Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_cs6m _database_code_CSD 168478 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Constable, E.' 'Housecroft, C. E.' 'Kariuki, Benson M.' 'Kelly, Natalie' 'Smith, Christopher B.' _publ_contact_author_name 'Prof E Constable' _publ_contact_author_address ; School of Chemistry University of Birmingham Edgbaston Birmingham B15 2TT UK ; _publ_contact_author_email 'E.C.CONSTABLE@BHAM.AC.UK' _publ_section_title ; A Polymeric sodium complex of 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H28 B N6 Na' _chemical_formula_weight 578.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Na' 'Na' 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.2064(4) _cell_length_b 12.4777(3) _cell_length_c 15.3058(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.5290(10) _cell_angle_gamma 90.00 _cell_volume 2965.27(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.738 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.7769 _exptl_absorpt_correction_T_max 0.9298 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD Diffractometer' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5413 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.55 _diffrn_reflns_theta_max 70.47 _reflns_number_total 2639 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0818P)^2^+0.6302P] 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 2639 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1432 _refine_ls_wR_factor_gt 0.1351 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 Na1 Na 0.5000 0.52984(7) 0.2500 0.0442(3) Uani 1 2 d S . . B1 B 0.5000 0.18528(18) 0.2500 0.0308(5) Uani 1 2 d S . . N1 N 0.55651(9) 0.43884(10) 0.07339(9) 0.0397(3) Uani 1 1 d . . . N2 N 0.51702(9) 0.51927(10) 0.09391(9) 0.0386(3) Uani 1 1 d . . . N3 N 0.42306(10) 0.67176(11) 0.13230(10) 0.0465(4) Uani 1 1 d . . . C1 C 0.46150(10) 0.57837(12) 0.01978(11) 0.0359(4) Uani 1 1 d . . . C2 C 0.41850(10) 0.66989(12) 0.04232(11) 0.0379(4) Uani 1 1 d . . . C3 C 0.37857(12) 0.74922(14) -0.02521(13) 0.0477(4) Uani 1 1 d . . . H3 H 0.3761 0.7453 -0.0870 0.057 Uiso 1 1 calc R . . C4 C 0.34236(14) 0.83464(14) 0.00156(15) 0.0571(5) Uani 1 1 d . . . H4 H 0.3155 0.8897 -0.0420 0.068 Uiso 1 1 calc R . . C5 C 0.34633(14) 0.83747(15) 0.09269(16) 0.0569(5) Uani 1 1 d . . . H5 H 0.3221 0.8940 0.1119 0.068 Uiso 1 1 calc R . . C6 C 0.38694(14) 0.75480(15) 0.15532(14) 0.0551(5) Uani 1 1 d . . . H6 H 0.3893 0.7571 0.2171 0.066 Uiso 1 1 calc R . . C7 C 0.43708(9) 0.26237(11) 0.16041(10) 0.0308(3) Uani 1 1 d . . . C8 C 0.41932(10) 0.24826(13) 0.06343(11) 0.0392(4) Uani 1 1 d . . . H8 H 0.4472 0.1932 0.0472 0.047 Uiso 1 1 calc R . . C9 C 0.36183(12) 0.31262(15) -0.01049(12) 0.0487(4) Uani 1 1 d . . . H9 H 0.3514 0.2993 -0.0744 0.058 Uiso 1 1 calc R . . C10 C 0.32025(12) 0.39615(14) 0.01096(13) 0.0506(5) Uani 1 1 d . . . H10 H 0.2824 0.4401 -0.0379 0.061 Uiso 1 1 calc R . . C11 C 0.33578(11) 0.41327(13) 0.10621(13) 0.0442(4) Uani 1 1 d . . . H11 H 0.3080 0.4690 0.1217 0.053 Uiso 1 1 calc R . . C12 C 0.39261(11) 0.34776(12) 0.17888(11) 0.0370(4) Uani 1 1 d . . . H12 H 0.4018 0.3607 0.2424 0.044 Uiso 1 1 calc R . . C13 C 0.56068(9) 0.10515(11) 0.21960(10) 0.0321(3) Uani 1 1 d . . . C14 C 0.52281(12) 0.02039(13) 0.15491(12) 0.0440(4) Uani 1 1 d . . . H14 H 0.4631 0.0150 0.1254 0.053 Uiso 1 1 calc R . . C15 C 0.57050(14) -0.05562(14) 0.13305(14) 0.0524(5) Uani 1 1 d . . . H15 H 0.5425 -0.1106 0.0899 0.063 Uiso 1 1 calc R . . C16 C 0.65907(14) -0.05019(15) 0.17490(15) 0.0548(5) Uani 1 1 d . . . H16 H 0.6913 -0.1017 0.1611 0.066 Uiso 1 1 calc R . . C17 C 0.69919(12) 0.03278(14) 0.23758(14) 0.0511(5) Uani 1 1 d . . . H17 H 0.7589 0.0381 0.2657 0.061 Uiso 1 1 calc R . . C18 C 0.65039(10) 0.10897(13) 0.25897(11) 0.0397(4) Uani 1 1 d . . . H18 H 0.6789 0.1645 0.3012 0.048 Uiso 1 1 calc 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 Na1 0.0647(6) 0.0422(5) 0.0328(5) 0.000 0.0279(4) 0.000 B1 0.0318(11) 0.0329(11) 0.0301(11) 0.000 0.0157(9) 0.000 N1 0.0481(8) 0.0429(7) 0.0323(7) 0.0027(5) 0.0213(6) 0.0026(6) N2 0.0477(8) 0.0409(7) 0.0323(7) 0.0018(5) 0.0220(6) 0.0014(6) N3 0.0654(10) 0.0410(8) 0.0400(8) -0.0033(5) 0.0292(7) 0.0025(7) C1 0.0443(9) 0.0359(8) 0.0333(8) 0.0013(6) 0.0221(7) -0.0041(7) C2 0.0424(9) 0.0365(8) 0.0385(8) -0.0016(6) 0.0210(7) -0.0048(7) C3 0.0513(10) 0.0486(10) 0.0466(9) 0.0081(7) 0.0245(8) 0.0044(8) C4 0.0568(12) 0.0449(10) 0.0695(13) 0.0110(8) 0.0272(10) 0.0086(9) C5 0.0606(12) 0.0420(10) 0.0743(13) -0.0076(8) 0.0349(10) 0.0033(9) C6 0.0734(13) 0.0489(10) 0.0523(10) -0.0088(8) 0.0358(10) 0.0045(9) C7 0.0307(7) 0.0325(7) 0.0324(7) -0.0008(5) 0.0165(6) -0.0051(6) C8 0.0422(9) 0.0417(8) 0.0365(8) -0.0005(6) 0.0196(7) -0.0002(7) C9 0.0537(10) 0.0572(10) 0.0298(8) 0.0018(7) 0.0128(7) -0.0030(8) C10 0.0425(9) 0.0512(10) 0.0482(10) 0.0132(7) 0.0100(8) 0.0034(8) C11 0.0382(9) 0.0404(9) 0.0559(10) 0.0053(7) 0.0220(8) 0.0046(7) C12 0.0420(9) 0.0363(8) 0.0379(8) 0.0002(6) 0.0221(7) 0.0001(7) C13 0.0364(8) 0.0331(7) 0.0307(7) 0.0022(5) 0.0181(6) 0.0009(6) C14 0.0449(10) 0.0424(9) 0.0503(10) -0.0092(7) 0.0259(8) -0.0056(7) C15 0.0692(13) 0.0430(9) 0.0603(11) -0.0152(8) 0.0422(10) -0.0075(9) C16 0.0687(13) 0.0459(10) 0.0719(12) -0.0023(8) 0.0511(11) 0.0087(9) C17 0.0436(10) 0.0576(11) 0.0608(11) 0.0018(8) 0.0309(9) 0.0086(8) C18 0.0381(9) 0.0423(9) 0.0404(8) -0.0035(6) 0.0186(7) 0.0007(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 Na1 N3 2.4654(15) 2_655 ? Na1 N3 2.4654(15) . ? Na1 N2 2.5327(12) 2_655 ? Na1 N2 2.5327(12) . ? Na1 C12 2.8333(17) . ? Na1 C12 2.8333(17) 2_655 ? Na1 C11 3.0957(18) . ? Na1 C11 3.0957(18) 2_655 ? B1 C7 1.6427(19) 2_655 ? B1 C7 1.6427(19) . ? B1 C13 1.6507(19) 2_655 ? B1 C13 1.6507(19) . ? N1 N2 1.3233(18) . ? N1 C1 1.3398(19) 5_665 ? N2 C1 1.345(2) . ? N3 C6 1.331(2) . ? N3 C2 1.3454(19) . ? C1 N1 1.3398(19) 5_665 ? C1 C2 1.480(2) . ? C2 C3 1.381(2) . ? C3 C4 1.383(3) . ? C4 C5 1.367(3) . ? C5 C6 1.376(3) . ? C7 C8 1.392(2) . ? C7 C12 1.410(2) . ? C8 C9 1.392(2) . ? C9 C10 1.381(3) . ? C10 C11 1.381(3) . ? C11 C12 1.387(2) . ? C13 C18 1.395(2) . ? C13 C14 1.403(2) . ? C14 C15 1.386(2) . ? C15 C16 1.377(3) . ? C16 C17 1.378(3) . ? C17 C18 1.398(2) . ? 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 N3 Na1 N3 88.18(7) 2_655 . ? N3 Na1 N2 65.93(4) 2_655 2_655 ? N3 Na1 N2 118.87(5) . 2_655 ? N3 Na1 N2 118.87(5) 2_655 . ? N3 Na1 N2 65.93(4) . . ? N2 Na1 N2 174.03(7) 2_655 . ? N3 Na1 C12 155.87(4) 2_655 . ? N3 Na1 C12 103.85(5) . . ? N2 Na1 C12 89.96(5) 2_655 . ? N2 Na1 C12 85.25(5) . . ? N3 Na1 C12 103.85(5) 2_655 2_655 ? N3 Na1 C12 155.87(4) . 2_655 ? N2 Na1 C12 85.25(5) 2_655 2_655 ? N2 Na1 C12 89.96(5) . 2_655 ? C12 Na1 C12 73.38(7) . 2_655 ? N3 Na1 C11 153.53(5) 2_655 . ? N3 Na1 C11 77.28(5) . . ? N2 Na1 C11 101.83(5) 2_655 . ? N2 Na1 C11 75.29(5) . . ? C12 Na1 C11 26.59(4) . . ? C12 Na1 C11 98.09(5) 2_655 . ? N3 Na1 C11 77.28(5) 2_655 2_655 ? N3 Na1 C11 153.53(5) . 2_655 ? N2 Na1 C11 75.29(5) 2_655 2_655 ? N2 Na1 C11 101.83(5) . 2_655 ? C12 Na1 C11 98.09(5) . 2_655 ? C12 Na1 C11 26.59(4) 2_655 2_655 ? C11 Na1 C11 123.95(7) . 2_655 ? C7 B1 C7 108.31(16) 2_655 . ? C7 B1 C13 112.88(7) 2_655 2_655 ? C7 B1 C13 108.70(7) . 2_655 ? C7 B1 C13 108.70(7) 2_655 . ? C7 B1 C13 112.88(7) . . ? C13 B1 C13 105.44(15) 2_655 . ? N2 N1 C1 117.85(13) . 5_665 ? N1 N2 C1 117.79(12) . . ? N1 N2 Na1 122.90(9) . . ? C1 N2 Na1 115.99(10) . . ? C6 N3 C2 117.15(15) . . ? C6 N3 Na1 122.04(11) . . ? C2 N3 Na1 120.77(10) . . ? N1 C1 N2 124.36(14) 5_665 . ? N1 C1 C2 117.53(14) 5_665 . ? N2 C1 C2 118.10(13) . . ? N3 C2 C3 122.98(15) . . ? N3 C2 C1 115.94(14) . . ? C3 C2 C1 121.05(14) . . ? C2 C3 C4 118.22(16) . . ? C5 C4 C3 119.43(17) . . ? C4 C5 C6 118.58(17) . . ? N3 C6 C5 123.63(16) . . ? C8 C7 C12 114.89(13) . . ? C8 C7 B1 125.38(12) . . ? C12 C7 B1 119.65(11) . . ? C7 C8 C9 123.10(15) . . ? C10 C9 C8 120.09(15) . . ? C11 C10 C9 118.90(15) . . ? C10 C11 C12 120.28(15) . . ? C10 C11 Na1 121.69(12) . . ? C12 C11 Na1 66.10(9) . . ? C11 C12 C7 122.73(14) . . ? C11 C12 Na1 87.32(10) . . ? C7 C12 Na1 111.26(10) . . ? C18 C13 C14 114.93(13) . . ? C18 C13 B1 125.03(12) . . ? C14 C13 B1 119.86(13) . . ? C15 C14 C13 122.90(16) . . ? C16 C15 C14 120.37(16) . . ? C15 C16 C17 118.88(16) . . ? C16 C17 C18 120.20(17) . . ? C13 C18 C17 122.70(15) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 70.47 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.206 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.049