Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry data_global _journal_year ? _journal_volume ? _journal_page_first ? _journal_name_full Org.Biomol.Chem. loop_ _publ_author_name J.E.Moses 'Jack E. Baldwin' 'Rodolfo Marquez' 'Robert M. Adlington' 'Andrew R. Cowley' _publ_contact_author 'Dr. Rodolfo Marquez' _journal_coden_Cambridge 0177 data_CRYSTALS_cif_compound_12 _database_code_CSD 190072 #========================================================================== # Diffractometer details #========================================================================== _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #========================================================================== # General computing #========================================================================== _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 15.0086(5) _cell_angle_alpha 90 _cell_length_b 8.0675(3) _cell_angle_beta 98.916(2) _cell_length_c 15.1036(5) _cell_angle_gamma 90 _cell_volume 1806.7 _symmetry_cell_setting 'Monoclinic ' _symmetry_space_group_name_H-M 'P 1 21/a 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C20 H23 N1 O4 ' _chemical_formula_moiety ' C20 H23 N1 O4 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 341.41 _cell_measurement_reflns_used 3963 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 728.204 _exptl_absorpt_coefficient_mu 0.087 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 12982 _reflns_number_total 4111 #4392 reflections measured including systematic absences _diffrn_reflns_av_R_equivalents 0.042 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_gt 2533 _diffrn_reflns_theta_min 5.18 _diffrn_reflns_theta_max 27.46 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _refine_diff_density_min -0.27 _refine_diff_density_max 0.29 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2533 _refine_ls_number_parameters 226 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.0527 _refine_ls_goodness_of_fit_ref 1.0561 _refine_ls_shift/su_max 0.000343 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.956 0.632 0.598 ; _refine_special_details ; The hydrogen atoms attached to the methyl C atoms C18-C20 were positioned geometrically after a difference Fourier map had shown which of the two likely orientations predominated. There is some evidence in this map to suggest that the H atoms may be disordered, but this could not be meaningfully modelled ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type N1 0.38234(11) 1.7337(2) 0.0257(1) 0.0320 1.0000 Uani O1 0.80262(11) 0.17710(19) 0.47237(9) 0.0430 1.0000 Uani O2 0.87403(9) 0.04052(16) 0.37426(8) 0.0311 1.0000 Uani O3 0.3088(1) 1.72339(19) -0.0227(1) 0.0447 1.0000 Uani O4 0.42421(11) 1.86436(17) 0.0395(1) 0.0419 1.0000 Uani C1 0.49817(12) 1.2961(2) 0.14908(11) 0.0272 1.0000 Uani C2 0.42263(13) 1.2886(2) 0.08193(12) 0.0290 1.0000 Uani C3 0.38297(12) 1.4313(2) 0.04276(12) 0.0291 1.0000 Uani C4 0.42126(12) 1.5826(2) 0.06972(11) 0.0271 1.0000 Uani C5 0.49585(13) 1.5961(2) 0.13560(13) 0.0321 1.0000 Uani C6 0.53349(13) 1.4523(2) 0.17548(12) 0.0319 1.0000 Uani C7 0.54095(12) 1.1414(2) 0.18590(12) 0.0292 1.0000 Uani C8 0.57436(12) 1.1091(2) 0.27212(12) 0.0273 1.0000 Uani C9 0.61942(12) 0.9514(2) 0.29972(11) 0.0274 1.0000 Uani C10 0.67949(11) 0.8643(2) 0.26036(11) 0.0257 1.0000 Uani C11 0.71071(12) 0.7090(2) 0.30498(11) 0.0258 1.0000 Uani C12 0.75767(11) 0.5792(2) 0.27978(11) 0.0265 1.0000 Uani C13 0.77605(11) 0.4435(2) 0.34443(11) 0.0270 1.0000 Uani C14 0.81627(12) 0.3001(2) 0.33104(11) 0.0299 1.0000 Uani C15 0.82860(12) 0.1710(2) 0.40052(12) 0.0298 1.0000 Uani C16 0.89105(13) -0.0958(2) 0.43715(12) 0.0309 1.0000 Uani C17 0.95230(14) -0.2145(3) 0.39887(14) 0.0385 1.0000 Uani C18 0.56266(13) 1.2215(3) 0.34975(12) 0.0342 1.0000 Uani C19 0.71645(14) 0.9272(2) 0.17936(13) 0.0349 1.0000 Uani C20 0.78999(15) 0.5545(3) 0.19118(12) 0.0374 1.0000 Uani H21 0.3968 1.1782 0.0618 0.0347 1.0000 Uiso H31 0.3280 1.4251 -0.0039 0.0348 1.0000 Uiso H51 0.5221 1.7070 0.1541 0.0385 1.0000 Uiso H61 0.5868 1.4603 0.2240 0.0377 1.0000 Uiso H71 0.5457 1.0503 0.1420 0.0352 1.0000 Uiso H91 0.6033 0.9013 0.3557 0.0329 1.0000 Uiso H111 0.6939 0.6967 0.3662 0.0309 1.0000 Uiso H131 0.7566 0.4598 0.4042 0.0324 1.0000 Uiso H141 0.8384 0.2802 0.2728 0.0361 1.0000 Uiso H161 0.9209 -0.0542 0.4968 0.0367 1.0000 Uiso H162 0.8331 -0.1520 0.4441 0.0367 1.0000 Uiso H171 0.9659 -0.3110 0.4403 0.0458 1.0000 Uiso H172 1.0097 -0.1568 0.3918 0.0458 1.0000 Uiso H173 0.9220 -0.2546 0.3391 0.0458 1.0000 Uiso H181 0.5317 1.3259 0.3263 0.0415 1.0000 Uiso H182 0.6232 1.2488 0.3844 0.0415 1.0000 Uiso H183 0.5254 1.1639 0.3898 0.0415 1.0000 Uiso H191 0.6865 1.0344 0.1592 0.0429 1.0000 Uiso H192 0.7830 0.9450 0.1952 0.0429 1.0000 Uiso H193 0.7044 0.8439 0.1299 0.0429 1.0000 Uiso H201 0.7740 0.6540 0.1524 0.0456 1.0000 Uiso H202 0.8569 0.5392 0.2014 0.0456 1.0000 Uiso H203 0.7605 0.4540 0.1609 0.0456 1.0000 Uiso 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 N1 0.0381(9) 0.0266(8) 0.0326(8) -0.0011(6) 0.0101(7) 0.0049(7) O1 0.0609(9) 0.0400(8) 0.0316(7) 0.0063(6) 0.0186(6) 0.0137(7) O2 0.0349(7) 0.0277(7) 0.0317(6) 0.0028(5) 0.0087(5) 0.0033(5) O3 0.0427(8) 0.0370(8) 0.0508(8) 0.0035(7) -0.0035(7) 0.0086(7) O4 0.0570(9) 0.0232(7) 0.0465(8) -0.0017(6) 0.0115(7) -0.0018(6) C1 0.0274(9) 0.0267(9) 0.0287(8) -0.0009(7) 0.0078(7) -0.0010(7) C2 0.032(1) 0.0243(9) 0.0303(8) -0.0032(7) 0.0046(7) -0.0030(7) C3 0.0282(9) 0.0300(9) 0.0287(8) -0.0025(7) 0.0032(7) 0.0002(7) C4 0.0296(9) 0.0248(9) 0.0289(8) -0.0002(7) 0.0105(7) 0.0037(7) C5 0.035(1) 0.0263(9) 0.0351(9) -0.0035(8) 0.0058(8) -0.0047(8) C6 0.0305(9) 0.031(1) 0.0329(9) -0.0008(8) 0.0009(7) -0.0045(8) C7 0.0297(9) 0.0257(9) 0.0326(9) -0.0021(7) 0.0059(7) -0.0009(7) C8 0.0240(8) 0.0276(9) 0.0312(8) -0.0015(7) 0.0072(7) -0.0012(7) C9 0.0271(8) 0.0286(9) 0.0266(8) 0.0001(7) 0.0041(7) -0.0028(7) C10 0.0265(8) 0.0271(9) 0.0234(8) 0.0006(7) 0.0036(6) -0.0017(7) C11 0.0252(8) 0.0293(9) 0.0228(7) 0.0011(7) 0.0034(6) -0.0040(7) C12 0.0254(8) 0.0290(9) 0.0248(8) 0.0004(7) 0.0032(6) -0.0021(7) C13 0.0252(8) 0.0291(9) 0.0266(8) 0.0002(7) 0.0039(6) -0.0022(7) C14 0.0297(9) 0.033(1) 0.0274(8) 0.0014(7) 0.0059(7) 0.0011(8) C15 0.0301(9) 0.0288(9) 0.0309(9) -0.0007(7) 0.0056(7) -0.0012(8) C16 0.034(1) 0.0248(9) 0.0330(9) 0.0028(7) 0.0020(7) 0.0002(8) C17 0.0374(11) 0.030(1) 0.0470(11) -0.0029(9) 0.0037(9) 0.0029(9) C18 0.037(1) 0.035(1) 0.0322(9) -0.0038(8) 0.0089(8) 0.0024(8) C19 0.040(1) 0.034(1) 0.0329(9) 0.0082(8) 0.0141(8) 0.0055(9) C20 0.0525(12) 0.0357(11) 0.0258(8) 0.0029(8) 0.0121(8) 0.0090(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . O3 . 1.229(2) yes N1 . O4 . 1.228(2) yes N1 . C4 . 1.466(2) yes O1 . C15 . 1.210(2) yes O2 . C15 . 1.347(2) yes O2 . C16 . 1.450(2) yes C1 . C2 . 1.400(3) yes C1 . C6 . 1.401(3) yes C1 . C7 . 1.472(3) yes C2 . C3 . 1.386(3) yes C2 . H21 . 1.0000 no C3 . C4 . 1.383(3) yes C3 . H31 . 1.0000 no C4 . C5 . 1.382(3) yes C5 . C6 . 1.386(3) yes C5 . H51 . 1.0000 no C6 . H61 . 1.0000 no C7 . C8 . 1.346(3) yes C7 . H71 . 1.0000 no C8 . C9 . 1.471(3) yes C8 . C18 . 1.514(3) yes C9 . C10 . 1.351(2) yes C9 . H91 . 1.0000 no C10 . C11 . 1.465(2) yes C10 . C19 . 1.507(2) yes C11 . C12 . 1.349(3) yes C11 . H111 . 1.0000 no C12 . C13 . 1.464(2) yes C12 . C20 . 1.506(2) yes C13 . C14 . 1.335(3) yes C13 . H131 . 1.0000 no C14 . C15 . 1.470(3) yes C14 . H141 . 1.0000 no C16 . C17 . 1.504(3) yes C16 . H161 . 1.0000 no C16 . H162 . 1.0000 no C17 . H171 . 1.000 no C17 . H172 . 1.000 no C17 . H173 . 1.000 no C18 . H181 . 1.000 no C18 . H182 . 1.000 no C18 . H183 . 1.000 no C19 . H191 . 1.0000 no C19 . H192 . 1.000 no C19 . H193 . 1.000 no C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 . N1 . O4 . 123.21(17) yes O3 . N1 . C4 . 118.13(16) yes O4 . N1 . C4 . 118.66(16) yes C15 . O2 . C16 . 116.47(14) yes C2 . C1 . C6 . 118.21(16) yes C2 . C1 . C7 . 119.61(16) yes C6 . C1 . C7 . 122.09(16) yes C1 . C2 . C3 . 121.31(16) yes C1 . C2 . H21 . 119.35 no C3 . C2 . H21 . 119.34 no C2 . C3 . C4 . 118.42(16) yes C2 . C3 . H31 . 120.79 no C4 . C3 . H31 . 120.79 no N1 . C4 . C3 . 118.84(16) yes N1 . C4 . C5 . 118.85(16) yes C3 . C4 . C5 . 122.31(16) yes C4 . C5 . C6 . 118.50(17) yes C4 . C5 . H51 . 120.75 no C6 . C5 . H51 . 120.75 no C1 . C6 . C5 . 121.22(16) yes C1 . C6 . H61 . 119.39 no C5 . C6 . H61 . 119.39 no C1 . C7 . C8 . 127.20(17) yes C1 . C7 . H71 . 116.40 no C8 . C7 . H71 . 116.40 no C7 . C8 . C9 . 121.83(16) yes C7 . C8 . C18 . 124.26(17) yes C9 . C8 . C18 . 113.71(15) yes C8 . C9 . C10 . 129.34(16) yes C8 . C9 . H91 . 115.33 no C10 . C9 . H91 . 115.33 no C9 . C10 . C11 . 115.46(15) yes C9 . C10 . C19 . 122.47(16) yes C11 . C10 . C19 . 121.97(15) yes C10 . C11 . C12 . 132.67(16) yes C10 . C11 . H111 . 113.67 no C12 . C11 . H111 . 113.67 no C11 . C12 . C13 . 116.39(15) yes C11 . C12 . C20 . 127.41(16) yes C13 . C12 . C20 . 116.14(16) yes C12 . C13 . C14 . 126.14(16) yes C12 . C13 . H131 . 116.93 no C14 . C13 . H131 . 116.93 no C13 . C14 . C15 . 121.06(16) yes C13 . C14 . H141 . 119.47 no C15 . C14 . H141 . 119.47 no O1 . C15 . O2 . 122.98(17) yes O1 . C15 . C14 . 126.10(18) yes O2 . C15 . C14 . 110.92(15) yes O2 . C16 . C17 . 106.69(15) yes O2 . C16 . H161 . 110.16 no C17 . C16 . H161 . 110.16 no O2 . C16 . H162 . 110.16 no C17 . C16 . H162 . 110.16 no H161 . C16 . H162 . 109.47 no C16 . C17 . H171 . 109.47 no C16 . C17 . H172 . 109.47 no H171 . C17 . H172 . 109.48 no C16 . C17 . H173 . 109.47 no H171 . C17 . H173 . 109.48 no H172 . C17 . H173 . 109.5 no C8 . C18 . H181 . 109.47 no C8 . C18 . H182 . 109.47 no H181 . C18 . H182 . 109.48 no C8 . C18 . H183 . 109.47 no H181 . C18 . H183 . 109.48 no H182 . C18 . H183 . 109.48 no C10 . C19 . H191 . 109.47 no C10 . C19 . H192 . 109.47 no H191 . C19 . H192 . 109.48 no C10 . C19 . H193 . 109.47 no H191 . C19 . H193 . 109.48 no H192 . C19 . H193 . 109.48 no C12 . C20 . H201 . 109.47 no C12 . C20 . H202 . 109.47 no H201 . C20 . H202 . 109.5 no C12 . C20 . H203 . 109.47 no H201 . C20 . H203 . 109.48 no H202 . C20 . H203 . 109.48 no data_CRYSTALS_cif_compound_54 _database_code_CSD 190073 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point 'not measured' _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 8.0506(4) _cell_angle_alpha 64.465(2) _cell_length_b 12.3846(5) _cell_angle_beta 86.930(2) _cell_length_c 13.2746(7) _cell_angle_gamma 73.060(2) _cell_volume 1138.4 _symmetry_cell_setting 'Triclinic ' _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C25 H23 N3 O8 ' _chemical_formula_moiety ' C25 H23 N3 O8 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 493.47 _cell_measurement_reflns_used 15400 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' plate ' _exptl_crystal_colour ' pale yellow ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.36 _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_meas 'not measured' _exptl_crystal_F_000 516.168 _exptl_absorpt_coefficient_mu 0.109 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 15400 _reflns_number_total 5161 _diffrn_reflns_av_R_equivalents 0.058 _diffrn_measured_fraction_theta_max 0.990 _reflns_number_gt 2992 _diffrn_reflns_theta_min 5.12 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min -14 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _refine_diff_density_min -0.43 _refine_diff_density_max 0.42 _reflns_threshold_expression >2.00\s(I) _refine_ls_number_reflns 2992 _refine_ls_number_parameters 325 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0578 _refine_ls_goodness_of_fit_ref 1.0525 _refine_ls_shift/su_max 0.005449 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 1.12 0.908 0.787 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type C1 0.8972(3) 0.2420(2) 0.54274(18) 0.0292 1.0000 Uani C2 0.9123(3) 0.1214(2) 0.57861(19) 0.0297 1.0000 Uani C3 0.7513(3) 0.0811(2) 0.61746(18) 0.0264 1.0000 Uani C4 0.6864(3) 0.1263(2) 0.71129(18) 0.0240 1.0000 Uani C5 0.6142(3) 0.2673(2) 0.64403(18) 0.0251 1.0000 Uani C6 0.7234(3) 0.3226(2) 0.54838(19) 0.0270 1.0000 Uani C7 0.5610(3) 0.2918(2) 0.52717(18) 0.0253 1.0000 Uani C8 0.6003(3) 0.1670(2) 0.52237(18) 0.0244 1.0000 Uani C9 1.0373(4) 0.3033(3) 0.4953(2) 0.0402 1.0000 Uani C10 0.7838(3) -0.0584(2) 0.6541(2) 0.0343 1.0000 Uani C11 0.5200(3) 0.3483(2) 0.7007(2) 0.0296 1.0000 Uani C12 0.5532(3) 0.0667(2) 0.77847(17) 0.0224 1.0000 Uani C13 0.6056(3) -0.0393(2) 0.88117(18) 0.0243 1.0000 Uani C14 0.4885(3) -0.0988(2) 0.94344(18) 0.0251 1.0000 Uani C15 0.3154(3) -0.0510(2) 0.90090(19) 0.0255 1.0000 Uani C16 0.2571(3) 0.0541(2) 0.80093(19) 0.0279 1.0000 Uani C17 0.3766(3) 0.1126(2) 0.74072(18) 0.0271 1.0000 Uani N1 0.1900(3) -0.11430(19) 0.96385(17) 0.0330 1.0000 Uani O1 0.2393(3) -0.2009(2) 1.05757(16) 0.0509 1.0000 Uani O2 0.0424(2) -0.0802(2) 0.92189(18) 0.0513 1.0000 Uani C18 0.6443(3) 0.1731(2) 0.40777(19) 0.0283 1.0000 Uani O3 0.4926(2) 0.26356(15) 0.33187(13) 0.0286 1.0000 Uani C19 0.5092(3) 0.2958(2) 0.22264(18) 0.0247 1.0000 Uani O4 0.6324(2) 0.24710(15) 0.18496(14) 0.0312 1.0000 Uani C20 0.3581(3) 0.4033(2) 0.15159(18) 0.0259 1.0000 Uani C21 0.2398(3) 0.4744(2) 0.19604(19) 0.0265 1.0000 Uani C22 0.1081(3) 0.5759(2) 0.12515(19) 0.0274 1.0000 Uani C23 0.0875(3) 0.6107(2) 0.01123(19) 0.0282 1.0000 Uani C24 0.2085(3) 0.5371(2) -0.02910(18) 0.0271 1.0000 Uani C25 0.3431(3) 0.4342(2) 0.03761(19) 0.0265 1.0000 Uani N2 -0.0198(3) 0.65030(19) 0.17185(18) 0.0328 1.0000 Uani O5 0.0143(3) 0.6353(2) 0.26631(16) 0.0486 1.0000 Uani O6 -0.1544(2) 0.72284(19) 0.11291(16) 0.0441 1.0000 Uani N3 0.1905(3) 0.56993(18) -0.14943(16) 0.0314 1.0000 Uani O7 0.0580(2) 0.65114(18) -0.20459(15) 0.0406 1.0000 Uani O8 0.3077(3) 0.51474(17) -0.18769(15) 0.0428 1.0000 Uani H21 1.0256 0.0597 0.5799 0.0321 1.0000 Uiso H41 0.7805 0.1017 0.7701 0.0262 1.0000 Uiso H61 0.7646 0.3986 0.5174 0.0310 1.0000 Uiso H71 0.4565 0.3410 0.4719 0.0276 1.0000 Uiso H81 0.4976 0.1342 0.5344 0.0277 1.0000 Uiso H91 1.1468 0.2384 0.4966 0.0479 1.0000 Uiso H92 1.0592 0.3444 0.5415 0.0479 1.0000 Uiso H93 0.9991 0.3677 0.4164 0.0479 1.0000 Uiso H101 0.6740 -0.0807 0.6790 0.0378 1.0000 Uiso H102 0.8768 -0.1073 0.7175 0.0378 1.0000 Uiso H103 0.8221 -0.0788 0.5898 0.0378 1.0000 Uiso H111 0.4815 0.4381 0.6443 0.0330 1.0000 Uiso H112 0.6004 0.3382 0.7612 0.0330 1.0000 Uiso H113 0.4159 0.3220 0.7342 0.0330 1.0000 Uiso H131 0.7310 -0.0730 0.9103 0.0275 1.0000 Uiso H141 0.5273 -0.1741 1.0171 0.0299 1.0000 Uiso H161 0.1314 0.0872 0.7725 0.0323 1.0000 Uiso H171 0.3356 0.1897 0.6685 0.0288 1.0000 Uiso H181 0.7501 0.2019 0.3847 0.0310 1.0000 Uiso H182 0.6654 0.0891 0.4085 0.0310 1.0000 Uiso H211 0.2499 0.4524 0.2778 0.0319 1.0000 Uiso H231 -0.0091 0.6845 -0.0388 0.0321 1.0000 Uiso H251 0.4275 0.3833 0.0051 0.0330 1.0000 Uiso 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 0.0265(12) 0.0382(13) 0.0186(11) -0.008(1) 0.0023(9) -0.010(1) C2 0.0250(11) 0.0335(12) 0.0217(11) -0.009(1) 0.0018(9) -0.0010(9) C3 0.0251(11) 0.0233(11) 0.0223(11) -0.0061(9) 0.0024(9) -0.0013(8) C4 0.0224(11) 0.0241(11) 0.019(1) -0.0057(9) 0.0009(8) -0.0032(8) C5 0.0245(11) 0.0228(11) 0.0220(11) -0.0070(9) 0.0008(8) -0.0028(8) C6 0.0281(12) 0.0237(11) 0.0257(11) -0.0065(9) 0.0038(9) -0.0096(9) C7 0.0240(11) 0.0250(11) 0.020(1) -0.0060(9) -0.0003(8) -0.0035(9) C8 0.0239(11) 0.023(1) 0.0224(11) -0.0090(9) 0.0020(8) -0.0027(8) C9 0.0384(14) 0.0491(16) 0.0323(14) -0.0133(12) 0.0057(11) -0.0193(12) C10 0.0417(14) 0.0223(11) 0.0306(13) -0.009(1) 0.005(1) -0.002(1) C11 0.0319(12) 0.0229(11) 0.0277(12) -0.0103(9) 0.0002(9) -0.0002(9) C12 0.0244(11) 0.022(1) 0.019(1) -0.0098(8) 0.0007(8) -0.0031(8) C13 0.0259(11) 0.021(1) 0.0215(11) -0.0076(9) -0.0008(8) -0.0034(8) C14 0.0305(12) 0.0225(11) 0.0218(11) -0.0093(9) 0.0019(9) -0.0075(9) C15 0.0286(12) 0.0243(11) 0.0239(11) -0.0100(9) 0.0037(9) -0.0092(9) C16 0.0218(11) 0.0307(12) 0.0282(12) -0.012(1) 0.0013(9) -0.0047(9) C17 0.0268(11) 0.0242(11) 0.0209(11) -0.0053(9) -0.0011(8) -0.0010(9) N1 0.0322(11) 0.0340(11) 0.0324(11) -0.0110(9) 0.0018(9) -0.0146(9) O1 0.0557(13) 0.0535(12) 0.031(1) 0.0045(9) -0.0042(9) -0.033(1) O2 0.029(1) 0.0518(12) 0.0565(13) -0.005(1) 0.0002(9) -0.0175(9) C18 0.0254(12) 0.0268(11) 0.0253(11) -0.0091(9) -0.0007(9) -0.0003(9) O3 0.0278(8) 0.0295(8) 0.0221(8) -0.0089(7) 0.0005(6) -0.0028(7) C19 0.0311(12) 0.023(1) 0.0219(11) -0.0099(9) 0.0022(9) -0.0110(9) O4 0.0365(9) 0.0290(9) 0.0255(8) -0.0129(7) 0.0034(7) -0.0047(7) C20 0.0302(12) 0.0249(11) 0.0225(11) -0.0090(9) -0.0003(9) -0.0096(9) C21 0.0276(11) 0.0284(11) 0.0236(11) -0.0095(9) 0.0026(9) -0.0114(9) C22 0.0253(11) 0.0278(11) 0.0287(12) -0.012(1) 0.0053(9) -0.0094(9) C23 0.0275(11) 0.0261(11) 0.0267(11) -0.0056(9) 0.0007(9) -0.0108(9) C24 0.0329(12) 0.0266(11) 0.0219(11) -0.0083(9) -0.0005(9) -0.0124(9) C25 0.0318(12) 0.0251(11) 0.0256(11) -0.0113(9) 0.0035(9) -0.0126(9) N2 0.0299(11) 0.030(1) 0.0328(11) -0.0107(9) 0.0060(9) -0.0056(9) O5 0.0521(12) 0.0531(12) 0.0334(11) -0.0240(9) 0.0022(8) 0.0029(9) O6 0.030(1) 0.0468(11) 0.0437(11) -0.0159(9) 0.0035(8) -0.0006(8) N3 0.0429(12) 0.028(1) 0.023(1) -0.0086(9) 0.0006(9) -0.0130(9) O7 0.0416(11) 0.042(1) 0.0284(9) -0.0063(8) -0.0091(8) -0.0110(8) O8 0.0620(13) 0.039(1) 0.0282(9) -0.0189(8) 0.0036(8) -0.0090(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.326(4) yes C1 . C6 . 1.483(3) yes C1 . C9 . 1.502(3) yes C2 . C3 . 1.510(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.581(3) yes C3 . C8 . 1.567(3) yes C3 . C10 . 1.521(3) yes C4 . C5 . 1.518(3) yes C4 . C12 . 1.511(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.528(3) yes C5 . C7 . 1.507(3) yes C5 . C11 . 1.514(3) yes C6 . C7 . 1.535(3) yes C6 . H61 . 1.000 no C7 . C8 . 1.514(3) yes C7 . H71 . 1.000 no C8 . C18 . 1.518(3) yes C8 . H81 . 1.000 no C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . H101 . 1.000 no C10 . H102 . 1.000 no C10 . H103 . 1.000 no C11 . H111 . 1.000 no C11 . H112 . 1.000 no C11 . H113 . 1.000 no C12 . C13 . 1.399(3) yes C12 . C17 . 1.398(3) yes C13 . C14 . 1.383(3) yes C13 . H131 . 1.000 no C14 . C15 . 1.388(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.377(3) yes C15 . N1 . 1.462(3) yes C16 . C17 . 1.384(3) yes C16 . H161 . 1.000 no C17 . H171 . 1.000 no N1 . O1 . 1.229(3) yes N1 . O2 . 1.215(3) yes C18 . O3 . 1.457(3) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no O3 . C19 . 1.338(3) yes C19 . O4 . 1.207(3) yes C19 . C20 . 1.496(3) yes C20 . C21 . 1.389(3) yes C20 . C25 . 1.394(3) yes C21 . C22 . 1.379(3) yes C21 . H211 . 1.000 no C22 . C23 . 1.387(3) yes C22 . N2 . 1.471(3) yes C23 . C24 . 1.383(3) yes C23 . H231 . 1.000 no C24 . C25 . 1.381(3) yes C24 . N3 . 1.472(3) yes C25 . H251 . 1.000 no N2 . O5 . 1.220(3) yes N2 . O6 . 1.229(3) yes N3 . O7 . 1.228(3) yes N3 . O8 . 1.220(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 115.9(2) yes C2 . C1 . C9 . 126.1(2) yes C6 . C1 . C9 . 118.0(2) yes C1 . C2 . C3 . 117.2(2) yes C1 . C2 . H21 . 121.4 no C3 . C2 . H21 . 121.4 no C2 . C3 . C4 . 106.05(19) yes C2 . C3 . C8 . 108.00(18) yes C4 . C3 . C8 . 101.20(16) yes C2 . C3 . C10 . 112.31(19) yes C4 . C3 . C10 . 114.55(18) yes C8 . C3 . C10 . 113.8(2) yes C3 . C4 . C5 . 102.45(16) yes C3 . C4 . C12 . 112.57(18) yes C5 . C4 . C12 . 113.22(18) yes C3 . C4 . H41 . 113.46 no C5 . C4 . H41 . 112.8 no C12 . C4 . H41 . 102.74 no C4 . C5 . C6 . 113.56(18) yes C4 . C5 . C7 . 107.23(18) yes C6 . C5 . C7 . 60.73(15) yes C4 . C5 . C11 . 120.23(19) yes C6 . C5 . C11 . 117.56(19) yes C7 . C5 . C11 . 123.46(19) yes C1 . C6 . C5 . 118.80(18) yes C1 . C6 . C7 . 118.5(2) yes C5 . C6 . C7 . 58.97(14) yes C1 . C6 . H61 . 91.63 no C5 . C6 . H61 . 135.3 no C7 . C6 . H61 . 135.6 no C5 . C7 . C6 . 60.30(14) yes C5 . C7 . C8 . 108.32(17) yes C6 . C7 . C8 . 114.03(18) yes C5 . C7 . H71 . 137.7 no C6 . C7 . H71 . 133.0 no C8 . C7 . H71 . 100.05 no C3 . C8 . C7 . 102.36(17) yes C3 . C8 . C18 . 114.59(18) yes C7 . C8 . C18 . 113.68(19) yes C3 . C8 . H81 . 112.47 no C7 . C8 . H81 . 113.40 no C18 . C8 . H81 . 100.85 no C1 . C9 . H91 . 109.5 no C1 . C9 . H92 . 109.5 no H91 . C9 . H92 . 109.5 no C1 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no C3 . C10 . H101 . 109.5 no C3 . C10 . H102 . 109.5 no H101 . C10 . H102 . 109.5 no C3 . C10 . H103 . 109.5 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no C5 . C11 . H111 . 109.5 no C5 . C11 . H112 . 109.5 no H111 . C11 . H112 . 109.5 no C5 . C11 . H113 . 109.5 no H111 . C11 . H113 . 109.5 no H112 . C11 . H113 . 109.5 no C4 . C12 . C13 . 119.97(19) yes C4 . C12 . C17 . 122.17(19) yes C13 . C12 . C17 . 117.8(2) yes C12 . C13 . C14 . 121.7(2) yes C12 . C13 . H131 . 119.2 no C14 . C13 . H131 . 119.2 no C13 . C14 . C15 . 118.1(2) yes C13 . C14 . H141 . 120.9 no C15 . C14 . H141 . 120.9 no C14 . C15 . C16 . 122.3(2) yes C14 . C15 . N1 . 119.1(2) yes C16 . C15 . N1 . 118.6(2) yes C15 . C16 . C17 . 118.4(2) yes C15 . C16 . H161 . 120.8 no C17 . C16 . H161 . 120.8 no C12 . C17 . C16 . 121.6(2) yes C12 . C17 . H171 . 119.2 no C16 . C17 . H171 . 119.2 no C15 . N1 . O1 . 118.2(2) yes C15 . N1 . O2 . 119.2(2) yes O1 . N1 . O2 . 122.6(2) yes C8 . C18 . O3 . 105.39(17) yes C8 . C18 . H181 . 110.5 no O3 . C18 . H181 . 110.5 no C8 . C18 . H182 . 110.5 no O3 . C18 . H182 . 110.5 no H181 . C18 . H182 . 109.5 no C18 . O3 . C19 . 116.20(17) yes O3 . C19 . O4 . 124.7(2) yes O3 . C19 . C20 . 111.71(18) yes O4 . C19 . C20 . 123.6(2) yes C19 . C20 . C21 . 121.4(2) yes C19 . C20 . C25 . 118.1(2) yes C21 . C20 . C25 . 120.5(2) yes C20 . C21 . C22 . 118.6(2) yes C20 . C21 . H211 . 120.7 no C22 . C21 . H211 . 120.7 no C21 . C22 . C23 . 123.2(2) yes C21 . C22 . N2 . 119.0(2) yes C23 . C22 . N2 . 117.8(2) yes C22 . C23 . C24 . 116.1(2) yes C22 . C23 . H231 . 122.0 no C24 . C23 . H231 . 122.0 no C23 . C24 . C25 . 123.5(2) yes C23 . C24 . N3 . 117.9(2) yes C25 . C24 . N3 . 118.6(2) yes C20 . C25 . C24 . 118.2(2) yes C20 . C25 . H251 . 120.9 no C24 . C25 . H251 . 120.9 no C22 . N2 . O5 . 117.96(19) yes C22 . N2 . O6 . 117.5(2) yes O5 . N2 . O6 . 124.6(2) yes C24 . N3 . O7 . 117.7(2) yes C24 . N3 . O8 . 117.97(19) yes O7 . N3 . O8 . 124.3(2) yes data_CRYSTALS_cif_compound_41 _database_code_CSD 209300 #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref #============================================================= _cell_length_a 9.5061(2) _cell_angle_alpha 73.7785(11) _cell_length_b 11.9924(3) _cell_angle_beta 84.7859(9) _cell_length_c 12.1678(3) _cell_angle_gamma 80.7467(13) _cell_volume 1313.0 _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C28 H27 N3 O8 ' _chemical_formula_moiety ' C28 H27 N3 O8 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 533.54 _cell_measurement_reflns_used 19776 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 2 _exptl_crystal_description ' block ' _exptl_crystal_colour ' yellow ' _exptl_crystal_size_min 0.35 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_meas ? _exptl_crystal_F_000 560. _exptl_absorpt_coefficient_mu 0.100 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 19776 _reflns_number_total 5959 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_gt 2987 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min -14 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _refine_diff_density_min -0.20 _refine_diff_density_max 0.18 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 2987 _refine_ls_number_parameters 352 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.0427 _refine_ls_goodness_of_fit_ref 1.0616 _refine_ls_shift/su_max 0.004343 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 0.398 0.189 0.141 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type C1 0.7519(2) 0.48666(17) 0.05601(17) 0.0250 1.0000 Uani C2 0.6737(2) 0.42618(18) 0.00697(18) 0.0278 1.0000 Uani C3 0.6786(2) 0.45013(19) -0.11127(19) 0.0283 1.0000 Uani C4 0.7563(2) 0.53229(19) -0.18337(18) 0.0288 1.0000 Uani C5 0.8330(2) 0.58968(18) -0.13077(18) 0.0269 1.0000 Uani C6 0.8334(2) 0.56907(18) -0.01365(18) 0.0258 1.0000 Uani C7 0.7546(2) 0.46603(18) 0.18241(18) 0.0263 1.0000 Uani O1 0.83147(16) 0.50967(14) 0.22704(13) 0.0364 1.0000 Uani O2 0.66289(15) 0.39446(13) 0.23946(12) 0.0321 1.0000 Uani C8 0.6603(2) 0.3696(2) 0.36557(19) 0.0349 1.0000 Uani C9 0.5472(2) 0.29389(19) 0.41268(18) 0.0307 1.0000 Uani C10 0.4324(2) 0.32740(19) 0.47289(18) 0.0285 1.0000 Uani C11 0.3158(2) 0.25922(18) 0.52309(17) 0.0255 1.0000 Uani C12 0.2050(2) 0.31086(17) 0.57651(17) 0.0254 1.0000 Uani C13 0.0669(2) 0.26948(17) 0.63386(17) 0.0247 1.0000 Uani C14 0.0028(2) 0.18974(19) 0.58142(18) 0.0279 1.0000 Uani C15 -0.0938(2) 0.12376(19) 0.64158(19) 0.0306 1.0000 Uani C16 -0.1267(2) 0.12026(19) 0.7627(2) 0.0320 1.0000 Uani C17 -0.0482(2) 0.16278(18) 0.82168(18) 0.0285 1.0000 Uani C18 0.0860(2) 0.21143(17) 0.76455(17) 0.0244 1.0000 Uani C19 0.2144(2) 0.11564(18) 0.78971(17) 0.0253 1.0000 Uani C20 0.3407(2) 0.14076(19) 0.8191(2) 0.0336 1.0000 Uani C21 0.4599(2) 0.0559(2) 0.8419(2) 0.0384 1.0000 Uani C22 0.4508(2) -0.05501(19) 0.83231(19) 0.0327 1.0000 Uani C23 0.3268(2) -0.08368(18) 0.80309(18) 0.0316 1.0000 Uani C24 0.2084(2) 0.00218(18) 0.78332(18) 0.0278 1.0000 Uani N1 0.5964(2) 0.38508(18) -0.16335(18) 0.0380 1.0000 Uani O3 0.5301(2) 0.3114(2) -0.09798(17) 0.0641 1.0000 Uani O4 0.59771(19) 0.40803(16) -0.26781(16) 0.0484 1.0000 Uani N2 0.9157(2) 0.67976(17) -0.20309(16) 0.0344 1.0000 Uani O5 0.8963(2) 0.70964(18) -0.30603(15) 0.0578 1.0000 Uani O6 0.99866(17) 0.71843(14) -0.15710(14) 0.0390 1.0000 Uani C25 0.3320(2) 0.13712(19) 0.5091(2) 0.0321 1.0000 Uani C26 -0.0453(2) 0.38085(19) 0.6213(2) 0.0320 1.0000 Uani C27 -0.1705(3) 0.0516(2) 0.5904(2) 0.0449 1.0000 Uani C28 -0.0768(3) 0.1583(2) 0.9459(2) 0.0419 1.0000 Uani N3 0.5763(2) -0.14517(18) 0.85255(18) 0.0429 1.0000 Uani O7 0.68380(19) -0.12229(17) 0.8850(2) 0.0668 1.0000 Uani O8 0.5668(2) -0.24056(17) 0.83612(18) 0.0621 1.0000 Uani H21 0.6152 0.3668 0.0559 0.0330 1.0000 Uiso H41 0.7567 0.5491 -0.2686 0.0334 1.0000 Uiso H61 0.8909 0.6123 0.0210 0.0307 1.0000 Uiso H81 0.6376 0.4445 0.3887 0.0428 1.0000 Uiso H82 0.7550 0.3277 0.3945 0.0428 1.0000 Uiso H91 0.5581 0.2147 0.3984 0.0373 1.0000 Uiso H101 0.4246 0.4072 0.4853 0.0345 1.0000 Uiso H121 0.2155 0.3918 0.5790 0.0305 1.0000 Uiso H141 0.0328 0.1863 0.5014 0.0334 1.0000 Uiso H161 -0.2120 0.0843 0.8023 0.0367 1.0000 Uiso H181 0.1041 0.2753 0.7972 0.0295 1.0000 Uiso H201 0.3462 0.2218 0.8241 0.0401 1.0000 Uiso H211 0.5501 0.0744 0.8648 0.0450 1.0000 Uiso H231 0.3226 -0.1643 0.7964 0.0363 1.0000 Uiso H241 0.1170 -0.0176 0.7641 0.0334 1.0000 Uiso H251 0.2472 0.0991 0.5462 0.0391 1.0000 Uiso H252 0.4204 0.0902 0.5461 0.0391 1.0000 Uiso H253 0.3393 0.1408 0.4257 0.0391 1.0000 Uiso H261 -0.1387 0.3580 0.6580 0.0371 1.0000 Uiso H262 -0.0124 0.4351 0.6597 0.0371 1.0000 Uiso H263 -0.0571 0.4213 0.5382 0.0371 1.0000 Uiso H271 -0.1381 0.0622 0.5081 0.0559 1.0000 Uiso H272 -0.2757 0.0777 0.5960 0.0559 1.0000 Uiso H273 -0.1489 -0.0330 0.6331 0.0559 1.0000 Uiso H281 -0.1674 0.1250 0.9742 0.0480 1.0000 Uiso H282 -0.0861 0.2394 0.9554 0.0480 1.0000 Uiso H283 0.0040 0.1077 0.9910 0.0480 1.0000 Uiso 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 0.0187(9) 0.0271(11) 0.0288(11) -0.0093(9) 0.0008(8) -0.0006(8) C2 0.022(1) 0.0288(11) 0.0315(12) -0.0089(9) 0.0008(8) -0.0012(9) C3 0.022(1) 0.0326(11) 0.0332(12) -0.0149(9) -0.0033(8) 0.0014(9) C4 0.024(1) 0.0331(12) 0.0260(11) -0.0080(9) -0.0023(8) 0.0051(9) C5 0.022(1) 0.0266(11) 0.0268(12) -0.0038(9) 0.0022(8) 0.0025(8) C6 0.0186(9) 0.0276(11) 0.0305(12) -0.0085(9) -0.0023(8) 0.0003(8) C7 0.022(1) 0.0294(11) 0.0269(11) -0.0077(9) 0.0036(8) -0.0056(9) O1 0.0387(9) 0.046(1) 0.0295(9) -0.0111(7) 0.0029(7) -0.0199(8) O2 0.0281(8) 0.0456(9) 0.0249(8) -0.0099(7) 0.0055(6) -0.0150(7) C8 0.0324(12) 0.0500(14) 0.0246(12) -0.011(1) 0.0060(9) -0.0153(11) C9 0.0308(11) 0.0362(12) 0.0261(12) -0.0077(9) 0.0032(9) -0.0116(9) C10 0.0302(11) 0.0310(11) 0.0251(11) -0.0062(9) 0.0015(9) -0.0104(9) C11 0.0286(11) 0.0267(11) 0.0198(11) -0.0026(8) 0.0002(8) -0.0068(9) C12 0.027(1) 0.024(1) 0.0255(11) -0.0043(9) -0.0008(8) -0.0082(8) C13 0.026(1) 0.023(1) 0.0242(11) -0.0048(8) 0.0014(8) -0.0046(8) C14 0.024(1) 0.0321(11) 0.0271(11) -0.0079(9) -0.0005(8) -0.0044(9) C15 0.0270(11) 0.0296(11) 0.0357(13) -0.0081(9) -0.0042(9) -0.0048(9) C16 0.023(1) 0.0294(11) 0.0391(13) -0.003(1) 0.0067(9) -0.0064(9) C17 0.026(1) 0.0275(11) 0.0279(12) -0.0044(9) 0.0050(9) -0.0004(9) C18 0.025(1) 0.024(1) 0.0251(11) -0.0080(8) 0.0018(8) -0.0039(8) C19 0.025(1) 0.026(1) 0.0228(11) -0.0041(8) 0.0024(8) -0.0031(8) C20 0.0299(12) 0.0307(12) 0.0397(14) -0.009(1) -0.002(1) -0.0038(9) C21 0.0269(11) 0.0389(14) 0.0466(15) -0.0061(11) -0.003(1) -0.006(1) C22 0.0270(11) 0.0318(12) 0.0311(12) -0.0012(9) 0.0038(9) 0.0043(9) C23 0.0357(12) 0.0275(11) 0.0274(12) -0.0049(9) 0.0035(9) 0.0003(9) C24 0.0277(11) 0.0286(11) 0.0270(12) -0.0078(9) -0.0001(9) -0.0039(9) N1 0.031(1) 0.0461(12) 0.0428(13) -0.023(1) -0.0056(9) -0.0029(9) O3 0.0729(14) 0.0843(15) 0.0532(13) -0.0292(11) 0.007(1) -0.0504(12) O4 0.0505(11) 0.0610(12) 0.0399(11) -0.0231(9) -0.0117(8) -0.0036(9) N2 0.032(1) 0.0359(11) 0.0286(12) 0.0002(9) 0.0021(8) -0.0037(8) O5 0.0665(13) 0.0719(13) 0.0279(11) 0.0074(9) -0.0037(8) -0.025(1) O6 0.0361(9) 0.0407(9) 0.040(1) -0.0076(8) 0.0018(7) -0.0130(7) C25 0.0304(11) 0.0320(12) 0.0353(13) -0.012(1) 0.0069(9) -0.0079(9) C26 0.0273(11) 0.0277(11) 0.0377(13) -0.005(1) -0.0001(9) -0.0026(9) C27 0.0374(13) 0.0480(15) 0.0543(17) -0.0157(12) -0.0044(11) -0.0159(11) C28 0.0413(13) 0.0465(14) 0.0323(13) -0.0083(11) 0.010(1) -0.0004(11) N3 0.0316(11) 0.0384(12) 0.0458(13) 0.000(1) 0.0057(9) 0.0070(9) O7 0.029(1) 0.0556(12) 0.1014(17) 0.0006(11) -0.011(1) 0.0016(9) O8 0.0541(12) 0.0465(12) 0.0804(15) -0.0223(11) -0.009(1) 0.0208(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.389(3) yes C1 . C6 . 1.398(3) yes C1 . C7 . 1.490(3) yes C2 . C3 . 1.384(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.385(3) yes C3 . N1 . 1.477(3) yes C4 . C5 . 1.382(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.377(3) yes C5 . N2 . 1.475(3) yes C6 . H61 . 1.000 no C7 . O1 . 1.207(2) yes C7 . O2 . 1.333(2) yes O2 . C8 . 1.478(3) yes C8 . C9 . 1.490(3) yes C8 . H81 . 1.000 no C8 . H82 . 1.000 no C9 . C10 . 1.330(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.470(3) yes C10 . H101 . 1.000 no C11 . C12 . 1.344(3) yes C11 . C25 . 1.503(3) yes C12 . C13 . 1.519(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.514(3) yes C13 . C18 . 1.562(3) yes C13 . C26 . 1.550(3) yes C14 . C15 . 1.339(3) yes C14 . H141 . 1.000 no C15 . C16 . 1.469(3) yes C15 . C27 . 1.501(3) yes C16 . C17 . 1.325(3) yes C16 . H161 . 1.000 no C17 . C18 . 1.517(3) yes C17 . C28 . 1.499(3) yes C18 . C19 . 1.525(3) yes C18 . H181 . 1.000 no C19 . C20 . 1.384(3) yes C19 . C24 . 1.395(3) yes C20 . C21 . 1.387(3) yes C20 . H201 . 1.000 no C21 . C22 . 1.384(3) yes C21 . H211 . 1.000 no C22 . C23 . 1.382(3) yes C22 . N3 . 1.464(3) yes C23 . C24 . 1.387(3) yes C23 . H231 . 1.000 no C24 . H241 . 1.000 no N1 . O3 . 1.227(3) yes N1 . O4 . 1.222(3) yes N2 . O5 . 1.225(2) yes N2 . O6 . 1.222(2) yes C25 . H251 . 1.000 no C25 . H252 . 1.000 no C25 . H253 . 1.000 no C26 . H261 . 1.000 no C26 . H262 . 1.000 no C26 . H263 . 1.000 no C27 . H271 . 1.000 no C27 . H272 . 1.000 no C27 . H273 . 1.000 no C28 . H281 . 1.000 no C28 . H282 . 1.000 no C28 . H283 . 1.000 no N3 . O7 . 1.224(3) yes N3 . O8 . 1.233(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 120.07(19) yes C2 . C1 . C7 . 122.32(18) yes C6 . C1 . C7 . 117.60(18) yes C1 . C2 . C3 . 118.37(19) yes C1 . C2 . H21 . 120.8 no C3 . C2 . H21 . 120.8 no C2 . C3 . C4 . 123.4(2) yes C2 . C3 . N1 . 118.37(19) yes C4 . C3 . N1 . 118.27(19) yes C3 . C4 . C5 . 116.21(19) yes C3 . C4 . H41 . 121.9 no C5 . C4 . H41 . 121.9 no C4 . C5 . C6 . 123.14(19) yes C4 . C5 . N2 . 118.71(19) yes C6 . C5 . N2 . 118.12(19) yes C1 . C6 . C5 . 118.83(19) yes C1 . C6 . H61 . 120.6 no C5 . C6 . H61 . 120.6 no C1 . C7 . O1 . 123.35(19) yes C1 . C7 . O2 . 112.23(18) yes O1 . C7 . O2 . 124.4(2) yes C7 . O2 . C8 . 115.21(16) yes O2 . C8 . C9 . 107.00(17) yes O2 . C8 . H81 . 110.1 no C9 . C8 . H81 . 110.09 no O2 . C8 . H82 . 110.09 no C9 . C8 . H82 . 110.1 no H81 . C8 . H82 . 109.5 no C8 . C9 . C10 . 122.6(2) yes C8 . C9 . H91 . 118.7 no C10 . C9 . H91 . 118.7 no C9 . C10 . C11 . 126.7(2) yes C9 . C10 . H101 . 116.7 no C11 . C10 . H101 . 116.65 no C10 . C11 . C12 . 117.74(19) yes C10 . C11 . C25 . 116.26(18) yes C12 . C11 . C25 . 126.01(18) yes C11 . C12 . C13 . 132.10(19) yes C11 . C12 . H121 . 113.95 no C13 . C12 . H121 . 113.95 no C12 . C13 . C14 . 116.31(17) yes C12 . C13 . C18 . 110.09(16) yes C14 . C13 . C18 . 110.25(16) yes C12 . C13 . C26 . 106.43(16) yes C14 . C13 . C26 . 105.44(17) yes C18 . C13 . C26 . 107.83(16) yes C13 . C14 . C15 . 120.40(19) yes C13 . C14 . H141 . 119.80 no C15 . C14 . H141 . 119.8 no C14 . C15 . C16 . 119.45(19) yes C14 . C15 . C27 . 122.6(2) yes C16 . C15 . C27 . 117.9(2) yes C15 . C16 . C17 . 122.73(19) yes C15 . C16 . H161 . 118.6 no C17 . C16 . H161 . 118.6 no C16 . C17 . C18 . 119.15(19) yes C16 . C17 . C28 . 124.1(2) yes C18 . C17 . C28 . 116.55(19) yes C13 . C18 . C17 . 110.73(17) yes C13 . C18 . C19 . 113.50(16) yes C17 . C18 . C19 . 109.82(17) yes C13 . C18 . H181 . 105.88 no C17 . C18 . H181 . 109.86 no C19 . C18 . H181 . 106.87 no C18 . C19 . C20 . 119.87(18) yes C18 . C19 . C24 . 121.51(18) yes C20 . C19 . C24 . 118.62(19) yes C19 . C20 . C21 . 121.4(2) yes C19 . C20 . H201 . 119.3 no C21 . C20 . H201 . 119.3 no C20 . C21 . C22 . 118.3(2) yes C20 . C21 . H211 . 120.8 no C22 . C21 . H211 . 120.8 no C21 . C22 . C23 . 122.1(2) yes C21 . C22 . N3 . 119.4(2) yes C23 . C22 . N3 . 118.5(2) yes C22 . C23 . C24 . 118.3(2) yes C22 . C23 . H231 . 120.9 no C24 . C23 . H231 . 120.9 no C19 . C24 . C23 . 121.2(2) yes C19 . C24 . H241 . 119.38 no C23 . C24 . H241 . 119.4 no C3 . N1 . O3 . 117.25(19) yes C3 . N1 . O4 . 118.6(2) yes O3 . N1 . O4 . 124.2(2) yes C5 . N2 . O5 . 116.89(19) yes C5 . N2 . O6 . 118.34(18) yes O5 . N2 . O6 . 124.77(19) yes C11 . C25 . H251 . 109.47 no C11 . C25 . H252 . 109.47 no H251 . C25 . H252 . 109.5 no C11 . C25 . H253 . 109.47 no H251 . C25 . H253 . 109.5 no H252 . C25 . H253 . 109.5 no C13 . C26 . H261 . 109.47 no C13 . C26 . H262 . 109.47 no H261 . C26 . H262 . 109.5 no C13 . C26 . H263 . 109.47 no H261 . C26 . H263 . 109.5 no H262 . C26 . H263 . 109.5 no C15 . C27 . H271 . 109.5 no C15 . C27 . H272 . 109.5 no H271 . C27 . H272 . 109.5 no C15 . C27 . H273 . 109.5 no H271 . C27 . H273 . 109.5 no H272 . C27 . H273 . 109.5 no C17 . C28 . H281 . 109.5 no C17 . C28 . H282 . 109.5 no H281 . C28 . H282 . 109.5 no C17 . C28 . H283 . 109.5 no H281 . C28 . H283 . 109.5 no H282 . C28 . H283 . 109.5 no C22 . N3 . O7 . 118.7(2) yes C22 . N3 . O8 . 117.5(2) yes O7 . N3 . O8 . 123.8(2) yes data_CRYSTALS_cif_compound_34 _database_code_CSD 209361 _chemical_name_common '4,6,8-trimethyldec-2,4,6,8-tetraenyl 3,5-dinitrobenzoate' #============================================================= # Diffractometer details #============================================================= _diffrn_measurement_device_type ; Nonius KappaCCD ; _diffrn_radiation_monochromator graphite _computing_data_collection ; KappaCCD software 'Collect' (Nonius, 2000) ; _computing_data_reduction ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; _computing_cell_refinement ; KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) ; #============================================================= # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al, 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al, 2001) ; _computing_structure_solution 'SIR92 (Giacovazzo et al, 1992)' _chemical_name_systematic # IUPAC name, in full ; 4,6,8-trimethyldec-2,4,6,8-tetraenyl 3,5-dinitrobenzoate ; _chemical_melting_point ? _refine_ls_matrix_type full _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #============================================================= _cell_length_a 13.1953(2) _cell_angle_alpha 90 _cell_length_b 8.0054(2) _cell_angle_beta 107.7083(8) _cell_length_c 19.1169(4) _cell_angle_gamma 90 _cell_volume 1923.7 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0020 0.0020 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0040 0.0030 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0080 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _chemical_formula_sum ' C20 H22 N2 O6 ' _chemical_formula_moiety ' C20 H22 N2 O6 ' _chemical_compound_source ; synthesis as described ; _chemical_formula_weight 386.40 _cell_measurement_reflns_used 16330 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _cell_formula_units_Z 4 _exptl_crystal_description ' block ' _exptl_crystal_colour ' orange ' _exptl_crystal_size_min 0.26 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_meas ? _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.099 _diffrn_measurement_method \w _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Denzo/Scalepack (Otwinowski & Minor, 1996) ; _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.97 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 150 _diffrn_reflns_number 16330 _reflns_number_total 4330 #4625 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.026 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_gt 3293 _diffrn_reflns_theta_min 5.14 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.27 _refine_diff_density_max 0.33 _reflns_threshold_expression >3.00\s(I) _refine_ls_number_reflns 3293 _refine_ls_number_parameters 301 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0513 _refine_ls_goodness_of_fit_ref 1.0033 _refine_ls_shift/su_max 0.010140 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin , 1979) 2.15 1.35 1.70 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type C1 0.31318(9) 0.38271(14) 0.44017(6) 0.0262 1.0000 Uani C2 0.38889(9) 0.39113(15) 0.50912(6) 0.0276 1.0000 Uani C3 0.36396(9) 0.47783(15) 0.56451(6) 0.0284 1.0000 Uani C4 0.26660(9) 0.55344(14) 0.55497(6) 0.0285 1.0000 Uani C5 0.19332(9) 0.54018(13) 0.48585(6) 0.0268 1.0000 Uani C6 0.21423(9) 0.45797(13) 0.42787(6) 0.0264 1.0000 Uani C7 0.34176(9) 0.28875(14) 0.38092(6) 0.0281 1.0000 Uani N1 0.44401(8) 0.48725(14) 0.63746(6) 0.0342 1.0000 Uani O1 0.52737(8) 0.41063(14) 0.64648(5) 0.0442 1.0000 Uani O2 0.42296(8) 0.57103(14) 0.68456(5) 0.0446 1.0000 Uani N2 0.08810(8) 0.61691(13) 0.47352(6) 0.0323 1.0000 Uani O3 0.06522(8) 0.66676(13) 0.52761(6) 0.0435 1.0000 Uani O4 0.02893(7) 0.62541(13) 0.41043(5) 0.0425 1.0000 Uani O5 0.42712(7) 0.22268(13) 0.39001(5) 0.0383 1.0000 Uani O6 0.26184(7) 0.28941(11) 0.31852(4) 0.0306 1.0000 Uani C8 0.2773(1) 0.19650(15) 0.25600(6) 0.0313 1.0000 Uani C9 0.31880(9) 0.30783(15) 0.20884(6) 0.0287 1.0000 Uani C10 0.26068(9) 0.34745(14) 0.14042(6) 0.0276 1.0000 Uani C11 0.29586(9) 0.44719(14) 0.08783(6) 0.0276 1.0000 Uani C12 0.22830(9) 0.45638(14) 0.01843(6) 0.0283 1.0000 Uani C13 0.2403(1) 0.52762(14) -0.04904(6) 0.0286 1.0000 Uani C14 0.1502(1) 0.54587(15) -0.10598(7) 0.0327 1.0000 Uani C15 0.13563(11) 0.60916(17) -0.18062(7) 0.0363 1.0000 Uani C16 0.19861(11) 0.72310(18) -0.19700(7) 0.0385 1.0000 Uani C17 0.18868(17) 0.7916(2) -0.2722(1) 0.0550 1.0000 Uani C18 0.4033(1) 0.52903(16) 0.11675(7) 0.0335 1.0000 Uani C19 0.34970(11) 0.56292(18) -0.05489(7) 0.0368 1.0000 Uani C20 0.03863(15) 0.5397(3) -0.23720(9) 0.0560 1.0000 Uani H21 0.4597 0.3358 0.5185 0.0330 1.0000 Uiso H41 0.2500 0.6145 0.5958 0.0345 1.0000 Uiso H61 0.1596 0.4529 0.3785 0.0313 1.0000 Uiso H81 0.3292 0.1039 0.2750 0.0375 1.0000 Uiso H82 0.2076 0.1486 0.2261 0.0375 1.0000 Uiso H91 0.3923 0.3545 0.2288 0.0348 1.0000 Uiso H101 0.1859 0.3049 0.1235 0.0334 1.0000 Uiso H121 0.1571 0.4049 0.0123 0.0342 1.0000 Uiso H141 0.0834 0.5110 -0.0957 0.0395 1.0000 Uiso H161 0.2583 0.7674 -0.1553 0.0467 1.0000 Uiso H171 0.261(2) 0.788(4) -0.2836(14) 0.098(8) 1.0000 Uiso H172 0.132(2) 0.722(4) -0.3121(15) 0.097(8) 1.0000 Uiso H173 0.166(3) 0.915(4) -0.2801(17) 0.11(1) 1.0000 Uiso H181 0.4174(15) 0.612(2) 0.085(1) 0.053(5) 1.0000 Uiso H182 0.4112(14) 0.583(2) 0.165(1) 0.049(5) 1.0000 Uiso H183 0.4606(16) 0.444(2) 0.127(1) 0.052(5) 1.0000 Uiso H191 0.3749(16) 0.678(3) -0.0384(11) 0.058(5) 1.0000 Uiso H192 0.4024(15) 0.481(2) -0.023(1) 0.049(5) 1.0000 Uiso H193 0.3497(15) 0.550(2) -0.1076(11) 0.053(5) 1.0000 Uiso H201 -0.026(3) 0.592(4) -0.2323(17) 0.11(1) 1.0000 Uiso H202 0.036(2) 0.413(4) -0.2327(14) 0.095(8) 1.0000 Uiso H203 0.034(2) 0.570(4) -0.2873(17) 0.102(9) 1.0000 Uiso 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 0.0270(5) 0.0274(5) 0.0246(5) 0.0031(4) 0.0087(4) -0.0026(4) C2 0.0237(5) 0.0304(5) 0.0284(5) 0.0034(4) 0.0073(4) -0.0007(4) C3 0.0280(5) 0.0311(5) 0.0237(5) 0.0029(4) 0.0042(4) -0.0046(4) C4 0.0313(6) 0.0274(5) 0.0276(5) 0.0007(4) 0.0100(4) -0.0033(4) C5 0.0257(5) 0.0257(5) 0.0290(5) 0.0035(4) 0.0085(4) -0.0005(4) C6 0.0273(5) 0.0272(5) 0.0238(5) 0.0038(4) 0.0064(4) -0.0028(4) C7 0.0290(5) 0.0305(5) 0.0257(5) 0.0029(4) 0.0098(4) -0.0020(4) N1 0.0300(5) 0.0417(6) 0.0277(5) -0.0001(4) 0.0037(4) -0.0064(4) O1 0.0311(5) 0.0557(6) 0.0375(5) -0.0001(4) -0.0020(4) 0.0017(4) O2 0.0419(5) 0.0601(6) 0.0286(4) -0.0106(4) 0.0058(4) -0.0076(5) N2 0.0300(5) 0.0313(5) 0.0355(5) 0.0012(4) 0.0097(4) 0.0023(4) O3 0.0405(5) 0.0502(6) 0.0420(5) -0.0065(4) 0.0158(4) 0.0094(4) O4 0.0327(5) 0.0528(6) 0.0373(5) 0.0035(4) 0.0036(4) 0.0099(4) O5 0.0313(4) 0.0488(5) 0.0353(5) -0.0021(4) 0.0107(4) 0.0068(4) O6 0.0318(4) 0.0377(5) 0.0219(4) 0.0003(3) 0.0078(3) 0.0021(3) C8 0.0365(6) 0.0327(6) 0.0245(5) -0.0028(4) 0.0088(4) -0.0017(5) C9 0.0312(5) 0.0293(5) 0.0265(5) -0.0044(4) 0.0100(4) -0.0018(4) C10 0.0284(5) 0.0284(5) 0.0267(5) -0.0037(4) 0.0096(4) -0.0008(4) C11 0.0304(6) 0.0258(5) 0.0280(5) -0.0032(4) 0.0109(4) 0.0008(4) C12 0.0287(5) 0.0270(5) 0.0297(6) -0.0017(4) 0.0097(4) -0.0002(4) C13 0.0337(6) 0.0250(5) 0.0283(5) -0.0019(4) 0.0112(5) 0.0006(4) C14 0.0335(6) 0.0355(6) 0.0298(6) 0.0004(5) 0.0107(5) -0.0009(5) C15 0.0374(6) 0.0407(6) 0.0302(6) 0.0013(5) 0.0092(5) 0.0032(5) C16 0.0432(7) 0.0398(7) 0.0337(6) 0.0026(5) 0.0133(5) 0.0035(5) C17 0.0683(11) 0.060(1) 0.0419(8) 0.0123(7) 0.0250(8) 0.0032(9) C18 0.0322(6) 0.0367(6) 0.0306(6) -0.0023(5) 0.0083(5) -0.0055(5) C19 0.0340(6) 0.0452(7) 0.0328(6) 0.0010(5) 0.0125(5) -0.0025(5) C20 0.0515(9) 0.0731(12) 0.0341(7) 0.0071(7) -0.0009(6) -0.0149(9) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.3924(15) yes C1 . C6 . 1.3915(16) yes C1 . C7 . 1.5004(16) yes C2 . C3 . 1.3868(17) yes C2 . H21 . 1.0000 no C3 . C4 . 1.3811(17) yes C3 . N1 . 1.4731(15) yes C4 . C5 . 1.3837(17) yes C4 . H41 . 1.0000 no C5 . C6 . 1.3871(16) yes C5 . N2 . 1.4701(15) yes C6 . H61 . 1.0000 no C7 . O5 . 1.2081(15) yes C7 . O6 . 1.3303(14) yes N1 . O1 . 1.2249(15) yes N1 . O2 . 1.2207(15) yes N2 . O3 . 1.2287(14) yes N2 . O4 . 1.2231(14) yes O6 . C8 . 1.4738(14) yes C8 . C9 . 1.4856(16) yes C8 . H81 . 1.0000 no C8 . H82 . 1.0000 no C9 . C10 . 1.3376(17) yes C9 . H91 . 1.0000 no C10 . C11 . 1.4656(16) yes C10 . H101 . 1.0000 no C11 . C12 . 1.3567(16) yes C11 . C18 . 1.5065(16) yes C12 . C13 . 1.4625(15) yes C12 . H121 . 1.0000 no C13 . C14 . 1.3537(17) yes C13 . C19 . 1.5075(17) yes C14 . C15 . 1.4706(17) yes C14 . H141 . 1.0000 no C15 . C16 . 1.334(2) yes C15 . C20 . 1.508(2) yes C16 . C17 . 1.506(2) yes C16 . H161 . 1.0000 no C17 . H171 . 1.05(3) no C17 . H172 . 1.05(3) no C17 . H173 . 1.03(3) no C18 . H181 . 0.96(2) no C18 . H182 . 0.993(19) no C18 . H183 . 0.99(2) no C19 . H191 . 1.00(2) no C19 . H192 . 1.010(19) no C19 . H193 . 1.014(19) no C20 . H201 . 0.98(3) no C20 . H202 . 1.02(3) no C20 . H203 . 0.97(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 120.3(1) yes C2 . C1 . C7 . 117.8(1) yes C6 . C1 . C7 . 121.9(1) yes C1 . C2 . C3 . 118.6(1) yes C1 . C2 . H21 . 120.70 no C3 . C2 . H21 . 120.71 no C2 . C3 . C4 . 123.07(11) yes C2 . C3 . N1 . 118.69(11) yes C4 . C3 . N1 . 118.23(11) yes C3 . C4 . C5 . 116.4(1) yes C3 . C4 . H41 . 121.81 no C5 . C4 . H41 . 121.81 no C4 . C5 . C6 . 123.26(11) yes C4 . C5 . N2 . 118.2(1) yes C6 . C5 . N2 . 118.5(1) yes C1 . C6 . C5 . 118.3(1) yes C1 . C6 . H61 . 120.83 no C5 . C6 . H61 . 120.83 no C1 . C7 . O5 . 123.25(11) yes C1 . C7 . O6 . 111.2(1) yes O5 . C7 . O6 . 125.51(11) yes C3 . N1 . O1 . 117.54(11) yes C3 . N1 . O2 . 117.89(11) yes O1 . N1 . O2 . 124.57(11) yes C5 . N2 . O3 . 117.6(1) yes C5 . N2 . O4 . 118.0(1) yes O3 . N2 . O4 . 124.42(11) yes C7 . O6 . C8 . 117.23(9) yes O6 . C8 . C9 . 110.91(9) yes O6 . C8 . H81 . 109.1 no C9 . C8 . H81 . 109.1 no O6 . C8 . H82 . 109.1 no C9 . C8 . H82 . 109.1 no H81 . C8 . H82 . 109.5 no C8 . C9 . C10 . 121.88(11) yes C8 . C9 . H91 . 119.1 no C10 . C9 . H91 . 119.1 no C9 . C10 . C11 . 126.37(11) yes C9 . C10 . H101 . 116.8 no C11 . C10 . H101 . 116.8 no C10 . C11 . C12 . 116.7(1) yes C10 . C11 . C18 . 116.4(1) yes C12 . C11 . C18 . 126.91(11) yes C11 . C12 . C13 . 131.93(11) yes C11 . C12 . H121 . 114.0 no C13 . C12 . H121 . 114.0 no C12 . C13 . C14 . 116.53(11) yes C12 . C13 . C19 . 120.11(11) yes C14 . C13 . C19 . 123.13(11) yes C13 . C14 . C15 . 129.88(11) yes C13 . C14 . H141 . 115.1 no C15 . C14 . H141 . 115.1 no C14 . C15 . C16 . 123.80(12) yes C14 . C15 . C20 . 113.64(12) yes C16 . C15 . C20 . 122.48(13) yes C15 . C16 . C17 . 126.40(14) yes C15 . C16 . H161 . 116.8 no C17 . C16 . H161 . 116.8 no C16 . C17 . H171 . 111.7(15) no C16 . C17 . H172 . 109.6(15) no H171 . C17 . H172 . 109.(2) no C16 . C17 . H173 . 115.2(17) no H171 . C17 . H173 . 103.9(23) no H172 . C17 . H173 . 106.8(24) no C11 . C18 . H181 . 114.3(12) no C11 . C18 . H182 . 110.6(10) no H181 . C18 . H182 . 107.5(15) no C11 . C18 . H183 . 110.4(11) no H181 . C18 . H183 . 109.0(16) no H182 . C18 . H183 . 104.7(15) no C13 . C19 . H191 . 112.5(11) no C13 . C19 . H192 . 109.6(10) no H191 . C19 . H192 . 108.0(15) no C13 . C19 . H193 . 110.1(11) no H191 . C19 . H193 . 108.1(15) no H192 . C19 . H193 . 108.4(14) no C15 . C20 . H201 . 110.5(19) no C15 . C20 . H202 . 110.6(15) no H201 . C20 . H202 . 111.(2) no C15 . C20 . H203 . 113.4(18) no H201 . C20 . H203 . 101.(2) no H202 . C20 . H203 . 110.(2) no