Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Yua-Kuang Chen ' 'Chun-Chen Liao' 'Rama Krishna Peddinti' _publ_contact_author_name 'Prof Chun-Chen Liao' _publ_contact_author_address ; Department of Chemistry National Tsing Hua University Hsinchu TAIWAN ; _publ_contact_author_email CCLIAO@MX.NTHU.EDU.TW data_ic6331 _database_code_CSD 160762 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H18 O4' _chemical_formula_weight 238.27 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 6.7251(2) _cell_length_b 24.8959(4) _cell_length_c 7.5943(3) _cell_angle_alpha 90.00 _cell_angle_beta 109.260(2) _cell_angle_gamma 90.00 _cell_volume 1200.33(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method ? _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3372 _diffrn_reflns_av_R_equivalents 0.0187 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2080 _reflns_number_observed 1792 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 27 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.1557P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(21) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2.72(124) _refine_ls_number_reflns 2053 _refine_ls_number_parameters 155 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_obs 0.0412 _refine_ls_wR_factor_all 0.1123 _refine_ls_wR_factor_obs 0.1070 _refine_ls_goodness_of_fit_all 1.039 _refine_ls_goodness_of_fit_obs 1.074 _refine_ls_restrained_S_all 1.039 _refine_ls_restrained_S_obs 1.073 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.9237(4) 0.90161(8) 0.7479(3) 0.0666(6) Uani 1 d . . O2 O 0.2227(3) 0.86623(10) 0.0859(3) 0.0659(6) Uani 1 d . . H2A H 0.1720(3) 0.84359(10) 0.0051(3) 0.099 Uiso 1 calc R . O3 O 0.5046(3) 0.91823(7) 0.5254(2) 0.0463(4) Uani 1 d . . O4 O 0.7311(3) 0.95039(6) 0.3741(2) 0.0426(4) Uani 1 d . . C1 C 0.6553(3) 0.90509(8) 0.4417(3) 0.0335(5) Uani 1 d . . C2 C 0.8347(4) 0.87759(9) 0.6027(3) 0.0390(5) Uani 1 d . . C3 C 0.8844(4) 0.82092(9) 0.5655(3) 0.0442(6) Uani 1 d . . H3A H 0.9886(4) 0.80440(9) 0.6742(3) 0.053 Uiso 1 calc R . C4 C 0.9598(4) 0.82219(10) 0.3928(4) 0.0467(6) Uani 1 d . . H4A H 1.0919(4) 0.84160(10) 0.4228(4) 0.056 Uiso 1 calc R . H4B H 0.9826(4) 0.78585(10) 0.3574(4) 0.056 Uiso 1 calc R . C5 C 0.7919(4) 0.84989(9) 0.2310(3) 0.0374(5) Uani 1 d . . H5A H 0.8505(4) 0.88375(9) 0.2042(3) 0.045 Uiso 1 calc R . C6 C 0.5907(3) 0.86298(8) 0.2824(3) 0.0324(4) Uani 1 d . . C7 C 0.5279(4) 0.81327(9) 0.3656(3) 0.0400(5) Uani 1 d . . H7A H 0.3938(4) 0.79847(9) 0.3185(3) 0.048 Uiso 1 calc R . C8 C 0.6762(4) 0.79222(9) 0.5098(4) 0.0461(6) Uani 1 d . . H8A H 0.6534(4) 0.76190(9) 0.5721(4) 0.055 Uiso 1 calc R . C9 C 0.4301(3) 0.87872(10) 0.0908(3) 0.0420(6) Uani 1 d . . H9A H 0.4408(3) 0.91729(10) 0.0698(3) 0.050 Uiso 1 calc R . C10 C 0.4975(5) 0.84682(14) -0.0536(4) 0.0644(8) Uani 1 d . . H10A H 0.3901(5) 0.82069(14) -0.1153(4) 0.077 Uiso 1 calc R . H10B H 0.5163(5) 0.87091(14) -0.1472(4) 0.077 Uiso 1 calc R . C11 C 0.7035(4) 0.81852(11) 0.0487(4) 0.0502(6) Uani 1 d . . H11A H 0.7991(4) 0.81994(11) -0.0229(4) 0.060 Uiso 1 calc R . H11B H 0.6791(4) 0.78125(11) 0.0728(4) 0.060 Uiso 1 calc R . C12 C 0.3298(5) 0.94995(14) 0.4186(5) 0.0681(9) Uani 1 d . . H12A H 0.2380(5) 0.95631(14) 0.4900(5) 0.102 Uiso 1 calc R . H12B H 0.2541(5) 0.93122(14) 0.3059(5) 0.102 Uiso 1 calc R . H12C H 0.3797(5) 0.98365(14) 0.3880(5) 0.102 Uiso 1 calc R . C13 C 0.8045(6) 0.99528(11) 0.4987(4) 0.0596(8) Uani 1 d . . H13A H 0.8517(6) 1.02335(11) 0.4353(4) 0.089 Uiso 1 calc R . H13B H 0.9190(6) 0.98394(11) 0.6058(4) 0.089 Uiso 1 calc R . H13C H 0.6916(6) 1.00843(11) 0.5379(4) 0.089 Uiso 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 0.0727(13) 0.0679(12) 0.0377(9) -0.0111(8) -0.0108(9) 0.0164(10) O2 0.0345(9) 0.111(2) 0.0433(11) 0.0104(10) 0.0014(8) -0.0008(10) O3 0.0476(10) 0.0558(9) 0.0405(9) 0.0044(7) 0.0215(8) 0.0132(8) O4 0.0615(11) 0.0348(8) 0.0343(8) -0.0014(6) 0.0194(7) -0.0068(7) C1 0.0360(12) 0.0364(10) 0.0279(10) 0.0051(8) 0.0101(8) 0.0051(8) C2 0.0382(11) 0.0463(12) 0.0300(10) 0.0035(9) 0.0077(9) 0.0017(9) C3 0.0390(12) 0.0429(12) 0.0419(12) 0.0107(9) 0.0014(10) 0.0087(9) C4 0.0379(12) 0.0476(12) 0.0534(15) -0.0024(10) 0.0135(11) 0.0095(10) C5 0.0381(12) 0.0402(11) 0.0359(11) -0.0028(8) 0.0147(10) -0.0022(9) C6 0.0308(10) 0.0377(11) 0.0266(10) 0.0030(8) 0.0067(8) -0.0003(8) C7 0.0404(12) 0.0400(11) 0.0380(12) 0.0016(9) 0.0107(9) -0.0043(9) C8 0.0547(15) 0.0382(12) 0.0447(13) 0.0107(9) 0.0155(11) -0.0004(10) C9 0.0371(13) 0.0529(13) 0.0290(11) 0.0059(9) 0.0014(9) -0.0023(10) C10 0.065(2) 0.093(2) 0.0311(12) -0.0083(13) 0.0105(12) -0.003(2) C11 0.057(2) 0.0550(15) 0.0430(13) -0.0122(10) 0.0234(12) -0.0078(11) C12 0.050(2) 0.076(2) 0.074(2) -0.0052(15) 0.015(2) 0.0207(14) C13 0.086(2) 0.0468(13) 0.050(2) -0.0121(11) 0.0277(15) -0.0127(13) _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 C2 1.223(3) . ? O2 C9 1.418(3) . ? O3 C1 1.401(3) . ? O3 C12 1.426(3) . ? O4 C1 1.403(3) . ? O4 C13 1.442(3) . ? C1 C6 1.551(3) . ? C1 C2 1.564(3) . ? C2 C3 1.498(3) . ? C3 C8 1.503(4) . ? C3 C4 1.555(4) . ? C4 C5 1.531(3) . ? C5 C11 1.529(3) . ? C5 C6 1.561(3) . ? C6 C7 1.512(3) . ? C6 C9 1.549(3) . ? C7 C8 1.322(3) . ? C9 C10 1.538(4) . ? C10 C11 1.520(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 O3 C12 117.1(2) . . ? C1 O4 C13 118.0(2) . . ? O3 C1 O4 112.5(2) . . ? O3 C1 C6 117.0(2) . . ? O4 C1 C6 107.4(2) . . ? O3 C1 C2 103.6(2) . . ? O4 C1 C2 111.0(2) . . ? C6 C1 C2 105.0(2) . . ? O1 C2 C3 123.8(2) . . ? O1 C2 C1 120.8(2) . . ? C3 C2 C1 115.3(2) . . ? C2 C3 C8 104.8(2) . . ? C2 C3 C4 107.2(2) . . ? C8 C3 C4 107.7(2) . . ? C5 C4 C3 109.1(2) . . ? C11 C5 C4 117.4(2) . . ? C11 C5 C6 102.9(2) . . ? C4 C5 C6 111.4(2) . . ? C7 C6 C9 113.3(2) . . ? C7 C6 C1 105.8(2) . . ? C9 C6 C1 119.4(2) . . ? C7 C6 C5 108.6(2) . . ? C9 C6 C5 102.2(2) . . ? C1 C6 C5 107.1(2) . . ? C8 C7 C6 115.6(2) . . ? C7 C8 C3 115.0(2) . . ? O2 C9 C10 112.7(2) . . ? O2 C9 C6 110.2(2) . . ? C10 C9 C6 105.1(2) . . ? C11 C10 C9 107.9(2) . . ? C10 C11 C5 104.0(2) . . ? _refine_diff_density_max 0.205 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.036 data_ic6347 _database_code_CSD 160763 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H17 Br O4' _chemical_formula_weight 317.18 _chemical_melting_point ? _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9569(2) _cell_length_b 12.4857(4) _cell_length_c 14.1058(3) _cell_angle_alpha 82.922(1) _cell_angle_beta 83.764(1) _cell_angle_gamma 77.597(1) _cell_volume 1353.35(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 5902 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method ? _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 3.041 _exptl_absorpt_correction_type ' empirical used sadabs' _exptl_absorpt_correction_T_min 0.5179 _exptl_absorpt_correction_T_max 0.6944 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Siemens SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13761 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5460 _reflns_number_observed 3823 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SAINT' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+1.5005P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5460 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_obs 0.0488 _refine_ls_wR_factor_all 0.1221 _refine_ls_wR_factor_obs 0.1096 _refine_ls_goodness_of_fit_all 1.041 _refine_ls_goodness_of_fit_obs 1.129 _refine_ls_restrained_S_all 1.041 _refine_ls_restrained_S_obs 1.129 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Br1 Br 0.23516(6) 0.68991(4) 0.84236(3) 0.0589(2) Uani 1 d . . Br2 Br 0.07238(10) 0.90102(5) 1.16704(5) 0.1000(3) Uani 1 d . . O1 O 0.7127(3) 0.8213(2) 0.5477(2) 0.0542(7) Uani 1 d . . O2 O 0.5791(3) 0.5892(2) 0.4893(2) 0.0489(7) Uani 1 d . . H2A H 0.5983(3) 0.5606(2) 0.4389(2) 0.073 Uiso 1 calc R . O3 O 0.5240(4) 0.9905(2) 0.6504(2) 0.0596(8) Uani 1 d . . O4 O 0.5933(4) 0.8357(2) 0.7603(2) 0.0513(7) Uani 1 d . . O5 O -0.3590(4) 0.6074(3) 1.2436(2) 0.0645(9) Uani 1 d . . O6 O -0.0854(4) 0.5568(3) 1.4221(2) 0.0571(8) Uani 1 d . . H6A H -0.0755(4) 0.5084(3) 1.4672(2) 0.086 Uiso 1 calc R . O7 O -0.2381(4) 0.6404(3) 1.0334(2) 0.0533(7) Uani 1 d . . O8 O -0.3361(4) 0.7950(3) 1.1160(2) 0.0669(9) Uani 1 d . . C1 C 0.5747(5) 0.8180(3) 0.5900(3) 0.0375(8) Uani 1 d . . C2 C 0.4422(4) 0.7597(3) 0.5614(2) 0.0346(8) Uani 1 d . . C3 C 0.3820(4) 0.6921(3) 0.6498(2) 0.0359(8) Uani 1 d . . H3A H 0.3889(4) 0.6164(3) 0.6531(2) 0.043 Uiso 1 calc R . C4 C 0.3191(5) 0.7504(3) 0.7217(3) 0.0398(9) Uani 1 d . . C5 C 0.3143(5) 0.8714(3) 0.7051(3) 0.0435(9) Uani 1 d . . H5A H 0.2648(5) 0.9084(3) 0.7622(3) 0.052 Uiso 1 calc R . C6 C 0.5037(5) 0.8825(3) 0.6785(3) 0.0424(9) Uani 1 d . . C7 C 0.4844(5) 0.6993(3) 0.4724(3) 0.0421(9) Uani 1 d . . H7A H 0.5524(5) 0.7402(3) 0.4248(3) 0.051 Uiso 1 calc R . C8 C 0.3088(6) 0.7050(4) 0.4352(3) 0.0608(12) Uani 1 d . . H8A H 0.2693(6) 0.6367(4) 0.4549(3) 0.073 Uiso 1 calc R . H8B H 0.3170(6) 0.7171(4) 0.3657(3) 0.073 Uiso 1 calc R . C9 C 0.1834(6) 0.8015(4) 0.4783(4) 0.0682(13) Uani 1 d . . H9A H 0.1282(6) 0.8529(4) 0.4280(4) 0.082 Uiso 1 calc R . H9B H 0.0947(6) 0.7750(4) 0.5218(4) 0.082 Uiso 1 calc R . C10 C 0.2905(5) 0.8569(3) 0.5315(3) 0.0456(10) Uani 1 d . . H10A H 0.3397(5) 0.9095(3) 0.4852(3) 0.055 Uiso 1 calc R . C11 C 0.2083(5) 0.9170(4) 0.6188(3) 0.0552(11) Uani 1 d . . H11A H 0.0907(5) 0.9066(4) 0.6339(3) 0.066 Uiso 1 calc R . H11B H 0.2052(5) 0.9954(4) 0.6045(3) 0.066 Uiso 1 calc R . C12 C 0.4594(8) 1.0656(4) 0.7205(4) 0.081(2) Uani 1 d . . H12A H 0.4782(8) 1.1376(4) 0.6957(4) 0.122 Uiso 1 calc R . H12B H 0.5185(8) 1.0411(4) 0.7775(4) 0.122 Uiso 1 calc R . H12C H 0.3379(8) 1.0687(4) 0.7354(4) 0.122 Uiso 1 calc R . C13 C 0.7710(6) 0.8423(5) 0.7545(4) 0.077(2) Uani 1 d . . H13A H 0.8194(6) 0.8085(5) 0.8131(4) 0.116 Uiso 1 calc R . H13B H 0.7808(6) 0.9182(5) 0.7448(4) 0.116 Uiso 1 calc R . H13C H 0.8324(6) 0.8046(5) 0.7018(4) 0.116 Uiso 1 calc R . C14 C -0.2249(5) 0.6287(3) 1.2064(2) 0.0378(8) Uani 1 d . . C15 C -0.0518(4) 0.5923(3) 1.2468(2) 0.0321(7) Uani 1 d . . C16 C 0.0012(5) 0.6989(3) 1.2574(3) 0.0415(9) Uani 1 d . . H16A H 0.0237(5) 0.7182(3) 1.3157(3) 0.050 Uiso 1 calc R . C17 C 0.0124(6) 0.7615(3) 1.1765(3) 0.0496(10) Uani 1 d . . C18 C -0.0264(5) 0.7180(3) 1.0882(3) 0.0448(9) Uani 1 d . . H18A H -0.0151(5) 0.7699(3) 1.0309(3) 0.054 Uiso 1 calc R . C19 C -0.2103(5) 0.6982(3) 1.1081(2) 0.0417(9) Uani 1 d . . C20 C -0.0371(5) 0.5081(3) 1.3345(2) 0.0451(9) Uani 1 d . . H20A H -0.1089(5) 0.4546(3) 1.3299(2) 0.054 Uiso 1 calc R . C21 C 0.1544(6) 0.4503(4) 1.3276(3) 0.0622(13) Uani 1 d . . H21A H 0.2164(6) 0.4785(4) 1.3713(3) 0.075 Uiso 1 calc R . H21B H 0.1654(6) 0.3716(4) 1.3445(3) 0.075 Uiso 1 calc R . C22 C 0.2277(5) 0.4732(4) 1.2253(3) 0.0557(11) Uani 1 d . . H22A H 0.2855(5) 0.4050(4) 1.1994(3) 0.067 Uiso 1 calc R . H22B H 0.3098(5) 0.5210(4) 1.2222(3) 0.067 Uiso 1 calc R . C23 C 0.0732(5) 0.5292(3) 1.1697(2) 0.0366(8) Uani 1 d . . H23A H 0.0195(5) 0.4718(3) 1.1517(2) 0.044 Uiso 1 calc R . C24 C 0.1030(5) 0.6072(3) 1.0800(3) 0.0412(9) Uani 1 d . . H24A H 0.0861(5) 0.5752(3) 1.0233(3) 0.049 Uiso 1 calc R . H24B H 0.2204(5) 0.6190(3) 1.0743(3) 0.049 Uiso 1 calc R . C25 C -0.4047(6) 0.6203(5) 1.0358(3) 0.0703(14) Uani 1 d . . H25A H -0.4120(6) 0.5808(5) 0.9827(3) 0.105 Uiso 1 calc R . H25B H -0.4865(6) 0.6891(5) 1.0317(3) 0.105 Uiso 1 calc R . H25C H -0.4301(6) 0.5771(5) 1.0947(3) 0.105 Uiso 1 calc R . C26 C -0.3508(10) 0.8731(5) 1.0326(4) 0.117(3) Uani 1 d . . H26A H -0.4401(10) 0.9359(5) 1.0457(4) 0.175 Uiso 1 calc R . H26B H -0.3790(10) 0.8396(5) 0.9804(4) 0.175 Uiso 1 calc R . H26C H -0.2430(10) 0.8964(5) 1.0157(4) 0.175 Uiso 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 Br1 0.0676(3) 0.0726(3) 0.0375(2) 0.0082(2) 0.0083(2) -0.0309(2) Br2 0.1396(6) 0.0573(3) 0.1177(5) -0.0102(3) -0.0073(4) -0.0536(4) O1 0.039(2) 0.069(2) 0.058(2) -0.0163(14) 0.0153(14) -0.0220(14) O2 0.048(2) 0.051(2) 0.0451(15) -0.0154(12) -0.0032(12) 0.0023(13) O3 0.084(2) 0.0370(15) 0.056(2) -0.0068(13) 0.022(2) -0.0217(15) O4 0.053(2) 0.059(2) 0.046(2) -0.0054(13) -0.0029(13) -0.0204(14) O5 0.034(2) 0.108(3) 0.050(2) -0.005(2) -0.0010(13) -0.017(2) O6 0.053(2) 0.082(2) 0.0267(13) 0.0001(13) 0.0001(12) 0.002(2) O7 0.047(2) 0.078(2) 0.0348(14) -0.0202(13) -0.0097(12) -0.0023(15) O8 0.075(2) 0.063(2) 0.048(2) -0.0091(14) -0.016(2) 0.028(2) C1 0.035(2) 0.035(2) 0.039(2) 0.0025(15) 0.001(2) -0.005(2) C2 0.031(2) 0.039(2) 0.031(2) 0.0024(14) 0.0006(14) -0.006(2) C3 0.031(2) 0.039(2) 0.037(2) 0.006(2) -0.002(2) -0.011(2) C4 0.035(2) 0.046(2) 0.036(2) 0.005(2) 0.003(2) -0.011(2) C5 0.046(2) 0.042(2) 0.037(2) -0.002(2) 0.011(2) -0.006(2) C6 0.048(2) 0.033(2) 0.044(2) -0.002(2) 0.007(2) -0.010(2) C7 0.038(2) 0.049(2) 0.038(2) -0.002(2) -0.002(2) -0.010(2) C8 0.050(3) 0.073(3) 0.062(3) -0.003(2) -0.025(2) -0.011(2) C9 0.044(3) 0.090(4) 0.065(3) -0.006(3) -0.016(2) 0.003(3) C10 0.036(2) 0.051(2) 0.039(2) 0.011(2) 0.001(2) 0.004(2) C11 0.042(2) 0.052(3) 0.058(3) 0.005(2) 0.006(2) 0.007(2) C12 0.124(5) 0.044(3) 0.075(3) -0.017(2) 0.029(3) -0.029(3) C13 0.061(3) 0.104(4) 0.080(3) -0.026(3) -0.013(3) -0.034(3) C14 0.034(2) 0.049(2) 0.031(2) -0.011(2) -0.004(2) -0.007(2) C15 0.028(2) 0.038(2) 0.030(2) -0.0061(14) -0.0024(14) -0.0036(15) C16 0.039(2) 0.047(2) 0.043(2) -0.014(2) -0.009(2) -0.010(2) C17 0.056(3) 0.039(2) 0.059(3) -0.008(2) -0.005(2) -0.018(2) C18 0.055(3) 0.043(2) 0.034(2) 0.008(2) -0.003(2) -0.013(2) C19 0.042(2) 0.045(2) 0.032(2) -0.009(2) -0.008(2) 0.010(2) C20 0.050(2) 0.053(2) 0.032(2) 0.000(2) -0.007(2) -0.010(2) C21 0.065(3) 0.065(3) 0.042(2) -0.003(2) -0.013(2) 0.020(2) C22 0.045(3) 0.063(3) 0.049(2) -0.003(2) -0.006(2) 0.010(2) C23 0.032(2) 0.041(2) 0.035(2) -0.0051(15) -0.0002(15) -0.005(2) C24 0.034(2) 0.053(2) 0.035(2) -0.004(2) 0.004(2) -0.010(2) C25 0.036(3) 0.118(4) 0.056(3) -0.017(3) -0.019(2) -0.003(3) C26 0.158(7) 0.076(4) 0.078(4) 0.014(3) -0.024(4) 0.054(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 Br1 C4 1.888(3) . ? Br2 C17 1.888(4) . ? O1 C1 1.198(4) . ? O2 C7 1.423(5) . ? O3 C6 1.395(4) . ? O3 C12 1.426(5) . ? O4 C6 1.419(5) . ? O4 C13 1.427(5) . ? O5 C14 1.205(4) . ? O6 C20 1.423(5) . ? O7 C25 1.397(5) . ? O7 C19 1.410(4) . ? O8 C19 1.402(4) . ? O8 C26 1.430(6) . ? C1 C2 1.516(5) . ? C1 C6 1.558(5) . ? C2 C3 1.511(4) . ? C2 C7 1.514(5) . ? C2 C10 1.569(5) . ? C3 C4 1.313(5) . ? C4 C5 1.493(5) . ? C5 C11 1.537(6) . ? C5 C6 1.544(5) . ? C7 C8 1.531(6) . ? C8 C9 1.532(6) . ? C9 C10 1.513(6) . ? C10 C11 1.533(6) . ? C14 C15 1.506(5) . ? C14 C19 1.549(5) . ? C15 C16 1.509(5) . ? C15 C20 1.518(5) . ? C15 C23 1.560(5) . ? C16 C17 1.308(5) . ? C17 C18 1.505(6) . ? C18 C19 1.527(6) . ? C18 C24 1.546(5) . ? C20 C21 1.537(6) . ? C21 C22 1.514(6) . ? C22 C23 1.523(5) . ? C23 C24 1.529(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 C6 O3 C12 114.7(3) . . ? C6 O4 C13 116.0(3) . . ? C25 O7 C19 115.1(3) . . ? C19 O8 C26 116.4(4) . . ? O1 C1 C2 125.6(3) . . ? O1 C1 C6 122.9(3) . . ? C2 C1 C6 111.3(3) . . ? C3 C2 C7 114.5(3) . . ? C3 C2 C1 107.6(3) . . ? C7 C2 C1 118.6(3) . . ? C3 C2 C10 109.5(3) . . ? C7 C2 C10 102.4(3) . . ? C1 C2 C10 103.4(3) . . ? C4 C3 C2 113.5(3) . . ? C3 C4 C5 117.0(3) . . ? C3 C4 Br1 123.8(3) . . ? C5 C4 Br1 119.2(3) . . ? C4 C5 C11 107.3(3) . . ? C4 C5 C6 105.5(3) . . ? C11 C5 C6 109.4(3) . . ? O3 C6 O4 111.8(3) . . ? O3 C6 C5 114.0(3) . . ? O4 C6 C5 105.9(3) . . ? O3 C6 C1 105.4(3) . . ? O4 C6 C1 111.5(3) . . ? C5 C6 C1 108.2(3) . . ? O2 C7 C2 113.7(3) . . ? O2 C7 C8 112.7(3) . . ? C2 C7 C8 104.4(3) . . ? C7 C8 C9 106.8(4) . . ? C10 C9 C8 106.3(3) . . ? C9 C10 C11 120.1(4) . . ? C9 C10 C2 102.8(3) . . ? C11 C10 C2 110.2(3) . . ? C10 C11 C5 109.6(3) . . ? O5 C14 C15 125.7(3) . . ? O5 C14 C19 123.1(3) . . ? C15 C14 C19 111.2(3) . . ? C14 C15 C16 103.9(3) . . ? C14 C15 C20 118.0(3) . . ? C16 C15 C20 115.5(3) . . ? C14 C15 C23 106.9(3) . . ? C16 C15 C23 110.0(3) . . ? C20 C15 C23 102.3(3) . . ? C17 C16 C15 113.3(3) . . ? C16 C17 C18 116.9(3) . . ? C16 C17 Br2 123.2(3) . . ? C18 C17 Br2 119.9(3) . . ? C17 C18 C19 105.9(3) . . ? C17 C18 C24 105.8(3) . . ? C19 C18 C24 110.1(3) . . ? O8 C19 O7 111.5(3) . . ? O8 C19 C18 113.7(3) . . ? O7 C19 C18 106.5(3) . . ? O8 C19 C14 105.5(3) . . ? O7 C19 C14 110.9(3) . . ? C18 C19 C14 108.7(3) . . ? O6 C20 C15 112.9(3) . . ? O6 C20 C21 111.3(3) . . ? C15 C20 C21 103.9(3) . . ? C22 C21 C20 107.6(3) . . ? C21 C22 C23 105.5(3) . . ? C22 C23 C24 118.4(3) . . ? C22 C23 C15 102.6(3) . . ? C24 C23 C15 110.7(3) . . ? C23 C24 C18 108.6(3) . . ? _refine_diff_density_max 0.821 _refine_diff_density_min -0.981 _refine_diff_density_rms 0.066 data_ic6403 _database_code_CSD 160764 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H20 N2 O9' _chemical_formula_weight 432.38 _chemical_melting_point ? _chemical_compound_source ? 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)/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 20.8010(1) _cell_length_b 12.5757(2) _cell_length_c 15.9854(2) _cell_angle_alpha 90.00 _cell_angle_beta 112.123(1) _cell_angle_gamma 90.00 _cell_volume 3873.72(8) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7981 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method ? _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type ' empirical used sadabs' _exptl_absorpt_correction_T_min 0.7292 _exptl_absorpt_correction_T_max 0.9280 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Siemens SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18200 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.06 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7835 _reflns_number_observed 5673 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SAINT' _computing_data_reduction 'Siemens SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0508P)^2^+1.8207P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 7835 _refine_ls_number_parameters 560 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_obs 0.0502 _refine_ls_wR_factor_all 0.1295 _refine_ls_wR_factor_obs 0.1174 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.118 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.118 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.02195(9) 0.14492(14) -0.17339(11) 0.0589(4) Uani 1 d . . O2 O 0.10829(7) 0.26798(12) -0.13778(8) 0.0407(3) Uani 1 d . . O3 O 0.00826(7) 0.36497(12) -0.15476(10) 0.0462(4) Uani 1 d . . O4 O 0.16104(8) 0.46680(12) 0.08929(9) 0.0483(4) Uani 1 d . . O5 O 0.17333(10) 0.61342(13) 0.01625(11) 0.0604(5) Uani 1 d . . O6 O 0.18691(12) 0.95505(15) 0.17174(14) 0.0808(6) Uani 1 d . . O7 O 0.17692(10) 0.96167(14) 0.30154(15) 0.0719(5) Uani 1 d . . O8 O 0.14694(13) 0.6384(2) 0.44406(13) 0.0857(7) Uani 1 d . . O9 O 0.13268(13) 0.4910(2) 0.37172(13) 0.0860(7) Uani 1 d . . C1 C 0.09590(10) 0.3209(2) -0.00122(12) 0.0333(4) Uani 1 d . . C2 C 0.15746(11) 0.3966(2) 0.01430(13) 0.0428(5) Uani 1 d . . H2A H 0.15179(11) 0.4373(2) -0.04032(13) 0.051 Uiso 1 calc R . C3 C 0.22327(12) 0.3273(2) 0.0441(2) 0.0592(7) Uani 1 d . . H3A H 0.24667(12) 0.3357(2) 0.0023(2) 0.071 Uiso 1 calc R . H3B H 0.25494(12) 0.3486(2) 0.1037(2) 0.071 Uiso 1 calc R . C4 C 0.20155(12) 0.2121(2) 0.04556(15) 0.0504(6) Uani 1 d . . H4A H 0.19564(12) 0.1763(2) -0.01061(15) 0.060 Uiso 1 calc R . H4B H 0.23524(12) 0.1734(2) 0.09539(15) 0.060 Uiso 1 calc R . C5 C 0.13280(11) 0.2229(2) 0.05778(13) 0.0412(5) Uani 1 d . . H5A H 0.14431(11) 0.2441(2) 0.12074(13) 0.049 Uiso 1 calc R . C6 C 0.08351(13) 0.1288(2) 0.0413(2) 0.0513(6) Uani 1 d . . H6A H 0.08626(13) 0.0988(2) 0.0985(2) 0.062 Uiso 1 calc R . H6B H 0.09622(13) 0.0740(2) 0.0076(2) 0.062 Uiso 1 calc R . C7 C 0.00834(12) 0.1682(2) -0.0133(2) 0.0496(6) Uani 1 d . . H7A H -0.02646(12) 0.1140(2) -0.0167(2) 0.060 Uiso 1 calc R . C8 C 0.00980(11) 0.1934(2) -0.10487(14) 0.0408(5) Uani 1 d . . C9 C 0.05724(10) 0.2895(2) -0.10277(12) 0.0342(4) Uani 1 d . . C10 C 0.03836(11) 0.3499(2) 0.03065(13) 0.0417(5) Uani 1 d . . H10A H 0.03394(11) 0.4172(2) 0.05209(13) 0.050 Uiso 1 calc R . C11 C -0.00504(12) 0.2714(2) 0.02538(15) 0.0476(5) Uani 1 d . . H11A H -0.04186(12) 0.2793(2) 0.04443(15) 0.057 Uiso 1 calc R . C12 C 0.08525(13) 0.2419(2) -0.23209(14) 0.0550(6) Uani 1 d . . H12A H 0.12477(13) 0.2290(2) -0.24783(14) 0.083 Uiso 1 calc R . H12B H 0.05879(13) 0.3001(2) -0.26736(14) 0.083 Uiso 1 calc R . H12C H 0.05678(13) 0.1793(2) -0.24408(14) 0.083 Uiso 1 calc R . C13 C 0.03282(14) 0.4659(2) -0.1708(2) 0.0643(7) Uani 1 d . . H13A H -0.00582(14) 0.5089(2) -0.2068(2) 0.096 Uiso 1 calc R . H13B H 0.06368(14) 0.4559(2) -0.2021(2) 0.096 Uiso 1 calc R . H13C H 0.05713(14) 0.5006(2) -0.1141(2) 0.096 Uiso 1 calc R . C14 C 0.16764(10) 0.5714(2) 0.08037(14) 0.0386(5) Uani 1 d . . C15 C 0.16757(10) 0.6304(2) 0.16167(13) 0.0372(5) Uani 1 d . . C16 C 0.17431(10) 0.7406(2) 0.16223(14) 0.0404(5) Uani 1 d . . H16A H 0.17966(10) 0.7758(2) 0.11407(14) 0.049 Uiso 1 calc R . C17 C 0.17289(10) 0.7968(2) 0.23600(15) 0.0419(5) Uani 1 d . . C18 C 0.16355(11) 0.7488(2) 0.30806(14) 0.0432(5) Uani 1 d . . H18A H 0.16200(11) 0.7880(2) 0.35659(14) 0.052 Uiso 1 calc R . C19 C 0.15663(11) 0.6399(2) 0.30455(14) 0.0412(5) Uani 1 d . . C20 C 0.15897(10) 0.5795(2) 0.23349(13) 0.0394(5) Uani 1 d . . H20A H 0.15484(10) 0.5058(2) 0.23394(13) 0.047 Uiso 1 calc R . N1 N 0.17906(10) 0.9133(2) 0.2360(2) 0.0544(5) Uani 1 d . . N2 N 0.14429(11) 0.5859(2) 0.37876(13) 0.0554(5) Uani 1 d . . O10 O 0.47623(9) 0.85709(15) 0.14599(12) 0.0635(5) Uani 1 d . . O11 O 0.60766(7) 0.73871(12) 0.24157(9) 0.0431(4) Uani 1 d . . O12 O 0.50877(8) 0.63744(13) 0.16359(10) 0.0482(4) Uani 1 d . . O13 O 0.66276(8) 0.53312(11) 0.07073(9) 0.0432(4) Uani 1 d . . O14 O 0.67054(9) 0.38770(12) 0.15616(10) 0.0510(4) Uani 1 d . . O15 O 0.70017(12) 0.04465(14) 0.02913(15) 0.0762(6) Uani 1 d . . O16 O 0.68089(12) 0.03003(15) -0.11262(15) 0.0847(6) Uani 1 d . . O17 O 0.63983(15) 0.3480(2) -0.29751(13) 0.1024(8) Uani 1 d . . O18 O 0.6430(2) 0.4984(2) -0.23744(14) 0.1119(10) Uani 1 d . . C21 C 0.59593(10) 0.6789(2) 0.09470(12) 0.0328(4) Uani 1 d . . C22 C 0.65778(11) 0.6044(2) 0.14152(13) 0.0396(5) Uani 1 d . . H22A H 0.65117(11) 0.5638(2) 0.19001(13) 0.047 Uiso 1 calc R . C23 C 0.72318(12) 0.6745(2) 0.1785(2) 0.0511(6) Uani 1 d . . H23A H 0.74344(12) 0.6702(2) 0.2439(2) 0.061 Uiso 1 calc R . H23B H 0.75739(12) 0.6506(2) 0.1549(2) 0.061 Uiso 1 calc R . C24 C 0.70175(11) 0.7885(2) 0.14897(15) 0.0462(5) Uani 1 d . . H24A H 0.73569(11) 0.8234(2) 0.13019(15) 0.055 Uiso 1 calc R . H24B H 0.69622(11) 0.8293(2) 0.19734(15) 0.055 Uiso 1 calc R . C25 C 0.63268(11) 0.7758(2) 0.06986(13) 0.0385(5) Uani 1 d . . H25A H 0.64397(11) 0.7529(2) 0.01840(13) 0.046 Uiso 1 calc R . C26 C 0.58336(12) 0.8701(2) 0.0367(2) 0.0478(5) Uani 1 d . . H26A H 0.58639(12) 0.8993(2) -0.0179(2) 0.057 Uiso 1 calc R . H26B H 0.59573(12) 0.9255(2) 0.0822(2) 0.057 Uiso 1 calc R . C27 C 0.50850(12) 0.8303(2) 0.01737(15) 0.0469(5) Uani 1 d . . H27A H 0.47366(12) 0.8838(2) -0.01468(15) 0.056 Uiso 1 calc R . C28 C 0.50879(11) 0.8078(2) 0.11020(15) 0.0422(5) Uani 1 d . . C29 C 0.55715(10) 0.7132(2) 0.15715(13) 0.0354(4) Uani 1 d . . C30 C 0.53869(11) 0.6475(2) 0.00708(13) 0.0405(5) Uani 1 d . . H30A H 0.53439(11) 0.5793(2) -0.01693(13) 0.049 Uiso 1 calc R . C31 C 0.49528(11) 0.7254(2) -0.03244(14) 0.0464(5) Uani 1 d . . H31A H 0.45873(11) 0.7162(2) -0.08765(14) 0.056 Uiso 1 calc R . C32 C 0.58407(14) 0.7669(2) 0.3126(2) 0.0613(7) Uani 1 d . . H32A H 0.62335(14) 0.7826(2) 0.3667(2) 0.092 Uiso 1 calc R . H32B H 0.55853(14) 0.7086(2) 0.3237(2) 0.092 Uiso 1 calc R . H32C H 0.55463(14) 0.8283(2) 0.2949(2) 0.092 Uiso 1 calc R . C33 C 0.53420(15) 0.5391(2) 0.2079(2) 0.0698(8) Uani 1 d . . H33A H 0.49590(15) 0.4960(2) 0.2072(2) 0.105 Uiso 1 calc R . H33B H 0.56445(15) 0.5525(2) 0.2693(2) 0.105 Uiso 1 calc R . H33C H 0.55937(15) 0.5025(2) 0.1772(2) 0.105 Uiso 1 calc R . C34 C 0.66742(10) 0.4288(2) 0.08677(13) 0.0363(4) Uani 1 d . . C35 C 0.66769(10) 0.3669(2) 0.00667(13) 0.0357(4) Uani 1 d . . C36 C 0.67722(10) 0.2572(2) 0.01620(14) 0.0403(5) Uani 1 d . . H36A H 0.68384(10) 0.2242(2) 0.07092(14) 0.048 Uiso 1 calc R . C37 C 0.67667(11) 0.1983(2) -0.0568(2) 0.0425(5) Uani 1 d . . C38 C 0.66561(11) 0.2425(2) -0.14004(15) 0.0439(5) Uani 1 d . . H38A H 0.66421(11) 0.2012(2) -0.18898(15) 0.053 Uiso 1 calc R . C39 C 0.65671(11) 0.3515(2) -0.14668(13) 0.0409(5) Uani 1 d . . C40 C 0.65762(10) 0.4147(2) -0.07526(13) 0.0392(5) Uani 1 d . . H40A H 0.65157(10) 0.4879(2) -0.08228(13) 0.047 Uiso 1 calc R . N3 N 0.68637(10) 0.0820(2) -0.0464(2) 0.0554(5) Uani 1 d . . N4 N 0.64540(11) 0.4029(2) -0.23373(13) 0.0565(5) Uani 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 O1 0.0577(10) 0.0632(11) 0.0513(10) -0.0156(8) 0.0154(8) -0.0170(9) O2 0.0430(8) 0.0564(9) 0.0257(7) -0.0060(6) 0.0162(6) -0.0002(7) O3 0.0436(8) 0.0484(9) 0.0430(8) 0.0125(7) 0.0123(7) 0.0049(7) O4 0.0723(11) 0.0414(9) 0.0350(8) -0.0109(6) 0.0244(7) -0.0111(8) O5 0.0906(13) 0.0516(10) 0.0518(10) -0.0004(8) 0.0414(9) -0.0072(9) O6 0.110(2) 0.0458(11) 0.0735(13) 0.0087(10) 0.0203(12) -0.0057(11) O7 0.0710(12) 0.0470(10) 0.1030(15) -0.0301(11) 0.0389(11) -0.0074(9) O8 0.136(2) 0.0834(15) 0.0585(12) -0.0147(11) 0.0599(13) -0.0038(13) O9 0.146(2) 0.0622(13) 0.0630(12) -0.0038(10) 0.0547(13) -0.0307(13) C1 0.0390(11) 0.0354(11) 0.0282(9) -0.0024(8) 0.0158(8) 0.0016(8) C2 0.0526(13) 0.0472(13) 0.0321(10) -0.0139(9) 0.0202(9) -0.0100(10) C3 0.0408(13) 0.083(2) 0.0542(14) -0.0222(13) 0.0187(11) -0.0052(12) C4 0.0452(13) 0.067(2) 0.0360(11) -0.0014(11) 0.0122(10) 0.0155(12) C5 0.0474(12) 0.0488(13) 0.0276(10) 0.0018(9) 0.0144(9) 0.0086(10) C6 0.069(2) 0.0455(13) 0.0436(12) 0.0090(10) 0.0264(11) 0.0079(12) C7 0.0547(14) 0.0488(13) 0.0527(13) 0.0035(11) 0.0286(11) -0.0098(11) C8 0.0372(11) 0.0430(12) 0.0412(11) -0.0027(10) 0.0135(9) 0.0004(9) C9 0.0376(10) 0.0367(11) 0.0292(9) 0.0006(8) 0.0136(8) 0.0031(9) C10 0.0491(12) 0.0445(12) 0.0378(11) -0.0017(9) 0.0235(10) 0.0080(10) C11 0.0461(12) 0.0620(15) 0.0434(12) 0.0041(11) 0.0267(10) 0.0053(11) C12 0.065(2) 0.072(2) 0.0311(11) -0.0104(11) 0.0209(11) -0.0041(13) C13 0.068(2) 0.052(2) 0.072(2) 0.0225(13) 0.0244(14) 0.0083(13) C14 0.0351(11) 0.0422(12) 0.0381(11) -0.0047(9) 0.0135(9) -0.0047(9) C15 0.0334(10) 0.0390(11) 0.0386(11) -0.0062(9) 0.0128(8) -0.0025(9) C16 0.0338(11) 0.0422(12) 0.0429(11) -0.0001(9) 0.0118(9) -0.0015(9) C17 0.0343(11) 0.0342(11) 0.0506(12) -0.0068(10) 0.0083(9) -0.0005(9) C18 0.0394(12) 0.0468(13) 0.0414(12) -0.0110(10) 0.0129(9) 0.0012(9) C19 0.0423(12) 0.0445(12) 0.0371(11) -0.0050(9) 0.0154(9) -0.0033(10) C20 0.0417(11) 0.0368(11) 0.0392(11) -0.0063(9) 0.0148(9) -0.0049(9) N1 0.0461(11) 0.0392(11) 0.0685(14) -0.0050(11) 0.0110(10) -0.0013(9) N2 0.0692(14) 0.0584(14) 0.0441(11) -0.0044(10) 0.0275(10) -0.0041(11) O10 0.0584(10) 0.0684(12) 0.0709(11) -0.0082(9) 0.0325(9) 0.0164(9) O11 0.0437(8) 0.0593(10) 0.0293(7) -0.0085(6) 0.0172(6) -0.0026(7) O12 0.0457(9) 0.0540(10) 0.0484(9) 0.0050(7) 0.0215(7) -0.0085(7) O13 0.0628(10) 0.0363(8) 0.0349(7) -0.0024(6) 0.0235(7) 0.0092(7) O14 0.0733(11) 0.0416(9) 0.0416(8) 0.0016(7) 0.0255(8) -0.0030(8) O15 0.101(2) 0.0425(10) 0.0895(15) 0.0074(10) 0.0408(12) 0.0010(10) O16 0.105(2) 0.0493(11) 0.0915(15) -0.0253(11) 0.0280(13) 0.0124(11) O17 0.182(3) 0.0809(15) 0.0440(11) -0.0161(10) 0.0416(13) 0.000(2) O18 0.226(3) 0.0606(14) 0.0610(13) 0.0057(11) 0.068(2) 0.003(2) C21 0.0384(10) 0.0332(10) 0.0268(9) -0.0024(8) 0.0124(8) 0.0009(8) C22 0.0515(12) 0.0391(11) 0.0301(10) -0.0029(8) 0.0177(9) 0.0087(10) C23 0.0438(12) 0.061(2) 0.0419(12) -0.0115(11) 0.0084(10) 0.0075(11) C24 0.0425(12) 0.0521(14) 0.0471(12) -0.0082(11) 0.0203(10) -0.0080(10) C25 0.0425(11) 0.0424(12) 0.0352(10) -0.0001(9) 0.0199(9) -0.0021(9) C26 0.0569(14) 0.0414(12) 0.0478(12) 0.0063(10) 0.0228(11) -0.0011(11) C27 0.0449(12) 0.0460(13) 0.0458(12) 0.0102(10) 0.0125(10) 0.0121(10) C28 0.0362(11) 0.0433(12) 0.0468(12) -0.0062(10) 0.0153(9) -0.0005(9) C29 0.0358(10) 0.0403(11) 0.0319(10) -0.0027(9) 0.0146(8) -0.0046(9) C30 0.0461(12) 0.0443(12) 0.0306(10) -0.0050(9) 0.0139(9) -0.0056(10) C31 0.0418(12) 0.0607(15) 0.0312(10) 0.0007(10) 0.0074(9) -0.0018(11) C32 0.067(2) 0.085(2) 0.0403(13) -0.0163(12) 0.0304(12) -0.0053(14) C33 0.073(2) 0.060(2) 0.078(2) 0.0198(15) 0.0310(15) -0.0113(14) C34 0.0338(10) 0.0359(11) 0.0381(11) -0.0019(9) 0.0123(8) -0.0002(8) C35 0.0308(10) 0.0366(11) 0.0386(11) -0.0053(9) 0.0119(8) -0.0013(8) C36 0.0364(11) 0.0386(12) 0.0444(12) -0.0029(9) 0.0135(9) -0.0008(9) C37 0.0354(11) 0.0335(11) 0.0571(14) -0.0088(10) 0.0156(10) -0.0020(9) C38 0.0399(12) 0.0453(13) 0.0460(12) -0.0149(10) 0.0158(10) -0.0025(10) C39 0.0409(11) 0.0448(12) 0.0360(11) -0.0062(9) 0.0134(9) -0.0031(10) C40 0.0410(11) 0.0364(11) 0.0395(11) -0.0042(9) 0.0144(9) 0.0012(9) N3 0.0514(12) 0.0389(11) 0.0745(15) -0.0095(11) 0.0218(11) -0.0002(9) N4 0.0756(14) 0.0561(13) 0.0393(11) -0.0074(10) 0.0232(10) -0.0002(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 O1 C8 1.210(2) . ? O2 C9 1.401(2) . ? O2 C12 1.437(2) . ? O3 C9 1.412(2) . ? O3 C13 1.426(3) . ? O4 C14 1.336(3) . ? O4 C2 1.468(2) . ? O5 C14 1.198(2) . ? O6 N1 1.218(3) . ? O7 N1 1.227(3) . ? O8 N2 1.219(2) . ? O9 N2 1.215(3) . ? C1 C10 1.511(3) . ? C1 C2 1.538(3) . ? C1 C5 1.566(3) . ? C1 C9 1.567(3) . ? C2 C3 1.539(3) . ? C3 C4 1.521(4) . ? C4 C5 1.521(3) . ? C5 C6 1.522(3) . ? C6 C7 1.557(3) . ? C7 C11 1.507(3) . ? C7 C8 1.510(3) . ? C8 C9 1.552(3) . ? C10 C11 1.319(3) . ? C14 C15 1.497(3) . ? C15 C20 1.384(3) . ? C15 C16 1.393(3) . ? C16 C17 1.384(3) . ? C17 C18 1.377(3) . ? C17 N1 1.471(3) . ? C18 C19 1.377(3) . ? C19 C20 1.383(3) . ? C19 N2 1.471(3) . ? O10 C28 1.209(2) . ? O11 C29 1.400(2) . ? O11 C32 1.441(2) . ? O12 C29 1.417(2) . ? O12 C33 1.425(3) . ? O13 C34 1.334(2) . ? O13 C22 1.477(2) . ? O14 C34 1.203(2) . ? O15 N3 1.225(3) . ? O16 N3 1.212(3) . ? O17 N4 1.200(2) . ? O18 N4 1.202(3) . ? C21 C30 1.510(3) . ? C21 C22 1.539(3) . ? C21 C29 1.562(3) . ? C21 C25 1.567(3) . ? C22 C23 1.540(3) . ? C23 C24 1.523(3) . ? C24 C25 1.523(3) . ? C25 C26 1.527(3) . ? C26 C27 1.552(3) . ? C27 C28 1.508(3) . ? C27 C31 1.512(3) . ? C28 C29 1.556(3) . ? C30 C31 1.321(3) . ? C34 C35 1.500(3) . ? C35 C40 1.383(3) . ? C35 C36 1.395(3) . ? C36 C37 1.379(3) . ? C37 C38 1.379(3) . ? C37 N3 1.477(3) . ? C38 C39 1.382(3) . ? C39 C40 1.385(3) . ? C39 N4 1.471(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 C9 O2 C12 117.4(2) . . ? C9 O3 C13 118.4(2) . . ? C14 O4 C2 118.7(2) . . ? C10 C1 C2 120.9(2) . . ? C10 C1 C5 104.9(2) . . ? C2 C1 C5 101.6(2) . . ? C10 C1 C9 104.3(2) . . ? C2 C1 C9 113.2(2) . . ? C5 C1 C9 111.7(2) . . ? O4 C2 C1 106.7(2) . . ? O4 C2 C3 108.8(2) . . ? C1 C2 C3 106.8(2) . . ? C4 C3 C2 108.0(2) . . ? C5 C4 C3 102.5(2) . . ? C4 C5 C6 120.9(2) . . ? C4 C5 C1 105.3(2) . . ? C6 C5 C1 111.2(2) . . ? C5 C6 C7 108.6(2) . . ? C11 C7 C8 106.9(2) . . ? C11 C7 C6 110.3(2) . . ? C8 C7 C6 103.1(2) . . ? O1 C8 C7 124.7(2) . . ? O1 C8 C9 122.5(2) . . ? C7 C8 C9 112.8(2) . . ? O2 C9 O3 112.5(2) . . ? O2 C9 C8 114.4(2) . . ? O3 C9 C8 101.5(2) . . ? O2 C9 C1 106.98(15) . . ? O3 C9 C1 114.5(2) . . ? C8 C9 C1 107.0(2) . . ? C11 C10 C1 114.1(2) . . ? C10 C11 C7 116.3(2) . . ? O5 C14 O4 125.0(2) . . ? O5 C14 C15 123.8(2) . . ? O4 C14 C15 111.2(2) . . ? C20 C15 C16 120.0(2) . . ? C20 C15 C14 122.2(2) . . ? C16 C15 C14 117.8(2) . . ? C17 C16 C15 118.6(2) . . ? C18 C17 C16 123.0(2) . . ? C18 C17 N1 118.4(2) . . ? C16 C17 N1 118.6(2) . . ? C17 C18 C19 116.5(2) . . ? C18 C19 C20 123.0(2) . . ? C18 C19 N2 118.3(2) . . ? C20 C19 N2 118.7(2) . . ? C19 C20 C15 118.9(2) . . ? O6 N1 O7 124.4(2) . . ? O6 N1 C17 118.0(2) . . ? O7 N1 C17 117.6(2) . . ? O9 N2 O8 123.7(2) . . ? O9 N2 C19 117.9(2) . . ? O8 N2 C19 118.4(2) . . ? C29 O11 C32 117.5(2) . . ? C29 O12 C33 118.6(2) . . ? C34 O13 C22 118.1(2) . . ? C30 C21 C22 120.9(2) . . ? C30 C21 C29 104.4(2) . . ? C22 C21 C29 113.3(2) . . ? C30 C21 C25 105.0(2) . . ? C22 C21 C25 101.5(2) . . ? C29 C21 C25 111.5(2) . . ? O13 C22 C21 106.50(15) . . ? O13 C22 C23 109.6(2) . . ? C21 C22 C23 107.0(2) . . ? C24 C23 C22 107.9(2) . . ? C23 C24 C25 103.5(2) . . ? C24 C25 C26 120.5(2) . . ? C24 C25 C21 105.6(2) . . ? C26 C25 C21 111.4(2) . . ? C25 C26 C27 108.1(2) . . ? C28 C27 C31 106.7(2) . . ? C28 C27 C26 103.5(2) . . ? C31 C27 C26 110.9(2) . . ? O10 C28 C27 125.0(2) . . ? O10 C28 C29 122.6(2) . . ? C27 C28 C29 112.4(2) . . ? O11 C29 O12 112.3(2) . . ? O11 C29 C28 113.8(2) . . ? O12 C29 C28 101.6(2) . . ? O11 C29 C21 107.37(15) . . ? O12 C29 C21 114.4(2) . . ? C28 C29 C21 107.3(2) . . ? C31 C30 C21 114.0(2) . . ? C30 C31 C27 116.1(2) . . ? O14 C34 O13 125.1(2) . . ? O14 C34 C35 123.2(2) . . ? O13 C34 C35 111.7(2) . . ? C40 C35 C36 119.9(2) . . ? C40 C35 C34 122.4(2) . . ? C36 C35 C34 117.8(2) . . ? C37 C36 C35 118.9(2) . . ? C38 C37 C36 123.1(2) . . ? C38 C37 N3 118.3(2) . . ? C36 C37 N3 118.6(2) . . ? C37 C38 C39 116.3(2) . . ? C38 C39 C40 123.1(2) . . ? C38 C39 N4 118.5(2) . . ? C40 C39 N4 118.4(2) . . ? C35 C40 C39 118.8(2) . . ? O16 N3 O15 124.3(2) . . ? O16 N3 C37 118.1(2) . . ? O15 N3 C37 117.5(2) . . ? O17 N4 O18 122.9(2) . . ? O17 N4 C39 118.7(2) . . ? O18 N4 C39 118.3(2) . . ? _refine_diff_density_max 0.251 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.040 data_my09m _database_code_CSD 160765 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O9' _chemical_formula_weight 446.41 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.3649(3) _cell_length_b 9.8499(4) _cell_length_c 17.6830(7) _cell_angle_alpha 82.19 _cell_angle_beta 85.9730(10) _cell_angle_gamma 72.0600(10) _cell_volume 1044.45(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4094 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 mm _exptl_crystal_size_mid 0.20 mm _exptl_crystal_size_min 0.10 mm _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8493 _exptl_absorpt_correction_T_max 0.9573 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 10153 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _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 1.16 _diffrn_reflns_theta_max 28.07 _reflns_number_total 4527 _reflns_number_gt 2985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0402P)^2^+0.4935P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4527 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0906 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1379 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 O1 O 0.4070(2) 0.20108(16) 0.32509(8) 0.0475(4) Uani 1 1 d . . . O2 O 0.5922(3) 0.0373(2) 0.41821(10) 0.0672(5) Uani 1 1 d . . . O3 O 0.7590(3) 0.10903(18) 0.21791(10) 0.0633(5) Uani 1 1 d . . . O4 O 0.6298(3) 0.25432(19) 0.05857(9) 0.0602(5) Uani 1 1 d . . . O5 O 0.9725(3) 0.2441(2) 0.10262(10) 0.0671(5) Uani 1 1 d . . . O6 O -0.0006(4) -0.2025(2) 0.17703(12) 0.0832(6) Uani 1 1 d . . . O7 O 0.2479(4) -0.1006(3) 0.13811(12) 0.0907(7) Uani 1 1 d . . . O8 O -0.1065(5) -0.3180(3) 0.44713(14) 0.1153(9) Uani 1 1 d . . . O9 O -0.0008(3) -0.2070(2) 0.52621(11) 0.0746(6) Uani 1 1 d . . . N1 N 0.1325(4) -0.1409(2) 0.18786(13) 0.0644(6) Uani 1 1 d . . . N2 N -0.0113(4) -0.2354(2) 0.46201(14) 0.0654(6) Uani 1 1 d . . . C1 C 0.7013(4) 0.2361(2) 0.19553(13) 0.0449(5) Uani 1 1 d . . . C2 C 0.7415(4) 0.2970(3) 0.11219(13) 0.0506(6) Uani 1 1 d . . . C3 C 0.6474(4) 0.4615(3) 0.10662(14) 0.0544(6) Uani 1 1 d . . . C4 C 0.7708(4) 0.5159(3) 0.16205(16) 0.0627(7) Uani 1 1 d . . . C5 C 0.7429(4) 0.4485(2) 0.24482(14) 0.0503(6) Uani 1 1 d . . . C6 C 0.6512(5) 0.5602(3) 0.30024(17) 0.0670(8) Uani 1 1 d . . . C7 C 0.6114(5) 0.4950(3) 0.38076(17) 0.0699(8) Uani 1 1 d . . . C8 C 0.4595(5) 0.4014(3) 0.38158(15) 0.0625(7) Uani 1 1 d . . . C9 C 0.5552(4) 0.2887(2) 0.32828(13) 0.0462(5) Uani 1 1 d . . . C10 C 0.5866(3) 0.3519(2) 0.24649(12) 0.0408(5) Uani 1 1 d . . . C11 C 0.3790(3) 0.4401(2) 0.20538(14) 0.0476(6) Uani 1 1 d . . . C12 C 0.4102(4) 0.4952(3) 0.13475(15) 0.0542(6) Uani 1 1 d . . . C13 C 0.4542(4) 0.0761(2) 0.37025(12) 0.0462(5) Uani 1 1 d . . . C14 C 0.3144(4) -0.0128(2) 0.35360(12) 0.0434(5) Uani 1 1 d . . . C15 C 0.2255(4) -0.0848(2) 0.41444(13) 0.0464(5) Uani 1 1 d . . . C16 C 0.0950(4) -0.1655(2) 0.39825(13) 0.0483(5) Uani 1 1 d . . . C17 C 0.0590(4) -0.1838(2) 0.32510(14) 0.0522(6) Uani 1 1 d . . . C18 C 0.1579(4) -0.1161(2) 0.26656(13) 0.0480(5) Uani 1 1 d . . . C19 C 0.2803(4) -0.0274(2) 0.27881(13) 0.0475(5) Uani 1 1 d . . . C20 C 0.6814(5) 0.1025(3) 0.05555(17) 0.0766(8) Uani 1 1 d . . . C21 C 1.0606(5) 0.2792(4) 0.02838(19) 0.0891(10) Uani 1 1 d . . . H3A H 0.6637 0.5037 0.0529 0.080 Uiso 1 1 d . . . H4A H 0.9318 0.4911 0.1430 0.080 Uiso 1 1 d . . . H4B H 0.7088 0.6242 0.1563 0.080 Uiso 1 1 d . . . H5A H 0.8887 0.3866 0.2596 0.080 Uiso 1 1 d . . . H6A H 0.5123 0.6297 0.2771 0.080 Uiso 1 1 d . . . H6B H 0.7444 0.6222 0.2992 0.080 Uiso 1 1 d . . . H7A H 0.7558 0.4355 0.4004 0.080 Uiso 1 1 d . . . H7B H 0.5505 0.5693 0.4123 0.080 Uiso 1 1 d . . . H8A H 0.3013 0.4631 0.3639 0.080 Uiso 1 1 d . . . H8B H 0.4399 0.3558 0.4303 0.080 Uiso 1 1 d . . . H9A H 0.7002 0.2187 0.3435 0.080 Uiso 1 1 d . . . H11A H 0.2432 0.4505 0.2305 0.080 Uiso 1 1 d . . . H12A H 0.2889 0.5541 0.1002 0.080 Uiso 1 1 d . . . H15A H 0.2492 -0.0751 0.4644 0.080 Uiso 1 1 d . . . H17A H -0.0390 -0.2390 0.3111 0.080 Uiso 1 1 d . . . H19A H 0.3451 0.0192 0.2363 0.080 Uiso 1 1 d . . . H20A H 0.8338 0.0558 0.0622 0.080 Uiso 1 1 d . . . H20B H 0.6230 0.0950 0.0052 0.080 Uiso 1 1 d . . . H20C H 0.6000 0.0621 0.0942 0.080 Uiso 1 1 d . . . H21A H 0.9904 0.2496 -0.0127 0.080 Uiso 1 1 d . . . H21B H 1.2069 0.2548 0.0314 0.080 Uiso 1 1 d . . . H21C H 1.0029 0.3851 0.0126 0.080 Uiso 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 O1 0.0524(9) 0.0475(9) 0.0495(9) -0.0003(7) -0.0076(7) -0.0264(7) O2 0.0797(12) 0.0789(12) 0.0554(11) 0.0142(9) -0.0242(9) -0.0467(10) O3 0.0818(13) 0.0451(10) 0.0552(10) -0.0021(8) -0.0050(9) -0.0088(9) O4 0.0552(10) 0.0733(12) 0.0525(10) -0.0071(8) -0.0110(8) -0.0179(9) O5 0.0387(9) 0.0900(13) 0.0633(11) 0.0026(9) -0.0020(8) -0.0107(9) O6 0.1126(17) 0.0722(13) 0.0796(14) -0.0263(10) -0.0309(12) -0.0361(12) O7 0.1242(19) 0.1086(17) 0.0488(12) -0.0222(11) 0.0022(12) -0.0448(15) O8 0.175(3) 0.1235(19) 0.0973(17) -0.0176(14) 0.0166(16) -0.121(2) O9 0.0977(15) 0.0780(13) 0.0566(12) -0.0032(10) 0.0076(10) -0.0432(11) N1 0.0837(17) 0.0548(13) 0.0548(14) -0.0168(10) -0.0145(12) -0.0140(12) N2 0.0823(16) 0.0558(13) 0.0684(16) -0.0036(11) 0.0060(12) -0.0394(12) C1 0.0396(12) 0.0489(13) 0.0471(13) -0.0010(10) -0.0090(10) -0.0150(10) C2 0.0373(12) 0.0640(15) 0.0484(13) 0.0015(11) -0.0051(10) -0.0151(11) C3 0.0481(13) 0.0627(15) 0.0523(14) 0.0126(11) -0.0097(11) -0.0229(12) C4 0.0584(15) 0.0654(16) 0.0717(17) 0.0110(13) -0.0105(13) -0.0356(13) C5 0.0441(13) 0.0499(13) 0.0623(15) 0.0023(11) -0.0143(11) -0.0233(11) C6 0.0769(18) 0.0510(15) 0.085(2) -0.0073(13) -0.0154(15) -0.0341(14) C7 0.091(2) 0.0585(16) 0.0722(19) -0.0206(13) -0.0098(15) -0.0322(15) C8 0.0780(18) 0.0634(16) 0.0563(15) -0.0173(12) 0.0037(13) -0.0334(14) C9 0.0516(13) 0.0472(12) 0.0485(13) -0.0044(10) -0.0067(10) -0.0271(11) C10 0.0390(11) 0.0404(11) 0.0468(12) -0.0019(9) -0.0073(9) -0.0178(9) C11 0.0362(12) 0.0473(13) 0.0617(15) -0.0041(11) -0.0080(10) -0.0156(10) C12 0.0430(13) 0.0529(14) 0.0647(16) 0.0039(12) -0.0152(11) -0.0133(11) C13 0.0548(14) 0.0523(13) 0.0373(11) -0.0038(10) -0.0017(10) -0.0253(11) C14 0.0485(13) 0.0416(12) 0.0430(12) -0.0047(9) -0.0037(10) -0.0172(10) C15 0.0550(14) 0.0438(12) 0.0443(12) -0.0046(9) -0.0055(10) -0.0199(10) C16 0.0565(14) 0.0411(12) 0.0510(13) -0.0050(10) -0.0005(11) -0.0207(10) C17 0.0598(15) 0.0436(12) 0.0596(15) -0.0126(11) -0.0082(12) -0.0207(11) C18 0.0577(14) 0.0413(12) 0.0462(13) -0.0129(10) -0.0109(11) -0.0116(10) C19 0.0572(14) 0.0439(12) 0.0418(12) -0.0057(9) -0.0033(10) -0.0153(11) C20 0.086(2) 0.080(2) 0.0659(18) -0.0184(15) -0.0088(15) -0.0235(17) C21 0.0513(16) 0.123(3) 0.081(2) 0.0064(19) 0.0146(15) -0.0196(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C13 1.335(3) . ? O1 C9 1.469(2) . ? O2 C13 1.203(3) . ? O3 C1 1.208(3) . ? O4 C2 1.404(3) . ? O4 C20 1.437(3) . ? O5 C2 1.407(3) . ? O5 C21 1.432(3) . ? O6 N1 1.222(3) . ? O7 N1 1.211(3) . ? O8 N2 1.218(3) . ? O9 N2 1.216(3) . ? N1 C18 1.473(3) . ? N2 C16 1.474(3) . ? C1 C10 1.523(3) . ? C1 C2 1.549(3) . ? C2 C3 1.536(3) . ? C3 C12 1.506(3) . ? C3 C4 1.541(4) . ? C4 C5 1.545(3) . ? C5 C6 1.527(4) . ? C5 C10 1.571(3) . ? C6 C7 1.518(4) . ? C7 C8 1.526(4) . ? C8 C9 1.510(3) . ? C9 C10 1.520(3) . ? C10 C11 1.511(3) . ? C11 C12 1.320(3) . ? C13 C14 1.494(3) . ? C14 C19 1.389(3) . ? C14 C15 1.391(3) . ? C15 C16 1.380(3) . ? C16 C17 1.374(3) . ? C17 C18 1.375(3) . ? C18 C19 1.382(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 C13 O1 C9 116.43(16) . . ? C2 O4 C20 116.77(19) . . ? C2 O5 C21 115.76(19) . . ? O7 N1 O6 124.2(2) . . ? O7 N1 C18 117.6(2) . . ? O6 N1 C18 118.2(2) . . ? O9 N2 O8 123.7(2) . . ? O9 N2 C16 118.6(2) . . ? O8 N2 C16 117.8(2) . . ? O3 C1 C10 123.6(2) . . ? O3 C1 C2 123.0(2) . . ? C10 C1 C2 113.43(18) . . ? O4 C2 O5 112.5(2) . . ? O4 C2 C3 106.10(18) . . ? O5 C2 C3 115.0(2) . . ? O4 C2 C1 113.33(19) . . ? O5 C2 C1 102.70(17) . . ? C3 C2 C1 107.33(19) . . ? C12 C3 C2 106.96(19) . . ? C12 C3 C4 107.1(2) . . ? C2 C3 C4 108.64(19) . . ? C3 C4 C5 110.53(18) . . ? C6 C5 C4 113.1(2) . . ? C6 C5 C10 109.39(19) . . ? C4 C5 C10 109.58(18) . . ? C7 C6 C5 113.3(2) . . ? C6 C7 C8 111.4(2) . . ? C9 C8 C7 109.3(2) . . ? O1 C9 C8 110.48(19) . . ? O1 C9 C10 106.07(16) . . ? C8 C9 C10 113.22(19) . . ? C11 C10 C9 116.37(18) . . ? C11 C10 C1 104.81(17) . . ? C9 C10 C1 112.05(17) . . ? C11 C10 C5 107.98(17) . . ? C9 C10 C5 109.38(17) . . ? C1 C10 C5 105.61(18) . . ? C12 C11 C10 115.4(2) . . ? C11 C12 C3 115.4(2) . . ? O2 C13 O1 125.2(2) . . ? O2 C13 C14 123.3(2) . . ? O1 C13 C14 111.48(19) . . ? C19 C14 C15 120.6(2) . . ? C19 C14 C13 120.62(19) . . ? C15 C14 C13 118.75(19) . . ? C16 C15 C14 118.1(2) . . ? C17 C16 C15 123.0(2) . . ? C17 C16 N2 118.2(2) . . ? C15 C16 N2 118.8(2) . . ? C16 C17 C18 117.1(2) . . ? C17 C18 C19 122.7(2) . . ? C17 C18 N1 118.1(2) . . ? C19 C18 N1 119.2(2) . . ? C18 C19 C14 118.3(2) . . ? _diffrn_measured_fraction_theta_max 0.891 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.891 _refine_diff_density_max 0.171 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.041