# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 _database_code_depnum_ccdc_archive 'CCDC 905569' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 N2 O4' _chemical_formula_sum 'C20 H20 N2 O4' _chemical_formula_weight 352.38 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 '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 8.8616(5) _cell_length_b 11.3859(6) _cell_length_c 9.5300(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.2220(10) _cell_angle_gamma 90.00 _cell_volume 951.67(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6618 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 30.50 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9662 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details ; program SADABS, Bruker (2001). ; _diffrn_ambient_temperature 173(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-Nonius X8kappa APEX II CCD area detector ; _diffrn_measurement_method 'phi and omega scans with narrow frames' _diffrn_detector_area_resol_mean 8.26 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11197 _diffrn_reflns_av_R_equivalents 0.0170 _diffrn_reflns_av_sigmaI/netI 0.0095 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1714 _reflns_number_gt 1432 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 Software Suite (Bruker, 2007)' _computing_cell_refinement 'APEX2 Software Suite (Bruker, 2007)' _computing_data_reduction 'APEX2 Software Suite (Bruker, 2007)' _computing_structure_solution 'SIR2002 (Burla et al., 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL and publCIF (Westrip, 2010)' _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^)+(0.0458P)^2^+0.1841P] 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 1714 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0337 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0848 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 1.16709(8) 0.29096(7) 0.67172(10) 0.0377(2) Uani 1 1 d . . . O2 O 1.11793(8) 0.44586(6) 0.80440(9) 0.0301(2) Uani 1 1 d . . . N1 N 0.92821(9) 0.47557(7) 0.50670(10) 0.0253(2) Uani 1 1 d . . . C1 C 1.08921(11) 0.37204(9) 0.69690(12) 0.0251(3) Uani 1 1 d . . . C2 C 0.93744(11) 0.40123(8) 0.60845(12) 0.0229(3) Uani 1 1 d . . . C3 C 0.80035(11) 0.34176(9) 0.64430(12) 0.0240(3) Uani 1 1 d . . . C4 C 0.81295(12) 0.25623(10) 0.74870(13) 0.0314(3) Uani 1 1 d . . . H4 H 0.9108 0.2347 0.7958 0.038 Uiso 1 1 calc R . . C5 C 0.68406(13) 0.20161(10) 0.78519(15) 0.0377(3) Uani 1 1 d . . . H5 H 0.6939 0.1431 0.8570 0.045 Uiso 1 1 calc R . . C6 C 0.54128(13) 0.23245(10) 0.71703(15) 0.0363(3) Uani 1 1 d . . . H6 H 0.4529 0.1952 0.7419 0.044 Uiso 1 1 calc R . . C7 C 0.52755(12) 0.31751(11) 0.61272(14) 0.0356(3) Uani 1 1 d . . . H7 H 0.4293 0.3388 0.5663 0.043 Uiso 1 1 calc R . . C8 C 0.65551(12) 0.37219(10) 0.57506(13) 0.0310(3) Uani 1 1 d . . . H8 H 0.6450 0.4301 0.5025 0.037 Uiso 1 1 calc R . . C9 C 1.26029(14) 0.42655(11) 0.89986(15) 0.0415(3) Uani 1 1 d . . . H9A H 1.3485 0.4327 0.8472 0.050 Uiso 1 1 calc R . . H9B H 1.2608 0.3475 0.9431 0.050 Uiso 1 1 calc R . . C10 C 1.26890(17) 0.51910(13) 1.01172(16) 0.0525(4) Uani 1 1 d . . . H10A H 1.2762 0.5965 0.9683 0.079 Uiso 1 1 calc R . . H10B H 1.3591 0.5057 1.0823 0.079 Uiso 1 1 calc R . . H10C H 1.1771 0.5158 1.0580 0.079 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 0.0283(4) 0.0371(5) 0.0473(6) -0.0063(4) 0.0039(4) 0.0073(3) O2 0.0291(4) 0.0331(4) 0.0266(5) -0.0021(3) -0.0014(3) 0.0008(3) N1 0.0219(4) 0.0294(5) 0.0257(6) -0.0003(4) 0.0068(3) -0.0028(3) C1 0.0232(5) 0.0266(5) 0.0265(7) 0.0015(4) 0.0074(4) -0.0032(4) C2 0.0231(5) 0.0238(5) 0.0226(6) -0.0037(4) 0.0056(4) 0.0002(4) C3 0.0238(5) 0.0255(5) 0.0234(6) -0.0040(4) 0.0058(4) -0.0026(4) C4 0.0263(5) 0.0343(6) 0.0330(7) 0.0045(5) 0.0020(4) -0.0030(4) C5 0.0375(6) 0.0374(6) 0.0388(8) 0.0093(5) 0.0069(5) -0.0077(5) C6 0.0285(6) 0.0400(6) 0.0420(8) -0.0018(5) 0.0107(5) -0.0115(5) C7 0.0227(5) 0.0443(7) 0.0394(8) 0.0001(5) 0.0029(5) -0.0034(4) C8 0.0265(5) 0.0353(6) 0.0309(7) 0.0036(5) 0.0037(4) -0.0007(4) C9 0.0343(6) 0.0467(7) 0.0391(8) 0.0024(6) -0.0103(5) -0.0018(5) C10 0.0592(9) 0.0564(8) 0.0365(9) -0.0025(6) -0.0113(6) -0.0121(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.1972(13) . ? O2 C1 1.3215(13) . ? O2 C9 1.4626(13) . ? N1 C2 1.2809(14) . ? N1 N1 1.4110(16) 3_766 ? C1 C2 1.5184(14) . ? C2 C3 1.4731(14) . ? C3 C4 1.3852(16) . ? C3 C8 1.4002(14) . ? C4 C5 1.3878(16) . ? C4 H4 0.9500 . ? C5 C6 1.3823(17) . ? C5 H5 0.9500 . ? C6 C7 1.3807(18) . ? C6 H6 0.9500 . ? C7 C8 1.3852(16) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.4932(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 C9 116.10(9) . . ? C2 N1 N1 111.60(10) . 3_766 ? O1 C1 O2 126.38(10) . . ? O1 C1 C2 123.21(10) . . ? O2 C1 C2 110.38(8) . . ? N1 C2 C3 120.92(9) . . ? N1 C2 C1 121.37(9) . . ? C3 C2 C1 117.71(9) . . ? C4 C3 C8 119.13(10) . . ? C4 C3 C2 120.35(9) . . ? C8 C3 C2 120.51(10) . . ? C3 C4 C5 120.68(10) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.95(11) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C7 C6 C5 119.80(10) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C6 C7 C8 120.71(10) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C7 C8 C3 119.73(11) . . ? C7 C8 H8 120.1 . . ? C3 C8 H8 120.1 . . ? O2 C9 C10 106.82(10) . . ? O2 C9 H9A 110.4 . . ? C10 C9 H9A 110.4 . . ? O2 C9 H9B 110.4 . . ? C10 C9 H9B 110.4 . . ? H9A C9 H9B 108.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 C9 O2 C1 O1 0.96(16) . . . . ? C9 O2 C1 C2 179.14(9) . . . . ? N1 N1 C2 C3 178.26(10) 3_766 . . . ? N1 N1 C2 C1 -1.24(15) 3_766 . . . ? O1 C1 C2 N1 -93.93(13) . . . . ? O2 C1 C2 N1 87.83(12) . . . . ? O1 C1 C2 C3 86.56(14) . . . . ? O2 C1 C2 C3 -91.68(10) . . . . ? N1 C2 C3 C4 175.97(10) . . . . ? C1 C2 C3 C4 -4.51(15) . . . . ? N1 C2 C3 C8 -5.07(16) . . . . ? C1 C2 C3 C8 174.45(10) . . . . ? C8 C3 C4 C5 -0.37(17) . . . . ? C2 C3 C4 C5 178.60(11) . . . . ? C3 C4 C5 C6 0.02(19) . . . . ? C4 C5 C6 C7 0.1(2) . . . . ? C5 C6 C7 C8 0.23(19) . . . . ? C6 C7 C8 C3 -0.59(18) . . . . ? C4 C3 C8 C7 0.65(17) . . . . ? C2 C3 C8 C7 -178.32(10) . . . . ? C1 O2 C9 C10 179.92(10) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.146 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 ###END