# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_LU30 _database_code_depnum_ccdc_archive 'CCDC 909977' ##################################################################### # CHEMICAL INFORMATION # ##################################################################### _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C11 H14 N2 O4' _chemical_formula_sum 'C11 H14 N2 O4' _chemical_formula_weight 238.24 _chemical_melting_point ? _chemical_compound_source ? ##################################################################### # UNIT CELL INFORMATION # ##################################################################### _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,y+1/2,-z+1/2 -x,-y,-z x-1/2,-y-1/2,z-1/2 _cell_length_a 11.0598(8) _cell_length_b 9.6504(6) _cell_length_c 12.3144(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.315(4) _cell_angle_gamma 90.00 _cell_volume 1215.90(15) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 22.23 _cell_measurement_theta_max 33.08 ##################################################################### # CRYSTAL INFORMATION # ##################################################################### _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_special_details ? ##################################################################### # ABSORPTION CORRECTION # ##################################################################### _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'DIFABS (Walker & Stuart, 1983)' _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.955 ##################################################################### # DATA COLLECTION # ##################################################################### _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens AED' _diffrn_measurement_method '\q/2\q scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 4660 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 69.83 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_theta_min 4.58 _diffrn_reflns_theta_max 69.83 _reflns_number_total 2294 _reflns_number_gt 1868 _reflns_threshold_expression I>2\s(I) ##################################################################### # COMPUTING PROGRAMS # ##################################################################### _computing_data_collection 'AED Software (Belletti et al., 1993)' _computing_cell_refinement AED _computing_data_reduction AED _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELX97-L (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? ##################################################################### # REFINEMENT INFORMATION # ##################################################################### _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^)+(0.0784P)^2^] 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 2294 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_abs_structure_Flack ? _refine_ls_abs_structure_details ? _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.117 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.038 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.10486(17) 0.0997(2) 0.19077(17) 0.1715(7) Uani 1 1 d . . . O2 O 0.22168(17) 0.2641(2) 0.28882(14) 0.1646(7) Uani 1 1 d . . . O3 O 0.41801(12) 0.05115(10) 0.08931(11) 0.1127(4) Uani 1 1 d . . . O4 O 0.45481(13) 0.09765(15) 0.26788(11) 0.1296(5) Uani 1 1 d . . . N1 N 0.17199(12) 0.19606(17) 0.19784(14) 0.1046(4) Uani 1 1 d . . . N2 N 0.41192(9) 0.12578(10) 0.16521(10) 0.0748(3) Uani 1 1 d . . . C1 C 0.19771(10) 0.24754(11) 0.08994(10) 0.0664(3) Uani 1 1 d . . . C2 C 0.13180(14) 0.38900(14) 0.06266(13) 0.0883(4) Uani 1 1 d . . . H2A H 0.1695 0.4487 0.1294 0.132 Uiso 1 1 calc R . . H2B H 0.0400 0.3787 0.0451 0.132 Uiso 1 1 calc R . . H2C H 0.1444 0.4287 -0.0038 0.132 Uiso 1 1 calc R . . C3 C 0.13762(14) 0.14689(16) -0.00941(16) 0.1029(5) Uani 1 1 d . . . H3A H 0.1784 0.0579 0.0125 0.154 Uiso 1 1 calc R . . H3B H 0.1504 0.1798 -0.0778 0.154 Uiso 1 1 calc R . . H3C H 0.0457 0.1388 -0.0263 0.154 Uiso 1 1 calc R . . C4 C 0.34663(9) 0.26481(9) 0.13043(9) 0.0596(3) Uani 1 1 d . . . H4 H 0.3755 0.3230 0.2009 0.072 Uiso 1 1 calc R . . C5 C 0.39279(11) 0.33377(12) 0.04210(10) 0.0696(3) Uani 1 1 d . . . H5A H 0.3618 0.2809 -0.0303 0.083 Uiso 1 1 calc R . . H5B H 0.3557 0.4261 0.0248 0.083 Uiso 1 1 calc R . . C6 C 0.54084(10) 0.34364(10) 0.08822(9) 0.0647(3) Uani 1 1 d . . . C7 C 0.61063(12) 0.26629(12) 0.03809(12) 0.0783(3) Uani 1 1 d . . . H7 H 0.5668 0.2096 -0.0259 0.094 Uiso 1 1 calc R . . C8 C 0.74589(14) 0.27256(15) 0.08261(14) 0.0918(4) Uani 1 1 d . . . H8 H 0.7920 0.2206 0.0475 0.110 Uiso 1 1 calc R . . C9 C 0.81263(12) 0.35392(14) 0.17721(13) 0.0870(4) Uani 1 1 d . . . H9 H 0.9035 0.3548 0.2084 0.104 Uiso 1 1 calc R . . C10 C 0.74345(13) 0.43466(15) 0.22570(11) 0.0859(4) Uani 1 1 d . . . H10 H 0.7879 0.4928 0.2884 0.103 Uiso 1 1 calc R . . C11 C 0.60816(12) 0.42997(12) 0.18171(11) 0.0754(3) Uani 1 1 d . . . H11 H 0.5623 0.4849 0.2150 0.090 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1432(12) 0.1842(15) 0.2028(15) 0.0697(13) 0.0833(11) -0.0396(11) O2 0.1839(15) 0.229(2) 0.1092(9) 0.0231(11) 0.0877(10) 0.0186(14) O3 0.1206(9) 0.0617(5) 0.1542(10) -0.0104(6) 0.0502(7) 0.0167(5) O4 0.1303(10) 0.1360(10) 0.1178(8) 0.0630(8) 0.0417(7) 0.0535(8) N1 0.0839(7) 0.1238(10) 0.1211(11) 0.0488(9) 0.0557(7) 0.0254(7) N2 0.0629(5) 0.0593(5) 0.1022(7) 0.0209(5) 0.0314(5) 0.0062(4) C1 0.0621(6) 0.0589(6) 0.0815(6) 0.0106(5) 0.0311(5) 0.0083(4) C2 0.0830(8) 0.0730(7) 0.1077(9) 0.0135(6) 0.0348(7) 0.0262(6) C3 0.0737(7) 0.0907(9) 0.1337(12) -0.0265(8) 0.0275(8) -0.0175(7) C4 0.0630(5) 0.0477(5) 0.0676(5) 0.0054(4) 0.0241(4) 0.0026(4) C5 0.0688(6) 0.0633(6) 0.0756(6) 0.0127(5) 0.0263(5) -0.0015(4) C6 0.0697(6) 0.0536(5) 0.0738(6) 0.0072(4) 0.0307(5) -0.0054(4) C7 0.0832(7) 0.0645(6) 0.0944(8) -0.0115(5) 0.0418(6) -0.0101(5) C8 0.0871(8) 0.0766(7) 0.1284(11) -0.0096(7) 0.0596(8) -0.0054(6) C9 0.0696(6) 0.0835(8) 0.1127(10) 0.0037(7) 0.0400(7) -0.0122(6) C10 0.0817(8) 0.0882(8) 0.0889(8) -0.0102(6) 0.0334(6) -0.0254(6) C11 0.0824(7) 0.0658(6) 0.0869(7) -0.0081(5) 0.0422(6) -0.0120(5) ##################################################################### # MOLECULAR GEOMETRY # ##################################################################### loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.173(2) . ? O2 N1 1.233(2) . ? O3 N2 1.2020(15) . ? O4 N2 1.2008(15) . ? N1 C1 1.5427(17) . ? N2 C4 1.5067(13) . ? C1 C3 1.5048(19) . ? C1 C2 1.5237(15) . ? C1 C4 1.5380(14) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.5194(14) . ? C4 H4 0.9800 . ? C5 C6 1.5188(15) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.3769(16) . ? C6 C11 1.3867(16) . ? C7 C8 1.3853(18) . ? C7 H7 0.9300 . ? C8 C9 1.366(2) . ? C8 H8 0.9300 . ? C9 C10 1.377(2) . ? C9 H9 0.9300 . ? C10 C11 1.3853(18) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? 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 O1 N1 O2 122.76(17) . . ? O1 N1 C1 120.67(18) . . ? O2 N1 C1 116.52(14) . . ? O4 N2 O3 124.54(11) . . ? O4 N2 C4 117.11(11) . . ? O3 N2 C4 118.35(10) . . ? C3 C1 C2 111.86(10) . . ? C3 C1 C4 114.93(10) . . ? C2 C1 C4 109.76(9) . . ? C3 C1 N1 108.87(12) . . ? C2 C1 N1 104.43(10) . . ? C4 C1 N1 106.30(8) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N2 C4 C5 109.78(9) . . ? N2 C4 C1 109.53(8) . . ? C5 C4 C1 115.15(8) . . ? N2 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C1 C4 H4 107.4 . . ? C6 C5 C4 111.55(8) . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C11 118.84(11) . . ? C7 C6 C5 120.44(10) . . ? C11 C6 C5 120.72(10) . . ? C6 C7 C8 120.25(11) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C9 C8 C7 121.02(12) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 119.07(12) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 120.50(12) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C11 C6 120.26(11) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? #=== END OF CIF