# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Doris Kunz' _publ_contact_author_address ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54- 8400' _publ_contact_author_fax '049 6221 54- 4205' _publ_contact_author_email doris.kunz@urz.uni-heidelberg.de _publ_requested_coeditor_name ? #=============================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; First X-ray Crystal Structures of 10\p- and 14\p-electron Pyrido-annelated N- heterocyclic Carbenes ; loop_ _publ_author_name _publ_author_address M.Nonnenmacher ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; D.Kunz ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; F.Rominger ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; T.Oeser ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; data_mn14 _database_code_depnum_ccdc_archive 'CCDC 292418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 1' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 N2' _chemical_formula_weight 280.40 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 12.052(7) _cell_length_b 11.180(6) _cell_length_c 11.965(7) _cell_angle_alpha 90.0 _cell_angle_beta 97.78(1) _cell_angle_gamma 90.0 _cell_volume 1597.2(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1980 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.25 _exptl_crystal_description irregular _exptl_crystal_colour yellow-orange _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9973 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7473 _diffrn_reflns_av_R_equivalents 0.0796 _diffrn_reflns_av_sigmaI/netI 0.0654 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 20.87 _reflns_number_total 1681 _reflns_number_gt 1227 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0487P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1681 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0530 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 N5 N 0.7654(2) 0.2231(2) 0.8760(2) 0.0173(7) Uani 1 1 d . . . N7 N 0.6156(2) 0.1305(2) 0.8225(2) 0.0193(7) Uani 1 1 d . . . C1 C 0.7910(2) 0.3570(3) 0.7206(2) 0.0162(8) Uani 1 1 d . . . H1 H 0.7644 0.3889 0.6484 0.019 Uiso 1 1 calc R . . C2 C 0.8898(2) 0.3967(2) 0.7762(2) 0.0149(8) Uani 1 1 d . . . C3 C 0.9241(3) 0.3483(3) 0.8866(2) 0.0176(8) Uani 1 1 d . . . H3 H 0.9921 0.3759 0.9280 0.021 Uiso 1 1 calc R . . C4 C 0.8643(3) 0.2656(3) 0.9338(3) 0.0201(8) Uani 1 1 d . . . H4 H 0.8902 0.2363 1.0072 0.024 Uiso 1 1 calc R . . C6 C 0.6979(3) 0.1366(3) 0.9139(3) 0.0236(8) Uani 1 1 d . . . C8 C 0.5230(3) 0.0558(3) 0.8124(3) 0.0242(9) Uani 1 1 d . . . H8 H 0.5151 -0.0010 0.8698 0.029 Uiso 1 1 calc R . . C9 C 0.4449(3) 0.0633(3) 0.7224(3) 0.0247(9) Uani 1 1 d . . . H9 H 0.3816 0.0120 0.7183 0.030 Uiso 1 1 calc R . . C10 C 0.4521(2) 0.1458(3) 0.6309(2) 0.0189(8) Uani 1 1 d . . . C11 C 0.5453(3) 0.2162(3) 0.6390(3) 0.0195(8) Uani 1 1 d . . . H11 H 0.5542 0.2704 0.5797 0.023 Uiso 1 1 calc R . . C11B C 0.7271(2) 0.2695(3) 0.7679(2) 0.0143(8) Uani 1 1 d . . . C11A C 0.6287(2) 0.2101(3) 0.7335(2) 0.0148(8) Uani 1 1 d . . . C12 C 0.9661(2) 0.4855(3) 0.7265(2) 0.0167(8) Uani 1 1 d . . . C13 C 0.9046(3) 0.5496(3) 0.6243(3) 0.0263(9) Uani 1 1 d . . . H13A H 0.8778 0.4907 0.5661 0.040 Uiso 1 1 calc R . . H13B H 0.9556 0.6057 0.5943 0.040 Uiso 1 1 calc R . . H13C H 0.8407 0.5935 0.6465 0.040 Uiso 1 1 calc R . . C14 C 1.0669(3) 0.4174(3) 0.6919(3) 0.0243(9) Uani 1 1 d . . . H14A H 1.0410 0.3614 0.6309 0.036 Uiso 1 1 calc R . . H14B H 1.1044 0.3730 0.7569 0.036 Uiso 1 1 calc R . . H14C H 1.1196 0.4744 0.6658 0.036 Uiso 1 1 calc R . . C15 C 1.0111(3) 0.5803(3) 0.8132(2) 0.0235(8) Uani 1 1 d . . . H15A H 1.0541 0.6400 0.7772 0.035 Uiso 1 1 calc R . . H15B H 1.0597 0.5420 0.8754 0.035 Uiso 1 1 calc R . . H15C H 0.9483 0.6194 0.8427 0.035 Uiso 1 1 calc R . . C16 C 0.3561(3) 0.1540(3) 0.5350(3) 0.0230(8) Uani 1 1 d . . . C17 C 0.2587(3) 0.2168(3) 0.5793(3) 0.0391(10) Uani 1 1 d . . . H17A H 0.2397 0.1741 0.6457 0.059 Uiso 1 1 calc R . . H17B H 0.1936 0.2174 0.5205 0.059 Uiso 1 1 calc R . . H17C H 0.2801 0.2992 0.6002 0.059 Uiso 1 1 calc R . . C18 C 0.3188(3) 0.0287(3) 0.4934(3) 0.0397(10) Uani 1 1 d . . . H18A H 0.3831 -0.0148 0.4714 0.060 Uiso 1 1 calc R . . H18B H 0.2604 0.0356 0.4283 0.060 Uiso 1 1 calc R . . H18C H 0.2892 -0.0147 0.5541 0.060 Uiso 1 1 calc R . . C19 C 0.3873(3) 0.2255(3) 0.4358(3) 0.0403(10) Uani 1 1 d . . . H19A H 0.4055 0.3078 0.4599 0.060 Uiso 1 1 calc R . . H19B H 0.3240 0.2260 0.3750 0.060 Uiso 1 1 calc R . . H19C H 0.4524 0.1887 0.4086 0.060 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 N5 0.0198(17) 0.0114(15) 0.0201(17) 0.0025(13) 0.0007(14) 0.0000(14) N7 0.0204(17) 0.0125(16) 0.0247(17) 0.0004(13) 0.0024(14) -0.0006(14) C1 0.0208(19) 0.0088(17) 0.0183(19) 0.0005(15) -0.0004(16) 0.0039(17) C2 0.018(2) 0.0063(17) 0.020(2) -0.0032(14) 0.0032(16) 0.0030(15) C3 0.0161(18) 0.0148(18) 0.020(2) -0.0050(16) -0.0031(16) 0.0005(17) C4 0.019(2) 0.017(2) 0.0218(19) 0.0009(16) -0.0045(17) 0.0039(17) C6 0.026(2) 0.015(2) 0.029(2) -0.0021(16) -0.0002(18) 0.0004(18) C8 0.027(2) 0.016(2) 0.029(2) 0.0003(16) 0.0018(18) -0.0048(18) C9 0.025(2) 0.018(2) 0.033(2) -0.0031(17) 0.0070(19) -0.0069(16) C10 0.018(2) 0.0137(18) 0.026(2) -0.0044(16) 0.0055(16) 0.0004(17) C11 0.024(2) 0.0129(19) 0.021(2) 0.0021(15) 0.0033(17) 0.0024(18) C11B 0.021(2) 0.0078(18) 0.0130(19) 0.0003(15) -0.0013(16) 0.0027(16) C11A 0.020(2) 0.0076(17) 0.017(2) -0.0002(15) 0.0024(17) 0.0017(16) C12 0.0194(18) 0.0121(18) 0.0173(19) -0.0029(15) -0.0018(15) -0.0006(16) C13 0.031(2) 0.017(2) 0.029(2) 0.0027(16) -0.0022(16) -0.0083(16) C14 0.025(2) 0.020(2) 0.029(2) -0.0009(16) 0.0053(16) -0.0025(16) C15 0.0245(19) 0.0184(19) 0.027(2) -0.0015(16) 0.0004(16) -0.0025(16) C16 0.019(2) 0.0201(19) 0.029(2) -0.0027(17) 0.0012(17) -0.0042(17) C17 0.025(2) 0.046(2) 0.045(2) -0.004(2) -0.0011(19) 0.006(2) C18 0.035(2) 0.031(2) 0.049(2) -0.0100(19) -0.0119(18) -0.0043(19) C19 0.030(2) 0.052(3) 0.035(2) 0.005(2) -0.0084(18) -0.010(2) _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 N5 C4 1.379(4) . ? N5 C6 1.380(4) . ? N5 C11B 1.411(4) . ? N7 C6 1.374(4) . ? N7 C8 1.386(4) . ? N7 C11A 1.413(4) . ? C1 C2 1.356(4) . ? C1 C11B 1.411(4) . ? C1 H1 0.9500 . ? C2 C3 1.436(4) . ? C2 C12 1.529(4) . ? C3 C4 1.343(4) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C8 C9 1.333(4) . ? C8 H8 0.9500 . ? C9 C10 1.443(4) . ? C9 H9 0.9500 . ? C10 C11 1.364(4) . ? C10 C16 1.518(4) . ? C11 C11A 1.410(4) . ? C11 H11 0.9500 . ? C11B C11A 1.372(4) . ? C12 C13 1.521(4) . ? C12 C15 1.530(4) . ? C12 C14 1.537(4) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C19 1.519(4) . ? C16 C17 1.522(4) . ? C16 C18 1.533(4) . ? 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 0.9800 . ? C19 H19C 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 C4 N5 C6 125.8(3) . . ? C4 N5 C11B 119.1(3) . . ? C6 N5 C11B 115.1(2) . . ? C6 N7 C8 125.8(3) . . ? C6 N7 C11A 115.2(3) . . ? C8 N7 C11A 119.0(3) . . ? C2 C1 C11B 121.4(3) . . ? C2 C1 H1 119.3 . . ? C11B C1 H1 119.3 . . ? C1 C2 C3 116.9(3) . . ? C1 C2 C12 123.8(3) . . ? C3 C2 C12 119.3(3) . . ? C4 C3 C2 122.8(3) . . ? C4 C3 H3 118.6 . . ? C2 C3 H3 118.6 . . ? C3 C4 N5 120.2(3) . . ? C3 C4 H4 119.9 . . ? N5 C4 H4 119.9 . . ? N7 C6 N5 99.6(2) . . ? C9 C8 N7 120.3(3) . . ? C9 C8 H8 119.8 . . ? N7 C8 H8 119.8 . . ? C8 C9 C10 123.0(3) . . ? C8 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 116.6(3) . . ? C11 C10 C16 123.7(3) . . ? C9 C10 C16 119.6(3) . . ? C10 C11 C11A 121.4(3) . . ? C10 C11 H11 119.3 . . ? C11A C11 H11 119.3 . . ? C11A C11B C1 135.4(3) . . ? C11A C11B N5 105.0(2) . . ? C1 C11B N5 119.6(3) . . ? C11B C11A C11 135.3(3) . . ? C11B C11A N7 105.0(2) . . ? C11 C11A N7 119.6(3) . . ? C13 C12 C2 111.4(2) . . ? C13 C12 C15 108.0(2) . . ? C2 C12 C15 111.3(2) . . ? C13 C12 C14 109.5(2) . . ? C2 C12 C14 108.8(2) . . ? C15 C12 C14 107.8(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 C19 112.2(3) . . ? C10 C16 C17 108.0(3) . . ? C19 C16 C17 108.3(3) . . ? C10 C16 C18 110.4(3) . . ? C19 C16 C18 108.6(3) . . ? C17 C16 C18 109.2(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 C11B C1 C2 C3 -2.0(4) . . . . ? C11B C1 C2 C12 176.1(3) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C12 C2 C3 C4 -176.7(3) . . . . ? C2 C3 C4 N5 0.2(4) . . . . ? C6 N5 C4 C3 178.4(3) . . . . ? C11B N5 C4 C3 -1.3(4) . . . . ? C8 N7 C6 N5 179.6(3) . . . . ? C11A N7 C6 N5 -1.4(3) . . . . ? C4 N5 C6 N7 -179.1(3) . . . . ? C11B N5 C6 N7 0.7(3) . . . . ? C6 N7 C8 C9 175.7(3) . . . . ? C11A N7 C8 C9 -3.2(4) . . . . ? N7 C8 C9 C10 1.1(5) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C8 C9 C10 C16 -176.2(3) . . . . ? C9 C10 C11 C11A -1.5(4) . . . . ? C16 C10 C11 C11A 175.9(3) . . . . ? C2 C1 C11B C11A -178.0(3) . . . . ? C2 C1 C11B N5 1.0(4) . . . . ? C4 N5 C11B C11A 180.0(3) . . . . ? C6 N5 C11B C11A 0.2(3) . . . . ? C4 N5 C11B C1 0.8(4) . . . . ? C6 N5 C11B C1 -179.0(3) . . . . ? C1 C11B C11A C11 -4.8(6) . . . . ? N5 C11B C11A C11 176.2(3) . . . . ? C1 C11B C11A N7 178.0(3) . . . . ? N5 C11B C11A N7 -1.0(3) . . . . ? C10 C11 C11A C11B -177.4(3) . . . . ? C10 C11 C11A N7 -0.6(4) . . . . ? C6 N7 C11A C11B 1.6(3) . . . . ? C8 N7 C11A C11B -179.3(2) . . . . ? C6 N7 C11A C11 -176.1(3) . . . . ? C8 N7 C11A C11 2.9(4) . . . . ? C1 C2 C12 C13 16.1(4) . . . . ? C3 C2 C12 C13 -165.8(2) . . . . ? C1 C2 C12 C15 136.7(3) . . . . ? C3 C2 C12 C15 -45.2(3) . . . . ? C1 C2 C12 C14 -104.7(3) . . . . ? C3 C2 C12 C14 73.4(3) . . . . ? C11 C10 C16 C19 14.4(4) . . . . ? C9 C10 C16 C19 -168.4(3) . . . . ? C11 C10 C16 C17 -104.9(3) . . . . ? C9 C10 C16 C17 72.3(3) . . . . ? C11 C10 C16 C18 135.8(3) . . . . ? C9 C10 C16 C18 -47.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 20.87 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.176 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.039 #===END data_mn9 _database_code_depnum_ccdc_archive 'CCDC 292419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'in paper 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N2' _chemical_formula_weight 132.16 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.0322(3) _cell_length_b 13.6913(3) _cell_length_c 10.4751(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.964(2) _cell_angle_gamma 90.00 _cell_volume 1436.87(7) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11357 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 24.11 _reflns_number_total 2390 _reflns_number_gt 1893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0502P)^2^+0.6789P] 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 0.012(2) _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 0(4) _refine_ls_number_reflns 2390 _refine_ls_number_parameters 427 _refine_ls_number_restraints 261 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1285 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.049 _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_1 C 0.1308(5) 0.0341(4) 0.7400(5) 0.0416(13) Uani 1 1 d D . . H1_1 H 0.159(5) 0.063(4) 0.668(5) 0.065(18) Uiso 1 1 d . . . N2_1 N 0.1578(4) -0.0624(3) 0.7678(4) 0.0371(10) Uani 1 1 d D . . C3_1 C 0.1219(5) -0.0918(3) 0.8836(5) 0.0397(13) Uani 1 1 d D . . N4_1 N 0.0670(4) -0.0060(3) 0.9287(3) 0.0337(9) Uani 1 1 d D . . C5_1 C 0.0104(4) 0.0071(4) 1.0464(4) 0.0413(13) Uani 1 1 d D . . H5_1 H 0.0078 -0.0456 1.1052 0.050 Uiso 1 1 calc R . . C6_1 C -0.0402(5) 0.0938(4) 1.0762(4) 0.0462(13) Uani 1 1 d D . . H6_1 H -0.0803 0.1017 1.1558 0.055 Uiso 1 1 calc R . . C7_1 C -0.0353(5) 0.1749(4) 0.9910(5) 0.0479(14) Uani 1 1 d D . . H7_1 H -0.0707 0.2364 1.0145 0.058 Uiso 1 1 calc R . . C8_1 C 0.0198(5) 0.1641(3) 0.8773(5) 0.0427(13) Uani 1 1 d D . . H8_1 H 0.0233 0.2179 0.8202 0.051 Uiso 1 1 calc R . . C8A_1 C 0.0726(4) 0.0722(3) 0.8430(4) 0.0349(19) Uani 1 1 d D . . C10_1 C 0.2265(5) -0.1271(4) 0.6796(5) 0.0555(15) Uani 1 1 d D . . H10A_1 H 0.3233 -0.1188 0.6928 0.083 Uiso 1 1 calc R . . H10B_1 H 0.1991 -0.1103 0.5912 0.083 Uiso 1 1 calc R . . H10C_1 H 0.2028 -0.1952 0.6964 0.083 Uiso 1 1 calc R . . C1_2 C 0.3509(5) 0.2549(4) 0.7537(5) 0.0414(13) Uani 1 1 d D . . H1_2 H 0.341(5) 0.235(4) 0.848(5) 0.055(15) Uiso 1 1 d . . . N2_2 N 0.3355(4) 0.3502(3) 0.7139(4) 0.0419(11) Uani 1 1 d D . . C3_2 C 0.3718(5) 0.3674(4) 0.5926(5) 0.0448(13) Uani 1 1 d D . . N4_2 N 0.4109(3) 0.2742(3) 0.5582(3) 0.0350(10) Uani 1 1 d D . . C5_2 C 0.4567(5) 0.2488(4) 0.4412(5) 0.0535(15) Uani 1 1 d D . . H5_2 H 0.4635 0.2969 0.3766 0.064 Uiso 1 1 calc R . . C6_2 C 0.4917(6) 0.1557(5) 0.4184(5) 0.0640(18) Uani 1 1 d D . . H6_2 H 0.5209 0.1375 0.3369 0.077 Uiso 1 1 calc R . . C7_2 C 0.4844(6) 0.0847(4) 0.5177(6) 0.0641(17) Uani 1 1 d D . . H7_2 H 0.5131 0.0198 0.5023 0.077 Uiso 1 1 calc R . . C8_2 C 0.4382(5) 0.1070(4) 0.6322(5) 0.0506(14) Uani 1 1 d D . . H8_2 H 0.4323 0.0584 0.6964 0.061 Uiso 1 1 calc R . . C8A_2 C 0.3984(4) 0.2050(3) 0.6554(4) 0.0361(12) Uani 1 1 d D . . C10_2 C 0.2818(6) 0.4264(5) 0.7947(6) 0.075(2) Uani 1 1 d D . . H10A_2 H 0.1852 0.4316 0.7771 0.112 Uiso 1 1 calc R . . H10B_2 H 0.3241 0.4890 0.7762 0.112 Uiso 1 1 calc R . . H10C_2 H 0.3002 0.4097 0.8848 0.112 Uiso 1 1 calc R . . C1_3 C 0.2477(5) 0.2999(4) 0.1545(4) 0.0410(12) Uani 1 1 d D . . H1_3 H 0.151(5) 0.292(3) 0.172(4) 0.034(12) Uiso 1 1 d . . . N2_3 N 0.3127(4) 0.3862(3) 0.1787(4) 0.0400(11) Uani 1 1 d D . . C3_3 C 0.4436(5) 0.3875(3) 0.1507(4) 0.0381(12) Uani 1 1 d D . . N4_3 N 0.4590(3) 0.2926(3) 0.1066(3) 0.0308(9) Uani 1 1 d D . . C5_3 C 0.5737(5) 0.2521(4) 0.0635(4) 0.0432(13) Uani 1 1 d D . . H5_3 H 0.6527 0.2901 0.0612 0.052 Uiso 1 1 calc R . . C6_3 C 0.5739(5) 0.1586(4) 0.0247(5) 0.0502(14) Uani 1 1 d D . . H6_3 H 0.6535 0.1306 -0.0044 0.060 Uiso 1 1 calc R . . C7_3 C 0.4558(6) 0.1010(4) 0.0266(5) 0.0551(15) Uani 1 1 d D . . H7_3 H 0.4567 0.0352 -0.0022 0.066 Uiso 1 1 calc R . . C8_3 C 0.3431(5) 0.1394(4) 0.0690(4) 0.0441(13) Uani 1 1 d D . . H8_3 H 0.2652 0.1002 0.0721 0.053 Uiso 1 1 calc R . . C8A_3 C 0.3399(4) 0.2375(3) 0.1089(4) 0.0349(12) Uani 1 1 d D . . C10_3 C 0.2480(6) 0.4718(4) 0.2353(6) 0.0646(18) Uani 1 1 d D . . H10A_3 H 0.1698 0.4908 0.1810 0.097 Uiso 1 1 calc R . . H10B_3 H 0.3114 0.5263 0.2414 0.097 Uiso 1 1 calc R . . H10C_3 H 0.2201 0.4550 0.3208 0.097 Uiso 1 1 calc R . . C1_4 C 0.7519(7) 0.2404(5) 0.6421(6) 0.0429(17) Uani 0.753(5) 1 d PD A 1 H1_4 H 0.668(6) 0.211(4) 0.658(5) 0.029(15) Uiso 0.753(5) 1 d P A 1 N2_4 N 0.7964(5) 0.3295(4) 0.6858(5) 0.0415(15) Uani 0.753(5) 1 d PD A 1 C3_4 C 0.9204(7) 0.3544(7) 0.6484(8) 0.042(2) Uani 0.753(5) 1 d PD A 1 N4_4 N 0.9493(5) 0.2736(4) 0.5754(4) 0.0361(14) Uani 0.753(5) 1 d PD A 1 C5_4 C 1.0655(6) 0.2605(5) 0.5102(6) 0.0456(18) Uani 0.753(5) 1 d PD A 1 H5_4 H 1.1340 0.3085 0.5162 0.055 Uiso 0.753(5) 1 calc PR A 1 C6_4 C 1.0807(9) 0.1798(5) 0.4388(7) 0.047(2) Uani 0.753(5) 1 d PD A 1 H6_4 H 1.1583 0.1726 0.3913 0.056 Uiso 0.753(5) 1 calc PR A 1 C7_4 C 0.9811(8) 0.1049(6) 0.4339(6) 0.050(2) Uani 0.753(5) 1 d PD A 1 H7_4 H 0.9941 0.0473 0.3855 0.061 Uiso 0.753(5) 1 calc PR A 1 C8_4 C 0.8688(8) 0.1159(5) 0.4980(7) 0.0427(19) Uani 0.753(5) 1 d PD A 1 H8_4 H 0.8034 0.0656 0.4954 0.051 Uiso 0.753(5) 1 calc PR A 1 C8A_4 C 0.8476(6) 0.2024(4) 0.5692(6) 0.0387(16) Uani 0.753(5) 1 d PD A 1 C10_4 C 0.7175(7) 0.3930(6) 0.7646(8) 0.062(2) Uani 0.753(5) 1 d PD A 1 H10A_4 H 0.7367 0.4614 0.7452 0.093 Uiso 0.753(5) 1 calc PR A 1 H10B_4 H 0.7405 0.3802 0.8551 0.093 Uiso 0.753(5) 1 calc PR A 1 H10C_4 H 0.6223 0.3800 0.7465 0.093 Uiso 0.753(5) 1 calc PR A 1 C1B_4 C 1.2475(16) -0.0150(12) 0.330(2) 0.053(6) Uiso 0.247(5) 1 d PD A 2 H1B_4 H 1.3370 0.0031 0.3160 0.063 Uiso 0.247(5) 1 calc PR A 2 N2B_4 N 1.1902(17) -0.1054(12) 0.310(2) 0.062(7) Uiso 0.247(5) 1 d PD A 2 C3B_4 C 1.061(2) -0.1120(13) 0.343(3) 0.051(11) Uiso 0.247(5) 1 d PD A 2 N4B_4 N 1.0399(12) -0.0184(10) 0.3853(15) 0.043(4) Uiso 0.247(5) 1 d PD A 2 C5B_4 C 0.9212(15) 0.0150(12) 0.4331(18) 0.043(5) Uiso 0.247(5) 1 d PD A 2 H5B_4 H 0.8486 -0.0280 0.4450 0.052 Uiso 0.247(5) 1 calc PR A 2 C6B_4 C 0.913(2) 0.1101(15) 0.462(4) 0.046(10) Uiso 0.247(5) 1 d PD A 2 H6B_4 H 0.8298 0.1367 0.4833 0.055 Uiso 0.247(5) 1 calc PR A 2 C7B_4 C 1.0271(19) 0.1722(15) 0.461(2) 0.037(8) Uiso 0.247(5) 1 d PD A 2 H7B_4 H 1.0205 0.2374 0.4905 0.044 Uiso 0.247(5) 1 calc PR A 2 C8B_4 C 1.1442(19) 0.1405(11) 0.418(2) 0.045(6) Uiso 0.247(5) 1 d PD A 2 H8B_4 H 1.2200 0.1821 0.4182 0.054 Uiso 0.247(5) 1 calc PR A 2 C8AB_4 C 1.1502(14) 0.0430(10) 0.3733(19) 0.043(5) Uiso 0.247(5) 1 d PD A 2 C10B_4 C 1.258(3) -0.1874(19) 0.251(4) 0.100(12) Uiso 0.247(5) 1 d PD A 2 H10D_4 H 1.3495 -0.1687 0.2347 0.151 Uiso 0.247(5) 1 calc PR A 2 H10E_4 H 1.2100 -0.2051 0.1707 0.151 Uiso 0.247(5) 1 calc PR A 2 H10F_4 H 1.2591 -0.2435 0.3096 0.151 Uiso 0.247(5) 1 calc PR A 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 C1_1 0.040(3) 0.046(3) 0.038(3) 0.012(3) -0.009(2) -0.006(2) N2_1 0.031(2) 0.043(3) 0.037(2) -0.004(2) -0.0031(18) -0.0009(19) C3_1 0.031(3) 0.042(3) 0.046(3) 0.006(2) -0.001(2) -0.004(2) N4_1 0.035(2) 0.032(2) 0.034(2) 0.0044(18) 0.0024(17) -0.0002(18) C5_1 0.035(3) 0.052(3) 0.037(3) 0.010(2) 0.004(2) 0.003(3) C6_1 0.042(3) 0.059(4) 0.038(3) 0.000(3) 0.004(2) -0.004(3) C7_1 0.042(3) 0.041(3) 0.059(4) -0.010(3) -0.014(3) 0.001(2) C8_1 0.041(3) 0.034(3) 0.052(3) 0.007(2) -0.010(2) -0.003(2) C8A_1 0.026(3) 0.041(3) 0.037(3) 0.007(2) -0.006(2) -0.005(2) C10_1 0.052(3) 0.066(4) 0.049(3) -0.015(3) 0.002(3) 0.006(3) C1_2 0.034(3) 0.054(4) 0.037(3) 0.003(3) 0.003(2) -0.006(2) N2_2 0.033(2) 0.040(3) 0.054(3) -0.008(2) 0.003(2) -0.0016(19) C3_2 0.045(3) 0.042(3) 0.047(3) 0.001(3) 0.001(2) 0.005(3) N4_2 0.030(2) 0.040(3) 0.035(2) 0.0038(19) 0.0064(17) 0.0006(19) C5_2 0.054(3) 0.071(4) 0.037(3) 0.010(3) 0.012(2) 0.014(3) C6_2 0.057(4) 0.088(5) 0.046(3) -0.013(3) -0.002(3) 0.028(3) C7_2 0.069(4) 0.048(4) 0.073(4) -0.013(3) -0.017(3) 0.022(3) C8_2 0.048(3) 0.040(3) 0.064(4) -0.004(3) -0.003(3) 0.001(3) C8A_2 0.033(3) 0.033(3) 0.042(3) 0.004(2) 0.002(2) 0.000(2) C10_2 0.066(4) 0.075(5) 0.085(5) -0.036(4) 0.014(4) 0.006(4) C1_3 0.033(3) 0.056(3) 0.033(3) -0.005(2) -0.005(2) -0.006(3) N2_3 0.037(2) 0.049(3) 0.033(2) -0.0044(19) -0.0093(19) 0.006(2) C3_3 0.040(3) 0.040(3) 0.033(3) 0.003(2) -0.002(2) 0.001(2) N4_3 0.026(2) 0.039(2) 0.027(2) 0.0006(17) -0.0006(15) 0.0009(18) C5_3 0.037(3) 0.053(3) 0.040(3) 0.003(2) 0.004(2) -0.003(2) C6_3 0.046(3) 0.063(4) 0.042(3) -0.009(3) 0.005(2) 0.010(3) C7_3 0.078(5) 0.044(3) 0.041(3) -0.002(3) -0.008(3) 0.005(3) C8_3 0.046(3) 0.043(3) 0.042(3) 0.005(2) -0.005(2) -0.006(3) C8A_3 0.034(3) 0.040(3) 0.030(2) 0.001(2) -0.003(2) -0.006(2) C10_3 0.056(4) 0.069(4) 0.068(4) -0.026(3) -0.008(3) 0.029(3) C1_4 0.037(4) 0.056(5) 0.036(4) 0.001(3) 0.003(3) -0.008(4) N2_4 0.034(4) 0.051(5) 0.039(4) 0.000(3) -0.010(3) 0.003(3) C3_4 0.042(5) 0.042(5) 0.041(5) -0.005(4) -0.004(3) -0.002(4) N4_4 0.031(3) 0.044(4) 0.033(3) 0.009(3) -0.006(2) -0.008(3) C5_4 0.042(4) 0.054(5) 0.040(4) 0.010(4) 0.000(3) -0.008(3) C6_4 0.039(5) 0.065(6) 0.036(4) 0.007(4) 0.004(4) 0.007(5) C7_4 0.056(6) 0.057(5) 0.038(4) -0.005(4) -0.006(4) 0.006(4) C8_4 0.050(5) 0.043(5) 0.034(5) 0.007(3) -0.008(4) -0.005(4) C8A_4 0.045(4) 0.041(4) 0.029(3) 0.004(3) -0.007(3) -0.005(3) C10_4 0.045(5) 0.079(6) 0.061(5) -0.024(4) 0.001(4) 0.005(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 C1_1 C8A_1 1.357(6) . ? C1_1 N2_1 1.377(6) . ? C1_1 H1_1 0.91(5) . ? N2_1 C3_1 1.344(6) . ? N2_1 C10_1 1.477(6) . ? C3_1 N4_1 1.391(6) . ? N4_1 C5_1 1.395(5) . ? N4_1 C8A_1 1.401(5) . ? C5_1 C6_1 1.334(7) . ? C5_1 H5_1 0.9500 . ? C6_1 C7_1 1.427(7) . ? C6_1 H6_1 0.9500 . ? C7_1 C8_1 1.347(7) . ? C7_1 H7_1 0.9500 . ? C8_1 C8A_1 1.419(6) . ? C8_1 H8_1 0.9500 . ? C10_1 H10A_1 0.9800 . ? C10_1 H10B_1 0.9800 . ? C10_1 H10C_1 0.9800 . ? C1_2 C8A_2 1.343(6) . ? C1_2 N2_2 1.376(6) . ? C1_2 H1_2 1.03(5) . ? N2_2 C3_2 1.360(6) . ? N2_2 C10_2 1.465(6) . ? C3_2 N4_2 1.388(6) . ? N4_2 C5_2 1.375(5) . ? N4_2 C8A_2 1.401(5) . ? C5_2 C6_2 1.347(7) . ? C5_2 H5_2 0.9500 . ? C6_2 C7_2 1.429(7) . ? C6_2 H6_2 0.9500 . ? C7_2 C8_2 1.343(7) . ? C7_2 H7_2 0.9500 . ? C8_2 C8A_2 1.425(6) . ? C8_2 H8_2 0.9500 . ? C10_2 H10A_2 0.9800 . ? C10_2 H10B_2 0.9800 . ? C10_2 H10C_2 0.9800 . ? C1_3 C8A_3 1.364(6) . ? C1_3 N2_3 1.367(6) . ? C1_3 H1_3 1.00(4) . ? N2_3 C3_3 1.360(6) . ? N2_3 C10_3 1.478(6) . ? C3_3 N4_3 1.389(5) . ? N4_3 C5_3 1.375(5) . ? N4_3 C8A_3 1.414(5) . ? C5_3 C6_3 1.344(7) . ? C5_3 H5_3 0.9500 . ? C6_3 C7_3 1.424(7) . ? C6_3 H6_3 0.9500 . ? C7_3 C8_3 1.343(6) . ? C7_3 H7_3 0.9500 . ? C8_3 C8A_3 1.407(6) . ? C8_3 H8_3 0.9500 . ? C10_3 H10A_3 0.9800 . ? C10_3 H10B_3 0.9800 . ? C10_3 H10C_3 0.9800 . ? C1_4 C8A_4 1.361(8) . ? C1_4 N2_4 1.369(8) . ? C1_4 H1_4 0.96(6) . ? N2_4 C3_4 1.367(8) . ? N2_4 C10_4 1.460(8) . ? C3_4 N4_4 1.384(9) . ? N4_4 C5_4 1.392(7) . ? N4_4 C8A_4 1.411(7) . ? C5_4 C6_4 1.348(9) . ? C5_4 H5_4 0.9500 . ? C6_4 C7_4 1.431(9) . ? C6_4 H6_4 0.9500 . ? C7_4 C8_4 1.350(10) . ? C7_4 H7_4 0.9500 . ? C8_4 C8A_4 1.421(8) . ? C8_4 H8_4 0.9500 . ? C10_4 H10A_4 0.9800 . ? C10_4 H10B_4 0.9800 . ? C10_4 H10C_4 0.9800 . ? C1B_4 C8AB_4 1.355(13) . ? C1B_4 N2B_4 1.376(13) . ? C1B_4 H1B_4 0.9500 . ? N2B_4 C3B_4 1.365(14) . ? N2B_4 C10B_4 1.463(14) . ? C3B_4 N4B_4 1.376(14) . ? N4B_4 C5B_4 1.394(12) . ? N4B_4 C8AB_4 1.400(13) . ? C5B_4 C6B_4 1.339(15) . ? C5B_4 H5B_4 0.9500 . ? C6B_4 C7B_4 1.426(15) . ? C6B_4 H6B_4 0.9500 . ? C7B_4 C8B_4 1.349(14) . ? C7B_4 H7B_4 0.9500 . ? C8B_4 C8AB_4 1.418(13) . ? C8B_4 H8B_4 0.9500 . ? C10B_4 H10D_4 0.9800 . ? C10B_4 H10E_4 0.9800 . ? C10B_4 H10F_4 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 C8A_1 C1_1 N2_1 106.7(4) . . ? C8A_1 C1_1 H1_1 131(4) . . ? N2_1 C1_1 H1_1 122(4) . . ? C3_1 N2_1 C1_1 114.8(4) . . ? C3_1 N2_1 C10_1 122.7(4) . . ? C1_1 N2_1 C10_1 122.4(4) . . ? N2_1 C3_1 N4_1 100.5(4) . . ? C3_1 N4_1 C5_1 126.6(4) . . ? C3_1 N4_1 C8A_1 113.4(3) . . ? C5_1 N4_1 C8A_1 120.0(4) . . ? C6_1 C5_1 N4_1 119.9(4) . . ? C6_1 C5_1 H5_1 120.0 . . ? N4_1 C5_1 H5_1 120.0 . . ? C5_1 C6_1 C7_1 121.3(4) . . ? C5_1 C6_1 H6_1 119.3 . . ? C7_1 C6_1 H6_1 119.3 . . ? C8_1 C7_1 C6_1 119.7(5) . . ? C8_1 C7_1 H7_1 120.1 . . ? C6_1 C7_1 H7_1 120.1 . . ? C7_1 C8_1 C8A_1 119.8(5) . . ? C7_1 C8_1 H8_1 120.1 . . ? C8A_1 C8_1 H8_1 120.1 . . ? C1_1 C8A_1 N4_1 104.4(4) . . ? C1_1 C8A_1 C8_1 136.4(4) . . ? N4_1 C8A_1 C8_1 119.2(4) . . ? N2_1 C10_1 H10A_1 109.5 . . ? N2_1 C10_1 H10B_1 109.5 . . ? H10A_1 C10_1 H10B_1 109.5 . . ? N2_1 C10_1 H10C_1 109.5 . . ? H10A_1 C10_1 H10C_1 109.5 . . ? H10B_1 C10_1 H10C_1 109.5 . . ? C8A_2 C1_2 N2_2 106.8(4) . . ? C8A_2 C1_2 H1_2 131(3) . . ? N2_2 C1_2 H1_2 122(3) . . ? C3_2 N2_2 C1_2 114.6(4) . . ? C3_2 N2_2 C10_2 122.7(5) . . ? C1_2 N2_2 C10_2 122.7(5) . . ? N2_2 C3_2 N4_2 100.1(4) . . ? C5_2 N4_2 C3_2 125.2(4) . . ? C5_2 N4_2 C8A_2 121.5(4) . . ? C3_2 N4_2 C8A_2 113.3(4) . . ? C6_2 C5_2 N4_2 120.0(5) . . ? C6_2 C5_2 H5_2 120.0 . . ? N4_2 C5_2 H5_2 120.0 . . ? C5_2 C6_2 C7_2 119.4(5) . . ? C5_2 C6_2 H6_2 120.3 . . ? C7_2 C6_2 H6_2 120.3 . . ? C8_2 C7_2 C6_2 121.9(5) . . ? C8_2 C7_2 H7_2 119.1 . . ? C6_2 C7_2 H7_2 119.1 . . ? C7_2 C8_2 C8A_2 118.6(5) . . ? C7_2 C8_2 H8_2 120.7 . . ? C8A_2 C8_2 H8_2 120.7 . . ? C1_2 C8A_2 N4_2 105.2(4) . . ? C1_2 C8A_2 C8_2 136.3(5) . . ? N4_2 C8A_2 C8_2 118.4(4) . . ? N2_2 C10_2 H10A_2 109.5 . . ? N2_2 C10_2 H10B_2 109.5 . . ? H10A_2 C10_2 H10B_2 109.5 . . ? N2_2 C10_2 H10C_2 109.5 . . ? H10A_2 C10_2 H10C_2 109.5 . . ? H10B_2 C10_2 H10C_2 109.5 . . ? C8A_3 C1_3 N2_3 106.3(4) . . ? C8A_3 C1_3 H1_3 133(3) . . ? N2_3 C1_3 H1_3 121(2) . . ? C3_3 N2_3 C1_3 115.3(4) . . ? C3_3 N2_3 C10_3 121.7(4) . . ? C1_3 N2_3 C10_3 123.0(4) . . ? N2_3 C3_3 N4_3 100.7(4) . . ? C5_3 N4_3 C3_3 126.6(4) . . ? C5_3 N4_3 C8A_3 120.8(4) . . ? C3_3 N4_3 C8A_3 112.6(3) . . ? C6_3 C5_3 N4_3 119.9(5) . . ? C6_3 C5_3 H5_3 120.1 . . ? N4_3 C5_3 H5_3 120.1 . . ? C5_3 C6_3 C7_3 120.6(5) . . ? C5_3 C6_3 H6_3 119.7 . . ? C7_3 C6_3 H6_3 119.7 . . ? C8_3 C7_3 C6_3 120.2(5) . . ? C8_3 C7_3 H7_3 119.9 . . ? C6_3 C7_3 H7_3 119.9 . . ? C7_3 C8_3 C8A_3 120.2(5) . . ? C7_3 C8_3 H8_3 119.9 . . ? C8A_3 C8_3 H8_3 119.9 . . ? C1_3 C8A_3 C8_3 136.7(4) . . ? C1_3 C8A_3 N4_3 105.1(4) . . ? C8_3 C8A_3 N4_3 118.2(4) . . ? N2_3 C10_3 H10A_3 109.5 . . ? N2_3 C10_3 H10B_3 109.5 . . ? H10A_3 C10_3 H10B_3 109.5 . . ? N2_3 C10_3 H10C_3 109.5 . . ? H10A_3 C10_3 H10C_3 109.5 . . ? H10B_3 C10_3 H10C_3 109.5 . . ? C8A_4 C1_4 N2_4 107.5(6) . . ? C8A_4 C1_4 H1_4 126(3) . . ? N2_4 C1_4 H1_4 126(3) . . ? C3_4 N2_4 C1_4 114.3(6) . . ? C3_4 N2_4 C10_4 122.8(6) . . ? C1_4 N2_4 C10_4 122.9(6) . . ? N2_4 C3_4 N4_4 100.3(7) . . ? C3_4 N4_4 C5_4 125.3(6) . . ? C3_4 N4_4 C8A_4 114.0(5) . . ? C5_4 N4_4 C8A_4 120.7(5) . . ? C6_4 C5_4 N4_4 120.0(7) . . ? C6_4 C5_4 H5_4 120.0 . . ? N4_4 C5_4 H5_4 120.0 . . ? C5_4 C6_4 C7_4 120.6(8) . . ? C5_4 C6_4 H6_4 119.7 . . ? C7_4 C6_4 H6_4 119.7 . . ? C8_4 C7_4 C6_4 120.1(7) . . ? C8_4 C7_4 H7_4 119.9 . . ? C6_4 C7_4 H7_4 119.9 . . ? C7_4 C8_4 C8A_4 120.4(6) . . ? C7_4 C8_4 H8_4 119.8 . . ? C8A_4 C8_4 H8_4 119.8 . . ? C1_4 C8A_4 N4_4 103.8(5) . . ? C1_4 C8A_4 C8_4 137.9(6) . . ? N4_4 C8A_4 C8_4 118.2(5) . . ? C8AB_4 C1B_4 N2B_4 106.0(12) . . ? C8AB_4 C1B_4 H1B_4 127.0 . . ? N2B_4 C1B_4 H1B_4 127.0 . . ? C3B_4 N2B_4 C1B_4 114.6(13) . . ? C3B_4 N2B_4 C10B_4 121.5(16) . . ? C1B_4 N2B_4 C10B_4 123.7(16) . . ? N2B_4 C3B_4 N4B_4 100.5(12) . . ? C3B_4 N4B_4 C5B_4 124.7(12) . . ? C3B_4 N4B_4 C8AB_4 113.4(11) . . ? C5B_4 N4B_4 C8AB_4 121.9(12) . . ? C6B_4 C5B_4 N4B_4 117.6(14) . . ? C6B_4 C5B_4 H5B_4 121.2 . . ? N4B_4 C5B_4 H5B_4 121.2 . . ? C5B_4 C6B_4 C7B_4 121.4(17) . . ? C5B_4 C6B_4 H6B_4 119.3 . . ? C7B_4 C6B_4 H6B_4 119.3 . . ? C8B_4 C7B_4 C6B_4 121.5(16) . . ? C8B_4 C7B_4 H7B_4 119.2 . . ? C6B_4 C7B_4 H7B_4 119.2 . . ? C7B_4 C8B_4 C8AB_4 117.7(14) . . ? C7B_4 C8B_4 H8B_4 121.2 . . ? C8AB_4 C8B_4 H8B_4 121.2 . . ? C1B_4 C8AB_4 N4B_4 105.4(11) . . ? C1B_4 C8AB_4 C8B_4 134.9(13) . . ? N4B_4 C8AB_4 C8B_4 119.3(12) . . ? N2B_4 C10B_4 H10D_4 109.5 . . ? N2B_4 C10B_4 H10E_4 109.5 . . ? H10D_4 C10B_4 H10E_4 109.5 . . ? N2B_4 C10B_4 H10F_4 109.5 . . ? H10D_4 C10B_4 H10F_4 109.5 . . ? H10E_4 C10B_4 H10F_4 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.206 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.048 #===END #_eof # End of Crystallographic Information File