Supplementary Material (ESI) for CrystEngComm This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Neil Champness' 'Alexander J. Blake' 'Neil S. Oxtoby' 'Claire Wilson' _publ_contact_author_name 'Dr Neil Champness' _publ_contact_author_address ; School of Chemistry University of Nottingham University Park Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email NEIL.CHAMPNESS@NOTTINGHAM.AC.UK _publ_requested_journal 'CrystEngComm' _publ_section_title ; The Role of 1,2,4,5-Tetrazine Rings in p-p Stacking Interactions ; data_PYPMON _database_code_CSD 204848 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,6-Di-pyridin-3-yl-1,2,4,5-tetrazine ; _chemical_name_common 3,3'-DPTZ _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 N6' _chemical_formula_sum 'C12 H8 N6' _chemical_formula_weight 236.24 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 P21/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 5.0842(8) _cell_length_b 5.4202(9) _cell_length_c 18.831(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.126(4) _cell_angle_gamma 90.00 _cell_volume 517.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 577 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 26.50 _exptl_crystal_description plate _exptl_crystal_colour pink _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.101 _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 150(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 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2326 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_av_sigmaI/netI 0.050 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.80 _reflns_number_total 1228 _reflns_number_gt 664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 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. 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^)+(0.0498P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1123 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_restrained_S_all 0.878 _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 N1 N 0.6793(3) 0.5406(3) 0.20431(7) 0.0284(4) Uani 1 1 d . . . C2 C 0.4762(3) 0.5706(3) 0.15620(8) 0.0247(4) Uani 1 1 d . . . H2A H 0.3675 0.7117 0.1604 0.030 Uiso 1 1 calc R . . C3 C 0.4130(3) 0.4072(3) 0.09993(8) 0.0209(4) Uani 1 1 d . . . C4 C 0.5709(3) 0.1970(3) 0.09564(9) 0.0253(4) Uani 1 1 d . . . H4A H 0.5331 0.0783 0.0592 0.030 Uiso 1 1 calc R . . C5 C 0.7814(3) 0.1641(3) 0.14479(9) 0.0269(4) Uani 1 1 d . . . H5A H 0.8924 0.0237 0.1425 0.032 Uiso 1 1 calc R . . C6 C 0.8287(3) 0.3393(3) 0.19755(9) 0.0272(4) Uani 1 1 d . . . H6A H 0.9756 0.3156 0.2310 0.033 Uiso 1 1 calc R . . C7 C 0.1929(3) 0.4572(3) 0.04700(8) 0.0209(4) Uani 1 1 d . . . N8 N 0.0482(3) 0.6625(2) 0.05473(7) 0.0245(4) Uani 1 1 d . . . N9 N -0.1499(3) 0.7062(2) 0.00682(7) 0.0255(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 N1 0.0263(9) 0.0291(8) 0.0292(8) -0.0031(7) -0.0031(7) 0.0016(7) C2 0.0231(10) 0.0239(9) 0.0269(9) -0.0004(7) 0.0009(8) 0.0015(7) C3 0.0206(9) 0.0213(8) 0.0211(9) 0.0021(7) 0.0029(8) -0.0029(7) C4 0.0290(11) 0.0215(9) 0.0251(9) -0.0028(7) 0.0002(8) 0.0004(7) C5 0.0278(11) 0.0229(9) 0.0301(10) 0.0016(8) 0.0021(9) 0.0036(8) C6 0.0240(11) 0.0305(10) 0.0265(10) 0.0040(8) -0.0018(8) 0.0010(8) C7 0.0212(10) 0.0211(8) 0.0208(9) 0.0009(7) 0.0045(8) -0.0009(7) N8 0.0241(8) 0.0240(7) 0.0246(8) -0.0017(6) -0.0027(7) 0.0033(6) N9 0.0270(9) 0.0256(8) 0.0233(8) -0.0026(6) -0.0017(7) 0.0023(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 C2 1.334(2) . ? N1 C6 1.341(2) . ? C2 C3 1.400(2) . ? C3 C4 1.400(2) . ? C3 C7 1.469(2) . ? C4 C5 1.375(2) . ? C5 C6 1.383(2) . ? C7 N8 1.348(2) . ? C7 N9 1.3518(19) 3_565 ? N8 N9 1.3244(18) . ? N9 C7 1.3518(19) 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 C2 N1 C6 116.80(15) . . ? N1 C2 C3 124.13(16) . . ? C4 C3 C2 117.22(16) . . ? C4 C3 C7 121.53(15) . . ? C2 C3 C7 121.25(15) . . ? C5 C4 C3 119.23(16) . . ? C4 C5 C6 118.77(16) . . ? N1 C6 C5 123.83(16) . . ? N8 C7 N9 124.17(15) . 3_565 ? N8 C7 C3 118.31(15) . . ? N9 C7 C3 117.52(14) 3_565 . ? N9 N8 C7 117.95(13) . . ? N8 N9 C7 117.88(13) . 3_565 ? _diffrn_measured_fraction_theta_max 0.841 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.172 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.044 #===END data_DPTZNT _database_code_CSD 204849 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,6-Di-4-pyridyl-1,2,4,5-tetrazine ; _chemical_name_common 3,6-Di-4-pyridyl-1,2,4,5-tetrazine _chemical_formula_moiety 'C12 H8 N6' _chemical_formula_sum 'C12 H8 N6' _chemical_formula_weight 236.24 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 5.0029(9) _cell_length_b 5.4035(10) _cell_length_c 18.788(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.776(4) _cell_angle_gamma 90.00 _cell_volume 507.30(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1173 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 28.15 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour pink _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.103 _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 150(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 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2799 _diffrn_reflns_av_R_equivalents 0.041 _diffrn_reflns_av_sigmaI/netI 0.024 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 28.57 _reflns_number_total 1273 _reflns_number_gt 888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 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. 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^)+(0.0845P)^2^+0.0399P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary 'direct methods' _atom_sites_solution_secondary 'difference Fourier synthesis' _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1155 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _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 N1 N 0.8358(2) 0.3580(2) 0.20244(7) 0.0237(3) Uani 1 1 d . . . C2 C 0.6745(3) 0.5552(3) 0.20419(8) 0.0229(4) Uani 1 1 d . . . H2A H 0.7099 0.6756 0.2403 0.027 Uiso 1 1 calc R . . C3 C 0.4587(3) 0.5940(3) 0.15635(7) 0.0200(3) Uani 1 1 d . . . H3A H 0.3469 0.7348 0.1606 0.024 Uiso 1 1 calc R . . C4 C 0.4090(3) 0.4227(2) 0.10200(7) 0.0177(3) Uani 1 1 d . . . C5 C 0.5739(3) 0.2155(3) 0.09958(8) 0.0212(3) Uani 1 1 d . . . H5A H 0.5450 0.0934 0.0637 0.025 Uiso 1 1 calc R . . C6 C 0.7818(3) 0.1916(3) 0.15091(8) 0.0236(4) Uani 1 1 d . . . H6A H 0.8921 0.0488 0.1494 0.028 Uiso 1 1 calc R . . C7 C 0.1888(3) 0.4637(2) 0.04756(7) 0.0175(3) Uani 1 1 d . . . N8 N 0.1538(2) 0.2929(2) -0.00421(6) 0.0209(3) Uani 1 1 d . . . N9 N 0.0414(2) 0.6699(2) 0.05297(6) 0.0207(3) 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 N1 0.0197(6) 0.0265(7) 0.0245(7) 0.0039(5) -0.0030(5) -0.0017(5) C2 0.0236(7) 0.0246(7) 0.0201(7) -0.0009(5) -0.0019(6) -0.0038(6) C3 0.0194(7) 0.0205(7) 0.0199(7) 0.0005(5) -0.0001(6) 0.0005(6) C4 0.0164(7) 0.0208(7) 0.0160(6) 0.0024(5) 0.0012(5) -0.0024(5) C5 0.0221(7) 0.0209(7) 0.0205(7) -0.0004(5) -0.0004(6) -0.0004(6) C6 0.0209(7) 0.0226(7) 0.0272(8) 0.0024(6) 0.0008(6) 0.0026(6) C7 0.0171(7) 0.0195(7) 0.0160(7) 0.0012(5) 0.0020(5) -0.0016(5) N8 0.0213(6) 0.0225(6) 0.0187(6) -0.0014(5) -0.0027(5) 0.0011(5) N9 0.0218(6) 0.0222(6) 0.0179(6) -0.0014(4) -0.0023(5) 0.0020(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 N1 C2 1.3378(19) . y N1 C6 1.3393(19) . y C2 C3 1.3869(19) . y C3 C4 1.3914(19) . y C4 C5 1.393(2) . y C4 C7 1.4829(18) . y C5 C6 1.390(2) . y C7 N9 1.3430(18) . y C7 N8 1.3461(18) . y N8 N9 1.3216(16) 3_565 y N9 N8 1.3216(16) 3_565 y 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 116.84(12) . . y N1 C2 C3 123.78(13) . . y C2 C3 C4 118.76(13) . . y C3 C4 C5 118.25(13) . . y C3 C4 C7 120.50(12) . . y C5 C4 C7 121.24(13) . . y C6 C5 C4 118.47(13) . . y N1 C6 C5 123.87(13) . . y N9 C7 N8 124.80(13) . . y N9 C7 C4 117.63(12) . . y N8 C7 C4 117.56(12) . . y N9 N8 C7 117.55(12) 3_565 . y N8 N9 C7 117.64(12) 3_565 . y _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.44 _refine_diff_density_min -0.19 _refine_diff_density_rms 0.06 #===END data_PZTZPZ _database_code_CSD 204850 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '3,6-Di-2-pyrazyl-1,2,4,5-tetrazine' ; _chemical_name_common Di-pyrazyl-tetrazine _chemical_formula_moiety 'C10 H6 N8' _chemical_formula_sum 'C10 H6 N8' _chemical_formula_weight 238.23 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 12.968(2) _cell_length_b 5.596(1) _cell_length_c 6.813(1) _cell_angle_alpha 90.00 _cell_angle_beta 92.099(3) _cell_angle_gamma 90.00 _cell_volume 494.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1848 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 28.3 _exptl_crystal_description tablet _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.112 _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 150(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 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 2859 _diffrn_reflns_av_R_equivalents 0.023 _diffrn_reflns_av_sigmaI/netI 0.012 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 28.62 _reflns_number_total 1259 _reflns_number_gt 1039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97; PLATON (Spek, 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. 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^)+(0.058P)^2^+0.147P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'differenc Fourier' _atom_sites_solution_hydrogens 'geomometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.021(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1141 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _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 C1 C 0.89952(8) -0.0166(2) 0.76328(16) 0.0231(3) Uani 1 1 d . . . H1A H 0.9699 -0.0265 0.8066 0.028 Uiso 1 1 calc R . . N2 N 0.86339(7) 0.19035(17) 0.68924(15) 0.0236(3) Uani 1 1 d . . . C3 C 0.76403(8) 0.1915(2) 0.62949(16) 0.0206(3) Uani 1 1 d . . . H3A H 0.7347 0.3347 0.5776 0.025 Uiso 1 1 calc R . . C4 C 0.70206(7) -0.01206(18) 0.64120(15) 0.0176(3) Uani 1 1 d . . . N5 N 0.73799(7) -0.21760(17) 0.71757(14) 0.0204(2) Uani 1 1 d . . . C6 C 0.83731(8) -0.2166(2) 0.77848(16) 0.0222(3) Uani 1 1 d . . . H6A H 0.8662 -0.3582 0.8342 0.027 Uiso 1 1 calc R . . C7 C 0.59321(7) -0.00737(18) 0.56650(14) 0.0172(3) Uani 1 1 d . . . N8 N 0.56765(7) 0.16762(17) 0.43895(13) 0.0203(2) Uani 1 1 d . . . N9 N 0.47104(7) 0.17602(17) 0.36931(14) 0.0205(2) 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 C1 0.0163(5) 0.0284(6) 0.0247(5) -0.0010(4) -0.0006(4) 0.0009(4) N2 0.0188(5) 0.0239(5) 0.0281(5) -0.0003(4) -0.0005(4) -0.0028(3) C3 0.0192(5) 0.0191(5) 0.0236(5) 0.0000(4) 0.0003(4) -0.0005(4) C4 0.0165(5) 0.0191(5) 0.0172(5) -0.0016(4) 0.0024(4) 0.0008(4) N5 0.0185(5) 0.0202(5) 0.0227(5) 0.0012(4) 0.0017(3) 0.0006(3) C6 0.0201(5) 0.0236(6) 0.0229(5) 0.0020(4) 0.0007(4) 0.0038(4) C7 0.0166(5) 0.0168(5) 0.0183(5) -0.0021(4) 0.0024(4) -0.0003(4) N8 0.0165(4) 0.0207(5) 0.0237(5) 0.0029(4) 0.0005(3) -0.0010(3) N9 0.0166(4) 0.0208(5) 0.0242(5) 0.0025(4) 0.0002(3) -0.0013(3) _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 C1 N2 1.3411(15) . ? C1 C6 1.3855(16) . ? N2 C3 1.3371(13) . ? C3 C4 1.3978(14) . ? C4 N5 1.3391(14) . ? C4 C7 1.4831(13) . ? N5 C6 1.3387(13) . ? C7 N8 1.3427(14) . ? C7 N9 1.3427(14) 3_656 ? N8 N9 1.3242(12) . ? N9 C7 1.3427(14) 3_656 ? 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 N2 C1 C6 121.96(9) . . ? C3 N2 C1 115.98(9) . . ? N2 C3 C4 121.90(10) . . ? N5 C4 C3 121.97(9) . . ? N5 C4 C7 117.50(9) . . ? C3 C4 C7 120.53(9) . . ? C6 N5 C4 115.72(9) . . ? N5 C6 C1 122.44(10) . . ? N8 C7 N9 125.60(9) . 3_656 ? N8 C7 C4 116.37(9) . . ? N9 C7 C4 118.03(9) 3_656 . ? N9 N8 C7 117.75(9) . . ? N8 N9 C7 116.65(9) . 3_656 ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.33 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04 #===END