# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:\determination\solution\621\new-kh621-abs1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Cl2 Hg1 N3 O1' _chemical_formula_weight 520.76 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 7.2155(8) _cell_length_b 11.6633(12) _cell_length_c 18.314(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.853(10) _cell_angle_gamma 90.00 _cell_volume 1526.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 12235 _cell_measurement_theta_min 2.07 _cell_measurement_theta_max 26.00 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 10.434 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.0322 _exptl_absorpt_correction_T_max 0.1117 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12235 _diffrn_reflns_av_R_equivalents 0.1180 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2999 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0770P)^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 2999 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.011 _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 1.6154(10) 0.4875(6) 0.5872(5) 0.0487(17) Uani 1 1 d . . . H1 H 1.6651 0.5599 0.5987 0.058 Uiso 1 1 calc R . . C2 C 1.7081(10) 0.4132(6) 0.5448(4) 0.0454(16) Uani 1 1 d . . . H2 H 1.8192 0.4370 0.5290 0.054 Uiso 1 1 calc R . . C3 C 1.4843(10) 0.2794(6) 0.5496(4) 0.0436(15) Uani 1 1 d . . . H3 H 1.4345 0.2072 0.5378 0.052 Uiso 1 1 calc R . . C4 C 1.3912(10) 0.3534(6) 0.5912(4) 0.0392(14) Uani 1 1 d . . . C5 C 1.2146(11) 0.3164(5) 0.6194(4) 0.0387(15) Uani 1 1 d . . . C6 C 1.0047(10) 0.3867(6) 0.7079(4) 0.0429(15) Uani 1 1 d . . . C7 C 0.8809(10) 0.2966(6) 0.7051(4) 0.0394(14) Uani 1 1 d . . . H7 H 0.8947 0.2338 0.6751 0.047 Uiso 1 1 calc R . . C8 C 0.7325(10) 0.3000(6) 0.7482(4) 0.0414(15) Uani 1 1 d . . . C9 C 0.5987(12) 0.2108(7) 0.7440(5) 0.0515(18) Uani 1 1 d . . . H9 H 0.6080 0.1485 0.7131 0.062 Uiso 1 1 calc R . . C10 C 0.4543(13) 0.2167(8) 0.7858(5) 0.060(2) Uani 1 1 d . . . H10 H 0.3677 0.1573 0.7836 0.072 Uiso 1 1 calc R . . C11 C 0.4358(14) 0.3105(8) 0.8316(5) 0.062(2) Uani 1 1 d . . . H11 H 0.3361 0.3137 0.8589 0.075 Uiso 1 1 calc R . . C12 C 0.5643(12) 0.3980(7) 0.8365(5) 0.0546(19) Uani 1 1 d . . . H12 H 0.5532 0.4595 0.8679 0.065 Uiso 1 1 calc R . . C13 C 0.7107(10) 0.3948(6) 0.7947(4) 0.0426(15) Uani 1 1 d . . . C14 C 0.8459(11) 0.4836(6) 0.7976(4) 0.0496(17) Uani 1 1 d . . . H14 H 0.8388 0.5451 0.8293 0.059 Uiso 1 1 calc R . . C15 C 0.9854(11) 0.4806(6) 0.7548(5) 0.0508(18) Uani 1 1 d . . . H15 H 1.0696 0.5413 0.7564 0.061 Uiso 1 1 calc R . . N1 N 1.4588(9) 0.4568(5) 0.6112(4) 0.0450(14) Uani 1 1 d . . . N2 N 1.6422(10) 0.3099(6) 0.5264(4) 0.0492(15) Uani 1 1 d . . . N3 N 1.1527(8) 0.3932(5) 0.6656(4) 0.0444(13) Uani 1 1 d . . . H3B H 1.2141 0.4566 0.6698 0.053 Uiso 1 1 calc R . . O1 O 1.1382(7) 0.2253(4) 0.6012(3) 0.0487(12) Uani 1 1 d . . . Hg1 Hg 0.88739(4) 0.16858(2) 0.477975(16) 0.04747(16) Uani 1 1 d . . . Cl1 Cl 0.7691(3) 0.01522(17) 0.53573(14) 0.0615(5) Uani 1 1 d . . . Cl2 Cl 1.0125(3) 0.31275(19) 0.41448(14) 0.0599(5) 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 0.041(4) 0.038(3) 0.067(5) 0.001(3) 0.007(3) -0.010(3) C2 0.041(4) 0.044(4) 0.052(4) 0.008(3) 0.012(3) -0.005(3) C3 0.041(4) 0.042(4) 0.049(4) -0.002(3) 0.010(3) -0.002(3) C4 0.039(3) 0.034(3) 0.044(3) 0.002(3) 0.004(3) 0.002(3) C5 0.041(4) 0.034(3) 0.040(3) 0.002(3) 0.002(3) 0.001(3) C6 0.040(4) 0.042(4) 0.046(4) 0.001(3) 0.000(3) 0.001(3) C7 0.042(4) 0.032(3) 0.045(3) 0.003(3) 0.009(3) 0.002(3) C8 0.040(4) 0.041(3) 0.041(3) 0.007(3) 0.001(3) 0.001(3) C9 0.055(5) 0.045(4) 0.055(4) 0.003(3) 0.007(4) -0.007(3) C10 0.054(5) 0.059(5) 0.067(5) 0.016(4) 0.014(4) -0.005(4) C11 0.055(5) 0.078(6) 0.057(5) 0.016(4) 0.018(4) 0.005(4) C12 0.056(5) 0.056(5) 0.053(4) 0.003(3) 0.012(4) 0.010(4) C13 0.043(4) 0.041(4) 0.043(4) 0.005(3) 0.003(3) 0.010(3) C14 0.051(4) 0.041(4) 0.056(4) -0.011(3) 0.006(3) 0.003(3) C15 0.044(4) 0.043(4) 0.066(5) -0.011(3) 0.009(3) -0.003(3) N1 0.048(3) 0.032(3) 0.054(3) -0.003(2) 0.005(3) -0.004(2) N2 0.042(3) 0.050(4) 0.056(4) 0.000(3) 0.009(3) 0.003(3) N3 0.039(3) 0.037(3) 0.059(4) -0.004(3) 0.018(3) -0.005(2) O1 0.048(3) 0.043(3) 0.056(3) 0.000(2) 0.008(2) -0.011(2) Hg1 0.0432(2) 0.0433(2) 0.0581(2) -0.00168(11) 0.01505(14) -0.00957(10) Cl1 0.0499(10) 0.0469(10) 0.0910(15) 0.0134(9) 0.0225(10) -0.0070(8) Cl2 0.0582(12) 0.0566(11) 0.0686(12) 0.0076(9) 0.0221(10) -0.0157(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 C1 N1 1.316(10) . ? C1 C2 1.396(11) . ? C1 H1 0.9300 . ? C2 N2 1.322(10) . ? C2 H2 0.9300 . ? C3 N2 1.317(10) . ? C3 C4 1.387(10) . ? C3 H3 0.9300 . ? C4 N1 1.333(9) . ? C4 C5 1.501(11) . ? C5 O1 1.223(8) . ? C5 N3 1.351(10) . ? C6 C7 1.375(10) . ? C6 N3 1.404(10) . ? C6 C15 1.411(11) . ? C7 C8 1.414(11) . ? C7 H7 0.9300 . ? C8 C9 1.413(11) . ? C8 C13 1.421(10) . ? C9 C10 1.377(13) . ? C9 H9 0.9300 . ? C10 C11 1.398(14) . ? C10 H10 0.9300 . ? C11 C12 1.373(13) . ? C11 H11 0.9300 . ? C12 C13 1.387(11) . ? C12 H12 0.9300 . ? C13 C14 1.418(11) . ? C14 C15 1.358(13) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N2 Hg1 2.660(7) 1_655 ? N3 H3B 0.8600 . ? Hg1 Cl2 2.295(2) . ? Hg1 Cl1 2.298(2) . ? Hg1 N2 2.660(7) 1_455 ? 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 N1 C1 C2 121.1(6) . . ? N1 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? N2 C2 C1 121.7(7) . . ? N2 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? N2 C3 C4 121.0(7) . . ? N2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? N1 C4 C3 121.9(7) . . ? N1 C4 C5 117.4(7) . . ? C3 C4 C5 120.6(6) . . ? O1 C5 N3 125.0(8) . . ? O1 C5 C4 121.8(7) . . ? N3 C5 C4 113.2(6) . . ? C7 C6 N3 123.9(7) . . ? C7 C6 C15 119.9(8) . . ? N3 C6 C15 116.1(7) . . ? C6 C7 C8 119.6(7) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 120.8(7) . . ? C9 C8 C13 118.3(7) . . ? C7 C8 C13 120.9(7) . . ? C10 C9 C8 119.7(8) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 121.1(9) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C12 C11 C10 120.1(9) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.1(8) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 122.1(7) . . ? C12 C13 C8 120.6(7) . . ? C14 C13 C8 117.3(7) . . ? C15 C14 C13 121.3(7) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C6 121.0(7) . . ? C14 C15 H15 119.5 . . ? C6 C15 H15 119.5 . . ? C1 N1 C4 116.8(7) . . ? C3 N2 C2 117.3(7) . . ? C3 N2 Hg1 125.8(5) . 1_655 ? C2 N2 Hg1 114.7(5) . 1_655 ? C5 N3 C6 130.7(6) . . ? C5 N3 H3B 114.6 . . ? C6 N3 H3B 114.6 . . ? Cl2 Hg1 Cl1 175.94(9) . . ? Cl2 Hg1 N2 92.32(17) . 1_455 ? Cl1 Hg1 N2 91.34(17) . 1_455 ? 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 C1 C2 N2 0.6(12) . . . . ? N2 C3 C4 N1 -1.7(11) . . . . ? N2 C3 C4 C5 -178.0(7) . . . . ? N1 C4 C5 O1 176.6(6) . . . . ? C3 C4 C5 O1 -6.9(10) . . . . ? N1 C4 C5 N3 -3.4(9) . . . . ? C3 C4 C5 N3 173.1(6) . . . . ? N3 C6 C7 C8 -177.8(6) . . . . ? C15 C6 C7 C8 1.3(10) . . . . ? C6 C7 C8 C9 177.3(7) . . . . ? C6 C7 C8 C13 -0.6(10) . . . . ? C7 C8 C9 C10 -179.3(7) . . . . ? C13 C8 C9 C10 -1.4(10) . . . . ? C8 C9 C10 C11 1.1(12) . . . . ? C9 C10 C11 C12 -1.1(13) . . . . ? C10 C11 C12 C13 1.4(12) . . . . ? C11 C12 C13 C14 179.5(7) . . . . ? C11 C12 C13 C8 -1.8(11) . . . . ? C9 C8 C13 C12 1.7(10) . . . . ? C7 C8 C13 C12 179.6(6) . . . . ? C9 C8 C13 C14 -179.5(6) . . . . ? C7 C8 C13 C14 -1.6(9) . . . . ? C12 C13 C14 C15 -178.2(7) . . . . ? C8 C13 C14 C15 3.0(10) . . . . ? C13 C14 C15 C6 -2.3(12) . . . . ? C7 C6 C15 C14 0.1(11) . . . . ? N3 C6 C15 C14 179.3(7) . . . . ? C2 C1 N1 C4 -1.9(11) . . . . ? C3 C4 N1 C1 2.4(10) . . . . ? C5 C4 N1 C1 178.9(6) . . . . ? C4 C3 N2 C2 0.3(11) . . . . ? C4 C3 N2 Hg1 162.8(5) . . . 1_655 ? C1 C2 N2 C3 0.2(11) . . . . ? C1 C2 N2 Hg1 -164.2(6) . . . 1_655 ? O1 C5 N3 C6 6.1(12) . . . . ? C4 C5 N3 C6 -173.8(7) . . . . ? C7 C6 N3 C5 -4.9(11) . . . . ? C15 C6 N3 C5 175.9(7) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.245 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.276 _database_code_depnum_ccdc_archive 'CCDC 956581' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:\determination\solution\625\new-kh625 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 Br2 Hg1 N3 O1' _chemical_formula_weight 609.66 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 7.446(3) _cell_length_b 11.885(5) _cell_length_c 18.079(8) _cell_angle_alpha 90.0 _cell_angle_beta 97.47(3) _cell_angle_gamma 90 _cell_volume 1586.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 13128 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 26.00 _exptl_crystal_description Needle _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.553 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 14.744 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.610 _exptl_absorpt_correction_T_max 0.671 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13128 _diffrn_reflns_av_R_equivalents 0.0987 _diffrn_reflns_av_sigmaI/netI 0.0955 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3134 _reflns_number_gt 2497 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0577P)^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 3134 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.005 _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 0.1052(12) 0.0148(8) 0.5902(6) 0.043(2) Uani 1 1 d . . . H1 H 0.1518 -0.0562 0.6032 0.052 Uiso 1 1 calc R . . C2 C 0.1969(12) 0.0857(8) 0.5474(6) 0.042(2) Uani 1 1 d . . . H2 H 0.3028 0.0602 0.5310 0.051 Uiso 1 1 calc R . . C3 C -0.0188(12) 0.2203(8) 0.5507(5) 0.0387(19) Uani 1 1 d . . . H3 H -0.0659 0.2911 0.5374 0.046 Uiso 1 1 calc R . . C4 C -0.1125(11) 0.1498(7) 0.5927(5) 0.0340(18) Uani 1 1 d . . . C5 C -0.2823(12) 0.1872(7) 0.6210(5) 0.0345(18) Uani 1 1 d . . . C6 C -0.4949(11) 0.1180(9) 0.7063(5) 0.038(2) Uani 1 1 d . . . C7 C -0.6131(13) 0.2079(8) 0.7026(5) 0.0379(19) Uani 1 1 d . . . H7 H -0.5954 0.2701 0.6730 0.045 Uiso 1 1 calc R . . C8 C -0.7629(12) 0.2046(8) 0.7447(5) 0.038(2) Uani 1 1 d . . . C9 C -0.8894(13) 0.2940(8) 0.7392(6) 0.041(2) Uani 1 1 d . . . H9 H -0.8757 0.3556 0.7084 0.050 Uiso 1 1 calc R . . C10 C -1.0321(15) 0.2883(11) 0.7797(7) 0.057(3) Uani 1 1 d . . . H10 H -1.1160 0.3466 0.7759 0.068 Uiso 1 1 calc R . . C11 C -1.0545(14) 0.1988(11) 0.8260(7) 0.058(3) Uani 1 1 d . . . H11 H -1.1521 0.1976 0.8533 0.070 Uiso 1 1 calc R . . C12 C -0.9354(15) 0.1119(10) 0.8322(6) 0.055(3) Uani 1 1 d . . . H12 H -0.9526 0.0518 0.8637 0.066 Uiso 1 1 calc R . . C13 C -0.7848(12) 0.1112(8) 0.7912(5) 0.038(2) Uani 1 1 d . . . C14 C -0.6586(13) 0.0250(8) 0.7951(5) 0.044(2) Uani 1 1 d . . . H14 H -0.6693 -0.0349 0.8276 0.053 Uiso 1 1 calc R . . C15 C -0.5195(14) 0.0249(9) 0.7530(6) 0.051(2) Uani 1 1 d . . . H15 H -0.4410 -0.0361 0.7550 0.061 Uiso 1 1 calc R . . N1 N -0.0505(10) 0.0472(7) 0.6132(4) 0.0393(17) Uani 1 1 d . . . N2 N 0.1396(10) 0.1894(7) 0.5286(5) 0.0448(19) Uani 1 1 d . . . N3 N -0.3466(10) 0.1106(7) 0.6655(5) 0.0451(19) Uani 1 1 d . . . H3A H -0.2889 0.0479 0.6699 0.054 Uiso 1 1 calc R . . O1 O -0.3538(9) 0.2787(6) 0.6022(4) 0.0469(16) Uani 1 1 d . . . Hg1 Hg 0.38345(5) 0.32688(3) 0.48033(2) 0.04552(17) Uani 1 1 d . . . Br1 Br 0.26597(13) 0.48766(9) 0.54156(7) 0.0530(3) Uani 1 1 d . . . Br2 Br 0.51207(15) 0.17756(9) 0.41229(6) 0.0533(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 C1 0.042(5) 0.029(5) 0.057(6) -0.005(4) 0.000(4) 0.005(4) C2 0.033(4) 0.040(5) 0.053(6) 0.000(4) 0.003(4) 0.009(4) C3 0.039(4) 0.033(5) 0.044(5) 0.001(4) 0.003(4) 0.004(4) C4 0.040(4) 0.029(4) 0.033(4) -0.004(4) 0.007(4) 0.001(3) C5 0.040(4) 0.030(5) 0.033(4) -0.003(4) 0.002(3) 0.006(3) C6 0.032(4) 0.042(5) 0.041(5) -0.001(4) 0.004(4) 0.001(4) C7 0.048(5) 0.033(5) 0.033(4) 0.001(4) 0.005(4) -0.001(4) C8 0.037(4) 0.041(5) 0.035(5) -0.005(4) 0.005(4) 0.002(4) C9 0.050(5) 0.033(5) 0.041(5) -0.002(4) 0.004(4) 0.005(4) C10 0.047(5) 0.055(7) 0.068(7) -0.016(6) 0.007(5) 0.010(5) C11 0.041(5) 0.065(8) 0.073(8) -0.008(6) 0.023(5) -0.002(5) C12 0.067(7) 0.053(7) 0.048(6) -0.002(5) 0.022(5) -0.015(5) C13 0.038(4) 0.037(5) 0.041(5) -0.002(4) 0.007(4) -0.003(4) C14 0.049(5) 0.037(5) 0.047(5) 0.010(4) 0.007(4) -0.006(4) C15 0.058(6) 0.036(5) 0.059(6) 0.012(5) 0.011(5) 0.006(4) N1 0.039(4) 0.030(4) 0.049(5) 0.002(3) 0.007(3) 0.004(3) N2 0.041(4) 0.041(5) 0.053(5) 0.002(4) 0.013(4) 0.001(3) N3 0.039(4) 0.039(5) 0.059(5) 0.003(4) 0.012(4) 0.006(3) O1 0.048(4) 0.043(4) 0.052(4) 0.001(3) 0.013(3) 0.011(3) Hg1 0.0490(2) 0.0378(2) 0.0518(3) 0.00061(17) 0.01415(16) 0.01100(16) Br1 0.0491(5) 0.0401(5) 0.0728(7) -0.0073(5) 0.0192(5) 0.0073(4) Br2 0.0560(6) 0.0492(6) 0.0574(6) -0.0065(5) 0.0167(5) 0.0144(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 C1 N1 1.340(12) . ? C1 C2 1.379(14) . ? C1 H1 0.9300 . ? C2 N2 1.333(13) . ? C2 H2 0.9300 . ? C3 N2 1.346(12) . ? C3 C4 1.375(13) . ? C3 H3 0.9300 . ? C4 N1 1.338(11) . ? C4 C5 1.493(12) . ? C5 O1 1.237(11) . ? C5 N3 1.340(12) . ? C6 C7 1.381(14) . ? C6 N3 1.408(11) . ? C6 C15 1.414(14) . ? C7 C8 1.430(13) . ? C7 H7 0.9300 . ? C8 C13 1.409(13) . ? C8 C9 1.417(13) . ? C9 C10 1.369(15) . ? C9 H9 0.9300 . ? C10 C11 1.372(18) . ? C10 H10 0.9300 . ? C11 C12 1.358(17) . ? C11 H11 0.9300 . ? C12 C13 1.422(13) . ? C12 H12 0.9300 . ? C13 C14 1.387(13) . ? C14 C15 1.362(14) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N2 Hg1 2.665(8) . ? N3 H3A 0.8600 . ? Hg1 Br2 2.4261(16) . ? Hg1 Br1 2.4277(16) . ? 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 N1 C1 C2 120.6(9) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? N2 C2 C1 122.5(8) . . ? N2 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? N2 C3 C4 121.6(9) . . ? N2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? N1 C4 C3 121.5(8) . . ? N1 C4 C5 117.2(8) . . ? C3 C4 C5 121.2(8) . . ? O1 C5 N3 125.6(8) . . ? O1 C5 C4 121.6(8) . . ? N3 C5 C4 112.7(7) . . ? C7 C6 N3 124.4(9) . . ? C7 C6 C15 120.0(9) . . ? N3 C6 C15 115.5(9) . . ? C6 C7 C8 119.6(9) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C13 C8 C9 120.3(8) . . ? C13 C8 C7 119.5(8) . . ? C9 C8 C7 120.2(9) . . ? C10 C9 C8 119.0(10) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C9 C10 C11 121.7(10) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 120.5(10) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.1(10) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C8 118.7(8) . . ? C14 C13 C12 123.8(9) . . ? C8 C13 C12 117.5(9) . . ? C15 C14 C13 122.4(9) . . ? C15 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C14 C15 C6 119.7(9) . . ? C14 C15 H15 120.2 . . ? C6 C15 H15 120.2 . . ? C4 N1 C1 117.4(8) . . ? C2 N2 C3 116.4(9) . . ? C2 N2 Hg1 115.9(6) . . ? C3 N2 Hg1 126.1(7) . . ? C5 N3 C6 129.4(8) . . ? C5 N3 H3A 115.3 . . ? C6 N3 H3A 115.3 . . ? Br2 Hg1 Br1 175.12(4) . . ? Br2 Hg1 N2 92.77(18) . . ? Br1 Hg1 N2 91.79(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 N1 C1 C2 N2 1.8(15) . . . . ? N2 C3 C4 N1 -0.1(14) . . . . ? N2 C3 C4 C5 176.3(8) . . . . ? N1 C4 C5 O1 -176.7(8) . . . . ? C3 C4 C5 O1 6.7(13) . . . . ? N1 C4 C5 N3 1.5(12) . . . . ? C3 C4 C5 N3 -175.1(9) . . . . ? N3 C6 C7 C8 177.9(8) . . . . ? C15 C6 C7 C8 -1.7(14) . . . . ? C6 C7 C8 C13 1.9(13) . . . . ? C6 C7 C8 C9 -177.4(9) . . . . ? C13 C8 C9 C10 0.3(14) . . . . ? C7 C8 C9 C10 179.6(9) . . . . ? C8 C9 C10 C11 0.5(16) . . . . ? C9 C10 C11 C12 -0.7(19) . . . . ? C10 C11 C12 C13 0.0(18) . . . . ? C9 C8 C13 C14 179.8(9) . . . . ? C7 C8 C13 C14 0.5(13) . . . . ? C9 C8 C13 C12 -0.9(13) . . . . ? C7 C8 C13 C12 179.8(9) . . . . ? C11 C12 C13 C14 -180.0(11) . . . . ? C11 C12 C13 C8 0.7(15) . . . . ? C8 C13 C14 C15 -3.2(15) . . . . ? C12 C13 C14 C15 177.5(10) . . . . ? C13 C14 C15 C6 3.4(16) . . . . ? C7 C6 C15 C14 -0.9(16) . . . . ? N3 C6 C15 C14 179.4(9) . . . . ? C3 C4 N1 C1 -1.2(13) . . . . ? C5 C4 N1 C1 -177.7(8) . . . . ? C2 C1 N1 C4 0.4(14) . . . . ? C1 C2 N2 C3 -3.0(14) . . . . ? C1 C2 N2 Hg1 163.2(7) . . . . ? C4 C3 N2 C2 2.2(14) . . . . ? C4 C3 N2 Hg1 -162.4(7) . . . . ? O1 C5 N3 C6 -6.5(16) . . . . ? C4 C5 N3 C6 175.4(9) . . . . ? C7 C6 N3 C5 5.1(16) . . . . ? C15 C6 N3 C5 -175.3(10) . . . . ? C2 N2 Hg1 Br2 38.4(7) . . . . ? C3 N2 Hg1 Br2 -156.9(8) . . . . ? C2 N2 Hg1 Br1 -143.3(7) . . . . ? C3 N2 Hg1 Br1 21.4(8) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.922 _refine_diff_density_min -1.220 _refine_diff_density_rms 0.593 _database_code_depnum_ccdc_archive 'CCDC 956582' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:\determination\solution\671\kh671-abs2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 Hg1 I2 N6 O2' _chemical_formula_weight 952.93 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 29.313(3) _cell_length_b 6.8788(4) _cell_length_c 15.5479(12) _cell_angle_alpha 90.00 _cell_angle_beta 111.401(7) _cell_angle_gamma 90.00 _cell_volume 2918.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 11496 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 26.00 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 7.428 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6363 _exptl_absorpt_correction_T_max 0.7786 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11496 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0708 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2874 _reflns_number_gt 1919 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.1721P)^2^+8.8526P] 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 SHELXL _refine_ls_extinction_coef 0.0009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2874 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.1818 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 C1 C 0.1806(5) 0.372(2) 0.4455(9) 0.056(3) Uani 1 1 d . . . H1 H 0.1961 0.3814 0.5092 0.067 Uiso 1 1 calc R . . C2 C 0.1301(5) 0.355(2) 0.4091(10) 0.061(3) Uani 1 1 d . . . H2 H 0.1126 0.3570 0.4483 0.073 Uiso 1 1 calc R . . C3 C 0.1337(4) 0.344(2) 0.2664(8) 0.049(3) Uani 1 1 d . . . H3 H 0.1182 0.3374 0.2025 0.059 Uiso 1 1 calc R . . C4 C 0.1839(4) 0.3609(19) 0.3042(8) 0.046(3) Uani 1 1 d . . . C5 C 0.2139(5) 0.362(2) 0.2413(9) 0.052(3) Uani 1 1 d . . . C6 C 0.3023(4) 0.3604(19) 0.2637(8) 0.047(3) Uani 1 1 d . . . C7 C 0.2988(4) 0.3609(18) 0.1719(8) 0.049(3) Uani 1 1 d . . . H7 H 0.2680 0.3681 0.1251 0.059 Uiso 1 1 calc R . . C8 C 0.3411(5) 0.3506(19) 0.1485(8) 0.050(3) Uani 1 1 d . . . C9 C 0.3389(5) 0.346(2) 0.0568(9) 0.058(3) Uani 1 1 d . . . H9 H 0.3086 0.3545 0.0089 0.069 Uiso 1 1 calc R . . C10 C 0.3810(6) 0.328(2) 0.0364(9) 0.064(4) Uani 1 1 d . . . H10 H 0.3790 0.3223 -0.0247 0.077 Uiso 1 1 calc R . . C11 C 0.4263(6) 0.317(2) 0.1081(11) 0.072(4) Uani 1 1 d . . . H11 H 0.4547 0.3126 0.0947 0.086 Uiso 1 1 calc R . . C12 C 0.4296(6) 0.315(2) 0.1974(11) 0.067(4) Uani 1 1 d . . . H12 H 0.4600 0.2995 0.2443 0.080 Uiso 1 1 calc R . . C13 C 0.3880(5) 0.334(2) 0.2200(8) 0.054(3) Uani 1 1 d . . . C14 C 0.3907(5) 0.334(2) 0.3140(9) 0.056(3) Uani 1 1 d . . . H14 H 0.4211 0.3277 0.3616 0.067 Uiso 1 1 calc R . . C15 C 0.3502(5) 0.344(2) 0.3350(8) 0.059(3) Uani 1 1 d . . . H15 H 0.3532 0.3408 0.3966 0.070 Uiso 1 1 calc R . . N1 N 0.2076(4) 0.3742(16) 0.3946(7) 0.051(2) Uani 1 1 d . . . N2 N 0.1066(4) 0.3369(17) 0.3196(8) 0.058(3) Uani 1 1 d . . . N3 N 0.2621(4) 0.3685(17) 0.2908(7) 0.052(2) Uani 1 1 d . . . H3B H 0.2694 0.3795 0.3494 0.063 Uiso 1 1 calc R . . O1 O 0.1964(4) 0.355(2) 0.1590(7) 0.077(3) Uani 1 1 d . . . Hg1 Hg 0.0000 0.28034(15) 0.2500 0.0828(5) Uani 1 2 d S . . I1 I 0.00188(4) 0.2805(2) 0.08567(6) 0.0759(5) 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 0.054(7) 0.059(8) 0.051(7) 0.005(6) 0.016(6) -0.010(6) C2 0.062(8) 0.063(8) 0.065(8) 0.005(7) 0.032(7) 0.006(6) C3 0.039(6) 0.066(8) 0.044(6) -0.003(5) 0.016(5) -0.001(5) C4 0.048(6) 0.047(6) 0.042(6) -0.002(5) 0.016(5) 0.003(5) C5 0.054(7) 0.050(7) 0.056(7) -0.002(6) 0.025(6) 0.001(6) C6 0.047(6) 0.060(7) 0.042(6) 0.007(5) 0.024(5) 0.005(5) C7 0.043(6) 0.049(6) 0.053(6) 0.002(5) 0.015(5) 0.001(5) C8 0.064(7) 0.044(6) 0.043(6) 0.002(5) 0.022(6) -0.006(6) C9 0.067(8) 0.070(8) 0.043(6) 0.003(6) 0.027(6) 0.004(7) C10 0.084(10) 0.079(10) 0.036(6) 0.004(6) 0.029(6) -0.012(8) C11 0.078(10) 0.084(11) 0.073(9) -0.022(8) 0.052(8) -0.025(8) C12 0.059(8) 0.077(10) 0.072(9) -0.016(7) 0.034(7) -0.013(7) C13 0.065(8) 0.055(7) 0.043(6) -0.007(5) 0.023(6) -0.018(6) C14 0.040(6) 0.079(9) 0.047(6) -0.005(6) 0.013(5) -0.012(6) C15 0.056(7) 0.090(10) 0.031(5) -0.006(6) 0.018(5) -0.013(7) N1 0.049(5) 0.060(6) 0.055(6) -0.002(5) 0.031(5) -0.006(5) N2 0.051(6) 0.063(7) 0.065(7) -0.004(5) 0.027(5) -0.001(5) N3 0.046(6) 0.067(7) 0.051(5) -0.003(5) 0.026(5) -0.003(5) O1 0.058(6) 0.120(9) 0.054(6) -0.004(6) 0.021(5) 0.003(6) Hg1 0.1396(10) 0.0740(7) 0.0572(6) 0.000 0.0625(6) 0.000 I1 0.0638(7) 0.1263(11) 0.0464(6) 0.0094(5) 0.0307(5) 0.0013(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 C1 N1 1.308(16) . ? C1 C2 1.383(19) . ? C1 H1 0.9300 . ? C2 N2 1.314(18) . ? C2 H2 0.9300 . ? C3 N2 1.341(16) . ? C3 C4 1.378(17) . ? C3 H3 0.9300 . ? C4 N1 1.325(16) . ? C4 C5 1.533(17) . ? C5 O1 1.193(16) . ? C5 N3 1.340(16) . ? C6 N3 1.392(15) . ? C6 C7 1.393(17) . ? C6 C15 1.441(17) . ? C7 C8 1.417(18) . ? C7 H7 0.9300 . ? C8 C9 1.402(17) . ? C8 C13 1.423(19) . ? C9 C10 1.39(2) . ? C9 H9 0.9300 . ? C10 C11 1.39(2) . ? C10 H10 0.9300 . ? C11 C12 1.36(2) . ? C11 H11 0.9300 . ? C12 C13 1.39(2) . ? C12 H12 0.9300 . ? C13 C14 1.436(18) . ? C14 C15 1.340(18) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? N3 H3B 0.8600 . ? Hg1 I1 2.5755(9) 2 ? Hg1 I1 2.5756(9) . ? 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 N1 C1 C2 123.2(12) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? N2 C2 C1 120.7(13) . . ? N2 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? N2 C3 C4 121.5(11) . . ? N2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? N1 C4 C3 121.5(11) . . ? N1 C4 C5 118.4(11) . . ? C3 C4 C5 120.0(10) . . ? O1 C5 N3 124.5(12) . . ? O1 C5 C4 124.2(12) . . ? N3 C5 C4 111.3(11) . . ? N3 C6 C7 123.8(11) . . ? N3 C6 C15 117.7(10) . . ? C7 C6 C15 118.5(11) . . ? C6 C7 C8 121.2(11) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 122.8(12) . . ? C9 C8 C13 117.8(12) . . ? C7 C8 C13 119.4(11) . . ? C10 C9 C8 121.2(13) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C11 C10 C9 119.4(12) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C12 C11 C10 120.8(14) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 121.0(15) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C8 119.7(12) . . ? C12 C13 C14 122.0(13) . . ? C8 C13 C14 118.3(12) . . ? C15 C14 C13 121.6(12) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C6 121.1(11) . . ? C14 C15 H15 119.5 . . ? C6 C15 H15 119.5 . . ? C1 N1 C4 116.3(11) . . ? C2 N2 C3 116.7(11) . . ? C5 N3 C6 131.1(11) . . ? C5 N3 H3B 114.5 . . ? C6 N3 H3B 114.5 . . ? I1 Hg1 I1 179.96(7) 2 . ? 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 C1 C2 N2 1(2) . . . . ? N2 C3 C4 N1 -1(2) . . . . ? N2 C3 C4 C5 178.1(12) . . . . ? N1 C4 C5 O1 -178.5(13) . . . . ? C3 C4 C5 O1 2(2) . . . . ? N1 C4 C5 N3 2.8(18) . . . . ? C3 C4 C5 N3 -176.5(13) . . . . ? N3 C6 C7 C8 -179.4(12) . . . . ? C15 C6 C7 C8 -1.5(19) . . . . ? C6 C7 C8 C9 178.3(13) . . . . ? C6 C7 C8 C13 1.9(19) . . . . ? C7 C8 C9 C10 -177.3(13) . . . . ? C13 C8 C9 C10 -1(2) . . . . ? C8 C9 C10 C11 -1(2) . . . . ? C9 C10 C11 C12 4(2) . . . . ? C10 C11 C12 C13 -4(2) . . . . ? C11 C12 C13 C8 2(2) . . . . ? C11 C12 C13 C14 -178.9(14) . . . . ? C9 C8 C13 C12 0(2) . . . . ? C7 C8 C13 C12 177.0(13) . . . . ? C9 C8 C13 C14 -178.6(13) . . . . ? C7 C8 C13 C14 -2.1(19) . . . . ? C12 C13 C14 C15 -177.0(15) . . . . ? C8 C13 C14 C15 2(2) . . . . ? C13 C14 C15 C6 -2(2) . . . . ? N3 C6 C15 C14 179.5(14) . . . . ? C7 C6 C15 C14 1(2) . . . . ? C2 C1 N1 C4 0(2) . . . . ? C3 C4 N1 C1 0(2) . . . . ? C5 C4 N1 C1 -179.7(11) . . . . ? C1 C2 N2 C3 -3(2) . . . . ? C4 C3 N2 C2 3(2) . . . . ? O1 C5 N3 C6 -3(3) . . . . ? C4 C5 N3 C6 175.7(13) . . . . ? C7 C6 N3 C5 6(2) . . . . ? C15 C6 N3 C5 -171.8(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.572 _refine_diff_density_min -1.452 _refine_diff_density_rms 0.326 _database_code_depnum_ccdc_archive 'CCDC 956583' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d:\determination\solution\817\kh817 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H11 N3 O1' _chemical_formula_weight 249.27 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8657(5) _cell_length_b 17.8891(17) _cell_length_c 22.837(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.930(8) _cell_angle_gamma 90.00 _cell_volume 2396.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 26370 _cell_measurement_theta_min 2.12 _cell_measurement_theta_max 29.25 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.090 _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 298(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 'STOE IPDS II' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26370 _diffrn_reflns_av_R_equivalents 0.0911 _diffrn_reflns_av_sigmaI/netI 0.0842 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 29.25 _reflns_number_total 6450 _reflns_number_gt 5874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0263P)^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 6450 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0957 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 0.920 _refine_ls_restrained_S_all 0.920 _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 0.3108(8) 0.0257(3) 0.3487(2) 0.0658(14) Uani 1 1 d . . . H1 H 0.4521 0.0022 0.3507 0.079 Uiso 1 1 calc R . . C2 C 0.1546(10) 0.0077(3) 0.3898(2) 0.0692(15) Uani 1 1 d . . . H2 H 0.1922 -0.0275 0.4184 0.083 Uiso 1 1 calc R . . C3 C -0.0886(8) 0.0886(3) 0.3481(2) 0.0690(15) Uani 1 1 d . . . H3 H -0.2283 0.1132 0.3470 0.083 Uiso 1 1 calc R . . C4 C 0.0665(8) 0.1059(2) 0.3060(2) 0.0516(12) Uani 1 1 d . . . C5 C 0.0079(8) 0.1600(3) 0.2576(2) 0.0581(13) Uani 1 1 d . . . C6 C 0.1812(8) 0.2158(3) 0.1688(2) 0.0547(13) Uani 1 1 d . . . C7 C 0.0095(7) 0.2637(3) 0.1530(2) 0.0545(13) Uani 1 1 d . . . H7 H -0.1185 0.2684 0.1763 0.065 Uiso 1 1 calc R . . C8 C 0.0284(7) 0.3069(3) 0.0999(2) 0.0509(12) Uani 1 1 d . . . C9 C -0.1392(8) 0.3579(3) 0.0830(2) 0.0671(15) Uani 1 1 d . . . H9 H -0.2644 0.3658 0.1066 0.081 Uiso 1 1 calc R . . C10 C -0.1202(9) 0.3963(3) 0.0316(2) 0.0695(15) Uani 1 1 d . . . H10 H -0.2352 0.4294 0.0203 0.083 Uiso 1 1 calc R . . C11 C 0.0684(9) 0.3871(3) -0.0046(2) 0.0710(15) Uani 1 1 d . . . H11 H 0.0794 0.4142 -0.0392 0.085 Uiso 1 1 calc R . . C12 C 0.2356(9) 0.3379(3) 0.0115(2) 0.0691(15) Uani 1 1 d . . . H12 H 0.3611 0.3313 -0.0123 0.083 Uiso 1 1 calc R . . C13 C 0.2194(7) 0.2962(3) 0.0653(2) 0.0530(12) Uani 1 1 d . . . C14 C 0.3893(7) 0.2469(3) 0.0817(2) 0.0652(15) Uani 1 1 d . . . H14 H 0.5153 0.2402 0.0581 0.078 Uiso 1 1 calc R . . C15 C 0.3717(8) 0.2076(3) 0.1331(2) 0.0614(14) Uani 1 1 d . . . H15 H 0.4879 0.1749 0.1443 0.074 Uiso 1 1 calc R . . C16 C 1.1675(7) 0.2118(3) -0.1166(2) 0.0556(13) Uani 1 1 d . . . H16 H 1.3062 0.2139 -0.1357 0.067 Uiso 1 1 calc R . . C17 C 0.9837(7) 0.2509(2) -0.1404(2) 0.0547(13) Uani 1 1 d . . . H17 H 1.0020 0.2779 -0.1748 0.066 Uiso 1 1 calc R . . C18 C 0.7671(7) 0.2097(3) -0.0667(2) 0.0573(13) Uani 1 1 d . . . H18 H 0.6281 0.2075 -0.0477 0.069 Uiso 1 1 calc R . . C19 C 0.9511(7) 0.1700(2) -0.04350(18) 0.0433(11) Uani 1 1 d . . . C20 C 0.9187(8) 0.1243(2) 0.01059(19) 0.0481(12) Uani 1 1 d . . . C21 C 1.1301(7) 0.0428(2) 0.08072(19) 0.0428(11) Uani 1 1 d . . . C22 C 0.9700(7) 0.0349(3) 0.12297(18) 0.0494(12) Uani 1 1 d . . . H22 H 0.8359 0.0625 0.1205 0.059 Uiso 1 1 calc R . . C23 C 1.0051(7) -0.0145(2) 0.17005(19) 0.0458(11) Uani 1 1 d . . . C24 C 0.8413(7) -0.0233(3) 0.2139(2) 0.0586(13) Uani 1 1 d . . . H24 H 0.7084 0.0050 0.2125 0.070 Uiso 1 1 calc R . . C25 C 0.8752(8) -0.0731(3) 0.2587(2) 0.0636(14) Uani 1 1 d . . . H25 H 0.7656 -0.0782 0.2873 0.076 Uiso 1 1 calc R . . C26 C 1.0733(9) -0.1163(3) 0.2616(2) 0.0677(15) Uani 1 1 d . . . H26 H 1.0927 -0.1508 0.2917 0.081 Uiso 1 1 calc R . . C27 C 1.2376(8) -0.1083(3) 0.2210(2) 0.0597(13) Uani 1 1 d . . . H27 H 1.3710 -0.1362 0.2242 0.072 Uiso 1 1 calc R . . C28 C 1.2071(8) -0.0578(2) 0.1736(2) 0.0499(12) Uani 1 1 d . . . C29 C 1.3691(7) -0.0472(3) 0.1295(2) 0.0544(12) Uani 1 1 d . . . H29 H 1.5046 -0.0742 0.1313 0.065 Uiso 1 1 calc R . . C30 C 1.3337(7) 0.0010(2) 0.0846(2) 0.0522(12) Uani 1 1 d . . . H30 H 1.4442 0.0067 0.0562 0.063 Uiso 1 1 calc R . . N1 N 0.2742(6) 0.0748(2) 0.30600(18) 0.0592(11) Uani 1 1 d . . . N2 N -0.0522(8) 0.0395(3) 0.39008(19) 0.0757(13) Uani 1 1 d . . . N3 N 0.1778(6) 0.1724(2) 0.22030(17) 0.0595(11) Uani 1 1 d . . . H3B H 0.3042 0.1504 0.2291 0.071 Uiso 1 1 calc R . . N4 N 1.1552(6) 0.1712(2) -0.06769(16) 0.0502(10) Uani 1 1 d . . . N5 N 0.7824(6) 0.2505(2) -0.11484(18) 0.0591(11) Uani 1 1 d . . . N6 N 1.1080(6) 0.0901(2) 0.03165(15) 0.0509(10) Uani 1 1 d . . . H6 H 1.2310 0.0983 0.0127 0.061 Uiso 1 1 calc R . . O1 O -0.1823(6) 0.1882(2) 0.25423(17) 0.0934(13) Uani 1 1 d . . . O2 O 0.7303(5) 0.11834(18) 0.03224(13) 0.0661(10) 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 0.062(3) 0.061(4) 0.075(4) 0.008(3) -0.011(3) 0.001(3) C2 0.090(4) 0.066(4) 0.051(3) 0.014(3) -0.009(3) 0.002(3) C3 0.070(3) 0.055(4) 0.082(4) 0.012(3) 0.025(3) 0.008(3) C4 0.061(3) 0.048(3) 0.046(3) 0.001(2) -0.004(2) -0.008(3) C5 0.056(3) 0.058(4) 0.060(3) -0.002(3) 0.006(3) -0.003(3) C6 0.057(3) 0.049(3) 0.057(3) -0.006(3) -0.003(3) -0.007(3) C7 0.050(3) 0.057(3) 0.057(3) -0.005(3) 0.003(2) -0.013(3) C8 0.044(3) 0.048(3) 0.061(3) -0.010(3) 0.004(2) -0.007(2) C9 0.059(3) 0.072(4) 0.070(4) -0.009(3) -0.004(3) -0.003(3) C10 0.084(4) 0.073(4) 0.051(3) 0.009(3) -0.013(3) -0.010(3) C11 0.086(4) 0.078(4) 0.049(3) 0.002(3) 0.005(3) -0.016(3) C12 0.088(4) 0.063(4) 0.056(4) -0.013(3) 0.008(3) -0.010(3) C13 0.051(3) 0.051(3) 0.057(3) -0.017(3) -0.010(2) 0.001(2) C14 0.052(3) 0.072(4) 0.072(4) -0.017(3) 0.020(3) -0.001(3) C15 0.063(3) 0.068(4) 0.053(3) -0.004(3) 0.007(3) -0.007(3) C16 0.045(3) 0.067(4) 0.055(3) 0.005(3) 0.003(2) -0.006(2) C17 0.052(3) 0.050(3) 0.062(4) 0.016(2) 0.001(3) -0.001(2) C18 0.049(3) 0.068(4) 0.054(3) 0.008(3) -0.001(2) 0.003(2) C19 0.047(3) 0.043(3) 0.040(3) -0.005(2) -0.002(2) -0.001(2) C20 0.050(3) 0.050(3) 0.044(3) 0.004(2) -0.002(2) -0.007(2) C21 0.044(3) 0.039(3) 0.045(3) -0.005(2) -0.007(2) 0.001(2) C22 0.047(3) 0.058(3) 0.043(3) 0.003(2) -0.002(2) 0.003(2) C23 0.050(3) 0.045(3) 0.042(3) -0.002(2) -0.003(2) -0.009(2) C24 0.054(3) 0.070(4) 0.052(3) 0.001(3) -0.007(2) -0.001(2) C25 0.073(3) 0.066(4) 0.052(3) 0.001(3) 0.002(3) -0.005(3) C26 0.089(4) 0.062(4) 0.052(3) 0.011(3) -0.008(3) -0.004(3) C27 0.056(3) 0.058(4) 0.065(4) 0.007(3) -0.014(3) 0.006(2) C28 0.059(3) 0.042(3) 0.048(3) -0.006(2) -0.007(2) -0.005(2) C29 0.040(2) 0.062(3) 0.061(3) 0.001(3) -0.010(2) 0.003(2) C30 0.048(3) 0.055(3) 0.054(3) -0.003(2) -0.004(2) -0.004(2) N1 0.053(2) 0.060(3) 0.065(3) 0.005(2) 0.000(2) -0.005(2) N2 0.091(3) 0.068(3) 0.068(3) 0.016(3) 0.015(3) 0.002(3) N3 0.058(2) 0.066(3) 0.054(3) 0.009(2) -0.004(2) -0.002(2) N4 0.043(2) 0.061(3) 0.046(2) 0.009(2) 0.0019(18) 0.0013(19) N5 0.049(2) 0.067(3) 0.061(3) 0.012(2) -0.003(2) 0.003(2) N6 0.044(2) 0.055(3) 0.054(3) 0.006(2) 0.0024(19) 0.0000(19) O1 0.070(2) 0.113(3) 0.098(3) 0.041(2) 0.021(2) 0.034(2) O2 0.0526(19) 0.083(3) 0.063(2) 0.0189(19) 0.0039(17) 0.0039(17) _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 N1 1.326(6) . ? C1 C2 1.362(6) . ? C1 H1 0.9300 . ? C2 N2 1.340(5) . ? C2 H2 0.9300 . ? C3 N2 1.315(6) . ? C3 C4 1.369(6) . ? C3 H3 0.9300 . ? C4 N1 1.340(5) . ? C4 C5 1.505(6) . ? C5 O1 1.226(5) . ? C5 N3 1.340(5) . ? C6 C7 1.365(6) . ? C6 C15 1.402(6) . ? C6 N3 1.410(6) . ? C7 C8 1.444(6) . ? C7 H7 0.9300 . ? C8 C9 1.392(6) . ? C8 C13 1.395(6) . ? C9 C10 1.367(6) . ? C9 H9 0.9300 . ? C10 C11 1.401(6) . ? C10 H10 0.9300 . ? C11 C12 1.364(6) . ? C11 H11 0.9300 . ? C12 C13 1.441(6) . ? C12 H12 0.9300 . ? C13 C14 1.379(6) . ? C14 C15 1.373(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 N4 1.336(5) . ? C16 C17 1.389(5) . ? C16 H16 0.9300 . ? C17 N5 1.326(5) . ? C17 H17 0.9300 . ? C18 N5 1.323(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9300 . ? C19 N4 1.327(5) . ? C19 C20 1.497(6) . ? C20 O2 1.223(4) . ? C20 N6 1.349(5) . ? C21 C22 1.365(5) . ? C21 N6 1.408(5) . ? C21 C30 1.411(5) . ? C22 C23 1.404(6) . ? C22 H22 0.9300 . ? C23 C24 1.409(5) . ? C23 C28 1.417(5) . ? C24 C25 1.367(6) . ? C24 H24 0.9300 . ? C25 C26 1.396(6) . ? C25 H25 0.9300 . ? C26 C27 1.355(6) . ? C26 H26 0.9300 . ? C27 C28 1.418(6) . ? C27 H27 0.9300 . ? C28 C29 1.409(6) . ? C29 C30 1.354(6) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? N3 H3B 0.8600 . ? N6 H6 0.8600 . ? 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 N1 C1 C2 124.1(5) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? N2 C2 C1 121.4(5) . . ? N2 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? N2 C3 C4 124.1(5) . . ? N2 C3 H3 118.0 . . ? C4 C3 H3 118.0 . . ? N1 C4 C3 121.4(4) . . ? N1 C4 C5 117.7(4) . . ? C3 C4 C5 120.9(5) . . ? O1 C5 N3 125.2(5) . . ? O1 C5 C4 120.6(5) . . ? N3 C5 C4 114.2(4) . . ? C7 C6 C15 120.3(5) . . ? C7 C6 N3 123.0(4) . . ? C15 C6 N3 116.7(4) . . ? C6 C7 C8 119.3(4) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C13 120.1(5) . . ? C9 C8 C7 121.4(4) . . ? C13 C8 C7 118.5(5) . . ? C10 C9 C8 120.1(5) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 121.6(5) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 119.2(5) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.5(5) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C8 121.1(5) . . ? C14 C13 C12 120.4(5) . . ? C8 C13 C12 118.5(5) . . ? C15 C14 C13 119.8(5) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C6 121.0(5) . . ? C14 C15 H15 119.5 . . ? C6 C15 H15 119.5 . . ? N4 C16 C17 123.3(4) . . ? N4 C16 H16 118.3 . . ? C17 C16 H16 118.3 . . ? N5 C17 C16 121.0(4) . . ? N5 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? N5 C18 C19 122.4(4) . . ? N5 C18 H18 118.8 . . ? C19 C18 H18 118.8 . . ? N4 C19 C18 122.3(4) . . ? N4 C19 C20 118.7(4) . . ? C18 C19 C20 119.1(4) . . ? O2 C20 N6 124.1(4) . . ? O2 C20 C19 120.6(4) . . ? N6 C20 C19 115.3(4) . . ? C22 C21 N6 124.7(4) . . ? C22 C21 C30 119.5(4) . . ? N6 C21 C30 115.8(4) . . ? C21 C22 C23 120.9(4) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C22 C23 C24 121.5(4) . . ? C22 C23 C28 120.0(4) . . ? C24 C23 C28 118.5(4) . . ? C25 C24 C23 120.8(5) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 120.5(5) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C27 C26 C25 120.7(5) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 120.4(5) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C23 117.3(4) . . ? C29 C28 C27 123.5(5) . . ? C23 C28 C27 119.2(4) . . ? C30 C29 C28 122.0(4) . . ? C30 C29 H29 119.0 . . ? C28 C29 H29 119.0 . . ? C29 C30 C21 120.3(4) . . ? C29 C30 H30 119.8 . . ? C21 C30 H30 119.8 . . ? C1 N1 C4 114.3(4) . . ? C3 N2 C2 114.6(4) . . ? C5 N3 C6 130.0(4) . . ? C5 N3 H3B 115.0 . . ? C6 N3 H3B 115.0 . . ? C19 N4 C16 114.7(4) . . ? C18 N5 C17 116.3(4) . . ? C20 N6 C21 128.3(4) . . ? C20 N6 H6 115.8 . . ? C21 N6 H6 115.8 . . ? 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 C1 C2 N2 -0.4(8) . . . . ? N2 C3 C4 N1 -2.3(8) . . . . ? N2 C3 C4 C5 177.0(5) . . . . ? N1 C4 C5 O1 177.4(5) . . . . ? C3 C4 C5 O1 -1.9(7) . . . . ? N1 C4 C5 N3 -1.7(6) . . . . ? C3 C4 C5 N3 178.9(5) . . . . ? C15 C6 C7 C8 -1.4(7) . . . . ? N3 C6 C7 C8 179.1(4) . . . . ? C6 C7 C8 C9 -178.1(4) . . . . ? C6 C7 C8 C13 2.2(7) . . . . ? C13 C8 C9 C10 1.7(7) . . . . ? C7 C8 C9 C10 -178.0(4) . . . . ? C8 C9 C10 C11 -1.5(8) . . . . ? C9 C10 C11 C12 0.8(8) . . . . ? C10 C11 C12 C13 -0.3(7) . . . . ? C9 C8 C13 C14 178.9(4) . . . . ? C7 C8 C13 C14 -1.4(7) . . . . ? C9 C8 C13 C12 -1.2(6) . . . . ? C7 C8 C13 C12 178.5(4) . . . . ? C11 C12 C13 C14 -179.6(5) . . . . ? C11 C12 C13 C8 0.5(7) . . . . ? C8 C13 C14 C15 -0.2(7) . . . . ? C12 C13 C14 C15 179.9(4) . . . . ? C13 C14 C15 C6 1.1(7) . . . . ? C7 C6 C15 C14 -0.2(7) . . . . ? N3 C6 C15 C14 179.3(4) . . . . ? N4 C16 C17 N5 0.6(7) . . . . ? N5 C18 C19 N4 0.9(7) . . . . ? N5 C18 C19 C20 -179.0(4) . . . . ? N4 C19 C20 O2 -175.8(4) . . . . ? C18 C19 C20 O2 4.1(6) . . . . ? N4 C19 C20 N6 2.8(6) . . . . ? C18 C19 C20 N6 -177.3(4) . . . . ? N6 C21 C22 C23 179.1(4) . . . . ? C30 C21 C22 C23 -0.2(6) . . . . ? C21 C22 C23 C24 -179.9(4) . . . . ? C21 C22 C23 C28 -1.1(6) . . . . ? C22 C23 C24 C25 178.2(4) . . . . ? C28 C23 C24 C25 -0.6(7) . . . . ? C23 C24 C25 C26 -0.1(7) . . . . ? C24 C25 C26 C27 1.6(7) . . . . ? C25 C26 C27 C28 -2.2(7) . . . . ? C22 C23 C28 C29 1.8(6) . . . . ? C24 C23 C28 C29 -179.3(4) . . . . ? C22 C23 C28 C27 -178.9(4) . . . . ? C24 C23 C28 C27 0.0(6) . . . . ? C26 C27 C28 C29 -179.3(5) . . . . ? C26 C27 C28 C23 1.4(7) . . . . ? C23 C28 C29 C30 -1.3(6) . . . . ? C27 C28 C29 C30 179.4(4) . . . . ? C28 C29 C30 C21 0.0(7) . . . . ? C22 C21 C30 C29 0.8(6) . . . . ? N6 C21 C30 C29 -178.6(4) . . . . ? C2 C1 N1 C4 -0.3(7) . . . . ? C3 C4 N1 C1 1.6(7) . . . . ? C5 C4 N1 C1 -177.8(4) . . . . ? C4 C3 N2 C2 1.5(8) . . . . ? C1 C2 N2 C3 -0.2(8) . . . . ? O1 C5 N3 C6 -2.9(8) . . . . ? C4 C5 N3 C6 176.3(4) . . . . ? C7 C6 N3 C5 10.6(8) . . . . ? C15 C6 N3 C5 -168.9(5) . . . . ? C18 C19 N4 C16 -1.6(6) . . . . ? C20 C19 N4 C16 178.3(4) . . . . ? C17 C16 N4 C19 0.9(7) . . . . ? C19 C18 N5 C17 0.7(7) . . . . ? C16 C17 N5 C18 -1.4(7) . . . . ? O2 C20 N6 C21 -0.3(7) . . . . ? C19 C20 N6 C21 -178.8(4) . . . . ? C22 C21 N6 C20 -13.9(7) . . . . ? C30 C21 N6 C20 165.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.25 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.204 _refine_diff_density_min -0.189 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 956584'