# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Frank King' _publ_contact_author_email FD.KING@BTINTERNET.COM _publ_section_title ; A synthesis of dibenzopyrroloazepines as tetracyclic allocolchicinoids - an unusual 1,2-phenyl shift ; loop_ _publ_author_name 'Frank King' 'Abil E. Aliev' 'Stephen Caddick' 'Richard J. Fitzmaurice' 'Derek A. Tocher' 'Liang Wu.' # Attachment 'STR0764.CIF' data_str0764 _database_code_depnum_ccdc_archive 'CCDC 748250' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H17 N O' _chemical_formula_weight 263.33 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 Pbca 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' '-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 18.680(2) _cell_length_b 7.2722(8) _cell_length_c 19.090(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2593.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9836 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20861 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3153 _reflns_number_gt 2278 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0654P)^2^+0.5933P] 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 ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3153 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1224 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.007 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 O1 O 0.14053(7) 0.06116(18) 1.01416(6) 0.0317(3) Uani 1 1 d . . . N1 N 0.06261(7) 0.11413(19) 0.92669(7) 0.0224(3) Uani 1 1 d . . . C1 C 0.11548(9) 0.0164(2) 0.95682(8) 0.0224(4) Uani 1 1 d . . . C2 C 0.13983(8) -0.1571(2) 0.92079(9) 0.0209(4) Uani 1 1 d . . . C3 C 0.16325(8) -0.2967(2) 0.96564(9) 0.0257(4) Uani 1 1 d . . . H3A H 0.1639 -0.2752 1.0147 0.031 Uiso 1 1 calc R . . C4 C 0.18543(9) -0.4651(3) 0.94027(9) 0.0285(4) Uani 1 1 d . . . H4A H 0.2014 -0.5577 0.9717 0.034 Uiso 1 1 calc R . . C5 C 0.18428(9) -0.4987(2) 0.86887(9) 0.0269(4) Uani 1 1 d . . . H5A H 0.1970 -0.6163 0.8512 0.032 Uiso 1 1 calc R . . C6 C 0.16444(8) -0.3591(2) 0.82352(9) 0.0232(4) Uani 1 1 d . . . H6A H 0.1651 -0.3818 0.7745 0.028 Uiso 1 1 calc R . . C7 C 0.14336(8) -0.1852(2) 0.84767(8) 0.0195(3) Uani 1 1 d . . . C8 C 0.13184(8) -0.0381(2) 0.79486(8) 0.0197(3) Uani 1 1 d . . . C9 C 0.17970(8) -0.0242(2) 0.73881(8) 0.0209(4) Uani 1 1 d . . . H9A H 0.2187 -0.1079 0.7362 0.025 Uiso 1 1 calc R . . C10 C 0.17206(9) 0.1086(2) 0.68665(8) 0.0213(4) Uani 1 1 d . . . C11 C 0.11500(9) 0.2306(2) 0.69215(9) 0.0260(4) Uani 1 1 d . . . H11A H 0.1086 0.3225 0.6574 0.031 Uiso 1 1 calc R . . C12 C 0.06735(9) 0.2198(2) 0.74780(9) 0.0260(4) Uani 1 1 d . . . H12A H 0.0290 0.3054 0.7506 0.031 Uiso 1 1 calc R . . C13 C 0.07454(8) 0.0864(2) 0.79939(8) 0.0208(4) Uani 1 1 d . . . C14 C 0.02461(8) 0.0657(2) 0.86119(8) 0.0211(4) Uani 1 1 d . . . H14A H 0.0081 -0.0648 0.8640 0.025 Uiso 1 1 calc R . . C15 C -0.04065(9) 0.1935(2) 0.86365(9) 0.0270(4) Uani 1 1 d . . . H15A H -0.0562 0.2281 0.8158 0.032 Uiso 1 1 calc R . . H15B H -0.0812 0.1342 0.8883 0.032 Uiso 1 1 calc R . . C16 C -0.01391(10) 0.3612(2) 0.90401(10) 0.0311(4) Uani 1 1 d . . . H16A H 0.0150 0.4429 0.8736 0.037 Uiso 1 1 calc R . . H16B H -0.0543 0.4322 0.9240 0.037 Uiso 1 1 calc R . . C17 C 0.03154(9) 0.2761(2) 0.96118(9) 0.0277(4) Uani 1 1 d . . . H17A H 0.0693 0.3620 0.9769 0.033 Uiso 1 1 calc R . . H17B H 0.0019 0.2400 1.0019 0.033 Uiso 1 1 calc R . . C18 C 0.22360(10) 0.1182(2) 0.62594(9) 0.0276(4) Uani 1 1 d . . . H18A H 0.2098 0.2193 0.5948 0.041 Uiso 1 1 calc R . . H18B H 0.2223 0.0020 0.6000 0.041 Uiso 1 1 calc R . . H18C H 0.2721 0.1395 0.6436 0.041 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 O1 0.0346(7) 0.0403(8) 0.0202(6) -0.0044(5) -0.0056(5) -0.0053(6) N1 0.0230(7) 0.0251(7) 0.0192(7) -0.0042(6) 0.0014(6) -0.0020(6) C1 0.0214(8) 0.0268(9) 0.0189(8) 0.0007(7) 0.0014(7) -0.0068(7) C2 0.0157(7) 0.0258(8) 0.0211(8) 0.0012(7) 0.0009(6) -0.0045(6) C3 0.0201(8) 0.0363(10) 0.0206(8) 0.0054(7) 0.0002(7) -0.0013(7) C4 0.0219(9) 0.0341(10) 0.0296(10) 0.0126(8) 0.0015(7) 0.0048(7) C5 0.0221(8) 0.0257(9) 0.0330(10) 0.0031(7) 0.0051(7) 0.0035(7) C6 0.0212(8) 0.0267(9) 0.0217(8) 0.0012(7) 0.0021(7) 0.0002(7) C7 0.0155(7) 0.0232(8) 0.0197(8) 0.0024(6) 0.0000(6) -0.0015(6) C8 0.0205(8) 0.0212(8) 0.0174(8) -0.0016(6) -0.0026(6) -0.0022(6) C9 0.0219(8) 0.0216(8) 0.0192(8) -0.0020(6) -0.0014(6) 0.0003(6) C10 0.0249(8) 0.0224(8) 0.0166(8) -0.0012(6) -0.0009(6) -0.0033(7) C11 0.0325(9) 0.0225(8) 0.0230(8) 0.0041(7) -0.0010(7) 0.0022(7) C12 0.0267(9) 0.0253(9) 0.0261(9) 0.0016(7) -0.0004(7) 0.0062(7) C13 0.0204(8) 0.0223(8) 0.0197(8) -0.0023(6) -0.0024(7) -0.0010(6) C14 0.0202(8) 0.0224(8) 0.0207(8) -0.0012(6) -0.0008(6) -0.0007(6) C15 0.0231(8) 0.0301(9) 0.0278(9) -0.0006(7) 0.0024(7) 0.0046(7) C16 0.0329(10) 0.0260(9) 0.0344(10) -0.0026(8) 0.0094(8) 0.0019(8) C17 0.0301(9) 0.0268(9) 0.0260(9) -0.0064(7) 0.0085(8) -0.0041(7) C18 0.0338(9) 0.0273(9) 0.0217(9) 0.0023(7) 0.0028(7) 0.0019(7) _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 O1 C1 1.2341(19) . ? N1 C1 1.346(2) . ? N1 C17 1.469(2) . ? N1 C14 1.480(2) . ? C1 C2 1.507(2) . ? C2 C3 1.398(2) . ? C2 C7 1.412(2) . ? C3 C4 1.381(2) . ? C4 C5 1.385(3) . ? C5 C6 1.385(2) . ? C6 C7 1.402(2) . ? C7 C8 1.486(2) . ? C8 C9 1.398(2) . ? C8 C13 1.405(2) . ? C9 C10 1.394(2) . ? C10 C11 1.391(2) . ? C10 C18 1.508(2) . ? C11 C12 1.388(2) . ? C12 C13 1.389(2) . ? C13 C14 1.511(2) . ? C14 C15 1.534(2) . ? C15 C16 1.526(2) . ? C16 C17 1.515(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 C1 N1 C17 121.45(14) . . ? C1 N1 C14 125.97(13) . . ? C17 N1 C14 112.32(13) . . ? O1 C1 N1 121.21(16) . . ? O1 C1 C2 120.72(15) . . ? N1 C1 C2 117.94(14) . . ? C3 C2 C7 119.03(15) . . ? C3 C2 C1 115.02(15) . . ? C7 C2 C1 125.90(15) . . ? C4 C3 C2 121.55(16) . . ? C3 C4 C5 119.78(16) . . ? C6 C5 C4 119.37(16) . . ? C5 C6 C7 122.05(15) . . ? C6 C7 C2 117.95(14) . . ? C6 C7 C8 117.84(14) . . ? C2 C7 C8 124.02(14) . . ? C9 C8 C13 119.20(15) . . ? C9 C8 C7 118.60(14) . . ? C13 C8 C7 122.20(14) . . ? C10 C9 C8 122.08(15) . . ? C11 C10 C9 117.80(15) . . ? C11 C10 C18 121.15(15) . . ? C9 C10 C18 121.04(15) . . ? C12 C11 C10 120.86(15) . . ? C11 C12 C13 121.36(16) . . ? C12 C13 C8 118.69(15) . . ? C12 C13 C14 124.29(14) . . ? C8 C13 C14 117.01(14) . . ? N1 C14 C13 109.86(12) . . ? N1 C14 C15 102.19(12) . . ? C13 C14 C15 117.02(14) . . ? C16 C15 C14 103.85(14) . . ? C17 C16 C15 102.74(14) . . ? N1 C17 C16 103.07(13) . . ? 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 C17 N1 C1 O1 -1.1(2) . . . . ? C14 N1 C1 O1 -174.84(15) . . . . ? C17 N1 C1 C2 174.78(14) . . . . ? C14 N1 C1 C2 1.1(2) . . . . ? O1 C1 C2 C3 28.2(2) . . . . ? N1 C1 C2 C3 -147.68(15) . . . . ? O1 C1 C2 C7 -149.10(16) . . . . ? N1 C1 C2 C7 35.0(2) . . . . ? C7 C2 C3 C4 -4.1(2) . . . . ? C1 C2 C3 C4 178.34(15) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C3 C4 C5 C6 3.4(3) . . . . ? C4 C5 C6 C7 -1.9(3) . . . . ? C5 C6 C7 C2 -2.6(2) . . . . ? C5 C6 C7 C8 172.54(14) . . . . ? C3 C2 C7 C6 5.5(2) . . . . ? C1 C2 C7 C6 -177.24(15) . . . . ? C3 C2 C7 C8 -169.33(14) . . . . ? C1 C2 C7 C8 7.9(2) . . . . ? C6 C7 C8 C9 -40.6(2) . . . . ? C2 C7 C8 C9 134.27(16) . . . . ? C6 C7 C8 C13 139.22(16) . . . . ? C2 C7 C8 C13 -45.9(2) . . . . ? C13 C8 C9 C10 -0.6(2) . . . . ? C7 C8 C9 C10 179.19(15) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C8 C9 C10 C18 -178.76(15) . . . . ? C9 C10 C11 C12 -0.1(2) . . . . ? C18 C10 C11 C12 179.35(16) . . . . ? C10 C11 C12 C13 -0.6(3) . . . . ? C11 C12 C13 C8 0.6(2) . . . . ? C11 C12 C13 C14 -179.68(16) . . . . ? C9 C8 C13 C12 0.0(2) . . . . ? C7 C8 C13 C12 -179.83(15) . . . . ? C9 C8 C13 C14 -179.75(14) . . . . ? C7 C8 C13 C14 0.4(2) . . . . ? C1 N1 C14 C13 -69.52(19) . . . . ? C17 N1 C14 C13 116.26(14) . . . . ? C1 N1 C14 C15 165.57(15) . . . . ? C17 N1 C14 C15 -8.65(17) . . . . ? C12 C13 C14 N1 -111.75(17) . . . . ? C8 C13 C14 N1 67.96(18) . . . . ? C12 C13 C14 C15 4.1(2) . . . . ? C8 C13 C14 C15 -176.18(14) . . . . ? N1 C14 C15 C16 29.78(16) . . . . ? C13 C14 C15 C16 -90.24(16) . . . . ? C14 C15 C16 C17 -40.16(17) . . . . ? C1 N1 C17 C16 169.44(15) . . . . ? C14 N1 C17 C16 -16.04(17) . . . . ? C15 C16 C17 N1 34.04(16) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.363 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.051 # Attachment 'STR0768.CIF' data_str0768 _database_code_depnum_ccdc_archive 'CCDC 748251' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 Cl N O4' _chemical_formula_weight 391.88 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 14.9657(13) _cell_length_b 12.7574(11) _cell_length_c 10.6945(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.813(2) _cell_angle_gamma 90.00 _cell_volume 2041.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9547 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17052 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.22 _reflns_number_total 4848 _reflns_number_gt 3722 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1677P)^2^+1.1514P] 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 ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4848 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0737 _refine_ls_wR_factor_ref 0.2511 _refine_ls_wR_factor_gt 0.2330 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 Cl1A Cl 0.95735(5) 0.26287(7) 0.17875(8) 0.0316(3) Uani 0.754(3) 1 d P . . Cl1B Cl 0.9866(2) 0.1305(3) -0.0618(3) 0.0444(10) Uani 0.246(3) 1 d P . . N1 N 0.11757(13) 0.12865(16) 0.25322(19) 0.0235(5) Uani 1 1 d . . . H1N H 0.0718 0.1748 0.2313 0.028 Uiso 1 1 calc R . . O1 O 0.31130(14) -0.25404(14) 0.1266(2) 0.0365(5) Uani 1 1 d . . . O2 O 0.21416(12) 0.40337(14) 0.36050(16) 0.0258(4) Uani 1 1 d . . . O3 O 0.35040(13) 0.50726(14) 0.22925(18) 0.0313(5) Uani 1 1 d . . . O4 O 0.45951(12) 0.40183(14) 0.08597(18) 0.0293(4) Uani 1 1 d . . . C1 C 0.15454(16) 0.0868(2) 0.1327(2) 0.0247(5) Uani 1 1 d . . . H1A H 0.1079 0.0450 0.0892 0.030 Uiso 1 1 calc R . . H1B H 0.1701 0.1464 0.0779 0.030 Uiso 1 1 calc R . . C2 C 0.23563(16) 0.02000(19) 0.1535(2) 0.0234(5) Uani 1 1 d . . . C3 C 0.23130(17) -0.08753(19) 0.1324(2) 0.0255(5) Uani 1 1 d . . . H3A H 0.1764 -0.1190 0.1073 0.031 Uiso 1 1 calc R . . C4 C 0.30788(17) -0.1490(2) 0.1482(2) 0.0269(5) Uani 1 1 d . . . C5 C 0.2349(2) -0.3013(2) 0.0701(3) 0.0424(7) Uani 1 1 d . . . H5A H 0.2454 -0.3766 0.0599 0.064 Uiso 1 1 calc R . . H5B H 0.2235 -0.2694 -0.0119 0.064 Uiso 1 1 calc R . . H5C H 0.1830 -0.2905 0.1235 0.064 Uiso 1 1 calc R . . C6 C 0.38733(18) -0.1025(2) 0.1878(3) 0.0299(6) Uani 1 1 d . . . H6A H 0.4391 -0.1444 0.2006 0.036 Uiso 1 1 calc R . . C7 C 0.39158(17) 0.0038(2) 0.2087(3) 0.0283(6) Uani 1 1 d . . . H7A H 0.4463 0.0344 0.2362 0.034 Uiso 1 1 calc R . . C8 C 0.31628(16) 0.06754(19) 0.1900(2) 0.0236(5) Uani 1 1 d . . . C9 C 0.32216(16) 0.18326(19) 0.2040(2) 0.0232(5) Uani 1 1 d . . . C10 C 0.39034(17) 0.23545(19) 0.1418(2) 0.0248(5) Uani 1 1 d . . . H10A H 0.4317 0.1964 0.0939 0.030 Uiso 1 1 calc R . . C11 C 0.39847(16) 0.34346(19) 0.1489(2) 0.0237(5) Uani 1 1 d . . . C12 C 0.51724(19) 0.3477(2) 0.0030(3) 0.0353(7) Uani 1 1 d . . . H12A H 0.5577 0.3979 -0.0363 0.053 Uiso 1 1 calc R . . H12B H 0.4814 0.3123 -0.0618 0.053 Uiso 1 1 calc R . . H12C H 0.5523 0.2956 0.0500 0.053 Uiso 1 1 calc R . . C13 C 0.34025(16) 0.40116(19) 0.2254(2) 0.0226(5) Uani 1 1 d . . . C14 C 0.3644(2) 0.5525(3) 0.3499(3) 0.0452(8) Uani 1 1 d . . . H14A H 0.3711 0.6286 0.3417 0.068 Uiso 1 1 calc R . . H14B H 0.4186 0.5229 0.3883 0.068 Uiso 1 1 calc R . . H14C H 0.3130 0.5371 0.4027 0.068 Uiso 1 1 calc R . . C15 C 0.27058(16) 0.34859(19) 0.2845(2) 0.0224(5) Uani 1 1 d . . . C16 C 0.1523(2) 0.4721(2) 0.2970(3) 0.0377(7) Uani 1 1 d . . . H16A H 0.1152 0.5078 0.3585 0.057 Uiso 1 1 calc R . . H16B H 0.1141 0.4311 0.2401 0.057 Uiso 1 1 calc R . . H16C H 0.1856 0.5243 0.2490 0.057 Uiso 1 1 calc R . . C17 C 0.25945(16) 0.23947(19) 0.2729(2) 0.0224(5) Uani 1 1 d . . . C18 C 0.18198(15) 0.18920(19) 0.3389(2) 0.0227(5) Uani 1 1 d . . . H18A H 0.1467 0.2477 0.3762 0.027 Uiso 1 1 calc R . . C19 C 0.20266(18) 0.1126(2) 0.4452(2) 0.0285(6) Uani 1 1 d . . . H19A H 0.2227 0.1497 0.5218 0.034 Uiso 1 1 calc R . . H19B H 0.2487 0.0610 0.4210 0.034 Uiso 1 1 calc R . . C20 C 0.11080(19) 0.0597(2) 0.4631(3) 0.0339(6) Uani 1 1 d . . . H20A H 0.1174 -0.0081 0.5074 0.041 Uiso 1 1 calc R . . H20B H 0.0703 0.1055 0.5110 0.041 Uiso 1 1 calc R . . C21 C 0.07595(19) 0.0435(2) 0.3316(3) 0.0326(6) Uani 1 1 d . . . H21A H 0.0100 0.0491 0.3288 0.039 Uiso 1 1 calc R . . H21B H 0.0932 -0.0265 0.3003 0.039 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 Cl1A 0.0256(5) 0.0316(5) 0.0374(5) 0.0015(3) -0.0025(3) 0.0146(3) Cl1B 0.0354(16) 0.051(2) 0.0461(18) -0.0063(14) -0.0094(13) 0.0148(13) N1 0.0210(10) 0.0252(11) 0.0242(10) 0.0009(8) -0.0004(8) -0.0007(8) O1 0.0359(11) 0.0196(9) 0.0540(13) -0.0021(8) 0.0005(9) 0.0022(7) O2 0.0279(9) 0.0255(9) 0.0242(9) -0.0016(7) 0.0031(7) 0.0039(7) O3 0.0386(11) 0.0211(9) 0.0344(10) -0.0030(7) 0.0069(8) -0.0022(7) O4 0.0280(9) 0.0239(9) 0.0364(10) 0.0007(7) 0.0120(8) -0.0015(7) C1 0.0248(12) 0.0265(12) 0.0227(11) -0.0009(9) -0.0006(9) 0.0018(9) C2 0.0259(12) 0.0228(12) 0.0215(11) 0.0019(9) 0.0007(9) 0.0001(9) C3 0.0254(12) 0.0227(12) 0.0285(12) 0.0006(9) 0.0003(10) -0.0020(9) C4 0.0297(13) 0.0209(12) 0.0301(12) 0.0018(10) 0.0020(10) 0.0016(9) C5 0.0411(16) 0.0235(14) 0.062(2) -0.0059(13) -0.0007(15) -0.0032(12) C6 0.0271(13) 0.0250(13) 0.0376(14) 0.0019(11) -0.0009(11) 0.0063(10) C7 0.0241(12) 0.0254(13) 0.0353(14) -0.0002(10) -0.0007(10) 0.0000(10) C8 0.0245(12) 0.0210(12) 0.0253(11) 0.0016(9) 0.0025(9) 0.0003(9) C9 0.0225(12) 0.0221(12) 0.0250(11) 0.0008(9) -0.0004(9) -0.0004(9) C10 0.0230(12) 0.0233(12) 0.0282(12) -0.0009(10) 0.0028(10) 0.0015(9) C11 0.0220(11) 0.0233(12) 0.0260(12) 0.0017(10) 0.0011(9) -0.0017(9) C12 0.0347(15) 0.0292(14) 0.0425(15) 0.0010(12) 0.0179(12) 0.0001(11) C13 0.0226(11) 0.0210(12) 0.0243(12) -0.0009(9) -0.0006(9) -0.0007(9) C14 0.0512(19) 0.0398(17) 0.0449(17) -0.0193(14) 0.0124(14) -0.0175(14) C15 0.0245(12) 0.0242(12) 0.0183(10) -0.0014(9) 0.0005(9) 0.0010(9) C16 0.0352(15) 0.0387(16) 0.0395(15) 0.0073(13) 0.0072(12) 0.0118(12) C17 0.0231(12) 0.0234(12) 0.0208(11) 0.0012(9) -0.0014(9) -0.0006(9) C18 0.0225(11) 0.0220(12) 0.0235(11) 0.0004(9) 0.0002(9) -0.0007(9) C19 0.0290(13) 0.0330(14) 0.0236(12) 0.0040(10) -0.0003(10) -0.0022(10) C20 0.0341(14) 0.0361(15) 0.0315(14) 0.0058(11) 0.0028(11) -0.0041(11) C21 0.0329(14) 0.0333(15) 0.0317(14) 0.0029(11) 0.0036(11) -0.0114(11) _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 C1 1.507(3) . ? N1 C21 1.511(3) . ? N1 C18 1.530(3) . ? O1 C4 1.361(3) . ? O1 C5 1.420(4) . ? O2 C15 1.372(3) . ? O2 C16 1.439(3) . ? O3 C13 1.363(3) . ? O3 C14 1.427(3) . ? O4 C11 1.363(3) . ? O4 C12 1.426(3) . ? C1 C2 1.497(3) . ? C2 C3 1.392(3) . ? C2 C8 1.401(3) . ? C3 C4 1.397(3) . ? C4 C6 1.390(4) . ? C6 C7 1.376(4) . ? C7 C8 1.402(3) . ? C8 C9 1.486(3) . ? C9 C10 1.395(3) . ? C9 C17 1.399(3) . ? C10 C11 1.385(3) . ? C11 C13 1.411(3) . ? C13 C15 1.398(3) . ? C15 C17 1.407(3) . ? C17 C18 1.509(3) . ? C18 C19 1.527(3) . ? C19 C20 1.546(4) . ? C20 C21 1.507(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 C1 N1 C21 112.3(2) . . ? C1 N1 C18 117.07(18) . . ? C21 N1 C18 106.97(19) . . ? C4 O1 C5 117.3(2) . . ? C15 O2 C16 115.3(2) . . ? C13 O3 C14 116.4(2) . . ? C11 O4 C12 117.3(2) . . ? C2 C1 N1 112.4(2) . . ? C3 C2 C8 120.6(2) . . ? C3 C2 C1 120.1(2) . . ? C8 C2 C1 119.2(2) . . ? C2 C3 C4 119.8(2) . . ? O1 C4 C6 116.0(2) . . ? O1 C4 C3 124.4(2) . . ? C6 C4 C3 119.6(2) . . ? C7 C6 C4 120.5(2) . . ? C6 C7 C8 120.9(2) . . ? C2 C8 C7 118.5(2) . . ? C2 C8 C9 120.5(2) . . ? C7 C8 C9 121.0(2) . . ? C10 C9 C17 120.5(2) . . ? C10 C9 C8 117.9(2) . . ? C17 C9 C8 121.6(2) . . ? C11 C10 C9 120.8(2) . . ? O4 C11 C10 125.1(2) . . ? O4 C11 C13 115.1(2) . . ? C10 C11 C13 119.7(2) . . ? O3 C13 C15 123.1(2) . . ? O3 C13 C11 117.8(2) . . ? C15 C13 C11 118.8(2) . . ? O2 C15 C13 119.5(2) . . ? O2 C15 C17 118.9(2) . . ? C13 C15 C17 121.5(2) . . ? C9 C17 C15 118.3(2) . . ? C9 C17 C18 123.6(2) . . ? C15 C17 C18 118.0(2) . . ? C17 C18 C19 118.1(2) . . ? C17 C18 N1 114.59(19) . . ? C19 C18 N1 104.00(19) . . ? C18 C19 C20 101.6(2) . . ? C21 C20 C19 103.9(2) . . ? C20 C21 N1 106.2(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 C21 N1 C1 C2 -69.7(3) . . . . ? C18 N1 C1 C2 54.6(3) . . . . ? N1 C1 C2 C3 110.5(3) . . . . ? N1 C1 C2 C8 -71.8(3) . . . . ? C8 C2 C3 C4 0.3(4) . . . . ? C1 C2 C3 C4 178.0(2) . . . . ? C5 O1 C4 C6 -171.7(3) . . . . ? C5 O1 C4 C3 7.9(4) . . . . ? C2 C3 C4 O1 -178.1(2) . . . . ? C2 C3 C4 C6 1.5(4) . . . . ? O1 C4 C6 C7 178.1(3) . . . . ? C3 C4 C6 C7 -1.5(4) . . . . ? C4 C6 C7 C8 -0.3(4) . . . . ? C3 C2 C8 C7 -2.1(4) . . . . ? C1 C2 C8 C7 -179.8(2) . . . . ? C3 C2 C8 C9 175.8(2) . . . . ? C1 C2 C8 C9 -1.9(3) . . . . ? C6 C7 C8 C2 2.1(4) . . . . ? C6 C7 C8 C9 -175.8(2) . . . . ? C2 C8 C9 C10 -128.0(3) . . . . ? C7 C8 C9 C10 49.9(3) . . . . ? C2 C8 C9 C17 49.3(3) . . . . ? C7 C8 C9 C17 -132.8(3) . . . . ? C17 C9 C10 C11 1.3(4) . . . . ? C8 C9 C10 C11 178.7(2) . . . . ? C12 O4 C11 C10 2.4(4) . . . . ? C12 O4 C11 C13 -177.2(2) . . . . ? C9 C10 C11 O4 -176.1(2) . . . . ? C9 C10 C11 C13 3.5(4) . . . . ? C14 O3 C13 C15 61.6(3) . . . . ? C14 O3 C13 C11 -124.1(3) . . . . ? O4 C11 C13 O3 -0.1(3) . . . . ? C10 C11 C13 O3 -179.8(2) . . . . ? O4 C11 C13 C15 174.4(2) . . . . ? C10 C11 C13 C15 -5.3(3) . . . . ? C16 O2 C15 C13 72.4(3) . . . . ? C16 O2 C15 C17 -110.7(3) . . . . ? O3 C13 C15 O2 -6.7(3) . . . . ? C11 C13 C15 O2 179.1(2) . . . . ? O3 C13 C15 C17 176.5(2) . . . . ? C11 C13 C15 C17 2.3(3) . . . . ? C10 C9 C17 C15 -4.2(3) . . . . ? C8 C9 C17 C15 178.5(2) . . . . ? C10 C9 C17 C18 177.7(2) . . . . ? C8 C9 C17 C18 0.5(4) . . . . ? O2 C15 C17 C9 -174.4(2) . . . . ? C13 C15 C17 C9 2.4(3) . . . . ? O2 C15 C17 C18 3.7(3) . . . . ? C13 C15 C17 C18 -179.5(2) . . . . ? C9 C17 C18 C19 63.5(3) . . . . ? C15 C17 C18 C19 -114.6(3) . . . . ? C9 C17 C18 N1 -59.6(3) . . . . ? C15 C17 C18 N1 122.4(2) . . . . ? C1 N1 C18 C17 25.2(3) . . . . ? C21 N1 C18 C17 152.1(2) . . . . ? C1 N1 C18 C19 -105.2(2) . . . . ? C21 N1 C18 C19 21.7(2) . . . . ? C17 C18 C19 C20 -166.3(2) . . . . ? N1 C18 C19 C20 -38.0(2) . . . . ? C18 C19 C20 C21 40.9(3) . . . . ? C19 C20 C21 N1 -27.9(3) . . . . ? C1 N1 C21 C20 133.7(2) . . . . ? C18 N1 C21 C20 4.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.297 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.106