# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Chowdhury, Chinmay' _publ_contact_author_email chinmay@iicb.res.in _publ_section_title ; An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones ; loop_ _publ_author_name C.Chowdhury A.Sasmal B.Achari # Attachment '- Cif of product 5a.cif' data_as355_0m _database_code_depnum_ccdc_archive 'CCDC 774490' #TrackingRef '- Cif of product 5a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common triazolobenzodiazepinone _chemical_melting_point 178-180 _chemical_formula_moiety C17H14N4O _chemical_formula_sum 'C17 H14 N4 O' _chemical_formula_weight 290.32 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 13.2985(12) _cell_length_b 7.5621(7) _cell_length_c 14.0449(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.240(4) _cell_angle_gamma 90.00 _cell_volume 1404.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2585 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 35.22 _exptl_crystal_description needle-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex 2' _diffrn_measurement_method 'Difference Vectors' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23805 _diffrn_reflns_av_R_equivalents 0.0265 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 35.22 _reflns_number_total 6221 _reflns_number_gt 4101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex 2, Bruker Kappa' _computing_cell_refinement 'Apex 2, Bruker Kappa' _computing_data_reduction 'Apex 2, Bruker Kappa' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.4254P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6221 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0803 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1747 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 0.845 _refine_ls_restrained_S_all 0.845 _refine_ls_shift/su_max 0.424 _refine_ls_shift/su_mean 0.008 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 C5 C 0.29784(9) 0.61487(15) -0.08122(8) 0.0386(2) Uani 1 1 d . . . C10 C 0.27618(8) 0.58728(14) 0.13298(7) 0.03350(19) Uani 1 1 d . . . C9 C 0.37602(8) 0.52316(14) 0.11082(8) 0.0367(2) Uani 1 1 d . . . H9A H 0.4178 0.4960 0.1700 0.044 Uiso 1 1 calc R . . H9B H 0.3674 0.4154 0.0734 0.044 Uiso 1 1 calc R . . C6 C 0.20885(9) 0.58309(15) -0.03952(7) 0.0378(2) Uani 1 1 d . . . C12 C 0.27017(8) 0.62246(14) 0.31552(7) 0.0367(2) Uani 1 1 d . . . C7 C 0.39355(9) 0.69718(15) -0.03430(8) 0.0392(2) Uani 1 1 d . . . C11 C 0.23074(8) 0.62744(15) 0.21395(8) 0.0365(2) Uani 1 1 d . . . C1 C 0.12233(10) 0.52145(18) -0.09414(9) 0.0479(3) Uani 1 1 d . . . H1 H 0.0633 0.5027 -0.0656 0.057 Uiso 1 1 calc R . . C13 C 0.20637(10) 0.57502(17) 0.38378(9) 0.0445(3) Uani 1 1 d . . . H13 H 0.1389 0.5489 0.3646 0.053 Uiso 1 1 calc R . . C17 C 0.36981(10) 0.66509(19) 0.34639(9) 0.0478(3) Uani 1 1 d . . . H17 H 0.4128 0.7012 0.3021 0.057 Uiso 1 1 calc R . . C4 C 0.29607(12) 0.58208(19) -0.17966(8) 0.0500(3) Uani 1 1 d . . . H4 H 0.3538 0.6046 -0.2096 0.060 Uiso 1 1 calc R . . C2 C 0.12382(13) 0.4881(2) -0.19052(10) 0.0563(3) Uani 1 1 d . . . H2 H 0.0661 0.4459 -0.2267 0.068 Uiso 1 1 calc R . . C8 C 0.51227(9) 0.7521(2) 0.10484(10) 0.0501(3) Uani 1 1 d . . . H8A H 0.5739 0.6989 0.0892 0.075 Uiso 1 1 calc R . . H8B H 0.5100 0.7478 0.1729 0.075 Uiso 1 1 calc R . . H8C H 0.5096 0.8730 0.0839 0.075 Uiso 1 1 calc R . . C14 C 0.24262(13) 0.56640(19) 0.47989(9) 0.0540(3) Uani 1 1 d . . . H14 H 0.1994 0.5348 0.5249 0.065 Uiso 1 1 calc R . . C16 C 0.40592(12) 0.6544(2) 0.44244(10) 0.0581(3) Uani 1 1 d . . . H16 H 0.4732 0.6811 0.4622 0.070 Uiso 1 1 calc R . . C3 C 0.21093(14) 0.5173(2) -0.23309(9) 0.0586(4) Uani 1 1 d . . . H3 H 0.2123 0.4934 -0.2979 0.070 Uiso 1 1 calc R . . C15 C 0.34235(14) 0.6044(2) 0.50896(10) 0.0592(4) Uani 1 1 d . . . H15 H 0.3669 0.5964 0.5734 0.071 Uiso 1 1 calc R . . N4 N 0.42648(7) 0.65626(13) 0.05730(7) 0.0386(2) Uani 1 1 d . . . N1 N 0.20271(7) 0.61258(13) 0.05962(6) 0.03774(19) Uani 1 1 d . . . N2 N 0.11527(8) 0.66451(17) 0.09246(8) 0.0481(2) Uani 1 1 d . . . N3 N 0.13242(8) 0.67306(17) 0.18560(8) 0.0471(2) Uani 1 1 d . . . O1 O 0.44017(8) 0.80042(15) -0.08108(7) 0.0555(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 C5 0.0446(6) 0.0349(5) 0.0358(4) 0.0023(4) 0.0021(4) 0.0008(4) C10 0.0313(4) 0.0335(4) 0.0353(4) 0.0020(3) 0.0018(3) -0.0020(3) C9 0.0347(5) 0.0354(5) 0.0398(5) 0.0035(4) 0.0030(4) 0.0033(4) C6 0.0395(5) 0.0370(5) 0.0354(4) 0.0023(4) -0.0023(4) -0.0015(4) C12 0.0387(5) 0.0343(5) 0.0376(4) -0.0017(4) 0.0059(4) -0.0024(4) C7 0.0389(5) 0.0384(5) 0.0413(5) 0.0015(4) 0.0086(4) 0.0006(4) C11 0.0329(5) 0.0389(5) 0.0380(4) 0.0005(4) 0.0047(3) -0.0026(4) C1 0.0453(6) 0.0497(7) 0.0457(6) 0.0026(5) -0.0081(5) -0.0052(5) C13 0.0475(6) 0.0430(6) 0.0446(5) -0.0004(4) 0.0124(5) -0.0042(5) C17 0.0432(6) 0.0576(7) 0.0422(5) -0.0025(5) 0.0032(4) -0.0089(5) C4 0.0647(8) 0.0491(7) 0.0365(5) 0.0030(5) 0.0058(5) 0.0039(6) C2 0.0661(9) 0.0530(7) 0.0449(6) 0.0004(5) -0.0162(6) -0.0055(6) C8 0.0349(5) 0.0575(7) 0.0569(7) -0.0008(6) 0.0008(5) -0.0065(5) C14 0.0749(9) 0.0480(7) 0.0417(6) 0.0006(5) 0.0178(6) -0.0023(6) C16 0.0566(8) 0.0673(9) 0.0478(6) -0.0070(6) -0.0067(6) -0.0088(7) C3 0.0823(10) 0.0554(8) 0.0354(5) -0.0012(5) -0.0060(6) 0.0014(7) C15 0.0835(11) 0.0550(8) 0.0376(5) -0.0028(5) -0.0006(6) -0.0005(7) N4 0.0321(4) 0.0420(5) 0.0418(4) 0.0014(3) 0.0047(3) -0.0028(3) N1 0.0311(4) 0.0435(5) 0.0379(4) 0.0018(3) 0.0002(3) -0.0013(3) N2 0.0318(4) 0.0649(7) 0.0469(5) 0.0012(5) 0.0013(4) 0.0028(4) N3 0.0338(5) 0.0612(7) 0.0466(5) -0.0005(4) 0.0058(4) 0.0019(4) O1 0.0534(5) 0.0602(6) 0.0545(5) 0.0115(4) 0.0134(4) -0.0114(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 C5 C6 1.3971(16) . ? C5 C4 1.4023(16) . ? C5 C7 1.5031(17) . ? C10 N1 1.3542(13) . ? C10 C11 1.3784(14) . ? C10 C9 1.4781(15) . ? C9 N4 1.4622(14) . ? C6 C1 1.3920(16) . ? C6 N1 1.4212(14) . ? C12 C17 1.3867(17) . ? C12 C13 1.3945(15) . ? C12 C11 1.4659(15) . ? C7 O1 1.2304(14) . ? C7 N4 1.3492(15) . ? C11 N3 1.3689(15) . ? C1 C2 1.3793(19) . ? C13 C14 1.3846(19) . ? C17 C16 1.3842(18) . ? C4 C3 1.378(2) . ? C2 C3 1.378(2) . ? C8 N4 1.4516(16) . ? C14 C15 1.375(2) . ? C16 C15 1.379(2) . ? N1 N2 1.3548(14) . ? N2 N3 1.3048(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C5 C4 117.30(11) . . ? C6 C5 C7 127.08(10) . . ? C4 C5 C7 115.35(11) . . ? N1 C10 C11 104.59(9) . . ? N1 C10 C9 118.45(9) . . ? C11 C10 C9 136.91(10) . . ? N4 C9 C10 110.82(9) . . ? C1 C6 C5 120.91(11) . . ? C1 C6 N1 117.41(11) . . ? C5 C6 N1 121.68(10) . . ? C17 C12 C13 118.49(11) . . ? C17 C12 C11 121.80(10) . . ? C13 C12 C11 119.71(10) . . ? O1 C7 N4 121.63(11) . . ? O1 C7 C5 118.72(11) . . ? N4 C7 C5 119.65(10) . . ? N3 C11 C10 107.82(9) . . ? N3 C11 C12 121.25(10) . . ? C10 C11 C12 130.90(10) . . ? C2 C1 C6 120.19(13) . . ? C14 C13 C12 120.59(13) . . ? C12 C17 C16 120.64(12) . . ? C3 C4 C5 121.62(14) . . ? C3 C2 C1 119.92(13) . . ? C15 C14 C13 120.14(13) . . ? C15 C16 C17 120.20(14) . . ? C2 C3 C4 120.02(12) . . ? C14 C15 C16 119.90(13) . . ? C7 N4 C8 118.78(10) . . ? C7 N4 C9 121.91(9) . . ? C8 N4 C9 119.27(10) . . ? C10 N1 N2 110.91(9) . . ? C10 N1 C6 127.57(10) . . ? N2 N1 C6 121.46(9) . . ? N3 N2 N1 107.02(9) . . ? N2 N3 C11 109.66(9) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 35.22 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.342 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.043 # Attachment '- Cif of product 6a.cif' data_as444_0m _database_code_depnum_ccdc_archive 'CCDC 775332' #TrackingRef '- Cif of product 6a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common triazolobenzodiazocine _chemical_melting_point 204-206 _chemical_formula_moiety C18H16N4O _chemical_formula_sum 'C18 H16 N4 O' _chemical_formula_weight 304.35 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.459(4) _cell_length_b 9.484(4) _cell_length_c 18.978(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1522.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1560 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle-shaped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex 2' _diffrn_measurement_method 'Difference Vectors' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2156 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1901 _reflns_number_gt 1706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex 2, Bruker Kappa' _computing_cell_refinement 'Apex 2, Bruker Kappa' _computing_data_reduction 'Apex 2, Bruker Kappa' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8217P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(3) _refine_ls_number_reflns 1901 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1274 _refine_ls_wR_factor_gt 0.1203 _refine_ls_goodness_of_fit_ref 0.782 _refine_ls_restrained_S_all 0.782 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.1634(3) 0.7639(3) 0.35323(17) 0.0383(7) Uani 1 1 d . . . N2 N -0.2351(3) 0.8707(3) 0.38926(19) 0.0466(8) Uani 1 1 d . . . N3 N -0.1248(3) 0.9389(3) 0.42254(19) 0.0451(8) Uani 1 1 d . . . N4 N 0.0160(3) 0.7051(3) 0.21155(18) 0.0400(7) Uani 1 1 d . . . O1 O -0.1776(3) 0.8274(2) 0.15631(16) 0.0508(7) Uani 1 1 d . . . C1 C -0.2655(3) 0.6701(3) 0.3153(2) 0.0379(9) Uani 1 1 d . . . C2 C -0.3785(3) 0.5976(3) 0.3536(2) 0.0466(9) Uani 1 1 d . . . H2 H -0.3822 0.6050 0.4024 0.056 Uiso 1 1 calc R . . C3 C -0.4859(3) 0.5138(4) 0.3180(3) 0.0553(11) Uani 1 1 d . . . H3 H -0.5606 0.4622 0.3430 0.066 Uiso 1 1 calc R . . C4 C -0.4821(4) 0.5066(4) 0.2452(3) 0.0569(12) Uani 1 1 d . . . H4 H -0.5562 0.4520 0.2214 0.068 Uiso 1 1 calc R . . C5 C -0.3687(3) 0.5804(4) 0.2076(2) 0.0484(10) Uani 1 1 d . . . H5 H -0.3671 0.5751 0.1587 0.058 Uiso 1 1 calc R . . C6 C -0.2574(3) 0.6622(3) 0.2426(2) 0.0401(9) Uani 1 1 d . . . C7 C -0.1365(3) 0.7393(3) 0.1998(2) 0.0391(8) Uani 1 1 d . . . C8 C 0.1424(4) 0.7735(4) 0.1716(2) 0.0518(10) Uani 1 1 d . . . H8A H 0.1892 0.7066 0.1399 0.078 Uiso 1 1 calc R . . H8B H 0.2215 0.8080 0.2036 0.078 Uiso 1 1 calc R . . H8C H 0.0994 0.8509 0.1452 0.078 Uiso 1 1 calc R . . C9 C 0.0652(3) 0.6003(3) 0.2626(2) 0.0392(8) Uani 1 1 d . . . H9A H 0.1544 0.5482 0.2437 0.047 Uiso 1 1 calc R . . H9B H -0.0207 0.5341 0.2700 0.047 Uiso 1 1 calc R . . C10 C 0.1117(3) 0.6644(3) 0.3329(2) 0.0392(8) Uani 1 1 d . . . H10A H 0.1291 0.5884 0.3662 0.047 Uiso 1 1 calc R . . H10B H 0.2116 0.7132 0.3269 0.047 Uiso 1 1 calc R . . C11 C -0.0044(3) 0.7654(3) 0.36451(19) 0.0330(7) Uani 1 1 d . . . C12 C 0.0179(3) 0.8777(3) 0.4092(2) 0.0360(8) Uani 1 1 d . . . C13 C 0.1624(3) 0.9355(3) 0.44160(19) 0.0373(8) Uani 1 1 d . . . C14 C 0.2972(4) 0.8547(3) 0.4531(2) 0.0431(9) Uani 1 1 d . . . H14 H 0.2961 0.7591 0.4423 0.052 Uiso 1 1 calc R . . C15 C 0.4319(4) 0.9146(4) 0.4803(2) 0.0482(9) Uani 1 1 d . . . H15 H 0.5221 0.8600 0.4865 0.058 Uiso 1 1 calc R . . C16 C 0.4335(4) 1.0557(4) 0.4983(2) 0.0550(10) Uani 1 1 d . . . H16 H 0.5249 1.0965 0.5164 0.066 Uiso 1 1 calc R . . C17 C 0.2995(4) 1.1356(4) 0.4895(3) 0.0551(11) Uani 1 1 d . . . H17 H 0.2999 1.2301 0.5024 0.066 Uiso 1 1 calc R . . C18 C 0.1650(4) 1.0767(3) 0.4616(2) 0.0455(9) Uani 1 1 d . . . H18 H 0.0748 1.1317 0.4560 0.055 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 N1 0.0354(12) 0.0399(14) 0.039(2) -0.0024(12) 0.0013(11) 0.0008(10) N2 0.0408(14) 0.0505(16) 0.049(2) -0.0110(15) 0.0034(12) 0.0080(12) N3 0.0444(14) 0.0458(15) 0.045(2) -0.0078(14) 0.0018(12) 0.0024(12) N4 0.0419(13) 0.0347(14) 0.043(2) 0.0001(12) 0.0055(12) 0.0001(10) O1 0.0616(13) 0.0405(12) 0.050(2) 0.0050(12) -0.0064(12) 0.0029(10) C1 0.0325(14) 0.0370(16) 0.044(3) -0.0015(14) 0.0022(13) 0.0027(11) C2 0.0401(15) 0.0510(19) 0.049(3) 0.0017(17) 0.0069(14) 0.0010(14) C3 0.0357(16) 0.054(2) 0.076(4) -0.002(2) 0.0077(17) -0.0093(14) C4 0.0397(17) 0.052(2) 0.079(4) -0.013(2) -0.0055(18) -0.0078(14) C5 0.0406(16) 0.056(2) 0.048(3) -0.0123(18) -0.0069(14) 0.0013(14) C6 0.0350(14) 0.0351(16) 0.050(3) -0.0029(14) -0.0016(14) 0.0012(12) C7 0.0471(16) 0.0318(17) 0.038(3) -0.0077(14) -0.0025(14) 0.0037(12) C8 0.0507(17) 0.053(2) 0.051(3) 0.0024(18) 0.0147(16) -0.0033(15) C9 0.0387(14) 0.0329(16) 0.046(3) -0.0024(14) 0.0031(14) 0.0055(12) C10 0.0390(14) 0.0378(16) 0.041(3) -0.0018(14) -0.0006(14) 0.0070(12) C11 0.0335(13) 0.0320(15) 0.034(2) 0.0006(13) 0.0012(12) 0.0025(12) C12 0.0347(14) 0.0356(16) 0.038(2) 0.0003(14) 0.0021(13) 0.0019(12) C13 0.0438(15) 0.0402(17) 0.028(2) 0.0006(14) 0.0019(13) -0.0010(13) C14 0.0483(17) 0.0430(18) 0.038(3) 0.0000(15) 0.0008(14) 0.0007(13) C15 0.0433(16) 0.065(2) 0.037(3) 0.0037(17) -0.0035(15) 0.0040(15) C16 0.0576(19) 0.062(2) 0.045(3) 0.0006(19) -0.0113(17) -0.0144(17) C17 0.073(2) 0.045(2) 0.047(3) -0.0051(17) -0.0132(19) -0.0066(16) C18 0.0522(17) 0.0396(18) 0.045(3) 0.0000(15) -0.0050(15) 0.0045(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C11 1.362(3) . ? N1 N2 1.365(4) . ? N1 C1 1.433(4) . ? N2 N3 1.299(4) . ? N3 C12 1.363(4) . ? N4 C7 1.349(4) . ? N4 C9 1.449(4) . ? N4 C8 1.462(4) . ? O1 C7 1.225(4) . ? C1 C2 1.384(5) . ? C1 C6 1.384(5) . ? C2 C3 1.383(5) . ? C3 C4 1.384(6) . ? C4 C5 1.385(5) . ? C5 C6 1.389(5) . ? C6 C7 1.496(5) . ? C9 C10 1.518(5) . ? C10 C11 1.497(4) . ? C11 C12 1.376(5) . ? C12 C13 1.473(4) . ? C13 C14 1.391(4) . ? C13 C18 1.392(5) . ? C14 C15 1.373(5) . ? C15 C16 1.382(6) . ? C16 C17 1.374(5) . ? C17 C18 1.374(5) . ? 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 C11 N1 N2 110.6(3) . . ? C11 N1 C1 132.9(3) . . ? N2 N1 C1 116.4(2) . . ? N3 N2 N1 107.1(2) . . ? N2 N3 C12 109.6(3) . . ? C7 N4 C9 123.4(3) . . ? C7 N4 C8 120.5(3) . . ? C9 N4 C8 116.2(3) . . ? C2 C1 C6 122.1(3) . . ? C2 C1 N1 117.5(4) . . ? C6 C1 N1 120.3(3) . . ? C3 C2 C1 118.9(4) . . ? C2 C3 C4 120.1(3) . . ? C3 C4 C5 120.4(3) . . ? C4 C5 C6 120.3(4) . . ? C1 C6 C5 118.2(3) . . ? C1 C6 C7 123.2(3) . . ? C5 C6 C7 118.5(4) . . ? O1 C7 N4 123.1(3) . . ? O1 C7 C6 120.3(3) . . ? N4 C7 C6 116.5(3) . . ? N4 C9 C10 112.8(3) . . ? C11 C10 C9 116.0(2) . . ? N1 C11 C12 103.9(2) . . ? N1 C11 C10 125.3(3) . . ? C12 C11 C10 130.7(2) . . ? N3 C12 C11 108.8(2) . . ? N3 C12 C13 120.0(3) . . ? C11 C12 C13 131.2(3) . . ? C14 C13 C18 118.3(3) . . ? C14 C13 C12 122.7(3) . . ? C18 C13 C12 119.0(3) . . ? C15 C14 C13 120.7(3) . . ? C14 C15 C16 120.1(3) . . ? C17 C16 C15 119.7(3) . . ? C18 C17 C16 120.4(3) . . ? C17 C18 C13 120.6(3) . . ? _diffrn_measured_fraction_theta_max 0.801 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.801 _refine_diff_density_max 0.164 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.041