data_global _audit_creation_method 'APEX2 v2012.4-3' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common Mayada_L14P_20_05_14 _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 N4 O8' _chemical_formula_iupac ? _chemical_formula_weight 450.45 _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.4582(9) _cell_length_b 6.4854(5) _cell_length_c 14.0935(11) _cell_angle_alpha 90 _cell_angle_beta 93.889(6) _cell_angle_gamma 90 _cell_volume 1044.89(14) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1762 _cell_measurement_theta_min 3.8668 _cell_measurement_theta_max 64.5065 _cell_measurement_temperature 296.(2) _exptl_crystal_description Block _exptl_crystal_colour 'clear light colourless' _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.040 _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 5605 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_theta_min 3.87 _diffrn_reflns_theta_max 66.64 _diffrn_reflns_theta_full 66.64 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measured_fraction_theta_full 0.973 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _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. ; _reflns_number_total 1804 _reflns_number_gt 1170 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.1091 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_gt 0.1649 _refine_ls_wR_factor_ref 0.1862 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.170 _refine_ls_number_reflns 1804 _refine_ls_number_parameters 153 _refine_ls_number_restraints 4 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.8157P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.260 _refine_diff_density_min -0.480 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Instrument Service v2012.4.0.0' _computing_cell_refinement 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_data_reduction 'SAINT V8.18C (Bruker AXS Inc., 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.3622(3) 0.1356(6) 0.3019(2) 0.0307(9) Uani d . 1 . . C C7 0.4771(3) 0.0582(6) 0.3341(3) 0.0340(9) Uani d . 1 . . H H7 0.5019 -0.0657 0.3091 0.041 Uiso calc R 1 . . C C3 0.2033(3) 0.3774(5) 0.3084(3) 0.0308(9) Uani d . 1 . . C C8 0.7310(3) 0.1311(6) 0.4792(3) 0.0299(9) Uani d . 1 . . C C4 0.1328(3) 0.2508(6) 0.2468(2) 0.0306(8) Uani d . 1 . . C C2 0.3169(3) 0.3209(5) 0.3341(3) 0.0310(9) Uani d . 1 . . H H2 0.3639 0.4069 0.3732 0.037 Uiso calc R 1 . . C C6 0.2923(3) 0.0150(6) 0.2395(3) 0.0397(10) Uani d . 1 . . H H6 0.3217 -0.1076 0.2165 0.048 Uiso calc R 1 . . C C5 0.1793(3) 0.0751(6) 0.2111(3) 0.0393(10) Uani d . 1 . . H H5 0.1347 -0.0046 0.1674 0.047 Uiso calc R 1 . . C C10 0.9504(3) 0.0724(6) 0.4831(3) 0.0333(9) Uani d . 1 . . H H10A 0.9642 0.2074 0.5113 0.04 Uiso calc R 1 . . H H10B 0.9492 0.0872 0.4146 0.04 Uiso calc R 1 . . C C9 0.8322(3) -0.0082(6) 0.5101(3) 0.0330(9) Uani d . 1 . . H H9A 0.8188 -0.1429 0.4816 0.04 Uiso calc R 1 . . H H9B 0.8344 -0.025 0.5786 0.04 Uiso calc R 1 . . N N2 0.6484(2) 0.0455(5) 0.4200(2) 0.0340(8) Uani d . 1 . . H H2A 0.6591 -0.0757 0.3975 0.041 Uiso calc R 1 . . N N1 0.5455(2) 0.1511(5) 0.3948(2) 0.0331(8) Uani d . 1 . . O O2 0.0214(2) 0.3130(4) 0.2273(2) 0.0458(8) Uani d . 1 . . H H2B -0.0177 0.2162 0.2052 0.069 Uiso calc R 1 . . O O3 0.7245(2) 0.3108(4) 0.5057(2) 0.0458(8) Uani d . 1 . . O O1 0.1517(2) 0.5497(4) 0.3421(2) 0.0507(9) Uani d . 1 . . H H1 0.1936 0.5983 0.3861 0.076 Uiso calc R 1 . . O O4 0.5601(4) 0.6431(6) 0.4326(3) 0.0791(12) Uani d D 1 . . H H4A 0.547(4) 0.686(9) 0.4854(17) 0.119 Uiso d D 1 . . H H4B 0.610(4) 0.554(7) 0.443(3) 0.119 Uiso d D 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0240(17) 0.039(2) 0.029(2) -0.0034(15) 0.0011(15) -0.0022(16) C7 0.0240(18) 0.036(2) 0.042(2) 0.0011(15) 0.0015(17) -0.0090(17) C3 0.0316(18) 0.0283(19) 0.031(2) 0.0006(15) -0.0075(16) 0.0004(15) C8 0.0201(16) 0.036(2) 0.034(2) 0.0041(15) -0.0020(15) 0.0029(16) C4 0.0256(17) 0.035(2) 0.030(2) -0.0026(15) -0.0057(15) 0.0018(16) C2 0.0253(17) 0.034(2) 0.032(2) -0.0022(15) -0.0071(15) -0.0031(16) C6 0.033(2) 0.045(2) 0.041(2) 0.0012(17) -0.0013(18) -0.0162(18) C5 0.032(2) 0.051(3) 0.034(2) -0.0070(18) -0.0048(17) -0.0121(19) C10 0.0230(17) 0.042(2) 0.035(2) 0.0070(16) 0.0021(15) 0.0039(18) C9 0.0216(17) 0.036(2) 0.041(2) 0.0052(15) 0.0016(16) 0.0030(17) N2 0.0220(15) 0.0340(17) 0.045(2) 0.0051(13) -0.0020(14) -0.0110(14) N1 0.0212(14) 0.0350(18) 0.0426(19) 0.0054(12) -0.0029(14) -0.0004(14) O2 0.0291(13) 0.0450(17) 0.0602(19) -0.0002(12) -0.0202(13) -0.0034(14) O3 0.0374(14) 0.0388(16) 0.0585(18) 0.0127(12) -0.0171(13) -0.0178(14) O1 0.0422(16) 0.0399(16) 0.065(2) 0.0146(13) -0.0286(15) -0.0184(14) O4 0.093(3) 0.062(3) 0.081(3) 0.012(2) 0.002(2) -0.008(2) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . 1.390(5) ? C1 C2 . 1.397(5) ? C1 C7 . 1.453(5) ? C7 N1 . 1.272(4) ? C3 O1 . 1.365(4) ? C3 C2 . 1.376(5) ? C3 C4 . 1.409(5) ? C8 O3 . 1.228(4) ? C8 N2 . 1.339(4) ? C8 C9 . 1.510(4) ? C4 O2 . 1.349(4) ? C4 C5 . 1.369(5) ? C6 C5 . 1.385(5) ? C10 C9 . 1.524(5) ? C10 C10 3_756 1.526(6) ? N2 N1 . 1.388(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 . . 118.6(3) ? C6 C1 C7 . . 118.3(3) ? C2 C1 C7 . . 123.0(3) ? N1 C7 C1 . . 123.4(3) ? O1 C3 C2 . . 123.4(3) ? O1 C3 C4 . . 116.6(3) ? C2 C3 C4 . . 120.0(3) ? O3 C8 N2 . . 121.9(3) ? O3 C8 C9 . . 122.7(3) ? N2 C8 C9 . . 115.4(3) ? O2 C4 C5 . . 124.1(3) ? O2 C4 C3 . . 116.6(3) ? C5 C4 C3 . . 119.4(3) ? C3 C2 C1 . . 120.6(3) ? C5 C6 C1 . . 120.8(4) ? C4 C5 C6 . . 120.5(3) ? C9 C10 C10 . 3_756 111.6(4) ? C8 C9 C10 . . 113.6(3) ? C8 N2 N1 . . 120.5(3) ? C7 N1 N2 . . 114.4(3) ?