11) B 0.0146(12) 0.0178(14) 0.0155(13) -0.0020(11) -0.0044(10) -0.0029(10) F1 0.0156(7) 0.0341(9) 0.0287(8) 0.0022(7) -0.0089(6) 0.0007(6) F2 0.0169(7) 0.0303(9) 0.0286(8) -0.0040(7) -0.0010(6) 0.0031(6) F3 0.0381(9) 0.0432(10) 0.0347(9) -0.0227(8) -0.0091(7) -0.0048(8) F4 0.0296(8) 0.0242(9) 0.0371(9) -0.0080(7) -0.0001(7) -0.0096(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 O C2 1.357(3) . ? O C7 1.442(3) . ? N C9 1.339(3) 2_665 ? N C8 1.341(3) . ? C1 C6 1.394(3) . ? C1 C2 1.399(3) . ? C1 C8 1.484(3) . ? C2 C3 1.399(3) . ? C3 C4 1.373(4) . ? C4 C5 1.395(4) . ? C5 C6 1.383(3) . ? C8 C9 1.404(3) . ? C9 N 1.339(3) 2_665 ? C9 C10 1.488(3) . ? B F3 1.370(3) . ? B F4 1.375(3) . ? B F2 1.385(3) . ? B F1 1.431(3) . ? 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 O C7 116.65(19) . . ? C9 N C8 126.2(2) 2_665 . ? C6 C1 C2 120.3(2) . . ? C6 C1 C8 119.5(2) . . ? C2 C1 C8 120.1(2) . . ? O C2 C1 115.9(2) . . ? O C2 C3 125.2(2) . . ? C1 C2 C3 118.9(2) . . ? C4 C3 C2 119.9(2) . . ? C3 C4 C5 121.6(2) . . ? C6 C5 C4 118.7(3) . . ? C5 C6 C1 120.5(2) . . ? N C8 C9 117.1(2) . . ? N C8 C1 119.3(2) . . ? C9 C8 C1 123.5(2) . . ? N C9 C8 116.7(2) 2_665 . ? N C9 C10 118.0(2) 2_665 . ? C8 C9 C10 125.3(2) . . ? F3 B F4 111.5(2) . . ? F3 B F2 110.4(2) . . ? F4 B F2 110.7(2) . . ? F3 B F1 108.0(2) . . ? F4 B F1 108.28(19) . . ? F2 B F1 107.80(19) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O C2 C1 176.6(2) . . . . ? O C2 C1 C8 3.1(3) . . . . ? C2 C1 C8 N 56.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N H1 F1 0.88(3) 1.83(3) 2.701(2) 172(3) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.350 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.062 #===============================================END data_(6) _database_code_CSD 207426 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-bis(6-methoxypyridin-3-yl)-3,6-dimethylpyrazine ; _chemical_name_common ? _chemical_melting_point '179--181 C' _chemical_formula_moiety 'C18 H18 N4 O2' _chemical_formula_sum 'C18 H18 N4 O2' _chemical_formula_weight 322.36 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' _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 3.803(1) _cell_length_b 23.231(7) _cell_length_c 8.955(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.21(1) _cell_angle_gamma 90.00 _cell_volume 776.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 820 _cell_measurement_theta_min 10.22 _cell_measurement_theta_max 25.36 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 5 sets of \w scans; each set at different \f and/or 2\q angles and each scan (10 sec exposure) covering 0.3\% in \w. Crystal to detector distance 4.42 cm. ; _diffrn_ambient_temperature 120(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 'SMART 1K CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 8090 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1774 _reflns_number_gt 1498 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART version 5.060 (Bruker, 1999)' _computing_cell_refinement 'SMART version 5.060 (Bruker, 1999)' _computing_data_reduction 'SAINT version 6.02A (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL version 5.10 (Bruker, 1997)' _computing_publication_material 'SHELXTL version 5.10 (Bruker, 1997)' _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. ; _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^)+(0.0514P)^2^+0.2846P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1774 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1036 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O O 0.6551(3) 0.32047(4) 0.60532(10) 0.0253(3) Uani 1 1 d . . . N1 N 0.3100(3) 0.33105(5) 0.36403(12) 0.0201(3) Uani 1 1 d . . . N2 N 0.0281(3) 0.51412(5) 0.15183(12) 0.0169(3) Uani 1 1 d . . . C2 C 0.1959(4) 0.36660(6) 0.24463(14) 0.0191(3) Uani 1 1 d . . . H2 H 0.030(4) 0.3487(7) 0.1576(19) 0.026(4) Uiso 1 1 d . . . C3 C 0.2901(3) 0.42382(6) 0.23970(13) 0.0166(3) Uani 1 1 d . . . C4 C 0.5200(3) 0.44629(6) 0.36892(14) 0.0178(3) Uani 1 1 d . . . H4 H 0.592(4) 0.4862(7) 0.3677(17) 0.018(4) Uiso 1 1 d . . . C5 C 0.6406(4) 0.41127(6) 0.49194(15) 0.0197(3) Uani 1 1 d . . . H5 H 0.801(4) 0.4256(7) 0.5819(19) 0.027(4) Uiso 1 1 d . . . C6 C 0.5279(3) 0.35397(6) 0.48264(14) 0.0188(3) Uani 1 1 d . . . C7 C 0.5367(5) 0.26178(7) 0.5990(2) 0.0329(4) Uani 1 1 d . . . H71 H 0.611(5) 0.2407(8) 0.510(2) 0.043(5) Uiso 1 1 d . . . H72 H 0.660(5) 0.2457(8) 0.692(2) 0.038(5) Uiso 1 1 d . . . H73 H 0.277(6) 0.2610(8) 0.594(2) 0.049(6) Uiso 1 1 d . . . C8 C 0.1405(3) 0.46254(5) 0.11117(14) 0.0158(3) Uani 1 1 d . . . C9 C 0.1142(3) 0.44823(5) -0.04354(14) 0.0163(3) Uani 1 1 d . . . C10 C 0.2449(4) 0.39265(6) -0.09928(15) 0.0202(3) Uani 1 1 d . . . H11 H 0.342(5) 0.4002(7) -0.189(2) 0.033(4) Uiso 1 1 d . . . H12 H 0.433(4) 0.3745(7) -0.0231(18) 0.023(4) Uiso 1 1 d . . . H13 H 0.050(5) 0.3640(7) -0.1240(18) 0.028(4) Uiso 1 1 d . . . 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 O 0.0340(6) 0.0231(5) 0.0184(5) 0.0068(4) 0.0038(4) 0.0043(4) N1 0.0220(6) 0.0180(6) 0.0207(6) 0.0014(4) 0.0053(4) 0.0015(4) N2 0.0162(5) 0.0187(6) 0.0154(5) 0.0000(4) 0.0020(4) -0.0008(4) C2 0.0194(6) 0.0207(7) 0.0168(6) -0.0005(5) 0.0025(5) 0.0009(5) C3 0.0164(6) 0.0198(7) 0.0140(6) 0.0002(5) 0.0035(5) 0.0026(5) C4 0.0199(7) 0.0172(6) 0.0168(6) -0.0012(5) 0.0050(5) 0.0010(5) C5 0.0205(7) 0.0239(7) 0.0144(6) -0.0009(5) 0.0022(5) 0.0019(5) C6 0.0211(6) 0.0207(7) 0.0156(6) 0.0033(5) 0.0062(5) 0.0046(5) C7 0.0362(9) 0.0264(8) 0.0359(9) 0.0145(7) 0.0064(7) 0.0024(6) C8 0.0142(6) 0.0176(6) 0.0153(6) 0.0002(5) 0.0019(4) -0.0015(5) C9 0.0143(6) 0.0180(6) 0.0162(6) -0.0004(5) 0.0018(4) -0.0003(5) C10 0.0223(7) 0.0210(7) 0.0167(6) -0.0012(5) 0.0022(5) 0.0036(5) _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 O C6 1.3565(15) . ? O C7 1.4335(19) . ? N1 C6 1.3252(17) . ? N1 C2 1.3539(17) . ? N2 C9 1.3394(16) 3_565 ? N2 C8 1.3460(17) . ? C10 C9 1.5032(18) . ? C5 C6 1.396(2) . ? C5 C4 1.3746(18) . ? C4 C3 1.4080(17) . ? C2 C3 1.3796(19) . ? C3 C8 1.4844(17) . ? C8 C9 1.4092(18) . ? C9 N2 1.3394(16) 3_565 ? 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 C6 O C7 116.99(11) . . ? C2 N1 C6 116.26(12) . . ? C9 N2 C8 119.36(11) 3_565 . ? N1 C6 O 119.18(12) . . ? N1 C6 C5 124.60(12) . . ? O C6 C5 116.22(12) . . ? C4 C5 C6 117.77(12) . . ? C3 C4 C5 119.76(12) . . ? C2 C3 C4 117.04(11) . . ? C2 C3 C8 123.09(11) . . ? C4 C3 C8 119.72(12) . . ? N1 C2 C3 124.58(12) . . ? N2 C8 C9 120.69(11) . . ? N2 C8 C3 115.07(11) . . ? C9 C8 C3 124.24(12) . . ? N2 C9 C8 119.95(12) 3_565 . ? N2 C9 C10 115.69(11) 3_565 . ? C8 C9 C10 124.35(11) . . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C6 O C7 -1.21(18) . . . . ? N2 C8 C3 C4 -42.14(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.044 #=============================================END