data_lovely1m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 N2 O4' _chemical_formula_weight 378.42 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 12.934(3) _cell_length_b 8.1387(18) _cell_length_c 17.792(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.906(3) _cell_angle_gamma 90.00 _cell_volume 1866.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2891 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 28.10 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12098 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.36 _reflns_number_total 4503 _reflns_number_gt 3028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4503 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.92144(9) -0.20848(13) 0.04150(6) 0.0288(3) Uani 1 1 d . . . O2 O 0.57439(8) 0.17642(13) 0.07355(6) 0.0244(3) Uani 1 1 d . . . O3 O 0.37460(8) 0.28648(13) 0.06023(6) 0.0246(3) Uani 1 1 d . . . O4 O 0.31894(8) 0.56208(13) 0.12786(6) 0.0292(3) Uani 1 1 d . . . N1 N 0.85625(10) 0.62683(16) 0.30007(7) 0.0235(3) Uani 1 1 d . . . N2 N 0.90767(10) 0.40369(17) 0.23764(7) 0.0263(3) Uani 1 1 d . . . C1 C 0.93492(13) 0.5247(2) 0.28399(9) 0.0272(4) Uani 1 1 d . . . H1 H 1.0044 0.5399 0.3048 0.033 Uiso 1 1 calc R . . C2 C 0.80139(12) 0.42910(19) 0.21951(8) 0.0215(3) Uani 1 1 d . . . C3 C 0.73294(12) 0.33812(19) 0.17201(8) 0.0209(3) Uani 1 1 d . . . C4 C 0.62770(12) 0.39212(18) 0.16261(8) 0.0195(3) Uani 1 1 d . . . C5 C 0.54829(12) 0.31090(18) 0.11484(8) 0.0207(3) Uani 1 1 d . . . C6 C 0.44871(12) 0.36989(19) 0.10566(8) 0.0214(4) Uani 1 1 d . . . C7 C 0.42071(12) 0.5163(2) 0.14285(9) 0.0231(4) Uani 1 1 d . . . C8 C 0.49287(12) 0.59713(19) 0.18908(9) 0.0230(4) Uani 1 1 d . . . H8 H 0.4737 0.6946 0.2138 0.028 Uiso 1 1 calc R . . C9 C 0.59650(12) 0.53856(19) 0.20111(8) 0.0204(3) Uani 1 1 d . . . C10 C 0.66819(12) 0.62543(19) 0.25041(8) 0.0214(3) Uani 1 1 d . . . H10 H 0.6478 0.7196 0.2770 0.026 Uiso 1 1 calc R . . C11 C 0.76817(12) 0.56920(18) 0.25854(8) 0.0209(3) Uani 1 1 d . . . C12 C 0.77487(12) 0.18945(19) 0.13559(8) 0.0209(3) Uani 1 1 d . . . C13 C 0.77871(12) 0.03855(19) 0.17183(8) 0.0228(4) Uani 1 1 d . . . H13 H 0.7487 0.0282 0.2185 0.027 Uiso 1 1 calc R . . C14 C 0.82504(12) -0.09774(19) 0.14209(9) 0.0230(4) Uani 1 1 d . . . H14 H 0.8259 -0.2001 0.1678 0.028 Uiso 1 1 calc R . . C15 C 0.87016(12) -0.08307(19) 0.07447(9) 0.0225(4) Uani 1 1 d . . . C16 C 0.86580(13) 0.0662(2) 0.03647(9) 0.0266(4) Uani 1 1 d . . . H16 H 0.8949 0.0758 -0.0106 0.032 Uiso 1 1 calc R . . C17 C 0.81949(12) 0.2003(2) 0.06682(9) 0.0255(4) Uani 1 1 d . . . H17 H 0.8178 0.3021 0.0406 0.031 Uiso 1 1 calc R . . C18 C 0.94831(14) -0.3484(2) 0.08760(10) 0.0340(4) Uani 1 1 d . . . H18A H 0.9837 -0.3122 0.1356 0.051 Uiso 1 1 calc R . . H18B H 0.9945 -0.4204 0.0616 0.051 Uiso 1 1 calc R . . H18C H 0.8852 -0.4087 0.0972 0.051 Uiso 1 1 calc R . . C19 C 0.53302(13) 0.0234(2) 0.09764(10) 0.0303(4) Uani 1 1 d . . . H19A H 0.5599 0.0010 0.1498 0.045 Uiso 1 1 calc R . . H19B H 0.5538 -0.0653 0.0649 0.045 Uiso 1 1 calc R . . H19C H 0.4571 0.0300 0.0947 0.045 Uiso 1 1 calc R . . C20 C 0.35471(13) 0.3620(2) -0.01288(9) 0.0296(4) Uani 1 1 d . . . H20A H 0.3309 0.4751 -0.0067 0.044 Uiso 1 1 calc R . . H20B H 0.3011 0.2995 -0.0429 0.044 Uiso 1 1 calc R . . H20C H 0.4186 0.3627 -0.0387 0.044 Uiso 1 1 calc R . . C21 C 0.29739(13) 0.7328(2) 0.13156(10) 0.0305(4) Uani 1 1 d . . . H21A H 0.3208 0.7743 0.1818 0.046 Uiso 1 1 calc R . . H21B H 0.2225 0.7508 0.1218 0.046 Uiso 1 1 calc R . . H21C H 0.3339 0.7910 0.0935 0.046 Uiso 1 1 calc R . . C22 C 0.86408(13) 0.7690(2) 0.35017(9) 0.0281(4) Uani 1 1 d . . . H22A H 0.9338 0.7734 0.3765 0.042 Uiso 1 1 calc R . . H22B H 0.8125 0.7596 0.3872 0.042 Uiso 1 1 calc R . . H22C H 0.8512 0.8695 0.3205 0.042 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 0.0366(7) 0.0252(6) 0.0250(6) -0.0010(5) 0.0046(5) 0.0053(5) O2 0.0267(6) 0.0234(6) 0.0225(6) -0.0033(5) -0.0010(5) 0.0001(5) O3 0.0231(6) 0.0269(6) 0.0226(6) 0.0010(5) -0.0051(4) -0.0043(5) O4 0.0203(6) 0.0258(7) 0.0406(7) -0.0036(5) -0.0029(5) 0.0015(5) N1 0.0241(7) 0.0257(7) 0.0196(7) -0.0001(5) -0.0042(5) 0.0000(6) N2 0.0238(8) 0.0302(8) 0.0237(8) -0.0015(6) -0.0053(6) 0.0023(6) C1 0.0248(9) 0.0309(10) 0.0247(9) 0.0032(7) -0.0043(7) 0.0021(7) C2 0.0219(8) 0.0253(9) 0.0169(8) 0.0039(6) 0.0000(6) 0.0018(7) C3 0.0230(8) 0.0228(8) 0.0168(8) 0.0031(6) 0.0004(6) -0.0003(7) C4 0.0224(8) 0.0213(8) 0.0148(8) 0.0025(6) 0.0007(6) -0.0005(6) C5 0.0258(9) 0.0198(8) 0.0165(8) 0.0017(6) 0.0016(6) -0.0007(7) C6 0.0231(9) 0.0221(8) 0.0184(8) 0.0014(6) -0.0022(6) -0.0057(7) C7 0.0189(8) 0.0259(9) 0.0244(9) 0.0031(7) 0.0010(6) 0.0005(7) C8 0.0243(9) 0.0233(9) 0.0212(8) -0.0009(6) 0.0014(7) 0.0009(7) C9 0.0229(8) 0.0222(9) 0.0160(8) 0.0017(6) 0.0014(6) -0.0011(7) C10 0.0249(9) 0.0215(8) 0.0174(8) 0.0003(6) -0.0001(6) 0.0000(7) C11 0.0237(8) 0.0224(8) 0.0160(8) 0.0023(6) -0.0024(6) -0.0028(7) C12 0.0187(8) 0.0243(9) 0.0189(8) -0.0004(6) -0.0036(6) -0.0008(6) C13 0.0242(8) 0.0264(9) 0.0177(8) 0.0012(6) 0.0007(6) -0.0012(7) C14 0.0234(8) 0.0229(9) 0.0220(8) 0.0017(6) -0.0019(6) -0.0011(7) C15 0.0225(8) 0.0235(9) 0.0208(8) -0.0040(6) -0.0023(6) 0.0004(7) C16 0.0321(10) 0.0295(9) 0.0183(8) 0.0021(7) 0.0029(7) 0.0004(7) C17 0.0290(9) 0.0251(9) 0.0221(8) 0.0028(7) 0.0008(7) 0.0010(7) C18 0.0445(11) 0.0262(10) 0.0314(10) 0.0003(7) 0.0035(8) 0.0073(8) C19 0.0337(10) 0.0215(9) 0.0343(10) -0.0012(7) -0.0043(8) -0.0005(7) C20 0.0320(10) 0.0325(10) 0.0225(9) 0.0017(7) -0.0083(7) -0.0018(8) C21 0.0271(9) 0.0315(10) 0.0314(10) -0.0043(8) -0.0054(7) 0.0066(8) C22 0.0298(9) 0.0294(9) 0.0237(9) -0.0046(7) -0.0058(7) -0.0016(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 C15 1.3757(18) . ? O1 C18 1.4288(19) . ? O2 C5 1.3762(18) . ? O2 C19 1.4355(19) . ? O3 C6 1.3785(18) . ? O3 C20 1.4418(19) . ? O4 C7 1.3720(18) . ? O4 C21 1.4196(19) . ? N1 C1 1.363(2) . ? N1 C11 1.386(2) . ? N1 C22 1.459(2) . ? N2 C1 1.313(2) . ? N2 C2 1.4002(19) . ? C1 H1 0.9500 . ? C2 C3 1.385(2) . ? C2 C11 1.420(2) . ? C3 C4 1.427(2) . ? C3 C12 1.496(2) . ? C4 C5 1.437(2) . ? C4 C9 1.449(2) . ? C5 C6 1.371(2) . ? C6 C7 1.425(2) . ? C7 C8 1.360(2) . ? C8 C9 1.421(2) . ? C8 H8 0.9500 . ? C9 C10 1.411(2) . ? C10 C11 1.368(2) . ? C10 H10 0.9500 . ? C12 C13 1.386(2) . ? C12 C17 1.400(2) . ? C13 C14 1.387(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C16 C17 1.378(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C15 O1 C18 116.68(12) . . ? C5 O2 C19 114.58(12) . . ? C6 O3 C20 112.37(12) . . ? C7 O4 C21 116.47(12) . . ? C1 N1 C11 106.03(13) . . ? C1 N1 C22 126.72(13) . . ? C11 N1 C22 127.25(13) . . ? C1 N2 C2 103.85(13) . . ? N2 C1 N1 115.09(15) . . ? N2 C1 H1 122.5 . . ? N1 C1 H1 122.5 . . ? C3 C2 N2 128.70(14) . . ? C3 C2 C11 121.54(14) . . ? N2 C2 C11 109.76(13) . . ? C2 C3 C4 117.42(14) . . ? C2 C3 C12 117.41(13) . . ? C4 C3 C12 125.17(13) . . ? C3 C4 C5 123.65(14) . . ? C3 C4 C9 119.97(14) . . ? C5 C4 C9 116.36(14) . . ? C6 C5 O2 119.06(13) . . ? C6 C5 C4 121.73(14) . . ? O2 C5 C4 119.08(13) . . ? C5 C6 O3 119.76(14) . . ? C5 C6 C7 120.73(14) . . ? O3 C6 C7 119.51(14) . . ? C8 C7 O4 125.70(15) . . ? C8 C7 C6 119.80(14) . . ? O4 C7 C6 114.49(13) . . ? C7 C8 C9 121.22(15) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 119.13(14) . . ? C10 C9 C4 120.75(14) . . ? C8 C9 C4 120.12(14) . . ? C11 C10 C9 117.60(14) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C10 C11 N1 132.06(15) . . ? C10 C11 C2 122.67(14) . . ? N1 C11 C2 105.25(13) . . ? C13 C12 C17 117.50(14) . . ? C13 C12 C3 121.01(13) . . ? C17 C12 C3 121.28(14) . . ? C12 C13 C14 122.05(14) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 119.32(14) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? O1 C15 C14 124.07(14) . . ? O1 C15 C16 116.24(13) . . ? C14 C15 C16 119.68(14) . . ? C17 C16 C15 120.20(15) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C12 121.21(15) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? O1 C18 H18A 109.5 . . ? O1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 C21 H21A 109.5 . . ? O4 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O4 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C22 H22A 109.5 . . ? N1 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N1 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.377 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.060