# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email chinaleejian@hotmail.com _publ_contact_author_name 'Jian Li' loop_ _publ_author_name 'Jian Li' 'Yuejin Liu' 'Chunju Li' 'Haohua Jie ' 'Xueshun Jia' data_110527b_0m _database_code_depnum_ccdc_archive 'CCDC 836562' #TrackingRef '110527b_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H13 N O5' _chemical_formula_weight 287.26 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 P2(1)/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 9.394(3) _cell_length_b 9.114(2) _cell_length_c 16.558(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.714(3) _cell_angle_gamma 90.00 _cell_volume 1371.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2113 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 22.95 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9791 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details sadabs _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 6888 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0294 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2429 _reflns_number_gt 1889 _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^)+(0.0415P)^2^+0.2648P] 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 0.049(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2429 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 1.07670(17) 0.67222(17) 0.29642(10) 0.0401(4) Uani 1 1 d . . . C2 C 1.20148(18) 0.6695(2) 0.36149(11) 0.0488(4) Uani 1 1 d . . . H2 H 1.2815 0.6105 0.3599 0.059 Uiso 1 1 calc R . . C3 C 1.20264(19) 0.7587(2) 0.42949(11) 0.0548(5) Uani 1 1 d . . . H3 H 1.2854 0.7596 0.4745 0.066 Uiso 1 1 calc R . . C4 C 1.0847(2) 0.8457(2) 0.43209(11) 0.0562(5) Uani 1 1 d . . . H4 H 1.0887 0.9045 0.4785 0.067 Uiso 1 1 calc R . . C5 C 0.95926(19) 0.84692(19) 0.36605(10) 0.0487(4) Uani 1 1 d . . . H5 H 0.8790 0.9055 0.3677 0.058 Uiso 1 1 calc R . . C6 C 0.95692(16) 0.75923(17) 0.29829(9) 0.0396(4) Uani 1 1 d . . . C7 C 0.83876(16) 0.73194(17) 0.21967(9) 0.0401(4) Uani 1 1 d . . . C8 C 0.91161(18) 0.61610(18) 0.17419(10) 0.0442(4) Uani 1 1 d . . . C9 C 0.58726(18) 0.7440(2) 0.19886(11) 0.0483(4) Uani 1 1 d . . . C10 C 0.63301(18) 0.86381(19) 0.15255(10) 0.0463(4) Uani 1 1 d . . . H10 H 0.5705 0.9322 0.1198 0.056 Uiso 1 1 calc R . . C11 C 0.77701(16) 0.85954(17) 0.16454(9) 0.0383(4) Uani 1 1 d . . . C12 C 0.87305(18) 0.95462(18) 0.12907(10) 0.0429(4) Uani 1 1 d . . . C13 C 0.8815(2) 1.1675(2) 0.04854(13) 0.0697(6) Uani 1 1 d . . . H13A H 0.9573 1.1182 0.0284 0.084 Uiso 1 1 calc R . . H13B H 0.9287 1.2369 0.0914 0.084 Uiso 1 1 calc R . . C14 C 0.7807(3) 1.2450(3) -0.02042(14) 0.0843(7) Uani 1 1 d . . . H14A H 0.7408 1.1771 -0.0647 0.126 Uiso 1 1 calc R . . H14B H 0.8332 1.3210 -0.0408 0.126 Uiso 1 1 calc R . . H14C H 0.7021 1.2877 -0.0009 0.126 Uiso 1 1 calc R . . C15 C 1.15337(19) 0.4925(2) 0.19884(12) 0.0567(5) Uani 1 1 d . . . H15A H 1.1127 0.4557 0.1435 0.085 Uiso 1 1 calc R . . H15B H 1.1745 0.4120 0.2374 0.085 Uiso 1 1 calc R . . H15C H 1.2425 0.5452 0.2004 0.085 Uiso 1 1 calc R . . N1 N 1.04804(14) 0.59043(15) 0.22194(8) 0.0440(4) Uani 1 1 d . . . O1 O 0.71011(11) 0.66639(13) 0.23727(7) 0.0488(3) Uani 1 1 d . . . O2 O 0.46899(13) 0.71005(16) 0.20681(9) 0.0709(4) Uani 1 1 d . . . O3 O 0.85219(14) 0.55966(14) 0.10783(8) 0.0620(4) Uani 1 1 d . . . O4 O 0.79817(12) 1.06072(13) 0.08298(7) 0.0526(3) Uani 1 1 d . . . O5 O 1.00250(13) 0.93314(15) 0.14056(8) 0.0634(4) 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 0.0388(8) 0.0371(9) 0.0432(9) 0.0031(7) 0.0085(7) -0.0013(7) C2 0.0393(9) 0.0524(11) 0.0523(11) 0.0065(8) 0.0074(8) 0.0045(8) C3 0.0490(10) 0.0634(12) 0.0455(10) 0.0051(9) 0.0000(8) -0.0001(9) C4 0.0625(12) 0.0614(12) 0.0416(10) -0.0046(9) 0.0072(9) 0.0020(10) C5 0.0503(10) 0.0490(11) 0.0466(10) -0.0001(8) 0.0119(8) 0.0083(8) C6 0.0388(8) 0.0389(9) 0.0398(9) 0.0051(7) 0.0073(7) 0.0013(7) C7 0.0362(8) 0.0397(9) 0.0430(9) 0.0037(7) 0.0079(7) -0.0008(7) C8 0.0458(9) 0.0389(9) 0.0458(10) -0.0005(8) 0.0075(8) -0.0010(8) C9 0.0385(9) 0.0502(11) 0.0549(11) -0.0009(8) 0.0095(8) -0.0011(8) C10 0.0420(9) 0.0438(10) 0.0496(10) 0.0038(8) 0.0050(8) 0.0050(7) C11 0.0382(8) 0.0376(9) 0.0373(8) -0.0023(7) 0.0063(7) 0.0007(7) C12 0.0444(9) 0.0427(10) 0.0400(9) 0.0005(7) 0.0081(7) 0.0014(8) C13 0.0756(13) 0.0630(13) 0.0695(13) 0.0205(11) 0.0165(11) -0.0130(11) C14 0.1039(18) 0.0783(16) 0.0735(15) 0.0313(12) 0.0279(13) 0.0130(13) C15 0.0525(10) 0.0514(11) 0.0702(13) -0.0036(9) 0.0230(9) 0.0072(9) N1 0.0400(7) 0.0408(8) 0.0501(8) -0.0035(6) 0.0096(6) 0.0050(6) O1 0.0409(6) 0.0478(7) 0.0571(7) 0.0110(5) 0.0114(6) -0.0025(5) O2 0.0434(7) 0.0769(10) 0.0947(11) 0.0080(8) 0.0217(7) -0.0076(7) O3 0.0626(8) 0.0599(9) 0.0559(8) -0.0153(6) 0.0011(6) 0.0018(6) O4 0.0527(7) 0.0501(7) 0.0535(7) 0.0150(6) 0.0110(6) 0.0015(6) O5 0.0442(7) 0.0690(9) 0.0793(9) 0.0209(7) 0.0198(7) 0.0044(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 C1 C2 1.376(2) . ? C1 C6 1.383(2) . ? C1 N1 1.407(2) . ? C2 C3 1.387(2) . ? C2 H2 0.9300 . ? C3 C4 1.372(2) . ? C3 H3 0.9300 . ? C4 C5 1.389(2) . ? C4 H4 0.9300 . ? C5 C6 1.373(2) . ? C5 H5 0.9300 . ? C6 C7 1.502(2) . ? C7 O1 1.4428(18) . ? C7 C11 1.501(2) . ? C7 C8 1.553(2) . ? C8 O3 1.2133(19) . ? C8 N1 1.345(2) . ? C9 O2 1.1923(19) . ? C9 O1 1.365(2) . ? C9 C10 1.460(2) . ? C10 C11 1.317(2) . ? C10 H10 0.9300 . ? C11 C12 1.476(2) . ? C12 O5 1.1983(19) . ? C12 O4 1.3190(19) . ? C13 O4 1.453(2) . ? C13 C14 1.466(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N1 1.454(2) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? 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 C2 C1 C6 121.91(16) . . ? C2 C1 N1 127.73(15) . . ? C6 C1 N1 110.34(13) . . ? C1 C2 C3 117.05(16) . . ? C1 C2 H2 121.5 . . ? C3 C2 H2 121.5 . . ? C4 C3 C2 121.62(16) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 120.68(17) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 118.22(16) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 120.50(15) . . ? C5 C6 C7 131.28(15) . . ? C1 C6 C7 108.18(13) . . ? O1 C7 C11 103.26(12) . . ? O1 C7 C6 111.48(12) . . ? C11 C7 C6 119.03(13) . . ? O1 C7 C8 108.14(13) . . ? C11 C7 C8 112.44(13) . . ? C6 C7 C8 102.31(12) . . ? O3 C8 N1 127.54(16) . . ? O3 C8 C7 124.70(15) . . ? N1 C8 C7 107.75(14) . . ? O2 C9 O1 121.02(16) . . ? O2 C9 C10 131.20(17) . . ? O1 C9 C10 107.78(14) . . ? C11 C10 C9 109.07(15) . . ? C11 C10 H10 125.5 . . ? C9 C10 H10 125.5 . . ? C10 C11 C12 129.12(15) . . ? C10 C11 C7 109.76(14) . . ? C12 C11 C7 121.05(13) . . ? O5 C12 O4 125.60(16) . . ? O5 C12 C11 122.63(15) . . ? O4 C12 C11 111.75(14) . . ? O4 C13 C14 108.83(17) . . ? O4 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? O4 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 N1 C1 111.39(13) . . ? C8 N1 C15 124.26(14) . . ? C1 N1 C15 124.35(13) . . ? C9 O1 C7 110.11(12) . . ? C12 O4 C13 117.18(14) . . ? 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 C6 C1 C2 C3 -0.2(2) . . . . ? N1 C1 C2 C3 -178.74(16) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C1 0.1(3) . . . . ? C4 C5 C6 C7 177.65(16) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? N1 C1 C6 C5 178.87(14) . . . . ? C2 C1 C6 C7 -177.94(15) . . . . ? N1 C1 C6 C7 0.79(18) . . . . ? C5 C6 C7 O1 -62.3(2) . . . . ? C1 C6 C7 O1 115.52(14) . . . . ? C5 C6 C7 C11 57.7(2) . . . . ? C1 C6 C7 C11 -124.46(15) . . . . ? C5 C6 C7 C8 -177.65(17) . . . . ? C1 C6 C7 C8 0.15(16) . . . . ? O1 C7 C8 O3 60.4(2) . . . . ? C11 C7 C8 O3 -53.0(2) . . . . ? C6 C7 C8 O3 178.14(16) . . . . ? O1 C7 C8 N1 -118.84(14) . . . . ? C11 C7 C8 N1 127.80(14) . . . . ? C6 C7 C8 N1 -1.07(16) . . . . ? O2 C9 C10 C11 178.1(2) . . . . ? O1 C9 C10 C11 -1.39(19) . . . . ? C9 C10 C11 C12 178.05(15) . . . . ? C9 C10 C11 C7 1.08(19) . . . . ? O1 C7 C11 C10 -0.40(17) . . . . ? C6 C7 C11 C10 -124.54(16) . . . . ? C8 C7 C11 C10 115.92(15) . . . . ? O1 C7 C11 C12 -177.66(13) . . . . ? C6 C7 C11 C12 58.2(2) . . . . ? C8 C7 C11 C12 -61.34(18) . . . . ? C10 C11 C12 O5 -174.81(18) . . . . ? C7 C11 C12 O5 1.9(2) . . . . ? C10 C11 C12 O4 3.7(2) . . . . ? C7 C11 C12 O4 -179.59(14) . . . . ? O3 C8 N1 C1 -177.56(17) . . . . ? C7 C8 N1 C1 1.62(18) . . . . ? O3 C8 N1 C15 3.4(3) . . . . ? C7 C8 N1 C15 -177.39(15) . . . . ? C2 C1 N1 C8 177.06(16) . . . . ? C6 C1 N1 C8 -1.58(19) . . . . ? C2 C1 N1 C15 -3.9(3) . . . . ? C6 C1 N1 C15 177.43(15) . . . . ? O2 C9 O1 C7 -178.39(16) . . . . ? C10 C9 O1 C7 1.12(18) . . . . ? C11 C7 O1 C9 -0.48(16) . . . . ? C6 C7 O1 C9 128.46(14) . . . . ? C8 C7 O1 C9 -119.81(14) . . . . ? O5 C12 O4 C13 -5.2(3) . . . . ? C11 C12 O4 C13 176.35(15) . . . . ? C14 C13 O4 C12 161.92(17) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.168 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.035 # Attachment '110615a_0m.cif' data_110615a_0m _database_code_depnum_ccdc_archive 'CCDC 836563' #TrackingRef '110615a_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 Cl N2 O4' _chemical_formula_weight 509.02 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.897(11) _cell_length_b 12.592(16) _cell_length_c 13.863(17) _cell_angle_alpha 99.404(16) _cell_angle_beta 108.029(17) _cell_angle_gamma 95.241(18) _cell_volume 1440(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1118 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 21.08 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9674 _exptl_absorpt_process_details sadabs _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 7235 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.04 _reflns_number_total 5006 _reflns_number_gt 2846 _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^)+(0.0892P)^2^+0.4314P] 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 5006 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0708 _refine_ls_wR_factor_ref 0.2046 _refine_ls_wR_factor_gt 0.1741 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Cl1 Cl 0.10767(16) 0.76010(10) 0.27154(10) 0.1064(5) Uani 1 1 d . . . C1 C 0.2172(3) 0.9199(3) 0.1914(2) 0.0464(8) Uani 1 1 d . . . C2 C 0.0922(4) 0.8755(3) 0.2181(3) 0.0627(10) Uani 1 1 d . . . C3 C -0.0470(4) 0.9265(4) 0.2025(3) 0.0736(11) Uani 1 1 d . . . H3 H -0.1325 0.8984 0.2206 0.088 Uiso 1 1 calc R . . C4 C -0.0533(5) 1.0175(4) 0.1604(3) 0.0737(11) Uani 1 1 d . . . H4 H -0.1454 1.0499 0.1497 0.088 Uiso 1 1 calc R . . C5 C 0.0682(4) 1.0632(3) 0.1334(3) 0.0598(9) Uani 1 1 d . . . H5 H 0.0605 1.1254 0.1052 0.072 Uiso 1 1 calc R . . C6 C 0.2035(4) 1.0136(3) 0.1497(2) 0.0465(8) Uani 1 1 d . . . C7 C 0.4498(4) 0.9756(3) 0.1534(2) 0.0531(8) Uani 1 1 d . . . C8 C 0.3757(4) 0.8847(2) 0.1961(2) 0.0471(8) Uani 1 1 d . . . C9 C 0.3754(4) 0.7727(3) 0.1381(2) 0.0543(9) Uani 1 1 d . . . C10 C 0.4690(4) 0.7204(3) 0.2012(3) 0.0651(10) Uani 1 1 d . . . H10 H 0.4908 0.6507 0.1819 0.078 Uiso 1 1 calc R . . C11 C 0.5337(4) 0.7868(3) 0.3052(3) 0.0558(9) Uani 1 1 d . . . C12 C 0.3681(5) 1.1377(3) 0.0803(3) 0.0709(11) Uani 1 1 d . . . H12A H 0.2780 1.1324 0.0177 0.085 Uiso 1 1 calc R . . H12B H 0.4631 1.1333 0.0605 0.085 Uiso 1 1 calc R . . C13 C 0.3868(5) 1.2459(3) 0.1493(3) 0.0675(10) Uani 1 1 d . . . C14 C 0.5003(5) 1.2713(3) 0.2465(3) 0.0818(12) Uani 1 1 d . . . H14 H 0.5629 1.2196 0.2702 0.098 Uiso 1 1 calc R . . C15 C 0.5223(7) 1.3723(4) 0.3091(4) 0.1105(18) Uani 1 1 d . . . H15 H 0.6010 1.3887 0.3740 0.133 Uiso 1 1 calc R . . C16 C 0.4306(10) 1.4474(5) 0.2770(6) 0.125(2) Uani 1 1 d . . . H16 H 0.4460 1.5152 0.3200 0.150 Uiso 1 1 calc R . . C17 C 0.3155(8) 1.4251(5) 0.1820(7) 0.143(3) Uani 1 1 d . . . H17 H 0.2516 1.4770 0.1606 0.172 Uiso 1 1 calc R . . C18 C 0.2941(6) 1.3243(4) 0.1172(5) 0.1137(18) Uani 1 1 d . . . H18 H 0.2169 1.3094 0.0518 0.136 Uiso 1 1 calc R . . C19 C 0.6793(4) 0.8289(3) 0.4883(3) 0.0617(9) Uani 1 1 d . . . C20 C 0.5369(5) 0.8517(4) 0.5231(3) 0.0862(13) Uani 1 1 d . . . H20A H 0.4711 0.8917 0.4777 0.129 Uiso 1 1 calc R . . H20B H 0.5744 0.8938 0.5926 0.129 Uiso 1 1 calc R . . H20C H 0.4754 0.7841 0.5210 0.129 Uiso 1 1 calc R . . C21 C 0.7735(5) 0.9359(3) 0.4874(3) 0.0852(13) Uani 1 1 d . . . H21A H 0.8541 0.9210 0.4565 0.128 Uiso 1 1 calc R . . H21B H 0.8234 0.9761 0.5571 0.128 Uiso 1 1 calc R . . H21C H 0.7023 0.9779 0.4479 0.128 Uiso 1 1 calc R . . C22 C 0.7775(5) 0.7632(3) 0.5646(3) 0.0770(12) Uani 1 1 d . . . H22A H 0.8120 0.8104 0.6326 0.092 Uiso 1 1 calc R . . H22B H 0.7021 0.7035 0.5665 0.092 Uiso 1 1 calc R . . C23 C 0.9237(5) 0.7137(3) 0.5549(3) 0.0731(11) Uani 1 1 d . . . C24 C 0.8996(7) 0.6389(5) 0.4546(4) 0.127(2) Uani 1 1 d . . . H24A H 0.9963 0.6095 0.4570 0.191 Uiso 1 1 calc R . . H24B H 0.8726 0.6784 0.3994 0.191 Uiso 1 1 calc R . . H24C H 0.8144 0.5806 0.4425 0.191 Uiso 1 1 calc R . . C25 C 0.9830(8) 0.6588(6) 0.6450(4) 0.147(3) Uani 1 1 d . . . H25A H 0.9044 0.5985 0.6394 0.220 Uiso 1 1 calc R . . H25B H 1.0014 0.7099 0.7085 0.220 Uiso 1 1 calc R . . H25C H 1.0811 0.6329 0.6447 0.220 Uiso 1 1 calc R . . C26 C 1.0662(7) 0.8048(5) 0.5674(6) 0.161(3) Uani 1 1 d . . . H26A H 1.0811 0.8600 0.6275 0.241 Uiso 1 1 calc R . . H26B H 1.0419 0.8368 0.5071 0.241 Uiso 1 1 calc R . . H26C H 1.1623 0.7731 0.5751 0.241 Uiso 1 1 calc R . . C27 C 0.2857(4) 0.7362(3) 0.0265(3) 0.0634(10) Uani 1 1 d . . . C28 C 0.2147(7) 0.5881(4) -0.1161(3) 0.1199(19) Uani 1 1 d . . . H28A H 0.1015 0.5935 -0.1353 0.144 Uiso 1 1 calc R . . H28B H 0.2606 0.6292 -0.1563 0.144 Uiso 1 1 calc R . . C29 C 0.2351(10) 0.4807(5) -0.1371(4) 0.188(4) Uani 1 1 d . . . H29A H 0.3468 0.4751 -0.1110 0.281 Uiso 1 1 calc R . . H29B H 0.1951 0.4535 -0.2106 0.281 Uiso 1 1 calc R . . H29C H 0.1777 0.4387 -0.1042 0.281 Uiso 1 1 calc R . . N1 N 0.3426(3) 1.0445(2) 0.1282(2) 0.0522(7) Uani 1 1 d . . . N2 N 0.6209(4) 0.7585(2) 0.3841(2) 0.0638(8) Uani 1 1 d . . . O1 O 0.4767(2) 0.88645(17) 0.29990(15) 0.0528(6) Uani 1 1 d . . . O2 O 0.2179(4) 0.7940(2) -0.0273(2) 0.0972(10) Uani 1 1 d . . . O3 O 0.2926(4) 0.6329(2) -0.00635(19) 0.0933(10) Uani 1 1 d . . . O4 O 0.5815(3) 0.9825(2) 0.1453(2) 0.0820(8) 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 0.1067(10) 0.1079(9) 0.1150(10) 0.0503(8) 0.0444(8) -0.0100(7) C1 0.0353(17) 0.056(2) 0.0412(17) 0.0038(15) 0.0073(14) 0.0043(14) C2 0.057(2) 0.073(2) 0.053(2) 0.0093(18) 0.0156(17) -0.0029(19) C3 0.038(2) 0.110(3) 0.065(2) 0.000(2) 0.0198(18) -0.005(2) C4 0.045(2) 0.101(3) 0.065(2) -0.001(2) 0.0107(19) 0.020(2) C5 0.043(2) 0.067(2) 0.059(2) 0.0058(17) 0.0039(17) 0.0191(17) C6 0.0394(18) 0.053(2) 0.0411(18) 0.0047(15) 0.0057(14) 0.0111(15) C7 0.042(2) 0.065(2) 0.051(2) 0.0103(16) 0.0134(16) 0.0103(17) C8 0.0406(18) 0.054(2) 0.0446(18) 0.0110(15) 0.0084(14) 0.0133(15) C9 0.058(2) 0.057(2) 0.0423(18) 0.0060(16) 0.0076(16) 0.0175(17) C10 0.080(3) 0.054(2) 0.049(2) 0.0027(17) 0.0049(18) 0.0263(19) C11 0.061(2) 0.053(2) 0.050(2) 0.0073(16) 0.0107(17) 0.0221(17) C12 0.085(3) 0.069(3) 0.057(2) 0.024(2) 0.017(2) 0.004(2) C13 0.072(3) 0.061(2) 0.068(3) 0.024(2) 0.016(2) 0.004(2) C14 0.093(3) 0.070(3) 0.070(3) 0.015(2) 0.012(2) -0.001(2) C15 0.152(5) 0.078(4) 0.085(3) 0.011(3) 0.028(3) -0.016(3) C16 0.162(6) 0.066(4) 0.151(6) 0.005(4) 0.070(5) 0.000(4) C17 0.122(5) 0.066(4) 0.220(8) 0.036(4) 0.022(5) 0.015(3) C18 0.108(4) 0.064(3) 0.141(5) 0.038(3) -0.005(3) 0.006(3) C19 0.066(2) 0.063(2) 0.047(2) 0.0056(17) 0.0045(17) 0.0206(19) C20 0.093(3) 0.107(3) 0.064(3) 0.015(2) 0.028(2) 0.039(3) C21 0.080(3) 0.085(3) 0.067(3) 0.002(2) -0.004(2) 0.011(2) C22 0.086(3) 0.091(3) 0.046(2) 0.012(2) 0.006(2) 0.030(2) C23 0.078(3) 0.081(3) 0.053(2) 0.011(2) 0.004(2) 0.038(2) C24 0.133(5) 0.137(5) 0.087(3) -0.008(3) 0.001(3) 0.079(4) C25 0.161(6) 0.216(7) 0.096(4) 0.082(4) 0.037(4) 0.120(5) C26 0.099(4) 0.155(6) 0.216(8) 0.023(5) 0.036(5) 0.039(4) C27 0.065(2) 0.069(3) 0.048(2) 0.0049(19) 0.0067(18) 0.0165(19) C28 0.163(5) 0.103(4) 0.052(3) -0.017(3) -0.007(3) 0.027(4) C29 0.306(11) 0.117(5) 0.081(4) -0.026(4) 0.004(5) 0.027(6) N1 0.0451(16) 0.0558(17) 0.0556(17) 0.0171(13) 0.0133(13) 0.0091(13) N2 0.076(2) 0.0581(18) 0.0480(17) 0.0051(14) 0.0058(15) 0.0268(15) O1 0.0540(13) 0.0517(13) 0.0440(13) 0.0058(10) 0.0026(10) 0.0196(11) O2 0.126(3) 0.094(2) 0.0535(16) 0.0154(15) -0.0032(16) 0.0449(19) O3 0.132(3) 0.0731(19) 0.0448(15) -0.0068(13) -0.0078(15) 0.0299(17) O4 0.0501(16) 0.107(2) 0.101(2) 0.0275(16) 0.0383(15) 0.0150(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 Cl1 C2 1.733(4) . ? C1 C2 1.377(5) . ? C1 C6 1.395(4) . ? C1 C8 1.502(4) . ? C2 C3 1.421(5) . ? C3 C4 1.366(6) . ? C3 H3 0.9300 . ? C4 C5 1.359(5) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 N1 1.396(4) . ? C7 O4 1.208(4) . ? C7 N1 1.351(4) . ? C7 C8 1.556(5) . ? C8 O1 1.436(4) . ? C8 C9 1.504(5) . ? C9 C10 1.315(4) . ? C9 C27 1.476(5) . ? C10 C11 1.454(5) . ? C10 H10 0.9300 . ? C11 N2 1.256(4) . ? C11 O1 1.401(4) . ? C12 N1 1.472(4) . ? C12 C13 1.495(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.377(5) . ? C13 C18 1.385(6) . ? C14 C15 1.378(6) . ? C14 H14 0.9300 . ? C15 C16 1.346(8) . ? C15 H15 0.9300 . ? C16 C17 1.361(8) . ? C16 H16 0.9300 . ? C17 C18 1.389(8) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N2 1.474(4) . ? C19 C20 1.523(5) . ? C19 C21 1.525(5) . ? C19 C22 1.553(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C23 1.525(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.490(6) . ? C23 C25 1.502(6) . ? C23 C26 1.577(7) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 O2 1.194(4) . ? C27 O3 1.320(4) . ? C28 C29 1.377(7) . ? C28 O3 1.453(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? 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 C2 C1 C6 119.1(3) . . ? C2 C1 C8 131.6(3) . . ? C6 C1 C8 109.3(3) . . ? C1 C2 C3 119.0(4) . . ? C1 C2 Cl1 119.9(3) . . ? C3 C2 Cl1 121.1(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 123.4(4) . . ? C5 C4 H4 118.3 . . ? C3 C4 H4 118.3 . . ? C4 C5 C6 117.3(4) . . ? C4 C5 H5 121.3 . . ? C6 C5 H5 121.3 . . ? C5 C6 C1 122.3(3) . . ? C5 C6 N1 128.0(3) . . ? C1 C6 N1 109.6(3) . . ? O4 C7 N1 126.6(3) . . ? O4 C7 C8 125.0(3) . . ? N1 C7 C8 108.5(3) . . ? O1 C8 C1 113.0(2) . . ? O1 C8 C9 103.9(2) . . ? C1 C8 C9 117.9(3) . . ? O1 C8 C7 108.9(2) . . ? C1 C8 C7 101.1(3) . . ? C9 C8 C7 112.0(3) . . ? C10 C9 C27 128.7(3) . . ? C10 C9 C8 109.2(3) . . ? C27 C9 C8 122.0(3) . . ? C9 C10 C11 110.5(3) . . ? C9 C10 H10 124.7 . . ? C11 C10 H10 124.7 . . ? N2 C11 O1 127.3(3) . . ? N2 C11 C10 126.3(3) . . ? O1 C11 C10 106.5(3) . . ? N1 C12 C13 113.8(3) . . ? N1 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N1 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C18 118.0(4) . . ? C14 C13 C12 120.5(4) . . ? C18 C13 C12 121.5(4) . . ? C13 C14 C15 120.8(4) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 120.4(5) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.6(6) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C18 119.6(5) . . ? C16 C17 H17 120.2 . . ? C18 C17 H17 120.2 . . ? C13 C18 C17 120.5(5) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? N2 C19 C20 109.1(3) . . ? N2 C19 C21 110.5(3) . . ? C20 C19 C21 109.7(3) . . ? N2 C19 C22 107.8(3) . . ? C20 C19 C22 106.1(3) . . ? C21 C19 C22 113.5(3) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C19 125.0(3) . . ? C23 C22 H22A 106.1 . . ? C19 C22 H22A 106.1 . . ? C23 C22 H22B 106.1 . . ? C19 C22 H22B 106.1 . . ? H22A C22 H22B 106.3 . . ? C24 C23 C25 111.6(4) . . ? C24 C23 C22 115.7(4) . . ? C25 C23 C22 107.6(4) . . ? C24 C23 C26 105.2(5) . . ? C25 C23 C26 105.1(5) . . ? C22 C23 C26 111.3(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 C27 O3 124.6(3) . . ? O2 C27 C9 123.9(4) . . ? O3 C27 C9 111.5(3) . . ? C29 C28 O3 109.3(4) . . ? C29 C28 H28A 109.8 . . ? O3 C28 H28A 109.8 . . ? C29 C28 H28B 109.8 . . ? O3 C28 H28B 109.8 . . ? H28A C28 H28B 108.3 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C7 N1 C6 111.5(3) . . ? C7 N1 C12 123.8(3) . . ? C6 N1 C12 124.6(3) . . ? C11 N2 C19 123.6(3) . . ? C11 O1 C8 109.9(2) . . ? C27 O3 C28 117.0(3) . . ? 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 C6 C1 C2 C3 -0.1(5) . . . . ? C8 C1 C2 C3 -178.5(3) . . . . ? C6 C1 C2 Cl1 -179.2(2) . . . . ? C8 C1 C2 Cl1 2.4(5) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? Cl1 C2 C3 C4 179.7(3) . . . . ? C2 C3 C4 C5 -0.8(6) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C4 C5 C6 C1 0.4(5) . . . . ? C4 C5 C6 N1 179.7(3) . . . . ? C2 C1 C6 C5 -0.5(5) . . . . ? C8 C1 C6 C5 178.3(3) . . . . ? C2 C1 C6 N1 -179.9(3) . . . . ? C8 C1 C6 N1 -1.1(3) . . . . ? C2 C1 C8 O1 -63.6(4) . . . . ? C6 C1 C8 O1 117.8(3) . . . . ? C2 C1 C8 C9 57.7(5) . . . . ? C6 C1 C8 C9 -120.9(3) . . . . ? C2 C1 C8 C7 -179.8(3) . . . . ? C6 C1 C8 C7 1.6(3) . . . . ? O4 C7 C8 O1 58.9(4) . . . . ? N1 C7 C8 O1 -120.8(3) . . . . ? O4 C7 C8 C1 178.1(3) . . . . ? N1 C7 C8 C1 -1.5(3) . . . . ? O4 C7 C8 C9 -55.5(4) . . . . ? N1 C7 C8 C9 124.9(3) . . . . ? O1 C8 C9 C10 -1.9(4) . . . . ? C1 C8 C9 C10 -127.8(3) . . . . ? C7 C8 C9 C10 115.5(3) . . . . ? O1 C8 C9 C27 -179.5(3) . . . . ? C1 C8 C9 C27 54.6(4) . . . . ? C7 C8 C9 C27 -62.1(4) . . . . ? C27 C9 C10 C11 180.0(3) . . . . ? C8 C9 C10 C11 2.6(4) . . . . ? C9 C10 C11 N2 176.5(4) . . . . ? C9 C10 C11 O1 -2.3(4) . . . . ? N1 C12 C13 C14 54.4(5) . . . . ? N1 C12 C13 C18 -127.1(4) . . . . ? C18 C13 C14 C15 -1.0(6) . . . . ? C12 C13 C14 C15 177.6(4) . . . . ? C13 C14 C15 C16 1.3(8) . . . . ? C14 C15 C16 C17 -0.4(9) . . . . ? C15 C16 C17 C18 -0.9(10) . . . . ? C14 C13 C18 C17 -0.3(7) . . . . ? C12 C13 C18 C17 -178.9(5) . . . . ? C16 C17 C18 C13 1.2(9) . . . . ? N2 C19 C22 C23 57.9(5) . . . . ? C20 C19 C22 C23 174.6(4) . . . . ? C21 C19 C22 C23 -64.9(5) . . . . ? C19 C22 C23 C24 -55.3(6) . . . . ? C19 C22 C23 C25 179.3(4) . . . . ? C19 C22 C23 C26 64.7(5) . . . . ? C10 C9 C27 O2 -171.1(4) . . . . ? C8 C9 C27 O2 6.0(6) . . . . ? C10 C9 C27 O3 7.7(6) . . . . ? C8 C9 C27 O3 -175.3(3) . . . . ? O4 C7 N1 C6 -178.6(3) . . . . ? C8 C7 N1 C6 1.0(3) . . . . ? O4 C7 N1 C12 3.6(5) . . . . ? C8 C7 N1 C12 -176.8(3) . . . . ? C5 C6 N1 C7 -179.3(3) . . . . ? C1 C6 N1 C7 0.1(4) . . . . ? C5 C6 N1 C12 -1.6(5) . . . . ? C1 C6 N1 C12 177.8(3) . . . . ? C13 C12 N1 C7 -112.3(4) . . . . ? C13 C12 N1 C6 70.2(4) . . . . ? O1 C11 N2 C19 0.2(6) . . . . ? C10 C11 N2 C19 -178.3(3) . . . . ? C20 C19 N2 C11 63.3(5) . . . . ? C21 C19 N2 C11 -57.3(5) . . . . ? C22 C19 N2 C11 178.0(3) . . . . ? N2 C11 O1 C8 -177.8(3) . . . . ? C10 C11 O1 C8 1.0(3) . . . . ? C1 C8 O1 C11 129.4(3) . . . . ? C9 C8 O1 C11 0.5(3) . . . . ? C7 C8 O1 C11 -119.1(3) . . . . ? O2 C27 O3 C28 1.4(6) . . . . ? C9 C27 O3 C28 -177.4(4) . . . . ? C29 C28 O3 C27 179.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.422 _refine_diff_density_min -0.375 _refine_diff_density_rms 0.046