# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d02282013_0m #TrackingRef 'web_deposit_cif_file_0_DavidSandoval_1365105172.d02282013_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H23 Br2 N O6' _chemical_formula_weight 617.28 _chemical_absolute_configuration ad 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.939(4) _cell_length_b 18.900(9) _cell_length_c 19.529(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2561(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 3.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4462 _exptl_absorpt_correction_T_max 0.9386 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12302 _diffrn_reflns_av_R_equivalents 0.2219 _diffrn_reflns_av_sigmaI/netI 0.3125 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 24.11 _reflns_number_total 4039 _reflns_number_gt 1863 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0894P)^2^+0.0000P] 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 0.0041(10) _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 0.00(3) _refine_ls_number_reflns 4039 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2205 _refine_ls_R_factor_gt 0.0951 _refine_ls_wR_factor_ref 0.2325 _refine_ls_wR_factor_gt 0.1869 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 Br1 Br 0.1655(2) 0.61370(8) 0.50283(11) 0.0388(6) Uani 1 1 d . . . Br2 Br 1.6881(3) 0.66243(10) 0.91733(11) 0.0480(7) Uani 1 1 d . . . C1 C 0.383(2) 0.6430(7) 0.5516(10) 0.0259(18) Uani 1 1 d . . . C2 C 0.394(2) 0.6361(7) 0.6228(10) 0.0259(18) Uani 1 1 d . . . H2 H 0.2875 0.6162 0.6466 0.031 Uiso 1 1 calc R . . C3 C 0.549(2) 0.6566(8) 0.6584(10) 0.0259(18) Uani 1 1 d . . . H3 H 0.5524 0.6511 0.7068 0.031 Uiso 1 1 calc R . . C4 C 0.705(2) 0.6863(7) 0.6239(9) 0.025(3) Uani 1 1 d . . . C5 C 0.701(2) 0.6928(7) 0.5530(9) 0.0259(18) Uani 1 1 d . . . H5 H 0.8093 0.7122 0.5297 0.031 Uiso 1 1 calc R . . C6 C 0.536(2) 0.6707(7) 0.5148(9) 0.0259(18) Uani 1 1 d . . . H6 H 0.5320 0.6747 0.4663 0.031 Uiso 1 1 calc R . . C7 C 0.870(2) 0.7157(8) 0.6591(11) 0.030(3) Uani 1 1 d . . . C8 C 0.960(2) 0.7563(9) 0.7674(10) 0.030(3) Uani 1 1 d . . . C9 C 1.124(2) 0.7319(7) 0.8071(9) 0.025(3) Uani 1 1 d . . . C10 C 1.222(2) 0.7771(9) 0.8531(9) 0.033(3) Uani 1 1 d . . . H10 H 1.1749 0.8238 0.8602 0.039 Uiso 1 1 calc R . . C11 C 1.384(2) 0.7545(9) 0.8882(10) 0.034(4) Uani 1 1 d . . . H11 H 1.4401 0.7844 0.9219 0.040 Uiso 1 1 calc R . . C12 C 1.466(2) 0.6896(7) 0.8749(9) 0.0259(18) Uani 1 1 d . . . C13 C 1.362(2) 0.6417(9) 0.8336(9) 0.034(4) Uani 1 1 d . . . H13 H 1.4063 0.5944 0.8288 0.040 Uiso 1 1 calc R . . C14 C 1.194(2) 0.6638(8) 0.7995(9) 0.033(3) Uani 1 1 d . . . H14 H 1.1281 0.6314 0.7708 0.039 Uiso 1 1 calc R . . C15 C 0.712(2) 0.9048(8) 0.7130(9) 0.031(5) Uani 1 1 d . . . C16 C 0.523(3) 0.9125(10) 0.6745(10) 0.036(5) Uani 1 1 d . . . C17 C 0.401(2) 0.8458(9) 0.6654(10) 0.038(4) Uani 1 1 d . . . H17A H 0.2759 0.8586 0.6457 0.057 Uiso 1 1 calc R . . H17B H 0.3814 0.8232 0.7100 0.057 Uiso 1 1 calc R . . H17C H 0.4675 0.8129 0.6347 0.057 Uiso 1 1 calc R . . C18 C 0.685(3) 0.9431(9) 0.7793(10) 0.030(3) Uani 1 1 d . . . C19 C 0.876(2) 0.9381(9) 0.6721(10) 0.038(4) Uani 1 1 d . . . H19A H 0.9995 0.9268 0.6940 0.057 Uiso 1 1 calc R . . H19B H 0.8593 0.9896 0.6707 0.057 Uiso 1 1 calc R . . H19C H 0.8755 0.9194 0.6253 0.057 Uiso 1 1 calc R . . C20 C 0.513(2) 0.9364(8) 0.8875(9) 0.025(3) Uani 1 1 d . . . C21 C 0.628(2) 0.9239(8) 0.9427(8) 0.018(4) Uiso 1 1 d . . . C22 C 0.556(2) 0.9483(8) 1.0025(10) 0.032(3) Uiso 1 1 d . . . H22 H 0.6300 0.9405 1.0428 0.038 Uiso 1 1 calc R . . C23 C 0.384(2) 0.9838(8) 1.0089(10) 0.029(4) Uiso 1 1 d . . . H23 H 0.3386 0.9990 1.0523 0.035 Uiso 1 1 calc R . . C24 C 0.280(2) 0.9967(9) 0.9496(9) 0.032(3) Uiso 1 1 d . . . H24 H 0.1612 1.0217 0.9522 0.038 Uiso 1 1 calc R . . C25 C 0.348(2) 0.9729(8) 0.8857(9) 0.026(4) Uiso 1 1 d . . . C26 C 0.811(2) 0.8837(9) 0.9392(10) 0.047(4) Uani 1 1 d . . . H26A H 0.7896 0.8388 0.9154 0.071 Uiso 1 1 calc R . . H26B H 0.8579 0.8743 0.9857 0.071 Uiso 1 1 calc R . . H26C H 0.9077 0.9115 0.9142 0.071 Uiso 1 1 calc R . . C27 C 0.234(3) 0.9853(9) 0.8234(10) 0.047(4) Uani 1 1 d . . . H27A H 0.3099 1.0130 0.7907 0.071 Uiso 1 1 calc R . . H27B H 0.1163 1.0113 0.8352 0.071 Uiso 1 1 calc R . . H27C H 0.1991 0.9397 0.8027 0.071 Uiso 1 1 calc R . . N N 0.9103(19) 0.8233(7) 0.7678(8) 0.033(4) Uani 1 1 d . . . O1 O 1.0076(16) 0.7470(5) 0.6340(6) 0.031(3) Uani 1 1 d . . . O2 O 0.8616(16) 0.7066(5) 0.7293(6) 0.032(3) Uani 1 1 d . . . O3 O 0.7473(15) 0.8307(5) 0.7227(6) 0.030(3) Uani 1 1 d . . . O4 O 0.4718(19) 0.9690(6) 0.6546(8) 0.052(4) Uani 1 1 d . . . O5 O 0.7496(16) 1.0017(6) 0.7939(6) 0.035(3) Uani 1 1 d . . . O6 O 0.5723(16) 0.9066(5) 0.8224(6) 0.030(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0329(10) 0.0205(9) 0.0630(14) -0.0032(10) -0.0033(13) -0.0019(9) Br2 0.0380(12) 0.0332(10) 0.0729(16) 0.0109(11) -0.0061(13) 0.0058(11) C1 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C2 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C3 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C4 0.019(6) 0.008(5) 0.048(8) 0.001(5) 0.013(5) 0.003(4) C5 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C6 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C7 0.018(6) 0.018(6) 0.053(8) -0.002(5) 0.003(6) 0.002(5) C8 0.018(6) 0.018(6) 0.053(8) -0.002(5) 0.003(6) 0.002(5) C9 0.019(6) 0.008(5) 0.048(8) 0.001(5) 0.013(5) 0.003(4) C10 0.037(8) 0.020(6) 0.041(9) 0.010(6) 0.004(8) -0.011(7) C11 0.024(8) 0.030(8) 0.046(10) 0.000(6) -0.013(7) 0.002(6) C12 0.025(4) 0.004(3) 0.049(5) -0.001(4) 0.013(4) 0.002(3) C13 0.024(8) 0.030(8) 0.046(10) 0.000(6) -0.013(7) 0.002(6) C14 0.037(8) 0.020(6) 0.041(9) 0.010(6) 0.004(8) -0.011(7) C15 0.032(11) 0.009(9) 0.051(14) 0.007(8) 0.006(10) -0.003(8) C16 0.037(13) 0.041(14) 0.029(14) -0.011(10) 0.002(10) -0.021(11) C17 0.033(8) 0.032(8) 0.049(10) 0.005(7) 0.005(7) 0.008(7) C18 0.018(6) 0.018(6) 0.053(8) -0.002(5) 0.003(6) 0.002(5) C19 0.033(8) 0.032(8) 0.049(10) 0.005(7) 0.005(7) 0.008(7) C20 0.019(6) 0.008(5) 0.048(8) 0.001(5) 0.013(5) 0.003(4) C26 0.044(9) 0.025(7) 0.073(11) -0.002(7) -0.005(8) -0.024(7) C27 0.044(9) 0.025(7) 0.073(11) -0.002(7) -0.005(8) -0.024(7) N 0.031(9) 0.018(9) 0.050(12) -0.005(8) 0.005(8) 0.002(7) O1 0.023(7) 0.015(6) 0.054(9) -0.006(6) -0.004(6) 0.000(6) O2 0.034(8) 0.025(6) 0.036(9) 0.003(6) 0.005(7) -0.002(6) O3 0.034(7) 0.012(6) 0.045(8) -0.005(6) 0.000(6) 0.006(5) O4 0.050(9) 0.018(8) 0.087(12) 0.003(7) -0.023(9) 0.011(7) O5 0.033(7) 0.025(7) 0.047(9) -0.006(6) 0.011(6) -0.004(5) O6 0.030(7) 0.009(6) 0.051(9) -0.003(6) 0.013(6) -0.002(5) _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 C1 1.869(17) . ? Br2 C12 1.825(17) . ? C1 C6 1.39(2) . ? C1 C2 1.40(2) . ? C2 C3 1.34(2) . ? C2 H2 0.9500 . ? C3 C4 1.39(2) . ? C3 H3 0.9500 . ? C4 C5 1.39(2) . ? C4 C7 1.45(2) . ? C5 C6 1.43(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.224(19) . ? C7 O2 1.38(2) . ? C8 N 1.312(19) . ? C8 O2 1.380(19) . ? C8 C9 1.45(2) . ? C9 C14 1.38(2) . ? C9 C10 1.41(2) . ? C10 C11 1.39(2) . ? C10 H10 0.9500 . ? C11 C12 1.38(2) . ? C11 H11 0.9500 . ? C12 C13 1.41(2) . ? C13 C14 1.41(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 O3 1.434(17) . ? C15 C18 1.49(2) . ? C15 C16 1.52(2) . ? C15 C19 1.53(2) . ? C16 O4 1.19(2) . ? C16 C17 1.53(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O5 1.229(18) . ? C18 O6 1.34(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C25 1.34(2) . ? C20 C21 1.36(2) . ? C20 O6 1.449(19) . ? C21 C22 1.35(2) . ? C21 C26 1.48(2) . ? C22 C23 1.38(2) . ? C22 H22 0.9500 . ? C23 C24 1.39(2) . ? C23 H23 0.9500 . ? C24 C25 1.41(2) . ? C24 H24 0.9500 . ? C25 C27 1.47(2) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? N O3 1.440(16) . ? 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 C1 C2 120.6(16) . . ? C6 C1 Br1 117.9(14) . . ? C2 C1 Br1 121.5(13) . . ? C3 C2 C1 122.2(17) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 119.3(18) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.3(17) . . ? C5 C4 C7 117.0(16) . . ? C3 C4 C7 122.6(17) . . ? C4 C5 C6 120.6(16) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 117.0(17) . . ? C1 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? O1 C7 O2 119.5(16) . . ? O1 C7 C4 127.7(19) . . ? O2 C7 C4 112.9(15) . . ? N C8 O2 122.0(15) . . ? N C8 C9 120.7(16) . . ? O2 C8 C9 117.4(14) . . ? C14 C9 C10 117.4(16) . . ? C14 C9 C8 121.0(17) . . ? C10 C9 C8 121.5(14) . . ? C11 C10 C9 121.2(16) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 121.1(18) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 118.1(15) . . ? C11 C12 Br2 120.9(14) . . ? C13 C12 Br2 120.7(11) . . ? C14 C13 C12 120.2(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C9 C14 C13 121.2(17) . . ? C9 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? O3 C15 C18 112.4(14) . . ? O3 C15 C16 107.9(13) . . ? C18 C15 C16 106.0(14) . . ? O3 C15 C19 110.0(13) . . ? C18 C15 C19 110.3(14) . . ? C16 C15 C19 110.2(14) . . ? O4 C16 C15 120.3(15) . . ? O4 C16 C17 122.4(17) . . ? C15 C16 C17 117.2(16) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O5 C18 O6 122.2(16) . . ? O5 C18 C15 126.2(17) . . ? O6 C18 C15 111.6(14) . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 127.7(17) . . ? C25 C20 O6 114.8(16) . . ? C21 C20 O6 117.5(13) . . ? C22 C21 C20 114.3(15) . . ? C22 C21 C26 121.9(16) . . ? C20 C21 C26 123.7(15) . . ? C21 C22 C23 124.3(18) . . ? C21 C22 H22 117.9 . . ? C23 C22 H22 117.9 . . ? C22 C23 C24 117.6(17) . . ? C22 C23 H23 121.2 . . ? C24 C23 H23 121.2 . . ? C23 C24 C25 120.5(15) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? C20 C25 C24 115.4(16) . . ? C20 C25 C27 124.4(16) . . ? C24 C25 C27 120.1(16) . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C8 N O3 107.4(13) . . ? C8 O2 C7 115.3(13) . . ? C15 O3 N 108.1(11) . . ? C18 O6 C20 121.0(12) . . ? 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 1(2) . . . . ? Br1 C1 C2 C3 179.8(11) . . . . ? C1 C2 C3 C4 0(2) . . . . ? C2 C3 C4 C5 -2(2) . . . . ? C2 C3 C4 C7 174.1(14) . . . . ? C3 C4 C5 C6 1(2) . . . . ? C7 C4 C5 C6 -174.6(12) . . . . ? C2 C1 C6 C5 -1(2) . . . . ? Br1 C1 C6 C5 180.0(10) . . . . ? C4 C5 C6 C1 0(2) . . . . ? C5 C4 C7 O1 1(2) . . . . ? C3 C4 C7 O1 -174.7(15) . . . . ? C5 C4 C7 O2 -179.8(13) . . . . ? C3 C4 C7 O2 4(2) . . . . ? N C8 C9 C14 -170.7(16) . . . . ? O2 C8 C9 C14 9(2) . . . . ? N C8 C9 C10 7(3) . . . . ? O2 C8 C9 C10 -173.3(14) . . . . ? C14 C9 C10 C11 1(2) . . . . ? C8 C9 C10 C11 -176.5(16) . . . . ? C9 C10 C11 C12 6(3) . . . . ? C10 C11 C12 C13 -11(3) . . . . ? C10 C11 C12 Br2 176.2(13) . . . . ? C11 C12 C13 C14 9(3) . . . . ? Br2 C12 C13 C14 -178.1(12) . . . . ? C10 C9 C14 C13 -3(2) . . . . ? C8 C9 C14 C13 174.7(15) . . . . ? C12 C13 C14 C9 -2(3) . . . . ? O3 C15 C16 O4 -172.7(17) . . . . ? C18 C15 C16 O4 67(2) . . . . ? C19 C15 C16 O4 -53(2) . . . . ? O3 C15 C16 C17 10(2) . . . . ? C18 C15 C16 C17 -110.8(17) . . . . ? C19 C15 C16 C17 129.8(16) . . . . ? O3 C15 C18 O5 138.8(16) . . . . ? C16 C15 C18 O5 -104(2) . . . . ? C19 C15 C18 O5 16(2) . . . . ? O3 C15 C18 O6 -43.4(19) . . . . ? C16 C15 C18 O6 74.2(17) . . . . ? C19 C15 C18 O6 -166.5(13) . . . . ? C25 C20 C21 C22 4(2) . . . . ? O6 C20 C21 C22 -174.9(13) . . . . ? C25 C20 C21 C26 -178.9(15) . . . . ? O6 C20 C21 C26 2(2) . . . . ? C20 C21 C22 C23 -1(2) . . . . ? C26 C21 C22 C23 -177.8(14) . . . . ? C21 C22 C23 C24 -1(2) . . . . ? C22 C23 C24 C25 1(2) . . . . ? C21 C20 C25 C24 -5(2) . . . . ? O6 C20 C25 C24 174.4(13) . . . . ? C21 C20 C25 C27 178.8(15) . . . . ? O6 C20 C25 C27 -2(2) . . . . ? C23 C24 C25 C20 2(2) . . . . ? C23 C24 C25 C27 178.5(15) . . . . ? O2 C8 N O3 -1(2) . . . . ? C9 C8 N O3 178.7(14) . . . . ? N C8 O2 C7 65(2) . . . . ? C9 C8 O2 C7 -115.0(16) . . . . ? O1 C7 O2 C8 26(2) . . . . ? C4 C7 O2 C8 -153.3(13) . . . . ? C18 C15 O3 N -55.2(16) . . . . ? C16 C15 O3 N -171.6(12) . . . . ? C19 C15 O3 N 68.1(16) . . . . ? C8 N O3 C15 -170.1(14) . . . . ? O5 C18 O6 C20 3(2) . . . . ? C15 C18 O6 C20 -174.7(14) . . . . ? C25 C20 O6 C18 90.1(17) . . . . ? C21 C20 O6 C18 -90.7(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.11 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.806 _refine_diff_density_min -1.123 _refine_diff_density_rms 0.168 _database_code_depnum_ccdc_archive 'CCDC 932616' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_l10192012_0m #TrackingRef '14933_web_deposit_cif_file_0_LeoniPalmer_1351097701.l10192012_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H25 N O6' _chemical_formula_weight 327.37 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 9.8524(4) _cell_length_b 15.9675(5) _cell_length_c 10.5673(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.813(2) _cell_angle_gamma 90.00 _cell_volume 1660.43(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7066 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Kappa Apex' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13745 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0118 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.17 _reflns_number_total 3678 _reflns_number_gt 3345 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0304P)^2^+0.8586P] 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 3678 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0351 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.67073(11) 0.04772(7) 0.75125(10) 0.0196(2) Uani 1 1 d . . . H1A H 0.7602 0.0281 0.7834 0.029 Uiso 1 1 calc R . . H1B H 0.5999 0.0211 0.7992 0.029 Uiso 1 1 calc R . . H1C H 0.6654 0.1087 0.7610 0.029 Uiso 1 1 calc R . . C2 C 0.65046(10) 0.02522(6) 0.61340(9) 0.0164(2) Uani 1 1 d . . . H2A H 0.6551 -0.0363 0.6022 0.020 Uiso 1 1 calc R . . H2B H 0.5606 0.0450 0.5796 0.020 Uiso 1 1 calc R . . C3 C 0.74196(10) 0.06945(6) 0.42208(9) 0.01329(19) Uani 1 1 d . . . C4 C 0.86502(9) 0.10838(6) 0.36135(8) 0.01090(18) Uani 1 1 d . . . C5 C 0.96063(10) 0.03865(6) 0.32008(9) 0.01309(19) Uani 1 1 d . . . H5A H 1.0508 0.0632 0.3053 0.016 Uiso 1 1 calc R . . H5B H 0.9727 -0.0027 0.3896 0.016 Uiso 1 1 calc R . . C6 C 0.90812(11) -0.00638(6) 0.20015(9) 0.0167(2) Uani 1 1 d . . . H6A H 0.9770 -0.0473 0.1742 0.020 Uiso 1 1 calc R . . H6B H 0.8243 -0.0376 0.2179 0.020 Uiso 1 1 calc R . . C7 C 0.87778(11) 0.05544(7) 0.09248(9) 0.0179(2) Uani 1 1 d . . . H7A H 0.8447 0.0246 0.0157 0.022 Uiso 1 1 calc R . . H7B H 0.9622 0.0853 0.0725 0.022 Uiso 1 1 calc R . . C8 C 0.77052(10) 0.11879(6) 0.12952(9) 0.0161(2) Uani 1 1 d . . . H8A H 0.7547 0.1600 0.0604 0.019 Uiso 1 1 calc R . . H8B H 0.6838 0.0896 0.1428 0.019 Uiso 1 1 calc R . . C9 C 0.81773(9) 0.16342(6) 0.24937(9) 0.01237(18) Uani 1 1 d . . . C10 C 0.87660(10) 0.24796(6) 0.24275(9) 0.01459(19) Uani 1 1 d . . . H10 H 0.8820 0.2721 0.1558 0.018 Uiso 1 1 calc R . . C11 C 0.98425(10) 0.27677(6) 0.33897(9) 0.01502(19) Uani 1 1 d . . . H11A H 1.0585 0.3051 0.2958 0.018 Uiso 1 1 calc R . . H11B H 0.9449 0.3172 0.3981 0.018 Uiso 1 1 calc R . . C12 C 1.14617(10) 0.20979(6) 0.49771(9) 0.01458(19) Uani 1 1 d . . . C13 C 1.35549(10) 0.29146(7) 0.53564(10) 0.0171(2) Uani 1 1 d . . . C14 C 1.44998(12) 0.21661(8) 0.53462(12) 0.0269(2) Uani 1 1 d . . . H14A H 1.4085 0.1694 0.5776 0.040 Uiso 1 1 calc R . . H14B H 1.5367 0.2310 0.5788 0.040 Uiso 1 1 calc R . . H14C H 1.4659 0.2011 0.4469 0.040 Uiso 1 1 calc R . . C15 C 1.32520(12) 0.31839(8) 0.66914(10) 0.0251(2) Uani 1 1 d . . . H15A H 1.2555 0.3622 0.6653 0.038 Uiso 1 1 calc R . . H15B H 1.4083 0.3401 0.7121 0.038 Uiso 1 1 calc R . . H15C H 1.2922 0.2702 0.7161 0.038 Uiso 1 1 calc R . . C16 C 1.40980(12) 0.36401(8) 0.46033(11) 0.0260(2) Uani 1 1 d . . . H16A H 1.4213 0.3462 0.3728 0.039 Uiso 1 1 calc R . . H16B H 1.4977 0.3819 0.4986 0.039 Uiso 1 1 calc R . . H16C H 1.3455 0.4108 0.4610 0.039 Uiso 1 1 calc R . . N2 N 1.03762(8) 0.20409(5) 0.40897(8) 0.01348(17) Uani 1 1 d . . . O1 O 0.75888(7) 0.06613(5) 0.54741(6) 0.01508(15) Uani 1 1 d . . . O2 O 0.64478(8) 0.04283(5) 0.36152(7) 0.02471(18) Uani 1 1 d . . . O3 O 0.92924(7) 0.15891(4) 0.46013(6) 0.01326(15) Uani 1 1 d . . . O4 O 0.74006(7) 0.23497(4) 0.28611(7) 0.01766(16) Uani 1 1 d . . . O5 O 1.16461(8) 0.16289(5) 0.58616(7) 0.02052(17) Uani 1 1 d . . . O6 O 1.22602(7) 0.27299(5) 0.46355(7) 0.01716(16) 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 0.0220(5) 0.0210(5) 0.0163(5) 0.0009(4) 0.0064(4) -0.0030(4) C2 0.0153(5) 0.0180(5) 0.0162(5) 0.0024(4) 0.0049(4) -0.0056(4) C3 0.0136(4) 0.0129(4) 0.0136(4) 0.0003(3) 0.0022(3) -0.0010(3) C4 0.0114(4) 0.0113(4) 0.0099(4) -0.0009(3) -0.0001(3) -0.0021(3) C5 0.0139(4) 0.0122(4) 0.0132(4) 0.0005(3) 0.0003(3) 0.0013(3) C6 0.0225(5) 0.0126(4) 0.0150(5) -0.0022(4) 0.0019(4) -0.0001(4) C7 0.0244(5) 0.0186(5) 0.0107(4) -0.0022(4) 0.0007(4) -0.0011(4) C8 0.0163(5) 0.0191(5) 0.0128(4) 0.0026(4) -0.0025(4) -0.0014(4) C9 0.0108(4) 0.0132(4) 0.0131(4) 0.0013(3) 0.0012(3) 0.0019(3) C10 0.0141(4) 0.0131(5) 0.0168(5) 0.0026(4) 0.0028(4) 0.0018(4) C11 0.0182(5) 0.0107(4) 0.0164(4) 0.0005(4) 0.0032(4) -0.0021(4) C12 0.0162(5) 0.0149(5) 0.0128(4) -0.0026(4) 0.0025(4) -0.0041(4) C13 0.0143(5) 0.0202(5) 0.0164(5) 0.0000(4) -0.0030(4) -0.0068(4) C14 0.0197(5) 0.0264(6) 0.0342(6) -0.0020(5) -0.0017(5) 0.0001(4) C15 0.0294(6) 0.0268(6) 0.0190(5) -0.0048(4) -0.0001(4) -0.0089(5) C16 0.0208(5) 0.0305(6) 0.0261(6) 0.0086(5) -0.0053(4) -0.0139(5) N2 0.0141(4) 0.0136(4) 0.0129(4) 0.0021(3) 0.0016(3) -0.0064(3) O1 0.0132(3) 0.0197(4) 0.0126(3) 0.0028(3) 0.0024(3) -0.0050(3) O2 0.0189(4) 0.0384(5) 0.0168(4) -0.0002(3) 0.0003(3) -0.0145(3) O3 0.0146(3) 0.0154(3) 0.0101(3) -0.0012(3) 0.0031(2) -0.0076(3) O4 0.0136(3) 0.0145(3) 0.0253(4) 0.0012(3) 0.0047(3) 0.0036(3) O5 0.0227(4) 0.0218(4) 0.0167(3) 0.0050(3) -0.0027(3) -0.0075(3) O6 0.0155(3) 0.0197(4) 0.0160(3) 0.0026(3) -0.0019(3) -0.0083(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.5042(14) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.4584(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O2 1.2029(12) . ? C3 O1 1.3278(12) . ? C3 C4 1.5311(12) . ? C4 O3 1.4408(11) . ? C4 C9 1.5282(13) . ? C4 C5 1.5355(13) . ? C5 C6 1.5252(13) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5247(14) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5278(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5067(13) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O4 1.4390(11) . ? C9 C10 1.4723(13) . ? C10 O4 1.4571(11) . ? C10 C11 1.5048(14) . ? C10 H10 1.0000 . ? C11 N2 1.4602(12) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O5 1.2044(12) . ? C12 O6 1.3398(12) . ? C12 N2 1.3904(13) . ? C13 O6 1.4829(11) . ? C13 C14 1.5154(15) . ? C13 C16 1.5177(14) . ? C13 C15 1.5184(14) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N2 O3 1.4176(10) . ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 106.89(8) . . ? O1 C2 H2A 110.3 . . ? C1 C2 H2A 110.3 . . ? O1 C2 H2B 110.3 . . ? C1 C2 H2B 110.3 . . ? H2A C2 H2B 108.6 . . ? O2 C3 O1 125.05(9) . . ? O2 C3 C4 123.13(9) . . ? O1 C3 C4 111.78(8) . . ? O3 C4 C3 104.62(7) . . ? O3 C4 C9 110.20(7) . . ? C3 C4 C9 109.90(7) . . ? O3 C4 C5 110.98(7) . . ? C3 C4 C5 109.51(8) . . ? C9 C4 C5 111.41(7) . . ? C6 C5 C4 112.96(8) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 111.16(8) . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 110.50(8) . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 109.85(8) . . ? C9 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? O4 C9 C10 60.05(6) . . ? O4 C9 C8 117.13(8) . . ? C10 C9 C8 119.99(8) . . ? O4 C9 C4 113.18(7) . . ? C10 C9 C4 117.27(8) . . ? C8 C9 C4 116.66(8) . . ? O4 C10 C9 58.84(6) . . ? O4 C10 C11 117.52(8) . . ? C9 C10 C11 120.96(8) . . ? O4 C10 H10 115.8 . . ? C9 C10 H10 115.8 . . ? C11 C10 H10 115.8 . . ? N2 C11 C10 108.88(8) . . ? N2 C11 H11A 109.9 . . ? C10 C11 H11A 109.9 . . ? N2 C11 H11B 109.9 . . ? C10 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O5 C12 O6 127.53(9) . . ? O5 C12 N2 124.36(9) . . ? O6 C12 N2 108.06(8) . . ? O6 C13 C14 110.66(8) . . ? O6 C13 C16 101.48(8) . . ? C14 C13 C16 111.46(9) . . ? O6 C13 C15 109.29(8) . . ? C14 C13 C15 112.26(9) . . ? C16 C13 C15 111.19(9) . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 N2 O3 110.18(7) . . ? C12 N2 C11 122.38(8) . . ? O3 N2 C11 109.78(7) . . ? C3 O1 C2 115.83(7) . . ? N2 O3 C4 108.72(6) . . ? C9 O4 C10 61.11(6) . . ? C12 O6 C13 120.86(8) . . ? 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 O2 C3 C4 O3 158.74(10) . . . . ? O1 C3 C4 O3 -23.66(10) . . . . ? O2 C3 C4 C9 40.45(13) . . . . ? O1 C3 C4 C9 -141.96(8) . . . . ? O2 C3 C4 C5 -82.24(12) . . . . ? O1 C3 C4 C5 95.35(9) . . . . ? O3 C4 C5 C6 -169.46(7) . . . . ? C3 C4 C5 C6 75.54(10) . . . . ? C9 C4 C5 C6 -46.25(10) . . . . ? C4 C5 C6 C7 54.49(11) . . . . ? C5 C6 C7 C8 -59.70(11) . . . . ? C6 C7 C8 C9 56.90(11) . . . . ? C7 C8 C9 O4 169.73(8) . . . . ? C7 C8 C9 C10 100.33(10) . . . . ? C7 C8 C9 C4 -51.50(11) . . . . ? O3 C4 C9 O4 -49.92(10) . . . . ? C3 C4 C9 O4 64.86(10) . . . . ? C5 C4 C9 O4 -173.57(7) . . . . ? O3 C4 C9 C10 17.11(11) . . . . ? C3 C4 C9 C10 131.89(8) . . . . ? C5 C4 C9 C10 -106.54(9) . . . . ? O3 C4 C9 C8 169.73(7) . . . . ? C3 C4 C9 C8 -75.49(10) . . . . ? C5 C4 C9 C8 46.08(11) . . . . ? C8 C9 C10 O4 105.97(9) . . . . ? C4 C9 C10 O4 -102.36(9) . . . . ? O4 C9 C10 C11 105.48(10) . . . . ? C8 C9 C10 C11 -148.55(9) . . . . ? C4 C9 C10 C11 3.12(13) . . . . ? O4 C10 C11 N2 82.68(10) . . . . ? C9 C10 C11 N2 14.26(12) . . . . ? O5 C12 N2 O3 21.81(13) . . . . ? O6 C12 N2 O3 -160.71(7) . . . . ? O5 C12 N2 C11 153.12(10) . . . . ? O6 C12 N2 C11 -29.41(12) . . . . ? C10 C11 N2 C12 174.79(8) . . . . ? C10 C11 N2 O3 -53.74(9) . . . . ? O2 C3 O1 C2 1.20(15) . . . . ? C4 C3 O1 C2 -176.34(8) . . . . ? C1 C2 O1 C3 -165.57(8) . . . . ? C12 N2 O3 C4 -143.06(8) . . . . ? C11 N2 O3 C4 79.33(9) . . . . ? C3 C4 O3 N2 -174.47(7) . . . . ? C9 C4 O3 N2 -56.39(9) . . . . ? C5 C4 O3 N2 67.51(9) . . . . ? C8 C9 O4 C10 -110.67(9) . . . . ? C4 C9 O4 C10 109.18(9) . . . . ? C11 C10 O4 C9 -111.27(9) . . . . ? O5 C12 O6 C13 1.18(15) . . . . ? N2 C12 O6 C13 -176.19(8) . . . . ? C14 C13 O6 C12 59.80(12) . . . . ? C16 C13 O6 C12 178.19(9) . . . . ? C15 C13 O6 C12 -64.31(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.17 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.406 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.040 _database_code_depnum_ccdc_archive 'CCDC 907696'