# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Pal, Manojit' _publ_contact_author_email manojitpal@rediffmail.com _publ_section_title ; A new three-component reaction: Green synthesis of novel isoindolo[2,1-a]quinazoline derivatives as potent inhibitors of TNF-a ; _publ_author_name M.Pal data_ils_drb_1_148_1a_1 _database_code_depnum_ccdc_archive 'CCDC 807140' #TrackingRef '- ILS_DRB_1_148_1A_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 Cl N2 O2' _chemical_formula_weight 374.81 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' 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 '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 11.6223(6) _cell_length_b 7.8255(4) _cell_length_c 19.9457(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.228(2) _cell_angle_gamma 90.00 _cell_volume 1772.91(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9978 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.95 _exptl_crystal_description block _exptl_crystal_colour transparant _exptl_crystal_size_max 0.005 _exptl_crystal_size_mid 0.004 _exptl_crystal_size_min 0.0018 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.236 _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 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 APEX-II CCD' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27323 _diffrn_reflns_av_R_equivalents 0.0465 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3833 _reflns_number_gt 3311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.5413P] 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 3833 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1616 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Cl1 Cl 0.54095(5) 0.77847(10) 0.19500(4) 0.0858(3) Uani 1 1 d . . . C15 C 0.99442(14) 0.1891(2) 0.11269(8) 0.0373(3) Uani 1 1 d . . . H15 H 1.0253 0.0789 0.1319 0.045 Uiso 1 1 calc R . . C9 C 0.85951(14) 0.4391(2) 0.21400(8) 0.0389(4) Uani 1 1 d . . . C7 C 1.13271(15) 0.4024(2) 0.17569(8) 0.0396(4) Uani 1 1 d . . . C6 C 1.20658(14) 0.3696(2) 0.12503(8) 0.0405(4) Uani 1 1 d . . . C16 C 0.86423(14) 0.1725(2) 0.08093(8) 0.0386(4) Uani 1 1 d . . . C8 C 0.96445(16) 0.3214(2) 0.22202(8) 0.0413(4) Uani 1 1 d . . . H8A H 1.0203 0.3523 0.2637 0.050 Uiso 1 1 calc R . . H8B H 0.9384 0.2056 0.2277 0.050 Uiso 1 1 calc R . . C1 C 1.16099(15) 0.2857(2) 0.06359(9) 0.0404(4) Uani 1 1 d . . . C12 C 0.66492(16) 0.6484(3) 0.20362(11) 0.0541(5) Uani 1 1 d . . . C10 C 0.83555(16) 0.5636(2) 0.16397(9) 0.0465(4) Uani 1 1 d . . . H10 H 0.8853 0.5769 0.1335 0.056 Uiso 1 1 calc R . . C5 C 1.32198(16) 0.4268(3) 0.13817(10) 0.0512(4) Uani 1 1 d . . . H5 H 1.3530 0.4826 0.1792 0.061 Uiso 1 1 calc R . . C21 C 0.84678(15) 0.2023(2) 0.01115(9) 0.0430(4) Uani 1 1 d . . . C22 C 0.96008(16) 0.2395(3) -0.00754(9) 0.0464(4) Uani 1 1 d . . . C20 C 0.73622(18) 0.1935(3) -0.03190(11) 0.0571(5) Uani 1 1 d . . . H20 H 0.7261 0.2132 -0.0788 0.069 Uiso 1 1 calc R . . C11 C 0.73812(18) 0.6691(3) 0.15860(10) 0.0537(5) Uani 1 1 d . . . H11 H 0.7226 0.7529 0.1248 0.064 Uiso 1 1 calc R . . C14 C 0.78623(19) 0.4242(3) 0.26015(11) 0.0559(5) Uani 1 1 d . . . H14 H 0.8028 0.3431 0.2950 0.067 Uiso 1 1 calc R . . C18 C 0.65924(17) 0.1230(3) 0.06700(11) 0.0561(5) Uani 1 1 d . . . H18 H 0.5944 0.0973 0.0856 0.067 Uiso 1 1 calc R . . C17 C 0.76991(16) 0.1286(2) 0.10988(9) 0.0472(4) Uani 1 1 d . . . H17 H 0.7805 0.1037 0.1564 0.057 Uiso 1 1 calc R . . C2 C 1.22946(18) 0.2625(3) 0.01526(10) 0.0545(5) Uani 1 1 d . . . H2 H 1.1987 0.2084 -0.0262 0.065 Uiso 1 1 calc R . . C3 C 1.34438(19) 0.3212(3) 0.02978(12) 0.0634(6) Uani 1 1 d . . . H3 H 1.3910 0.3062 -0.0024 0.076 Uiso 1 1 calc R . . C4 C 1.39097(17) 0.4014(3) 0.09084(12) 0.0616(5) Uani 1 1 d . . . H4 H 1.4688 0.4383 0.1001 0.074 Uiso 1 1 calc R . . C13 C 0.68832(19) 0.5289(3) 0.25503(13) 0.0643(6) Uani 1 1 d . . . H13 H 0.6392 0.5181 0.2860 0.077 Uiso 1 1 calc R . . C19 C 0.64217(17) 0.1547(3) -0.00280(11) 0.0606(5) Uani 1 1 d . . . H19 H 0.5667 0.1497 -0.0301 0.073 Uiso 1 1 calc R . . O2 O 1.16641(12) 0.49649(18) 0.22479(7) 0.0538(3) Uani 1 1 d . . . O1 O 0.97968(14) 0.2707(3) -0.06362(7) 0.0733(5) Uani 1 1 d . . . N2 N 1.02531(12) 0.32355(17) 0.16508(7) 0.0382(3) Uani 1 1 d . . . N1 N 1.04365(12) 0.23021(19) 0.05313(7) 0.0407(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 Cl1 0.0457(3) 0.0903(5) 0.1169(6) -0.0311(4) 0.0068(3) 0.0184(3) C15 0.0398(8) 0.0353(8) 0.0379(8) 0.0009(6) 0.0104(6) 0.0024(6) C9 0.0399(8) 0.0374(8) 0.0413(8) -0.0052(6) 0.0129(6) -0.0045(6) C7 0.0420(8) 0.0358(8) 0.0412(8) -0.0023(6) 0.0091(6) 0.0043(6) C6 0.0392(8) 0.0385(8) 0.0445(8) -0.0004(6) 0.0108(7) 0.0043(6) C16 0.0403(8) 0.0341(8) 0.0425(8) -0.0009(6) 0.0108(6) 0.0000(6) C8 0.0464(9) 0.0440(9) 0.0355(8) 0.0026(6) 0.0135(7) 0.0037(7) C1 0.0359(8) 0.0423(9) 0.0444(8) -0.0012(7) 0.0115(6) 0.0039(6) C12 0.0361(9) 0.0504(10) 0.0755(13) -0.0188(9) 0.0110(8) -0.0004(8) C10 0.0487(9) 0.0480(9) 0.0458(9) 0.0009(7) 0.0169(7) 0.0034(7) C5 0.0433(9) 0.0552(11) 0.0546(10) -0.0064(8) 0.0092(8) -0.0039(8) C21 0.0392(9) 0.0466(9) 0.0433(9) 0.0019(7) 0.0086(7) 0.0012(7) C22 0.0419(9) 0.0580(10) 0.0399(8) 0.0013(7) 0.0100(7) 0.0001(8) C20 0.0458(10) 0.0706(13) 0.0513(10) 0.0057(9) 0.0022(8) 0.0029(9) C11 0.0545(11) 0.0514(10) 0.0540(10) -0.0005(8) 0.0086(8) 0.0083(8) C14 0.0623(12) 0.0487(10) 0.0659(12) 0.0048(9) 0.0346(10) -0.0009(9) C18 0.0432(9) 0.0585(11) 0.0704(12) -0.0041(9) 0.0209(9) -0.0062(8) C17 0.0498(10) 0.0453(9) 0.0498(9) -0.0015(7) 0.0179(8) -0.0066(7) C2 0.0466(10) 0.0693(12) 0.0515(10) -0.0141(9) 0.0192(8) -0.0008(9) C3 0.0459(10) 0.0827(15) 0.0683(13) -0.0129(11) 0.0275(9) 0.0006(10) C4 0.0377(9) 0.0737(14) 0.0751(13) -0.0087(11) 0.0158(9) -0.0053(9) C13 0.0538(11) 0.0620(12) 0.0889(15) -0.0086(11) 0.0417(11) -0.0081(10) C19 0.0383(9) 0.0717(14) 0.0682(13) 0.0000(10) 0.0035(9) 0.0004(9) O2 0.0558(8) 0.0553(8) 0.0514(7) -0.0178(6) 0.0141(6) -0.0063(6) O1 0.0569(9) 0.1235(15) 0.0411(7) 0.0118(8) 0.0143(6) -0.0080(9) N2 0.0406(7) 0.0392(7) 0.0365(7) -0.0016(5) 0.0118(5) 0.0020(5) N1 0.0370(7) 0.0499(8) 0.0370(7) -0.0043(6) 0.0119(5) -0.0009(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C12 1.7426(19) . ? C15 N1 1.459(2) . ? C15 N2 1.473(2) . ? C15 C16 1.517(2) . ? C9 C10 1.380(2) . ? C9 C14 1.385(2) . ? C9 C8 1.510(2) . ? C7 O2 1.222(2) . ? C7 N2 1.368(2) . ? C7 C6 1.480(2) . ? C6 C5 1.385(2) . ? C6 C1 1.393(2) . ? C16 C21 1.383(2) . ? C16 C17 1.386(2) . ? C8 N2 1.460(2) . ? C1 C2 1.386(2) . ? C1 N1 1.404(2) . ? C12 C11 1.371(3) . ? C12 C13 1.372(3) . ? C10 C11 1.387(3) . ? C5 C4 1.376(3) . ? C21 C20 1.388(3) . ? C21 C22 1.472(2) . ? C22 O1 1.213(2) . ? C22 N1 1.384(2) . ? C20 C19 1.376(3) . ? C14 C13 1.388(3) . ? C18 C19 1.386(3) . ? C18 C17 1.386(3) . ? C2 C3 1.384(3) . ? C3 C4 1.375(3) . ? 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 C15 N2 109.97(13) . . ? N1 C15 C16 101.97(12) . . ? N2 C15 C16 115.41(13) . . ? C10 C9 C14 118.80(16) . . ? C10 C9 C8 122.82(14) . . ? C14 C9 C8 118.35(16) . . ? O2 C7 N2 121.54(15) . . ? O2 C7 C6 121.17(16) . . ? N2 C7 C6 117.29(14) . . ? C5 C6 C1 119.44(16) . . ? C5 C6 C7 119.56(16) . . ? C1 C6 C7 120.98(15) . . ? C21 C16 C17 120.04(16) . . ? C21 C16 C15 109.05(14) . . ? C17 C16 C15 130.86(15) . . ? N2 C8 C9 115.11(13) . . ? C2 C1 C6 120.43(16) . . ? C2 C1 N1 122.61(16) . . ? C6 C1 N1 116.95(14) . . ? C11 C12 C13 121.18(18) . . ? C11 C12 Cl1 118.77(17) . . ? C13 C12 Cl1 120.05(16) . . ? C9 C10 C11 120.82(17) . . ? C4 C5 C6 120.33(18) . . ? C16 C21 C20 122.24(17) . . ? C16 C21 C22 109.87(15) . . ? C20 C21 C22 127.88(17) . . ? O1 C22 N1 125.66(17) . . ? O1 C22 C21 128.79(17) . . ? N1 C22 C21 105.55(14) . . ? C19 C20 C21 117.65(19) . . ? C12 C11 C10 119.26(19) . . ? C9 C14 C13 120.74(19) . . ? C19 C18 C17 122.05(18) . . ? C16 C17 C18 117.59(17) . . ? C3 C2 C1 118.82(18) . . ? C4 C3 C2 121.22(18) . . ? C3 C4 C5 119.74(18) . . ? C12 C13 C14 119.14(18) . . ? C20 C19 C18 120.38(18) . . ? C7 N2 C8 117.47(13) . . ? C7 N2 C15 120.61(13) . . ? C8 N2 C15 117.29(13) . . ? C22 N1 C1 126.40(15) . . ? C22 N1 C15 113.57(14) . . ? C1 N1 C15 118.89(13) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.633 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.042 # Attachment '- MP.cif' data_ils_drb_1_148_1_5 _database_code_depnum_ccdc_archive 'CCDC 807141' #TrackingRef '- MP.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H17 Cl N2 O3' _chemical_formula_weight 392.83 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 21.631(5) _cell_length_b 7.5648(12) _cell_length_c 22.783(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3728.1(12) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1048 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 19.03 _exptl_crystal_description BLOCK _exptl_crystal_colour TRANSPARANT _exptl_crystal_size_max 0.003 _exptl_crystal_size_mid 0.002 _exptl_crystal_size_min 0.0015 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.231 _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 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 '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 8092 _diffrn_reflns_av_R_equivalents 0.0794 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 19.78 _reflns_number_total 1634 _reflns_number_gt 1098 _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^)+(0.1000P)^2^+0.1525P] 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 1634 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1509 _refine_ls_wR_factor_gt 0.1278 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _refine_ls_shift/su_max 2.206 _refine_ls_shift/su_mean 0.047 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 Cl1 Cl 0.15176(10) 1.12433(18) 0.17849(7) 0.0879(8) Uani 1 1 d . . . O2 O 0.28577(18) 0.7344(4) 0.01080(15) 0.0443(10) Uani 1 1 d . . . N2 N 0.1826(2) 0.6886(5) 0.00953(17) 0.0324(11) Uani 1 1 d . . . C8 C 0.1301(2) 0.5938(6) -0.0172(2) 0.0346(14) Uani 1 1 d . . . H8 H 0.1305 0.4700 -0.0046 0.042 Uiso 1 1 calc R . . C9 C 0.1779(2) 0.7174(6) 0.0711(2) 0.0329(13) Uani 1 1 d . . . C15 C 0.2406(3) 0.6813(6) -0.0152(2) 0.0308(13) Uani 1 1 d . . . C11 C 0.1615(3) 0.9111(7) 0.1524(3) 0.0478(16) Uani 1 1 d . . . N1 N 0.1341(2) 0.6025(5) -0.07992(19) 0.0392(12) Uani 1 1 d . . . C7 C 0.0677(2) 0.6736(6) -0.0049(2) 0.0378(14) Uani 1 1 d . . . C2 C 0.0404(3) 0.7200(6) -0.0574(3) 0.0439(15) Uani 1 1 d . . . C21 C 0.1909(3) 0.5673(6) -0.1070(2) 0.0402(15) Uani 1 1 d . . . C16 C 0.2434(3) 0.6068(6) -0.0750(2) 0.0360(14) Uani 1 1 d . . . C10 C 0.1714(2) 0.8877(6) 0.0928(2) 0.0403(15) Uani 1 1 d . . . H10 H 0.1737 0.9846 0.0678 0.048 Uiso 1 1 calc R . . C13 C 0.1657(3) 0.6044(7) 0.1678(3) 0.0628(19) Uani 1 1 d . . . H13 H 0.1642 0.5080 0.1931 0.075 Uiso 1 1 calc R . . C14 C 0.1763(3) 0.5765(7) 0.1091(2) 0.0455(16) Uani 1 1 d . . . H14 H 0.1824 0.4624 0.0950 0.055 Uiso 1 1 calc R . . C17 C 0.3006(3) 0.5728(7) -0.1002(3) 0.0513(16) Uani 1 1 d . . . H17 H 0.3363 0.5958 -0.0788 0.062 Uiso 1 1 calc R . . C20 C 0.1950(4) 0.4978(7) -0.1628(3) 0.0564(18) Uani 1 1 d . . . H20 H 0.1594 0.4710 -0.1838 0.068 Uiso 1 1 calc R . . C18 C 0.3054(4) 0.5052(8) -0.1566(3) 0.0637(19) Uani 1 1 d . . . H18 H 0.3438 0.4850 -0.1736 0.076 Uiso 1 1 calc R . . C12 C 0.1571(3) 0.7714(8) 0.1901(2) 0.0549(17) Uani 1 1 d . . . H12 H 0.1486 0.7888 0.2297 0.066 Uiso 1 1 calc R . . C19 C 0.2520(4) 0.4688(7) -0.1867(3) 0.0622(19) Uani 1 1 d . . . H19 H 0.2546 0.4230 -0.2245 0.075 Uiso 1 1 calc R . . O1 O 0.0764(2) 0.7022(5) -0.15782(19) 0.0737(14) Uani 1 1 d . . . C6 C 0.0355(3) 0.6939(6) 0.0462(3) 0.0490(16) Uani 1 1 d . . . H6 H 0.0528 0.6606 0.0819 0.059 Uiso 1 1 calc R . . C3 C -0.0194(3) 0.7906(7) -0.0597(3) 0.0616(18) Uani 1 1 d . . . H3 H -0.0374 0.8211 -0.0954 0.074 Uiso 1 1 calc R . . C1 C 0.0833(3) 0.6787(7) -0.1055(3) 0.0475(16) Uani 1 1 d . . . C4 C -0.0501(3) 0.8132(7) -0.0086(4) 0.0647(19) Uani 1 1 d . . . H4 H -0.0897 0.8617 -0.0091 0.078 Uiso 1 1 calc R . . C5 C -0.0242(3) 0.7661(7) 0.0436(3) 0.0629(19) Uani 1 1 d . . . H5 H -0.0465 0.7821 0.0782 0.075 Uiso 1 1 calc R . . C22 C 0.9769(15) 0.603(8) 0.7567(12) 0.57(2) Uani 1 1 d . . . H22A H 1.0182 0.6033 0.7721 0.862 Uiso 1 1 calc R . . H22B H 0.9640 0.4840 0.7494 0.862 Uiso 1 1 calc R . . H22C H 0.9494 0.6570 0.7847 0.862 Uiso 1 1 calc R . . O3 O 0.9754(11) 0.704(5) 0.7019(7) 0.57(2) Uani 1 1 d . . . H4A H 0.9560 0.6482 0.6771 0.862 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 Cl1 0.141(2) 0.0516(10) 0.0708(13) -0.0145(8) -0.0091(11) 0.0163(10) O2 0.030(2) 0.055(2) 0.048(2) 0.0025(17) -0.006(2) -0.0086(19) N2 0.031(3) 0.037(2) 0.029(3) 0.0003(19) -0.004(2) -0.003(2) C8 0.024(4) 0.036(3) 0.044(4) 0.002(2) -0.008(3) -0.003(3) C9 0.024(3) 0.040(3) 0.034(4) 0.003(3) -0.005(2) -0.001(2) C15 0.030(4) 0.028(3) 0.034(4) 0.009(2) 0.002(3) 0.001(3) C11 0.054(5) 0.044(3) 0.045(4) -0.010(3) -0.005(3) 0.002(3) N1 0.037(4) 0.048(3) 0.033(3) 0.001(2) -0.007(3) 0.000(2) C7 0.035(4) 0.036(3) 0.043(4) 0.005(3) -0.002(3) -0.011(3) C2 0.035(5) 0.042(3) 0.055(4) 0.005(3) -0.007(4) -0.008(3) C21 0.048(5) 0.037(3) 0.036(4) 0.000(3) 0.000(4) 0.003(3) C16 0.035(4) 0.034(3) 0.039(4) 0.006(3) 0.005(3) 0.006(3) C10 0.051(4) 0.035(3) 0.035(4) 0.004(3) -0.009(3) -0.002(3) C13 0.097(6) 0.045(4) 0.047(5) 0.013(3) -0.008(3) -0.004(3) C14 0.066(5) 0.037(3) 0.034(4) 0.003(3) -0.007(3) 0.001(3) C17 0.051(5) 0.060(4) 0.043(4) 0.013(3) -0.001(3) 0.006(3) C20 0.070(6) 0.050(4) 0.049(5) 0.000(3) -0.002(4) 0.000(3) C18 0.065(6) 0.070(4) 0.056(5) 0.012(4) 0.020(4) 0.018(4) C12 0.080(5) 0.047(4) 0.038(4) 0.002(3) 0.000(3) -0.001(3) C19 0.092(7) 0.056(4) 0.038(4) -0.003(3) 0.015(5) 0.011(4) O1 0.068(4) 0.099(3) 0.054(3) 0.013(2) -0.024(2) -0.002(3) C6 0.040(5) 0.040(3) 0.067(5) -0.003(3) -0.004(4) -0.003(3) C3 0.031(5) 0.051(4) 0.103(6) 0.021(4) -0.022(4) 0.000(3) C1 0.054(5) 0.048(3) 0.040(5) 0.007(3) -0.020(4) -0.014(3) C4 0.031(4) 0.051(4) 0.112(6) 0.012(4) 0.005(5) 0.000(3) C5 0.046(6) 0.044(3) 0.099(6) -0.002(3) 0.016(4) -0.001(4) C22 0.298(18) 1.18(6) 0.241(19) -0.21(4) 0.05(2) -0.03(3) O3 0.298(18) 1.18(6) 0.241(19) -0.21(4) 0.05(2) -0.03(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C11 1.732(5) . ? O2 C15 1.212(6) . ? N2 C15 1.376(6) . ? N2 C9 1.423(6) . ? N2 C8 1.475(6) . ? C8 N1 1.433(6) . ? C8 C7 1.505(7) . ? C9 C14 1.373(6) . ? C9 C10 1.387(6) . ? C15 C16 1.475(7) . ? C11 C12 1.365(7) . ? C11 C10 1.385(7) . ? N1 C1 1.373(7) . ? N1 C21 1.400(7) . ? C7 C6 1.365(7) . ? C7 C2 1.379(7) . ? C2 C3 1.400(8) . ? C2 C1 1.469(8) . ? C21 C20 1.377(7) . ? C21 C16 1.382(7) . ? C16 C17 1.388(7) . ? C13 C12 1.374(7) . ? C13 C14 1.374(7) . ? C17 C18 1.388(8) . ? C20 C19 1.366(8) . ? C18 C19 1.371(9) . ? O1 C1 1.214(6) . ? C6 C5 1.404(8) . ? C3 C4 1.352(8) . ? C4 C5 1.363(8) . ? C22 O3 1.46(4) . ? 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 C15 N2 C9 118.4(4) . . ? C15 N2 C8 120.8(4) . . ? C9 N2 C8 115.2(4) . . ? N1 C8 N2 110.0(4) . . ? N1 C8 C7 102.8(4) . . ? N2 C8 C7 114.8(4) . . ? C14 C9 C10 119.6(5) . . ? C14 C9 N2 120.3(4) . . ? C10 C9 N2 120.1(4) . . ? O2 C15 N2 121.4(5) . . ? O2 C15 C16 123.0(5) . . ? N2 C15 C16 115.6(5) . . ? C12 C11 C10 121.9(5) . . ? C12 C11 Cl1 119.8(5) . . ? C10 C11 Cl1 118.3(4) . . ? C1 N1 C21 126.6(5) . . ? C1 N1 C8 113.2(5) . . ? C21 N1 C8 119.0(4) . . ? C6 C7 C2 119.6(5) . . ? C6 C7 C8 131.3(5) . . ? C2 C7 C8 109.0(5) . . ? C7 C2 C3 121.6(6) . . ? C7 C2 C1 108.8(5) . . ? C3 C2 C1 129.5(6) . . ? C20 C21 C16 121.1(6) . . ? C20 C21 N1 122.4(6) . . ? C16 C21 N1 116.5(5) . . ? C21 C16 C17 118.3(5) . . ? C21 C16 C15 122.4(5) . . ? C17 C16 C15 119.2(6) . . ? C11 C10 C9 118.9(4) . . ? C12 C13 C14 121.5(5) . . ? C9 C14 C13 119.9(5) . . ? C16 C17 C18 121.1(6) . . ? C19 C20 C21 119.2(6) . . ? C19 C18 C17 118.3(6) . . ? C11 C12 C13 118.1(5) . . ? C20 C19 C18 121.9(6) . . ? C7 C6 C5 118.5(6) . . ? C4 C3 C2 118.1(6) . . ? O1 C1 N1 125.2(6) . . ? O1 C1 C2 128.6(6) . . ? N1 C1 C2 106.2(5) . . ? C3 C4 C5 121.1(6) . . ? C4 C5 C6 121.1(6) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 19.78 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.362 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.047